2,4,5-Triphenyl-1-(prop-2-en-1-yl)-1H-imidazole.

In the title compound, C24H20N2, one of the ring C atoms and one of the ring N atoms are disordered over two sets of sites in a 0.615 (3):0.385 (3) ratio. The two parts of the disordered imidazole ring adopt an envelope conformation, with the undisordered ring N atom as the flap, displaced by -0.118 (6) and 0.226 (7) Å, respectively, in the two disorder components from the plane through the other ring atoms. The crystal structure features C-H⋯N hydrogen bonds and C-H⋯π inter-actions, which lead to the formation of infinite chains along [010].

Related literature

For the biological significance of imidazole derivatives, see, for example: Kumar (2010 ▶); Castaño et al. (2008 ▶); Banfi et al. (2006 ▶); Bogle et al. (1994 ▶). For the synthesis and the structures of similar imidazoles, see: Mohamed et al. (2013a ▶,b ▶); Akkurt et al. (2013 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H20N2

M = 336.42

Monoclinic,

a = 10.362 (3) Å

b = 8.938 (2) Å

c = 19.387 (5) Å

β = 90.340 (5)°

V = 1795.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.14 × 0.14 × 0.003 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ▶) T min = 0.990, T max = 1.000

17127 measured reflections

3168 independent reflections

2442 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.183

S = 1.04

3168 reflections

299 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014104/zp2005sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) shelxl. DOI: 10.1107/S1600536813014104/zp2005Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014104/zp2005Isup3.cml

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

C24H20N2	F(000) = 712
Mr = 336.42	Dx = 1.245 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2698 reflections
a = 10.362 (3) Å	θ = 2.2–21.5°
b = 8.938 (2) Å	µ = 0.07 mm−1
c = 19.387 (5) Å	T = 100 K
β = 90.340 (5)°	Plate, colourless
V = 1795.5 (8) Å3	0.14 × 0.14 × 0.003 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3168 independent reflections
Radiation source: sealed tube	2442 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
phi and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	h = −12→12
Tmin = 0.990, Tmax = 1.000	k = −10→10
17127 measured reflections	l = −23→23

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0987P)2 + 0.7593P] where P = (Fo2 + 2Fc2)/3
3168 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.49 e Å−3
12 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
N1	−0.08400 (18)	0.74686 (19)	0.49897 (9)	0.0410 (6)
N2A	0.1170 (5)	0.7384 (5)	0.5420 (2)	0.0353 (16)	0.615 (3)
C1	−0.0060 (2)	0.8077 (2)	0.45077 (12)	0.0403 (7)
C2A	0.1231 (6)	0.8099 (6)	0.4794 (3)	0.0360 (17)	0.615 (3)
C3	−0.0081 (2)	0.6952 (2)	0.54940 (11)	0.0402 (7)
C4	−0.0590 (2)	0.6243 (2)	0.61210 (11)	0.0394 (7)
C5	0.0089 (2)	0.5150 (2)	0.64866 (11)	0.0437 (7)
C6	−0.0425 (2)	0.4520 (3)	0.70782 (12)	0.0486 (8)
C7	−0.1627 (3)	0.4953 (3)	0.73117 (12)	0.0515 (8)
C8	−0.2316 (2)	0.6021 (3)	0.69493 (13)	0.0489 (8)
C9	−0.1804 (2)	0.6654 (3)	0.63597 (13)	0.0454 (8)
C10	−0.0566 (2)	0.8751 (2)	0.38715 (11)	0.0390 (7)
C11	−0.1781 (2)	0.8326 (3)	0.36242 (12)	0.0441 (8)
C12	−0.2281 (2)	0.8935 (3)	0.30231 (12)	0.0482 (8)
C13	−0.1588 (2)	0.9992 (3)	0.26605 (12)	0.0496 (8)
C14	−0.0392 (2)	1.0439 (3)	0.29035 (12)	0.0494 (8)
C15	0.0118 (2)	0.9824 (2)	0.35016 (11)	0.0429 (7)
C16A	0.2459 (4)	0.8604 (4)	0.44996 (18)	0.0334 (11)	0.615 (3)
C17A	0.2941 (6)	0.9947 (9)	0.4667 (4)	0.0396 (16)	0.615 (3)
C18A	0.4150 (3)	1.0459 (4)	0.43689 (18)	0.0403 (11)	0.615 (3)
C19A	0.4771 (4)	0.9553 (5)	0.39306 (19)	0.0470 (14)	0.615 (3)
C20A	0.4300 (4)	0.8172 (5)	0.3761 (2)	0.0543 (14)	0.615 (3)
C21A	0.3143 (5)	0.7684 (5)	0.4041 (2)	0.0500 (16)	0.615 (3)
C22A	0.2230 (4)	0.7339 (5)	0.5920 (2)	0.0505 (10)	0.615 (3)
C23A	0.3217 (4)	0.6142 (5)	0.5810 (2)	0.0505 (10)	0.615 (3)
C24A	0.3129 (6)	0.5098 (6)	0.5380 (2)	0.0505 (10)	0.615 (3)
C24B	0.3213 (17)	0.999 (2)	0.4606 (8)	0.060 (2)	0.385 (3)
C17B	0.2961 (4)	0.5016 (5)	0.5314 (2)	0.085 (4)	0.385 (3)
C18B	0.4132 (4)	0.4561 (4)	0.5598 (2)	0.0480 (19)	0.385 (3)
C19B	0.4774 (3)	0.5477 (5)	0.6067 (2)	0.058 (2)	0.385 (3)
C20B	0.4245 (4)	0.6848 (5)	0.6252 (2)	0.063 (3)	0.385 (3)
N2B	0.1125 (8)	0.7634 (8)	0.4574 (4)	0.039 (2)	0.385 (3)
C2B	0.1184 (10)	0.6892 (9)	0.5210 (5)	0.038 (3)	0.385 (3)
C16B	0.2432 (3)	0.6387 (5)	0.5499 (2)	0.0393 (19)	0.385 (3)
C23B	0.3136 (8)	0.8876 (10)	0.4214 (4)	0.060 (2)	0.385 (3)
C21B	0.3074 (4)	0.7303 (4)	0.5968 (2)	0.059 (3)	0.385 (3)
C22B	0.2197 (8)	0.7681 (9)	0.4076 (4)	0.060 (2)	0.385 (3)
H6	0.00520	0.37850	0.73250	0.0580*
H7	−0.19750	0.45210	0.77180	0.0620*
H8	−0.31430	0.63210	0.71050	0.0590*
H9	−0.22900	0.73820	0.61130	0.0540*
H5	0.09120	0.48350	0.63290	0.0530*
H22B	0.26730	0.83200	0.59130	0.0610*	0.615 (3)
H23A	0.39730	0.61750	0.60890	0.0610*	0.615 (3)
H24A	0.23890	0.50240	0.50900	0.0610*	0.615 (3)
H24B	0.38020	0.43820	0.53430	0.0610*	0.615 (3)
H11	−0.22710	0.76080	0.38720	0.0530*
H12	−0.31050	0.86250	0.28590	0.0580*
H13	−0.19300	1.04080	0.22470	0.0600*
H14	0.00840	1.11730	0.26590	0.0590*
H15	0.09440	1.01370	0.36610	0.0510*
H17A	0.24920	1.05690	0.49830	0.0480*	0.615 (3)
H18A	0.44920	1.14150	0.44820	0.0490*	0.615 (3)
H19A	0.55590	0.98800	0.37330	0.0560*	0.615 (3)
H20A	0.47620	0.75470	0.34530	0.0650*	0.615 (3)
H21A	0.28130	0.67260	0.39230	0.0600*	0.615 (3)
H22A	0.18590	0.72080	0.63850	0.0610*	0.615 (3)
H17B	0.25230	0.43900	0.49930	0.1020*	0.385 (3)
H18B	0.44940	0.36250	0.54720	0.0570*	0.385 (3)
H19B	0.55740	0.51670	0.62610	0.0700*	0.385 (3)
H20B	0.46830	0.74740	0.65720	0.0760*	0.385 (3)
H21B	0.27130	0.82390	0.60940	0.0710*	0.385 (3)
H22C	0.26510	0.67060	0.40850	0.0730*	0.385 (3)
H22D	0.18350	0.78200	0.36070	0.0730*	0.385 (3)
H23B	0.38800	0.87800	0.39330	0.0730*	0.385 (3)
H24C	0.25300	1.02150	0.49140	0.0730*	0.385 (3)
H24D	0.39560	1.06170	0.45950	0.0730*	0.385 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0465 (10)	0.0351 (10)	0.0414 (11)	−0.0013 (8)	0.0027 (9)	0.0000 (8)
N2A	0.046 (2)	0.028 (3)	0.032 (3)	0.004 (2)	−0.0003 (18)	0.0005 (16)
C1	0.0441 (13)	0.0320 (12)	0.0449 (13)	0.0033 (9)	0.0037 (10)	0.0038 (9)
C2A	0.049 (3)	0.029 (3)	0.030 (3)	0.005 (2)	−0.003 (2)	−0.0054 (18)
C3	0.0446 (13)	0.0327 (12)	0.0432 (13)	0.0008 (9)	0.0022 (10)	0.0040 (9)
C4	0.0460 (13)	0.0309 (11)	0.0413 (12)	−0.0001 (9)	0.0022 (10)	−0.0008 (9)
C5	0.0513 (14)	0.0391 (12)	0.0409 (12)	0.0048 (10)	0.0069 (10)	0.0014 (10)
C6	0.0609 (16)	0.0417 (13)	0.0433 (13)	0.0056 (11)	0.0074 (11)	0.0063 (10)
C7	0.0666 (16)	0.0457 (14)	0.0422 (13)	−0.0032 (12)	0.0094 (12)	0.0021 (11)
C8	0.0518 (14)	0.0391 (13)	0.0559 (15)	−0.0005 (11)	0.0143 (12)	−0.0039 (11)
C9	0.0502 (14)	0.0319 (12)	0.0540 (14)	0.0001 (10)	0.0025 (11)	0.0034 (10)
C10	0.0455 (13)	0.0305 (11)	0.0411 (12)	0.0009 (9)	0.0034 (10)	−0.0004 (9)
C11	0.0456 (13)	0.0334 (12)	0.0533 (14)	0.0013 (10)	0.0012 (11)	−0.0001 (10)
C12	0.0486 (14)	0.0419 (13)	0.0539 (14)	−0.0003 (11)	−0.0080 (11)	−0.0054 (11)
C13	0.0610 (15)	0.0465 (14)	0.0413 (13)	0.0024 (12)	−0.0080 (11)	0.0011 (11)
C14	0.0612 (16)	0.0450 (14)	0.0418 (13)	−0.0069 (12)	−0.0030 (11)	0.0060 (11)
C15	0.0500 (13)	0.0384 (12)	0.0401 (12)	−0.0043 (10)	−0.0033 (10)	0.0009 (10)
C16A	0.0321 (19)	0.041 (2)	0.0270 (18)	0.0065 (16)	0.0013 (15)	−0.0007 (15)
C17A	0.030 (3)	0.038 (2)	0.051 (3)	0.005 (2)	0.010 (2)	0.000 (2)
C18A	0.0308 (19)	0.050 (2)	0.040 (2)	−0.0044 (17)	0.0001 (15)	−0.0003 (17)
C19A	0.041 (2)	0.059 (3)	0.041 (2)	0.0007 (18)	−0.0045 (16)	−0.0068 (18)
C20A	0.050 (2)	0.063 (3)	0.050 (2)	0.000 (2)	0.0207 (19)	−0.020 (2)
C21A	0.064 (3)	0.048 (3)	0.038 (2)	−0.006 (2)	0.003 (2)	−0.0151 (18)
C22A	0.0504 (16)	0.061 (2)	0.0401 (14)	0.0030 (14)	0.0057 (13)	0.0122 (12)
C23A	0.0504 (16)	0.061 (2)	0.0401 (14)	0.0030 (14)	0.0057 (13)	0.0122 (12)
C24A	0.0504 (16)	0.061 (2)	0.0401 (14)	0.0030 (14)	0.0057 (13)	0.0122 (12)
C24B	0.060 (4)	0.073 (4)	0.048 (3)	−0.007 (3)	−0.011 (3)	0.010 (2)
C17B	0.080 (7)	0.040 (5)	0.136 (10)	−0.013 (5)	0.001 (7)	−0.001 (5)
C18B	0.033 (3)	0.066 (4)	0.045 (3)	−0.002 (3)	−0.002 (3)	0.004 (3)
C19B	0.060 (4)	0.055 (4)	0.060 (4)	−0.009 (3)	0.029 (3)	−0.015 (3)
C20B	0.058 (4)	0.069 (5)	0.062 (4)	−0.004 (4)	−0.031 (4)	−0.018 (4)
N2B	0.053 (4)	0.036 (4)	0.029 (4)	−0.008 (3)	0.001 (3)	0.003 (3)
C2B	0.052 (4)	0.024 (5)	0.039 (5)	−0.005 (4)	−0.004 (4)	0.000 (3)
C16B	0.037 (3)	0.050 (4)	0.031 (3)	−0.014 (3)	0.003 (3)	−0.008 (3)
C23B	0.060 (4)	0.073 (4)	0.048 (3)	−0.007 (3)	−0.011 (3)	0.010 (2)
C21B	0.085 (6)	0.052 (4)	0.040 (4)	0.007 (4)	0.004 (4)	−0.018 (3)
C22B	0.060 (4)	0.073 (4)	0.048 (3)	−0.007 (3)	−0.011 (3)	0.010 (2)

N1—C1	1.353 (3)	C20A—C21A	1.389 (6)
N1—C3	1.334 (3)	C20B—C21B	1.390 (6)
N2A—C2A	1.373 (7)	C22A—C23A	1.496 (6)
N2A—C3	1.361 (6)	C22B—C23B	1.468 (12)
N2A—C22A	1.461 (6)	C23A—C24A	1.254 (6)
N2B—C2B	1.401 (12)	C23B—C24B	1.255 (19)
N2B—C22B	1.477 (11)	C5—H5	0.9500
N2B—C1	1.296 (8)	C6—H6	0.9500
C1—C2A	1.445 (7)	C7—H7	0.9500
C1—C10	1.467 (3)	C8—H8	0.9500
C2A—C16A	1.469 (7)	C9—H9	0.9500
C2B—C3	1.426 (10)	C11—H11	0.9500
C2B—C16B	1.477 (11)	C12—H12	0.9500
C3—C4	1.471 (3)	C13—H13	0.9500
C4—C5	1.395 (3)	C14—H14	0.9500
C4—C9	1.392 (3)	C15—H15	0.9500
C5—C6	1.387 (3)	C17A—H17A	0.9500
C6—C7	1.383 (4)	C17B—H17B	0.9500
C7—C8	1.382 (4)	C18A—H18A	0.9500
C8—C9	1.384 (4)	C18B—H18B	0.9500
C10—C11	1.397 (3)	C19A—H19A	0.9500
C10—C15	1.394 (3)	C19B—H19B	0.9500
C11—C12	1.384 (3)	C20A—H20A	0.9500
C12—C13	1.381 (3)	C20B—H20B	0.9500
C13—C14	1.382 (3)	C21A—H21A	0.9500
C14—C15	1.385 (3)	C21B—H21B	0.9500
C16A—C17A	1.339 (9)	C22A—H22A	0.9900
C16A—C21A	1.406 (6)	C22A—H22B	0.9900
C16B—C17B	1.390 (6)	C22B—H22C	0.9900
C16B—C21B	1.390 (6)	C22B—H22D	0.9900
C17A—C18A	1.457 (7)	C23A—H23A	0.9500
C17B—C18B	1.390 (6)	C23B—H23B	0.9500
C18A—C19A	1.341 (5)	C24A—H24A	0.9500
C18B—C19B	1.390 (6)	C24A—H24B	0.9500
C19A—C20A	1.367 (6)	C24B—H24C	0.9500
C19B—C20B	1.390 (6)	C24B—H24D	0.9500
C1—N1—C3	107.06 (18)	C6—C5—H5	120.00
C2A—N2A—C3	105.9 (4)	C5—C6—H6	120.00
C2A—N2A—C22A	124.1 (5)	C7—C6—H6	120.00
C3—N2A—C22A	129.4 (3)	C6—C7—H7	120.00
C2B—N2B—C22B	124.0 (8)	C8—C7—H7	120.00
C1—N2B—C2B	105.6 (7)	C7—C8—H8	120.00
C1—N2B—C22B	130.0 (7)	C9—C8—H8	120.00
N1—C1—C2A	107.2 (3)	C4—C9—H9	119.00
N2B—C1—C10	122.9 (4)	C8—C9—H9	119.00
N1—C1—C10	122.26 (19)	C10—C11—H11	120.00
N1—C1—N2B	112.2 (4)	C12—C11—H11	120.00
C2A—C1—C10	130.0 (3)	C11—C12—H12	120.00
N2A—C2A—C1	106.6 (5)	C13—C12—H12	120.00
N2A—C2A—C16A	122.1 (5)	C12—C13—H13	120.00
C1—C2A—C16A	131.1 (4)	C14—C13—H13	120.00
N2B—C2B—C3	106.7 (7)	C13—C14—H14	120.00
C3—C2B—C16B	132.1 (7)	C15—C14—H14	120.00
N2B—C2B—C16B	120.8 (8)	C10—C15—H15	120.00
C2B—C3—C4	129.6 (4)	C14—C15—H15	120.00
N1—C3—C4	122.82 (19)	C16A—C17A—H17A	120.00
N1—C3—C2B	105.6 (4)	C18A—C17A—H17A	120.00
N1—C3—N2A	112.5 (2)	C16B—C17B—H17B	120.00
N2A—C3—C4	123.8 (2)	C18B—C17B—H17B	120.00
C5—C4—C9	118.0 (2)	C17A—C18A—H18A	121.00
C3—C4—C5	122.63 (19)	C19A—C18A—H18A	121.00
C3—C4—C9	119.34 (19)	C17B—C18B—H18B	120.00
C4—C5—C6	120.6 (2)	C19B—C18B—H18B	120.00
C5—C6—C7	120.5 (2)	C18A—C19A—H19A	119.00
C6—C7—C8	119.4 (2)	C20A—C19A—H19A	119.00
C7—C8—C9	120.2 (2)	C18B—C19B—H19B	120.00
C4—C9—C8	121.2 (2)	C20B—C19B—H19B	120.00
C11—C10—C15	118.1 (2)	C19A—C20A—H20A	120.00
C1—C10—C11	119.59 (19)	C21A—C20A—H20A	120.00
C1—C10—C15	122.34 (19)	C19B—C20B—H20B	120.00
C10—C11—C12	120.9 (2)	C21B—C20B—H20B	120.00
C11—C12—C13	120.3 (2)	C16A—C21A—H21A	120.00
C12—C13—C14	119.5 (2)	C20A—C21A—H21A	120.00
C13—C14—C15	120.5 (2)	C20B—C21B—H21B	120.00
C10—C15—C14	120.7 (2)	C16B—C21B—H21B	120.00
C17A—C16A—C21A	119.3 (5)	N2A—C22A—H22B	108.00
C2A—C16A—C21A	120.5 (4)	N2A—C22A—H22A	108.00
C2A—C16A—C17A	120.3 (4)	H22A—C22A—H22B	107.00
C2B—C16B—C17B	121.1 (5)	C23A—C22A—H22A	108.00
C17B—C16B—C21B	120.0 (3)	C23A—C22A—H22B	108.00
C2B—C16B—C21B	118.9 (5)	N2B—C22B—H22D	109.00
C16A—C17A—C18A	120.4 (6)	H22C—C22B—H22D	108.00
C16B—C17B—C18B	120.0 (4)	C23B—C22B—H22C	109.00
C17A—C18A—C19A	118.6 (4)	C23B—C22B—H22D	109.00
C17B—C18B—C19B	120.0 (4)	N2B—C22B—H22C	109.00
C18A—C19A—C20A	121.7 (4)	C22A—C23A—H23A	117.00
C18B—C19B—C20B	120.0 (3)	C24A—C23A—H23A	117.00
C19A—C20A—C21A	119.8 (4)	C22B—C23B—H23B	112.00
C19B—C20B—C21B	120.0 (4)	C24B—C23B—H23B	112.00
C16A—C21A—C20A	120.2 (4)	H24A—C24A—H24B	120.00
C16B—C21B—C20B	120.0 (4)	C23A—C24A—H24A	120.00
N2A—C22A—C23A	115.9 (4)	C23A—C24A—H24B	120.00
N2B—C22B—C23B	113.7 (7)	C23B—C24B—H24C	120.00
C22A—C23A—C24A	125.4 (4)	C23B—C24B—H24D	120.00
C22B—C23B—C24B	136.7 (11)	H24C—C24B—H24D	120.00
C4—C5—H5	120.00
C3—N1—C1—C2A	−8.2 (3)	N1—C3—C4—C5	150.5 (2)
C3—N1—C1—C10	179.56 (17)	N2A—C3—C4—C9	139.5 (3)
C1—N1—C3—N2A	9.1 (3)	C9—C4—C5—C6	−1.4 (3)
C1—N1—C3—C4	178.39 (17)	C3—C4—C5—C6	179.5 (2)
C3—N2A—C22A—C23A	105.6 (5)	C5—C4—C9—C8	1.2 (3)
C2A—N2A—C3—N1	−6.0 (4)	C3—C4—C9—C8	−179.6 (2)
C22A—N2A—C3—N1	165.4 (4)	C4—C5—C6—C7	0.7 (3)
C2A—N2A—C3—C4	−175.2 (3)	C5—C6—C7—C8	0.1 (4)
C22A—N2A—C3—C4	−3.8 (6)	C6—C7—C8—C9	−0.2 (4)
C3—N2A—C2A—C16A	−174.0 (4)	C7—C8—C9—C4	−0.4 (4)
C3—N2A—C2A—C1	0.6 (5)	C1—C10—C11—C12	−179.6 (2)
C22A—N2A—C2A—C1	−171.4 (4)	C11—C10—C15—C14	−0.5 (3)
C2A—N2A—C22A—C23A	−84.4 (6)	C1—C10—C15—C14	−179.8 (2)
C22A—N2A—C2A—C16A	14.0 (8)	C15—C10—C11—C12	1.1 (3)
N1—C1—C10—C11	−23.1 (3)	C10—C11—C12—C13	−0.8 (4)
N1—C1—C2A—N2A	4.7 (4)	C11—C12—C13—C14	−0.1 (4)
C2A—C1—C10—C15	−14.0 (4)	C12—C13—C14—C15	0.7 (4)
C2A—C1—C10—C11	166.6 (3)	C13—C14—C15—C10	−0.4 (3)
N1—C1—C2A—C16A	178.7 (5)	C2A—C16A—C17A—C18A	−179.2 (5)
C10—C1—C2A—N2A	176.1 (3)	C17A—C16A—C21A—C20A	−0.6 (7)
C10—C1—C2A—C16A	−9.9 (7)	C21A—C16A—C17A—C18A	1.0 (8)
N1—C1—C10—C15	156.25 (19)	C2A—C16A—C21A—C20A	179.6 (4)
N2A—C2A—C16A—C17A	−86.4 (7)	C16A—C17A—C18A—C19A	−0.6 (8)
N2A—C2A—C16A—C21A	93.4 (6)	C17A—C18A—C19A—C20A	−0.2 (6)
C1—C2A—C16A—C21A	−79.8 (6)	C18A—C19A—C20A—C21A	0.6 (6)
C1—C2A—C16A—C17A	100.4 (7)	C19A—C20A—C21A—C16A	−0.2 (6)
N1—C3—C4—C9	−28.6 (3)	N2A—C22A—C23A—C24A	−8.4 (7)
N2A—C3—C4—C5	−41.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C17A—H17A···N1i	0.95	2.45	3.246 (8)	141
C24A—H24A···N2A	0.95	2.54	2.882 (8)	101
C21A—H21A···Cg3ii	0.95	2.98	3.888 (5)	160
C21B—H21B···Cg4i	0.95	2.99	3.914 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C4–C9 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17A—H17A⋯N1i	0.95	2.45	3.246 (8)	141
C21A—H21A⋯Cg3ii	0.95	2.98	3.888 (5)	160
C21B—H21B⋯Cg4i	0.95	2.99	3.914 (4)	163

Symmetry codes: (i) ; (ii) .