Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2790
https://doi.org/10.1107/S1600536809042214

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

M. Umadevi,a R. Sureshbabu,b A. K. Mohanakrishnan,b G. Chakkaravarthic and V. Manivannand*

aDepartment of Chemistry, Pallavan College of Engineering, Kanchipuram 631 502, Tamilnadu, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: manivan_1999@yahoo.com

(Received 13 October 2009; accepted 14 October 2009; online 17 October 2009)

In the title compound, C30H32O8S2, the dihedral angle between the two benzene rings is 18.8 (1)°. The mol­ecular structure is stabilized by weak intra­molecular C—H⋯O hydrogen bonds. In the crystal structure, the mol­ecules are linked via weak inter­molecular C—H⋯O hydrogen bonds and π–π inter­actions between two benzene rings [centroid–centroid distance = 3.672 (1) Å].

Related literature

For the biological activity of thio­phene derivatives, see: Tapia et al. (2003[Tapia, R. A., Alegria, L., Pessoa, C. D., Salas, C., Cortes, M. J., Valderrama, J. A., Sarciron, M. E., Pautet, F., Walchshofer, N. & Fillion, H. (2003). Bioorg. Med. Chem. 11, 2175-2182.]); Dallemagne et al. (2003[Dallemagne, P., Khanh, L. P., Alsaidi, A., Varlet, I., Collot, V., Paillet, M., Bureau, R. & Rault, S. (2003). Bioorg. Chem. 11, 1161-1167.]). For related structures, see: Dufresne & Skene (2008[Dufresne, S. & Skene, W. G. (2008). Acta Cryst. E64, o782.]); Gunasekaran et al. (2009[Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.])

[Scheme 1]

Experimental

Crystal data

  • C30H32O8S2

  • Mr = 584.68

  • Triclinic, [P \overline 1]

  • a = 9.9439 (3) Å

  • b = 10.8163 (3) Å

  • c = 14.7536 (5) Å

  • α = 82.610 (2)°

  • β = 89.490 (2)°

  • γ = 64.983 (1)°

  • V = 1424.20 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 295 K

  • 0.24 × 0.20 × 0.18 mm
Data collection

  • Bruker Kappa APEX2 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.945, Tmax = 0.959

  • 40341 measured reflections

  • 11207 independent reflections

  • 7512 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.130

  • S = 1.02

  • 11207 reflections

  • 367 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C13—H13B⋯O2 0.97 2.43 2.9923 (17) 117
C22—H22B⋯O4 0.97 2.38 3.0169 (16) 123
C17—H17⋯O2i 0.93 2.43 3.3267 (16) 162
C25—H25⋯O4ii 0.93 2.51 3.2280 (16) 134
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809042214/bt5095sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042214/bt5095Isup2.hkl

checkCIF report


Comment top

In continuation of our studies on thiophene derivatives which exhibit biological activities such as anti-protozoal (Tapia et al., 2003), antitumor (Dallemagne et al., 2003), we report the crystal structure of the title compound. The geometric parameters of the title compound (Fig. 1) agree with the reported similar structures (Dufresne & Skene, 2008; Gunasekaran et al., 2009). The dihedral angle between the phenyl rings C14—C19 and C23—C28 is 18.8 (1)°.

The molecular structure is stabilized by intramolecular C—H···O hydrogen bonds. In the crystal structure, the molecules are linked via intermolecular C—H···O hydrogen bonds (see, Fig. 2), and are further consolidated by π···π [Cg4···Cg4 (1 - x, -y, -z) = 3.672 (1) Å; Cg4 is the centroid of C23—C28 ring] interactions. The intermolecular C17—H17···O2 hydrogen bond generates a twenty-membered ring, with a graph-set motif of R22(20) (Bernstein et al., 1995).

Related literature top

For the biological activity of thiophene derivatives, see: Tapia et al. (2003); Dallemagne et al. (2003). For related structures, see: Dufresne & Skene (2008); Gunasekaran et al. (2009). For graph-set notation, see: Bernstein et al. (1995)

Experimental top

To a solution of Diethyl 3,4-bis-(acetoxymethyl) thieno[2,3,-b]thiophene-2,5-dicarboxylate (0.7 g, 1.63 mmol) in dry 1,2-dichloroethane (10 ml), Ferric Chloride (0.05 g, 0.32 mmol) and 1,4-dimethoxybenzene (0.54 g, 3.92 mmol) were added under nitrogen atmosphere. The reaction mixture was refluxed for 20 hr, then it was poured over crushed ice (40 g) containing 1 ml of Conc.HCl. Ferric chloride was carefully filtered off and the filtrate was evaporated under reduced pressure giving crude product and it was crystallized from methanol affording pure product.

Refinement top

H atoms were positioned geometrically and refined using a riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, with C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for methylene and C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl.

Structure description top

In continuation of our studies on thiophene derivatives which exhibit biological activities such as anti-protozoal (Tapia et al., 2003), antitumor (Dallemagne et al., 2003), we report the crystal structure of the title compound. The geometric parameters of the title compound (Fig. 1) agree with the reported similar structures (Dufresne & Skene, 2008; Gunasekaran et al., 2009). The dihedral angle between the phenyl rings C14—C19 and C23—C28 is 18.8 (1)°.

The molecular structure is stabilized by intramolecular C—H···O hydrogen bonds. In the crystal structure, the molecules are linked via intermolecular C—H···O hydrogen bonds (see, Fig. 2), and are further consolidated by π···π [Cg4···Cg4 (1 - x, -y, -z) = 3.672 (1) Å; Cg4 is the centroid of C23—C28 ring] interactions. The intermolecular C17—H17···O2 hydrogen bond generates a twenty-membered ring, with a graph-set motif of R22(20) (Bernstein et al., 1995).

For the biological activity of thiophene derivatives, see: Tapia et al. (2003); Dallemagne et al. (2003). For related structures, see: Dufresne & Skene (2008); Gunasekaran et al. (2009). For graph-set notation, see: Bernstein et al. (1995)

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. C—H···O hydrogen bonds of the title compound. Hydrogen bonds are shown as dashed lines.
Diethyl 3,4-bis(2,5-dimethoxybenzyl)thieno[2,3-b]thiophene-2,5-dicarboxylate top
Crystal data top
C30H32O8S2Z = 2
Mr = 584.68F(000) = 616
Triclinic, P1Dx = 1.363 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.9439 (3) ÅCell parameters from 7622 reflections
b = 10.8163 (3) Åθ = 2.3–32.6°
c = 14.7536 (5) ŵ = 0.24 mm−1
α = 82.610 (2)°T = 295 K
β = 89.490 (2)°Block, colourless
γ = 64.983 (1)°0.24 × 0.20 × 0.18 mm
V = 1424.20 (8) Å3
Data collection top
Bruker Kappa APEX2 CCD
diffractometer		11207 independent reflections
Radiation source: fine-focus sealed tube7512 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω and φ scansθmax = 33.6°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→13
Tmin = 0.945, Tmax = 0.959k = −16→16
40341 measured reflectionsl = −22→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0618P)2 + 0.2259P]
where P = (Fo2 + 2Fc2)/3
11207 reflections(Δ/σ)max < 0.001
367 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C30H32O8S2γ = 64.983 (1)°
Mr = 584.68V = 1424.20 (8) Å3
Triclinic, P1Z = 2
a = 9.9439 (3) ÅMo Kα radiation
b = 10.8163 (3) ŵ = 0.24 mm−1
c = 14.7536 (5) ÅT = 295 K
α = 82.610 (2)°0.24 × 0.20 × 0.18 mm
β = 89.490 (2)°
Data collection top
Bruker Kappa APEX2 CCD
diffractometer		11207 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7512 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.959Rint = 0.028
40341 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.02Δρmax = 0.38 e Å−3
11207 reflectionsΔρmin = −0.21 e Å−3
367 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.33884 (12)0.45771 (12)0.29435 (9)0.0319 (2)
C20.45021 (11)0.29918 (12)0.43341 (9)0.0311 (2)
C30.50197 (11)0.23469 (11)0.35827 (8)0.0279 (2)
C40.43974 (11)0.32916 (11)0.27586 (8)0.0279 (2)
C50.45557 (11)0.32473 (11)0.17974 (8)0.0281 (2)
C60.36170 (13)0.44795 (12)0.13047 (9)0.0325 (2)
C70.48843 (12)0.24180 (13)0.53018 (9)0.0352 (3)
C80.4489 (2)0.30018 (16)0.68064 (10)0.0521 (4)
H8A0.55470.26320.69560.062*
H8B0.41480.23030.70210.062*
C90.3674 (2)0.42647 (18)0.72430 (12)0.0566 (4)
H9A0.39690.49710.69910.085*
H9B0.39040.40570.78910.085*
H9C0.26250.45800.71280.085*
C100.33664 (14)0.48317 (12)0.03113 (9)0.0363 (3)
C110.17568 (19)0.64930 (15)−0.08706 (10)0.0504 (4)
H11A0.26220.6182−0.12380.060*
H11B0.12660.7491−0.09910.060*
C120.07259 (19)0.5918 (2)−0.11375 (13)0.0612 (4)
H12A0.12260.4930−0.10470.092*
H12B0.04080.6239−0.17700.092*
H12C−0.01240.6213−0.07680.092*
C130.60622 (11)0.08518 (11)0.36206 (9)0.0307 (2)
H13A0.58510.05150.30860.037*
H13B0.58670.03420.41560.037*
C140.76908 (11)0.05525 (12)0.36583 (8)0.0309 (2)
C150.81823 (12)0.15692 (13)0.35845 (10)0.0371 (3)
H150.74930.24870.34920.045*
C160.96928 (13)0.12566 (15)0.36447 (10)0.0424 (3)
C171.07178 (14)−0.00949 (16)0.37866 (12)0.0522 (4)
H171.1727−0.03130.38350.063*
C181.02365 (14)−0.11288 (15)0.38571 (12)0.0520 (4)
H181.0930−0.20450.39500.062*
C190.87411 (13)−0.08212 (13)0.37913 (10)0.0389 (3)
C201.15560 (18)0.2084 (2)0.36269 (15)0.0663 (5)
H20A1.19850.15740.42140.099*
H20B1.16590.29330.35510.099*
H20C1.20590.15500.31540.099*
C210.92037 (18)−0.31882 (15)0.40392 (16)0.0665 (5)
H21A0.9815−0.34310.35250.100*
H21B0.8675−0.37550.41360.100*
H21C0.9818−0.33290.45760.100*
C220.56168 (12)0.20106 (11)0.13954 (9)0.0306 (2)
H22A0.65330.15830.17730.037*
H22B0.58500.23140.07910.037*
C230.50319 (12)0.09487 (11)0.13174 (8)0.0284 (2)
C240.60272 (12)−0.03646 (11)0.11506 (8)0.0303 (2)
C250.55198 (14)−0.13381 (12)0.10341 (9)0.0347 (3)
H250.6187−0.22040.09130.042*
C260.40264 (14)−0.10439 (13)0.10943 (9)0.0365 (3)
H260.3693−0.17090.10160.044*
C270.30409 (13)0.02372 (13)0.12702 (10)0.0368 (3)
C280.35525 (13)0.12273 (12)0.13736 (9)0.0341 (3)
H280.28790.20980.14830.041*
C290.85392 (16)−0.19303 (15)0.10302 (15)0.0629 (5)
H29A0.8512−0.25430.15550.094*
H29B0.9515−0.19540.10000.094*
H29C0.8306−0.22140.04850.094*
C300.09936 (18)−0.03504 (18)0.13132 (16)0.0695 (6)
H30A0.1141−0.06520.07210.104*
H30B−0.00480.00390.14220.104*
H30C0.1515−0.11220.17740.104*
O10.41917 (11)0.34007 (10)0.58310 (7)0.0441 (2)
O20.57034 (11)0.12509 (10)0.55927 (7)0.0472 (2)
O30.22256 (12)0.60698 (10)0.00899 (7)0.0478 (2)
O40.40665 (12)0.41188 (10)−0.02441 (7)0.0465 (2)
O51.00283 (11)0.23685 (12)0.35686 (9)0.0599 (3)
O60.81740 (10)−0.17839 (10)0.38624 (9)0.0527 (3)
O70.74872 (9)−0.05753 (9)0.11046 (7)0.0422 (2)
O80.15417 (11)0.06544 (10)0.13456 (9)0.0567 (3)
S10.25637 (3)0.57151 (3)0.19869 (2)0.03757 (9)
S20.32384 (3)0.47150 (3)0.40793 (2)0.03599 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0286 (5)0.0222 (5)0.0380 (6)−0.0045 (4)−0.0017 (4)−0.0035 (5)
C20.0230 (4)0.0262 (5)0.0381 (6)−0.0055 (4)−0.0013 (4)−0.0014 (5)
C30.0186 (4)0.0217 (5)0.0395 (6)−0.0059 (4)−0.0011 (4)−0.0009 (4)
C40.0219 (4)0.0202 (5)0.0391 (6)−0.0061 (4)−0.0003 (4)−0.0049 (4)
C50.0260 (5)0.0193 (5)0.0389 (6)−0.0090 (4)0.0005 (4)−0.0058 (4)
C60.0346 (5)0.0215 (5)0.0380 (6)−0.0082 (4)−0.0005 (5)−0.0058 (5)
C70.0258 (5)0.0351 (6)0.0410 (7)−0.0103 (4)−0.0003 (4)−0.0022 (5)
C80.0692 (10)0.0439 (8)0.0348 (7)−0.0176 (7)−0.0034 (7)0.0002 (6)
C90.0710 (10)0.0516 (9)0.0457 (9)−0.0236 (8)0.0054 (7)−0.0103 (7)
C100.0423 (6)0.0236 (5)0.0406 (7)−0.0119 (5)−0.0031 (5)−0.0032 (5)
C110.0619 (9)0.0350 (7)0.0397 (8)−0.0092 (6)−0.0058 (6)0.0049 (6)
C120.0542 (9)0.0628 (11)0.0544 (10)−0.0139 (8)−0.0071 (7)−0.0045 (8)
C130.0217 (4)0.0215 (5)0.0438 (7)−0.0053 (4)−0.0014 (4)−0.0009 (5)
C140.0207 (4)0.0281 (5)0.0375 (6)−0.0051 (4)−0.0006 (4)−0.0011 (5)
C150.0253 (5)0.0309 (6)0.0500 (8)−0.0089 (4)−0.0035 (5)0.0016 (5)
C160.0282 (5)0.0422 (7)0.0562 (9)−0.0161 (5)−0.0016 (5)0.0002 (6)
C170.0221 (5)0.0527 (9)0.0744 (11)−0.0104 (5)−0.0014 (6)−0.0026 (8)
C180.0233 (5)0.0375 (7)0.0813 (11)−0.0014 (5)−0.0018 (6)−0.0013 (7)
C190.0250 (5)0.0287 (6)0.0546 (8)−0.0041 (4)−0.0006 (5)−0.0021 (6)
C200.0417 (8)0.0801 (13)0.0891 (14)−0.0394 (9)0.0021 (8)−0.0048 (10)
C210.0420 (8)0.0258 (7)0.1165 (17)−0.0014 (6)0.0003 (9)−0.0035 (8)
C220.0275 (5)0.0214 (5)0.0413 (7)−0.0080 (4)0.0039 (4)−0.0080 (5)
C230.0305 (5)0.0195 (5)0.0325 (6)−0.0079 (4)−0.0004 (4)−0.0040 (4)
C240.0312 (5)0.0224 (5)0.0333 (6)−0.0074 (4)−0.0010 (4)−0.0040 (4)
C250.0398 (6)0.0213 (5)0.0392 (7)−0.0086 (4)−0.0008 (5)−0.0066 (5)
C260.0436 (6)0.0259 (6)0.0423 (7)−0.0169 (5)−0.0042 (5)−0.0041 (5)
C270.0325 (5)0.0290 (6)0.0489 (8)−0.0136 (5)−0.0018 (5)−0.0029 (5)
C280.0318 (5)0.0234 (5)0.0454 (7)−0.0095 (4)0.0026 (5)−0.0070 (5)
C290.0359 (7)0.0305 (7)0.1111 (16)−0.0009 (6)0.0019 (8)−0.0191 (8)
C300.0446 (8)0.0443 (9)0.1278 (18)−0.0277 (7)−0.0021 (9)−0.0076 (10)
O10.0496 (5)0.0361 (5)0.0352 (5)−0.0082 (4)−0.0011 (4)−0.0010 (4)
O20.0403 (5)0.0374 (5)0.0461 (6)−0.0019 (4)−0.0060 (4)0.0038 (4)
O30.0566 (6)0.0305 (5)0.0384 (5)−0.0021 (4)−0.0070 (4)−0.0016 (4)
O40.0572 (6)0.0320 (5)0.0414 (5)−0.0092 (4)0.0003 (4)−0.0094 (4)
O50.0373 (5)0.0541 (7)0.0934 (9)−0.0274 (5)−0.0039 (5)0.0010 (6)
O60.0291 (4)0.0249 (4)0.0941 (9)−0.0031 (3)−0.0010 (5)−0.0033 (5)
O70.0295 (4)0.0246 (4)0.0677 (7)−0.0052 (3)0.0021 (4)−0.0119 (4)
O80.0339 (5)0.0339 (5)0.1055 (10)−0.0176 (4)0.0040 (5)−0.0095 (6)
S10.03985 (16)0.02006 (14)0.03953 (18)0.00000 (11)−0.00335 (12)−0.00368 (12)
S20.03251 (14)0.02638 (15)0.03817 (17)−0.00160 (11)0.00029 (11)−0.00594 (12)
Geometric parameters (Å, º) top
C1—C41.3882 (15)C16—O51.3691 (17)
C1—S21.7010 (13)C16—C171.373 (2)
C1—S11.7028 (12)C17—C181.383 (2)
C2—C31.3658 (17)C17—H170.9300
C2—C71.4664 (18)C18—C191.3810 (17)
C2—S21.7440 (11)C18—H180.9300
C3—C41.4367 (16)C19—O61.3713 (16)
C3—C131.5009 (15)C20—O51.4175 (17)
C4—C51.4302 (17)C20—H20A0.9600
C5—C61.3736 (16)C20—H20B0.9600
C5—C221.5011 (15)C20—H20C0.9600
C6—C101.4622 (18)C21—O61.4182 (16)
C6—S11.7434 (12)C21—H21A0.9600
C7—O21.1993 (15)C21—H21B0.9600
C7—O11.3411 (16)C21—H21C0.9600
C8—O11.4438 (17)C22—C231.5070 (15)
C8—C91.489 (2)C22—H22A0.9700
C8—H8A0.9700C22—H22B0.9700
C8—H8B0.9700C23—C281.3753 (16)
C9—H9A0.9600C23—C241.3980 (15)
C9—H9B0.9600C24—O71.3735 (14)
C9—H9C0.9600C24—C251.3749 (17)
C10—O41.2038 (16)C25—C261.3856 (18)
C10—O31.3402 (15)C25—H250.9300
C11—O31.4489 (17)C26—C271.3738 (18)
C11—C121.484 (3)C26—H260.9300
C11—H11A0.9700C27—O81.3709 (15)
C11—H11B0.9700C27—C281.3904 (17)
C12—H12A0.9600C28—H280.9300
C12—H12B0.9600C29—O71.4132 (16)
C12—H12C0.9600C29—H29A0.9600
C13—C141.5113 (14)C29—H29B0.9600
C13—H13A0.9700C29—H29C0.9600
C13—H13B0.9700C30—O81.4126 (18)
C14—C151.3723 (17)C30—H30A0.9600
C14—C191.3976 (16)C30—H30B0.9600
C15—C161.3940 (16)C30—H30C0.9600
C15—H150.9300
C4—C1—S2113.79 (9)C16—C17—H17120.3
C4—C1—S1113.60 (10)C18—C17—H17120.3
S2—C1—S1132.60 (7)C19—C18—C17120.97 (13)
C3—C2—C7128.19 (11)C19—C18—H18119.5
C3—C2—S2114.17 (9)C17—C18—H18119.5
C7—C2—S2117.65 (9)O6—C19—C18124.55 (12)
C2—C3—C4110.44 (10)O6—C19—C14115.56 (10)
C2—C3—C13124.37 (11)C18—C19—C14119.89 (12)
C4—C3—C13125.17 (11)O5—C20—H20A109.5
C1—C4—C5111.91 (10)O5—C20—H20B109.5
C1—C4—C3111.79 (11)H20A—C20—H20B109.5
C5—C4—C3136.30 (10)O5—C20—H20C109.5
C6—C5—C4110.87 (10)H20A—C20—H20C109.5
C6—C5—C22125.33 (11)H20B—C20—H20C109.5
C4—C5—C22123.80 (10)O6—C21—H21A109.5
C5—C6—C10128.19 (11)O6—C21—H21B109.5
C5—C6—S1113.52 (10)H21A—C21—H21B109.5
C10—C6—S1118.23 (9)O6—C21—H21C109.5
O2—C7—O1123.98 (13)H21A—C21—H21C109.5
O2—C7—C2126.05 (13)H21B—C21—H21C109.5
O1—C7—C2109.97 (10)C5—C22—C23113.91 (9)
O1—C8—C9106.89 (12)C5—C22—H22A108.8
O1—C8—H8A110.3C23—C22—H22A108.8
C9—C8—H8A110.3C5—C22—H22B108.8
O1—C8—H8B110.3C23—C22—H22B108.8
C9—C8—H8B110.3H22A—C22—H22B107.7
H8A—C8—H8B108.6C28—C23—C24118.43 (10)
C8—C9—H9A109.5C28—C23—C22122.87 (10)
C8—C9—H9B109.5C24—C23—C22118.67 (10)
H9A—C9—H9B109.5O7—C24—C25124.38 (10)
C8—C9—H9C109.5O7—C24—C23115.46 (10)
H9A—C9—H9C109.5C25—C24—C23120.15 (10)
H9B—C9—H9C109.5C24—C25—C26120.79 (11)
O4—C10—O3123.61 (13)C24—C25—H25119.6
O4—C10—C6125.62 (12)C26—C25—H25119.6
O3—C10—C6110.77 (11)C27—C26—C25119.58 (11)
O3—C11—C12111.27 (13)C27—C26—H26120.2
O3—C11—H11A109.4C25—C26—H26120.2
C12—C11—H11A109.4O8—C27—C26125.18 (11)
O3—C11—H11B109.4O8—C27—C28115.27 (11)
C12—C11—H11B109.4C26—C27—C28119.55 (11)
H11A—C11—H11B108.0C23—C28—C27121.49 (11)
C11—C12—H12A109.5C23—C28—H28119.3
C11—C12—H12B109.5C27—C28—H28119.3
H12A—C12—H12B109.5O7—C29—H29A109.5
C11—C12—H12C109.5O7—C29—H29B109.5
H12A—C12—H12C109.5H29A—C29—H29B109.5
H12B—C12—H12C109.5O7—C29—H29C109.5
C3—C13—C14114.58 (9)H29A—C29—H29C109.5
C3—C13—H13A108.6H29B—C29—H29C109.5
C14—C13—H13A108.6O8—C30—H30A109.5
C3—C13—H13B108.6O8—C30—H30B109.5
C14—C13—H13B108.6H30A—C30—H30B109.5
H13A—C13—H13B107.6O8—C30—H30C109.5
C15—C14—C19118.60 (10)H30A—C30—H30C109.5
C15—C14—C13122.91 (10)H30B—C30—H30C109.5
C19—C14—C13118.49 (10)C7—O1—C8116.59 (11)
C14—C15—C16121.43 (12)C10—O3—C11116.74 (11)
C14—C15—H15119.3C16—O5—C20116.70 (13)
C16—C15—H15119.3C19—O6—C21117.14 (11)
O5—C16—C17124.94 (12)C24—O7—C29116.74 (11)
O5—C16—C15115.38 (12)C27—O8—C30117.02 (12)
C17—C16—C15119.67 (13)C1—S1—C690.05 (6)
C16—C17—C18119.44 (12)C1—S2—C289.71 (6)
C7—C2—C3—C4−178.22 (11)C13—C14—C19—O60.95 (18)
S2—C2—C3—C41.40 (12)C15—C14—C19—C180.8 (2)
C7—C2—C3—C133.19 (18)C13—C14—C19—C18−178.01 (14)
S2—C2—C3—C13−177.18 (8)C6—C5—C22—C23−97.49 (14)
S2—C1—C4—C5−176.41 (8)C4—C5—C22—C2382.76 (13)
S1—C1—C4—C52.66 (13)C5—C22—C23—C2816.39 (17)
S2—C1—C4—C33.39 (13)C5—C22—C23—C24−165.78 (11)
S1—C1—C4—C3−177.54 (8)C28—C23—C24—O7−179.86 (11)
C2—C3—C4—C1−3.00 (13)C22—C23—C24—O72.21 (16)
C13—C3—C4—C1175.58 (10)C28—C23—C24—C250.90 (18)
C2—C3—C4—C5176.74 (12)C22—C23—C24—C25−177.03 (11)
C13—C3—C4—C5−4.7 (2)O7—C24—C25—C26179.78 (12)
C1—C4—C5—C6−2.46 (14)C23—C24—C25—C26−1.05 (19)
C3—C4—C5—C6177.81 (12)C24—C25—C26—C270.2 (2)
C1—C4—C5—C22177.32 (10)C25—C26—C27—O8179.97 (13)
C3—C4—C5—C22−2.4 (2)C25—C26—C27—C280.8 (2)
C4—C5—C6—C10−175.76 (12)C24—C23—C28—C270.12 (19)
C22—C5—C6—C104.5 (2)C22—C23—C28—C27177.95 (12)
C4—C5—C6—S11.26 (13)O8—C27—C28—C23179.79 (12)
C22—C5—C6—S1−178.52 (9)C26—C27—C28—C23−1.0 (2)
C3—C2—C7—O2−2.2 (2)O2—C7—O1—C80.9 (2)
S2—C2—C7—O2178.21 (11)C2—C7—O1—C8−178.40 (11)
C3—C2—C7—O1177.11 (11)C9—C8—O1—C7176.97 (12)
S2—C2—C7—O1−2.51 (14)O4—C10—O3—C115.4 (2)
C5—C6—C10—O4−7.8 (2)C6—C10—O3—C11−174.08 (12)
S1—C6—C10—O4175.33 (11)C12—C11—O3—C1083.66 (17)
C5—C6—C10—O3171.65 (12)C17—C16—O5—C201.1 (2)
S1—C6—C10—O3−5.24 (15)C15—C16—O5—C20−179.98 (15)
C2—C3—C13—C14−89.64 (14)C18—C19—O6—C211.7 (2)
C4—C3—C13—C1491.98 (13)C14—C19—O6—C21−177.22 (15)
C3—C13—C14—C15−5.37 (18)C25—C24—O7—C29−7.0 (2)
C3—C13—C14—C19173.40 (12)C23—C24—O7—C29173.75 (14)
C19—C14—C15—C16−0.4 (2)C26—C27—O8—C305.4 (2)
C13—C14—C15—C16178.40 (13)C28—C27—O8—C30−175.40 (15)
C14—C15—C16—O5−179.37 (13)C4—C1—S1—C6−1.63 (10)
C14—C15—C16—C17−0.4 (2)S2—C1—S1—C6177.21 (10)
O5—C16—C17—C18179.61 (16)C5—C6—S1—C10.17 (10)
C15—C16—C17—C180.8 (3)C10—C6—S1—C1177.51 (10)
C16—C17—C18—C19−0.3 (3)C4—C1—S2—C2−2.18 (9)
C17—C18—C19—O6−179.35 (16)S1—C1—S2—C2178.98 (10)
C17—C18—C19—C14−0.5 (3)C3—C2—S2—C10.39 (9)
C15—C14—C19—O6179.78 (13)C7—C2—S2—C1−179.94 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13B···O20.972.432.9923 (17)117
C22—H22B···O40.972.383.0169 (16)123
C17—H17···O2i0.932.433.3267 (16)162
C25—H25···O4ii0.932.513.2280 (16)134
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formulaC30H32O8S2
Mr584.68
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.9439 (3), 10.8163 (3), 14.7536 (5)
α, β, γ (°)82.610 (2), 89.490 (2), 64.983 (1)
V (Å3)1424.20 (8)
Z2
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.24 × 0.20 × 0.18
Data collection
DiffractometerBruker Kappa APEX2 CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.945, 0.959
No. of measured, independent and
observed [I > 2σ(I)] reflections		40341, 11207, 7512
Rint0.028
(sin θ/λ)max (Å−1)0.778
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.130, 1.02
No. of reflections11207
No. of parameters367
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.38, −0.21

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13B···O20.972.432.9923 (17)117
C22—H22B···O40.972.383.0169 (16)123
C17—H17···O2i0.932.433.3267 (16)162
C25—H25···O4ii0.932.513.2280 (16)134
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z.
 

Acknowledgements

The authors thank the SAIF, IIT, Madras, India, for the data collection.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDallemagne, P., Khanh, L. P., Alsaidi, A., Varlet, I., Collot, V., Paillet, M., Bureau, R. & Rault, S. (2003). Bioorg. Chem. 11, 1161–1167.  CrossRef CAS Google Scholar
 First citationDufresne, S. & Skene, W. G. (2008). Acta Cryst. E64, o782.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTapia, R. A., Alegria, L., Pessoa, C. D., Salas, C., Cortes, M. J., Valderrama, J. A., Sarciron, M. E., Pautet, F., Walchshofer, N. & Fillion, H. (2003). Bioorg. Med. Chem. 11, 2175–2182.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2790
https://doi.org/10.1107/S1600536809042214
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS