



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809042214/bt5095sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809042214/bt5095Isup2.hkl |
CCDC reference: 754355
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C)= 0.002 Å
- R factor = 0.045
- wR factor = 0.130
- Data-to-parameter ratio = 30.5
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
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.
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.
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)
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).
C30H32O8S2 | Z = 2 |
Mr = 584.68 | F(000) = 616 |
Triclinic, P1 | Dx = 1.363 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9439 (3) Å | Cell parameters from 7622 reflections |
b = 10.8163 (3) Å | θ = 2.3–32.6° |
c = 14.7536 (5) Å | µ = 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 |
Bruker Kappa APEX2 CCD diffractometer | 11207 independent reflections |
Radiation source: fine-focus sealed tube | 7512 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and φ scans | θmax = 33.6°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→13 |
Tmin = 0.945, Tmax = 0.959 | k = −16→16 |
40341 measured reflections | l = −22→22 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-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 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C30H32O8S2 | γ = 64.983 (1)° |
Mr = 584.68 | V = 1424.20 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.9439 (3) Å | Mo Kα radiation |
b = 10.8163 (3) Å | µ = 0.24 mm−1 |
c = 14.7536 (5) Å | T = 295 K |
α = 82.610 (2)° | 0.24 × 0.20 × 0.18 mm |
β = 89.490 (2)° |
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 = 0.959 | Rint = 0.028 |
40341 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.38 e Å−3 |
11207 reflections | Δρmin = −0.21 e Å−3 |
367 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.33884 (12) | 0.45771 (12) | 0.29435 (9) | 0.0319 (2) | |
C2 | 0.45021 (11) | 0.29918 (12) | 0.43341 (9) | 0.0311 (2) | |
C3 | 0.50197 (11) | 0.23469 (11) | 0.35827 (8) | 0.0279 (2) | |
C4 | 0.43974 (11) | 0.32916 (11) | 0.27586 (8) | 0.0279 (2) | |
C5 | 0.45557 (11) | 0.32473 (11) | 0.17974 (8) | 0.0281 (2) | |
C6 | 0.36170 (13) | 0.44795 (12) | 0.13047 (9) | 0.0325 (2) | |
C7 | 0.48843 (12) | 0.24180 (13) | 0.53018 (9) | 0.0352 (3) | |
C8 | 0.4489 (2) | 0.30018 (16) | 0.68064 (10) | 0.0521 (4) | |
H8A | 0.5547 | 0.2632 | 0.6956 | 0.062* | |
H8B | 0.4148 | 0.2303 | 0.7021 | 0.062* | |
C9 | 0.3674 (2) | 0.42647 (18) | 0.72430 (12) | 0.0566 (4) | |
H9A | 0.3969 | 0.4971 | 0.6991 | 0.085* | |
H9B | 0.3904 | 0.4057 | 0.7891 | 0.085* | |
H9C | 0.2625 | 0.4580 | 0.7128 | 0.085* | |
C10 | 0.33664 (14) | 0.48317 (12) | 0.03113 (9) | 0.0363 (3) | |
C11 | 0.17568 (19) | 0.64930 (15) | −0.08706 (10) | 0.0504 (4) | |
H11A | 0.2622 | 0.6182 | −0.1238 | 0.060* | |
H11B | 0.1266 | 0.7491 | −0.0991 | 0.060* | |
C12 | 0.07259 (19) | 0.5918 (2) | −0.11375 (13) | 0.0612 (4) | |
H12A | 0.1226 | 0.4930 | −0.1047 | 0.092* | |
H12B | 0.0408 | 0.6239 | −0.1770 | 0.092* | |
H12C | −0.0124 | 0.6213 | −0.0768 | 0.092* | |
C13 | 0.60622 (11) | 0.08518 (11) | 0.36206 (9) | 0.0307 (2) | |
H13A | 0.5851 | 0.0515 | 0.3086 | 0.037* | |
H13B | 0.5867 | 0.0342 | 0.4156 | 0.037* | |
C14 | 0.76908 (11) | 0.05525 (12) | 0.36583 (8) | 0.0309 (2) | |
C15 | 0.81823 (12) | 0.15692 (13) | 0.35845 (10) | 0.0371 (3) | |
H15 | 0.7493 | 0.2487 | 0.3492 | 0.045* | |
C16 | 0.96928 (13) | 0.12566 (15) | 0.36447 (10) | 0.0424 (3) | |
C17 | 1.07178 (14) | −0.00949 (16) | 0.37866 (12) | 0.0522 (4) | |
H17 | 1.1727 | −0.0313 | 0.3835 | 0.063* | |
C18 | 1.02365 (14) | −0.11288 (15) | 0.38571 (12) | 0.0520 (4) | |
H18 | 1.0930 | −0.2045 | 0.3950 | 0.062* | |
C19 | 0.87411 (13) | −0.08212 (13) | 0.37913 (10) | 0.0389 (3) | |
C20 | 1.15560 (18) | 0.2084 (2) | 0.36269 (15) | 0.0663 (5) | |
H20A | 1.1985 | 0.1574 | 0.4214 | 0.099* | |
H20B | 1.1659 | 0.2933 | 0.3551 | 0.099* | |
H20C | 1.2059 | 0.1550 | 0.3154 | 0.099* | |
C21 | 0.92037 (18) | −0.31882 (15) | 0.40392 (16) | 0.0665 (5) | |
H21A | 0.9815 | −0.3431 | 0.3525 | 0.100* | |
H21B | 0.8675 | −0.3755 | 0.4136 | 0.100* | |
H21C | 0.9818 | −0.3329 | 0.4576 | 0.100* | |
C22 | 0.56168 (12) | 0.20106 (11) | 0.13954 (9) | 0.0306 (2) | |
H22A | 0.6533 | 0.1583 | 0.1773 | 0.037* | |
H22B | 0.5850 | 0.2314 | 0.0791 | 0.037* | |
C23 | 0.50319 (12) | 0.09487 (11) | 0.13174 (8) | 0.0284 (2) | |
C24 | 0.60272 (12) | −0.03646 (11) | 0.11506 (8) | 0.0303 (2) | |
C25 | 0.55198 (14) | −0.13381 (12) | 0.10341 (9) | 0.0347 (3) | |
H25 | 0.6187 | −0.2204 | 0.0913 | 0.042* | |
C26 | 0.40264 (14) | −0.10439 (13) | 0.10943 (9) | 0.0365 (3) | |
H26 | 0.3693 | −0.1709 | 0.1016 | 0.044* | |
C27 | 0.30409 (13) | 0.02372 (13) | 0.12702 (10) | 0.0368 (3) | |
C28 | 0.35525 (13) | 0.12273 (12) | 0.13736 (9) | 0.0341 (3) | |
H28 | 0.2879 | 0.2098 | 0.1483 | 0.041* | |
C29 | 0.85392 (16) | −0.19303 (15) | 0.10302 (15) | 0.0629 (5) | |
H29A | 0.8512 | −0.2543 | 0.1555 | 0.094* | |
H29B | 0.9515 | −0.1954 | 0.1000 | 0.094* | |
H29C | 0.8306 | −0.2214 | 0.0485 | 0.094* | |
C30 | 0.09936 (18) | −0.03504 (18) | 0.13132 (16) | 0.0695 (6) | |
H30A | 0.1141 | −0.0652 | 0.0721 | 0.104* | |
H30B | −0.0048 | 0.0039 | 0.1422 | 0.104* | |
H30C | 0.1515 | −0.1122 | 0.1774 | 0.104* | |
O1 | 0.41917 (11) | 0.34007 (10) | 0.58310 (7) | 0.0441 (2) | |
O2 | 0.57034 (11) | 0.12509 (10) | 0.55927 (7) | 0.0472 (2) | |
O3 | 0.22256 (12) | 0.60698 (10) | 0.00899 (7) | 0.0478 (2) | |
O4 | 0.40665 (12) | 0.41188 (10) | −0.02441 (7) | 0.0465 (2) | |
O5 | 1.00283 (11) | 0.23685 (12) | 0.35686 (9) | 0.0599 (3) | |
O6 | 0.81740 (10) | −0.17839 (10) | 0.38624 (9) | 0.0527 (3) | |
O7 | 0.74872 (9) | −0.05753 (9) | 0.11046 (7) | 0.0422 (2) | |
O8 | 0.15417 (11) | 0.06544 (10) | 0.13456 (9) | 0.0567 (3) | |
S1 | 0.25637 (3) | 0.57151 (3) | 0.19869 (2) | 0.03757 (9) | |
S2 | 0.32384 (3) | 0.47150 (3) | 0.40793 (2) | 0.03599 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0286 (5) | 0.0222 (5) | 0.0380 (6) | −0.0045 (4) | −0.0017 (4) | −0.0035 (5) |
C2 | 0.0230 (4) | 0.0262 (5) | 0.0381 (6) | −0.0055 (4) | −0.0013 (4) | −0.0014 (5) |
C3 | 0.0186 (4) | 0.0217 (5) | 0.0395 (6) | −0.0059 (4) | −0.0011 (4) | −0.0009 (4) |
C4 | 0.0219 (4) | 0.0202 (5) | 0.0391 (6) | −0.0061 (4) | −0.0003 (4) | −0.0049 (4) |
C5 | 0.0260 (5) | 0.0193 (5) | 0.0389 (6) | −0.0090 (4) | 0.0005 (4) | −0.0058 (4) |
C6 | 0.0346 (5) | 0.0215 (5) | 0.0380 (6) | −0.0082 (4) | −0.0005 (5) | −0.0058 (5) |
C7 | 0.0258 (5) | 0.0351 (6) | 0.0410 (7) | −0.0103 (4) | −0.0003 (4) | −0.0022 (5) |
C8 | 0.0692 (10) | 0.0439 (8) | 0.0348 (7) | −0.0176 (7) | −0.0034 (7) | 0.0002 (6) |
C9 | 0.0710 (10) | 0.0516 (9) | 0.0457 (9) | −0.0236 (8) | 0.0054 (7) | −0.0103 (7) |
C10 | 0.0423 (6) | 0.0236 (5) | 0.0406 (7) | −0.0119 (5) | −0.0031 (5) | −0.0032 (5) |
C11 | 0.0619 (9) | 0.0350 (7) | 0.0397 (8) | −0.0092 (6) | −0.0058 (6) | 0.0049 (6) |
C12 | 0.0542 (9) | 0.0628 (11) | 0.0544 (10) | −0.0139 (8) | −0.0071 (7) | −0.0045 (8) |
C13 | 0.0217 (4) | 0.0215 (5) | 0.0438 (7) | −0.0053 (4) | −0.0014 (4) | −0.0009 (5) |
C14 | 0.0207 (4) | 0.0281 (5) | 0.0375 (6) | −0.0051 (4) | −0.0006 (4) | −0.0011 (5) |
C15 | 0.0253 (5) | 0.0309 (6) | 0.0500 (8) | −0.0089 (4) | −0.0035 (5) | 0.0016 (5) |
C16 | 0.0282 (5) | 0.0422 (7) | 0.0562 (9) | −0.0161 (5) | −0.0016 (5) | 0.0002 (6) |
C17 | 0.0221 (5) | 0.0527 (9) | 0.0744 (11) | −0.0104 (5) | −0.0014 (6) | −0.0026 (8) |
C18 | 0.0233 (5) | 0.0375 (7) | 0.0813 (11) | −0.0014 (5) | −0.0018 (6) | −0.0013 (7) |
C19 | 0.0250 (5) | 0.0287 (6) | 0.0546 (8) | −0.0041 (4) | −0.0006 (5) | −0.0021 (6) |
C20 | 0.0417 (8) | 0.0801 (13) | 0.0891 (14) | −0.0394 (9) | 0.0021 (8) | −0.0048 (10) |
C21 | 0.0420 (8) | 0.0258 (7) | 0.1165 (17) | −0.0014 (6) | 0.0003 (9) | −0.0035 (8) |
C22 | 0.0275 (5) | 0.0214 (5) | 0.0413 (7) | −0.0080 (4) | 0.0039 (4) | −0.0080 (5) |
C23 | 0.0305 (5) | 0.0195 (5) | 0.0325 (6) | −0.0079 (4) | −0.0004 (4) | −0.0040 (4) |
C24 | 0.0312 (5) | 0.0224 (5) | 0.0333 (6) | −0.0074 (4) | −0.0010 (4) | −0.0040 (4) |
C25 | 0.0398 (6) | 0.0213 (5) | 0.0392 (7) | −0.0086 (4) | −0.0008 (5) | −0.0066 (5) |
C26 | 0.0436 (6) | 0.0259 (6) | 0.0423 (7) | −0.0169 (5) | −0.0042 (5) | −0.0041 (5) |
C27 | 0.0325 (5) | 0.0290 (6) | 0.0489 (8) | −0.0136 (5) | −0.0018 (5) | −0.0029 (5) |
C28 | 0.0318 (5) | 0.0234 (5) | 0.0454 (7) | −0.0095 (4) | 0.0026 (5) | −0.0070 (5) |
C29 | 0.0359 (7) | 0.0305 (7) | 0.1111 (16) | −0.0009 (6) | 0.0019 (8) | −0.0191 (8) |
C30 | 0.0446 (8) | 0.0443 (9) | 0.1278 (18) | −0.0277 (7) | −0.0021 (9) | −0.0076 (10) |
O1 | 0.0496 (5) | 0.0361 (5) | 0.0352 (5) | −0.0082 (4) | −0.0011 (4) | −0.0010 (4) |
O2 | 0.0403 (5) | 0.0374 (5) | 0.0461 (6) | −0.0019 (4) | −0.0060 (4) | 0.0038 (4) |
O3 | 0.0566 (6) | 0.0305 (5) | 0.0384 (5) | −0.0021 (4) | −0.0070 (4) | −0.0016 (4) |
O4 | 0.0572 (6) | 0.0320 (5) | 0.0414 (5) | −0.0092 (4) | 0.0003 (4) | −0.0094 (4) |
O5 | 0.0373 (5) | 0.0541 (7) | 0.0934 (9) | −0.0274 (5) | −0.0039 (5) | 0.0010 (6) |
O6 | 0.0291 (4) | 0.0249 (4) | 0.0941 (9) | −0.0031 (3) | −0.0010 (5) | −0.0033 (5) |
O7 | 0.0295 (4) | 0.0246 (4) | 0.0677 (7) | −0.0052 (3) | 0.0021 (4) | −0.0119 (4) |
O8 | 0.0339 (5) | 0.0339 (5) | 0.1055 (10) | −0.0176 (4) | 0.0040 (5) | −0.0095 (6) |
S1 | 0.03985 (16) | 0.02006 (14) | 0.03953 (18) | 0.00000 (11) | −0.00335 (12) | −0.00368 (12) |
S2 | 0.03251 (14) | 0.02638 (15) | 0.03817 (17) | −0.00160 (11) | 0.00029 (11) | −0.00594 (12) |
C1—C4 | 1.3882 (15) | C16—O5 | 1.3691 (17) |
C1—S2 | 1.7010 (13) | C16—C17 | 1.373 (2) |
C1—S1 | 1.7028 (12) | C17—C18 | 1.383 (2) |
C2—C3 | 1.3658 (17) | C17—H17 | 0.9300 |
C2—C7 | 1.4664 (18) | C18—C19 | 1.3810 (17) |
C2—S2 | 1.7440 (11) | C18—H18 | 0.9300 |
C3—C4 | 1.4367 (16) | C19—O6 | 1.3713 (16) |
C3—C13 | 1.5009 (15) | C20—O5 | 1.4175 (17) |
C4—C5 | 1.4302 (17) | C20—H20A | 0.9600 |
C5—C6 | 1.3736 (16) | C20—H20B | 0.9600 |
C5—C22 | 1.5011 (15) | C20—H20C | 0.9600 |
C6—C10 | 1.4622 (18) | C21—O6 | 1.4182 (16) |
C6—S1 | 1.7434 (12) | C21—H21A | 0.9600 |
C7—O2 | 1.1993 (15) | C21—H21B | 0.9600 |
C7—O1 | 1.3411 (16) | C21—H21C | 0.9600 |
C8—O1 | 1.4438 (17) | C22—C23 | 1.5070 (15) |
C8—C9 | 1.489 (2) | C22—H22A | 0.9700 |
C8—H8A | 0.9700 | C22—H22B | 0.9700 |
C8—H8B | 0.9700 | C23—C28 | 1.3753 (16) |
C9—H9A | 0.9600 | C23—C24 | 1.3980 (15) |
C9—H9B | 0.9600 | C24—O7 | 1.3735 (14) |
C9—H9C | 0.9600 | C24—C25 | 1.3749 (17) |
C10—O4 | 1.2038 (16) | C25—C26 | 1.3856 (18) |
C10—O3 | 1.3402 (15) | C25—H25 | 0.9300 |
C11—O3 | 1.4489 (17) | C26—C27 | 1.3738 (18) |
C11—C12 | 1.484 (3) | C26—H26 | 0.9300 |
C11—H11A | 0.9700 | C27—O8 | 1.3709 (15) |
C11—H11B | 0.9700 | C27—C28 | 1.3904 (17) |
C12—H12A | 0.9600 | C28—H28 | 0.9300 |
C12—H12B | 0.9600 | C29—O7 | 1.4132 (16) |
C12—H12C | 0.9600 | C29—H29A | 0.9600 |
C13—C14 | 1.5113 (14) | C29—H29B | 0.9600 |
C13—H13A | 0.9700 | C29—H29C | 0.9600 |
C13—H13B | 0.9700 | C30—O8 | 1.4126 (18) |
C14—C15 | 1.3723 (17) | C30—H30A | 0.9600 |
C14—C19 | 1.3976 (16) | C30—H30B | 0.9600 |
C15—C16 | 1.3940 (16) | C30—H30C | 0.9600 |
C15—H15 | 0.9300 | ||
C4—C1—S2 | 113.79 (9) | C16—C17—H17 | 120.3 |
C4—C1—S1 | 113.60 (10) | C18—C17—H17 | 120.3 |
S2—C1—S1 | 132.60 (7) | C19—C18—C17 | 120.97 (13) |
C3—C2—C7 | 128.19 (11) | C19—C18—H18 | 119.5 |
C3—C2—S2 | 114.17 (9) | C17—C18—H18 | 119.5 |
C7—C2—S2 | 117.65 (9) | O6—C19—C18 | 124.55 (12) |
C2—C3—C4 | 110.44 (10) | O6—C19—C14 | 115.56 (10) |
C2—C3—C13 | 124.37 (11) | C18—C19—C14 | 119.89 (12) |
C4—C3—C13 | 125.17 (11) | O5—C20—H20A | 109.5 |
C1—C4—C5 | 111.91 (10) | O5—C20—H20B | 109.5 |
C1—C4—C3 | 111.79 (11) | H20A—C20—H20B | 109.5 |
C5—C4—C3 | 136.30 (10) | O5—C20—H20C | 109.5 |
C6—C5—C4 | 110.87 (10) | H20A—C20—H20C | 109.5 |
C6—C5—C22 | 125.33 (11) | H20B—C20—H20C | 109.5 |
C4—C5—C22 | 123.80 (10) | O6—C21—H21A | 109.5 |
C5—C6—C10 | 128.19 (11) | O6—C21—H21B | 109.5 |
C5—C6—S1 | 113.52 (10) | H21A—C21—H21B | 109.5 |
C10—C6—S1 | 118.23 (9) | O6—C21—H21C | 109.5 |
O2—C7—O1 | 123.98 (13) | H21A—C21—H21C | 109.5 |
O2—C7—C2 | 126.05 (13) | H21B—C21—H21C | 109.5 |
O1—C7—C2 | 109.97 (10) | C5—C22—C23 | 113.91 (9) |
O1—C8—C9 | 106.89 (12) | C5—C22—H22A | 108.8 |
O1—C8—H8A | 110.3 | C23—C22—H22A | 108.8 |
C9—C8—H8A | 110.3 | C5—C22—H22B | 108.8 |
O1—C8—H8B | 110.3 | C23—C22—H22B | 108.8 |
C9—C8—H8B | 110.3 | H22A—C22—H22B | 107.7 |
H8A—C8—H8B | 108.6 | C28—C23—C24 | 118.43 (10) |
C8—C9—H9A | 109.5 | C28—C23—C22 | 122.87 (10) |
C8—C9—H9B | 109.5 | C24—C23—C22 | 118.67 (10) |
H9A—C9—H9B | 109.5 | O7—C24—C25 | 124.38 (10) |
C8—C9—H9C | 109.5 | O7—C24—C23 | 115.46 (10) |
H9A—C9—H9C | 109.5 | C25—C24—C23 | 120.15 (10) |
H9B—C9—H9C | 109.5 | C24—C25—C26 | 120.79 (11) |
O4—C10—O3 | 123.61 (13) | C24—C25—H25 | 119.6 |
O4—C10—C6 | 125.62 (12) | C26—C25—H25 | 119.6 |
O3—C10—C6 | 110.77 (11) | C27—C26—C25 | 119.58 (11) |
O3—C11—C12 | 111.27 (13) | C27—C26—H26 | 120.2 |
O3—C11—H11A | 109.4 | C25—C26—H26 | 120.2 |
C12—C11—H11A | 109.4 | O8—C27—C26 | 125.18 (11) |
O3—C11—H11B | 109.4 | O8—C27—C28 | 115.27 (11) |
C12—C11—H11B | 109.4 | C26—C27—C28 | 119.55 (11) |
H11A—C11—H11B | 108.0 | C23—C28—C27 | 121.49 (11) |
C11—C12—H12A | 109.5 | C23—C28—H28 | 119.3 |
C11—C12—H12B | 109.5 | C27—C28—H28 | 119.3 |
H12A—C12—H12B | 109.5 | O7—C29—H29A | 109.5 |
C11—C12—H12C | 109.5 | O7—C29—H29B | 109.5 |
H12A—C12—H12C | 109.5 | H29A—C29—H29B | 109.5 |
H12B—C12—H12C | 109.5 | O7—C29—H29C | 109.5 |
C3—C13—C14 | 114.58 (9) | H29A—C29—H29C | 109.5 |
C3—C13—H13A | 108.6 | H29B—C29—H29C | 109.5 |
C14—C13—H13A | 108.6 | O8—C30—H30A | 109.5 |
C3—C13—H13B | 108.6 | O8—C30—H30B | 109.5 |
C14—C13—H13B | 108.6 | H30A—C30—H30B | 109.5 |
H13A—C13—H13B | 107.6 | O8—C30—H30C | 109.5 |
C15—C14—C19 | 118.60 (10) | H30A—C30—H30C | 109.5 |
C15—C14—C13 | 122.91 (10) | H30B—C30—H30C | 109.5 |
C19—C14—C13 | 118.49 (10) | C7—O1—C8 | 116.59 (11) |
C14—C15—C16 | 121.43 (12) | C10—O3—C11 | 116.74 (11) |
C14—C15—H15 | 119.3 | C16—O5—C20 | 116.70 (13) |
C16—C15—H15 | 119.3 | C19—O6—C21 | 117.14 (11) |
O5—C16—C17 | 124.94 (12) | C24—O7—C29 | 116.74 (11) |
O5—C16—C15 | 115.38 (12) | C27—O8—C30 | 117.02 (12) |
C17—C16—C15 | 119.67 (13) | C1—S1—C6 | 90.05 (6) |
C16—C17—C18 | 119.44 (12) | C1—S2—C2 | 89.71 (6) |
C7—C2—C3—C4 | −178.22 (11) | C13—C14—C19—O6 | 0.95 (18) |
S2—C2—C3—C4 | 1.40 (12) | C15—C14—C19—C18 | 0.8 (2) |
C7—C2—C3—C13 | 3.19 (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—C23 | 82.76 (13) |
S1—C1—C4—C5 | 2.66 (13) | C5—C22—C23—C28 | 16.39 (17) |
S2—C1—C4—C3 | 3.39 (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—O7 | 2.21 (16) |
C13—C3—C4—C1 | 175.58 (10) | C28—C23—C24—C25 | 0.90 (18) |
C2—C3—C4—C5 | 176.74 (12) | C22—C23—C24—C25 | −177.03 (11) |
C13—C3—C4—C5 | −4.7 (2) | O7—C24—C25—C26 | 179.78 (12) |
C1—C4—C5—C6 | −2.46 (14) | C23—C24—C25—C26 | −1.05 (19) |
C3—C4—C5—C6 | 177.81 (12) | C24—C25—C26—C27 | 0.2 (2) |
C1—C4—C5—C22 | 177.32 (10) | C25—C26—C27—O8 | 179.97 (13) |
C3—C4—C5—C22 | −2.4 (2) | C25—C26—C27—C28 | 0.8 (2) |
C4—C5—C6—C10 | −175.76 (12) | C24—C23—C28—C27 | 0.12 (19) |
C22—C5—C6—C10 | 4.5 (2) | C22—C23—C28—C27 | 177.95 (12) |
C4—C5—C6—S1 | 1.26 (13) | O8—C27—C28—C23 | 179.79 (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—C8 | 0.9 (2) |
S2—C2—C7—O2 | 178.21 (11) | C2—C7—O1—C8 | −178.40 (11) |
C3—C2—C7—O1 | 177.11 (11) | C9—C8—O1—C7 | 176.97 (12) |
S2—C2—C7—O1 | −2.51 (14) | O4—C10—O3—C11 | 5.4 (2) |
C5—C6—C10—O4 | −7.8 (2) | C6—C10—O3—C11 | −174.08 (12) |
S1—C6—C10—O4 | 175.33 (11) | C12—C11—O3—C10 | 83.66 (17) |
C5—C6—C10—O3 | 171.65 (12) | C17—C16—O5—C20 | 1.1 (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—C21 | 1.7 (2) |
C4—C3—C13—C14 | 91.98 (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—C19 | 173.40 (12) | C23—C24—O7—C29 | 173.75 (14) |
C19—C14—C15—C16 | −0.4 (2) | C26—C27—O8—C30 | 5.4 (2) |
C13—C14—C15—C16 | 178.40 (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—C6 | 177.21 (10) |
O5—C16—C17—C18 | 179.61 (16) | C5—C6—S1—C1 | 0.17 (10) |
C15—C16—C17—C18 | 0.8 (3) | C10—C6—S1—C1 | 177.51 (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—C2 | 178.98 (10) |
C17—C18—C19—C14 | −0.5 (3) | C3—C2—S2—C1 | 0.39 (9) |
C15—C14—C19—O6 | 179.78 (13) | C7—C2—S2—C1 | −179.94 (10) |
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. |
Experimental details
Crystal data | |
Chemical formula | C30H32O8S2 |
Mr | 584.68 |
Crystal system, space group | Triclinic, 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) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.24 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker Kappa APEX2 CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.945, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40341, 11207, 7512 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.778 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.130, 1.02 |
No. of reflections | 11207 |
No. of parameters | 367 |
H-atom treatment | H-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).
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. |
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).