Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006068/na6216sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006068/na6216Isup2.hkl |
CCDC reference: 209970
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.138
- Data-to-parameter ratio = 17.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
A mixture of 5-(4-dimethylaminophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole (2) (1.00 g, 3.77 mmol), 1-hydroxymethylbenzotriazole (3) (0.57 g, 3.83 mmol) and ethanol (5 ml) was heated to reflux for 30 min. After cooling, the white solid which formed was filtered off and washed with ethanol (90% yield; m.p. 449 K). 1H NMR (300 MHz, DMSO-d6, p.p.m.): 2.93 (1H, dd, J = 16.4, J = 14.4 Hz), 2.95 (3H, s), 3.30 (1H, dd, J = 16.4, J = 10.1 Hz), 4.14 (1H, dd, J = 14.5, J = 10.1 Hz), 5.58 (1H, d, J = 15.0 Hz), 6.33 (1H,, d, J = 15.0 Hz), 6.87 (2H, d, 8.5 Hz), 7.31–7.54 (6H, m), 7.56–7.60 (3H, m), 8.03 (2H, d, J = 8.3 Hz); 13C NMR (75 MHz, DMSO-d6, p.p.m.): 40.5, 41.4, 62.3, 65.1, 112.1, 112.9, 118.9, 124.0, 125.7, 127.2, 128.6, 128.8, 129.1, 132.1, 133.4, 145.2, 150.0, 151.1; MS (70 eV): m/e (%) 396 (12), 278 (74, M - Bt), 277 (100, M - BtH), 174 (58), 146 (41), 104 (32), 77 (57). Crystals suitable for single-crystal X-ray diffraction were grown from a solution in ethanol (96%).
The title compound crystallized in the monoclinic system; space group P21/c was assumed from the systematic absences. H atoms were treated as riding atoms with C—H distances in the range 0.95–1.00 Å.
Data collection: KappaCCD 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C24H24N6 | Dx = 1.249 Mg m−3 |
Mr = 396.49 | Melting point: C24 H24 N6 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8485 (2) Å | Cell parameters from 4800 reflections |
b = 14.4584 (4) Å | θ = 3.0–27.5° |
c = 14.0433 (4) Å | µ = 0.08 mm−1 |
β = 106.840 (1)° | T = 120 K |
V = 2108.26 (9) Å3 | Needle, colourless |
Z = 4 | 0.56 × 0.20 × 0.12 mm |
F(000) = 840 |
Nonius KappaCCD diffractometer | 4800 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3236 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 = −13→14 |
Tmin = 0.958, Tmax = 0.991 | k = −18→18 |
24082 measured reflections | l = −15→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.4464P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4800 reflections | Δρmax = 0.24 e Å−3 |
274 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.033 (2) |
C24H24N6 | V = 2108.26 (9) Å3 |
Mr = 396.49 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.8485 (2) Å | µ = 0.08 mm−1 |
b = 14.4584 (4) Å | T = 120 K |
c = 14.0433 (4) Å | 0.56 × 0.20 × 0.12 mm |
β = 106.840 (1)° |
Nonius KappaCCD diffractometer | 4800 independent reflections |
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997) | 3236 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.991 | Rint = 0.093 |
24082 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.24 e Å−3 |
4800 reflections | Δρmin = −0.20 e Å−3 |
274 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) 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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.66421 (13) | 0.14036 (10) | 0.53692 (10) | 0.0342 (3) | |
N2 | 0.65909 (15) | 0.10099 (11) | 0.44759 (11) | 0.0442 (4) | |
N3 | 0.75730 (15) | 0.12995 (12) | 0.41976 (12) | 0.0488 (4) | |
C3A | 0.82845 (17) | 0.18896 (13) | 0.49208 (14) | 0.0410 (4) | |
C4 | 0.9414 (2) | 0.23812 (14) | 0.49774 (18) | 0.0554 (6) | |
C5 | 0.9898 (2) | 0.29235 (16) | 0.5792 (2) | 0.0666 (7) | |
C6 | 0.9284 (2) | 0.29945 (15) | 0.65459 (19) | 0.0614 (6) | |
C7 | 0.81738 (19) | 0.25248 (13) | 0.65083 (15) | 0.0454 (5) | |
C7A | 0.76893 (15) | 0.19646 (11) | 0.56739 (12) | 0.0342 (4) | |
C1 | 0.56315 (16) | 0.12098 (11) | 0.58349 (13) | 0.0345 (4) | |
N11 | 0.50517 (13) | 0.27370 (9) | 0.61806 (10) | 0.0314 (3) | |
N12 | 0.46352 (12) | 0.19039 (9) | 0.56663 (9) | 0.0308 (3) | |
C13 | 0.39547 (15) | 0.21302 (11) | 0.46149 (11) | 0.0305 (4) | |
C31 | 0.29953 (15) | 0.14059 (11) | 0.41045 (12) | 0.0313 (4) | |
C32 | 0.30106 (16) | 0.10442 (12) | 0.31943 (12) | 0.0355 (4) | |
C33 | 0.20840 (16) | 0.04225 (13) | 0.26792 (13) | 0.0401 (4) | |
C34 | 0.10917 (16) | 0.01397 (12) | 0.30604 (13) | 0.0368 (4) | |
N34 | 0.01385 (16) | −0.04616 (12) | 0.25446 (13) | 0.0528 (4) | |
C342 | −0.0985 (2) | −0.06248 (17) | 0.28735 (19) | 0.0655 (6) | |
C341 | 0.0143 (2) | −0.07984 (19) | 0.15867 (18) | 0.0729 (7) | |
C35 | 0.10937 (16) | 0.04889 (12) | 0.39918 (13) | 0.0385 (4) | |
C36 | 0.20323 (15) | 0.11008 (12) | 0.44964 (12) | 0.0357 (4) | |
C14 | 0.34088 (16) | 0.30815 (12) | 0.47408 (12) | 0.0344 (4) | |
C15 | 0.43691 (15) | 0.34071 (11) | 0.56879 (11) | 0.0299 (4) | |
C51 | 0.44733 (15) | 0.43597 (11) | 0.60556 (12) | 0.0315 (4) | |
C52 | 0.54134 (17) | 0.46136 (12) | 0.69310 (13) | 0.0370 (4) | |
C53 | 0.54769 (19) | 0.55154 (13) | 0.72729 (15) | 0.0442 (5) | |
C54 | 0.4617 (2) | 0.61764 (13) | 0.67547 (15) | 0.0488 (5) | |
C55 | 0.3695 (2) | 0.59342 (13) | 0.58883 (15) | 0.0487 (5) | |
C56 | 0.36188 (18) | 0.50326 (12) | 0.55373 (14) | 0.0402 (4) | |
H4 | 0.9827 | 0.2338 | 0.4468 | 0.066* | |
H5 | 1.0667 | 0.3262 | 0.5853 | 0.080* | |
H6 | 0.9654 | 0.3382 | 0.7101 | 0.074* | |
H7 | 0.7761 | 0.2577 | 0.7017 | 0.054* | |
H1A | 0.5229 | 0.0610 | 0.5582 | 0.041* | |
H1B | 0.6031 | 0.1145 | 0.6561 | 0.041* | |
H13 | 0.4606 | 0.2204 | 0.4242 | 0.037* | |
H32 | 0.3673 | 0.1227 | 0.2916 | 0.043* | |
H33 | 0.2125 | 0.0186 | 0.2058 | 0.048* | |
H34A | −0.0721 | −0.0895 | 0.3542 | 0.098* | |
H34B | −0.1565 | −0.1052 | 0.2413 | 0.098* | |
H34C | −0.1430 | −0.0038 | 0.2889 | 0.098* | |
H34D | −0.0063 | −0.0291 | 0.1104 | 0.109* | |
H34E | −0.0503 | −0.1289 | 0.1376 | 0.109* | |
H34F | 0.0996 | −0.1046 | 0.1625 | 0.109* | |
H35 | 0.0441 | 0.0302 | 0.4279 | 0.046* | |
H36 | 0.2018 | 0.1320 | 0.5131 | 0.043* | |
H14A | 0.3392 | 0.3494 | 0.4175 | 0.041* | |
H14B | 0.2531 | 0.3035 | 0.4816 | 0.041* | |
H52 | 0.6009 | 0.4166 | 0.7291 | 0.044* | |
H53 | 0.6116 | 0.5683 | 0.7868 | 0.053* | |
H54 | 0.4663 | 0.6793 | 0.6995 | 0.059* | |
H55 | 0.3107 | 0.6387 | 0.5529 | 0.058* | |
H56 | 0.2980 | 0.4873 | 0.4939 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0317 (8) | 0.0347 (8) | 0.0328 (8) | 0.0078 (6) | 0.0041 (6) | −0.0037 (6) |
N2 | 0.0370 (9) | 0.0520 (10) | 0.0413 (9) | 0.0112 (7) | 0.0076 (7) | −0.0117 (7) |
N3 | 0.0443 (10) | 0.0578 (11) | 0.0439 (9) | 0.0144 (8) | 0.0122 (8) | −0.0033 (8) |
C3A | 0.0378 (10) | 0.0391 (10) | 0.0460 (10) | 0.0131 (8) | 0.0119 (8) | 0.0052 (8) |
C4 | 0.0506 (13) | 0.0481 (12) | 0.0758 (15) | 0.0099 (10) | 0.0315 (11) | 0.0104 (11) |
C5 | 0.0496 (13) | 0.0513 (13) | 0.104 (2) | −0.0075 (10) | 0.0312 (13) | −0.0006 (14) |
C6 | 0.0509 (13) | 0.0491 (13) | 0.0801 (16) | −0.0097 (10) | 0.0123 (11) | −0.0158 (11) |
C7 | 0.0434 (11) | 0.0412 (11) | 0.0491 (11) | −0.0017 (8) | 0.0097 (9) | −0.0074 (9) |
C7A | 0.0300 (9) | 0.0300 (9) | 0.0396 (9) | 0.0069 (7) | 0.0053 (7) | 0.0027 (7) |
C1 | 0.0337 (9) | 0.0293 (9) | 0.0384 (9) | 0.0048 (7) | 0.0071 (7) | 0.0014 (7) |
N11 | 0.0349 (8) | 0.0289 (7) | 0.0306 (7) | 0.0015 (6) | 0.0100 (6) | 0.0000 (6) |
N12 | 0.0316 (7) | 0.0278 (7) | 0.0308 (7) | 0.0032 (5) | 0.0056 (6) | 0.0002 (6) |
C13 | 0.0277 (8) | 0.0349 (9) | 0.0280 (8) | 0.0025 (7) | 0.0067 (7) | 0.0023 (7) |
C31 | 0.0265 (8) | 0.0349 (9) | 0.0308 (9) | 0.0065 (7) | 0.0057 (7) | 0.0015 (7) |
C32 | 0.0294 (9) | 0.0432 (10) | 0.0343 (9) | 0.0050 (7) | 0.0098 (7) | −0.0021 (8) |
C33 | 0.0353 (10) | 0.0465 (11) | 0.0358 (9) | 0.0072 (8) | 0.0060 (8) | −0.0073 (8) |
C34 | 0.0283 (9) | 0.0349 (9) | 0.0412 (10) | 0.0056 (7) | 0.0008 (7) | −0.0027 (8) |
N34 | 0.0397 (9) | 0.0578 (11) | 0.0546 (10) | −0.0073 (8) | 0.0037 (8) | −0.0182 (8) |
C342 | 0.0459 (13) | 0.0680 (15) | 0.0779 (16) | −0.0188 (11) | 0.0107 (11) | −0.0116 (12) |
C341 | 0.0558 (15) | 0.0844 (18) | 0.0699 (16) | −0.0084 (12) | 0.0047 (12) | −0.0370 (14) |
C35 | 0.0318 (9) | 0.0426 (10) | 0.0407 (10) | −0.0006 (7) | 0.0098 (8) | 0.0011 (8) |
C36 | 0.0333 (9) | 0.0424 (10) | 0.0320 (9) | 0.0004 (7) | 0.0102 (7) | −0.0021 (7) |
C14 | 0.0320 (9) | 0.0350 (10) | 0.0345 (9) | 0.0052 (7) | 0.0069 (7) | 0.0036 (7) |
C15 | 0.0287 (9) | 0.0326 (9) | 0.0300 (8) | 0.0027 (7) | 0.0108 (7) | 0.0044 (7) |
C51 | 0.0337 (9) | 0.0314 (9) | 0.0339 (9) | 0.0029 (7) | 0.0169 (7) | 0.0024 (7) |
C52 | 0.0373 (10) | 0.0376 (10) | 0.0396 (10) | −0.0002 (7) | 0.0169 (8) | 0.0007 (8) |
C53 | 0.0488 (11) | 0.0411 (11) | 0.0491 (11) | −0.0080 (8) | 0.0245 (9) | −0.0091 (9) |
C54 | 0.0713 (14) | 0.0301 (10) | 0.0588 (13) | −0.0033 (9) | 0.0405 (11) | −0.0025 (9) |
C55 | 0.0670 (14) | 0.0318 (10) | 0.0566 (13) | 0.0128 (9) | 0.0323 (11) | 0.0109 (9) |
C56 | 0.0465 (11) | 0.0367 (10) | 0.0403 (10) | 0.0077 (8) | 0.0174 (8) | 0.0056 (8) |
N1—C7A | 1.360 (2) | C33—H33 | 0.95 |
N1—N2 | 1.3639 (19) | C34—N34 | 1.384 (2) |
N1—C1 | 1.457 (2) | C34—C35 | 1.401 (2) |
N2—N3 | 1.306 (2) | N34—C341 | 1.432 (3) |
N3—C3A | 1.379 (2) | N34—C342 | 1.442 (3) |
C3A—C7A | 1.394 (2) | C342—H34A | 0.98 |
C3A—C4 | 1.399 (3) | C342—H34B | 0.98 |
C4—C5 | 1.360 (3) | C342—H34C | 0.98 |
C4—H4 | 0.95 | C341—H34D | 0.98 |
C5—C6 | 1.408 (3) | C341—H34E | 0.98 |
C5—H5 | 0.95 | C341—H34F | 0.98 |
C6—C7 | 1.371 (3) | C35—C36 | 1.380 (2) |
C6—H6 | 0.95 | C35—H35 | 0.95 |
C7—C7A | 1.396 (3) | C36—H36 | 0.95 |
C7—H7 | 0.95 | C14—C15 | 1.508 (2) |
C1—N12 | 1.443 (2) | C14—H14A | 0.99 |
C1—H1A | 0.99 | C14—H14B | 0.99 |
C1—H1B | 0.99 | C15—C51 | 1.464 (2) |
N11—C15 | 1.292 (2) | C51—C56 | 1.395 (2) |
N11—N12 | 1.4098 (18) | C51—C52 | 1.400 (2) |
N12—C13 | 1.483 (2) | C52—C53 | 1.384 (2) |
C13—C31 | 1.504 (2) | C52—H52 | 0.95 |
C13—C14 | 1.528 (2) | C53—C54 | 1.386 (3) |
C13—H13 | 1.00 | C53—H53 | 0.95 |
C31—C32 | 1.386 (2) | C54—C55 | 1.378 (3) |
C31—C36 | 1.386 (2) | C54—H54 | 0.95 |
C32—C33 | 1.386 (2) | C55—C56 | 1.388 (3) |
C32—H32 | 0.95 | C55—H55 | 0.95 |
C33—C34 | 1.395 (3) | C56—H56 | 0.95 |
C7A—N1—N2 | 110.24 (14) | C33—C34—C35 | 117.38 (16) |
C7A—N1—C1 | 129.93 (14) | C34—N34—C341 | 120.01 (18) |
N2—N1—C1 | 119.81 (14) | C34—N34—C342 | 120.50 (17) |
N3—N2—N1 | 108.79 (15) | C341—N34—C342 | 118.56 (17) |
N2—N3—C3A | 108.01 (15) | N34—C342—H34A | 109.5 |
N3—C3A—C7A | 108.88 (16) | N34—C342—H34B | 109.5 |
N3—C3A—C4 | 130.58 (18) | H34A—C342—H34B | 109.5 |
C7A—C3A—C4 | 120.54 (18) | N34—C342—H34C | 109.5 |
C5—C4—C3A | 117.3 (2) | H34A—C342—H34C | 109.5 |
C5—C4—H4 | 121.3 | H34B—C342—H34C | 109.5 |
C3A—C4—H4 | 121.3 | N34—C341—H34D | 109.5 |
C4—C5—C6 | 121.6 (2) | N34—C341—H34E | 109.5 |
C4—C5—H5 | 119.2 | H34D—C341—H34E | 109.5 |
C6—C5—H5 | 119.2 | N34—C341—H34F | 109.5 |
C7—C6—C5 | 122.4 (2) | H34D—C341—H34F | 109.5 |
C7—C6—H6 | 118.8 | H34E—C341—H34F | 109.5 |
C5—C6—H6 | 118.8 | C36—C35—C34 | 120.78 (16) |
C6—C7—C7A | 115.65 (19) | C36—C35—H35 | 119.6 |
C6—C7—H7 | 122.2 | C34—C35—H35 | 119.6 |
C7A—C7—H7 | 122.2 | C35—C36—C31 | 121.94 (16) |
N1—C7A—C3A | 104.08 (15) | C35—C36—H36 | 119.0 |
N1—C7A—C7 | 133.41 (16) | C31—C36—H36 | 119.0 |
C3A—C7A—C7 | 122.52 (17) | C15—C14—C13 | 101.03 (13) |
N12—C1—N1 | 114.69 (13) | C15—C14—H14A | 111.6 |
N12—C1—H1A | 108.6 | C13—C14—H14A | 111.6 |
N1—C1—H1A | 108.6 | C15—C14—H14B | 111.6 |
N12—C1—H1B | 108.6 | C13—C14—H14B | 111.6 |
N1—C1—H1B | 108.6 | H14A—C14—H14B | 109.4 |
H1A—C1—H1B | 107.6 | N11—C15—C51 | 122.89 (15) |
C15—N11—N12 | 108.51 (13) | N11—C15—C14 | 112.38 (14) |
N11—N12—C1 | 113.35 (12) | C51—C15—C14 | 124.61 (14) |
N11—N12—C13 | 108.34 (12) | C56—C51—C52 | 118.70 (16) |
C1—N12—C13 | 116.73 (13) | C56—C51—C15 | 120.05 (15) |
N12—C13—C31 | 113.39 (13) | C52—C51—C15 | 121.25 (15) |
N12—C13—C14 | 100.44 (12) | C53—C52—C51 | 120.13 (17) |
C31—C13—C14 | 116.37 (13) | C53—C52—H52 | 119.9 |
N12—C13—H13 | 108.7 | C51—C52—H52 | 119.9 |
C31—C13—H13 | 108.7 | C52—C53—C54 | 120.61 (18) |
C14—C13—H13 | 108.7 | C52—C53—H53 | 119.7 |
C32—C31—C36 | 117.25 (16) | C54—C53—H53 | 119.7 |
C32—C31—C13 | 120.73 (15) | C55—C54—C53 | 119.65 (17) |
C36—C31—C13 | 121.96 (14) | C55—C54—H54 | 120.2 |
C31—C32—C33 | 121.72 (16) | C53—C54—H54 | 120.2 |
C31—C32—H32 | 119.1 | C54—C55—C56 | 120.36 (18) |
C33—C32—H32 | 119.1 | C54—C55—H55 | 119.8 |
C32—C33—C34 | 120.89 (16) | C56—C55—H55 | 119.8 |
C32—C33—H33 | 119.6 | C55—C56—C51 | 120.53 (18) |
C34—C33—H33 | 119.6 | C55—C56—H56 | 119.7 |
N34—C34—C33 | 121.72 (16) | C51—C56—H56 | 119.7 |
N34—C34—C35 | 120.91 (16) | ||
C7A—N1—N2—N3 | 0.08 (18) | C14—C13—C31—C36 | −62.0 (2) |
C1—N1—N2—N3 | 178.51 (14) | C36—C31—C32—C33 | 1.8 (2) |
N1—N2—N3—C3A | 0.26 (19) | C13—C31—C32—C33 | −175.62 (15) |
N2—N3—C3A—C7A | −0.5 (2) | C31—C32—C33—C34 | 0.3 (3) |
N2—N3—C3A—C4 | −179.78 (19) | C32—C33—C34—N34 | 178.27 (16) |
N3—C3A—C4—C5 | 179.49 (19) | C32—C33—C34—C35 | −1.7 (3) |
C7A—C3A—C4—C5 | 0.3 (3) | C33—C34—N34—C341 | −1.0 (3) |
C3A—C4—C5—C6 | −0.4 (3) | C35—C34—N34—C341 | 178.98 (19) |
C4—C5—C6—C7 | 0.1 (4) | C33—C34—N34—C342 | −169.84 (19) |
C5—C6—C7—C7A | 0.3 (3) | C35—C34—N34—C342 | 10.2 (3) |
N2—N1—C7A—C3A | −0.37 (17) | N34—C34—C35—C36 | −178.86 (16) |
C1—N1—C7A—C3A | −178.60 (15) | C33—C34—C35—C36 | 1.1 (2) |
N2—N1—C7A—C7 | 179.27 (18) | C34—C35—C36—C31 | 0.9 (3) |
C1—N1—C7A—C7 | 1.0 (3) | C32—C31—C36—C35 | −2.4 (2) |
N3—C3A—C7A—N1 | 0.52 (18) | C13—C31—C36—C35 | 174.98 (15) |
C4—C3A—C7A—N1 | 179.89 (16) | N12—C13—C14—C15 | 26.84 (15) |
N3—C3A—C7A—C7 | −179.17 (16) | C31—C13—C14—C15 | 149.66 (13) |
C4—C3A—C7A—C7 | 0.2 (3) | N12—N11—C15—C51 | 174.64 (13) |
C6—C7—C7A—N1 | 179.92 (19) | N12—N11—C15—C14 | −1.52 (17) |
C6—C7—C7A—C3A | −0.5 (3) | C13—C14—C15—N11 | −17.16 (17) |
C7A—N1—C1—N12 | 80.6 (2) | C13—C14—C15—C51 | 166.75 (14) |
N2—N1—C1—N12 | −97.47 (17) | N11—C15—C51—C56 | −173.43 (15) |
C15—N11—N12—C1 | 152.10 (13) | C14—C15—C51—C56 | 2.3 (2) |
C15—N11—N12—C13 | 20.85 (16) | N11—C15—C51—C52 | 5.9 (2) |
N1—C1—N12—N11 | −71.05 (17) | C14—C15—C51—C52 | −178.39 (15) |
N1—C1—N12—C13 | 55.92 (19) | C56—C51—C52—C53 | 0.6 (2) |
N11—N12—C13—C31 | −154.93 (12) | C15—C51—C52—C53 | −178.80 (15) |
C1—N12—C13—C31 | 75.69 (17) | C51—C52—C53—C54 | −0.2 (3) |
N11—N12—C13—C14 | −30.05 (15) | C52—C53—C54—C55 | −0.3 (3) |
C1—N12—C13—C14 | −159.44 (13) | C53—C54—C55—C56 | 0.4 (3) |
N12—C13—C31—C32 | −129.01 (15) | C54—C55—C56—C51 | 0.0 (3) |
C14—C13—C31—C32 | 115.22 (17) | C52—C51—C56—C55 | −0.5 (2) |
N12—C13—C31—C36 | 53.7 (2) | C15—C51—C56—C55 | 178.88 (15) |
Experimental details
Crystal data | |
Chemical formula | C24H24N6 |
Mr | 396.49 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 10.8485 (2), 14.4584 (4), 14.0433 (4) |
β (°) | 106.840 (1) |
V (Å3) | 2108.26 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.56 × 0.20 × 0.12 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO–SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.958, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24082, 4800, 3236 |
Rint | 0.093 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.138, 1.03 |
No. of reflections | 4800 |
No. of parameters | 274 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.20 |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO–SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2003), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
N1—C7A | 1.360 (2) | C6—C7 | 1.371 (3) |
N1—N2 | 1.3639 (19) | C7—C7A | 1.396 (3) |
N1—C1 | 1.457 (2) | C1—N12 | 1.443 (2) |
N2—N3 | 1.306 (2) | N11—C15 | 1.292 (2) |
N3—C3A | 1.379 (2) | N11—N12 | 1.4098 (18) |
C3A—C7A | 1.394 (2) | N12—C13 | 1.483 (2) |
C3A—C4 | 1.399 (3) | C13—C14 | 1.528 (2) |
C4—C5 | 1.360 (3) | C14—C15 | 1.508 (2) |
C5—C6 | 1.408 (3) | ||
C7A—N1—N2 | 110.24 (14) | N1—C7A—C3A | 104.08 (15) |
C7A—N1—C1 | 129.93 (14) | N1—C7A—C7 | 133.41 (16) |
N2—N1—C1 | 119.81 (14) | C3A—C7A—C7 | 122.52 (17) |
N3—N2—N1 | 108.79 (15) | N12—C1—N1 | 114.69 (13) |
N2—N3—C3A | 108.01 (15) | C15—N11—N12 | 108.51 (13) |
N3—C3A—C7A | 108.88 (16) | N11—N12—C1 | 113.35 (12) |
N3—C3A—C4 | 130.58 (18) | N11—N12—C13 | 108.34 (12) |
C7A—C3A—C4 | 120.54 (18) | C1—N12—C13 | 116.73 (13) |
C5—C4—C3A | 117.3 (2) | N12—C13—C14 | 100.44 (12) |
C4—C5—C6 | 121.6 (2) | C15—C14—C13 | 101.03 (13) |
C7—C6—C5 | 122.4 (2) | N11—C15—C14 | 112.38 (14) |
C6—C7—C7A | 115.65 (19) | ||
C7A—N1—C1—N12 | 80.6 (2) | N1—C1—N12—N11 | −71.05 (17) |
N2—N1—C1—N12 | −97.47 (17) | N1—C1—N12—C13 | 55.92 (19) |
The title compound, (I), was prepared to be used as an intermediate in the preparation of new heterocycles containing pyrazoline and benzazepine rings, following the benzotriazole methodology (see Scheme below) (Abonia et al., 2001; Colotta et al., 1996; Burckhalter et al., 1952).
There are no unusual bonds or angles in (I) nor are there any intermolecular contacts less than 3.5 Å. The molecule has the R conformation at the chiral centre C13 (Fig. 1).