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Acta Cryst. (2009). E65, o249    [ doi:10.1107/S1600536809000051 ]

1-(2,6-Dichlorobenzoyl)-3-(2,3,5,6-tetrachlorophenyl)thiourea trichloromethane hemisolvate

M. Khawar Rauf, M. Bolte and S. Anwar

Abstract top

The title compound, C14H6Cl6N2OS·0.5CHCl3, crystallizes with four 1-(2,6-dichlorobenzoyl)-3-(2,3,5,6-tetrachlorophenyl)thiourea molecules and two trichloromethane molecules in the asymmetric unit. The thiourea molecules exist in the solid state in their thione forms with typical thiourea C-S and C-O bonds lengths, as well as shortened C-N bonds. The -NH-C(=S)-NH-C(=O)- plane is almost perpendicular to the benzene ring in each thiourea molecule. Intramolecular N-H...O hydrogen bonds stabilize the molecular conformation and intermolecular N-H...S hydrogen bonds stabilize the packing arrangement.

Comment top

The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Khawar Rauf et al., 2006a, 2007). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006b). The molecule exists in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. The thiocarbonyl and carbonyl groups are almost coplanar. The molecule features an intramolecular N—H···O hydrogen bond (see the table of hydrogen bond geometry; Fig 2).

Related literature top

For related compounds, see: Khawar Rauf et al. (2006a,b, 2007). For standard bond-length data, see: Allen (2002).

Experimental top

Freshly prepared and steam distillated 2,6-dichlorobenzoyl isothiocyanate (2.32 g, 10 mmol) was stirred in acetone (50 ml) for 20 minutes. Neat 2,3,5,6-tetrachloroaniline (2.30 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was then poured into acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol–1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall yield of 85%.

Refinement top

H atoms bonded to C were included in calculated positions and refined as riding on their parent C atom with C—H = 0.95 Å Uiso(H) = 1.2Ueq(C). The H atoms bonded to N were freely refined. The highest peak in the final difference map (1.64 e Å-3) is located at 1.04 Å from Cl13 and the deepest hole (-1.40 e Å-3) is located at 0.75 Å from Cl22.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of (I) with a view onto the ac plane. H atoms omitted for clarity.
1-(2,6-Dichlorobenzoyl)-3-(2,3,5,6-tetrachlorophenyl)thiourea trichloromethane hemisolvate top
Crystal data top
C14H6Cl6N2OS·0.5CHCl3F(000) = 4144
Mr = 522.65Dx = 1.777 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 111596 reflections
a = 26.7213 (6) Åθ = 1.6–30.3°
b = 8.6580 (2) ŵ = 1.20 mm−1
c = 36.1046 (9) ÅT = 173 K
β = 110.683 (2)°Block, colourless
V = 7814.6 (3) Å30.43 × 0.41 × 0.38 mm
Z = 16
Data collection top
Stoe IPDS II two-circle
diffractometer		22452 independent reflections
Radiation source: fine-focus sealed tube17143 reflections with I > 2σ(I)
graphiteRint = 0.052
ω scansθmax = 29.9°, θmin = 1.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)		h = −37→37
Tmin = 0.627, Tmax = 0.659k = −12→12
156440 measured reflectionsl = −50→50
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0852P)2 + 3.006P]
where P = (Fo2 + 2Fc2)/3
22452 reflections(Δ/σ)max = 0.001
969 parametersΔρmax = 1.64 e Å−3
0 restraintsΔρmin = −1.40 e Å−3
Crystal data top
C14H6Cl6N2OS·0.5CHCl3V = 7814.6 (3) Å3
Mr = 522.65Z = 16
Monoclinic, P21/nMo Kα radiation
a = 26.7213 (6) ŵ = 1.20 mm−1
b = 8.6580 (2) ÅT = 173 K
c = 36.1046 (9) Å0.43 × 0.41 × 0.38 mm
β = 110.683 (2)°
Data collection top
Stoe IPDS II two-circle
diffractometer		22452 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)		17143 reflections with I > 2σ(I)
Tmin = 0.627, Tmax = 0.659Rint = 0.052
156440 measured reflectionsθmax = 29.9°
Refinement top
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147Δρmax = 1.64 e Å−3
S = 1.08Δρmin = −1.40 e Å−3
22452 reflectionsAbsolute structure: ?
969 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.66337 (3)−0.02992 (9)0.44477 (2)0.04817 (16)
Cl20.70980 (3)0.57423 (8)0.47582 (3)0.05017 (17)
Cl30.89534 (3)0.45616 (7)0.58259 (2)0.03868 (14)
Cl40.99807 (3)0.38781 (8)0.65838 (2)0.04692 (16)
Cl50.96884 (3)−0.21933 (7)0.632157 (19)0.03678 (13)
Cl60.86205 (2)−0.15449 (7)0.559103 (19)0.03543 (12)
C10.73240 (8)0.2335 (3)0.49034 (6)0.0269 (4)
O10.73085 (7)0.2042 (2)0.52283 (5)0.0355 (4)
N10.77829 (7)0.2323 (2)0.48119 (6)0.0271 (4)
H10.7775 (13)0.251 (4)0.4593 (10)0.042 (9)*
C20.83002 (9)0.2035 (3)0.50686 (7)0.0269 (4)
S10.88115 (2)0.20537 (9)0.490438 (19)0.03819 (15)
N20.83492 (8)0.1760 (2)0.54445 (6)0.0270 (4)
H20.8084 (14)0.177 (4)0.5489 (10)0.048 (10)*
C110.68259 (9)0.2763 (3)0.45622 (7)0.0306 (5)
C120.64776 (10)0.1631 (3)0.43414 (7)0.0367 (5)
C130.60002 (11)0.2023 (4)0.40395 (8)0.0483 (7)
H130.57670.12420.38890.058*
C140.58724 (11)0.3558 (5)0.39636 (8)0.0512 (8)
H140.55480.38280.37580.061*
C150.62035 (11)0.4715 (4)0.41784 (9)0.0468 (7)
H150.61090.57710.41240.056*
C160.66784 (10)0.4306 (3)0.44760 (8)0.0372 (5)
C210.88435 (8)0.1473 (3)0.57509 (6)0.0264 (4)
C220.91506 (9)0.2696 (3)0.59669 (7)0.0291 (4)
C230.96117 (9)0.2387 (3)0.62935 (7)0.0313 (5)
C240.97723 (9)0.0884 (3)0.63984 (7)0.0320 (5)
H241.00870.06850.66200.038*
C250.94752 (9)−0.0332 (3)0.61811 (7)0.0288 (4)
C260.90057 (9)−0.0050 (3)0.58587 (7)0.0275 (4)
Cl1A0.33429 (3)1.13982 (9)0.35021 (3)0.0584 (2)
Cl2A0.29196 (3)0.53262 (10)0.32256 (2)0.05094 (18)
Cl3A0.48739 (2)0.40796 (7)0.435585 (18)0.03423 (12)
Cl4A0.59504 (2)0.34253 (7)0.507834 (18)0.03507 (13)
Cl5A0.62697 (3)0.94952 (8)0.53263 (2)0.04705 (16)
Cl6A0.52213 (3)1.01845 (7)0.45831 (2)0.03947 (14)
C1A0.35869 (9)0.8016 (3)0.36676 (7)0.0277 (4)
O1A0.35767 (7)0.7870 (2)0.40003 (5)0.0376 (4)
N1A0.40400 (7)0.7872 (2)0.35718 (6)0.0260 (4)
H1A0.3987 (11)0.797 (3)0.3331 (9)0.029 (7)*
C2A0.45572 (8)0.7577 (3)0.38303 (6)0.0260 (4)
S1A0.50641 (2)0.74921 (8)0.366168 (17)0.03312 (13)
N2A0.46098 (8)0.7394 (2)0.42084 (6)0.0276 (4)
H2A0.4358 (13)0.744 (4)0.4256 (10)0.043 (9)*
C11A0.30878 (9)0.8396 (3)0.33229 (7)0.0329 (5)
C12A0.29322 (10)0.9926 (4)0.32277 (8)0.0420 (6)
C13A0.24564 (12)1.0307 (5)0.29284 (10)0.0568 (9)
H13A0.23581.13550.28660.068*
C14A0.21276 (12)0.9113 (5)0.27230 (9)0.0626 (11)
H14A0.17990.93570.25190.075*
C15A0.22641 (11)0.7601 (5)0.28069 (9)0.0565 (9)
H15A0.20350.68020.26620.068*
C16A0.27470 (10)0.7241 (4)0.31097 (8)0.0401 (6)
C21A0.51069 (8)0.7098 (3)0.45135 (6)0.0256 (4)
C22A0.52656 (8)0.5578 (3)0.46208 (6)0.0259 (4)
C23A0.57383 (9)0.5290 (3)0.49375 (7)0.0280 (4)
C24A0.60455 (9)0.6499 (3)0.51502 (7)0.0307 (5)
H24A0.63650.62940.53670.037*
C25A0.58857 (9)0.8013 (3)0.50456 (7)0.0314 (5)
C26A0.54184 (9)0.8319 (3)0.47255 (7)0.0294 (4)
Cl1B0.95781 (3)0.58907 (8)0.42725 (2)0.04137 (14)
Cl2B0.91397 (3)−0.01830 (8)0.39847 (2)0.04339 (15)
Cl3B0.75253 (2)0.00790 (7)0.312422 (18)0.03588 (13)
Cl4B0.64711 (3)−0.04636 (8)0.238690 (19)0.03914 (14)
Cl5B0.62441 (3)0.56373 (8)0.214061 (19)0.04155 (15)
Cl6B0.73026 (2)0.62207 (7)0.287247 (18)0.03314 (12)
C1B0.88859 (8)0.3185 (3)0.38354 (7)0.0284 (4)
O1B0.88943 (7)0.3517 (3)0.35104 (5)0.0415 (4)
N1B0.84291 (7)0.3071 (2)0.39269 (6)0.0260 (4)
H1B0.8450 (11)0.289 (3)0.4157 (9)0.032 (7)*
C2B0.79047 (8)0.3128 (2)0.36654 (6)0.0246 (4)
S1B0.73988 (2)0.29118 (8)0.383021 (17)0.03172 (12)
N2B0.78424 (7)0.3360 (2)0.32837 (5)0.0255 (4)
H2B0.8096 (14)0.356 (4)0.3235 (10)0.047 (9)*
C11B0.93940 (8)0.2807 (3)0.41760 (7)0.0283 (4)
C12B0.97398 (9)0.3963 (3)0.43896 (7)0.0325 (5)
C13B1.02204 (10)0.3602 (4)0.46905 (8)0.0408 (6)
H13B1.04530.43960.48350.049*
C14B1.03531 (10)0.2061 (4)0.47748 (8)0.0430 (6)
H14B1.06780.18080.49820.052*
C15B1.00233 (10)0.0880 (4)0.45648 (8)0.0389 (6)
H15B1.0120−0.01710.46240.047*
C16B0.95474 (9)0.1279 (3)0.42664 (7)0.0325 (5)
C21B0.73496 (8)0.3127 (3)0.29691 (6)0.0255 (4)
C22B0.71628 (9)0.1617 (3)0.28614 (7)0.0275 (4)
C23B0.66976 (9)0.1384 (3)0.25347 (7)0.0300 (4)
C24B0.64140 (9)0.2618 (3)0.23173 (7)0.0331 (5)
H24B0.60940.24450.20970.040*
C25B0.65990 (9)0.4111 (3)0.24221 (7)0.0307 (5)
C26B0.70672 (9)0.4370 (3)0.27466 (6)0.0272 (4)
Cl1C0.57911 (3)1.09097 (10)0.30254 (3)0.0564 (2)
Cl2C0.53972 (4)0.48383 (10)0.27287 (3)0.0648 (2)
Cl3C0.38248 (2)0.50322 (6)0.186926 (18)0.03258 (12)
Cl4C0.27591 (2)0.43823 (7)0.113810 (18)0.03400 (12)
Cl5C0.24486 (3)1.04537 (8)0.08911 (2)0.04316 (15)
Cl6C0.34925 (3)1.11411 (7)0.162963 (18)0.03610 (13)
C1C0.51367 (8)0.8182 (3)0.25740 (7)0.0283 (4)
O1C0.51427 (7)0.8408 (3)0.22432 (5)0.0401 (4)
N1C0.46813 (7)0.8199 (2)0.26692 (6)0.0259 (4)
H1C0.4729 (11)0.807 (3)0.2916 (9)0.031 (7)*
C2C0.41553 (8)0.8246 (2)0.24069 (6)0.0243 (4)
S1C0.36491 (2)0.81802 (8)0.257634 (17)0.03250 (13)
N2C0.40942 (8)0.8333 (2)0.20232 (6)0.0267 (4)
H2C0.4359 (12)0.842 (3)0.1987 (9)0.031 (7)*
C11C0.56415 (9)0.7834 (3)0.29148 (7)0.0327 (5)
C12C0.59717 (10)0.9001 (4)0.31357 (8)0.0436 (7)
C13C0.64558 (12)0.8641 (6)0.34403 (9)0.0632 (11)
H13C0.66800.94370.35920.076*
C14C0.65995 (12)0.7110 (7)0.35156 (10)0.0773 (15)
H14C0.69260.68610.37210.093*
C15C0.62825 (13)0.5938 (5)0.33010 (11)0.0668 (12)
H15C0.63890.48910.33560.080*
C16C0.58052 (11)0.6305 (4)0.30025 (9)0.0450 (7)
C21C0.35997 (8)0.8054 (3)0.17128 (6)0.0244 (4)
C22C0.34374 (8)0.6527 (2)0.16039 (6)0.0251 (4)
C23C0.29691 (9)0.6247 (3)0.12831 (7)0.0276 (4)
C24C0.26655 (9)0.7460 (3)0.10667 (7)0.0300 (4)
H24C0.23480.72580.08470.036*
C25C0.28269 (9)0.8969 (3)0.11721 (7)0.0296 (4)
C26C0.32928 (9)0.9273 (3)0.14963 (6)0.0269 (4)
C1L0.82936 (12)0.7588 (4)0.43119 (9)0.0493 (7)
H1L0.86330.81970.43910.059*
Cl110.81304 (3)0.70372 (9)0.38139 (2)0.04810 (17)
Cl120.84087 (3)0.59360 (9)0.46202 (2)0.04500 (15)
Cl130.78014 (5)0.87597 (12)0.43717 (4)0.0790 (3)
C2L0.4292 (3)0.2482 (6)0.30034 (16)0.119 (2)
H2L0.39160.21330.29500.143*
Cl210.46414 (3)0.12027 (9)0.33740 (2)0.04996 (17)
Cl220.42585 (6)0.42989 (12)0.31435 (4)0.0903 (4)
Cl230.43463 (5)0.21729 (10)0.25600 (3)0.0710 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0458 (4)0.0489 (4)0.0468 (4)−0.0022 (3)0.0126 (3)−0.0124 (3)
Cl20.0427 (3)0.0391 (3)0.0703 (5)0.0037 (3)0.0219 (3)0.0085 (3)
Cl30.0428 (3)0.0285 (3)0.0403 (3)0.0043 (2)0.0092 (3)0.0039 (2)
Cl40.0430 (3)0.0405 (3)0.0435 (4)−0.0040 (3)−0.0018 (3)−0.0083 (3)
Cl50.0414 (3)0.0333 (3)0.0370 (3)0.0116 (2)0.0154 (2)0.0100 (2)
Cl60.0358 (3)0.0322 (3)0.0368 (3)−0.0028 (2)0.0111 (2)−0.0031 (2)
C10.0243 (9)0.0323 (11)0.0230 (10)0.0024 (8)0.0072 (8)0.0006 (8)
O10.0277 (8)0.0544 (11)0.0250 (8)0.0026 (7)0.0099 (6)0.0046 (7)
N10.0220 (8)0.0381 (10)0.0211 (9)0.0050 (7)0.0073 (7)0.0046 (7)
C20.0260 (10)0.0301 (10)0.0242 (10)0.0050 (8)0.0082 (8)0.0038 (8)
S10.0246 (3)0.0632 (4)0.0285 (3)0.0111 (3)0.0114 (2)0.0136 (3)
N20.0225 (8)0.0366 (10)0.0218 (9)0.0042 (7)0.0078 (7)0.0051 (7)
C110.0228 (9)0.0454 (13)0.0242 (10)0.0052 (9)0.0091 (8)0.0044 (9)
C120.0275 (11)0.0558 (16)0.0272 (12)0.0039 (10)0.0099 (9)0.0002 (11)
C130.0274 (12)0.084 (2)0.0286 (13)0.0037 (13)0.0042 (10)−0.0025 (13)
C140.0268 (12)0.095 (3)0.0287 (13)0.0138 (14)0.0062 (10)0.0135 (14)
C150.0332 (12)0.071 (2)0.0406 (15)0.0213 (13)0.0177 (11)0.0259 (14)
C160.0278 (11)0.0503 (15)0.0360 (13)0.0078 (10)0.0144 (10)0.0129 (11)
C210.0240 (9)0.0317 (11)0.0225 (10)0.0035 (8)0.0070 (8)0.0039 (8)
C220.0289 (10)0.0300 (11)0.0271 (11)0.0020 (8)0.0082 (8)0.0023 (8)
C230.0284 (10)0.0323 (11)0.0297 (11)0.0007 (8)0.0060 (9)0.0003 (9)
C240.0293 (10)0.0367 (12)0.0271 (11)0.0039 (9)0.0065 (9)0.0018 (9)
C250.0292 (10)0.0328 (11)0.0255 (10)0.0054 (8)0.0111 (8)0.0037 (8)
C260.0272 (10)0.0301 (10)0.0256 (10)0.0017 (8)0.0098 (8)0.0006 (8)
Cl1A0.0528 (4)0.0425 (4)0.0862 (6)0.0098 (3)0.0325 (4)0.0141 (4)
Cl2A0.0479 (4)0.0557 (4)0.0491 (4)−0.0063 (3)0.0171 (3)−0.0151 (3)
Cl3A0.0348 (3)0.0318 (3)0.0345 (3)−0.0036 (2)0.0103 (2)−0.0033 (2)
Cl4A0.0396 (3)0.0327 (3)0.0343 (3)0.0103 (2)0.0150 (2)0.0092 (2)
Cl5A0.0457 (3)0.0398 (3)0.0408 (3)−0.0070 (3)−0.0031 (3)−0.0068 (3)
Cl6A0.0448 (3)0.0279 (3)0.0401 (3)0.0040 (2)0.0080 (3)0.0034 (2)
C1A0.0247 (9)0.0333 (11)0.0234 (10)0.0035 (8)0.0063 (8)0.0013 (8)
O1A0.0277 (8)0.0605 (12)0.0253 (8)0.0073 (8)0.0103 (7)0.0046 (8)
N1A0.0225 (8)0.0352 (10)0.0192 (9)0.0048 (7)0.0061 (7)0.0031 (7)
C2A0.0251 (9)0.0280 (10)0.0226 (10)0.0041 (8)0.0056 (8)0.0033 (8)
S1A0.0240 (2)0.0498 (3)0.0259 (3)0.0083 (2)0.0092 (2)0.0073 (2)
N2A0.0222 (8)0.0387 (10)0.0207 (9)0.0037 (7)0.0063 (7)0.0039 (7)
C11A0.0229 (10)0.0525 (15)0.0242 (11)0.0085 (9)0.0094 (8)0.0066 (10)
C12A0.0316 (12)0.0587 (17)0.0413 (14)0.0139 (11)0.0198 (11)0.0183 (13)
C13A0.0412 (15)0.088 (3)0.0486 (17)0.0324 (16)0.0253 (14)0.0369 (17)
C14A0.0297 (13)0.126 (3)0.0297 (14)0.0210 (17)0.0080 (11)0.0198 (18)
C15A0.0277 (12)0.110 (3)0.0282 (14)0.0069 (15)0.0052 (10)−0.0055 (16)
C16A0.0259 (11)0.0652 (18)0.0286 (12)0.0050 (11)0.0089 (9)−0.0015 (12)
C21A0.0243 (9)0.0314 (11)0.0197 (9)0.0028 (8)0.0060 (8)0.0020 (8)
C22A0.0256 (9)0.0309 (10)0.0209 (10)0.0006 (8)0.0079 (8)0.0011 (8)
C23A0.0269 (10)0.0322 (11)0.0242 (10)0.0043 (8)0.0083 (8)0.0040 (8)
C24A0.0263 (10)0.0368 (12)0.0253 (11)0.0027 (9)0.0044 (8)0.0030 (9)
C25A0.0290 (10)0.0328 (11)0.0285 (11)−0.0011 (9)0.0051 (9)0.0000 (9)
C26A0.0294 (10)0.0304 (11)0.0261 (11)0.0028 (8)0.0069 (8)0.0016 (8)
Cl1B0.0377 (3)0.0419 (3)0.0425 (3)−0.0017 (2)0.0118 (3)−0.0043 (3)
Cl2B0.0402 (3)0.0387 (3)0.0488 (4)−0.0030 (3)0.0127 (3)0.0018 (3)
Cl3B0.0396 (3)0.0296 (3)0.0351 (3)0.0034 (2)0.0090 (2)0.0017 (2)
Cl4B0.0449 (3)0.0378 (3)0.0347 (3)−0.0121 (2)0.0139 (3)−0.0110 (2)
Cl5B0.0358 (3)0.0440 (3)0.0344 (3)0.0054 (2)−0.0006 (2)0.0089 (3)
Cl6B0.0352 (3)0.0300 (3)0.0312 (3)−0.0020 (2)0.0080 (2)0.0011 (2)
C1B0.0230 (9)0.0377 (12)0.0232 (10)−0.0002 (8)0.0064 (8)0.0018 (8)
O1B0.0260 (8)0.0725 (14)0.0246 (8)−0.0039 (8)0.0073 (7)0.0081 (8)
N1B0.0226 (8)0.0345 (10)0.0194 (9)0.0014 (7)0.0054 (7)0.0021 (7)
C2B0.0226 (9)0.0274 (10)0.0219 (10)0.0011 (7)0.0056 (7)0.0009 (8)
S1B0.0221 (2)0.0493 (3)0.0234 (3)0.0031 (2)0.0076 (2)0.0035 (2)
N2B0.0219 (8)0.0333 (9)0.0196 (8)−0.0011 (7)0.0051 (7)0.0018 (7)
C11B0.0204 (9)0.0420 (12)0.0219 (10)0.0007 (8)0.0065 (8)0.0014 (9)
C12B0.0247 (10)0.0442 (13)0.0278 (11)−0.0001 (9)0.0083 (9)−0.0019 (9)
C13B0.0259 (11)0.0624 (17)0.0300 (13)−0.0027 (11)0.0049 (9)−0.0043 (12)
C14B0.0247 (11)0.0710 (19)0.0282 (12)0.0064 (11)0.0030 (9)0.0071 (12)
C15B0.0316 (11)0.0540 (16)0.0319 (13)0.0100 (11)0.0121 (10)0.0126 (11)
C16B0.0275 (10)0.0423 (13)0.0287 (11)0.0011 (9)0.0112 (9)0.0044 (9)
C21B0.0235 (9)0.0311 (10)0.0199 (9)−0.0009 (8)0.0052 (8)0.0003 (8)
C22B0.0285 (10)0.0303 (10)0.0231 (10)−0.0011 (8)0.0085 (8)−0.0011 (8)
C23B0.0300 (10)0.0347 (11)0.0249 (11)−0.0038 (9)0.0092 (9)−0.0036 (9)
C24B0.0266 (10)0.0438 (13)0.0241 (11)−0.0034 (9)0.0032 (8)−0.0022 (9)
C25B0.0266 (10)0.0377 (12)0.0254 (11)0.0009 (9)0.0060 (8)0.0022 (9)
C26B0.0267 (10)0.0317 (11)0.0222 (10)−0.0006 (8)0.0073 (8)0.0002 (8)
Cl1C0.0552 (4)0.0615 (5)0.0609 (5)−0.0207 (4)0.0309 (4)−0.0264 (4)
Cl2C0.0592 (5)0.0416 (4)0.1051 (8)0.0033 (3)0.0433 (5)0.0134 (4)
Cl3C0.0338 (3)0.0281 (3)0.0340 (3)0.0046 (2)0.0097 (2)0.0054 (2)
Cl4C0.0394 (3)0.0286 (3)0.0347 (3)−0.0078 (2)0.0140 (2)−0.0072 (2)
Cl5C0.0435 (3)0.0346 (3)0.0368 (3)0.0066 (2)−0.0039 (3)0.0066 (2)
Cl6C0.0418 (3)0.0253 (2)0.0345 (3)−0.0023 (2)0.0052 (2)−0.0022 (2)
C1C0.0235 (9)0.0347 (11)0.0244 (10)−0.0023 (8)0.0058 (8)0.0002 (8)
O1C0.0276 (8)0.0680 (13)0.0246 (8)−0.0053 (8)0.0092 (7)0.0033 (8)
N1C0.0233 (8)0.0335 (9)0.0194 (8)−0.0007 (7)0.0057 (7)0.0007 (7)
C2C0.0226 (9)0.0260 (9)0.0215 (10)−0.0006 (7)0.0041 (7)−0.0003 (7)
S1C0.0224 (2)0.0505 (3)0.0238 (3)0.0004 (2)0.0072 (2)−0.0006 (2)
N2C0.0222 (8)0.0347 (10)0.0216 (9)−0.0024 (7)0.0056 (7)0.0009 (7)
C11C0.0208 (9)0.0529 (15)0.0233 (11)0.0001 (9)0.0065 (8)0.0064 (10)
C12C0.0276 (11)0.077 (2)0.0273 (12)−0.0119 (12)0.0107 (10)−0.0077 (12)
C13C0.0280 (13)0.131 (4)0.0284 (14)−0.0114 (17)0.0075 (11)−0.0089 (18)
C14C0.0267 (14)0.166 (5)0.0360 (17)0.015 (2)0.0073 (12)0.029 (2)
C15C0.0396 (16)0.110 (3)0.059 (2)0.0335 (19)0.0279 (15)0.048 (2)
C16C0.0315 (12)0.0619 (18)0.0450 (16)0.0087 (12)0.0177 (11)0.0197 (13)
C21C0.0239 (9)0.0276 (10)0.0201 (9)−0.0021 (7)0.0057 (7)−0.0006 (7)
C22C0.0264 (9)0.0254 (10)0.0232 (10)−0.0001 (7)0.0086 (8)0.0002 (8)
C23C0.0295 (10)0.0299 (10)0.0237 (10)−0.0024 (8)0.0099 (8)−0.0003 (8)
C24C0.0289 (10)0.0338 (11)0.0232 (10)−0.0017 (8)0.0042 (8)−0.0018 (8)
C25C0.0283 (10)0.0311 (11)0.0252 (11)0.0017 (8)0.0044 (8)0.0025 (8)
C26C0.0288 (10)0.0263 (10)0.0229 (10)−0.0004 (8)0.0060 (8)−0.0002 (8)
C1L0.0428 (14)0.0476 (16)0.0485 (17)−0.0054 (12)0.0050 (12)−0.0016 (13)
Cl110.0525 (4)0.0443 (4)0.0376 (3)0.0007 (3)0.0036 (3)0.0001 (3)
Cl120.0405 (3)0.0493 (4)0.0421 (4)−0.0008 (3)0.0108 (3)0.0033 (3)
Cl130.0952 (7)0.0521 (5)0.0853 (7)0.0218 (5)0.0263 (6)−0.0128 (5)
C2L0.203 (7)0.088 (4)0.078 (3)0.085 (4)0.064 (4)0.043 (3)
Cl210.0380 (3)0.0529 (4)0.0520 (4)0.0034 (3)0.0072 (3)0.0148 (3)
Cl220.1235 (10)0.0455 (5)0.0873 (8)0.0224 (6)0.0191 (7)−0.0095 (5)
Cl230.1051 (7)0.0389 (4)0.0421 (4)−0.0021 (4)−0.0074 (4)0.0015 (3)
Geometric parameters (Å, °) top
Cl1—C121.732 (3)Cl5B—C25B1.731 (2)
Cl2—C161.742 (3)Cl6B—C26B1.723 (2)
Cl3—C221.719 (2)C1B—O1B1.216 (3)
Cl4—C231.734 (3)C1B—N1B1.376 (3)
Cl5—C251.725 (2)C1B—C11B1.511 (3)
Cl6—C261.722 (2)N1B—C2B1.387 (3)
C1—O11.215 (3)N1B—H1B0.83 (3)
C1—N11.378 (3)C2B—N2B1.343 (3)
C1—C111.506 (3)C2B—S1B1.669 (2)
N1—C21.388 (3)N2B—C21B1.417 (3)
N1—H10.80 (3)N2B—H2B0.78 (3)
C2—N21.338 (3)C11B—C16B1.390 (4)
C2—S11.670 (2)C11B—C12B1.395 (3)
N2—C211.414 (3)C12B—C13B1.394 (3)
N2—H20.78 (3)C13B—C14B1.386 (4)
C11—C121.392 (4)C13B—H13B0.9500
C11—C161.397 (4)C14B—C15B1.387 (4)
C12—C131.396 (3)C14B—H14B0.9500
C13—C141.375 (5)C15B—C16B1.389 (3)
C13—H130.9500C15B—H15B0.9500
C14—C151.380 (5)C21B—C26B1.395 (3)
C14—H140.9500C21B—C22B1.404 (3)
C15—C161.388 (3)C22B—C23B1.393 (3)
C15—H150.9500C23B—C24B1.383 (4)
C21—C221.397 (3)C24B—C25B1.388 (4)
C21—C261.400 (3)C24B—H24B0.9500
C22—C231.398 (3)C25B—C26B1.397 (3)
C23—C241.380 (3)Cl1C—C12C1.728 (4)
C24—C251.384 (3)Cl2C—C16C1.737 (4)
C24—H240.9500Cl3C—C22C1.722 (2)
C25—C261.399 (3)Cl4C—C23C1.729 (2)
Cl1A—C12A1.745 (3)Cl5C—C25C1.726 (2)
Cl2A—C16A1.732 (3)Cl6C—C26C1.718 (2)
Cl3A—C22A1.728 (2)C1C—O1C1.216 (3)
Cl4A—C23A1.727 (2)C1C—N1C1.377 (3)
Cl5A—C25A1.730 (2)C1C—C11C1.501 (3)
Cl6A—C26A1.721 (2)N1C—C2C1.391 (3)
C1A—O1A1.218 (3)N1C—H1C0.86 (3)
C1A—N1A1.377 (3)C2C—N2C1.338 (3)
C1A—C11A1.505 (3)C2C—S1C1.671 (2)
N1A—C2A1.391 (3)N2C—C21C1.419 (3)
N1A—H1A0.84 (3)N2C—H2C0.77 (3)
C2A—N2A1.332 (3)C11C—C12C1.393 (4)
C2A—S1A1.671 (2)C11C—C16C1.395 (4)
N2A—C21A1.418 (3)C12C—C13C1.405 (4)
N2A—H2A0.75 (3)C13C—C14C1.379 (7)
C11A—C16A1.388 (4)C13C—H13C0.9500
C11A—C12A1.394 (4)C14C—C15C1.373 (7)
C12A—C13A1.386 (4)C14C—H14C0.9500
C13A—C14A1.389 (6)C15C—C16C1.385 (4)
C13A—H13A0.9500C15C—H15C0.9500
C14A—C15A1.364 (6)C21C—C26C1.394 (3)
C14A—H14A0.9500C21C—C22C1.404 (3)
C15A—C16A1.400 (4)C22C—C23C1.394 (3)
C15A—H15A0.9500C23C—C24C1.387 (3)
C21A—C26A1.395 (3)C24C—C25C1.386 (3)
C21A—C22A1.395 (3)C24C—H24C0.9500
C22A—C23A1.395 (3)C25C—C26C1.400 (3)
C23A—C24A1.383 (3)C1L—Cl131.734 (3)
C24A—C25A1.389 (3)C1L—Cl111.760 (3)
C24A—H24A0.9500C1L—Cl121.771 (3)
C25A—C26A1.395 (3)C1L—H1L1.0000
Cl1B—C12B1.739 (3)C2L—Cl221.664 (6)
Cl2B—C16B1.744 (3)C2L—Cl231.679 (5)
Cl3B—C22B1.721 (2)C2L—Cl211.734 (4)
Cl4B—C23B1.727 (2)C2L—H2L1.0000
O1—C1—N1124.5 (2)N2B—C2B—N1B115.65 (19)
O1—C1—C11121.3 (2)N2B—C2B—S1B124.06 (16)
N1—C1—C11114.20 (19)N1B—C2B—S1B120.28 (16)
C1—N1—C2127.01 (19)C2B—N2B—C21B122.98 (19)
C1—N1—H1121 (2)C2B—N2B—H2B118 (3)
C2—N1—H1112 (2)C21B—N2B—H2B119 (3)
N2—C2—N1115.25 (19)C16B—C11B—C12B118.1 (2)
N2—C2—S1124.24 (17)C16B—C11B—C1B120.2 (2)
N1—C2—S1120.51 (17)C12B—C11B—C1B121.6 (2)
C2—N2—C21123.69 (19)C13B—C12B—C11B121.2 (3)
C2—N2—H2116 (3)C13B—C12B—Cl1B119.1 (2)
C21—N2—H2120 (3)C11B—C12B—Cl1B119.66 (18)
C12—C11—C16117.8 (2)C14B—C13B—C12B118.7 (3)
C12—C11—C1121.0 (2)C14B—C13B—H13B120.6
C16—C11—C1121.1 (2)C12B—C13B—H13B120.6
C11—C12—C13121.2 (3)C13B—C14B—C15B121.7 (2)
C11—C12—Cl1119.48 (19)C13B—C14B—H14B119.1
C13—C12—Cl1119.3 (2)C15B—C14B—H14B119.1
C14—C13—C12119.0 (3)C14B—C15B—C16B118.1 (3)
C14—C13—H13120.5C14B—C15B—H15B120.9
C12—C13—H13120.5C16B—C15B—H15B120.9
C13—C14—C15121.7 (3)C15B—C16B—C11B122.1 (2)
C13—C14—H14119.2C15B—C16B—Cl2B119.0 (2)
C15—C14—H14119.2C11B—C16B—Cl2B118.85 (18)
C14—C15—C16118.6 (3)C26B—C21B—C22B119.45 (19)
C14—C15—H15120.7C26B—C21B—N2B120.8 (2)
C16—C15—H15120.7C22B—C21B—N2B119.6 (2)
C15—C16—C11121.7 (3)C23B—C22B—C21B119.5 (2)
C15—C16—Cl2119.6 (2)C23B—C22B—Cl3B120.96 (18)
C11—C16—Cl2118.68 (19)C21B—C22B—Cl3B119.45 (17)
C22—C21—C26119.7 (2)C24B—C23B—C22B121.0 (2)
C22—C21—N2120.4 (2)C24B—C23B—Cl4B118.59 (18)
C26—C21—N2119.7 (2)C22B—C23B—Cl4B120.43 (19)
C21—C22—C23119.6 (2)C23B—C24B—C25B119.6 (2)
C21—C22—Cl3119.26 (17)C23B—C24B—H24B120.2
C23—C22—Cl3121.09 (19)C25B—C24B—H24B120.2
C24—C23—C22120.5 (2)C24B—C25B—C26B120.3 (2)
C24—C23—Cl4118.72 (18)C24B—C25B—Cl5B118.83 (18)
C22—C23—Cl4120.70 (19)C26B—C25B—Cl5B120.84 (19)
C23—C24—C25120.1 (2)C21B—C26B—C25B120.1 (2)
C23—C24—H24120.0C21B—C26B—Cl6B119.53 (17)
C25—C24—H24120.0C25B—C26B—Cl6B120.37 (18)
C24—C25—C26120.4 (2)O1C—C1C—N1C124.3 (2)
C24—C25—Cl5118.72 (18)O1C—C1C—C11C121.2 (2)
C26—C25—Cl5120.89 (19)N1C—C1C—C11C114.53 (19)
C25—C26—C21119.6 (2)C1C—N1C—C2C126.88 (19)
C25—C26—Cl6121.24 (18)C1C—N1C—H1C115.9 (19)
C21—C26—Cl6119.14 (17)C2C—N1C—H1C116.9 (19)
O1A—C1A—N1A124.5 (2)N2C—C2C—N1C115.53 (19)
O1A—C1A—C11A121.1 (2)N2C—C2C—S1C124.22 (16)
N1A—C1A—C11A114.40 (19)N1C—C2C—S1C120.25 (16)
C1A—N1A—C2A126.97 (19)C2C—N2C—C21C123.16 (19)
C1A—N1A—H1A114.3 (19)C2C—N2C—H2C113 (2)
C2A—N1A—H1A118.7 (19)C21C—N2C—H2C123 (2)
N2A—C2A—N1A115.45 (19)C12C—C11C—C16C118.3 (2)
N2A—C2A—S1A124.23 (16)C12C—C11C—C1C121.9 (3)
N1A—C2A—S1A120.32 (16)C16C—C11C—C1C119.7 (2)
C2A—N2A—C21A123.26 (19)C11C—C12C—C13C120.6 (3)
C2A—N2A—H2A117 (3)C11C—C12C—Cl1C119.5 (2)
C21A—N2A—H2A120 (3)C13C—C12C—Cl1C119.8 (3)
C16A—C11A—C12A117.9 (2)C14C—C13C—C12C118.9 (4)
C16A—C11A—C1A121.2 (2)C14C—C13C—H13C120.6
C12A—C11A—C1A120.8 (2)C12C—C13C—H13C120.6
C13A—C12A—C11A122.0 (3)C15C—C14C—C13C121.7 (3)
C13A—C12A—Cl1A119.2 (3)C15C—C14C—H14C119.1
C11A—C12A—Cl1A118.8 (2)C13C—C14C—H14C119.1
C12A—C13A—C14A118.2 (3)C14C—C15C—C16C119.0 (4)
C12A—C13A—H13A120.9C14C—C15C—H15C120.5
C14A—C13A—H13A120.9C16C—C15C—H15C120.5
C15A—C14A—C13A121.7 (3)C15C—C16C—C11C121.6 (3)
C15A—C14A—H14A119.1C15C—C16C—Cl2C119.7 (3)
C13A—C14A—H14A119.1C11C—C16C—Cl2C118.8 (2)
C14A—C15A—C16A119.2 (3)C26C—C21C—C22C119.56 (19)
C14A—C15A—H15A120.4C26C—C21C—N2C120.9 (2)
C16A—C15A—H15A120.4C22C—C21C—N2C119.38 (19)
C11A—C16A—C15A121.1 (3)C23C—C22C—C21C119.7 (2)
C11A—C16A—Cl2A119.27 (19)C23C—C22C—Cl3C121.21 (17)
C15A—C16A—Cl2A119.6 (3)C21C—C22C—Cl3C119.13 (16)
C26A—C21A—C22A119.9 (2)C24C—C23C—C22C120.7 (2)
C26A—C21A—N2A120.2 (2)C24C—C23C—Cl4C118.29 (17)
C22A—C21A—N2A119.7 (2)C22C—C23C—Cl4C120.97 (18)
C23A—C22A—C21A119.6 (2)C25C—C24C—C23C119.7 (2)
C23A—C22A—Cl3A121.07 (18)C25C—C24C—H24C120.1
C21A—C22A—Cl3A119.28 (16)C23C—C24C—H24C120.1
C24A—C23A—C22A120.5 (2)C24C—C25C—C26C120.3 (2)
C24A—C23A—Cl4A118.36 (17)C24C—C25C—Cl5C118.67 (17)
C22A—C23A—Cl4A121.08 (18)C26C—C25C—Cl5C120.99 (18)
C23A—C24A—C25A119.9 (2)C21C—C26C—C25C120.0 (2)
C23A—C24A—H24A120.1C21C—C26C—Cl6C119.50 (16)
C25A—C24A—H24A120.1C25C—C26C—Cl6C120.50 (17)
C24A—C25A—C26A120.2 (2)Cl13—C1L—Cl11111.14 (17)
C24A—C25A—Cl5A118.63 (18)Cl13—C1L—Cl12111.4 (2)
C26A—C25A—Cl5A121.11 (19)Cl11—C1L—Cl12110.41 (18)
C25A—C26A—C21A119.8 (2)Cl13—C1L—H1L107.9
C25A—C26A—Cl6A121.06 (19)Cl11—C1L—H1L107.9
C21A—C26A—Cl6A119.15 (17)Cl12—C1L—H1L107.9
O1B—C1B—N1B124.7 (2)Cl22—C2L—Cl23118.2 (3)
O1B—C1B—C11B121.3 (2)Cl22—C2L—Cl21116.2 (4)
N1B—C1B—C11B114.02 (19)Cl23—C2L—Cl21115.5 (3)
C1B—N1B—C2B127.06 (19)Cl22—C2L—H2L100.7
C1B—N1B—H1B120 (2)Cl23—C2L—H2L100.7
C2B—N1B—H1B113 (2)Cl21—C2L—H2L100.7
O1—C1—N1—C2−2.3 (4)O1B—C1B—N1B—C2B8.1 (4)
C11—C1—N1—C2177.2 (2)C11B—C1B—N1B—C2B−170.0 (2)
C1—N1—C2—N2−0.9 (4)C1B—N1B—C2B—N2B−1.8 (3)
C1—N1—C2—S1179.49 (19)C1B—N1B—C2B—S1B178.02 (19)
N1—C2—N2—C21−178.7 (2)N1B—C2B—N2B—C21B166.2 (2)
S1—C2—N2—C210.9 (3)S1B—C2B—N2B—C21B−13.6 (3)
O1—C1—C11—C12−81.7 (3)O1B—C1B—C11B—C16B−96.7 (3)
N1—C1—C11—C1298.7 (3)N1B—C1B—C11B—C16B81.5 (3)
O1—C1—C11—C1693.4 (3)O1B—C1B—C11B—C12B78.7 (3)
N1—C1—C11—C16−86.1 (3)N1B—C1B—C11B—C12B−103.1 (3)
C16—C11—C12—C131.0 (4)C16B—C11B—C12B—C13B−1.3 (4)
C1—C11—C12—C13176.3 (2)C1B—C11B—C12B—C13B−176.8 (2)
C16—C11—C12—Cl1−178.02 (19)C16B—C11B—C12B—Cl1B177.23 (18)
C1—C11—C12—Cl1−2.7 (3)C1B—C11B—C12B—Cl1B1.7 (3)
C11—C12—C13—C14−0.7 (4)C11B—C12B—C13B—C14B0.3 (4)
Cl1—C12—C13—C14178.3 (2)Cl1B—C12B—C13B—C14B−178.3 (2)
C12—C13—C14—C15−0.1 (4)C12B—C13B—C14B—C15B0.7 (4)
C13—C14—C15—C160.5 (4)C13B—C14B—C15B—C16B−0.6 (4)
C14—C15—C16—C11−0.1 (4)C14B—C15B—C16B—C11B−0.4 (4)
C14—C15—C16—Cl2−178.8 (2)C14B—C15B—C16B—Cl2B177.4 (2)
C12—C11—C16—C15−0.6 (4)C12B—C11B—C16B—C15B1.4 (4)
C1—C11—C16—C15−175.9 (2)C1B—C11B—C16B—C15B176.9 (2)
C12—C11—C16—Cl2178.10 (18)C12B—C11B—C16B—Cl2B−176.42 (18)
C1—C11—C16—Cl22.8 (3)C1B—C11B—C16B—Cl2B−0.9 (3)
C2—N2—C21—C2288.3 (3)C2B—N2B—C21B—C26B112.3 (3)
C2—N2—C21—C26−96.7 (3)C2B—N2B—C21B—C22B−72.4 (3)
C26—C21—C22—C23−1.2 (3)C26B—C21B—C22B—C23B−0.2 (3)
N2—C21—C22—C23173.8 (2)N2B—C21B—C22B—C23B−175.5 (2)
C26—C21—C22—Cl3178.82 (18)C26B—C21B—C22B—Cl3B177.49 (17)
N2—C21—C22—Cl3−6.2 (3)N2B—C21B—C22B—Cl3B2.1 (3)
C21—C22—C23—C241.5 (4)C21B—C22B—C23B—C24B−0.7 (3)
Cl3—C22—C23—C24−178.55 (19)Cl3B—C22B—C23B—C24B−178.28 (19)
C21—C22—C23—Cl4−176.41 (18)C21B—C22B—C23B—Cl4B177.96 (17)
Cl3—C22—C23—Cl43.5 (3)Cl3B—C22B—C23B—Cl4B0.4 (3)
C22—C23—C24—C25−0.3 (4)C22B—C23B—C24B—C25B0.9 (4)
Cl4—C23—C24—C25177.67 (19)Cl4B—C23B—C24B—C25B−177.72 (19)
C23—C24—C25—C26−1.2 (4)C23B—C24B—C25B—C26B−0.4 (4)
C23—C24—C25—Cl5−179.95 (19)C23B—C24B—C25B—Cl5B178.89 (19)
C24—C25—C26—C211.4 (3)C22B—C21B—C26B—C25B0.7 (3)
Cl5—C25—C26—C21−179.82 (17)N2B—C21B—C26B—C25B176.0 (2)
C24—C25—C26—Cl6−178.41 (18)C22B—C21B—C26B—Cl6B−178.78 (17)
Cl5—C25—C26—Cl60.3 (3)N2B—C21B—C26B—Cl6B−3.4 (3)
C22—C21—C26—C25−0.2 (3)C24B—C25B—C26B—C21B−0.5 (4)
N2—C21—C26—C25−175.3 (2)Cl5B—C25B—C26B—C21B−179.70 (18)
C22—C21—C26—Cl6179.63 (18)C24B—C25B—C26B—Cl6B179.03 (19)
N2—C21—C26—Cl64.6 (3)Cl5B—C25B—C26B—Cl6B−0.2 (3)
O1A—C1A—N1A—C2A−1.6 (4)O1C—C1C—N1C—C2C10.0 (4)
C11A—C1A—N1A—C2A177.8 (2)C11C—C1C—N1C—C2C−169.2 (2)
C1A—N1A—C2A—N2A1.2 (3)C1C—N1C—C2C—N2C−2.2 (3)
C1A—N1A—C2A—S1A−178.15 (19)C1C—N1C—C2C—S1C177.26 (19)
N1A—C2A—N2A—C21A−179.5 (2)N1C—C2C—N2C—C21C165.8 (2)
S1A—C2A—N2A—C21A−0.2 (3)S1C—C2C—N2C—C21C−13.7 (3)
O1A—C1A—C11A—C16A−87.3 (3)O1C—C1C—C11C—C12C85.8 (3)
N1A—C1A—C11A—C16A93.3 (3)N1C—C1C—C11C—C12C−95.0 (3)
O1A—C1A—C11A—C12A87.6 (3)O1C—C1C—C11C—C16C−90.5 (3)
N1A—C1A—C11A—C12A−91.8 (3)N1C—C1C—C11C—C16C88.6 (3)
C16A—C11A—C12A—C13A−0.6 (4)C16C—C11C—C12C—C13C−0.3 (4)
C1A—C11A—C12A—C13A−175.6 (2)C1C—C11C—C12C—C13C−176.7 (2)
C16A—C11A—C12A—Cl1A177.91 (19)C16C—C11C—C12C—Cl1C178.1 (2)
C1A—C11A—C12A—Cl1A2.8 (3)C1C—C11C—C12C—Cl1C1.7 (3)
C11A—C12A—C13A—C14A0.6 (4)C11C—C12C—C13C—C14C0.3 (4)
Cl1A—C12A—C13A—C14A−177.9 (2)Cl1C—C12C—C13C—C14C−178.1 (2)
C12A—C13A—C14A—C15A−0.5 (5)C12C—C13C—C14C—C15C0.0 (5)
C13A—C14A—C15A—C16A0.4 (5)C13C—C14C—C15C—C16C−0.3 (5)
C12A—C11A—C16A—C15A0.4 (4)C14C—C15C—C16C—C11C0.2 (5)
C1A—C11A—C16A—C15A175.5 (2)C14C—C15C—C16C—Cl2C−179.8 (2)
C12A—C11A—C16A—Cl2A−178.72 (19)C12C—C11C—C16C—C15C0.1 (4)
C1A—C11A—C16A—Cl2A−3.7 (3)C1C—C11C—C16C—C15C176.5 (2)
C14A—C15A—C16A—C11A−0.4 (4)C12C—C11C—C16C—Cl2C−179.93 (19)
C14A—C15A—C16A—Cl2A178.8 (2)C1C—C11C—C16C—Cl2C−3.5 (3)
C2A—N2A—C21A—C26A91.8 (3)C2C—N2C—C21C—C26C104.0 (3)
C2A—N2A—C21A—C22A−92.9 (3)C2C—N2C—C21C—C22C−80.7 (3)
C26A—C21A—C22A—C23A−0.7 (3)C26C—C21C—C22C—C23C−0.6 (3)
N2A—C21A—C22A—C23A−175.9 (2)N2C—C21C—C22C—C23C−176.0 (2)
C26A—C21A—C22A—Cl3A179.80 (17)C26C—C21C—C22C—Cl3C179.09 (17)
N2A—C21A—C22A—Cl3A4.5 (3)N2C—C21C—C22C—Cl3C3.7 (3)
C21A—C22A—C23A—C24A1.2 (3)C21C—C22C—C23C—C24C0.9 (3)
Cl3A—C22A—C23A—C24A−179.30 (18)Cl3C—C22C—C23C—C24C−178.75 (18)
C21A—C22A—C23A—Cl4A−179.68 (17)C21C—C22C—C23C—Cl4C179.53 (17)
Cl3A—C22A—C23A—Cl4A−0.2 (3)Cl3C—C22C—C23C—Cl4C−0.2 (3)
C22A—C23A—C24A—C25A−0.7 (4)C22C—C23C—C24C—C25C−0.5 (4)
Cl4A—C23A—C24A—C25A−179.82 (19)Cl4C—C23C—C24C—C25C−179.13 (18)
C23A—C24A—C25A—C26A−0.4 (4)C23C—C24C—C25C—C26C−0.3 (4)
C23A—C24A—C25A—Cl5A178.24 (19)C23C—C24C—C25C—Cl5C178.69 (18)
C24A—C25A—C26A—C21A0.9 (4)C22C—C21C—C26C—C25C−0.2 (3)
Cl5A—C25A—C26A—C21A−177.70 (18)N2C—C21C—C26C—C25C175.1 (2)
C24A—C25A—C26A—Cl6A−178.40 (19)C22C—C21C—C26C—Cl6C−179.91 (17)
Cl5A—C25A—C26A—Cl6A3.0 (3)N2C—C21C—C26C—Cl6C−4.6 (3)
C22A—C21A—C26A—C25A−0.4 (3)C24C—C25C—C26C—C21C0.6 (4)
N2A—C21A—C26A—C25A174.9 (2)Cl5C—C25C—C26C—C21C−178.33 (18)
C22A—C21A—C26A—Cl6A178.94 (17)C24C—C25C—C26C—Cl6C−179.64 (19)
N2A—C21A—C26A—Cl6A−5.8 (3)Cl5C—C25C—C26C—Cl6C1.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1B0.80 (3)2.60 (3)3.362 (2)160 (3)
N2—H2···O10.78 (3)1.96 (3)2.621 (2)142 (3)
N2—H2···Cl4Ci0.78 (3)2.94 (3)3.539 (2)135 (3)
N1A—H1A···S1C0.84 (3)2.55 (3)3.381 (2)170 (3)
N2A—H2A···O1A0.75 (3)2.00 (3)2.625 (3)141 (3)
N2A—H2A···Cl4Aii0.75 (3)2.90 (3)3.478 (2)136 (3)
N1B—H1B···S10.83 (3)2.63 (3)3.425 (2)162 (3)
N2B—H2B···O1B0.78 (3)2.01 (3)2.639 (2)138 (3)
N1C—H1C···S1A0.86 (3)2.57 (3)3.416 (2)168 (3)
N2C—H2C···O1C0.77 (3)1.97 (3)2.629 (3)144 (3)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1B0.80 (3)2.60 (3)3.362 (2)160 (3)
N2—H2···O10.78 (3)1.96 (3)2.621 (2)142 (3)
N2—H2···Cl4Ci0.78 (3)2.94 (3)3.539 (2)135 (3)
N1A—H1A···S1C0.84 (3)2.55 (3)3.381 (2)170 (3)
N2A—H2A···O1A0.75 (3)2.00 (3)2.625 (3)141 (3)
N2A—H2A···Cl4Aii0.75 (3)2.90 (3)3.478 (2)136 (3)
N1B—H1B···S10.83 (3)2.63 (3)3.425 (2)162 (3)
N2B—H2B···O1B0.78 (3)2.01 (3)2.639 (2)138 (3)
N1C—H1C···S1A0.86 (3)2.57 (3)3.416 (2)168 (3)
N2C—H2C···O1C0.77 (3)1.97 (3)2.629 (3)144 (3)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1.
Acknowledgements top

MKR is grateful to the HEC, Pakistan, for financial support for a PhD programme under scholarship No. ILC-0363104.

references
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