(E)-3-(3,4-Dimethoxy-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

The title compound, C(15)H(14)O(3)S, has two symmetry-independent mol-ecules in the asymmetric unit with almost identical geometry. The dihedral angle between the benzene and thio-phene rings is 1.61 (11)° in one mol-ecule and 7.21 (11)° in the other. In both mol-ecules, C-H⋯O hydrogen bonds generate rings of graph-set motif S(5). The crystal structure is stabilized by C-H⋯O hydrogen bonds, C-H⋯π inter-actions and π-π inter-actions involving the benzene and thio-phene rings, with centroid-centroid distances of 3.5249 (13) and 3.6057 (13) Å.

Related literature

For related literature on the biological and non-linear optical properties of chalcone derivatives, see: Agrinskaya et al. (1999 ▶); Chopra et al. (2007 ▶); Patil et al. (2006 ▶); Patil, Ng et al. (2007 ▶); Patil, Fun et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H14O3S

M = 274.32

Monoclinic,

a = 12.1509 (3) Å

b = 14.3118 (3) Å

c = 16.3692 (4) Å

β = 106.570 (2)°

V = 2728.41 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 100.0 (1) K

0.60 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.871, T max = 0.974

31879 measured reflections

7997 independent reflections

4723 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.158

S = 1.07

7997 reflections

347 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.44 e Å−3

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/S1600536808020631/ci2626sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020631/ci2626Isup2.hkl

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

C15H14O3S	F000 = 1152
Mr = 274.32	Dx = 1.336 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3182 reflections
a = 12.1509 (3) Å	θ = 2.3–22.9º
b = 14.3118 (3) Å	µ = 0.24 mm−1
c = 16.3692 (4) Å	T = 100.0 (1) K
β = 106.570 (2)º	Needle, white
V = 2728.41 (11) Å3	0.60 × 0.17 × 0.11 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	7997 independent reflections
Radiation source: fine-focus sealed tube	4723 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.074
T = 100.0(1) K	θmax = 30.1º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −16→17
Tmin = 0.871, Tmax = 0.974	k = −20→20
31879 measured reflections	l = −23→23

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.0849P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
7997 reflections	Δρmax = 0.46 e Å−3
347 parameters	Δρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The 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
S1A	0.30263 (5)	0.34458 (4)	0.21155 (4)	0.03061 (17)
O1A	0.29234 (14)	0.52178 (12)	0.12000 (11)	0.0341 (4)
O2A	−0.29137 (13)	0.76488 (11)	−0.01772 (10)	0.0271 (4)
O3A	−0.23198 (13)	0.90679 (11)	−0.08963 (10)	0.0263 (4)
C1A	0.2263 (2)	0.26572 (18)	0.24872 (16)	0.0347 (6)
H1AA	0.2582	0.2124	0.2787	0.042*
C2A	0.1135 (2)	0.28805 (18)	0.23049 (18)	0.0381 (6)
H2AA	0.0602	0.2516	0.2470	0.046*
C3A	0.08511 (19)	0.37196 (15)	0.18408 (14)	0.0241 (5)
H3AA	0.0117	0.3975	0.1660	0.029*
C4A	0.18303 (19)	0.41151 (16)	0.16895 (14)	0.0254 (5)
C5A	0.1974 (2)	0.49958 (16)	0.12684 (14)	0.0261 (5)
C6A	0.09567 (19)	0.56023 (16)	0.09447 (14)	0.0276 (5)
H6AA	0.0244	0.5411	0.0987	0.033*
C7A	0.1065 (2)	0.64255 (17)	0.05911 (15)	0.0294 (5)
H7AA	0.1800	0.6572	0.0565	0.035*
C8A	0.01813 (19)	0.71264 (17)	0.02396 (14)	0.0273 (5)
C9A	0.0492 (2)	0.79240 (17)	−0.01259 (15)	0.0302 (5)
H9AA	0.1255	0.8011	−0.0114	0.036*
C10A	−0.03157 (19)	0.85911 (17)	−0.05077 (14)	0.0279 (5)
H10A	−0.0096	0.9119	−0.0753	0.034*
C11A	−0.14488 (19)	0.84704 (16)	−0.05229 (13)	0.0241 (5)
C12A	−0.17800 (18)	0.76786 (16)	−0.01398 (14)	0.0228 (5)
C13A	−0.09658 (19)	0.70150 (16)	0.02383 (14)	0.0248 (5)
H13A	−0.1181	0.6492	0.0493	0.030*
C14A	−0.3308 (2)	0.67985 (16)	0.01146 (17)	0.0321 (6)
H14A	−0.4124	0.6830	0.0020	0.048*
H14B	−0.2937	0.6720	0.0712	0.048*
H14C	−0.3127	0.6278	−0.0194	0.048*
C15A	−0.2024 (2)	0.98748 (17)	−0.13146 (16)	0.0323 (6)
H15A	−0.2698	1.0247	−0.1547	0.048*
H15B	−0.1719	0.9677	−0.1766	0.048*
H15C	−0.1459	1.0238	−0.0910	0.048*
S1B	0.37037 (5)	0.38880 (4)	0.72047 (4)	0.03122 (17)
O1B	0.16770 (14)	0.30240 (11)	0.59734 (11)	0.0326 (4)
O2B	−0.10219 (14)	0.60874 (11)	0.21110 (10)	0.0298 (4)
O3B	−0.24951 (13)	0.49172 (11)	0.12281 (10)	0.0307 (4)
C1B	0.45590 (19)	0.48496 (18)	0.73969 (15)	0.0318 (6)
H1BA	0.5199	0.4913	0.7868	0.038*
C2B	0.42056 (19)	0.55139 (17)	0.67877 (15)	0.0293 (5)
H2BA	0.4578	0.6082	0.6791	0.035*
C3B	0.32112 (18)	0.52442 (15)	0.61500 (14)	0.0236 (5)
H3BA	0.2847	0.5621	0.5690	0.028*
C4B	0.28323 (18)	0.43643 (15)	0.62777 (14)	0.0230 (5)
C5B	0.18737 (18)	0.38180 (16)	0.57549 (14)	0.0240 (5)
C6B	0.11733 (18)	0.42482 (16)	0.49650 (14)	0.0240 (5)
H6BA	0.1316	0.4863	0.4842	0.029*
C7B	0.03331 (19)	0.37724 (16)	0.44176 (15)	0.0262 (5)
H7BA	0.0214	0.3165	0.4577	0.031*
C8B	−0.04199 (18)	0.40867 (16)	0.36023 (14)	0.0236 (5)
C9B	−0.12424 (19)	0.34745 (16)	0.31244 (14)	0.0254 (5)
H9BA	−0.1315	0.2884	0.3340	0.030*
C10B	−0.19590 (19)	0.37269 (16)	0.23295 (14)	0.0249 (5)
H10B	−0.2502	0.3307	0.2018	0.030*
C11B	−0.18609 (18)	0.45996 (16)	0.20059 (14)	0.0237 (5)
C12B	−0.10419 (18)	0.52376 (15)	0.24885 (14)	0.0218 (5)
C13B	−0.03375 (18)	0.49828 (16)	0.32695 (14)	0.0231 (5)
H13B	0.0200	0.5406	0.3583	0.028*
C14B	−0.0190 (2)	0.67467 (17)	0.25647 (16)	0.0336 (6)
H14D	−0.0230	0.7300	0.2226	0.050*
H14E	0.0563	0.6478	0.2683	0.050*
H14F	−0.0345	0.6906	0.3091	0.050*
C15B	−0.3363 (2)	0.43030 (18)	0.07416 (16)	0.0374 (6)
H15D	−0.3730	0.4583	0.0199	0.056*
H15E	−0.3923	0.4193	0.1043	0.056*
H15F	−0.3020	0.3720	0.0656	0.056*

	U11	U22	U33	U12	U13	U23
S1A	0.0259 (3)	0.0293 (3)	0.0321 (3)	0.0024 (2)	0.0008 (2)	−0.0001 (3)
O1A	0.0258 (9)	0.0367 (10)	0.0373 (10)	0.0039 (7)	0.0047 (7)	0.0070 (8)
O2A	0.0241 (8)	0.0226 (9)	0.0342 (9)	0.0016 (7)	0.0076 (7)	0.0018 (7)
O3A	0.0254 (8)	0.0255 (9)	0.0270 (9)	0.0027 (7)	0.0060 (7)	0.0050 (7)
C1A	0.0423 (15)	0.0250 (13)	0.0364 (15)	0.0033 (11)	0.0104 (12)	−0.0002 (11)
C2A	0.0387 (15)	0.0299 (15)	0.0513 (17)	−0.0063 (11)	0.0219 (13)	−0.0096 (13)
C3A	0.0225 (11)	0.0194 (12)	0.0285 (12)	0.0018 (9)	0.0041 (9)	−0.0080 (10)
C4A	0.0240 (11)	0.0258 (13)	0.0236 (12)	0.0038 (9)	0.0021 (9)	−0.0081 (10)
C5A	0.0283 (12)	0.0251 (13)	0.0205 (11)	0.0043 (10)	0.0001 (9)	−0.0052 (10)
C6A	0.0247 (11)	0.0285 (14)	0.0261 (12)	0.0042 (10)	0.0015 (9)	−0.0030 (10)
C7A	0.0256 (12)	0.0331 (14)	0.0261 (13)	0.0038 (10)	0.0017 (10)	−0.0016 (11)
C8A	0.0245 (11)	0.0309 (14)	0.0214 (12)	0.0037 (10)	−0.0015 (9)	−0.0015 (10)
C9A	0.0237 (12)	0.0369 (15)	0.0271 (13)	0.0002 (10)	0.0027 (10)	0.0032 (11)
C10A	0.0276 (12)	0.0289 (13)	0.0251 (12)	−0.0016 (10)	0.0040 (10)	0.0036 (10)
C11A	0.0262 (11)	0.0273 (13)	0.0157 (11)	0.0042 (10)	0.0009 (9)	−0.0006 (9)
C12A	0.0229 (11)	0.0249 (12)	0.0203 (11)	0.0015 (9)	0.0054 (9)	−0.0034 (9)
C13A	0.0300 (12)	0.0215 (12)	0.0220 (12)	0.0008 (9)	0.0059 (9)	−0.0002 (9)
C14A	0.0343 (13)	0.0246 (13)	0.0423 (15)	−0.0019 (10)	0.0185 (12)	0.0014 (11)
C15A	0.0313 (13)	0.0298 (14)	0.0351 (14)	0.0028 (10)	0.0082 (11)	0.0120 (11)
S1B	0.0260 (3)	0.0321 (4)	0.0313 (3)	0.0046 (2)	0.0013 (2)	0.0055 (3)
O1B	0.0321 (9)	0.0229 (9)	0.0387 (10)	−0.0015 (7)	0.0036 (8)	0.0055 (8)
O2B	0.0342 (9)	0.0224 (9)	0.0284 (9)	−0.0067 (7)	0.0017 (7)	0.0020 (7)
O3B	0.0332 (9)	0.0256 (9)	0.0260 (9)	−0.0052 (7)	−0.0034 (7)	0.0010 (7)
C1B	0.0221 (11)	0.0390 (15)	0.0312 (13)	0.0035 (10)	0.0027 (10)	−0.0071 (12)
C2B	0.0239 (11)	0.0277 (13)	0.0344 (13)	−0.0022 (10)	0.0054 (10)	−0.0032 (11)
C3B	0.0219 (11)	0.0222 (12)	0.0243 (12)	0.0016 (9)	0.0027 (9)	0.0017 (10)
C4B	0.0227 (11)	0.0224 (12)	0.0233 (12)	0.0032 (9)	0.0058 (9)	−0.0011 (9)
C5B	0.0236 (11)	0.0230 (12)	0.0263 (12)	0.0019 (9)	0.0083 (9)	−0.0018 (10)
C6B	0.0253 (11)	0.0200 (12)	0.0253 (12)	−0.0010 (9)	0.0048 (9)	0.0014 (9)
C7B	0.0263 (12)	0.0198 (12)	0.0315 (13)	0.0013 (9)	0.0068 (10)	0.0034 (10)
C8B	0.0225 (11)	0.0257 (13)	0.0220 (11)	−0.0024 (9)	0.0053 (9)	−0.0029 (9)
C9B	0.0262 (11)	0.0233 (12)	0.0251 (12)	−0.0024 (9)	0.0048 (9)	0.0001 (10)
C10B	0.0240 (11)	0.0211 (12)	0.0274 (12)	−0.0037 (9)	0.0036 (9)	−0.0055 (10)
C11B	0.0229 (11)	0.0239 (12)	0.0218 (11)	0.0003 (9)	0.0025 (9)	−0.0007 (10)
C12B	0.0247 (11)	0.0164 (11)	0.0255 (12)	−0.0007 (9)	0.0091 (9)	0.0014 (9)
C13B	0.0229 (11)	0.0214 (12)	0.0240 (12)	−0.0037 (9)	0.0052 (9)	−0.0041 (9)
C14B	0.0400 (14)	0.0223 (13)	0.0343 (14)	−0.0124 (11)	0.0041 (11)	−0.0027 (11)
C15B	0.0413 (15)	0.0332 (15)	0.0284 (14)	−0.0105 (12)	−0.0051 (11)	0.0002 (11)

S1A—C1A	1.681 (3)	S1B—C1B	1.699 (3)
S1A—C4A	1.714 (2)	S1B—C4B	1.724 (2)
O1A—C5A	1.232 (3)	O1B—C5B	1.235 (3)
O2A—C12A	1.362 (2)	O2B—C12B	1.368 (3)
O2A—C14A	1.439 (3)	O2B—C14B	1.426 (3)
O3A—C11A	1.362 (3)	O3B—C11B	1.364 (3)
O3A—C15A	1.439 (3)	O3B—C15B	1.429 (3)
C1A—C2A	1.355 (3)	C1B—C2B	1.356 (3)
C1A—H1AA	0.93	C1B—H1BA	0.93
C2A—C3A	1.410 (3)	C2B—C3B	1.407 (3)
C2A—H2AA	0.93	C2B—H2BA	0.93
C3A—C4A	1.402 (3)	C3B—C4B	1.377 (3)
C3A—H3AA	0.93	C3B—H3BA	0.93
C4A—C5A	1.471 (3)	C4B—C5B	1.460 (3)
C5A—C6A	1.479 (3)	C5B—C6B	1.466 (3)
C6A—C7A	1.336 (3)	C6B—C7B	1.337 (3)
C6A—H6AA	0.93	C6B—H6BA	0.93
C7A—C8A	1.462 (3)	C7B—C8B	1.457 (3)
C7A—H7AA	0.93	C7B—H7BA	0.93
C8A—C9A	1.390 (3)	C8B—C9B	1.390 (3)
C8A—C13A	1.402 (3)	C8B—C13B	1.408 (3)
C9A—C10A	1.384 (3)	C9B—C10B	1.391 (3)
C9A—H9AA	0.93	C9B—H9BA	0.93
C10A—C11A	1.381 (3)	C10B—C11B	1.375 (3)
C10A—H10A	0.93	C10B—H10B	0.93
C11A—C12A	1.408 (3)	C11B—C12B	1.414 (3)
C12A—C13A	1.384 (3)	C12B—C13B	1.370 (3)
C13A—H13A	0.93	C13B—H13B	0.93
C14A—H14A	0.96	C14B—H14D	0.96
C14A—H14B	0.96	C14B—H14E	0.96
C14A—H14C	0.96	C14B—H14F	0.96
C15A—H15A	0.96	C15B—H15D	0.96
C15A—H15B	0.96	C15B—H15E	0.96
C15A—H15C	0.96	C15B—H15F	0.96
C1A—S1A—C4A	91.80 (12)	C1B—S1B—C4B	91.86 (12)
C12A—O2A—C14A	116.11 (17)	C12B—O2B—C14B	117.02 (18)
C11A—O3A—C15A	116.73 (17)	C11B—O3B—C15B	116.49 (18)
C2A—C1A—S1A	112.9 (2)	C2B—C1B—S1B	112.52 (18)
C2A—C1A—H1AA	123.5	C2B—C1B—H1BA	123.7
S1A—C1A—H1AA	123.5	S1B—C1B—H1BA	123.7
C1A—C2A—C3A	113.4 (2)	C1B—C2B—C3B	112.2 (2)
C1A—C2A—H2AA	123.3	C1B—C2B—H2BA	123.9
C3A—C2A—H2AA	123.3	C3B—C2B—H2BA	123.9
C4A—C3A—C2A	110.4 (2)	C4B—C3B—C2B	113.1 (2)
C4A—C3A—H3AA	124.8	C4B—C3B—H3BA	123.5
C2A—C3A—H3AA	124.8	C2B—C3B—H3BA	123.5
C3A—C4A—C5A	130.5 (2)	C3B—C4B—C5B	130.2 (2)
C3A—C4A—S1A	111.49 (18)	C3B—C4B—S1B	110.32 (17)
C5A—C4A—S1A	118.01 (16)	C5B—C4B—S1B	119.42 (17)
O1A—C5A—C4A	120.2 (2)	O1B—C5B—C4B	120.7 (2)
O1A—C5A—C6A	121.6 (2)	O1B—C5B—C6B	122.0 (2)
C4A—C5A—C6A	118.2 (2)	C4B—C5B—C6B	117.2 (2)
C7A—C6A—C5A	119.8 (2)	C7B—C6B—C5B	121.2 (2)
C7A—C6A—H6AA	120.1	C7B—C6B—H6BA	119.4
C5A—C6A—H6AA	120.1	C5B—C6B—H6BA	119.4
C6A—C7A—C8A	128.6 (2)	C6B—C7B—C8B	128.1 (2)
C6A—C7A—H7AA	115.7	C6B—C7B—H7BA	116.0
C8A—C7A—H7AA	115.7	C8B—C7B—H7BA	116.0
C9A—C8A—C13A	119.0 (2)	C9B—C8B—C13B	118.4 (2)
C9A—C8A—C7A	118.3 (2)	C9B—C8B—C7B	118.9 (2)
C13A—C8A—C7A	122.7 (2)	C13B—C8B—C7B	122.7 (2)
C10A—C9A—C8A	121.1 (2)	C8B—C9B—C10B	121.4 (2)
C10A—C9A—H9AA	119.5	C8B—C9B—H9BA	119.3
C8A—C9A—H9AA	119.5	C10B—C9B—H9BA	119.3
C11A—C10A—C9A	119.8 (2)	C11B—C10B—C9B	119.7 (2)
C11A—C10A—H10A	120.1	C11B—C10B—H10B	120.1
C9A—C10A—H10A	120.1	C9B—C10B—H10B	120.1
O3A—C11A—C10A	124.9 (2)	O3B—C11B—C10B	125.0 (2)
O3A—C11A—C12A	114.88 (19)	O3B—C11B—C12B	115.24 (19)
C10A—C11A—C12A	120.2 (2)	C10B—C11B—C12B	119.7 (2)
O2A—C12A—C13A	125.7 (2)	O2B—C12B—C13B	124.9 (2)
O2A—C12A—C11A	114.77 (19)	O2B—C12B—C11B	114.97 (19)
C13A—C12A—C11A	119.53 (19)	C13B—C12B—C11B	120.2 (2)
C12A—C13A—C8A	120.4 (2)	C12B—C13B—C8B	120.6 (2)
C12A—C13A—H13A	119.8	C12B—C13B—H13B	119.7
C8A—C13A—H13A	119.8	C8B—C13B—H13B	119.7
O2A—C14A—H14A	109.5	O2B—C14B—H14D	109.5
O2A—C14A—H14B	109.5	O2B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
O2A—C14A—H14C	109.5	O2B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
O3A—C15A—H15A	109.5	O3B—C15B—H15D	109.5
O3A—C15A—H15B	109.5	O3B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O3A—C15A—H15C	109.5	O3B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—S1A—C1A—C2A	−0.2 (2)	C4B—S1B—C1B—C2B	0.18 (19)
S1A—C1A—C2A—C3A	0.3 (3)	S1B—C1B—C2B—C3B	0.5 (3)
C1A—C2A—C3A—C4A	−0.3 (3)	C1B—C2B—C3B—C4B	−1.1 (3)
C2A—C3A—C4A—C5A	−177.2 (2)	C2B—C3B—C4B—C5B	−177.3 (2)
C2A—C3A—C4A—S1A	0.1 (2)	C2B—C3B—C4B—S1B	1.2 (2)
C1A—S1A—C4A—C3A	0.04 (18)	C1B—S1B—C4B—C3B	−0.78 (17)
C1A—S1A—C4A—C5A	177.78 (18)	C1B—S1B—C4B—C5B	177.88 (17)
C3A—C4A—C5A—O1A	−180.0 (2)	C3B—C4B—C5B—O1B	178.9 (2)
S1A—C4A—C5A—O1A	2.8 (3)	S1B—C4B—C5B—O1B	0.6 (3)
C3A—C4A—C5A—C6A	0.8 (3)	C3B—C4B—C5B—C6B	−0.5 (3)
S1A—C4A—C5A—C6A	−176.47 (16)	S1B—C4B—C5B—C6B	−178.83 (15)
O1A—C5A—C6A—C7A	−2.0 (3)	O1B—C5B—C6B—C7B	−4.4 (3)
C4A—C5A—C6A—C7A	177.2 (2)	C4B—C5B—C6B—C7B	175.0 (2)
C5A—C6A—C7A—C8A	−179.6 (2)	C5B—C6B—C7B—C8B	−178.5 (2)
C6A—C7A—C8A—C9A	−177.7 (2)	C6B—C7B—C8B—C9B	179.7 (2)
C6A—C7A—C8A—C13A	0.7 (4)	C6B—C7B—C8B—C13B	0.8 (4)
C13A—C8A—C9A—C10A	−1.7 (3)	C13B—C8B—C9B—C10B	1.1 (3)
C7A—C8A—C9A—C10A	176.7 (2)	C7B—C8B—C9B—C10B	−177.9 (2)
C8A—C9A—C10A—C11A	0.5 (4)	C8B—C9B—C10B—C11B	−0.2 (3)
C15A—O3A—C11A—C10A	1.0 (3)	C15B—O3B—C11B—C10B	3.4 (3)
C15A—O3A—C11A—C12A	−178.46 (19)	C15B—O3B—C11B—C12B	−177.40 (19)
C9A—C10A—C11A—O3A	−178.4 (2)	C9B—C10B—C11B—O3B	178.4 (2)
C9A—C10A—C11A—C12A	1.0 (3)	C9B—C10B—C11B—C12B	−0.8 (3)
C14A—O2A—C12A—C13A	−7.8 (3)	C14B—O2B—C12B—C13B	1.0 (3)
C14A—O2A—C12A—C11A	172.71 (19)	C14B—O2B—C12B—C11B	−178.52 (19)
O3A—C11A—C12A—O2A	−2.1 (3)	O3B—C11B—C12B—O2B	1.3 (3)
C10A—C11A—C12A—O2A	178.4 (2)	C10B—C11B—C12B—O2B	−179.50 (19)
O3A—C11A—C12A—C13A	178.34 (19)	O3B—C11B—C12B—C13B	−178.29 (18)
C10A—C11A—C12A—C13A	−1.1 (3)	C10B—C11B—C12B—C13B	1.0 (3)
O2A—C12A—C13A—C8A	−179.7 (2)	O2B—C12B—C13B—C8B	−179.62 (19)
C11A—C12A—C13A—C8A	−0.2 (3)	C11B—C12B—C13B—C8B	−0.1 (3)
C9A—C8A—C13A—C12A	1.6 (3)	C9B—C8B—C13B—C12B	−0.9 (3)
C7A—C8A—C13A—C12A	−176.8 (2)	C7B—C8B—C13B—C12B	178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AA···O1A	0.93	2.43	2.792 (3)	103
C1B—H1BA···O1Ai	0.93	2.36	3.261 (3)	162
C7B—H7BA···O1B	0.93	2.47	2.816 (3)	102
C14B—H14F···O1Bii	0.96	2.53	3.401 (3)	151
C15A—H15A···Cg1iii	0.96	2.92	3.616 (3)	130
C10A—H10A···Cg3iv	0.93	2.84	3.636 (3)	144
C3A—H3AA···Cg4	0.93	2.79	3.370 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7AA⋯O1A	0.93	2.43	2.792 (3)	103
C1B—H1BA⋯O1Ai	0.93	2.36	3.261 (3)	162
C7B—H7BA⋯O1B	0.93	2.47	2.816 (3)	102
C14B—H14F⋯O1Bii	0.96	2.53	3.401 (3)	151
C15A—H15A⋯Cg1iii	0.96	2.92	3.616 (3)	130
C10A—H10A⋯Cg3iv	0.93	2.84	3.636 (3)	144
C3A—H3AA⋯Cg4	0.93	2.79	3.370 (3)	122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1, Cg3 and Cg4 are the centroids of the S1A/C1A–C4A, S1B/C1B–C4B and C8B–C13B rings, respectively.