(E)-1-(4-Nitro-benzyl-idene)-2,2-diphenyl-hydrazine.

The asymmetric unit of the title compound, C(19)H(15)N(3)O(2), contains two mol-ecules, both of which show an E conformation of the imine bond. The dihedral angles between the phenyl rings in the phenyl-hydrazine groups are 86.09 (6) and 83.41 (5)° in the two mol-ecules. The 4-nitrobenzene rings show torsion angles of 4.4 (2) and 10.9 (2)° from the two C=N-N planes. In the crystal, C-H⋯π inter-actions and C-H⋯O hydrogen bonds are observed growing along the a, b and c axes, resulting in a complex supramolecular array.

Related literature

For applications of hydrazones, see: Angell et al. (2006 ▶); Vicini et al. (2002 ▶); Rollas et al. (2002 ▶).

Experimental

Crystal data

C19H15N3O2

M = 317.34

Triclinic,

a = 10.8648 (6) Å

b = 11.1477 (6) Å

c = 16.2075 (7) Å

α = 72.084 (4)°

β = 89.037 (4)°

γ = 62.084 (6)°

V = 1631.47 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.6 × 0.36 × 0.29 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.963, T max = 0.98

11850 measured reflections

6432 independent reflections

3566 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 0.89

6432 reflections

434 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043681/bt6850sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043681/bt6850Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043681/bt6850Isup3.cml

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

C19H15N3O2	Z = 4
Mr = 317.34	F(000) = 664
Triclinic, P1	Dx = 1.292 Mg m−3
a = 10.8648 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1477 (6) Å	Cell parameters from 4346 reflections
c = 16.2075 (7) Å	θ = 3.6–26.0°
α = 72.084 (4)°	µ = 0.09 mm−1
β = 89.037 (4)°	T = 298 K
γ = 62.084 (6)°	Prism, yellow
V = 1631.47 (18) Å3	0.6 × 0.36 × 0.29 mm

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	6432 independent reflections
Graphite monochromator	3566 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.020
ω scans	θmax = 26.1°, θmin = 3.6°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −13→12
Tmin = 0.963, Tmax = 0.98	k = −13→11
11850 measured reflections	l = −20→19

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0527P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max = 0.001
6432 reflections	Δρmax = 0.19 e Å−3
434 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0160 (12)

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 > 2σ(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
N5	0.37912 (13)	0.62485 (13)	0.71748 (7)	0.0518 (3)
N4	0.48398 (13)	0.55837 (13)	0.78710 (7)	0.0570 (3)
N2	0.10818 (12)	0.73321 (14)	0.28854 (8)	0.0526 (3)
N1	0.00738 (13)	0.84107 (14)	0.22028 (8)	0.0583 (3)
N6	−0.13482 (15)	0.81987 (18)	0.42567 (8)	0.0646 (4)
C1	0.14313 (15)	0.60094 (17)	0.30146 (9)	0.0516 (4)
H1	0.0981	0.5785	0.2651	0.062*
C21	0.20067 (15)	0.62924 (15)	0.63192 (8)	0.0476 (4)
C2	0.25354 (14)	0.48631 (16)	0.37320 (9)	0.0468 (4)
C20	0.31425 (15)	0.56008 (16)	0.70491 (9)	0.0533 (4)
H20	0.34	0.4676	0.7429	0.064*
C27	0.53186 (15)	0.41316 (15)	0.84431 (9)	0.0466 (4)
C24	−0.01820 (15)	0.75367 (16)	0.49692 (9)	0.0495 (4)
C22	0.12647 (16)	0.55958 (17)	0.62402 (9)	0.0571 (4)
H22	0.1513	0.4694	0.665	0.068*
O4	−0.18158 (13)	0.74572 (15)	0.41247 (7)	0.0865 (4)
C33	0.54160 (15)	0.64120 (16)	0.80149 (8)	0.0473 (4)
C26	0.16313 (16)	0.76359 (16)	0.56908 (9)	0.0532 (4)
H26	0.2123	0.8115	0.5729	0.064*
C25	0.05410 (16)	0.82557 (16)	0.50160 (9)	0.0550 (4)
H25	0.0295	0.9149	0.4597	0.066*
C8	−0.06809 (15)	0.81009 (15)	0.16531 (9)	0.0520 (4)
C7	0.30787 (16)	0.34361 (17)	0.37839 (9)	0.0569 (4)
H7	0.2716	0.3222	0.3367	0.068*
C3	0.30811 (15)	0.51500 (17)	0.43730 (9)	0.0557 (4)
H3	0.2742	0.61	0.4344	0.067*
C34	0.47117 (17)	0.79007 (16)	0.76366 (9)	0.0542 (4)
H34	0.382	0.8372	0.7309	0.065*
C5	0.46458 (16)	0.26540 (17)	0.50650 (10)	0.0563 (4)
C14	−0.01841 (15)	0.98197 (17)	0.20603 (10)	0.0526 (4)
C38	0.67299 (16)	0.57297 (17)	0.85254 (9)	0.0565 (4)
H38	0.7203	0.4733	0.8798	0.068*
O3	−0.17919 (15)	0.94622 (16)	0.38125 (9)	0.0982 (4)
N3	0.57624 (17)	0.14956 (19)	0.57804 (11)	0.0811 (5)
C23	0.01649 (16)	0.62102 (18)	0.55673 (9)	0.0575 (4)
H23	−0.0329	0.5735	0.5521	0.069*
C4	0.41121 (16)	0.40499 (18)	0.50469 (10)	0.0595 (4)
H4	0.4445	0.4247	0.5486	0.071*
C28	0.49956 (15)	0.38849 (17)	0.92809 (9)	0.0564 (4)
H28	0.4457	0.4657	0.9472	0.068*
C15	0.05885 (17)	1.00997 (19)	0.25729 (10)	0.0625 (4)
H15	0.1297	0.9343	0.3021	0.075*
C37	0.73250 (18)	0.6538 (2)	0.86244 (11)	0.0686 (5)
H37	0.8207	0.6077	0.8962	0.082*
C6	0.41473 (17)	0.23299 (17)	0.44433 (10)	0.0607 (4)
H6	0.4522	0.1379	0.4464	0.073*
C35	0.53307 (19)	0.86828 (18)	0.77451 (10)	0.0659 (4)
H35	0.4858	0.9682	0.7484	0.079*
C32	0.60992 (16)	0.29899 (18)	0.81561 (10)	0.0569 (4)
H32	0.6309	0.3155	0.7587	0.068*
C31	0.65662 (17)	0.16031 (18)	0.87176 (12)	0.0688 (5)
H31	0.7096	0.0827	0.8528	0.083*
C12	−0.25571 (18)	0.76574 (19)	0.13928 (11)	0.0705 (5)
H12	−0.3363	0.7609	0.1554	0.085*
C29	0.54716 (17)	0.2492 (2)	0.98368 (10)	0.0678 (5)
H29	0.5259	0.2324	1.0406	0.081*
C13	−0.18622 (17)	0.80211 (17)	0.18977 (10)	0.0611 (4)
H13	−0.2195	0.8211	0.2401	0.073*
C9	−0.01978 (17)	0.78373 (18)	0.09056 (10)	0.0669 (5)
H9	0.0593	0.7909	0.0733	0.08*
O1	0.60017 (18)	0.17750 (16)	0.64075 (10)	0.1282 (6)
C18	−0.1473 (2)	1.2352 (2)	0.12438 (13)	0.0797 (5)
H18	−0.2168	1.3114	0.0791	0.096*
C19	−0.12189 (17)	1.09637 (18)	0.13879 (11)	0.0664 (4)
H19	−0.1743	1.0796	0.1034	0.08*
C30	0.62518 (18)	0.13607 (19)	0.95579 (12)	0.0718 (5)
H30	0.6573	0.0421	0.9937	0.086*
C36	0.6644 (2)	0.8003 (2)	0.82365 (12)	0.0739 (5)
H36	0.7061	0.8537	0.8303	0.089*
C16	0.0311 (2)	1.1497 (2)	0.24218 (13)	0.0757 (5)
H16	0.0825	1.1675	0.2775	0.091*
O2	0.64046 (17)	0.02998 (17)	0.57238 (10)	0.1191 (6)
C10	−0.0895 (2)	0.7465 (2)	0.04114 (11)	0.0798 (5)
H10	−0.0568	0.7279	−0.0093	0.096*
C17	−0.0716 (2)	1.2626 (2)	0.17568 (14)	0.0809 (5)
H17	−0.0895	1.3565	0.1656	0.097*
C11	−0.2058 (2)	0.73704 (19)	0.06594 (12)	0.0763 (5)
H11	−0.2516	0.7108	0.0327	0.092*

	U11	U22	U33	U12	U13	U23
N5	0.0556 (8)	0.0518 (8)	0.0430 (7)	−0.0262 (7)	−0.0071 (6)	−0.0092 (6)
N4	0.0652 (8)	0.0481 (8)	0.0504 (7)	−0.0299 (7)	−0.0176 (6)	−0.0023 (6)
N2	0.0429 (7)	0.0548 (9)	0.0509 (7)	−0.0187 (7)	−0.0022 (6)	−0.0142 (6)
N1	0.0501 (8)	0.0528 (8)	0.0600 (8)	−0.0181 (7)	−0.0122 (6)	−0.0144 (7)
N6	0.0588 (9)	0.0766 (11)	0.0497 (8)	−0.0272 (9)	−0.0037 (7)	−0.0193 (8)
C1	0.0475 (9)	0.0592 (11)	0.0478 (9)	−0.0247 (8)	0.0018 (7)	−0.0195 (8)
C21	0.0536 (9)	0.0470 (9)	0.0411 (8)	−0.0247 (8)	0.0008 (7)	−0.0129 (7)
C2	0.0406 (8)	0.0528 (10)	0.0449 (8)	−0.0219 (8)	0.0053 (7)	−0.0151 (7)
C20	0.0615 (10)	0.0488 (9)	0.0443 (8)	−0.0285 (8)	−0.0058 (7)	−0.0056 (7)
C27	0.0457 (8)	0.0468 (9)	0.0421 (8)	−0.0218 (7)	−0.0053 (7)	−0.0090 (7)
C24	0.0472 (9)	0.0550 (10)	0.0402 (8)	−0.0195 (8)	−0.0019 (7)	−0.0170 (8)
C22	0.0676 (10)	0.0580 (10)	0.0466 (9)	−0.0378 (9)	−0.0011 (8)	−0.0068 (8)
O4	0.0908 (9)	0.1161 (11)	0.0650 (7)	−0.0651 (9)	−0.0125 (6)	−0.0210 (7)
C33	0.0509 (9)	0.0502 (9)	0.0422 (8)	−0.0259 (8)	0.0020 (7)	−0.0151 (7)
C26	0.0630 (10)	0.0475 (9)	0.0506 (9)	−0.0292 (8)	−0.0043 (8)	−0.0140 (8)
C25	0.0665 (10)	0.0428 (9)	0.0475 (9)	−0.0212 (8)	−0.0045 (8)	−0.0130 (7)
C8	0.0478 (9)	0.0496 (9)	0.0476 (9)	−0.0182 (8)	−0.0061 (7)	−0.0106 (7)
C7	0.0664 (10)	0.0591 (11)	0.0465 (9)	−0.0314 (9)	0.0041 (8)	−0.0183 (8)
C3	0.0507 (9)	0.0525 (10)	0.0601 (10)	−0.0208 (8)	−0.0022 (8)	−0.0209 (8)
C34	0.0571 (10)	0.0516 (10)	0.0507 (9)	−0.0256 (9)	0.0046 (7)	−0.0142 (8)
C5	0.0541 (10)	0.0544 (10)	0.0526 (9)	−0.0277 (9)	−0.0044 (7)	−0.0055 (8)
C14	0.0430 (9)	0.0544 (10)	0.0580 (9)	−0.0202 (8)	0.0097 (7)	−0.0217 (8)
C38	0.0546 (10)	0.0560 (10)	0.0563 (9)	−0.0236 (8)	−0.0023 (8)	−0.0206 (8)
O3	0.0915 (10)	0.0763 (10)	0.0864 (9)	−0.0217 (8)	−0.0377 (8)	−0.0048 (8)
N3	0.0853 (12)	0.0663 (12)	0.0739 (11)	−0.0364 (10)	−0.0212 (9)	−0.0002 (9)
C23	0.0615 (10)	0.0703 (11)	0.0501 (9)	−0.0422 (9)	0.0017 (8)	−0.0155 (9)
C4	0.0587 (10)	0.0658 (12)	0.0561 (9)	−0.0324 (9)	−0.0049 (8)	−0.0191 (9)
C28	0.0526 (9)	0.0550 (10)	0.0468 (9)	−0.0148 (8)	−0.0024 (7)	−0.0168 (8)
C15	0.0593 (10)	0.0665 (12)	0.0648 (10)	−0.0310 (9)	0.0082 (8)	−0.0257 (9)
C37	0.0586 (10)	0.0853 (14)	0.0743 (11)	−0.0373 (11)	0.0047 (9)	−0.0389 (11)
C6	0.0704 (11)	0.0482 (10)	0.0559 (9)	−0.0256 (9)	0.0012 (9)	−0.0128 (8)
C35	0.0798 (13)	0.0569 (11)	0.0693 (11)	−0.0374 (10)	0.0163 (10)	−0.0254 (9)
C32	0.0579 (10)	0.0623 (11)	0.0560 (9)	−0.0320 (9)	0.0119 (8)	−0.0226 (9)
C31	0.0585 (10)	0.0509 (11)	0.0900 (13)	−0.0186 (9)	0.0073 (9)	−0.0280 (10)
C12	0.0676 (11)	0.0750 (12)	0.0608 (11)	−0.0430 (10)	−0.0103 (9)	0.0020 (9)
C29	0.0643 (11)	0.0710 (13)	0.0465 (9)	−0.0261 (10)	−0.0008 (8)	−0.0032 (9)
C13	0.0571 (10)	0.0698 (11)	0.0460 (9)	−0.0299 (9)	−0.0028 (8)	−0.0074 (8)
C9	0.0501 (9)	0.0771 (12)	0.0603 (10)	−0.0206 (9)	0.0024 (8)	−0.0233 (9)
O1	0.1500 (15)	0.0965 (11)	0.1025 (11)	−0.0444 (11)	−0.0683 (10)	−0.0096 (9)
C18	0.0667 (12)	0.0581 (12)	0.0895 (13)	−0.0163 (10)	0.0093 (10)	−0.0166 (11)
C19	0.0527 (10)	0.0562 (11)	0.0771 (11)	−0.0188 (9)	−0.0012 (9)	−0.0179 (9)
C30	0.0653 (11)	0.0499 (11)	0.0726 (12)	−0.0215 (10)	−0.0104 (9)	0.0048 (9)
C36	0.0821 (14)	0.0855 (15)	0.0879 (12)	−0.0570 (12)	0.0223 (11)	−0.0460 (11)
C16	0.0828 (14)	0.0824 (14)	0.0848 (13)	−0.0501 (12)	0.0265 (11)	−0.0419 (12)
O2	0.1206 (13)	0.0599 (9)	0.1231 (12)	−0.0158 (9)	−0.0382 (10)	−0.0062 (9)
C10	0.0748 (13)	0.0883 (14)	0.0648 (11)	−0.0240 (12)	−0.0008 (10)	−0.0364 (10)
C17	0.0874 (14)	0.0638 (13)	0.0968 (15)	−0.0358 (12)	0.0329 (12)	−0.0368 (12)
C11	0.0857 (14)	0.0690 (12)	0.0677 (12)	−0.0353 (11)	−0.0172 (10)	−0.0174 (10)

N5—C20	1.2774 (17)	C14—C15	1.386 (2)
N5—N4	1.3632 (15)	C14—C19	1.386 (2)
N4—C33	1.4062 (17)	C38—C37	1.376 (2)
N4—C27	1.4335 (17)	C38—H38	0.93
N2—C1	1.2847 (18)	N3—O2	1.2142 (19)
N2—N1	1.3633 (16)	N3—O1	1.2154 (18)
N1—C14	1.4021 (19)	C23—H23	0.93
N1—C8	1.4368 (18)	C4—H4	0.93
N6—O3	1.2192 (17)	C28—C29	1.376 (2)
N6—O4	1.2217 (16)	C28—H28	0.93
N6—C24	1.4605 (19)	C15—C16	1.380 (2)
C1—C2	1.4564 (19)	C15—H15	0.93
C1—H1	0.93	C37—C36	1.365 (2)
C21—C22	1.3856 (19)	C37—H37	0.93
C21—C26	1.3966 (19)	C6—H6	0.93
C21—C20	1.4538 (19)	C35—C36	1.378 (2)
C2—C7	1.388 (2)	C35—H35	0.93
C2—C3	1.3914 (19)	C32—C31	1.375 (2)
C20—H20	0.93	C32—H32	0.93
C27—C28	1.3738 (19)	C31—C30	1.374 (2)
C27—C32	1.377 (2)	C31—H31	0.93
C24—C23	1.370 (2)	C12—C11	1.363 (2)
C24—C25	1.3762 (19)	C12—C13	1.384 (2)
C22—C23	1.380 (2)	C12—H12	0.93
C22—H22	0.93	C29—C30	1.361 (2)
C33—C34	1.3843 (19)	C29—H29	0.93
C33—C38	1.3917 (19)	C13—H13	0.93
C26—C25	1.3745 (19)	C9—C10	1.381 (2)
C26—H26	0.93	C9—H9	0.93
C25—H25	0.93	C18—C17	1.369 (2)
C8—C13	1.371 (2)	C18—C19	1.381 (2)
C8—C9	1.372 (2)	C18—H18	0.93
C7—C6	1.379 (2)	C19—H19	0.93
C7—H7	0.93	C30—H30	0.93
C3—C4	1.372 (2)	C36—H36	0.93
C3—H3	0.93	C16—C17	1.372 (2)
C34—C35	1.375 (2)	C16—H16	0.93
C34—H34	0.93	C10—C11	1.361 (2)
C5—C6	1.366 (2)	C10—H10	0.93
C5—C4	1.373 (2)	C17—H17	0.93
C5—N3	1.464 (2)	C11—H11	0.93
C20—N5—N4	119.59 (12)	O1—N3—C5	118.34 (17)
N5—N4—C33	116.35 (11)	C24—C23—C22	118.37 (14)
N5—N4—C27	122.46 (11)	C24—C23—H23	120.8
C33—N4—C27	121.17 (11)	C22—C23—H23	120.8
C1—N2—N1	120.25 (12)	C3—C4—C5	119.16 (14)
N2—N1—C14	117.33 (12)	C3—C4—H4	120.4
N2—N1—C8	120.82 (12)	C5—C4—H4	120.4
C14—N1—C8	121.85 (12)	C27—C28—C29	119.80 (15)
O3—N6—O4	123.20 (14)	C27—C28—H28	120.1
O3—N6—C24	118.16 (15)	C29—C28—H28	120.1
O4—N6—C24	118.63 (15)	C16—C15—C14	120.27 (16)
N2—C1—C2	119.80 (13)	C16—C15—H15	119.9
N2—C1—H1	120.1	C14—C15—H15	119.9
C2—C1—H1	120.1	C36—C37—C38	121.16 (16)
C22—C21—C26	118.45 (13)	C36—C37—H37	119.4
C22—C21—C20	118.98 (13)	C38—C37—H37	119.4
C26—C21—C20	122.57 (13)	C5—C6—C7	118.90 (14)
C7—C2—C3	118.23 (13)	C5—C6—H6	120.6
C7—C2—C1	119.76 (13)	C7—C6—H6	120.6
C3—C2—C1	122.00 (13)	C34—C35—C36	120.75 (16)
N5—C20—C21	120.75 (13)	C34—C35—H35	119.6
N5—C20—H20	119.6	C36—C35—H35	119.6
C21—C20—H20	119.6	C31—C32—C27	119.51 (14)
C28—C27—C32	120.13 (14)	C31—C32—H32	120.2
C28—C27—N4	119.59 (14)	C27—C32—H32	120.2
C32—C27—N4	120.28 (13)	C30—C31—C32	120.17 (16)
C23—C24—C25	122.04 (13)	C30—C31—H31	119.9
C23—C24—N6	118.78 (14)	C32—C31—H31	119.9
C25—C24—N6	119.18 (14)	C11—C12—C13	119.87 (16)
C23—C22—C21	121.46 (14)	C11—C12—H12	120.1
C23—C22—H22	119.3	C13—C12—H12	120.1
C21—C22—H22	119.3	C30—C29—C28	120.25 (15)
C34—C33—C38	119.20 (13)	C30—C29—H29	119.9
C34—C33—N4	120.96 (12)	C28—C29—H29	119.9
C38—C33—N4	119.82 (13)	C8—C13—C12	119.74 (15)
C25—C26—C21	120.58 (14)	C8—C13—H13	120.1
C25—C26—H26	119.7	C12—C13—H13	120.1
C21—C26—H26	119.7	C8—C9—C10	119.48 (16)
C26—C25—C24	119.09 (14)	C8—C9—H9	120.3
C26—C25—H25	120.5	C10—C9—H9	120.3
C24—C25—H25	120.5	C17—C18—C19	121.06 (18)
C13—C8—C9	120.19 (14)	C17—C18—H18	119.5
C13—C8—N1	119.42 (14)	C19—C18—H18	119.5
C9—C8—N1	120.35 (14)	C18—C19—C14	120.02 (17)
C6—C7—C2	121.11 (14)	C18—C19—H19	120
C6—C7—H7	119.4	C14—C19—H19	120
C2—C7—H7	119.4	C29—C30—C31	120.14 (16)
C4—C3—C2	120.89 (14)	C29—C30—H30	119.9
C4—C3—H3	119.6	C31—C30—H30	119.9
C2—C3—H3	119.6	C37—C36—C35	119.25 (16)
C35—C34—C33	119.97 (14)	C37—C36—H36	120.4
C35—C34—H34	120	C35—C36—H36	120.4
C33—C34—H34	120	C17—C16—C15	120.79 (18)
C6—C5—C4	121.65 (14)	C17—C16—H16	119.6
C6—C5—N3	119.90 (15)	C15—C16—H16	119.6
C4—C5—N3	118.45 (15)	C11—C10—C9	120.34 (17)
C15—C14—C19	118.75 (15)	C11—C10—H10	119.8
C15—C14—N1	121.37 (14)	C9—C10—H10	119.8
C19—C14—N1	119.87 (14)	C18—C17—C16	119.10 (18)
C37—C38—C33	119.64 (15)	C18—C17—H17	120.4
C37—C38—H38	120.2	C16—C17—H17	120.4
C33—C38—H38	120.2	C10—C11—C12	120.37 (17)
O2—N3—O1	122.90 (17)	C10—C11—H11	119.8
O2—N3—C5	118.76 (17)	C12—C11—H11	119.8
C20—N5—N4—C33	−174.28 (13)	C34—C33—C38—C37	−1.9 (2)
C20—N5—N4—C27	4.3 (2)	N4—C33—C38—C37	176.39 (13)
C1—N2—N1—C14	−175.43 (13)	C6—C5—N3—O2	13.3 (2)
C1—N2—N1—C8	4.2 (2)	C4—C5—N3—O2	−167.54 (17)
N1—N2—C1—C2	178.39 (11)	C6—C5—N3—O1	−166.41 (17)
N2—C1—C2—C7	−169.14 (13)	C4—C5—N3—O1	12.7 (2)
N2—C1—C2—C3	10.4 (2)	C25—C24—C23—C22	0.8 (2)
N4—N5—C20—C21	179.12 (12)	N6—C24—C23—C22	−179.75 (13)
C22—C21—C20—N5	−175.58 (14)	C21—C22—C23—C24	0.2 (2)
C26—C21—C20—N5	4.5 (2)	C2—C3—C4—C5	2.6 (2)
N5—N4—C27—C28	−108.19 (16)	C6—C5—C4—C3	−1.9 (2)
C33—N4—C27—C28	70.35 (18)	N3—C5—C4—C3	178.97 (13)
N5—N4—C27—C32	71.90 (19)	C32—C27—C28—C29	0.9 (2)
C33—N4—C27—C32	−109.55 (15)	N4—C27—C28—C29	−178.97 (13)
O3—N6—C24—C23	168.64 (15)	C19—C14—C15—C16	1.1 (2)
O4—N6—C24—C23	−12.6 (2)	N1—C14—C15—C16	−179.74 (14)
O3—N6—C24—C25	−11.9 (2)	C33—C38—C37—C36	0.6 (2)
O4—N6—C24—C25	166.90 (14)	C4—C5—C6—C7	−0.2 (2)
C26—C21—C22—C23	−0.9 (2)	N3—C5—C6—C7	178.90 (13)
C20—C21—C22—C23	179.14 (14)	C2—C7—C6—C5	1.7 (2)
N5—N4—C33—C34	17.35 (19)	C33—C34—C35—C36	−0.8 (2)
C27—N4—C33—C34	−161.29 (13)	C28—C27—C32—C31	−0.8 (2)
N5—N4—C33—C38	−160.95 (12)	N4—C27—C32—C31	179.12 (13)
C27—N4—C33—C38	20.4 (2)	C27—C32—C31—C30	0.2 (2)
C22—C21—C26—C25	0.7 (2)	C27—C28—C29—C30	−0.5 (2)
C20—C21—C26—C25	−179.39 (14)	C9—C8—C13—C12	0.7 (2)
C21—C26—C25—C24	0.3 (2)	N1—C8—C13—C12	−177.01 (13)
C23—C24—C25—C26	−1.0 (2)	C11—C12—C13—C8	0.5 (2)
N6—C24—C25—C26	179.51 (13)	C13—C8—C9—C10	−1.2 (2)
N2—N1—C8—C13	86.15 (18)	N1—C8—C9—C10	176.53 (14)
C14—N1—C8—C13	−94.20 (17)	C17—C18—C19—C14	0.0 (3)
N2—N1—C8—C9	−91.60 (17)	C15—C14—C19—C18	−0.6 (2)
C14—N1—C8—C9	88.05 (18)	N1—C14—C19—C18	−179.78 (14)
C3—C2—C7—C6	−1.1 (2)	C28—C29—C30—C31	−0.1 (3)
C1—C2—C7—C6	178.45 (13)	C32—C31—C30—C29	0.3 (2)
C7—C2—C3—C4	−1.1 (2)	C38—C37—C36—C35	0.7 (2)
C1—C2—C3—C4	179.40 (13)	C34—C35—C36—C37	−0.6 (2)
C38—C33—C34—C35	2.0 (2)	C14—C15—C16—C17	−1.0 (3)
N4—C33—C34—C35	−176.28 (13)	C8—C9—C10—C11	0.5 (3)
N2—N1—C14—C15	2.2 (2)	C19—C18—C17—C16	0.1 (3)
C8—N1—C14—C15	−177.42 (13)	C15—C16—C17—C18	0.4 (3)
N2—N1—C14—C19	−178.56 (12)	C9—C10—C11—C12	0.8 (3)
C8—N1—C14—C19	1.8 (2)	C13—C12—C11—C10	−1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1i	0.93	2.92	3.4080 (18)	114
C29—H29···Cg2ii	0.93	2.80	3.6875 (18)	161
C7—H7···Cg2	0.93	2.83	3.4223 (16)	123
C30—H30···Cg3iii	0.93	2.84	3.698 (2)	154
C6—H6···O2iv	0.93	2.60	3.342 (3)	138
C15—H15···N2	0.93	2.43	2.750 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C33–C38 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1i	0.93	2.92	3.4080 (18)	114
C29—H29⋯Cg2ii	0.93	2.80	3.6875 (18)	161
C7—H7⋯Cg2	0.93	2.83	3.4223 (16)	123
C30—H30⋯Cg3iii	0.93	2.84	3.698 (2)	154
C6—H6⋯O2iv	0.93	2.60	3.342 (3)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .