Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615024956/xk5025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615024956/xk50251066psup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615024956/xk50251061sup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615024956/xk5025sup4.pdf |
CCDC references: 1444950; 1444951
For both compounds, data collection: Oxford Diffraction (2010). CrysAlis CCD, Version 1.171.33.42; cell refinement: Oxford Diffraction (2010). CrysAlis RED, Version 1.171.33.42; data reduction: Oxford Diffraction (2010). CrysAlis RED, Version 1.171.33.42; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular Structure Visualisation, University of Bonn, Germany; software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).
C6H6N4O4 | F(000) = 204 |
Mr = 198.15 | Dx = 1.547 Mg m−3 Dm = 1.54 Mg m−3 Dm measured by floatation |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.1964 (3) Å | Cell parameters from 1345 reflections |
b = 7.0129 (5) Å | θ = 3.0–29.4° |
c = 14.4528 (10) Å | µ = 0.13 mm−1 |
β = 90.924 (7)° | T = 295 K |
V = 425.28 (5) Å3 | Parallelepiped, yellow |
Z = 2 | 0.24 × 0.22 × 0.16 mm |
KUMA KM-4 CCD diffractometer | 1893 independent reflections |
Radiation source: fine-focus sealed tube | 1386 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 1024x1024 with blocks 2x2 pixels mm-1 | θmax = 29.4°, θmin = 2.8° |
ω–scan | h = −5→5 |
Absorption correction: numerical Oxford Diffraction (2010). CrysAlis Red, Version 1.171.33.42 | k = −7→9 |
Tmin = 0.974, Tmax = 0.984 | l = −19→19 |
5895 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.027P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.059 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.10 e Å−3 |
1893 reflections | Δρmin = −0.10 e Å−3 |
136 parameters | Absolute structure: Flack x determined using 449 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: −0.1 (1) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4383 (3) | 0.3386 (2) | 0.22542 (8) | 0.0459 (3) | |
C1 | 0.6066 (5) | 0.3173 (4) | 0.14708 (13) | 0.0459 (5) | |
C2 | 0.5733 (5) | 0.1441 (4) | 0.10957 (14) | 0.0566 (6) | |
H2 | 0.6671 | 0.0992 | 0.0559 | 0.068* | |
C3 | 0.3674 (5) | 0.0438 (4) | 0.16786 (14) | 0.0542 (6) | |
H3 | 0.2976 | −0.0812 | 0.1605 | 0.065* | |
C4 | 0.2904 (4) | 0.1661 (3) | 0.23720 (12) | 0.0412 (5) | |
N1 | 0.7921 (5) | 0.4765 (3) | 0.12053 (13) | 0.0609 (5) | |
O2 | 0.9453 (4) | 0.4585 (3) | 0.04943 (11) | 0.0849 (6) | |
O3 | 0.7958 (5) | 0.6193 (3) | 0.16871 (13) | 0.0914 (6) | |
C5 | 0.0920 (4) | 0.1536 (3) | 0.31757 (12) | 0.0411 (5) | |
H5 | 0.0562 | 0.2599 | 0.3544 | 0.049* | |
N2 | −0.0334 (3) | −0.0075 (2) | 0.33688 (10) | 0.0415 (4) | |
N3 | −0.2195 (4) | −0.0118 (2) | 0.41303 (11) | 0.0432 (4) | |
H1 | −0.276 (5) | 0.095 (3) | 0.4419 (14) | 0.052* | |
C6 | −0.3527 (5) | −0.1777 (3) | 0.44125 (12) | 0.0433 (5) | |
O4 | −0.5107 (4) | −0.17866 (19) | 0.51261 (9) | 0.0526 (4) | |
N4 | −0.3018 (6) | −0.3317 (3) | 0.39040 (16) | 0.0697 (6) | |
H41 | −0.207 (6) | −0.327 (4) | 0.3380 (17) | 0.084* | |
H42 | −0.387 (6) | −0.439 (4) | 0.4090 (17) | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0465 (7) | 0.0500 (9) | 0.0415 (7) | 0.0037 (7) | 0.0135 (6) | 0.0046 (7) |
C1 | 0.0392 (10) | 0.0605 (13) | 0.0384 (10) | 0.0064 (12) | 0.0114 (9) | 0.0094 (12) |
C2 | 0.0458 (11) | 0.0825 (18) | 0.0419 (11) | 0.0076 (13) | 0.0105 (10) | −0.0077 (14) |
C3 | 0.0510 (12) | 0.0594 (14) | 0.0525 (12) | 0.0008 (11) | 0.0090 (11) | −0.0110 (11) |
C4 | 0.0364 (9) | 0.0448 (12) | 0.0423 (11) | 0.0035 (10) | 0.0014 (9) | 0.0011 (11) |
N1 | 0.0581 (11) | 0.0729 (14) | 0.0521 (11) | 0.0063 (11) | 0.0154 (10) | 0.0172 (11) |
O2 | 0.0801 (11) | 0.1127 (16) | 0.0629 (10) | 0.0028 (11) | 0.0343 (9) | 0.0236 (10) |
O3 | 0.1134 (14) | 0.0678 (13) | 0.0942 (13) | −0.0168 (11) | 0.0420 (12) | 0.0029 (12) |
C5 | 0.0405 (9) | 0.0437 (13) | 0.0394 (10) | 0.0038 (11) | 0.0062 (9) | 0.0016 (11) |
N2 | 0.0402 (9) | 0.0436 (11) | 0.0408 (9) | 0.0056 (8) | 0.0088 (8) | 0.0027 (8) |
N3 | 0.0507 (9) | 0.0359 (11) | 0.0435 (9) | 0.0037 (9) | 0.0149 (8) | −0.0014 (8) |
C6 | 0.0542 (11) | 0.0338 (10) | 0.0422 (11) | 0.0051 (11) | 0.0080 (9) | 0.0031 (11) |
O4 | 0.0757 (9) | 0.0357 (8) | 0.0471 (7) | −0.0004 (9) | 0.0224 (7) | 0.0025 (7) |
N4 | 0.1099 (17) | 0.0356 (11) | 0.0650 (12) | −0.0034 (11) | 0.0421 (12) | −0.0020 (10) |
O1—C1 | 1.352 (2) | N1—O2 | 1.228 (2) |
O1—C4 | 1.372 (3) | C5—N2 | 1.278 (3) |
C1—C2 | 1.336 (3) | C5—H5 | 0.9300 |
C1—N1 | 1.418 (3) | N2—N3 | 1.360 (2) |
C2—C3 | 1.405 (3) | N3—C6 | 1.357 (3) |
C2—H2 | 0.9300 | N3—H1 | 0.89 (2) |
C3—C4 | 1.362 (3) | C6—O4 | 1.235 (2) |
C3—H3 | 0.9300 | C6—N4 | 1.326 (3) |
C4—C5 | 1.443 (2) | N4—H41 | 0.86 (2) |
N1—O3 | 1.220 (3) | N4—H42 | 0.88 (3) |
C1—O1—C4 | 104.45 (18) | O2—N1—C1 | 116.3 (2) |
C2—C1—O1 | 112.82 (19) | N2—C5—C4 | 118.33 (18) |
C2—C1—N1 | 131.31 (19) | N2—C5—H5 | 120.8 |
O1—C1—N1 | 115.8 (2) | C4—C5—H5 | 120.8 |
C1—C2—C3 | 105.82 (19) | C5—N2—N3 | 116.11 (16) |
C1—C2—H2 | 127.1 | C6—N3—N2 | 120.47 (17) |
C3—C2—H2 | 127.1 | C6—N3—H1 | 117.7 (14) |
C4—C3—C2 | 106.4 (2) | N2—N3—H1 | 121.5 (14) |
C4—C3—H3 | 126.8 | O4—C6—N4 | 123.5 (2) |
C2—C3—H3 | 126.8 | O4—C6—N3 | 119.02 (19) |
C3—C4—O1 | 110.54 (17) | N4—C6—N3 | 117.47 (16) |
C3—C4—C5 | 134.5 (2) | C6—N4—H41 | 123 (2) |
O1—C4—C5 | 114.95 (16) | C6—N4—H42 | 117.5 (17) |
O3—N1—O2 | 124.1 (2) | H41—N4—H42 | 120 (3) |
O3—N1—C1 | 119.61 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1···O4i | 0.89 (2) | 1.94 (2) | 2.817 (2) | 166.6 (19) |
N4—H41···O3ii | 0.86 (2) | 2.48 (2) | 3.255 (3) | 151 (2) |
N4—H42···O4iii | 0.88 (3) | 2.07 (3) | 2.922 (2) | 162 (2) |
Symmetry codes: (i) −x−1, y+1/2, −z+1; (ii) x−1, y−1, z; (iii) −x−1, y−1/2, −z+1. |
C6H6N4O4 | F(000) = 408 |
Mr = 198.15 | Dx = 1.592 Mg m−3 Dm = 1.59 Mg m−3 Dm measured by floatation |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.5703 (6) Å | Cell parameters from 1345 reflections |
b = 7.8254 (3) Å | θ = 3.0–29.4° |
c = 7.9677 (4) Å | µ = 0.14 mm−1 |
β = 102.260 (4)° | T = 295 K |
V = 826.82 (6) Å3 | Parallelepiped, orange |
Z = 4 | 0.31 × 0.27 × 0.22 mm |
KUMA KM-4 with CCD detector diffractometer | 2127 independent reflections |
Radiation source: fine-focus sealed tube | 1614 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 1024x1024 with blocks 2x2 pixels mm-1 | θmax = 29.4°, θmin = 3.0° |
ω–scan | h = −18→17 |
Absorption correction: numerical Oxford Diffraction (2010). CrysAlis Red, Version 1.171.33.42 | k = −10→10 |
Tmin = 0.961, Tmax = 0.976 | l = −10→10 |
11142 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.0108P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
2127 reflections | Δρmax = 0.13 e Å−3 |
136 parameters | Δρmin = −0.17 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.23439 (4) | 0.16292 (7) | 0.51987 (7) | 0.03382 (16) | |
C1 | 0.15329 (6) | 0.13258 (11) | 0.58773 (11) | 0.0340 (2) | |
C2 | 0.10884 (7) | 0.27700 (12) | 0.62574 (12) | 0.0413 (2) | |
H2 | 0.0519 | 0.2863 | 0.6727 | 0.050* | |
C3 | 0.16699 (7) | 0.41115 (12) | 0.57904 (12) | 0.0405 (2) | |
H3 | 0.1561 | 0.5276 | 0.5899 | 0.049* | |
C4 | 0.24227 (6) | 0.33758 (11) | 0.51490 (10) | 0.03248 (19) | |
N1 | 0.12908 (6) | −0.04135 (10) | 0.60652 (10) | 0.0428 (2) | |
O2 | 0.05919 (6) | −0.07059 (11) | 0.67792 (10) | 0.0605 (2) | |
O3 | 0.17783 (7) | −0.15180 (9) | 0.55223 (12) | 0.0687 (3) | |
C5 | 0.32308 (6) | 0.39903 (10) | 0.44028 (11) | 0.0338 (2) | |
H5 | 0.3657 | 0.3223 | 0.4018 | 0.041* | |
N2 | 0.33598 (5) | 0.56055 (9) | 0.42712 (9) | 0.03357 (18) | |
N3 | 0.41281 (6) | 0.60742 (9) | 0.35253 (9) | 0.03636 (19) | |
H3N | 0.4528 (8) | 0.5333 (14) | 0.3129 (13) | 0.044* | |
C6 | 0.43657 (7) | 0.77623 (11) | 0.34068 (11) | 0.0361 (2) | |
O4 | 0.51014 (6) | 0.81353 (9) | 0.28090 (10) | 0.0538 (2) | |
N4 | 0.37769 (7) | 0.88891 (11) | 0.39663 (13) | 0.0512 (2) | |
H41 | 0.3235 (10) | 0.8565 (15) | 0.4398 (15) | 0.061* | |
H42 | 0.3926 (9) | 0.9933 (17) | 0.3896 (15) | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0349 (3) | 0.0241 (3) | 0.0465 (3) | −0.0035 (2) | 0.0178 (3) | 0.0008 (2) |
C1 | 0.0336 (4) | 0.0312 (4) | 0.0402 (4) | −0.0067 (3) | 0.0145 (4) | 0.0015 (3) |
C2 | 0.0396 (5) | 0.0407 (5) | 0.0493 (5) | −0.0024 (4) | 0.0224 (4) | −0.0020 (4) |
C3 | 0.0452 (5) | 0.0290 (4) | 0.0518 (5) | −0.0019 (4) | 0.0206 (4) | −0.0026 (4) |
C4 | 0.0365 (4) | 0.0244 (4) | 0.0379 (4) | −0.0041 (3) | 0.0110 (3) | 0.0006 (3) |
N1 | 0.0426 (4) | 0.0357 (4) | 0.0527 (5) | −0.0115 (3) | 0.0160 (4) | 0.0039 (3) |
O2 | 0.0564 (5) | 0.0596 (5) | 0.0735 (5) | −0.0212 (4) | 0.0314 (4) | 0.0094 (4) |
O3 | 0.0774 (6) | 0.0284 (4) | 0.1119 (7) | −0.0068 (3) | 0.0466 (5) | −0.0026 (4) |
C5 | 0.0361 (4) | 0.0262 (4) | 0.0429 (5) | −0.0022 (3) | 0.0165 (4) | 0.0003 (3) |
N2 | 0.0354 (4) | 0.0277 (3) | 0.0418 (4) | −0.0034 (3) | 0.0176 (3) | 0.0006 (3) |
N3 | 0.0420 (4) | 0.0228 (3) | 0.0524 (4) | −0.0014 (3) | 0.0284 (4) | −0.0009 (3) |
C6 | 0.0378 (5) | 0.0258 (4) | 0.0470 (5) | −0.0018 (3) | 0.0145 (4) | 0.0058 (3) |
O4 | 0.0472 (4) | 0.0351 (4) | 0.0885 (5) | −0.0040 (3) | 0.0356 (4) | 0.0141 (3) |
N4 | 0.0582 (6) | 0.0235 (4) | 0.0803 (6) | 0.0016 (4) | 0.0335 (5) | −0.0002 (4) |
O1—C1 | 1.3464 (10) | N1—O2 | 1.2266 (11) |
O1—C4 | 1.3722 (10) | C5—N2 | 1.2834 (11) |
C1—C2 | 1.3455 (13) | C5—H5 | 0.9300 |
C1—N1 | 1.4155 (11) | N2—N3 | 1.3557 (10) |
C2—C3 | 1.4099 (13) | N3—C6 | 1.3678 (11) |
C2—H2 | 0.9300 | N3—H3N | 0.896 (12) |
C3—C4 | 1.3631 (13) | C6—O4 | 1.2291 (11) |
C3—H3 | 0.9300 | C6—N4 | 1.3289 (12) |
C4—C5 | 1.4367 (12) | N4—H41 | 0.911 (13) |
N1—O3 | 1.2221 (11) | N4—H42 | 0.846 (13) |
C1—O1—C4 | 105.22 (6) | O2—N1—C1 | 116.62 (9) |
C2—C1—O1 | 112.71 (7) | N2—C5—C4 | 119.52 (8) |
C2—C1—N1 | 131.20 (8) | N2—C5—H5 | 120.2 |
O1—C1—N1 | 116.10 (8) | C4—C5—H5 | 120.2 |
C1—C2—C3 | 105.26 (8) | C5—N2—N3 | 115.67 (7) |
C1—C2—H2 | 127.4 | N2—N3—C6 | 120.41 (7) |
C3—C2—H2 | 127.4 | N2—N3—H3N | 124.0 (7) |
C4—C3—C2 | 106.89 (8) | C6—N3—H3N | 115.6 (7) |
C4—C3—H3 | 126.6 | O4—C6—N4 | 124.62 (8) |
C2—C3—H3 | 126.6 | O4—C6—N3 | 118.62 (8) |
C3—C4—O1 | 109.92 (7) | N4—C6—N3 | 116.76 (8) |
C3—C4—C5 | 135.44 (9) | C6—N4—H41 | 122.2 (8) |
O1—C4—C5 | 114.60 (7) | C6—N4—H42 | 116.7 (9) |
O3—N1—O2 | 124.21 (8) | H41—N4—H42 | 121.2 (12) |
O3—N1—C1 | 119.17 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O4i | 0.896 (12) | 1.982 (12) | 2.8258 (10) | 156.3 (10) |
N4—H41···O3ii | 0.911 (13) | 2.338 (13) | 3.2283 (13) | 165.4 (11) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y+1, z. |