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

The asymmetric unit of the title compound, C₁₄H₉Cl₃N₂OS, contains two independent mol­ecules with slightly different conformations with respect to the aromatic ring planes. These two independent mol­ecules form dimers via inter­molecular N—H...S hydrogen bonds and which are stacked along [100].

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.083
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C2      ..       6.11 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1A    -   C2A     ..       5.28 su
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O1A     ..       3.23 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2A   ..  S1A     ..       3.46 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  S1A    ..  C12A    ..       3.24 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

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

Crystal data

C14H9Cl3N2OS	F(000) = 728
Mr = 359.64	Dx = 1.584 Mg m^−3
Triclinic, P1	Melting point: 473 K
a = 7.8338 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.4275 (9) Å	Cell parameters from 21597 reflections
c = 14.545 (1) Å	θ = 3.5–27.2°
α = 100.858 (5)°	µ = 0.74 mm^−1
β = 104.460 (6)°	T = 173 K
γ = 101.767 (5)°	Block, colourless
V = 1507.91 (18) Å^3	0.34 × 0.32 × 0.27 mm
Z = 4

Data collection

Stoe IPDS-II two-circle diffractometer	6903 independent reflections
Radiation source: fine-focus sealed tube	6338 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −10→10
Tmin = 0.786, Tmax = 0.824	k = −18→18
21597 measured reflections	l = −15→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.6473P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6903 reflections	Δρmax = 0.33 e Å^−3
396 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0162 (10)

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
C1	0.08210 (18)	0.36760 (10)	−0.00631 (10)	0.0164 (2)
O1	0.00159 (14)	0.33547 (9)	0.04825 (8)	0.0249 (2)
N1	0.27169 (16)	0.39578 (9)	0.01771 (9)	0.0161 (2)
H1	0.314 (3)	0.4273 (15)	−0.0160 (16)	0.028 (5)*
C2	0.39839 (18)	0.38057 (9)	0.09614 (10)	0.0156 (2)
S1	0.62160 (5)	0.41755 (3)	0.10883 (3)	0.02296 (9)
N2	0.32761 (16)	0.33592 (9)	0.15672 (9)	0.0176 (2)
H2	0.208 (3)	0.3203 (15)	0.1421 (15)	0.029 (5)*
C11	−0.01919 (18)	0.37900 (9)	−0.10382 (10)	0.0153 (2)
C12	0.05234 (18)	0.37144 (10)	−0.18346 (10)	0.0176 (3)
H12	0.1695	0.3600	−0.1770	0.021*
C13	−0.05196 (19)	0.38110 (10)	−0.27236 (10)	0.0190 (3)
C14	−0.22228 (19)	0.39996 (10)	−0.28299 (11)	0.0202 (3)
H14	−0.2896	0.4084	−0.3435	0.024*
C15	−0.29275 (19)	0.40626 (10)	−0.20336 (11)	0.0206 (3)
H15	−0.4089	0.4190	−0.2098	0.025*
C16	−0.19341 (18)	0.39399 (10)	−0.11447 (10)	0.0179 (3)
H16	−0.2438	0.3958	−0.0614	0.021*
Cl1	0.03336 (6)	0.36996 (4)	−0.37247 (3)	0.03537 (11)
C21	0.42776 (18)	0.29338 (10)	0.22608 (10)	0.0164 (3)
C22	0.52249 (19)	0.34521 (10)	0.32329 (10)	0.0186 (3)
C23	0.6075 (2)	0.29931 (12)	0.39128 (11)	0.0237 (3)
H23	0.6727	0.3356	0.4568	0.028*
C24	0.5958 (2)	0.20012 (12)	0.36207 (12)	0.0262 (3)
H24	0.6511	0.1685	0.4085	0.031*
C25	0.5043 (2)	0.14658 (11)	0.26578 (12)	0.0248 (3)
H25	0.4980	0.0790	0.2460	0.030*
C26	0.42172 (19)	0.19387 (10)	0.19868 (11)	0.0204 (3)
Cl2	0.53560 (5)	0.46836 (3)	0.36222 (3)	0.02748 (10)
Cl3	0.31038 (6)	0.12890 (3)	0.07743 (3)	0.03502 (11)
C1A	0.25524 (18)	0.23090 (10)	0.49583 (10)	0.0164 (3)
O1A	0.38440 (14)	0.29922 (7)	0.54926 (8)	0.0224 (2)
N1A	0.20686 (16)	0.14199 (8)	0.51944 (9)	0.0167 (2)
H1A	0.102 (3)	0.0991 (15)	0.4820 (15)	0.027 (5)*
C2A	0.30089 (18)	0.11286 (9)	0.59911 (10)	0.0151 (2)
S1A	0.21852 (5)	0.00360 (2)	0.61748 (3)	0.02075 (9)
N2A	0.45756 (16)	0.17633 (9)	0.65797 (9)	0.0177 (2)
H2A	0.489 (3)	0.2337 (16)	0.6439 (16)	0.033 (5)*
C11A	0.13665 (18)	0.23864 (10)	0.40059 (10)	0.0164 (2)
C12A	0.05501 (19)	0.15696 (10)	0.32029 (10)	0.0179 (3)
H12A	0.0755	0.0949	0.3241	0.022*
C13A	−0.05700 (19)	0.16864 (11)	0.23457 (10)	0.0207 (3)
C14A	−0.0875 (2)	0.25901 (12)	0.22643 (11)	0.0235 (3)
H14A	−0.1654	0.2652	0.1677	0.028*
C15A	−0.0015 (2)	0.34019 (11)	0.30621 (12)	0.0254 (3)
H15A	−0.0198	0.4024	0.3015	0.030*
C16A	0.1114 (2)	0.33063 (11)	0.39301 (11)	0.0216 (3)
H16A	0.1709	0.3863	0.4467	0.026*
Cl1A	−0.16683 (6)	0.06582 (3)	0.13608 (3)	0.03406 (11)
C21A	0.57398 (18)	0.15348 (9)	0.73796 (10)	0.0167 (3)
C22A	0.7271 (2)	0.12172 (10)	0.72732 (11)	0.0207 (3)
C23A	0.8481 (2)	0.10365 (11)	0.80627 (13)	0.0264 (3)
H23A	0.9524	0.0830	0.7983	0.032*
C24A	0.8145 (2)	0.11617 (11)	0.89622 (12)	0.0281 (3)
H24A	0.8964	0.1039	0.9499	0.034*
C25A	0.6623 (2)	0.14652 (11)	0.90928 (11)	0.0260 (3)
H25A	0.6393	0.1540	0.9710	0.031*
C26A	0.54439 (19)	0.16575 (10)	0.83017 (11)	0.0197 (3)
Cl2A	0.76385 (6)	0.10163 (4)	0.61294 (3)	0.03649 (11)
Cl3A	0.35813 (6)	0.20711 (3)	0.84642 (3)	0.03105 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0153 (6)	0.0174 (6)	0.0156 (6)	0.0040 (5)	0.0026 (5)	0.0052 (5)
O1	0.0174 (5)	0.0378 (6)	0.0204 (5)	0.0033 (4)	0.0044 (4)	0.0151 (4)
N1	0.0146 (5)	0.0204 (5)	0.0138 (5)	0.0035 (4)	0.0030 (4)	0.0084 (4)
C2	0.0166 (6)	0.0156 (6)	0.0140 (6)	0.0048 (5)	0.0031 (5)	0.0040 (5)
S1	0.01353 (16)	0.0354 (2)	0.02265 (18)	0.00520 (13)	0.00451 (13)	0.01625 (15)
N2	0.0143 (5)	0.0226 (6)	0.0173 (6)	0.0048 (4)	0.0029 (4)	0.0110 (4)
C11	0.0148 (6)	0.0144 (6)	0.0142 (6)	0.0016 (5)	0.0014 (5)	0.0038 (4)
C12	0.0153 (6)	0.0198 (6)	0.0172 (6)	0.0051 (5)	0.0035 (5)	0.0050 (5)
C13	0.0210 (6)	0.0214 (6)	0.0135 (6)	0.0031 (5)	0.0050 (5)	0.0049 (5)
C14	0.0196 (6)	0.0204 (6)	0.0166 (6)	0.0035 (5)	−0.0008 (5)	0.0060 (5)
C15	0.0164 (6)	0.0219 (7)	0.0218 (7)	0.0060 (5)	0.0021 (5)	0.0055 (5)
C16	0.0168 (6)	0.0189 (6)	0.0173 (6)	0.0043 (5)	0.0045 (5)	0.0045 (5)
Cl1	0.0346 (2)	0.0575 (3)	0.01862 (19)	0.01339 (19)	0.01299 (16)	0.01232 (17)
C21	0.0153 (6)	0.0202 (6)	0.0166 (6)	0.0053 (5)	0.0052 (5)	0.0099 (5)
C22	0.0179 (6)	0.0219 (6)	0.0178 (7)	0.0067 (5)	0.0056 (5)	0.0073 (5)
C23	0.0231 (7)	0.0346 (8)	0.0164 (7)	0.0124 (6)	0.0043 (6)	0.0103 (6)
C24	0.0282 (7)	0.0336 (8)	0.0269 (8)	0.0170 (6)	0.0101 (6)	0.0190 (6)
C25	0.0282 (7)	0.0221 (7)	0.0304 (8)	0.0108 (6)	0.0116 (6)	0.0135 (6)
C26	0.0204 (6)	0.0217 (7)	0.0196 (7)	0.0044 (5)	0.0060 (5)	0.0075 (5)
Cl2	0.0323 (2)	0.02163 (17)	0.02467 (19)	0.00920 (14)	0.00214 (15)	0.00308 (13)
Cl3	0.0461 (2)	0.02582 (19)	0.0236 (2)	0.00557 (16)	0.00129 (17)	0.00032 (14)
C1A	0.0166 (6)	0.0178 (6)	0.0147 (6)	0.0051 (5)	0.0029 (5)	0.0059 (5)
O1A	0.0216 (5)	0.0191 (5)	0.0205 (5)	−0.0001 (4)	−0.0014 (4)	0.0070 (4)
N1A	0.0160 (5)	0.0166 (5)	0.0138 (5)	0.0017 (4)	−0.0015 (4)	0.0060 (4)
C2A	0.0166 (6)	0.0167 (6)	0.0118 (6)	0.0057 (5)	0.0021 (5)	0.0043 (5)
S1A	0.02094 (17)	0.01646 (16)	0.01959 (17)	0.00077 (12)	−0.00273 (13)	0.00853 (12)
N2A	0.0173 (5)	0.0166 (5)	0.0156 (6)	0.0020 (4)	−0.0013 (4)	0.0067 (4)
C11A	0.0144 (6)	0.0202 (6)	0.0148 (6)	0.0036 (5)	0.0027 (5)	0.0085 (5)
C12A	0.0189 (6)	0.0216 (6)	0.0152 (6)	0.0065 (5)	0.0047 (5)	0.0084 (5)
C13A	0.0197 (6)	0.0275 (7)	0.0153 (6)	0.0055 (5)	0.0046 (5)	0.0083 (5)
C14A	0.0203 (7)	0.0341 (8)	0.0207 (7)	0.0090 (6)	0.0049 (6)	0.0177 (6)
C15A	0.0264 (7)	0.0245 (7)	0.0298 (8)	0.0086 (6)	0.0071 (6)	0.0172 (6)
C16A	0.0229 (7)	0.0201 (6)	0.0226 (7)	0.0048 (5)	0.0057 (6)	0.0098 (5)
Cl1A	0.0432 (2)	0.0367 (2)	0.01446 (17)	0.01006 (17)	−0.00224 (16)	0.00315 (14)
C21A	0.0159 (6)	0.0157 (6)	0.0141 (6)	0.0021 (5)	−0.0019 (5)	0.0042 (5)
C22A	0.0196 (6)	0.0196 (6)	0.0204 (7)	0.0048 (5)	0.0026 (5)	0.0045 (5)
C23A	0.0188 (7)	0.0228 (7)	0.0335 (9)	0.0066 (5)	−0.0010 (6)	0.0081 (6)
C24A	0.0244 (7)	0.0255 (7)	0.0263 (8)	0.0028 (6)	−0.0074 (6)	0.0120 (6)
C25A	0.0298 (8)	0.0269 (7)	0.0156 (7)	0.0026 (6)	−0.0010 (6)	0.0074 (5)
C26A	0.0194 (6)	0.0192 (6)	0.0173 (7)	0.0037 (5)	0.0015 (5)	0.0042 (5)
Cl2A	0.0387 (2)	0.0502 (3)	0.0283 (2)	0.02049 (19)	0.01667 (18)	0.00951 (18)
Cl3A	0.0308 (2)	0.0390 (2)	0.0278 (2)	0.01551 (16)	0.01269 (16)	0.00688 (16)

Geometric parameters (Å, º)

C1—O1	1.2296 (17)	C1A—O1A	1.2293 (17)
C1—N1	1.3908 (17)	C1A—N1A	1.3928 (17)
C1—C11	1.4991 (18)	C1A—C11A	1.5008 (18)
N1—C2	1.3973 (17)	N1A—C2A	1.3947 (17)
N1—H1	0.81 (2)	N1A—H1A	0.89 (2)
C2—N2	1.3457 (18)	C2A—N2A	1.3414 (17)
C2—S1	1.6726 (14)	C2A—S1A	1.6741 (14)
N2—C21	1.4298 (17)	N2A—C21A	1.4252 (17)
N2—H2	0.87 (2)	N2A—H2A	0.89 (2)
C11—C16	1.4003 (18)	C11A—C12A	1.4010 (19)
C11—C12	1.4032 (19)	C11A—C16A	1.4014 (19)
C12—C13	1.3949 (19)	C12A—C13A	1.3950 (19)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.392 (2)	C13A—C14A	1.394 (2)
C13—Cl1	1.7420 (14)	C13A—Cl1A	1.7482 (15)
C14—C15	1.398 (2)	C14A—C15A	1.396 (2)
C14—H14	0.9500	C14A—H14A	0.9500
C15—C16	1.396 (2)	C15A—C16A	1.397 (2)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500
C21—C22	1.400 (2)	C21A—C22A	1.4012 (19)
C21—C26	1.4034 (19)	C21A—C26A	1.402 (2)
C22—C23	1.399 (2)	C22A—C23A	1.398 (2)
C22—Cl2	1.7337 (14)	C22A—Cl2A	1.7395 (16)
C23—C24	1.391 (2)	C23A—C24A	1.384 (2)
C23—H23	0.9500	C23A—H23A	0.9500
C24—C25	1.392 (2)	C24A—C25A	1.394 (2)
C24—H24	0.9500	C24A—H24A	0.9500
C25—C26	1.397 (2)	C25A—C26A	1.396 (2)
C25—H25	0.9500	C25A—H25A	0.9500
C26—Cl3	1.7393 (15)	C26A—Cl3A	1.7365 (15)
O1—C1—N1	122.73 (13)	O1A—C1A—N1A	122.87 (12)
O1—C1—C11	121.75 (12)	O1A—C1A—C11A	121.78 (12)
N1—C1—C11	115.52 (12)	N1A—C1A—C11A	115.34 (11)
C1—N1—C2	127.58 (12)	C1A—N1A—C2A	127.10 (11)
C1—N1—H1	116.2 (15)	C1A—N1A—H1A	118.0 (13)
C2—N1—H1	116.1 (15)	C2A—N1A—H1A	114.9 (13)
N2—C2—N1	115.73 (12)	N2A—C2A—N1A	116.49 (12)
N2—C2—S1	124.84 (11)	N2A—C2A—S1A	123.12 (10)
N1—C2—S1	119.43 (10)	N1A—C2A—S1A	120.39 (10)
C2—N2—C21	123.94 (12)	C2A—N2A—C21A	122.49 (11)
C2—N2—H2	115.9 (14)	C2A—N2A—H2A	117.0 (14)
C21—N2—H2	118.4 (14)	C21A—N2A—H2A	120.5 (14)
C16—C11—C12	120.36 (13)	C12A—C11A—C16A	120.32 (13)
C16—C11—C1	117.44 (12)	C12A—C11A—C1A	121.44 (12)
C12—C11—C1	122.15 (12)	C16A—C11A—C1A	118.24 (12)
C13—C12—C11	118.67 (12)	C13A—C12A—C11A	118.59 (13)
C13—C12—H12	120.7	C13A—C12A—H12A	120.7
C11—C12—H12	120.7	C11A—C12A—H12A	120.7
C14—C13—C12	121.65 (13)	C14A—C13A—C12A	121.92 (14)
C14—C13—Cl1	119.13 (11)	C14A—C13A—Cl1A	119.37 (11)
C12—C13—Cl1	119.22 (11)	C12A—C13A—Cl1A	118.68 (11)
C13—C14—C15	119.06 (13)	C13A—C14A—C15A	118.80 (13)
C13—C14—H14	120.5	C13A—C14A—H14A	120.6
C15—C14—H14	120.5	C15A—C14A—H14A	120.6
C16—C15—C14	120.38 (13)	C14A—C15A—C16A	120.51 (14)
C16—C15—H15	119.8	C14A—C15A—H15A	119.7
C14—C15—H15	119.8	C16A—C15A—H15A	119.7
C15—C16—C11	119.79 (13)	C15A—C16A—C11A	119.82 (14)
C15—C16—H16	120.1	C15A—C16A—H16A	120.1
C11—C16—H16	120.1	C11A—C16A—H16A	120.1
C22—C21—C26	117.88 (12)	C22A—C21A—C26A	117.97 (13)
C22—C21—N2	122.66 (12)	C22A—C21A—N2A	120.33 (13)
C26—C21—N2	119.31 (12)	C26A—C21A—N2A	121.64 (12)
C23—C22—C21	121.19 (13)	C23A—C22A—C21A	121.22 (14)
C23—C22—Cl2	118.45 (11)	C23A—C22A—Cl2A	119.52 (12)
C21—C22—Cl2	120.36 (11)	C21A—C22A—Cl2A	119.25 (11)
C24—C23—C22	119.39 (14)	C24A—C23A—C22A	119.31 (14)
C24—C23—H23	120.3	C24A—C23A—H23A	120.3
C22—C23—H23	120.3	C22A—C23A—H23A	120.3
C23—C24—C25	120.93 (14)	C23A—C24A—C25A	121.10 (14)
C23—C24—H24	119.5	C23A—C24A—H24A	119.4
C25—C24—H24	119.5	C25A—C24A—H24A	119.4
C24—C25—C26	118.86 (14)	C24A—C25A—C26A	118.90 (15)
C24—C25—H25	120.6	C24A—C25A—H25A	120.6
C26—C25—H25	120.6	C26A—C25A—H25A	120.6
C25—C26—C21	121.73 (14)	C25A—C26A—C21A	121.49 (14)
C25—C26—Cl3	119.61 (11)	C25A—C26A—Cl3A	119.37 (12)
C21—C26—Cl3	118.66 (11)	C21A—C26A—Cl3A	119.14 (11)
O1—C1—N1—C2	9.8 (2)	O1A—C1A—N1A—C2A	−6.0 (2)
C11—C1—N1—C2	−170.26 (12)	C11A—C1A—N1A—C2A	174.85 (12)
C1—N1—C2—N2	−2.1 (2)	C1A—N1A—C2A—N2A	−1.9 (2)
C1—N1—C2—S1	177.85 (11)	C1A—N1A—C2A—S1A	178.35 (11)
N1—C2—N2—C21	164.59 (12)	N1A—C2A—N2A—C21A	−175.51 (12)
S1—C2—N2—C21	−15.4 (2)	S1A—C2A—N2A—C21A	4.21 (19)
O1—C1—C11—C16	27.34 (19)	O1A—C1A—C11A—C12A	148.31 (14)
N1—C1—C11—C16	−152.59 (12)	N1A—C1A—C11A—C12A	−32.53 (18)
O1—C1—C11—C12	−150.24 (14)	O1A—C1A—C11A—C16A	−30.6 (2)
N1—C1—C11—C12	29.82 (18)	N1A—C1A—C11A—C16A	148.52 (13)
C16—C11—C12—C13	1.3 (2)	C16A—C11A—C12A—C13A	−2.5 (2)
C1—C11—C12—C13	178.78 (12)	C1A—C11A—C12A—C13A	178.58 (12)
C11—C12—C13—C14	1.4 (2)	C11A—C12A—C13A—C14A	0.9 (2)
C11—C12—C13—Cl1	−178.98 (10)	C11A—C12A—C13A—Cl1A	−177.30 (10)
C12—C13—C14—C15	−2.1 (2)	C12A—C13A—C14A—C15A	0.7 (2)
Cl1—C13—C14—C15	178.29 (11)	Cl1A—C13A—C14A—C15A	178.90 (11)
C13—C14—C15—C16	0.1 (2)	C13A—C14A—C15A—C16A	−0.8 (2)
C14—C15—C16—C11	2.5 (2)	C14A—C15A—C16A—C11A	−0.9 (2)
C12—C11—C16—C15	−3.2 (2)	C12A—C11A—C16A—C15A	2.5 (2)
C1—C11—C16—C15	179.22 (12)	C1A—C11A—C16A—C15A	−178.53 (13)
C2—N2—C21—C22	92.05 (17)	C2A—N2A—C21A—C22A	98.10 (16)
C2—N2—C21—C26	−92.52 (17)	C2A—N2A—C21A—C26A	−84.63 (17)
C26—C21—C22—C23	−0.4 (2)	C26A—C21A—C22A—C23A	−0.6 (2)
N2—C21—C22—C23	175.08 (13)	N2A—C21A—C22A—C23A	176.75 (13)
C26—C21—C22—Cl2	179.97 (10)	C26A—C21A—C22A—Cl2A	177.80 (10)
N2—C21—C22—Cl2	−4.53 (19)	N2A—C21A—C22A—Cl2A	−4.83 (18)
C21—C22—C23—C24	−0.8 (2)	C21A—C22A—C23A—C24A	0.9 (2)
Cl2—C22—C23—C24	178.81 (12)	Cl2A—C22A—C23A—C24A	−177.55 (12)
C22—C23—C24—C25	1.4 (2)	C22A—C23A—C24A—C25A	−0.1 (2)
C23—C24—C25—C26	−0.8 (2)	C23A—C24A—C25A—C26A	−0.9 (2)
C24—C25—C26—C21	−0.5 (2)	C24A—C25A—C26A—C21A	1.2 (2)
C24—C25—C26—Cl3	178.78 (12)	C24A—C25A—C26A—Cl3A	−178.09 (12)
C22—C21—C26—C25	1.1 (2)	C22A—C21A—C26A—C25A	−0.4 (2)
N2—C21—C26—C25	−174.59 (13)	N2A—C21A—C26A—C25A	−177.75 (13)
C22—C21—C26—Cl3	−178.19 (10)	C22A—C21A—C26A—Cl3A	178.86 (10)
N2—C21—C26—Cl3	6.16 (18)	N2A—C21A—C26A—Cl3A	1.53 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1^i	0.81 (2)	2.85 (2)	3.6135 (13)	158.0 (18)
N2—H2···O1	0.87 (2)	1.92 (2)	2.6437 (16)	139.0 (19)
N1A—H1A···S1A^ii	0.89 (2)	2.54 (2)	3.4261 (13)	171.6 (17)
N2A—H2A···O1A	0.89 (2)	1.92 (2)	2.6440 (16)	136.8 (19)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z+1.