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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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809042214/bt5095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809042214/bt5095Isup2.hkl
Contains datablock I

CCDC reference: 754355

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.045
  • wR factor = 0.130
  • Data-to-parameter ratio = 30.5

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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 m3
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 mm1
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 = 1513
Tmin = 0.945, Tmax = 0.959k = 1616
40341 measured reflectionsl = 2222
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 Å3
0 restraintsΔρmin = 0.21 e Å3
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 mm1
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 Å3
11207 reflectionsΔρmin = 0.21 e Å3
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)
H11A0.26220.61820.12380.060*
H11B0.12660.74910.09910.060*
C120.07259 (19)0.5918 (2)0.11375 (13)0.0612 (4)
H12A0.12260.49300.10470.092*
H12B0.04080.62390.17700.092*
H12C0.01240.62130.07680.092*
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)
H171.17270.03130.38350.063*
C181.02365 (14)0.11288 (15)0.38571 (12)0.0520 (4)
H181.09300.20450.39500.062*
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)
H21A0.98150.34310.35250.100*
H21B0.86750.37550.41360.100*
H21C0.98180.33290.45760.100*
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)
H250.61870.22040.09130.042*
C260.40264 (14)0.10439 (13)0.10943 (9)0.0365 (3)
H260.36930.17090.10160.044*
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)
H29A0.85120.25430.15550.094*
H29B0.95150.19540.10000.094*
H29C0.83060.22140.04850.094*
C300.09936 (18)0.03504 (18)0.13132 (16)0.0695 (6)
H30A0.11410.06520.07210.104*
H30B0.00480.00390.14220.104*
H30C0.15150.11220.17740.104*
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—C4178.22 (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—C18178.01 (14)
S2—C2—C3—C13177.18 (8)C6—C5—C22—C2397.49 (14)
S2—C1—C4—C5176.41 (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—C24165.78 (11)
S1—C1—C4—C3177.54 (8)C28—C23—C24—O7179.86 (11)
C2—C3—C4—C13.00 (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—C25177.03 (11)
C13—C3—C4—C54.7 (2)O7—C24—C25—C26179.78 (12)
C1—C4—C5—C62.46 (14)C23—C24—C25—C261.05 (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—C222.4 (2)C25—C26—C27—C280.8 (2)
C4—C5—C6—C10175.76 (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—S1178.52 (9)C26—C27—C28—C231.0 (2)
C3—C2—C7—O22.2 (2)O2—C7—O1—C80.9 (2)
S2—C2—C7—O2178.21 (11)C2—C7—O1—C8178.40 (11)
C3—C2—C7—O1177.11 (11)C9—C8—O1—C7176.97 (12)
S2—C2—C7—O12.51 (14)O4—C10—O3—C115.4 (2)
C5—C6—C10—O47.8 (2)C6—C10—O3—C11174.08 (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—O35.24 (15)C15—C16—O5—C20179.98 (15)
C2—C3—C13—C1489.64 (14)C18—C19—O6—C211.7 (2)
C4—C3—C13—C1491.98 (13)C14—C19—O6—C21177.22 (15)
C3—C13—C14—C155.37 (18)C25—C24—O7—C297.0 (2)
C3—C13—C14—C19173.40 (12)C23—C24—O7—C29173.75 (14)
C19—C14—C15—C160.4 (2)C26—C27—O8—C305.4 (2)
C13—C14—C15—C16178.40 (13)C28—C27—O8—C30175.40 (15)
C14—C15—C16—O5179.37 (13)C4—C1—S1—C61.63 (10)
C14—C15—C16—C170.4 (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—C190.3 (3)C4—C1—S2—C22.18 (9)
C17—C18—C19—O6179.35 (16)S1—C1—S2—C2178.98 (10)
C17—C18—C19—C140.5 (3)C3—C2—S2—C10.39 (9)
C15—C14—C19—O6179.78 (13)C7—C2—S2—C1179.94 (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)
V3)1424.20 (8)
Z2
Radiation typeMo Kα
µ (mm1)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)max1)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 Å3)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.
 

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