5,6-Dimethyl-2-(5-methyl-thio-phen-2-yl)-1-[(5-methyl-thio-phen-2-yl)meth-yl]-1H-benzimidazole.

The title mol-ecule, C20H20N2S2, is T-shaped and consists of a nearly flat 5,6-dimethyl-2-(5-methyl-thio-phen-2-yl)benzimidazole system approximately perpendicular to the 5-methyl-thio-phen-2-ylmethyl substituent. The 5,6-dimethyl-2-(5-meth-yl-thio-phen-2-yl)benzimidazole system is rotationally disordered about the two imidazole N atoms as approximated by a twofold rotation axis with a refined major/minor occupancy ratio of 0.884 (2):0.116 (2). The benzimidazole ring system is essentially planar, the largest deviations being 0.026 (2) and 0.044 (18) Å in the major and minor components, respectively. The inter-planar angles between the benzimidazole unit and the 5-methyl-thio-phen-2-yl substituent are 10.8 (3) and 8(3)° in the major and minor components, respectively, and the corresponding angles with the 5-methyl-thio-phen-2-ylmethyl substituent are 88.12 (8) and 89.5 (4)°. In the crystal, mol-ecules are oriented with their 2-(5-methyl-thio-phen-2-yl)benzimidazole mean planes approximately parallel to (11[Formula: see text]) and appear to be held together by π-π [2-thiophene⋯imidazole centroid-centroid distance = 4.1383 (7) Å] and C-H⋯π contacts. A weak C-H⋯N hydrogen bond generates infinite chains parallel to [100].

Related literature

For the structure of 5,6-di­methyl­benzimidazole, see: Lee & Scheidt (1986 ▶). For the structure of 2-(thio­phen-2-yl)-1-(thio­phen-2-ylmeth­yl)-1H-benzimidazole, see: Geiger et al. (2012 ▶). For the 5-chloro derivative, see: Geiger & Nellist (2013a ▶), the 6-chloro derivative, see: Geiger & Nellist (2013b ▶) and the 6-bromo derivative, see: Geiger & Destefano (2012 ▶). Reich et al. (2004 ▶) provide examples of benzimidazole synthesis via inter­molecular aldimine coupling. For a discussion of the biological activity of benzimidazole derivatives, see: López-Rodríguez et al. (1999 ▶); Horton et al. (2003 ▶).

Experimental

Crystal data

C20H20N2S2

M = 352.50

Triclinic,

a = 6.4453 (11) Å

b = 10.0228 (18) Å

c = 14.249 (3) Å

α = 79.171 (5)°

β = 83.694 (5)°

γ = 83.625 (6)°

V = 894.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 200 K

0.40 × 0.40 × 0.40 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.60, T max = 0.89

10964 measured reflections

3121 independent reflections

2420 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.03

3121 reflections

276 parameters

47 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814006333/qk2065sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006333/qk2065Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006333/qk2065Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006333/qk2065Isup4.cml

CCDC reference: 993009

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H20N2S2	Z = 2
Mr = 352.50	F(000) = 372
Triclinic, P1	Dx = 1.308 Mg m−3
a = 6.4453 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0228 (18) Å	Cell parameters from 6329 reflections
c = 14.249 (3) Å	θ = 2.3–24.9°
α = 79.171 (5)°	µ = 0.30 mm−1
β = 83.694 (5)°	T = 200 K
γ = 83.625 (6)°	Block, yellow
V = 894.8 (3) Å3	0.40 × 0.40 × 0.40 mm

Bruker SMART X2S benchtop diffractometer	3121 independent reflections
Radiation source: XOS X-beam microfocus source	2420 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.037
ω scans	θmax = 25.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −7→7
Tmin = 0.60, Tmax = 0.89	k = −11→11
10964 measured reflections	l = −16→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.397P] where P = (Fo2 + 2Fc2)/3
3121 reflections	(Δ/σ)max < 0.001
276 parameters	Δρmax = 0.26 e Å−3
47 restraints	Δρmin = −0.30 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	Occ. (<1)
C1	0.9366 (4)	0.2289 (3)	0.2305 (2)	0.0381 (7)	0.884 (2)
C2	0.7398 (4)	0.2498 (3)	0.19474 (18)	0.0373 (6)	0.884 (2)
C3	0.6040 (8)	0.3653 (6)	0.2051 (5)	0.0429 (12)	0.884 (2)
H3	0.473	0.3818	0.1783	0.052*	0.884 (2)
C4	0.6713 (5)	0.4579 (3)	0.2581 (2)	0.0449 (8)	0.884 (2)
C5	0.8692 (6)	0.4337 (4)	0.2962 (3)	0.0465 (9)	0.884 (2)
C6	1.0024 (9)	0.3197 (8)	0.2824 (7)	0.0454 (8)	0.884 (2)
H6	1.1353	0.3033	0.3075	0.054*	0.884 (2)
C41	0.5284 (6)	0.5834 (4)	0.2728 (3)	0.0626 (10)	0.884 (2)
H41A	0.3988	0.584	0.2426	0.094*	0.884 (2)
H41B	0.5986	0.6651	0.2436	0.094*	0.884 (2)
H41C	0.4951	0.5827	0.3416	0.094*	0.884 (2)
C51	0.9359 (6)	0.5297 (4)	0.3547 (2)	0.0683 (10)	0.884 (2)
H51A	0.845	0.5256	0.4148	0.102*	0.884 (2)
H51B	0.9244	0.623	0.3182	0.102*	0.884 (2)
H51C	1.0815	0.5029	0.369	0.102*	0.884 (2)
N1	1.0278 (3)	0.1079 (2)	0.20560 (15)	0.0366 (6)	0.884 (2)
C7	0.8828 (4)	0.0601 (3)	0.15921 (17)	0.0358 (6)	0.884 (2)
N2	0.7102 (5)	0.1432 (3)	0.1501 (3)	0.0376 (7)	0.884 (2)
C8	0.9077 (4)	−0.0691 (3)	0.1266 (2)	0.0384 (7)	0.884 (2)
C9	1.0526 (6)	−0.1817 (4)	0.1428 (2)	0.0522 (12)	0.884 (2)
H9	1.1686	−0.1863	0.1794	0.063*	0.884 (2)
C10	1.0088 (6)	−0.2882 (4)	0.0990 (3)	0.0586 (11)	0.884 (2)
H10	1.0942	−0.3723	0.1028	0.07*	0.884 (2)
C11	0.8341 (5)	−0.2615 (4)	0.0507 (2)	0.0492 (8)	0.884 (2)
S1	0.72042 (12)	−0.10176 (9)	0.05845 (6)	0.0447 (3)	0.884 (2)
C61	0.7391 (6)	−0.3515 (4)	−0.0025 (3)	0.0652 (10)	0.884 (2)
H61C	0.8254	−0.3586	−0.0627	0.098*	0.884 (2)
H61A	0.5973	−0.3124	−0.0165	0.098*	0.884 (2)
H61B	0.7324	−0.4425	0.037	0.098*	0.884 (2)
C201	0.978 (3)	−0.058 (2)	0.1416 (17)	0.0381 (7)	0.116 (2)
C202	0.775 (3)	−0.0185 (17)	0.1147 (13)	0.0373 (6)	0.116 (2)
C203	0.653 (4)	−0.098 (3)	0.073 (2)	0.0429 (12)	0.116 (2)
H203	0.5116	−0.0714	0.0591	0.052*	0.116 (2)
C204	0.769 (4)	−0.224 (3)	0.054 (2)	0.0449 (8)	0.116 (2)
C205	0.980 (4)	−0.263 (2)	0.072 (2)	0.0465 (9)	0.116 (2)
C206	1.079 (4)	−0.178 (3)	0.116 (2)	0.0454 (8)	0.116 (2)
H206	1.2211	−0.203	0.1294	0.054*	0.116 (2)
C241	0.655 (5)	−0.313 (3)	0.005 (3)	0.0626 (10)	0.116 (2)
H24A	0.5239	−0.2625	−0.0162	0.094*	0.116 (2)
H24B	0.6226	−0.3958	0.0506	0.094*	0.116 (2)
H24C	0.7437	−0.3376	−0.0505	0.094*	0.116 (2)
C251	1.108 (4)	−0.392 (2)	0.0553 (19)	0.0683 (10)	0.116 (2)
H25A	1.2486	−0.3923	0.0761	0.102*	0.116 (2)
H25B	1.1202	−0.3962	−0.0131	0.102*	0.116 (2)
H25C	1.0405	−0.4704	0.0921	0.102*	0.116 (2)
N201	1.034 (2)	0.0443 (17)	0.1869 (13)	0.0366 (6)	0.116 (2)
C207	0.865 (3)	0.1387 (16)	0.1827 (13)	0.0358 (6)	0.116 (2)
N202	0.704 (4)	0.104 (3)	0.147 (3)	0.0376 (7)	0.116 (2)
C208	0.859 (3)	0.258 (2)	0.2257 (18)	0.0384 (7)	0.116 (2)
C209	0.999 (8)	0.305 (7)	0.277 (7)	0.0522 (12)	0.116 (2)
H209	1.1339	0.2609	0.2893	0.063*	0.116 (2)
C210	0.914 (6)	0.425 (4)	0.309 (4)	0.0586 (11)	0.116 (2)
H210	0.9855	0.4688	0.3481	0.07*	0.116 (2)
C211	0.724 (5)	0.475 (3)	0.280 (2)	0.0492 (8)	0.116 (2)
S201	0.644 (2)	0.3748 (17)	0.2127 (12)	0.0447 (3)	0.116 (2)
C261	0.592 (5)	0.606 (3)	0.295 (2)	0.0652 (10)	0.116 (2)
H26A	0.4495	0.5851	0.3204	0.098*	0.116 (2)
H26B	0.5866	0.6687	0.2331	0.098*	0.116 (2)
H26C	0.6544	0.6485	0.34	0.098*	0.116 (2)
C12	1.2465 (3)	0.0569 (3)	0.21561 (16)	0.0415 (6)
H12A	1.3325	0.1352	0.2052	0.05*
H12B	1.2956	0.0014	0.1655	0.05*
C13	1.2791 (3)	−0.0285 (2)	0.31259 (15)	0.0373 (5)
C14	1.1370 (4)	−0.0773 (3)	0.38263 (18)	0.0579 (8)
H14	0.9901	−0.0631	0.3777	0.069*
C15	1.2288 (4)	−0.1530 (3)	0.46544 (18)	0.0588 (8)
H15	1.1487	−0.1949	0.521	0.071*
C16	1.4376 (4)	−0.1594 (3)	0.45742 (16)	0.0446 (6)
S2	1.52848 (9)	−0.07226 (7)	0.34707 (4)	0.0434 (2)
C71	1.5901 (5)	−0.2263 (3)	0.52863 (18)	0.0596 (8)
H71B	1.513	−0.2596	0.5902	0.089*
H71C	1.6838	−0.1597	0.5373	0.089*
H71A	1.673	−0.303	0.5048	0.089*

	U11	U22	U33	U12	U13	U23
C1	0.0329 (16)	0.0515 (18)	0.0243 (13)	−0.0065 (13)	−0.0050 (13)	0.0103 (12)
C2	0.0303 (14)	0.0493 (16)	0.0253 (13)	−0.0046 (12)	−0.0030 (11)	0.0117 (11)
C3	0.042 (3)	0.052 (2)	0.034 (2)	−0.003 (2)	−0.0122 (19)	−0.0002 (14)
C4	0.052 (2)	0.0523 (18)	0.0265 (17)	−0.0064 (15)	−0.0026 (12)	0.0042 (13)
C5	0.055 (3)	0.0557 (19)	0.0268 (19)	−0.0138 (19)	−0.0042 (16)	0.0024 (15)
C6	0.0436 (16)	0.066 (3)	0.023 (2)	−0.0082 (16)	−0.0055 (12)	0.0039 (17)
C41	0.070 (3)	0.062 (2)	0.055 (2)	0.0029 (18)	−0.0082 (17)	−0.0137 (17)
C51	0.082 (2)	0.077 (2)	0.049 (2)	−0.0076 (19)	−0.0123 (18)	−0.0167 (17)
N1	0.0297 (11)	0.0525 (16)	0.0247 (12)	−0.0061 (11)	−0.0048 (9)	0.0029 (10)
C7	0.0302 (13)	0.0514 (17)	0.0210 (13)	−0.0071 (12)	−0.0036 (10)	0.0081 (11)
N2	0.0299 (11)	0.048 (2)	0.0298 (11)	−0.0043 (13)	−0.0057 (8)	0.0071 (17)
C8	0.0327 (17)	0.0553 (17)	0.0235 (14)	−0.0060 (14)	−0.0049 (12)	0.0052 (12)
C9	0.050 (2)	0.063 (2)	0.041 (3)	0.0093 (16)	−0.0188 (19)	−0.0037 (18)
C10	0.061 (2)	0.061 (2)	0.053 (3)	0.0119 (17)	−0.0163 (17)	−0.0114 (18)
C11	0.055 (2)	0.063 (2)	0.0258 (14)	−0.0114 (15)	−0.0017 (17)	0.0022 (15)
S1	0.0416 (5)	0.0579 (5)	0.0325 (5)	−0.0058 (4)	−0.0125 (4)	0.0036 (3)
C61	0.084 (3)	0.072 (3)	0.0420 (19)	−0.015 (2)	−0.012 (2)	−0.0070 (18)
C201	0.0329 (16)	0.0515 (18)	0.0243 (13)	−0.0065 (13)	−0.0050 (13)	0.0103 (12)
C202	0.0303 (14)	0.0493 (16)	0.0253 (13)	−0.0046 (12)	−0.0030 (11)	0.0117 (11)
C203	0.042 (3)	0.052 (2)	0.034 (2)	−0.003 (2)	−0.0122 (19)	−0.0002 (14)
C204	0.052 (2)	0.0523 (18)	0.0265 (17)	−0.0064 (15)	−0.0026 (12)	0.0042 (13)
C205	0.055 (3)	0.0557 (19)	0.0268 (19)	−0.0138 (19)	−0.0042 (16)	0.0024 (15)
C206	0.0436 (16)	0.066 (3)	0.023 (2)	−0.0082 (16)	−0.0055 (12)	0.0039 (17)
C241	0.070 (3)	0.062 (2)	0.055 (2)	0.0029 (18)	−0.0082 (17)	−0.0137 (17)
C251	0.082 (2)	0.077 (2)	0.049 (2)	−0.0076 (19)	−0.0123 (18)	−0.0167 (17)
N201	0.0297 (11)	0.0525 (16)	0.0247 (12)	−0.0061 (11)	−0.0048 (9)	0.0029 (10)
C207	0.0302 (13)	0.0514 (17)	0.0210 (13)	−0.0071 (12)	−0.0036 (10)	0.0081 (11)
N202	0.0299 (11)	0.048 (2)	0.0298 (11)	−0.0043 (13)	−0.0057 (8)	0.0071 (17)
C208	0.0327 (17)	0.0553 (17)	0.0235 (14)	−0.0060 (14)	−0.0049 (12)	0.0052 (12)
C209	0.050 (2)	0.063 (2)	0.041 (3)	0.0093 (16)	−0.0188 (19)	−0.0037 (18)
C210	0.061 (2)	0.061 (2)	0.053 (3)	0.0119 (17)	−0.0163 (17)	−0.0114 (18)
C211	0.055 (2)	0.063 (2)	0.0258 (14)	−0.0114 (15)	−0.0017 (17)	0.0022 (15)
S201	0.0416 (5)	0.0579 (5)	0.0325 (5)	−0.0058 (4)	−0.0125 (4)	0.0036 (3)
C261	0.084 (3)	0.072 (3)	0.0420 (19)	−0.015 (2)	−0.012 (2)	−0.0070 (18)
C12	0.0289 (12)	0.0621 (16)	0.0289 (12)	−0.0047 (11)	−0.0071 (10)	0.0067 (11)
C13	0.0326 (12)	0.0502 (14)	0.0269 (12)	−0.0030 (10)	−0.0071 (10)	0.0011 (10)
C14	0.0376 (14)	0.091 (2)	0.0374 (14)	−0.0103 (14)	−0.0063 (12)	0.0137 (14)
C15	0.0536 (17)	0.083 (2)	0.0293 (14)	−0.0117 (15)	−0.0015 (12)	0.0181 (13)
C16	0.0531 (16)	0.0521 (15)	0.0250 (12)	−0.0016 (12)	−0.0086 (11)	0.0034 (10)
S2	0.0351 (4)	0.0610 (4)	0.0287 (3)	−0.0006 (3)	−0.0088 (2)	0.0068 (3)
C71	0.0706 (19)	0.0691 (19)	0.0331 (14)	0.0073 (15)	−0.0167 (13)	0.0052 (13)

C1—N1	1.379 (4)	C204—C205	1.413 (17)
C1—C2	1.399 (4)	C204—C241	1.515 (18)
C1—C6	1.400 (5)	C205—C206	1.390 (19)
C2—N2	1.382 (4)	C205—C251	1.500 (18)
C2—C3	1.392 (7)	C206—H206	0.95
C3—C4	1.429 (6)	C241—H24A	0.98
C3—H3	0.95	C241—H24B	0.98
C4—C5	1.419 (4)	C241—H24C	0.98
C4—C41	1.508 (4)	C251—H25A	0.98
C5—C6	1.382 (5)	C251—H25B	0.98
C5—C51	1.509 (5)	C251—H25C	0.98
C6—H6	0.95	N201—C207	1.357 (15)
C41—H41A	0.98	N201—C12	1.498 (15)
C41—H41B	0.98	C207—N202	1.312 (16)
C41—H41C	0.98	C207—C208	1.435 (16)
C51—H51A	0.98	C208—C209	1.393 (19)
C51—H51B	0.98	C208—S201	1.716 (17)
C51—H51C	0.98	C209—C210	1.40 (2)
N1—C7	1.377 (3)	C209—H209	0.95
N1—C12	1.458 (3)	C210—C211	1.351 (18)
C7—N2	1.317 (4)	C210—H210	0.95
C7—C8	1.443 (4)	C211—C261	1.516 (18)
C8—C9	1.384 (4)	C211—S201	1.666 (17)
C8—S1	1.723 (3)	C261—H26A	0.98
C9—C10	1.402 (5)	C261—H26B	0.98
C9—H9	0.95	C261—H26C	0.98
C10—C11	1.359 (5)	C12—C13	1.505 (3)
C10—H10	0.95	C12—H12A	0.99
C11—C61	1.498 (4)	C12—H12B	0.99
C11—S1	1.703 (4)	C13—C14	1.338 (3)
C61—H61C	0.98	C13—S2	1.718 (2)
C61—H61A	0.98	C14—C15	1.426 (3)
C61—H61B	0.98	C14—H14	0.95
C201—C206	1.396 (18)	C15—C16	1.333 (4)
C201—C202	1.397 (16)	C15—H15	0.95
C201—N201	1.406 (16)	C16—C71	1.504 (3)
C202—N202	1.403 (18)	C16—S2	1.724 (2)
C202—C203	1.425 (17)	C71—H71B	0.98
C203—C204	1.450 (18)	C71—H71C	0.98
C203—H203	0.95	C71—H71A	0.98
N1—C1—C2	105.5 (2)	C206—C205—C251	114.9 (18)
N1—C1—C6	132.9 (3)	C204—C205—C251	127.0 (18)
C2—C1—C6	121.6 (3)	C205—C206—C201	122 (2)
N2—C2—C3	128.4 (3)	C205—C206—H206	118.9
N2—C2—C1	110.1 (2)	C201—C206—H206	118.9
C3—C2—C1	121.5 (3)	C204—C241—H24A	109.5
C2—C3—C4	116.8 (3)	C204—C241—H24B	109.5
C2—C3—H3	121.6	H24A—C241—H24B	109.5
C4—C3—H3	121.6	C204—C241—H24C	109.5
C5—C4—C3	121.2 (4)	H24A—C241—H24C	109.5
C5—C4—C41	120.0 (3)	H24B—C241—H24C	109.5
C3—C4—C41	118.8 (3)	C205—C251—H25A	109.5
C6—C5—C4	120.5 (3)	C205—C251—H25B	109.5
C6—C5—C51	118.7 (3)	H25A—C251—H25B	109.5
C4—C5—C51	120.8 (3)	C205—C251—H25C	109.5
C5—C6—C1	118.4 (4)	H25A—C251—H25C	109.5
C5—C6—H6	120.8	H25B—C251—H25C	109.5
C1—C6—H6	120.8	C207—N201—C201	104.4 (13)
C4—C41—H41A	109.5	C207—N201—C12	128.0 (13)
C4—C41—H41B	109.5	C201—N201—C12	126.7 (13)
H41A—C41—H41B	109.5	N202—C207—N201	114.7 (14)
C4—C41—H41C	109.5	N202—C207—C208	123.7 (15)
H41A—C41—H41C	109.5	N201—C207—C208	121.2 (14)
H41B—C41—H41C	109.5	C207—N202—C202	105.3 (15)
C5—C51—H51A	109.5	C209—C208—C207	133.4 (18)
C5—C51—H51B	109.5	C209—C208—S201	108.7 (15)
H51A—C51—H51B	109.5	C207—C208—S201	117.9 (15)
C5—C51—H51C	109.5	C208—C209—C210	111 (2)
H51A—C51—H51C	109.5	C208—C209—H209	124.3
H51B—C51—H51C	109.5	C210—C209—H209	124.3
C7—N1—C1	106.5 (2)	C211—C210—C209	115 (2)
C7—N1—C12	128.7 (2)	C211—C210—H210	122.5
C1—N1—C12	124.2 (2)	C209—C210—H210	122.5
N2—C7—N1	112.8 (3)	C210—C211—C261	130 (2)
N2—C7—C8	122.1 (2)	C210—C211—S201	110.0 (15)
N1—C7—C8	125.1 (2)	C261—C211—S201	120.0 (18)
C7—N2—C2	105.1 (2)	C211—S201—C208	94.6 (11)
C9—C8—C7	132.5 (3)	C211—C261—H26A	109.5
C9—C8—S1	109.7 (3)	C211—C261—H26B	109.5
C7—C8—S1	117.7 (2)	H26A—C261—H26B	109.5
C8—C9—C10	112.3 (3)	C211—C261—H26C	109.5
C8—C9—H9	123.8	H26A—C261—H26C	109.5
C10—C9—H9	123.8	H26B—C261—H26C	109.5
C11—C10—C9	114.6 (3)	N1—C12—C13	112.70 (19)
C11—C10—H10	122.7	N201—C12—C13	110.9 (7)
C9—C10—H10	122.7	N1—C12—H12A	109.1
C10—C11—C61	129.0 (3)	C13—C12—H12A	109.1
C10—C11—S1	110.1 (3)	N1—C12—H12B	109.1
C61—C11—S1	120.9 (3)	C13—C12—H12B	109.1
C11—S1—C8	93.33 (15)	H12A—C12—H12B	107.8
C11—C61—H61C	109.5	C14—C13—C12	129.4 (2)
C11—C61—H61A	109.5	C14—C13—S2	110.64 (18)
H61C—C61—H61A	109.5	C12—C13—S2	119.96 (16)
C11—C61—H61B	109.5	C13—C14—C15	113.1 (2)
H61C—C61—H61B	109.5	C13—C14—H14	123.5
H61A—C61—H61B	109.5	C15—C14—H14	123.5
C206—C201—C202	117.6 (16)	C16—C15—C14	113.6 (2)
C206—C201—N201	135.0 (17)	C16—C15—H15	123.2
C202—C201—N201	107.3 (13)	C14—C15—H15	123.2
C201—C202—N202	108.0 (13)	C15—C16—C71	129.8 (2)
C201—C202—C203	125.5 (15)	C15—C16—S2	110.34 (18)
N202—C202—C203	126.1 (15)	C71—C16—S2	119.9 (2)
C202—C203—C204	112.3 (17)	C13—S2—C16	92.37 (11)
C202—C203—H203	123.8	C16—C71—H71B	109.5
C204—C203—H203	123.8	C16—C71—H71C	109.5
C205—C204—C203	124.0 (17)	H71B—C71—H71C	109.5
C205—C204—C241	119.6 (17)	C16—C71—H71A	109.5
C203—C204—C241	116.2 (17)	H71B—C71—H71A	109.5
C206—C205—C204	118.0 (17)	H71C—C71—H71A	109.5
N1—C1—C2—N2	0.8 (3)	C241—C204—C205—C251	−5 (5)
C6—C1—C2—N2	−177.5 (6)	C204—C205—C206—C201	0 (5)
N1—C1—C2—C3	−178.7 (4)	C251—C205—C206—C201	−176 (3)
C6—C1—C2—C3	3.1 (7)	C202—C201—C206—C205	−5 (5)
N2—C2—C3—C4	177.7 (4)	N201—C201—C206—C205	179 (3)
C1—C2—C3—C4	−2.9 (7)	C206—C201—N201—C207	175 (3)
C2—C3—C4—C5	1.3 (8)	C202—C201—N201—C207	−1 (2)
C2—C3—C4—C41	−179.0 (4)	C206—C201—N201—C12	6 (5)
C3—C4—C5—C6	0.3 (9)	C202—C201—N201—C12	−170.8 (17)
C41—C4—C5—C6	−179.4 (7)	C201—N201—C207—N202	5 (3)
C3—C4—C5—C51	−178.0 (4)	C12—N201—C207—N202	174 (2)
C41—C4—C5—C51	2.3 (6)	C201—N201—C207—C208	177 (2)
C4—C5—C6—C1	−0.3 (12)	C12—N201—C207—C208	−13 (3)
C51—C5—C6—C1	178.1 (6)	N201—C207—N202—C202	−6 (4)
N1—C1—C6—C5	−179.0 (5)	C208—C207—N202—C202	−179 (2)
C2—C1—C6—C5	−1.4 (12)	C201—C202—N202—C207	5 (3)
C2—C1—N1—C7	−1.6 (3)	C203—C202—N202—C207	178 (3)
C6—C1—N1—C7	176.3 (7)	N202—C207—C208—C209	171 (7)
C2—C1—N1—C12	170.2 (2)	N201—C207—C208—C209	−1 (8)
C6—C1—N1—C12	−11.8 (8)	N202—C207—C208—S201	−11 (4)
C1—N1—C7—N2	2.1 (3)	N201—C207—C208—S201	177.4 (18)
C12—N1—C7—N2	−169.3 (3)	C207—C208—C209—C210	−177 (4)
C1—N1—C7—C8	−175.5 (2)	S201—C208—C209—C210	5 (9)
C12—N1—C7—C8	13.1 (4)	C208—C209—C210—C211	−3 (11)
N1—C7—N2—C2	−1.6 (4)	C209—C210—C211—C261	−176 (6)
C8—C7—N2—C2	176.1 (3)	C209—C210—C211—S201	0 (8)
C3—C2—N2—C7	179.8 (4)	C210—C211—S201—C208	3 (4)
C1—C2—N2—C7	0.5 (4)	C261—C211—S201—C208	179 (3)
N2—C7—C8—C9	−166.6 (4)	C209—C208—S201—C211	−4 (5)
N1—C7—C8—C9	10.7 (5)	C207—C208—S201—C211	177 (2)
N2—C7—C8—S1	9.6 (4)	C7—N1—C12—N201	−9.2 (15)
N1—C7—C8—S1	−173.04 (19)	C1—N1—C12—N201	−179.2 (17)
C7—C8—C9—C10	177.2 (3)	C7—N1—C12—C13	−101.5 (3)
S1—C8—C9—C10	0.8 (4)	C1—N1—C12—C13	88.5 (3)
C8—C9—C10—C11	−0.6 (5)	C207—N201—C12—N1	8.3 (10)
C9—C10—C11—C61	−178.8 (4)	C201—N201—C12—N1	176 (3)
C9—C10—C11—S1	0.2 (4)	C207—N201—C12—C13	107.7 (18)
C10—C11—S1—C8	0.2 (3)	C201—N201—C12—C13	−85 (2)
C61—C11—S1—C8	179.3 (3)	N1—C12—C13—C14	10.1 (4)
C9—C8—S1—C11	−0.6 (3)	N201—C12—C13—C14	−20.7 (7)
C7—C8—S1—C11	−177.6 (2)	N1—C12—C13—S2	−168.13 (18)
C206—C201—C202—N202	−180 (3)	N201—C12—C13—S2	161.1 (6)
N201—C201—C202—N202	−2 (3)	C12—C13—C14—C15	−179.1 (3)
C206—C201—C202—C203	8 (4)	S2—C13—C14—C15	−0.7 (3)
N201—C201—C202—C203	−175 (2)	C13—C14—C15—C16	0.6 (4)
C201—C202—C203—C204	−4 (4)	C14—C15—C16—C71	178.7 (3)
N202—C202—C203—C204	−176 (3)	C14—C15—C16—S2	−0.1 (3)
C202—C203—C204—C205	−1 (5)	C14—C13—S2—C16	0.6 (2)
C202—C203—C204—C241	−177 (3)	C12—C13—S2—C16	179.1 (2)
C203—C204—C205—C206	4 (5)	C15—C16—S2—C13	−0.3 (2)
C241—C204—C205—C206	180 (3)	C71—C16—S2—C13	−179.2 (2)
C203—C204—C205—C251	179 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N2i	0.99	2.48	3.195 (4)	129
C71—H71B···S201ii	0.98	2.94	3.912 (17)	170
C61—H61B···C3iii	0.98	2.88	3.793 (8)	155
C71—H71B···C4ii	0.98	2.89	3.815 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯N2i	0.99	2.48	3.195 (4)	129
C61—H61B⋯C3ii	0.98	2.88	3.793 (8)	155
C71—H71B⋯C4iii	0.98	2.89	3.815 (4)	157

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