3-(4-Chloro-anilino)-5,5-dimethyl-cyclo-hex-2-en-1-one.

The asymmetric unit of the title compound, C(14)H(16)ClNO, contains two independent mol-ecules, both with the cyclo-hexene ring in a sofa conformation. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules related by translation along the a axis into two crystallographically independent chains. Weak C-H⋯π inter-actions are also observed.

Related literature

For related structures, see: Bertolasi et al. (1998 ▶); Mehdi et al. (2010 ▶). For general background to enamines as versatile substrates for the preparation of bioactive alkaloids, see: Heller & Natarajan (2006 ▶); Katritzky et al. (1993 ▶); Campaigine & Lake (1959 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H16ClNO

M = 249.73

Monoclinic,

a = 7.4103 (2) Å

b = 15.1916 (5) Å

c = 11.6408 (4) Å

β = 99.443 (3)°

V = 1292.70 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.961, T max = 1.000

19792 measured reflections

5570 independent reflections

4069 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.03

5570 reflections

319 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 2721 Friedel pairs

Flack parameter: −0.04 (5)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010495/cv5258sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010495/cv5258Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010495/cv5258Isup3.cml

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

C14H16ClNO	F(000) = 528
Mr = 249.73	Dx = 1.283 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 7292 reflections
a = 7.4103 (2) Å	θ = 3.5–29.1°
b = 15.1916 (5) Å	µ = 0.28 mm−1
c = 11.6408 (4) Å	T = 293 K
β = 99.443 (3)°	Block, white
V = 1292.70 (7) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5570 independent reflections
Radiation source: fine-focus sealed tube	4069 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 0 pixels mm-1	θmax = 27.0°, θmin = 3.6°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −19→19
Tmin = 0.961, Tmax = 1.000	l = −14→14
19792 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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0374P)2 + 0.1217P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
5570 reflections	Δρmax = 0.15 e Å−3
319 parameters	Δρmin = −0.21 e Å−3
2 restraints	Absolute structure: Flack (1983), 2721 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (5)

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1A	0.02376 (10)	0.84221 (5)	−0.37777 (6)	0.0695 (3)
N1A	0.1625 (3)	0.86014 (14)	0.13741 (18)	0.0394 (5)
C1A	0.6616 (3)	0.87416 (14)	0.2364 (2)	0.0361 (6)
C3A	0.3290 (3)	0.86484 (13)	0.20386 (19)	0.0307 (5)
O1A	0.8071 (2)	0.88210 (13)	0.19728 (17)	0.0576 (6)
C6A	0.6634 (3)	0.87541 (16)	0.3650 (2)	0.0418 (6)
H61A	0.7716	0.9066	0.4022	0.050*
H62A	0.6712	0.8154	0.3938	0.050*
C4A	0.3259 (3)	0.87268 (15)	0.3326 (2)	0.0400 (6)
H42A	0.3182	0.8142	0.3649	0.048*
H41A	0.2170	0.9048	0.3440	0.048*
C12A	0.0607 (3)	0.84585 (15)	−0.2259 (2)	0.0404 (6)
C13A	0.1651 (3)	0.78103 (16)	−0.1636 (2)	0.0441 (7)
H13	0.2131	0.7353	−0.2022	0.053*
C2A	0.4897 (3)	0.86468 (14)	0.1616 (2)	0.0322 (5)
H2A	0.4875	0.8582	0.0820	0.039*
C10A	0.0213 (3)	0.91674 (15)	−0.0498 (2)	0.0422 (6)
H10A	−0.0282	0.9621	−0.0111	0.051*
C14A	0.1978 (3)	0.78474 (15)	−0.0433 (2)	0.0399 (6)
H14A	0.2665	0.7410	−0.0007	0.048*
C11A	−0.0134 (3)	0.91349 (15)	−0.1705 (2)	0.0431 (6)
H11A	−0.0853	0.9562	−0.2130	0.052*
C5A	0.4937 (3)	0.91935 (15)	0.39910 (19)	0.0366 (6)
C9A	0.1283 (3)	0.85343 (14)	0.0136 (2)	0.0340 (6)
C7A	0.4922 (3)	1.01738 (15)	0.3674 (2)	0.0436 (6)
H72A	0.3848	1.0447	0.3876	0.065*
H73A	0.4916	1.0236	0.2853	0.065*
H71A	0.5993	1.0453	0.4095	0.065*
C8A	0.4948 (4)	0.9102 (2)	0.5304 (2)	0.0578 (8)
H83A	0.4911	0.8490	0.5503	0.087*
H81A	0.3899	0.9396	0.5509	0.087*
H82A	0.6042	0.9364	0.5721	0.087*
Cl1B	0.53853 (10)	0.65806 (5)	−0.33380 (7)	0.0718 (3)
C1B	1.1802 (3)	0.62985 (15)	0.2807 (2)	0.0398 (6)
C11B	0.6804 (3)	0.71986 (15)	−0.1197 (2)	0.0431 (6)
H11B	0.7258	0.7663	−0.1585	0.052*
C12B	0.5780 (3)	0.65421 (16)	−0.1819 (2)	0.0429 (6)
C3B	0.8480 (3)	0.63611 (14)	0.2483 (2)	0.0342 (6)
N1B	0.6810 (3)	0.64009 (13)	0.1810 (2)	0.0416 (6)
C4B	0.8453 (3)	0.62493 (15)	0.3765 (2)	0.0395 (6)
H42B	0.7358	0.5929	0.3866	0.047*
H41B	0.8391	0.6826	0.4116	0.047*
C2B	1.0094 (3)	0.64015 (14)	0.2057 (2)	0.0376 (6)
H2B	1.0074	0.6497	0.1266	0.045*
C6B	1.1831 (3)	0.62237 (15)	0.4087 (2)	0.0420 (6)
H62B	1.1919	0.6809	0.4424	0.050*
H61B	1.2914	0.5899	0.4428	0.050*
C14B	0.5403 (3)	0.58314 (15)	−0.0062 (2)	0.0448 (7)
H14B	0.4913	0.5376	0.0323	0.054*
C10B	0.7145 (3)	0.71586 (15)	−0.0002 (2)	0.0397 (6)
H10B	0.7831	0.7598	0.0422	0.048*
C9B	0.6466 (3)	0.64625 (15)	0.0577 (2)	0.0351 (6)
C13B	0.5053 (3)	0.58639 (16)	−0.1263 (2)	0.0480 (7)
H13'	0.4337	0.5434	−0.1688	0.058*
O1B	1.3270 (2)	0.62702 (14)	0.24154 (19)	0.0645 (6)
C5B	1.0126 (3)	0.57602 (14)	0.4406 (2)	0.0374 (6)
C7B	1.0128 (4)	0.58084 (17)	0.5718 (2)	0.0543 (7)
H73B	0.9032	0.5541	0.5896	0.081*
H72B	1.0177	0.6413	0.5961	0.081*
H71B	1.1175	0.5501	0.6122	0.081*
C8B	1.0106 (3)	0.47940 (15)	0.4026 (2)	0.0467 (7)
H83B	0.9045	0.4508	0.4225	0.070*
H81B	1.1189	0.4505	0.4414	0.070*
H82B	1.0072	0.4763	0.3199	0.070*
H1B	0.587 (4)	0.6320 (16)	0.210 (2)	0.057 (8)*
H1A	0.067 (4)	0.8708 (15)	0.167 (2)	0.047 (7)*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0762 (7)	0.0863 (6)	0.0423 (6)	0.0071 (4)	−0.0012 (7)	−0.0017 (4)
N1A	0.0234 (11)	0.0560 (13)	0.0409 (14)	−0.0008 (8)	0.0113 (10)	−0.0050 (9)
C1A	0.0256 (13)	0.0372 (13)	0.0465 (16)	0.0029 (9)	0.0089 (11)	−0.0111 (10)
C3A	0.0266 (12)	0.0317 (11)	0.0347 (14)	−0.0023 (9)	0.0074 (11)	−0.0006 (9)
O1A	0.0259 (10)	0.0883 (14)	0.0613 (13)	−0.0067 (9)	0.0147 (9)	−0.0300 (10)
C6A	0.0349 (14)	0.0495 (15)	0.0380 (15)	0.0096 (11)	−0.0029 (12)	−0.0020 (11)
C4A	0.0364 (14)	0.0477 (14)	0.0394 (15)	−0.0050 (11)	0.0173 (12)	0.0029 (11)
C12A	0.0329 (13)	0.0518 (14)	0.0352 (15)	−0.0047 (10)	0.0017 (11)	−0.0027 (11)
C13A	0.0347 (14)	0.0463 (14)	0.0489 (18)	0.0058 (10)	−0.0005 (13)	−0.0120 (11)
C2A	0.0254 (12)	0.0430 (13)	0.0299 (13)	0.0000 (9)	0.0096 (10)	−0.0046 (10)
C10A	0.0315 (14)	0.0429 (14)	0.0533 (18)	0.0042 (11)	0.0104 (12)	−0.0051 (12)
C14A	0.0305 (13)	0.0387 (13)	0.0480 (17)	0.0047 (10)	−0.0004 (12)	−0.0019 (11)
C11A	0.0356 (14)	0.0414 (14)	0.0509 (18)	0.0066 (10)	0.0034 (13)	0.0041 (11)
C5A	0.0370 (14)	0.0443 (13)	0.0297 (14)	0.0021 (10)	0.0091 (12)	0.0028 (10)
C9A	0.0194 (11)	0.0412 (13)	0.0418 (16)	−0.0026 (9)	0.0062 (11)	−0.0016 (10)
C7A	0.0457 (15)	0.0436 (14)	0.0430 (15)	0.0041 (11)	0.0117 (12)	−0.0065 (11)
C8A	0.0677 (19)	0.0769 (19)	0.0302 (15)	0.0024 (15)	0.0121 (14)	0.0026 (13)
Cl1B	0.0730 (7)	0.0900 (7)	0.0497 (7)	−0.0030 (4)	0.0022 (7)	−0.0010 (4)
C1B	0.0206 (12)	0.0401 (14)	0.0596 (19)	−0.0018 (9)	0.0088 (12)	0.0049 (11)
C11B	0.0362 (14)	0.0375 (13)	0.0562 (19)	−0.0032 (10)	0.0097 (13)	0.0027 (12)
C12B	0.0318 (13)	0.0513 (15)	0.0445 (16)	0.0063 (11)	0.0030 (12)	0.0011 (11)
C3B	0.0225 (12)	0.0338 (12)	0.0472 (17)	0.0035 (9)	0.0080 (11)	0.0011 (10)
N1B	0.0189 (11)	0.0573 (13)	0.0504 (15)	−0.0005 (9)	0.0114 (11)	0.0061 (10)
C4B	0.0274 (13)	0.0462 (14)	0.0473 (16)	0.0048 (10)	0.0128 (12)	0.0029 (11)
C2B	0.0241 (13)	0.0433 (13)	0.0464 (16)	0.0008 (9)	0.0089 (12)	0.0061 (11)
C6B	0.0278 (13)	0.0411 (13)	0.0546 (18)	−0.0048 (10)	−0.0003 (12)	0.0032 (11)
C14B	0.0284 (13)	0.0435 (15)	0.062 (2)	−0.0059 (10)	0.0055 (13)	0.0062 (12)
C10B	0.0282 (12)	0.0382 (13)	0.0532 (17)	−0.0041 (9)	0.0082 (12)	−0.0037 (11)
C9B	0.0188 (11)	0.0391 (12)	0.0479 (17)	0.0027 (9)	0.0073 (12)	0.0027 (10)
C13B	0.0324 (14)	0.0439 (15)	0.065 (2)	−0.0054 (11)	−0.0008 (13)	−0.0058 (13)
O1B	0.0222 (10)	0.0935 (15)	0.0808 (17)	0.0033 (9)	0.0176 (11)	0.0169 (11)
C5B	0.0312 (13)	0.0379 (13)	0.0435 (16)	−0.0014 (10)	0.0071 (12)	0.0027 (10)
C7B	0.0528 (17)	0.0598 (17)	0.0499 (18)	−0.0035 (13)	0.0075 (14)	0.0030 (13)
C8B	0.0389 (14)	0.0401 (14)	0.0627 (19)	−0.0020 (11)	0.0127 (13)	0.0049 (12)

Cl1A—C12A	1.744 (3)	Cl1B—C12B	1.745 (3)
N1A—C3A	1.346 (3)	C1B—O1B	1.247 (3)
N1A—C9A	1.426 (3)	C1B—C2B	1.424 (3)
N1A—H1A	0.85 (3)	C1B—C6B	1.491 (4)
C1A—O1A	1.244 (3)	C11B—C10B	1.374 (3)
C1A—C2A	1.427 (3)	C11B—C12B	1.383 (3)
C1A—C6A	1.495 (3)	C11B—H11B	0.9300
C3A—C2A	1.361 (3)	C12B—C13B	1.373 (3)
C3A—C4A	1.508 (3)	C3B—N1B	1.353 (3)
C6A—C5A	1.533 (3)	C3B—C2B	1.370 (3)
C6A—H61A	0.9700	C3B—C4B	1.506 (3)
C6A—H62A	0.9700	N1B—C9B	1.418 (3)
C4A—C5A	1.527 (3)	N1B—H1B	0.83 (3)
C4A—H42A	0.9700	C4B—C5B	1.530 (3)
C4A—H41A	0.9700	C4B—H42B	0.9700
C12A—C11A	1.375 (3)	C4B—H41B	0.9700
C12A—C13A	1.382 (3)	C2B—H2B	0.9300
C13A—C14A	1.382 (3)	C6B—C5B	1.544 (3)
C13A—H13	0.9300	C6B—H62B	0.9700
C2A—H2A	0.9300	C6B—H61B	0.9700
C10A—C9A	1.381 (3)	C14B—C9B	1.379 (3)
C10A—C11A	1.387 (3)	C14B—C13B	1.380 (3)
C10A—H10A	0.9300	C14B—H14B	0.9300
C14A—C9A	1.380 (3)	C10B—C9B	1.392 (3)
C14A—H14A	0.9300	C10B—H10B	0.9300
C11A—H11A	0.9300	C13B—H13'	0.9300
C5A—C8A	1.533 (3)	C5B—C7B	1.529 (4)
C5A—C7A	1.534 (3)	C5B—C8B	1.533 (3)
C7A—H72A	0.9600	C7B—H73B	0.9600
C7A—H73A	0.9600	C7B—H72B	0.9600
C7A—H71A	0.9600	C7B—H71B	0.9600
C8A—H83A	0.9600	C8B—H83B	0.9600
C8A—H81A	0.9600	C8B—H81B	0.9600
C8A—H82A	0.9600	C8B—H82B	0.9600
C3A—N1A—C9A	125.35 (19)	O1B—C1B—C2B	121.4 (3)
C3A—N1A—H1A	120.2 (18)	O1B—C1B—C6B	119.5 (2)
C9A—N1A—H1A	113.6 (18)	C2B—C1B—C6B	119.1 (2)
O1A—C1A—C2A	121.8 (2)	C10B—C11B—C12B	119.5 (2)
O1A—C1A—C6A	120.0 (2)	C10B—C11B—H11B	120.3
C2A—C1A—C6A	118.2 (2)	C12B—C11B—H11B	120.3
N1A—C3A—C2A	124.5 (2)	C13B—C12B—C11B	121.2 (3)
N1A—C3A—C4A	114.42 (19)	C13B—C12B—Cl1B	119.3 (2)
C2A—C3A—C4A	121.1 (2)	C11B—C12B—Cl1B	119.5 (2)
C1A—C6A—C5A	113.10 (17)	N1B—C3B—C2B	123.9 (2)
C1A—C6A—H61A	109.0	N1B—C3B—C4B	114.8 (2)
C5A—C6A—H61A	109.0	C2B—C3B—C4B	121.2 (2)
C1A—C6A—H62A	109.0	C3B—N1B—C9B	125.8 (2)
C5A—C6A—H62A	109.0	C3B—N1B—H1B	121 (2)
H61A—C6A—H62A	107.8	C9B—N1B—H1B	113 (2)
C3A—C4A—C5A	113.37 (18)	C3B—C4B—C5B	113.35 (19)
C3A—C4A—H42A	108.9	C3B—C4B—H42B	108.9
C5A—C4A—H42A	108.9	C5B—C4B—H42B	108.9
C3A—C4A—H41A	108.9	C3B—C4B—H41B	108.9
C5A—C4A—H41A	108.9	C5B—C4B—H41B	108.9
H42A—C4A—H41A	107.7	H42B—C4B—H41B	107.7
C11A—C12A—C13A	121.2 (2)	C3B—C2B—C1B	121.0 (2)
C11A—C12A—Cl1A	119.41 (19)	C3B—C2B—H2B	119.5
C13A—C12A—Cl1A	119.40 (19)	C1B—C2B—H2B	119.5
C14A—C13A—C12A	119.5 (2)	C1B—C6B—C5B	113.41 (19)
C14A—C13A—H13	120.2	C1B—C6B—H62B	108.9
C12A—C13A—H13	120.2	C5B—C6B—H62B	108.9
C3A—C2A—C1A	121.7 (2)	C1B—C6B—H61B	108.9
C3A—C2A—H2A	119.1	C5B—C6B—H61B	108.9
C1A—C2A—H2A	119.1	H62B—C6B—H61B	107.7
C9A—C10A—C11A	120.7 (2)	C9B—C14B—C13B	121.2 (2)
C9A—C10A—H10A	119.6	C9B—C14B—H14B	119.4
C11A—C10A—H10A	119.6	C13B—C14B—H14B	119.4
C9A—C14A—C13A	120.0 (2)	C11B—C10B—C9B	120.2 (2)
C9A—C14A—H14A	120.0	C11B—C10B—H10B	119.9
C13A—C14A—H14A	120.0	C9B—C10B—H10B	119.9
C12A—C11A—C10A	118.7 (2)	C14B—C9B—C10B	119.1 (2)
C12A—C11A—H11A	120.6	C14B—C9B—N1B	119.5 (2)
C10A—C11A—H11A	120.6	C10B—C9B—N1B	121.4 (2)
C4A—C5A—C6A	107.51 (19)	C12B—C13B—C14B	118.8 (2)
C4A—C5A—C8A	109.5 (2)	C12B—C13B—H13'	120.6
C6A—C5A—C8A	110.39 (19)	C14B—C13B—H13'	120.6
C4A—C5A—C7A	110.86 (19)	C7B—C5B—C4B	109.3 (2)
C6A—C5A—C7A	109.52 (19)	C7B—C5B—C8B	109.45 (19)
C8A—C5A—C7A	109.0 (2)	C4B—C5B—C8B	110.84 (19)
C14A—C9A—C10A	119.8 (2)	C7B—C5B—C6B	110.6 (2)
C14A—C9A—N1A	121.4 (2)	C4B—C5B—C6B	106.90 (18)
C10A—C9A—N1A	118.8 (2)	C8B—C5B—C6B	109.67 (19)
C5A—C7A—H72A	109.5	C5B—C7B—H73B	109.5
C5A—C7A—H73A	109.5	C5B—C7B—H72B	109.5
H72A—C7A—H73A	109.5	H73B—C7B—H72B	109.5
C5A—C7A—H71A	109.5	C5B—C7B—H71B	109.5
H72A—C7A—H71A	109.5	H73B—C7B—H71B	109.5
H73A—C7A—H71A	109.5	H72B—C7B—H71B	109.5
C5A—C8A—H83A	109.5	C5B—C8B—H83B	109.5
C5A—C8A—H81A	109.5	C5B—C8B—H81B	109.5
H83A—C8A—H81A	109.5	H83B—C8B—H81B	109.5
C5A—C8A—H82A	109.5	C5B—C8B—H82B	109.5
H83A—C8A—H82A	109.5	H83B—C8B—H82B	109.5
H81A—C8A—H82A	109.5	H81B—C8B—H82B	109.5
C9A—N1A—C3A—C2A	0.7 (4)	C10B—C11B—C12B—C13B	1.9 (4)
C9A—N1A—C3A—C4A	179.28 (19)	C10B—C11B—C12B—Cl1B	−178.72 (17)
O1A—C1A—C6A—C5A	145.2 (2)	C2B—C3B—N1B—C9B	2.0 (4)
C2A—C1A—C6A—C5A	−34.1 (3)	C4B—C3B—N1B—C9B	−176.87 (19)
N1A—C3A—C4A—C5A	−153.0 (2)	N1B—C3B—C4B—C5B	150.9 (2)
C2A—C3A—C4A—C5A	25.6 (3)	C2B—C3B—C4B—C5B	−28.0 (3)
C11A—C12A—C13A—C14A	−0.8 (4)	N1B—C3B—C2B—C1B	−175.9 (2)
Cl1A—C12A—C13A—C14A	178.69 (18)	C4B—C3B—C2B—C1B	2.9 (3)
N1A—C3A—C2A—C1A	176.9 (2)	O1B—C1B—C2B—C3B	174.7 (2)
C4A—C3A—C2A—C1A	−1.6 (3)	C6B—C1B—C2B—C3B	−5.3 (3)
O1A—C1A—C2A—C3A	−173.3 (2)	O1B—C1B—C6B—C5B	−147.5 (2)
C6A—C1A—C2A—C3A	6.0 (3)	C2B—C1B—C6B—C5B	32.5 (3)
C12A—C13A—C14A—C9A	−0.8 (3)	C12B—C11B—C10B—C9B	0.1 (3)
C13A—C12A—C11A—C10A	1.2 (4)	C13B—C14B—C9B—C10B	2.1 (3)
Cl1A—C12A—C11A—C10A	−178.33 (17)	C13B—C14B—C9B—N1B	−179.3 (2)
C9A—C10A—C11A—C12A	0.1 (3)	C11B—C10B—C9B—C14B	−2.0 (3)
C3A—C4A—C5A—C6A	−50.4 (2)	C11B—C10B—C9B—N1B	179.46 (19)
C3A—C4A—C5A—C8A	−170.3 (2)	C3B—N1B—C9B—C14B	122.7 (2)
C3A—C4A—C5A—C7A	69.3 (2)	C3B—N1B—C9B—C10B	−58.8 (3)
C1A—C6A—C5A—C4A	54.9 (2)	C11B—C12B—C13B—C14B	−1.8 (4)
C1A—C6A—C5A—C8A	174.3 (2)	Cl1B—C12B—C13B—C14B	178.80 (18)
C1A—C6A—C5A—C7A	−65.6 (2)	C9B—C14B—C13B—C12B	−0.2 (4)
C13A—C14A—C9A—C10A	2.1 (3)	C3B—C4B—C5B—C7B	171.04 (19)
C13A—C14A—C9A—N1A	−178.7 (2)	C3B—C4B—C5B—C8B	−68.2 (3)
C11A—C10A—C9A—C14A	−1.8 (3)	C3B—C4B—C5B—C6B	51.3 (3)
C11A—C10A—C9A—N1A	179.1 (2)	C1B—C6B—C5B—C7B	−172.9 (2)
C3A—N1A—C9A—C14A	58.4 (3)	C1B—C6B—C5B—C4B	−53.9 (2)
C3A—N1A—C9A—C10A	−122.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1Ai	0.85 (3)	2.02 (3)	2.852 (3)	165 (2)
N1B—H1B···O1Bi	0.83 (3)	2.02 (3)	2.833 (3)	165 (2)
C7A—H72A···Cg1ii	0.96	2.71	3.637 (3)	163
C8B—H83B···Cg2iii	0.96	2.70	3.640 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9A–C14A and C9B–C14B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O1Ai	0.85 (3)	2.02 (3)	2.852 (3)	165 (2)
N1B—H1B⋯O1Bi	0.83 (3)	2.02 (3)	2.833 (3)	165 (2)
C7A—H72A⋯Cg1ii	0.96	2.71	3.637 (3)	163
C8B—H83B⋯Cg2iii	0.96	2.70	3.640 (3)	167

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