N'-Phenyl-N'-[3-(2,4,5-triphenyl-2,5-di-hydro-1H-pyrazol-3-yl)quinoxalin-2-yl]benzohydrazide.

The mol-ecule of the title compound, C42H32N6O, is built up from one pyrazole ring linked to three phenyl rings and to an approximately planar [maximum deviation = 0.0455 (15) Å] quinoxaline system connected to a phenyl-benzohydrazide group. The pyrazole ring assumes an envelope conformation, the C atom attached to the quinoxalin-3-yl ring system being the flap atom. The dihedral angle between the two phenyl rings of the phenyl-benzohydrazide group is of 58.27 (9)°. The mean plane through the pyrazole ring is nearly perpendicular to the quinoxaline ring system and to the phenyl ring attached to the opposite side, forming dihedral angles of 82.58 (7) and 87.29 (9)°, respectively. An intra-molecular C-H⋯O hydrogen bond is present. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers, which are further connected by C-H⋯N hydrogen bonds into chains parallel to the b axis.

Related literature

For the biological activity of quinoxaline derivatives, see: El-Sabbagh et al. (2009 ▶); Bemis & Duffy (2005 ▶); Corona et al. (2008 ▶); Ghadage & Shirote (2011 ▶); Yang et al. (2012 ▶).

Experimental

Crystal data

C42H32N6O

M = 636.74

Monoclinic,

a = 12.0127 (3) Å

b = 19.4679 (5) Å

c = 15.2083 (4) Å

β = 106.045 (1)°

V = 3418.09 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.41 × 0.32 × 0.21 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

39727 measured reflections

8306 independent reflections

4919 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.117

S = 1.00

8306 reflections

443 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813020035/rz5080sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020035/rz5080Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020035/rz5080Isup3.cml

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

C42H32N6O	F(000) = 1336
Mr = 636.74	Dx = 1.237 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8306 reflections
a = 12.0127 (3) Å	θ = 2.7–28.2°
b = 19.4679 (5) Å	µ = 0.08 mm−1
c = 15.2083 (4) Å	T = 296 K
β = 106.045 (1)°	Block, colourless
V = 3418.09 (15) Å3	0.41 × 0.32 × 0.21 mm
Z = 4

Bruker X8 APEXII area-detector diffractometer	4919 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Graphite monochromator	θmax = 28.2°, θmin = 2.7°
φ and ω scans	h = −15→15
39727 measured reflections	k = −25→25
8306 independent reflections	l = −20→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.4886P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
8306 reflections	Δρmax = 0.20 e Å−3
443 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (4)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > σ(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	0.13275 (13)	0.33151 (8)	0.47673 (10)	0.0316 (3)
C2	0.06730 (13)	0.27133 (8)	0.42495 (9)	0.0297 (3)
H2	0.1159	0.2304	0.4300	0.036*
C3	−0.02281 (13)	0.26028 (7)	0.47999 (9)	0.0274 (3)
H3	−0.0999	0.2478	0.4403	0.033*
C4	0.02100 (12)	0.20572 (8)	0.55295 (9)	0.0267 (3)
C5	0.10980 (12)	0.17641 (8)	0.70169 (9)	0.0299 (3)
C6	0.15065 (14)	0.19551 (9)	0.79455 (10)	0.0412 (4)
H6	0.1456	0.2410	0.8118	0.049*
C7	0.19740 (15)	0.14740 (10)	0.85869 (11)	0.0467 (5)
H7	0.2221	0.1599	0.9201	0.056*
C8	0.20864 (15)	0.07971 (10)	0.83350 (11)	0.0482 (5)
H8	0.2426	0.0476	0.8782	0.058*
C9	0.17070 (14)	0.05958 (9)	0.74423 (11)	0.0430 (4)
H9	0.1795	0.0142	0.7281	0.052*
C10	0.11820 (13)	0.10795 (8)	0.67679 (10)	0.0310 (4)
C11	0.02421 (12)	0.13436 (8)	0.52876 (9)	0.0278 (3)
C12	−0.14430 (13)	0.11813 (7)	0.39499 (10)	0.0295 (3)
C13	−0.22002 (14)	0.11864 (9)	0.44837 (11)	0.0399 (4)
H13	−0.1918	0.1180	0.5118	0.048*
C14	−0.33859 (15)	0.12013 (10)	0.40724 (13)	0.0529 (5)
H14	−0.3896	0.1213	0.4434	0.064*
C15	−0.38114 (16)	0.11984 (10)	0.31384 (13)	0.0527 (5)
H15	−0.4607	0.1196	0.2867	0.063*
C16	−0.30551 (16)	0.11984 (9)	0.26043 (11)	0.0463 (5)
H16	−0.3343	0.1200	0.1970	0.056*
C17	−0.18744 (15)	0.11955 (8)	0.30003 (10)	0.0369 (4)
H17	−0.1368	0.1203	0.2635	0.044*
C18	0.14618 (14)	0.07099 (8)	0.40332 (10)	0.0336 (4)
C19	0.20182 (14)	0.01078 (8)	0.37266 (10)	0.0325 (4)
C20	0.32110 (15)	0.00497 (9)	0.40344 (12)	0.0454 (4)
H20	0.3639	0.0382	0.4424	0.055*
C21	0.37670 (17)	−0.04982 (11)	0.37664 (13)	0.0565 (5)
H21	0.4569	−0.0536	0.3978	0.068*
C22	0.31412 (18)	−0.09881 (11)	0.31888 (14)	0.0588 (5)
H22	0.3518	−0.1360	0.3015	0.071*
C23	0.19607 (18)	−0.09299 (10)	0.28676 (13)	0.0553 (5)
H23	0.1539	−0.1260	0.2472	0.066*
C24	0.13965 (15)	−0.03813 (9)	0.31305 (11)	0.0409 (4)
H24	0.0597	−0.0341	0.2906	0.049*
C25	0.01238 (13)	0.28786 (8)	0.32437 (10)	0.0320 (4)
C26	−0.03921 (14)	0.35066 (9)	0.29610 (11)	0.0416 (4)
H26	−0.0372	0.3850	0.3390	0.050*
C27	−0.09401 (15)	0.36282 (11)	0.20433 (12)	0.0502 (5)
H27	−0.1286	0.4052	0.1862	0.060*
C28	−0.09737 (16)	0.31247 (12)	0.14017 (12)	0.0543 (5)
H28	−0.1353	0.3204	0.0789	0.065*
C29	−0.04462 (17)	0.25073 (11)	0.16706 (12)	0.0561 (5)
H29	−0.0458	0.2168	0.1237	0.067*
C30	0.01064 (15)	0.23837 (9)	0.25863 (11)	0.0437 (4)
H30	0.0469	0.1964	0.2760	0.052*
C31	0.24876 (14)	0.35178 (9)	0.47640 (11)	0.0392 (4)
C32	0.30152 (18)	0.40906 (10)	0.52508 (15)	0.0610 (6)
H32	0.2604	0.4363	0.5555	0.073*
C33	0.4142 (2)	0.42592 (13)	0.52862 (17)	0.0765 (7)
H33	0.4485	0.4643	0.5616	0.092*
C34	0.47581 (19)	0.38669 (14)	0.48410 (16)	0.0713 (7)
H34	0.5516	0.3986	0.4865	0.086*
C35	0.42580 (17)	0.32967 (13)	0.43584 (13)	0.0617 (6)
H35	0.4681	0.3028	0.4060	0.074*
C36	0.31229 (15)	0.31201 (10)	0.43149 (11)	0.0485 (5)
H36	0.2787	0.2735	0.3985	0.058*
C37	−0.09873 (14)	0.35058 (9)	0.57148 (10)	0.0412 (4)
C38	−0.17521 (16)	0.30522 (11)	0.59395 (11)	0.0528 (5)
H38	−0.1776	0.2596	0.5754	0.063*
C39	−0.24821 (19)	0.32803 (16)	0.64427 (14)	0.0816 (8)
H39	−0.2991	0.2972	0.6596	0.098*
C40	−0.2468 (2)	0.3944 (2)	0.67158 (17)	0.1044 (12)
H40	−0.2959	0.4090	0.7056	0.125*
C41	−0.1725 (2)	0.43964 (16)	0.64864 (17)	0.0931 (10)
H41	−0.1718	0.4852	0.6671	0.112*
C42	−0.09776 (17)	0.41894 (11)	0.59825 (13)	0.0621 (6)
H42	−0.0480	0.4503	0.5827	0.075*
N1	−0.02553 (12)	0.32888 (7)	0.51901 (8)	0.0360 (3)
N2	0.07573 (12)	0.36378 (7)	0.52524 (8)	0.0365 (3)
N3	0.06255 (10)	0.22567 (6)	0.63778 (8)	0.0305 (3)
N4	0.07247 (10)	0.08697 (6)	0.58766 (8)	0.0322 (3)
N5	−0.02142 (10)	0.11631 (6)	0.43538 (8)	0.0301 (3)
N6	0.03408 (11)	0.06146 (6)	0.40476 (8)	0.0315 (3)
H6N	0.0090	0.0199	0.4130	0.038*
O3	0.19716 (10)	0.12528 (6)	0.42520 (9)	0.0483 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0384 (9)	0.0283 (8)	0.0266 (7)	−0.0008 (7)	0.0065 (6)	0.0005 (6)
C2	0.0350 (8)	0.0305 (9)	0.0258 (7)	0.0031 (7)	0.0120 (6)	0.0010 (6)
C3	0.0316 (8)	0.0283 (8)	0.0227 (7)	0.0024 (6)	0.0080 (6)	−0.0022 (6)
C4	0.0265 (8)	0.0307 (8)	0.0243 (7)	0.0003 (6)	0.0092 (6)	0.0001 (6)
C5	0.0289 (8)	0.0351 (9)	0.0246 (7)	−0.0037 (7)	0.0056 (6)	0.0023 (6)
C6	0.0477 (10)	0.0451 (10)	0.0278 (8)	−0.0042 (8)	0.0055 (7)	−0.0024 (7)
C7	0.0504 (11)	0.0584 (13)	0.0251 (8)	−0.0131 (9)	0.0003 (7)	0.0044 (8)
C8	0.0462 (11)	0.0504 (12)	0.0384 (9)	−0.0104 (9)	−0.0042 (8)	0.0183 (8)
C9	0.0456 (10)	0.0337 (10)	0.0415 (9)	−0.0068 (8)	−0.0019 (8)	0.0072 (7)
C10	0.0283 (8)	0.0335 (9)	0.0280 (8)	−0.0065 (7)	0.0025 (6)	0.0024 (6)
C11	0.0257 (8)	0.0323 (9)	0.0247 (7)	−0.0026 (6)	0.0056 (6)	−0.0019 (6)
C12	0.0321 (8)	0.0243 (8)	0.0289 (7)	−0.0007 (6)	0.0031 (6)	0.0003 (6)
C13	0.0368 (10)	0.0503 (11)	0.0298 (8)	−0.0034 (8)	0.0046 (7)	0.0070 (7)
C14	0.0336 (10)	0.0737 (14)	0.0501 (11)	−0.0021 (9)	0.0093 (8)	0.0127 (10)
C15	0.0355 (10)	0.0604 (13)	0.0514 (11)	0.0016 (9)	−0.0057 (8)	0.0078 (9)
C16	0.0513 (11)	0.0452 (11)	0.0317 (9)	0.0052 (9)	−0.0066 (8)	0.0000 (8)
C17	0.0449 (10)	0.0352 (9)	0.0271 (8)	0.0021 (7)	0.0044 (7)	−0.0008 (7)
C18	0.0358 (9)	0.0328 (9)	0.0300 (8)	−0.0011 (7)	0.0055 (6)	−0.0008 (7)
C19	0.0385 (9)	0.0339 (9)	0.0263 (7)	0.0015 (7)	0.0109 (6)	0.0008 (6)
C20	0.0406 (10)	0.0531 (12)	0.0404 (9)	0.0029 (9)	0.0077 (8)	−0.0092 (8)
C21	0.0453 (11)	0.0694 (14)	0.0545 (11)	0.0153 (10)	0.0134 (9)	−0.0075 (10)
C22	0.0640 (14)	0.0554 (13)	0.0649 (13)	0.0130 (11)	0.0310 (11)	−0.0118 (10)
C23	0.0609 (13)	0.0563 (13)	0.0550 (11)	−0.0055 (10)	0.0268 (10)	−0.0256 (10)
C24	0.0436 (10)	0.0463 (11)	0.0359 (9)	−0.0039 (8)	0.0162 (7)	−0.0084 (8)
C25	0.0326 (8)	0.0401 (10)	0.0255 (7)	−0.0034 (7)	0.0118 (6)	0.0011 (7)
C26	0.0435 (10)	0.0490 (11)	0.0355 (9)	0.0079 (8)	0.0165 (7)	0.0055 (8)
C27	0.0403 (10)	0.0705 (13)	0.0422 (10)	0.0101 (9)	0.0155 (8)	0.0204 (9)
C28	0.0460 (11)	0.0864 (16)	0.0278 (9)	−0.0107 (11)	0.0058 (8)	0.0084 (10)
C29	0.0724 (14)	0.0671 (14)	0.0277 (9)	−0.0174 (11)	0.0118 (9)	−0.0082 (9)
C30	0.0582 (11)	0.0427 (10)	0.0316 (9)	−0.0071 (9)	0.0149 (8)	−0.0038 (7)
C31	0.0411 (10)	0.0404 (10)	0.0326 (8)	−0.0055 (8)	0.0045 (7)	0.0098 (7)
C32	0.0616 (13)	0.0434 (12)	0.0770 (14)	−0.0163 (10)	0.0174 (11)	−0.0011 (10)
C33	0.0644 (16)	0.0673 (16)	0.0924 (18)	−0.0295 (13)	0.0124 (13)	0.0041 (13)
C34	0.0465 (13)	0.0953 (19)	0.0690 (14)	−0.0217 (13)	0.0107 (11)	0.0265 (13)
C35	0.0463 (12)	0.0937 (17)	0.0469 (11)	−0.0061 (12)	0.0158 (9)	0.0149 (11)
C36	0.0431 (10)	0.0685 (13)	0.0335 (9)	−0.0076 (9)	0.0099 (8)	0.0054 (9)
C37	0.0419 (10)	0.0559 (11)	0.0213 (7)	0.0202 (9)	0.0015 (7)	−0.0044 (7)
C38	0.0468 (11)	0.0794 (15)	0.0353 (9)	0.0193 (10)	0.0163 (8)	0.0075 (9)
C39	0.0543 (13)	0.152 (3)	0.0448 (12)	0.0297 (15)	0.0233 (10)	−0.0010 (14)
C40	0.0635 (17)	0.186 (4)	0.0622 (16)	0.045 (2)	0.0141 (13)	−0.0477 (19)
C41	0.0745 (18)	0.121 (2)	0.0693 (16)	0.0436 (17)	−0.0047 (13)	−0.0553 (16)
C42	0.0590 (13)	0.0691 (14)	0.0478 (11)	0.0231 (11)	−0.0027 (9)	−0.0262 (10)
N1	0.0459 (8)	0.0333 (8)	0.0305 (7)	0.0053 (6)	0.0134 (6)	−0.0026 (6)
N2	0.0450 (8)	0.0322 (8)	0.0295 (7)	−0.0006 (6)	0.0057 (6)	−0.0005 (6)
N3	0.0335 (7)	0.0341 (8)	0.0233 (6)	0.0004 (6)	0.0065 (5)	−0.0008 (5)
N4	0.0326 (7)	0.0299 (7)	0.0308 (7)	−0.0031 (6)	0.0035 (5)	0.0007 (6)
N5	0.0322 (7)	0.0304 (7)	0.0256 (6)	0.0025 (6)	0.0044 (5)	−0.0066 (5)
N6	0.0371 (7)	0.0268 (7)	0.0308 (7)	−0.0005 (6)	0.0097 (5)	−0.0047 (5)
O3	0.0401 (7)	0.0346 (7)	0.0697 (8)	−0.0045 (6)	0.0146 (6)	−0.0104 (6)

C1—N2	1.2990 (19)	C21—C22	1.372 (3)
C1—C31	1.450 (2)	C21—H21	0.9300
C1—C2	1.506 (2)	C22—C23	1.371 (3)
C2—C25	1.5235 (19)	C22—H22	0.9300
C2—C3	1.555 (2)	C23—C24	1.382 (2)
C2—H2	0.9784	C23—H23	0.9300
C3—N1	1.4655 (19)	C24—H24	0.9300
C3—C4	1.5211 (19)	C25—C30	1.384 (2)
C3—H3	0.9858	C25—C26	1.384 (2)
C4—N3	1.3071 (17)	C26—C27	1.389 (2)
C4—C11	1.440 (2)	C26—H26	0.9300
C5—N3	1.3717 (18)	C27—C28	1.376 (3)
C5—C10	1.397 (2)	C27—H27	0.9300
C5—C6	1.411 (2)	C28—C29	1.368 (3)
C6—C7	1.357 (2)	C28—H28	0.9300
C6—H6	0.9300	C29—C30	1.388 (2)
C7—C8	1.389 (3)	C29—H29	0.9300
C7—H7	0.9300	C30—H30	0.9300
C8—C9	1.365 (2)	C31—C32	1.391 (2)
C8—H8	0.9300	C31—C36	1.392 (2)
C9—C10	1.407 (2)	C32—C33	1.379 (3)
C9—H9	0.9300	C32—H32	0.9300
C10—N4	1.3764 (18)	C33—C34	1.366 (3)
C11—N4	1.3049 (18)	C33—H33	0.9300
C11—N5	1.4178 (17)	C34—C35	1.374 (3)
C12—C13	1.377 (2)	C34—H34	0.9300
C12—C17	1.393 (2)	C35—C36	1.390 (3)
C12—N5	1.4340 (19)	C35—H35	0.9300
C13—C14	1.389 (2)	C36—H36	0.9300
C13—H13	0.9300	C37—C38	1.384 (3)
C14—C15	1.370 (2)	C37—C42	1.391 (3)
C14—H14	0.9300	C37—N1	1.406 (2)
C15—C16	1.376 (3)	C38—C39	1.387 (3)
C15—H15	0.9300	C38—H38	0.9300
C16—C17	1.379 (2)	C39—C40	1.357 (4)
C16—H16	0.9300	C39—H39	0.9300
C17—H17	0.9300	C40—C41	1.366 (4)
C18—O3	1.2207 (18)	C40—H40	0.9300
C18—N6	1.365 (2)	C41—C42	1.391 (3)
C18—C19	1.487 (2)	C41—H41	0.9300
C19—C24	1.383 (2)	C42—H42	0.9300
C19—C20	1.384 (2)	N1—N2	1.3735 (18)
C20—C21	1.379 (2)	N5—N6	1.4047 (16)
C20—H20	0.9300	N6—H6N	0.8852
N2—C1—C31	121.91 (14)	C22—C23—C24	120.17 (17)
N2—C1—C2	113.08 (13)	C22—C23—H23	119.9
C31—C1—C2	124.98 (14)	C24—C23—H23	119.9
C1—C2—C25	112.28 (12)	C23—C24—C19	120.18 (16)
C1—C2—C3	99.59 (11)	C23—C24—H24	119.9
C25—C2—C3	113.38 (12)	C19—C24—H24	119.9
C1—C2—H2	112.3	C30—C25—C26	118.31 (15)
C25—C2—H2	109.5	C30—C25—C2	119.60 (15)
C3—C2—H2	109.5	C26—C25—C2	122.06 (14)
N1—C3—C4	112.51 (11)	C25—C26—C27	120.64 (16)
N1—C3—C2	100.88 (11)	C25—C26—H26	119.7
C4—C3—C2	109.70 (11)	C27—C26—H26	119.7
N1—C3—H3	110.5	C28—C27—C26	120.27 (18)
C4—C3—H3	110.6	C28—C27—H27	119.9
C2—C3—H3	112.3	C26—C27—H27	119.9
N3—C4—C11	120.59 (13)	C29—C28—C27	119.59 (16)
N3—C4—C3	118.25 (13)	C29—C28—H28	120.2
C11—C4—C3	121.03 (12)	C27—C28—H28	120.2
N3—C5—C10	121.45 (13)	C28—C29—C30	120.39 (18)
N3—C5—C6	119.09 (14)	C28—C29—H29	119.8
C10—C5—C6	119.45 (14)	C30—C29—H29	119.8
C7—C6—C5	119.86 (16)	C25—C30—C29	120.76 (18)
C7—C6—H6	120.1	C25—C30—H30	119.6
C5—C6—H6	120.1	C29—C30—H30	119.6
C6—C7—C8	120.60 (15)	C32—C31—C36	118.45 (17)
C6—C7—H7	119.7	C32—C31—C1	120.90 (17)
C8—C7—H7	119.7	C36—C31—C1	120.55 (15)
C9—C8—C7	121.02 (16)	C33—C32—C31	120.6 (2)
C9—C8—H8	119.5	C33—C32—H32	119.7
C7—C8—H8	119.5	C31—C32—H32	119.7
C8—C9—C10	119.49 (16)	C34—C33—C32	120.5 (2)
C8—C9—H9	120.3	C34—C33—H33	119.7
C10—C9—H9	120.3	C32—C33—H33	119.7
N4—C10—C5	120.74 (13)	C33—C34—C35	120.0 (2)
N4—C10—C9	119.73 (14)	C33—C34—H34	120.0
C5—C10—C9	119.50 (14)	C35—C34—H34	120.0
N4—C11—N5	119.19 (13)	C34—C35—C36	120.2 (2)
N4—C11—C4	123.01 (13)	C34—C35—H35	119.9
N5—C11—C4	117.69 (12)	C36—C35—H35	119.9
C13—C12—C17	119.61 (14)	C35—C36—C31	120.19 (19)
C13—C12—N5	121.14 (12)	C35—C36—H36	119.9
C17—C12—N5	119.24 (14)	C31—C36—H36	119.9
C12—C13—C14	119.81 (15)	C38—C37—C42	119.39 (17)
C12—C13—H13	120.1	C38—C37—N1	120.72 (16)
C14—C13—H13	120.1	C42—C37—N1	119.85 (18)
C15—C14—C13	120.61 (18)	C37—C38—C39	119.8 (2)
C15—C14—H14	119.7	C37—C38—H38	120.1
C13—C14—H14	119.7	C39—C38—H38	120.1
C14—C15—C16	119.61 (17)	C40—C39—C38	121.2 (3)
C14—C15—H15	120.2	C40—C39—H39	119.4
C16—C15—H15	120.2	C38—C39—H39	119.4
C15—C16—C17	120.62 (15)	C39—C40—C41	119.3 (2)
C15—C16—H16	119.7	C39—C40—H40	120.4
C17—C16—H16	119.7	C41—C40—H40	120.4
C16—C17—C12	119.71 (16)	C40—C41—C42	121.4 (3)
C16—C17—H17	120.1	C40—C41—H41	119.3
C12—C17—H17	120.1	C42—C41—H41	119.3
O3—C18—N6	122.41 (14)	C37—C42—C41	118.9 (2)
O3—C18—C19	122.20 (15)	C37—C42—H42	120.5
N6—C18—C19	115.39 (14)	C41—C42—H42	120.5
C24—C19—C20	119.13 (15)	N2—N1—C37	119.55 (13)
C24—C19—C18	122.71 (14)	N2—N1—C3	111.11 (12)
C20—C19—C18	118.14 (14)	C37—N1—C3	126.24 (14)
C21—C20—C19	120.29 (16)	C1—N2—N1	108.52 (12)
C21—C20—H20	119.9	C4—N3—C5	117.51 (13)
C19—C20—H20	119.9	C11—N4—C10	116.54 (13)
C22—C21—C20	120.18 (18)	N6—N5—C11	115.65 (11)
C22—C21—H21	119.9	N6—N5—C12	113.80 (11)
C20—C21—H21	119.9	C11—N5—C12	119.36 (12)
C21—C22—C23	120.03 (18)	C18—N6—N5	117.56 (12)
C21—C22—H22	120.0	C18—N6—H6N	120.2
C23—C22—H22	120.0	N5—N6—H6N	115.9

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3	0.98	2.28	3.2425 (19)	169
N6—H6N···N4i	0.89	2.30	3.1754 (18)	172
C16—H16···N2ii	0.93	2.56	3.4799 (19)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3	0.98	2.28	3.2425 (19)	169
N6—H6N⋯N4i	0.89	2.30	3.1754 (18)	172
C16—H16⋯N2ii	0.93	2.56	3.4799 (19)	172

Symmetry codes: (i) ; (ii) .