5-Dichloro-acetyl-4-methyl-2,3,4,5-tetra-hydro-1H-1,5-benzodiazepin-2-one hemihydrate.

There are two crystallographically independent organic mol-ecules in the asymmetric unit of the title compound, C(12)H(12)Cl(2)N(2)O(2)·0.5H(2)O. The benzodiazepine ring adopts a distorted boat conformation in both molecules. The crystal packing is controlled by N-H⋯O, C-H⋯O and O-H⋯O intra- and inter-molecular hydrogen bonds. A graph-set motif of R(3) (3)(14) dimer formation by a combination of N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds stabilizes the mol-ecules and extends along a axis.

Related literature

For the anti­convulsant activity of benzodiazepine, see: MacDonald (2002 ▶). For their hypnotic effect, see: Gringauz (1999 ▶). For their use in the treatment of gastrointestinal and central nervous system disorders, see: Rahbaek et al. (1999 ▶). For other therapeutic applications, see: Albright et al. (1998 ▶); Lee et al. (1999 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For details of the preparation of the title compound, see: Venkatraj et al. (2008 ▶).

Experimental

Crystal data

C12H12Cl2N2O2·0.5H2O

M = 592.29

Monoclinic,

a = 8.5470 (3) Å

b = 18.0837 (6) Å

c = 8.8697 (3) Å

β = 95.405 (2)°

V = 1364.82 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.48 mm−1

T = 293 K

0.26 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.884, T max = 0.901

14191 measured reflections

5599 independent reflections

4873 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.110

S = 1.04

5599 reflections

352 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.62 e Å−3

Absolute structure: Flack (1983 ▶), 2698 Friedel pairs

Flack parameter: 0.06 (6)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036940/bt5048sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036940/bt5048Isup2.hkl

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

C12H12Cl2N2O2·0.5H2O	F(000) = 612
Mr = 592.29	Dx = 1.441 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4629 reflections
a = 8.5470 (3) Å	θ = 2.3–26.5°
b = 18.0837 (6) Å	µ = 0.48 mm−1
c = 8.8697 (3) Å	T = 293 K
β = 95.405 (2)°	Block, colourless
V = 1364.82 (8) Å3	0.26 × 0.24 × 0.22 mm
Z = 2

Bruker Kappa APEXII area-detector diffractometer	5599 independent reflections
Radiation source: fine-focus sealed tube	4873 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω and φ scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.884, Tmax = 0.901	k = −22→22
14191 measured reflections	l = −11→10

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.7028P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.006
5599 reflections	Δρmax = 0.46 e Å−3
352 parameters	Δρmin = −0.62 e Å−3
1 restraint	Absolute structure: Flack (1983),2698 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (6)

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	1.62028 (16)	−0.29670 (7)	1.77856 (13)	0.0941 (4)
Cl1B	1.04826 (15)	0.13662 (6)	0.96558 (15)	0.0906 (4)
Cl2A	1.48485 (16)	−0.15064 (6)	1.74118 (13)	0.0858 (3)
Cl2B	0.8172 (2)	0.15716 (9)	1.17529 (14)	0.1300 (7)
O1A	1.5519 (3)	−0.46993 (14)	1.2925 (3)	0.0594 (6)
O1B	1.0719 (3)	−0.07368 (15)	0.6539 (2)	0.0573 (6)
O2A	1.6504 (3)	−0.20942 (14)	1.4809 (3)	0.0635 (7)
O2B	0.7429 (3)	0.02505 (17)	1.0049 (4)	0.0852 (9)
O3	1.2224 (4)	−0.56267 (15)	1.5161 (4)	0.0677 (7)
H1W	1.279 (6)	−0.601 (3)	1.502 (6)	0.108 (19)*
H2W	1.140 (5)	−0.570 (2)	1.467 (4)	0.059 (11)*
N1A	1.3405 (3)	−0.42583 (13)	1.3919 (3)	0.0403 (5)
H1A	1.325 (4)	−0.469 (2)	1.432 (4)	0.057 (10)*
N1B	1.2097 (3)	−0.03383 (14)	0.8658 (3)	0.0399 (5)
H1B	1.261 (3)	−0.0095 (17)	0.811 (3)	0.031 (7)*
C2A	1.4518 (3)	−0.42199 (16)	1.2939 (3)	0.0420 (6)
C2B	1.1026 (3)	−0.07798 (16)	0.7907 (3)	0.0410 (6)
C3A	1.4398 (4)	−0.35821 (17)	1.1848 (3)	0.0462 (7)
H3A	1.3314	−0.3539	1.1423	0.055*
H3B	1.5028	−0.3694	1.1023	0.055*
C3B	1.0275 (4)	−0.13513 (16)	0.8847 (3)	0.0465 (7)
H3C	1.1089	−0.1594	0.9505	0.056*
H3D	0.9773	−0.1723	0.8178	0.056*
C4A	1.4920 (3)	−0.28414 (16)	1.2521 (3)	0.0441 (7)
H4A	1.6071	−0.2832	1.2637	0.053*
C4B	0.9057 (4)	−0.10270 (17)	0.9813 (4)	0.0490 (7)
H4B	0.8130	−0.0886	0.9140	0.059*
N5A	1.4357 (2)	−0.27668 (12)	1.4044 (2)	0.0368 (5)
N5B	0.9699 (3)	−0.03578 (14)	1.0580 (2)	0.0403 (5)
C6A	1.2763 (3)	−0.29648 (16)	1.4220 (3)	0.0355 (5)
C6B	1.1307 (3)	−0.03545 (15)	1.1206 (3)	0.0363 (6)
C7A	1.1664 (3)	−0.24204 (17)	1.4443 (3)	0.0457 (7)
H7A	1.1961	−0.1926	1.4462	0.055*
C7B	1.1690 (4)	−0.03548 (18)	1.2758 (3)	0.0485 (7)
H7B	1.0906	−0.0415	1.3407	0.058*
C8A	1.0148 (3)	−0.2607 (2)	1.4635 (4)	0.0548 (8)
H8A	0.9424	−0.2242	1.4820	0.066*
C8B	1.3225 (4)	−0.0267 (2)	1.3344 (4)	0.0587 (9)
H8B	1.3482	−0.0259	1.4386	0.070*
C9A	0.9695 (3)	−0.3334 (2)	1.4554 (4)	0.0530 (8)
H9A	0.8658	−0.3458	1.4675	0.064*
C9B	1.4383 (4)	−0.01891 (19)	1.2369 (4)	0.0571 (9)
H9B	1.5418	−0.0109	1.2758	0.069*
C10A	1.0749 (3)	−0.38800 (17)	1.4298 (4)	0.0467 (7)
H10A	1.0422	−0.4370	1.4237	0.056*
C10B	1.4017 (3)	−0.02294 (17)	1.0826 (4)	0.0461 (7)
H10B	1.4812	−0.0194	1.0182	0.055*
C11A	1.2304 (3)	−0.37036 (15)	1.4130 (3)	0.0353 (5)
C11B	1.2482 (3)	−0.03216 (15)	1.0231 (3)	0.0363 (5)
C12A	1.4358 (6)	−0.2213 (2)	1.1517 (4)	0.0707 (11)
H12A	1.3230	−0.2210	1.1396	0.106*
H12B	1.4751	−0.2271	1.0544	0.106*
H12C	1.4733	−0.1755	1.1964	0.106*
C12B	0.8546 (5)	−0.1577 (3)	1.0958 (5)	0.0806 (12)
H12D	0.9429	−0.1705	1.1660	0.121*
H12E	0.8147	−0.2015	1.0443	0.121*
H12F	0.7738	−0.1361	1.1498	0.121*
C13A	1.5282 (3)	−0.23943 (16)	1.5082 (3)	0.0425 (6)
C13B	0.8785 (3)	0.02480 (19)	1.0567 (3)	0.0483 (7)
C14A	1.4827 (4)	−0.2412 (2)	1.6705 (3)	0.0516 (7)
H14A	1.3773	−0.2624	1.6720	0.062*
C14B	0.9587 (5)	0.0969 (2)	1.1152 (4)	0.0651 (10)
H14B	1.0379	0.0860	1.1995	0.078*

	U11	U22	U33	U12	U13	U23
Cl1A	0.1134 (9)	0.0939 (8)	0.0740 (7)	0.0444 (7)	0.0047 (6)	0.0100 (6)
Cl1B	0.1093 (9)	0.0570 (6)	0.1045 (8)	−0.0225 (6)	0.0047 (7)	0.0035 (6)
Cl2A	0.1158 (9)	0.0691 (6)	0.0740 (6)	0.0202 (6)	0.0169 (6)	−0.0282 (5)
Cl2B	0.1609 (13)	0.1493 (13)	0.0748 (7)	0.1052 (12)	−0.0141 (7)	−0.0412 (8)
O1A	0.0640 (14)	0.0558 (13)	0.0609 (13)	0.0228 (12)	0.0193 (11)	0.0018 (11)
O1B	0.0562 (13)	0.0768 (16)	0.0377 (11)	−0.0032 (12)	−0.0020 (9)	−0.0029 (11)
O2A	0.0445 (12)	0.0707 (16)	0.0778 (16)	−0.0228 (11)	0.0190 (11)	−0.0222 (13)
O2B	0.0332 (12)	0.087 (2)	0.133 (3)	0.0137 (13)	−0.0012 (14)	0.0200 (19)
O3	0.0578 (16)	0.0485 (14)	0.093 (2)	0.0005 (13)	−0.0113 (15)	0.0087 (13)
N1A	0.0465 (13)	0.0319 (13)	0.0435 (13)	0.0045 (10)	0.0100 (10)	0.0037 (10)
N1B	0.0367 (12)	0.0480 (13)	0.0360 (12)	−0.0030 (11)	0.0087 (10)	0.0039 (11)
C2A	0.0474 (16)	0.0378 (15)	0.0408 (14)	0.0031 (13)	0.0035 (12)	−0.0043 (12)
C2B	0.0388 (14)	0.0439 (16)	0.0400 (15)	0.0031 (12)	0.0026 (11)	−0.0056 (12)
C3A	0.0575 (18)	0.0471 (16)	0.0348 (13)	0.0020 (14)	0.0083 (12)	−0.0023 (12)
C3B	0.0504 (17)	0.0371 (15)	0.0511 (16)	−0.0102 (13)	−0.0010 (13)	−0.0056 (12)
C4A	0.0461 (16)	0.0472 (17)	0.0404 (14)	−0.0062 (13)	0.0108 (12)	−0.0014 (13)
C4B	0.0382 (15)	0.0495 (18)	0.0588 (19)	−0.0087 (13)	0.0016 (13)	0.0007 (14)
N5A	0.0328 (11)	0.0392 (12)	0.0394 (11)	−0.0022 (9)	0.0082 (9)	−0.0032 (9)
N5B	0.0282 (11)	0.0521 (14)	0.0409 (12)	0.0018 (10)	0.0047 (9)	0.0010 (11)
C6A	0.0277 (12)	0.0417 (14)	0.0367 (13)	0.0022 (11)	0.0010 (10)	0.0018 (11)
C6B	0.0334 (13)	0.0375 (13)	0.0372 (13)	0.0031 (11)	−0.0004 (10)	0.0018 (11)
C7A	0.0420 (15)	0.0402 (16)	0.0552 (17)	0.0070 (12)	0.0057 (13)	0.0037 (13)
C7B	0.0540 (17)	0.0523 (17)	0.0390 (14)	0.0062 (14)	0.0031 (12)	0.0047 (13)
C8A	0.0372 (16)	0.057 (2)	0.071 (2)	0.0182 (14)	0.0091 (14)	0.0025 (16)
C8B	0.071 (2)	0.060 (2)	0.0419 (16)	0.0053 (18)	−0.0129 (15)	−0.0005 (15)
C9A	0.0292 (15)	0.065 (2)	0.0648 (19)	−0.0016 (14)	0.0056 (13)	0.0010 (17)
C9B	0.0434 (17)	0.057 (2)	0.066 (2)	−0.0052 (15)	−0.0182 (15)	0.0001 (16)
C10A	0.0376 (15)	0.0460 (17)	0.0563 (17)	−0.0072 (12)	0.0031 (13)	−0.0004 (13)
C10B	0.0328 (13)	0.0472 (17)	0.0568 (17)	−0.0013 (12)	−0.0033 (12)	0.0023 (14)
C11A	0.0356 (13)	0.0376 (14)	0.0326 (12)	−0.0005 (11)	0.0032 (10)	−0.0005 (11)
C11B	0.0342 (13)	0.0347 (13)	0.0393 (13)	0.0007 (11)	0.0009 (10)	0.0015 (11)
C12A	0.104 (3)	0.049 (2)	0.061 (2)	−0.0015 (19)	0.019 (2)	0.0172 (17)
C12B	0.083 (3)	0.075 (3)	0.087 (3)	−0.036 (2)	0.026 (2)	0.004 (2)
C13A	0.0333 (14)	0.0402 (15)	0.0551 (16)	−0.0060 (12)	0.0107 (12)	−0.0084 (13)
C13B	0.0353 (15)	0.0581 (19)	0.0525 (17)	0.0096 (14)	0.0086 (13)	0.0103 (15)
C14A	0.0420 (15)	0.064 (2)	0.0482 (16)	0.0011 (14)	0.0015 (12)	−0.0146 (15)
C14B	0.073 (2)	0.064 (2)	0.0539 (19)	0.0303 (18)	−0.0134 (17)	−0.0112 (16)

Cl1A—C14A	1.759 (3)	N5B—C13B	1.345 (4)
Cl1B—C14B	1.748 (4)	N5B—C6B	1.432 (3)
Cl2A—C14A	1.754 (3)	C6A—C7A	1.388 (4)
Cl2B—C14B	1.748 (4)	C6A—C11A	1.393 (4)
O1A—C2A	1.219 (4)	C6B—C7B	1.385 (4)
O1B—C2B	1.220 (3)	C6B—C11B	1.387 (4)
O2A—C13A	1.221 (3)	C7A—C8A	1.365 (4)
O2B—C13B	1.206 (4)	C7A—H7A	0.9300
O3—H1W	0.86 (6)	C7B—C8B	1.374 (5)
O3—H2W	0.80 (4)	C7B—H7B	0.9300
N1A—C2A	1.349 (4)	C8A—C9A	1.370 (5)
N1A—C11A	1.400 (4)	C8A—H8A	0.9300
N1A—H1A	0.87 (4)	C8B—C9B	1.381 (5)
N1B—C2B	1.343 (4)	C8B—H8B	0.9300
N1B—C11B	1.403 (3)	C9A—C10A	1.370 (4)
N1B—H1B	0.81 (3)	C9A—H9A	0.9300
C2A—C3A	1.503 (4)	C9B—C10B	1.376 (5)
C2B—C3B	1.508 (4)	C9B—H9B	0.9300
C3A—C4A	1.516 (4)	C10A—C11A	1.389 (4)
C3A—H3A	0.9700	C10A—H10A	0.9300
C3A—H3B	0.9700	C10B—C11B	1.378 (4)
C3B—C4B	1.527 (5)	C10B—H10B	0.9300
C3B—H3C	0.9700	C12A—H12A	0.9600
C3B—H3D	0.9700	C12A—H12B	0.9600
C4A—N5A	1.482 (3)	C12A—H12C	0.9600
C4A—C12A	1.495 (5)	C12B—H12D	0.9600
C4A—H4A	0.9800	C12B—H12E	0.9600
C4B—N5B	1.469 (4)	C12B—H12F	0.9600
C4B—C12B	1.515 (5)	C13A—C14A	1.526 (4)
C4B—H4B	0.9800	C13B—C14B	1.540 (5)
N5A—C13A	1.338 (4)	C14A—H14A	0.9800
N5A—C6A	1.431 (3)	C14B—H14B	0.9800
H1W—O3—H2W	106 (5)	C7A—C8A—C9A	119.9 (3)
C2A—N1A—C11A	125.0 (2)	C7A—C8A—H8A	120.1
C2A—N1A—H1A	117 (2)	C9A—C8A—H8A	120.1
C11A—N1A—H1A	117 (2)	C7B—C8B—C9B	119.4 (3)
C2B—N1B—C11B	126.2 (3)	C7B—C8B—H8B	120.3
C2B—N1B—H1B	114 (2)	C9B—C8B—H8B	120.3
C11B—N1B—H1B	119 (2)	C10A—C9A—C8A	120.9 (3)
O1A—C2A—N1A	120.5 (3)	C10A—C9A—H9A	119.6
O1A—C2A—C3A	123.0 (3)	C8A—C9A—H9A	119.6
N1A—C2A—C3A	116.4 (3)	C10B—C9B—C8B	120.5 (3)
O1B—C2B—N1B	121.9 (3)	C10B—C9B—H9B	119.7
O1B—C2B—C3B	122.0 (3)	C8B—C9B—H9B	119.7
N1B—C2B—C3B	116.1 (2)	C9A—C10A—C11A	120.2 (3)
C2A—C3A—C4A	115.1 (2)	C9A—C10A—H10A	119.9
C2A—C3A—H3A	108.5	C11A—C10A—H10A	119.9
C4A—C3A—H3A	108.5	C9B—C10B—C11B	120.4 (3)
C2A—C3A—H3B	108.5	C9B—C10B—H10B	119.8
C4A—C3A—H3B	108.5	C11B—C10B—H10B	119.8
H3A—C3A—H3B	107.5	C10A—C11A—C6A	118.8 (2)
C2B—C3B—C4B	113.3 (2)	C10A—C11A—N1A	120.8 (3)
C2B—C3B—H3C	108.9	C6A—C11A—N1A	120.4 (2)
C4B—C3B—H3C	108.9	C10B—C11B—C6B	119.0 (3)
C2B—C3B—H3D	108.9	C10B—C11B—N1B	120.6 (3)
C4B—C3B—H3D	108.9	C6B—C11B—N1B	120.3 (2)
H3C—C3B—H3D	107.7	C4A—C12A—H12A	109.5
N5A—C4A—C12A	111.1 (3)	C4A—C12A—H12B	109.5
N5A—C4A—C3A	109.3 (2)	H12A—C12A—H12B	109.5
C12A—C4A—C3A	111.8 (3)	C4A—C12A—H12C	109.5
N5A—C4A—H4A	108.2	H12A—C12A—H12C	109.5
C12A—C4A—H4A	108.2	H12B—C12A—H12C	109.5
C3A—C4A—H4A	108.2	C4B—C12B—H12D	109.5
N5B—C4B—C12B	110.4 (3)	C4B—C12B—H12E	109.5
N5B—C4B—C3B	109.4 (2)	H12D—C12B—H12E	109.5
C12B—C4B—C3B	112.3 (3)	C4B—C12B—H12F	109.5
N5B—C4B—H4B	108.2	H12D—C12B—H12F	109.5
C12B—C4B—H4B	108.2	H12E—C12B—H12F	109.5
C3B—C4B—H4B	108.2	O2A—C13A—N5A	123.3 (3)
C13A—N5A—C6A	123.9 (2)	O2A—C13A—C14A	119.7 (3)
C13A—N5A—C4A	116.8 (2)	N5A—C13A—C14A	116.9 (2)
C6A—N5A—C4A	118.1 (2)	O2B—C13B—N5B	122.9 (3)
C13B—N5B—C6B	122.4 (3)	O2B—C13B—C14B	120.4 (3)
C13B—N5B—C4B	118.4 (2)	N5B—C13B—C14B	116.5 (3)
C6B—N5B—C4B	119.1 (2)	C13A—C14A—Cl2A	108.8 (2)
C7A—C6A—C11A	119.8 (2)	C13A—C14A—Cl1A	108.0 (2)
C7A—C6A—N5A	120.2 (3)	Cl2A—C14A—Cl1A	110.73 (17)
C11A—C6A—N5A	120.0 (2)	C13A—C14A—H14A	109.7
C7B—C6B—C11B	120.2 (2)	Cl2A—C14A—H14A	109.7
C7B—C6B—N5B	120.9 (3)	Cl1A—C14A—H14A	109.7
C11B—C6B—N5B	118.8 (2)	C13B—C14B—Cl2B	109.4 (3)
C8A—C7A—C6A	120.4 (3)	C13B—C14B—Cl1B	107.7 (2)
C8A—C7A—H7A	119.8	Cl2B—C14B—Cl1B	109.9 (2)
C6A—C7A—H7A	119.8	C13B—C14B—H14B	109.9
C8B—C7B—C6B	120.2 (3)	Cl2B—C14B—H14B	109.9
C8B—C7B—H7B	119.9	Cl1B—C14B—H14B	109.9
C6B—C7B—H7B	119.9
C11A—N1A—C2A—O1A	173.3 (3)	C7B—C8B—C9B—C10B	−2.6 (5)
C11A—N1A—C2A—C3A	−9.3 (4)	C8A—C9A—C10A—C11A	0.6 (5)
C11B—N1B—C2B—O1B	177.0 (3)	C8B—C9B—C10B—C11B	2.3 (5)
C11B—N1B—C2B—C3B	−5.4 (4)	C9A—C10A—C11A—C6A	−0.2 (4)
O1A—C2A—C3A—C4A	−106.8 (3)	C9A—C10A—C11A—N1A	177.8 (3)
N1A—C2A—C3A—C4A	75.9 (3)	C7A—C6A—C11A—C10A	−1.4 (4)
O1B—C2B—C3B—C4B	−107.2 (3)	N5A—C6A—C11A—C10A	−179.7 (2)
N1B—C2B—C3B—C4B	75.2 (3)	C7A—C6A—C11A—N1A	−179.4 (2)
C2A—C3A—C4A—N5A	−40.6 (4)	N5A—C6A—C11A—N1A	2.2 (4)
C2A—C3A—C4A—C12A	−164.0 (3)	C2A—N1A—C11A—C10A	138.6 (3)
C2B—C3B—C4B—N5B	−46.2 (3)	C2A—N1A—C11A—C6A	−43.4 (4)
C2B—C3B—C4B—C12B	−169.2 (3)	C9B—C10B—C11B—C6B	1.6 (4)
C12A—C4A—N5A—C13A	−90.1 (3)	C9B—C10B—C11B—N1B	177.9 (3)
C3A—C4A—N5A—C13A	146.1 (3)	C7B—C6B—C11B—C10B	−5.2 (4)
C12A—C4A—N5A—C6A	78.1 (3)	N5B—C6B—C11B—C10B	172.3 (3)
C3A—C4A—N5A—C6A	−45.7 (3)	C7B—C6B—C11B—N1B	178.5 (3)
C12B—C4B—N5B—C13B	−102.0 (3)	N5B—C6B—C11B—N1B	−3.9 (4)
C3B—C4B—N5B—C13B	134.0 (3)	C2B—N1B—C11B—C10B	141.2 (3)
C12B—C4B—N5B—C6B	83.0 (3)	C2B—N1B—C11B—C6B	−42.6 (4)
C3B—C4B—N5B—C6B	−41.1 (3)	C6A—N5A—C13A—O2A	−164.1 (3)
C13A—N5A—C6A—C7A	58.9 (4)	C4A—N5A—C13A—O2A	3.3 (4)
C4A—N5A—C6A—C7A	−108.3 (3)	C6A—N5A—C13A—C14A	21.3 (4)
C13A—N5A—C6A—C11A	−122.8 (3)	C4A—N5A—C13A—C14A	−171.3 (3)
C4A—N5A—C6A—C11A	70.0 (3)	C6B—N5B—C13B—O2B	−179.7 (3)
C13B—N5B—C6B—C7B	75.4 (4)	C4B—N5B—C13B—O2B	5.4 (4)
C4B—N5B—C6B—C7B	−109.8 (3)	C6B—N5B—C13B—C14B	4.5 (4)
C13B—N5B—C6B—C11B	−102.1 (3)	C4B—N5B—C13B—C14B	−170.4 (3)
C4B—N5B—C6B—C11B	72.7 (3)	O2A—C13A—C14A—Cl2A	53.9 (3)
C11A—C6A—C7A—C8A	2.6 (4)	N5A—C13A—C14A—Cl2A	−131.2 (2)
N5A—C6A—C7A—C8A	−179.0 (3)	O2A—C13A—C14A—Cl1A	−66.3 (3)
C11B—C6B—C7B—C8B	4.9 (5)	N5A—C13A—C14A—Cl1A	108.5 (3)
N5B—C6B—C7B—C8B	−172.6 (3)	O2B—C13B—C14B—Cl2B	27.4 (4)
C6A—C7A—C8A—C9A	−2.3 (5)	N5B—C13B—C14B—Cl2B	−156.7 (2)
C6B—C7B—C8B—C9B	−1.0 (5)	O2B—C13B—C14B—Cl1B	−92.0 (3)
C7A—C8A—C9A—C10A	0.7 (5)	N5B—C13B—C14B—Cl1B	84.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4A···O2A	0.98	2.34	2.694 (4)	100
C4B—H4B···O2B	0.98	2.31	2.715 (4)	104
N1A—H1A···O3	0.87 (4)	2.08 (4)	2.927 (4)	164 (3)
O3—H2W···O1Bi	0.80 (4)	2.02 (4)	2.815 (4)	173 (4)
C3A—H3A···O2Bi	0.97	2.60	3.038 (4)	108
C8A—H8A···O2Aii	0.93	2.51	3.268 (4)	139
C10B—H10B···O2Biii	0.93	2.39	3.179 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O3	0.87 (4)	2.08 (4)	2.927 (4)	164 (3)
O3—H2W⋯O1Bi	0.80 (4)	2.02 (4)	2.815 (4)	173 (4)
C8A—H8A⋯O2Aii	0.93	2.51	3.268 (4)	139
C10B—H10B⋯O2Biii	0.93	2.39	3.179 (4)	143

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