3-(2-Chloro-6-fluoro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

The title chalcone derivative, C(13)H(8)ClFOS, crystallized as an inversion twin with two independent mol-ecules in the asymmetric unit. The thio-phene rings in both mol-ecules are disordered over two sites: the ratios of occupancies for the major and minor components in the two mol-ecules are 0.820 (2):0.180 (2) and 0.853 (2):0.147 (2). The dihedral angles between the major and minor components of the thio-phene and benzene rings are 1.13 (18) and 2.2 (6)°, respectively, in one mol-ecule, with corresponding values 6.09 (17) and 1.3 (6)° in the other. Weak intra-molecular C-H⋯O and C-H⋯F inter-actions involving the prop-2-en-1-one group generate an S(5)S(5) ring motif, whereas a weak intra-molecular C-H⋯Cl contact generates an S(6) ring motif. In the crystal structure, mol-ecules of both the major and minor components are linked into infinite one-dimensional chains along the b axis. The crystal structure is stabilized by weak C-H⋯O, C-H⋯F, C-H⋯Cl and C-H⋯π inter-actions.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see, for example: Fun et al. (2008 ▶); Patil et al. (2007b ▶,c ▶). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ▶); Chopra et al. (2007 ▶). Patil et al. (2007a ▶).

Experimental

Crystal data

C13H8ClFOS

M = 266.71

Monoclinic,

a = 12.1137 (3) Å

b = 10.5012 (3) Å

c = 18.6689 (5) Å

β = 107.882 (3)°

V = 2260.11 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.51 mm−1

T = 100.0 (1) K

0.38 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.830, T max = 0.911

26405 measured reflections

6525 independent reflections

5474 reflections with I > 2σ(I)

R int = 0.084

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.171

S = 1.05

6525 reflections

347 parameters

233 restraints

H-atom parameters constrained

Δρmax = 0.83 e Å−3

Δρmin = −0.92 e Å−3

Absolute structure: Flack (1983 ▶), 3231 Friedel pairs

Flack parameter: 0.43 (7)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024872/sj2529sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024872/sj2529Isup2.hkl

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

C13H8ClFOS	F000 = 1088
Mr = 266.71	Dx = 1.568 Mg m−3
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6525 reflections
a = 12.1137 (3) Å	θ = 2.3–30.0º
b = 10.5012 (3) Å	µ = 0.51 mm−1
c = 18.6689 (5) Å	T = 100.0 (1) K
β = 107.882 (3)º	Block, colorless
V = 2260.11 (11) Å3	0.38 × 0.27 × 0.19 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	6525 independent reflections
Radiation source: fine-focus sealed tube	5474 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.084
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 2.3º
ω scans	h = −17→17
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −14→14
Tmin = 0.830, Tmax = 0.911	l = −26→26
26405 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.063	w = 1/[σ2(Fo2) + (0.089P)2 + 4.5385P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.171	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.83 e Å−3
6525 reflections	Δρmin = −0.91 e Å−3
347 parameters	Extinction correction: none
233 restraints	Absolute structure: Flack (1983), 3231 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.43 (7)
Secondary atom site location: difference Fourier map

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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)
Cl1A	0.16981 (8)	0.06049 (9)	0.04048 (5)	0.0439 (2)
F1A	−0.22351 (13)	−0.16353 (19)	−0.01215 (9)	0.0282 (4)
O1A	−0.23551 (18)	0.1662 (2)	−0.18144 (12)	0.0271 (5)
C1A	0.0753 (3)	−0.0405 (3)	0.05750 (18)	0.0304 (7)
C2A	0.1172 (3)	−0.1253 (3)	0.11799 (18)	0.0368 (8)
H2AA	0.1943	−0.1208	0.1478	0.044*
C3A	0.0444 (4)	−0.2155 (3)	0.1335 (2)	0.0450 (9)
H3AA	0.0725	−0.2701	0.1744	0.054*
C4A	−0.0684 (4)	−0.2251 (3)	0.0895 (2)	0.0408 (9)
H4AA	−0.1171	−0.2870	0.0989	0.049*
C5A	−0.1078 (3)	−0.1421 (3)	0.03161 (18)	0.0326 (7)
C6A	−0.0413 (3)	−0.0465 (3)	0.01129 (16)	0.0248 (6)
C7A	−0.0979 (3)	0.0341 (3)	−0.05309 (16)	0.0240 (6)
H7AA	−0.1764	0.0172	−0.0752	0.029*
C8A	−0.0570 (3)	0.1277 (3)	−0.08580 (17)	0.0250 (6)
H8AA	0.0204	0.1516	−0.0661	0.030*
C9A	−0.1314 (2)	0.1940 (2)	−0.15224 (16)	0.0209 (6)
C10A	−0.0801 (2)	0.2973 (2)	−0.18457 (15)	0.0206 (5)
S1A	−0.16312 (8)	0.37629 (9)	−0.26092 (5)	0.0256 (2)	0.821 (2)
C11A	0.0339 (4)	0.3415 (5)	−0.1616 (3)	0.0319 (11)	0.821 (2)
H11A	0.0922	0.3078	−0.1212	0.038*	0.821 (2)
C12A	0.0509 (4)	0.4447 (4)	−0.2072 (2)	0.0288 (9)	0.821 (2)
H12A	0.1206	0.4877	−0.1997	0.035*	0.821 (2)
C13A	−0.0498 (3)	0.4716 (3)	−0.2634 (2)	0.0244 (8)	0.821 (2)
H13A	−0.0557	0.5350	−0.2992	0.029*	0.821 (2)
S1X	0.0540 (5)	0.3451 (5)	−0.1503 (3)	0.0244 (12)*	0.179 (2)
C11X	−0.1495 (13)	0.3737 (17)	−0.2410 (11)	0.035 (5)*	0.179 (2)
H11B	−0.2300	0.3692	−0.2597	0.042*	0.179 (2)
C12X	−0.0788 (12)	0.4597 (16)	−0.2659 (9)	0.020 (4)*	0.179 (2)
H12B	−0.1050	0.5093	−0.3091	0.025*	0.179 (2)
C13X	0.0334 (13)	0.4609 (17)	−0.2182 (10)	0.026 (4)*	0.179 (2)
H13B	0.0906	0.5170	−0.2222	0.031*	0.179 (2)
Cl1B	−0.16932 (8)	0.69186 (9)	−0.16305 (5)	0.0416 (2)
F1B	0.22038 (13)	0.9255 (2)	−0.10610 (9)	0.0291 (4)
O1B	0.23296 (17)	0.60229 (19)	0.06450 (12)	0.0267 (5)
C1B	−0.0721 (3)	0.7932 (3)	−0.18114 (17)	0.0250 (6)
C2B	−0.1171 (3)	0.8706 (4)	−0.24489 (19)	0.0353 (8)
H2BA	−0.1930	0.8603	−0.2758	0.042*
C3B	−0.0460 (3)	0.9621 (3)	−0.2606 (2)	0.0352 (7)
H3BA	−0.0743	1.0140	−0.3026	0.042*
C4B	0.0651 (3)	0.9774 (3)	−0.21507 (17)	0.0341 (7)
H4BA	0.1127	1.0397	−0.2254	0.041*
C5B	0.1055 (3)	0.8987 (3)	−0.15358 (16)	0.0248 (6)
C6B	0.0415 (2)	0.8020 (3)	−0.13370 (16)	0.0206 (5)
C7B	0.0981 (2)	0.7253 (2)	−0.06705 (15)	0.0205 (5)
H7BA	0.1726	0.7514	−0.0401	0.025*
C8B	0.0591 (3)	0.6225 (3)	−0.03853 (16)	0.0232 (6)
H8BA	−0.0136	0.5885	−0.0629	0.028*
C9B	0.1334 (3)	0.5649 (3)	0.03181 (16)	0.0229 (6)
C10B	0.0835 (2)	0.4603 (3)	0.06389 (15)	0.0195 (5)
S1B	0.16576 (7)	0.39734 (8)	0.14734 (5)	0.02200 (18)	0.853 (2)
C11B	0.0601 (3)	0.2918 (4)	0.1489 (2)	0.0220 (9)	0.853 (2)
H11C	0.0662	0.2341	0.1877	0.026*	0.853 (2)
C12B	−0.0348 (3)	0.3014 (4)	0.0865 (2)	0.0243 (8)	0.853 (2)
H12C	−0.1007	0.2507	0.0773	0.029*	0.853 (2)
C13B	−0.0199 (4)	0.3982 (4)	0.0380 (2)	0.0222 (8)	0.853 (2)
H13C	−0.0755	0.4179	−0.0074	0.027*	0.853 (2)
S1Y	−0.0509 (5)	0.4042 (6)	0.0261 (3)	0.0182 (12)	0.147 (2)
C11Y	−0.0421 (15)	0.293 (2)	0.0931 (12)	0.028 (5)*	0.147 (2)
H11D	−0.1016	0.2380	0.0947	0.034*	0.147 (2)
C12Y	0.0663 (16)	0.295 (2)	0.1448 (13)	0.028 (6)*	0.147 (2)
H12D	0.0912	0.2418	0.1863	0.033*	0.147 (2)
C13Y	0.1343 (15)	0.3903 (17)	0.1263 (10)	0.028 (5)*	0.147 (2)
H13D	0.2106	0.4045	0.1555	0.034*	0.147 (2)

	U11	U22	U33	U12	U13	U23
Cl1A	0.0386 (4)	0.0458 (5)	0.0426 (5)	−0.0123 (4)	0.0056 (4)	0.0065 (4)
F1A	0.0116 (6)	0.0517 (10)	0.0204 (7)	−0.0127 (7)	0.0036 (6)	0.0033 (7)
O1A	0.0269 (9)	0.0264 (9)	0.0285 (10)	−0.0043 (8)	0.0090 (8)	0.0000 (8)
C1A	0.0317 (15)	0.0328 (15)	0.0268 (14)	0.0066 (12)	0.0090 (12)	−0.0026 (12)
C2A	0.0403 (17)	0.0429 (17)	0.0254 (15)	0.0147 (15)	0.0074 (14)	−0.0034 (13)
C3A	0.081 (2)	0.0263 (14)	0.0353 (16)	0.0153 (16)	0.0295 (17)	0.0072 (12)
C4A	0.069 (2)	0.0250 (14)	0.0328 (16)	0.0000 (16)	0.0216 (16)	0.0028 (13)
C5A	0.0544 (17)	0.0239 (13)	0.0264 (13)	−0.0046 (13)	0.0225 (12)	−0.0031 (11)
C6A	0.0343 (14)	0.0207 (11)	0.0227 (12)	0.0018 (11)	0.0138 (11)	−0.0031 (9)
C7A	0.0270 (12)	0.0229 (12)	0.0233 (12)	0.0017 (11)	0.0094 (10)	−0.0029 (10)
C8A	0.0279 (13)	0.0218 (12)	0.0264 (13)	−0.0039 (10)	0.0102 (11)	0.0016 (10)
C9A	0.0295 (13)	0.0158 (10)	0.0185 (11)	0.0010 (10)	0.0089 (10)	−0.0008 (9)
C10A	0.0254 (12)	0.0199 (11)	0.0193 (11)	−0.0015 (10)	0.0110 (10)	−0.0031 (9)
S1A	0.0276 (4)	0.0256 (4)	0.0234 (4)	−0.0015 (3)	0.0078 (3)	0.0045 (3)
C11A	0.0287 (19)	0.044 (2)	0.0208 (18)	−0.0121 (17)	0.0050 (15)	−0.0007 (15)
C12A	0.0340 (17)	0.0274 (17)	0.0274 (18)	−0.0059 (15)	0.0130 (14)	−0.0062 (14)
C13A	0.0245 (15)	0.0188 (14)	0.0354 (17)	−0.0091 (13)	0.0172 (13)	−0.0001 (12)
Cl1B	0.0370 (4)	0.0403 (4)	0.0428 (4)	−0.0098 (3)	0.0053 (4)	0.0077 (4)
F1B	0.0074 (6)	0.0587 (11)	0.0163 (7)	−0.0102 (7)	−0.0037 (5)	0.0189 (7)
O1B	0.0227 (9)	0.0250 (9)	0.0307 (10)	−0.0037 (8)	0.0059 (8)	0.0044 (8)
C1B	0.0251 (13)	0.0275 (13)	0.0227 (13)	0.0006 (11)	0.0076 (11)	0.0039 (11)
C2B	0.0312 (15)	0.0475 (18)	0.0287 (15)	0.0180 (14)	0.0111 (12)	0.0114 (13)
C3B	0.0498 (17)	0.0322 (14)	0.0287 (14)	0.0198 (14)	0.0196 (13)	0.0133 (12)
C4B	0.0592 (19)	0.0254 (13)	0.0247 (14)	0.0095 (13)	0.0235 (13)	0.0042 (11)
C5B	0.0328 (14)	0.0222 (12)	0.0212 (12)	−0.0005 (11)	0.0108 (11)	−0.0018 (10)
C6B	0.0231 (12)	0.0189 (11)	0.0222 (12)	0.0012 (9)	0.0108 (10)	−0.0025 (9)
C7B	0.0229 (11)	0.0195 (11)	0.0210 (12)	0.0001 (10)	0.0096 (10)	0.0004 (9)
C8B	0.0256 (13)	0.0210 (12)	0.0220 (12)	−0.0015 (10)	0.0059 (10)	−0.0003 (10)
C9B	0.0278 (13)	0.0172 (11)	0.0253 (13)	−0.0019 (10)	0.0108 (11)	−0.0005 (10)
C10B	0.0208 (11)	0.0191 (11)	0.0187 (11)	0.0013 (10)	0.0061 (9)	−0.0008 (9)
S1B	0.0200 (4)	0.0232 (3)	0.0219 (4)	−0.0004 (3)	0.0051 (3)	0.0069 (3)
C11B	0.0279 (15)	0.0198 (15)	0.0219 (15)	0.0022 (12)	0.0132 (12)	0.0063 (11)
C12B	0.0255 (15)	0.0203 (14)	0.0292 (17)	−0.0052 (12)	0.0117 (13)	−0.0045 (12)
C13B	0.0195 (16)	0.0220 (15)	0.0212 (16)	0.0032 (13)	0.0005 (13)	0.0009 (12)
S1Y	0.006 (2)	0.029 (2)	0.015 (2)	−0.0037 (18)	−0.0044 (16)	0.0052 (18)

Cl1A—C1A	1.661 (4)	Cl1B—C1B	1.697 (3)
F1A—C5A	1.407 (4)	F1B—C5B	1.430 (3)
O1A—C9A	1.245 (3)	O1B—C9B	1.237 (3)
C1A—C2A	1.405 (5)	C1B—C6B	1.392 (4)
C1A—C6A	1.413 (4)	C1B—C2B	1.405 (4)
C2A—C3A	1.385 (6)	C2B—C3B	1.380 (5)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.365 (6)	C3B—C4B	1.363 (5)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.355 (5)	C4B—C5B	1.377 (4)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.410 (4)	C5B—C6B	1.395 (4)
C6A—C7A	1.458 (4)	C6B—C7B	1.464 (4)
C7A—C8A	1.331 (4)	C7B—C8B	1.351 (4)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.466 (4)	C8B—C9B	1.474 (4)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.470 (4)	C9B—C10B	1.467 (4)
C10A—C11X	1.384 (14)	C10B—C13Y	1.355 (14)
C10A—C11A	1.394 (5)	C10B—C13B	1.363 (5)
C10A—S1X	1.631 (6)	C10B—S1Y	1.671 (6)
C10A—S1A	1.688 (3)	C10B—S1B	1.704 (3)
S1A—C13A	1.712 (4)	S1B—C11B	1.700 (4)
C11A—C12A	1.431 (6)	C11B—C12B	1.366 (5)
C11A—H11A	0.9300	C11B—H11C	0.9300
C12A—C13A	1.372 (5)	C12B—C13B	1.409 (6)
C12A—H12A	0.9300	C12B—H12C	0.9300
C13A—H13A	0.9300	C13B—H13C	0.9300
S1X—C13X	1.718 (14)	S1Y—C11Y	1.692 (16)
C11X—C12X	1.418 (16)	C11Y—C12Y	1.369 (16)
C11X—H11B	0.9300	C11Y—H11D	0.9300
C12X—C13X	1.377 (15)	C12Y—C13Y	1.402 (17)
C12X—H12B	0.9300	C12Y—H12D	0.9300
C13X—H13B	0.9300	C13Y—H13D	0.9300
C2A—C1A—C6A	120.6 (3)	C6B—C1B—C2B	123.5 (3)
C2A—C1A—Cl1A	117.3 (3)	C6B—C1B—Cl1B	121.7 (2)
C6A—C1A—Cl1A	122.0 (2)	C2B—C1B—Cl1B	114.7 (2)
C3A—C2A—C1A	120.4 (3)	C3B—C2B—C1B	118.5 (3)
C3A—C2A—H2AA	119.8	C3B—C2B—H2BA	120.8
C1A—C2A—H2AA	119.8	C1B—C2B—H2BA	120.8
C4A—C3A—C2A	120.5 (3)	C4B—C3B—C2B	120.7 (3)
C4A—C3A—H3AA	119.7	C4B—C3B—H3BA	119.6
C2A—C3A—H3AA	119.7	C2B—C3B—H3BA	119.6
C5A—C4A—C3A	118.4 (4)	C3B—C4B—C5B	118.6 (3)
C5A—C4A—H4AA	120.8	C3B—C4B—H4BA	120.7
C3A—C4A—H4AA	120.8	C5B—C4B—H4BA	120.7
C4A—C5A—F1A	113.8 (3)	C4B—C5B—C6B	125.1 (3)
C4A—C5A—C6A	125.6 (3)	C4B—C5B—F1B	115.3 (3)
F1A—C5A—C6A	120.5 (3)	C6B—C5B—F1B	119.5 (2)
C5A—C6A—C1A	114.5 (3)	C1B—C6B—C5B	113.6 (3)
C5A—C6A—C7A	118.2 (3)	C1B—C6B—C7B	128.1 (3)
C1A—C6A—C7A	127.4 (3)	C5B—C6B—C7B	118.3 (2)
C8A—C7A—C6A	131.3 (3)	C8B—C7B—C6B	130.2 (3)
C8A—C7A—H7AA	114.4	C8B—C7B—H7BA	114.9
C6A—C7A—H7AA	114.4	C6B—C7B—H7BA	114.9
C7A—C8A—C9A	121.3 (3)	C7B—C8B—C9B	119.2 (3)
C7A—C8A—H8AA	119.4	C7B—C8B—H8BA	120.4
C9A—C8A—H8AA	119.4	C9B—C8B—H8BA	120.4
O1A—C9A—C8A	122.5 (3)	O1B—C9B—C10B	119.8 (3)
O1A—C9A—C10A	119.5 (2)	O1B—C9B—C8B	123.0 (3)
C8A—C9A—C10A	118.0 (2)	C10B—C9B—C8B	117.1 (2)
C11X—C10A—C11A	110.8 (7)	C13Y—C10B—C13B	99.8 (8)
C11X—C10A—C9A	120.4 (7)	C13Y—C10B—C9B	128.5 (8)
C11A—C10A—C9A	128.6 (3)	C13B—C10B—C9B	131.5 (3)
C11X—C10A—S1X	114.8 (7)	C13Y—C10B—S1Y	107.3 (8)
C9A—C10A—S1X	124.2 (3)	C9B—C10B—S1Y	124.2 (3)
C11A—C10A—S1A	111.9 (3)	C13B—C10B—S1B	110.7 (3)
C9A—C10A—S1A	119.5 (2)	C9B—C10B—S1B	117.7 (2)
S1X—C10A—S1A	116.3 (3)	S1Y—C10B—S1B	118.0 (3)
C10A—S1A—C13A	92.04 (16)	C11B—S1B—C10B	92.09 (15)
C10A—C11A—C12A	112.2 (4)	C12B—C11B—S1B	112.3 (3)
C10A—C11A—H11A	123.9	C12B—C11B—H11C	123.9
C12A—C11A—H11A	123.9	S1B—C11B—H11C	123.9
C13A—C12A—C11A	110.8 (4)	C11B—C12B—C13B	111.1 (3)
C13A—C12A—H12A	124.6	C11B—C12B—H12C	124.4
C11A—C12A—H12A	124.6	C13B—C12B—H12C	124.4
C12A—C13A—S1A	112.9 (3)	C10B—C13B—C12B	113.8 (3)
C12A—C13A—H13A	123.5	C10B—C13B—H13C	123.1
S1A—C13A—H13A	123.5	C12B—C13B—H13C	123.1
C10A—S1X—C13X	91.6 (6)	C10B—S1Y—C11Y	95.7 (6)
C10A—C11X—C12X	109.3 (11)	C12Y—C11Y—S1Y	109.6 (13)
C10A—C11X—H11B	125.3	C12Y—C11Y—H11D	125.2
C12X—C11X—H11B	125.3	S1Y—C11Y—H11D	125.2
C13X—C12X—C11X	111.7 (13)	C11Y—C12Y—C13Y	110.5 (15)
C13X—C12X—H12B	124.1	C11Y—C12Y—H12D	124.7
C11X—C12X—H12B	124.1	C13Y—C12Y—H12D	124.7
C12X—C13X—S1X	111.1 (11)	C10B—C13Y—C12Y	116.8 (13)
C12X—C13X—H13B	124.4	C10B—C13Y—H13D	121.6
S1X—C13X—H13B	124.4	C12Y—C13Y—H13D	121.6
C6A—C1A—C2A—C3A	−0.5 (5)	C6B—C1B—C2B—C3B	−1.5 (5)
Cl1A—C1A—C2A—C3A	−177.4 (3)	Cl1B—C1B—C2B—C3B	175.4 (3)
C1A—C2A—C3A—C4A	1.3 (5)	C1B—C2B—C3B—C4B	−0.2 (5)
C2A—C3A—C4A—C5A	−1.7 (5)	C2B—C3B—C4B—C5B	0.7 (5)
C3A—C4A—C5A—F1A	177.4 (3)	C3B—C4B—C5B—C6B	0.6 (5)
C3A—C4A—C5A—C6A	1.4 (5)	C3B—C4B—C5B—F1B	−176.4 (3)
C4A—C5A—C6A—C1A	−0.5 (5)	C2B—C1B—C6B—C5B	2.5 (4)
F1A—C5A—C6A—C1A	−176.3 (3)	Cl1B—C1B—C6B—C5B	−174.2 (2)
C4A—C5A—C6A—C7A	179.7 (3)	C2B—C1B—C6B—C7B	−178.7 (3)
F1A—C5A—C6A—C7A	3.9 (4)	Cl1B—C1B—C6B—C7B	4.6 (4)
C2A—C1A—C6A—C5A	0.1 (4)	C4B—C5B—C6B—C1B	−2.1 (4)
Cl1A—C1A—C6A—C5A	176.8 (2)	F1B—C5B—C6B—C1B	174.8 (3)
C2A—C1A—C6A—C7A	179.8 (3)	C4B—C5B—C6B—C7B	179.0 (3)
Cl1A—C1A—C6A—C7A	−3.4 (5)	F1B—C5B—C6B—C7B	−4.1 (4)
C5A—C6A—C7A—C8A	−177.9 (3)	C1B—C6B—C7B—C8B	5.9 (5)
C1A—C6A—C7A—C8A	2.3 (5)	C5B—C6B—C7B—C8B	−175.4 (3)
C6A—C7A—C8A—C9A	178.5 (3)	C6B—C7B—C8B—C9B	−178.0 (3)
C7A—C8A—C9A—O1A	−0.3 (4)	C7B—C8B—C9B—O1B	−3.7 (4)
C7A—C8A—C9A—C10A	179.3 (3)	C7B—C8B—C9B—C10B	175.0 (3)
O1A—C9A—C10A—C11X	8.0 (11)	O1B—C9B—C10B—C13Y	−3.0 (13)
C8A—C9A—C10A—C11X	−171.6 (11)	C8B—C9B—C10B—C13Y	178.2 (12)
O1A—C9A—C10A—C11A	−178.8 (4)	O1B—C9B—C10B—C13B	−176.5 (4)
C8A—C9A—C10A—C11A	1.6 (5)	C8B—C9B—C10B—C13B	4.7 (5)
O1A—C9A—C10A—S1X	178.4 (3)	O1B—C9B—C10B—S1Y	178.4 (4)
C8A—C9A—C10A—S1X	−1.2 (4)	C8B—C9B—C10B—S1Y	−0.4 (5)
O1A—C9A—C10A—S1A	−0.2 (4)	O1B—C9B—C10B—S1B	1.6 (4)
C8A—C9A—C10A—S1A	−179.8 (2)	C8B—C9B—C10B—S1B	−177.1 (2)
C11X—C10A—S1A—C13A	81 (5)	C13Y—C10B—S1B—C11B	−19 (5)
C11A—C10A—S1A—C13A	−1.0 (3)	C13B—C10B—S1B—C11B	−1.8 (3)
C9A—C10A—S1A—C13A	−179.7 (2)	C9B—C10B—S1B—C11B	179.7 (3)
S1X—C10A—S1A—C13A	1.6 (3)	S1Y—C10B—S1B—C11B	2.7 (3)
C11X—C10A—C11A—C12A	−6.0 (11)	C10B—S1B—C11B—C12B	1.5 (3)
C9A—C10A—C11A—C12A	−179.8 (3)	S1B—C11B—C12B—C13B	−0.9 (5)
S1X—C10A—C11A—C12A	−151 (5)	C13Y—C10B—C13B—C12B	5.0 (11)
S1A—C10A—C11A—C12A	1.6 (5)	C9B—C10B—C13B—C12B	179.9 (3)
C10A—C11A—C12A—C13A	−1.5 (6)	S1Y—C10B—C13B—C12B	−150 (3)
C11A—C12A—C13A—S1A	0.8 (5)	S1B—C10B—C13B—C12B	1.6 (4)
C10A—S1A—C13A—C12A	0.1 (3)	C11B—C12B—C13B—C10B	−0.5 (5)
C11X—C10A—S1X—C13X	−7.8 (13)	C13Y—C10B—S1Y—C11Y	1.6 (14)
C11A—C10A—S1X—C13X	29 (4)	C13B—C10B—S1Y—C11Y	28 (2)
C9A—C10A—S1X—C13X	−178.6 (8)	C9B—C10B—S1Y—C11Y	−179.5 (10)
S1A—C10A—S1X—C13X	0.0 (8)	S1B—C10B—S1Y—C11Y	−2.8 (10)
C11A—C10A—C11X—C12X	9.6 (18)	C10B—S1Y—C11Y—C12Y	−1(2)
C9A—C10A—C11X—C12X	−176.1 (11)	S1Y—C11Y—C12Y—C13Y	1(3)
S1X—C10A—C11X—C12X	12.7 (19)	C13B—C10B—C13Y—C12Y	−5(2)
S1A—C10A—C11X—C12X	−91 (6)	C9B—C10B—C13Y—C12Y	179.7 (16)
C10A—C11X—C12X—C13X	−12 (2)	S1Y—C10B—C13Y—C12Y	−1(2)
C11X—C12X—C13X—S1X	7(2)	S1B—C10B—C13Y—C12Y	159 (6)
C10A—S1X—C13X—C12X	0.4 (16)	C11Y—C12Y—C13Y—C10B	0(3)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AA···F1A	0.93	2.39	2.814 (4)	107
C7A—H7AA···O1A	0.93	2.45	2.827 (4)	104
C8A—H8AA···Cl1A	0.93	2.44	3.103 (3)	129
C7B—H7BA···F1B	0.93	2.37	2.794 (3)	107
C7B—H7BA···O1B	0.93	2.43	2.812 (3)	104
C8B—H8BA···Cl1B	0.93	2.46	3.105 (3)	126
C11A—H11A···F1Ai	0.93	2.54	3.375 (6)	150
C12A—H12A···O1Ai	0.93	2.51	3.402 (5)	161
C12B—H12C···O1Bii	0.93	2.50	3.427 (4)	174
C3A—H3AA···Cg1iii	0.93	3.06	3.748 (4)	132
C3A—H3AA···Cg3iii	0.93	3.14	3.825 (7)	132
C3B—H3BA···Cg5iv	0.93	3.02	3.778 (4)	140
C11B—H11C···Cg6v	0.93	2.81	3.677 (4)	155
C13A—H13A···Cg2iv	0.93	2.82	3.608 (4)	143
C13A—H13A···Cg4iv	0.93	2.82	3.625 (8)	145
C12X—H12B···Cg2iv	0.93	3.21	3.835 (16)	126
C12X—H12B···Cg4iv	0.93	3.18	3.840 (18)	129
C12Y—H12D···Cg6v	0.93	3.04	3.79 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7AA⋯F1A	0.93	2.39	2.814 (4)	107
C7A—H7AA⋯O1A	0.93	2.45	2.827 (4)	104
C8A—H8AA⋯Cl1A	0.93	2.44	3.103 (3)	129
C7B—H7BA⋯F1B	0.93	2.37	2.794 (3)	107
C7B—H7BA⋯O1B	0.93	2.43	2.812 (3)	104
C8B—H8BA⋯Cl1B	0.93	2.46	3.105 (3)	126
C11A—H11A⋯F1Ai	0.93	2.54	3.375 (6)	150
C12A—H12A⋯O1Ai	0.93	2.51	3.402 (5)	161
C12B—H12C⋯O1Bii	0.93	2.50	3.427 (4)	174
C3A—H3AA⋯Cg1iii	0.93	3.06	3.748 (4)	132
C3A—H3AA⋯Cg3iii	0.93	3.14	3.825 (7)	132
C3B—H3BA⋯Cg5iv	0.93	3.02	3.778 (4)	140
C11B—H11C⋯Cg6v	0.93	2.81	3.677 (4)	155
C13A—H13A⋯Cg2iv	0.93	2.82	3.608 (4)	143
C13A—H13A⋯Cg4iv	0.93	2.82	3.625 (8)	145
C12X—H12B⋯Cg2iv	0.93	3.21	3.835 (16)	126
C12X—H12B⋯Cg4iv	0.93	3.18	3.840 (18)	129
C12Y—H12D⋯Cg6v	0.93	3.04	3.79 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the S1A/C10A–C13A, S1B/C10B–C13B, S1X/C10A/C10X–C13X, S1Y/C10B/C11Y–C13Y, C1A–C6A and C1B–C6B rings, respectively.