Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010851/cf6184sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010851/cf6184Isup2.hkl |
CCDC reference: 189907
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.058
- wR factor = 0.155
- Data-to-parameter ratio = 14.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
C15H12N4O3 | F(000) = 616 |
Mr = 296.29 | Dx = 1.501 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.9554 (2) Å | Cell parameters from 2852 reflections |
b = 6.9671 (3) Å | θ = 3.0–27.5° |
c = 31.8248 (13) Å | µ = 0.11 mm−1 |
β = 96.8560 (17)° | T = 120 K |
V = 1311.03 (9) Å3 | Prism, orange |
Z = 4 | 0.50 × 0.35 × 0.08 mm |
Nonius KappaCCD diffractometer | 2852 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1820 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.093 |
φ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −7→5 |
Tmin = 0.927, Tmax = 0.991 | k = −9→8 |
6931 measured reflections | l = −40→41 |
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) = 0.155 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.079P)2] where P = (Fo2 + 2Fc2)/3 |
2852 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox, G·C. & Holmes, K·C., 1966, Acta Cryst. 20, 886–891) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
Geometry. Mean-plane data from the final SHELXL97 (Sheldrick, 1997) refinement run. Cg1 and Cg2 are the centroids of theC3A/C4/C5/C6/C7/C7A and C11/C12/C13/C14/C15/C16 rings, respectively. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.3867 (3) | 0.0255 (3) | 0.30503 (5) | 0.0221 (4) | |
N2 | 0.5877 (3) | 0.0778 (3) | 0.29285 (5) | 0.0262 (5) | |
C1 | 0.2013 (4) | −0.0410 (3) | 0.27379 (6) | 0.0244 (5) | |
C2 | 0.2318 (4) | 0.0403 (3) | 0.23038 (6) | 0.0227 (5) | |
C3 | 0.0328 (4) | −0.0047 (3) | 0.19785 (6) | 0.0212 (5) | |
O3 | −0.1408 (3) | −0.0761 (2) | 0.20713 (4) | 0.0282 (4) | |
N3 | 0.7214 (3) | 0.1381 (3) | 0.32595 (5) | 0.0259 (5) | |
C3A | 0.6024 (4) | 0.1241 (3) | 0.36072 (6) | 0.0207 (5) | |
C4 | 0.6692 (4) | 0.1706 (3) | 0.40345 (6) | 0.0235 (5) | |
C5 | 0.5134 (4) | 0.1383 (3) | 0.43113 (6) | 0.0243 (5) | |
C6 | 0.2988 (4) | 0.0628 (3) | 0.41780 (6) | 0.0230 (5) | |
C7 | 0.2296 (4) | 0.0174 (3) | 0.37601 (6) | 0.0217 (5) | |
C7A | 0.3885 (4) | 0.0518 (3) | 0.34777 (6) | 0.0199 (5) | |
C11 | 0.0542 (4) | 0.0508 (3) | 0.15266 (6) | 0.0214 (5) | |
C12 | 0.2512 (4) | 0.1330 (3) | 0.14131 (6) | 0.0236 (5) | |
C13 | 0.2689 (4) | 0.1819 (3) | 0.09939 (6) | 0.0240 (5) | |
C14 | 0.0853 (4) | 0.1473 (3) | 0.06987 (6) | 0.0227 (5) | |
N14 | 0.1031 (4) | 0.1998 (3) | 0.02543 (5) | 0.0298 (5) | |
O141 | −0.0714 (3) | 0.2151 (3) | 0.00109 (5) | 0.0399 (5) | |
O142 | 0.2927 (3) | 0.2255 (3) | 0.01534 (5) | 0.0487 (6) | |
C15 | −0.1150 (4) | 0.0673 (3) | 0.07984 (6) | 0.0254 (5) | |
C16 | −0.1279 (4) | 0.0179 (3) | 0.12167 (6) | 0.0213 (5) | |
H1A | 0.0546 | 0.0017 | 0.2822 | 0.029* | |
H1B | 0.2010 | −0.1830 | 0.2726 | 0.029* | |
H2A | 0.2509 | 0.1813 | 0.2326 | 0.027* | |
H2B | 0.3710 | −0.0139 | 0.2209 | 0.027* | |
H4 | 0.8147 | 0.2217 | 0.4126 | 0.028* | |
H5 | 0.5523 | 0.1680 | 0.4602 | 0.029* | |
H6 | 0.1972 | 0.0422 | 0.4382 | 0.028* | |
H7 | 0.0839 | −0.0338 | 0.3670 | 0.026* | |
H12 | 0.3751 | 0.1562 | 0.1624 | 0.028* | |
H13 | 0.4034 | 0.2373 | 0.0915 | 0.029* | |
H15 | −0.2393 | 0.0471 | 0.0587 | 0.031* | |
H16 | −0.2622 | −0.0390 | 0.1293 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0226 (11) | 0.0313 (11) | 0.0121 (8) | −0.0016 (9) | 0.0014 (7) | 0.0009 (7) |
N2 | 0.0244 (10) | 0.0370 (12) | 0.0170 (9) | −0.0033 (9) | 0.0012 (8) | 0.0016 (8) |
C1 | 0.0259 (13) | 0.0330 (13) | 0.0130 (10) | −0.0038 (11) | −0.0038 (9) | −0.0015 (9) |
C2 | 0.0281 (13) | 0.0268 (12) | 0.0130 (10) | 0.0021 (10) | 0.0021 (9) | 0.0028 (9) |
C3 | 0.0253 (13) | 0.0217 (12) | 0.0166 (10) | 0.0010 (10) | 0.0023 (9) | −0.0023 (9) |
O3 | 0.0302 (10) | 0.0363 (10) | 0.0179 (8) | −0.0049 (8) | 0.0024 (7) | −0.0011 (7) |
N3 | 0.0244 (11) | 0.0372 (12) | 0.0156 (9) | −0.0043 (9) | 0.0006 (8) | −0.0006 (8) |
C3A | 0.0224 (12) | 0.0252 (12) | 0.0143 (10) | −0.0007 (10) | 0.0010 (8) | 0.0002 (8) |
C4 | 0.0234 (13) | 0.0287 (13) | 0.0169 (10) | −0.0033 (10) | −0.0034 (9) | −0.0010 (9) |
C5 | 0.0295 (13) | 0.0271 (13) | 0.0150 (10) | 0.0021 (11) | −0.0023 (9) | −0.0032 (9) |
C6 | 0.0260 (13) | 0.0299 (13) | 0.0137 (10) | 0.0006 (10) | 0.0045 (9) | 0.0004 (9) |
C7 | 0.0224 (13) | 0.0259 (13) | 0.0160 (10) | −0.0013 (10) | −0.0006 (8) | 0.0015 (9) |
C7A | 0.0260 (13) | 0.0214 (12) | 0.0115 (9) | 0.0023 (10) | −0.0011 (8) | 0.0002 (8) |
C11 | 0.0266 (13) | 0.0224 (12) | 0.0148 (10) | 0.0022 (10) | 0.0006 (9) | −0.0006 (9) |
C12 | 0.0279 (13) | 0.0287 (13) | 0.0132 (10) | −0.0017 (11) | −0.0020 (9) | −0.0016 (9) |
C13 | 0.0286 (13) | 0.0259 (13) | 0.0179 (11) | −0.0025 (10) | 0.0049 (9) | −0.0002 (9) |
C14 | 0.0314 (13) | 0.0257 (12) | 0.0111 (10) | 0.0047 (10) | 0.0029 (9) | 0.0018 (9) |
N14 | 0.0390 (13) | 0.0345 (12) | 0.0157 (9) | −0.0024 (10) | 0.0019 (9) | 0.0011 (8) |
O141 | 0.0458 (12) | 0.0546 (12) | 0.0174 (8) | 0.0088 (10) | −0.0042 (8) | 0.0064 (8) |
O142 | 0.0507 (12) | 0.0774 (15) | 0.0189 (8) | −0.0183 (11) | 0.0084 (8) | 0.0039 (9) |
C15 | 0.0309 (14) | 0.0291 (13) | 0.0148 (10) | 0.0031 (11) | −0.0037 (9) | −0.0033 (9) |
C16 | 0.0211 (13) | 0.0243 (12) | 0.0183 (10) | −0.0011 (10) | 0.0016 (9) | −0.0006 (9) |
N1—N2 | 1.351 (2) | C5—H5 | 0.950 |
N1—C7A | 1.371 (2) | C6—C7 | 1.381 (3) |
N1—C1 | 1.469 (2) | C6—H6 | 0.950 |
N2—N3 | 1.312 (2) | C7—C7A | 1.402 (3) |
C1—C2 | 1.524 (3) | C7—H7 | 0.950 |
C1—H1A | 0.990 | C11—C12 | 1.392 (3) |
C1—H1B | 0.990 | C11—C16 | 1.395 (3) |
C2—C3 | 1.511 (3) | C12—C13 | 1.393 (3) |
C2—H2A | 0.990 | C12—H12 | 0.950 |
C2—H2B | 0.990 | C13—C14 | 1.375 (3) |
C3—O3 | 1.215 (3) | C13—H13 | 0.950 |
C3—C11 | 1.509 (3) | C14—C15 | 1.387 (3) |
N3—C3A | 1.387 (3) | C14—N14 | 1.477 (2) |
C3A—C7A | 1.386 (3) | N14—O142 | 1.223 (3) |
C3A—C4 | 1.408 (3) | N14—O141 | 1.224 (2) |
C4—C5 | 1.372 (3) | C15—C16 | 1.386 (3) |
C4—H4 | 0.950 | C15—H15 | 0.950 |
C5—C6 | 1.400 (3) | C16—H16 | 0.950 |
N2—N1—C7A | 110.24 (17) | C7—C6—H6 | 118.8 |
N2—N1—C1 | 120.71 (16) | C5—C6—H6 | 118.8 |
C7A—N1—C1 | 129.01 (18) | C6—C7—C7A | 115.6 (2) |
N3—N2—N1 | 109.27 (16) | C6—C7—H7 | 122.2 |
N1—C1—C2 | 109.55 (18) | C7A—C7—H7 | 122.2 |
N1—C1—H1A | 109.8 | N1—C7A—C3A | 104.00 (18) |
C2—C1—H1A | 109.8 | N1—C7A—C7 | 133.4 (2) |
N1—C1—H1B | 109.8 | C3A—C7A—C7 | 122.57 (18) |
C2—C1—H1B | 109.8 | C12—C11—C16 | 119.52 (18) |
H1A—C1—H1B | 108.2 | C12—C11—C3 | 121.49 (18) |
C3—C2—C1 | 112.06 (19) | C16—C11—C3 | 118.99 (19) |
C3—C2—H2A | 109.2 | C11—C12—C13 | 120.77 (19) |
C1—C2—H2A | 109.2 | C11—C12—H12 | 119.6 |
C3—C2—H2B | 109.2 | C13—C12—H12 | 119.6 |
C1—C2—H2B | 109.2 | C14—C13—C12 | 117.8 (2) |
H2A—C2—H2B | 107.9 | C14—C13—H13 | 121.1 |
O3—C3—C11 | 120.50 (19) | C12—C13—H13 | 121.1 |
O3—C3—C2 | 122.61 (18) | C13—C14—C15 | 123.33 (19) |
C11—C3—C2 | 116.85 (19) | C13—C14—N14 | 118.0 (2) |
N2—N3—C3A | 107.38 (18) | C15—C14—N14 | 118.70 (19) |
C7A—C3A—N3 | 109.11 (18) | O142—N14—O141 | 124.16 (19) |
C7A—C3A—C4 | 121.0 (2) | O142—N14—C14 | 117.47 (19) |
N3—C3A—C4 | 129.9 (2) | O141—N14—C14 | 118.36 (19) |
C5—C4—C3A | 116.6 (2) | C16—C15—C14 | 117.86 (19) |
C5—C4—H4 | 121.7 | C16—C15—H15 | 121.1 |
C3A—C4—H4 | 121.7 | C14—C15—H15 | 121.1 |
C4—C5—C6 | 121.98 (19) | C15—C16—C11 | 120.7 (2) |
C4—C5—H5 | 119.0 | C15—C16—H16 | 119.7 |
C6—C5—H5 | 119.0 | C11—C16—H16 | 119.7 |
C7—C6—C5 | 122.3 (2) | ||
C7A—N1—N2—N3 | −0.2 (2) | C4—C3A—C7A—C7 | −1.2 (3) |
C1—N1—N2—N3 | 177.64 (19) | C6—C7—C7A—N1 | 179.4 (2) |
N2—N1—C1—C2 | −24.6 (3) | C6—C7—C7A—C3A | 0.8 (3) |
C7A—N1—C1—C2 | 152.8 (2) | O3—C3—C11—C12 | 179.9 (2) |
N1—C1—C2—C3 | −173.63 (17) | C2—C3—C11—C12 | 2.3 (3) |
C1—C2—C3—O3 | 8.6 (3) | O3—C3—C11—C16 | −0.4 (3) |
C1—C2—C3—C11 | −173.89 (19) | C2—C3—C11—C16 | −177.93 (19) |
N1—N2—N3—C3A | 0.0 (2) | C16—C11—C12—C13 | −0.3 (3) |
N2—N3—C3A—C7A | 0.2 (3) | C3—C11—C12—C13 | 179.4 (2) |
N2—N3—C3A—C4 | −180.0 (2) | C11—C12—C13—C14 | 0.4 (3) |
C7A—C3A—C4—C5 | 0.7 (3) | C12—C13—C14—C15 | 0.2 (4) |
N3—C3A—C4—C5 | −179.1 (2) | C12—C13—C14—N14 | 179.70 (19) |
C3A—C4—C5—C6 | 0.1 (3) | C13—C14—N14—O142 | 17.8 (3) |
C4—C5—C6—C7 | −0.4 (4) | C15—C14—N14—O142 | −162.7 (2) |
C5—C6—C7—C7A | 0.0 (3) | C13—C14—N14—O141 | −162.2 (2) |
N2—N1—C7A—C3A | 0.3 (2) | C15—C14—N14—O141 | 17.4 (3) |
C1—N1—C7A—C3A | −177.3 (2) | C13—C14—C15—C16 | −0.9 (4) |
N2—N1—C7A—C7 | −178.5 (2) | N14—C14—C15—C16 | 179.60 (19) |
C1—N1—C7A—C7 | 3.9 (4) | C14—C15—C16—C11 | 1.0 (3) |
N3—C3A—C7A—N1 | −0.3 (2) | C12—C11—C16—C15 | −0.4 (3) |
C4—C3A—C7A—N1 | 179.8 (2) | C3—C11—C16—C15 | 179.8 (2) |
N3—C3A—C7A—C7 | 178.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O141i | 0.95 | 2.59 | 3.286 (3) | 131 |
C5—H5···O142ii | 0.95 | 2.58 | 3.264 (3) | 129 |
C4—H4···Cg2iii | 0.95 | 2.84 | 3.425 (2) | 121 |
C7—H7···Cg2iv | 0.95 | 2.83 | 3.464 (2) | 125 |
C13—H13···Cg1iii | 0.95 | 2.68 | 3.321 (2) | 125 |
C16—H16···Cg1iv | 0.95 | 2.83 | 3.516 (2) | 130 |
Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2. |
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