1-(Benzotriazol-1-yl­methyl)-5-(4-di­methyl­amino­phenyl)-3-phenyl-4,5-di­hydro-1H-pyrazole

Low, J.N.; Cobo, J.; Arroyabe, F.; Torres, H.; Abonia, R.; Nogueras, M.

doi:10.1107/S1600536803006068

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1-(Benzotriazol-1-ylmethyl)-5-(4-dimethylaminophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole

J. N. Low, J. Cobo, F. Arroyabe, H. Torres, R. Abonia and M. Nogueras

The title compound, C₂₄H₂₄N₆, shows no unusual features. There is no hydrogen bonding or π–π stacking.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006068/na6216sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006068/na6216Isup2.hkl Contains datablock I

CCDC reference: 209970

checkCIF report

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

Comment top

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).

Experimental top

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%).

Computing details top

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).

Figures top

Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

1-(Benzotriazol-1-ylmethyl)-5-(4-dimethylaminophenyl)-3- phenyl-4,5-dihydro-1H-pyrazole top

Crystal data top

C₂₄H₂₄N₆	D_x = 1.249 Mg m⁻³
M_r = 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

Data collection top

Nonius KappaCCD diffractometer	4800 independent reflections
Radiation source: fine-focus sealed X-ray tube	3236 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ϕ scans and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997)	h = −13→14
T_min = 0.958, T_max = 0.991	k = −18→18
24082 measured reflections	l = −15→18

Refinement top

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(F_o²) + (0.0573P)² + 0.4464P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4800 reflections	Δρ_max = 0.24 e Å⁻³
274 parameters	Δρ_min = −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)

Crystal data top

C₂₄H₂₄N₆	V = 2108.26 (9) Å³
M_r = 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)°

Data collection top

Nonius KappaCCD diffractometer	4800 independent reflections
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997)	3236 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.991	R_int = 0.093
24082 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
4800 reflections	Δρ_min = −0.20 e Å⁻³
274 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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)
T_min, T_max	0.958, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	24082, 4800, 3236
R_int	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
Δρ_max, Δρ_min (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).

Selected geometric parameters (Å, º) top

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)

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