5-Chloro-2-(thio-phen-2-yl)-1-(thio-phen-2-ylmeth-yl)-1H-benzimidazole-6-chloro-2-(thiophen-2-yl)-1-(thiophen-2-ylmethyl)-1H-benzimidazole (0.94/0.06).

There are two independent mol-ecules in the asymmetric unit of the title compound, C16H11ClN2S2. The structure exhibits rotational disorder of the 2-thio-phen-2-yl substituent in each of the unique mol-ecules with a major:minor component ratio of 0.927 (2):0.073 (2). For one of the symmetry-unique molecules, 6.0 (2)% of the sites are occupied by the 6-chloro-isomer. The major component thio-phene rings make dihedral angles of 38.90 (12) and 36.32 (11)° with the benzimidazole rings in the two independent mol-ecules. In the crystal, mol-ecules are linked into chains parallel to [100] via weak C-H⋯N inter-actions.

Related literature

For the structure of 6-chloro-2-(thio­phen-2-yl)-1-(thio­phen-2-ylmeth­yl)-1H-benzimidazole, see: Geiger & Nellist (2013 ▶). For the structure of the 5-bromo analogue, see: Geiger & Destefano (2012 ▶).

Experimental

Crystal data

C16H11ClN2S2

M = 330.84

Monoclinic,

a = 12.7407 (11) Å

b = 10.5126 (8) Å

c = 22.955 (2) Å

β = 100.461 (3)°

V = 3023.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.52 mm−1

T = 200 K

0.80 × 0.40 × 0.20 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.62, T max = 0.90

32145 measured reflections

5356 independent reflections

4419 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.08

5356 reflections

420 parameters

227 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024999/fj2642sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024999/fj2642Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024999/fj2642Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024999/fj2642Isup4.cml

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

C16H11ClN2S2	F(000) = 1360
Mr = 330.84	Dx = 1.454 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.7407 (11) Å	Cell parameters from 9493 reflections
b = 10.5126 (8) Å	θ = 2.6–24.9°
c = 22.955 (2) Å	µ = 0.52 mm−1
β = 100.461 (3)°	T = 200 K
V = 3023.4 (4) Å3	Plate, colourless
Z = 8	0.80 × 0.40 × 0.20 mm

Bruker SMART X2S benchtop diffractometer	5356 independent reflections
Radiation source: XOS X-beam microfocus source	4419 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.072
ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −15→14
Tmin = 0.62, Tmax = 0.90	k = −12→11
32145 measured reflections	l = −27→27

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0256P)2 + 1.7458P] where P = (Fo2 + 2Fc2)/3
5356 reflections	(Δ/σ)max < 0.001
420 parameters	Δρmax = 0.34 e Å−3
227 restraints	Δρmin = −0.44 e Å−3

Experimental. 1H NMR spectrum (CDCl3, 400 MHz, p.p.m.). 7.71 (1 H, d), 7.53 (1 H, d), 7.48 (1 H, d), 7.34 (1 H, s), 7.28 (2 H, m), 7.17 (1 H, t), 6.96 (1 H, t), 6.91 (1 H, d), 5.60 (2 H, s).

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	Occ. (<1)
Cl1	0.61379 (6)	0.64223 (7)	0.03514 (3)	0.0429 (2)	0.9401 (19)
Cl11	0.8208 (9)	0.6153 (12)	0.0775 (5)	0.049 (4)	0.0599 (19)
Cl2	0.24867 (6)	0.62779 (8)	0.45858 (3)	0.0552 (2)
S1	0.46460 (5)	0.23990 (8)	0.31622 (3)	0.0333 (2)	0.9272 (19)
C8	0.5695 (2)	0.3464 (3)	0.32835 (12)	0.0277 (5)	0.9272 (19)
C9	0.6012 (3)	0.3670 (5)	0.3868 (2)	0.0408 (11)	0.9272 (19)
H9	0.6582	0.4227	0.4023	0.049*	0.9272 (19)
C10	0.5428 (4)	0.2989 (4)	0.42304 (16)	0.0457 (9)	0.9272 (19)
H10	0.5555	0.3036	0.4651	0.055*	0.9272 (19)
C11	0.4661 (3)	0.2258 (4)	0.39051 (14)	0.0415 (8)	0.9272 (19)
H11	0.4188	0.1728	0.4071	0.05*	0.9272 (19)
S201	0.6207 (13)	0.3828 (18)	0.3975 (8)	0.0333 (2)	0.0728 (19)
C208	0.5691 (18)	0.347 (2)	0.3258 (8)	0.0277 (5)	0.0728 (19)
C209	0.495 (3)	0.255 (4)	0.3208 (14)	0.0408 (11)	0.0728 (19)
H209	0.4615	0.2198	0.284	0.049*	0.0728 (19)
C210	0.471 (4)	0.218 (5)	0.3759 (17)	0.0457 (9)	0.0728 (19)
H210	0.4162	0.1597	0.3805	0.055*	0.0728 (19)
C211	0.537 (4)	0.274 (5)	0.4217 (14)	0.0415 (8)	0.0728 (19)
H211	0.5372	0.2563	0.4623	0.05*	0.0728 (19)
S3	−0.08034 (5)	0.24052 (8)	0.17321 (4)	0.0362 (2)	0.9272 (19)
C24	0.0189 (2)	0.3445 (3)	0.16210 (12)	0.0291 (5)	0.9272 (19)
C25	0.0157 (3)	0.3639 (5)	0.10334 (19)	0.0409 (10)	0.9272 (19)
H25	0.0635	0.419	0.0883	0.049*	0.9272 (19)
C26	−0.0651 (3)	0.2945 (3)	0.06668 (15)	0.0427 (9)	0.9272 (19)
H26	−0.0773	0.2968	0.0246	0.051*	0.9272 (19)
C27	−0.1236 (2)	0.2238 (4)	0.09864 (14)	0.0416 (8)	0.9272 (19)
H27	−0.1818	0.1713	0.0816	0.05*	0.9272 (19)
S203	0.0313 (13)	0.3664 (18)	0.0909 (8)	0.0362 (2)	0.0728 (19)
C204	0.0221 (18)	0.345 (2)	0.1633 (8)	0.0291 (5)	0.0728 (19)
C205	−0.055 (3)	0.263 (4)	0.1702 (14)	0.0409 (10)	0.0728 (19)
H205	−0.0717	0.2402	0.2076	0.049*	0.0728 (19)
C206	−0.110 (3)	0.214 (5)	0.1156 (16)	0.0427 (9)	0.0728 (19)
H206	−0.168	0.1558	0.1121	0.051*	0.0728 (19)
C207	−0.071 (4)	0.261 (5)	0.0688 (14)	0.0416 (8)	0.0728 (19)
H207	−0.0973	0.2385	0.0287	0.05*	0.0728 (19)
N1	0.70729 (13)	0.43276 (18)	0.27330 (8)	0.0266 (4)
N2	0.53427 (13)	0.43584 (18)	0.22876 (9)	0.0289 (4)
N3	0.19102 (13)	0.43204 (18)	0.21832 (8)	0.0274 (4)
N4	0.04623 (13)	0.43177 (18)	0.26202 (9)	0.0284 (4)
C1	0.59642 (16)	0.4881 (2)	0.19105 (10)	0.0268 (5)
C2	0.70448 (16)	0.4859 (2)	0.21790 (10)	0.0260 (5)
C3	0.78547 (17)	0.5283 (2)	0.18928 (11)	0.0318 (6)
H3	0.8583	0.5262	0.2081	0.038*
C4	0.75470 (18)	0.5735 (2)	0.13244 (11)	0.0345 (6)
H4	0.8073	0.6019	0.1109	0.041*	0.9401 (19)
C5	0.64661 (19)	0.5781 (2)	0.10605 (11)	0.0315 (5)
H5	0.628	0.6115	0.0671	0.038*	0.0599 (19)
C6	0.56597 (17)	0.5361 (2)	0.13409 (10)	0.0306 (5)
H6	0.4932	0.5399	0.1154	0.037*
C7	0.60260 (16)	0.4044 (2)	0.27688 (10)	0.0262 (5)
C12	0.80522 (16)	0.4025 (2)	0.31486 (10)	0.0289 (5)
H12A	0.8618	0.3815	0.2921	0.035*
H12B	0.7926	0.3259	0.3377	0.035*
C17	0.22345 (16)	0.4840 (2)	0.27401 (10)	0.0258 (5)
C18	0.13203 (16)	0.4836 (2)	0.30049 (10)	0.0267 (5)
C19	0.13799 (17)	0.5298 (2)	0.35781 (11)	0.0306 (5)
H19	0.077	0.5334	0.3762	0.037*
C20	0.23665 (18)	0.5700 (2)	0.38649 (10)	0.0321 (5)
C21	0.32827 (17)	0.5684 (2)	0.36057 (11)	0.0317 (5)
H21	0.3946	0.5964	0.3827	0.038*
C22	0.32240 (16)	0.5266 (2)	0.30348 (10)	0.0292 (5)
H22	0.3832	0.5266	0.2849	0.035*
C23	0.08426 (15)	0.4026 (2)	0.21395 (10)	0.0262 (5)
C28	0.26310 (16)	0.4040 (2)	0.17696 (10)	0.0284 (5)
H28A	0.2356	0.3289	0.1529	0.034*
H28B	0.3341	0.3815	0.2	0.034*
S2	0.86470 (5)	0.66077 (6)	0.33429 (3)	0.03759 (17)
C13	0.84454 (16)	0.5082 (2)	0.35767 (11)	0.0282 (5)
C14	0.87606 (16)	0.4981 (2)	0.41784 (11)	0.0325 (6)
H14	0.8725	0.4213	0.4392	0.039*
C15	0.91451 (18)	0.6146 (3)	0.44476 (12)	0.0396 (6)
H15	0.939	0.6246	0.4861	0.047*
C16	0.91244 (19)	0.7094 (3)	0.40503 (12)	0.0418 (6)
H16	0.935	0.7939	0.4153	0.05*
S4	0.31336 (5)	0.66291 (6)	0.16150 (3)	0.03820 (17)
C29	0.27602 (16)	0.5123 (2)	0.13586 (11)	0.0294 (5)
C30	0.26814 (17)	0.5050 (2)	0.07566 (11)	0.0351 (6)
H30	0.2493	0.4297	0.0533	0.042*
C31	0.29151 (19)	0.6233 (3)	0.05033 (12)	0.0403 (6)
H31	0.2902	0.6356	0.0092	0.048*
C32	0.3156 (2)	0.7157 (3)	0.09140 (12)	0.0431 (7)
H32	0.332	0.8008	0.0823	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.0563 (4)	0.0435 (4)	0.0311 (4)	0.0043 (3)	0.0138 (3)	0.0081 (3)
Cl11	0.051 (6)	0.063 (9)	0.034 (7)	−0.011 (5)	0.009 (5)	0.000 (6)
Cl2	0.0515 (4)	0.0819 (6)	0.0331 (4)	−0.0096 (4)	0.0102 (3)	−0.0183 (4)
S1	0.0295 (4)	0.0352 (4)	0.0347 (4)	−0.0119 (3)	0.0046 (3)	0.0021 (3)
C8	0.0231 (10)	0.0265 (13)	0.0337 (14)	−0.0024 (9)	0.0057 (9)	0.0012 (11)
C9	0.033 (2)	0.052 (2)	0.038 (2)	−0.0188 (16)	0.0054 (16)	−0.0017 (18)
C10	0.0437 (16)	0.063 (3)	0.0309 (16)	−0.0155 (16)	0.0080 (12)	0.0035 (15)
C11	0.0361 (14)	0.0511 (19)	0.038 (2)	−0.0146 (13)	0.0099 (15)	0.0091 (17)
S201	0.0295 (4)	0.0352 (4)	0.0347 (4)	−0.0119 (3)	0.0046 (3)	0.0021 (3)
C208	0.0231 (10)	0.0265 (13)	0.0337 (14)	−0.0024 (9)	0.0057 (9)	0.0012 (11)
C209	0.033 (2)	0.052 (2)	0.038 (2)	−0.0188 (16)	0.0054 (16)	−0.0017 (18)
C210	0.0437 (16)	0.063 (3)	0.0309 (16)	−0.0155 (16)	0.0080 (12)	0.0035 (15)
C211	0.0361 (14)	0.0511 (19)	0.038 (2)	−0.0146 (13)	0.0099 (15)	0.0091 (17)
S3	0.0271 (4)	0.0369 (5)	0.0435 (4)	−0.0089 (3)	0.0037 (3)	−0.0040 (3)
C24	0.0210 (10)	0.0310 (13)	0.0346 (14)	0.0000 (9)	0.0032 (9)	−0.0021 (11)
C25	0.0257 (19)	0.054 (2)	0.043 (3)	−0.0045 (15)	0.0062 (13)	−0.0012 (19)
C26	0.0367 (14)	0.053 (3)	0.0351 (16)	0.0008 (15)	−0.0030 (12)	−0.0060 (15)
C27	0.0280 (14)	0.0468 (19)	0.046 (2)	−0.0060 (13)	−0.0046 (13)	−0.0113 (17)
S203	0.0271 (4)	0.0369 (5)	0.0435 (4)	−0.0089 (3)	0.0037 (3)	−0.0040 (3)
C204	0.0210 (10)	0.0310 (13)	0.0346 (14)	0.0000 (9)	0.0032 (9)	−0.0021 (11)
C205	0.0257 (19)	0.054 (2)	0.043 (3)	−0.0045 (15)	0.0062 (13)	−0.0012 (19)
C206	0.0367 (14)	0.053 (3)	0.0351 (16)	0.0008 (15)	−0.0030 (12)	−0.0060 (15)
C207	0.0280 (14)	0.0468 (19)	0.046 (2)	−0.0060 (13)	−0.0046 (13)	−0.0113 (17)
N1	0.0219 (8)	0.0274 (11)	0.0308 (11)	−0.0016 (7)	0.0059 (8)	0.0029 (9)
N2	0.0232 (9)	0.0330 (11)	0.0311 (11)	−0.0019 (8)	0.0067 (8)	0.0024 (9)
N3	0.0216 (9)	0.0320 (11)	0.0291 (11)	−0.0019 (8)	0.0059 (7)	−0.0055 (9)
N4	0.0207 (9)	0.0320 (11)	0.0325 (11)	−0.0012 (8)	0.0048 (8)	−0.0009 (9)
C1	0.0269 (11)	0.0248 (13)	0.0299 (13)	0.0019 (9)	0.0086 (9)	−0.0013 (10)
C2	0.0261 (10)	0.0214 (12)	0.0315 (13)	0.0016 (9)	0.0078 (9)	−0.0009 (10)
C3	0.0259 (11)	0.0303 (14)	0.0413 (15)	−0.0001 (9)	0.0118 (10)	0.0007 (11)
C4	0.0391 (13)	0.0263 (14)	0.0438 (16)	−0.0008 (10)	0.0230 (11)	0.0012 (12)
C5	0.0433 (13)	0.0223 (13)	0.0317 (14)	0.0043 (10)	0.0145 (11)	0.0018 (11)
C6	0.0294 (11)	0.0306 (14)	0.0324 (14)	0.0053 (10)	0.0071 (10)	0.0012 (11)
C7	0.0230 (10)	0.0262 (13)	0.0299 (13)	−0.0024 (9)	0.0065 (9)	−0.0026 (10)
C12	0.0217 (10)	0.0290 (13)	0.0356 (14)	0.0020 (9)	0.0042 (9)	0.0053 (11)
C17	0.0239 (10)	0.0252 (13)	0.0283 (13)	0.0015 (9)	0.0047 (9)	−0.0006 (10)
C18	0.0224 (10)	0.0266 (13)	0.0307 (13)	0.0017 (9)	0.0038 (9)	0.0019 (10)
C19	0.0262 (11)	0.0350 (14)	0.0320 (14)	0.0040 (10)	0.0093 (10)	−0.0001 (11)
C20	0.0376 (12)	0.0325 (14)	0.0259 (13)	0.0004 (10)	0.0049 (10)	−0.0035 (11)
C21	0.0269 (11)	0.0323 (14)	0.0346 (14)	−0.0033 (10)	0.0020 (10)	−0.0024 (11)
C22	0.0213 (10)	0.0323 (14)	0.0346 (14)	0.0005 (9)	0.0070 (9)	−0.0021 (11)
C23	0.0202 (10)	0.0260 (13)	0.0315 (13)	−0.0002 (9)	0.0022 (9)	0.0013 (10)
C28	0.0233 (10)	0.0315 (13)	0.0314 (13)	0.0000 (9)	0.0078 (9)	−0.0082 (11)
S2	0.0398 (3)	0.0302 (4)	0.0410 (4)	−0.0011 (3)	0.0027 (3)	0.0069 (3)
C13	0.0192 (10)	0.0301 (13)	0.0359 (14)	0.0002 (9)	0.0067 (9)	0.0052 (11)
C14	0.0259 (11)	0.0348 (14)	0.0367 (15)	−0.0021 (10)	0.0056 (10)	0.0079 (12)
C15	0.0312 (12)	0.0489 (17)	0.0368 (15)	0.0022 (11)	0.0013 (10)	−0.0028 (13)
C16	0.0397 (13)	0.0332 (15)	0.0501 (17)	−0.0011 (11)	0.0018 (12)	−0.0039 (13)
S4	0.0412 (3)	0.0324 (4)	0.0424 (4)	0.0001 (3)	0.0117 (3)	−0.0055 (3)
C29	0.0193 (10)	0.0344 (14)	0.0353 (14)	0.0007 (9)	0.0070 (9)	−0.0054 (11)
C30	0.0282 (11)	0.0452 (16)	0.0336 (14)	−0.0016 (11)	0.0100 (10)	−0.0029 (12)
C31	0.0371 (13)	0.0501 (18)	0.0352 (15)	0.0061 (12)	0.0103 (11)	0.0070 (13)
C32	0.0464 (14)	0.0340 (15)	0.0520 (18)	0.0050 (12)	0.0176 (13)	0.0077 (14)

Cl1—C5	1.741 (2)	N3—C17	1.383 (3)
Cl11—C4	1.696 (10)	N3—C28	1.466 (3)
Cl2—C20	1.743 (2)	N4—C23	1.319 (3)
S1—C11	1.708 (3)	N4—C18	1.386 (3)
S1—C8	1.728 (3)	C1—C6	1.390 (3)
C8—C9	1.347 (5)	C1—C2	1.403 (3)
C8—C7	1.457 (3)	C2—C3	1.393 (3)
C9—C10	1.408 (5)	C3—C4	1.377 (3)
C9—H9	0.95	C3—H3	0.95
C10—C11	1.355 (4)	C4—C5	1.401 (3)
C10—H10	0.95	C4—H4	0.95
C11—H11	0.95	C5—C6	1.380 (3)
S201—C208	1.701 (16)	C5—H5	0.95
S201—C211	1.719 (16)	C6—H6	0.95
C208—C209	1.337 (16)	C12—C13	1.507 (3)
C208—C7	1.410 (17)	C12—H12A	0.99
C209—C210	1.410 (16)	C12—H12B	0.99
C209—H209	0.95	C17—C22	1.392 (3)
C210—C211	1.359 (16)	C17—C18	1.408 (3)
C210—H210	0.95	C18—C19	1.392 (3)
C211—H211	0.95	C19—C20	1.375 (3)
S3—C27	1.709 (3)	C19—H19	0.95
S3—C24	1.725 (3)	C20—C21	1.403 (3)
C24—C25	1.358 (5)	C21—C22	1.371 (3)
C24—C23	1.457 (3)	C21—H21	0.95
C25—C26	1.410 (5)	C22—H22	0.95
C25—H25	0.95	C28—C29	1.507 (3)
C26—C27	1.358 (4)	C28—H28A	0.99
C26—H26	0.95	C28—H28B	0.99
C27—H27	0.95	S2—C16	1.706 (3)
S203—C204	1.703 (16)	S2—C13	1.725 (2)
S203—C207	1.717 (16)	C13—C14	1.371 (3)
C204—C205	1.340 (16)	C14—C15	1.418 (4)
C204—C23	1.419 (16)	C14—H14	0.95
C205—C206	1.415 (16)	C15—C16	1.348 (4)
C205—H205	0.95	C15—H15	0.95
C206—C207	1.357 (15)	C16—H16	0.95
C206—H206	0.95	S4—C32	1.707 (3)
C207—H207	0.95	S4—C29	1.726 (2)
N1—C2	1.383 (3)	C29—C30	1.369 (3)
N1—C7	1.384 (3)	C30—C31	1.427 (4)
N1—C12	1.461 (3)	C30—H30	0.95
N2—C7	1.319 (3)	C31—C32	1.350 (4)
N2—C1	1.388 (3)	C31—H31	0.95
N3—C23	1.381 (3)	C32—H32	0.95
C11—S1—C8	91.57 (14)	C6—C5—Cl1	119.14 (19)
C9—C8—C7	131.5 (3)	C4—C5—Cl1	117.90 (18)
C9—C8—S1	110.3 (2)	C6—C5—H5	118.5
C7—C8—S1	118.0 (2)	C4—C5—H5	118.5
C8—C9—C10	114.3 (3)	Cl1—C5—H5	1.2
C8—C9—H9	122.8	C5—C6—C1	116.8 (2)
C10—C9—H9	122.8	C5—C6—H6	121.6
C11—C10—C9	111.6 (3)	C1—C6—H6	121.6
C11—C10—H10	124.2	N2—C7—N1	113.1 (2)
C9—C10—H10	124.2	N2—C7—C208	121.8 (10)
C10—C11—S1	112.2 (2)	N1—C7—C208	125.1 (10)
C10—C11—H11	123.9	N2—C7—C8	122.7 (2)
S1—C11—H11	123.9	N1—C7—C8	124.2 (2)
C208—S201—C211	90.7 (11)	C208—C7—C8	1.3 (12)
C209—C208—C7	123 (2)	N1—C12—C13	114.12 (18)
C209—C208—S201	112.8 (13)	N1—C12—H12A	108.7
C7—C208—S201	123.7 (19)	C13—C12—H12A	108.7
C208—C209—C210	112.7 (16)	N1—C12—H12B	108.7
C208—C209—H209	123.6	C13—C12—H12B	108.7
C210—C209—H209	123.6	H12A—C12—H12B	107.6
C211—C210—C209	111.7 (17)	N3—C17—C22	132.0 (2)
C211—C210—H210	124.2	N3—C17—C18	105.43 (18)
C209—C210—H210	124.2	C22—C17—C18	122.6 (2)
C210—C211—S201	111.9 (15)	N4—C18—C19	129.87 (19)
C210—C211—H211	124.1	N4—C18—C17	110.2 (2)
S201—C211—H211	124.1	C19—C18—C17	120.0 (2)
C27—S3—C24	91.65 (14)	C20—C19—C18	116.6 (2)
C25—C24—C23	131.2 (3)	C20—C19—H19	121.7
C25—C24—S3	110.6 (2)	C18—C19—H19	121.7
C23—C24—S3	118.1 (2)	C19—C20—C21	123.5 (2)
C24—C25—C26	113.7 (3)	C19—C20—Cl2	118.46 (18)
C24—C25—H25	123.1	C21—C20—Cl2	118.05 (18)
C26—C25—H25	123.1	C22—C21—C20	120.3 (2)
C27—C26—C25	111.9 (3)	C22—C21—H21	119.9
C27—C26—H26	124.0	C20—C21—H21	119.9
C25—C26—H26	124.0	C21—C22—C17	117.1 (2)
C26—C27—S3	112.1 (2)	C21—C22—H22	121.5
C26—C27—H27	123.9	C17—C22—H22	121.5
S3—C27—H27	123.9	N4—C23—N3	113.17 (19)
C204—S203—C207	91.1 (11)	N4—C23—C204	123.4 (10)
C205—C204—C23	120 (2)	N3—C23—C204	123.5 (10)
C205—C204—S203	112.5 (13)	N4—C23—C24	122.6 (2)
C23—C204—S203	128.0 (19)	N3—C23—C24	124.3 (2)
C204—C205—C206	112.7 (16)	C204—C23—C24	1.0 (9)
C204—C205—H205	123.7	N3—C28—C29	113.96 (18)
C206—C205—H205	123.7	N3—C28—H28A	108.8
C207—C206—C205	112.1 (17)	C29—C28—H28A	108.8
C207—C206—H206	124.0	N3—C28—H28B	108.8
C205—C206—H206	124.0	C29—C28—H28B	108.8
C206—C207—S203	111.6 (15)	H28A—C28—H28B	107.7
C206—C207—H207	124.2	C16—S2—C13	91.71 (13)
S203—C207—H207	124.2	C14—C13—C12	127.0 (2)
C2—N1—C7	106.10 (18)	C14—C13—S2	110.64 (18)
C2—N1—C12	124.36 (17)	C12—C13—S2	122.21 (18)
C7—N1—C12	129.22 (19)	C13—C14—C15	112.8 (2)
C7—N2—C1	104.91 (17)	C13—C14—H14	123.6
C23—N3—C17	106.32 (17)	C15—C14—H14	123.6
C23—N3—C28	129.24 (19)	C16—C15—C14	112.4 (2)
C17—N3—C28	124.14 (17)	C16—C15—H15	123.8
C23—N4—C18	104.92 (17)	C14—C15—H15	123.8
N2—C1—C6	129.6 (2)	C15—C16—S2	112.5 (2)
N2—C1—C2	110.2 (2)	C15—C16—H16	123.8
C6—C1—C2	120.2 (2)	S2—C16—H16	123.8
N1—C2—C3	131.7 (2)	C32—S4—C29	91.59 (13)
N1—C2—C1	105.68 (18)	C30—C29—C28	126.4 (2)
C3—C2—C1	122.6 (2)	C30—C29—S4	111.14 (19)
C4—C3—C2	116.7 (2)	C28—C29—S4	122.31 (17)
C4—C3—H3	121.6	C29—C30—C31	112.3 (2)
C2—C3—H3	121.6	C29—C30—H30	123.8
C3—C4—C5	120.7 (2)	C31—C30—H30	123.8
C3—C4—Cl11	134.4 (4)	C32—C31—C30	112.4 (2)
C5—C4—Cl11	104.5 (4)	C32—C31—H31	123.8
C3—C4—H4	119.7	C30—C31—H31	123.8
C5—C4—H4	119.7	C31—C32—S4	112.6 (2)
Cl11—C4—H4	16.2	C31—C32—H32	123.7
C6—C5—C4	123.0 (2)	S4—C32—H32	123.7
C11—S1—C8—C9	0.0 (3)	C9—C8—C7—N1	41.4 (5)
C11—S1—C8—C7	−175.5 (2)	S1—C8—C7—N1	−144.2 (2)
C7—C8—C9—C10	174.6 (3)	C9—C8—C7—C208	180.100
S1—C8—C9—C10	−0.1 (5)	S1—C8—C7—C208	−10.40
C8—C9—C10—C11	0.2 (6)	C2—N1—C12—C13	91.6 (3)
C9—C10—C11—S1	−0.2 (5)	C7—N1—C12—C13	−95.8 (3)
C8—S1—C11—C10	0.1 (3)	C23—N3—C17—C22	177.4 (2)
C211—S201—C208—C209	−1 (3)	C28—N3—C17—C22	3.2 (4)
C211—S201—C208—C7	179.9 (16)	C23—N3—C17—C18	−0.4 (2)
C7—C208—C209—C210	−177 (2)	C28—N3—C17—C18	−174.5 (2)
S201—C208—C209—C210	4 (4)	C23—N4—C18—C19	−179.4 (2)
C208—C209—C210—C211	−6 (5)	C23—N4—C18—C17	−0.3 (3)
C209—C210—C211—S201	5 (5)	N3—C17—C18—N4	0.4 (3)
C208—S201—C211—C210	−2 (4)	C22—C17—C18—N4	−177.6 (2)
C27—S3—C24—C25	0.5 (3)	N3—C17—C18—C19	179.6 (2)
C27—S3—C24—C23	176.1 (2)	C22—C17—C18—C19	1.6 (4)
C23—C24—C25—C26	−175.6 (3)	N4—C18—C19—C20	176.7 (2)
S3—C24—C25—C26	−0.8 (5)	C17—C18—C19—C20	−2.3 (3)
C24—C25—C26—C27	0.7 (5)	C18—C19—C20—C21	1.2 (4)
C25—C26—C27—S3	−0.4 (4)	C18—C19—C20—Cl2	−179.58 (17)
C24—S3—C27—C26	−0.1 (3)	C19—C20—C21—C22	0.7 (4)
C207—S203—C204—C205	−1 (3)	Cl2—C20—C21—C22	−178.49 (19)
C207—S203—C204—C23	−179.9 (18)	C20—C21—C22—C17	−1.5 (3)
C23—C204—C205—C206	180 (2)	N3—C17—C22—C21	−177.1 (2)
S203—C204—C205—C206	0 (3)	C18—C17—C22—C21	0.3 (3)
C204—C205—C206—C207	0 (5)	C18—N4—C23—N3	0.1 (3)
C205—C206—C207—S203	−1 (5)	C18—N4—C23—C204	179.0 (12)
C204—S203—C207—C206	1 (4)	C18—N4—C23—C24	179.8 (2)
C7—N2—C1—C6	179.3 (2)	C17—N3—C23—N4	0.2 (3)
C7—N2—C1—C2	0.6 (2)	C28—N3—C23—N4	174.0 (2)
C7—N1—C2—C3	−177.6 (2)	C17—N3—C23—C204	−178.8 (12)
C12—N1—C2—C3	−3.6 (4)	C28—N3—C23—C204	−5.0 (12)
C7—N1—C2—C1	0.8 (2)	C17—N3—C23—C24	−179.5 (2)
C12—N1—C2—C1	174.8 (2)	C28—N3—C23—C24	−5.7 (4)
N2—C1—C2—N1	−0.9 (2)	C205—C204—C23—N4	−33 (2)
C6—C1—C2—N1	−179.8 (2)	S203—C204—C23—N4	146.3 (13)
N2—C1—C2—C3	177.7 (2)	C205—C204—C23—N3	146 (2)
C6—C1—C2—C3	−1.2 (3)	S203—C204—C23—N3	−35 (2)
N1—C2—C3—C4	178.1 (2)	C205—C204—C23—C24	−70.80
C1—C2—C3—C4	0.0 (3)	S203—C204—C23—C24	110.80
C2—C3—C4—C5	1.3 (3)	C25—C24—C23—N4	141.0 (4)
C2—C3—C4—Cl11	−170.1 (6)	S3—C24—C23—N4	−33.6 (3)
C3—C4—C5—C6	−1.4 (4)	C25—C24—C23—N3	−39.4 (5)
Cl11—C4—C5—C6	172.3 (5)	S3—C24—C23—N3	146.1 (2)
C3—C4—C5—Cl1	177.54 (19)	C25—C24—C23—C204	−80.80
Cl11—C4—C5—Cl1	−8.8 (5)	S3—C24—C23—C204	110.80
C4—C5—C6—C1	0.1 (3)	C23—N3—C28—C29	96.9 (3)
Cl1—C5—C6—C1	−178.77 (17)	C17—N3—C28—C29	−90.3 (3)
N2—C1—C6—C5	−177.5 (2)	N1—C12—C13—C14	132.0 (2)
C2—C1—C6—C5	1.1 (3)	N1—C12—C13—S2	−52.9 (2)
C1—N2—C7—N1	−0.1 (3)	C16—S2—C13—C14	−1.03 (17)
C1—N2—C7—C208	−179.4 (12)	C16—S2—C13—C12	−176.80 (18)
C1—N2—C7—C8	179.5 (2)	C12—C13—C14—C15	176.60 (19)
C2—N1—C7—N2	−0.5 (3)	S2—C13—C14—C15	1.1 (2)
C12—N1—C7—N2	−174.1 (2)	C13—C14—C15—C16	−0.6 (3)
C2—N1—C7—C208	178.9 (13)	C14—C15—C16—S2	−0.2 (3)
C12—N1—C7—C208	5.3 (13)	C13—S2—C16—C15	0.73 (19)
C2—N1—C7—C8	179.9 (2)	N3—C28—C29—C30	−131.2 (2)
C12—N1—C7—C8	6.4 (4)	N3—C28—C29—S4	53.8 (2)
C209—C208—C7—N2	41 (2)	C32—S4—C29—C30	1.10 (18)
S201—C208—C7—N2	−140.1 (12)	C32—S4—C29—C28	176.82 (18)
C209—C208—C7—N1	−138 (2)	C28—C29—C30—C31	−176.18 (19)
S201—C208—C7—N1	41 (2)	S4—C29—C30—C31	−0.7 (2)
C209—C208—C7—C8	180.100	C29—C30—C31—C32	−0.3 (3)
S201—C208—C7—C8	0.40	C30—C31—C32—S4	1.1 (3)
C9—C8—C7—N2	−138.1 (4)	C29—S4—C32—C31	−1.3 (2)
S1—C8—C7—N2	36.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N2	0.95	2.68	3.581 (3)	159
C28—H28B···N2	0.99	2.58	3.460 (3)	148
C3i—H3i···N4	0.95	2.68	3.584 (3)	159
C12i—H12Ai···N4	0.99	2.62	3.514 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯N2	0.95	2.68	3.581 (3)	159
C28—H28B⋯N2	0.99	2.58	3.460 (3)	148
C3i—H3i⋯N4	0.95	2.68	3.584 (3)	159
C12i—H12A i⋯N4	0.99	2.62	3.514 (3)	150

Symmetry code: (i) .