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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2790.
Published online 2009 October 17. doi:  10.1107/S1600536809042214
PMCID: PMC2971147

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

Abstract

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 [triangle]); Dallemagne et al. (2003 [triangle]). For related structures, see: Dufresne & Skene (2008 [triangle]); Gunasekaran et al. (2009 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle])

An external file that holds a picture, illustration, etc.
Object name is e-65-o2790-scheme1.jpg

Experimental

Crystal data

  • C30H32O8S2
  • M r = 584.68
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2790-efi1.jpg
  • 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 [triangle]) T min = 0.945, T max = 0.959
  • 40341 measured reflections
  • 11207 independent reflections
  • 7512 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042214/bt5095Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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

Crystal data

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

Bruker Kappa APEX2 CCD diffractometer11207 independent reflections
Radiation source: fine-focus sealed tube7512 reflections with I > 2σ(I)
graphiteRint = 0.028
ω and [var phi] 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

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 = 1.01w = 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

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5095).

References

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