The structures of six symmetrically 4,6-disubstituted 2-aminopyrimidines, four of them containing a 5-nitroso substituent, have been determined. The nitroso compounds, in particular, exhibit polarized molecular–electronic structures leading to extensive charge-assisted hydrogen bonding. The intermolecular interactions observed include hard hydrogen bonds of N—H
N and N—H
O types together with O—H
O and O—H
N types in 2-amino-4,6-bis(2-hydroxyethylamino)-5-nitrosopyrimidine; soft hydrogen bonds of the C—H
O type in both 2-amino-4,6-bis(morpholino)-5-nitrosopyrimidine (3) and 2-amino-4,6-bis(benzylamino)-5-nitrosopyrimidine (4), and of the C—H
π(arene) type in both 2-amino-4,6-bis(piperidino)pyrimidine (1) and 2-amino-5-nitroso-4,6-bis(3-pyridylmethoxy)pyrimidine (5); and aromatic π
π stacking interactions in 2-amino-5-nitroso-4,6-bis(3-pyridylmethoxy)pyrimidine. The supramolecular structures formed by the hard hydrogen bonds are finite, zero-dimensional in (1), one-dimensional in 2-amino-4,6-bis(3-pyridylmethoxy)pyrimidine (2), two-dimensional in both (3) and (4), and three-dimensional in both (5) and 2-amino-4,6-bis(2-hydroxyethylamino)-5-nitrosopyrimidine.
Supporting information
CCDC references: 230845; 230846; 230847; 230848; 230849; 230850
For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b) for (I), (II), (III), (VI); SHELXS97 (Sheldrick, 1997)b for (IV); SHELXS972-66 (Sheldrick, 1997b) for (V). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a) for (I), (II), (III), (IV), (VI). Molecular graphics: PLATON (Spek, 2003) for (I), (II), (IV); PLATON (Spek, 2002) for (III), (VI). For all compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).
(I) 2-Amino-4,6-bis(piperidino)pyrimidine
top
Crystal data top
C14H23N5 | F(000) = 568 |
Mr = 261.37 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3100 reflections |
a = 12.1473 (4) Å | θ = 3.1–27.5° |
b = 9.8811 (3) Å | µ = 0.08 mm−1 |
c = 11.4068 (3) Å | T = 120 K |
β = 96.6490 (1)° | Block, orange |
V = 1359.93 (7) Å3 | 0.35 × 0.30 × 0.22 mm |
Z = 4 | |
Data collection top
Kappa-CCD diffractometer | 3100 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2195 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −15→15 |
Tmin = 0.968, Tmax = 0.983 | k = −10→12 |
13657 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.176P] where P = (Fo2 + 2Fc2)/3 |
3100 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Crystal data top
C14H23N5 | V = 1359.93 (7) Å3 |
Mr = 261.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1473 (4) Å | µ = 0.08 mm−1 |
b = 9.8811 (3) Å | T = 120 K |
c = 11.4068 (3) Å | 0.35 × 0.30 × 0.22 mm |
β = 96.6490 (1)° | |
Data collection top
Kappa-CCD diffractometer | 3100 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2195 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.983 | Rint = 0.069 |
13657 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.20 e Å−3 |
3100 reflections | Δρmin = −0.29 e Å−3 |
172 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.39389 (9) | 0.53485 (12) | 0.34772 (10) | 0.0179 (3) | |
C2 | 0.35055 (11) | 0.62533 (14) | 0.41702 (11) | 0.0169 (3) | |
N2 | 0.38927 (10) | 0.62161 (13) | 0.53323 (10) | 0.0220 (3) | |
N3 | 0.27377 (9) | 0.72041 (12) | 0.38535 (9) | 0.0176 (3) | |
C4 | 0.23614 (11) | 0.72498 (14) | 0.26940 (11) | 0.0172 (3) | |
C42 | 0.11193 (12) | 0.84765 (16) | 0.11484 (12) | 0.0244 (3) | |
C43 | −0.01295 (12) | 0.83474 (17) | 0.09880 (13) | 0.0278 (4) | |
C44 | −0.06520 (13) | 0.92704 (18) | 0.18430 (14) | 0.0310 (4) | |
C45 | −0.01323 (13) | 0.90069 (18) | 0.31031 (13) | 0.0304 (4) | |
C46 | 0.11195 (13) | 0.90994 (17) | 0.32031 (13) | 0.0284 (4) | |
N4 | 0.15553 (10) | 0.81933 (14) | 0.23639 (10) | 0.0269 (3) | |
C5 | 0.27625 (11) | 0.63700 (14) | 0.18796 (11) | 0.0172 (3) | |
C6 | 0.35579 (11) | 0.54212 (14) | 0.23137 (12) | 0.0175 (3) | |
N6 | 0.40198 (10) | 0.45221 (13) | 0.15855 (10) | 0.0230 (3) | |
C62 | 0.36417 (12) | 0.44574 (15) | 0.03232 (12) | 0.0222 (3) | |
C63 | 0.27085 (12) | 0.34419 (15) | 0.00609 (12) | 0.0226 (3) | |
C64 | 0.30803 (13) | 0.20559 (16) | 0.05383 (13) | 0.0267 (4) | |
C65 | 0.35250 (14) | 0.21353 (17) | 0.18382 (13) | 0.0309 (4) | |
C66 | 0.44216 (14) | 0.32068 (17) | 0.20522 (14) | 0.0329 (4) | |
H2A | 0.4401 | 0.5620 | 0.5594 | 0.026* | |
H2B | 0.3636 | 0.6788 | 0.5826 | 0.026* | |
H42A | 0.1442 | 0.7834 | 0.0616 | 0.029* | |
H42B | 0.1332 | 0.9404 | 0.0936 | 0.029* | |
H43A | −0.0339 | 0.7397 | 0.1125 | 0.033* | |
H43B | −0.0417 | 0.8589 | 0.0167 | 0.033* | |
H44A | −0.0537 | 1.0228 | 0.1634 | 0.037* | |
H44B | −0.1460 | 0.9101 | 0.1782 | 0.037* | |
H45A | −0.0416 | 0.9678 | 0.3638 | 0.036* | |
H45B | −0.0349 | 0.8095 | 0.3353 | 0.036* | |
H46A | 0.1341 | 1.0041 | 0.3048 | 0.034* | |
H46B | 0.1436 | 0.8856 | 0.4015 | 0.034* | |
H5 | 0.2503 | 0.6417 | 0.1062 | 0.021* | |
H62A | 0.4270 | 0.4197 | −0.0110 | 0.027* | |
H62B | 0.3382 | 0.5363 | 0.0043 | 0.027* | |
H63A | 0.2496 | 0.3385 | −0.0802 | 0.027* | |
H63B | 0.2053 | 0.3743 | 0.0432 | 0.027* | |
H64A | 0.2446 | 0.1421 | 0.0435 | 0.032* | |
H64B | 0.3665 | 0.1701 | 0.0085 | 0.032* | |
H65A | 0.2911 | 0.2354 | 0.2306 | 0.037* | |
H65B | 0.3833 | 0.1245 | 0.2105 | 0.037* | |
H66A | 0.4655 | 0.3287 | 0.2910 | 0.039* | |
H66B | 0.5075 | 0.2930 | 0.1665 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0186 (6) | 0.0180 (6) | 0.0165 (6) | 0.0001 (5) | −0.0008 (4) | −0.0016 (4) |
C2 | 0.0159 (7) | 0.0161 (7) | 0.0184 (7) | −0.0036 (5) | 0.0009 (5) | 0.0010 (5) |
N2 | 0.0248 (7) | 0.0236 (7) | 0.0164 (6) | 0.0076 (5) | −0.0031 (4) | −0.0018 (5) |
N3 | 0.0170 (6) | 0.0202 (6) | 0.0154 (6) | 0.0015 (5) | 0.0011 (4) | 0.0005 (4) |
C4 | 0.0141 (7) | 0.0202 (7) | 0.0174 (7) | −0.0013 (6) | 0.0014 (5) | 0.0012 (5) |
C42 | 0.0248 (8) | 0.0315 (9) | 0.0164 (7) | 0.0090 (6) | 0.0011 (5) | 0.0021 (6) |
C43 | 0.0255 (8) | 0.0335 (9) | 0.0233 (8) | 0.0010 (7) | −0.0027 (6) | −0.0017 (6) |
C44 | 0.0190 (8) | 0.0444 (11) | 0.0296 (9) | 0.0056 (7) | 0.0023 (6) | −0.0010 (7) |
C45 | 0.0320 (9) | 0.0357 (9) | 0.0248 (8) | 0.0098 (7) | 0.0087 (6) | 0.0009 (6) |
C46 | 0.0306 (9) | 0.0345 (9) | 0.0188 (8) | 0.0144 (7) | −0.0027 (6) | −0.0064 (6) |
N4 | 0.0264 (7) | 0.0384 (8) | 0.0153 (6) | 0.0172 (6) | −0.0009 (5) | −0.0013 (5) |
C5 | 0.0167 (7) | 0.0207 (7) | 0.0138 (7) | −0.0020 (5) | −0.0002 (5) | 0.0000 (5) |
C6 | 0.0153 (7) | 0.0176 (7) | 0.0195 (7) | −0.0026 (6) | 0.0017 (5) | −0.0018 (5) |
N6 | 0.0229 (6) | 0.0253 (7) | 0.0195 (6) | 0.0041 (5) | −0.0032 (5) | −0.0086 (5) |
C62 | 0.0240 (8) | 0.0241 (8) | 0.0191 (7) | 0.0006 (6) | 0.0053 (5) | −0.0050 (6) |
C63 | 0.0212 (7) | 0.0266 (8) | 0.0194 (7) | 0.0000 (6) | −0.0005 (5) | −0.0022 (6) |
C64 | 0.0261 (8) | 0.0242 (8) | 0.0290 (8) | −0.0020 (7) | −0.0001 (6) | −0.0030 (6) |
C65 | 0.0399 (10) | 0.0277 (9) | 0.0250 (8) | 0.0115 (7) | 0.0033 (6) | 0.0022 (6) |
C66 | 0.0342 (9) | 0.0310 (9) | 0.0300 (9) | 0.0167 (7) | −0.0109 (6) | −0.0121 (7) |
Geometric parameters (Å, º) top
N1—C2 | 1.3408 (18) | C46—N4 | 1.4545 (19) |
N1—C6 | 1.3559 (17) | C46—H46A | 0.99 |
C2—N3 | 1.3435 (17) | C46—H46B | 0.99 |
C2—N2 | 1.3548 (17) | C5—C6 | 1.3954 (19) |
N2—H2A | 0.88 | C5—H5 | 0.95 |
N2—H2B | 0.88 | C6—N6 | 1.3791 (18) |
N3—C4 | 1.3492 (17) | N6—C62 | 1.4612 (18) |
C4—N4 | 1.3728 (18) | N6—C66 | 1.466 (2) |
C4—C5 | 1.4003 (19) | C62—C63 | 1.518 (2) |
C42—N4 | 1.4529 (17) | C62—H62A | 0.99 |
C42—C43 | 1.512 (2) | C62—H62B | 0.99 |
C42—H42A | 0.99 | C63—C64 | 1.523 (2) |
C42—H42B | 0.99 | C63—H63A | 0.99 |
C43—C44 | 1.526 (2) | C63—H63B | 0.99 |
C43—H43A | 0.99 | C64—C65 | 1.520 (2) |
C43—H43B | 0.99 | C64—H64A | 0.99 |
C44—C45 | 1.524 (2) | C64—H64B | 0.99 |
C44—H44A | 0.99 | C65—C66 | 1.518 (2) |
C44—H44B | 0.99 | C65—H65A | 0.99 |
C45—C46 | 1.514 (2) | C65—H65B | 0.99 |
C45—H45A | 0.99 | C66—H66A | 0.99 |
C45—H45B | 0.99 | C66—H66B | 0.99 |
| | | |
C2—N1—C6 | 115.40 (11) | C4—N4—C46 | 122.68 (11) |
N1—C2—N3 | 127.99 (12) | C42—N4—C46 | 112.91 (11) |
N1—C2—N2 | 116.31 (12) | C6—C5—C4 | 117.48 (12) |
N3—C2—N2 | 115.69 (12) | C6—C5—H5 | 121.3 |
C2—N2—H2A | 120.0 | C4—C5—H5 | 121.3 |
C2—N2—H2B | 120.0 | N1—C6—N6 | 116.03 (12) |
H2A—N2—H2B | 120.0 | N1—C6—C5 | 121.79 (12) |
C2—N3—C4 | 115.64 (11) | N6—C6—C5 | 122.16 (12) |
N3—C4—N4 | 116.20 (11) | C6—N6—C62 | 121.22 (12) |
N3—C4—C5 | 121.69 (12) | C6—N6—C66 | 119.59 (12) |
N4—C4—C5 | 122.11 (12) | C62—N6—C66 | 111.86 (11) |
N4—C42—C43 | 110.42 (12) | N6—C62—C63 | 111.44 (12) |
N4—C42—H42A | 109.6 | N6—C62—H62A | 109.3 |
C43—C42—H42A | 109.6 | C63—C62—H62A | 109.3 |
N4—C42—H42B | 109.6 | N6—C62—H62B | 109.3 |
C43—C42—H42B | 109.6 | C63—C62—H62B | 109.3 |
H42A—C42—H42B | 108.1 | H62A—C62—H62B | 108.0 |
C42—C43—C44 | 110.97 (12) | C62—C63—C64 | 109.89 (12) |
C42—C43—H43A | 109.4 | C62—C63—H63A | 109.7 |
C44—C43—H43A | 109.4 | C64—C63—H63A | 109.7 |
C42—C43—H43B | 109.4 | C62—C63—H63B | 109.7 |
C44—C43—H43B | 109.4 | C64—C63—H63B | 109.7 |
H43A—C43—H43B | 108.0 | H63A—C63—H63B | 108.2 |
C45—C44—C43 | 110.07 (13) | C65—C64—C63 | 111.07 (12) |
C45—C44—H44A | 109.6 | C65—C64—H64A | 109.4 |
C43—C44—H44A | 109.6 | C63—C64—H64A | 109.4 |
C45—C44—H44B | 109.6 | C65—C64—H64B | 109.4 |
C43—C44—H44B | 109.6 | C63—C64—H64B | 109.4 |
H44A—C44—H44B | 108.2 | H64A—C64—H64B | 108.0 |
C46—C45—C44 | 111.31 (12) | C66—C65—C64 | 111.11 (13) |
C46—C45—H45A | 109.4 | C66—C65—H65A | 109.4 |
C44—C45—H45A | 109.4 | C64—C65—H65A | 109.4 |
C46—C45—H45B | 109.4 | C66—C65—H65B | 109.4 |
C44—C45—H45B | 109.4 | C64—C65—H65B | 109.4 |
H45A—C45—H45B | 108.0 | H65A—C65—H65B | 108.0 |
N4—C46—C45 | 110.61 (12) | N6—C66—C65 | 110.93 (12) |
N4—C46—H46A | 109.5 | N6—C66—H66A | 109.5 |
C45—C46—H46A | 109.5 | C65—C66—H66A | 109.5 |
N4—C46—H46B | 109.5 | N6—C66—H66B | 109.5 |
C45—C46—H46B | 109.5 | C65—C66—H66B | 109.5 |
H46A—C46—H46B | 108.1 | H66A—C66—H66B | 108.0 |
C4—N4—C42 | 124.21 (11) | | |
| | | |
C6—N1—C2—N3 | 0.8 (2) | N3—C4—C5—C6 | 1.05 (19) |
C6—N1—C2—N2 | −178.64 (11) | N4—C4—C5—C6 | −178.07 (13) |
N1—C2—N3—C4 | −0.1 (2) | C2—N1—C6—N6 | 178.21 (12) |
N2—C2—N3—C4 | 179.31 (12) | C2—N1—C6—C5 | −0.50 (19) |
C2—N3—C4—N4 | 178.33 (12) | C4—C5—C6—N1 | −0.34 (19) |
C2—N3—C4—C5 | −0.83 (19) | C4—C5—C6—N6 | −178.97 (12) |
N4—C42—C43—C44 | 56.19 (17) | N1—C6—N6—C62 | 177.09 (12) |
C42—C43—C44—C45 | −53.41 (18) | C5—C6—N6—C62 | −4.2 (2) |
C43—C44—C45—C46 | 52.82 (18) | N1—C6—N6—C66 | 29.43 (19) |
C44—C45—C46—N4 | −54.93 (18) | C5—C6—N6—C66 | −151.86 (13) |
N3—C4—N4—C42 | 174.30 (13) | C6—N6—C62—C63 | −90.61 (16) |
C5—C4—N4—C42 | −6.5 (2) | C66—N6—C62—C63 | 59.31 (16) |
N3—C4—N4—C46 | −0.1 (2) | N6—C62—C63—C64 | −56.44 (15) |
C5—C4—N4—C46 | 179.06 (14) | C62—C63—C64—C65 | 53.52 (16) |
C43—C42—N4—C4 | 125.81 (15) | C63—C64—C65—C66 | −53.19 (17) |
C43—C42—N4—C46 | −59.30 (17) | C6—N6—C66—C65 | 92.50 (15) |
C45—C46—N4—C4 | −126.42 (15) | C62—N6—C66—C65 | −57.97 (17) |
C45—C46—N4—C42 | 58.60 (17) | C64—C65—C66—N6 | 54.77 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.88 | 2.37 | 3.216 (2) | 162 |
C66—H66B···Cg1ii | 0.99 | 2.68 | 3.518 (2) | 142 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2. |
(II) 2-Amino-4,6-bis(3-pyridylmethoxy)pyrimidine
top
Crystal data top
C16H15N5O2 | Z = 6 |
Mr = 309.33 | F(000) = 972 |
Triclinic, P1 | Dx = 1.401 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3545 (3) Å | Cell parameters from 9847 reflections |
b = 12.7528 (4) Å | θ = 2.9–27.5° |
c = 16.9511 (6) Å | µ = 0.10 mm−1 |
α = 70.038 (1)° | T = 120 K |
β = 73.206 (1)° | Plate, colourless |
γ = 79.626 (1)° | 0.40 × 0.20 × 0.05 mm |
V = 2199.62 (12) Å3 | |
Data collection top
Kappa-CCD diffractometer | 4349 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.086 |
Graphite monochromator | θmax = 27.5°, θmin = 2.9° |
ϕ scans, and ω scans with κ offsets | h = −14→14 |
32137 measured reflections | k = −16→16 |
9847 independent reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0648P)2] where P = (Fo2 + 2Fc2)/3 |
9847 reflections | (Δ/σ)max < 0.001 |
622 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Crystal data top
C16H15N5O2 | γ = 79.626 (1)° |
Mr = 309.33 | V = 2199.62 (12) Å3 |
Triclinic, P1 | Z = 6 |
a = 11.3545 (3) Å | Mo Kα radiation |
b = 12.7528 (4) Å | µ = 0.10 mm−1 |
c = 16.9511 (6) Å | T = 120 K |
α = 70.038 (1)° | 0.40 × 0.20 × 0.05 mm |
β = 73.206 (1)° | |
Data collection top
Kappa-CCD diffractometer | 4349 reflections with I > 2σ(I) |
32137 measured reflections | Rint = 0.086 |
9847 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.30 e Å−3 |
9847 reflections | Δρmin = −0.34 e Å−3 |
622 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 0.87818 (18) | 0.94519 (16) | −0.06184 (12) | 0.0223 (5) | |
N12 | 0.77832 (19) | 0.99790 (17) | 0.05942 (13) | 0.0289 (5) | |
C12 | 0.8026 (2) | 0.92063 (19) | 0.01890 (15) | 0.0212 (6) | |
O14 | 0.72837 (16) | 0.64697 (13) | 0.06292 (10) | 0.0268 (4) | |
N13 | 0.74856 (18) | 0.82393 (16) | 0.06230 (13) | 0.0232 (5) | |
C14 | 0.7762 (2) | 0.7475 (2) | 0.02195 (15) | 0.0219 (6) | |
C141 | 0.6409 (2) | 0.5098 (2) | 0.19496 (15) | 0.0242 (6) | |
C142 | 0.5349 (2) | 0.4758 (2) | 0.25884 (16) | 0.0279 (6) | |
N143 | 0.5199 (2) | 0.36945 (18) | 0.30868 (13) | 0.0327 (6) | |
C144 | 0.6137 (3) | 0.2934 (2) | 0.29504 (17) | 0.0352 (7) | |
C145 | 0.7214 (3) | 0.3176 (2) | 0.23109 (16) | 0.0323 (7) | |
C146 | 0.7357 (2) | 0.4278 (2) | 0.18103 (16) | 0.0270 (6) | |
C147 | 0.6543 (2) | 0.6321 (2) | 0.15030 (15) | 0.0244 (6) | |
C15 | 0.8524 (2) | 0.7625 (2) | −0.06099 (16) | 0.0253 (6) | |
C16 | 0.9004 (2) | 0.8651 (2) | −0.09824 (15) | 0.0224 (6) | |
C161 | 1.0966 (2) | 0.99845 (19) | −0.30979 (15) | 0.0206 (6) | |
C162 | 1.1502 (2) | 1.0970 (2) | −0.36206 (16) | 0.0250 (6) | |
N163 | 1.21208 (19) | 1.11470 (17) | −0.44527 (13) | 0.0260 (5) | |
C164 | 1.2220 (2) | 1.0319 (2) | −0.47883 (16) | 0.0254 (6) | |
C165 | 1.1728 (2) | 0.9311 (2) | −0.43273 (16) | 0.0288 (6) | |
C166 | 1.1083 (2) | 0.9150 (2) | −0.34687 (16) | 0.0266 (6) | |
C167 | 1.0290 (2) | 0.9902 (2) | −0.21792 (15) | 0.0237 (6) | |
O16 | 0.97701 (16) | 0.88369 (14) | −0.17938 (10) | 0.0282 (4) | |
N21 | 0.30633 (17) | 0.84508 (16) | 0.20722 (12) | 0.0202 (5) | |
C22 | 0.2483 (2) | 0.7498 (2) | 0.24840 (15) | 0.0203 (6) | |
N22 | 0.27140 (18) | 0.67304 (16) | 0.20787 (13) | 0.0248 (5) | |
N23 | 0.16874 (17) | 0.72582 (16) | 0.32861 (12) | 0.0197 (5) | |
C24 | 0.1523 (2) | 0.8023 (2) | 0.36803 (15) | 0.0183 (5) | |
C241 | −0.0494 (2) | 0.6680 (2) | 0.57715 (15) | 0.0187 (5) | |
C242 | −0.0981 (2) | 0.5668 (2) | 0.62922 (15) | 0.0234 (6) | |
N243 | −0.16557 (19) | 0.54836 (16) | 0.71060 (13) | 0.0254 (5) | |
C244 | −0.1874 (2) | 0.6335 (2) | 0.74329 (16) | 0.0283 (6) | |
C245 | −0.1450 (2) | 0.7376 (2) | 0.69758 (16) | 0.0285 (6) | |
C246 | −0.0748 (2) | 0.7549 (2) | 0.61256 (15) | 0.0234 (6) | |
C247 | 0.0222 (2) | 0.6780 (2) | 0.48558 (15) | 0.0213 (6) | |
O24 | 0.07882 (15) | 0.78180 (13) | 0.45002 (10) | 0.0224 (4) | |
C25 | 0.2058 (2) | 0.9033 (2) | 0.33307 (15) | 0.0208 (5) | |
C26 | 0.2823 (2) | 0.9186 (2) | 0.25018 (15) | 0.0196 (5) | |
C261 | 0.4596 (2) | 1.14720 (19) | 0.09434 (15) | 0.0194 (5) | |
C262 | 0.5217 (2) | 1.1880 (2) | 0.00743 (16) | 0.0228 (6) | |
N263 | 0.56746 (19) | 1.28729 (17) | −0.02859 (13) | 0.0262 (5) | |
C264 | 0.5524 (2) | 1.3505 (2) | 0.02269 (16) | 0.0264 (6) | |
C265 | 0.4930 (2) | 1.3180 (2) | 0.10921 (16) | 0.0263 (6) | |
C266 | 0.4465 (2) | 1.2143 (2) | 0.14529 (16) | 0.0237 (6) | |
C267 | 0.4133 (2) | 1.0333 (2) | 0.12567 (15) | 0.0217 (6) | |
O26 | 0.33516 (15) | 1.01680 (13) | 0.21214 (10) | 0.0239 (4) | |
N31 | 0.22324 (18) | 0.38269 (16) | 0.59576 (12) | 0.0219 (5) | |
C32 | 0.2989 (2) | 0.40907 (19) | 0.51456 (15) | 0.0209 (6) | |
N32 | 0.32180 (19) | 0.33374 (17) | 0.47243 (13) | 0.0257 (5) | |
N33 | 0.35435 (18) | 0.50520 (16) | 0.47244 (12) | 0.0210 (5) | |
C34 | 0.3326 (2) | 0.57747 (19) | 0.51663 (15) | 0.0197 (5) | |
O34 | 0.13685 (15) | 0.43706 (14) | 0.71833 (10) | 0.0261 (4) | |
C341 | 0.0034 (2) | 0.33037 (19) | 0.84513 (15) | 0.0205 (5) | |
C342 | −0.0415 (2) | 0.2296 (2) | 0.90127 (15) | 0.0241 (6) | |
N343 | −0.11559 (19) | 0.21831 (17) | 0.98053 (13) | 0.0258 (5) | |
C344 | −0.1454 (2) | 0.3102 (2) | 1.00570 (16) | 0.0276 (6) | |
C345 | −0.1053 (2) | 0.4133 (2) | 0.95551 (16) | 0.0300 (6) | |
C346 | −0.0290 (2) | 0.4230 (2) | 0.87357 (16) | 0.0252 (6) | |
C347 | 0.0799 (2) | 0.3334 (2) | 0.75599 (16) | 0.0240 (6) | |
C35 | 0.2598 (2) | 0.5599 (2) | 0.60073 (16) | 0.0241 (6) | |
C36 | 0.2081 (2) | 0.4587 (2) | 0.63568 (15) | 0.0207 (6) | |
C361 | 0.5078 (2) | 0.8069 (2) | 0.36260 (15) | 0.0203 (5) | |
C362 | 0.5814 (2) | 0.8438 (2) | 0.27872 (16) | 0.0243 (6) | |
N363 | 0.62695 (19) | 0.94416 (17) | 0.24304 (13) | 0.0260 (5) | |
C364 | 0.5989 (2) | 1.0116 (2) | 0.29219 (16) | 0.0255 (6) | |
C365 | 0.5275 (2) | 0.9826 (2) | 0.37621 (16) | 0.0284 (6) | |
C366 | 0.4822 (2) | 0.8784 (2) | 0.41204 (16) | 0.0248 (6) | |
C367 | 0.4603 (2) | 0.69374 (19) | 0.39224 (15) | 0.0220 (6) | |
O36 | 0.38392 (15) | 0.67679 (13) | 0.47868 (10) | 0.0244 (4) | |
H12A | 0.7292 | 0.9847 | 0.1119 | 0.035* | |
H12B | 0.8114 | 1.0621 | 0.0338 | 0.035* | |
H142 | 0.4688 | 0.5312 | 0.2679 | 0.033* | |
H144 | 0.6062 | 0.2181 | 0.3313 | 0.042* | |
H145 | 0.7843 | 0.2598 | 0.2217 | 0.039* | |
H146 | 0.8096 | 0.4472 | 0.1375 | 0.032* | |
H14A | 0.5718 | 0.6735 | 0.1493 | 0.029* | |
H14B | 0.6944 | 0.6618 | 0.1819 | 0.029* | |
H15 | 0.8699 | 0.7069 | −0.0895 | 0.030* | |
H162 | 1.1424 | 1.1552 | −0.3373 | 0.030* | |
H164 | 1.2652 | 1.0432 | −0.5377 | 0.031* | |
H165 | 1.1828 | 0.8740 | −0.4589 | 0.035* | |
H166 | 1.0723 | 0.8466 | −0.3138 | 0.032* | |
H16A | 1.0866 | 0.9952 | −0.1855 | 0.028* | |
H16B | 0.9627 | 1.0521 | −0.2165 | 0.028* | |
H22A | 0.3227 | 0.6850 | 0.1562 | 0.030* | |
H22B | 0.2354 | 0.6102 | 0.2326 | 0.030* | |
H242 | −0.0821 | 0.5070 | 0.6050 | 0.028* | |
H244 | −0.2348 | 0.6218 | 0.8013 | 0.034* | |
H245 | −0.1633 | 0.7959 | 0.7234 | 0.034* | |
H246 | −0.0446 | 0.8257 | 0.5793 | 0.028* | |
H24A | 0.0864 | 0.6142 | 0.4847 | 0.026* | |
H24B | −0.0338 | 0.6768 | 0.4507 | 0.026* | |
H25 | 0.1914 | 0.9570 | 0.3630 | 0.025* | |
H262 | 0.5319 | 1.1419 | −0.0283 | 0.027* | |
H264 | 0.5844 | 1.4217 | −0.0018 | 0.032* | |
H265 | 0.4840 | 1.3658 | 0.1434 | 0.032* | |
H266 | 0.4058 | 1.1896 | 0.2050 | 0.028* | |
H26A | 0.3659 | 1.0280 | 0.0867 | 0.026* | |
H26B | 0.4838 | 0.9749 | 0.1261 | 0.026* | |
H32A | 0.3708 | 0.3479 | 0.4199 | 0.031* | |
H32B | 0.2879 | 0.2698 | 0.4971 | 0.031* | |
H342 | −0.0183 | 0.1651 | 0.8822 | 0.029* | |
H344 | −0.1977 | 0.3039 | 1.0618 | 0.033* | |
H345 | −0.1292 | 0.4762 | 0.9764 | 0.036* | |
H346 | 0.0007 | 0.4930 | 0.8373 | 0.030* | |
H34A | 0.1440 | 0.2692 | 0.7593 | 0.029* | |
H34B | 0.0271 | 0.3288 | 0.7201 | 0.029* | |
H35 | 0.2467 | 0.6127 | 0.6314 | 0.029* | |
H362 | 0.6006 | 0.7947 | 0.2445 | 0.029* | |
H364 | 0.6297 | 1.0833 | 0.2682 | 0.031* | |
H365 | 0.5098 | 1.0334 | 0.4090 | 0.034* | |
H366 | 0.4340 | 0.8563 | 0.4701 | 0.030* | |
H36A | 0.4116 | 0.6906 | 0.3533 | 0.026* | |
H36B | 0.5301 | 0.6347 | 0.3916 | 0.026* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0243 (12) | 0.0214 (11) | 0.0177 (11) | −0.0049 (9) | −0.0018 (9) | −0.0029 (10) |
N12 | 0.0368 (13) | 0.0227 (11) | 0.0217 (11) | −0.0120 (10) | 0.0067 (10) | −0.0066 (10) |
C12 | 0.0230 (14) | 0.0178 (13) | 0.0192 (13) | −0.0042 (11) | −0.0043 (11) | −0.0006 (11) |
O14 | 0.0383 (11) | 0.0214 (9) | 0.0162 (9) | −0.0147 (8) | 0.0040 (8) | −0.0031 (8) |
N13 | 0.0259 (12) | 0.0187 (10) | 0.0220 (11) | −0.0060 (9) | −0.0032 (9) | −0.0028 (10) |
C14 | 0.0238 (14) | 0.0188 (13) | 0.0207 (13) | −0.0062 (11) | −0.0054 (11) | −0.0009 (11) |
C141 | 0.0313 (15) | 0.0230 (13) | 0.0190 (13) | −0.0095 (12) | −0.0040 (11) | −0.0056 (11) |
C142 | 0.0350 (16) | 0.0249 (14) | 0.0230 (14) | −0.0099 (12) | −0.0007 (12) | −0.0082 (12) |
N143 | 0.0466 (15) | 0.0275 (12) | 0.0231 (12) | −0.0159 (11) | 0.0002 (11) | −0.0075 (11) |
C144 | 0.060 (2) | 0.0192 (13) | 0.0238 (14) | −0.0123 (14) | −0.0040 (14) | −0.0048 (12) |
C145 | 0.0452 (18) | 0.0234 (14) | 0.0270 (14) | −0.0023 (13) | −0.0056 (13) | −0.0091 (12) |
C146 | 0.0323 (15) | 0.0269 (14) | 0.0234 (13) | −0.0036 (12) | −0.0051 (12) | −0.0107 (12) |
C147 | 0.0297 (15) | 0.0212 (13) | 0.0185 (13) | −0.0075 (11) | −0.0010 (11) | −0.0027 (11) |
C15 | 0.0334 (15) | 0.0197 (13) | 0.0226 (14) | −0.0052 (12) | −0.0066 (12) | −0.0051 (12) |
C16 | 0.0228 (14) | 0.0240 (13) | 0.0166 (13) | −0.0046 (11) | −0.0019 (11) | −0.0026 (12) |
C161 | 0.0165 (13) | 0.0219 (13) | 0.0192 (13) | −0.0014 (11) | −0.0027 (10) | −0.0027 (11) |
C162 | 0.0286 (15) | 0.0215 (13) | 0.0243 (14) | −0.0043 (11) | −0.0046 (12) | −0.0069 (12) |
N163 | 0.0258 (12) | 0.0237 (11) | 0.0233 (11) | −0.0058 (9) | −0.0004 (9) | −0.0035 (10) |
C164 | 0.0238 (14) | 0.0296 (14) | 0.0217 (13) | −0.0046 (11) | −0.0027 (11) | −0.0077 (12) |
C165 | 0.0317 (15) | 0.0278 (14) | 0.0271 (14) | −0.0072 (12) | −0.0013 (12) | −0.0115 (13) |
C166 | 0.0288 (15) | 0.0247 (13) | 0.0259 (14) | −0.0096 (11) | −0.0036 (12) | −0.0061 (12) |
C167 | 0.0258 (14) | 0.0199 (13) | 0.0231 (13) | −0.0073 (11) | −0.0026 (11) | −0.0040 (12) |
O16 | 0.0378 (11) | 0.0216 (9) | 0.0176 (9) | −0.0114 (8) | 0.0055 (8) | −0.0025 (8) |
N21 | 0.0191 (11) | 0.0221 (11) | 0.0178 (11) | −0.0057 (9) | −0.0043 (9) | −0.0024 (10) |
C22 | 0.0175 (13) | 0.0209 (13) | 0.0196 (13) | −0.0042 (11) | −0.0053 (11) | −0.0006 (12) |
N22 | 0.0304 (12) | 0.0226 (11) | 0.0185 (11) | −0.0117 (10) | 0.0036 (9) | −0.0059 (10) |
N23 | 0.0199 (11) | 0.0194 (10) | 0.0171 (11) | −0.0056 (9) | −0.0013 (9) | −0.0028 (9) |
C24 | 0.0157 (13) | 0.0222 (13) | 0.0135 (12) | −0.0013 (10) | −0.0020 (10) | −0.0025 (11) |
C241 | 0.0145 (13) | 0.0240 (13) | 0.0177 (12) | −0.0033 (11) | −0.0042 (10) | −0.0054 (11) |
C242 | 0.0268 (15) | 0.0239 (13) | 0.0183 (13) | −0.0068 (11) | −0.0013 (11) | −0.0063 (12) |
N243 | 0.0287 (12) | 0.0213 (11) | 0.0210 (11) | −0.0068 (9) | 0.0008 (9) | −0.0038 (10) |
C244 | 0.0278 (15) | 0.0317 (15) | 0.0191 (13) | −0.0054 (12) | 0.0042 (11) | −0.0070 (13) |
C245 | 0.0309 (15) | 0.0265 (14) | 0.0263 (14) | −0.0064 (12) | 0.0003 (12) | −0.0101 (13) |
C246 | 0.0229 (14) | 0.0211 (13) | 0.0217 (13) | −0.0076 (11) | −0.0015 (11) | −0.0015 (12) |
C247 | 0.0222 (14) | 0.0214 (13) | 0.0192 (13) | −0.0082 (11) | −0.0012 (10) | −0.0048 (11) |
O24 | 0.0246 (9) | 0.0218 (9) | 0.0176 (9) | −0.0113 (7) | 0.0028 (7) | −0.0041 (8) |
C25 | 0.0201 (13) | 0.0220 (13) | 0.0192 (13) | −0.0047 (11) | −0.0019 (11) | −0.0058 (11) |
C26 | 0.0160 (13) | 0.0210 (13) | 0.0193 (13) | −0.0064 (11) | −0.0037 (10) | −0.0013 (12) |
C261 | 0.0169 (13) | 0.0187 (12) | 0.0190 (13) | −0.0032 (10) | −0.0013 (10) | −0.0031 (11) |
C262 | 0.0276 (14) | 0.0187 (13) | 0.0195 (13) | −0.0061 (11) | −0.0019 (11) | −0.0039 (11) |
N263 | 0.0283 (12) | 0.0229 (11) | 0.0221 (11) | −0.0067 (9) | 0.0007 (9) | −0.0038 (10) |
C264 | 0.0269 (15) | 0.0175 (12) | 0.0294 (15) | −0.0071 (11) | 0.0001 (12) | −0.0035 (12) |
C265 | 0.0315 (15) | 0.0243 (13) | 0.0248 (14) | −0.0078 (11) | −0.0018 (12) | −0.0112 (12) |
C266 | 0.0259 (14) | 0.0231 (13) | 0.0183 (13) | −0.0050 (11) | −0.0019 (11) | −0.0032 (11) |
C267 | 0.0244 (14) | 0.0237 (13) | 0.0144 (12) | −0.0087 (11) | 0.0010 (10) | −0.0042 (11) |
O26 | 0.0269 (10) | 0.0210 (9) | 0.0186 (9) | −0.0108 (8) | 0.0035 (7) | −0.0030 (8) |
N31 | 0.0218 (11) | 0.0236 (11) | 0.0177 (11) | −0.0061 (9) | −0.0025 (9) | −0.0030 (9) |
C32 | 0.0191 (13) | 0.0200 (13) | 0.0197 (13) | −0.0046 (11) | −0.0048 (11) | 0.0001 (11) |
N32 | 0.0321 (13) | 0.0238 (11) | 0.0197 (11) | −0.0129 (9) | 0.0021 (9) | −0.0066 (10) |
N33 | 0.0196 (11) | 0.0208 (11) | 0.0211 (11) | −0.0047 (9) | −0.0043 (9) | −0.0037 (10) |
C34 | 0.0209 (13) | 0.0174 (12) | 0.0195 (13) | −0.0057 (10) | −0.0061 (11) | −0.0014 (11) |
O34 | 0.0312 (10) | 0.0244 (9) | 0.0191 (9) | −0.0129 (8) | 0.0027 (8) | −0.0044 (8) |
C341 | 0.0192 (13) | 0.0218 (13) | 0.0187 (12) | −0.0044 (11) | −0.0032 (10) | −0.0041 (11) |
C342 | 0.0280 (14) | 0.0208 (13) | 0.0202 (13) | −0.0055 (11) | −0.0017 (11) | −0.0041 (11) |
N343 | 0.0255 (12) | 0.0249 (12) | 0.0242 (12) | −0.0070 (9) | −0.0024 (9) | −0.0048 (10) |
C344 | 0.0303 (15) | 0.0303 (15) | 0.0186 (13) | −0.0053 (12) | 0.0005 (11) | −0.0070 (12) |
C345 | 0.0377 (16) | 0.0213 (13) | 0.0279 (14) | −0.0055 (12) | −0.0023 (13) | −0.0070 (12) |
C346 | 0.0299 (15) | 0.0199 (13) | 0.0227 (14) | −0.0061 (11) | −0.0043 (12) | −0.0023 (12) |
C347 | 0.0249 (14) | 0.0227 (13) | 0.0228 (13) | −0.0096 (11) | −0.0008 (11) | −0.0053 (12) |
C35 | 0.0255 (14) | 0.0244 (13) | 0.0222 (13) | −0.0073 (11) | −0.0028 (11) | −0.0069 (12) |
C36 | 0.0177 (13) | 0.0266 (14) | 0.0173 (13) | −0.0027 (11) | −0.0036 (10) | −0.0063 (12) |
C361 | 0.0184 (13) | 0.0215 (13) | 0.0199 (13) | −0.0020 (10) | −0.0049 (11) | −0.0047 (11) |
C362 | 0.0279 (15) | 0.0207 (13) | 0.0220 (13) | −0.0064 (11) | −0.0024 (11) | −0.0045 (12) |
N363 | 0.0285 (12) | 0.0228 (11) | 0.0246 (12) | −0.0070 (10) | −0.0032 (10) | −0.0049 (10) |
C364 | 0.0272 (15) | 0.0188 (13) | 0.0295 (14) | −0.0046 (11) | −0.0060 (12) | −0.0058 (12) |
C365 | 0.0340 (16) | 0.0240 (13) | 0.0260 (14) | −0.0068 (12) | −0.0002 (12) | −0.0102 (12) |
C366 | 0.0214 (14) | 0.0294 (14) | 0.0197 (13) | −0.0060 (11) | 0.0028 (11) | −0.0075 (12) |
C367 | 0.0239 (14) | 0.0211 (13) | 0.0174 (12) | −0.0059 (11) | −0.0005 (11) | −0.0032 (11) |
O36 | 0.0303 (10) | 0.0198 (9) | 0.0177 (9) | −0.0130 (8) | 0.0035 (7) | −0.0015 (8) |
Geometric parameters (Å, º) top
N11—C16 | 1.318 (3) | C247—O24 | 1.438 (3) |
N11—C12 | 1.354 (3) | C247—H24A | 0.99 |
N12—C12 | 1.332 (3) | C247—H24B | 0.99 |
N12—H12A | 0.88 | C25—C26 | 1.391 (3) |
N12—H12B | 0.88 | C25—H25 | 0.95 |
C12—N13 | 1.353 (3) | C26—O26 | 1.357 (3) |
O14—C14 | 1.359 (3) | C261—C266 | 1.373 (3) |
O14—C147 | 1.443 (3) | C261—C262 | 1.395 (3) |
N13—C14 | 1.318 (3) | C261—C267 | 1.502 (3) |
C14—C15 | 1.391 (3) | C262—N263 | 1.332 (3) |
C141—C142 | 1.387 (3) | C262—H262 | 0.95 |
C141—C146 | 1.387 (3) | N263—C264 | 1.333 (3) |
C141—C147 | 1.497 (3) | C264—C265 | 1.375 (3) |
C142—N143 | 1.341 (3) | C264—H264 | 0.95 |
C142—H142 | 0.95 | C265—C266 | 1.384 (3) |
N143—C144 | 1.329 (3) | C265—H265 | 0.95 |
C144—C145 | 1.381 (4) | C266—H266 | 0.95 |
C144—H144 | 0.95 | C267—O26 | 1.444 (3) |
C145—C146 | 1.382 (4) | C267—H26A | 0.99 |
C145—H145 | 0.95 | C267—H26B | 0.99 |
C146—H146 | 0.95 | N31—C36 | 1.322 (3) |
C147—H14A | 0.99 | N31—C32 | 1.361 (3) |
C147—H14B | 0.99 | C32—N32 | 1.331 (3) |
C15—C16 | 1.378 (3) | C32—N33 | 1.352 (3) |
C15—H15 | 0.95 | N32—H32A | 0.88 |
C16—O16 | 1.366 (3) | N32—H32B | 0.88 |
C161—C166 | 1.380 (3) | N33—C34 | 1.324 (3) |
C161—C162 | 1.392 (3) | C34—O36 | 1.360 (3) |
C161—C167 | 1.500 (3) | C34—C35 | 1.391 (3) |
C162—N163 | 1.342 (3) | O34—C36 | 1.362 (3) |
C162—H162 | 0.95 | O34—C347 | 1.438 (3) |
N163—C164 | 1.334 (3) | C341—C346 | 1.376 (3) |
C164—C165 | 1.377 (3) | C341—C342 | 1.392 (3) |
C164—H164 | 0.95 | C341—C347 | 1.501 (3) |
C165—C166 | 1.390 (3) | C342—N343 | 1.339 (3) |
C165—H165 | 0.95 | C342—H342 | 0.95 |
C166—H166 | 0.95 | N343—C344 | 1.337 (3) |
C167—O16 | 1.442 (3) | C344—C345 | 1.374 (3) |
C167—H16A | 0.99 | C344—H344 | 0.95 |
C167—H16B | 0.99 | C345—C346 | 1.386 (3) |
N21—C26 | 1.320 (3) | C345—H345 | 0.95 |
N21—C22 | 1.357 (3) | C346—H346 | 0.95 |
C22—N22 | 1.327 (3) | C347—H34A | 0.99 |
C22—N23 | 1.365 (3) | C347—H34B | 0.99 |
N22—H22A | 0.88 | C35—C36 | 1.383 (3) |
N22—H22B | 0.88 | C35—H35 | 0.95 |
N23—C24 | 1.319 (3) | C361—C366 | 1.380 (3) |
C24—O24 | 1.363 (3) | C361—C362 | 1.393 (3) |
C24—C25 | 1.390 (3) | C361—C367 | 1.502 (3) |
C241—C246 | 1.382 (3) | C362—N363 | 1.342 (3) |
C241—C242 | 1.396 (3) | C362—H362 | 0.95 |
C241—C247 | 1.503 (3) | N363—C364 | 1.331 (3) |
C242—N243 | 1.333 (3) | C364—C365 | 1.380 (3) |
C242—H242 | 0.95 | C364—H364 | 0.95 |
N243—C244 | 1.335 (3) | C365—C366 | 1.383 (3) |
C244—C245 | 1.381 (3) | C365—H365 | 0.95 |
C244—H244 | 0.95 | C366—H366 | 0.95 |
C245—C246 | 1.394 (3) | C367—O36 | 1.436 (3) |
C245—H245 | 0.95 | C367—H36A | 0.99 |
C246—H246 | 0.95 | C367—H36B | 0.99 |
| | | |
C16—N11—C12 | 115.1 (2) | H24A—C247—H24B | 108.4 |
C12—N12—H12A | 120.0 | C24—O24—C247 | 116.16 (18) |
C12—N12—H12B | 120.0 | C24—C25—C26 | 113.8 (2) |
H12A—N12—H12B | 120.0 | C24—C25—H25 | 123.1 |
N12—C12—N13 | 116.7 (2) | C26—C25—H25 | 123.1 |
N12—C12—N11 | 117.7 (2) | N21—C26—O26 | 118.8 (2) |
N13—C12—N11 | 125.5 (2) | N21—C26—C25 | 124.8 (2) |
C14—O14—C147 | 115.60 (18) | O26—C26—C25 | 116.4 (2) |
C14—N13—C12 | 115.8 (2) | C266—C261—C262 | 117.2 (2) |
N13—C14—O14 | 118.9 (2) | C266—C261—C267 | 124.8 (2) |
N13—C14—C15 | 124.2 (2) | C262—C261—C267 | 118.0 (2) |
O14—C14—C15 | 116.9 (2) | N263—C262—C261 | 124.2 (2) |
C142—C141—C146 | 117.5 (2) | N263—C262—H262 | 117.9 |
C142—C141—C147 | 119.7 (2) | C261—C262—H262 | 117.9 |
C146—C141—C147 | 122.5 (2) | C262—N263—C264 | 117.0 (2) |
N143—C142—C141 | 124.0 (3) | N263—C264—C265 | 123.4 (2) |
N143—C142—H142 | 118.0 | N263—C264—H264 | 118.3 |
C141—C142—H142 | 118.0 | C265—C264—H264 | 118.3 |
C144—N143—C142 | 116.9 (2) | C264—C265—C266 | 118.5 (2) |
N143—C144—C145 | 123.7 (2) | C264—C265—H265 | 120.7 |
N143—C144—H144 | 118.2 | C266—C265—H265 | 120.7 |
C145—C144—H144 | 118.2 | C261—C266—C265 | 119.7 (2) |
C144—C145—C146 | 118.5 (3) | C261—C266—H266 | 120.2 |
C144—C145—H145 | 120.7 | C265—C266—H266 | 120.2 |
C146—C145—H145 | 120.7 | O26—C267—C261 | 108.22 (19) |
C145—C146—C141 | 119.3 (2) | O26—C267—H26A | 110.1 |
C145—C146—H146 | 120.4 | C261—C267—H26A | 110.1 |
C141—C146—H146 | 120.4 | O26—C267—H26B | 110.1 |
O14—C147—C141 | 108.93 (19) | C261—C267—H26B | 110.1 |
O14—C147—H14A | 109.9 | H26A—C267—H26B | 108.4 |
C141—C147—H14A | 109.9 | C26—O26—C267 | 116.40 (18) |
O14—C147—H14B | 109.9 | C36—N31—C32 | 114.8 (2) |
C141—C147—H14B | 109.9 | N32—C32—N33 | 116.5 (2) |
H14A—C147—H14B | 108.3 | N32—C32—N31 | 117.6 (2) |
C16—C15—C14 | 114.1 (2) | N33—C32—N31 | 125.9 (2) |
C16—C15—H15 | 122.9 | C32—N32—H32A | 120.0 |
C14—C15—H15 | 122.9 | C32—N32—H32B | 120.0 |
N11—C16—O16 | 118.2 (2) | H32A—N32—H32B | 120.0 |
N11—C16—C15 | 125.3 (2) | C34—N33—C32 | 115.3 (2) |
O16—C16—C15 | 116.5 (2) | N33—C34—O36 | 119.1 (2) |
C166—C161—C162 | 117.2 (2) | N33—C34—C35 | 124.7 (2) |
C166—C161—C167 | 124.3 (2) | O36—C34—C35 | 116.2 (2) |
C162—C161—C167 | 118.4 (2) | C36—O34—C347 | 117.47 (18) |
N163—C162—C161 | 123.9 (2) | C346—C341—C342 | 117.9 (2) |
N163—C162—H162 | 118.0 | C346—C341—C347 | 123.6 (2) |
C161—C162—H162 | 118.0 | C342—C341—C347 | 118.5 (2) |
C164—N163—C162 | 117.2 (2) | N343—C342—C341 | 123.7 (2) |
N163—C164—C165 | 123.6 (2) | N343—C342—H342 | 118.1 |
N163—C164—H164 | 118.2 | C341—C342—H342 | 118.1 |
C165—C164—H164 | 118.2 | C344—N343—C342 | 116.7 (2) |
C164—C165—C166 | 118.3 (2) | N343—C344—C345 | 124.1 (2) |
C164—C165—H165 | 120.9 | N343—C344—H344 | 117.9 |
C166—C165—H165 | 120.9 | C345—C344—H344 | 117.9 |
C161—C166—C165 | 119.8 (2) | C344—C345—C346 | 118.2 (2) |
C161—C166—H166 | 120.1 | C344—C345—H345 | 120.9 |
C165—C166—H166 | 120.1 | C346—C345—H345 | 120.9 |
O16—C167—C161 | 107.68 (19) | C341—C346—C345 | 119.5 (2) |
O16—C167—H16A | 110.2 | C341—C346—H346 | 120.3 |
C161—C167—H16A | 110.2 | C345—C346—H346 | 120.3 |
O16—C167—H16B | 110.2 | O34—C347—C341 | 107.68 (19) |
C161—C167—H16B | 110.2 | O34—C347—H34A | 110.2 |
H16A—C167—H16B | 108.5 | C341—C347—H34A | 110.2 |
C16—O16—C167 | 116.66 (19) | O34—C347—H34B | 110.2 |
C26—N21—C22 | 115.6 (2) | C341—C347—H34B | 110.2 |
N22—C22—N21 | 117.5 (2) | H34A—C347—H34B | 108.5 |
N22—C22—N23 | 117.2 (2) | C36—C35—C34 | 113.8 (2) |
N21—C22—N23 | 125.3 (2) | C36—C35—H35 | 123.1 |
C22—N22—H22A | 120.0 | C34—C35—H35 | 123.1 |
C22—N22—H22B | 120.0 | N31—C36—O34 | 118.5 (2) |
H22A—N22—H22B | 120.0 | N31—C36—C35 | 125.4 (2) |
C24—N23—C22 | 115.2 (2) | O34—C36—C35 | 116.1 (2) |
N23—C24—O24 | 118.6 (2) | C366—C361—C362 | 117.2 (2) |
N23—C24—C25 | 125.2 (2) | C366—C361—C367 | 124.7 (2) |
O24—C24—C25 | 116.3 (2) | C362—C361—C367 | 118.0 (2) |
C246—C241—C242 | 117.3 (2) | N363—C362—C361 | 124.3 (2) |
C246—C241—C247 | 124.0 (2) | N363—C362—H362 | 117.8 |
C242—C241—C247 | 118.7 (2) | C361—C362—H362 | 117.8 |
N243—C242—C241 | 124.4 (2) | C364—N363—C362 | 116.8 (2) |
N243—C242—H242 | 117.8 | N363—C364—C365 | 123.3 (2) |
C241—C242—H242 | 117.8 | N363—C364—H364 | 118.4 |
C242—N243—C244 | 116.9 (2) | C365—C364—H364 | 118.4 |
N243—C244—C245 | 123.8 (2) | C364—C365—C366 | 119.0 (2) |
N243—C244—H244 | 118.1 | C364—C365—H365 | 120.5 |
C245—C244—H244 | 118.1 | C366—C365—H365 | 120.5 |
C244—C245—C246 | 118.3 (2) | C361—C366—C365 | 119.3 (2) |
C244—C245—H245 | 120.9 | C361—C366—H366 | 120.3 |
C246—C245—H245 | 120.9 | C365—C366—H366 | 120.3 |
C241—C246—C245 | 119.4 (2) | O36—C367—C361 | 107.52 (19) |
C241—C246—H246 | 120.3 | O36—C367—H36A | 110.2 |
C245—C246—H246 | 120.3 | C361—C367—H36A | 110.2 |
O24—C247—C241 | 108.25 (19) | O36—C367—H36B | 110.2 |
O24—C247—H24A | 110.0 | C361—C367—H36B | 110.2 |
C241—C247—H24A | 110.0 | H36A—C367—H36B | 108.5 |
O24—C247—H24B | 110.0 | C34—O36—C367 | 115.89 (18) |
C241—C247—H24B | 110.0 | | |
| | | |
C16—N11—C12—N12 | 179.0 (2) | N23—C24—C25—C26 | −0.6 (4) |
C16—N11—C12—N13 | −1.3 (3) | O24—C24—C25—C26 | 178.4 (2) |
N12—C12—N13—C14 | −178.4 (2) | C22—N21—C26—O26 | −178.7 (2) |
N11—C12—N13—C14 | 2.0 (3) | C22—N21—C26—C25 | 1.4 (3) |
C12—N13—C14—O14 | 177.9 (2) | C24—C25—C26—N21 | −1.4 (3) |
C12—N13—C14—C15 | −1.9 (3) | C24—C25—C26—O26 | 178.8 (2) |
C147—O14—C14—N13 | −2.5 (3) | C266—C261—C262—N263 | −0.6 (4) |
C147—O14—C14—C15 | 177.3 (2) | C267—C261—C262—N263 | −179.9 (2) |
C146—C141—C142—N143 | 1.4 (4) | C261—C262—N263—C264 | 0.2 (4) |
C147—C141—C142—N143 | −172.6 (2) | C262—N263—C264—C265 | 0.0 (4) |
C141—C142—N143—C144 | 0.1 (4) | N263—C264—C265—C266 | 0.2 (4) |
C142—N143—C144—C145 | −2.6 (4) | C262—C261—C266—C265 | 0.8 (4) |
N143—C144—C145—C146 | 3.3 (4) | C267—C261—C266—C265 | −180.0 (2) |
C144—C145—C146—C141 | −1.6 (4) | C264—C265—C266—C261 | −0.6 (4) |
C142—C141—C146—C145 | −0.6 (4) | C266—C261—C267—O26 | 10.3 (3) |
C147—C141—C146—C145 | 173.3 (2) | C262—C261—C267—O26 | −170.5 (2) |
C14—O14—C147—C141 | −163.1 (2) | N21—C26—O26—C267 | 0.9 (3) |
C142—C141—C147—O14 | −149.5 (2) | C25—C26—O26—C267 | −179.2 (2) |
C146—C141—C147—O14 | 36.8 (3) | C261—C267—O26—C26 | 178.4 (2) |
N13—C14—C15—C16 | 1.3 (4) | C36—N31—C32—N32 | 177.3 (2) |
O14—C14—C15—C16 | −178.5 (2) | C36—N31—C32—N33 | −2.2 (3) |
C12—N11—C16—O16 | −179.3 (2) | N32—C32—N33—C34 | −178.4 (2) |
C12—N11—C16—C15 | 0.6 (4) | N31—C32—N33—C34 | 1.2 (3) |
C14—C15—C16—N11 | −0.6 (4) | C32—N33—C34—O36 | −179.4 (2) |
C14—C15—C16—O16 | 179.3 (2) | C32—N33—C34—C35 | 0.6 (3) |
C166—C161—C162—N163 | −0.3 (4) | C346—C341—C342—N343 | 1.0 (4) |
C167—C161—C162—N163 | −179.5 (2) | C347—C341—C342—N343 | −176.6 (2) |
C161—C162—N163—C164 | 0.0 (4) | C341—C342—N343—C344 | −0.7 (4) |
C162—N163—C164—C165 | −0.2 (4) | C342—N343—C344—C345 | 0.2 (4) |
N163—C164—C165—C166 | 0.7 (4) | N343—C344—C345—C346 | 0.0 (4) |
C162—C161—C166—C165 | 0.8 (4) | C342—C341—C346—C345 | −0.8 (4) |
C167—C161—C166—C165 | 180.0 (2) | C347—C341—C346—C345 | 176.7 (2) |
C164—C165—C166—C161 | −1.0 (4) | C344—C345—C346—C341 | 0.3 (4) |
C166—C161—C167—O16 | −2.2 (3) | C36—O34—C347—C341 | −178.0 (2) |
C162—C161—C167—O16 | 177.0 (2) | C346—C341—C347—O34 | 15.0 (3) |
N11—C16—O16—C167 | 1.0 (3) | C342—C341—C347—O34 | −167.6 (2) |
C15—C16—O16—C167 | −179.0 (2) | N33—C34—C35—C36 | −1.1 (4) |
C161—C167—O16—C16 | −173.2 (2) | O36—C34—C35—C36 | 178.9 (2) |
C26—N21—C22—N22 | −179.1 (2) | C32—N31—C36—O34 | −177.9 (2) |
C26—N21—C22—N23 | 0.4 (3) | C32—N31—C36—C35 | 1.6 (3) |
N22—C22—N23—C24 | 177.4 (2) | C347—O34—C36—N31 | −1.6 (3) |
N21—C22—N23—C24 | −2.1 (3) | C347—O34—C36—C35 | 178.9 (2) |
C22—N23—C24—O24 | −176.8 (2) | C34—C35—C36—N31 | −0.1 (4) |
C22—N23—C24—C25 | 2.2 (3) | C34—C35—C36—O34 | 179.4 (2) |
C246—C241—C242—N243 | −0.9 (4) | C366—C361—C362—N363 | −1.0 (4) |
C247—C241—C242—N243 | −178.4 (2) | C367—C361—C362—N363 | 178.0 (2) |
C241—C242—N243—C244 | 0.2 (4) | C361—C362—N363—C364 | 0.1 (4) |
C242—N243—C244—C245 | 0.4 (4) | C362—N363—C364—C365 | 0.4 (4) |
N243—C244—C245—C246 | −0.4 (4) | N363—C364—C365—C366 | 0.0 (4) |
C242—C241—C246—C245 | 0.9 (3) | C362—C361—C366—C365 | 1.4 (4) |
C247—C241—C246—C245 | 178.2 (2) | C367—C361—C366—C365 | −177.4 (2) |
C244—C245—C246—C241 | −0.3 (4) | C364—C365—C366—C361 | −1.0 (4) |
C246—C241—C247—O24 | 11.7 (3) | C366—C361—C367—O36 | 1.0 (3) |
C242—C241—C247—O24 | −171.0 (2) | C362—C361—C367—O36 | −177.9 (2) |
N23—C24—O24—C247 | −1.8 (3) | N33—C34—O36—C367 | −0.8 (3) |
C25—C24—O24—C247 | 179.1 (2) | C35—C34—O36—C367 | 179.2 (2) |
C241—C247—O24—C24 | 177.3 (2) | C361—C367—O36—C34 | −179.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12A···N363 | 0.88 | 2.12 | 2.998 (3) | 174 |
N12—H12B···N343i | 0.88 | 2.10 | 2.977 (3) | 176 |
N22—H22A···N263ii | 0.88 | 2.11 | 2.985 (3) | 175 |
N22—H22B···N243iii | 0.88 | 2.11 | 2.987 (3) | 175 |
N32—H32A···N143 | 0.88 | 2.11 | 2.978 (3) | 167 |
N32—H32B···N163iv | 0.88 | 2.10 | 2.982 (3) | 178 |
Symmetry codes: (i) x+1, y+1, z−1; (ii) −x+1, −y+2, −z; (iii) −x, −y+1, −z+1; (iv) x−1, y−1, z+1. |
(III) 2-Amino-4,6-bis(morpholino)-5-nitrosopirimidine
top
Crystal data top
C12H18N6O3 | F(000) = 624 |
Mr = 294.32 | Dx = 1.428 Mg m−3 |
Monoclinic, P21/c | Melting point: 483K K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0037 (4) Å | Cell parameters from 3096 reflections |
b = 9.1130 (3) Å | θ = 3.0–27.5° |
c = 12.4892 (3) Å | µ = 0.11 mm−1 |
β = 112.3400 (12)° | T = 120 K |
V = 1368.92 (7) Å3 | Block, blue |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Kappa-CCD diffractometer | 2391 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.047 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
ϕ scans, and ω scans with κ offsets | h = −16→16 |
10906 measured reflections | k = −11→10 |
3096 independent reflections | l = −14→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0615P)2 + 0.2156P] where P = (Fo2 + 2Fc2)/3 |
3096 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C12H18N6O3 | V = 1368.92 (7) Å3 |
Mr = 294.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.0037 (4) Å | µ = 0.11 mm−1 |
b = 9.1130 (3) Å | T = 120 K |
c = 12.4892 (3) Å | 0.30 × 0.20 × 0.20 mm |
β = 112.3400 (12)° | |
Data collection top
Kappa-CCD diffractometer | 2391 reflections with I > 2σ(I) |
10906 measured reflections | Rint = 0.047 |
3096 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.41 e Å−3 |
3096 reflections | Δρmin = −0.28 e Å−3 |
190 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.32218 (9) | 0.47876 (13) | 0.07040 (9) | 0.0169 (3) | |
C2 | 0.26526 (11) | 0.46319 (15) | −0.04405 (11) | 0.0161 (3) | |
N2 | 0.30168 (10) | 0.35938 (14) | −0.09559 (10) | 0.0207 (3) | |
N3 | 0.17212 (9) | 0.53626 (12) | −0.11111 (9) | 0.0169 (3) | |
C5 | 0.21761 (11) | 0.70363 (15) | 0.05196 (11) | 0.0163 (3) | |
C4 | 0.14534 (11) | 0.65304 (15) | −0.06249 (11) | 0.0155 (3) | |
N4 | 0.05260 (9) | 0.72681 (13) | −0.12493 (10) | 0.0176 (3) | |
C42 | −0.01378 (12) | 0.68569 (16) | −0.24524 (12) | 0.0195 (3) | |
C43 | −0.11548 (12) | 0.60041 (16) | −0.24993 (12) | 0.0224 (3) | |
O44 | −0.17954 (8) | 0.68593 (11) | −0.20170 (8) | 0.0220 (3) | |
C45 | −0.11579 (12) | 0.72391 (16) | −0.08401 (12) | 0.0201 (3) | |
C46 | −0.01272 (11) | 0.81093 (15) | −0.07314 (12) | 0.0185 (3) | |
N5 | 0.24536 (10) | 0.84568 (13) | 0.08381 (10) | 0.0203 (3) | |
O5 | 0.19317 (9) | 0.94670 (11) | 0.01494 (9) | 0.0253 (3) | |
C6 | 0.29515 (11) | 0.59347 (15) | 0.12109 (11) | 0.0165 (3) | |
N6 | 0.34601 (10) | 0.60405 (13) | 0.23642 (10) | 0.0204 (3) | |
C62 | 0.43500 (13) | 0.50290 (17) | 0.30270 (12) | 0.0269 (4) | |
C63 | 0.53472 (12) | 0.59131 (18) | 0.37680 (13) | 0.0260 (3) | |
O64 | 0.50652 (8) | 0.68598 (11) | 0.45292 (8) | 0.0222 (2) | |
C65 | 0.41941 (12) | 0.78462 (16) | 0.38953 (12) | 0.0214 (3) | |
C66 | 0.31654 (12) | 0.70298 (16) | 0.31231 (12) | 0.0191 (3) | |
H2A | 0.3598 | 0.3059 | −0.0549 | 0.025* | |
H2B | 0.2677 | 0.3441 | −0.1704 | 0.025* | |
H42A | 0.0315 | 0.6247 | −0.2763 | 0.023* | |
H42B | −0.0371 | 0.7751 | −0.2935 | 0.023* | |
H43A | −0.1615 | 0.5754 | −0.3313 | 0.027* | |
H43B | −0.0921 | 0.5078 | −0.2059 | 0.027* | |
H45A | −0.0933 | 0.6332 | −0.0372 | 0.024* | |
H45B | −0.1623 | 0.7828 | −0.0531 | 0.024* | |
H46A | −0.0346 | 0.9064 | −0.1132 | 0.022* | |
H46B | 0.0324 | 0.8302 | 0.0095 | 0.022* | |
H62A | 0.4550 | 0.4393 | 0.2493 | 0.032* | |
H62B | 0.4097 | 0.4395 | 0.3522 | 0.032* | |
H63A | 0.5952 | 0.5241 | 0.4229 | 0.031* | |
H63B | 0.5619 | 0.6508 | 0.3266 | 0.031* | |
H65A | 0.4455 | 0.8496 | 0.3415 | 0.026* | |
H65B | 0.4005 | 0.8469 | 0.4444 | 0.026* | |
H66A | 0.2852 | 0.6460 | 0.3603 | 0.023* | |
H66B | 0.2595 | 0.7738 | 0.2653 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0182 (6) | 0.0176 (6) | 0.0138 (5) | 0.0005 (5) | 0.0048 (5) | −0.0004 (5) |
C2 | 0.0164 (7) | 0.0155 (7) | 0.0162 (6) | −0.0026 (5) | 0.0058 (5) | 0.0005 (5) |
N2 | 0.0209 (6) | 0.0234 (7) | 0.0136 (6) | 0.0045 (5) | 0.0017 (5) | −0.0032 (5) |
N3 | 0.0177 (6) | 0.0173 (6) | 0.0147 (5) | −0.0004 (5) | 0.0050 (5) | −0.0008 (5) |
C5 | 0.0169 (7) | 0.0176 (7) | 0.0139 (6) | −0.0006 (5) | 0.0054 (5) | −0.0004 (5) |
C4 | 0.0168 (7) | 0.0156 (7) | 0.0151 (6) | −0.0023 (5) | 0.0073 (5) | 0.0020 (5) |
N4 | 0.0172 (6) | 0.0197 (6) | 0.0143 (5) | 0.0020 (5) | 0.0041 (5) | −0.0011 (5) |
C42 | 0.0204 (7) | 0.0234 (8) | 0.0119 (6) | 0.0021 (6) | 0.0029 (5) | −0.0008 (5) |
C43 | 0.0261 (8) | 0.0203 (8) | 0.0174 (7) | −0.0009 (6) | 0.0043 (6) | −0.0017 (6) |
O44 | 0.0186 (5) | 0.0269 (6) | 0.0177 (5) | −0.0017 (4) | 0.0038 (4) | 0.0004 (4) |
C45 | 0.0203 (7) | 0.0235 (8) | 0.0157 (6) | 0.0005 (6) | 0.0058 (6) | 0.0012 (6) |
C46 | 0.0197 (7) | 0.0183 (7) | 0.0163 (7) | 0.0026 (6) | 0.0053 (6) | −0.0010 (5) |
N5 | 0.0233 (7) | 0.0172 (6) | 0.0204 (6) | −0.0007 (5) | 0.0085 (5) | 0.0010 (5) |
O5 | 0.0271 (6) | 0.0197 (5) | 0.0262 (5) | 0.0003 (5) | 0.0069 (5) | 0.0033 (4) |
C6 | 0.0171 (7) | 0.0180 (7) | 0.0145 (6) | −0.0034 (5) | 0.0061 (5) | −0.0006 (5) |
N6 | 0.0240 (7) | 0.0205 (6) | 0.0134 (5) | 0.0061 (5) | 0.0033 (5) | −0.0017 (5) |
C62 | 0.0348 (9) | 0.0239 (8) | 0.0155 (7) | 0.0116 (7) | 0.0024 (6) | −0.0011 (6) |
C63 | 0.0239 (8) | 0.0311 (9) | 0.0221 (7) | 0.0093 (7) | 0.0077 (6) | 0.0004 (6) |
O64 | 0.0205 (5) | 0.0228 (6) | 0.0183 (5) | 0.0028 (4) | 0.0020 (4) | −0.0029 (4) |
C65 | 0.0213 (7) | 0.0187 (8) | 0.0221 (7) | 0.0015 (6) | 0.0060 (6) | −0.0023 (6) |
C66 | 0.0203 (7) | 0.0219 (8) | 0.0150 (6) | 0.0013 (6) | 0.0067 (6) | −0.0018 (5) |
Geometric parameters (Å, º) top
N1—C6 | 1.3365 (18) | C45—H45A | 0.99 |
N1—C2 | 1.3442 (17) | C45—H45B | 0.99 |
C2—N2 | 1.3286 (18) | C46—H46A | 0.99 |
C2—N3 | 1.3568 (17) | C46—H46B | 0.99 |
N2—H2A | 0.88 | N5—O5 | 1.2665 (15) |
N2—H2B | 0.88 | C6—N6 | 1.3406 (17) |
N3—C4 | 1.3354 (18) | N6—C66 | 1.4608 (17) |
C5—N5 | 1.3619 (18) | N6—C62 | 1.4648 (19) |
C5—C6 | 1.4519 (19) | C62—C63 | 1.508 (2) |
C5—C4 | 1.4553 (18) | C62—H62A | 0.99 |
C4—N4 | 1.3415 (18) | C62—H62B | 0.99 |
N4—C46 | 1.4645 (17) | C63—O64 | 1.4311 (17) |
N4—C42 | 1.4688 (17) | C63—H63A | 0.99 |
C42—C43 | 1.516 (2) | C63—H63B | 0.99 |
C42—H42A | 0.99 | O64—C65 | 1.4269 (17) |
C42—H42B | 0.99 | C65—C66 | 1.514 (2) |
C43—O44 | 1.4303 (18) | C65—H65A | 0.99 |
C43—H43A | 0.9900 | C65—H65B | 0.99 |
C43—H43B | 0.9900 | C66—H66A | 0.99 |
O44—C45 | 1.4287 (16) | C66—H66B | 0.99 |
C45—C46 | 1.518 (2) | | |
| | | |
C6—N1—C2 | 116.66 (12) | N4—C46—H46A | 109.9 |
N2—C2—N1 | 115.90 (12) | C45—C46—H46A | 109.9 |
N2—C2—N3 | 116.70 (12) | N4—C46—H46B | 109.9 |
N1—C2—N3 | 127.31 (12) | C45—C46—H46B | 109.9 |
C2—N2—H2A | 120.0 | H46A—C46—H46B | 108.3 |
C2—N2—H2B | 120.0 | O5—N5—C5 | 118.58 (11) |
H2A—N2—H2B | 120.0 | N1—C6—N6 | 117.00 (12) |
C4—N3—C2 | 115.87 (11) | N1—C6—C5 | 120.49 (11) |
N5—C5—C6 | 115.88 (12) | N6—C6—C5 | 122.46 (12) |
N5—C5—C4 | 126.05 (12) | C6—N6—C66 | 126.69 (12) |
C6—C5—C4 | 114.10 (11) | C6—N6—C62 | 121.53 (11) |
N3—C4—N4 | 117.86 (12) | C66—N6—C62 | 111.56 (11) |
N3—C4—C5 | 121.09 (12) | N6—C62—C63 | 108.72 (12) |
N4—C4—C5 | 120.96 (12) | N6—C62—H62A | 109.9 |
C4—N4—C46 | 123.35 (11) | C63—C62—H62A | 109.9 |
C4—N4—C42 | 121.04 (11) | N6—C62—H62B | 109.9 |
C46—N4—C42 | 111.80 (11) | C63—C62—H62B | 109.9 |
N4—C42—C43 | 109.59 (11) | H62A—C62—H62B | 108.3 |
N4—C42—H42A | 109.8 | O64—C63—C62 | 110.61 (12) |
C43—C42—H42A | 109.8 | O64—C63—H63A | 109.5 |
N4—C42—H42B | 109.8 | C62—C63—H63A | 109.5 |
C43—C42—H42B | 109.8 | O64—C63—H63B | 109.5 |
H42A—C42—H42B | 108.2 | C62—C63—H63B | 109.5 |
O44—C43—C42 | 110.10 (11) | H63A—C63—H63B | 108.1 |
O44—C43—H43A | 109.6 | C65—O64—C63 | 111.16 (10) |
C42—C43—H43A | 109.6 | O64—C65—C66 | 111.52 (11) |
O44—C43—H43B | 109.6 | O64—C65—H65A | 109.3 |
C42—C43—H43B | 109.6 | C66—C65—H65A | 109.3 |
H43A—C43—H43B | 108.2 | O64—C65—H65B | 109.3 |
C45—O44—C43 | 111.23 (10) | C66—C65—H65B | 109.3 |
O44—C45—C46 | 111.46 (11) | H65A—C65—H65B | 108.0 |
O44—C45—H45A | 109.3 | N6—C66—C65 | 109.29 (11) |
C46—C45—H45A | 109.3 | N6—C66—H66A | 109.8 |
O44—C45—H45B | 109.3 | C65—C66—H66A | 109.8 |
C46—C45—H45B | 109.3 | N6—C66—H66B | 109.8 |
H45A—C45—H45B | 108.0 | C65—C66—H66B | 109.8 |
N4—C46—C45 | 109.12 (11) | H66A—C66—H66B | 108.3 |
| | | |
C6—N1—C2—N2 | 172.34 (12) | O44—C45—C46—N4 | −55.83 (15) |
C6—N1—C2—N3 | −11.2 (2) | C6—C5—N5—O5 | 166.84 (11) |
N2—C2—N3—C4 | −171.14 (12) | C4—C5—N5—O5 | 10.7 (2) |
N1—C2—N3—C4 | 12.45 (19) | C2—N1—C6—N6 | 175.47 (12) |
C2—N3—C4—N4 | −178.69 (11) | C2—N1—C6—C5 | −7.14 (18) |
C2—N3—C4—C5 | 4.71 (18) | N5—C5—C6—N1 | −137.55 (13) |
N5—C5—C4—N3 | 136.28 (14) | C4—C5—C6—N1 | 21.43 (18) |
C6—C5—C4—N3 | −20.20 (18) | N5—C5—C6—N6 | 39.70 (18) |
N5—C5—C4—N4 | −40.2 (2) | C4—C5—C6—N6 | −161.32 (12) |
C6—C5—C4—N4 | 163.31 (12) | N1—C6—N6—C66 | −168.39 (12) |
N3—C4—N4—C46 | 152.71 (12) | C5—C6—N6—C66 | 14.3 (2) |
C5—C4—N4—C46 | −30.69 (19) | N1—C6—N6—C62 | 5.8 (2) |
N3—C4—N4—C42 | −3.50 (19) | C5—C6—N6—C62 | −171.51 (13) |
C5—C4—N4—C42 | 173.10 (12) | C6—N6—C62—C63 | 127.17 (14) |
C4—N4—C42—C43 | 102.23 (14) | C66—N6—C62—C63 | −57.81 (15) |
C46—N4—C42—C43 | −56.49 (15) | N6—C62—C63—O64 | 58.45 (15) |
N4—C42—C43—O44 | 57.52 (15) | C62—C63—O64—C65 | −59.19 (15) |
C42—C43—O44—C45 | −59.45 (14) | C63—O64—C65—C66 | 57.64 (15) |
C43—O44—C45—C46 | 59.07 (15) | C6—N6—C66—C65 | −129.16 (14) |
C4—N4—C46—C45 | −103.05 (14) | C62—N6—C66—C65 | 56.13 (15) |
C42—N4—C46—C45 | 55.10 (15) | O64—C65—C66—N6 | −55.39 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O64i | 0.88 | 2.04 | 2.918 (2) | 177 |
N2—H2B···O44ii | 0.88 | 2.13 | 2.894 (2) | 144 |
C43—H43A···O5ii | 0.99 | 2.47 | 3.376 (2) | 152 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y−1/2, −z−1/2. |
(IV) 2-Amino-4,6-bis(benzylamino)-5-nitrosopyrimidine
top
Crystal data top
C18H18N6O | F(000) = 704 |
Mr = 334.38 | Dx = 1.398 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3618 reflections |
a = 12.9416 (1) Å | θ = 3.3–27.5° |
b = 6.6816 (3) Å | µ = 0.09 mm−1 |
c = 20.0033 (5) Å | T = 120 K |
β = 113.3020 (12)° | Plate, purple |
V = 1588.61 (8) Å3 | 0.42 × 0.12 × 0.03 mm |
Z = 4 | |
Data collection top
Kappa-CCD diffractometer | 3618 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2492 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.099 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −16→16 |
Tmin = 0.957, Tmax = 0.997 | k = −8→8 |
27586 measured reflections | l = −25→25 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0597P)2 + 0.3316P] where P = (Fo2 + 2Fc2)/3 |
3618 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Crystal data top
C18H18N6O | V = 1588.61 (8) Å3 |
Mr = 334.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.9416 (1) Å | µ = 0.09 mm−1 |
b = 6.6816 (3) Å | T = 120 K |
c = 20.0033 (5) Å | 0.42 × 0.12 × 0.03 mm |
β = 113.3020 (12)° | |
Data collection top
Kappa-CCD diffractometer | 3618 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2492 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.997 | Rint = 0.099 |
27586 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.27 e Å−3 |
3618 reflections | Δρmin = −0.34 e Å−3 |
226 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.33577 (11) | 0.84162 (19) | 0.20935 (7) | 0.0158 (3) | |
C2 | 0.39878 (13) | 0.9984 (2) | 0.24680 (8) | 0.0149 (3) | |
N2 | 0.50593 (11) | 0.9986 (2) | 0.25476 (7) | 0.0173 (3) | |
N3 | 0.36605 (11) | 1.15517 (19) | 0.27714 (7) | 0.0153 (3) | |
C4 | 0.25925 (13) | 1.1526 (2) | 0.27140 (8) | 0.0145 (3) | |
N4 | 0.22099 (11) | 1.30115 (19) | 0.29972 (7) | 0.0163 (3) | |
C47 | 0.29104 (14) | 1.4571 (2) | 0.34737 (9) | 0.0179 (4) | |
C41 | 0.33596 (13) | 1.4021 (3) | 0.42764 (8) | 0.0178 (4) | |
C42 | 0.36786 (14) | 1.2078 (3) | 0.45173 (9) | 0.0210 (4) | |
C43 | 0.41066 (15) | 1.1621 (3) | 0.52538 (9) | 0.0240 (4) | |
C44 | 0.42185 (15) | 1.3108 (3) | 0.57609 (9) | 0.0255 (4) | |
C45 | 0.39044 (15) | 1.5049 (3) | 0.55276 (9) | 0.0256 (4) | |
C46 | 0.34766 (14) | 1.5509 (3) | 0.47891 (9) | 0.0217 (4) | |
C5 | 0.18352 (13) | 0.9904 (2) | 0.23483 (8) | 0.0142 (3) | |
N5 | 0.08014 (11) | 1.0005 (2) | 0.23510 (7) | 0.0170 (3) | |
O5 | 0.00954 (10) | 0.86113 (17) | 0.20251 (6) | 0.0206 (3) | |
C6 | 0.22881 (13) | 0.8366 (2) | 0.20293 (8) | 0.0143 (3) | |
N6 | 0.16166 (11) | 0.6876 (2) | 0.16666 (7) | 0.0176 (3) | |
C67 | 0.18896 (14) | 0.5396 (2) | 0.12282 (9) | 0.0198 (4) | |
C61 | 0.14731 (13) | 0.5977 (2) | 0.04300 (9) | 0.0186 (4) | |
C62 | 0.14399 (14) | 0.4510 (3) | −0.00734 (9) | 0.0223 (4) | |
C63 | 0.10857 (15) | 0.4990 (3) | −0.08063 (9) | 0.0258 (4) | |
C64 | 0.07491 (15) | 0.6918 (3) | −0.10478 (9) | 0.0260 (4) | |
C65 | 0.07738 (15) | 0.8381 (3) | −0.05510 (9) | 0.0248 (4) | |
C66 | 0.11374 (14) | 0.7909 (3) | 0.01851 (9) | 0.0220 (4) | |
H2A | 0.5318 | 0.9007 | 0.2362 | 0.021* | |
H2B | 0.5509 | 1.0965 | 0.2786 | 0.021* | |
H4 | 0.1482 | 1.3057 | 0.2889 | 0.020* | |
H47A | 0.2463 | 1.5816 | 0.3396 | 0.021* | |
H47B | 0.3553 | 1.4844 | 0.3337 | 0.021* | |
H42 | 0.3603 | 1.1049 | 0.4173 | 0.025* | |
H43 | 0.4323 | 1.0286 | 0.5411 | 0.029* | |
H44 | 0.4509 | 1.2797 | 0.6265 | 0.031* | |
H45 | 0.3981 | 1.6073 | 0.5874 | 0.031* | |
H46 | 0.3263 | 1.6846 | 0.4634 | 0.026* | |
H6 | 0.0956 | 0.6779 | 0.1694 | 0.021* | |
H67A | 0.1551 | 0.4097 | 0.1269 | 0.024* | |
H67B | 0.2716 | 0.5217 | 0.1424 | 0.024* | |
H62 | 0.1660 | 0.3178 | 0.0085 | 0.027* | |
H63 | 0.1074 | 0.3985 | −0.1145 | 0.031* | |
H64 | 0.0503 | 0.7236 | −0.1550 | 0.031* | |
H65 | 0.0542 | 0.9707 | −0.0712 | 0.030* | |
H66 | 0.1156 | 0.8921 | 0.0523 | 0.026* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0144 (7) | 0.0164 (7) | 0.0168 (7) | −0.0007 (5) | 0.0066 (6) | 0.0003 (5) |
C2 | 0.0153 (8) | 0.0161 (8) | 0.0133 (8) | 0.0012 (6) | 0.0057 (6) | 0.0034 (6) |
N2 | 0.0141 (7) | 0.0157 (7) | 0.0236 (7) | −0.0002 (5) | 0.0090 (6) | −0.0029 (6) |
N3 | 0.0132 (7) | 0.0160 (7) | 0.0169 (7) | 0.0000 (5) | 0.0063 (6) | −0.0003 (5) |
C4 | 0.0155 (8) | 0.0171 (8) | 0.0117 (7) | 0.0019 (6) | 0.0061 (6) | 0.0036 (6) |
N4 | 0.0126 (7) | 0.0182 (7) | 0.0184 (7) | 0.0003 (5) | 0.0067 (6) | −0.0016 (5) |
C47 | 0.0182 (9) | 0.0169 (8) | 0.0197 (8) | −0.0004 (6) | 0.0087 (7) | −0.0027 (6) |
C41 | 0.0122 (8) | 0.0228 (9) | 0.0195 (8) | −0.0020 (6) | 0.0076 (7) | −0.0029 (7) |
C42 | 0.0205 (9) | 0.0230 (9) | 0.0200 (8) | −0.0016 (7) | 0.0086 (7) | −0.0029 (7) |
C43 | 0.0203 (9) | 0.0255 (9) | 0.0258 (9) | −0.0012 (7) | 0.0087 (8) | 0.0024 (7) |
C44 | 0.0202 (9) | 0.0381 (11) | 0.0180 (9) | −0.0035 (8) | 0.0071 (8) | −0.0004 (8) |
C45 | 0.0224 (10) | 0.0333 (10) | 0.0211 (9) | −0.0019 (8) | 0.0085 (8) | −0.0091 (8) |
C46 | 0.0179 (9) | 0.0227 (9) | 0.0250 (9) | 0.0011 (7) | 0.0090 (7) | −0.0024 (7) |
C5 | 0.0133 (8) | 0.0168 (8) | 0.0136 (7) | −0.0002 (6) | 0.0066 (6) | 0.0008 (6) |
N5 | 0.0161 (7) | 0.0193 (7) | 0.0156 (7) | −0.0032 (6) | 0.0062 (6) | −0.0003 (6) |
O5 | 0.0167 (6) | 0.0233 (6) | 0.0219 (6) | −0.0054 (5) | 0.0079 (5) | −0.0035 (5) |
C6 | 0.0148 (8) | 0.0163 (8) | 0.0116 (7) | 0.0003 (6) | 0.0052 (6) | 0.0027 (6) |
N6 | 0.0152 (7) | 0.0190 (7) | 0.0200 (7) | −0.0033 (6) | 0.0086 (6) | −0.0030 (6) |
C67 | 0.0176 (9) | 0.0181 (8) | 0.0233 (9) | −0.0010 (7) | 0.0075 (7) | −0.0057 (7) |
C61 | 0.0125 (8) | 0.0223 (9) | 0.0217 (9) | −0.0039 (7) | 0.0077 (7) | −0.0052 (7) |
C62 | 0.0149 (9) | 0.0231 (9) | 0.0286 (10) | −0.0015 (7) | 0.0082 (7) | −0.0061 (7) |
C63 | 0.0178 (9) | 0.0350 (11) | 0.0235 (9) | −0.0036 (8) | 0.0070 (7) | −0.0142 (8) |
C64 | 0.0199 (9) | 0.0382 (11) | 0.0190 (9) | −0.0009 (8) | 0.0068 (7) | −0.0035 (8) |
C65 | 0.0224 (10) | 0.0274 (10) | 0.0254 (9) | 0.0015 (7) | 0.0101 (8) | 0.0000 (8) |
C66 | 0.0217 (9) | 0.0233 (9) | 0.0223 (9) | −0.0022 (7) | 0.0101 (8) | −0.0064 (7) |
Geometric parameters (Å, º) top
N1—C6 | 1.339 (2) | C45—H45 | 0.95 |
N1—C2 | 1.357 (2) | C46—H46 | 0.95 |
C2—N2 | 1.332 (2) | C5—N5 | 1.3417 (19) |
C2—N3 | 1.3594 (19) | C5—C6 | 1.450 (2) |
N2—H2A | 0.88 | N5—O5 | 1.2868 (17) |
N2—H2B | 0.88 | C6—N6 | 1.332 (2) |
N3—C4 | 1.341 (2) | N6—C67 | 1.455 (2) |
C4—N4 | 1.332 (2) | N6—H6 | 0.88 |
C4—C5 | 1.450 (2) | C67—C61 | 1.520 (2) |
N4—C47 | 1.460 (2) | C67—H67A | 0.99 |
N4—H4 | 0.88 | C67—H67B | 0.99 |
C47—C41 | 1.521 (2) | C61—C66 | 1.388 (2) |
C47—H47A | 0.99 | C61—C62 | 1.394 (2) |
C47—H47B | 0.99 | C62—C63 | 1.389 (2) |
C41—C42 | 1.390 (2) | C62—H62 | 0.95 |
C41—C46 | 1.393 (2) | C63—C64 | 1.385 (3) |
C42—C43 | 1.388 (2) | C63—H63 | 0.95 |
C42—H42 | 0.95 | C64—C65 | 1.385 (2) |
C43—C44 | 1.386 (3) | C64—H64 | 0.95 |
C43—H43 | 0.95 | C65—C66 | 1.393 (2) |
C44—C45 | 1.384 (3) | C65—H65 | 0.95 |
C44—H44 | 0.95 | C66—H66 | 0.95 |
C45—C46 | 1.392 (2) | | |
| | | |
C6—N1—C2 | 116.41 (13) | C45—C46—H46 | 119.8 |
N2—C2—N1 | 115.89 (13) | C41—C46—H46 | 119.8 |
N2—C2—N3 | 116.08 (14) | N5—C5—C6 | 127.93 (14) |
N1—C2—N3 | 128.04 (14) | N5—C5—C4 | 115.87 (13) |
C2—N2—H2A | 120.0 | C6—C5—C4 | 116.19 (13) |
C2—N2—H2B | 120.0 | O5—N5—C5 | 118.09 (13) |
H2A—N2—H2B | 120.0 | N6—C6—N1 | 119.85 (14) |
C4—N3—C2 | 116.39 (13) | N6—C6—C5 | 118.64 (14) |
N4—C4—N3 | 119.87 (14) | N1—C6—C5 | 121.52 (14) |
N4—C4—C5 | 118.74 (14) | C6—N6—C67 | 125.08 (13) |
N3—C4—C5 | 121.39 (13) | C6—N6—H6 | 117.5 |
C4—N4—C47 | 124.77 (14) | C67—N6—H6 | 117.5 |
C4—N4—H4 | 117.6 | N6—C67—C61 | 112.94 (13) |
C47—N4—H4 | 117.6 | N6—C67—H67A | 109.0 |
N4—C47—C41 | 113.33 (13) | C61—C67—H67A | 109.0 |
N4—C47—H47A | 108.9 | N6—C67—H67B | 109.0 |
C41—C47—H47A | 108.9 | C61—C67—H67B | 109.0 |
N4—C47—H47B | 108.9 | H67A—C67—H67B | 107.8 |
C41—C47—H47B | 108.9 | C66—C61—C62 | 118.90 (15) |
H47A—C47—H47B | 107.7 | C66—C61—C67 | 122.68 (14) |
C42—C41—C46 | 118.74 (15) | C62—C61—C67 | 118.42 (15) |
C42—C41—C47 | 121.93 (14) | C63—C62—C61 | 120.20 (16) |
C46—C41—C47 | 119.31 (15) | C63—C62—H62 | 119.9 |
C43—C42—C41 | 120.86 (16) | C61—C62—H62 | 119.9 |
C43—C42—H42 | 119.6 | C64—C63—C62 | 120.65 (16) |
C41—C42—H42 | 119.6 | C64—C63—H63 | 119.7 |
C44—C43—C42 | 120.10 (17) | C62—C63—H63 | 119.7 |
C44—C43—H43 | 119.9 | C63—C64—C65 | 119.44 (16) |
C42—C43—H43 | 119.9 | C63—C64—H64 | 120.3 |
C45—C44—C43 | 119.57 (16) | C65—C64—H64 | 120.3 |
C45—C44—H44 | 120.2 | C64—C65—C66 | 120.07 (17) |
C43—C44—H44 | 120.2 | C64—C65—H65 | 120.0 |
C44—C45—C46 | 120.35 (16) | C66—C65—H65 | 120.0 |
C44—C45—H45 | 119.8 | C61—C66—C65 | 120.74 (15) |
C46—C45—H45 | 119.8 | C61—C66—H66 | 119.6 |
C45—C46—C41 | 120.37 (16) | C65—C66—H66 | 119.6 |
| | | |
C6—N1—C2—N2 | 178.01 (13) | N3—C4—C5—C6 | −2.1 (2) |
C6—N1—C2—N3 | −2.0 (2) | C6—C5—N5—O5 | −1.3 (2) |
N2—C2—N3—C4 | −177.88 (13) | C4—C5—N5—O5 | 179.15 (13) |
N1—C2—N3—C4 | 2.1 (2) | C2—N1—C6—N6 | 179.75 (13) |
C2—N3—C4—N4 | −179.94 (13) | C2—N1—C6—C5 | −0.4 (2) |
C2—N3—C4—C5 | 0.1 (2) | N5—C5—C6—N6 | 2.6 (2) |
N3—C4—N4—C47 | −9.9 (2) | C4—C5—C6—N6 | −177.86 (13) |
C5—C4—N4—C47 | 170.07 (14) | N5—C5—C6—N1 | −177.27 (14) |
C4—N4—C47—C41 | −89.40 (17) | C4—C5—C6—N1 | 2.3 (2) |
N4—C47—C41—C42 | 36.4 (2) | N1—C6—N6—C67 | −9.7 (2) |
N4—C47—C41—C46 | −144.84 (15) | C5—C6—N6—C67 | 170.45 (14) |
C46—C41—C42—C43 | 0.0 (2) | C6—N6—C67—C61 | −93.12 (18) |
C47—C41—C42—C43 | 178.74 (15) | N6—C67—C61—C66 | 15.6 (2) |
C41—C42—C43—C44 | 0.2 (3) | N6—C67—C61—C62 | −165.07 (14) |
C42—C43—C44—C45 | −0.2 (3) | C66—C61—C62—C63 | 0.6 (2) |
C43—C44—C45—C46 | 0.1 (3) | C67—C61—C62—C63 | −178.72 (15) |
C44—C45—C46—C41 | 0.0 (3) | C61—C62—C63—C64 | −0.8 (3) |
C42—C41—C46—C45 | −0.1 (2) | C62—C63—C64—C65 | 0.4 (3) |
C47—C41—C46—C45 | −178.86 (15) | C63—C64—C65—C66 | 0.2 (3) |
N4—C4—C5—N5 | −2.5 (2) | C62—C61—C66—C65 | −0.1 (2) |
N3—C4—C5—N5 | 177.46 (13) | C67—C61—C66—C65 | 179.23 (15) |
N4—C4—C5—C6 | 177.94 (13) | C64—C65—C66—C61 | −0.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N3i | 0.88 | 2.19 | 3.042 (2) | 163 |
N2—H2B···N1ii | 0.88 | 2.15 | 2.967 (2) | 155 |
N4—H4···O5iii | 0.88 | 2.15 | 2.993 (2) | 161 |
N6—H6···O5 | 0.88 | 1.94 | 2.617 (2) | 133 |
C63—H63···O5iv | 0.95 | 2.51 | 3.335 (2) | 146 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, −y+1, −z. |
(V) 2-Amino-5-nitroso-4,6-bis(3-pyridylmethoxy)pyrimidine
top
Crystal data top
C16H14N6O3 | F(000) = 704 |
Mr = 338.33 | Dx = 1.461 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2026 reflections |
a = 6.881 (2) Å | θ = 3.3–27.5° |
b = 9.140 (3) Å | µ = 0.11 mm−1 |
c = 24.4636 (10) Å | T = 120 K |
V = 1538.6 (7) Å3 | Plate, colourless |
Z = 4 | 0.45 × 0.12 × 0.04 mm |
Data collection top
Kappa-CCD diffractometer | 1369 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.067 |
Graphite monochromator | θmax = 27.5°, θmin = 3.3° |
ϕ scans, and ω scans with κ offsets | h = −7→8 |
8813 measured reflections | k = −11→8 |
2026 independent reflections | l = −29→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0483P)2] where P = (Fo2 + 2Fc2)/3 |
2026 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C16H14N6O3 | V = 1538.6 (7) Å3 |
Mr = 338.33 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.881 (2) Å | µ = 0.11 mm−1 |
b = 9.140 (3) Å | T = 120 K |
c = 24.4636 (10) Å | 0.45 × 0.12 × 0.04 mm |
Data collection top
Kappa-CCD diffractometer | 1369 reflections with I > 2σ(I) |
8813 measured reflections | Rint = 0.067 |
2026 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.21 e Å−3 |
2026 reflections | Δρmin = −0.28 e Å−3 |
226 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.0674 (3) | 0.6159 (3) | 0.09921 (10) | 0.0212 (6) | |
C2 | 0.1069 (4) | 0.4982 (3) | 0.13185 (12) | 0.0218 (7) | |
N2 | −0.0158 (4) | 0.3891 (3) | 0.13100 (10) | 0.0262 (6) | |
N3 | 0.2646 (3) | 0.4844 (3) | 0.16516 (10) | 0.0222 (6) | |
C4 | 0.3907 (4) | 0.5912 (3) | 0.16322 (12) | 0.0217 (7) | |
C41 | 0.7479 (4) | 0.4628 (3) | 0.26183 (12) | 0.0232 (7) | |
C42 | 0.7851 (4) | 0.5863 (4) | 0.29238 (13) | 0.0272 (8) | |
N43 | 0.9420 (4) | 0.6031 (3) | 0.32434 (11) | 0.0310 (7) | |
C44 | 1.0661 (4) | 0.4898 (3) | 0.32717 (13) | 0.0276 (8) | |
C45 | 1.0396 (4) | 0.3622 (4) | 0.29918 (13) | 0.0275 (8) | |
C46 | 0.8792 (4) | 0.3490 (3) | 0.26567 (12) | 0.0248 (7) | |
C47 | 0.5674 (5) | 0.4501 (3) | 0.22746 (13) | 0.0274 (8) | |
O4 | 0.5487 (3) | 0.5831 (2) | 0.19553 (9) | 0.0262 (5) | |
C5 | 0.3746 (4) | 0.7162 (3) | 0.12907 (12) | 0.0195 (7) | |
N5 | 0.5231 (4) | 0.8161 (3) | 0.13111 (11) | 0.0272 (6) | |
O5 | 0.5131 (3) | 0.9247 (2) | 0.10003 (9) | 0.0357 (6) | |
C6 | 0.1985 (4) | 0.7200 (3) | 0.09741 (12) | 0.0190 (7) | |
C61 | −0.0218 (4) | 0.9674 (3) | 0.00058 (12) | 0.0212 (7) | |
C62 | 0.1210 (4) | 0.9966 (3) | −0.03825 (12) | 0.0240 (7) | |
N63 | 0.1216 (4) | 1.1128 (3) | −0.07152 (10) | 0.0255 (6) | |
C64 | −0.0289 (4) | 1.2054 (3) | −0.06733 (13) | 0.0244 (7) | |
C65 | −0.1778 (5) | 1.1870 (3) | −0.03061 (13) | 0.0268 (8) | |
C66 | −0.1740 (4) | 1.0660 (3) | 0.00399 (13) | 0.0253 (8) | |
C67 | −0.0138 (4) | 0.8328 (3) | 0.03406 (12) | 0.0231 (7) | |
O6 | 0.1680 (3) | 0.8340 (2) | 0.06504 (9) | 0.0230 (5) | |
H2A | 0.0055 | 0.3113 | 0.1514 | 0.031* | |
H2B | −0.1196 | 0.3933 | 0.1101 | 0.031* | |
H42 | 0.6941 | 0.6643 | 0.2907 | 0.033* | |
H44 | 1.1777 | 0.4990 | 0.3498 | 0.033* | |
H45 | 1.1298 | 0.2841 | 0.3027 | 0.033* | |
H46 | 0.8591 | 0.2618 | 0.2453 | 0.030* | |
H41A | 0.5773 | 0.3642 | 0.2029 | 0.033* | |
H41B | 0.4521 | 0.4372 | 0.2512 | 0.033* | |
H62 | 0.2255 | 0.9292 | −0.0413 | 0.029* | |
H64 | −0.0327 | 1.2879 | −0.0909 | 0.029* | |
H65 | −0.2814 | 1.2555 | −0.0288 | 0.032* | |
H66 | −0.2753 | 1.0512 | 0.0298 | 0.030* | |
H61A | −0.1260 | 0.8294 | 0.0594 | 0.028* | |
H61B | −0.0190 | 0.7454 | 0.0102 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0211 (14) | 0.0218 (14) | 0.0207 (14) | 0.0006 (11) | −0.0006 (11) | 0.0031 (12) |
C2 | 0.0196 (15) | 0.0252 (17) | 0.0205 (17) | 0.0022 (15) | 0.0002 (13) | 0.0000 (15) |
N2 | 0.0234 (14) | 0.0244 (15) | 0.0309 (15) | −0.0055 (12) | −0.0087 (11) | 0.0088 (13) |
N3 | 0.0206 (14) | 0.0242 (15) | 0.0217 (14) | −0.0022 (12) | −0.0027 (11) | 0.0018 (12) |
C4 | 0.0190 (16) | 0.0269 (18) | 0.0191 (17) | 0.0007 (14) | 0.0002 (13) | −0.0009 (14) |
C41 | 0.0195 (16) | 0.0254 (18) | 0.0247 (19) | −0.0031 (13) | −0.0005 (13) | 0.0001 (15) |
C42 | 0.0208 (17) | 0.0280 (19) | 0.033 (2) | 0.0041 (14) | −0.0048 (14) | 0.0062 (16) |
N43 | 0.0296 (16) | 0.0279 (16) | 0.0355 (17) | −0.0024 (13) | −0.0081 (13) | 0.0015 (13) |
C44 | 0.0220 (17) | 0.031 (2) | 0.0295 (18) | 0.0030 (15) | −0.0050 (14) | 0.0067 (17) |
C45 | 0.0232 (18) | 0.0314 (19) | 0.0281 (18) | 0.0038 (14) | 0.0025 (14) | 0.0041 (16) |
C46 | 0.0224 (17) | 0.0281 (18) | 0.0241 (18) | −0.0027 (14) | 0.0033 (13) | 0.0009 (15) |
C47 | 0.0243 (18) | 0.0247 (18) | 0.0333 (19) | −0.0049 (13) | −0.0071 (14) | 0.0081 (15) |
O4 | 0.0242 (12) | 0.0243 (12) | 0.0302 (12) | −0.0020 (10) | −0.0069 (9) | 0.0053 (10) |
C5 | 0.0172 (15) | 0.0206 (16) | 0.0208 (17) | −0.0021 (13) | 0.0010 (12) | −0.0019 (14) |
N5 | 0.0266 (15) | 0.0260 (15) | 0.0289 (16) | −0.0013 (12) | 0.0017 (12) | 0.0022 (13) |
O5 | 0.0310 (14) | 0.0340 (14) | 0.0422 (15) | −0.0080 (11) | −0.0027 (11) | 0.0128 (12) |
C6 | 0.0168 (16) | 0.0220 (17) | 0.0182 (17) | 0.0003 (13) | 0.0048 (12) | −0.0017 (14) |
C61 | 0.0196 (16) | 0.0223 (16) | 0.0218 (16) | −0.0015 (13) | −0.0030 (13) | −0.0017 (14) |
C62 | 0.0203 (17) | 0.0207 (17) | 0.0310 (19) | 0.0047 (14) | −0.0009 (14) | −0.0015 (16) |
N63 | 0.0257 (14) | 0.0249 (14) | 0.0259 (15) | −0.0008 (12) | −0.0016 (11) | 0.0027 (13) |
C64 | 0.0274 (18) | 0.0222 (16) | 0.0235 (17) | 0.0008 (14) | −0.0026 (14) | 0.0007 (14) |
C65 | 0.0263 (18) | 0.0240 (18) | 0.0301 (19) | 0.0077 (14) | 0.0002 (14) | 0.0000 (16) |
C66 | 0.0204 (17) | 0.0299 (19) | 0.0255 (18) | −0.0008 (14) | 0.0035 (14) | −0.0007 (16) |
C67 | 0.0199 (16) | 0.0253 (17) | 0.0243 (17) | −0.0015 (13) | −0.0029 (13) | 0.0020 (14) |
O6 | 0.0206 (11) | 0.0223 (11) | 0.0261 (12) | −0.0020 (9) | −0.0033 (9) | 0.0043 (10) |
Geometric parameters (Å, º) top
N1—C6 | 1.312 (4) | C47—H41A | 0.99 |
N1—C2 | 1.367 (4) | C47—H41B | 0.99 |
C2—N2 | 1.307 (4) | C5—N5 | 1.372 (4) |
C2—N3 | 1.363 (4) | C5—C6 | 1.438 (4) |
N2—H2A | 0.88 | N5—O5 | 1.252 (3) |
N2—H2B | 0.88 | C6—O6 | 1.325 (4) |
N3—C4 | 1.307 (4) | C61—C66 | 1.384 (4) |
C4—O4 | 1.346 (3) | C61—C62 | 1.392 (4) |
C4—C5 | 1.420 (4) | C61—C67 | 1.479 (4) |
C41—C42 | 1.378 (4) | C62—N63 | 1.338 (4) |
C41—C46 | 1.381 (4) | C62—H62 | 0.95 |
C41—C47 | 1.504 (4) | N63—C64 | 1.342 (4) |
C42—N43 | 1.342 (4) | C64—C65 | 1.373 (4) |
C42—H42 | 0.95 | C64—H64 | 0.95 |
N43—C44 | 1.344 (4) | C65—C66 | 1.393 (4) |
C44—C45 | 1.365 (4) | C65—H65 | 0.95 |
C44—H44 | 0.95 | C66—H66 | 0.95 |
C45—C46 | 1.380 (4) | C67—O6 | 1.463 (3) |
C45—H45 | 0.95 | C67—H61A | 0.99 |
C46—H46 | 0.95 | C67—H61B | 0.99 |
C47—O4 | 1.451 (3) | | |
| | | |
C6—N1—C2 | 117.0 (2) | H41A—C47—H41B | 108.4 |
N2—C2—N3 | 116.9 (3) | C4—O4—C47 | 115.7 (2) |
N2—C2—N1 | 117.6 (3) | N5—C5—C4 | 117.2 (2) |
N3—C2—N1 | 125.5 (3) | N5—C5—C6 | 129.1 (3) |
C2—N2—H2A | 120.0 | C4—C5—C6 | 113.7 (2) |
C2—N2—H2B | 120.0 | O5—N5—C5 | 117.7 (2) |
H2A—N2—H2B | 120.0 | N1—C6—O6 | 118.8 (2) |
C4—N3—C2 | 116.0 (3) | N1—C6—C5 | 122.9 (3) |
N3—C4—O4 | 118.3 (3) | O6—C6—C5 | 118.3 (2) |
N3—C4—C5 | 124.8 (3) | C66—C61—C62 | 116.8 (3) |
O4—C4—C5 | 116.9 (2) | C66—C61—C67 | 122.4 (3) |
C42—C41—C46 | 117.3 (3) | C62—C61—C67 | 120.7 (3) |
C42—C41—C47 | 121.3 (3) | N63—C62—C61 | 124.7 (3) |
C46—C41—C47 | 121.3 (3) | N63—C62—H62 | 117.6 |
N43—C42—C41 | 124.0 (3) | C61—C62—H62 | 117.6 |
N43—C42—H42 | 118.0 | C62—N63—C64 | 116.9 (3) |
C41—C42—H42 | 118.0 | N63—C64—C65 | 123.3 (3) |
C42—N43—C44 | 116.9 (3) | N63—C64—H64 | 118.4 |
N43—C44—C45 | 123.2 (3) | C65—C64—H64 | 118.4 |
N43—C44—H44 | 118.4 | C64—C65—C66 | 118.8 (3) |
C45—C44—H44 | 118.4 | C64—C65—H65 | 120.6 |
C44—C45—C46 | 118.6 (3) | C66—C65—H65 | 120.6 |
C44—C45—H45 | 120.7 | C61—C66—C65 | 119.6 (3) |
C46—C45—H45 | 120.7 | C61—C66—H66 | 120.2 |
C45—C46—C41 | 119.9 (3) | C65—C66—H66 | 120.2 |
C45—C46—H46 | 120.1 | O6—C67—C61 | 108.2 (2) |
C41—C46—H46 | 120.1 | O6—C67—H61A | 110.1 |
O4—C47—C41 | 108.0 (2) | C61—C67—H61A | 110.1 |
O4—C47—H41A | 110.1 | O6—C67—H61B | 110.1 |
C41—C47—H41A | 110.1 | C61—C67—H61B | 110.1 |
O4—C47—H41B | 110.1 | H61A—C67—H61B | 108.4 |
C41—C47—H41B | 110.1 | C6—O6—C67 | 116.0 (2) |
| | | |
C6—N1—C2—N2 | −175.2 (3) | O4—C4—C5—C6 | −177.6 (2) |
C6—N1—C2—N3 | 4.4 (4) | C4—C5—N5—O5 | 178.0 (3) |
N2—C2—N3—C4 | 176.4 (3) | C6—C5—N5—O5 | −3.2 (4) |
N1—C2—N3—C4 | −3.2 (4) | C2—N1—C6—O6 | 178.1 (3) |
C2—N3—C4—O4 | 179.7 (3) | C2—N1—C6—C5 | −1.9 (4) |
C2—N3—C4—C5 | −0.6 (4) | N5—C5—C6—N1 | 179.8 (3) |
C46—C41—C42—N43 | 1.5 (5) | C4—C5—C6—N1 | −1.4 (4) |
C47—C41—C42—N43 | 179.1 (3) | N5—C5—C6—O6 | −0.2 (5) |
C41—C42—N43—C44 | −1.7 (5) | C4—C5—C6—O6 | 178.6 (2) |
C42—N43—C44—C45 | 0.5 (5) | C66—C61—C62—N63 | 0.8 (4) |
N43—C44—C45—C46 | 0.9 (5) | C67—C61—C62—N63 | 177.6 (3) |
C44—C45—C46—C41 | −1.1 (4) | C61—C62—N63—C64 | −1.2 (4) |
C42—C41—C46—C45 | 0.0 (4) | C62—N63—C64—C65 | 1.0 (4) |
C47—C41—C46—C45 | −177.6 (3) | N63—C64—C65—C66 | −0.3 (5) |
C42—C41—C47—O4 | 48.4 (4) | C62—C61—C66—C65 | 0.0 (4) |
C46—C41—C47—O4 | −134.1 (3) | C67—C61—C66—C65 | −176.8 (3) |
N3—C4—O4—C47 | 3.4 (4) | C64—C65—C66—C61 | −0.2 (4) |
C5—C4—O4—C47 | −176.3 (3) | C66—C61—C67—O6 | −123.6 (3) |
C41—C47—O4—C4 | −178.5 (2) | C62—C61—C67—O6 | 59.8 (3) |
N3—C4—C5—N5 | −178.3 (3) | N1—C6—O6—C67 | 0.4 (4) |
O4—C4—C5—N5 | 1.4 (4) | C5—C6—O6—C67 | −179.6 (2) |
N3—C4—C5—C6 | 2.7 (4) | C61—C67—O6—C6 | −179.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N43i | 0.88 | 2.03 | 2.878 (4) | 163 |
N2—H2B···N63ii | 0.88 | 2.02 | 2.888 (4) | 171 |
C65—H65···Cg2iii | 0.95 | 2.69 | 3.526 (4) | 148 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z; (iii) x−1/2, −y+5/2, −z. |
(VI) 2-Amino-4,6-bis(2-hydroxyethylamino)-5-nitrosopyrimidine
top
Crystal data top
C8H14N6O3 | F(000) = 512 |
Mr = 242.25 | Dx = 1.556 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2366 reflections |
a = 9.6487 (1) Å | θ = 3.1–27.5° |
b = 14.8594 (2) Å | µ = 0.12 mm−1 |
c = 7.3497 (2) Å | T = 120 K |
β = 101.097 (1)° | Rod, orange |
V = 1034.05 (3) Å3 | 0.20 × 0.06 × 0.04 mm |
Z = 4 | |
Data collection top
Kappa-CCD diffractometer | 1928 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.039 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
ϕ scans, and ω scans with κ offsets | h = −12→12 |
14888 measured reflections | k = −19→19 |
2366 independent reflections | l = −9→8 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0886P)2 + 1.0053P] where P = (Fo2 + 2Fc2)/3 |
2366 reflections | (Δ/σ)max = 0.001 |
180 parameters | Δρmax = 0.55 e Å−3 |
11 restraints | Δρmin = −0.37 e Å−3 |
Crystal data top
C8H14N6O3 | V = 1034.05 (3) Å3 |
Mr = 242.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.6487 (1) Å | µ = 0.12 mm−1 |
b = 14.8594 (2) Å | T = 120 K |
c = 7.3497 (2) Å | 0.20 × 0.06 × 0.04 mm |
β = 101.097 (1)° | |
Data collection top
Kappa-CCD diffractometer | 1928 reflections with I > 2σ(I) |
14888 measured reflections | Rint = 0.039 |
2366 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.066 | 11 restraints |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.55 e Å−3 |
2366 reflections | Δρmin = −0.37 e Å−3 |
180 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.36042 (17) | 0.22258 (12) | 0.0872 (3) | 0.0280 (4) | |
N2 | 0.36388 (18) | 0.06965 (13) | 0.0998 (3) | 0.0373 (5) | |
C2 | 0.4314 (2) | 0.14488 (14) | 0.0711 (3) | 0.0267 (4) | |
N3 | 0.56145 (16) | 0.13395 (12) | 0.0300 (2) | 0.0238 (4) | |
N4 | 0.76382 (18) | 0.20569 (12) | −0.0139 (2) | 0.0273 (4) | |
C4 | 0.6325 (2) | 0.20989 (14) | 0.0141 (3) | 0.0230 (4) | |
C41 | 0.84213 (18) | 0.12222 (13) | −0.0150 (3) | 0.0325 (5) | |
C42 | 0.98242 (18) | 0.13999 (13) | −0.0707 (3) | 0.0267 (8) | 0.819 (3) |
O4 | 1.05773 (18) | 0.20277 (12) | 0.0656 (3) | 0.0294 (5) | 0.819 (3) |
C421 | 0.9853 (9) | 0.1493 (13) | −0.048 (3) | 0.030* | 0.181 (3) |
O41 | 1.0470 (9) | 0.0613 (6) | −0.0744 (11) | 0.030* | 0.181 (3) |
C5 | 0.57073 (19) | 0.29767 (13) | 0.0296 (3) | 0.0233 (4) | |
N5 | 0.6318 (7) | 0.3787 (3) | 0.022 (2) | 0.0315 (15) | 0.68 |
O5 | 0.7592 (2) | 0.38242 (16) | −0.0047 (3) | 0.0326 (5) | 0.68 |
N51 | 0.6588 (14) | 0.3673 (4) | 0.025 (5) | 0.038 (4) | 0.32 |
O51 | 0.6123 (5) | 0.4452 (3) | 0.0401 (8) | 0.0366 (11) | 0.32 |
C6 | 0.4282 (2) | 0.29869 (14) | 0.0661 (3) | 0.0241 (4) | |
N6 | 0.36753 (17) | 0.37779 (13) | 0.0829 (2) | 0.0285 (4) | |
C61 | 0.22774 (17) | 0.39091 (13) | 0.1253 (2) | 0.0324 (5) | |
C62 | 0.11478 (17) | 0.40081 (13) | −0.0457 (2) | 0.0291 (8) | 0.819 (3) |
O6 | 0.14364 (18) | 0.46683 (12) | −0.1692 (3) | 0.0302 (5) | 0.819 (3) |
C621 | 0.1147 (9) | 0.3804 (15) | −0.0461 (11) | 0.0291 (8) | 0.181 (3) |
O61 | −0.0344 (7) | 0.3610 (6) | −0.0706 (12) | 0.0302 (5) | 0.181 (3) |
H2A | 0.4041 | 0.0170 | 0.0916 | 0.045* | |
H2B | 0.2791 | 0.0725 | 0.1269 | 0.045* | |
H4 | 0.8061 | 0.2563 | −0.0329 | 0.033* | |
H41A | 0.7865 | 0.0794 | −0.1034 | 0.039* | 0.819 (3) |
H41B | 0.8581 | 0.0947 | 0.1099 | 0.039* | 0.819 (3) |
H41C | 0.7945 | 0.0820 | −0.1152 | 0.039* | 0.181 (3) |
H41D | 0.8502 | 0.0905 | 0.1051 | 0.039* | 0.181 (3) |
H42A | 1.0365 | 0.0833 | −0.0704 | 0.032* | 0.819 (3) |
H42B | 0.9680 | 0.1665 | −0.1965 | 0.032* | 0.819 (3) |
H4A | 1.1369 | 0.2146 | 0.0398 | 0.035* | 0.819 (3) |
H42C | 0.9782 | 0.1876 | −0.1593 | 0.036* | 0.181 (3) |
H42D | 1.0404 | 0.1813 | 0.0608 | 0.036* | 0.181 (3) |
H41 | 1.0087 | 0.0217 | −0.0192 | 0.036* | 0.181 (3) |
H6 | 0.4160 | 0.4263 | 0.0670 | 0.034* | |
H61A | 0.2288 | 0.4455 | 0.2029 | 0.039* | 0.819 (3) |
H61B | 0.2046 | 0.3389 | 0.1983 | 0.039* | 0.819 (3) |
H61C | 0.2217 | 0.4518 | 0.1779 | 0.039* | 0.181 (3) |
H61D | 0.2121 | 0.3464 | 0.2196 | 0.039* | 0.181 (3) |
H62A | 0.1023 | 0.3423 | −0.1112 | 0.035* | 0.819 (3) |
H62B | 0.0245 | 0.4158 | −0.0077 | 0.035* | 0.819 (3) |
H6A | 0.1529 | 0.5170 | −0.1154 | 0.036* | 0.819 (3) |
H62C | 0.1191 | 0.4372 | −0.1154 | 0.035* | 0.181 (3) |
H62D | 0.1519 | 0.3333 | −0.1190 | 0.035* | 0.181 (3) |
H61 | −0.0475 | 0.3055 | −0.0876 | 0.036* | 0.181 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0160 (8) | 0.0340 (10) | 0.0349 (10) | −0.0001 (6) | 0.0076 (7) | 0.0089 (7) |
N2 | 0.0189 (8) | 0.0323 (10) | 0.0646 (13) | 0.0020 (7) | 0.0178 (8) | 0.0134 (9) |
C2 | 0.0172 (9) | 0.0341 (11) | 0.0291 (10) | −0.0002 (7) | 0.0050 (7) | 0.0062 (8) |
N3 | 0.0149 (8) | 0.0336 (9) | 0.0234 (8) | −0.0045 (6) | 0.0051 (6) | −0.0002 (6) |
N4 | 0.0180 (8) | 0.0311 (9) | 0.0353 (10) | −0.0072 (6) | 0.0115 (7) | −0.0093 (7) |
C4 | 0.0174 (9) | 0.0345 (11) | 0.0173 (9) | −0.0049 (7) | 0.0037 (7) | −0.0048 (7) |
C41 | 0.0250 (10) | 0.0291 (11) | 0.0484 (13) | −0.0086 (8) | 0.0196 (9) | −0.0123 (9) |
C42 | 0.0206 (11) | 0.0252 (14) | 0.0386 (19) | −0.0055 (9) | 0.0164 (11) | −0.0095 (11) |
O4 | 0.0172 (8) | 0.0308 (10) | 0.0415 (11) | −0.0037 (7) | 0.0090 (7) | 0.0003 (7) |
C5 | 0.0151 (9) | 0.0322 (11) | 0.0221 (9) | −0.0041 (7) | 0.0026 (7) | −0.0010 (7) |
N5 | 0.0133 (16) | 0.053 (4) | 0.028 (2) | −0.0092 (18) | 0.0036 (18) | −0.005 (3) |
O5 | 0.0172 (11) | 0.0338 (12) | 0.0494 (14) | −0.0069 (9) | 0.0128 (10) | −0.0089 (10) |
N51 | 0.043 (9) | 0.026 (4) | 0.041 (6) | −0.016 (4) | 0.002 (9) | 0.004 (4) |
O51 | 0.028 (3) | 0.019 (2) | 0.060 (3) | −0.002 (2) | 0.005 (2) | −0.002 (2) |
C6 | 0.0159 (9) | 0.0346 (11) | 0.0214 (9) | 0.0003 (7) | 0.0025 (7) | 0.0034 (7) |
N6 | 0.0190 (8) | 0.0338 (10) | 0.0337 (9) | 0.0000 (7) | 0.0073 (7) | 0.0043 (7) |
C61 | 0.0238 (10) | 0.0401 (12) | 0.0360 (11) | 0.0057 (9) | 0.0123 (9) | 0.0073 (9) |
C62 | 0.0214 (10) | 0.024 (2) | 0.0424 (13) | 0.0010 (9) | 0.0083 (8) | 0.0171 (10) |
O6 | 0.0263 (9) | 0.0259 (9) | 0.0375 (10) | −0.0037 (7) | 0.0040 (7) | 0.0109 (7) |
C621 | 0.0214 (10) | 0.024 (2) | 0.0424 (13) | 0.0010 (9) | 0.0083 (8) | 0.0171 (10) |
O61 | 0.0263 (9) | 0.0259 (9) | 0.0375 (10) | −0.0037 (7) | 0.0040 (7) | 0.0109 (7) |
Geometric parameters (Å, º) top
N1—C6 | 1.331 (3) | O41—H41 | 0.84 |
N1—C2 | 1.359 (3) | C5—N51 | 1.344 (5) |
N2—C2 | 1.331 (3) | C5—N5 | 1.346 (4) |
N2—H2A | 0.88 | C5—C6 | 1.451 (3) |
N2—H2B | 0.88 | N5—O5 | 1.284 (4) |
C2—N3 | 1.356 (2) | N51—O51 | 1.254 (5) |
N3—C4 | 1.337 (3) | C6—N6 | 1.330 (3) |
N4—C4 | 1.323 (2) | N6—C61 | 1.455 (2) |
N4—C41 | 1.453 (3) | N6—H6 | 0.88 |
N4—H4 | 0.88 | C61—C62 | 1.5042 |
C4—C5 | 1.448 (3) | C61—C621 | 1.507 (5) |
C41—C421 | 1.502 (5) | C61—H61A | 0.99 |
C41—C42 | 1.5108 | C61—H61B | 0.99 |
C41—H41A | 0.99 | C61—H61C | 0.99 |
C41—H41B | 0.99 | C61—H61D | 0.99 |
C41—H41C | 0.99 | C62—O6 | 1.400 (2) |
C41—H41D | 0.99 | C62—H62A | 0.99 |
C42—O4 | 1.457 (3) | C62—H62B | 0.99 |
C42—H42A | 0.99 | O6—H6A | 0.84 |
C42—H42B | 0.99 | C621—O61 | 1.444 (5) |
O4—H4A | 0.84 | C621—H62C | 0.99 |
C421—O41 | 1.47 (2) | C621—H62D | 0.99 |
C421—H42C | 0.99 | O61—H61 | 0.84 |
C421—H42D | 0.99 | | |
| | | |
C6—N1—C2 | 116.39 (17) | N51—C5—C4 | 114.8 (4) |
C2—N2—H2A | 120.0 | N5—C5—C4 | 127.8 (3) |
C2—N2—H2B | 120.0 | N51—C5—C6 | 128.6 (4) |
H2A—N2—H2B | 120.0 | N5—C5—C6 | 115.8 (3) |
N2—C2—N3 | 115.90 (19) | C4—C5—C6 | 116.30 (16) |
N2—C2—N1 | 115.44 (18) | O5—N5—C5 | 118.9 (4) |
N3—C2—N1 | 128.66 (18) | O51—N51—C5 | 118.0 (6) |
C4—N3—C2 | 115.51 (17) | N6—C6—N1 | 120.34 (18) |
C4—N4—C41 | 123.74 (16) | N6—C6—C5 | 118.47 (17) |
C4—N4—H4 | 118.1 | N1—C6—C5 | 121.17 (18) |
C41—N4—H4 | 118.1 | C6—N6—C61 | 125.57 (17) |
N4—C4—N3 | 119.75 (18) | C6—N6—H6 | 117.2 |
N4—C4—C5 | 118.39 (17) | C61—N6—H6 | 117.2 |
N3—C4—C5 | 121.84 (17) | N6—C61—C62 | 112.74 (10) |
N4—C41—C421 | 105.5 (8) | N6—C61—C621 | 111.0 (5) |
N4—C41—C42 | 110.26 (9) | N6—C61—H61A | 109.0 |
N4—C41—H41A | 109.6 | C62—C61—H61A | 109.0 |
C421—C41—H41A | 117.8 | C621—C61—H61A | 119.4 |
C42—C41—H41A | 109.6 | N6—C61—H61B | 109.0 |
N4—C41—H41B | 109.6 | C62—C61—H61B | 109.0 |
C421—C41—H41B | 105.9 | C621—C61—H61B | 99.8 |
C42—C41—H41B | 109.6 | H61A—C61—H61B | 107.8 |
H41A—C41—H41B | 108.1 | N6—C61—H61C | 109.4 |
N4—C41—H41C | 110.6 | C62—C61—H61C | 98.6 |
C421—C41—H41C | 110.6 | C621—C61—H61C | 109.4 |
C42—C41—H41C | 102.5 | H61B—C61—H61C | 117.8 |
H41B—C41—H41C | 114.1 | N6—C61—H61D | 109.4 |
N4—C41—H41D | 110.6 | C62—C61—H61D | 117.8 |
C421—C41—H41D | 110.6 | C621—C61—H61D | 109.4 |
C42—C41—H41D | 113.8 | H61A—C61—H61D | 97.5 |
H41A—C41—H41D | 102.7 | H61C—C61—H61D | 108.0 |
H41C—C41—H41D | 108.8 | O6—C62—C61 | 114.06 (10) |
O4—C42—C41 | 106.25 (9) | O6—C62—H62A | 108.7 |
O4—C42—H42A | 110.5 | C61—C62—H62A | 108.7 |
C41—C42—H42A | 110.5 | O6—C62—H62B | 108.7 |
O4—C42—H42B | 110.5 | C61—C62—H62B | 108.7 |
C41—C42—H42B | 110.5 | H62A—C62—H62B | 107.6 |
H42A—C42—H42B | 108.7 | C62—O6—H6A | 109.5 |
C42—O4—H4A | 109.5 | O61—C621—C61 | 131.9 (8) |
O41—C421—C41 | 101.1 (10) | O61—C621—H62C | 104.3 |
O41—C421—H42C | 111.6 | C61—C621—H62C | 104.3 |
C41—C421—H42C | 111.6 | O61—C621—H62D | 104.3 |
O41—C421—H42D | 111.6 | C61—C621—H62D | 104.3 |
C41—C421—H42D | 111.6 | H62C—C621—H62D | 105.6 |
H42C—C421—H42D | 109.4 | C621—O61—H61 | 109.5 |
C421—O41—H41 | 109.5 | | |
| | | |
C6—N1—C2—N2 | 177.52 (19) | C4—C5—N5—O5 | 1.4 (17) |
C6—N1—C2—N3 | −2.4 (3) | C6—C5—N5—O5 | 178.2 (9) |
N2—C2—N3—C4 | −175.56 (18) | N5—C5—N51—O51 | 10 (7) |
N1—C2—N3—C4 | 4.3 (3) | C4—C5—N51—O51 | −179 (2) |
C41—N4—C4—N3 | −4.8 (3) | C6—C5—N51—O51 | −5 (4) |
C41—N4—C4—C5 | 174.18 (18) | C2—N1—C6—N6 | −178.81 (18) |
C2—N3—C4—N4 | 175.66 (17) | C2—N1—C6—C5 | −0.6 (3) |
C2—N3—C4—C5 | −3.3 (3) | N51—C5—C6—N6 | 6 (2) |
C4—N4—C41—C421 | −178.9 (9) | N5—C5—C6—N6 | 2.3 (8) |
C4—N4—C41—C42 | 174.01 (15) | C4—C5—C6—N6 | 179.47 (16) |
N4—C41—C42—O4 | 59.55 (13) | N51—C5—C6—N1 | −172 (2) |
C421—C41—C42—O4 | 4 (5) | N5—C5—C6—N1 | −176.0 (8) |
N4—C41—C421—O41 | −171.8 (8) | C4—C5—C6—N1 | 1.2 (3) |
C42—C41—C421—O41 | −46 (5) | N1—C6—N6—C61 | 0.4 (3) |
N4—C4—C5—N51 | −3.8 (18) | C5—C6—N6—C61 | −177.87 (17) |
N3—C4—C5—N51 | 175.2 (17) | C6—N6—C61—C62 | −93.46 (19) |
N4—C4—C5—N5 | −1.3 (9) | C6—N6—C61—C621 | −81.2 (10) |
N3—C4—C5—N5 | 177.7 (9) | N6—C61—C62—O6 | −52.66 (14) |
N4—C4—C5—C6 | −178.10 (16) | C621—C61—C62—O6 | −136 (2) |
N3—C4—C5—C6 | 0.9 (3) | N6—C61—C621—O61 | 159.1 (17) |
N51—C5—N5—O5 | 12 (8) | C62—C61—C621—O61 | −100 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N3i | 0.88 | 2.46 | 3.293 (3) | 158 |
N2—H2B···O6ii | 0.88 | 2.25 | 3.014 (3) | 146 |
N4—H4···O5 | 0.88 | 1.95 | 2.628 (2) | 133 |
O4—H4A···N1iii | 0.84 | 2.12 | 2.909 (2) | 156 |
O6—H6A···O5iv | 0.84 | 1.86 | 2.659 (4) | 159 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+1/2, z+1/2; (iii) x+1, y, z; (iv) −x+1, −y+1, −z. |
Experimental details
| (I) | (II) | (III) | (IV) |
Crystal data |
Chemical formula | C14H23N5 | C16H15N5O2 | C12H18N6O3 | C18H18N6O |
Mr | 261.37 | 309.33 | 294.32 | 334.38 |
Crystal system, space group | Monoclinic, P21/c | Triclinic, P1 | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 12.1473 (4), 9.8811 (3), 11.4068 (3) | 11.3545 (3), 12.7528 (4), 16.9511 (6) | 13.0037 (4), 9.1130 (3), 12.4892 (3) | 12.9416 (1), 6.6816 (3), 20.0033 (5) |
α, β, γ (°) | 90, 96.6490 (1), 90 | 70.038 (1), 73.206 (1), 79.626 (1) | 90, 112.3400 (12), 90 | 90, 113.3020 (12), 90 |
V (Å3) | 1359.93 (7) | 2199.62 (12) | 1368.92 (7) | 1588.61 (8) |
Z | 4 | 6 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.10 | 0.11 | 0.09 |
Crystal size (mm) | 0.35 × 0.30 × 0.22 | 0.40 × 0.20 × 0.05 | 0.30 × 0.20 × 0.20 | 0.42 × 0.12 × 0.03 |
|
Data collection |
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | – | – | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.968, 0.983 | – | – | 0.957, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13657, 3100, 2195 | 32137, 9847, 4349 | 10906, 3096, 2391 | 27586, 3618, 2492 |
Rint | 0.069 | 0.086 | 0.047 | 0.099 |
(sin θ/λ)max (Å−1) | 0.649 | 0.650 | 0.649 | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.128, 1.02 | 0.058, 0.148, 0.90 | 0.043, 0.114, 1.04 | 0.046, 0.120, 1.01 |
No. of reflections | 3100 | 9847 | 3096 | 3618 |
No. of parameters | 172 | 622 | 190 | 226 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.29 | 0.30, −0.34 | 0.41, −0.28 | 0.27, −0.34 |
| (V) | (VI) |
Crystal data |
Chemical formula | C16H14N6O3 | C8H14N6O3 |
Mr | 338.33 | 242.25 |
Crystal system, space group | Orthorhombic, P212121 | Monoclinic, P21/c |
Temperature (K) | 120 | 120 |
a, b, c (Å) | 6.881 (2), 9.140 (3), 24.4636 (10) | 9.6487 (1), 14.8594 (2), 7.3497 (2) |
α, β, γ (°) | 90, 90, 90 | 90, 101.097 (1), 90 |
V (Å3) | 1538.6 (7) | 1034.05 (3) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.12 |
Crystal size (mm) | 0.45 × 0.12 × 0.04 | 0.20 × 0.06 × 0.04 |
|
Data collection |
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | – | – |
Tmin, Tmax | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8813, 2026, 1369 | 14888, 2366, 1928 |
Rint | 0.067 | 0.039 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.100, 1.00 | 0.066, 0.180, 1.04 |
No. of reflections | 2026 | 2366 |
No. of parameters | 226 | 180 |
No. of restraints | 0 | 11 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.28 | 0.55, −0.37 |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.88 | 2.37 | 3.216 (2) | 162 |
C66—H66B···Cg1ii | 0.99 | 2.68 | 3.518 (2) | 142 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12A···N363 | 0.88 | 2.12 | 2.998 (3) | 174 |
N12—H12B···N343i | 0.88 | 2.10 | 2.977 (3) | 176 |
N22—H22A···N263ii | 0.88 | 2.11 | 2.985 (3) | 175 |
N22—H22B···N243iii | 0.88 | 2.11 | 2.987 (3) | 175 |
N32—H32A···N143 | 0.88 | 2.11 | 2.978 (3) | 167 |
N32—H32B···N163iv | 0.88 | 2.10 | 2.982 (3) | 178 |
Symmetry codes: (i) x+1, y+1, z−1; (ii) −x+1, −y+2, −z; (iii) −x, −y+1, −z+1; (iv) x−1, y−1, z+1. |
Hydrogen-bond geometry (Å, º) for (III) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O64i | 0.88 | 2.04 | 2.918 (2) | 177 |
N2—H2B···O44ii | 0.88 | 2.13 | 2.894 (2) | 144 |
C43—H43A···O5ii | 0.99 | 2.47 | 3.376 (2) | 152 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y−1/2, −z−1/2. |
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N3i | 0.88 | 2.19 | 3.042 (2) | 163 |
N2—H2B···N1ii | 0.88 | 2.15 | 2.967 (2) | 155 |
N4—H4···O5iii | 0.88 | 2.15 | 2.993 (2) | 161 |
N6—H6···O5 | 0.88 | 1.94 | 2.617 (2) | 133 |
C63—H63···O5iv | 0.95 | 2.51 | 3.335 (2) | 146 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) for (V) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N43i | 0.88 | 2.03 | 2.878 (4) | 163 |
N2—H2B···N63ii | 0.88 | 2.02 | 2.888 (4) | 171 |
C65—H65···Cg2iii | 0.95 | 2.69 | 3.526 (4) | 148 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z; (iii) x−1/2, −y+5/2, −z. |
Hydrogen-bond geometry (Å, º) for (VI) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N3i | 0.88 | 2.46 | 3.293 (3) | 158 |
N2—H2B···O6ii | 0.88 | 2.25 | 3.014 (3) | 146 |
N4—H4···O5 | 0.88 | 1.95 | 2.628 (2) | 133 |
O4—H4A···N1iii | 0.84 | 2.12 | 2.909 (2) | 156 |
O6—H6A···O5iv | 0.84 | 1.86 | 2.659 (4) | 159 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+1/2, z+1/2; (iii) x+1, y, z; (iv) −x+1, −y+1, −z. |
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