Diethyl 3,4-bis(acetoxy­meth­yl)thieno[2,3-b]thio­phene-2,5-dicarboxyl­ate

Gunasekaran, B.; Sureshbabu, R.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809036149

Diethyl 3,4-bis(acetoxymethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate

B. Gunasekaran, R. Sureshbabu, A. K. Mohanakrishnan, G. Chakkaravarthi and V. Manivannan

In the title compound, C₁₈H₂₀O₈S₂, the dihedral angle between the two thiophene rings is 2.33 (7)°. The methyl C atoms of the ester groups are disordered over two positions; the site-occupancy factors of the terminal methyl C atoms are 0.632 (18):0.368 (18) and 0.623 (17):0.377 (17). The molecular structure is stabilized by weak intramolecular C—H

O interactions and the crystal structure is stabilized through weak intermolecular C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809036149/bt5053sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809036149/bt5053Isup2.hkl Contains datablock I

CCDC reference: 750699

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.057
wR factor = 0.188
Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.67 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.43 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14

Alert level G
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................       7.00 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Thiophene derivatives exhibit anti-inflammatory (Graff et al., 2005; Hymete et al., 2005), anti-protozoal (Tapia et al., 2003) and antitumor (Dallemagne et al., 2003) activities. The geometric parameters of the title compound (Fig. 1) agree with the reported similar structures (Dufresne & Skene, 2008; Khan et al., 2004).

The dihedral angle between the two thiophene rings is 2.33 (7)°. The terminal C atoms of the ester groups are disordered over two positions (the site occupancies of C9 and C9A are 0.37 (2) and 0.63 (2), respectively and C18 and C18A are 0.62 (2) and 0.38 (2), respectively).

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal structure is through weak intermolecular C—H···O interactions. The intramolecular C17—H17C···O8 interaction generate five-membered ring, with graph set motif S(5) and C10—H10A···O2 and C13—H13B···O8 interactions generate six-membered rings, each with graph set motif S(6). The intermolecular C10—H10B···O6 interaction generates an eighteen-membered ring, with graph set motif of R₂²(18) (Bernstein et al., 1995).

Related literature top

For the biological activity of thiophene derivatives, see: Graff et al. (2005); Hymete et al. (2005); Tapia et al. (2003); Dallemagne et al. (2003). For related structures see: Dufresne & Skene (2008); Khan et al. (2004). For graph-set notation see: Bernstein et al. (1995).

Experimental top

To a solution of diethyl 3,4-dibromomethylthieno[2,3,-b]thiophene-2,5-dicarboxylate (2 g, 4.25 mmol) in dimethyl formamide (10 ml) was added potassium acetate (1.67 g, 17.0 mmol). The reaction mixture was allowed to stir at room temperature for 5 h under nitrogen atmosphere. The reaction mixture was poured over crushed ice (50 g) containing 1 ml of conc. HCl. The obtained solid was filtered and dried. Recrystallization from methanol afforded the compound.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, viewed down the C axis. Hydrogen bonds are shown as dashed lines.

Diethyl 3,4-bis(acetoxymethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate top

Crystal data top

C₁₈H₂₀O₈S₂	Z = 2
M_r = 428.46	F(000) = 448
Triclinic, P1	D_x = 1.458 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3214 (5) Å	Cell parameters from 5319 reflections
b = 10.2416 (6) Å	θ = 2.7–31.0°
c = 10.6622 (6) Å	µ = 0.32 mm⁻¹
α = 84.952 (3)°	T = 295 K
β = 82.814 (4)°	Needle, colourless
γ = 75.432 (3)°	0.29 × 0.14 × 0.12 mm
V = 975.72 (9) Å³

Data collection top

Bruker Kappa APEX2 CCD diffractometer	6686 independent reflections
Radiation source: fine-focus sealed tube	4444 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 0 pixels mm^-1	θ_max = 32.0°, θ_min = 1.9°
ω and ϕ scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→13
T_min = 0.914, T_max = 0.963	l = −15→15
25739 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0945P)² + 0.3857P] where P = (F_o² + 2F_c²)/3
6686 reflections	(Δ/σ)_max < 0.001
279 parameters	Δρ_max = 0.82 e Å⁻³
4 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₈H₂₀O₈S₂	γ = 75.432 (3)°
M_r = 428.46	V = 975.72 (9) Å³
Triclinic, P1	Z = 2
a = 9.3214 (5) Å	Mo Kα radiation
b = 10.2416 (6) Å	µ = 0.32 mm⁻¹
c = 10.6622 (6) Å	T = 295 K
α = 84.952 (3)°	0.29 × 0.14 × 0.12 mm
β = 82.814 (4)°

Data collection top

Bruker Kappa APEX2 CCD diffractometer	6686 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4444 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.963	R_int = 0.025
25739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	4 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.04	Δρ_max = 0.82 e Å⁻³
6686 reflections	Δρ_min = −0.59 e Å⁻³
279 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.02951 (5)	0.21624 (6)	0.28483 (5)	0.04706 (15)
S2	−0.08189 (5)	0.30619 (5)	0.55975 (5)	0.04537 (15)
O1	0.1876 (2)	0.1299 (2)	0.05271 (17)	0.0747 (5)
O2	0.4020 (2)	0.1825 (3)	0.0622 (2)	0.0920 (7)
O3	0.51977 (16)	0.15799 (15)	0.36366 (18)	0.0544 (4)
O4	0.70351 (19)	0.25297 (19)	0.3848 (2)	0.0719 (5)
O5	0.40617 (17)	0.27623 (16)	0.65075 (16)	0.0533 (4)
O6	0.5449 (3)	0.4048 (2)	0.7014 (3)	0.0978 (8)
O7	−0.1209 (3)	0.3926 (2)	0.80902 (18)	0.0821 (6)
O8	0.1045 (3)	0.4242 (3)	0.8232 (2)	0.1029 (9)
C1	0.2123 (2)	0.2247 (2)	0.2352 (2)	0.0483 (5)
C2	0.2772 (2)	0.2731 (2)	0.3227 (2)	0.0463 (4)
C3	0.1771 (2)	0.30467 (19)	0.4351 (2)	0.0424 (4)
C4	0.1817 (2)	0.3531 (2)	0.5561 (2)	0.0469 (5)
C5	0.0511 (3)	0.3560 (2)	0.6319 (2)	0.0483 (5)
C6	0.0398 (2)	0.2773 (2)	0.42631 (19)	0.0406 (4)
C7	0.2789 (3)	0.1791 (3)	0.1093 (2)	0.0592 (6)
C8	0.2451 (5)	0.0815 (5)	−0.0725 (3)	0.0994 (12)
H8A	0.3523	0.0700	−0.0854	0.119*	0.368 (18)
H8B	0.2009	0.1469	−0.1369	0.119*	0.368 (18)
H8C	0.2708	0.1540	−0.1285	0.119*	0.632 (18)
H8D	0.3340	0.0087	−0.0667	0.119*	0.632 (18)
C9	0.208 (3)	−0.0509 (13)	−0.0829 (17)	0.148 (7)	0.368 (18)
H9A	0.1181	−0.0543	−0.0286	0.223*	0.368 (18)
H9B	0.2880	−0.1235	−0.0579	0.223*	0.368 (18)
H9C	0.1924	−0.0595	−0.1689	0.223*	0.368 (18)
C9A	0.1272 (9)	0.0290 (14)	−0.1206 (8)	0.112 (4)	0.632 (18)
H9A1	0.1651	−0.0102	−0.2003	0.168*	0.632 (18)
H9A2	0.0413	0.1020	−0.1316	0.168*	0.632 (18)
H9A3	0.0998	−0.0385	−0.0606	0.168*	0.632 (18)
C10	0.4373 (2)	0.2825 (2)	0.3058 (3)	0.0538 (5)
H10A	0.4724	0.2915	0.2167	0.065*
H10B	0.4480	0.3596	0.3472	0.065*
C11	0.6524 (2)	0.1574 (2)	0.3979 (2)	0.0457 (4)
C12	0.7265 (3)	0.0225 (3)	0.4536 (3)	0.0755 (8)
H12A	0.7131	−0.0469	0.4044	0.113*
H12B	0.6830	0.0110	0.5391	0.113*
H12C	0.8310	0.0164	0.4532	0.113*
C13	0.3113 (3)	0.3958 (2)	0.5957 (3)	0.0562 (6)
H13A	0.3653	0.4326	0.5231	0.067*
H13B	0.2769	0.4644	0.6572	0.067*
C14	0.5192 (2)	0.2971 (2)	0.7048 (2)	0.0508 (5)
C15	0.6043 (3)	0.1712 (3)	0.7674 (3)	0.0684 (7)
H15A	0.7092	0.1640	0.7472	0.103*
H15B	0.5792	0.0946	0.7381	0.103*
H15C	0.5796	0.1736	0.8575	0.103*
C16	0.0166 (4)	0.3957 (3)	0.7634 (2)	0.0638 (6)
C17	−0.1557 (5)	0.4318 (5)	0.9381 (3)	0.1211 (17)
H17A	−0.1449	0.5229	0.9429	0.145*	0.368 (18)
H17B	−0.0876	0.3714	0.9916	0.145*	0.368 (18)
H17C	−0.0621	0.4205	0.9736	0.145*	0.632 (18)
H17D	−0.2071	0.5267	0.9393	0.145*	0.632 (18)
C18	−0.3127 (7)	0.4253 (12)	0.9829 (7)	0.097 (3)	0.623 (17)
H18A	−0.3228	0.3352	0.9769	0.146*	0.623 (17)
H18B	−0.3796	0.4871	0.9311	0.146*	0.623 (17)
H18C	−0.3361	0.4495	1.0693	0.146*	0.623 (17)
C18A	−0.238 (2)	0.3432 (15)	1.0223 (10)	0.107 (5)	0.377 (17)
H18D	−0.2882	0.3907	1.0951	0.161*	0.377 (17)
H18E	−0.1680	0.2625	1.0491	0.161*	0.377 (17)
H18F	−0.3090	0.3197	0.9766	0.161*	0.377 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0368 (2)	0.0638 (3)	0.0455 (3)	−0.0180 (2)	−0.00627 (18)	−0.0101 (2)
S2	0.0411 (2)	0.0553 (3)	0.0445 (3)	−0.0177 (2)	−0.00618 (19)	−0.0085 (2)
O1	0.0760 (12)	0.1018 (15)	0.0518 (10)	−0.0349 (11)	0.0117 (9)	−0.0219 (10)
O2	0.0605 (12)	0.1266 (19)	0.0884 (15)	−0.0303 (12)	0.0247 (11)	−0.0275 (14)
O3	0.0380 (7)	0.0491 (8)	0.0796 (11)	−0.0164 (6)	−0.0142 (7)	0.0062 (7)
O4	0.0470 (9)	0.0678 (11)	0.1098 (16)	−0.0236 (8)	−0.0231 (9)	−0.0044 (10)
O5	0.0529 (8)	0.0509 (8)	0.0645 (10)	−0.0197 (7)	−0.0264 (7)	0.0003 (7)
O6	0.0878 (15)	0.0713 (13)	0.158 (2)	−0.0391 (11)	−0.0728 (16)	0.0083 (14)
O7	0.1042 (16)	0.1005 (15)	0.0523 (10)	−0.0420 (13)	0.0034 (10)	−0.0294 (10)
O8	0.129 (2)	0.140 (2)	0.0676 (13)	−0.0686 (18)	−0.0257 (13)	−0.0312 (14)
C1	0.0373 (9)	0.0561 (12)	0.0520 (11)	−0.0139 (8)	−0.0019 (8)	−0.0022 (9)
C2	0.0342 (8)	0.0440 (10)	0.0619 (13)	−0.0129 (7)	−0.0082 (8)	0.0040 (9)
C3	0.0367 (8)	0.0394 (9)	0.0552 (11)	−0.0144 (7)	−0.0140 (8)	0.0029 (8)
C4	0.0493 (10)	0.0414 (10)	0.0585 (12)	−0.0200 (8)	−0.0232 (9)	0.0021 (8)
C5	0.0560 (11)	0.0487 (11)	0.0474 (11)	−0.0197 (9)	−0.0174 (9)	−0.0040 (8)
C6	0.0351 (8)	0.0462 (10)	0.0440 (10)	−0.0136 (7)	−0.0092 (7)	−0.0034 (8)
C7	0.0542 (12)	0.0617 (14)	0.0585 (14)	−0.0143 (11)	0.0064 (10)	−0.0038 (11)
C8	0.118 (3)	0.129 (3)	0.0556 (17)	−0.046 (3)	0.0230 (18)	−0.0279 (19)
C9	0.175 (18)	0.139 (13)	0.103 (11)	0.008 (13)	0.002 (11)	−0.009 (10)
C9A	0.131 (7)	0.137 (8)	0.078 (5)	−0.048 (6)	0.011 (4)	−0.048 (5)
C10	0.0348 (9)	0.0542 (12)	0.0741 (15)	−0.0175 (8)	−0.0085 (9)	0.0105 (10)
C11	0.0328 (8)	0.0577 (12)	0.0477 (11)	−0.0132 (8)	−0.0030 (7)	−0.0046 (9)
C12	0.0527 (13)	0.0770 (18)	0.091 (2)	−0.0086 (12)	−0.0177 (13)	0.0174 (15)
C13	0.0596 (12)	0.0508 (12)	0.0706 (15)	−0.0270 (10)	−0.0316 (11)	0.0037 (10)
C14	0.0434 (10)	0.0628 (13)	0.0514 (12)	−0.0186 (9)	−0.0118 (8)	−0.0057 (10)
C15	0.0544 (13)	0.0790 (17)	0.0714 (17)	−0.0135 (12)	−0.0198 (12)	0.0090 (13)
C16	0.0896 (19)	0.0617 (14)	0.0500 (13)	−0.0309 (13)	−0.0161 (12)	−0.0082 (11)
C17	0.176 (5)	0.139 (4)	0.064 (2)	−0.071 (3)	0.028 (2)	−0.050 (2)
C18	0.103 (5)	0.136 (8)	0.059 (4)	−0.038 (5)	0.005 (3)	−0.033 (4)
C18A	0.135 (12)	0.115 (10)	0.071 (6)	−0.025 (9)	−0.014 (7)	−0.018 (6)

Geometric parameters (Å, º) top

S1—C6	1.705 (2)	C9—H9A	0.9600
S1—C1	1.741 (2)	C9—H9B	0.9600
S2—C6	1.703 (2)	C9—H9C	0.9600
S2—C5	1.736 (2)	C9A—H9A1	0.9600
O1—C7	1.319 (3)	C9A—H9A2	0.9600
O1—C8	1.455 (3)	C9A—H9A3	0.9600
O2—C7	1.200 (3)	C10—H10A	0.9700
O3—C11	1.331 (2)	C10—H10B	0.9700
O3—C10	1.443 (3)	C11—C12	1.489 (3)
O4—C11	1.183 (3)	C12—H12A	0.9600
O5—C14	1.332 (2)	C12—H12B	0.9600
O5—C13	1.444 (3)	C12—H12C	0.9600
O6—C14	1.182 (3)	C13—H13A	0.9700
O7—C16	1.320 (4)	C13—H13B	0.9700
O7—C17	1.443 (4)	C14—C15	1.485 (3)
O8—C16	1.203 (3)	C15—H15A	0.9600
C1—C2	1.362 (3)	C15—H15B	0.9600
C1—C7	1.471 (3)	C15—H15C	0.9600
C2—C3	1.431 (3)	C17—C18	1.4972 (10)
C2—C10	1.507 (3)	C17—C18A	1.4987 (10)
C3—C6	1.393 (2)	C17—H17A	0.9700
C3—C4	1.431 (3)	C17—H17B	0.9700
C4—C5	1.369 (3)	C17—H17C	0.9700
C4—C13	1.503 (3)	C17—H17D	0.9700
C5—C16	1.469 (3)	C18—H18A	0.9600
C8—C9A	1.4988 (10)	C18—H18B	0.9600
C8—C9	1.4994 (10)	C18—H18C	0.9600
C8—H8A	0.9700	C18A—H18D	0.9600
C8—H8B	0.9700	C18A—H18E	0.9600
C8—H8C	0.9700	C18A—H18F	0.9600
C8—H8D	0.9700

C6—S1—C1	90.24 (10)	C2—C10—H10A	110.7
C6—S2—C5	89.62 (10)	O3—C10—H10B	110.7
C7—O1—C8	115.4 (2)	C2—C10—H10B	110.7
C11—O3—C10	117.10 (16)	H10A—C10—H10B	108.8
C14—O5—C13	115.27 (17)	O4—C11—O3	123.4 (2)
C16—O7—C17	112.2 (3)	O4—C11—C12	125.0 (2)
C2—C1—C7	127.8 (2)	O3—C11—C12	111.5 (2)
C2—C1—S1	113.60 (17)	C11—C12—H12A	109.5
C7—C1—S1	118.60 (17)	C11—C12—H12B	109.5
C1—C2—C3	111.29 (17)	H12A—C12—H12B	109.5
C1—C2—C10	123.9 (2)	C11—C12—H12C	109.5
C3—C2—C10	124.7 (2)	H12A—C12—H12C	109.5
C6—C3—C4	111.15 (19)	H12B—C12—H12C	109.5
C6—C3—C2	111.75 (18)	O5—C13—C4	106.55 (16)
C4—C3—C2	137.07 (18)	O5—C13—H13A	110.4
C5—C4—C3	110.97 (17)	C4—C13—H13A	110.4
C5—C4—C13	124.0 (2)	O5—C13—H13B	110.4
C3—C4—C13	125.0 (2)	C4—C13—H13B	110.4
C4—C5—C16	126.5 (2)	H13A—C13—H13B	108.6
C4—C5—S2	114.14 (16)	O6—C14—O5	122.2 (2)
C16—C5—S2	119.35 (19)	O6—C14—C15	125.9 (2)
C3—C6—S2	114.09 (15)	O5—C14—C15	111.9 (2)
C3—C6—S1	113.12 (15)	C14—C15—H15A	109.5
S2—C6—S1	132.76 (11)	C14—C15—H15B	109.5
O2—C7—O1	122.8 (3)	H15A—C15—H15B	109.5
O2—C7—C1	125.5 (3)	C14—C15—H15C	109.5
O1—C7—C1	111.7 (2)	H15A—C15—H15C	109.5
O1—C8—C9A	107.7 (3)	H15B—C15—H15C	109.5
O1—C8—C9	108.9 (7)	O8—C16—O7	124.1 (3)
O1—C8—H8A	109.9	O8—C16—C5	124.0 (3)
C9A—C8—H8A	139.2	O7—C16—C5	111.9 (2)
C9—C8—H8A	109.9	O7—C17—C18	108.9 (3)
O1—C8—H8B	109.9	O7—C17—C18A	113.7 (5)
C9A—C8—H8B	72.5	O7—C17—H17A	109.9
C9—C8—H8B	109.9	C18—C17—H17A	109.9
H8A—C8—H8B	108.3	C18A—C17—H17A	133.7
O1—C8—H8C	110.2	O7—C17—H17B	109.9
C9A—C8—H8C	111.5	C18—C17—H17B	109.9
C9—C8—H8C	138.2	C18A—C17—H17B	70.5
H8A—C8—H8C	69.4	H17A—C17—H17B	108.3
O1—C8—H8D	109.8	O7—C17—H17C	107.6
C9A—C8—H8D	109.2	C18—C17—H17C	138.3
C9—C8—H8D	70.6	C18A—C17—H17C	105.0
H8B—C8—H8D	137.3	H17A—C17—H17C	75.1
H8C—C8—H8D	108.5	O7—C17—H17D	109.6
C8—C9—H9A	109.5	C18—C17—H17D	78.0
H8D—C9—H9A	131.3	C18A—C17—H17D	112.7
C8—C9—H9B	109.5	H17B—C17—H17D	134.0
H8D—C9—H9B	72.5	H17C—C17—H17D	107.8
C8—C9—H9C	109.5	C17—C18—H18A	109.5
H8D—C9—H9C	115.5	C17—C18—H18B	109.5
C8—C9A—H9A1	109.5	C17—C18—H18C	109.5
C8—C9A—H9A2	109.5	C17—C18A—H18D	109.5
H9A1—C9A—H9A2	109.5	C17—C18A—H18E	109.5
C8—C9A—H9A3	109.5	H18D—C18A—H18E	109.5
H9A1—C9A—H9A3	109.5	C17—C18A—H18F	109.5
H9A2—C9A—H9A3	109.5	H18D—C18A—H18F	109.5
O3—C10—C2	105.38 (16)	H18E—C18A—H18F	109.5
O3—C10—H10A	110.7

C6—S1—C1—C2	−0.51 (18)	C1—S1—C6—S2	−176.94 (17)
C6—S1—C1—C7	178.72 (19)	C8—O1—C7—O2	−1.0 (5)
C7—C1—C2—C3	−178.9 (2)	C8—O1—C7—C1	−179.6 (3)
S1—C1—C2—C3	0.2 (2)	C2—C1—C7—O2	−2.8 (4)
C7—C1—C2—C10	−2.9 (4)	S1—C1—C7—O2	178.1 (2)
S1—C1—C2—C10	176.25 (16)	C2—C1—C7—O1	175.8 (2)
C1—C2—C3—C6	0.2 (3)	S1—C1—C7—O1	−3.3 (3)
C10—C2—C3—C6	−175.73 (18)	C7—O1—C8—C9A	179.6 (6)
C1—C2—C3—C4	177.8 (2)	C7—O1—C8—C9	136.4 (11)
C10—C2—C3—C4	1.9 (4)	C11—O3—C10—C2	−159.1 (2)
C6—C3—C4—C5	1.7 (2)	C1—C2—C10—O3	−92.8 (3)
C2—C3—C4—C5	−175.9 (2)	C3—C2—C10—O3	82.6 (3)
C6—C3—C4—C13	−178.15 (18)	C10—O3—C11—O4	1.0 (3)
C2—C3—C4—C13	4.3 (4)	C10—O3—C11—C12	−178.8 (2)
C3—C4—C5—C16	178.0 (2)	C14—O5—C13—C4	−172.7 (2)
C13—C4—C5—C16	−2.2 (4)	C5—C4—C13—O5	91.0 (3)
C3—C4—C5—S2	−1.9 (2)	C3—C4—C13—O5	−89.2 (3)
C13—C4—C5—S2	177.97 (16)	C13—O5—C14—O6	−4.2 (4)
C6—S2—C5—C4	1.19 (17)	C13—O5—C14—C15	175.7 (2)
C6—S2—C5—C16	−178.7 (2)	C17—O7—C16—O8	2.0 (5)
C4—C3—C6—S2	−0.8 (2)	C17—O7—C16—C5	−179.9 (3)
C2—C3—C6—S2	177.42 (14)	C4—C5—C16—O8	−4.2 (4)
C4—C3—C6—S1	−178.87 (14)	S2—C5—C16—O8	175.6 (2)
C2—C3—C6—S1	−0.6 (2)	C4—C5—C16—O7	177.6 (2)
C5—S2—C6—C3	−0.18 (16)	S2—C5—C16—O7	−2.5 (3)
C5—S2—C6—S1	177.39 (17)	C16—O7—C17—C18	−179.8 (6)
C1—S1—C6—C3	0.64 (16)	C16—O7—C17—C18A	−136.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2	0.97	2.31	2.959 (4)	123
C13—H13B···O8	0.97	2.32	2.891 (4)	117
C17—H17C···O8	0.97	2.09	2.563 (5)	108
C10—H10B···O6ⁱ	0.97	2.44	3.243 (3)	140
C15—H15C···O2ⁱⁱ	0.96	2.56	3.453 (4)	154

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀O₈S₂
M_r	428.46
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.3214 (5), 10.2416 (6), 10.6622 (6)
α, β, γ (°)	84.952 (3), 82.814 (4), 75.432 (3)
V (Å³)	975.72 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.29 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEX2 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.914, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	25739, 6686, 4444
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.745

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.188, 1.04
No. of reflections	6686
No. of parameters	279
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.59

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).