5-Bromo-2-(thio-phen-2-yl)-1-(thio-phen-2-ylmeth-yl)-1H-benzimidazole.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(16)H(11)BrN(2)S(2). In the crystal, weak C-H⋯N hydrogen bonds and C-H⋯thio-phene ring inter-actions link the mol-ecules into chains along [100]. The structure exhibits disorder of the 2-thio-phen-2-yl substituent of one of the symmetry-unique mol-ecules with a major:minor component ratio of 0.914 (3):0.086 (3).

Related literature

For the characterization of 2-(thio­phen-2-yl)-1-(thio­phen-2-ylmeth­yl)-1H-benzimidazole, see: Geiger et al. (2012 ▶). For examples of pharmacological uses of benzimidazoles, see: López-Rodríguez et al. (1999 ▶); Varala et al. (2007 ▶); Horton et al. (2003 ▶). For the synthesis of substituted benzimidazoles, see: Grimmett (1997 ▶).

Experimental

Crystal data

C16H11BrN2S2

M = 375.30

Monoclinic,

a = 12.6753 (17) Å

b = 10.5413 (11) Å

c = 23.581 (3) Å

β = 100.878 (4)°

V = 3094.1 (6) Å3

Z = 8

Mo Kα radiation

μ = 2.92 mm−1

T = 200 K

0.60 × 0.20 × 0.10 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.46, T max = 0.76

19813 measured reflections

5581 independent reflections

4191 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.091

S = 1.02

5581 reflections

392 parameters

91 restraints

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.80 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: XSHELL (Bruker, 2004 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042146/lr2085sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042146/lr2085Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042146/lr2085Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042146/lr2085Isup4.cml

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

C16H11BrN2S2	F(000) = 1504
Mr = 375.30	Dx = 1.611 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.6753 (17) Å	Cell parameters from 6104 reflections
b = 10.5413 (11) Å	θ = 2.5–24.4°
c = 23.581 (3) Å	µ = 2.92 mm−1
β = 100.878 (4)°	T = 200 K
V = 3094.1 (6) Å3	Plate, colourless
Z = 8	0.60 × 0.20 × 0.10 mm

Bruker SMART X2S benchtop diffractometer	5581 independent reflections
Radiation source: XOS X-beam microfocus source	4191 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.059
Detector resolution: 8.3330 pixels mm-1	θmax = 25.4°, θmin = 2.1°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	k = −12→12
Tmin = 0.46, Tmax = 0.76	l = −28→24
19813 measured reflections

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) = 0.091	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.036P)2 + 0.884P] where P = (Fo2 + 2Fc2)/3
5581 reflections	(Δ/σ)max = 0.001
392 parameters	Δρmax = 0.65 e Å−3
91 restraints	Δρmin = −0.80 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)
Br1	0.75134 (3)	1.11709 (4)	0.458735 (16)	0.05101 (14)
Br2	0.11272 (3)	1.13960 (3)	0.03496 (14)	0.03685 (12)
S1	0.41783 (7)	0.73442 (9)	0.17228 (4)	0.0370 (2)
S2	0.81366 (8)	1.15655 (8)	0.16253 (4)	0.0354 (2)
S3	−0.03440 (10)	0.73244 (14)	0.31444 (5)	0.0301 (3)	0.914 (3)
C24	0.0711 (5)	0.8382 (6)	0.32690 (16)	0.0225 (9)	0.914 (3)
C25	0.1030 (6)	0.8601 (8)	0.3841 (3)	0.0350 (16)	0.914 (3)
H25	0.1597	0.9164	0.3994	0.042*	0.914 (3)
C26	0.0435 (4)	0.7907 (4)	0.41889 (18)	0.0348 (12)	0.914 (3)
H26	0.0558	0.795	0.4598	0.042*	0.914 (3)
C27	−0.0325 (4)	0.7179 (4)	0.38673 (17)	0.0331 (11)	0.914 (3)
H27	−0.0798	0.6643	0.4026	0.04*	0.914 (3)
S300	0.118 (2)	0.872 (3)	0.3950 (10)	0.0301 (3)	0.086 (3)
C240	0.062 (5)	0.846 (7)	0.3243 (10)	0.0225 (9)	0.086 (3)
C250	−0.013 (4)	0.753 (6)	0.3166 (15)	0.0350 (16)	0.086 (3)
H250	−0.0504	0.7253	0.2801	0.042*	0.086 (3)
C260	−0.028 (4)	0.702 (5)	0.3704 (17)	0.0348 (12)	0.086 (3)
H260	−0.08	0.6398	0.3741	0.042*	0.086 (3)
C270	0.041 (5)	0.753 (5)	0.4156 (15)	0.0331 (11)	0.086 (3)
H270	0.0454	0.7255	0.4544	0.04*	0.086 (3)
S4	0.36606 (8)	1.15559 (8)	0.33291 (4)	0.0359 (2)
C29	0.3469 (2)	1.0042 (3)	0.35642 (13)	0.0243 (7)
C30	0.37895 (19)	0.9943 (2)	0.41524 (11)	0.0290 (8)
H30	0.3759	0.9179	0.4363	0.035*
C31	0.41740 (19)	1.1124 (2)	0.44115 (11)	0.0372 (9)
H31	0.4422	1.1238	0.4814	0.045*
C32	0.4144 (3)	1.2058 (3)	0.40164 (15)	0.0383 (9)
H32	0.4367	1.2905	0.4111	0.046*
N1	0.6914 (2)	0.9247 (2)	0.21670 (11)	0.0237 (6)
N2	0.5457 (2)	0.9232 (3)	0.25919 (11)	0.0259 (6)
N3	0.2090 (2)	0.9262 (2)	0.27375 (11)	0.0232 (6)
N4	0.0354 (2)	0.9291 (2)	0.22968 (11)	0.0233 (6)
C1	0.7240 (2)	0.9759 (3)	0.27135 (13)	0.0222 (7)
C2	0.6323 (2)	0.9745 (3)	0.29708 (13)	0.0225 (7)
C3	0.6388 (3)	1.0186 (3)	0.35289 (14)	0.0272 (8)
H3	0.5777	1.0208	0.3708	0.033*
C4	0.7381 (3)	1.0590 (3)	0.38108 (13)	0.0279 (8)
C5	0.8299 (3)	1.0590 (3)	0.35640 (14)	0.0275 (8)
H5	0.8967	1.0864	0.3783	0.033*
C6	0.8232 (2)	1.0189 (3)	0.30016 (14)	0.0252 (7)
H6	0.8839	1.0208	0.2819	0.03*
C7	0.5840 (3)	0.8946 (3)	0.21240 (14)	0.0241 (7)
C8	0.5183 (2)	0.8366 (3)	0.16143 (14)	0.0266 (7)
C9	0.5175 (3)	0.8543 (3)	0.10299 (15)	0.0317 (8)
H9	0.5664	0.9071	0.088	0.038*
C10	0.4344 (3)	0.7835 (4)	0.06878 (16)	0.0420 (10)
H10	0.4213	0.7838	0.0278	0.05*
C11	0.3754 (3)	0.7156 (3)	0.09998 (16)	0.0399 (9)
H11	0.3168	0.6631	0.0834	0.048*
C12	0.7635 (3)	0.8988 (3)	0.17647 (13)	0.0252 (7)
H12A	0.7361	0.824	0.1528	0.03*
H12B	0.8352	0.8766	0.199	0.03*
C13	0.7760 (2)	1.0068 (3)	0.13666 (14)	0.0260 (8)
C14	0.7663 (3)	1.0014 (3)	0.07791 (14)	0.0310 (8)
H14	0.7466	0.9271	0.0557	0.037*
C15	0.7891 (3)	1.1198 (3)	0.05394 (16)	0.0369 (9)
H15	0.7866	1.1329	0.0139	0.044*
C16	0.8147 (3)	1.2113 (4)	0.09412 (17)	0.0408 (10)
H16	0.8314	1.2962	0.0855	0.049*
C17	0.2065 (2)	0.9796 (3)	0.21996 (13)	0.0228 (7)
C18	0.0977 (2)	0.9815 (3)	0.19334 (13)	0.0230 (7)
C19	0.0678 (3)	1.0299 (3)	0.13786 (14)	0.0251 (7)
H19	−0.0053	1.0341	0.1191	0.03*
C20	0.1492 (3)	1.0714 (3)	0.11131 (13)	0.0262 (7)
C21	0.2576 (3)	1.0675 (3)	0.13697 (14)	0.0283 (8)
H21	0.3104	1.0956	0.1161	0.034*
C22	0.2882 (3)	1.0226 (3)	0.19272 (14)	0.0273 (8)
H22	0.3614	1.0211	0.2115	0.033*
C23	0.1038 (2)	0.8981 (3)	0.27693 (14)	0.0226 (7)
C28	0.3078 (2)	0.8977 (3)	0.31505 (13)	0.0244 (7)
H28A	0.365	0.8763	0.2933	0.029*
H28B	0.2952	0.8218	0.3376	0.029*

	U11	U22	U33	U12	U13	U23
Br1	0.0473 (3)	0.0758 (3)	0.0317 (2)	−0.0111 (2)	0.01178 (18)	−0.0179 (2)
Br2	0.0475 (2)	0.0365 (2)	0.02852 (19)	0.00007 (17)	0.01243 (17)	0.00434 (16)
S1	0.0262 (5)	0.0372 (6)	0.0474 (6)	−0.0087 (4)	0.0061 (4)	−0.0036 (4)
S2	0.0361 (5)	0.0294 (5)	0.0426 (5)	−0.0005 (4)	0.0121 (4)	−0.0066 (4)
S3	0.0251 (7)	0.0301 (8)	0.0354 (6)	−0.0096 (4)	0.0067 (4)	0.0013 (4)
C24	0.016 (2)	0.021 (2)	0.0304 (17)	−0.0001 (16)	0.0044 (14)	0.0012 (14)
C25	0.027 (4)	0.044 (4)	0.035 (3)	−0.012 (2)	0.008 (3)	0.000 (3)
C26	0.035 (2)	0.040 (3)	0.030 (2)	−0.009 (2)	0.0067 (17)	0.0000 (19)
C27	0.027 (2)	0.039 (3)	0.035 (2)	−0.0082 (19)	0.011 (2)	0.007 (2)
S300	0.0251 (7)	0.0301 (8)	0.0354 (6)	−0.0096 (4)	0.0067 (4)	0.0013 (4)
C240	0.016 (2)	0.021 (2)	0.0304 (17)	−0.0001 (16)	0.0044 (14)	0.0012 (14)
C250	0.027 (4)	0.044 (4)	0.035 (3)	−0.012 (2)	0.008 (3)	0.000 (3)
C260	0.035 (2)	0.040 (3)	0.030 (2)	−0.009 (2)	0.0067 (17)	0.0000 (19)
C270	0.027 (2)	0.039 (3)	0.035 (2)	−0.0082 (19)	0.011 (2)	0.007 (2)
S4	0.0356 (5)	0.0281 (5)	0.0425 (5)	−0.0021 (4)	0.0030 (4)	0.0085 (4)
C29	0.0116 (16)	0.0272 (19)	0.0346 (18)	0.0006 (13)	0.0053 (14)	0.0074 (15)
C30	0.0213 (18)	0.027 (2)	0.039 (2)	−0.0034 (15)	0.0060 (15)	0.0092 (16)
C31	0.031 (2)	0.039 (2)	0.038 (2)	0.0003 (17)	−0.0014 (17)	−0.0018 (18)
C32	0.036 (2)	0.030 (2)	0.046 (2)	−0.0029 (17)	0.0019 (18)	−0.0006 (18)
N1	0.0152 (14)	0.0286 (15)	0.0279 (14)	−0.0007 (12)	0.0058 (11)	−0.0034 (12)
N2	0.0166 (15)	0.0289 (16)	0.0322 (15)	0.0000 (12)	0.0050 (12)	−0.0014 (12)
N3	0.0155 (14)	0.0252 (15)	0.0297 (14)	−0.0007 (11)	0.0061 (11)	0.0038 (12)
N4	0.0148 (14)	0.0265 (15)	0.0292 (14)	0.0007 (11)	0.0061 (12)	0.0019 (12)
C1	0.0171 (16)	0.0238 (18)	0.0266 (17)	0.0030 (14)	0.0067 (14)	−0.0006 (14)
C2	0.0165 (17)	0.0208 (18)	0.0302 (17)	0.0008 (14)	0.0045 (14)	0.0024 (14)
C3	0.0212 (18)	0.0292 (19)	0.0333 (18)	0.0021 (14)	0.0107 (15)	0.0007 (15)
C4	0.030 (2)	0.029 (2)	0.0252 (17)	0.0014 (15)	0.0072 (15)	−0.0043 (15)
C5	0.0208 (18)	0.0253 (19)	0.0352 (19)	−0.0024 (14)	0.0020 (15)	−0.0021 (15)
C6	0.0151 (16)	0.0267 (19)	0.0348 (18)	−0.0023 (14)	0.0074 (14)	−0.0028 (15)
C7	0.0183 (17)	0.0214 (18)	0.0325 (18)	0.0005 (14)	0.0044 (14)	0.0006 (14)
C8	0.0178 (17)	0.0275 (19)	0.0335 (18)	0.0000 (14)	0.0026 (14)	−0.0014 (15)
C9	0.0187 (18)	0.034 (2)	0.040 (2)	−0.0031 (15)	−0.0003 (15)	−0.0033 (16)
C10	0.034 (2)	0.053 (3)	0.037 (2)	0.0028 (19)	−0.0003 (18)	−0.0079 (19)
C11	0.025 (2)	0.042 (2)	0.050 (2)	−0.0056 (17)	−0.0014 (17)	−0.0116 (19)
C12	0.0171 (17)	0.0298 (19)	0.0306 (18)	0.0018 (14)	0.0093 (14)	−0.0056 (15)
C13	0.0165 (17)	0.0286 (19)	0.0343 (19)	0.0028 (14)	0.0085 (15)	−0.0044 (15)
C14	0.0251 (19)	0.033 (2)	0.0362 (19)	−0.0008 (15)	0.0101 (15)	−0.0055 (16)
C15	0.034 (2)	0.044 (2)	0.034 (2)	0.0089 (17)	0.0108 (17)	0.0057 (18)
C16	0.039 (2)	0.032 (2)	0.056 (2)	0.0057 (18)	0.0203 (19)	0.007 (2)
C17	0.0191 (17)	0.0190 (17)	0.0311 (17)	−0.0001 (13)	0.0067 (14)	−0.0001 (14)
C18	0.0173 (17)	0.0217 (18)	0.0314 (18)	0.0012 (14)	0.0081 (14)	−0.0014 (14)
C19	0.0192 (17)	0.0238 (18)	0.0338 (18)	0.0019 (14)	0.0090 (14)	−0.0020 (15)
C20	0.032 (2)	0.0222 (18)	0.0269 (17)	0.0025 (15)	0.0111 (15)	−0.0013 (14)
C21	0.0270 (19)	0.0242 (19)	0.0378 (19)	−0.0022 (15)	0.0167 (16)	0.0000 (16)
C22	0.0184 (17)	0.0248 (19)	0.0404 (19)	−0.0018 (14)	0.0099 (15)	0.0005 (16)
C23	0.0169 (16)	0.0198 (18)	0.0325 (18)	−0.0020 (13)	0.0085 (14)	−0.0005 (14)
C28	0.0171 (17)	0.0234 (18)	0.0327 (18)	0.0005 (14)	0.0047 (14)	0.0066 (14)

Br1—C4	1.908 (3)	N3—C28	1.465 (4)
Br2—C20	1.912 (3)	N4—C23	1.317 (4)
S1—C11	1.700 (4)	N4—C18	1.384 (4)
S1—C8	1.723 (3)	C1—C6	1.387 (4)
S2—C16	1.716 (4)	C1—C2	1.409 (4)
S2—C13	1.727 (3)	C2—C3	1.384 (4)
S3—C27	1.707 (4)	C3—C4	1.376 (4)
S3—C24	1.723 (4)	C3—H3	0.95
C24—C25	1.352 (6)	C4—C5	1.396 (4)
C24—C23	1.464 (4)	C5—C6	1.379 (4)
C25—C26	1.417 (7)	C5—H5	0.95
C25—H25	0.95	C6—H6	0.95
C26—C27	1.348 (5)	C7—C8	1.461 (4)
C26—H26	0.95	C8—C9	1.389 (5)
C27—H27	0.95	C9—C10	1.412 (5)
S300—C240	1.707 (17)	C9—H9	0.95
S300—C270	1.721 (17)	C10—C11	1.349 (5)
C240—C250	1.353 (17)	C10—H10	0.95
C240—C23	1.430 (17)	C11—H11	0.95
C250—C260	1.422 (17)	C12—C13	1.503 (4)
C250—H250	0.95	C12—H12A	0.99
C260—C270	1.349 (16)	C12—H12B	0.99
C260—H260	0.95	C13—C14	1.369 (4)
C270—H270	0.95	C14—C15	1.422 (5)
S4—C32	1.705 (4)	C14—H14	0.95
S4—C29	1.722 (3)	C15—C16	1.348 (5)
C29—C30	1.374 (4)	C15—H15	0.95
C29—C28	1.509 (4)	C16—H16	0.95
C30—C31	1.4313	C17—C22	1.393 (4)
C30—H30	0.95	C17—C18	1.404 (4)
C31—C32	1.351 (4)	C18—C19	1.388 (4)
C31—H31	0.95	C19—C20	1.375 (4)
C32—H32	0.95	C19—H19	0.95
N1—C7	1.383 (4)	C20—C21	1.393 (4)
N1—C1	1.386 (4)	C21—C22	1.382 (4)
N1—C12	1.461 (4)	C21—H21	0.95
N2—C7	1.321 (4)	C22—H22	0.95
N2—C2	1.387 (4)	C28—H28A	0.99
N3—C23	1.383 (4)	C28—H28B	0.99
N3—C17	1.383 (4)
C11—S1—C8	91.52 (17)	C5—C6—H6	121.4
C16—S2—C13	91.50 (17)	C1—C6—H6	121.4
C27—S3—C24	91.35 (18)	N2—C7—N1	113.4 (3)
C25—C24—C23	130.8 (5)	N2—C7—C8	122.7 (3)
C25—C24—S3	110.9 (4)	N1—C7—C8	123.8 (3)
C23—C24—S3	118.0 (3)	C9—C8—C7	131.0 (3)
C24—C25—C26	113.5 (5)	C9—C8—S1	111.3 (2)
C24—C25—H25	123.3	C7—C8—S1	117.5 (2)
C26—C25—H25	123.3	C8—C9—C10	111.2 (3)
C27—C26—C25	111.7 (4)	C8—C9—H9	124.4
C27—C26—H26	124.2	C10—C9—H9	124.4
C25—C26—H26	124.2	C11—C10—C9	113.5 (3)
C26—C27—S3	112.6 (3)	C11—C10—H10	123.2
C26—C27—H27	123.7	C9—C10—H10	123.2
S3—C27—H27	123.7	C10—C11—S1	112.5 (3)
C240—S300—C270	90.3 (11)	C10—C11—H11	123.8
C250—C240—C23	122 (3)	S1—C11—H11	123.8
C250—C240—S300	113.4 (14)	N1—C12—C13	114.7 (3)
C23—C240—S300	124 (2)	N1—C12—H12A	108.6
C240—C250—C260	111.3 (17)	C13—C12—H12A	108.6
C240—C250—H250	124.3	N1—C12—H12B	108.6
C260—C250—H250	124.3	C13—C12—H12B	108.6
C270—C260—C250	112.5 (18)	H12A—C12—H12B	107.6
C270—C260—H260	123.8	C14—C13—C12	127.0 (3)
C250—C260—H260	123.8	C14—C13—S2	111.2 (3)
C260—C270—S300	112.3 (16)	C12—C13—S2	121.8 (2)
C260—C270—H270	123.8	C13—C14—C15	112.3 (3)
S300—C270—H270	123.8	C13—C14—H14	123.8
C32—S4—C29	91.66 (16)	C15—C14—H14	123.8
C30—C29—C28	126.5 (3)	C16—C15—C14	112.9 (3)
C30—C29—S4	111.3 (2)	C16—C15—H15	123.6
C28—C29—S4	122.1 (2)	C14—C15—H15	123.6
C29—C30—C31	112.13 (16)	C15—C16—S2	112.1 (3)
C29—C30—H30	123.9	C15—C16—H16	123.9
C31—C30—H30	123.9	S2—C16—H16	123.9
C32—C31—C30	112.13 (19)	N3—C17—C22	131.7 (3)
C32—C31—H31	123.9	N3—C17—C18	105.5 (3)
C30—C31—H31	123.9	C22—C17—C18	122.9 (3)
C31—C32—S4	112.8 (3)	N4—C18—C19	130.1 (3)
C31—C32—H32	123.6	N4—C18—C17	110.1 (3)
S4—C32—H32	123.6	C19—C18—C17	119.7 (3)
C7—N1—C1	105.9 (2)	C20—C19—C18	116.9 (3)
C7—N1—C12	129.5 (3)	C20—C19—H19	121.6
C1—N1—C12	124.3 (3)	C18—C19—H19	121.6
C7—N2—C2	104.9 (3)	C19—C20—C21	123.7 (3)
C23—N3—C17	106.4 (2)	C19—C20—Br2	118.7 (3)
C23—N3—C28	129.2 (3)	C21—C20—Br2	117.6 (2)
C17—N3—C28	124.2 (3)	C22—C21—C20	120.0 (3)
C23—N4—C18	105.2 (3)	C22—C21—H21	120.0
N1—C1—C6	131.8 (3)	C20—C21—H21	120.0
N1—C1—C2	105.7 (3)	C21—C22—C17	116.7 (3)
C6—C1—C2	122.5 (3)	C21—C22—H22	121.6
C3—C2—N2	129.9 (3)	C17—C22—H22	121.6
C3—C2—C1	120.0 (3)	N4—C23—N3	112.8 (3)
N2—C2—C1	110.1 (3)	N4—C23—C240	118 (2)
C4—C3—C2	116.6 (3)	N3—C23—C240	129 (2)
C4—C3—H3	121.7	N4—C23—C24	123.2 (3)
C2—C3—H3	121.7	N3—C23—C24	124.0 (3)
C3—C4—C5	123.9 (3)	C240—C23—C24	6 (3)
C3—C4—Br1	118.0 (2)	N3—C28—C29	114.4 (3)
C5—C4—Br1	118.1 (2)	N3—C28—H28A	108.7
C6—C5—C4	119.8 (3)	C29—C28—H28A	108.7
C6—C5—H5	120.1	N3—C28—H28B	108.7
C4—C5—H5	120.1	C29—C28—H28B	108.7
C5—C6—C1	117.2 (3)	H28A—C28—H28B	107.6

D—H···A	D—H	H···A	D···A	D—H···A
C12i—H12Bi···N4	0.99	2.57	3.454 (4)	149
C22—H22···N2	0.95	2.61	3.504 (4)	158
C28—H28A···N2	0.99	2.61	3.522 (4)	152
C6i—H6i···N4	0.95	2.65	3.547 (4)	157
C3—H3···Cg4	0.95	2.68	3.578 (4)	158
C19—H19···Cg2i	0.95	2.62	3.512 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the S2,C13–C16 and S4,C29–C32 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12i—H12B i⋯N4	0.99	2.57	3.454 (4)	149
C22—H22⋯N2	0.95	2.61	3.504 (4)	158
C28—H28A⋯N2	0.99	2.61	3.522 (4)	152
C6i—H6i⋯N4	0.95	2.65	3.547 (4)	157
C3—H3⋯Cg4	0.95	2.68	3.578 (4)	158
C19—H19⋯Cg2i	0.95	2.62	3.512 (4)	157

Symmetry code: (i) .