1,3-Dibenzyl-1,2,3,4-tetra-hydro-quinazoline-2,4-dione.

The asymmetric unit of the title compound, C(22)H(18)N(2)O(2), contains two independent mol-ecules, which differ in the orientations of the benzyl groups with respect to the planar (r.m.s. deviations of 0.031 and 0.020 Å) quinazoline-2,4-dione skeletons [dihedral angles of 73.97 (4) and 70.07 (4)° in the first mol-ecule and 75.63 (4) and 63.52 (3)° in the second]. The crystal structure is stabilized by weak inter-molecular C-H⋯O and C-H⋯π interactions and aromatic π-π stacking inter-actions [centroid-centroid distance = 3.735 (2) Å].

Related literature

For the synthesis of the title compound, see: Hedayatullah (1981 ▶). For the synthesis of quinazoline-2,4-dione derivatives, see: Shi et al. (2007 ▶); Kuryazov et al. (2008 ▶). For the biological activity of quinazoline-2,4-dione derivatives, see: Colottaa et al. (2004 ▶); Yakhontov et al. (1977 ▶). For related structures, see: Mazza et al. (1988 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H18N2O2

M = 342.38

Orthorhombic,

a = 17.8989 (4) Å

b = 14.0071 (4) Å

c = 27.7222 (6) Å

V = 6950.3 (3) Å3

Z = 16

Cu Kα radiation

μ = 0.68 mm−1

T = 293 K

0.5 × 0.4 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.804, T max = 1.000

18947 measured reflections

7088 independent reflections

4141 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 0.90

7088 reflections

470 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.14 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019938/fj2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019938/fj2301Isup2.hkl

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

C22H18N2O2	Dx = 1.309 Mg m−3
Mr = 342.38	Melting point: 398(2) K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2463 reflections
a = 17.8989 (4) Å	θ = 3.5–35.8°
b = 14.0071 (4) Å	µ = 0.68 mm−1
c = 27.7222 (6) Å	T = 293 K
V = 6950.3 (3) Å3	Prism, colourless
Z = 16	0.5 × 0.4 × 0.35 mm
F(000) = 2880

Oxford Diffraction Xcalibur Ruby diffractometer	7088 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4141 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 10.2576 pixels mm-1	θmax = 75.8°, θmin = 4.0°
ω scans	h = −22→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→17
Tmin = 0.804, Tmax = 1.000	l = −31→34
18947 measured reflections

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0587P)2] where P = (Fo2 + 2Fc2)/3
S = 0.90	(Δ/σ)max = 0.002
7088 reflections	Δρmax = 0.28 e Å−3
470 parameters	Δρmin = −0.14 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: 0.00081 (5)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
O1A	0.90039 (7)	0.27786 (11)	0.72998 (5)	0.0745 (4)
O2A	0.85328 (8)	0.30319 (11)	0.89063 (5)	0.0770 (4)
N1A	0.77945 (8)	0.27259 (10)	0.75417 (5)	0.0498 (4)
N3A	0.87693 (8)	0.29234 (10)	0.81052 (6)	0.0531 (4)
C2A	0.85450 (10)	0.28112 (13)	0.76252 (7)	0.0538 (5)
C4A	0.82872 (11)	0.29654 (13)	0.84973 (7)	0.0542 (5)
C4AA	0.74920 (10)	0.29394 (11)	0.83793 (6)	0.0476 (4)
C5A	0.69582 (11)	0.30185 (13)	0.87449 (7)	0.0596 (5)
H5A	0.7113	0.3091	0.9063	0.072*
C6A	0.62102 (11)	0.29916 (14)	0.86422 (8)	0.0639 (5)
H6A	0.5859	0.3033	0.8888	0.077*
C7A	0.59835 (11)	0.29017 (13)	0.81658 (8)	0.0627 (5)
H7A	0.5476	0.2894	0.8094	0.075*
C8A	0.64939 (10)	0.28232 (13)	0.77977 (7)	0.0563 (5)
H8A	0.6332	0.2767	0.7480	0.068*
C8AA	0.72575 (9)	0.28287 (11)	0.79034 (6)	0.0454 (4)
C9A	0.75706 (10)	0.24198 (13)	0.70537 (6)	0.0531 (4)
H9AA	0.7164	0.1965	0.7084	0.064*
H9AB	0.7988	0.2089	0.6906	0.064*
C10A	0.73253 (9)	0.32101 (13)	0.67192 (6)	0.0480 (4)
C11A	0.76693 (11)	0.40913 (13)	0.67155 (7)	0.0583 (5)
H11A	0.8039	0.4228	0.6941	0.070*
C12A	0.74673 (12)	0.47754 (15)	0.63777 (8)	0.0722 (6)
H12A	0.7701	0.5368	0.6377	0.087*
C13A	0.69229 (13)	0.45750 (18)	0.60452 (8)	0.0775 (7)
H13A	0.6785	0.5035	0.5820	0.093*
C14A	0.65844 (13)	0.37067 (19)	0.60429 (8)	0.0801 (7)
H14A	0.6220	0.3572	0.5814	0.096*
C15A	0.67784 (11)	0.30240 (16)	0.63795 (7)	0.0671 (5)
H15A	0.6539	0.2434	0.6378	0.081*
C16A	0.95826 (10)	0.29432 (13)	0.81973 (8)	0.0627 (5)
H16A	0.9681	0.3332	0.8480	0.075*
H16C	0.9834	0.3235	0.7925	0.075*
C17A	0.98951 (9)	0.19523 (13)	0.82771 (7)	0.0530 (4)
C18A	1.00645 (10)	0.13649 (14)	0.78927 (8)	0.0617 (5)
H18A	1.0011	0.1593	0.7579	0.074*
C19A	1.03111 (11)	0.04455 (16)	0.79674 (9)	0.0748 (6)
H19A	1.0409	0.0049	0.7706	0.090*
C20A	1.04120 (12)	0.01171 (18)	0.84297 (10)	0.0873 (7)
H20A	1.0579	−0.0503	0.8481	0.105*
C21A	1.02667 (12)	0.07020 (18)	0.88159 (9)	0.0853 (7)
H21A	1.0346	0.0482	0.9128	0.102*
C22A	1.00042 (10)	0.16140 (16)	0.87410 (7)	0.0684 (6)
H22A	0.9900	0.2005	0.9004	0.082*
O1B	0.61180 (7)	0.06448 (9)	0.98324 (5)	0.0633 (4)
O2B	0.54505 (7)	0.03102 (10)	0.82607 (5)	0.0668 (4)
N1B	0.70512 (7)	0.06323 (10)	0.92718 (5)	0.0467 (3)
N3B	0.57889 (7)	0.04627 (9)	0.90467 (5)	0.0455 (3)
C2B	0.63124 (9)	0.05873 (12)	0.94108 (7)	0.0480 (4)
C4AB	0.67396 (9)	0.04264 (11)	0.84349 (6)	0.0444 (4)
C4B	0.59496 (9)	0.03999 (12)	0.85581 (6)	0.0476 (4)
C5B	0.69580 (10)	0.03363 (12)	0.79517 (6)	0.0542 (5)
H5B	0.6597	0.0278	0.7712	0.065*
C6B	0.76984 (11)	0.03330 (13)	0.78293 (7)	0.0599 (5)
H6B	0.7842	0.0264	0.7509	0.072*
C7B	0.82289 (10)	0.04332 (13)	0.81853 (7)	0.0576 (5)
H7B	0.8732	0.0429	0.8102	0.069*
C8AB	0.72776 (9)	0.05321 (11)	0.87922 (6)	0.0435 (4)
C8B	0.80291 (9)	0.05388 (12)	0.86611 (7)	0.0533 (4)
H8B	0.8396	0.0615	0.8896	0.064*
C9B	0.76085 (10)	0.07851 (12)	0.96557 (6)	0.0545 (5)
H9B	0.7359	0.1041	0.9938	0.065*
H9D	0.7968	0.1257	0.9547	0.065*
C10B	0.80190 (10)	−0.01121 (13)	0.97963 (6)	0.0498 (4)
C11B	0.76367 (11)	−0.08904 (13)	0.99740 (7)	0.0588 (5)
H11B	0.7120	−0.0862	1.0005	0.071*
C12B	0.80122 (13)	−0.17137 (15)	1.01063 (8)	0.0711 (6)
H12B	0.7749	−0.2229	1.0233	0.085*
C13B	0.87748 (13)	−0.17699 (17)	1.00508 (8)	0.0769 (6)
H13B	0.9026	−0.2329	1.0131	0.092*
C14B	0.91636 (12)	−0.09989 (17)	0.98765 (8)	0.0736 (6)
H14B	0.9679	−0.1035	0.9840	0.088*
C15B	0.87924 (10)	−0.01730 (15)	0.97548 (7)	0.0617 (5)
H15B	0.9061	0.0351	0.9644	0.074*
C16B	0.50000 (9)	0.03632 (12)	0.91967 (7)	0.0511 (4)
H16B	0.4981	−0.0001	0.9494	0.061*
H16D	0.4733	0.0004	0.8952	0.061*
C17B	0.46085 (8)	0.13002 (12)	0.92738 (6)	0.0458 (4)
C18B	0.44536 (10)	0.16354 (14)	0.97336 (7)	0.0588 (5)
H18B	0.4611	0.1286	1.0000	0.071*
C19B	0.40708 (11)	0.24777 (15)	0.98023 (8)	0.0698 (6)
H19B	0.3966	0.2689	1.0113	0.084*
C20B	0.38446 (11)	0.30048 (14)	0.94116 (8)	0.0667 (6)
H20B	0.3591	0.3577	0.9456	0.080*
C21B	0.39945 (10)	0.26832 (14)	0.89542 (8)	0.0636 (5)
H21B	0.3841	0.3040	0.8689	0.076*
C22B	0.43716 (10)	0.18334 (13)	0.88838 (7)	0.0546 (4)
H22B	0.4466	0.1620	0.8572	0.066*

	U11	U22	U33	U12	U13	U23
O1A	0.0545 (8)	0.1060 (12)	0.0629 (9)	0.0081 (8)	0.0042 (7)	0.0195 (8)
O2A	0.0782 (10)	0.0927 (11)	0.0600 (8)	0.0061 (8)	−0.0186 (8)	−0.0133 (8)
N1A	0.0497 (8)	0.0526 (8)	0.0470 (8)	−0.0007 (7)	−0.0019 (7)	0.0021 (7)
N3A	0.0485 (8)	0.0514 (9)	0.0592 (9)	−0.0013 (7)	−0.0091 (7)	0.0050 (7)
C2A	0.0508 (10)	0.0543 (11)	0.0564 (11)	0.0043 (8)	−0.0011 (9)	0.0129 (9)
C4A	0.0613 (11)	0.0454 (10)	0.0558 (11)	0.0007 (9)	−0.0080 (10)	−0.0016 (9)
C4AA	0.0562 (10)	0.0357 (8)	0.0509 (10)	0.0001 (8)	−0.0025 (8)	−0.0001 (8)
C5A	0.0755 (13)	0.0490 (11)	0.0544 (11)	−0.0009 (10)	0.0017 (10)	−0.0074 (9)
C6A	0.0621 (12)	0.0599 (12)	0.0699 (13)	−0.0041 (10)	0.0134 (11)	−0.0085 (10)
C7A	0.0521 (11)	0.0594 (12)	0.0765 (14)	−0.0048 (9)	0.0008 (10)	−0.0087 (11)
C8A	0.0519 (10)	0.0581 (11)	0.0589 (11)	−0.0027 (9)	−0.0024 (9)	−0.0011 (10)
C8AA	0.0496 (9)	0.0364 (8)	0.0501 (10)	−0.0015 (7)	0.0003 (8)	0.0025 (8)
C9A	0.0567 (10)	0.0526 (10)	0.0500 (10)	0.0017 (9)	−0.0012 (9)	−0.0030 (9)
C10A	0.0447 (9)	0.0556 (10)	0.0436 (9)	0.0055 (8)	0.0024 (8)	−0.0033 (8)
C11A	0.0571 (11)	0.0617 (12)	0.0561 (11)	0.0052 (9)	−0.0041 (9)	−0.0008 (10)
C12A	0.0811 (15)	0.0588 (12)	0.0766 (14)	0.0096 (11)	0.0074 (12)	0.0109 (11)
C13A	0.0798 (15)	0.0928 (17)	0.0599 (13)	0.0336 (14)	0.0013 (12)	0.0178 (13)
C14A	0.0747 (15)	0.1002 (18)	0.0653 (14)	0.0219 (14)	−0.0215 (12)	−0.0031 (14)
C15A	0.0579 (11)	0.0750 (14)	0.0684 (13)	0.0040 (10)	−0.0115 (10)	−0.0061 (11)
C16A	0.0493 (10)	0.0628 (12)	0.0758 (14)	−0.0107 (9)	−0.0113 (10)	0.0083 (10)
C17A	0.0356 (8)	0.0619 (11)	0.0616 (11)	−0.0065 (8)	−0.0052 (8)	0.0112 (10)
C18A	0.0470 (10)	0.0761 (14)	0.0621 (12)	−0.0012 (10)	0.0051 (9)	0.0156 (11)
C19A	0.0567 (12)	0.0811 (15)	0.0867 (16)	0.0119 (11)	0.0168 (11)	0.0081 (13)
C20A	0.0631 (14)	0.0857 (17)	0.113 (2)	0.0246 (12)	0.0145 (14)	0.0336 (16)
C21A	0.0695 (14)	0.110 (2)	0.0764 (16)	0.0181 (14)	0.0016 (12)	0.0386 (15)
C22A	0.0568 (12)	0.0878 (15)	0.0607 (12)	0.0031 (11)	−0.0043 (10)	0.0106 (12)
O1B	0.0576 (8)	0.0803 (9)	0.0520 (8)	0.0075 (7)	0.0021 (6)	0.0003 (7)
O2B	0.0490 (7)	0.0854 (10)	0.0661 (8)	−0.0013 (7)	−0.0096 (7)	−0.0101 (7)
N1B	0.0412 (7)	0.0463 (8)	0.0525 (8)	0.0014 (6)	−0.0047 (6)	−0.0038 (7)
N3B	0.0388 (7)	0.0430 (8)	0.0545 (9)	0.0020 (6)	−0.0008 (6)	0.0011 (7)
C2B	0.0468 (9)	0.0414 (9)	0.0558 (11)	0.0049 (8)	−0.0025 (8)	0.0012 (8)
C4AB	0.0451 (9)	0.0342 (8)	0.0539 (10)	0.0011 (7)	−0.0002 (8)	−0.0014 (8)
C4B	0.0430 (9)	0.0424 (9)	0.0573 (11)	0.0001 (8)	−0.0052 (8)	−0.0026 (8)
C5B	0.0563 (11)	0.0509 (10)	0.0556 (11)	0.0017 (9)	−0.0021 (9)	−0.0032 (9)
C6B	0.0647 (12)	0.0540 (11)	0.0610 (12)	0.0016 (9)	0.0103 (10)	0.0006 (10)
C7B	0.0469 (10)	0.0493 (10)	0.0766 (14)	−0.0005 (8)	0.0122 (9)	0.0075 (10)
C8AB	0.0410 (9)	0.0329 (8)	0.0567 (10)	−0.0001 (7)	−0.0021 (8)	0.0006 (8)
C8B	0.0426 (9)	0.0503 (10)	0.0670 (12)	−0.0011 (8)	−0.0036 (9)	0.0051 (9)
C9B	0.0515 (10)	0.0515 (10)	0.0605 (11)	0.0012 (8)	−0.0098 (9)	−0.0124 (9)
C10B	0.0493 (10)	0.0514 (10)	0.0486 (10)	0.0019 (8)	−0.0101 (8)	−0.0098 (8)
C11B	0.0569 (11)	0.0610 (12)	0.0584 (11)	0.0023 (9)	−0.0048 (9)	−0.0066 (10)
C12B	0.0818 (15)	0.0609 (13)	0.0704 (13)	0.0033 (11)	−0.0094 (12)	0.0060 (11)
C13B	0.0835 (16)	0.0728 (15)	0.0745 (15)	0.0234 (13)	−0.0169 (13)	0.0020 (12)
C14B	0.0555 (12)	0.0895 (16)	0.0759 (14)	0.0186 (12)	−0.0117 (11)	0.0002 (13)
C15B	0.0499 (11)	0.0696 (13)	0.0654 (12)	0.0003 (10)	−0.0100 (9)	−0.0030 (10)
C16B	0.0393 (9)	0.0478 (10)	0.0662 (12)	−0.0032 (8)	0.0020 (8)	0.0087 (9)
C17B	0.0338 (8)	0.0465 (10)	0.0570 (10)	−0.0023 (7)	0.0011 (8)	0.0081 (8)
C18B	0.0556 (11)	0.0633 (12)	0.0574 (12)	0.0069 (9)	0.0038 (9)	0.0122 (10)
C19B	0.0674 (13)	0.0741 (14)	0.0679 (14)	0.0142 (11)	0.0075 (11)	−0.0061 (12)
C20B	0.0549 (11)	0.0543 (12)	0.0908 (16)	0.0124 (9)	0.0031 (11)	−0.0005 (11)
C21B	0.0558 (11)	0.0586 (12)	0.0764 (14)	0.0083 (9)	−0.0088 (10)	0.0154 (11)
C22B	0.0502 (10)	0.0575 (11)	0.0561 (11)	0.0037 (9)	−0.0032 (9)	0.0078 (9)

O1A—C2A	1.221 (2)	O1B—C2B	1.222 (2)
O2A—C4A	1.220 (2)	O2B—C4B	1.2222 (19)
N1A—C2A	1.368 (2)	N1B—C2B	1.379 (2)
N1A—C8AA	1.397 (2)	N1B—C8AB	1.397 (2)
N1A—C9A	1.474 (2)	N1B—C9B	1.474 (2)
N3A—C4A	1.389 (2)	N3B—C4B	1.387 (2)
N3A—C2A	1.399 (2)	N3B—C2B	1.388 (2)
N3A—C16A	1.478 (2)	N3B—C16B	1.479 (2)
C4A—C4AA	1.461 (2)	C4AB—C8AB	1.389 (2)
C4AA—C8AA	1.393 (2)	C4AB—C5B	1.401 (2)
C4AA—C5A	1.397 (2)	C4AB—C4B	1.455 (2)
C5A—C6A	1.369 (3)	C5B—C6B	1.368 (2)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.387 (3)	C6B—C7B	1.377 (3)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.374 (2)	C7B—C8B	1.375 (2)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C8AA	1.398 (2)	C8AB—C8B	1.393 (2)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.510 (2)	C9B—C10B	1.507 (2)
C9A—H9AA	0.9700	C9B—H9B	0.9700
C9A—H9AB	0.9700	C9B—H9D	0.9700
C10A—C11A	1.379 (2)	C10B—C11B	1.378 (2)
C10A—C15A	1.383 (2)	C10B—C15B	1.392 (2)
C11A—C12A	1.388 (3)	C11B—C12B	1.384 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.370 (3)	C12B—C13B	1.376 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.359 (3)	C13B—C14B	1.373 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.380 (3)	C14B—C15B	1.376 (3)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.513 (2)	C16B—C17B	1.503 (2)
C16A—H16A	0.9700	C16B—H16B	0.9700
C16A—H16C	0.9700	C16B—H16D	0.9700
C17A—C18A	1.380 (3)	C17B—C22B	1.381 (2)
C17A—C22A	1.384 (3)	C17B—C18B	1.386 (2)
C18A—C19A	1.377 (3)	C18B—C19B	1.378 (2)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.374 (3)	C19B—C20B	1.372 (3)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—C21A	1.373 (3)	C20B—C21B	1.372 (3)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C22A	1.377 (3)	C21B—C22B	1.382 (2)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—H22A	0.9300	C22B—H22B	0.9300
C2A—N1A—C8AA	123.03 (15)	C2B—N1B—C8AB	122.66 (14)
C2A—N1A—C9A	116.58 (15)	C2B—N1B—C9B	116.98 (14)
C8AA—N1A—C9A	120.11 (14)	C8AB—N1B—C9B	120.36 (14)
C4A—N3A—C2A	124.81 (15)	C4B—N3B—C2B	125.30 (14)
C4A—N3A—C16A	118.42 (15)	C4B—N3B—C16B	117.80 (14)
C2A—N3A—C16A	116.68 (16)	C2B—N3B—C16B	116.87 (14)
O1A—C2A—N1A	122.15 (17)	O1B—C2B—N1B	122.51 (16)
O1A—C2A—N3A	120.93 (17)	O1B—C2B—N3B	120.76 (16)
N1A—C2A—N3A	116.91 (16)	N1B—C2B—N3B	116.73 (15)
O2A—C4A—N3A	120.45 (18)	C8AB—C4AB—C5B	119.85 (16)
O2A—C4A—C4AA	124.14 (18)	C8AB—C4AB—C4B	120.59 (16)
N3A—C4A—C4AA	115.41 (16)	C5B—C4AB—C4B	119.56 (16)
C8AA—C4AA—C5A	119.31 (16)	O2B—C4B—N3B	120.91 (15)
C8AA—C4AA—C4A	120.56 (16)	O2B—C4B—C4AB	123.68 (17)
C5A—C4AA—C4A	120.13 (16)	N3B—C4B—C4AB	115.40 (15)
C6A—C5A—C4AA	121.04 (18)	C6B—C5B—C4AB	120.52 (17)
C6A—C5A—H5A	119.5	C6B—C5B—H5B	119.7
C4AA—C5A—H5A	119.5	C4AB—C5B—H5B	119.7
C5A—C6A—C7A	119.11 (19)	C5B—C6B—C7B	119.34 (18)
C5A—C6A—H6A	120.4	C5B—C6B—H6B	120.3
C7A—C6A—H6A	120.4	C7B—C6B—H6B	120.3
C8A—C7A—C6A	121.32 (18)	C8B—C7B—C6B	121.30 (18)
C8A—C7A—H7A	119.3	C8B—C7B—H7B	119.4
C6A—C7A—H7A	119.3	C6B—C7B—H7B	119.4
C7A—C8A—C8AA	119.60 (18)	C4AB—C8AB—C8B	118.93 (16)
C7A—C8A—H8A	120.2	C4AB—C8AB—N1B	119.22 (15)
C8AA—C8A—H8A	120.2	C8B—C8AB—N1B	121.84 (15)
C4AA—C8AA—N1A	118.95 (15)	C7B—C8B—C8AB	120.05 (17)
C4AA—C8AA—C8A	119.60 (17)	C7B—C8B—H8B	120.0
N1A—C8AA—C8A	121.45 (16)	C8AB—C8B—H8B	120.0
N1A—C9A—C10A	115.43 (14)	N1B—C9B—C10B	113.29 (14)
N1A—C9A—H9AA	108.4	N1B—C9B—H9B	108.9
C10A—C9A—H9AA	108.4	C10B—C9B—H9B	108.9
N1A—C9A—H9AB	108.4	N1B—C9B—H9D	108.9
C10A—C9A—H9AB	108.4	C10B—C9B—H9D	108.9
H9AA—C9A—H9AB	107.5	H9B—C9B—H9D	107.7
C11A—C10A—C15A	118.66 (18)	C11B—C10B—C15B	118.35 (17)
C11A—C10A—C9A	122.06 (16)	C11B—C10B—C9B	120.66 (16)
C15A—C10A—C9A	119.08 (17)	C15B—C10B—C9B	120.98 (17)
C10A—C11A—C12A	120.43 (19)	C10B—C11B—C12B	120.85 (19)
C10A—C11A—H11A	119.8	C10B—C11B—H11B	119.6
C12A—C11A—H11A	119.8	C12B—C11B—H11B	119.6
C13A—C12A—C11A	119.9 (2)	C13B—C12B—C11B	120.0 (2)
C13A—C12A—H12A	120.1	C13B—C12B—H12B	120.0
C11A—C12A—H12A	120.1	C11B—C12B—H12B	120.0
C14A—C13A—C12A	120.2 (2)	C14B—C13B—C12B	119.8 (2)
C14A—C13A—H13A	119.9	C14B—C13B—H13B	120.1
C12A—C13A—H13A	119.9	C12B—C13B—H13B	120.1
C13A—C14A—C15A	120.3 (2)	C13B—C14B—C15B	120.2 (2)
C13A—C14A—H14A	119.8	C13B—C14B—H14B	119.9
C15A—C14A—H14A	119.8	C15B—C14B—H14B	119.9
C14A—C15A—C10A	120.5 (2)	C14B—C15B—C10B	120.8 (2)
C14A—C15A—H15A	119.7	C14B—C15B—H15B	119.6
C10A—C15A—H15A	119.7	C10B—C15B—H15B	119.6
N3A—C16A—C17A	111.85 (14)	N3B—C16B—C17B	113.76 (13)
N3A—C16A—H16A	109.2	N3B—C16B—H16B	108.8
C17A—C16A—H16A	109.2	C17B—C16B—H16B	108.8
N3A—C16A—H16C	109.2	N3B—C16B—H16D	108.8
C17A—C16A—H16C	109.2	C17B—C16B—H16D	108.8
H16A—C16A—H16C	107.9	H16B—C16B—H16D	107.7
C18A—C17A—C22A	118.84 (19)	C22B—C17B—C18B	118.39 (16)
C18A—C17A—C16A	121.02 (17)	C22B—C17B—C16B	120.26 (16)
C22A—C17A—C16A	120.13 (19)	C18B—C17B—C16B	121.31 (16)
C19A—C18A—C17A	120.79 (19)	C19B—C18B—C17B	121.10 (18)
C19A—C18A—H18A	119.6	C19B—C18B—H18B	119.5
C17A—C18A—H18A	119.6	C17B—C18B—H18B	119.5
C20A—C19A—C18A	119.7 (2)	C20B—C19B—C18B	119.9 (2)
C20A—C19A—H19A	120.1	C20B—C19B—H19B	120.0
C18A—C19A—H19A	120.1	C18B—C19B—H19B	120.0
C21A—C20A—C19A	120.2 (2)	C19B—C20B—C21B	119.68 (18)
C21A—C20A—H20A	119.9	C19B—C20B—H20B	120.2
C19A—C20A—H20A	119.9	C21B—C20B—H20B	120.2
C20A—C21A—C22A	120.1 (2)	C20B—C21B—C22B	120.58 (19)
C20A—C21A—H21A	120.0	C20B—C21B—H21B	119.7
C22A—C21A—H21A	120.0	C22B—C21B—H21B	119.7
C21A—C22A—C17A	120.4 (2)	C17B—C22B—C21B	120.34 (18)
C21A—C22A—H22A	119.8	C17B—C22B—H22B	119.8
C17A—C22A—H22A	119.8	C21B—C22B—H22B	119.8
C8AA—N1A—C2A—O1A	−175.32 (16)	C8AB—N1B—C2B—O1B	177.61 (15)
C9A—N1A—C2A—O1A	10.7 (3)	C9B—N1B—C2B—O1B	−1.9 (2)
C8AA—N1A—C2A—N3A	5.7 (3)	C8AB—N1B—C2B—N3B	−1.8 (2)
C9A—N1A—C2A—N3A	−168.28 (14)	C9B—N1B—C2B—N3B	178.73 (13)
C4A—N3A—C2A—O1A	−179.83 (17)	C4B—N3B—C2B—O1B	179.24 (16)
C16A—N3A—C2A—O1A	−3.4 (3)	C16B—N3B—C2B—O1B	−2.5 (2)
C4A—N3A—C2A—N1A	−0.8 (3)	C4B—N3B—C2B—N1B	−1.4 (2)
C16A—N3A—C2A—N1A	175.60 (15)	C16B—N3B—C2B—N1B	176.87 (13)
C2A—N3A—C4A—O2A	177.49 (17)	C2B—N3B—C4B—O2B	−178.43 (16)
C16A—N3A—C4A—O2A	1.1 (3)	C16B—N3B—C4B—O2B	3.4 (2)
C2A—N3A—C4A—C4AA	−3.4 (3)	C2B—N3B—C4B—C4AB	2.9 (2)
C16A—N3A—C4A—C4AA	−179.81 (14)	C16B—N3B—C4B—C4AB	−175.28 (13)
O2A—C4A—C4AA—C8AA	−177.75 (17)	C8AB—C4AB—C4B—O2B	179.88 (16)
N3A—C4A—C4AA—C8AA	3.2 (2)	C5B—C4AB—C4B—O2B	−0.7 (3)
O2A—C4A—C4AA—C5A	1.8 (3)	C8AB—C4AB—C4B—N3B	−1.5 (2)
N3A—C4A—C4AA—C5A	−177.27 (15)	C5B—C4AB—C4B—N3B	177.94 (15)
C8AA—C4AA—C5A—C6A	−0.2 (3)	C8AB—C4AB—C5B—C6B	1.3 (3)
C4A—C4AA—C5A—C6A	−179.71 (17)	C4B—C4AB—C5B—C6B	−178.20 (16)
C4AA—C5A—C6A—C7A	−1.2 (3)	C4AB—C5B—C6B—C7B	−0.9 (3)
C5A—C6A—C7A—C8A	1.1 (3)	C5B—C6B—C7B—C8B	−0.2 (3)
C6A—C7A—C8A—C8AA	0.3 (3)	C5B—C4AB—C8AB—C8B	−0.5 (2)
C5A—C4AA—C8AA—N1A	−178.40 (15)	C4B—C4AB—C8AB—C8B	178.98 (15)
C4A—C4AA—C8AA—N1A	1.1 (2)	C5B—C4AB—C8AB—N1B	179.26 (15)
C5A—C4AA—C8AA—C8A	1.6 (3)	C4B—C4AB—C8AB—N1B	−1.3 (2)
C4A—C4AA—C8AA—C8A	−178.84 (16)	C2B—N1B—C8AB—C4AB	3.1 (2)
C2A—N1A—C8AA—C4AA	−5.9 (2)	C9B—N1B—C8AB—C4AB	−177.48 (14)
C9A—N1A—C8AA—C4AA	167.91 (15)	C2B—N1B—C8AB—C8B	−177.20 (15)
C2A—N1A—C8AA—C8A	174.10 (16)	C9B—N1B—C8AB—C8B	2.3 (2)
C9A—N1A—C8AA—C8A	−12.1 (2)	C6B—C7B—C8B—C8AB	0.9 (3)
C7A—C8A—C8AA—C4AA	−1.7 (3)	C4AB—C8AB—C8B—C7B	−0.6 (2)
C7A—C8A—C8AA—N1A	178.33 (16)	N1B—C8AB—C8B—C7B	179.66 (15)
C2A—N1A—C9A—C10A	−99.51 (18)	C2B—N1B—C9B—C10B	102.55 (18)
C8AA—N1A—C9A—C10A	86.33 (19)	C8AB—N1B—C9B—C10B	−76.95 (19)
N1A—C9A—C10A—C11A	38.0 (2)	N1B—C9B—C10B—C11B	−60.1 (2)
N1A—C9A—C10A—C15A	−147.14 (17)	N1B—C9B—C10B—C15B	120.61 (18)
C15A—C10A—C11A—C12A	0.1 (3)	C15B—C10B—C11B—C12B	−0.2 (3)
C9A—C10A—C11A—C12A	174.99 (16)	C9B—C10B—C11B—C12B	−179.58 (17)
C10A—C11A—C12A—C13A	0.0 (3)	C10B—C11B—C12B—C13B	−1.5 (3)
C11A—C12A—C13A—C14A	−0.5 (3)	C11B—C12B—C13B—C14B	1.8 (3)
C12A—C13A—C14A—C15A	0.9 (3)	C12B—C13B—C14B—C15B	−0.4 (3)
C13A—C14A—C15A—C10A	−0.8 (3)	C13B—C14B—C15B—C10B	−1.4 (3)
C11A—C10A—C15A—C14A	0.3 (3)	C11B—C10B—C15B—C14B	1.7 (3)
C9A—C10A—C15A—C14A	−174.73 (18)	C9B—C10B—C15B—C14B	−178.98 (17)
C4A—N3A—C16A—C17A	88.4 (2)	C4B—N3B—C16B—C17B	−97.31 (18)
C2A—N3A—C16A—C17A	−88.3 (2)	C2B—N3B—C16B—C17B	84.33 (18)
N3A—C16A—C17A—C18A	81.3 (2)	N3B—C16B—C17B—C22B	76.8 (2)
N3A—C16A—C17A—C22A	−97.6 (2)	N3B—C16B—C17B—C18B	−105.44 (19)
C22A—C17A—C18A—C19A	2.4 (3)	C22B—C17B—C18B—C19B	0.2 (3)
C16A—C17A—C18A—C19A	−176.51 (17)	C16B—C17B—C18B—C19B	−177.63 (17)
C17A—C18A—C19A—C20A	−2.0 (3)	C17B—C18B—C19B—C20B	−0.8 (3)
C18A—C19A—C20A—C21A	0.1 (3)	C18B—C19B—C20B—C21B	0.7 (3)
C19A—C20A—C21A—C22A	1.4 (4)	C19B—C20B—C21B—C22B	0.0 (3)
C20A—C21A—C22A—C17A	−0.9 (3)	C18B—C17B—C22B—C21B	0.5 (3)
C18A—C17A—C22A—C21A	−1.0 (3)	C16B—C17B—C22B—C21B	178.34 (16)
C16A—C17A—C22A—C21A	177.99 (18)	C20B—C21B—C22B—C17B	−0.6 (3)

Cg4 and Cg8 are the centroids of the C17A–C22A and C10B–C15B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19A—H19A···O2bi	0.93	2.70	3.419 (3)	134
C6B—H6B···C11aii	0.93	2.89	3.604 (3)	134
C21B—H21B···C11aiii	0.93	2.80	3.600 (3)	145
C19A—H19A···O2bi	0.93	2.70	3.419 (3)	134
C7B—H7B···Cg4	0.93	2.78	3.586 (2)	146
C5A—H5A···Cg8ii	0.93	2.90	3.641 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 and Cg8 are the centroids of the C17A–C22A and C10B–C15B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19A—H19A⋯O2bi	0.93	2.70	3.419 (3)	134
C6B—H6B⋯C11aii	0.93	2.89	3.604 (3)	134
C21B—H21B⋯C11aiii	0.93	2.80	3.600 (3)	145
C19A—H19A⋯O2bi	0.93	2.70	3.419 (3)	134
C7B—H7B⋯Cg4	0.93	2.78	3.586 (2)	146
C5A—H5A⋯Cg8ii	0.93	2.90	3.641 (2)	138

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