Diethyl 3,4-bis(acetoxy-meth-yl)thieno[2,3-b]thio-phene-2,5-dicarboxyl-ate.

In the title compound, C(18)H(20)O(8)S(2), the dihedral angle between the two thio-phene 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 mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions and the crystal structure is stabilized through weak inter-molecular C-H⋯O inter-actions.

Related literature

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

Crystal data

C18H20O8S2

M = 428.46

Triclinic,

a = 9.3214 (5) Å

b = 10.2416 (6) Å

c = 10.6622 (6) Å

α = 84.952 (3)°

β = 82.814 (4)°

γ = 75.432 (3)°

V = 975.72 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 295 K

0.29 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.914, T max = 0.963

25739 measured reflections

6686 independent reflections

4444 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.188

S = 1.04

6686 reflections

279 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036149/bt5053sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036149/bt5053Isup2.hkl

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

C18H20O8S2	Z = 2
Mr = 428.46	F(000) = 448
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0945P)2 + 0.3857P] where P = (Fo2 + 2Fc2)/3
6686 reflections	(Δ/σ)max < 0.001
279 parameters	Δρmax = 0.82 e Å−3
4 restraints	Δρmin = −0.59 e Å−3

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .