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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768103024856/na5007sup1.cif
Contains datablocks global, I, II, III, IV, V, VI

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103024856/na5007Isup2.fcf
Contains datablock I

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103024856/na5007IIsup3.fcf
Contains datablock 267

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103024856/na5007IIIsup4.fcf
Contains datablock 258

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103024856/na5007IVsup5.fcf
Contains datablock 329

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103024856/na5007Vsup6.fcf
Contains datablock V

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103024856/na5007VIsup7.fcf
Contains datablock 264

CCDC references: 230845; 230846; 230847; 230848; 230849; 230850

Comment top

In full text version

Experimental top

In full text version

Refinement top

In full text version

Computing details top

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).

Figures top
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In full text version
(I) 2-Amino-4,6-bis(piperidino)pyrimidine top
Crystal data top
C14H23N5F(000) = 568
Mr = 261.37Dx = 1.277 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3100 reflections
a = 12.1473 (4) Åθ = 3.1–27.5°
b = 9.8811 (3) ŵ = 0.08 mm1
c = 11.4068 (3) ÅT = 120 K
β = 96.6490 (1)°Block, orange
V = 1359.93 (7) Å30.35 × 0.30 × 0.22 mm
Z = 4
Data collection top
Kappa-CCD
diffractometer
3100 independent reflections
Radiation source: fine-focus sealed X-ray tube2195 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1515
Tmin = 0.968, Tmax = 0.983k = 1012
13657 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-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 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C14H23N5V = 1359.93 (7) Å3
Mr = 261.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1473 (4) ŵ = 0.08 mm1
b = 9.8811 (3) ÅT = 120 K
c = 11.4068 (3) Å0.35 × 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 = 0.983Rint = 0.069
13657 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.02Δρmax = 0.20 e Å3
3100 reflectionsΔρmin = 0.29 e Å3
172 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.39389 (9)0.53485 (12)0.34772 (10)0.0179 (3)
C20.35055 (11)0.62533 (14)0.41702 (11)0.0169 (3)
N20.38927 (10)0.62161 (13)0.53323 (10)0.0220 (3)
N30.27377 (9)0.72041 (12)0.38535 (9)0.0176 (3)
C40.23614 (11)0.72498 (14)0.26940 (11)0.0172 (3)
C420.11193 (12)0.84765 (16)0.11484 (12)0.0244 (3)
C430.01295 (12)0.83474 (17)0.09880 (13)0.0278 (4)
C440.06520 (13)0.92704 (18)0.18430 (14)0.0310 (4)
C450.01323 (13)0.90069 (18)0.31031 (13)0.0304 (4)
C460.11195 (13)0.90994 (17)0.32031 (13)0.0284 (4)
N40.15553 (10)0.81933 (14)0.23639 (10)0.0269 (3)
C50.27625 (11)0.63700 (14)0.18796 (11)0.0172 (3)
C60.35579 (11)0.54212 (14)0.23137 (12)0.0175 (3)
N60.40198 (10)0.45221 (13)0.15855 (10)0.0230 (3)
C620.36417 (12)0.44574 (15)0.03232 (12)0.0222 (3)
C630.27085 (12)0.34419 (15)0.00609 (12)0.0226 (3)
C640.30803 (13)0.20559 (16)0.05383 (13)0.0267 (4)
C650.35250 (14)0.21353 (17)0.18382 (13)0.0309 (4)
C660.44216 (14)0.32068 (17)0.20522 (14)0.0329 (4)
H2A0.44010.56200.55940.026*
H2B0.36360.67880.58260.026*
H42A0.14420.78340.06160.029*
H42B0.13320.94040.09360.029*
H43A0.03390.73970.11250.033*
H43B0.04170.85890.01670.033*
H44A0.05371.02280.16340.037*
H44B0.14600.91010.17820.037*
H45A0.04160.96780.36380.036*
H45B0.03490.80950.33530.036*
H46A0.13411.00410.30480.034*
H46B0.14360.88560.40150.034*
H50.25030.64170.10620.021*
H62A0.42700.41970.01100.027*
H62B0.33820.53630.00430.027*
H63A0.24960.33850.08020.027*
H63B0.20530.37430.04320.027*
H64A0.24460.14210.04350.032*
H64B0.36650.17010.00850.032*
H65A0.29110.23540.23060.037*
H65B0.38330.12450.21050.037*
H66A0.46550.32870.29100.039*
H66B0.50750.29300.16650.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0186 (6)0.0180 (6)0.0165 (6)0.0001 (5)0.0008 (4)0.0016 (4)
C20.0159 (7)0.0161 (7)0.0184 (7)0.0036 (5)0.0009 (5)0.0010 (5)
N20.0248 (7)0.0236 (7)0.0164 (6)0.0076 (5)0.0031 (4)0.0018 (5)
N30.0170 (6)0.0202 (6)0.0154 (6)0.0015 (5)0.0011 (4)0.0005 (4)
C40.0141 (7)0.0202 (7)0.0174 (7)0.0013 (6)0.0014 (5)0.0012 (5)
C420.0248 (8)0.0315 (9)0.0164 (7)0.0090 (6)0.0011 (5)0.0021 (6)
C430.0255 (8)0.0335 (9)0.0233 (8)0.0010 (7)0.0027 (6)0.0017 (6)
C440.0190 (8)0.0444 (11)0.0296 (9)0.0056 (7)0.0023 (6)0.0010 (7)
C450.0320 (9)0.0357 (9)0.0248 (8)0.0098 (7)0.0087 (6)0.0009 (6)
C460.0306 (9)0.0345 (9)0.0188 (8)0.0144 (7)0.0027 (6)0.0064 (6)
N40.0264 (7)0.0384 (8)0.0153 (6)0.0172 (6)0.0009 (5)0.0013 (5)
C50.0167 (7)0.0207 (7)0.0138 (7)0.0020 (5)0.0002 (5)0.0000 (5)
C60.0153 (7)0.0176 (7)0.0195 (7)0.0026 (6)0.0017 (5)0.0018 (5)
N60.0229 (6)0.0253 (7)0.0195 (6)0.0041 (5)0.0032 (5)0.0086 (5)
C620.0240 (8)0.0241 (8)0.0191 (7)0.0006 (6)0.0053 (5)0.0050 (6)
C630.0212 (7)0.0266 (8)0.0194 (7)0.0000 (6)0.0005 (5)0.0022 (6)
C640.0261 (8)0.0242 (8)0.0290 (8)0.0020 (7)0.0001 (6)0.0030 (6)
C650.0399 (10)0.0277 (9)0.0250 (8)0.0115 (7)0.0033 (6)0.0022 (6)
C660.0342 (9)0.0310 (9)0.0300 (9)0.0167 (7)0.0109 (6)0.0121 (7)
Geometric parameters (Å, º) top
N1—C21.3408 (18)C46—N41.4545 (19)
N1—C61.3559 (17)C46—H46A0.99
C2—N31.3435 (17)C46—H46B0.99
C2—N21.3548 (17)C5—C61.3954 (19)
N2—H2A0.88C5—H50.95
N2—H2B0.88C6—N61.3791 (18)
N3—C41.3492 (17)N6—C621.4612 (18)
C4—N41.3728 (18)N6—C661.466 (2)
C4—C51.4003 (19)C62—C631.518 (2)
C42—N41.4529 (17)C62—H62A0.99
C42—C431.512 (2)C62—H62B0.99
C42—H42A0.99C63—C641.523 (2)
C42—H42B0.99C63—H63A0.99
C43—C441.526 (2)C63—H63B0.99
C43—H43A0.99C64—C651.520 (2)
C43—H43B0.99C64—H64A0.99
C44—C451.524 (2)C64—H64B0.99
C44—H44A0.99C65—C661.518 (2)
C44—H44B0.99C65—H65A0.99
C45—C461.514 (2)C65—H65B0.99
C45—H45A0.99C66—H66A0.99
C45—H45B0.99C66—H66B0.99
C2—N1—C6115.40 (11)C4—N4—C46122.68 (11)
N1—C2—N3127.99 (12)C42—N4—C46112.91 (11)
N1—C2—N2116.31 (12)C6—C5—C4117.48 (12)
N3—C2—N2115.69 (12)C6—C5—H5121.3
C2—N2—H2A120.0C4—C5—H5121.3
C2—N2—H2B120.0N1—C6—N6116.03 (12)
H2A—N2—H2B120.0N1—C6—C5121.79 (12)
C2—N3—C4115.64 (11)N6—C6—C5122.16 (12)
N3—C4—N4116.20 (11)C6—N6—C62121.22 (12)
N3—C4—C5121.69 (12)C6—N6—C66119.59 (12)
N4—C4—C5122.11 (12)C62—N6—C66111.86 (11)
N4—C42—C43110.42 (12)N6—C62—C63111.44 (12)
N4—C42—H42A109.6N6—C62—H62A109.3
C43—C42—H42A109.6C63—C62—H62A109.3
N4—C42—H42B109.6N6—C62—H62B109.3
C43—C42—H42B109.6C63—C62—H62B109.3
H42A—C42—H42B108.1H62A—C62—H62B108.0
C42—C43—C44110.97 (12)C62—C63—C64109.89 (12)
C42—C43—H43A109.4C62—C63—H63A109.7
C44—C43—H43A109.4C64—C63—H63A109.7
C42—C43—H43B109.4C62—C63—H63B109.7
C44—C43—H43B109.4C64—C63—H63B109.7
H43A—C43—H43B108.0H63A—C63—H63B108.2
C45—C44—C43110.07 (13)C65—C64—C63111.07 (12)
C45—C44—H44A109.6C65—C64—H64A109.4
C43—C44—H44A109.6C63—C64—H64A109.4
C45—C44—H44B109.6C65—C64—H64B109.4
C43—C44—H44B109.6C63—C64—H64B109.4
H44A—C44—H44B108.2H64A—C64—H64B108.0
C46—C45—C44111.31 (12)C66—C65—C64111.11 (13)
C46—C45—H45A109.4C66—C65—H65A109.4
C44—C45—H45A109.4C64—C65—H65A109.4
C46—C45—H45B109.4C66—C65—H65B109.4
C44—C45—H45B109.4C64—C65—H65B109.4
H45A—C45—H45B108.0H65A—C65—H65B108.0
N4—C46—C45110.61 (12)N6—C66—C65110.93 (12)
N4—C46—H46A109.5N6—C66—H66A109.5
C45—C46—H46A109.5C65—C66—H66A109.5
N4—C46—H46B109.5N6—C66—H66B109.5
C45—C46—H46B109.5C65—C66—H66B109.5
H46A—C46—H46B108.1H66A—C66—H66B108.0
C4—N4—C42124.21 (11)
C6—N1—C2—N30.8 (2)N3—C4—C5—C61.05 (19)
C6—N1—C2—N2178.64 (11)N4—C4—C5—C6178.07 (13)
N1—C2—N3—C40.1 (2)C2—N1—C6—N6178.21 (12)
N2—C2—N3—C4179.31 (12)C2—N1—C6—C50.50 (19)
C2—N3—C4—N4178.33 (12)C4—C5—C6—N10.34 (19)
C2—N3—C4—C50.83 (19)C4—C5—C6—N6178.97 (12)
N4—C42—C43—C4456.19 (17)N1—C6—N6—C62177.09 (12)
C42—C43—C44—C4553.41 (18)C5—C6—N6—C624.2 (2)
C43—C44—C45—C4652.82 (18)N1—C6—N6—C6629.43 (19)
C44—C45—C46—N454.93 (18)C5—C6—N6—C66151.86 (13)
N3—C4—N4—C42174.30 (13)C6—N6—C62—C6390.61 (16)
C5—C4—N4—C426.5 (2)C66—N6—C62—C6359.31 (16)
N3—C4—N4—C460.1 (2)N6—C62—C63—C6456.44 (15)
C5—C4—N4—C46179.06 (14)C62—C63—C64—C6553.52 (16)
C43—C42—N4—C4125.81 (15)C63—C64—C65—C6653.19 (17)
C43—C42—N4—C4659.30 (17)C6—N6—C66—C6592.50 (15)
C45—C46—N4—C4126.42 (15)C62—N6—C66—C6557.97 (17)
C45—C46—N4—C4258.60 (17)C64—C65—C66—N654.77 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.882.373.216 (2)162
C66—H66B···Cg1ii0.992.683.518 (2)142
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+1/2.
(II) 2-Amino-4,6-bis(3-pyridylmethoxy)pyrimidine top
Crystal data top
C16H15N5O2Z = 6
Mr = 309.33F(000) = 972
Triclinic, P1Dx = 1.401 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.3545 (3) ÅCell parameters from 9847 reflections
b = 12.7528 (4) Åθ = 2.9–27.5°
c = 16.9511 (6) ŵ = 0.10 mm1
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 tubeRint = 0.086
Graphite monochromatorθmax = 27.5°, θmin = 2.9°
ϕ scans, and ω scans with κ offsetsh = 1414
32137 measured reflectionsk = 1616
9847 independent reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-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 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C16H15N5O2γ = 79.626 (1)°
Mr = 309.33V = 2199.62 (12) Å3
Triclinic, P1Z = 6
a = 11.3545 (3) ÅMo Kα radiation
b = 12.7528 (4) ŵ = 0.10 mm1
c = 16.9511 (6) ÅT = 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 reflectionsRint = 0.086
9847 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 0.90Δρmax = 0.30 e Å3
9847 reflectionsΔρmin = 0.34 e Å3
622 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.87818 (18)0.94519 (16)0.06184 (12)0.0223 (5)
N120.77832 (19)0.99790 (17)0.05942 (13)0.0289 (5)
C120.8026 (2)0.92063 (19)0.01890 (15)0.0212 (6)
O140.72837 (16)0.64697 (13)0.06292 (10)0.0268 (4)
N130.74856 (18)0.82393 (16)0.06230 (13)0.0232 (5)
C140.7762 (2)0.7475 (2)0.02195 (15)0.0219 (6)
C1410.6409 (2)0.5098 (2)0.19496 (15)0.0242 (6)
C1420.5349 (2)0.4758 (2)0.25884 (16)0.0279 (6)
N1430.5199 (2)0.36945 (18)0.30868 (13)0.0327 (6)
C1440.6137 (3)0.2934 (2)0.29504 (17)0.0352 (7)
C1450.7214 (3)0.3176 (2)0.23109 (16)0.0323 (7)
C1460.7357 (2)0.4278 (2)0.18103 (16)0.0270 (6)
C1470.6543 (2)0.6321 (2)0.15030 (15)0.0244 (6)
C150.8524 (2)0.7625 (2)0.06099 (16)0.0253 (6)
C160.9004 (2)0.8651 (2)0.09824 (15)0.0224 (6)
C1611.0966 (2)0.99845 (19)0.30979 (15)0.0206 (6)
C1621.1502 (2)1.0970 (2)0.36206 (16)0.0250 (6)
N1631.21208 (19)1.11470 (17)0.44527 (13)0.0260 (5)
C1641.2220 (2)1.0319 (2)0.47883 (16)0.0254 (6)
C1651.1728 (2)0.9311 (2)0.43273 (16)0.0288 (6)
C1661.1083 (2)0.9150 (2)0.34687 (16)0.0266 (6)
C1671.0290 (2)0.9902 (2)0.21792 (15)0.0237 (6)
O160.97701 (16)0.88369 (14)0.17938 (10)0.0282 (4)
N210.30633 (17)0.84508 (16)0.20722 (12)0.0202 (5)
C220.2483 (2)0.7498 (2)0.24840 (15)0.0203 (6)
N220.27140 (18)0.67304 (16)0.20787 (13)0.0248 (5)
N230.16874 (17)0.72582 (16)0.32861 (12)0.0197 (5)
C240.1523 (2)0.8023 (2)0.36803 (15)0.0183 (5)
C2410.0494 (2)0.6680 (2)0.57715 (15)0.0187 (5)
C2420.0981 (2)0.5668 (2)0.62922 (15)0.0234 (6)
N2430.16557 (19)0.54836 (16)0.71060 (13)0.0254 (5)
C2440.1874 (2)0.6335 (2)0.74329 (16)0.0283 (6)
C2450.1450 (2)0.7376 (2)0.69758 (16)0.0285 (6)
C2460.0748 (2)0.7549 (2)0.61256 (15)0.0234 (6)
C2470.0222 (2)0.6780 (2)0.48558 (15)0.0213 (6)
O240.07882 (15)0.78180 (13)0.45002 (10)0.0224 (4)
C250.2058 (2)0.9033 (2)0.33307 (15)0.0208 (5)
C260.2823 (2)0.9186 (2)0.25018 (15)0.0196 (5)
C2610.4596 (2)1.14720 (19)0.09434 (15)0.0194 (5)
C2620.5217 (2)1.1880 (2)0.00743 (16)0.0228 (6)
N2630.56746 (19)1.28729 (17)0.02859 (13)0.0262 (5)
C2640.5524 (2)1.3505 (2)0.02269 (16)0.0264 (6)
C2650.4930 (2)1.3180 (2)0.10921 (16)0.0263 (6)
C2660.4465 (2)1.2143 (2)0.14529 (16)0.0237 (6)
C2670.4133 (2)1.0333 (2)0.12567 (15)0.0217 (6)
O260.33516 (15)1.01680 (13)0.21214 (10)0.0239 (4)
N310.22324 (18)0.38269 (16)0.59576 (12)0.0219 (5)
C320.2989 (2)0.40907 (19)0.51456 (15)0.0209 (6)
N320.32180 (19)0.33374 (17)0.47243 (13)0.0257 (5)
N330.35435 (18)0.50520 (16)0.47244 (12)0.0210 (5)
C340.3326 (2)0.57747 (19)0.51663 (15)0.0197 (5)
O340.13685 (15)0.43706 (14)0.71833 (10)0.0261 (4)
C3410.0034 (2)0.33037 (19)0.84513 (15)0.0205 (5)
C3420.0415 (2)0.2296 (2)0.90127 (15)0.0241 (6)
N3430.11559 (19)0.21831 (17)0.98053 (13)0.0258 (5)
C3440.1454 (2)0.3102 (2)1.00570 (16)0.0276 (6)
C3450.1053 (2)0.4133 (2)0.95551 (16)0.0300 (6)
C3460.0290 (2)0.4230 (2)0.87357 (16)0.0252 (6)
C3470.0799 (2)0.3334 (2)0.75599 (16)0.0240 (6)
C350.2598 (2)0.5599 (2)0.60073 (16)0.0241 (6)
C360.2081 (2)0.4587 (2)0.63568 (15)0.0207 (6)
C3610.5078 (2)0.8069 (2)0.36260 (15)0.0203 (5)
C3620.5814 (2)0.8438 (2)0.27872 (16)0.0243 (6)
N3630.62695 (19)0.94416 (17)0.24304 (13)0.0260 (5)
C3640.5989 (2)1.0116 (2)0.29219 (16)0.0255 (6)
C3650.5275 (2)0.9826 (2)0.37621 (16)0.0284 (6)
C3660.4822 (2)0.8784 (2)0.41204 (16)0.0248 (6)
C3670.4603 (2)0.69374 (19)0.39224 (15)0.0220 (6)
O360.38392 (15)0.67679 (13)0.47868 (10)0.0244 (4)
H12A0.72920.98470.11190.035*
H12B0.81141.06210.03380.035*
H1420.46880.53120.26790.033*
H1440.60620.21810.33130.042*
H1450.78430.25980.22170.039*
H1460.80960.44720.13750.032*
H14A0.57180.67350.14930.029*
H14B0.69440.66180.18190.029*
H150.86990.70690.08950.030*
H1621.14241.15520.33730.030*
H1641.26521.04320.53770.031*
H1651.18280.87400.45890.035*
H1661.07230.84660.31380.032*
H16A1.08660.99520.18550.028*
H16B0.96271.05210.21650.028*
H22A0.32270.68500.15620.030*
H22B0.23540.61020.23260.030*
H2420.08210.50700.60500.028*
H2440.23480.62180.80130.034*
H2450.16330.79590.72340.034*
H2460.04460.82570.57930.028*
H24A0.08640.61420.48470.026*
H24B0.03380.67680.45070.026*
H250.19140.95700.36300.025*
H2620.53191.14190.02830.027*
H2640.58441.42170.00180.032*
H2650.48401.36580.14340.032*
H2660.40581.18960.20500.028*
H26A0.36591.02800.08670.026*
H26B0.48380.97490.12610.026*
H32A0.37080.34790.41990.031*
H32B0.28790.26980.49710.031*
H3420.01830.16510.88220.029*
H3440.19770.30391.06180.033*
H3450.12920.47620.97640.036*
H3460.00070.49300.83730.030*
H34A0.14400.26920.75930.029*
H34B0.02710.32880.72010.029*
H350.24670.61270.63140.029*
H3620.60060.79470.24450.029*
H3640.62971.08330.26820.031*
H3650.50981.03340.40900.034*
H3660.43400.85630.47010.030*
H36A0.41160.69060.35330.026*
H36B0.53010.63470.39160.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0243 (12)0.0214 (11)0.0177 (11)0.0049 (9)0.0018 (9)0.0029 (10)
N120.0368 (13)0.0227 (11)0.0217 (11)0.0120 (10)0.0067 (10)0.0066 (10)
C120.0230 (14)0.0178 (13)0.0192 (13)0.0042 (11)0.0043 (11)0.0006 (11)
O140.0383 (11)0.0214 (9)0.0162 (9)0.0147 (8)0.0040 (8)0.0031 (8)
N130.0259 (12)0.0187 (10)0.0220 (11)0.0060 (9)0.0032 (9)0.0028 (10)
C140.0238 (14)0.0188 (13)0.0207 (13)0.0062 (11)0.0054 (11)0.0009 (11)
C1410.0313 (15)0.0230 (13)0.0190 (13)0.0095 (12)0.0040 (11)0.0056 (11)
C1420.0350 (16)0.0249 (14)0.0230 (14)0.0099 (12)0.0007 (12)0.0082 (12)
N1430.0466 (15)0.0275 (12)0.0231 (12)0.0159 (11)0.0002 (11)0.0075 (11)
C1440.060 (2)0.0192 (13)0.0238 (14)0.0123 (14)0.0040 (14)0.0048 (12)
C1450.0452 (18)0.0234 (14)0.0270 (14)0.0023 (13)0.0056 (13)0.0091 (12)
C1460.0323 (15)0.0269 (14)0.0234 (13)0.0036 (12)0.0051 (12)0.0107 (12)
C1470.0297 (15)0.0212 (13)0.0185 (13)0.0075 (11)0.0010 (11)0.0027 (11)
C150.0334 (15)0.0197 (13)0.0226 (14)0.0052 (12)0.0066 (12)0.0051 (12)
C160.0228 (14)0.0240 (13)0.0166 (13)0.0046 (11)0.0019 (11)0.0026 (12)
C1610.0165 (13)0.0219 (13)0.0192 (13)0.0014 (11)0.0027 (10)0.0027 (11)
C1620.0286 (15)0.0215 (13)0.0243 (14)0.0043 (11)0.0046 (12)0.0069 (12)
N1630.0258 (12)0.0237 (11)0.0233 (11)0.0058 (9)0.0004 (9)0.0035 (10)
C1640.0238 (14)0.0296 (14)0.0217 (13)0.0046 (11)0.0027 (11)0.0077 (12)
C1650.0317 (15)0.0278 (14)0.0271 (14)0.0072 (12)0.0013 (12)0.0115 (13)
C1660.0288 (15)0.0247 (13)0.0259 (14)0.0096 (11)0.0036 (12)0.0061 (12)
C1670.0258 (14)0.0199 (13)0.0231 (13)0.0073 (11)0.0026 (11)0.0040 (12)
O160.0378 (11)0.0216 (9)0.0176 (9)0.0114 (8)0.0055 (8)0.0025 (8)
N210.0191 (11)0.0221 (11)0.0178 (11)0.0057 (9)0.0043 (9)0.0024 (10)
C220.0175 (13)0.0209 (13)0.0196 (13)0.0042 (11)0.0053 (11)0.0006 (12)
N220.0304 (12)0.0226 (11)0.0185 (11)0.0117 (10)0.0036 (9)0.0059 (10)
N230.0199 (11)0.0194 (10)0.0171 (11)0.0056 (9)0.0013 (9)0.0028 (9)
C240.0157 (13)0.0222 (13)0.0135 (12)0.0013 (10)0.0020 (10)0.0025 (11)
C2410.0145 (13)0.0240 (13)0.0177 (12)0.0033 (11)0.0042 (10)0.0054 (11)
C2420.0268 (15)0.0239 (13)0.0183 (13)0.0068 (11)0.0013 (11)0.0063 (12)
N2430.0287 (12)0.0213 (11)0.0210 (11)0.0068 (9)0.0008 (9)0.0038 (10)
C2440.0278 (15)0.0317 (15)0.0191 (13)0.0054 (12)0.0042 (11)0.0070 (13)
C2450.0309 (15)0.0265 (14)0.0263 (14)0.0064 (12)0.0003 (12)0.0101 (13)
C2460.0229 (14)0.0211 (13)0.0217 (13)0.0076 (11)0.0015 (11)0.0015 (12)
C2470.0222 (14)0.0214 (13)0.0192 (13)0.0082 (11)0.0012 (10)0.0048 (11)
O240.0246 (9)0.0218 (9)0.0176 (9)0.0113 (7)0.0028 (7)0.0041 (8)
C250.0201 (13)0.0220 (13)0.0192 (13)0.0047 (11)0.0019 (11)0.0058 (11)
C260.0160 (13)0.0210 (13)0.0193 (13)0.0064 (11)0.0037 (10)0.0013 (12)
C2610.0169 (13)0.0187 (12)0.0190 (13)0.0032 (10)0.0013 (10)0.0031 (11)
C2620.0276 (14)0.0187 (13)0.0195 (13)0.0061 (11)0.0019 (11)0.0039 (11)
N2630.0283 (12)0.0229 (11)0.0221 (11)0.0067 (9)0.0007 (9)0.0038 (10)
C2640.0269 (15)0.0175 (12)0.0294 (15)0.0071 (11)0.0001 (12)0.0035 (12)
C2650.0315 (15)0.0243 (13)0.0248 (14)0.0078 (11)0.0018 (12)0.0112 (12)
C2660.0259 (14)0.0231 (13)0.0183 (13)0.0050 (11)0.0019 (11)0.0032 (11)
C2670.0244 (14)0.0237 (13)0.0144 (12)0.0087 (11)0.0010 (10)0.0042 (11)
O260.0269 (10)0.0210 (9)0.0186 (9)0.0108 (8)0.0035 (7)0.0030 (8)
N310.0218 (11)0.0236 (11)0.0177 (11)0.0061 (9)0.0025 (9)0.0030 (9)
C320.0191 (13)0.0200 (13)0.0197 (13)0.0046 (11)0.0048 (11)0.0001 (11)
N320.0321 (13)0.0238 (11)0.0197 (11)0.0129 (9)0.0021 (9)0.0066 (10)
N330.0196 (11)0.0208 (11)0.0211 (11)0.0047 (9)0.0043 (9)0.0037 (10)
C340.0209 (13)0.0174 (12)0.0195 (13)0.0057 (10)0.0061 (11)0.0014 (11)
O340.0312 (10)0.0244 (9)0.0191 (9)0.0129 (8)0.0027 (8)0.0044 (8)
C3410.0192 (13)0.0218 (13)0.0187 (12)0.0044 (11)0.0032 (10)0.0041 (11)
C3420.0280 (14)0.0208 (13)0.0202 (13)0.0055 (11)0.0017 (11)0.0041 (11)
N3430.0255 (12)0.0249 (12)0.0242 (12)0.0070 (9)0.0024 (9)0.0048 (10)
C3440.0303 (15)0.0303 (15)0.0186 (13)0.0053 (12)0.0005 (11)0.0070 (12)
C3450.0377 (16)0.0213 (13)0.0279 (14)0.0055 (12)0.0023 (13)0.0070 (12)
C3460.0299 (15)0.0199 (13)0.0227 (14)0.0061 (11)0.0043 (12)0.0023 (12)
C3470.0249 (14)0.0227 (13)0.0228 (13)0.0096 (11)0.0008 (11)0.0053 (12)
C350.0255 (14)0.0244 (13)0.0222 (13)0.0073 (11)0.0028 (11)0.0069 (12)
C360.0177 (13)0.0266 (14)0.0173 (13)0.0027 (11)0.0036 (10)0.0063 (12)
C3610.0184 (13)0.0215 (13)0.0199 (13)0.0020 (10)0.0049 (11)0.0047 (11)
C3620.0279 (15)0.0207 (13)0.0220 (13)0.0064 (11)0.0024 (11)0.0045 (12)
N3630.0285 (12)0.0228 (11)0.0246 (12)0.0070 (10)0.0032 (10)0.0049 (10)
C3640.0272 (15)0.0188 (13)0.0295 (14)0.0046 (11)0.0060 (12)0.0058 (12)
C3650.0340 (16)0.0240 (13)0.0260 (14)0.0068 (12)0.0002 (12)0.0102 (12)
C3660.0214 (14)0.0294 (14)0.0197 (13)0.0060 (11)0.0028 (11)0.0075 (12)
C3670.0239 (14)0.0211 (13)0.0174 (12)0.0059 (11)0.0005 (11)0.0032 (11)
O360.0303 (10)0.0198 (9)0.0177 (9)0.0130 (8)0.0035 (7)0.0015 (8)
Geometric parameters (Å, º) top
N11—C161.318 (3)C247—O241.438 (3)
N11—C121.354 (3)C247—H24A0.99
N12—C121.332 (3)C247—H24B0.99
N12—H12A0.88C25—C261.391 (3)
N12—H12B0.88C25—H250.95
C12—N131.353 (3)C26—O261.357 (3)
O14—C141.359 (3)C261—C2661.373 (3)
O14—C1471.443 (3)C261—C2621.395 (3)
N13—C141.318 (3)C261—C2671.502 (3)
C14—C151.391 (3)C262—N2631.332 (3)
C141—C1421.387 (3)C262—H2620.95
C141—C1461.387 (3)N263—C2641.333 (3)
C141—C1471.497 (3)C264—C2651.375 (3)
C142—N1431.341 (3)C264—H2640.95
C142—H1420.95C265—C2661.384 (3)
N143—C1441.329 (3)C265—H2650.95
C144—C1451.381 (4)C266—H2660.95
C144—H1440.95C267—O261.444 (3)
C145—C1461.382 (4)C267—H26A0.99
C145—H1450.95C267—H26B0.99
C146—H1460.95N31—C361.322 (3)
C147—H14A0.99N31—C321.361 (3)
C147—H14B0.99C32—N321.331 (3)
C15—C161.378 (3)C32—N331.352 (3)
C15—H150.95N32—H32A0.88
C16—O161.366 (3)N32—H32B0.88
C161—C1661.380 (3)N33—C341.324 (3)
C161—C1621.392 (3)C34—O361.360 (3)
C161—C1671.500 (3)C34—C351.391 (3)
C162—N1631.342 (3)O34—C361.362 (3)
C162—H1620.95O34—C3471.438 (3)
N163—C1641.334 (3)C341—C3461.376 (3)
C164—C1651.377 (3)C341—C3421.392 (3)
C164—H1640.95C341—C3471.501 (3)
C165—C1661.390 (3)C342—N3431.339 (3)
C165—H1650.95C342—H3420.95
C166—H1660.95N343—C3441.337 (3)
C167—O161.442 (3)C344—C3451.374 (3)
C167—H16A0.99C344—H3440.95
C167—H16B0.99C345—C3461.386 (3)
N21—C261.320 (3)C345—H3450.95
N21—C221.357 (3)C346—H3460.95
C22—N221.327 (3)C347—H34A0.99
C22—N231.365 (3)C347—H34B0.99
N22—H22A0.88C35—C361.383 (3)
N22—H22B0.88C35—H350.95
N23—C241.319 (3)C361—C3661.380 (3)
C24—O241.363 (3)C361—C3621.393 (3)
C24—C251.390 (3)C361—C3671.502 (3)
C241—C2461.382 (3)C362—N3631.342 (3)
C241—C2421.396 (3)C362—H3620.95
C241—C2471.503 (3)N363—C3641.331 (3)
C242—N2431.333 (3)C364—C3651.380 (3)
C242—H2420.95C364—H3640.95
N243—C2441.335 (3)C365—C3661.383 (3)
C244—C2451.381 (3)C365—H3650.95
C244—H2440.95C366—H3660.95
C245—C2461.394 (3)C367—O361.436 (3)
C245—H2450.95C367—H36A0.99
C246—H2460.95C367—H36B0.99
C16—N11—C12115.1 (2)H24A—C247—H24B108.4
C12—N12—H12A120.0C24—O24—C247116.16 (18)
C12—N12—H12B120.0C24—C25—C26113.8 (2)
H12A—N12—H12B120.0C24—C25—H25123.1
N12—C12—N13116.7 (2)C26—C25—H25123.1
N12—C12—N11117.7 (2)N21—C26—O26118.8 (2)
N13—C12—N11125.5 (2)N21—C26—C25124.8 (2)
C14—O14—C147115.60 (18)O26—C26—C25116.4 (2)
C14—N13—C12115.8 (2)C266—C261—C262117.2 (2)
N13—C14—O14118.9 (2)C266—C261—C267124.8 (2)
N13—C14—C15124.2 (2)C262—C261—C267118.0 (2)
O14—C14—C15116.9 (2)N263—C262—C261124.2 (2)
C142—C141—C146117.5 (2)N263—C262—H262117.9
C142—C141—C147119.7 (2)C261—C262—H262117.9
C146—C141—C147122.5 (2)C262—N263—C264117.0 (2)
N143—C142—C141124.0 (3)N263—C264—C265123.4 (2)
N143—C142—H142118.0N263—C264—H264118.3
C141—C142—H142118.0C265—C264—H264118.3
C144—N143—C142116.9 (2)C264—C265—C266118.5 (2)
N143—C144—C145123.7 (2)C264—C265—H265120.7
N143—C144—H144118.2C266—C265—H265120.7
C145—C144—H144118.2C261—C266—C265119.7 (2)
C144—C145—C146118.5 (3)C261—C266—H266120.2
C144—C145—H145120.7C265—C266—H266120.2
C146—C145—H145120.7O26—C267—C261108.22 (19)
C145—C146—C141119.3 (2)O26—C267—H26A110.1
C145—C146—H146120.4C261—C267—H26A110.1
C141—C146—H146120.4O26—C267—H26B110.1
O14—C147—C141108.93 (19)C261—C267—H26B110.1
O14—C147—H14A109.9H26A—C267—H26B108.4
C141—C147—H14A109.9C26—O26—C267116.40 (18)
O14—C147—H14B109.9C36—N31—C32114.8 (2)
C141—C147—H14B109.9N32—C32—N33116.5 (2)
H14A—C147—H14B108.3N32—C32—N31117.6 (2)
C16—C15—C14114.1 (2)N33—C32—N31125.9 (2)
C16—C15—H15122.9C32—N32—H32A120.0
C14—C15—H15122.9C32—N32—H32B120.0
N11—C16—O16118.2 (2)H32A—N32—H32B120.0
N11—C16—C15125.3 (2)C34—N33—C32115.3 (2)
O16—C16—C15116.5 (2)N33—C34—O36119.1 (2)
C166—C161—C162117.2 (2)N33—C34—C35124.7 (2)
C166—C161—C167124.3 (2)O36—C34—C35116.2 (2)
C162—C161—C167118.4 (2)C36—O34—C347117.47 (18)
N163—C162—C161123.9 (2)C346—C341—C342117.9 (2)
N163—C162—H162118.0C346—C341—C347123.6 (2)
C161—C162—H162118.0C342—C341—C347118.5 (2)
C164—N163—C162117.2 (2)N343—C342—C341123.7 (2)
N163—C164—C165123.6 (2)N343—C342—H342118.1
N163—C164—H164118.2C341—C342—H342118.1
C165—C164—H164118.2C344—N343—C342116.7 (2)
C164—C165—C166118.3 (2)N343—C344—C345124.1 (2)
C164—C165—H165120.9N343—C344—H344117.9
C166—C165—H165120.9C345—C344—H344117.9
C161—C166—C165119.8 (2)C344—C345—C346118.2 (2)
C161—C166—H166120.1C344—C345—H345120.9
C165—C166—H166120.1C346—C345—H345120.9
O16—C167—C161107.68 (19)C341—C346—C345119.5 (2)
O16—C167—H16A110.2C341—C346—H346120.3
C161—C167—H16A110.2C345—C346—H346120.3
O16—C167—H16B110.2O34—C347—C341107.68 (19)
C161—C167—H16B110.2O34—C347—H34A110.2
H16A—C167—H16B108.5C341—C347—H34A110.2
C16—O16—C167116.66 (19)O34—C347—H34B110.2
C26—N21—C22115.6 (2)C341—C347—H34B110.2
N22—C22—N21117.5 (2)H34A—C347—H34B108.5
N22—C22—N23117.2 (2)C36—C35—C34113.8 (2)
N21—C22—N23125.3 (2)C36—C35—H35123.1
C22—N22—H22A120.0C34—C35—H35123.1
C22—N22—H22B120.0N31—C36—O34118.5 (2)
H22A—N22—H22B120.0N31—C36—C35125.4 (2)
C24—N23—C22115.2 (2)O34—C36—C35116.1 (2)
N23—C24—O24118.6 (2)C366—C361—C362117.2 (2)
N23—C24—C25125.2 (2)C366—C361—C367124.7 (2)
O24—C24—C25116.3 (2)C362—C361—C367118.0 (2)
C246—C241—C242117.3 (2)N363—C362—C361124.3 (2)
C246—C241—C247124.0 (2)N363—C362—H362117.8
C242—C241—C247118.7 (2)C361—C362—H362117.8
N243—C242—C241124.4 (2)C364—N363—C362116.8 (2)
N243—C242—H242117.8N363—C364—C365123.3 (2)
C241—C242—H242117.8N363—C364—H364118.4
C242—N243—C244116.9 (2)C365—C364—H364118.4
N243—C244—C245123.8 (2)C364—C365—C366119.0 (2)
N243—C244—H244118.1C364—C365—H365120.5
C245—C244—H244118.1C366—C365—H365120.5
C244—C245—C246118.3 (2)C361—C366—C365119.3 (2)
C244—C245—H245120.9C361—C366—H366120.3
C246—C245—H245120.9C365—C366—H366120.3
C241—C246—C245119.4 (2)O36—C367—C361107.52 (19)
C241—C246—H246120.3O36—C367—H36A110.2
C245—C246—H246120.3C361—C367—H36A110.2
O24—C247—C241108.25 (19)O36—C367—H36B110.2
O24—C247—H24A110.0C361—C367—H36B110.2
C241—C247—H24A110.0H36A—C367—H36B108.5
O24—C247—H24B110.0C34—O36—C367115.89 (18)
C241—C247—H24B110.0
C16—N11—C12—N12179.0 (2)N23—C24—C25—C260.6 (4)
C16—N11—C12—N131.3 (3)O24—C24—C25—C26178.4 (2)
N12—C12—N13—C14178.4 (2)C22—N21—C26—O26178.7 (2)
N11—C12—N13—C142.0 (3)C22—N21—C26—C251.4 (3)
C12—N13—C14—O14177.9 (2)C24—C25—C26—N211.4 (3)
C12—N13—C14—C151.9 (3)C24—C25—C26—O26178.8 (2)
C147—O14—C14—N132.5 (3)C266—C261—C262—N2630.6 (4)
C147—O14—C14—C15177.3 (2)C267—C261—C262—N263179.9 (2)
C146—C141—C142—N1431.4 (4)C261—C262—N263—C2640.2 (4)
C147—C141—C142—N143172.6 (2)C262—N263—C264—C2650.0 (4)
C141—C142—N143—C1440.1 (4)N263—C264—C265—C2660.2 (4)
C142—N143—C144—C1452.6 (4)C262—C261—C266—C2650.8 (4)
N143—C144—C145—C1463.3 (4)C267—C261—C266—C265180.0 (2)
C144—C145—C146—C1411.6 (4)C264—C265—C266—C2610.6 (4)
C142—C141—C146—C1450.6 (4)C266—C261—C267—O2610.3 (3)
C147—C141—C146—C145173.3 (2)C262—C261—C267—O26170.5 (2)
C14—O14—C147—C141163.1 (2)N21—C26—O26—C2670.9 (3)
C142—C141—C147—O14149.5 (2)C25—C26—O26—C267179.2 (2)
C146—C141—C147—O1436.8 (3)C261—C267—O26—C26178.4 (2)
N13—C14—C15—C161.3 (4)C36—N31—C32—N32177.3 (2)
O14—C14—C15—C16178.5 (2)C36—N31—C32—N332.2 (3)
C12—N11—C16—O16179.3 (2)N32—C32—N33—C34178.4 (2)
C12—N11—C16—C150.6 (4)N31—C32—N33—C341.2 (3)
C14—C15—C16—N110.6 (4)C32—N33—C34—O36179.4 (2)
C14—C15—C16—O16179.3 (2)C32—N33—C34—C350.6 (3)
C166—C161—C162—N1630.3 (4)C346—C341—C342—N3431.0 (4)
C167—C161—C162—N163179.5 (2)C347—C341—C342—N343176.6 (2)
C161—C162—N163—C1640.0 (4)C341—C342—N343—C3440.7 (4)
C162—N163—C164—C1650.2 (4)C342—N343—C344—C3450.2 (4)
N163—C164—C165—C1660.7 (4)N343—C344—C345—C3460.0 (4)
C162—C161—C166—C1650.8 (4)C342—C341—C346—C3450.8 (4)
C167—C161—C166—C165180.0 (2)C347—C341—C346—C345176.7 (2)
C164—C165—C166—C1611.0 (4)C344—C345—C346—C3410.3 (4)
C166—C161—C167—O162.2 (3)C36—O34—C347—C341178.0 (2)
C162—C161—C167—O16177.0 (2)C346—C341—C347—O3415.0 (3)
N11—C16—O16—C1671.0 (3)C342—C341—C347—O34167.6 (2)
C15—C16—O16—C167179.0 (2)N33—C34—C35—C361.1 (4)
C161—C167—O16—C16173.2 (2)O36—C34—C35—C36178.9 (2)
C26—N21—C22—N22179.1 (2)C32—N31—C36—O34177.9 (2)
C26—N21—C22—N230.4 (3)C32—N31—C36—C351.6 (3)
N22—C22—N23—C24177.4 (2)C347—O34—C36—N311.6 (3)
N21—C22—N23—C242.1 (3)C347—O34—C36—C35178.9 (2)
C22—N23—C24—O24176.8 (2)C34—C35—C36—N310.1 (4)
C22—N23—C24—C252.2 (3)C34—C35—C36—O34179.4 (2)
C246—C241—C242—N2430.9 (4)C366—C361—C362—N3631.0 (4)
C247—C241—C242—N243178.4 (2)C367—C361—C362—N363178.0 (2)
C241—C242—N243—C2440.2 (4)C361—C362—N363—C3640.1 (4)
C242—N243—C244—C2450.4 (4)C362—N363—C364—C3650.4 (4)
N243—C244—C245—C2460.4 (4)N363—C364—C365—C3660.0 (4)
C242—C241—C246—C2450.9 (3)C362—C361—C366—C3651.4 (4)
C247—C241—C246—C245178.2 (2)C367—C361—C366—C365177.4 (2)
C244—C245—C246—C2410.3 (4)C364—C365—C366—C3611.0 (4)
C246—C241—C247—O2411.7 (3)C366—C361—C367—O361.0 (3)
C242—C241—C247—O24171.0 (2)C362—C361—C367—O36177.9 (2)
N23—C24—O24—C2471.8 (3)N33—C34—O36—C3670.8 (3)
C25—C24—O24—C247179.1 (2)C35—C34—O36—C367179.2 (2)
C241—C247—O24—C24177.3 (2)C361—C367—O36—C34179.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H12A···N3630.882.122.998 (3)174
N12—H12B···N343i0.882.102.977 (3)176
N22—H22A···N263ii0.882.112.985 (3)175
N22—H22B···N243iii0.882.112.987 (3)175
N32—H32A···N1430.882.112.978 (3)167
N32—H32B···N163iv0.882.102.982 (3)178
Symmetry codes: (i) x+1, y+1, z1; (ii) x+1, y+2, z; (iii) x, y+1, z+1; (iv) x1, y1, z+1.
(III) 2-Amino-4,6-bis(morpholino)-5-nitrosopirimidine top
Crystal data top
C12H18N6O3F(000) = 624
Mr = 294.32Dx = 1.428 Mg m3
Monoclinic, P21/cMelting point: 483K K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.0037 (4) ÅCell parameters from 3096 reflections
b = 9.1130 (3) Åθ = 3.0–27.5°
c = 12.4892 (3) ŵ = 0.11 mm1
β = 112.3400 (12)°T = 120 K
V = 1368.92 (7) Å3Block, blue
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Kappa-CCD
diffractometer
2391 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.047
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
ϕ scans, and ω scans with κ offsetsh = 1616
10906 measured reflectionsk = 1110
3096 independent reflectionsl = 1416
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-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 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C12H18N6O3V = 1368.92 (7) Å3
Mr = 294.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.0037 (4) ŵ = 0.11 mm1
b = 9.1130 (3) ÅT = 120 K
c = 12.4892 (3) Å0.30 × 0.20 × 0.20 mm
β = 112.3400 (12)°
Data collection top
Kappa-CCD
diffractometer
2391 reflections with I > 2σ(I)
10906 measured reflectionsRint = 0.047
3096 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.04Δρmax = 0.41 e Å3
3096 reflectionsΔρmin = 0.28 e Å3
190 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.32218 (9)0.47876 (13)0.07040 (9)0.0169 (3)
C20.26526 (11)0.46319 (15)0.04405 (11)0.0161 (3)
N20.30168 (10)0.35938 (14)0.09559 (10)0.0207 (3)
N30.17212 (9)0.53626 (12)0.11111 (9)0.0169 (3)
C50.21761 (11)0.70363 (15)0.05196 (11)0.0163 (3)
C40.14534 (11)0.65304 (15)0.06249 (11)0.0155 (3)
N40.05260 (9)0.72681 (13)0.12493 (10)0.0176 (3)
C420.01378 (12)0.68569 (16)0.24524 (12)0.0195 (3)
C430.11548 (12)0.60041 (16)0.24993 (12)0.0224 (3)
O440.17954 (8)0.68593 (11)0.20170 (8)0.0220 (3)
C450.11579 (12)0.72391 (16)0.08401 (12)0.0201 (3)
C460.01272 (11)0.81093 (15)0.07314 (12)0.0185 (3)
N50.24536 (10)0.84568 (13)0.08381 (10)0.0203 (3)
O50.19317 (9)0.94670 (11)0.01494 (9)0.0253 (3)
C60.29515 (11)0.59347 (15)0.12109 (11)0.0165 (3)
N60.34601 (10)0.60405 (13)0.23642 (10)0.0204 (3)
C620.43500 (13)0.50290 (17)0.30270 (12)0.0269 (4)
C630.53472 (12)0.59131 (18)0.37680 (13)0.0260 (3)
O640.50652 (8)0.68598 (11)0.45292 (8)0.0222 (2)
C650.41941 (12)0.78462 (16)0.38953 (12)0.0214 (3)
C660.31654 (12)0.70298 (16)0.31231 (12)0.0191 (3)
H2A0.35980.30590.05490.025*
H2B0.26770.34410.17040.025*
H42A0.03150.62470.27630.023*
H42B0.03710.77510.29350.023*
H43A0.16150.57540.33130.027*
H43B0.09210.50780.20590.027*
H45A0.09330.63320.03720.024*
H45B0.16230.78280.05310.024*
H46A0.03460.90640.11320.022*
H46B0.03240.83020.00950.022*
H62A0.45500.43930.24930.032*
H62B0.40970.43950.35220.032*
H63A0.59520.52410.42290.031*
H63B0.56190.65080.32660.031*
H65A0.44550.84960.34150.026*
H65B0.40050.84690.44440.026*
H66A0.28520.64600.36030.023*
H66B0.25950.77380.26530.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0182 (6)0.0176 (6)0.0138 (5)0.0005 (5)0.0048 (5)0.0004 (5)
C20.0164 (7)0.0155 (7)0.0162 (6)0.0026 (5)0.0058 (5)0.0005 (5)
N20.0209 (6)0.0234 (7)0.0136 (6)0.0045 (5)0.0017 (5)0.0032 (5)
N30.0177 (6)0.0173 (6)0.0147 (5)0.0004 (5)0.0050 (5)0.0008 (5)
C50.0169 (7)0.0176 (7)0.0139 (6)0.0006 (5)0.0054 (5)0.0004 (5)
C40.0168 (7)0.0156 (7)0.0151 (6)0.0023 (5)0.0073 (5)0.0020 (5)
N40.0172 (6)0.0197 (6)0.0143 (5)0.0020 (5)0.0041 (5)0.0011 (5)
C420.0204 (7)0.0234 (8)0.0119 (6)0.0021 (6)0.0029 (5)0.0008 (5)
C430.0261 (8)0.0203 (8)0.0174 (7)0.0009 (6)0.0043 (6)0.0017 (6)
O440.0186 (5)0.0269 (6)0.0177 (5)0.0017 (4)0.0038 (4)0.0004 (4)
C450.0203 (7)0.0235 (8)0.0157 (6)0.0005 (6)0.0058 (6)0.0012 (6)
C460.0197 (7)0.0183 (7)0.0163 (7)0.0026 (6)0.0053 (6)0.0010 (5)
N50.0233 (7)0.0172 (6)0.0204 (6)0.0007 (5)0.0085 (5)0.0010 (5)
O50.0271 (6)0.0197 (5)0.0262 (5)0.0003 (5)0.0069 (5)0.0033 (4)
C60.0171 (7)0.0180 (7)0.0145 (6)0.0034 (5)0.0061 (5)0.0006 (5)
N60.0240 (7)0.0205 (6)0.0134 (5)0.0061 (5)0.0033 (5)0.0017 (5)
C620.0348 (9)0.0239 (8)0.0155 (7)0.0116 (7)0.0024 (6)0.0011 (6)
C630.0239 (8)0.0311 (9)0.0221 (7)0.0093 (7)0.0077 (6)0.0004 (6)
O640.0205 (5)0.0228 (6)0.0183 (5)0.0028 (4)0.0020 (4)0.0029 (4)
C650.0213 (7)0.0187 (8)0.0221 (7)0.0015 (6)0.0060 (6)0.0023 (6)
C660.0203 (7)0.0219 (8)0.0150 (6)0.0013 (6)0.0067 (6)0.0018 (5)
Geometric parameters (Å, º) top
N1—C61.3365 (18)C45—H45A0.99
N1—C21.3442 (17)C45—H45B0.99
C2—N21.3286 (18)C46—H46A0.99
C2—N31.3568 (17)C46—H46B0.99
N2—H2A0.88N5—O51.2665 (15)
N2—H2B0.88C6—N61.3406 (17)
N3—C41.3354 (18)N6—C661.4608 (17)
C5—N51.3619 (18)N6—C621.4648 (19)
C5—C61.4519 (19)C62—C631.508 (2)
C5—C41.4553 (18)C62—H62A0.99
C4—N41.3415 (18)C62—H62B0.99
N4—C461.4645 (17)C63—O641.4311 (17)
N4—C421.4688 (17)C63—H63A0.99
C42—C431.516 (2)C63—H63B0.99
C42—H42A0.99O64—C651.4269 (17)
C42—H42B0.99C65—C661.514 (2)
C43—O441.4303 (18)C65—H65A0.99
C43—H43A0.9900C65—H65B0.99
C43—H43B0.9900C66—H66A0.99
O44—C451.4287 (16)C66—H66B0.99
C45—C461.518 (2)
C6—N1—C2116.66 (12)N4—C46—H46A109.9
N2—C2—N1115.90 (12)C45—C46—H46A109.9
N2—C2—N3116.70 (12)N4—C46—H46B109.9
N1—C2—N3127.31 (12)C45—C46—H46B109.9
C2—N2—H2A120.0H46A—C46—H46B108.3
C2—N2—H2B120.0O5—N5—C5118.58 (11)
H2A—N2—H2B120.0N1—C6—N6117.00 (12)
C4—N3—C2115.87 (11)N1—C6—C5120.49 (11)
N5—C5—C6115.88 (12)N6—C6—C5122.46 (12)
N5—C5—C4126.05 (12)C6—N6—C66126.69 (12)
C6—C5—C4114.10 (11)C6—N6—C62121.53 (11)
N3—C4—N4117.86 (12)C66—N6—C62111.56 (11)
N3—C4—C5121.09 (12)N6—C62—C63108.72 (12)
N4—C4—C5120.96 (12)N6—C62—H62A109.9
C4—N4—C46123.35 (11)C63—C62—H62A109.9
C4—N4—C42121.04 (11)N6—C62—H62B109.9
C46—N4—C42111.80 (11)C63—C62—H62B109.9
N4—C42—C43109.59 (11)H62A—C62—H62B108.3
N4—C42—H42A109.8O64—C63—C62110.61 (12)
C43—C42—H42A109.8O64—C63—H63A109.5
N4—C42—H42B109.8C62—C63—H63A109.5
C43—C42—H42B109.8O64—C63—H63B109.5
H42A—C42—H42B108.2C62—C63—H63B109.5
O44—C43—C42110.10 (11)H63A—C63—H63B108.1
O44—C43—H43A109.6C65—O64—C63111.16 (10)
C42—C43—H43A109.6O64—C65—C66111.52 (11)
O44—C43—H43B109.6O64—C65—H65A109.3
C42—C43—H43B109.6C66—C65—H65A109.3
H43A—C43—H43B108.2O64—C65—H65B109.3
C45—O44—C43111.23 (10)C66—C65—H65B109.3
O44—C45—C46111.46 (11)H65A—C65—H65B108.0
O44—C45—H45A109.3N6—C66—C65109.29 (11)
C46—C45—H45A109.3N6—C66—H66A109.8
O44—C45—H45B109.3C65—C66—H66A109.8
C46—C45—H45B109.3N6—C66—H66B109.8
H45A—C45—H45B108.0C65—C66—H66B109.8
N4—C46—C45109.12 (11)H66A—C66—H66B108.3
C6—N1—C2—N2172.34 (12)O44—C45—C46—N455.83 (15)
C6—N1—C2—N311.2 (2)C6—C5—N5—O5166.84 (11)
N2—C2—N3—C4171.14 (12)C4—C5—N5—O510.7 (2)
N1—C2—N3—C412.45 (19)C2—N1—C6—N6175.47 (12)
C2—N3—C4—N4178.69 (11)C2—N1—C6—C57.14 (18)
C2—N3—C4—C54.71 (18)N5—C5—C6—N1137.55 (13)
N5—C5—C4—N3136.28 (14)C4—C5—C6—N121.43 (18)
C6—C5—C4—N320.20 (18)N5—C5—C6—N639.70 (18)
N5—C5—C4—N440.2 (2)C4—C5—C6—N6161.32 (12)
C6—C5—C4—N4163.31 (12)N1—C6—N6—C66168.39 (12)
N3—C4—N4—C46152.71 (12)C5—C6—N6—C6614.3 (2)
C5—C4—N4—C4630.69 (19)N1—C6—N6—C625.8 (2)
N3—C4—N4—C423.50 (19)C5—C6—N6—C62171.51 (13)
C5—C4—N4—C42173.10 (12)C6—N6—C62—C63127.17 (14)
C4—N4—C42—C43102.23 (14)C66—N6—C62—C6357.81 (15)
C46—N4—C42—C4356.49 (15)N6—C62—C63—O6458.45 (15)
N4—C42—C43—O4457.52 (15)C62—C63—O64—C6559.19 (15)
C42—C43—O44—C4559.45 (14)C63—O64—C65—C6657.64 (15)
C43—O44—C45—C4659.07 (15)C6—N6—C66—C65129.16 (14)
C4—N4—C46—C45103.05 (14)C62—N6—C66—C6556.13 (15)
C42—N4—C46—C4555.10 (15)O64—C65—C66—N655.39 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O64i0.882.042.918 (2)177
N2—H2B···O44ii0.882.132.894 (2)144
C43—H43A···O5ii0.992.473.376 (2)152
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y1/2, z1/2.
(IV) 2-Amino-4,6-bis(benzylamino)-5-nitrosopyrimidine top
Crystal data top
C18H18N6OF(000) = 704
Mr = 334.38Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3618 reflections
a = 12.9416 (1) Åθ = 3.3–27.5°
b = 6.6816 (3) ŵ = 0.09 mm1
c = 20.0033 (5) ÅT = 120 K
β = 113.3020 (12)°Plate, purple
V = 1588.61 (8) Å30.42 × 0.12 × 0.03 mm
Z = 4
Data collection top
Kappa-CCD
diffractometer
3618 independent reflections
Radiation source: fine-focus sealed X-ray tube2492 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.099
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1616
Tmin = 0.957, Tmax = 0.997k = 88
27586 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-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 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C18H18N6OV = 1588.61 (8) Å3
Mr = 334.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.9416 (1) ŵ = 0.09 mm1
b = 6.6816 (3) ÅT = 120 K
c = 20.0033 (5) Å0.42 × 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 = 0.997Rint = 0.099
27586 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.01Δρmax = 0.27 e Å3
3618 reflectionsΔρmin = 0.34 e Å3
226 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.33577 (11)0.84162 (19)0.20935 (7)0.0158 (3)
C20.39878 (13)0.9984 (2)0.24680 (8)0.0149 (3)
N20.50593 (11)0.9986 (2)0.25476 (7)0.0173 (3)
N30.36605 (11)1.15517 (19)0.27714 (7)0.0153 (3)
C40.25925 (13)1.1526 (2)0.27140 (8)0.0145 (3)
N40.22099 (11)1.30115 (19)0.29972 (7)0.0163 (3)
C470.29104 (14)1.4571 (2)0.34737 (9)0.0179 (4)
C410.33596 (13)1.4021 (3)0.42764 (8)0.0178 (4)
C420.36786 (14)1.2078 (3)0.45173 (9)0.0210 (4)
C430.41066 (15)1.1621 (3)0.52538 (9)0.0240 (4)
C440.42185 (15)1.3108 (3)0.57609 (9)0.0255 (4)
C450.39044 (15)1.5049 (3)0.55276 (9)0.0256 (4)
C460.34766 (14)1.5509 (3)0.47891 (9)0.0217 (4)
C50.18352 (13)0.9904 (2)0.23483 (8)0.0142 (3)
N50.08014 (11)1.0005 (2)0.23510 (7)0.0170 (3)
O50.00954 (10)0.86113 (17)0.20251 (6)0.0206 (3)
C60.22881 (13)0.8366 (2)0.20293 (8)0.0143 (3)
N60.16166 (11)0.6876 (2)0.16666 (7)0.0176 (3)
C670.18896 (14)0.5396 (2)0.12282 (9)0.0198 (4)
C610.14731 (13)0.5977 (2)0.04300 (9)0.0186 (4)
C620.14399 (14)0.4510 (3)0.00734 (9)0.0223 (4)
C630.10857 (15)0.4990 (3)0.08063 (9)0.0258 (4)
C640.07491 (15)0.6918 (3)0.10478 (9)0.0260 (4)
C650.07738 (15)0.8381 (3)0.05510 (9)0.0248 (4)
C660.11374 (14)0.7909 (3)0.01851 (9)0.0220 (4)
H2A0.53180.90070.23620.021*
H2B0.55091.09650.27860.021*
H40.14821.30570.28890.020*
H47A0.24631.58160.33960.021*
H47B0.35531.48440.33370.021*
H420.36031.10490.41730.025*
H430.43231.02860.54110.029*
H440.45091.27970.62650.031*
H450.39811.60730.58740.031*
H460.32631.68460.46340.026*
H60.09560.67790.16940.021*
H67A0.15510.40970.12690.024*
H67B0.27160.52170.14240.024*
H620.16600.31780.00850.027*
H630.10740.39850.11450.031*
H640.05030.72360.15500.031*
H650.05420.97070.07120.030*
H660.11560.89210.05230.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0144 (7)0.0164 (7)0.0168 (7)0.0007 (5)0.0066 (6)0.0003 (5)
C20.0153 (8)0.0161 (8)0.0133 (8)0.0012 (6)0.0057 (6)0.0034 (6)
N20.0141 (7)0.0157 (7)0.0236 (7)0.0002 (5)0.0090 (6)0.0029 (6)
N30.0132 (7)0.0160 (7)0.0169 (7)0.0000 (5)0.0063 (6)0.0003 (5)
C40.0155 (8)0.0171 (8)0.0117 (7)0.0019 (6)0.0061 (6)0.0036 (6)
N40.0126 (7)0.0182 (7)0.0184 (7)0.0003 (5)0.0067 (6)0.0016 (5)
C470.0182 (9)0.0169 (8)0.0197 (8)0.0004 (6)0.0087 (7)0.0027 (6)
C410.0122 (8)0.0228 (9)0.0195 (8)0.0020 (6)0.0076 (7)0.0029 (7)
C420.0205 (9)0.0230 (9)0.0200 (8)0.0016 (7)0.0086 (7)0.0029 (7)
C430.0203 (9)0.0255 (9)0.0258 (9)0.0012 (7)0.0087 (8)0.0024 (7)
C440.0202 (9)0.0381 (11)0.0180 (9)0.0035 (8)0.0071 (8)0.0004 (8)
C450.0224 (10)0.0333 (10)0.0211 (9)0.0019 (8)0.0085 (8)0.0091 (8)
C460.0179 (9)0.0227 (9)0.0250 (9)0.0011 (7)0.0090 (7)0.0024 (7)
C50.0133 (8)0.0168 (8)0.0136 (7)0.0002 (6)0.0066 (6)0.0008 (6)
N50.0161 (7)0.0193 (7)0.0156 (7)0.0032 (6)0.0062 (6)0.0003 (6)
O50.0167 (6)0.0233 (6)0.0219 (6)0.0054 (5)0.0079 (5)0.0035 (5)
C60.0148 (8)0.0163 (8)0.0116 (7)0.0003 (6)0.0052 (6)0.0027 (6)
N60.0152 (7)0.0190 (7)0.0200 (7)0.0033 (6)0.0086 (6)0.0030 (6)
C670.0176 (9)0.0181 (8)0.0233 (9)0.0010 (7)0.0075 (7)0.0057 (7)
C610.0125 (8)0.0223 (9)0.0217 (9)0.0039 (7)0.0077 (7)0.0052 (7)
C620.0149 (9)0.0231 (9)0.0286 (10)0.0015 (7)0.0082 (7)0.0061 (7)
C630.0178 (9)0.0350 (11)0.0235 (9)0.0036 (8)0.0070 (7)0.0142 (8)
C640.0199 (9)0.0382 (11)0.0190 (9)0.0009 (8)0.0068 (7)0.0035 (8)
C650.0224 (10)0.0274 (10)0.0254 (9)0.0015 (7)0.0101 (8)0.0000 (8)
C660.0217 (9)0.0233 (9)0.0223 (9)0.0022 (7)0.0101 (8)0.0064 (7)
Geometric parameters (Å, º) top
N1—C61.339 (2)C45—H450.95
N1—C21.357 (2)C46—H460.95
C2—N21.332 (2)C5—N51.3417 (19)
C2—N31.3594 (19)C5—C61.450 (2)
N2—H2A0.88N5—O51.2868 (17)
N2—H2B0.88C6—N61.332 (2)
N3—C41.341 (2)N6—C671.455 (2)
C4—N41.332 (2)N6—H60.88
C4—C51.450 (2)C67—C611.520 (2)
N4—C471.460 (2)C67—H67A0.99
N4—H40.88C67—H67B0.99
C47—C411.521 (2)C61—C661.388 (2)
C47—H47A0.99C61—C621.394 (2)
C47—H47B0.99C62—C631.389 (2)
C41—C421.390 (2)C62—H620.95
C41—C461.393 (2)C63—C641.385 (3)
C42—C431.388 (2)C63—H630.95
C42—H420.95C64—C651.385 (2)
C43—C441.386 (3)C64—H640.95
C43—H430.95C65—C661.393 (2)
C44—C451.384 (3)C65—H650.95
C44—H440.95C66—H660.95
C45—C461.392 (2)
C6—N1—C2116.41 (13)C45—C46—H46119.8
N2—C2—N1115.89 (13)C41—C46—H46119.8
N2—C2—N3116.08 (14)N5—C5—C6127.93 (14)
N1—C2—N3128.04 (14)N5—C5—C4115.87 (13)
C2—N2—H2A120.0C6—C5—C4116.19 (13)
C2—N2—H2B120.0O5—N5—C5118.09 (13)
H2A—N2—H2B120.0N6—C6—N1119.85 (14)
C4—N3—C2116.39 (13)N6—C6—C5118.64 (14)
N4—C4—N3119.87 (14)N1—C6—C5121.52 (14)
N4—C4—C5118.74 (14)C6—N6—C67125.08 (13)
N3—C4—C5121.39 (13)C6—N6—H6117.5
C4—N4—C47124.77 (14)C67—N6—H6117.5
C4—N4—H4117.6N6—C67—C61112.94 (13)
C47—N4—H4117.6N6—C67—H67A109.0
N4—C47—C41113.33 (13)C61—C67—H67A109.0
N4—C47—H47A108.9N6—C67—H67B109.0
C41—C47—H47A108.9C61—C67—H67B109.0
N4—C47—H47B108.9H67A—C67—H67B107.8
C41—C47—H47B108.9C66—C61—C62118.90 (15)
H47A—C47—H47B107.7C66—C61—C67122.68 (14)
C42—C41—C46118.74 (15)C62—C61—C67118.42 (15)
C42—C41—C47121.93 (14)C63—C62—C61120.20 (16)
C46—C41—C47119.31 (15)C63—C62—H62119.9
C43—C42—C41120.86 (16)C61—C62—H62119.9
C43—C42—H42119.6C64—C63—C62120.65 (16)
C41—C42—H42119.6C64—C63—H63119.7
C44—C43—C42120.10 (17)C62—C63—H63119.7
C44—C43—H43119.9C63—C64—C65119.44 (16)
C42—C43—H43119.9C63—C64—H64120.3
C45—C44—C43119.57 (16)C65—C64—H64120.3
C45—C44—H44120.2C64—C65—C66120.07 (17)
C43—C44—H44120.2C64—C65—H65120.0
C44—C45—C46120.35 (16)C66—C65—H65120.0
C44—C45—H45119.8C61—C66—C65120.74 (15)
C46—C45—H45119.8C61—C66—H66119.6
C45—C46—C41120.37 (16)C65—C66—H66119.6
C6—N1—C2—N2178.01 (13)N3—C4—C5—C62.1 (2)
C6—N1—C2—N32.0 (2)C6—C5—N5—O51.3 (2)
N2—C2—N3—C4177.88 (13)C4—C5—N5—O5179.15 (13)
N1—C2—N3—C42.1 (2)C2—N1—C6—N6179.75 (13)
C2—N3—C4—N4179.94 (13)C2—N1—C6—C50.4 (2)
C2—N3—C4—C50.1 (2)N5—C5—C6—N62.6 (2)
N3—C4—N4—C479.9 (2)C4—C5—C6—N6177.86 (13)
C5—C4—N4—C47170.07 (14)N5—C5—C6—N1177.27 (14)
C4—N4—C47—C4189.40 (17)C4—C5—C6—N12.3 (2)
N4—C47—C41—C4236.4 (2)N1—C6—N6—C679.7 (2)
N4—C47—C41—C46144.84 (15)C5—C6—N6—C67170.45 (14)
C46—C41—C42—C430.0 (2)C6—N6—C67—C6193.12 (18)
C47—C41—C42—C43178.74 (15)N6—C67—C61—C6615.6 (2)
C41—C42—C43—C440.2 (3)N6—C67—C61—C62165.07 (14)
C42—C43—C44—C450.2 (3)C66—C61—C62—C630.6 (2)
C43—C44—C45—C460.1 (3)C67—C61—C62—C63178.72 (15)
C44—C45—C46—C410.0 (3)C61—C62—C63—C640.8 (3)
C42—C41—C46—C450.1 (2)C62—C63—C64—C650.4 (3)
C47—C41—C46—C45178.86 (15)C63—C64—C65—C660.2 (3)
N4—C4—C5—N52.5 (2)C62—C61—C66—C650.1 (2)
N3—C4—C5—N5177.46 (13)C67—C61—C66—C65179.23 (15)
N4—C4—C5—C6177.94 (13)C64—C65—C66—C610.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N3i0.882.193.042 (2)163
N2—H2B···N1ii0.882.152.967 (2)155
N4—H4···O5iii0.882.152.993 (2)161
N6—H6···O50.881.942.617 (2)133
C63—H63···O5iv0.952.513.335 (2)146
Symmetry codes: (i) x+1, y1/2, 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
C16H14N6O3F(000) = 704
Mr = 338.33Dx = 1.461 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2026 reflections
a = 6.881 (2) Åθ = 3.3–27.5°
b = 9.140 (3) ŵ = 0.11 mm1
c = 24.4636 (10) ÅT = 120 K
V = 1538.6 (7) Å3Plate, colourless
Z = 40.45 × 0.12 × 0.04 mm
Data collection top
Kappa-CCD
diffractometer
1369 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.067
Graphite monochromatorθmax = 27.5°, θmin = 3.3°
ϕ scans, and ω scans with κ offsetsh = 78
8813 measured reflectionsk = 118
2026 independent reflectionsl = 2931
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C16H14N6O3V = 1538.6 (7) Å3
Mr = 338.33Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.881 (2) ŵ = 0.11 mm1
b = 9.140 (3) ÅT = 120 K
c = 24.4636 (10) Å0.45 × 0.12 × 0.04 mm
Data collection top
Kappa-CCD
diffractometer
1369 reflections with I > 2σ(I)
8813 measured reflectionsRint = 0.067
2026 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.00Δρmax = 0.21 e Å3
2026 reflectionsΔρmin = 0.28 e Å3
226 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0674 (3)0.6159 (3)0.09921 (10)0.0212 (6)
C20.1069 (4)0.4982 (3)0.13185 (12)0.0218 (7)
N20.0158 (4)0.3891 (3)0.13100 (10)0.0262 (6)
N30.2646 (3)0.4844 (3)0.16516 (10)0.0222 (6)
C40.3907 (4)0.5912 (3)0.16322 (12)0.0217 (7)
C410.7479 (4)0.4628 (3)0.26183 (12)0.0232 (7)
C420.7851 (4)0.5863 (4)0.29238 (13)0.0272 (8)
N430.9420 (4)0.6031 (3)0.32434 (11)0.0310 (7)
C441.0661 (4)0.4898 (3)0.32717 (13)0.0276 (8)
C451.0396 (4)0.3622 (4)0.29918 (13)0.0275 (8)
C460.8792 (4)0.3490 (3)0.26567 (12)0.0248 (7)
C470.5674 (5)0.4501 (3)0.22746 (13)0.0274 (8)
O40.5487 (3)0.5831 (2)0.19553 (9)0.0262 (5)
C50.3746 (4)0.7162 (3)0.12907 (12)0.0195 (7)
N50.5231 (4)0.8161 (3)0.13111 (11)0.0272 (6)
O50.5131 (3)0.9247 (2)0.10003 (9)0.0357 (6)
C60.1985 (4)0.7200 (3)0.09741 (12)0.0190 (7)
C610.0218 (4)0.9674 (3)0.00058 (12)0.0212 (7)
C620.1210 (4)0.9966 (3)0.03825 (12)0.0240 (7)
N630.1216 (4)1.1128 (3)0.07152 (10)0.0255 (6)
C640.0289 (4)1.2054 (3)0.06733 (13)0.0244 (7)
C650.1778 (5)1.1870 (3)0.03061 (13)0.0268 (8)
C660.1740 (4)1.0660 (3)0.00399 (13)0.0253 (8)
C670.0138 (4)0.8328 (3)0.03406 (12)0.0231 (7)
O60.1680 (3)0.8340 (2)0.06504 (9)0.0230 (5)
H2A0.00550.31130.15140.031*
H2B0.11960.39330.11010.031*
H420.69410.66430.29070.033*
H441.17770.49900.34980.033*
H451.12980.28410.30270.033*
H460.85910.26180.24530.030*
H41A0.57730.36420.20290.033*
H41B0.45210.43720.25120.033*
H620.22550.92920.04130.029*
H640.03271.28790.09090.029*
H650.28141.25550.02880.032*
H660.27531.05120.02980.030*
H61A0.12600.82940.05940.028*
H61B0.01900.74540.01020.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0211 (14)0.0218 (14)0.0207 (14)0.0006 (11)0.0006 (11)0.0031 (12)
C20.0196 (15)0.0252 (17)0.0205 (17)0.0022 (15)0.0002 (13)0.0000 (15)
N20.0234 (14)0.0244 (15)0.0309 (15)0.0055 (12)0.0087 (11)0.0088 (13)
N30.0206 (14)0.0242 (15)0.0217 (14)0.0022 (12)0.0027 (11)0.0018 (12)
C40.0190 (16)0.0269 (18)0.0191 (17)0.0007 (14)0.0002 (13)0.0009 (14)
C410.0195 (16)0.0254 (18)0.0247 (19)0.0031 (13)0.0005 (13)0.0001 (15)
C420.0208 (17)0.0280 (19)0.033 (2)0.0041 (14)0.0048 (14)0.0062 (16)
N430.0296 (16)0.0279 (16)0.0355 (17)0.0024 (13)0.0081 (13)0.0015 (13)
C440.0220 (17)0.031 (2)0.0295 (18)0.0030 (15)0.0050 (14)0.0067 (17)
C450.0232 (18)0.0314 (19)0.0281 (18)0.0038 (14)0.0025 (14)0.0041 (16)
C460.0224 (17)0.0281 (18)0.0241 (18)0.0027 (14)0.0033 (13)0.0009 (15)
C470.0243 (18)0.0247 (18)0.0333 (19)0.0049 (13)0.0071 (14)0.0081 (15)
O40.0242 (12)0.0243 (12)0.0302 (12)0.0020 (10)0.0069 (9)0.0053 (10)
C50.0172 (15)0.0206 (16)0.0208 (17)0.0021 (13)0.0010 (12)0.0019 (14)
N50.0266 (15)0.0260 (15)0.0289 (16)0.0013 (12)0.0017 (12)0.0022 (13)
O50.0310 (14)0.0340 (14)0.0422 (15)0.0080 (11)0.0027 (11)0.0128 (12)
C60.0168 (16)0.0220 (17)0.0182 (17)0.0003 (13)0.0048 (12)0.0017 (14)
C610.0196 (16)0.0223 (16)0.0218 (16)0.0015 (13)0.0030 (13)0.0017 (14)
C620.0203 (17)0.0207 (17)0.0310 (19)0.0047 (14)0.0009 (14)0.0015 (16)
N630.0257 (14)0.0249 (14)0.0259 (15)0.0008 (12)0.0016 (11)0.0027 (13)
C640.0274 (18)0.0222 (16)0.0235 (17)0.0008 (14)0.0026 (14)0.0007 (14)
C650.0263 (18)0.0240 (18)0.0301 (19)0.0077 (14)0.0002 (14)0.0000 (16)
C660.0204 (17)0.0299 (19)0.0255 (18)0.0008 (14)0.0035 (14)0.0007 (16)
C670.0199 (16)0.0253 (17)0.0243 (17)0.0015 (13)0.0029 (13)0.0020 (14)
O60.0206 (11)0.0223 (11)0.0261 (12)0.0020 (9)0.0033 (9)0.0043 (10)
Geometric parameters (Å, º) top
N1—C61.312 (4)C47—H41A0.99
N1—C21.367 (4)C47—H41B0.99
C2—N21.307 (4)C5—N51.372 (4)
C2—N31.363 (4)C5—C61.438 (4)
N2—H2A0.88N5—O51.252 (3)
N2—H2B0.88C6—O61.325 (4)
N3—C41.307 (4)C61—C661.384 (4)
C4—O41.346 (3)C61—C621.392 (4)
C4—C51.420 (4)C61—C671.479 (4)
C41—C421.378 (4)C62—N631.338 (4)
C41—C461.381 (4)C62—H620.95
C41—C471.504 (4)N63—C641.342 (4)
C42—N431.342 (4)C64—C651.373 (4)
C42—H420.95C64—H640.95
N43—C441.344 (4)C65—C661.393 (4)
C44—C451.365 (4)C65—H650.95
C44—H440.95C66—H660.95
C45—C461.380 (4)C67—O61.463 (3)
C45—H450.95C67—H61A0.99
C46—H460.95C67—H61B0.99
C47—O41.451 (3)
C6—N1—C2117.0 (2)H41A—C47—H41B108.4
N2—C2—N3116.9 (3)C4—O4—C47115.7 (2)
N2—C2—N1117.6 (3)N5—C5—C4117.2 (2)
N3—C2—N1125.5 (3)N5—C5—C6129.1 (3)
C2—N2—H2A120.0C4—C5—C6113.7 (2)
C2—N2—H2B120.0O5—N5—C5117.7 (2)
H2A—N2—H2B120.0N1—C6—O6118.8 (2)
C4—N3—C2116.0 (3)N1—C6—C5122.9 (3)
N3—C4—O4118.3 (3)O6—C6—C5118.3 (2)
N3—C4—C5124.8 (3)C66—C61—C62116.8 (3)
O4—C4—C5116.9 (2)C66—C61—C67122.4 (3)
C42—C41—C46117.3 (3)C62—C61—C67120.7 (3)
C42—C41—C47121.3 (3)N63—C62—C61124.7 (3)
C46—C41—C47121.3 (3)N63—C62—H62117.6
N43—C42—C41124.0 (3)C61—C62—H62117.6
N43—C42—H42118.0C62—N63—C64116.9 (3)
C41—C42—H42118.0N63—C64—C65123.3 (3)
C42—N43—C44116.9 (3)N63—C64—H64118.4
N43—C44—C45123.2 (3)C65—C64—H64118.4
N43—C44—H44118.4C64—C65—C66118.8 (3)
C45—C44—H44118.4C64—C65—H65120.6
C44—C45—C46118.6 (3)C66—C65—H65120.6
C44—C45—H45120.7C61—C66—C65119.6 (3)
C46—C45—H45120.7C61—C66—H66120.2
C45—C46—C41119.9 (3)C65—C66—H66120.2
C45—C46—H46120.1O6—C67—C61108.2 (2)
C41—C46—H46120.1O6—C67—H61A110.1
O4—C47—C41108.0 (2)C61—C67—H61A110.1
O4—C47—H41A110.1O6—C67—H61B110.1
C41—C47—H41A110.1C61—C67—H61B110.1
O4—C47—H41B110.1H61A—C67—H61B108.4
C41—C47—H41B110.1C6—O6—C67116.0 (2)
C6—N1—C2—N2175.2 (3)O4—C4—C5—C6177.6 (2)
C6—N1—C2—N34.4 (4)C4—C5—N5—O5178.0 (3)
N2—C2—N3—C4176.4 (3)C6—C5—N5—O53.2 (4)
N1—C2—N3—C43.2 (4)C2—N1—C6—O6178.1 (3)
C2—N3—C4—O4179.7 (3)C2—N1—C6—C51.9 (4)
C2—N3—C4—C50.6 (4)N5—C5—C6—N1179.8 (3)
C46—C41—C42—N431.5 (5)C4—C5—C6—N11.4 (4)
C47—C41—C42—N43179.1 (3)N5—C5—C6—O60.2 (5)
C41—C42—N43—C441.7 (5)C4—C5—C6—O6178.6 (2)
C42—N43—C44—C450.5 (5)C66—C61—C62—N630.8 (4)
N43—C44—C45—C460.9 (5)C67—C61—C62—N63177.6 (3)
C44—C45—C46—C411.1 (4)C61—C62—N63—C641.2 (4)
C42—C41—C46—C450.0 (4)C62—N63—C64—C651.0 (4)
C47—C41—C46—C45177.6 (3)N63—C64—C65—C660.3 (5)
C42—C41—C47—O448.4 (4)C62—C61—C66—C650.0 (4)
C46—C41—C47—O4134.1 (3)C67—C61—C66—C65176.8 (3)
N3—C4—O4—C473.4 (4)C64—C65—C66—C610.2 (4)
C5—C4—O4—C47176.3 (3)C66—C61—C67—O6123.6 (3)
C41—C47—O4—C4178.5 (2)C62—C61—C67—O659.8 (3)
N3—C4—C5—N5178.3 (3)N1—C6—O6—C670.4 (4)
O4—C4—C5—N51.4 (4)C5—C6—O6—C67179.6 (2)
N3—C4—C5—C62.7 (4)C61—C67—O6—C6179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N43i0.882.032.878 (4)163
N2—H2B···N63ii0.882.022.888 (4)171
C65—H65···Cg2iii0.952.693.526 (4)148
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x1/2, y+3/2, z; (iii) x1/2, y+5/2, z.
(VI) 2-Amino-4,6-bis(2-hydroxyethylamino)-5-nitrosopyrimidine top
Crystal data top
C8H14N6O3F(000) = 512
Mr = 242.25Dx = 1.556 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2366 reflections
a = 9.6487 (1) Åθ = 3.1–27.5°
b = 14.8594 (2) ŵ = 0.12 mm1
c = 7.3497 (2) ÅT = 120 K
β = 101.097 (1)°Rod, orange
V = 1034.05 (3) Å30.20 × 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 tubeRint = 0.039
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ϕ scans, and ω scans with κ offsetsh = 1212
14888 measured reflectionsk = 1919
2366 independent reflectionsl = 98
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-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 parametersΔρmax = 0.55 e Å3
11 restraintsΔρmin = 0.37 e Å3
Crystal data top
C8H14N6O3V = 1034.05 (3) Å3
Mr = 242.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.6487 (1) ŵ = 0.12 mm1
b = 14.8594 (2) ÅT = 120 K
c = 7.3497 (2) Å0.20 × 0.06 × 0.04 mm
β = 101.097 (1)°
Data collection top
Kappa-CCD
diffractometer
1928 reflections with I > 2σ(I)
14888 measured reflectionsRint = 0.039
2366 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06611 restraints
wR(F2) = 0.180H-atom parameters constrained
S = 1.04Δρmax = 0.55 e Å3
2366 reflectionsΔρmin = 0.37 e Å3
180 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.36042 (17)0.22258 (12)0.0872 (3)0.0280 (4)
N20.36388 (18)0.06965 (13)0.0998 (3)0.0373 (5)
C20.4314 (2)0.14488 (14)0.0711 (3)0.0267 (4)
N30.56145 (16)0.13395 (12)0.0300 (2)0.0238 (4)
N40.76382 (18)0.20569 (12)0.0139 (2)0.0273 (4)
C40.6325 (2)0.20989 (14)0.0141 (3)0.0230 (4)
C410.84213 (18)0.12222 (13)0.0150 (3)0.0325 (5)
C420.98242 (18)0.13999 (13)0.0707 (3)0.0267 (8)0.819 (3)
O41.05773 (18)0.20277 (12)0.0656 (3)0.0294 (5)0.819 (3)
C4210.9853 (9)0.1493 (13)0.048 (3)0.030*0.181 (3)
O411.0470 (9)0.0613 (6)0.0744 (11)0.030*0.181 (3)
C50.57073 (19)0.29767 (13)0.0296 (3)0.0233 (4)
N50.6318 (7)0.3787 (3)0.022 (2)0.0315 (15)0.68
O50.7592 (2)0.38242 (16)0.0047 (3)0.0326 (5)0.68
N510.6588 (14)0.3673 (4)0.025 (5)0.038 (4)0.32
O510.6123 (5)0.4452 (3)0.0401 (8)0.0366 (11)0.32
C60.4282 (2)0.29869 (14)0.0661 (3)0.0241 (4)
N60.36753 (17)0.37779 (13)0.0829 (2)0.0285 (4)
C610.22774 (17)0.39091 (13)0.1253 (2)0.0324 (5)
C620.11478 (17)0.40081 (13)0.0457 (2)0.0291 (8)0.819 (3)
O60.14364 (18)0.46683 (12)0.1692 (3)0.0302 (5)0.819 (3)
C6210.1147 (9)0.3804 (15)0.0461 (11)0.0291 (8)0.181 (3)
O610.0344 (7)0.3610 (6)0.0706 (12)0.0302 (5)0.181 (3)
H2A0.40410.01700.09160.045*
H2B0.27910.07250.12690.045*
H40.80610.25630.03290.033*
H41A0.78650.07940.10340.039*0.819 (3)
H41B0.85810.09470.10990.039*0.819 (3)
H41C0.79450.08200.11520.039*0.181 (3)
H41D0.85020.09050.10510.039*0.181 (3)
H42A1.03650.08330.07040.032*0.819 (3)
H42B0.96800.16650.19650.032*0.819 (3)
H4A1.13690.21460.03980.035*0.819 (3)
H42C0.97820.18760.15930.036*0.181 (3)
H42D1.04040.18130.06080.036*0.181 (3)
H411.00870.02170.01920.036*0.181 (3)
H60.41600.42630.06700.034*
H61A0.22880.44550.20290.039*0.819 (3)
H61B0.20460.33890.19830.039*0.819 (3)
H61C0.22170.45180.17790.039*0.181 (3)
H61D0.21210.34640.21960.039*0.181 (3)
H62A0.10230.34230.11120.035*0.819 (3)
H62B0.02450.41580.00770.035*0.819 (3)
H6A0.15290.51700.11540.036*0.819 (3)
H62C0.11910.43720.11540.035*0.181 (3)
H62D0.15190.33330.11900.035*0.181 (3)
H610.04750.30550.08760.036*0.181 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0160 (8)0.0340 (10)0.0349 (10)0.0001 (6)0.0076 (7)0.0089 (7)
N20.0189 (8)0.0323 (10)0.0646 (13)0.0020 (7)0.0178 (8)0.0134 (9)
C20.0172 (9)0.0341 (11)0.0291 (10)0.0002 (7)0.0050 (7)0.0062 (8)
N30.0149 (8)0.0336 (9)0.0234 (8)0.0045 (6)0.0051 (6)0.0002 (6)
N40.0180 (8)0.0311 (9)0.0353 (10)0.0072 (6)0.0115 (7)0.0093 (7)
C40.0174 (9)0.0345 (11)0.0173 (9)0.0049 (7)0.0037 (7)0.0048 (7)
C410.0250 (10)0.0291 (11)0.0484 (13)0.0086 (8)0.0196 (9)0.0123 (9)
C420.0206 (11)0.0252 (14)0.0386 (19)0.0055 (9)0.0164 (11)0.0095 (11)
O40.0172 (8)0.0308 (10)0.0415 (11)0.0037 (7)0.0090 (7)0.0003 (7)
C50.0151 (9)0.0322 (11)0.0221 (9)0.0041 (7)0.0026 (7)0.0010 (7)
N50.0133 (16)0.053 (4)0.028 (2)0.0092 (18)0.0036 (18)0.005 (3)
O50.0172 (11)0.0338 (12)0.0494 (14)0.0069 (9)0.0128 (10)0.0089 (10)
N510.043 (9)0.026 (4)0.041 (6)0.016 (4)0.002 (9)0.004 (4)
O510.028 (3)0.019 (2)0.060 (3)0.002 (2)0.005 (2)0.002 (2)
C60.0159 (9)0.0346 (11)0.0214 (9)0.0003 (7)0.0025 (7)0.0034 (7)
N60.0190 (8)0.0338 (10)0.0337 (9)0.0000 (7)0.0073 (7)0.0043 (7)
C610.0238 (10)0.0401 (12)0.0360 (11)0.0057 (9)0.0123 (9)0.0073 (9)
C620.0214 (10)0.024 (2)0.0424 (13)0.0010 (9)0.0083 (8)0.0171 (10)
O60.0263 (9)0.0259 (9)0.0375 (10)0.0037 (7)0.0040 (7)0.0109 (7)
C6210.0214 (10)0.024 (2)0.0424 (13)0.0010 (9)0.0083 (8)0.0171 (10)
O610.0263 (9)0.0259 (9)0.0375 (10)0.0037 (7)0.0040 (7)0.0109 (7)
Geometric parameters (Å, º) top
N1—C61.331 (3)O41—H410.84
N1—C21.359 (3)C5—N511.344 (5)
N2—C21.331 (3)C5—N51.346 (4)
N2—H2A0.88C5—C61.451 (3)
N2—H2B0.88N5—O51.284 (4)
C2—N31.356 (2)N51—O511.254 (5)
N3—C41.337 (3)C6—N61.330 (3)
N4—C41.323 (2)N6—C611.455 (2)
N4—C411.453 (3)N6—H60.88
N4—H40.88C61—C621.5042
C4—C51.448 (3)C61—C6211.507 (5)
C41—C4211.502 (5)C61—H61A0.99
C41—C421.5108C61—H61B0.99
C41—H41A0.99C61—H61C0.99
C41—H41B0.99C61—H61D0.99
C41—H41C0.99C62—O61.400 (2)
C41—H41D0.99C62—H62A0.99
C42—O41.457 (3)C62—H62B0.99
C42—H42A0.99O6—H6A0.84
C42—H42B0.99C621—O611.444 (5)
O4—H4A0.84C621—H62C0.99
C421—O411.47 (2)C621—H62D0.99
C421—H42C0.99O61—H610.84
C421—H42D0.99
C6—N1—C2116.39 (17)N51—C5—C4114.8 (4)
C2—N2—H2A120.0N5—C5—C4127.8 (3)
C2—N2—H2B120.0N51—C5—C6128.6 (4)
H2A—N2—H2B120.0N5—C5—C6115.8 (3)
N2—C2—N3115.90 (19)C4—C5—C6116.30 (16)
N2—C2—N1115.44 (18)O5—N5—C5118.9 (4)
N3—C2—N1128.66 (18)O51—N51—C5118.0 (6)
C4—N3—C2115.51 (17)N6—C6—N1120.34 (18)
C4—N4—C41123.74 (16)N6—C6—C5118.47 (17)
C4—N4—H4118.1N1—C6—C5121.17 (18)
C41—N4—H4118.1C6—N6—C61125.57 (17)
N4—C4—N3119.75 (18)C6—N6—H6117.2
N4—C4—C5118.39 (17)C61—N6—H6117.2
N3—C4—C5121.84 (17)N6—C61—C62112.74 (10)
N4—C41—C421105.5 (8)N6—C61—C621111.0 (5)
N4—C41—C42110.26 (9)N6—C61—H61A109.0
N4—C41—H41A109.6C62—C61—H61A109.0
C421—C41—H41A117.8C621—C61—H61A119.4
C42—C41—H41A109.6N6—C61—H61B109.0
N4—C41—H41B109.6C62—C61—H61B109.0
C421—C41—H41B105.9C621—C61—H61B99.8
C42—C41—H41B109.6H61A—C61—H61B107.8
H41A—C41—H41B108.1N6—C61—H61C109.4
N4—C41—H41C110.6C62—C61—H61C98.6
C421—C41—H41C110.6C621—C61—H61C109.4
C42—C41—H41C102.5H61B—C61—H61C117.8
H41B—C41—H41C114.1N6—C61—H61D109.4
N4—C41—H41D110.6C62—C61—H61D117.8
C421—C41—H41D110.6C621—C61—H61D109.4
C42—C41—H41D113.8H61A—C61—H61D97.5
H41A—C41—H41D102.7H61C—C61—H61D108.0
H41C—C41—H41D108.8O6—C62—C61114.06 (10)
O4—C42—C41106.25 (9)O6—C62—H62A108.7
O4—C42—H42A110.5C61—C62—H62A108.7
C41—C42—H42A110.5O6—C62—H62B108.7
O4—C42—H42B110.5C61—C62—H62B108.7
C41—C42—H42B110.5H62A—C62—H62B107.6
H42A—C42—H42B108.7C62—O6—H6A109.5
C42—O4—H4A109.5O61—C621—C61131.9 (8)
O41—C421—C41101.1 (10)O61—C621—H62C104.3
O41—C421—H42C111.6C61—C621—H62C104.3
C41—C421—H42C111.6O61—C621—H62D104.3
O41—C421—H42D111.6C61—C621—H62D104.3
C41—C421—H42D111.6H62C—C621—H62D105.6
H42C—C421—H42D109.4C621—O61—H61109.5
C421—O41—H41109.5
C6—N1—C2—N2177.52 (19)C4—C5—N5—O51.4 (17)
C6—N1—C2—N32.4 (3)C6—C5—N5—O5178.2 (9)
N2—C2—N3—C4175.56 (18)N5—C5—N51—O5110 (7)
N1—C2—N3—C44.3 (3)C4—C5—N51—O51179 (2)
C41—N4—C4—N34.8 (3)C6—C5—N51—O515 (4)
C41—N4—C4—C5174.18 (18)C2—N1—C6—N6178.81 (18)
C2—N3—C4—N4175.66 (17)C2—N1—C6—C50.6 (3)
C2—N3—C4—C53.3 (3)N51—C5—C6—N66 (2)
C4—N4—C41—C421178.9 (9)N5—C5—C6—N62.3 (8)
C4—N4—C41—C42174.01 (15)C4—C5—C6—N6179.47 (16)
N4—C41—C42—O459.55 (13)N51—C5—C6—N1172 (2)
C421—C41—C42—O44 (5)N5—C5—C6—N1176.0 (8)
N4—C41—C421—O41171.8 (8)C4—C5—C6—N11.2 (3)
C42—C41—C421—O4146 (5)N1—C6—N6—C610.4 (3)
N4—C4—C5—N513.8 (18)C5—C6—N6—C61177.87 (17)
N3—C4—C5—N51175.2 (17)C6—N6—C61—C6293.46 (19)
N4—C4—C5—N51.3 (9)C6—N6—C61—C62181.2 (10)
N3—C4—C5—N5177.7 (9)N6—C61—C62—O652.66 (14)
N4—C4—C5—C6178.10 (16)C621—C61—C62—O6136 (2)
N3—C4—C5—C60.9 (3)N6—C61—C621—O61159.1 (17)
N51—C5—N5—O512 (8)C62—C61—C621—O61100 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N3i0.882.463.293 (3)158
N2—H2B···O6ii0.882.253.014 (3)146
N4—H4···O50.881.952.628 (2)133
O4—H4A···N1iii0.842.122.909 (2)156
O6—H6A···O5iv0.841.862.659 (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 formulaC14H23N5C16H15N5O2C12H18N6O3C18H18N6O
Mr261.37309.33294.32334.38
Crystal system, space groupMonoclinic, P21/cTriclinic, P1Monoclinic, P21/cMonoclinic, P21/c
Temperature (K)120120120120
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), 9070.038 (1), 73.206 (1), 79.626 (1)90, 112.3400 (12), 9090, 113.3020 (12), 90
V3)1359.93 (7)2199.62 (12)1368.92 (7)1588.61 (8)
Z4644
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.080.100.110.09
Crystal size (mm)0.35 × 0.30 × 0.220.40 × 0.20 × 0.050.30 × 0.20 × 0.200.42 × 0.12 × 0.03
Data collection
DiffractometerKappa-CCD
diffractometer
Kappa-CCD
diffractometer
Kappa-CCD
diffractometer
Kappa-CCD
diffractometer
Absorption correctionMulti-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Tmin, Tmax0.968, 0.9830.957, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
13657, 3100, 2195 32137, 9847, 4349 10906, 3096, 2391 27586, 3618, 2492
Rint0.0690.0860.0470.099
(sin θ/λ)max1)0.6490.6500.6490.649
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 reflections3100984730963618
No. of parameters172622190226
No. of restraints0000
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.290.30, 0.340.41, 0.280.27, 0.34


(V)(VI)
Crystal data
Chemical formulaC16H14N6O3C8H14N6O3
Mr338.33242.25
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21/c
Temperature (K)120120
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, 9090, 101.097 (1), 90
V3)1538.6 (7)1034.05 (3)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.110.12
Crystal size (mm)0.45 × 0.12 × 0.040.20 × 0.06 × 0.04
Data collection
DiffractometerKappa-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
Rint0.0670.039
(sin θ/λ)max1)0.6490.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.100, 1.00 0.066, 0.180, 1.04
No. of reflections20262366
No. of parameters226180
No. of restraints011
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.280.55, 0.37

Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997b), SHELXS97 (Sheldrick, 1997)b, SHELXS972-66 (Sheldrick, 1997b), PLATON (Spek, 2003), PLATON (Spek, 2002), SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.882.373.216 (2)162
C66—H66B···Cg1ii0.992.683.518 (2)142
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N12—H12A···N3630.882.122.998 (3)174
N12—H12B···N343i0.882.102.977 (3)176
N22—H22A···N263ii0.882.112.985 (3)175
N22—H22B···N243iii0.882.112.987 (3)175
N32—H32A···N1430.882.112.978 (3)167
N32—H32B···N163iv0.882.102.982 (3)178
Symmetry codes: (i) x+1, y+1, z1; (ii) x+1, y+2, z; (iii) x, y+1, z+1; (iv) x1, y1, z+1.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O64i0.882.042.918 (2)177
N2—H2B···O44ii0.882.132.894 (2)144
C43—H43A···O5ii0.992.473.376 (2)152
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N3i0.882.193.042 (2)163
N2—H2B···N1ii0.882.152.967 (2)155
N4—H4···O5iii0.882.152.993 (2)161
N6—H6···O50.881.942.617 (2)133
C63—H63···O5iv0.952.513.335 (2)146
Symmetry codes: (i) x+1, y1/2, 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···AD—HH···AD···AD—H···A
N2—H2A···N43i0.882.032.878 (4)163
N2—H2B···N63ii0.882.022.888 (4)171
C65—H65···Cg2iii0.952.693.526 (4)148
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x1/2, y+3/2, z; (iii) x1/2, y+5/2, z.
Hydrogen-bond geometry (Å, º) for (VI) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N3i0.882.463.293 (3)158
N2—H2B···O6ii0.882.253.014 (3)146
N4—H4···O50.881.952.628 (2)133
O4—H4A···N1iii0.842.122.909 (2)156
O6—H6A···O5iv0.841.862.659 (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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