(E)-1-(Thio-phen-2-yl)-3-(2,4,6-tri-meth-oxy-phen-yl)prop-2-en-1-one.

There are two crystallograpically independent mol-ecules in the asymmetric unit of the title heteroaryl chalcone derivative, C(16)H(16)O(4)S, with slightly different conformations. The thienyl ring of one mol-ecule is disordered over two positions, with a refined site-occupancy ratio of 0.713 (5):0.287 (5). The mol-ecules are twisted: the dihedral angle between the thienyl and benzene rings is 9.72 (19)° in the ordered mol-ecule, and 3.8 (4) and 2.1 (8)° for the major and minor components, respectively, in the disordered mol-ecule. In both mol-ecules, all three substituted meth-oxy groups are coplanar with the benzene ring to which they are attached. In each mol-ecule, a weak intra-molecular C-H⋯O inter-action generates an S(6) ring motif. In the crystal structure, adjacent mol-ecules are linked into a three-dimensional network by weak C-H⋯O inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2009 ▶); Fun et al. (2010 ▶, 2011 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Go et al. (2005 ▶); Liu et al. (2008 ▶); Ng et al. (2009 ▶); Ni et al. (2004 ▶); Suwunwong et al. (2011 ▶); Tewtrakul et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H16O4S

M = 304.36

Orthorhombic,

a = 22.8482 (10) Å

b = 31.2117 (13) Å

c = 3.9876 (2) Å

V = 2843.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.60 × 0.06 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.869, T max = 0.988

20029 measured reflections

8085 independent reflections

5348 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.178

S = 1.01

8085 reflections

402 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), with 3389 Friedel pairs

Flack parameter: 0.09 (11)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536811042930/rz2650sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042930/rz2650Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042930/rz2650Isup3.cml

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

C16H16O4S	Dx = 1.422 Mg m−3
Mr = 304.36	Melting point = 381–382 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8085 reflections
a = 22.8482 (10) Å	θ = 1.3–30.0°
b = 31.2117 (13) Å	µ = 0.24 mm−1
c = 3.9876 (2) Å	T = 100 K
V = 2843.7 (2) Å3	Needle, pale yellow
Z = 8	0.60 × 0.06 × 0.05 mm
F(000) = 1280

Bruker APEXII CCD area-detector diffractometer	8085 independent reflections
Radiation source: sealed tube	5348 reflections with I > 2σ(I)
graphite	Rint = 0.065
φ and ω scans	θmax = 30.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→32
Tmin = 0.869, Tmax = 0.988	k = −43→40
20029 measured reflections	l = −5→5

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.178	w = 1/[σ2(Fo2) + (0.0951P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
8085 reflections	Δρmax = 1.08 e Å−3
402 parameters	Δρmin = −0.56 e Å−3
1 restraint	Absolute structure: Flack (1983), with 3389 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (11)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
S1A	0.13970 (4)	0.41398 (3)	1.0329 (3)	0.0270 (2)
O1A	0.21057 (10)	0.48128 (7)	0.7262 (8)	0.0228 (6)
O2A	0.27887 (11)	0.61480 (7)	0.4202 (7)	0.0213 (6)
O3A	0.19621 (10)	0.75129 (7)	0.6341 (7)	0.0206 (6)
O4A	0.09780 (10)	0.62191 (7)	0.9862 (7)	0.0211 (6)
C1A	0.07345 (15)	0.40255 (11)	1.2033 (10)	0.0217 (8)
H1A	0.0622	0.3752	1.2684	0.026*
C2A	0.03841 (16)	0.43786 (10)	1.2349 (11)	0.0241 (8)
H2A	0.0005	0.4367	1.3198	0.029*
C3A	0.06544 (15)	0.47698 (12)	1.1249 (10)	0.0236 (8)
H3A	0.0483	0.5040	1.1312	0.028*
C4A	0.12232 (15)	0.46779 (10)	1.0057 (10)	0.0192 (7)
C5A	0.16654 (15)	0.49669 (10)	0.8497 (10)	0.0198 (7)
C6A	0.15415 (15)	0.54312 (10)	0.8687 (10)	0.0209 (8)
H6A	0.1214	0.5529	0.9841	0.025*
C7A	0.19013 (15)	0.57103 (10)	0.7198 (10)	0.0187 (7)
H7A	0.2213	0.5587	0.6051	0.022*
C8A	0.18848 (15)	0.61784 (10)	0.7077 (10)	0.0166 (7)
C9A	0.23464 (15)	0.64009 (10)	0.5441 (10)	0.0175 (7)
C10A	0.23602 (15)	0.68428 (10)	0.5233 (10)	0.0177 (7)
H10A	0.2669	0.6980	0.4162	0.021*
C11A	0.19052 (15)	0.70813 (10)	0.6647 (10)	0.0170 (7)
C12A	0.14394 (15)	0.68798 (10)	0.8199 (10)	0.0190 (7)
H12A	0.1135	0.7040	0.9108	0.023*
C13A	0.14324 (14)	0.64351 (10)	0.8385 (10)	0.0185 (7)
C14A	0.32476 (14)	0.63633 (10)	0.2398 (10)	0.0190 (7)
H14A	0.3511	0.6155	0.1470	0.029*
H14B	0.3458	0.6548	0.3900	0.029*
H14C	0.3080	0.6531	0.0619	0.029*
C15A	0.15164 (15)	0.77720 (10)	0.7938 (11)	0.0208 (8)
H15A	0.1602	0.8070	0.7584	0.031*
H15B	0.1511	0.7713	1.0300	0.031*
H15C	0.1141	0.7705	0.6989	0.031*
C16A	0.05059 (16)	0.64661 (11)	1.1205 (11)	0.0232 (8)
H16A	0.0221	0.6278	1.2182	0.035*
H16B	0.0327	0.6629	0.9441	0.035*
H16C	0.0653	0.6657	1.2892	0.035*
S1B	0.42377 (10)	0.79935 (8)	1.2577 (7)	0.0198 (5)	0.713 (5)
O1B	0.52996 (11)	0.74766 (7)	1.3193 (8)	0.0283 (7)
O2B	0.65708 (9)	0.63419 (7)	1.2581 (7)	0.0199 (6)
O3B	0.62447 (10)	0.49871 (7)	0.7051 (7)	0.0192 (5)
O4B	0.47249 (10)	0.60034 (7)	0.8092 (7)	0.0194 (5)
C1B	0.3535 (4)	0.8012 (3)	1.105 (2)	0.0191 (18)	0.713 (5)
H1B	0.3290	0.8248	1.1252	0.023*	0.713 (5)
C2B	0.3376 (4)	0.7629 (3)	0.947 (3)	0.027 (2)	0.713 (5)
H2B	0.3018	0.7578	0.8433	0.032*	0.713 (5)
C3B	0.3838 (5)	0.7331 (4)	0.968 (3)	0.032 (3)	0.713 (5)
H3B	0.3804	0.7050	0.8923	0.038*	0.713 (5)
S1X	0.3779 (3)	0.7288 (2)	0.9029 (17)	0.0168 (13)*	0.287 (5)
C1X	0.3356 (11)	0.7722 (7)	0.978 (7)	0.013 (5)*	0.287 (5)
H1BX	0.2977	0.7753	0.8964	0.015*	0.287 (5)
C2X	0.3631 (11)	0.8023 (9)	1.170 (6)	0.018 (6)*	0.287 (5)
H2BX	0.3451	0.8268	1.2552	0.022*	0.287 (5)
C3X	0.4244 (12)	0.7909 (7)	1.225 (7)	0.014 (6)*	0.287 (5)
H3BX	0.4524	0.8086	1.3225	0.017*	0.287 (5)
C4B	0.43447 (15)	0.74896 (10)	1.1089 (10)	0.0189 (7)
C5B	0.49125 (15)	0.72746 (10)	1.1768 (10)	0.0195 (8)
C6B	0.49764 (15)	0.68308 (10)	1.0567 (11)	0.0213 (8)
H6B	0.4682	0.6704	0.9301	0.026*
C7B	0.54678 (15)	0.66094 (10)	1.1323 (10)	0.0200 (8)
H7B	0.5731	0.6754	1.2698	0.024*
C8B	0.56499 (15)	0.61804 (9)	1.0324 (10)	0.0175 (7)
C9B	0.62300 (16)	0.60488 (10)	1.0981 (10)	0.0188 (7)
C10B	0.64515 (15)	0.56527 (10)	0.9991 (11)	0.0192 (7)
H10B	0.6836	0.5575	1.0465	0.023*
C11B	0.60766 (15)	0.53768 (10)	0.8260 (10)	0.0182 (7)
C12B	0.54957 (14)	0.54812 (10)	0.7577 (10)	0.0176 (7)
H12B	0.5253	0.5291	0.6446	0.021*
C13B	0.52869 (15)	0.58828 (11)	0.8645 (10)	0.0184 (7)
C14B	0.71693 (15)	0.62351 (11)	1.3201 (11)	0.0239 (8)
H14D	0.7362	0.6474	1.4246	0.036*
H14E	0.7360	0.6169	1.1117	0.036*
H14F	0.7188	0.5991	1.4657	0.036*
C15B	0.68437 (15)	0.48626 (11)	0.7563 (12)	0.0270 (9)
H15D	0.6916	0.4596	0.6443	0.040*
H15E	0.6917	0.4830	0.9920	0.040*
H15F	0.7098	0.5079	0.6669	0.040*
C16B	0.43513 (15)	0.57035 (11)	0.6405 (10)	0.0209 (8)
H16D	0.3961	0.5817	0.6297	0.031*
H16E	0.4348	0.5438	0.7615	0.031*
H16F	0.4495	0.5655	0.4174	0.031*

	U11	U22	U33	U12	U13	U23
S1A	0.0279 (5)	0.0170 (4)	0.0359 (6)	−0.0005 (4)	0.0025 (5)	0.0010 (4)
O1A	0.0172 (11)	0.0159 (11)	0.0354 (17)	0.0015 (9)	0.0028 (12)	−0.0011 (11)
O2A	0.0188 (12)	0.0160 (11)	0.0290 (15)	0.0019 (9)	0.0044 (11)	0.0041 (10)
O3A	0.0194 (12)	0.0099 (10)	0.0326 (16)	0.0006 (9)	0.0018 (11)	0.0029 (10)
O4A	0.0174 (12)	0.0135 (11)	0.0324 (16)	−0.0022 (9)	0.0064 (12)	−0.0005 (11)
C1A	0.0233 (17)	0.0186 (16)	0.023 (2)	−0.0046 (14)	0.0012 (16)	0.0030 (14)
C2A	0.0229 (17)	0.0171 (16)	0.032 (2)	−0.0014 (13)	0.0067 (18)	0.0011 (16)
C3A	0.0213 (18)	0.0237 (17)	0.026 (2)	−0.0096 (14)	0.0046 (16)	0.0041 (15)
C4A	0.0231 (17)	0.0125 (14)	0.0219 (19)	−0.0005 (12)	−0.0008 (16)	−0.0015 (14)
C5A	0.0195 (17)	0.0135 (15)	0.026 (2)	0.0001 (12)	−0.0029 (16)	−0.0021 (14)
C6A	0.0208 (17)	0.0131 (15)	0.029 (2)	0.0009 (12)	0.0005 (16)	−0.0023 (14)
C7A	0.0206 (16)	0.0141 (14)	0.0214 (19)	0.0022 (12)	0.0010 (15)	0.0019 (15)
C8A	0.0159 (15)	0.0132 (14)	0.0207 (19)	−0.0015 (12)	−0.0011 (14)	−0.0012 (13)
C9A	0.0201 (16)	0.0141 (14)	0.0181 (18)	0.0018 (12)	−0.0025 (15)	0.0027 (14)
C10A	0.0186 (16)	0.0145 (14)	0.0199 (18)	−0.0024 (12)	−0.0009 (15)	0.0019 (14)
C11A	0.0148 (15)	0.0098 (14)	0.026 (2)	0.0010 (12)	−0.0032 (14)	0.0013 (13)
C12A	0.0163 (15)	0.0144 (15)	0.026 (2)	0.0043 (12)	−0.0027 (15)	0.0001 (14)
C13A	0.0123 (15)	0.0177 (15)	0.026 (2)	−0.0050 (12)	−0.0013 (14)	0.0003 (14)
C14A	0.0170 (16)	0.0170 (15)	0.023 (2)	0.0005 (12)	0.0005 (16)	0.0023 (15)
C15A	0.0229 (17)	0.0099 (14)	0.030 (2)	0.0017 (12)	−0.0045 (16)	0.0019 (15)
C16A	0.0217 (18)	0.0180 (16)	0.030 (2)	−0.0017 (13)	0.0027 (16)	−0.0041 (15)
S1B	0.0189 (8)	0.0084 (8)	0.0322 (10)	0.0019 (7)	0.0018 (7)	−0.0026 (8)
O1B	0.0207 (12)	0.0134 (11)	0.051 (2)	0.0005 (9)	−0.0075 (14)	−0.0025 (12)
O2B	0.0140 (11)	0.0120 (10)	0.0339 (16)	−0.0022 (8)	−0.0061 (12)	−0.0020 (11)
O3B	0.0193 (12)	0.0106 (10)	0.0276 (15)	0.0017 (8)	−0.0013 (11)	0.0009 (10)
O4B	0.0166 (11)	0.0112 (10)	0.0304 (16)	−0.0005 (8)	−0.0018 (11)	−0.0001 (10)
C1B	0.016 (4)	0.020 (3)	0.022 (5)	0.005 (2)	−0.004 (3)	0.005 (3)
C2B	0.027 (4)	0.020 (4)	0.033 (5)	−0.004 (3)	0.003 (3)	−0.008 (4)
C3B	0.044 (5)	0.021 (4)	0.031 (6)	0.004 (3)	−0.007 (4)	0.001 (4)
C4B	0.0195 (17)	0.0149 (15)	0.022 (2)	−0.0038 (13)	0.0001 (15)	0.0014 (14)
C5B	0.0176 (16)	0.0120 (15)	0.029 (2)	−0.0003 (13)	0.0051 (15)	0.0019 (13)
C6B	0.0210 (17)	0.0118 (14)	0.031 (2)	−0.0005 (12)	−0.0013 (17)	−0.0014 (16)
C7B	0.0179 (16)	0.0152 (15)	0.027 (2)	−0.0043 (13)	−0.0013 (15)	−0.0005 (14)
C8B	0.0196 (16)	0.0113 (13)	0.0215 (18)	−0.0004 (12)	0.0031 (15)	−0.0009 (14)
C9B	0.0216 (17)	0.0143 (15)	0.020 (2)	−0.0038 (13)	0.0010 (15)	0.0039 (13)
C10B	0.0184 (16)	0.0136 (15)	0.026 (2)	−0.0001 (12)	0.0005 (16)	0.0022 (15)
C11B	0.0218 (17)	0.0103 (14)	0.022 (2)	−0.0003 (12)	0.0023 (15)	0.0003 (13)
C12B	0.0196 (15)	0.0103 (13)	0.0229 (19)	−0.0015 (12)	−0.0013 (16)	0.0023 (14)
C13B	0.0198 (17)	0.0169 (15)	0.0184 (18)	−0.0013 (13)	0.0021 (15)	−0.0001 (14)
C14B	0.0178 (16)	0.0197 (16)	0.034 (2)	−0.0041 (13)	−0.0060 (17)	0.0000 (16)
C15B	0.0227 (18)	0.0125 (15)	0.046 (3)	0.0051 (13)	−0.0004 (19)	0.0013 (18)
C16B	0.0190 (17)	0.0185 (16)	0.025 (2)	−0.0040 (13)	−0.0026 (15)	0.0000 (14)

S1A—C1A	1.697 (4)	O2B—C14B	1.429 (4)
S1A—C4A	1.729 (3)	O3B—C11B	1.364 (4)
O1A—C5A	1.219 (4)	O3B—C15B	1.437 (4)
O2A—C9A	1.374 (4)	O4B—C13B	1.356 (4)
O2A—C14A	1.438 (4)	O4B—C16B	1.434 (4)
O3A—C11A	1.359 (4)	C1B—C2B	1.399 (13)
O3A—C15A	1.448 (4)	C1B—H1B	0.9300
O4A—C13A	1.371 (4)	C2B—C3B	1.408 (15)
O4A—C16A	1.430 (4)	C2B—H2B	0.9300
C1A—C2A	1.368 (5)	C3B—C4B	1.380 (12)
C1A—H1A	0.9300	C3B—H3B	0.9300
C2A—C3A	1.437 (5)	S1X—C4B	1.657 (7)
C2A—H2A	0.9300	S1X—C1X	1.69 (2)
C3A—C4A	1.413 (5)	C1X—C2X	1.37 (3)
C3A—H3A	0.9300	C1X—H1BX	0.9300
C4A—C5A	1.491 (5)	C2X—C3X	1.46 (3)
C5A—C6A	1.478 (4)	C2X—H2BX	0.9300
C6A—C7A	1.337 (5)	C3X—C4B	1.41 (2)
C6A—H6A	0.9300	C3X—H3BX	0.9300
C7A—C8A	1.462 (4)	C4B—C5B	1.485 (5)
C7A—H7A	0.9300	C5B—C6B	1.473 (5)
C8A—C13A	1.408 (5)	C6B—C7B	1.353 (5)
C8A—C9A	1.421 (5)	C6B—H6B	0.9300
C9A—C10A	1.382 (4)	C7B—C8B	1.458 (4)
C10A—C11A	1.397 (5)	C7B—H7B	0.9300
C10A—H10A	0.9300	C8B—C9B	1.412 (5)
C11A—C12A	1.383 (5)	C8B—C13B	1.414 (5)
C12A—C13A	1.390 (4)	C9B—C10B	1.393 (5)
C12A—H12A	0.9300	C10B—C11B	1.397 (5)
C14A—H14A	0.9600	C10B—H10B	0.9300
C14A—H14B	0.9600	C11B—C12B	1.394 (5)
C14A—H14C	0.9600	C12B—C13B	1.407 (5)
C15A—H15A	0.9600	C12B—H12B	0.9300
C15A—H15B	0.9600	C14B—H14D	0.9600
C15A—H15C	0.9600	C14B—H14E	0.9600
C16A—H16A	0.9600	C14B—H14F	0.9600
C16A—H16B	0.9600	C15B—H15D	0.9600
C16A—H16C	0.9600	C15B—H15E	0.9600
S1B—C4B	1.699 (4)	C15B—H15F	0.9600
S1B—C1B	1.717 (10)	C16B—H16D	0.9600
O1B—C5B	1.226 (4)	C16B—H16E	0.9600
O2B—C9B	1.360 (4)	C16B—H16F	0.9600
C1A—S1A—C4A	91.40 (17)	C1B—C2B—H2B	125.0
C9A—O2A—C14A	116.6 (3)	C3B—C2B—H2B	125.0
C11A—O3A—C15A	116.5 (3)	C4B—C3B—C2B	114.6 (9)
C13A—O4A—C16A	117.8 (3)	C4B—C3B—H3B	122.7
C2A—C1A—S1A	112.9 (3)	C2B—C3B—H3B	122.7
C2A—C1A—H1A	123.5	C4B—S1X—C1X	93.0 (9)
S1A—C1A—H1A	123.5	C2X—C1X—S1X	113 (2)
C1A—C2A—C3A	113.9 (3)	C2X—C1X—H1BX	123.6
C1A—C2A—H2A	123.1	S1X—C1X—H1BX	123.6
C3A—C2A—H2A	123.1	C1X—C2X—C3X	111 (2)
C4A—C3A—C2A	109.0 (3)	C1X—C2X—H2BX	124.6
C4A—C3A—H3A	125.5	C3X—C2X—H2BX	124.6
C2A—C3A—H3A	125.5	C4B—C3X—C2X	110 (2)
C3A—C4A—C5A	129.9 (3)	C4B—C3X—H3BX	125.2
C3A—C4A—S1A	112.8 (3)	C2X—C3X—H3BX	125.2
C5A—C4A—S1A	117.3 (3)	C3B—C4B—C3X	109.3 (12)
O1A—C5A—C6A	124.4 (3)	C3B—C4B—C5B	130.2 (6)
O1A—C5A—C4A	119.3 (3)	C3X—C4B—C5B	120.2 (12)
C6A—C5A—C4A	116.2 (3)	C3X—C4B—S1X	112.9 (12)
C7A—C6A—C5A	119.9 (3)	C5B—C4B—S1X	126.9 (4)
C7A—C6A—H6A	120.1	C3B—C4B—S1B	110.7 (5)
C5A—C6A—H6A	120.1	C5B—C4B—S1B	118.7 (3)
C6A—C7A—C8A	130.5 (3)	S1X—C4B—S1B	114.4 (3)
C6A—C7A—H7A	114.7	O1B—C5B—C6B	124.3 (3)
C8A—C7A—H7A	114.7	O1B—C5B—C4B	118.8 (3)
C13A—C8A—C9A	115.9 (3)	C6B—C5B—C4B	116.9 (3)
C13A—C8A—C7A	125.1 (3)	C7B—C6B—C5B	119.4 (3)
C9A—C8A—C7A	119.0 (3)	C7B—C6B—H6B	120.3
O2A—C9A—C10A	122.3 (3)	C5B—C6B—H6B	120.3
O2A—C9A—C8A	115.5 (3)	C6B—C7B—C8B	130.2 (3)
C10A—C9A—C8A	122.1 (3)	C6B—C7B—H7B	114.9
C9A—C10A—C11A	119.4 (3)	C8B—C7B—H7B	114.9
C9A—C10A—H10A	120.3	C9B—C8B—C13B	116.6 (3)
C11A—C10A—H10A	120.3	C9B—C8B—C7B	119.0 (3)
O3A—C11A—C12A	124.4 (3)	C13B—C8B—C7B	124.4 (3)
O3A—C11A—C10A	114.9 (3)	O2B—C9B—C10B	121.5 (3)
C12A—C11A—C10A	120.7 (3)	O2B—C9B—C8B	115.4 (3)
C11A—C12A—C13A	119.1 (3)	C10B—C9B—C8B	123.1 (3)
C11A—C12A—H12A	120.4	C9B—C10B—C11B	117.7 (3)
C13A—C12A—H12A	120.4	C9B—C10B—H10B	121.2
O4A—C13A—C12A	121.5 (3)	C11B—C10B—H10B	121.2
O4A—C13A—C8A	115.8 (3)	O3B—C11B—C12B	114.1 (3)
C12A—C13A—C8A	122.7 (3)	O3B—C11B—C10B	123.5 (3)
O2A—C14A—H14A	109.5	C12B—C11B—C10B	122.4 (3)
O2A—C14A—H14B	109.5	C11B—C12B—C13B	118.2 (3)
H14A—C14A—H14B	109.5	C11B—C12B—H12B	120.9
O2A—C14A—H14C	109.5	C13B—C12B—H12B	120.9
H14A—C14A—H14C	109.5	O4B—C13B—C12B	121.3 (3)
H14B—C14A—H14C	109.5	O4B—C13B—C8B	116.7 (3)
O3A—C15A—H15A	109.5	C12B—C13B—C8B	122.0 (3)
O3A—C15A—H15B	109.5	O2B—C14B—H14D	109.5
H15A—C15A—H15B	109.5	O2B—C14B—H14E	109.5
O3A—C15A—H15C	109.5	H14D—C14B—H14E	109.5
H15A—C15A—H15C	109.5	O2B—C14B—H14F	109.5
H15B—C15A—H15C	109.5	H14D—C14B—H14F	109.5
O4A—C16A—H16A	109.5	H14E—C14B—H14F	109.5
O4A—C16A—H16B	109.5	O3B—C15B—H15D	109.5
H16A—C16A—H16B	109.5	O3B—C15B—H15E	109.5
O4A—C16A—H16C	109.5	H15D—C15B—H15E	109.5
H16A—C16A—H16C	109.5	O3B—C15B—H15F	109.5
H16B—C16A—H16C	109.5	H15D—C15B—H15F	109.5
C4B—S1B—C1B	92.4 (4)	H15E—C15B—H15F	109.5
C9B—O2B—C14B	118.2 (3)	O4B—C16B—H16D	109.5
C11B—O3B—C15B	117.3 (3)	O4B—C16B—H16E	109.5
C13B—O4B—C16B	117.3 (3)	H16D—C16B—H16E	109.5
C2B—C1B—S1B	112.0 (7)	O4B—C16B—H16F	109.5
C2B—C1B—H1B	124.0	H16D—C16B—H16F	109.5
S1B—C1B—H1B	124.0	H16E—C16B—H16F	109.5
C1B—C2B—C3B	110.0 (10)
C4A—S1A—C1A—C2A	1.0 (3)	C2B—C3B—C4B—S1B	6.2 (11)
S1A—C1A—C2A—C3A	−1.3 (5)	C2X—C3X—C4B—C3B	3(2)
C1A—C2A—C3A—C4A	0.9 (5)	C2X—C3X—C4B—C5B	−171.8 (15)
C2A—C3A—C4A—C5A	176.5 (4)	C2X—C3X—C4B—S1X	8(2)
C2A—C3A—C4A—S1A	−0.2 (5)	C1X—S1X—C4B—C3B	51 (7)
C1A—S1A—C4A—C3A	−0.5 (3)	C1X—S1X—C4B—C3X	−3.7 (16)
C1A—S1A—C4A—C5A	−177.6 (3)	C1X—S1X—C4B—C5B	176.0 (10)
C3A—C4A—C5A—O1A	−171.1 (4)	C1X—S1X—C4B—S1B	−3.0 (10)
S1A—C4A—C5A—O1A	5.4 (5)	C1B—S1B—C4B—C3B	−4.2 (7)
C3A—C4A—C5A—C6A	11.1 (6)	C1B—S1B—C4B—C5B	−178.0 (4)
S1A—C4A—C5A—C6A	−172.3 (3)	C1B—S1B—C4B—S1X	1.1 (5)
O1A—C5A—C6A—C7A	5.8 (6)	C3B—C4B—C5B—O1B	−176.9 (7)
C4A—C5A—C6A—C7A	−176.6 (4)	C3X—C4B—C5B—O1B	−3.9 (14)
C5A—C6A—C7A—C8A	−178.5 (4)	S1X—C4B—C5B—O1B	176.4 (5)
C6A—C7A—C8A—C13A	−5.4 (7)	S1B—C4B—C5B—O1B	−4.6 (5)
C6A—C7A—C8A—C9A	176.6 (4)	C3B—C4B—C5B—C6B	4.9 (9)
C14A—O2A—C9A—C10A	−5.3 (5)	C3X—C4B—C5B—C6B	177.9 (13)
C14A—O2A—C9A—C8A	177.2 (3)	S1X—C4B—C5B—C6B	−1.7 (6)
C13A—C8A—C9A—O2A	179.4 (3)	S1B—C4B—C5B—C6B	177.3 (3)
C7A—C8A—C9A—O2A	−2.4 (5)	O1B—C5B—C6B—C7B	6.6 (6)
C13A—C8A—C9A—C10A	1.9 (5)	C4B—C5B—C6B—C7B	−175.3 (4)
C7A—C8A—C9A—C10A	−179.9 (4)	C5B—C6B—C7B—C8B	−176.7 (4)
O2A—C9A—C10A—C11A	−177.8 (4)	C6B—C7B—C8B—C9B	169.3 (4)
C8A—C9A—C10A—C11A	−0.5 (6)	C6B—C7B—C8B—C13B	−9.2 (7)
C15A—O3A—C11A—C12A	3.7 (5)	C14B—O2B—C9B—C10B	0.6 (5)
C15A—O3A—C11A—C10A	−176.6 (3)	C14B—O2B—C9B—C8B	−177.6 (3)
C9A—C10A—C11A—O3A	179.4 (3)	C13B—C8B—C9B—O2B	179.6 (3)
C9A—C10A—C11A—C12A	−1.0 (6)	C7B—C8B—C9B—O2B	1.0 (5)
O3A—C11A—C12A—C13A	−179.4 (3)	C13B—C8B—C9B—C10B	1.5 (6)
C10A—C11A—C12A—C13A	1.0 (6)	C7B—C8B—C9B—C10B	−177.1 (4)
C16A—O4A—C13A—C12A	0.3 (5)	O2B—C9B—C10B—C11B	−177.9 (3)
C16A—O4A—C13A—C8A	−179.5 (3)	C8B—C9B—C10B—C11B	0.2 (6)
C11A—C12A—C13A—O4A	−179.2 (4)	C15B—O3B—C11B—C12B	178.0 (3)
C11A—C12A—C13A—C8A	0.6 (6)	C15B—O3B—C11B—C10B	−1.0 (5)
C9A—C8A—C13A—O4A	177.9 (3)	C9B—C10B—C11B—O3B	177.6 (3)
C7A—C8A—C13A—O4A	−0.2 (6)	C9B—C10B—C11B—C12B	−1.4 (6)
C9A—C8A—C13A—C12A	−1.9 (5)	O3B—C11B—C12B—C13B	−178.2 (3)
C7A—C8A—C13A—C12A	−180.0 (4)	C10B—C11B—C12B—C13B	0.9 (6)
C4B—S1B—C1B—C2B	1.4 (8)	C16B—O4B—C13B—C12B	0.6 (5)
S1B—C1B—C2B—C3B	1.8 (12)	C16B—O4B—C13B—C8B	−179.7 (3)
C1B—C2B—C3B—C4B	−5.1 (14)	C11B—C12B—C13B—O4B	−179.4 (3)
C4B—S1X—C1X—C2X	−2(2)	C11B—C12B—C13B—C8B	0.9 (6)
S1X—C1X—C2X—C3X	7(3)	C9B—C8B—C13B—O4B	178.2 (3)
C1X—C2X—C3X—C4B	−9(3)	C7B—C8B—C13B—O4B	−3.2 (6)
C2B—C3B—C4B—C3X	5.4 (16)	C9B—C8B—C13B—C12B	−2.1 (6)
C2B—C3B—C4B—C5B	179.0 (7)	C7B—C8B—C13B—C12B	176.5 (4)
C2B—C3B—C4B—S1X	−121 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C2B—H2B···O3A	0.93	2.56	3.482 (10)	171
C6A—H6A···O4A	0.93	2.22	2.815 (4)	121
C6B—H6B···O4B	0.93	2.24	2.824 (4)	120
C15A—H15C···O1Bi	0.96	2.51	3.451 (5)	166
C15B—H15F···O1Aii	0.96	2.55	3.355 (5)	141
C16B—H16E···O3Biii	0.96	2.59	3.401 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2B—H2B⋯O3A	0.93	2.56	3.482 (10)	171
C6A—H6A⋯O4A	0.93	2.22	2.815 (4)	121
C6B—H6B⋯O4B	0.93	2.24	2.824 (4)	120
C15A—H15C⋯O1Bi	0.96	2.51	3.451 (5)	166
C15B—H15F⋯O1Aii	0.96	2.55	3.355 (5)	141
C16B—H16E⋯O3Biii	0.96	2.59	3.401 (4)	142

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