(E)-1-Benzyl-idene-2,2-diphenyl-hydrazine.

The asymmetric unit of the title compound, C(19)H(16)N(2), contains two independent mol-ecules, both of which show an E configuration with respect to the C=N bond. The dihedral angles between the phenyl rings bonded to the hydrazine group are 81.00 (10) and 88.34 (8)° in the two mol-ecules. Inter-molecular C-H⋯π inter-actions are observed in the crystal structure.

Related literature

For biological applications of hydrazones, see: Guniz & Rollas (2002 ▶); Ibañez et al. (2002 ▶); Vicini et al. (2002 ▶); Rollas et al. (2002 ▶). For related structures, see: Clulow et al. (2008 ▶); Mendoza et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H16N2

M = 272.34

Triclinic,

a = 10.283 (3) Å

b = 10.558 (3) Å

c = 16.409 (5) Å

α = 75.70 (4)°

β = 85.40 (2)°

γ = 63.403 (15)°

V = 1542.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.5 × 0.4 × 0.2 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.924, T max = 0.97

9357 measured reflections

8060 independent reflections

4867 reflections with I > 2σ(I)

R int = 0.089

3 standard reflections every 97 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.176

S = 1.02

8060 reflections

380 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: XSCANS (Siemens, 1994 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000657/is5046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000657/is5046Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000657/is5046Isup3.cml

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

C19H16N2	Z = 4
Mr = 272.34	F(000) = 576
Triclinic, P1	Dx = 1.173 Mg m−3
a = 10.283 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.558 (3) Å	Cell parameters from 41 reflections
c = 16.409 (5) Å	θ = 4.3–12.6°
α = 75.70 (4)°	µ = 0.07 mm−1
β = 85.40 (2)°	T = 298 K
γ = 63.403 (15)°	Prism, colorless
V = 1542.6 (8) Å3	0.5 × 0.4 × 0.2 mm

Siemens P4 diffractometer	Rint = 0.089
graphite	θmax = 29.0°, θmin = 2.2°
2θ/ω scans	h = −1→13
Absorption correction: ψ scan (North et al., 1968)	k = −12→13
Tmin = 0.924, Tmax = 0.97	l = −22→22
9357 measured reflections	3 standard reflections every 97 reflections
8060 independent reflections	intensity decay: 1%
4867 reflections with I > 2σ(I)

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.0803P)2 + 0.1084P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
8060 reflections	Δρmax = 0.16 e Å−3
380 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (3)

Experimental. UV λmax = 340.13 nm. FT IR (film): (cm-1): 1586, 1490 n(C=N). 1H NMR (400 MHz, (CD3)2CO: (d/p.p.m.): 7.64–7.62 (m, 2H), 7.48–7.44 (m, 4H), 7.36–7.33 (m, 2H), 7.28–7.18 (m, 8H). 13C NMR (400 MHz, (CD3)2CO: (d/ p.p.m.): 143.66, 136.26, 135.18, 129.87, 128.55, 128.11, 126.18, 124.58, 122.35. MS—EI: m/z = 272 M+. C19H16N2.

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
N4	0.66701 (13)	0.13335 (14)	0.09112 (8)	0.0577 (3)
C20	0.63112 (16)	0.02550 (15)	0.23094 (9)	0.0553 (3)
C14	0.75034 (16)	0.49413 (16)	0.28985 (10)	0.0599 (4)
C33	0.71087 (16)	0.25152 (16)	−0.04454 (9)	0.0555 (3)
N3	0.57712 (13)	0.09670 (16)	0.14774 (8)	0.0648 (3)
N1	0.74949 (16)	0.36007 (14)	0.51727 (8)	0.0670 (4)
N2	0.75818 (14)	0.36776 (13)	0.43264 (8)	0.0593 (3)
C32	0.61652 (16)	0.21588 (16)	0.01844 (9)	0.0579 (4)
H32	0.5178	0.2539	0.0055	0.069*
C7	0.78137 (16)	0.22139 (17)	0.57040 (10)	0.0582 (4)
C13	0.74545 (17)	0.48540 (17)	0.38070 (10)	0.0617 (4)
H13	0.7331	0.5653	0.4004	0.074*
C1	0.73689 (17)	0.47714 (16)	0.55251 (9)	0.0575 (4)
C38	0.65030 (19)	0.34881 (17)	−0.12140 (10)	0.0653 (4)
H38	0.5501	0.3916	−0.1313	0.078*
C25	0.54528 (17)	−0.01815 (17)	0.28984 (10)	0.0636 (4)
H25	0.4526	0	0.2739	0.076*
C3	0.8446 (2)	0.5908 (2)	0.61514 (11)	0.0714 (4)
H3	0.927	0.5924	0.6335	0.086*
C31	0.32350 (18)	0.27985 (18)	0.13879 (11)	0.0672 (4)
H31	0.3513	0.3366	0.1618	0.081*
C27	0.38484 (17)	0.06357 (17)	0.09176 (10)	0.0609 (4)
H27	0.4541	−0.0258	0.0833	0.073*
C15	0.75028 (19)	0.61704 (19)	0.23438 (11)	0.0735 (5)
H15	0.746	0.6933	0.255	0.088*
C37	0.7370 (2)	0.38223 (18)	−0.18280 (10)	0.0704 (4)
H37	0.6947	0.449	−0.2332	0.084*
C6	0.60157 (18)	0.58601 (19)	0.56083 (11)	0.0682 (4)
H6	0.5189	0.5855	0.542	0.082*
C5	0.58795 (19)	0.69641 (19)	0.59711 (12)	0.0734 (5)
H5	0.4962	0.7695	0.603	0.088*
C24	0.5964 (2)	−0.08800 (19)	0.37158 (11)	0.0759 (5)
H24	0.5381	−0.117	0.4103	0.091*
C19	0.75539 (19)	0.38216 (19)	0.25709 (11)	0.0695 (4)
H19	0.7548	0.2993	0.2932	0.083*
C34	0.86116 (18)	0.1890 (2)	−0.03245 (11)	0.0704 (4)
H34	0.9044	0.125	0.0185	0.085*
C2	0.85940 (18)	0.48028 (18)	0.57871 (10)	0.0652 (4)
H2	0.9514	0.4085	0.5719	0.078*
C16	0.7566 (2)	0.6266 (2)	0.14858 (12)	0.0849 (6)
H16	0.757	0.7091	0.1119	0.102*
C36	0.8848 (2)	0.3178 (2)	−0.17017 (11)	0.0780 (5)
H36	0.9432	0.3393	−0.2121	0.094*
C21	0.76949 (18)	−0.00257 (19)	0.25626 (11)	0.0687 (4)
H21	0.8288	0.0257	0.218	0.082*
C26	0.42597 (15)	0.14762 (16)	0.12623 (9)	0.0544 (3)
C12	0.8288 (2)	0.09859 (18)	0.53921 (11)	0.0715 (4)
H12	0.8359	0.1065	0.4815	0.086*
C17	0.76235 (19)	0.5146 (2)	0.11706 (12)	0.0821 (6)
H17	0.7669	0.5212	0.0594	0.099*
C8	0.7669 (2)	0.2061 (2)	0.65620 (11)	0.0803 (5)
H8	0.7307	0.2881	0.6783	0.096*
C4	0.7097 (2)	0.69792 (19)	0.62438 (11)	0.0704 (4)
H4	0.7007	0.7717	0.6491	0.084*
C29	0.13758 (18)	0.2447 (2)	0.08227 (11)	0.0707 (4)
H29	0.0405	0.2776	0.0672	0.085*
C28	0.24001 (18)	0.11309 (19)	0.06995 (11)	0.0687 (4)
H28	0.2121	0.0566	0.0468	0.082*
C30	0.17860 (18)	0.32819 (19)	0.11703 (12)	0.0748 (5)
H30	0.1089	0.4172	0.1259	0.09*
C18	0.7613 (2)	0.3935 (2)	0.17156 (12)	0.0809 (5)
H18	0.7646	0.318	0.1505	0.097*
C35	0.9464 (2)	0.2210 (2)	−0.09511 (12)	0.0847 (6)
H35	1.0469	0.1766	−0.0866	0.102*
C9	0.8057 (3)	0.0704 (2)	0.70945 (12)	0.0894 (6)
H9	0.7979	0.0617	0.7672	0.107*
C11	0.8656 (2)	−0.0360 (2)	0.59365 (14)	0.0867 (6)
H11	0.8983	−0.1181	0.5719	0.104*
C10	0.8554 (2)	−0.0514 (2)	0.67862 (13)	0.0843 (6)
H10	0.8816	−0.1428	0.7147	0.101*
C22	0.8179 (2)	−0.0727 (2)	0.33864 (13)	0.0862 (6)
H22	0.9104	−0.0914	0.3552	0.103*
C23	0.7331 (2)	−0.1152 (2)	0.39642 (12)	0.0864 (6)
H23	0.7672	−0.162	0.4517	0.104*

	U11	U22	U33	U12	U13	U23
N4	0.0519 (7)	0.0667 (7)	0.0524 (7)	−0.0265 (6)	0.0002 (5)	−0.0097 (6)
C20	0.0544 (8)	0.0515 (8)	0.0517 (8)	−0.0179 (6)	−0.0030 (6)	−0.0077 (6)
C14	0.0514 (8)	0.0574 (8)	0.0584 (9)	−0.0166 (7)	0.0011 (6)	−0.0067 (7)
C33	0.0595 (9)	0.0565 (8)	0.0510 (8)	−0.0257 (7)	−0.0009 (6)	−0.0126 (6)
N3	0.0496 (7)	0.0842 (9)	0.0530 (7)	−0.0297 (6)	−0.0034 (5)	−0.0017 (6)
N1	0.0903 (10)	0.0572 (7)	0.0514 (7)	−0.0310 (7)	−0.0002 (6)	−0.0116 (6)
N2	0.0620 (7)	0.0589 (7)	0.0521 (7)	−0.0234 (6)	0.0010 (5)	−0.0113 (6)
C32	0.0521 (8)	0.0631 (9)	0.0534 (8)	−0.0224 (7)	−0.0034 (6)	−0.0095 (7)
C7	0.0593 (8)	0.0601 (9)	0.0571 (8)	−0.0301 (7)	−0.0006 (6)	−0.0091 (7)
C13	0.0643 (9)	0.0572 (9)	0.0596 (9)	−0.0240 (7)	0.0009 (7)	−0.0124 (7)
C1	0.0635 (9)	0.0561 (8)	0.0517 (8)	−0.0261 (7)	0.0016 (6)	−0.0115 (6)
C38	0.0677 (10)	0.0621 (9)	0.0566 (9)	−0.0222 (8)	−0.0035 (7)	−0.0090 (7)
C25	0.0591 (9)	0.0626 (9)	0.0599 (9)	−0.0218 (7)	−0.0001 (7)	−0.0084 (7)
C3	0.0724 (11)	0.0759 (11)	0.0749 (11)	−0.0423 (9)	−0.0052 (8)	−0.0122 (9)
C31	0.0669 (10)	0.0660 (10)	0.0701 (10)	−0.0274 (8)	−0.0015 (8)	−0.0211 (8)
C27	0.0580 (9)	0.0611 (9)	0.0576 (9)	−0.0205 (7)	0.0024 (7)	−0.0153 (7)
C15	0.0702 (10)	0.0670 (10)	0.0708 (11)	−0.0260 (8)	0.0032 (8)	−0.0037 (8)
C37	0.0917 (13)	0.0649 (10)	0.0504 (9)	−0.0339 (9)	0.0007 (8)	−0.0076 (7)
C6	0.0591 (9)	0.0722 (10)	0.0738 (10)	−0.0273 (8)	−0.0021 (8)	−0.0203 (8)
C5	0.0656 (10)	0.0679 (10)	0.0817 (12)	−0.0226 (8)	0.0110 (8)	−0.0257 (9)
C24	0.0823 (12)	0.0702 (10)	0.0585 (10)	−0.0261 (9)	0.0047 (8)	−0.0026 (8)
C19	0.0743 (11)	0.0676 (10)	0.0586 (9)	−0.0260 (8)	−0.0003 (8)	−0.0112 (8)
C34	0.0635 (10)	0.0920 (12)	0.0564 (9)	−0.0396 (9)	−0.0037 (7)	−0.0069 (8)
C2	0.0569 (9)	0.0624 (9)	0.0690 (10)	−0.0230 (7)	0.0023 (7)	−0.0100 (7)
C16	0.0705 (11)	0.0873 (13)	0.0689 (11)	−0.0267 (10)	0.0016 (9)	0.0129 (10)
C36	0.0918 (13)	0.1001 (13)	0.0590 (10)	−0.0592 (11)	0.0123 (9)	−0.0182 (9)
C21	0.0595 (9)	0.0724 (10)	0.0663 (10)	−0.0281 (8)	−0.0115 (7)	−0.0008 (8)
C26	0.0475 (7)	0.0624 (8)	0.0484 (7)	−0.0225 (6)	0.0000 (6)	−0.0077 (6)
C12	0.0849 (12)	0.0635 (10)	0.0661 (10)	−0.0344 (9)	0.0062 (8)	−0.0133 (8)
C17	0.0622 (10)	0.1023 (15)	0.0548 (10)	−0.0176 (10)	−0.0015 (7)	−0.0085 (10)
C8	0.1113 (15)	0.0789 (12)	0.0610 (10)	−0.0526 (11)	0.0066 (9)	−0.0146 (9)
C4	0.0890 (12)	0.0679 (10)	0.0635 (10)	−0.0412 (9)	0.0080 (8)	−0.0203 (8)
C29	0.0521 (9)	0.0836 (11)	0.0682 (10)	−0.0246 (8)	−0.0039 (7)	−0.0132 (9)
C28	0.0672 (10)	0.0787 (11)	0.0669 (10)	−0.0358 (9)	−0.0051 (8)	−0.0193 (8)
C30	0.0588 (10)	0.0677 (10)	0.0801 (12)	−0.0104 (8)	0.0022 (8)	−0.0215 (9)
C18	0.0795 (12)	0.0866 (12)	0.0641 (11)	−0.0241 (10)	−0.0019 (9)	−0.0201 (9)
C35	0.0685 (11)	0.1229 (16)	0.0691 (11)	−0.0526 (11)	0.0020 (9)	−0.0135 (11)
C9	0.1234 (17)	0.1000 (15)	0.0604 (10)	−0.0717 (14)	−0.0005 (10)	−0.0010 (10)
C11	0.1050 (15)	0.0634 (11)	0.0913 (15)	−0.0409 (10)	0.0075 (11)	−0.0116 (10)
C10	0.0920 (13)	0.0766 (12)	0.0842 (13)	−0.0506 (11)	−0.0073 (10)	0.0103 (10)
C22	0.0771 (12)	0.0893 (13)	0.0755 (12)	−0.0306 (10)	−0.0280 (10)	0.0063 (10)
C23	0.0938 (14)	0.0823 (12)	0.0595 (10)	−0.0260 (11)	−0.0161 (10)	0.0041 (9)

N4—C32	1.278 (2)	C6—C5	1.384 (2)
N4—N3	1.3681 (18)	C6—H6	0.93
C20—C25	1.390 (2)	C5—C4	1.371 (3)
C20—C21	1.393 (2)	C5—H5	0.93
C20—N3	1.406 (2)	C24—C23	1.377 (3)
C14—C15	1.389 (2)	C24—H24	0.93
C14—C19	1.394 (2)	C19—C18	1.377 (2)
C14—C13	1.469 (2)	C19—H19	0.93
C33—C34	1.391 (2)	C34—C35	1.374 (2)
C33—C38	1.395 (2)	C34—H34	0.93
C33—C32	1.458 (2)	C2—H2	0.93
N3—C26	1.4406 (19)	C16—C17	1.380 (3)
N1—N2	1.3689 (18)	C16—H16	0.93
N1—C7	1.413 (2)	C36—C35	1.373 (3)
N1—C1	1.441 (2)	C36—H36	0.93
N2—C13	1.279 (2)	C21—C22	1.381 (2)
C32—H32	0.93	C21—H21	0.93
C7—C12	1.379 (2)	C12—C11	1.380 (3)
C7—C8	1.380 (2)	C12—H12	0.93
C13—H13	0.93	C17—C18	1.372 (3)
C1—C6	1.375 (2)	C17—H17	0.93
C1—C2	1.380 (2)	C8—C9	1.379 (3)
C38—C37	1.377 (2)	C8—H8	0.93
C38—H38	0.93	C4—H4	0.93
C25—C24	1.377 (2)	C29—C28	1.369 (2)
C25—H25	0.93	C29—C30	1.379 (3)
C3—C4	1.368 (3)	C29—H29	0.93
C3—C2	1.384 (2)	C28—H28	0.93
C3—H3	0.93	C30—H30	0.93
C31—C26	1.376 (2)	C18—H18	0.93
C31—C30	1.386 (2)	C35—H35	0.93
C31—H31	0.93	C9—C10	1.365 (3)
C27—C26	1.382 (2)	C9—H9	0.93
C27—C28	1.384 (2)	C11—C10	1.364 (3)
C27—H27	0.93	C11—H11	0.93
C15—C16	1.385 (3)	C10—H10	0.93
C15—H15	0.93	C22—C23	1.368 (3)
C37—C36	1.368 (3)	C22—H22	0.93
C37—H37	0.93	C23—H23	0.93
C32—N4—N3	119.93 (13)	C14—C19—H19	119.8
C25—C20—C21	118.74 (15)	C35—C34—C33	120.61 (16)
C25—C20—N3	119.73 (14)	C35—C34—H34	119.7
C21—C20—N3	121.53 (14)	C33—C34—H34	119.7
C15—C14—C19	118.52 (16)	C1—C2—C3	119.64 (15)
C15—C14—C13	119.47 (16)	C1—C2—H2	120.2
C19—C14—C13	122.00 (14)	C3—C2—H2	120.2
C34—C33—C38	117.84 (14)	C17—C16—C15	120.51 (18)
C34—C33—C32	122.66 (14)	C17—C16—H16	119.7
C38—C33—C32	119.48 (14)	C15—C16—H16	119.7
N4—N3—C20	117.82 (12)	C37—C36—C35	119.54 (17)
N4—N3—C26	120.99 (12)	C37—C36—H36	120.2
C20—N3—C26	120.60 (12)	C35—C36—H36	120.2
N2—N1—C7	116.32 (13)	C22—C21—C20	119.51 (16)
N2—N1—C1	122.62 (12)	C22—C21—H21	120.2
C7—N1—C1	120.01 (13)	C20—C21—H21	120.2
C13—N2—N1	120.28 (14)	C31—C26—C27	120.16 (14)
N4—C32—C33	121.20 (14)	C31—C26—N3	120.32 (14)
N4—C32—H32	119.4	C27—C26—N3	119.52 (14)
C33—C32—H32	119.4	C7—C12—C11	120.01 (17)
C12—C7—C8	118.27 (15)	C7—C12—H12	120
C12—C7—N1	121.85 (15)	C11—C12—H12	120
C8—C7—N1	119.87 (15)	C18—C17—C16	119.36 (18)
N2—C13—C14	119.90 (15)	C18—C17—H17	120.3
N2—C13—H13	120.1	C16—C17—H17	120.3
C14—C13—H13	120.1	C9—C8—C7	120.65 (18)
C6—C1—C2	119.68 (15)	C9—C8—H8	119.7
C6—C1—N1	119.74 (14)	C7—C8—H8	119.7
C2—C1—N1	120.58 (14)	C3—C4—C5	119.94 (16)
C37—C38—C33	120.81 (16)	C3—C4—H4	120
C37—C38—H38	119.6	C5—C4—H4	120
C33—C38—H38	119.6	C28—C29—C30	119.89 (16)
C24—C25—C20	120.52 (16)	C28—C29—H29	120.1
C24—C25—H25	119.7	C30—C29—H29	120.1
C20—C25—H25	119.7	C29—C28—C27	120.42 (16)
C4—C3—C2	120.54 (16)	C29—C28—H28	119.8
C4—C3—H3	119.7	C27—C28—H28	119.8
C2—C3—H3	119.7	C29—C30—C31	120.15 (16)
C26—C31—C30	119.71 (16)	C29—C30—H30	119.9
C26—C31—H31	120.1	C31—C30—H30	119.9
C30—C31—H31	120.1	C17—C18—C19	120.8 (2)
C26—C27—C28	119.67 (15)	C17—C18—H18	119.6
C26—C27—H27	120.2	C19—C18—H18	119.6
C28—C27—H27	120.2	C36—C35—C34	120.75 (18)
C16—C15—C14	120.34 (19)	C36—C35—H35	119.6
C16—C15—H15	119.8	C34—C35—H35	119.6
C14—C15—H15	119.8	C10—C9—C8	120.96 (19)
C36—C37—C38	120.43 (16)	C10—C9—H9	119.5
C36—C37—H37	119.8	C8—C9—H9	119.5
C38—C37—H37	119.8	C10—C11—C12	121.58 (19)
C1—C6—C5	120.22 (16)	C10—C11—H11	119.2
C1—C6—H6	119.9	C12—C11—H11	119.2
C5—C6—H6	119.9	C11—C10—C9	118.46 (17)
C4—C5—C6	119.97 (16)	C11—C10—H10	120.8
C4—C5—H5	120	C9—C10—H10	120.8
C6—C5—H5	120	C23—C22—C21	121.57 (18)
C23—C24—C25	120.58 (17)	C23—C22—H22	119.2
C23—C24—H24	119.7	C21—C22—H22	119.2
C25—C24—H24	119.7	C22—C23—C24	119.07 (17)
C18—C19—C14	120.44 (17)	C22—C23—H23	120.5
C18—C19—H19	119.8	C24—C23—H23	120.5
C32—N4—N3—C20	−170.05 (14)	C6—C1—C2—C3	1.7 (2)
C32—N4—N3—C26	1.2 (2)	N1—C1—C2—C3	−177.69 (14)
C25—C20—N3—N4	−177.82 (13)	C4—C3—C2—C1	−0.8 (3)
C21—C20—N3—N4	2.3 (2)	C14—C15—C16—C17	0.3 (3)
C25—C20—N3—C26	10.9 (2)	C38—C37—C36—C35	−1.1 (3)
C21—C20—N3—C26	−168.98 (15)	C25—C20—C21—C22	0.0 (3)
C7—N1—N2—C13	−172.96 (14)	N3—C20—C21—C22	179.94 (17)
C1—N1—N2—C13	−4.7 (2)	C30—C31—C26—C27	0.3 (2)
N3—N4—C32—C33	−177.21 (13)	C30—C31—C26—N3	179.36 (15)
C34—C33—C32—N4	5.7 (2)	C28—C27—C26—C31	0.0 (2)
C38—C33—C32—N4	−176.26 (14)	C28—C27—C26—N3	−179.11 (14)
N2—N1—C7—C12	4.5 (2)	N4—N3—C26—C31	−87.86 (19)
C1—N1—C7—C12	−164.03 (15)	C20—N3—C26—C31	83.1 (2)
N2—N1—C7—C8	−176.26 (15)	N4—N3—C26—C27	91.25 (19)
C1—N1—C7—C8	15.2 (2)	C20—N3—C26—C27	−97.77 (18)
N1—N2—C13—C14	−178.09 (13)	C8—C7—C12—C11	−2.4 (3)
C15—C14—C13—N2	−173.94 (15)	N1—C7—C12—C11	176.78 (17)
C19—C14—C13—N2	5.9 (2)	C15—C16—C17—C18	0.2 (3)
N2—N1—C1—C6	88.2 (2)	C12—C7—C8—C9	3.1 (3)
C7—N1—C1—C6	−103.97 (18)	N1—C7—C8—C9	−176.16 (17)
N2—N1—C1—C2	−92.37 (19)	C2—C3—C4—C5	−0.3 (3)
C7—N1—C1—C2	75.4 (2)	C6—C5—C4—C3	0.5 (3)
C34—C33—C38—C37	−0.5 (2)	C30—C29—C28—C27	−0.3 (3)
C32—C33—C38—C37	−178.62 (14)	C26—C27—C28—C29	0.0 (3)
C21—C20—C25—C24	−0.1 (2)	C28—C29—C30—C31	0.6 (3)
N3—C20—C25—C24	180.00 (14)	C26—C31—C30—C29	−0.6 (3)
C19—C14—C15—C16	−0.6 (2)	C16—C17—C18—C19	−0.4 (3)
C13—C14—C15—C16	179.23 (15)	C14—C19—C18—C17	0.0 (3)
C33—C38—C37—C36	1.5 (3)	C37—C36—C35—C34	−0.4 (3)
C2—C1—C6—C5	−1.5 (3)	C33—C34—C35—C36	1.5 (3)
N1—C1—C6—C5	177.89 (15)	C7—C8—C9—C10	−1.8 (3)
C1—C6—C5—C4	0.4 (3)	C7—C12—C11—C10	0.6 (3)
C20—C25—C24—C23	0.3 (3)	C12—C11—C10—C9	0.7 (3)
C15—C14—C19—C18	0.5 (2)	C8—C9—C10—C11	−0.1 (3)
C13—C14—C19—C18	−179.39 (16)	C20—C21—C22—C23	−0.1 (3)
C38—C33—C34—C35	−1.0 (3)	C21—C22—C23—C24	0.3 (3)
C32—C33—C34—C35	177.06 (16)	C25—C24—C23—C22	−0.4 (3)

Cg1, Cg2 and Cg4 are the centroids of the C1–C6, C7–C12 and C20–C25 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg4i	0.93	2.93	3.851 (2)	171
C22—H22···Cg2ii	0.93	2.88	3.788 (3)	166
C37—H37···Cg1iii	0.93	2.99	3.828 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the C1–C6, C7–C12 and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg4i	0.93	2.93	3.851 (2)	171
C22—H22⋯Cg2ii	0.93	2.88	3.788 (3)	166
C37—H37⋯Cg1iii	0.93	2.99	3.828 (2)	150

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