1-Benzoyl-3-(2,6-dichloro­phen­yl)thio­urea

The asymmetric unit of the title compound, C₁₄H₁₀Cl₂N₂OS, contains two independent mol­ecules with slightly different conformations with respect to the aromatic ring planes. The two independent mol­ecules form dimers via inter­molecular N—H...S hydrogen bonds; the dimers are stacked along [100].

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.078
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1A    -   C8A     ..       5.02 su
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1B    ..  H7B     ..       1.99 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C14 H10 Cl2 N2 O S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-Benzoyl-3-(2,6-dichlorophenyl)thiourea

Crystal data

C14H10Cl2N2OS	Z = 4
Mr = 325.20	F(000) = 664
Triclinic, P1	Dx = 1.548 Mg m^−3
Hall symbol: -P 1	Melting point: 458 K
a = 8.2731 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.9178 (7) Å	Cell parameters from 9938 reflections
c = 14.1746 (7) Å	θ = 2.5–28.3°
α = 70.500 (1)°	µ = 0.61 mm^−1
β = 85.118 (1)°	T = 120 K
γ = 77.804 (1)°	Prism, colorless
V = 1395.55 (12) Å^3	0.48 × 0.45 × 0.38 mm

Data collection

Bruker SMART-CCD area-detector diffractometer	6714 independent reflections
Radiation source: sealed tube	6195 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 28.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.759, Tmax = 0.801	k = −17→17
13966 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: difference Fourier map
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0416P)^2 + 0.4524P] where P = (Fo^2 + 2Fc^2)/3
6714 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1A	0.51102 (4)	0.55550 (3)	0.36191 (3)	0.03034 (8)
Cl2A	1.08720 (4)	0.69797 (3)	0.23645 (3)	0.02719 (8)
S1A	0.79195 (4)	0.84270 (3)	0.35221 (2)	0.02233 (8)
O1A	0.45021 (13)	0.81530 (8)	0.13303 (8)	0.0313 (2)
N1A	0.57665 (12)	0.90821 (8)	0.20738 (8)	0.0196 (2)
H1A	0.5809	0.9757	0.2074	0.024*
N2A	0.70805 (13)	0.72294 (8)	0.24931 (8)	0.0204 (2)
H2A	0.6564	0.7221	0.1979	0.024*
C1A	0.45705 (15)	0.90172 (10)	0.14836 (9)	0.0209 (2)
C2A	0.33446 (14)	1.00721 (10)	0.10533 (9)	0.0200 (2)
C3A	0.24183 (16)	1.01242 (11)	0.02556 (10)	0.0251 (3)
H3A	0.2591	0.9508	0.0010	0.030*
C4A	0.12466 (17)	1.10742 (12)	−0.01791 (11)	0.0298 (3)
H4A	0.0622	1.1111	−0.0726	0.036*
C5A	0.09831 (16)	1.19724 (12)	0.01836 (11)	0.0297 (3)
H5A	0.0187	1.2626	−0.0120	0.036*
C6A	0.18768 (16)	1.19169 (11)	0.09867 (11)	0.0266 (3)
H6A	0.1683	1.2528	0.1239	0.032*
C7A	0.30592 (15)	1.09678 (10)	0.14250 (10)	0.0223 (2)
H7A	0.3671	1.0930	0.1977	0.027*
C8A	0.69083 (14)	0.82067 (10)	0.26655 (9)	0.0185 (2)
C9A	0.80423 (15)	0.62085 (10)	0.30881 (9)	0.0199 (2)
C10A	0.72486 (16)	0.53383 (10)	0.36493 (10)	0.0224 (2)
C11A	0.81190 (18)	0.43088 (11)	0.42162 (10)	0.0276 (3)
H11A	0.7551	0.3729	0.4589	0.033*
C12A	0.98283 (19)	0.41323 (11)	0.42343 (10)	0.0288 (3)
H12A	1.0436	0.3432	0.4629	0.035*
C13A	1.06523 (17)	0.49698 (11)	0.36808 (10)	0.0257 (3)
H13A	1.1825	0.4846	0.3696	0.031*
C14A	0.97685 (16)	0.59936 (10)	0.31015 (9)	0.0216 (2)
Cl1B	0.89345 (4)	1.47251 (3)	0.11438 (3)	0.03729 (9)
Cl2B	0.37601 (4)	1.28188 (3)	0.29306 (2)	0.02703 (8)
S1B	0.67093 (4)	1.17068 (3)	0.13985 (2)	0.02285 (8)
O1B	1.00070 (12)	1.19991 (8)	0.36405 (8)	0.0297 (2)
N1B	0.89065 (13)	1.10707 (8)	0.28218 (8)	0.0202 (2)
H1B	0.8960	1.0405	0.2769	0.024*
N2B	0.74146 (13)	1.28770 (8)	0.24883 (8)	0.0207 (2)
H2B	0.7967	1.2908	0.2979	0.025*
C1B	1.00411 (15)	1.11445 (10)	0.34446 (9)	0.0202 (2)
C2B	1.13331 (14)	1.01219 (10)	0.38544 (9)	0.0200 (2)
C3B	1.22861 (16)	1.01048 (11)	0.46281 (10)	0.0245 (3)
H3B	1.2092	1.0726	0.4868	0.029*
C4B	1.35152 (16)	0.91838 (12)	0.50473 (10)	0.0286 (3)
H4B	1.4149	0.9168	0.5582	0.034*
C5B	1.38187 (16)	0.82880 (11)	0.46868 (11)	0.0280 (3)
H5B	1.4666	0.7660	0.4973	0.034*
C6B	1.28924 (16)	0.83016 (11)	0.39106 (10)	0.0262 (3)
H6B	1.3110	0.7686	0.3664	0.031*
C7B	1.16443 (15)	0.92175 (10)	0.34931 (10)	0.0219 (2)
H7B	1.1006	0.9226	0.2963	0.026*
C8B	0.76951 (14)	1.19206 (10)	0.22713 (9)	0.0186 (2)
C9B	0.62659 (15)	1.38406 (10)	0.19613 (9)	0.0200 (2)
C10B	0.45600 (15)	1.39129 (10)	0.20855 (9)	0.0210 (2)
C11B	0.34629 (17)	1.48604 (11)	0.15645 (10)	0.0261 (3)
H11B	0.2305	1.4884	0.1642	0.031*
C12B	0.40638 (18)	1.57776 (11)	0.09274 (10)	0.0297 (3)
H12B	0.3312	1.6434	0.0575	0.036*
C13B	0.57443 (19)	1.57442 (11)	0.08022 (10)	0.0297 (3)
H13B	0.6155	1.6375	0.0370	0.036*
C14B	0.68211 (16)	1.47801 (11)	0.13150 (10)	0.0239 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.02616 (16)	0.02675 (16)	0.04046 (19)	−0.00826 (12)	0.00309 (13)	−0.01294 (14)
Cl2A	0.02278 (15)	0.02440 (15)	0.03230 (17)	−0.00306 (11)	0.00201 (12)	−0.00799 (12)
S1A	0.02508 (15)	0.01805 (14)	0.02491 (15)	−0.00194 (11)	−0.00602 (11)	−0.00835 (11)
O1A	0.0356 (5)	0.0205 (5)	0.0404 (6)	−0.0001 (4)	−0.0153 (4)	−0.0130 (4)
N1A	0.0207 (5)	0.0135 (4)	0.0240 (5)	−0.0014 (4)	−0.0034 (4)	−0.0056 (4)
N2A	0.0227 (5)	0.0156 (5)	0.0228 (5)	−0.0004 (4)	−0.0056 (4)	−0.0070 (4)
C1A	0.0220 (6)	0.0186 (6)	0.0216 (6)	−0.0034 (4)	−0.0016 (4)	−0.0059 (5)
C2A	0.0186 (5)	0.0184 (5)	0.0208 (6)	−0.0038 (4)	0.0006 (4)	−0.0037 (4)
C3A	0.0264 (6)	0.0240 (6)	0.0243 (6)	−0.0041 (5)	−0.0027 (5)	−0.0070 (5)
C4A	0.0272 (6)	0.0309 (7)	0.0274 (7)	−0.0032 (5)	−0.0079 (5)	−0.0040 (5)
C5A	0.0225 (6)	0.0236 (6)	0.0345 (7)	0.0012 (5)	−0.0041 (5)	−0.0008 (5)
C6A	0.0229 (6)	0.0202 (6)	0.0347 (7)	−0.0016 (5)	0.0018 (5)	−0.0087 (5)
C7A	0.0192 (5)	0.0221 (6)	0.0251 (6)	−0.0032 (4)	−0.0002 (4)	−0.0074 (5)
C8A	0.0181 (5)	0.0163 (5)	0.0204 (5)	−0.0028 (4)	0.0005 (4)	−0.0056 (4)
C9A	0.0242 (6)	0.0143 (5)	0.0214 (6)	−0.0004 (4)	−0.0032 (4)	−0.0074 (4)
C10A	0.0252 (6)	0.0198 (6)	0.0247 (6)	−0.0035 (5)	−0.0003 (5)	−0.0109 (5)
C11A	0.0394 (7)	0.0168 (6)	0.0261 (6)	−0.0051 (5)	−0.0009 (5)	−0.0065 (5)
C12A	0.0403 (7)	0.0170 (6)	0.0263 (6)	0.0038 (5)	−0.0088 (5)	−0.0072 (5)
C13A	0.0264 (6)	0.0228 (6)	0.0277 (6)	0.0040 (5)	−0.0062 (5)	−0.0116 (5)
C14A	0.0245 (6)	0.0185 (6)	0.0226 (6)	−0.0023 (5)	−0.0013 (5)	−0.0089 (5)
Cl1B	0.02914 (17)	0.03076 (18)	0.0517 (2)	−0.01118 (14)	0.01365 (15)	−0.01325 (16)
Cl2B	0.02457 (15)	0.02408 (15)	0.03062 (16)	−0.00658 (12)	0.00394 (12)	−0.00642 (12)
S1B	0.02746 (15)	0.01748 (14)	0.02443 (15)	−0.00207 (11)	−0.00577 (12)	−0.00801 (12)
O1B	0.0305 (5)	0.0222 (5)	0.0405 (6)	−0.0017 (4)	−0.0098 (4)	−0.0155 (4)
N1B	0.0213 (5)	0.0147 (5)	0.0252 (5)	−0.0018 (4)	−0.0028 (4)	−0.0077 (4)
N2B	0.0212 (5)	0.0166 (5)	0.0254 (5)	−0.0013 (4)	−0.0031 (4)	−0.0088 (4)
C1B	0.0198 (5)	0.0191 (6)	0.0224 (6)	−0.0045 (4)	0.0007 (4)	−0.0076 (5)
C2B	0.0176 (5)	0.0196 (6)	0.0215 (6)	−0.0047 (4)	0.0016 (4)	−0.0049 (4)
C3B	0.0245 (6)	0.0250 (6)	0.0249 (6)	−0.0063 (5)	−0.0006 (5)	−0.0082 (5)
C4B	0.0236 (6)	0.0326 (7)	0.0264 (6)	−0.0081 (5)	−0.0041 (5)	−0.0030 (5)
C5B	0.0199 (6)	0.0244 (6)	0.0318 (7)	−0.0022 (5)	−0.0003 (5)	−0.0001 (5)
C6B	0.0229 (6)	0.0213 (6)	0.0317 (7)	−0.0022 (5)	0.0028 (5)	−0.0073 (5)
C7B	0.0198 (5)	0.0210 (6)	0.0245 (6)	−0.0034 (4)	0.0000 (4)	−0.0073 (5)
C8B	0.0183 (5)	0.0157 (5)	0.0214 (6)	−0.0034 (4)	0.0013 (4)	−0.0058 (4)
C9B	0.0229 (6)	0.0157 (5)	0.0223 (6)	−0.0009 (4)	−0.0005 (4)	−0.0090 (5)
C10B	0.0238 (6)	0.0181 (6)	0.0215 (6)	−0.0039 (4)	0.0009 (4)	−0.0074 (5)
C11B	0.0242 (6)	0.0258 (6)	0.0263 (6)	0.0028 (5)	−0.0022 (5)	−0.0104 (5)
C12B	0.0371 (7)	0.0214 (6)	0.0247 (6)	0.0048 (5)	−0.0024 (5)	−0.0057 (5)
C13B	0.0419 (8)	0.0186 (6)	0.0254 (6)	−0.0037 (5)	0.0057 (6)	−0.0059 (5)
C14B	0.0265 (6)	0.0200 (6)	0.0268 (6)	−0.0051 (5)	0.0061 (5)	−0.0108 (5)

Geometric parameters (Å, º)

Cl1A—C10A	1.7337 (13)	Cl1B—C14B	1.7343 (14)
Cl2A—C14A	1.7286 (13)	Cl2B—C10B	1.7321 (13)
S1A—C8A	1.6611 (12)	S1B—C8B	1.6634 (12)
O1A—C1A	1.2196 (15)	O1B—C1B	1.2193 (15)
N1A—C1A	1.3816 (15)	N1B—C1B	1.3801 (15)
N1A—C8A	1.3874 (15)	N1B—C8B	1.3839 (15)
N1A—H1A	0.8800	N1B—H1B	0.8800
N2A—C8A	1.3409 (15)	N2B—C8B	1.3399 (15)
N2A—C9A	1.4184 (15)	N2B—C9B	1.4181 (15)
N2A—H2A	0.8800	N2B—H2B	0.8800
C1A—C2A	1.4914 (16)	C1B—C2B	1.4905 (16)
C2A—C7A	1.3936 (18)	C2B—C7B	1.3941 (17)
C2A—C3A	1.3948 (17)	C2B—C3B	1.3958 (17)
C3A—C4A	1.3854 (18)	C3B—C4B	1.3864 (19)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.389 (2)	C4B—C5B	1.383 (2)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.384 (2)	C5B—C6B	1.387 (2)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.3908 (17)	C6B—C7B	1.3916 (17)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—H7A	0.9500	C7B—H7B	0.9500
C9A—C14A	1.3967 (17)	C9B—C10B	1.3944 (17)
C9A—C10A	1.3977 (17)	C9B—C14B	1.3945 (17)
C10A—C11A	1.3832 (18)	C10B—C11B	1.3815 (17)
C11A—C12A	1.385 (2)	C11B—C12B	1.387 (2)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.380 (2)	C12B—C13B	1.380 (2)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.3879 (17)	C13B—C14B	1.3821 (19)
C13A—H13A	0.9500	C13B—H13B	0.9500
C1A—N1A—C8A	127.52 (10)	C1B—N1B—C8B	127.64 (10)
C1A—N1A—H1A	116.2	C1B—N1B—H1B	116.2
C8A—N1A—H1A	116.2	C8B—N1B—H1B	116.2
C8A—N2A—C9A	124.10 (10)	C8B—N2B—C9B	122.80 (10)
C8A—N2A—H2A	118.0	C8B—N2B—H2B	118.6
C9A—N2A—H2A	118.0	C9B—N2B—H2B	118.6
O1A—C1A—N1A	122.53 (11)	O1B—C1B—N1B	122.19 (11)
O1A—C1A—C2A	121.80 (11)	O1B—C1B—C2B	121.68 (11)
N1A—C1A—C2A	115.67 (10)	N1B—C1B—C2B	116.12 (10)
C7A—C2A—C3A	119.73 (11)	C7B—C2B—C3B	119.66 (11)
C7A—C2A—C1A	123.60 (11)	C7B—C2B—C1B	123.63 (11)
C3A—C2A—C1A	116.64 (11)	C3B—C2B—C1B	116.70 (11)
C4A—C3A—C2A	120.00 (12)	C4B—C3B—C2B	120.14 (12)
C4A—C3A—H3A	120.0	C4B—C3B—H3B	119.9
C2A—C3A—H3A	120.0	C2B—C3B—H3B	119.9
C3A—C4A—C5A	120.10 (13)	C5B—C4B—C3B	119.99 (13)
C3A—C4A—H4A	120.0	C5B—C4B—H4B	120.0
C5A—C4A—H4A	120.0	C3B—C4B—H4B	120.0
C6A—C5A—C4A	120.14 (12)	C4B—C5B—C6B	120.36 (12)
C6A—C5A—H5A	119.9	C4B—C5B—H5B	119.8
C4A—C5A—H5A	119.9	C6B—C5B—H5B	119.8
C5A—C6A—C7A	120.11 (13)	C5B—C6B—C7B	120.01 (13)
C5A—C6A—H6A	119.9	C5B—C6B—H6B	120.0
C7A—C6A—H6A	119.9	C7B—C6B—H6B	120.0
C6A—C7A—C2A	119.91 (12)	C6B—C7B—C2B	119.83 (12)
C6A—C7A—H7A	120.0	C6B—C7B—H7B	120.1
C2A—C7A—H7A	120.0	C2B—C7B—H7B	120.1
N2A—C8A—N1A	115.49 (10)	N2B—C8B—N1B	116.03 (10)
N2A—C8A—S1A	125.36 (9)	N2B—C8B—S1B	124.66 (9)
N1A—C8A—S1A	119.15 (9)	N1B—C8B—S1B	119.31 (9)
C14A—C9A—C10A	117.33 (11)	C10B—C9B—C14B	117.22 (11)
C14A—C9A—N2A	123.43 (11)	C10B—C9B—N2B	122.46 (11)
C10A—C9A—N2A	119.13 (11)	C14B—C9B—N2B	120.28 (11)
C11A—C10A—C9A	121.98 (12)	C11B—C10B—C9B	121.49 (12)
C11A—C10A—Cl1A	119.22 (10)	C11B—C10B—Cl2B	118.10 (10)
C9A—C10A—Cl1A	118.80 (9)	C9B—C10B—Cl2B	120.38 (9)
C10A—C11A—C12A	119.24 (13)	C10B—C11B—C12B	119.53 (13)
C10A—C11A—H11A	120.4	C10B—C11B—H11B	120.2
C12A—C11A—H11A	120.4	C12B—C11B—H11B	120.2
C13A—C12A—C11A	120.28 (12)	C13B—C12B—C11B	120.52 (12)
C13A—C12A—H12A	119.9	C13B—C12B—H12B	119.7
C11A—C12A—H12A	119.9	C11B—C12B—H12B	119.7
C12A—C13A—C14A	120.02 (13)	C12B—C13B—C14B	119.02 (13)
C12A—C13A—H13A	120.0	C12B—C13B—H13B	120.5
C14A—C13A—H13A	120.0	C14B—C13B—H13B	120.5
C13A—C14A—C9A	121.11 (12)	C13B—C14B—C9B	122.17 (12)
C13A—C14A—Cl2A	117.94 (10)	C13B—C14B—Cl1B	119.21 (10)
C9A—C14A—Cl2A	120.91 (9)	C9B—C14B—Cl1B	118.62 (10)
C8A—N1A—C1A—O1A	−8.4 (2)	C8B—N1B—C1B—O1B	5.9 (2)
C8A—N1A—C1A—C2A	170.81 (11)	C8B—N1B—C1B—C2B	−173.19 (11)
O1A—C1A—C2A—C7A	160.42 (13)	O1B—C1B—C2B—C7B	−165.77 (12)
N1A—C1A—C2A—C7A	−18.76 (18)	N1B—C1B—C2B—C7B	13.32 (17)
O1A—C1A—C2A—C3A	−17.57 (18)	O1B—C1B—C2B—C3B	12.84 (18)
N1A—C1A—C2A—C3A	163.25 (11)	N1B—C1B—C2B—C3B	−168.06 (11)
C7A—C2A—C3A—C4A	1.48 (19)	C7B—C2B—C3B—C4B	−1.20 (19)
C1A—C2A—C3A—C4A	179.56 (12)	C1B—C2B—C3B—C4B	−179.87 (11)
C2A—C3A—C4A—C5A	−0.5 (2)	C2B—C3B—C4B—C5B	1.2 (2)
C3A—C4A—C5A—C6A	−0.7 (2)	C3B—C4B—C5B—C6B	−0.4 (2)
C4A—C5A—C6A—C7A	0.9 (2)	C4B—C5B—C6B—C7B	−0.3 (2)
C5A—C6A—C7A—C2A	0.07 (19)	C5B—C6B—C7B—C2B	0.26 (19)
C3A—C2A—C7A—C6A	−1.26 (19)	C3B—C2B—C7B—C6B	0.49 (18)
C1A—C2A—C7A—C6A	−179.20 (11)	C1B—C2B—C7B—C6B	179.07 (11)
C9A—N2A—C8A—N1A	−172.77 (11)	C9B—N2B—C8B—N1B	177.17 (11)
C9A—N2A—C8A—S1A	6.40 (18)	C9B—N2B—C8B—S1B	−2.38 (17)
C1A—N1A—C8A—N2A	14.13 (18)	C1B—N1B—C8B—N2B	−11.69 (18)
C1A—N1A—C8A—S1A	−165.10 (10)	C1B—N1B—C8B—S1B	167.88 (10)
C8A—N2A—C9A—C14A	−70.45 (17)	C8B—N2B—C9B—C10B	73.45 (16)
C8A—N2A—C9A—C10A	113.52 (14)	C8B—N2B—C9B—C14B	−108.83 (14)
C14A—C9A—C10A—C11A	1.36 (18)	C14B—C9B—C10B—C11B	2.19 (18)
N2A—C9A—C10A—C11A	177.64 (11)	N2B—C9B—C10B—C11B	179.97 (12)
C14A—C9A—C10A—Cl1A	−177.84 (9)	C14B—C9B—C10B—Cl2B	−176.07 (9)
N2A—C9A—C10A—Cl1A	−1.57 (16)	N2B—C9B—C10B—Cl2B	1.71 (17)
C9A—C10A—C11A—C12A	0.3 (2)	C9B—C10B—C11B—C12B	−2.2 (2)
Cl1A—C10A—C11A—C12A	179.50 (10)	Cl2B—C10B—C11B—C12B	176.11 (10)
C10A—C11A—C12A—C13A	−1.0 (2)	C10B—C11B—C12B—C13B	0.8 (2)
C11A—C12A—C13A—C14A	−0.1 (2)	C11B—C12B—C13B—C14B	0.5 (2)
C12A—C13A—C14A—C9A	1.84 (19)	C12B—C13B—C14B—C9B	−0.5 (2)
C12A—C13A—C14A—Cl2A	−176.08 (10)	C12B—C13B—C14B—Cl1B	178.91 (11)
C10A—C9A—C14A—C13A	−2.42 (18)	C10B—C9B—C14B—C13B	−0.86 (19)
N2A—C9A—C14A—C13A	−178.53 (11)	N2B—C9B—C14B—C13B	−178.69 (12)
C10A—C9A—C14A—Cl2A	175.43 (9)	C10B—C9B—C14B—Cl1B	179.78 (9)
N2A—C9A—C14A—Cl2A	−0.67 (17)	N2B—C9B—C14B—Cl1B	1.95 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···S1B	0.88	2.62	3.4414 (11)	155
N2A—H2A···O1A	0.88	1.97	2.6269 (14)	131
N1B—H1B···S1A	0.88	2.71	3.4772 (11)	146
N2B—H2B···O1B	0.88	1.95	2.6240 (14)	132