1-(5-Bromo-4-phenyl-1,3-thia-zol-2-yl)pyrrolidin-2-one.

The asymmetric unit of the title compound, C(13)H(11)BrN(2)OS, consists of two crystallographically independent mol-ecules (A and B). In each mol-ecule, the pyrrolidine ring adopts an envelope conformation with a methyl-ene C atom as the flap atom. In mol-ecule A, the central thia-zole ring makes a dihedral angle of 36.69 (11)° with the adjacent phenyl ring, whereas the corresponding angle is 36.85 (12)° in mol-ecule B. The pyrrolidine ring is slightly twisted from the thia-zole ring, with C-N-C-N torsion angles of 4.8 (3) and 3.0 (4)° in mol-ecules A and B, respectively. In the crystal, C-H⋯π and π-π [centroid-to-centroid distance = 3.7539 (14) Å] inter-actions are observed. The crystal studied was a pseudo-merohedral twin with twin law (-100 0-10 101) and a refined component ratio of 0.7188 (5):0.2812 (5).

Related literature

For background to thiazoles, see: Bishayee et al. (1997 ▶); Chitamber & Wereley (1997 ▶); Bhaskar et al. (2008 ▶); Sharma et al. (2009 ▶); Bhattacharya et al. (2005 ▶); Spector et al. (1998 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H11BrN2OS

M = 323.21

Monoclinic,

a = 7.5243 (3) Å

b = 14.1861 (6) Å

c = 12.4488 (6) Å

β = 107.508 (1)°

V = 1267.23 (10) Å3

Z = 4

Mo Kα radiation

μ = 3.40 mm−1

T = 100 K

0.26 × 0.14 × 0.14 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.466, T max = 0.646

30838 measured reflections

9338 independent reflections

8701 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.051

S = 0.99

9338 reflections

326 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.46 e Å−3

Absolute structure: Flack (1983 ▶), with 4219 Friedel pairs

Flack parameter: 0.017 (4)

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201954X/is5131sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201954X/is5131Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201954X/is5131Isup3.cml

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

C13H11BrN2OS	F(000) = 648
Mr = 323.21	Dx = 1.694 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9880 reflections
a = 7.5243 (3) Å	θ = 2.2–32.0°
b = 14.1861 (6) Å	µ = 3.40 mm−1
c = 12.4488 (6) Å	T = 100 K
β = 107.508 (1)°	Block, colourless
V = 1267.23 (10) Å3	0.26 × 0.14 × 0.14 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	9338 independent reflections
Radiation source: fine-focus sealed tube	8701 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 33.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.466, Tmax = 0.646	k = −21→21
30838 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.051	w = 1/[σ2(Fo2) + (0.0136P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
9338 reflections	Δρmax = 0.58 e Å−3
326 parameters	Δρmin = −0.46 e Å−3
1 restraint	Absolute structure: Flack (1983), with 4219 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.017 (4)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Br1A	1.01261 (3)	0.351681 (14)	0.70723 (2)	0.02637 (6)
S1A	0.68748 (7)	0.33990 (4)	0.48703 (5)	0.01897 (10)
O1A	0.4724 (3)	0.32508 (11)	0.26929 (13)	0.0249 (3)
N1A	0.4385 (2)	0.34234 (16)	0.59269 (14)	0.0167 (3)
N2A	0.3089 (3)	0.33380 (14)	0.39687 (16)	0.0189 (4)
C1A	0.7366 (3)	0.39986 (15)	0.87748 (19)	0.0214 (4)
H1AA	0.8276	0.4358	0.8601	0.026*
C2A	0.7282 (3)	0.39718 (17)	0.98699 (19)	0.0243 (5)
H2AA	0.8110	0.4331	1.0423	0.029*
C3A	0.5979 (3)	0.34160 (19)	1.01478 (19)	0.0246 (5)
H3AA	0.5954	0.3389	1.0890	0.030*
C4A	0.4701 (3)	0.28953 (17)	0.93178 (19)	0.0225 (4)
H4AA	0.3815	0.2524	0.9501	0.027*
C5A	0.4761 (3)	0.29351 (16)	0.82224 (18)	0.0179 (4)
H5AA	0.3905	0.2590	0.7667	0.022*
C6A	0.6091 (3)	0.34881 (16)	0.79332 (17)	0.0162 (4)
C7A	0.6099 (3)	0.34893 (16)	0.67534 (17)	0.0167 (4)
C8A	0.7554 (3)	0.34945 (18)	0.63183 (17)	0.0176 (4)
C9A	0.4600 (3)	0.33758 (15)	0.49273 (18)	0.0166 (4)
C10A	0.1169 (3)	0.34222 (19)	0.40144 (19)	0.0225 (4)
H10A	0.0897	0.4061	0.4195	0.027*
H10B	0.0937	0.2992	0.4563	0.027*
C11A	0.0021 (4)	0.31523 (16)	0.2810 (2)	0.0244 (5)
H11A	−0.1123	0.3515	0.2568	0.029*
H11B	−0.0288	0.2487	0.2762	0.029*
C12A	0.1303 (3)	0.33887 (18)	0.20894 (19)	0.0267 (5)
H12A	0.1118	0.2946	0.1471	0.032*
H12B	0.1068	0.4022	0.1786	0.032*
C13A	0.3242 (3)	0.33079 (14)	0.28908 (19)	0.0212 (4)
Br1B	0.15444 (3)	0.079853 (14)	0.69491 (2)	0.02544 (5)
S1B	0.24659 (7)	0.09024 (4)	0.46979 (4)	0.01913 (10)
O1B	0.2343 (3)	0.11605 (13)	0.25040 (14)	0.0269 (4)
N1B	0.6031 (2)	0.08191 (17)	0.56770 (14)	0.0179 (3)
N2B	0.5265 (3)	0.09060 (15)	0.37119 (14)	0.0191 (3)
C1B	0.5995 (3)	0.02734 (16)	0.85721 (18)	0.0220 (4)
H1BA	0.4904	−0.0079	0.8416	0.026*
C2B	0.7207 (4)	0.03050 (17)	0.96597 (19)	0.0253 (5)
H2BA	0.6929	−0.0037	1.0226	0.030*
C3B	0.8816 (3)	0.0835 (2)	0.99154 (18)	0.0260 (5)
H3BA	0.9604	0.0860	1.0651	0.031*
C4B	0.9255 (3)	0.13339 (18)	0.9064 (2)	0.0234 (5)
H4BA	1.0339	0.1692	0.9229	0.028*
C5B	0.8065 (3)	0.12933 (17)	0.79710 (18)	0.0188 (4)
H5BA	0.8372	0.1619	0.7403	0.023*
C6B	0.6420 (3)	0.07735 (17)	0.77091 (17)	0.0167 (4)
C7B	0.5198 (3)	0.07758 (17)	0.65372 (15)	0.0160 (3)
C8B	0.3295 (3)	0.0800 (2)	0.61500 (18)	0.0194 (4)
C9B	0.4773 (3)	0.08761 (18)	0.47029 (16)	0.0170 (4)
C10B	0.7195 (3)	0.0830 (2)	0.37033 (17)	0.0212 (4)
H10C	0.7822	0.0302	0.4157	0.025*
H10D	0.7884	0.1404	0.3975	0.025*
C11B	0.6969 (4)	0.06701 (18)	0.2457 (2)	0.0272 (5)
H11C	0.7981	0.0963	0.2246	0.033*
H11D	0.6946	0.0002	0.2287	0.033*
C12B	0.5114 (4)	0.11300 (18)	0.18401 (19)	0.0242 (5)
H12C	0.5289	0.1781	0.1657	0.029*
H12D	0.4496	0.0793	0.1151	0.029*
C13B	0.4007 (3)	0.10679 (15)	0.2667 (2)	0.0219 (5)

	U11	U22	U33	U12	U13	U23
Br1A	0.01407 (9)	0.02869 (12)	0.03443 (13)	−0.00219 (9)	0.00438 (9)	0.00372 (11)
S1A	0.0193 (2)	0.0182 (2)	0.0212 (2)	0.0000 (2)	0.00885 (19)	0.0019 (2)
O1A	0.0317 (9)	0.0245 (8)	0.0207 (7)	−0.0017 (7)	0.0111 (7)	0.0014 (6)
N1A	0.0130 (8)	0.0190 (9)	0.0170 (8)	0.0014 (7)	0.0028 (6)	0.0004 (7)
N2A	0.0210 (9)	0.0174 (9)	0.0172 (8)	0.0011 (7)	0.0040 (7)	−0.0007 (7)
C1A	0.0223 (11)	0.0151 (9)	0.0232 (10)	−0.0031 (8)	0.0016 (9)	0.0011 (8)
C2A	0.0289 (12)	0.0215 (10)	0.0162 (10)	0.0000 (9)	−0.0029 (9)	−0.0020 (8)
C3A	0.0295 (11)	0.0239 (11)	0.0185 (10)	0.0055 (10)	0.0042 (9)	0.0003 (10)
C4A	0.0231 (11)	0.0249 (10)	0.0208 (11)	0.0014 (9)	0.0084 (9)	−0.0008 (9)
C5A	0.0158 (9)	0.0199 (10)	0.0170 (10)	−0.0001 (7)	0.0032 (8)	−0.0018 (7)
C6A	0.0134 (8)	0.0172 (9)	0.0162 (8)	0.0039 (8)	0.0015 (7)	0.0023 (8)
C7A	0.0154 (8)	0.0143 (8)	0.0186 (9)	−0.0006 (8)	0.0023 (7)	0.0007 (8)
C8A	0.0133 (8)	0.0187 (9)	0.0193 (9)	−0.0007 (9)	0.0024 (7)	0.0020 (9)
C9A	0.0151 (9)	0.0164 (8)	0.0171 (9)	0.0017 (8)	0.0031 (8)	0.0013 (7)
C10A	0.0180 (10)	0.0251 (11)	0.0212 (10)	0.0043 (9)	0.0013 (8)	−0.0024 (9)
C11A	0.0264 (12)	0.0250 (9)	0.0191 (10)	0.0000 (9)	0.0031 (9)	−0.0020 (9)
C12A	0.0322 (13)	0.0242 (11)	0.0193 (10)	−0.0004 (10)	0.0008 (9)	0.0020 (9)
C13A	0.0292 (11)	0.0148 (9)	0.0180 (9)	0.0006 (8)	0.0047 (10)	0.0016 (7)
Br1B	0.02277 (10)	0.02499 (10)	0.03492 (12)	−0.00498 (9)	0.01830 (9)	−0.00685 (11)
S1B	0.0166 (2)	0.0177 (2)	0.0224 (2)	0.0005 (2)	0.00493 (19)	−0.0016 (2)
O1B	0.0266 (9)	0.0261 (8)	0.0232 (8)	0.0029 (7)	0.0002 (7)	−0.0029 (7)
N1B	0.0194 (8)	0.0191 (7)	0.0175 (7)	0.0016 (9)	0.0092 (6)	0.0007 (8)
N2B	0.0216 (9)	0.0206 (8)	0.0159 (7)	0.0007 (8)	0.0068 (7)	0.0003 (7)
C1B	0.0279 (11)	0.0214 (10)	0.0198 (10)	−0.0028 (9)	0.0117 (9)	−0.0028 (8)
C2B	0.0368 (13)	0.0242 (11)	0.0183 (11)	0.0021 (9)	0.0134 (10)	−0.0002 (8)
C3B	0.0294 (12)	0.0310 (11)	0.0174 (9)	0.0074 (12)	0.0067 (8)	−0.0033 (11)
C4B	0.0180 (10)	0.0266 (11)	0.0262 (12)	0.0014 (9)	0.0075 (9)	−0.0016 (9)
C5B	0.0176 (10)	0.0220 (11)	0.0191 (10)	0.0051 (8)	0.0089 (9)	0.0024 (8)
C6B	0.0214 (9)	0.0134 (8)	0.0182 (9)	0.0021 (9)	0.0104 (7)	−0.0008 (9)
C7B	0.0190 (8)	0.0132 (7)	0.0189 (8)	0.0000 (8)	0.0105 (7)	0.0000 (8)
C8B	0.0200 (9)	0.0165 (8)	0.0246 (10)	−0.0014 (9)	0.0113 (8)	−0.0022 (10)
C9B	0.0171 (9)	0.0168 (8)	0.0178 (9)	0.0027 (8)	0.0061 (7)	0.0037 (9)
C10B	0.0200 (10)	0.0269 (10)	0.0168 (9)	−0.0025 (11)	0.0058 (7)	−0.0016 (11)
C11B	0.0349 (13)	0.0291 (13)	0.0215 (10)	−0.0019 (10)	0.0146 (10)	−0.0015 (9)
C12B	0.0358 (13)	0.0206 (10)	0.0168 (10)	0.0016 (10)	0.0086 (9)	−0.0012 (8)
C13B	0.0285 (12)	0.0156 (10)	0.0195 (10)	0.0018 (8)	0.0042 (9)	−0.0019 (7)

Br1A—C8A	1.880 (2)	Br1B—C8B	1.874 (2)
S1A—C8A	1.725 (2)	S1B—C8B	1.732 (2)
S1A—C9A	1.7349 (19)	S1B—C9B	1.734 (2)
O1A—C13A	1.214 (3)	O1B—C13B	1.214 (3)
N1A—C9A	1.304 (3)	N1B—C9B	1.297 (3)
N1A—C7A	1.390 (3)	N1B—C7B	1.395 (2)
N2A—C9A	1.379 (3)	N2B—C13B	1.379 (3)
N2A—C13A	1.381 (3)	N2B—C9B	1.391 (3)
N2A—C10A	1.468 (3)	N2B—C10B	1.460 (3)
C1A—C2A	1.384 (3)	C1B—C2B	1.387 (3)
C1A—C6A	1.392 (3)	C1B—C6B	1.402 (3)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.381 (4)	C2B—C3B	1.379 (4)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.393 (3)	C3B—C4B	1.393 (4)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.379 (3)	C4B—C5B	1.387 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.401 (3)	C5B—C6B	1.393 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.471 (3)	C6B—C7B	1.472 (3)
C7A—C8A	1.360 (3)	C7B—C8B	1.367 (3)
C10A—C11A	1.536 (3)	C10B—C11B	1.526 (3)
C10A—H10A	0.9700	C10B—H10C	0.9700
C10A—H10B	0.9700	C10B—H10D	0.9700
C11A—C12A	1.539 (4)	C11B—C12B	1.522 (4)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—C13A	1.504 (3)	C12B—C13B	1.509 (4)
C12A—H12A	0.9700	C12B—H12C	0.9700
C12A—H12B	0.9700	C12B—H12D	0.9700
C8A—S1A—C9A	86.83 (10)	C8B—S1B—C9B	87.07 (10)
C9A—N1A—C7A	110.89 (17)	C9B—N1B—C7B	110.50 (17)
C9A—N2A—C13A	123.6 (2)	C13B—N2B—C9B	123.5 (2)
C9A—N2A—C10A	121.85 (18)	C13B—N2B—C10B	114.04 (18)
C13A—N2A—C10A	114.25 (19)	C9B—N2B—C10B	122.35 (17)
C2A—C1A—C6A	120.1 (2)	C2B—C1B—C6B	119.8 (2)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	120.1
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	120.1
C3A—C2A—C1A	120.6 (2)	C3B—C2B—C1B	121.1 (2)
C3A—C2A—H2AA	119.7	C3B—C2B—H2BA	119.4
C1A—C2A—H2AA	119.7	C1B—C2B—H2BA	119.4
C2A—C3A—C4A	120.1 (2)	C2B—C3B—C4B	119.6 (2)
C2A—C3A—H3AA	120.0	C2B—C3B—H3BA	120.2
C4A—C3A—H3AA	120.0	C4B—C3B—H3BA	120.2
C5A—C4A—C3A	119.4 (2)	C5B—C4B—C3B	119.6 (2)
C5A—C4A—H4AA	120.3	C5B—C4B—H4BA	120.2
C3A—C4A—H4AA	120.3	C3B—C4B—H4BA	120.2
C4A—C5A—C6A	121.0 (2)	C4B—C5B—C6B	121.2 (2)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.4
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.4
C1A—C6A—C5A	118.8 (2)	C5B—C6B—C1B	118.7 (2)
C1A—C6A—C7A	122.8 (2)	C5B—C6B—C7B	118.49 (19)
C5A—C6A—C7A	118.37 (19)	C1B—C6B—C7B	122.8 (2)
C8A—C7A—N1A	112.61 (18)	C8B—C7B—N1B	113.14 (17)
C8A—C7A—C6A	130.06 (18)	C8B—C7B—C6B	128.69 (17)
N1A—C7A—C6A	117.22 (18)	N1B—C7B—C6B	118.04 (17)
C7A—C8A—S1A	113.25 (15)	C7B—C8B—S1B	112.33 (15)
C7A—C8A—Br1A	129.24 (16)	C7B—C8B—Br1B	129.92 (16)
S1A—C8A—Br1A	117.40 (11)	S1B—C8B—Br1B	117.67 (11)
N1A—C9A—N2A	121.45 (18)	N1B—C9B—N2B	121.12 (18)
N1A—C9A—S1A	116.41 (15)	N1B—C9B—S1B	116.93 (15)
N2A—C9A—S1A	122.11 (16)	N2B—C9B—S1B	121.95 (15)
N2A—C10A—C11A	102.29 (19)	N2B—C10B—C11B	102.22 (17)
N2A—C10A—H10A	111.3	N2B—C10B—H10C	111.3
C11A—C10A—H10A	111.3	C11B—C10B—H10C	111.3
N2A—C10A—H10B	111.3	N2B—C10B—H10D	111.3
C11A—C10A—H10B	111.3	C11B—C10B—H10D	111.3
H10A—C10A—H10B	109.2	H10C—C10B—H10D	109.2
C10A—C11A—C12A	104.3 (2)	C12B—C11B—C10B	104.71 (19)
C10A—C11A—H11A	110.9	C12B—C11B—H11C	110.8
C12A—C11A—H11A	110.9	C10B—C11B—H11C	110.8
C10A—C11A—H11B	110.9	C12B—C11B—H11D	110.8
C12A—C11A—H11B	110.9	C10B—C11B—H11D	110.8
H11A—C11A—H11B	108.9	H11C—C11B—H11D	108.9
C13A—C12A—C11A	104.47 (19)	C13B—C12B—C11B	103.98 (18)
C13A—C12A—H12A	110.9	C13B—C12B—H12C	111.0
C11A—C12A—H12A	110.9	C11B—C12B—H12C	111.0
C13A—C12A—H12B	110.9	C13B—C12B—H12D	111.0
C11A—C12A—H12B	110.9	C11B—C12B—H12D	111.0
H12A—C12A—H12B	108.9	H12C—C12B—H12D	109.0
O1A—C13A—N2A	123.3 (2)	O1B—C13B—N2B	123.8 (2)
O1A—C13A—C12A	129.6 (2)	O1B—C13B—C12B	129.3 (2)
N2A—C13A—C12A	107.1 (2)	N2B—C13B—C12B	106.9 (2)
C6A—C1A—C2A—C3A	2.2 (3)	C6B—C1B—C2B—C3B	1.2 (4)
C1A—C2A—C3A—C4A	−1.7 (4)	C1B—C2B—C3B—C4B	−1.3 (4)
C2A—C3A—C4A—C5A	0.5 (4)	C2B—C3B—C4B—C5B	0.2 (4)
C3A—C4A—C5A—C6A	0.2 (3)	C3B—C4B—C5B—C6B	1.0 (3)
C2A—C1A—C6A—C5A	−1.4 (3)	C4B—C5B—C6B—C1B	−1.1 (3)
C2A—C1A—C6A—C7A	179.7 (2)	C4B—C5B—C6B—C7B	178.7 (2)
C4A—C5A—C6A—C1A	0.2 (3)	C2B—C1B—C6B—C5B	0.0 (3)
C4A—C5A—C6A—C7A	179.1 (2)	C2B—C1B—C6B—C7B	−179.8 (2)
C9A—N1A—C7A—C8A	0.4 (3)	C9B—N1B—C7B—C8B	0.3 (3)
C9A—N1A—C7A—C6A	−176.2 (2)	C9B—N1B—C7B—C6B	−175.9 (2)
C1A—C6A—C7A—C8A	38.0 (4)	C5B—C6B—C7B—C8B	−141.2 (3)
C5A—C6A—C7A—C8A	−140.9 (3)	C1B—C6B—C7B—C8B	38.6 (4)
C1A—C6A—C7A—N1A	−146.1 (2)	C5B—C6B—C7B—N1B	34.3 (3)
C5A—C6A—C7A—N1A	35.1 (3)	C1B—C6B—C7B—N1B	−145.9 (2)
N1A—C7A—C8A—S1A	−1.0 (3)	N1B—C7B—C8B—S1B	−1.3 (3)
C6A—C7A—C8A—S1A	175.1 (2)	C6B—C7B—C8B—S1B	174.4 (2)
N1A—C7A—C8A—Br1A	−176.95 (19)	N1B—C7B—C8B—Br1B	−177.9 (2)
C6A—C7A—C8A—Br1A	−0.8 (4)	C6B—C7B—C8B—Br1B	−2.2 (4)
C9A—S1A—C8A—C7A	0.9 (2)	C9B—S1B—C8B—C7B	1.4 (2)
C9A—S1A—C8A—Br1A	177.41 (16)	C9B—S1B—C8B—Br1B	178.51 (17)
C7A—N1A—C9A—N2A	−177.8 (2)	C7B—N1B—C9B—N2B	−178.5 (2)
C7A—N1A—C9A—S1A	0.3 (3)	C7B—N1B—C9B—S1B	0.9 (3)
C13A—N2A—C9A—N1A	178.5 (2)	C13B—N2B—C9B—N1B	−172.8 (2)
C10A—N2A—C9A—N1A	4.8 (3)	C10B—N2B—C9B—N1B	3.0 (4)
C13A—N2A—C9A—S1A	0.5 (3)	C13B—N2B—C9B—S1B	7.8 (3)
C10A—N2A—C9A—S1A	−173.23 (18)	C10B—N2B—C9B—S1B	−176.4 (2)
C8A—S1A—C9A—N1A	−0.7 (2)	C8B—S1B—C9B—N1B	−1.4 (2)
C8A—S1A—C9A—N2A	177.4 (2)	C8B—S1B—C9B—N2B	178.1 (2)
C9A—N2A—C10A—C11A	−169.7 (2)	C13B—N2B—C10B—C11B	−16.4 (3)
C13A—N2A—C10A—C11A	16.0 (3)	C9B—N2B—C10B—C11B	167.4 (2)
N2A—C10A—C11A—C12A	−25.5 (2)	N2B—C10B—C11B—C12B	26.6 (3)
C10A—C11A—C12A—C13A	26.6 (2)	C10B—C11B—C12B—C13B	−27.8 (3)
C9A—N2A—C13A—O1A	4.9 (3)	C9B—N2B—C13B—O1B	−3.2 (4)
C10A—N2A—C13A—O1A	179.1 (2)	C10B—N2B—C13B—O1B	−179.3 (2)
C9A—N2A—C13A—C12A	−173.4 (2)	C9B—N2B—C13B—C12B	175.1 (2)
C10A—N2A—C13A—C12A	0.8 (3)	C10B—N2B—C13B—C12B	−1.0 (3)
C11A—C12A—C13A—O1A	164.4 (2)	C11B—C12B—C13B—O1B	−163.6 (2)
C11A—C12A—C13A—N2A	−17.4 (2)	C11B—C12B—C13B—N2B	18.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12A—H12B···Cg1i	0.97	2.89	3.767 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1B–C6B ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12A—H12B⋯Cg1i	0.97	2.89	3.767 (3)	151

Symmetry code: (i) .