![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
5,7-Bis(1-benzothiophen-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine
aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: mnpsy2004@yahoo.com
In the title compound, C22H14O2S3, the dioxane ring is disordered over two sites [site occupancies = 0.623 (3) and 0.377 (3)]; both components adopt half-chair conformations. The two benzothiophene ring systems are asymmetrically twisted away from the attached thiophene ring [dihedral angles = 20.57 (3) and 6.70 (3)°] and are oriented at an angle of 26.83 (3)°. No significant hydrogen bonding or π–π interactions are observed in the crystal structure.
Related literature
For related literature, see: Cohen et al. (1977); Csaszar & Morvay (1983
); Dzhurayev et al. (1992
); EI-Maghraby et al. (1984
); Gewald et al. (1996
); Lakshmi et al. (1985
); Pellis & West (1968
). For the synthesis, see: Amaladass et al. (2007
).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2004); cell APEX2; 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, 2003
); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995
).
Supporting information
10.1107/S1600536808012324/ci2577sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808012324/ci2577Isup2.hkl
The title compound was prepared according to the procedure reported by Amaladass et al. (2007). Single crystals suitable for X-ray analysis were obtained by slow evaporation method.
The methylene C atoms of the dioxane ring are disordered over two positions (C11A/C11B and C12A/C12B) with refined occupancies of 0.623 (3) and 0.377 (3). The corresponding bond distances involving the disordered atoms were restrained to be equal, and also the same Uij parameters were used for atoms C11A and C11B, and C12A and C12B. H atoms were positioned geometrically (C—H = 0.93 Å or 0.97 Å) and were treated as riding on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 (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, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995). ![]() | Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Both disorder components are shown. |
C22H14O2S3 | F(000) = 840 |
Mr = 406.51 | Dx = 1.478 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4583 reflections |
a = 16.1602 (5) Å | θ = 2.8–33.8° |
b = 8.3524 (3) Å | µ = 0.42 mm−1 |
c = 14.1814 (4) Å | T = 293 K |
β = 107.428 (2)° | Block, light green |
V = 1826.28 (10) Å3 | 0.15 × 0.13 × 0.10 mm |
Z = 4 |
Bruker Kappa APEXII area-detector diffractometer | 4551 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 33.4°, θmin = 2.8° |
ω and ϕ scans | h = −24→24 |
26571 measured reflections | k = −12→10 |
7059 independent reflections | l = −21→19 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0749P)2 + 0.444P] where P = (Fo2 + 2Fc2)/3 |
7059 reflections | (Δ/σ)max < 0.001 |
251 parameters | Δρmax = 0.61 e Å−3 |
3 restraints | Δρmin = −0.43 e Å−3 |
C22H14O2S3 | V = 1826.28 (10) Å3 |
Mr = 406.51 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.1602 (5) Å | µ = 0.42 mm−1 |
b = 8.3524 (3) Å | T = 293 K |
c = 14.1814 (4) Å | 0.15 × 0.13 × 0.10 mm |
β = 107.428 (2)° |
Bruker Kappa APEXII area-detector diffractometer | 4551 reflections with I > 2σ(I) |
26571 measured reflections | Rint = 0.028 |
7059 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 3 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.61 e Å−3 |
7059 reflections | Δρmin = −0.43 e Å−3 |
251 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | −0.28863 (11) | 0.4031 (2) | −0.01894 (14) | 0.0499 (4) | |
H1 | −0.2949 | 0.3569 | −0.0804 | 0.060* | |
C2 | −0.35994 (12) | 0.4572 (3) | 0.00498 (16) | 0.0578 (5) | |
H2 | −0.4145 | 0.4490 | −0.0412 | 0.069* | |
C3 | −0.35223 (12) | 0.5241 (2) | 0.09694 (18) | 0.0597 (5) | |
H3 | −0.4017 | 0.5590 | 0.1115 | 0.072* | |
C4 | −0.27258 (12) | 0.5395 (2) | 0.16681 (16) | 0.0533 (4) | |
H4 | −0.2674 | 0.5837 | 0.2285 | 0.064* | |
C5 | −0.19971 (10) | 0.48665 (19) | 0.14227 (13) | 0.0419 (3) | |
C6 | −0.20599 (10) | 0.41809 (19) | 0.05007 (12) | 0.0400 (3) | |
C7 | −0.12301 (10) | 0.3765 (2) | 0.03966 (13) | 0.0430 (3) | |
H7 | −0.1153 | 0.3287 | −0.0164 | 0.052* | |
C8 | −0.05619 (10) | 0.41564 (19) | 0.12239 (11) | 0.0374 (3) | |
C9 | 0.03586 (9) | 0.39615 (18) | 0.13747 (11) | 0.0364 (3) | |
C10 | 0.07580 (9) | 0.29651 (18) | 0.08760 (11) | 0.0357 (3) | |
C11A | 0.08383 (17) | 0.1322 (5) | −0.0432 (2) | 0.0502 (8) | 0.623 (3) |
H11A | 0.0937 | 0.2125 | −0.0881 | 0.060* | 0.623 (3) |
H11B | 0.0543 | 0.0420 | −0.0820 | 0.060* | 0.623 (3) |
C12A | 0.16828 (17) | 0.0790 (3) | 0.0260 (2) | 0.0485 (6) | 0.623 (3) |
H12A | 0.1574 | −0.0005 | 0.0707 | 0.058* | 0.623 (3) |
H12B | 0.2022 | 0.0283 | −0.0117 | 0.058* | 0.623 (3) |
C11B | 0.0915 (3) | 0.0850 (5) | −0.0061 (4) | 0.0502 (8) | 0.377 (3) |
H11C | 0.0623 | 0.0295 | −0.0670 | 0.060* | 0.377 (3) |
H11D | 0.1046 | 0.0059 | 0.0464 | 0.060* | 0.377 (3) |
C12B | 0.1754 (3) | 0.1472 (7) | −0.0147 (2) | 0.0485 (6) | 0.377 (3) |
H12C | 0.2092 | 0.0622 | −0.0318 | 0.058* | 0.377 (3) |
H12D | 0.1658 | 0.2309 | −0.0643 | 0.058* | 0.377 (3) |
C13 | 0.16712 (9) | 0.30254 (18) | 0.12251 (11) | 0.0365 (3) | |
C14 | 0.19858 (9) | 0.40987 (19) | 0.19816 (11) | 0.0362 (3) | |
C15 | 0.28812 (9) | 0.44752 (19) | 0.24924 (11) | 0.0352 (3) | |
C16 | 0.36041 (10) | 0.3755 (2) | 0.23942 (12) | 0.0416 (3) | |
H16 | 0.3587 | 0.2893 | 0.1973 | 0.050* | |
C17 | 0.43920 (10) | 0.44442 (19) | 0.29966 (11) | 0.0380 (3) | |
C18 | 0.52506 (11) | 0.4008 (2) | 0.30912 (15) | 0.0512 (4) | |
H18 | 0.5366 | 0.3159 | 0.2725 | 0.061* | |
C19 | 0.59199 (11) | 0.4840 (2) | 0.37253 (15) | 0.0521 (4) | |
H19 | 0.6489 | 0.4558 | 0.3781 | 0.062* | |
C20 | 0.57576 (11) | 0.6105 (2) | 0.42876 (14) | 0.0483 (4) | |
H20 | 0.6220 | 0.6645 | 0.4722 | 0.058* | |
C21 | 0.49236 (11) | 0.6563 (2) | 0.42076 (13) | 0.0469 (4) | |
H21 | 0.4816 | 0.7414 | 0.4578 | 0.056* | |
C22 | 0.42398 (9) | 0.57260 (19) | 0.35592 (11) | 0.0374 (3) | |
O1 | 0.03162 (7) | 0.19777 (15) | 0.01304 (9) | 0.0476 (3) | |
O2 | 0.21883 (7) | 0.21067 (15) | 0.08407 (9) | 0.0467 (3) | |
S1 | 0.11311 (2) | 0.50367 (5) | 0.22588 (3) | 0.04068 (11) | |
S2 | 0.31369 (3) | 0.60648 (5) | 0.33305 (3) | 0.04677 (12) | |
S3 | −0.09260 (3) | 0.49989 (6) | 0.21576 (3) | 0.04834 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0415 (8) | 0.0560 (10) | 0.0467 (9) | −0.0071 (7) | 0.0047 (7) | 0.0089 (8) |
C2 | 0.0338 (8) | 0.0654 (12) | 0.0667 (12) | −0.0030 (8) | 0.0037 (8) | 0.0162 (10) |
C3 | 0.0355 (8) | 0.0585 (11) | 0.0856 (15) | 0.0057 (8) | 0.0188 (9) | 0.0054 (10) |
C4 | 0.0418 (9) | 0.0515 (10) | 0.0684 (12) | 0.0037 (7) | 0.0192 (8) | −0.0063 (9) |
C5 | 0.0336 (7) | 0.0393 (8) | 0.0529 (9) | −0.0002 (6) | 0.0131 (6) | 0.0001 (7) |
C6 | 0.0355 (7) | 0.0390 (8) | 0.0445 (8) | −0.0019 (6) | 0.0103 (6) | 0.0061 (6) |
C7 | 0.0352 (7) | 0.0473 (9) | 0.0470 (8) | 0.0003 (6) | 0.0132 (6) | 0.0079 (7) |
C8 | 0.0331 (7) | 0.0393 (8) | 0.0401 (7) | 0.0004 (5) | 0.0114 (5) | 0.0008 (6) |
C9 | 0.0316 (6) | 0.0395 (8) | 0.0378 (7) | −0.0003 (5) | 0.0098 (5) | 0.0003 (6) |
C10 | 0.0332 (6) | 0.0376 (7) | 0.0353 (7) | −0.0025 (5) | 0.0086 (5) | −0.0015 (6) |
C11A | 0.0450 (11) | 0.070 (2) | 0.0369 (17) | −0.0104 (12) | 0.0148 (13) | −0.0198 (14) |
C12A | 0.0432 (11) | 0.0540 (18) | 0.0478 (15) | 0.0009 (11) | 0.0128 (11) | −0.0150 (11) |
C11B | 0.0450 (11) | 0.070 (2) | 0.0369 (17) | −0.0104 (12) | 0.0148 (13) | −0.0198 (14) |
C12B | 0.0432 (11) | 0.0540 (18) | 0.0478 (15) | 0.0009 (11) | 0.0128 (11) | −0.0150 (11) |
C13 | 0.0340 (7) | 0.0378 (8) | 0.0383 (7) | 0.0019 (5) | 0.0116 (5) | −0.0024 (6) |
C14 | 0.0317 (6) | 0.0395 (8) | 0.0368 (7) | −0.0001 (5) | 0.0095 (5) | −0.0018 (6) |
C15 | 0.0338 (7) | 0.0372 (7) | 0.0349 (7) | −0.0016 (5) | 0.0106 (5) | −0.0026 (6) |
C16 | 0.0363 (7) | 0.0423 (8) | 0.0461 (8) | −0.0022 (6) | 0.0122 (6) | −0.0089 (7) |
C17 | 0.0338 (7) | 0.0402 (8) | 0.0411 (7) | −0.0023 (6) | 0.0130 (6) | −0.0008 (6) |
C18 | 0.0364 (8) | 0.0547 (10) | 0.0645 (11) | 0.0013 (7) | 0.0181 (7) | −0.0109 (8) |
C19 | 0.0328 (8) | 0.0577 (11) | 0.0659 (11) | −0.0027 (7) | 0.0153 (7) | −0.0001 (9) |
C20 | 0.0360 (8) | 0.0509 (10) | 0.0535 (9) | −0.0103 (7) | 0.0066 (7) | 0.0011 (8) |
C21 | 0.0402 (8) | 0.0486 (9) | 0.0495 (9) | −0.0081 (7) | 0.0096 (7) | −0.0090 (7) |
C22 | 0.0324 (7) | 0.0401 (8) | 0.0394 (7) | −0.0029 (6) | 0.0103 (5) | −0.0005 (6) |
O1 | 0.0379 (6) | 0.0534 (7) | 0.0495 (6) | −0.0055 (5) | 0.0100 (5) | −0.0169 (5) |
O2 | 0.0355 (5) | 0.0520 (7) | 0.0520 (6) | 0.0028 (5) | 0.0121 (5) | −0.0160 (5) |
S1 | 0.03413 (18) | 0.0475 (2) | 0.0409 (2) | −0.00031 (15) | 0.01199 (14) | −0.00916 (16) |
S2 | 0.03469 (19) | 0.0501 (2) | 0.0539 (2) | −0.00041 (16) | 0.01081 (16) | −0.01687 (18) |
S3 | 0.0361 (2) | 0.0621 (3) | 0.0464 (2) | 0.00043 (17) | 0.01175 (16) | −0.01084 (19) |
C1—C2 | 1.372 (3) | C11B—O1 | 1.434 (2) |
C1—C6 | 1.405 (2) | C11B—C12B | 1.490 (3) |
C1—H1 | 0.93 | C11B—H11C | 0.97 |
C2—C3 | 1.390 (3) | C11B—H11D | 0.97 |
C2—H2 | 0.93 | C12B—O2 | 1.465 (3) |
C3—C4 | 1.375 (3) | C12B—H12C | 0.97 |
C3—H3 | 0.93 | C12B—H12D | 0.97 |
C4—C5 | 1.396 (2) | C13—O2 | 1.3627 (18) |
C4—H4 | 0.93 | C13—C14 | 1.373 (2) |
C5—C6 | 1.403 (2) | C14—C15 | 1.445 (2) |
C5—S3 | 1.7361 (17) | C14—S1 | 1.7325 (15) |
C6—C7 | 1.435 (2) | C15—C16 | 1.358 (2) |
C7—C8 | 1.375 (2) | C15—S2 | 1.7470 (15) |
C7—H7 | 0.93 | C16—C17 | 1.425 (2) |
C8—C9 | 1.447 (2) | C16—H16 | 0.93 |
C8—S3 | 1.7496 (16) | C17—C22 | 1.400 (2) |
C9—C10 | 1.372 (2) | C17—C18 | 1.401 (2) |
C9—S1 | 1.7318 (15) | C18—C19 | 1.371 (3) |
C10—O1 | 1.3622 (18) | C18—H18 | 0.93 |
C10—C13 | 1.410 (2) | C19—C20 | 1.395 (3) |
C11A—O1 | 1.433 (2) | C19—H19 | 0.93 |
C11A—C12A | 1.490 (3) | C20—C21 | 1.373 (2) |
C11A—H11A | 0.97 | C20—H20 | 0.93 |
C11A—H11B | 0.97 | C21—C22 | 1.395 (2) |
C12A—O2 | 1.467 (2) | C21—H21 | 0.93 |
C12A—H12A | 0.97 | C22—S2 | 1.7365 (15) |
C12A—H12B | 0.97 | ||
C2—C1—C6 | 119.47 (18) | C12B—C11B—H11D | 107.8 |
C2—C1—H1 | 120.3 | H11C—C11B—H11D | 107.2 |
C6—C1—H1 | 120.3 | O2—C12B—C11B | 103.6 (3) |
C1—C2—C3 | 121.26 (17) | O2—C12B—H12C | 111.0 |
C1—C2—H2 | 119.4 | C11B—C12B—H12C | 111.0 |
C3—C2—H2 | 119.4 | O2—C12B—H12D | 111.0 |
C4—C3—C2 | 121.00 (18) | C11B—C12B—H12D | 111.0 |
C4—C3—H3 | 119.5 | H12C—C12B—H12D | 109.0 |
C2—C3—H3 | 119.5 | O2—C13—C14 | 123.51 (13) |
C3—C4—C5 | 117.93 (19) | O2—C13—C10 | 122.83 (13) |
C3—C4—H4 | 121.0 | C14—C13—C10 | 113.66 (13) |
C5—C4—H4 | 121.0 | C13—C14—C15 | 127.90 (14) |
C4—C5—C6 | 122.04 (16) | C13—C14—S1 | 109.79 (11) |
C4—C5—S3 | 126.46 (15) | C15—C14—S1 | 122.30 (12) |
C6—C5—S3 | 111.48 (12) | C16—C15—C14 | 127.96 (14) |
C5—C6—C1 | 118.29 (16) | C16—C15—S2 | 111.78 (11) |
C5—C6—C7 | 112.69 (14) | C14—C15—S2 | 120.24 (11) |
C1—C6—C7 | 129.00 (17) | C15—C16—C17 | 113.66 (14) |
C8—C7—C6 | 111.96 (15) | C15—C16—H16 | 123.2 |
C8—C7—H7 | 124.0 | C17—C16—H16 | 123.2 |
C6—C7—H7 | 124.0 | C22—C17—C18 | 118.81 (15) |
C7—C8—C9 | 127.53 (14) | C22—C17—C16 | 111.87 (13) |
C7—C8—S3 | 112.65 (12) | C18—C17—C16 | 129.32 (16) |
C9—C8—S3 | 119.82 (11) | C19—C18—C17 | 119.69 (17) |
C10—C9—C8 | 127.84 (14) | C19—C18—H18 | 120.2 |
C10—C9—S1 | 109.84 (11) | C17—C18—H18 | 120.2 |
C8—C9—S1 | 122.33 (12) | C18—C19—C20 | 120.82 (16) |
O1—C10—C9 | 123.31 (13) | C18—C19—H19 | 119.6 |
O1—C10—C13 | 122.97 (13) | C20—C19—H19 | 119.6 |
C9—C10—C13 | 113.69 (13) | C21—C20—C19 | 120.79 (16) |
O1—C11A—C12A | 108.9 (2) | C21—C20—H20 | 119.6 |
O1—C11A—H11A | 109.9 | C19—C20—H20 | 119.6 |
C12A—C11A—H11A | 109.9 | C20—C21—C22 | 118.62 (17) |
O1—C11A—H11B | 109.9 | C20—C21—H21 | 120.7 |
C12A—C11A—H11B | 109.9 | C22—C21—H21 | 120.7 |
H11A—C11A—H11B | 108.3 | C21—C22—C17 | 121.27 (15) |
O2—C12A—C11A | 113.1 (2) | C21—C22—S2 | 127.40 (13) |
O2—C12A—H12A | 109.0 | C17—C22—S2 | 111.34 (11) |
C11A—C12A—H12A | 109.0 | C10—O1—C11A | 113.88 (16) |
O2—C12A—H12B | 109.0 | C10—O1—C11B | 108.6 (3) |
C11A—C12A—H12B | 109.0 | C13—O2—C12B | 114.2 (2) |
H12A—C12A—H12B | 107.8 | C13—O2—C12A | 109.99 (15) |
O1—C11B—C12B | 117.9 (4) | C9—S1—C14 | 92.98 (7) |
O1—C11B—H11C | 107.8 | C22—S2—C15 | 91.35 (7) |
C12B—C11B—H11C | 107.8 | C5—S3—C8 | 91.20 (8) |
O1—C11B—H11D | 107.8 | ||
C6—C1—C2—C3 | −1.2 (3) | C15—C16—C17—C18 | 179.46 (17) |
C1—C2—C3—C4 | 0.6 (3) | C22—C17—C18—C19 | −0.2 (3) |
C2—C3—C4—C5 | 0.4 (3) | C16—C17—C18—C19 | −179.69 (18) |
C3—C4—C5—C6 | −0.7 (3) | C17—C18—C19—C20 | 0.8 (3) |
C3—C4—C5—S3 | 177.48 (15) | C18—C19—C20—C21 | −1.0 (3) |
C4—C5—C6—C1 | 0.1 (2) | C19—C20—C21—C22 | 0.7 (3) |
S3—C5—C6—C1 | −178.33 (13) | C20—C21—C22—C17 | −0.1 (3) |
C4—C5—C6—C7 | 178.37 (16) | C20—C21—C22—S2 | 179.76 (14) |
S3—C5—C6—C7 | −0.02 (18) | C18—C17—C22—C21 | −0.2 (2) |
C2—C1—C6—C5 | 0.8 (2) | C16—C17—C22—C21 | 179.43 (15) |
C2—C1—C6—C7 | −177.15 (17) | C18—C17—C22—S2 | 179.96 (13) |
C5—C6—C7—C8 | −0.8 (2) | C16—C17—C22—S2 | −0.43 (18) |
C1—C6—C7—C8 | 177.27 (16) | C9—C10—O1—C11A | 166.6 (2) |
C6—C7—C8—C9 | −177.96 (15) | C13—C10—O1—C11A | −15.2 (3) |
C6—C7—C8—S3 | 1.29 (18) | C9—C10—O1—C11B | −166.3 (3) |
C7—C8—C9—C10 | −20.4 (3) | C13—C10—O1—C11B | 11.9 (3) |
S3—C8—C9—C10 | 160.45 (14) | C12A—C11A—O1—C10 | 43.7 (3) |
C7—C8—C9—S1 | 159.31 (14) | C12A—C11A—O1—C11B | −39.6 (5) |
S3—C8—C9—S1 | −19.89 (18) | C12B—C11B—O1—C10 | −46.7 (5) |
C8—C9—C10—O1 | 0.2 (3) | C12B—C11B—O1—C11A | 60.0 (5) |
S1—C9—C10—O1 | −179.48 (12) | C14—C13—O2—C12B | −160.2 (3) |
C8—C9—C10—C13 | −178.15 (15) | C10—C13—O2—C12B | 19.4 (3) |
S1—C9—C10—C13 | 2.15 (17) | C14—C13—O2—C12A | 163.91 (19) |
O1—C11A—C12A—O2 | −62.3 (4) | C10—C13—O2—C12A | −16.4 (2) |
O1—C11B—C12B—O2 | 64.4 (6) | C11B—C12B—O2—C13 | −46.1 (4) |
O1—C10—C13—O2 | 0.4 (2) | C11B—C12B—O2—C12A | 43.8 (2) |
C9—C10—C13—O2 | 178.81 (14) | C11A—C12A—O2—C13 | 47.1 (3) |
O1—C10—C13—C14 | −179.88 (14) | C11A—C12A—O2—C12B | −56.9 (4) |
C9—C10—C13—C14 | −1.5 (2) | C10—C9—S1—C14 | −1.77 (12) |
O2—C13—C14—C15 | 0.8 (3) | C8—C9—S1—C14 | 178.51 (13) |
C10—C13—C14—C15 | −178.84 (15) | C13—C14—S1—C9 | 0.95 (13) |
O2—C13—C14—S1 | 179.79 (12) | C15—C14—S1—C9 | 179.96 (13) |
C10—C13—C14—S1 | 0.11 (17) | C21—C22—S2—C15 | −179.22 (16) |
C13—C14—C15—C16 | −6.2 (3) | C17—C22—S2—C15 | 0.63 (13) |
S1—C14—C15—C16 | 174.99 (14) | C16—C15—S2—C22 | −0.69 (13) |
C13—C14—C15—S2 | 171.90 (13) | C14—C15—S2—C22 | −179.06 (13) |
S1—C14—C15—S2 | −6.92 (19) | C4—C5—S3—C8 | −177.68 (17) |
C14—C15—C16—C17 | 178.79 (15) | C6—C5—S3—C8 | 0.63 (13) |
S2—C15—C16—C17 | 0.57 (19) | C7—C8—S3—C5 | −1.11 (13) |
C15—C16—C17—C22 | −0.1 (2) | C9—C8—S3—C5 | 178.20 (13) |
Experimental details
Crystal data | |
Chemical formula | C22H14O2S3 |
Mr | 406.51 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 16.1602 (5), 8.3524 (3), 14.1814 (4) |
β (°) | 107.428 (2) |
V (Å3) | 1826.28 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.42 |
Crystal size (mm) | 0.15 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Bruker Kappa APEXII area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26571, 7059, 4551 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.774 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.143, 0.99 |
No. of reflections | 7059 |
No. of parameters | 251 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.61, −0.43 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).
Acknowledgements
PS and SR thank Mr P. Charles for his help in solving the structure.
References
Amaladass, P., Clement, J. A. & Mohanakrishnan, A. K. (2007). Tetrahedron, 63, 10363–1067. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2004). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cohen, V. I., Rist, N. & Duponchel, C. (1977). J. Pharm. Sci. 66, 1322–1334. PubMed Web of Science Google Scholar
Csaszar, J. & Morvay, J. (1983). Acta Pharm. Hung. 53, 121–128. CAS PubMed Google Scholar
Dzhurayev, A. D., Karimkulov, K. M., Makhsumov, A. G. & Amanov, N. (1992). Khim. Farm. Zh. 26, 73–75. CAS Google Scholar
EI-Maghraby, A. A., Haroun, B. & Mohammed, N. A. (1984). Egypt. J. Pharm. Sci. 23, 327–336. Google Scholar
Gewald, K., Schinke, E. & Botcher, H. (1996). Chem. Ber. 99, 99–100. Google Scholar
Lakshmi, V. V., Sridhar, P. & Polasa, H. (1985). Indian J. Pharm. Sci. 47, 202–204. CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Pellis, G. & West, G. B. (1968). Progress in Medicinal Chemistry, Vol. 5, pp. 320–324. London: Butterworth & Co. Ltd. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals 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.
Sulfur containing Schiff bases (Pellis & West, 1968; Cohen et al., 1977; Csaszar & Morvay,1983; Lakshmi et al., 1985) and their thiophen derivatives (EI-Maghraby et al., 1984; Dzhurayev et al., 1992) possess pharmacological activities such as anti-bacterial, anti-cancer, anti-inflammatory and anti-toxic properties (Gewald et al., 1996). Benzo[b]thiophene analogs have been shown to possess interesting estrogenic and antiestrogenic effects. We report here the crystal structure of the title compound.
The C1—C8/S3 and C15—C22/S2 benzothiophene ring systems are essentially planar and are oriented at angles of 20.57 (3)° and 6.70 (3)°, respectively, with respect to the thiophene ring. The dihedral angle between the two benzothiophene ring systems is 26.83 (3)°. Both the major and minor conformers of the disordered dioxane ring adopt half-chair conformations. The crystal packing is stabilized by van der Waals forces.