Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007542/na6221sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007542/na6221Isup2.hkl |
CCDC reference: 214600
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.056
- wR factor = 0.151
- Data-to-parameter ratio = 15.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) <H(6C)
Author response: ...The atoms are part of a disordered group and are in fact attached. |
PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) <H(6D)
Author response: ...The atoms are part of a disordered group and are in fact attached. |
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(8) - H(8) ?
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Glacial acetic acid (1 ml) was added to a solution of 4,5-diamino-3-methyl-1-phenylpyrazole (3.2 mmol) and 1-(1,3-benzodioxol-5-yl)-3-phenyl-2-propen-1-one (3.2 mmol) in 10 ml absolute ethanol and then refluxed for 6 h (reaction monitored by TLC). The resulting precipitate was filtered, washed with ethanol, dried and recrystallized from ethanol to afford crystals suitable for X-ray diffraction. 90% yield. Mp. 450, Anal. Calcd. for C26H22N4O2: C, 73.92; H, 5.25; N, 13.26. Found: C, 73.96; H, 5.19; N, 13.15.
Molecule (I) crystallized in the triclinic system; space group P-1 assumed and confirmed by the analysis. H atoms were treated as riding atoms, with C—H 0.95 to 1.00 Å, N—H 0.88 Å. Atom C6A of the minor component was fixed at 1.520 (2) Å from atoms C5 and C7 by means of the DFIX command. Atoms C6 and C6A were constrained to have the same anisotropic displacement parameters by use of the EADP command.
Data collection: Kappa-CCD 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: ORTEP (Johnson, 1976), PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
Fig. 1. A view of the major (top) and minor (bottom) components of (I), with our numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C26H22N4O2 | F(000) = 444 |
Mr = 422.48 | Dx = 1.379 Mg m−3 |
Triclinic, P1 | Melting point: 450 K |
a = 10.2608 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9910 (6) Å | Cell parameters from 4524 reflections |
c = 11.2485 (8) Å | θ = 3.0–27.4° |
α = 63.656 (4)° | µ = 0.09 mm−1 |
β = 63.573 (3)° | T = 120 K |
γ = 77.080 (5)° | Plate, orange |
V = 1017.49 (12) Å3 | 0.20 × 0.20 × 0.05 mm |
Z = 2 |
Kappa-CCD diffractometer | 4524 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2909 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
ϕ scans and ω scans with κ offsets | θmax = 27.4°, θmin = 3.0° |
Absorption correction: multi-scan DENZO–SMN (Otwinowski & Minor, 1997) | h = −13→13 |
Tmin = 0.982, Tmax = 0.996 | k = −13→14 |
13871 measured reflections | l = −14→14 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0677P)2 + 0.1359P] where P = (Fo2 + 2Fc2)/3 |
4524 reflections | (Δ/σ)max < 0.001 |
294 parameters | Δρmax = 0.52 e Å−3 |
2 restraints | Δρmin = −0.35 e Å−3 |
C26H22N4O2 | γ = 77.080 (5)° |
Mr = 422.48 | V = 1017.49 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.2608 (8) Å | Mo Kα radiation |
b = 10.9910 (6) Å | µ = 0.09 mm−1 |
c = 11.2485 (8) Å | T = 120 K |
α = 63.656 (4)° | 0.20 × 0.20 × 0.05 mm |
β = 63.573 (3)° |
Kappa-CCD diffractometer | 4524 independent reflections |
Absorption correction: multi-scan DENZO–SMN (Otwinowski & Minor, 1997) | 2909 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.996 | Rint = 0.094 |
13871 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 2 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.52 e Å−3 |
4524 reflections | Δρmin = −0.35 e Å−3 |
294 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.51087 (17) | 0.23431 (16) | 0.90014 (16) | 0.0294 (4) | |
C11 | 0.6064 (2) | 0.16187 (19) | 0.9717 (2) | 0.0291 (5) | |
C12 | 0.6770 (2) | 0.04204 (19) | 0.9611 (2) | 0.0316 (5) | |
C13 | 0.7669 (2) | −0.0258 (2) | 1.0345 (2) | 0.0359 (5) | |
C14 | 0.7838 (2) | 0.0222 (2) | 1.1202 (2) | 0.0391 (5) | |
C15 | 0.7110 (2) | 0.1409 (2) | 1.1322 (2) | 0.0401 (5) | |
C16 | 0.6230 (2) | 0.2118 (2) | 1.0574 (2) | 0.0346 (5) | |
N2 | 0.39136 (17) | 0.30282 (17) | 0.96710 (18) | 0.0346 (4) | |
C3 | 0.3252 (2) | 0.3606 (2) | 0.8773 (2) | 0.0332 (5) | |
C31 | 0.1895 (2) | 0.4450 (3) | 0.9127 (3) | 0.0478 (6) | |
C3A | 0.3972 (2) | 0.33116 (19) | 0.7528 (2) | 0.0279 (4) | |
N4 | 0.34511 (17) | 0.38207 (16) | 0.64429 (17) | 0.0298 (4) | |
C5 | 0.3889 (2) | 0.3398 (2) | 0.5430 (2) | 0.0328 (5) | |
C51 | 0.32212 (19) | 0.40531 (19) | 0.4356 (2) | 0.0290 (4) | |
C52 | 0.21902 (19) | 0.51283 (18) | 0.4483 (2) | 0.0274 (4) | |
C5A | 0.1560 (2) | 0.56986 (18) | 0.3512 (2) | 0.0273 (4) | |
O51 | 0.05687 (15) | 0.67723 (13) | 0.34120 (15) | 0.0372 (4) | |
C53 | 0.0234 (2) | 0.6973 (2) | 0.2232 (2) | 0.0353 (5) | |
O52 | 0.09884 (16) | 0.59358 (14) | 0.17073 (16) | 0.0422 (4) | |
C5B | 0.1836 (2) | 0.5229 (2) | 0.2479 (2) | 0.0314 (5) | |
C54 | 0.2832 (2) | 0.4202 (2) | 0.2307 (2) | 0.0398 (5) | |
C55 | 0.3525 (2) | 0.3631 (2) | 0.3270 (2) | 0.0368 (5) | |
C6 | 0.4934 (2) | 0.2180 (2) | 0.5394 (3) | 0.0332 (8) | 0.895 (7) |
C6A | 0.5512 (4) | 0.3338 (15) | 0.4533 (6) | 0.0332 (8) | 0.10 |
C7 | 0.6373 (2) | 0.2323 (2) | 0.5380 (2) | 0.0397 (5) | |
C71 | 0.7602 (2) | 0.1501 (2) | 0.4678 (2) | 0.0346 (5) | |
C72 | 0.7480 (2) | 0.0116 (2) | 0.5135 (2) | 0.0401 (5) | |
C73 | 0.8610 (2) | −0.0641 (2) | 0.4488 (2) | 0.0410 (5) | |
C74 | 0.9865 (2) | −0.0011 (2) | 0.3388 (2) | 0.0394 (5) | |
C75 | 1.0000 (2) | 0.1352 (2) | 0.2935 (2) | 0.0419 (5) | |
C76 | 0.8870 (2) | 0.2102 (2) | 0.3582 (2) | 0.0402 (5) | |
N8 | 0.62696 (17) | 0.19241 (15) | 0.68393 (16) | 0.0290 (4) | |
C8A | 0.5175 (2) | 0.25056 (18) | 0.7706 (2) | 0.0269 (4) | |
H12 | 0.6639 | 0.0067 | 0.9040 | 0.038* | |
H13 | 0.8177 | −0.1069 | 1.0253 | 0.043* | |
H14 | 0.8450 | −0.0258 | 1.1710 | 0.047* | |
H15 | 0.7216 | 0.1741 | 1.1922 | 0.048* | |
H16 | 0.5742 | 0.2941 | 1.0647 | 0.042* | |
H31A | 0.1561 | 0.4367 | 1.0122 | 0.072* | |
H31B | 0.1140 | 0.4137 | 0.9028 | 0.072* | |
H31C | 0.2091 | 0.5402 | 0.8464 | 0.072* | |
H52 | 0.1946 | 0.5442 | 0.5222 | 0.033* | |
H53A | 0.0544 | 0.7879 | 0.1454 | 0.042* | |
H53B | −0.0828 | 0.6922 | 0.2557 | 0.042* | |
H54 | 0.3044 | 0.3891 | 0.1574 | 0.048* | |
H55 | 0.4236 | 0.2922 | 0.3172 | 0.044* | |
H6A | 0.4542 | 0.1339 | 0.6256 | 0.040* | 0.895 (7) |
H6B | 0.5169 | 0.2029 | 0.4514 | 0.040* | 0.895 (7) |
H6C | 0.5718 | 0.3124 | 0.3698 | 0.040* | 0.105 (7) |
H6D | 0.5936 | 0.4232 | 0.4129 | 0.040* | 0.105 (7) |
H7 | 0.6629 | 0.3301 | 0.4823 | 0.048* | 0.895 (7) |
H7A | 0.7065 | 0.3045 | 0.5005 | 0.048* | 0.105 (7) |
H72 | 0.6613 | −0.0317 | 0.5900 | 0.048* | |
H73 | 0.8517 | −0.1587 | 0.4801 | 0.049* | |
H74 | 1.0643 | −0.0523 | 0.2939 | 0.047* | |
H75 | 1.0872 | 0.1782 | 0.2177 | 0.050* | |
H76 | 0.8971 | 0.3047 | 0.3264 | 0.048* | |
H8 | 0.7127 | 0.1821 | 0.6878 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0264 (9) | 0.0400 (9) | 0.0272 (8) | 0.0088 (7) | −0.0128 (7) | −0.0201 (8) |
C11 | 0.0242 (10) | 0.0378 (11) | 0.0239 (10) | 0.0031 (8) | −0.0102 (8) | −0.0123 (9) |
C12 | 0.0294 (11) | 0.0379 (11) | 0.0274 (10) | 0.0009 (8) | −0.0118 (8) | −0.0131 (9) |
C13 | 0.0327 (11) | 0.0364 (12) | 0.0325 (11) | 0.0054 (9) | −0.0142 (9) | −0.0102 (10) |
C14 | 0.0346 (12) | 0.0526 (13) | 0.0308 (11) | 0.0072 (10) | −0.0194 (9) | −0.0145 (10) |
C15 | 0.0363 (12) | 0.0586 (14) | 0.0329 (11) | 0.0045 (10) | −0.0175 (9) | −0.0232 (11) |
C16 | 0.0319 (11) | 0.0444 (12) | 0.0318 (11) | 0.0068 (9) | −0.0139 (9) | −0.0209 (10) |
N2 | 0.0300 (9) | 0.0486 (10) | 0.0346 (9) | 0.0152 (8) | −0.0164 (7) | −0.0282 (8) |
C3 | 0.0323 (11) | 0.0411 (12) | 0.0350 (11) | 0.0095 (9) | −0.0179 (9) | −0.0228 (10) |
C31 | 0.0451 (14) | 0.0672 (15) | 0.0476 (14) | 0.0278 (11) | −0.0274 (11) | −0.0409 (13) |
C3A | 0.0280 (10) | 0.0326 (10) | 0.0285 (10) | 0.0062 (8) | −0.0136 (8) | −0.0173 (9) |
N4 | 0.0269 (9) | 0.0375 (9) | 0.0302 (9) | 0.0063 (7) | −0.0142 (7) | −0.0182 (7) |
C5 | 0.0273 (11) | 0.0450 (12) | 0.0336 (11) | 0.0090 (9) | −0.0156 (9) | −0.0228 (10) |
C51 | 0.0235 (10) | 0.0382 (11) | 0.0285 (10) | 0.0038 (8) | −0.0111 (8) | −0.0172 (9) |
C52 | 0.0268 (10) | 0.0329 (10) | 0.0279 (10) | 0.0012 (8) | −0.0117 (8) | −0.0167 (9) |
C5A | 0.0243 (10) | 0.0267 (10) | 0.0304 (10) | 0.0024 (8) | −0.0104 (8) | −0.0127 (9) |
O51 | 0.0398 (8) | 0.0388 (8) | 0.0402 (8) | 0.0147 (6) | −0.0240 (7) | −0.0209 (7) |
C53 | 0.0329 (11) | 0.0401 (12) | 0.0356 (11) | 0.0083 (9) | −0.0183 (9) | −0.0166 (10) |
O52 | 0.0482 (9) | 0.0490 (9) | 0.0464 (9) | 0.0187 (7) | −0.0335 (7) | −0.0274 (8) |
C5B | 0.0319 (11) | 0.0371 (11) | 0.0317 (10) | 0.0048 (9) | −0.0188 (9) | −0.0156 (9) |
C54 | 0.0465 (13) | 0.0504 (13) | 0.0371 (12) | 0.0146 (10) | −0.0246 (10) | −0.0288 (10) |
C55 | 0.0368 (12) | 0.0454 (12) | 0.0362 (11) | 0.0164 (9) | −0.0199 (9) | −0.0256 (10) |
C6 | 0.0307 (13) | 0.0417 (14) | 0.0368 (14) | 0.0077 (10) | −0.0168 (10) | −0.0241 (11) |
C6A | 0.0307 (13) | 0.0417 (14) | 0.0368 (14) | 0.0077 (10) | −0.0168 (10) | −0.0241 (11) |
C7 | 0.0388 (12) | 0.0553 (13) | 0.0364 (12) | 0.0185 (10) | −0.0212 (10) | −0.0305 (11) |
C71 | 0.0387 (12) | 0.0436 (12) | 0.0329 (11) | 0.0166 (9) | −0.0235 (9) | −0.0236 (10) |
C72 | 0.0319 (12) | 0.0542 (14) | 0.0329 (11) | 0.0071 (10) | −0.0114 (9) | −0.0213 (11) |
C73 | 0.0417 (13) | 0.0427 (12) | 0.0454 (13) | 0.0125 (10) | −0.0225 (11) | −0.0243 (11) |
C74 | 0.0338 (12) | 0.0530 (14) | 0.0381 (12) | 0.0199 (10) | −0.0180 (9) | −0.0296 (11) |
C75 | 0.0356 (12) | 0.0517 (14) | 0.0397 (12) | 0.0087 (10) | −0.0151 (10) | −0.0237 (11) |
C76 | 0.0435 (13) | 0.0428 (12) | 0.0422 (12) | 0.0116 (10) | −0.0232 (10) | −0.0231 (11) |
N8 | 0.0234 (8) | 0.0415 (9) | 0.0272 (9) | 0.0092 (7) | −0.0127 (7) | −0.0198 (8) |
C8A | 0.0264 (10) | 0.0314 (10) | 0.0266 (10) | 0.0028 (8) | −0.0110 (8) | −0.0157 (8) |
N1—C8A | 1.359 (2) | C53—O52 | 1.429 (2) |
N1—N2 | 1.381 (2) | C53—H53A | 0.99 |
N1—C11 | 1.423 (2) | C53—H53B | 0.99 |
C11—C12 | 1.382 (3) | O52—C5B | 1.373 (2) |
C11—C16 | 1.384 (3) | C5B—C54 | 1.363 (3) |
C12—C13 | 1.383 (3) | C54—C55 | 1.398 (3) |
C12—H12 | 0.95 | C54—H54 | 0.95 |
C13—C14 | 1.371 (3) | C55—H55 | 0.95 |
C13—H13 | 0.95 | C6—C7 | 1.511 (3) |
C14—C15 | 1.381 (3) | C6—H6A | 0.99 |
C14—H14 | 0.95 | C6—H6B | 0.99 |
C15—C16 | 1.383 (3) | C6A—C7 | 1.516 (2) |
C15—H15 | 0.95 | C6A—H6B | 1.5664 |
C16—H16 | 0.95 | C6A—H6C | 0.99 |
N2—C3 | 1.316 (2) | C6A—H6D | 0.99 |
C3—C3A | 1.410 (3) | C6A—H7 | 1.3123 |
C3—C31 | 1.488 (3) | C7—N8 | 1.458 (2) |
C31—H31A | 0.98 | C7—C71 | 1.505 (3) |
C31—H31B | 0.98 | C7—H7 | 1.00 |
C31—H31C | 0.98 | C7—H7A | 1.00 |
C3A—C8A | 1.387 (3) | C71—C76 | 1.372 (3) |
C3A—N4 | 1.389 (2) | C71—C72 | 1.390 (3) |
N4—C5 | 1.280 (2) | C72—C73 | 1.386 (3) |
C5—C51 | 1.480 (3) | C72—H72 | 0.95 |
C5—C6A | 1.520 (2) | C73—C74 | 1.375 (3) |
C5—C6 | 1.521 (3) | C73—H73 | 0.95 |
C51—C55 | 1.379 (3) | C74—C75 | 1.370 (3) |
C51—C52 | 1.411 (3) | C74—H74 | 0.95 |
C52—C5A | 1.358 (3) | C75—C76 | 1.381 (3) |
C52—H52 | 0.95 | C75—H75 | 0.95 |
C5A—C5B | 1.368 (3) | C76—H76 | 0.95 |
C5A—O51 | 1.374 (2) | N8—C8A | 1.370 (2) |
O51—C53 | 1.428 (2) | N8—H8 | 0.88 |
C8A—N1—N2 | 111.69 (14) | C51—C55—C54 | 122.87 (18) |
C8A—N1—C11 | 130.40 (16) | C51—C55—H55 | 118.6 |
N2—N1—C11 | 117.90 (15) | C54—C55—H55 | 118.6 |
C12—C11—C16 | 120.35 (17) | C7—C6—C5 | 114.19 (19) |
C12—C11—N1 | 121.38 (18) | C7—C6—H6A | 103.9 |
C16—C11—N1 | 118.23 (17) | C5—C6—H6A | 112.5 |
C11—C12—C13 | 119.2 (2) | C7—C6—H6B | 106.3 |
C11—C12—H12 | 120.4 | C5—C6—H6B | 110.3 |
C13—C12—H12 | 120.4 | H6A—C6—H6B | 109.3 |
C14—C13—C12 | 120.99 (19) | C7—C6A—C5 | 114.0 (2) |
C14—C13—H13 | 119.5 | C7—C6A—H6B | 82.2 |
C12—C13—H13 | 119.5 | C5—C6A—H6B | 84.9 |
C13—C14—C15 | 119.45 (18) | C7—C6A—H6C | 107.8 |
C13—C14—H14 | 120.3 | C5—C6A—H6C | 112.1 |
C15—C14—H14 | 120.3 | H6B—C6A—H6C | 50.7 |
C14—C15—C16 | 120.5 (2) | C7—C6A—H6D | 106.0 |
C14—C15—H15 | 119.8 | C5—C6A—H6D | 110.2 |
C16—C15—H15 | 119.8 | H6B—C6A—H6D | 156.9 |
C15—C16—C11 | 119.45 (19) | H6C—C6A—H6D | 106.3 |
C15—C16—H16 | 120.3 | C7—C6A—H7 | 40.6 |
C11—C16—H16 | 120.3 | C5—C6A—H7 | 130.1 |
C3—N2—N1 | 104.67 (15) | H6B—C6A—H7 | 118.7 |
N2—C3—C3A | 112.27 (16) | H6C—C6A—H7 | 116.7 |
N2—C3—C31 | 120.55 (18) | H6D—C6A—H7 | 65.4 |
C3A—C3—C31 | 127.18 (18) | N8—C7—C71 | 108.09 (15) |
C3—C31—H31A | 109.5 | N8—C7—C6 | 111.23 (18) |
C3—C31—H31B | 109.5 | C71—C7—C6 | 113.35 (18) |
H31A—C31—H31B | 109.5 | N8—C7—C6A | 132.8 (5) |
C3—C31—H31C | 109.5 | C71—C7—C6A | 119.1 (5) |
H31A—C31—H31C | 109.5 | C6—C7—C6A | 50.1 (5) |
H31B—C31—H31C | 109.5 | N8—C7—H7 | 108.0 |
C8A—C3A—N4 | 133.61 (17) | C71—C7—H7 | 108.0 |
C8A—C3A—C3 | 104.84 (17) | C6—C7—H7 | 108.0 |
N4—C3A—C3 | 121.55 (16) | C6A—C7—H7 | 58.7 |
C5—N4—C3A | 124.19 (16) | N8—C7—H7A | 90.2 |
N4—C5—C51 | 117.32 (17) | C71—C7—H7A | 90.1 |
N4—C5—C6A | 119.0 (7) | C6—C7—H7A | 139.5 |
C51—C5—C6A | 104.6 (3) | C6A—C7—H7A | 90.0 |
N4—C5—C6 | 122.20 (18) | H7—C7—H7A | 31.5 |
C51—C5—C6 | 120.18 (18) | C76—C71—C72 | 118.61 (19) |
C6A—C5—C6 | 49.9 (5) | C76—C71—C7 | 120.7 (2) |
C55—C51—C52 | 118.71 (17) | C72—C71—C7 | 120.7 (2) |
C55—C51—C5 | 123.01 (17) | C73—C72—C71 | 120.7 (2) |
C52—C51—C5 | 118.25 (17) | C73—C72—H72 | 119.6 |
C5A—C52—C51 | 117.66 (17) | C71—C72—H72 | 119.6 |
C5A—C52—H52 | 121.2 | C74—C73—C72 | 119.4 (2) |
C51—C52—H52 | 121.2 | C74—C73—H73 | 120.3 |
C52—C5A—C5B | 122.59 (17) | C72—C73—H73 | 120.3 |
C52—C5A—O51 | 127.33 (18) | C75—C74—C73 | 120.4 (2) |
C5B—C5A—O51 | 110.08 (16) | C75—C74—H74 | 119.8 |
C5A—O51—C53 | 105.67 (14) | C73—C74—H74 | 119.8 |
O51—C53—O52 | 108.25 (15) | C74—C75—C76 | 120.0 (2) |
O51—C53—H53A | 110.0 | C74—C75—H75 | 120.0 |
O52—C53—H53A | 110.0 | C76—C75—H75 | 120.0 |
O51—C53—H53B | 110.0 | C71—C76—C75 | 120.9 (2) |
O52—C53—H53B | 110.0 | C71—C76—H76 | 119.5 |
H53A—C53—H53B | 108.4 | C75—C76—H76 | 119.5 |
C5B—O52—C53 | 105.54 (15) | C8A—N8—C7 | 118.18 (15) |
C54—C5B—C5A | 121.72 (17) | C8A—N8—H8 | 116.6 |
C54—C5B—O52 | 128.07 (18) | C7—N8—H8 | 112.7 |
C5A—C5B—O52 | 110.21 (16) | N1—C8A—N8 | 122.35 (16) |
C5B—C54—C55 | 116.35 (19) | N1—C8A—C3A | 106.52 (16) |
C5B—C54—H54 | 121.8 | N8—C8A—C3A | 131.12 (18) |
C55—C54—H54 | 121.8 | ||
C8A—N1—C11—C12 | −35.1 (3) | C5A—C5B—C54—C55 | 1.7 (3) |
N2—N1—C11—C12 | 146.04 (18) | O52—C5B—C54—C55 | −178.46 (19) |
C8A—N1—C11—C16 | 147.4 (2) | C52—C51—C55—C54 | −1.5 (3) |
N2—N1—C11—C16 | −31.5 (3) | C5—C51—C55—C54 | 176.3 (2) |
C16—C11—C12—C13 | −1.4 (3) | C5B—C54—C55—C51 | 0.9 (3) |
N1—C11—C12—C13 | −178.97 (17) | N4—C5—C6—C7 | −58.5 (3) |
C11—C12—C13—C14 | 1.7 (3) | C51—C5—C6—C7 | 127.9 (2) |
C12—C13—C14—C15 | −0.7 (3) | C6A—C5—C6—C7 | 44.2 (7) |
C13—C14—C15—C16 | −0.7 (3) | N4—C5—C6A—C7 | 65.3 (14) |
C14—C15—C16—C11 | 1.0 (3) | C51—C5—C6A—C7 | −161.3 (10) |
C12—C11—C16—C15 | 0.1 (3) | C6—C5—C6A—C7 | −43.9 (7) |
N1—C11—C16—C15 | 177.72 (18) | C5—C6—C7—N8 | 84.6 (2) |
C8A—N1—N2—C3 | 0.2 (2) | C5—C6—C7—C71 | −153.36 (18) |
C11—N1—N2—C3 | 179.26 (17) | C5—C6—C7—C6A | −44.1 (7) |
N1—N2—C3—C3A | 0.5 (2) | C5—C6A—C7—N8 | −38.4 (18) |
N1—N2—C3—C31 | −179.87 (19) | C5—C6A—C7—C71 | 141.3 (9) |
N2—C3—C3A—C8A | −1.0 (2) | C5—C6A—C7—C6 | 44.1 (7) |
C31—C3—C3A—C8A | 179.5 (2) | N8—C7—C71—C76 | −109.6 (2) |
N2—C3—C3A—N4 | 179.91 (18) | C6—C7—C71—C76 | 126.7 (2) |
C31—C3—C3A—N4 | 0.3 (3) | C6A—C7—C71—C76 | 70.7 (7) |
C8A—C3A—N4—C5 | 14.6 (3) | N8—C7—C71—C72 | 69.9 (2) |
C3—C3A—N4—C5 | −166.59 (19) | C6—C7—C71—C72 | −53.8 (3) |
C3A—N4—C5—C51 | −179.92 (17) | C6A—C7—C71—C72 | −109.8 (7) |
C3A—N4—C5—C6A | −52.3 (5) | C76—C71—C72—C73 | −0.7 (3) |
C3A—N4—C5—C6 | 6.3 (3) | C7—C71—C72—C73 | 179.84 (18) |
N4—C5—C51—C55 | −175.53 (19) | C71—C72—C73—C74 | 0.4 (3) |
C6A—C5—C51—C55 | 50.1 (8) | C72—C73—C74—C75 | 0.0 (3) |
C6—C5—C51—C55 | −1.6 (3) | C73—C74—C75—C76 | −0.2 (3) |
N4—C5—C51—C52 | 2.3 (3) | C72—C71—C76—C75 | 0.5 (3) |
C6A—C5—C51—C52 | −132.1 (8) | C7—C71—C76—C75 | 179.99 (18) |
C6—C5—C51—C52 | 176.22 (18) | C74—C75—C76—C71 | −0.1 (3) |
C55—C51—C52—C5A | −0.6 (3) | C71—C7—N8—C8A | −177.23 (17) |
C5—C51—C52—C5A | −178.47 (17) | C6—C7—N8—C8A | −52.2 (2) |
C51—C52—C5A—C5B | 3.2 (3) | C6A—C7—N8—C8A | 2.5 (9) |
C51—C52—C5A—O51 | −178.03 (17) | N2—N1—C8A—N8 | 179.77 (16) |
C52—C5A—O51—C53 | −179.47 (19) | C11—N1—C8A—N8 | 0.8 (3) |
C5B—C5A—O51—C53 | −0.6 (2) | N2—N1—C8A—C3A | −0.8 (2) |
C5A—O51—C53—O52 | 3.5 (2) | C11—N1—C8A—C3A | −179.71 (18) |
O51—C53—O52—C5B | −5.1 (2) | C7—N8—C8A—N1 | −170.78 (18) |
C52—C5A—C5B—C54 | −3.9 (3) | C7—N8—C8A—C3A | 9.9 (3) |
O51—C5A—C5B—C54 | 177.14 (19) | N4—C3A—C8A—N1 | 180.0 (2) |
C52—C5A—C5B—O52 | 176.24 (17) | C3—C3A—C8A—N1 | 1.0 (2) |
O51—C5A—C5B—O52 | −2.7 (2) | N4—C3A—C8A—N8 | −0.6 (4) |
C53—O52—C5B—C54 | −175.1 (2) | C3—C3A—C8A—N8 | −179.6 (2) |
C53—O52—C5B—C5A | 4.8 (2) |
Experimental details
Crystal data | |
Chemical formula | C26H22N4O2 |
Mr | 422.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 10.2608 (8), 10.9910 (6), 11.2485 (8) |
α, β, γ (°) | 63.656 (4), 63.573 (3), 77.080 (5) |
V (Å3) | 1017.49 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 0.20 × 0.05 |
Data collection | |
Diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO–SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.982, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13871, 4524, 2909 |
Rint | 0.094 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.151, 1.04 |
No. of reflections | 4524 |
No. of parameters | 294 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.35 |
Computer programs: Kappa-CCD Server Software (Nonius, 1997), DENZO–SMN (Otwinowski & Minor, 1997), DENZO–SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1976), PLATON (Spek, 2003), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
N1—C8A | 1.359 (2) | N4—C5 | 1.280 (2) |
N1—N2 | 1.381 (2) | C5—C6 | 1.521 (3) |
N2—C3 | 1.316 (2) | C6—C7 | 1.511 (3) |
C3—C3A | 1.410 (3) | C7—N8 | 1.458 (2) |
C3A—N4 | 1.389 (2) | N8—C8A | 1.370 (2) |
C8A—N1—N2 | 111.69 (14) | N4—C5—C6 | 122.20 (18) |
C3—N2—N1 | 104.67 (15) | C7—C6—C5 | 114.19 (19) |
N2—C3—C3A | 112.27 (16) | N8—C7—C6 | 111.23 (18) |
C8A—C3A—N4 | 133.61 (17) | C8A—N8—C7 | 118.18 (15) |
C8A—C3A—C3 | 104.84 (17) | N1—C8A—N8 | 122.35 (16) |
N4—C3A—C3 | 121.55 (16) | N1—C8A—C3A | 106.52 (16) |
C5—N4—C3A | 124.19 (16) | N8—C8A—C3A | 131.12 (18) |
C8A—N1—C11—C12 | −35.1 (3) | C6—C5—C51—C55 | −1.6 (3) |
N2—N1—C11—C12 | 146.04 (18) | N4—C5—C51—C52 | 2.3 (3) |
C8A—N1—C11—C16 | 147.4 (2) | N8—C7—C71—C76 | −109.6 (2) |
N2—N1—C11—C16 | −31.5 (3) | C6—C7—C71—C76 | 126.7 (2) |
N4—C5—C51—C55 | −175.53 (19) | N8—C7—C71—C72 | 69.9 (2) |
C6A—C5—C51—C55 | 50.1 (8) | C6—C7—C71—C72 | −53.8 (3) |
Benzodiazepines are an important class of psychotherapeutic compounds. In recent years, some examples of heterocyclic rings fused to the seven-member diazepine ring system have been reported (Kelly et al., 1997, and references therein). In particular, good CNS activity was reported for various pyrazolodiazepines (DeWald et al., 1981). Some of these compounds are known to have activities as psychotropics (Chimirri et al., 1993, and references therein).
The diazepine ring in the title compound, (I), is disordered, with atom C6 taking up two possible sites. The major component has a site occupancy of 0.895 (7). There are no unusual bonds or angles nor are there any intermolecular contacts less than van der Waals radii.