(Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine

Liu, Y.-T.; Chu, G.

doi:10.1107/S1600536814004437

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o384

doi:10.1107/S1600536814004437

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(Z)-5-(3,4,5-Trimethoxystyryl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

Yu-Tao Liu ^a and Gang Chu ^b ^*

^aDepartment of Pharmacy, Yantaishan Hospital, Yantai 264000, Shandong, People's Republic of China, and ^bNanjing Sanhome Pharmaceutical Co. Ltd, Nanjing 210038, Jiangsu, People's Republic of China
^*Correspondence e-mail: chugang_1981@163.com

(Received 22 February 2014; accepted 26 February 2014; online 5 March 2014)

In the title compound, C₁₇H₁₈O₅S, an analogue of the potent anticancer agent combretastatin A-4, the alkene C=C bond has a cis conformation and the C—C=C—C torsion angle is 9.0 (3)°. The dihedral angle between the benzene and thiophene rings is 54.07 (4)°. The dioxene ring adopts a half-chair conformation, with the C atoms of the methylene groups displaced by −0.325 (2) and 0.341 (3) Å from the plane of the other atoms. The C atoms of the two meta-methoxy groups are close to being coplanar with their attached benzene ring [displacements = −0.025 (2) and −0.196 (2) Å], whereas the C atom of the para-methoxy group is significantly displaced [by −1.107 (2) Å]. In the crystal, C—H⋯O hydrogen bonds link the molecules into [0-11] chains, which feature two different types of R₂²(6) loops.

CCDC reference: 988810

Related literature

For background to combretastatin [systematic name: (Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)phenol], see Pettit et al. (1987 , 1995 ); Dark et al. (1997 ); Thorpe et al. (2003 ); Tozer et al. (2005 ). For further synthesis details, see Mohannkrishnan et al. (1999 ).

Experimental

Crystal data

C₁₇H₁₈O₅S
M_r = 334.37
Triclinic, $[P \overline 1]$
a = 8.197 (2) Å
b = 8.4527 (15) Å
c = 11.835 (3) Å
α = 88.774 (1)°
β = 85.484 (3)°
γ = 76.422 (2)°
V = 794.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.26 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.963, T_max = 0.985
4342 measured reflections
3059 independent reflections
2766 reflections with I > 2σ(I)
R_int = 0.159

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.179
S = 0.99
3059 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O1ⁱ	0.96	2.57	3.477 (3)	157
C17—H17B⋯O3ⁱⁱ	0.96	2.57	3.266 (3)	129
Symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 988810

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814004437/hb7200sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004437/hb7200Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814004437/hb7200Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536814004437/hb7200Isup4.cml

checkCIF report

Comment top

Combretastatins are natural products with extraordinary anticancer activity, which were isolated from tree Combretum caffrum (Pettit et al.1987). Among these compounds, combretastatin A-4 ((Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)phenol, CA-4) possesses the most potent antitumor activity as a result of specifically targeting the vasculature of tumors. (Pettit et al. 1995; Dark et al. 1997). Its disodium phosphate prodrug has already developed and entered clinical trials (Thorpe et al.2003; Tozer et al. 2005). Therefore, CA-4 is a very attractive leading compound because of the relatively simple structure and the strong potency against a broad spectrum of human cancer cell lines. The title compound is a new CA-4 analogue, which was prepared by the Wittig reaction (Mohannkrishnan et al. 1999). The antitumor activities of the title compound against HL-60, SMMC-7721 and A549 cancer cell lines in vitro are closely to the natural CA-4. We now report the structure of the title compound (Fig. 1). The C=C bond length is 1.335 (2) Å and two aryl units are on the same sides of the double bond plane. Therefore, it exists as Z configuration. The planes of the two aryl units, benzene ring and thiophene ring, in the molecule make a dihedral angle of 54.07 (4)°. Therefore, the structure of the title compound is very similar as that of the natural combretastatin A-4 (CA-4). In the crystal structure of the title compound, the C—H···O interactions extend the molecules into a zigzag supramolecular array with dangling thiophene rings (Fig. 2).

Related literature top

For background to combretastatin [systematic name: (Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)phenol], see Pettit et al. (1987, 1995); Dark et al. (1997); Thorpe et al. (2003); Tozer et al. (2005). For further synthesis details, see Mohannkrishnan et al. (1999).

Experimental top

To the bromotriphenyl(3,4,5-trimethoxybenzyl)phosphonium salt (5.2 g,10.0 mmol) in dry THF (60 ml) at -78 °C, was added 2.5 Mn-BuLi in hexane (4.0 ml,10.0 mmol) with stirring. After 20 min., a solution of 2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde (1.7 g,10.0 mmol) in dry THF (20 ml) was added and resulting mixture stirred at room temperature for 2 h. Then, the mixture was poured into crushed ice, extracted with ethyl acetate (3*30 ml), dried with MgSO₄, and concentrated in vacuo. The resulting solid was purified by column chromatography (petroleum ether/ ethyl acetate, V:V = 5:1) to give white product (1.38 g). Yield: 41.9%. mp. 122–123 °C. The ¹H NMR, ¹³CNMR, MS spectra and elemental analysis are in accord with the assigned structures. Colourless blocks of the title compound were obtained by the slow evaporation of a petroleum ether/ ethyl acetate solution.

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound, showing 50% probability ellipsoids.
	Fig. 2. A hydrogen-bonded chain in the title compound.

(Z)-5-(3,4,5-Trimethoxystyryl)-2,3-dihydrothieno[3,4-b][1,4]dioxine top

Crystal data top

C₁₇H₁₈O₅S	Z = 2
M_r = 334.37	F(000) = 352
Triclinic, P1	D_x = 1.397 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.197 (2) Å	Cell parameters from 3471 reflections
b = 8.4527 (15) Å	θ = 2.5–28.3°
c = 11.835 (3) Å	µ = 0.23 mm⁻¹
α = 88.774 (1)°	T = 296 K
β = 85.484 (3)°	Block, colorless
γ = 76.422 (2)°	0.30 × 0.28 × 0.26 mm
V = 794.6 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	3059 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.159
ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→5
T_min = 0.963, T_max = 0.985	k = −10→10
4342 measured reflections	l = −14→14

Refinement top

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) = 0.179	w = 1/[σ²(F_o²) + (0.1373P)² + 0.0901P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
3059 reflections	Δρ_max = 0.57 e Å⁻³
212 parameters	Δρ_min = −0.69 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.75 (5)

Crystal data top

C₁₇H₁₈O₅S	γ = 76.422 (2)°
M_r = 334.37	V = 794.6 (3) Å³
Triclinic, P1	Z = 2
a = 8.197 (2) Å	Mo Kα radiation
b = 8.4527 (15) Å	µ = 0.23 mm⁻¹
c = 11.835 (3) Å	T = 296 K
α = 88.774 (1)°	0.30 × 0.28 × 0.26 mm
β = 85.484 (3)°

Data collection top

Bruker SMART CCD diffractometer	3059 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2766 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.985	R_int = 0.159
4342 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 0.99	Δρ_max = 0.57 e Å⁻³
3059 reflections	Δρ_min = −0.69 e Å⁻³
212 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7976 (2)	0.5843 (2)	0.05341 (13)	0.0332 (4)
H1	0.7750	0.6054	−0.0219	0.040*
C2	0.8766 (2)	0.6846 (2)	0.10955 (14)	0.0341 (4)
C3	0.9126 (2)	0.6527 (2)	0.22295 (14)	0.0346 (4)
C4	0.8656 (2)	0.5213 (2)	0.27815 (13)	0.0339 (4)
C5	0.7875 (2)	0.4201 (2)	0.22159 (13)	0.0339 (4)
H5	0.7591	0.3311	0.2588	0.041*
C6	0.75215 (19)	0.4526 (2)	0.10883 (13)	0.0319 (4)
C7	0.6789 (2)	0.3434 (2)	0.04398 (13)	0.0358 (4)
H7	0.7074	0.3418	−0.0337	0.043*
C8	0.5779 (2)	0.2464 (2)	0.07919 (14)	0.0362 (4)
H8	0.5606	0.1761	0.0243	0.043*
C9	0.4900 (2)	0.2326 (2)	0.19020 (14)	0.0354 (4)
C10	0.3068 (3)	0.2738 (3)	0.37088 (18)	0.0544 (6)
H10	0.2395	0.3115	0.4362	0.065*
C11	0.3539 (2)	0.1146 (3)	0.33906 (15)	0.0439 (5)
C12	0.4559 (2)	0.0932 (2)	0.23456 (13)	0.0340 (4)
C13	0.4314 (3)	−0.1752 (2)	0.23211 (18)	0.0548 (6)
H13A	0.4955	−0.2826	0.2088	0.066*
H13B	0.3206	−0.1585	0.2040	0.066*
C14	0.4144 (4)	−0.1663 (3)	0.3584 (2)	0.0671 (7)
H14A	0.3653	−0.2536	0.3888	0.081*
H14B	0.5250	−0.1809	0.3865	0.081*
C15	0.8706 (3)	0.8662 (2)	−0.04727 (16)	0.0465 (5)
H15A	0.9172	0.7818	−0.1016	0.070*
H15B	0.9068	0.9631	−0.0697	0.070*
H15C	0.7500	0.8883	−0.0437	0.070*
C16	0.9071 (3)	0.9017 (3)	0.3128 (2)	0.0597 (6)
H16A	0.8508	0.9574	0.2502	0.090*
H16B	0.9818	0.9629	0.3387	0.090*
H16C	0.8253	0.8909	0.3734	0.090*
C17	0.8570 (3)	0.3659 (3)	0.44741 (16)	0.0570 (6)
H17A	0.7378	0.3771	0.4470	0.085*
H17B	0.8873	0.3637	0.5243	0.085*
H17C	0.9152	0.2664	0.4103	0.085*
O1	0.92692 (17)	0.81485 (16)	0.06163 (10)	0.0434 (4)
O2	1.00158 (17)	0.74368 (16)	0.27742 (11)	0.0449 (4)
O3	0.90251 (18)	0.49911 (17)	0.38942 (10)	0.0426 (4)
O4	0.3099 (2)	−0.0118 (2)	0.39693 (13)	0.0637 (5)
O5	0.51392 (17)	−0.05526 (15)	0.18353 (10)	0.0418 (4)
S1	0.38731 (7)	0.39573 (6)	0.27505 (5)	0.0536 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0339 (8)	0.0410 (9)	0.0268 (7)	−0.0138 (7)	0.0016 (6)	−0.0030 (6)
C2	0.0317 (8)	0.0386 (9)	0.0341 (8)	−0.0145 (7)	0.0038 (6)	−0.0020 (7)
C3	0.0356 (8)	0.0388 (9)	0.0329 (8)	−0.0154 (7)	−0.0012 (6)	−0.0075 (7)
C4	0.0352 (8)	0.0407 (9)	0.0268 (8)	−0.0111 (7)	0.0003 (6)	−0.0067 (6)
C5	0.0393 (9)	0.0349 (8)	0.0301 (8)	−0.0149 (7)	0.0010 (6)	−0.0021 (6)
C6	0.0315 (8)	0.0367 (8)	0.0289 (7)	−0.0119 (6)	0.0029 (6)	−0.0069 (6)
C7	0.0449 (9)	0.0405 (9)	0.0253 (7)	−0.0174 (7)	0.0006 (6)	−0.0057 (6)
C8	0.0430 (9)	0.0380 (9)	0.0314 (8)	−0.0172 (7)	0.0007 (6)	−0.0084 (6)
C9	0.0344 (8)	0.0391 (9)	0.0347 (8)	−0.0130 (7)	0.0016 (6)	−0.0094 (7)
C10	0.0538 (11)	0.0611 (13)	0.0480 (11)	−0.0191 (10)	0.0214 (9)	−0.0226 (9)
C11	0.0442 (10)	0.0529 (11)	0.0366 (9)	−0.0185 (8)	0.0090 (7)	−0.0094 (8)
C12	0.0341 (8)	0.0391 (9)	0.0300 (8)	−0.0121 (7)	0.0030 (6)	−0.0093 (6)
C13	0.0737 (14)	0.0382 (10)	0.0539 (12)	−0.0231 (10)	0.0185 (10)	−0.0036 (8)
C14	0.0922 (18)	0.0546 (13)	0.0543 (13)	−0.0253 (13)	0.0184 (12)	0.0081 (10)
C15	0.0553 (11)	0.0502 (11)	0.0403 (9)	−0.0253 (9)	−0.0041 (8)	0.0072 (8)
C16	0.0674 (14)	0.0547 (12)	0.0625 (13)	−0.0240 (11)	−0.0031 (10)	−0.0239 (10)
C17	0.0788 (15)	0.0702 (14)	0.0343 (9)	−0.0404 (12)	−0.0135 (9)	0.0104 (9)
O1	0.0514 (8)	0.0488 (8)	0.0388 (7)	−0.0296 (6)	−0.0044 (5)	0.0062 (6)
O2	0.0485 (8)	0.0448 (8)	0.0480 (7)	−0.0216 (6)	−0.0104 (6)	−0.0074 (6)
O3	0.0574 (8)	0.0486 (7)	0.0284 (6)	−0.0242 (6)	−0.0078 (5)	−0.0003 (5)
O4	0.0793 (11)	0.0662 (10)	0.0479 (8)	−0.0317 (9)	0.0283 (7)	−0.0076 (7)
O5	0.0534 (8)	0.0344 (7)	0.0382 (7)	−0.0164 (6)	0.0142 (5)	−0.0073 (5)
S1	0.0570 (4)	0.0406 (4)	0.0624 (4)	−0.0154 (3)	0.0180 (3)	−0.0209 (2)

Geometric parameters (Å, º) top

C1—C2	1.389 (2)	C11—C12	1.427 (2)
C1—C6	1.391 (2)	C12—O5	1.368 (2)
C1—H1	0.9300	C13—O5	1.432 (2)
C2—O1	1.3611 (19)	C13—C14	1.492 (3)
C2—C3	1.404 (2)	C13—H13A	0.9700
C3—O2	1.3778 (18)	C13—H13B	0.9700
C3—C4	1.392 (2)	C14—O4	1.444 (3)
C4—O3	1.3734 (19)	C14—H14A	0.9700
C4—C5	1.393 (2)	C14—H14B	0.9700
C5—C6	1.396 (2)	C15—O1	1.428 (2)
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.471 (2)	C15—H15B	0.9600
C7—C8	1.335 (2)	C15—H15C	0.9600
C7—H7	0.9300	C16—O2	1.431 (3)
C8—C9	1.464 (2)	C16—H16A	0.9600
C8—H8	0.9300	C16—H16B	0.9600
C9—C12	1.359 (2)	C16—H16C	0.9600
C9—S1	1.7322 (17)	C17—O3	1.415 (2)
C10—C11	1.363 (3)	C17—H17A	0.9600
C10—S1	1.713 (2)	C17—H17B	0.9600
C10—H10	0.9300	C17—H17C	0.9600
C11—O4	1.360 (2)

C2—C1—C6	120.60 (14)	O5—C13—C14	111.46 (17)
C2—C1—H1	119.7	O5—C13—H13A	109.3
C6—C1—H1	119.7	C14—C13—H13A	109.3
O1—C2—C1	124.50 (15)	O5—C13—H13B	109.3
O1—C2—C3	115.47 (14)	C14—C13—H13B	109.3
C1—C2—C3	120.02 (15)	H13A—C13—H13B	108.0
O2—C3—C4	120.04 (14)	O4—C14—C13	111.1 (2)
O2—C3—C2	120.78 (15)	O4—C14—H14A	109.4
C4—C3—C2	119.08 (14)	C13—C14—H14A	109.4
O3—C4—C3	115.81 (14)	O4—C14—H14B	109.4
O3—C4—C5	123.31 (15)	C13—C14—H14B	109.4
C3—C4—C5	120.88 (14)	H14A—C14—H14B	108.0
C4—C5—C6	119.71 (15)	O1—C15—H15A	109.5
C4—C5—H5	120.1	O1—C15—H15B	109.5
C6—C5—H5	120.1	H15A—C15—H15B	109.5
C1—C6—C5	119.70 (14)	O1—C15—H15C	109.5
C1—C6—C7	118.70 (14)	H15A—C15—H15C	109.5
C5—C6—C7	121.44 (14)	H15B—C15—H15C	109.5
C8—C7—C6	130.10 (14)	O2—C16—H16A	109.5
C8—C7—H7	115.0	O2—C16—H16B	109.5
C6—C7—H7	115.0	H16A—C16—H16B	109.5
C7—C8—C9	130.45 (14)	O2—C16—H16C	109.5
C7—C8—H8	114.8	H16A—C16—H16C	109.5
C9—C8—H8	114.8	H16B—C16—H16C	109.5
C12—C9—C8	125.05 (15)	O3—C17—H17A	109.5
C12—C9—S1	109.52 (12)	O3—C17—H17B	109.5
C8—C9—S1	124.81 (13)	H17A—C17—H17B	109.5
C11—C10—S1	111.34 (14)	O3—C17—H17C	109.5
C11—C10—H10	124.3	H17A—C17—H17C	109.5
S1—C10—H10	124.3	H17B—C17—H17C	109.5
O4—C11—C10	125.54 (17)	C2—O1—C15	117.07 (13)
O4—C11—C12	122.54 (17)	C3—O2—C16	114.95 (14)
C10—C11—C12	111.91 (18)	C4—O3—C17	117.00 (13)
C9—C12—O5	123.02 (14)	C11—O4—C14	111.51 (15)
C9—C12—C11	114.32 (16)	C12—O5—C13	112.21 (13)
O5—C12—C11	122.66 (16)	C10—S1—C9	92.85 (9)

C6—C1—C2—O1	179.31 (15)	S1—C9—C12—O5	177.21 (13)
C6—C1—C2—C3	0.5 (2)	C8—C9—C12—C11	−173.91 (17)
O1—C2—C3—O2	−3.6 (2)	S1—C9—C12—C11	−2.66 (19)
C1—C2—C3—O2	175.28 (15)	O4—C11—C12—C9	−178.64 (16)
O1—C2—C3—C4	−179.85 (14)	C10—C11—C12—C9	2.1 (2)
C1—C2—C3—C4	−1.0 (3)	O4—C11—C12—O5	1.5 (3)
O2—C3—C4—O3	4.7 (2)	C10—C11—C12—O5	−177.77 (17)
C2—C3—C4—O3	−179.03 (15)	O5—C13—C14—O4	63.0 (3)
O2—C3—C4—C5	−174.82 (15)	C1—C2—O1—C15	10.4 (3)
C2—C3—C4—C5	1.5 (3)	C3—C2—O1—C15	−170.77 (16)
O3—C4—C5—C6	179.03 (15)	C4—C3—O2—C16	−106.9 (2)
C3—C4—C5—C6	−1.5 (3)	C2—C3—O2—C16	76.9 (2)
C2—C1—C6—C5	−0.6 (2)	C3—C4—O3—C17	−179.64 (17)
C2—C1—C6—C7	−176.03 (15)	C5—C4—O3—C17	−0.2 (3)
C4—C5—C6—C1	1.0 (2)	C10—C11—O4—C14	−164.6 (2)
C4—C5—C6—C7	176.38 (15)	C12—C11—O4—C14	16.3 (3)
C1—C6—C7—C8	−155.46 (19)	C13—C14—O4—C11	−46.7 (3)
C5—C6—C7—C8	29.2 (3)	C9—C12—O5—C13	−166.87 (17)
C6—C7—C8—C9	9.0 (3)	C11—C12—O5—C13	13.0 (2)
C7—C8—C9—C12	−148.21 (19)	C14—C13—O5—C12	−43.6 (2)
C7—C8—C9—S1	41.8 (3)	C11—C10—S1—C9	−0.85 (18)
S1—C10—C11—O4	−179.73 (16)	C12—C9—S1—C10	2.00 (14)
S1—C10—C11—C12	−0.5 (2)	C8—C9—S1—C10	173.28 (16)
C8—C9—C12—O5	5.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O1ⁱ	0.96	2.57	3.477 (3)	157
C17—H17B···O3ⁱⁱ	0.96	2.57	3.266 (3)	129

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O1ⁱ	0.96	2.57	3.477 (3)	157
C17—H17B···O3ⁱⁱ	0.96	2.57	3.266 (3)	129

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+2, −y+1, −z+1.

References

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