N'-[(E)-4-Chloro-benzyl-idene]pyridine-4-carbohydrazide monohydrate.

The asymmetric unit of the title compound, C(13)H(10)ClN(3)O·H(2)O, consists of two crystallographically independent Schiff base mol-ecules which exist in an E conformation with respect to the C=N double bond, and two independent water mol-ecules. In the crystal, the Schiff base and water mol-ecules are linked into a three-dimensional network via N-H⋯O, O-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds. The crystal studied was a pseudo-merohedral twin with twin law (101 0-10 00-1) and a component ratio of 0.792 (2):0.208 (2).

Related literature

For background to terphenyls, see: Naveenkumar et al. (2010 ▶); Chen (2006 ▶). For related structures, see: Fun, Quah, Shetty et al. (2012 ▶); Fun, Quah, Shyma et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H10ClN3O·H2O

M = 277.71

Monoclinic,

a = 14.1645 (7) Å

b = 14.6276 (7) Å

c = 14.0817 (7) Å

β = 119.220 (2)°

V = 2546.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.47 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.871, T max = 0.931

20683 measured reflections

4458 independent reflections

3995 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.205

S = 1.06

4458 reflections

360 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.80 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029121/is5159sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029121/is5159Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029121/is5159Isup3.cml

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

C13H10ClN3O·H2O	F(000) = 1152
Mr = 277.71	Dx = 1.449 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8764 reflections
a = 14.1645 (7) Å	θ = 2.8–29.9°
b = 14.6276 (7) Å	µ = 0.30 mm−1
c = 14.0817 (7) Å	T = 100 K
β = 119.220 (2)°	Block, yellow
V = 2546.4 (2) Å3	0.47 × 0.26 × 0.24 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	4458 independent reflections
Radiation source: fine-focus sealed tube	3995 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.871, Tmax = 0.931	k = −17→13
20683 measured reflections	l = −16→16

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.123P)2 + 5.736P] where P = (Fo2 + 2Fc2)/3
4458 reflections	(Δ/σ)max = 0.001
360 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.07219 (10)	1.37835 (8)	0.59204 (11)	0.0295 (3)
O1A	0.1241 (3)	0.7654 (2)	0.6526 (3)	0.0223 (7)
N1A	0.4094 (3)	0.5253 (3)	0.7583 (3)	0.0237 (9)
H1NA	0.3567	0.8519	0.7510	0.035*
N2A	0.2758 (3)	0.8520 (3)	0.7089 (3)	0.0191 (8)
H1NB	0.1442	0.1632	0.8694	0.029*
N3A	0.2166 (3)	0.9323 (3)	0.6802 (3)	0.0206 (8)
C1A	0.4010 (4)	0.6845 (3)	0.7977 (4)	0.0222 (10)
H1AA	0.4371	0.7375	0.8380	0.027*
C2A	0.4562 (4)	0.6018 (3)	0.8149 (4)	0.0247 (11)
H2AA	0.5303	0.5994	0.8690	0.030*
C3A	0.3042 (4)	0.5298 (3)	0.6855 (4)	0.0233 (10)
H3AA	0.2700	0.4761	0.6454	0.028*
C4A	0.2420 (4)	0.6080 (3)	0.6647 (4)	0.0228 (10)
H4AA	0.1669	0.6073	0.6138	0.027*
C5A	0.2924 (4)	0.6874 (3)	0.7204 (4)	0.0188 (10)
C6A	0.2226 (4)	0.7718 (3)	0.6916 (4)	0.0179 (10)
C7A	0.2727 (4)	1.0055 (3)	0.6964 (4)	0.0213 (10)
H7AA	0.3488	1.0011	0.7256	0.026*
C8A	0.2212 (4)	1.0954 (3)	0.6706 (4)	0.0208 (10)
C9A	0.1071 (4)	1.1091 (3)	0.6206 (4)	0.0225 (11)
H9AA	0.0609	1.0574	0.6028	0.027*
C10A	0.0632 (4)	1.1930 (3)	0.5980 (4)	0.0230 (10)
H10A	−0.0130	1.2005	0.5646	0.028*
C11A	0.1303 (4)	1.2690 (3)	0.6241 (4)	0.0192 (10)
C12A	0.2426 (4)	1.2607 (3)	0.6729 (4)	0.0223 (10)
H12A	0.2875	1.3132	0.6904	0.027*
C13A	0.2864 (4)	1.1740 (3)	0.6951 (4)	0.0220 (10)
H13A	0.3627	1.1671	0.7278	0.026*
O1WA	0.4993 (3)	0.8952 (3)	0.8295 (4)	0.0354 (9)
Cl1B	0.42027 (11)	−0.36679 (8)	1.05982 (11)	0.0290 (3)
O1B	0.3756 (3)	0.2301 (2)	1.0041 (3)	0.0270 (8)
N1B	0.1149 (3)	0.4890 (3)	0.8468 (3)	0.0241 (9)
N2B	0.2152 (3)	0.1541 (3)	0.9120 (3)	0.0188 (8)
N3B	0.2689 (3)	0.0713 (3)	0.9449 (3)	0.0225 (9)
C1B	0.1096 (4)	0.3298 (3)	0.8844 (4)	0.0210 (10)
H1BA	0.0696	0.2791	0.8881	0.025*
C2B	0.0618 (4)	0.4152 (3)	0.8538 (4)	0.0211 (10)
H2BA	−0.0114	0.4220	0.8371	0.025*
C3B	0.2179 (4)	0.4770 (3)	0.8718 (4)	0.0231 (10)
H3BA	0.2562	0.5286	0.8673	0.028*
C4B	0.2721 (4)	0.3956 (3)	0.9034 (4)	0.0225 (10)
H4BA	0.3457	0.3915	0.9205	0.027*
C5B	0.2176 (4)	0.3195 (3)	0.9099 (4)	0.0192 (10)
C6B	0.2767 (4)	0.2306 (3)	0.9467 (4)	0.0179 (10)
C7B	0.2105 (4)	−0.0009 (3)	0.9066 (4)	0.0214 (10)
H7BA	0.1351	0.0042	0.8576	0.026*
C8B	0.2620 (4)	−0.0915 (3)	0.9397 (4)	0.0213 (10)
C9B	0.3751 (4)	−0.1005 (4)	1.0003 (4)	0.0273 (11)
H9BA	0.4189	−0.0473	1.0168	0.033*
C10B	0.4230 (4)	−0.1829 (4)	1.0357 (4)	0.0258 (11)
H10B	0.4995	−0.1876	1.0767	0.031*
C11B	0.3585 (4)	−0.2605 (3)	1.0112 (4)	0.0202 (10)
C12B	0.2471 (4)	−0.2557 (3)	0.9494 (4)	0.0202 (10)
H12B	0.2042	−0.3095	0.9315	0.024*
C13B	0.1991 (4)	−0.1706 (3)	0.9140 (4)	0.0219 (10)
H13B	0.1226	−0.1661	0.8719	0.026*
O1WB	0.9892 (3)	0.1399 (3)	0.7853 (4)	0.0367 (10)
H1WA	0.520 (6)	0.914 (5)	0.783 (6)	0.05 (2)*
H2WA	0.551 (7)	0.876 (6)	0.890 (8)	0.08 (3)*
H1WB	0.960 (7)	0.101 (6)	0.739 (7)	0.06 (3)*
H2WB	0.955 (6)	0.155 (5)	0.808 (6)	0.04 (2)*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0284 (7)	0.0147 (6)	0.0418 (8)	0.0036 (5)	0.0143 (6)	−0.0003 (5)
O1A	0.0173 (16)	0.0182 (18)	0.0292 (18)	0.0014 (13)	0.0097 (14)	0.0030 (14)
N1A	0.031 (2)	0.017 (2)	0.029 (2)	0.0044 (17)	0.0186 (19)	0.0044 (17)
N2A	0.0169 (19)	0.0136 (19)	0.025 (2)	0.0003 (16)	0.0090 (17)	0.0039 (16)
N3A	0.023 (2)	0.014 (2)	0.024 (2)	0.0019 (16)	0.0108 (17)	0.0050 (16)
C1A	0.028 (3)	0.015 (2)	0.023 (2)	0.000 (2)	0.013 (2)	0.0009 (19)
C2A	0.029 (3)	0.020 (2)	0.024 (2)	0.008 (2)	0.012 (2)	0.004 (2)
C3A	0.028 (3)	0.015 (2)	0.032 (3)	0.003 (2)	0.018 (2)	0.000 (2)
C4A	0.024 (3)	0.018 (2)	0.026 (3)	0.003 (2)	0.011 (2)	0.002 (2)
C5A	0.021 (2)	0.017 (2)	0.023 (2)	0.0025 (19)	0.0151 (19)	0.0068 (19)
C6A	0.020 (2)	0.016 (2)	0.019 (2)	0.0012 (18)	0.0097 (19)	0.0030 (18)
C7A	0.020 (2)	0.017 (2)	0.024 (2)	0.0002 (19)	0.009 (2)	0.004 (2)
C8A	0.031 (3)	0.012 (2)	0.021 (2)	−0.002 (2)	0.014 (2)	−0.0017 (19)
C9A	0.036 (3)	0.017 (2)	0.016 (2)	−0.014 (2)	0.013 (2)	−0.0015 (18)
C10A	0.023 (2)	0.023 (3)	0.024 (2)	−0.003 (2)	0.012 (2)	−0.004 (2)
C11A	0.024 (2)	0.014 (2)	0.021 (2)	−0.0035 (18)	0.013 (2)	−0.0058 (18)
C12A	0.025 (2)	0.011 (2)	0.030 (3)	−0.0074 (19)	0.013 (2)	−0.0045 (19)
C13A	0.017 (2)	0.018 (2)	0.027 (2)	−0.0012 (19)	0.007 (2)	0.000 (2)
O1WA	0.0234 (19)	0.034 (2)	0.038 (2)	−0.0067 (17)	0.0060 (18)	0.0152 (18)
Cl1B	0.0340 (7)	0.0176 (6)	0.0350 (7)	0.0075 (5)	0.0164 (6)	0.0055 (5)
O1B	0.0162 (17)	0.024 (2)	0.0332 (19)	0.0029 (14)	0.0061 (15)	0.0080 (15)
N1B	0.029 (2)	0.015 (2)	0.026 (2)	0.0047 (17)	0.0112 (18)	0.0035 (16)
N2B	0.0162 (19)	0.0140 (19)	0.022 (2)	0.0025 (16)	0.0062 (16)	0.0010 (16)
N3B	0.023 (2)	0.013 (2)	0.031 (2)	0.0042 (17)	0.0123 (18)	−0.0022 (17)
C1B	0.025 (2)	0.016 (2)	0.022 (2)	0.0002 (19)	0.011 (2)	0.0015 (19)
C2B	0.021 (2)	0.015 (2)	0.024 (2)	0.0032 (19)	0.009 (2)	0.0004 (19)
C3B	0.025 (3)	0.015 (2)	0.028 (3)	−0.004 (2)	0.011 (2)	0.002 (2)
C4B	0.023 (2)	0.017 (2)	0.027 (2)	−0.002 (2)	0.012 (2)	0.000 (2)
C5B	0.019 (2)	0.018 (2)	0.019 (2)	0.0040 (19)	0.0082 (19)	0.0029 (19)
C6B	0.022 (2)	0.019 (3)	0.015 (2)	0.0032 (19)	0.0102 (19)	0.0037 (18)
C7B	0.023 (2)	0.013 (2)	0.027 (2)	0.0012 (19)	0.011 (2)	−0.0044 (19)
C8B	0.028 (3)	0.015 (2)	0.023 (2)	0.002 (2)	0.013 (2)	0.0004 (19)
C9B	0.037 (3)	0.021 (3)	0.035 (3)	−0.012 (2)	0.026 (2)	−0.012 (2)
C10B	0.018 (2)	0.038 (3)	0.021 (2)	0.010 (2)	0.008 (2)	0.008 (2)
C11B	0.025 (2)	0.016 (2)	0.021 (2)	0.006 (2)	0.012 (2)	0.0010 (18)
C12B	0.027 (2)	0.011 (2)	0.021 (2)	0.002 (2)	0.011 (2)	−0.0016 (18)
C13B	0.021 (2)	0.020 (2)	0.022 (2)	−0.003 (2)	0.009 (2)	−0.003 (2)
O1WB	0.024 (2)	0.031 (2)	0.053 (3)	−0.0026 (17)	0.017 (2)	−0.022 (2)

Cl1A—C11A	1.754 (5)	Cl1B—C11B	1.751 (5)
O1A—C6A	1.228 (6)	O1B—C6B	1.229 (6)
N1A—C3A	1.336 (7)	N1B—C3B	1.335 (6)
N1A—C2A	1.345 (7)	N1B—C2B	1.346 (6)
N2A—C6A	1.351 (6)	N2B—C6B	1.355 (6)
N2A—N3A	1.385 (5)	N2B—N3B	1.384 (5)
N2A—H1NA	1.0006	N2B—H1NB	0.8938
N3A—C7A	1.286 (6)	N3B—C7B	1.286 (6)
C1A—C5A	1.385 (7)	C1B—C2B	1.386 (7)
C1A—C2A	1.396 (7)	C1B—C5B	1.398 (7)
C1A—H1AA	0.9500	C1B—H1BA	0.9500
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.385 (7)	C3B—C4B	1.368 (7)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.388 (7)	C4B—C5B	1.384 (7)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.508 (6)	C5B—C6B	1.495 (6)
C7A—C8A	1.460 (6)	C7B—C8B	1.475 (7)
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C8A—C13A	1.408 (7)	C8B—C13B	1.395 (7)
C8A—C9A	1.428 (7)	C8B—C9B	1.405 (7)
C9A—C10A	1.342 (7)	C9B—C10B	1.354 (8)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.390 (7)	C10B—C11B	1.391 (7)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.396 (7)	C11B—C12B	1.383 (7)
C12A—C13A	1.379 (7)	C12B—C13B	1.389 (7)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
O1WA—H1WA	0.89 (8)	O1WB—H1WB	0.81 (9)
O1WA—H2WA	0.86 (9)	O1WB—H2WB	0.73 (7)
C3A—N1A—C2A	117.1 (4)	C3B—N1B—C2B	116.9 (4)
C6A—N2A—N3A	118.6 (4)	C6B—N2B—N3B	116.8 (4)
C6A—N2A—H1NA	118.9	C6B—N2B—H1NB	115.7
N3A—N2A—H1NA	121.9	N3B—N2B—H1NB	127.6
C7A—N3A—N2A	114.9 (4)	C7B—N3B—N2B	116.2 (4)
C5A—C1A—C2A	118.4 (5)	C2B—C1B—C5B	119.0 (4)
C5A—C1A—H1AA	120.8	C2B—C1B—H1BA	120.5
C2A—C1A—H1AA	120.8	C5B—C1B—H1BA	120.5
N1A—C2A—C1A	123.1 (5)	N1B—C2B—C1B	122.7 (4)
N1A—C2A—H2AA	118.5	N1B—C2B—H2BA	118.7
C1A—C2A—H2AA	118.5	C1B—C2B—H2BA	118.7
N1A—C3A—C4A	124.0 (5)	N1B—C3B—C4B	124.6 (4)
N1A—C3A—H3AA	118.0	N1B—C3B—H3BA	117.7
C4A—C3A—H3AA	118.0	C4B—C3B—H3BA	117.7
C3A—C4A—C5A	118.2 (5)	C3B—C4B—C5B	118.6 (4)
C3A—C4A—H4AA	120.9	C3B—C4B—H4BA	120.7
C5A—C4A—H4AA	120.9	C5B—C4B—H4BA	120.7
C1A—C5A—C4A	119.1 (4)	C4B—C5B—C1B	118.2 (4)
C1A—C5A—C6A	124.6 (4)	C4B—C5B—C6B	119.1 (4)
C4A—C5A—C6A	116.4 (4)	C1B—C5B—C6B	122.7 (4)
O1A—C6A—N2A	123.9 (4)	O1B—C6B—N2B	123.9 (4)
O1A—C6A—C5A	120.7 (4)	O1B—C6B—C5B	120.0 (4)
N2A—C6A—C5A	115.3 (4)	N2B—C6B—C5B	116.1 (4)
N3A—C7A—C8A	121.0 (4)	N3B—C7B—C8B	119.2 (4)
N3A—C7A—H7AA	119.5	N3B—C7B—H7BA	120.4
C8A—C7A—H7AA	119.5	C8B—C7B—H7BA	120.4
C13A—C8A—C9A	117.1 (4)	C13B—C8B—C9B	118.3 (5)
C13A—C8A—C7A	119.1 (4)	C13B—C8B—C7B	120.5 (4)
C9A—C8A—C7A	123.8 (4)	C9B—C8B—C7B	121.1 (4)
C10A—C9A—C8A	121.8 (4)	C10B—C9B—C8B	121.6 (5)
C10A—C9A—H9AA	119.1	C10B—C9B—H9BA	119.2
C8A—C9A—H9AA	119.1	C8B—C9B—H9BA	119.2
C9A—C10A—C11A	119.4 (5)	C9B—C10B—C11B	119.0 (4)
C9A—C10A—H10A	120.3	C9B—C10B—H10B	120.5
C11A—C10A—H10A	120.3	C11B—C10B—H10B	120.5
C10A—C11A—C12A	121.8 (4)	C12B—C11B—C10B	121.6 (4)
C10A—C11A—Cl1A	119.1 (4)	C12B—C11B—Cl1B	119.4 (4)
C12A—C11A—Cl1A	119.1 (3)	C10B—C11B—Cl1B	119.1 (4)
C13A—C12A—C11A	118.1 (4)	C11B—C12B—C13B	118.7 (4)
C13A—C12A—H12A	120.9	C11B—C12B—H12B	120.7
C11A—C12A—H12A	120.9	C13B—C12B—H12B	120.7
C12A—C13A—C8A	121.7 (4)	C12B—C13B—C8B	120.7 (4)
C12A—C13A—H13A	119.1	C12B—C13B—H13B	119.6
C8A—C13A—H13A	119.1	C8B—C13B—H13B	119.6
H1WA—O1WA—H2WA	114 (8)	H1WB—O1WB—H2WB	111 (8)
C6A—N2A—N3A—C7A	−178.2 (4)	C6B—N2B—N3B—C7B	−176.3 (4)
C3A—N1A—C2A—C1A	−2.4 (7)	C3B—N1B—C2B—C1B	−0.6 (7)
C5A—C1A—C2A—N1A	1.4 (7)	C5B—C1B—C2B—N1B	0.4 (7)
C2A—N1A—C3A—C4A	0.6 (7)	C2B—N1B—C3B—C4B	0.2 (7)
N1A—C3A—C4A—C5A	2.1 (7)	N1B—C3B—C4B—C5B	0.3 (8)
C2A—C1A—C5A—C4A	1.3 (7)	C3B—C4B—C5B—C1B	−0.5 (7)
C2A—C1A—C5A—C6A	−179.1 (4)	C3B—C4B—C5B—C6B	−178.7 (4)
C3A—C4A—C5A—C1A	−3.0 (7)	C2B—C1B—C5B—C4B	0.1 (7)
C3A—C4A—C5A—C6A	177.4 (4)	C2B—C1B—C5B—C6B	178.2 (4)
N3A—N2A—C6A—O1A	−0.6 (7)	N3B—N2B—C6B—O1B	0.4 (7)
N3A—N2A—C6A—C5A	177.3 (4)	N3B—N2B—C6B—C5B	179.6 (4)
C1A—C5A—C6A—O1A	−155.3 (4)	C4B—C5B—C6B—O1B	24.6 (7)
C4A—C5A—C6A—O1A	24.3 (6)	C1B—C5B—C6B—O1B	−153.5 (5)
C1A—C5A—C6A—N2A	26.7 (6)	C4B—C5B—C6B—N2B	−154.6 (4)
C4A—C5A—C6A—N2A	−153.8 (4)	C1B—C5B—C6B—N2B	27.3 (6)
N2A—N3A—C7A—C8A	−179.6 (4)	N2B—N3B—C7B—C8B	−178.9 (4)
N3A—C7A—C8A—C13A	176.6 (4)	N3B—C7B—C8B—C13B	169.7 (4)
N3A—C7A—C8A—C9A	−3.9 (7)	N3B—C7B—C8B—C9B	−8.5 (7)
C13A—C8A—C9A—C10A	−0.3 (7)	C13B—C8B—C9B—C10B	−1.5 (7)
C7A—C8A—C9A—C10A	−179.8 (4)	C7B—C8B—C9B—C10B	176.7 (4)
C8A—C9A—C10A—C11A	−0.1 (7)	C8B—C9B—C10B—C11B	0.1 (7)
C9A—C10A—C11A—C12A	0.2 (7)	C9B—C10B—C11B—C12B	1.6 (7)
C9A—C10A—C11A—Cl1A	178.8 (4)	C9B—C10B—C11B—Cl1B	−178.5 (4)
C10A—C11A—C12A—C13A	0.1 (7)	C10B—C11B—C12B—C13B	−1.9 (7)
Cl1A—C11A—C12A—C13A	−178.5 (4)	Cl1B—C11B—C12B—C13B	178.2 (4)
C11A—C12A—C13A—C8A	−0.5 (7)	C11B—C12B—C13B—C8B	0.4 (7)
C9A—C8A—C13A—C12A	0.6 (7)	C9B—C8B—C13B—C12B	1.2 (7)
C7A—C8A—C13A—C12A	−179.9 (5)	C7B—C8B—C13B—C12B	−177.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···O1WA	1.00	1.88	2.838 (7)	160
N2B—H1NB···O1WBi	0.89	1.95	2.810 (7)	161
O1WA—H1WA···N1Aii	0.88 (9)	2.14 (8)	2.896 (7)	144 (6)
O1WA—H2WA···O1Biii	0.86 (10)	2.05 (9)	2.817 (6)	149 (9)
O1WA—H2WA···N3Biii	0.86 (10)	2.59 (10)	3.306 (6)	142 (8)
O1WB—H2WB···O1Aiv	0.73 (9)	2.19 (8)	2.843 (6)	150 (8)
O1WB—H1WB···N1Biv	0.81 (9)	2.00 (9)	2.798 (6)	166 (11)
C1A—H1AA···O1WA	0.95	2.49	3.321 (6)	146
C1A—H1AA···O1Biii	0.95	2.54	3.277 (7)	135
C7A—H7AA···O1WA	0.95	2.46	3.247 (7)	141
C1B—H1BA···O1WBi	0.95	2.43	3.201 (7)	138
C1B—H1BA···O1Av	0.95	2.52	3.230 (8)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1NA⋯O1WA	1.00	1.88	2.838 (7)	160
N2B—H1NB⋯O1WB i	0.89	1.95	2.810 (7)	161
O1WA—H1WA⋯N1A ii	0.88 (9)	2.14 (8)	2.896 (7)	144 (6)
O1WA—H2WA⋯O1B iii	0.86 (10)	2.05 (9)	2.817 (6)	149 (9)
O1WA—H2WA⋯N3B iii	0.86 (10)	2.59 (10)	3.306 (6)	142 (8)
O1WB—H2WB⋯O1A iv	0.73 (9)	2.19 (8)	2.843 (6)	150 (8)
O1WB—H1WB⋯N1B iv	0.81 (9)	2.00 (9)	2.798 (6)	166 (11)
C1A—H1AA⋯O1WA	0.95	2.49	3.321 (6)	146
C1A—H1AA⋯O1B iii	0.95	2.54	3.277 (7)	135
C7A—H7AA⋯O1WA	0.95	2.46	3.247 (7)	141
C1B—H1BA⋯O1WB i	0.95	2.43	3.201 (7)	138
C1B—H1BA⋯O1A v	0.95	2.52	3.230 (8)	131

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