1-(4-Chloro-benzo-yl)-3-(2,4,6-trichloro-phen-yl)thio-urea hemihydrate.

The asymmetric unit of the title compound, C(14)H(8)Cl(4)N(2)OS·0.5H(2)O, contains two independent mol-ecules with different conformations with respect to the aromatic ring planes, and one water mol-ecule. The bond lengths and angles are typical of thio-urea compounds of this class. The mol-ecule exists in the solid state in its thione form with typical thio-urea C-S and C-O bonds lengths, as well as shortened C-N bonds. The dihedral angles between the two aromatic planes are 66.93 (8) and 60.44 (9)° in the two independent mol-ecules. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation and the crystal packing is characterized by N-H⋯O, O-H⋯S and O-H⋯Cl hydrogen bonds.

Related literature

For background and related structures, see: Khawar Rauf et al. (2006a ▶,b ▶,c ▶,d ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C14H8Cl4N2OS·0.5H2O

M = 403.09

Monoclinic,

a = 16.1428 (9) Å

b = 13.7340 (7) Å

c = 16.2850 (9) Å

β = 112.216 (4)°

V = 3342.4 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.84 mm−1

T = 173 (2) K

0.38 × 0.37 × 0.35 mm

Data collection

STOE IPDS II two-circle-diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.741, T max = 0.758

23391 measured reflections

7172 independent reflections

5964 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.02

7172 reflections

428 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.94 e Å−3

Δρmin = −0.60 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041251/si2141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041251/si2141Isup2.hkl

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

C14H8Cl4N2OS·0.5H2O	F(000) = 1624
Mr = 403.09	Dx = 1.602 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21741 reflections
a = 16.1428 (9) Å	θ = 2.2–27.1°
b = 13.7340 (7) Å	µ = 0.84 mm−1
c = 16.2850 (9) Å	T = 173 K
β = 112.216 (4)°	Block, colourless
V = 3342.4 (3) Å3	0.38 × 0.37 × 0.35 mm
Z = 8

STOE IPDS II two-circle-diffractometer	7172 independent reflections
Radiation source: fine-focus sealed tube	5964 reflections with I > 2σ(I)
graphite	Rint = 0.068
ω scans	θmax = 26.9°, θmin = 2.1°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −17→20
Tmin = 0.741, Tmax = 0.758	k = −17→17
23391 measured reflections	l = −20→20

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0647P)2 + 1.5427P] where P = (Fo2 + 2Fc2)/3
7172 reflections	(Δ/σ)max = 0.001
428 parameters	Δρmax = 0.94 e Å−3
7 restraints	Δρmin = −0.60 e Å−3

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
C1	0.37638 (14)	0.52532 (16)	0.57504 (15)	0.0302 (5)
O1	0.38255 (10)	0.53995 (13)	0.50312 (11)	0.0357 (4)
N1	0.29511 (12)	0.50614 (15)	0.58141 (13)	0.0324 (4)
H1	0.2955 (19)	0.497 (2)	0.6343 (10)	0.041 (8)*
C2	0.21054 (14)	0.50210 (17)	0.51379 (15)	0.0325 (5)
N2	0.20766 (12)	0.52155 (15)	0.43208 (13)	0.0332 (4)
H2	0.2559 (13)	0.537 (2)	0.4227 (19)	0.045 (8)*
S1	0.12057 (4)	0.47441 (6)	0.53583 (4)	0.04717 (18)
Cl1	0.71014 (4)	0.55572 (5)	0.90337 (4)	0.04341 (16)
Cl2	0.15939 (5)	0.34487 (6)	0.31698 (6)	0.0673 (2)
Cl3	−0.13692 (5)	0.54231 (9)	0.12131 (5)	0.0773 (3)
Cl4	0.11099 (5)	0.71115 (5)	0.40822 (5)	0.05120 (18)
C11	0.45662 (14)	0.52864 (16)	0.65923 (15)	0.0295 (4)
C12	0.45243 (15)	0.53432 (17)	0.74359 (15)	0.0333 (5)
H12	0.3960	0.5332	0.7492	0.040*
C13	0.53058 (16)	0.54156 (18)	0.81928 (15)	0.0355 (5)
H13	0.5278	0.5454	0.8764	0.043*
C14	0.61249 (15)	0.54311 (17)	0.80970 (15)	0.0337 (5)
C15	0.61818 (15)	0.53658 (18)	0.72711 (16)	0.0359 (5)
H15	0.6748	0.5374	0.7219	0.043*
C16	0.54017 (15)	0.52882 (17)	0.65206 (15)	0.0332 (5)
H16	0.5436	0.5236	0.5953	0.040*
C21	0.12477 (14)	0.52657 (18)	0.35815 (15)	0.0335 (5)
C22	0.09467 (16)	0.44876 (19)	0.29937 (18)	0.0406 (6)
C23	0.01410 (17)	0.4524 (2)	0.22662 (18)	0.0473 (7)
H23	−0.0059	0.3986	0.1874	0.057*
C24	−0.03568 (16)	0.5362 (2)	0.21313 (18)	0.0492 (7)
C25	−0.00886 (16)	0.6165 (2)	0.26850 (18)	0.0461 (6)
H25	−0.0447	0.6735	0.2577	0.055*
C26	0.07260 (15)	0.61070 (19)	0.34072 (16)	0.0371 (5)
C1A	0.24641 (14)	0.78726 (17)	0.78708 (15)	0.0314 (5)
O1A	0.28145 (10)	0.86354 (12)	0.82401 (11)	0.0359 (4)
N1A	0.27773 (12)	0.69679 (15)	0.82106 (13)	0.0328 (4)
H1A	0.2541 (18)	0.6458 (14)	0.7884 (16)	0.044 (8)*
C2A	0.34638 (14)	0.67443 (17)	0.90195 (15)	0.0313 (5)
N2A	0.38814 (13)	0.75109 (15)	0.95146 (13)	0.0344 (4)
H2A	0.374 (2)	0.8114 (10)	0.934 (2)	0.052 (9)*
S1A	0.37231 (4)	0.55898 (5)	0.93165 (4)	0.03769 (15)
Cl1A	−0.07853 (4)	0.81919 (6)	0.45000 (5)	0.05347 (19)
Cl2A	0.57143 (5)	0.76385 (6)	0.94715 (5)	0.05124 (18)
Cl3A	0.68978 (5)	0.70470 (5)	1.29886 (5)	0.0547 (2)
Cl4A	0.33577 (4)	0.72377 (6)	1.10872 (5)	0.04826 (17)
C11A	0.16642 (14)	0.78908 (17)	0.70221 (15)	0.0313 (5)
C12A	0.10421 (16)	0.71386 (19)	0.67392 (17)	0.0386 (5)
H12A	0.1136	0.6557	0.7079	0.046*
C13A	0.02828 (16)	0.7229 (2)	0.59643 (17)	0.0419 (6)
H13A	−0.0144	0.6717	0.5778	0.050*
C14A	0.01600 (15)	0.8069 (2)	0.54725 (16)	0.0387 (5)
C15A	0.07758 (16)	0.8833 (2)	0.57343 (17)	0.0425 (6)
H15A	0.0686	0.9405	0.5384	0.051*
C16A	0.15197 (15)	0.87407 (18)	0.65141 (16)	0.0369 (5)
H16A	0.1937	0.9261	0.6706	0.044*
C21A	0.45990 (15)	0.73872 (17)	1.03485 (15)	0.0332 (5)
C22A	0.54822 (16)	0.74224 (18)	1.04103 (16)	0.0357 (5)
C23A	0.61967 (16)	0.72962 (18)	1.12165 (18)	0.0405 (6)
H23A	0.6796	0.7304	1.1248	0.049*
C24A	0.60090 (17)	0.71594 (18)	1.19714 (17)	0.0401 (6)
C25A	0.51466 (17)	0.71352 (18)	1.19431 (16)	0.0389 (5)
H25A	0.5032	0.7042	1.2469	0.047*
C26A	0.44472 (15)	0.72506 (17)	1.11274 (16)	0.0346 (5)
O1W	0.23342 (15)	0.51628 (16)	0.73321 (13)	0.0524 (5)
H1WA	0.250 (2)	0.487 (2)	0.7831 (12)	0.063*
H1WB	0.1870 (15)	0.495 (2)	0.6911 (16)	0.063*

	U11	U22	U33	U12	U13	U23
C1	0.0239 (10)	0.0309 (11)	0.0321 (11)	0.0011 (8)	0.0063 (8)	−0.0005 (9)
O1	0.0247 (7)	0.0512 (10)	0.0287 (8)	0.0024 (7)	0.0073 (6)	0.0029 (7)
N1	0.0257 (9)	0.0420 (11)	0.0255 (9)	−0.0055 (8)	0.0054 (7)	0.0023 (8)
C2	0.0249 (10)	0.0349 (11)	0.0321 (11)	−0.0035 (9)	0.0045 (8)	−0.0004 (9)
N2	0.0203 (8)	0.0445 (11)	0.0294 (10)	−0.0007 (8)	0.0033 (7)	0.0021 (8)
S1	0.0294 (3)	0.0704 (5)	0.0407 (3)	−0.0145 (3)	0.0121 (3)	−0.0018 (3)
Cl1	0.0274 (3)	0.0557 (4)	0.0352 (3)	−0.0004 (2)	−0.0016 (2)	−0.0011 (3)
Cl2	0.0476 (4)	0.0498 (4)	0.0882 (6)	0.0034 (3)	0.0070 (4)	−0.0203 (4)
Cl3	0.0285 (3)	0.1409 (9)	0.0451 (4)	−0.0121 (4)	−0.0059 (3)	0.0145 (5)
Cl4	0.0482 (4)	0.0483 (4)	0.0538 (4)	0.0070 (3)	0.0156 (3)	−0.0073 (3)
C11	0.0243 (10)	0.0318 (11)	0.0283 (11)	−0.0001 (8)	0.0051 (8)	0.0008 (9)
C12	0.0244 (10)	0.0415 (12)	0.0309 (11)	−0.0046 (9)	0.0069 (8)	−0.0018 (10)
C13	0.0325 (11)	0.0442 (13)	0.0266 (11)	−0.0031 (10)	0.0074 (9)	−0.0009 (10)
C14	0.0266 (10)	0.0337 (11)	0.0328 (12)	0.0005 (9)	0.0022 (9)	0.0001 (9)
C15	0.0239 (10)	0.0450 (13)	0.0357 (12)	0.0045 (9)	0.0076 (9)	0.0004 (10)
C16	0.0266 (10)	0.0403 (12)	0.0310 (11)	0.0042 (9)	0.0091 (9)	0.0000 (9)
C21	0.0193 (9)	0.0481 (13)	0.0278 (11)	−0.0036 (9)	0.0030 (8)	0.0015 (10)
C22	0.0274 (11)	0.0459 (14)	0.0442 (14)	−0.0050 (10)	0.0088 (10)	−0.0036 (11)
C23	0.0320 (12)	0.0644 (18)	0.0400 (14)	−0.0158 (12)	0.0072 (10)	−0.0089 (13)
C24	0.0245 (11)	0.079 (2)	0.0371 (13)	−0.0095 (12)	0.0043 (10)	0.0078 (13)
C25	0.0254 (11)	0.0633 (17)	0.0447 (14)	0.0073 (11)	0.0078 (10)	0.0131 (13)
C26	0.0259 (10)	0.0467 (14)	0.0363 (12)	0.0020 (10)	0.0090 (9)	0.0027 (11)
C1A	0.0234 (10)	0.0387 (12)	0.0305 (11)	−0.0002 (9)	0.0084 (8)	0.0006 (9)
O1A	0.0302 (8)	0.0364 (9)	0.0341 (8)	−0.0032 (7)	0.0043 (6)	−0.0006 (7)
N1A	0.0277 (9)	0.0350 (10)	0.0300 (10)	−0.0005 (8)	0.0045 (7)	−0.0024 (8)
C2A	0.0239 (10)	0.0400 (12)	0.0288 (11)	−0.0017 (9)	0.0084 (8)	−0.0006 (9)
N2A	0.0297 (9)	0.0375 (11)	0.0272 (9)	−0.0005 (8)	0.0008 (8)	0.0005 (8)
S1A	0.0343 (3)	0.0375 (3)	0.0342 (3)	0.0004 (2)	0.0049 (2)	0.0024 (2)
Cl1A	0.0317 (3)	0.0725 (5)	0.0405 (3)	0.0089 (3)	−0.0041 (2)	0.0019 (3)
Cl2A	0.0459 (4)	0.0694 (5)	0.0421 (3)	−0.0076 (3)	0.0207 (3)	−0.0047 (3)
Cl3A	0.0466 (4)	0.0533 (4)	0.0410 (4)	0.0015 (3)	−0.0098 (3)	0.0064 (3)
Cl4A	0.0348 (3)	0.0623 (4)	0.0491 (4)	−0.0024 (3)	0.0173 (3)	0.0007 (3)
C11A	0.0233 (10)	0.0395 (12)	0.0289 (11)	0.0003 (9)	0.0073 (8)	−0.0008 (9)
C12A	0.0285 (11)	0.0437 (13)	0.0362 (12)	−0.0029 (10)	0.0037 (9)	0.0037 (10)
C13A	0.0290 (11)	0.0490 (14)	0.0396 (13)	−0.0052 (10)	0.0038 (10)	−0.0033 (11)
C14A	0.0254 (10)	0.0526 (15)	0.0326 (12)	0.0073 (10)	0.0049 (9)	−0.0016 (11)
C15A	0.0351 (12)	0.0481 (14)	0.0400 (13)	0.0070 (11)	0.0094 (10)	0.0071 (11)
C16A	0.0275 (10)	0.0403 (13)	0.0383 (12)	0.0005 (9)	0.0073 (9)	0.0012 (10)
C21A	0.0288 (11)	0.0338 (11)	0.0303 (11)	−0.0003 (9)	0.0035 (9)	−0.0011 (9)
C22A	0.0314 (11)	0.0377 (12)	0.0339 (12)	−0.0021 (9)	0.0077 (9)	−0.0026 (10)
C23A	0.0273 (11)	0.0412 (13)	0.0454 (14)	−0.0015 (9)	0.0052 (10)	−0.0031 (11)
C24A	0.0385 (13)	0.0328 (12)	0.0359 (12)	0.0004 (10)	−0.0009 (10)	0.0013 (10)
C25A	0.0428 (13)	0.0375 (13)	0.0311 (12)	−0.0013 (10)	0.0078 (10)	0.0023 (10)
C26A	0.0282 (11)	0.0373 (12)	0.0335 (12)	0.0003 (9)	0.0064 (9)	0.0008 (10)
O1W	0.0528 (12)	0.0601 (13)	0.0406 (11)	−0.0075 (10)	0.0133 (9)	−0.0067 (9)

C1—O1	1.229 (3)	C1A—N1A	1.376 (3)
C1—N1	1.380 (3)	C1A—C11A	1.493 (3)
C1—C11	1.489 (3)	N1A—C2A	1.398 (3)
N1—C2	1.394 (3)	N1A—H1A	0.874 (10)
N1—H1	0.866 (10)	C2A—N2A	1.342 (3)
C2—N2	1.341 (3)	C2A—S1A	1.664 (2)
C2—S1	1.666 (2)	N2A—C21A	1.423 (3)
N2—C21	1.424 (3)	N2A—H2A	0.877 (10)
N2—H2	0.873 (10)	Cl1A—C14A	1.743 (2)
Cl1—C14	1.739 (2)	Cl2A—C22A	1.732 (3)
Cl2—C22	1.727 (3)	Cl3A—C24A	1.741 (2)
Cl3—C24	1.751 (3)	Cl4A—C26A	1.735 (2)
Cl4—C26	1.726 (3)	C11A—C12A	1.392 (3)
C11—C16	1.397 (3)	C11A—C16A	1.398 (3)
C11—C12	1.403 (3)	C12A—C13A	1.393 (3)
C12—C13	1.395 (3)	C12A—H12A	0.9500
C12—H12	0.9500	C13A—C14A	1.376 (4)
C13—C14	1.389 (3)	C13A—H13A	0.9500
C13—H13	0.9500	C14A—C15A	1.396 (4)
C14—C15	1.385 (3)	C15A—C16A	1.385 (3)
C15—C16	1.388 (3)	C15A—H15A	0.9500
C15—H15	0.9500	C16A—H16A	0.9500
C16—H16	0.9500	C21A—C26A	1.393 (3)
C21—C22	1.394 (4)	C21A—C22A	1.392 (3)
C21—C26	1.394 (3)	C22A—C23A	1.392 (3)
C22—C23	1.390 (4)	C23A—C24A	1.386 (4)
C23—C24	1.372 (4)	C23A—H23A	0.9500
C23—H23	0.9500	C24A—C25A	1.376 (4)
C24—C25	1.386 (4)	C25A—C26A	1.389 (3)
C25—C26	1.396 (3)	C25A—H25A	0.9500
C25—H25	0.9500	O1W—H1WA	0.855 (10)
C1A—O1A	1.234 (3)	O1W—H1WB	0.855 (10)
O1—C1—N1	121.66 (19)	O1A—C1A—C11A	120.9 (2)
O1—C1—C11	121.1 (2)	N1A—C1A—C11A	116.4 (2)
N1—C1—C11	117.2 (2)	C1A—N1A—C2A	128.1 (2)
C1—N1—C2	128.6 (2)	C1A—N1A—H1A	118.0 (19)
C1—N1—H1	116.8 (19)	C2A—N1A—H1A	113.9 (19)
C2—N1—H1	114.6 (19)	N2A—C2A—N1A	115.6 (2)
N2—C2—N1	115.6 (2)	N2A—C2A—S1A	123.96 (17)
N2—C2—S1	123.59 (16)	N1A—C2A—S1A	120.39 (17)
N1—C2—S1	120.80 (18)	C2A—N2A—C21A	121.5 (2)
C2—N2—C21	121.19 (19)	C2A—N2A—H2A	122 (2)
C2—N2—H2	121 (2)	C21A—N2A—H2A	116 (2)
C21—N2—H2	117 (2)	C12A—C11A—C16A	119.0 (2)
C16—C11—C12	119.2 (2)	C12A—C11A—C1A	123.9 (2)
C16—C11—C1	117.0 (2)	C16A—C11A—C1A	117.0 (2)
C12—C11—C1	123.8 (2)	C11A—C12A—C13A	120.8 (2)
C13—C12—C11	120.5 (2)	C11A—C12A—H12A	119.6
C13—C12—H12	119.8	C13A—C12A—H12A	119.6
C11—C12—H12	119.8	C14A—C13A—C12A	119.1 (2)
C14—C13—C12	118.9 (2)	C14A—C13A—H13A	120.5
C14—C13—H13	120.6	C12A—C13A—H13A	120.5
C12—C13—H13	120.6	C13A—C14A—C15A	121.5 (2)
C15—C14—C13	121.6 (2)	C13A—C14A—Cl1A	119.6 (2)
C15—C14—Cl1	119.17 (18)	C15A—C14A—Cl1A	118.9 (2)
C13—C14—Cl1	119.25 (19)	C16A—C15A—C14A	118.8 (2)
C14—C15—C16	119.3 (2)	C16A—C15A—H15A	120.6
C14—C15—H15	120.4	C14A—C15A—H15A	120.6
C16—C15—H15	120.4	C15A—C16A—C11A	120.8 (2)
C15—C16—C11	120.6 (2)	C15A—C16A—H16A	119.6
C15—C16—H16	119.7	C11A—C16A—H16A	119.6
C11—C16—H16	119.7	C26A—C21A—C22A	117.8 (2)
C22—C21—C26	117.9 (2)	C26A—C21A—N2A	121.7 (2)
C22—C21—N2	121.1 (2)	C22A—C21A—N2A	120.5 (2)
C26—C21—N2	121.0 (2)	C21A—C22A—C23A	121.6 (2)
C23—C22—C21	121.9 (3)	C21A—C22A—Cl2A	119.99 (18)
C23—C22—Cl2	118.9 (2)	C23A—C22A—Cl2A	118.4 (2)
C21—C22—Cl2	119.17 (18)	C24A—C23A—C22A	118.2 (2)
C24—C23—C22	118.0 (3)	C24A—C23A—H23A	120.9
C24—C23—H23	121.0	C22A—C23A—H23A	120.9
C22—C23—H23	121.0	C25A—C24A—C23A	122.1 (2)
C23—C24—C25	122.9 (2)	C25A—C24A—Cl3A	119.3 (2)
C23—C24—Cl3	118.6 (2)	C23A—C24A—Cl3A	118.6 (2)
C25—C24—Cl3	118.6 (2)	C24A—C25A—C26A	118.4 (2)
C24—C25—C26	117.8 (3)	C24A—C25A—H25A	120.8
C24—C25—H25	121.1	C26A—C25A—H25A	120.8
C26—C25—H25	121.1	C25A—C26A—C21A	121.8 (2)
C21—C26—C25	121.5 (2)	C25A—C26A—Cl4A	118.7 (2)
C21—C26—Cl4	119.26 (17)	C21A—C26A—Cl4A	119.46 (17)
C25—C26—Cl4	119.2 (2)	H1WA—O1W—H1WB	118 (3)
O1A—C1A—N1A	122.7 (2)
O1—C1—N1—C2	−1.6 (4)	O1A—C1A—N1A—C2A	5.1 (4)
C11—C1—N1—C2	177.8 (2)	C11A—C1A—N1A—C2A	−174.6 (2)
C1—N1—C2—N2	−1.6 (4)	C1A—N1A—C2A—N2A	−1.7 (3)
C1—N1—C2—S1	178.25 (19)	C1A—N1A—C2A—S1A	178.52 (19)
N1—C2—N2—C21	−175.6 (2)	N1A—C2A—N2A—C21A	−179.3 (2)
S1—C2—N2—C21	4.6 (3)	S1A—C2A—N2A—C21A	0.4 (3)
O1—C1—C11—C16	−12.9 (3)	O1A—C1A—C11A—C12A	−155.0 (2)
N1—C1—C11—C16	167.7 (2)	N1A—C1A—C11A—C12A	24.7 (3)
O1—C1—C11—C12	165.2 (2)	O1A—C1A—C11A—C16A	21.6 (3)
N1—C1—C11—C12	−14.1 (3)	N1A—C1A—C11A—C16A	−158.7 (2)
C16—C11—C12—C13	1.0 (4)	C16A—C11A—C12A—C13A	−0.3 (4)
C1—C11—C12—C13	−177.1 (2)	C1A—C11A—C12A—C13A	176.2 (2)
C11—C12—C13—C14	0.0 (4)	C11A—C12A—C13A—C14A	0.9 (4)
C12—C13—C14—C15	−0.7 (4)	C12A—C13A—C14A—C15A	−0.3 (4)
C12—C13—C14—Cl1	178.12 (19)	C12A—C13A—C14A—Cl1A	179.9 (2)
C13—C14—C15—C16	0.3 (4)	C13A—C14A—C15A—C16A	−0.9 (4)
Cl1—C14—C15—C16	−178.50 (19)	Cl1A—C14A—C15A—C16A	179.0 (2)
C14—C15—C16—C11	0.7 (4)	C14A—C15A—C16A—C11A	1.4 (4)
C12—C11—C16—C15	−1.4 (4)	C12A—C11A—C16A—C15A	−0.8 (4)
C1—C11—C16—C15	176.9 (2)	C1A—C11A—C16A—C15A	−177.6 (2)
C2—N2—C21—C22	−100.5 (3)	C2A—N2A—C21A—C26A	−85.7 (3)
C2—N2—C21—C26	81.6 (3)	C2A—N2A—C21A—C22A	95.8 (3)
C26—C21—C22—C23	−1.8 (4)	C26A—C21A—C22A—C23A	2.0 (4)
N2—C21—C22—C23	−179.8 (2)	N2A—C21A—C22A—C23A	−179.5 (2)
C26—C21—C22—Cl2	177.95 (19)	C26A—C21A—C22A—Cl2A	−177.46 (18)
N2—C21—C22—Cl2	0.0 (3)	N2A—C21A—C22A—Cl2A	1.1 (3)
C21—C22—C23—C24	0.7 (4)	C21A—C22A—C23A—C24A	−1.8 (4)
Cl2—C22—C23—C24	−179.1 (2)	Cl2A—C22A—C23A—C24A	177.66 (19)
C22—C23—C24—C25	0.2 (4)	C22A—C23A—C24A—C25A	0.7 (4)
C22—C23—C24—Cl3	179.5 (2)	C22A—C23A—C24A—Cl3A	−177.60 (19)
C23—C24—C25—C26	0.1 (4)	C23A—C24A—C25A—C26A	0.1 (4)
Cl3—C24—C25—C26	−179.2 (2)	Cl3A—C24A—C25A—C26A	178.41 (19)
C22—C21—C26—C25	2.1 (4)	C24A—C25A—C26A—C21A	0.1 (4)
N2—C21—C26—C25	−179.9 (2)	C24A—C25A—C26A—Cl4A	−179.14 (19)
C22—C21—C26—Cl4	−176.13 (19)	C22A—C21A—C26A—C25A	−1.1 (4)
N2—C21—C26—Cl4	1.8 (3)	N2A—C21A—C26A—C25A	−179.6 (2)
C24—C25—C26—C21	−1.3 (4)	C22A—C21A—C26A—Cl4A	178.12 (18)
C24—C25—C26—Cl4	176.9 (2)	N2A—C21A—C26A—Cl4A	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.87 (1)	2.21 (2)	2.997 (3)	151 (3)
N2—H2···O1	0.87 (1)	1.97 (2)	2.627 (2)	131 (3)
N2—H2···O1Ai	0.87 (1)	2.26 (2)	2.931 (3)	133 (2)
N1A—H1A···O1W	0.87 (1)	1.96 (1)	2.816 (3)	164 (3)
N2A—H2A···O1A	0.88 (1)	1.98 (3)	2.637 (3)	130 (3)
N2A—H2A···O1ii	0.88 (1)	2.31 (2)	3.001 (3)	136 (3)
O1W—H1WA···S1A	0.86 (1)	2.67 (3)	3.215 (2)	123 (3)
O1W—H1WA···Cl3iii	0.86 (1)	2.84 (3)	3.388 (2)	123 (3)
O1W—H1WB···S1	0.86 (1)	2.36 (2)	3.091 (2)	144 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1W	0.866 (10)	2.211 (17)	2.997 (3)	151 (3)
N2—H2⋯O1	0.873 (10)	1.97 (2)	2.627 (2)	131 (3)
N2—H2⋯O1Ai	0.873 (10)	2.26 (2)	2.931 (3)	133 (2)
N1A—H1A⋯O1W	0.874 (10)	1.964 (13)	2.816 (3)	164 (3)
N2A—H2A⋯O1A	0.877 (10)	1.98 (3)	2.637 (3)	130 (3)
N2A—H2A⋯O1ii	0.877 (10)	2.31 (2)	3.001 (3)	136 (3)
O1W—H1WA⋯S1A	0.855 (10)	2.67 (3)	3.215 (2)	123 (3)
O1W—H1WA⋯Cl3iii	0.855 (10)	2.84 (3)	3.388 (2)	123 (3)
O1W—H1WB⋯S1	0.855 (10)	2.36 (2)	3.091 (2)	144 (3)

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