(E)-3,5-Dimethyl-1-p-tolyl-4-(p-tolyl-diazen-yl)-1H-pyrazole.

There are two independent mol-ecules, A and B, in the asymmetric unit of the title compound, C(19)H(20)N(4), in each of which the N=N double bond has an E conformation. The dihedral angles between the pyrazole ring and the p-tolyl rings in the 1- and 4-positions are 22.54 (8) and 35.73 (7)°, respectively, in mol-ecule A. The corresponding dihedral angles in mol-ecule B are 28.13 (8) and 22.18 (8)°. In the crystal, the A and B mol-ecules are linked by weak C-H⋯π inter-actions, leading to inversion dimers in each case.

Related literature

For related syntheses, see: Bustos et al. (2007 ▶, 2009 ▶). For the biological activity of compounds with pyrazole nuclei, see: Card et al. (2005 ▶); Daidone et al. (1998 ▶); Devi et al. (1983 ▶); Eid et al. (1978 ▶); El-Emary & Bakhite (1999 ▶); Elguero et al. (2002 ▶); Habit & Tawil (1981 ▶); Haufel & Breitmaier (1974 ▶); Menozzi et al. (1997 ▶); Pathak & Bahel (1980 ▶); Penning et al. (1997 ▶); Rathelot et al. (1995 ▶); Tedlaouti et al. (1990 ▶, 1991 ▶); Terrett et al. (1996 ▶); Wustrow et al. (1998 ▶). For related structures, see: Duprez & Heumann (2004 ▶); Rojas et al. (2004 ▶).

Experimental

Crystal data

C19H20N4

M = 304.39

Monoclinic,

a = 9.4320 (8) Å

b = 19.1552 (17) Å

c = 18.4511 (16) Å

β = 101.931 (1)°

V = 3261.6 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.37 × 0.20 × 0.15 mm

Data collection

Bruker D8 Discover with a SMART CCD area-detector diffractometer

25935 measured reflections

6641 independent reflections

4272 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.121

S = 0.90

6641 reflections

423 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-PC (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000360/lx2212sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000360/lx2212Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000360/lx2212Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H20N4	F(000) = 1296
Mr = 304.39	Dx = 1.240 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 999 reflections
a = 9.4320 (8) Å	θ = 2.1–26.3°
b = 19.1552 (17) Å	µ = 0.08 mm−1
c = 18.4511 (16) Å	T = 150 K
β = 101.931 (1)°	Block, yellow
V = 3261.6 (5) Å3	0.37 × 0.20 × 0.15 mm
Z = 8

Bruker D8 Discover with a SMART CCD area-detector diffractometer	4272 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 26.3°, θmin = 2.1°
Detector resolution: 10.0 pixels mm-1	h = −11→11
φ and ω scans	k = −23→23
25935 measured reflections	l = −23→23
6641 independent reflections

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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F2) = 0.121	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0649P)2] where P = (Fo2 + 2Fc2)/3
6641 reflections	(Δ/σ)max < 0.001
423 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.26 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
C1	0.62673 (19)	0.86483 (8)	0.38328 (9)	0.0404 (4)
H1A	0.7211	0.8655	0.4176	0.061*
H1B	0.5578	0.8934	0.4034	0.061*
H1C	0.6369	0.8837	0.3353	0.061*
C2	0.57203 (17)	0.79090 (8)	0.37339 (8)	0.0294 (4)
C3	0.42693 (17)	0.77661 (8)	0.34211 (9)	0.0309 (4)
H3	0.3614	0.8141	0.3276	0.037*
C4	0.37747 (17)	0.70868 (8)	0.33201 (9)	0.0302 (4)
H4	0.2787	0.6998	0.3103	0.036*
C5	0.47198 (16)	0.65319 (8)	0.35359 (8)	0.0257 (4)
C6	0.61738 (16)	0.66681 (8)	0.38429 (8)	0.0289 (4)
H6	0.6832	0.6293	0.3983	0.035*
C7	0.66515 (17)	0.73470 (8)	0.39426 (8)	0.0297 (4)
H7	0.7640	0.7434	0.4159	0.036*
C8	0.20938 (17)	0.48098 (8)	0.24859 (9)	0.0358 (4)
H8A	0.2579	0.5048	0.2134	0.054*
H8B	0.1594	0.5155	0.2736	0.054*
H8C	0.1387	0.4476	0.2219	0.054*
C9	0.31931 (16)	0.44308 (8)	0.30478 (8)	0.0277 (4)
C10	0.43929 (16)	0.46954 (8)	0.35718 (8)	0.0275 (4)
C11	0.50928 (17)	0.41225 (8)	0.39333 (9)	0.0280 (4)
C12	0.64728 (17)	0.40997 (8)	0.45042 (9)	0.0349 (4)
H12A	0.6249	0.4062	0.4998	0.052*
H12B	0.7027	0.4528	0.4475	0.052*
H12C	0.7046	0.3695	0.4413	0.052*
C13	0.5456 (2)	0.06412 (8)	0.41684 (10)	0.0429 (5)
H13A	0.6297	0.0582	0.4576	0.064*
H13B	0.5658	0.0426	0.3718	0.064*
H13C	0.4609	0.0416	0.4298	0.064*
C14	0.51564 (17)	0.14079 (8)	0.40347 (9)	0.0301 (4)
C15	0.54384 (16)	0.18874 (8)	0.46061 (9)	0.0294 (4)
H15	0.5840	0.1727	0.5093	0.035*
C16	0.51557 (16)	0.25916 (8)	0.44941 (8)	0.0285 (4)
H16	0.5337	0.2907	0.4900	0.034*
C17	0.46036 (15)	0.28334 (8)	0.37817 (8)	0.0255 (4)
C18	0.42990 (17)	0.23632 (8)	0.31976 (9)	0.0306 (4)
H18	0.3910	0.2525	0.2710	0.037*
C19	0.45630 (17)	0.16604 (8)	0.33258 (9)	0.0335 (4)
H19	0.4337	0.1342	0.2924	0.040*
C20	−0.0388 (2)	0.93105 (8)	0.58778 (10)	0.0443 (5)
H20A	−0.1275	0.9382	0.5502	0.066*
H20B	0.0436	0.9517	0.5707	0.066*
H20C	−0.0492	0.9533	0.6342	0.066*
C21	−0.01315 (18)	0.85406 (8)	0.60040 (9)	0.0310 (4)
C22	−0.12431 (17)	0.80610 (8)	0.58325 (9)	0.0313 (4)
H22	−0.2188	0.8221	0.5613	0.038*
C23	−0.10280 (16)	0.73558 (8)	0.59691 (9)	0.0293 (4)
H23	−0.1822	0.7041	0.5860	0.035*
C24	0.03503 (16)	0.71101 (8)	0.62659 (8)	0.0252 (3)
C25	0.14958 (16)	0.75778 (8)	0.64444 (8)	0.0293 (4)
H25	0.2444	0.7414	0.6650	0.035*
C26	0.12464 (17)	0.82825 (8)	0.63203 (9)	0.0330 (4)
H26	0.2030	0.8600	0.6453	0.040*
C27	−0.13084 (17)	0.58129 (8)	0.54119 (9)	0.0320 (4)
H27A	−0.2230	0.5878	0.5570	0.048*
H27B	−0.1322	0.5366	0.5152	0.048*
H27C	−0.1170	0.6194	0.5079	0.048*
C28	−0.00930 (16)	0.58146 (8)	0.60756 (8)	0.0267 (4)
C29	0.05751 (16)	0.52430 (8)	0.64582 (8)	0.0271 (4)
C30	0.17037 (16)	0.55115 (8)	0.70209 (9)	0.0296 (4)
C31	0.28088 (17)	0.51354 (9)	0.75777 (9)	0.0384 (4)
H31A	0.3512	0.5471	0.7844	0.058*
H31B	0.3310	0.4793	0.7325	0.058*
H31C	0.2331	0.4894	0.7930	0.058*
C32	−0.09013 (19)	0.12593 (8)	0.59920 (10)	0.0405 (4)
H32A	−0.0023	0.1010	0.5936	0.061*
H32B	−0.1624	0.1233	0.5527	0.061*
H32C	−0.1293	0.1045	0.6391	0.061*
C33	−0.05381 (16)	0.20119 (8)	0.61788 (9)	0.0295 (4)
C34	0.02167 (16)	0.22054 (8)	0.68803 (9)	0.0300 (4)
H34	0.0494	0.1858	0.7250	0.036*
C35	0.05680 (16)	0.28949 (8)	0.70455 (8)	0.0293 (4)
H35	0.1087	0.3017	0.7526	0.035*
C36	0.01679 (16)	0.34114 (8)	0.65136 (8)	0.0260 (4)
C37	−0.05932 (16)	0.32253 (8)	0.58129 (9)	0.0286 (4)
H37	−0.0880	0.3575	0.5446	0.034*
C38	−0.09334 (16)	0.25366 (8)	0.56474 (9)	0.0302 (4)
H38	−0.1445	0.2415	0.5165	0.036*
N1	0.41335 (14)	0.58491 (6)	0.33852 (7)	0.0294 (3)
N2	0.49150 (14)	0.53715 (7)	0.37309 (7)	0.0294 (3)
N3	0.31487 (13)	0.37412 (7)	0.30873 (7)	0.0302 (3)
N4	0.43238 (13)	0.35578 (7)	0.36404 (7)	0.0271 (3)
N5	0.06006 (13)	0.63840 (7)	0.64137 (7)	0.0273 (3)
N6	0.17222 (14)	0.62012 (7)	0.69907 (7)	0.0310 (3)
N7	0.01172 (13)	0.45662 (7)	0.62604 (7)	0.0297 (3)
N8	0.06300 (14)	0.41041 (6)	0.67314 (7)	0.0297 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0460 (11)	0.0336 (10)	0.0415 (11)	−0.0041 (8)	0.0091 (9)	0.0020 (8)
C2	0.0366 (9)	0.0282 (9)	0.0253 (9)	−0.0023 (7)	0.0103 (7)	−0.0010 (7)
C3	0.0339 (9)	0.0289 (9)	0.0299 (9)	0.0062 (7)	0.0068 (7)	0.0019 (7)
C4	0.0271 (8)	0.0341 (10)	0.0293 (9)	0.0008 (7)	0.0053 (7)	0.0004 (7)
C5	0.0300 (8)	0.0257 (9)	0.0221 (8)	−0.0015 (7)	0.0071 (7)	−0.0002 (7)
C6	0.0296 (9)	0.0305 (9)	0.0262 (9)	0.0022 (7)	0.0046 (7)	0.0006 (7)
C7	0.0286 (8)	0.0323 (9)	0.0279 (9)	−0.0017 (7)	0.0051 (7)	−0.0011 (7)
C8	0.0342 (9)	0.0347 (10)	0.0359 (10)	0.0009 (8)	0.0009 (8)	0.0022 (8)
C9	0.0283 (8)	0.0291 (9)	0.0266 (9)	−0.0001 (7)	0.0075 (7)	0.0002 (7)
C10	0.0287 (8)	0.0275 (9)	0.0272 (9)	−0.0016 (7)	0.0081 (7)	0.0002 (7)
C11	0.0283 (8)	0.0291 (9)	0.0268 (9)	−0.0033 (7)	0.0062 (7)	−0.0013 (7)
C12	0.0321 (9)	0.0356 (10)	0.0334 (10)	−0.0063 (7)	−0.0017 (8)	0.0007 (8)
C13	0.0526 (12)	0.0315 (10)	0.0438 (11)	0.0017 (9)	0.0084 (9)	0.0024 (8)
C14	0.0298 (8)	0.0279 (9)	0.0337 (10)	−0.0026 (7)	0.0088 (7)	−0.0003 (8)
C15	0.0289 (9)	0.0337 (10)	0.0251 (9)	0.0002 (7)	0.0043 (7)	0.0031 (7)
C16	0.0291 (8)	0.0314 (9)	0.0251 (9)	−0.0016 (7)	0.0059 (7)	−0.0033 (7)
C17	0.0216 (8)	0.0270 (9)	0.0284 (9)	−0.0012 (7)	0.0063 (7)	0.0005 (7)
C18	0.0334 (9)	0.0335 (10)	0.0245 (9)	−0.0035 (7)	0.0050 (7)	0.0016 (7)
C19	0.0406 (10)	0.0310 (10)	0.0297 (9)	−0.0067 (8)	0.0088 (8)	−0.0058 (8)
C20	0.0500 (12)	0.0304 (10)	0.0517 (12)	0.0022 (8)	0.0084 (10)	0.0011 (9)
C21	0.0407 (10)	0.0255 (9)	0.0280 (9)	0.0004 (8)	0.0095 (8)	−0.0002 (7)
C22	0.0304 (9)	0.0302 (9)	0.0325 (9)	0.0057 (7)	0.0049 (7)	0.0012 (7)
C23	0.0269 (8)	0.0284 (9)	0.0326 (9)	−0.0006 (7)	0.0057 (7)	0.0009 (7)
C24	0.0287 (8)	0.0237 (8)	0.0238 (8)	0.0018 (7)	0.0072 (7)	0.0001 (7)
C25	0.0266 (8)	0.0317 (9)	0.0287 (9)	−0.0004 (7)	0.0038 (7)	−0.0023 (7)
C26	0.0327 (9)	0.0293 (9)	0.0376 (10)	−0.0053 (7)	0.0083 (8)	−0.0024 (8)
C27	0.0327 (9)	0.0315 (9)	0.0300 (9)	−0.0036 (7)	0.0025 (7)	−0.0013 (7)
C28	0.0269 (8)	0.0265 (9)	0.0278 (9)	−0.0003 (7)	0.0077 (7)	−0.0008 (7)
C29	0.0287 (8)	0.0265 (9)	0.0269 (9)	0.0006 (7)	0.0073 (7)	−0.0003 (7)
C30	0.0307 (9)	0.0277 (9)	0.0305 (9)	0.0032 (7)	0.0066 (7)	−0.0006 (7)
C31	0.0383 (10)	0.0376 (10)	0.0358 (10)	0.0066 (8)	−0.0003 (8)	0.0017 (8)
C32	0.0454 (11)	0.0294 (10)	0.0439 (11)	−0.0024 (8)	0.0027 (9)	0.0003 (8)
C33	0.0266 (8)	0.0282 (9)	0.0344 (10)	0.0009 (7)	0.0080 (7)	0.0005 (7)
C34	0.0328 (9)	0.0282 (9)	0.0291 (9)	0.0034 (7)	0.0068 (7)	0.0052 (7)
C35	0.0310 (9)	0.0318 (9)	0.0249 (9)	0.0021 (7)	0.0049 (7)	0.0012 (7)
C36	0.0231 (8)	0.0258 (9)	0.0298 (9)	0.0006 (7)	0.0067 (7)	−0.0009 (7)
C37	0.0270 (8)	0.0294 (9)	0.0282 (9)	0.0000 (7)	0.0029 (7)	0.0047 (7)
C38	0.0291 (9)	0.0344 (10)	0.0258 (9)	−0.0011 (7)	0.0025 (7)	−0.0006 (7)
N1	0.0297 (7)	0.0274 (8)	0.0306 (8)	0.0009 (6)	0.0054 (6)	−0.0002 (6)
N2	0.0315 (7)	0.0290 (8)	0.0282 (8)	−0.0009 (6)	0.0071 (6)	−0.0003 (6)
N3	0.0287 (7)	0.0325 (8)	0.0277 (8)	0.0006 (6)	0.0019 (6)	0.0021 (6)
N4	0.0240 (7)	0.0283 (8)	0.0272 (7)	0.0000 (6)	0.0015 (6)	0.0011 (6)
N5	0.0262 (7)	0.0268 (7)	0.0275 (7)	0.0024 (6)	0.0021 (6)	0.0013 (6)
N6	0.0299 (7)	0.0307 (8)	0.0297 (8)	0.0030 (6)	0.0001 (6)	−0.0009 (6)
N7	0.0305 (7)	0.0282 (8)	0.0310 (8)	−0.0003 (6)	0.0077 (6)	0.0004 (6)
N8	0.0311 (7)	0.0257 (8)	0.0324 (8)	0.0018 (6)	0.0067 (6)	0.0012 (6)

C1—C2	1.505 (2)	C20—H20B	0.9800
C1—H1A	0.9800	C20—H20C	0.9800
C1—H1B	0.9800	C21—C22	1.381 (2)
C1—H1C	0.9800	C21—C26	1.400 (2)
C2—C7	1.392 (2)	C22—C23	1.381 (2)
C2—C3	1.398 (2)	C22—H22	0.9500
C3—C4	1.382 (2)	C23—C24	1.385 (2)
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.391 (2)	C24—C25	1.390 (2)
C4—H4	0.9500	C24—N5	1.4277 (18)
C5—C6	1.396 (2)	C25—C26	1.381 (2)
C5—N1	1.4250 (18)	C25—H25	0.9500
C6—C7	1.376 (2)	C26—H26	0.9500
C6—H6	0.9500	C27—C28	1.494 (2)
C7—H7	0.9500	C27—H27A	0.9800
C8—C9	1.494 (2)	C27—H27B	0.9800
C8—H8A	0.9800	C27—H27C	0.9800
C8—H8B	0.9800	C28—N5	1.3557 (18)
C8—H8C	0.9800	C28—C29	1.382 (2)
C9—N3	1.3241 (19)	C29—N7	1.3912 (18)
C9—C10	1.421 (2)	C29—C30	1.421 (2)
C10—C11	1.380 (2)	C30—N6	1.3226 (19)
C10—N2	1.3949 (18)	C30—C31	1.489 (2)
C11—N4	1.3513 (18)	C31—H31A	0.9800
C11—C12	1.496 (2)	C31—H31B	0.9800
C12—H12A	0.9800	C31—H31C	0.9800
C12—H12B	0.9800	C32—C33	1.505 (2)
C12—H12C	0.9800	C32—H32A	0.9800
C13—C14	1.506 (2)	C32—H32B	0.9800
C13—H13A	0.9800	C32—H32C	0.9800
C13—H13B	0.9800	C33—C34	1.392 (2)
C13—H13C	0.9800	C33—C38	1.400 (2)
C14—C15	1.382 (2)	C34—C35	1.380 (2)
C14—C19	1.398 (2)	C34—H34	0.9500
C15—C16	1.382 (2)	C35—C36	1.390 (2)
C15—H15	0.9500	C35—H35	0.9500
C16—C17	1.390 (2)	C36—C37	1.389 (2)
C16—H16	0.9500	C36—N8	1.4281 (18)
C17—C18	1.388 (2)	C37—C38	1.377 (2)
C17—N4	1.4265 (18)	C37—H37	0.9500
C18—C19	1.381 (2)	C38—H38	0.9500
C18—H18	0.9500	N1—N2	1.2620 (16)
C19—H19	0.9500	N3—N4	1.3877 (16)
C20—C21	1.505 (2)	N5—N6	1.3818 (16)
C20—H20A	0.9800	N7—N8	1.2646 (17)
C2—C1—H1A	109.5	C22—C21—C26	117.12 (14)
C2—C1—H1B	109.5	C22—C21—C20	121.78 (15)
H1A—C1—H1B	109.5	C26—C21—C20	121.08 (15)
C2—C1—H1C	109.5	C21—C22—C23	122.21 (15)
H1A—C1—H1C	109.5	C21—C22—H22	118.9
H1B—C1—H1C	109.5	C23—C22—H22	118.9
C7—C2—C3	118.06 (14)	C22—C23—C24	119.67 (15)
C7—C2—C1	120.87 (15)	C22—C23—H23	120.2
C3—C2—C1	121.06 (15)	C24—C23—H23	120.2
C4—C3—C2	120.96 (15)	C23—C24—C25	119.68 (14)
C4—C3—H3	119.5	C23—C24—N5	120.75 (13)
C2—C3—H3	119.5	C25—C24—N5	119.54 (13)
C3—C4—C5	120.15 (15)	C26—C25—C24	119.55 (15)
C3—C4—H4	119.9	C26—C25—H25	120.2
C5—C4—H4	119.9	C24—C25—H25	120.2
C4—C5—C6	119.40 (14)	C25—C26—C21	121.73 (15)
C4—C5—N1	116.46 (13)	C25—C26—H26	119.1
C6—C5—N1	124.04 (14)	C21—C26—H26	119.1
C7—C6—C5	119.86 (15)	C28—C27—H27A	109.5
C7—C6—H6	120.1	C28—C27—H27B	109.5
C5—C6—H6	120.1	H27A—C27—H27B	109.5
C6—C7—C2	121.55 (15)	C28—C27—H27C	109.5
C6—C7—H7	119.2	H27A—C27—H27C	109.5
C2—C7—H7	119.2	H27B—C27—H27C	109.5
C9—C8—H8A	109.5	N5—C28—C29	106.05 (14)
C9—C8—H8B	109.5	N5—C28—C27	126.45 (14)
H8A—C8—H8B	109.5	C29—C28—C27	127.48 (14)
C9—C8—H8C	109.5	C28—C29—N7	121.34 (14)
H8A—C8—H8C	109.5	C28—C29—C30	106.27 (13)
H8B—C8—H8C	109.5	N7—C29—C30	132.38 (14)
N3—C9—C10	110.37 (14)	N6—C30—C29	110.19 (14)
N3—C9—C8	119.84 (14)	N6—C30—C31	119.92 (14)
C10—C9—C8	129.75 (14)	C29—C30—C31	129.85 (15)
C11—C10—N2	121.59 (14)	C30—C31—H31A	109.5
C11—C10—C9	106.22 (13)	C30—C31—H31B	109.5
N2—C10—C9	132.15 (14)	H31A—C31—H31B	109.5
N4—C11—C10	106.25 (14)	C30—C31—H31C	109.5
N4—C11—C12	125.10 (14)	H31A—C31—H31C	109.5
C10—C11—C12	128.56 (14)	H31B—C31—H31C	109.5
C11—C12—H12A	109.5	C33—C32—H32A	109.5
C11—C12—H12B	109.5	C33—C32—H32B	109.5
H12A—C12—H12B	109.5	H32A—C32—H32B	109.5
C11—C12—H12C	109.5	C33—C32—H32C	109.5
H12A—C12—H12C	109.5	H32A—C32—H32C	109.5
H12B—C12—H12C	109.5	H32B—C32—H32C	109.5
C14—C13—H13A	109.5	C34—C33—C38	118.10 (14)
C14—C13—H13B	109.5	C34—C33—C32	121.09 (14)
H13A—C13—H13B	109.5	C38—C33—C32	120.81 (15)
C14—C13—H13C	109.5	C35—C34—C33	120.89 (15)
H13A—C13—H13C	109.5	C35—C34—H34	119.6
H13B—C13—H13C	109.5	C33—C34—H34	119.6
C15—C14—C19	117.42 (15)	C34—C35—C36	120.50 (15)
C15—C14—C13	121.53 (15)	C34—C35—H35	119.8
C19—C14—C13	121.04 (15)	C36—C35—H35	119.8
C14—C15—C16	122.26 (15)	C37—C36—C35	119.15 (14)
C14—C15—H15	118.9	C37—C36—N8	124.70 (14)
C16—C15—H15	118.9	C35—C36—N8	116.12 (14)
C15—C16—C17	119.32 (14)	C38—C37—C36	120.27 (15)
C15—C16—H16	120.3	C38—C37—H37	119.9
C17—C16—H16	120.3	C36—C37—H37	119.9
C18—C17—C16	119.68 (14)	C37—C38—C33	121.10 (15)
C18—C17—N4	119.24 (14)	C37—C38—H38	119.5
C16—C17—N4	121.08 (14)	C33—C38—H38	119.5
C19—C18—C17	119.90 (15)	N2—N1—C5	113.85 (13)
C19—C18—H18	120.0	N1—N2—C10	115.00 (13)
C17—C18—H18	120.0	C9—N3—N4	105.28 (12)
C18—C19—C14	121.37 (15)	C11—N4—N3	111.87 (12)
C18—C19—H19	119.3	C11—N4—C17	129.93 (13)
C14—C19—H19	119.3	N3—N4—C17	118.04 (12)
C21—C20—H20A	109.5	C28—N5—N6	111.74 (12)
C21—C20—H20B	109.5	C28—N5—C24	130.61 (13)
H20A—C20—H20B	109.5	N6—N5—C24	117.65 (12)
C21—C20—H20C	109.5	C30—N6—N5	105.72 (12)
H20A—C20—H20C	109.5	N8—N7—C29	114.72 (13)
H20B—C20—H20C	109.5	N7—N8—C36	113.94 (13)
C7—C2—C3—C4	−0.2 (2)	N7—C29—C30—C31	2.1 (3)
C1—C2—C3—C4	178.96 (14)	C38—C33—C34—C35	−0.2 (2)
C2—C3—C4—C5	0.5 (2)	C32—C33—C34—C35	178.94 (14)
C3—C4—C5—C6	−1.1 (2)	C33—C34—C35—C36	0.3 (2)
C3—C4—C5—N1	−177.62 (13)	C34—C35—C36—C37	0.1 (2)
C4—C5—C6—C7	1.3 (2)	C34—C35—C36—N8	−177.74 (13)
N1—C5—C6—C7	177.54 (13)	C35—C36—C37—C38	−0.6 (2)
C5—C6—C7—C2	−0.9 (2)	N8—C36—C37—C38	177.05 (14)
C3—C2—C7—C6	0.4 (2)	C36—C37—C38—C33	0.7 (2)
C1—C2—C7—C6	−178.76 (14)	C34—C33—C38—C37	−0.3 (2)
N3—C9—C10—C11	0.47 (17)	C32—C33—C38—C37	−179.43 (14)
C8—C9—C10—C11	−177.43 (15)	C4—C5—N1—N2	−165.00 (13)
N3—C9—C10—N2	178.31 (15)	C6—C5—N1—N2	18.6 (2)
C8—C9—C10—N2	0.4 (3)	C5—N1—N2—C10	−177.65 (12)
N2—C10—C11—N4	−178.96 (13)	C11—C10—N2—N1	−176.78 (14)
C9—C10—C11—N4	−0.84 (17)	C9—C10—N2—N1	5.6 (2)
N2—C10—C11—C12	−2.3 (3)	C10—C9—N3—N4	0.10 (16)
C9—C10—C11—C12	175.78 (15)	C8—C9—N3—N4	178.24 (13)
C19—C14—C15—C16	−0.1 (2)	C10—C11—N4—N3	0.96 (17)
C13—C14—C15—C16	−179.32 (14)	C12—C11—N4—N3	−175.82 (14)
C14—C15—C16—C17	−1.7 (2)	C10—C11—N4—C17	176.29 (13)
C15—C16—C17—C18	2.1 (2)	C12—C11—N4—C17	−0.5 (3)
C15—C16—C17—N4	−178.76 (13)	C9—N3—N4—C11	−0.66 (16)
C16—C17—C18—C19	−0.8 (2)	C9—N3—N4—C17	−176.61 (12)
N4—C17—C18—C19	−179.95 (13)	C18—C17—N4—C11	−141.55 (16)
C17—C18—C19—C14	−1.0 (2)	C16—C17—N4—C11	39.3 (2)
C15—C14—C19—C18	1.4 (2)	C18—C17—N4—N3	33.53 (19)
C13—C14—C19—C18	−179.32 (15)	C16—C17—N4—N3	−145.59 (14)
C26—C21—C22—C23	0.5 (2)	C29—C28—N5—N6	1.63 (17)
C20—C21—C22—C23	−177.80 (15)	C27—C28—N5—N6	−176.99 (14)
C21—C22—C23—C24	−2.1 (2)	C29—C28—N5—C24	−178.40 (13)
C22—C23—C24—C25	2.0 (2)	C27—C28—N5—C24	3.0 (3)
C22—C23—C24—N5	179.86 (13)	C23—C24—N5—C28	29.9 (2)
C23—C24—C25—C26	−0.3 (2)	C25—C24—N5—C28	−152.21 (15)
N5—C24—C25—C26	−178.23 (13)	C23—C24—N5—N6	−150.15 (14)
C24—C25—C26—C21	−1.3 (2)	C25—C24—N5—N6	27.76 (19)
C22—C21—C26—C25	1.2 (2)	C29—C30—N6—N5	0.50 (16)
C20—C21—C26—C25	179.52 (15)	C31—C30—N6—N5	178.53 (13)
N5—C28—C29—N7	179.31 (12)	C28—N5—N6—C30	−1.35 (16)
C27—C28—C29—N7	−2.1 (2)	C24—N5—N6—C30	178.68 (12)
N5—C28—C29—C30	−1.24 (17)	C28—C29—N7—N8	−167.46 (14)
C27—C28—C29—C30	177.37 (15)	C30—C29—N7—N8	13.3 (2)
C28—C29—C30—N6	0.46 (18)	C29—N7—N8—C36	−178.99 (12)
N7—C29—C30—N6	179.83 (15)	C37—C36—N8—N7	9.3 (2)
C28—C29—C30—C31	−177.31 (16)	C35—C36—N8—N7	−172.99 (13)

Cg1 and Cg2 are the centroids of the C33–C38 benzene ring and the N4/N3/C9–C11 pyrazole ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1i	0.95	2.76	3.4847 (18)	133
C27—H27A···Cg2ii	0.98	2.72	3.6322 (18)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C33–C38 benzene ring and the N4/N3/C9–C11 pyrazole ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1i	0.95	2.76	3.4847 (18)	133
C27—H27A⋯Cg2ii	0.98	2.72	3.6322 (18)	156

Symmetry codes: (i) ; (ii) .