Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802005986/ci6108sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802005986/ci6108Isup2.hkl |
CCDC reference: 185776
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.116
- Data-to-parameter ratio = 11.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Colourless single crystals of the title compound were obtained as transparent needles from its saturated solution in methanol by slow evaporation at room temperature.
All the H atoms were located from a difference Fourier map and were included in refinement with isotropic displacement parameters. The C—H distances range from 0.90 (3) to 0.99 (3) Å.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C30H20Cl2O4S | F(000) = 1128 |
Mr = 547.42 | Dx = 1.385 Mg m−3 |
Monoclinic, P21/c | Melting point: 157(1) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.0724 (17) Å | Cell parameters from 25 reflections |
b = 16.3184 (16) Å | θ = 8–13° |
c = 11.768 (3) Å | µ = 0.36 mm−1 |
β = 103.66 (2)° | T = 293 K |
V = 2626.0 (8) Å3 | Needle, colourless |
Z = 4 | 0.43 × 0.32 × 0.25 mm |
Enraf-Nonius CAD-4 diffractometer | 3241 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.014 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω–2θ scans | h = −16→16 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→19 |
Tmin = 0.84, Tmax = 0.91 | l = 0→13 |
4835 measured reflections | 2 standard reflections every 60 min |
4587 independent reflections | intensity decay: <2% |
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) = 0.116 | All H-atom parameters refined |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.9486P] where P = (Fo2 + 2Fc2)/3 |
4587 reflections | (Δ/σ)max < 0.001 |
414 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C30H20Cl2O4S | V = 2626.0 (8) Å3 |
Mr = 547.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.0724 (17) Å | µ = 0.36 mm−1 |
b = 16.3184 (16) Å | T = 293 K |
c = 11.768 (3) Å | 0.43 × 0.32 × 0.25 mm |
β = 103.66 (2)° |
Enraf-Nonius CAD-4 diffractometer | 3241 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.014 |
Tmin = 0.84, Tmax = 0.91 | 2 standard reflections every 60 min |
4835 measured reflections | intensity decay: <2% |
4587 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.116 | All H-atom parameters refined |
S = 1.11 | Δρmax = 0.24 e Å−3 |
4587 reflections | Δρmin = −0.35 e Å−3 |
414 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 | ||
Cl1 | 0.02500 (7) | 0.29560 (6) | 0.49783 (10) | 0.0971 (3) | |
Cl1' | 0.88584 (5) | 0.49366 (6) | 0.40510 (7) | 0.0730 (3) | |
S1 | 0.39182 (5) | 0.47228 (4) | 0.31217 (5) | 0.04482 (18) | |
O1 | 0.30838 (14) | 0.38156 (12) | 0.11740 (15) | 0.0596 (5) | |
O1' | 0.41833 (13) | 0.63302 (11) | 0.27413 (15) | 0.0518 (5) | |
O2 | 0.49349 (17) | 0.37525 (17) | 0.08187 (17) | 0.0884 (8) | |
O2' | 0.29636 (15) | 0.56429 (15) | 0.01881 (16) | 0.0704 (6) | |
C1 | 0.39180 (19) | 0.38917 (16) | 0.2125 (2) | 0.0475 (6) | |
C1' | 0.38650 (18) | 0.55804 (15) | 0.2149 (2) | 0.0425 (6) | |
C2 | 0.3206 (2) | 0.32129 (18) | 0.2089 (3) | 0.0567 (7) | |
C2' | 0.47509 (19) | 0.59922 (16) | 0.1974 (2) | 0.0478 (6) | |
C3 | 0.24644 (19) | 0.31651 (16) | 0.2791 (3) | 0.0537 (7) | |
C3' | 0.57680 (18) | 0.57421 (15) | 0.2510 (2) | 0.0435 (6) | |
C4 | 0.1679 (2) | 0.36992 (19) | 0.2628 (3) | 0.0608 (8) | |
C4' | 0.6136 (2) | 0.57065 (19) | 0.3717 (2) | 0.0557 (7) | |
C5 | 0.0995 (2) | 0.3637 (2) | 0.3282 (3) | 0.0667 (9) | |
C5' | 0.7076 (2) | 0.5472 (2) | 0.4186 (2) | 0.0595 (8) | |
C6 | 0.1095 (2) | 0.30344 (18) | 0.4118 (3) | 0.0625 (8) | |
C6' | 0.76716 (18) | 0.52692 (17) | 0.3457 (2) | 0.0510 (7) | |
C7 | 0.1854 (2) | 0.2493 (2) | 0.4288 (3) | 0.0667 (8) | |
C7' | 0.7334 (2) | 0.53037 (18) | 0.2264 (2) | 0.0529 (7) | |
C8 | 0.2533 (2) | 0.25561 (19) | 0.3628 (3) | 0.0633 (8) | |
C8' | 0.6386 (2) | 0.55418 (17) | 0.1798 (2) | 0.0504 (7) | |
C9 | 0.4877 (2) | 0.36998 (17) | 0.1821 (2) | 0.0531 (7) | |
C9' | 0.2922 (2) | 0.56770 (16) | 0.1205 (2) | 0.0490 (6) | |
C10 | 0.57080 (19) | 0.34187 (15) | 0.2760 (2) | 0.0466 (6) | |
C10' | 0.19918 (19) | 0.58210 (15) | 0.1551 (2) | 0.0478 (6) | |
C11 | 0.6625 (2) | 0.33480 (18) | 0.2532 (3) | 0.0572 (7) | |
C11' | 0.1120 (2) | 0.5799 (2) | 0.0693 (3) | 0.0639 (8) | |
C12 | 0.7402 (2) | 0.3049 (2) | 0.3366 (4) | 0.0742 (10) | |
C12' | 0.0240 (2) | 0.5926 (2) | 0.0982 (4) | 0.0813 (10) | |
C13 | 0.7268 (3) | 0.2810 (2) | 0.4434 (4) | 0.0766 (10) | |
C13' | 0.0208 (3) | 0.6076 (2) | 0.2128 (4) | 0.0803 (10) | |
C14 | 0.6366 (3) | 0.2886 (2) | 0.4692 (3) | 0.0702 (9) | |
C14' | 0.1063 (2) | 0.6108 (2) | 0.2972 (3) | 0.0701 (9) | |
C15 | 0.5582 (2) | 0.31847 (18) | 0.3858 (2) | 0.0553 (7) | |
C15' | 0.1949 (2) | 0.59803 (19) | 0.2695 (3) | 0.0575 (7) | |
H2 | 0.3423 (18) | 0.2708 (17) | 0.188 (2) | 0.052 (8)* | |
H2' | 0.4696 (19) | 0.6282 (17) | 0.129 (2) | 0.055 (8)* | |
H4 | 0.1621 (19) | 0.4090 (18) | 0.205 (3) | 0.059 (8)* | |
H4' | 0.5691 (19) | 0.5840 (16) | 0.414 (2) | 0.054 (8)* | |
H5 | 0.046 (2) | 0.401 (2) | 0.315 (3) | 0.087 (11)* | |
H5' | 0.733 (2) | 0.5422 (18) | 0.497 (3) | 0.066 (9)* | |
H7 | 0.190 (2) | 0.206 (2) | 0.486 (3) | 0.079 (10)* | |
H7' | 0.774 (2) | 0.5168 (17) | 0.181 (2) | 0.058 (8)* | |
H8 | 0.304 (2) | 0.2204 (19) | 0.371 (3) | 0.074 (10)* | |
H8' | 0.6152 (19) | 0.5571 (17) | 0.101 (3) | 0.058 (8)* | |
H11 | 0.669 (2) | 0.3501 (17) | 0.181 (3) | 0.061 (9)* | |
H11' | 0.116 (2) | 0.5705 (19) | −0.009 (3) | 0.075 (10)* | |
H12 | 0.804 (2) | 0.301 (2) | 0.320 (3) | 0.081 (10)* | |
H12' | −0.034 (3) | 0.591 (2) | 0.037 (3) | 0.099 (12)* | |
H13 | 0.782 (2) | 0.257 (2) | 0.503 (3) | 0.083 (10)* | |
H13' | −0.042 (2) | 0.6194 (19) | 0.233 (3) | 0.079 (10)* | |
H14 | 0.627 (2) | 0.271 (2) | 0.542 (3) | 0.084 (11)* | |
H14' | 0.105 (3) | 0.617 (2) | 0.375 (3) | 0.092 (12)* | |
H15 | 0.4971 (19) | 0.3251 (16) | 0.402 (2) | 0.050 (8)* | |
H15' | 0.252 (2) | 0.5996 (16) | 0.330 (2) | 0.054 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0980 (7) | 0.0851 (6) | 0.1232 (9) | 0.0002 (5) | 0.0562 (6) | 0.0049 (6) |
Cl1' | 0.0505 (4) | 0.0934 (6) | 0.0690 (5) | 0.0062 (4) | 0.0021 (4) | 0.0037 (4) |
S1 | 0.0546 (4) | 0.0477 (4) | 0.0313 (3) | 0.0023 (3) | 0.0083 (3) | −0.0001 (3) |
O1 | 0.0664 (12) | 0.0643 (12) | 0.0403 (10) | −0.0008 (10) | −0.0032 (9) | −0.0077 (9) |
O1' | 0.0582 (11) | 0.0458 (10) | 0.0509 (10) | 0.0041 (8) | 0.0119 (9) | −0.0080 (9) |
O2 | 0.0930 (16) | 0.138 (2) | 0.0377 (12) | 0.0303 (15) | 0.0235 (11) | 0.0139 (13) |
O2' | 0.0709 (13) | 0.1043 (17) | 0.0332 (10) | 0.0112 (12) | 0.0066 (9) | −0.0033 (11) |
C1 | 0.0545 (15) | 0.0495 (15) | 0.0335 (13) | 0.0037 (12) | 0.0005 (11) | −0.0015 (11) |
C1' | 0.0511 (14) | 0.0420 (13) | 0.0323 (12) | 0.0049 (11) | 0.0057 (11) | −0.0043 (11) |
C2 | 0.0634 (18) | 0.0481 (16) | 0.0529 (17) | 0.0022 (14) | 0.0026 (14) | −0.0077 (14) |
C2' | 0.0578 (16) | 0.0477 (15) | 0.0373 (14) | 0.0018 (12) | 0.0097 (12) | 0.0029 (12) |
C3 | 0.0504 (15) | 0.0435 (15) | 0.0615 (18) | −0.0028 (12) | 0.0017 (13) | −0.0050 (13) |
C3' | 0.0465 (14) | 0.0448 (14) | 0.0378 (13) | −0.0030 (11) | 0.0069 (11) | 0.0013 (11) |
C4 | 0.0600 (18) | 0.0516 (17) | 0.0645 (19) | 0.0026 (14) | 0.0023 (15) | 0.0098 (16) |
C4' | 0.0501 (16) | 0.078 (2) | 0.0393 (15) | −0.0010 (14) | 0.0106 (13) | −0.0081 (14) |
C5 | 0.0533 (17) | 0.0571 (19) | 0.086 (2) | 0.0079 (15) | 0.0098 (17) | 0.0079 (17) |
C5' | 0.0552 (17) | 0.088 (2) | 0.0324 (14) | −0.0046 (15) | 0.0039 (13) | −0.0022 (15) |
C6 | 0.0557 (17) | 0.0553 (17) | 0.075 (2) | −0.0042 (14) | 0.0132 (15) | −0.0011 (16) |
C6' | 0.0454 (14) | 0.0564 (16) | 0.0475 (15) | −0.0035 (12) | 0.0035 (12) | 0.0002 (13) |
C7 | 0.0625 (19) | 0.0592 (19) | 0.074 (2) | −0.0015 (16) | 0.0075 (16) | 0.0165 (17) |
C7' | 0.0514 (16) | 0.0645 (18) | 0.0450 (15) | 0.0009 (14) | 0.0158 (13) | −0.0005 (14) |
C8 | 0.0500 (16) | 0.0474 (17) | 0.087 (2) | 0.0058 (14) | 0.0061 (16) | 0.0093 (16) |
C8' | 0.0607 (17) | 0.0585 (17) | 0.0313 (14) | −0.0039 (13) | 0.0096 (13) | 0.0014 (13) |
C9 | 0.0649 (17) | 0.0545 (16) | 0.0399 (15) | 0.0073 (13) | 0.0124 (13) | −0.0022 (12) |
C9' | 0.0590 (16) | 0.0465 (15) | 0.0387 (15) | 0.0060 (12) | 0.0056 (12) | 0.0014 (12) |
C10 | 0.0566 (15) | 0.0392 (14) | 0.0429 (14) | 0.0022 (11) | 0.0098 (12) | −0.0034 (11) |
C10' | 0.0500 (14) | 0.0445 (14) | 0.0461 (15) | 0.0056 (12) | 0.0060 (12) | 0.0017 (12) |
C11 | 0.0624 (18) | 0.0509 (17) | 0.0601 (19) | −0.0011 (14) | 0.0182 (16) | −0.0106 (15) |
C11' | 0.0590 (18) | 0.067 (2) | 0.0577 (19) | 0.0029 (15) | −0.0015 (15) | 0.0007 (16) |
C12 | 0.056 (2) | 0.064 (2) | 0.097 (3) | 0.0017 (16) | 0.008 (2) | −0.018 (2) |
C12' | 0.0511 (19) | 0.095 (3) | 0.089 (3) | 0.0068 (18) | −0.0019 (19) | 0.002 (2) |
C13 | 0.076 (2) | 0.061 (2) | 0.077 (2) | 0.0135 (17) | −0.012 (2) | −0.0081 (18) |
C13' | 0.056 (2) | 0.085 (2) | 0.104 (3) | 0.0121 (18) | 0.029 (2) | 0.011 (2) |
C14 | 0.093 (3) | 0.0616 (19) | 0.0480 (18) | 0.0090 (18) | 0.0002 (18) | 0.0072 (16) |
C14' | 0.068 (2) | 0.081 (2) | 0.066 (2) | 0.0151 (17) | 0.0255 (18) | 0.0086 (18) |
C15 | 0.0652 (19) | 0.0544 (17) | 0.0451 (16) | 0.0092 (14) | 0.0107 (14) | 0.0035 (13) |
C15' | 0.0567 (17) | 0.0641 (18) | 0.0504 (17) | 0.0102 (14) | 0.0103 (14) | 0.0003 (14) |
Cl1—C6 | 1.738 (3) | C6'—C7' | 1.374 (4) |
Cl1'—C6' | 1.738 (3) | C7—C8 | 1.370 (5) |
S1—C1 | 1.793 (3) | C7—H7 | 0.96 (3) |
S1—C1' | 1.798 (3) | C7'—C8' | 1.373 (4) |
O1—C1 | 1.423 (3) | C7'—H7' | 0.90 (3) |
O1—C2 | 1.438 (3) | C8—H8 | 0.90 (3) |
O1'—C1' | 1.427 (3) | C8'—H8' | 0.91 (3) |
O1'—C2' | 1.449 (3) | C9—C10 | 1.479 (4) |
O2—C9 | 1.205 (3) | C9'—C10' | 1.479 (4) |
O2'—C9' | 1.213 (3) | C10—C11 | 1.383 (4) |
C1—C2 | 1.488 (4) | C10—C15 | 1.398 (4) |
C1—C9 | 1.509 (4) | C10'—C15' | 1.387 (4) |
C1'—C2' | 1.473 (4) | C10'—C11' | 1.393 (4) |
C1'—C9' | 1.525 (3) | C11—C12 | 1.375 (5) |
C2—C3 | 1.478 (4) | C11—H11 | 0.91 (3) |
C2—H2 | 0.93 (3) | C11'—C12' | 1.375 (5) |
C2'—C3' | 1.479 (4) | C11'—H11' | 0.95 (3) |
C2'—H2' | 0.92 (3) | C12—C13 | 1.372 (5) |
C3—C4 | 1.385 (4) | C12—H12 | 0.97 (3) |
C3—C8 | 1.386 (4) | C12'—C13' | 1.382 (5) |
C3'—C8' | 1.381 (4) | C12'—H12' | 0.95 (4) |
C3'—C4' | 1.393 (4) | C13—C14 | 1.378 (5) |
C4—C5 | 1.371 (5) | C13—H13 | 0.99 (3) |
C4—H4 | 0.92 (3) | C13'—C14' | 1.369 (5) |
C4'—C5' | 1.363 (4) | C13'—H13' | 0.98 (3) |
C4'—H4' | 0.91 (3) | C14—C15 | 1.381 (4) |
C5—C6 | 1.375 (4) | C14—H14 | 0.94 (3) |
C5—H5 | 0.96 (3) | C14'—C15' | 1.376 (4) |
C5'—C6' | 1.373 (4) | C14'—H14' | 0.93 (4) |
C5'—H5' | 0.91 (3) | C15—H15 | 0.93 (3) |
C6—C7 | 1.365 (4) | C15'—H15' | 0.94 (3) |
C1—S1—C1' | 100.30 (11) | C8—C7—H7 | 120.5 (19) |
C1—O1—C2 | 62.65 (17) | C8'—C7'—C6' | 119.3 (3) |
C1'—O1'—C2' | 61.63 (16) | C8'—C7'—H7' | 121.5 (18) |
O1—C1—C2 | 59.18 (17) | C6'—C7'—H7' | 119.2 (18) |
O1—C1—C9 | 114.4 (2) | C7—C8—C3 | 121.1 (3) |
C2—C1—C9 | 118.2 (2) | C7—C8—H8 | 122 (2) |
O1—C1—S1 | 116.94 (18) | C3—C8—H8 | 117 (2) |
C2—C1—S1 | 118.5 (2) | C7'—C8'—C3' | 121.1 (3) |
C9—C1—S1 | 116.75 (19) | C7'—C8'—H8' | 120.4 (17) |
O1'—C1'—C2' | 59.92 (16) | C3'—C8'—H8' | 118.6 (17) |
O1'—C1'—C9' | 112.72 (19) | O2—C9—C10 | 122.0 (3) |
C2'—C1'—C9' | 118.1 (2) | O2—C9—C1 | 119.2 (2) |
O1'—C1'—S1 | 113.31 (16) | C10—C9—C1 | 118.8 (2) |
C2'—C1'—S1 | 122.33 (18) | O2'—C9'—C10' | 122.1 (2) |
C9'—C1'—S1 | 116.27 (18) | O2'—C9'—C1' | 118.5 (2) |
O1—C2—C3 | 118.6 (2) | C10'—C9'—C1' | 119.4 (2) |
O1—C2—C1 | 58.17 (16) | C11—C10—C15 | 118.9 (3) |
C3—C2—C1 | 125.7 (3) | C11—C10—C9 | 119.3 (3) |
O1—C2—H2 | 113.4 (17) | C15—C10—C9 | 121.6 (2) |
C3—C2—H2 | 114.8 (16) | C15'—C10'—C11' | 118.4 (3) |
C1—C2—H2 | 113.9 (16) | C15'—C10'—C9' | 122.8 (2) |
O1'—C2'—C1' | 58.45 (15) | C11'—C10'—C9' | 118.8 (3) |
O1'—C2'—C3' | 117.4 (2) | C12—C11—C10 | 120.8 (3) |
C1'—C2'—C3' | 125.5 (2) | C12—C11—H11 | 121.9 (18) |
O1'—C2'—H2' | 113.9 (17) | C10—C11—H11 | 117.2 (18) |
C1'—C2'—H2' | 117.2 (16) | C12'—C11'—C10' | 120.5 (3) |
C3'—C2'—H2' | 112.8 (16) | C12'—C11'—H11' | 122.2 (19) |
C4—C3—C8 | 118.0 (3) | C10'—C11'—H11' | 117.2 (19) |
C4—C3—C2 | 122.3 (3) | C13—C12—C11 | 119.8 (3) |
C8—C3—C2 | 119.7 (3) | C13—C12—H12 | 120 (2) |
C8'—C3'—C4' | 118.2 (2) | C11—C12—H12 | 120 (2) |
C8'—C3'—C2' | 119.4 (2) | C11'—C12'—C13' | 120.4 (3) |
C4'—C3'—C2' | 122.4 (2) | C11'—C12'—H12' | 118 (2) |
C5—C4—C3 | 121.2 (3) | C13'—C12'—H12' | 121 (2) |
C5—C4—H4 | 120.9 (17) | C12—C13—C14 | 120.6 (3) |
C3—C4—H4 | 117.9 (18) | C12—C13—H13 | 120.1 (19) |
C5'—C4'—C3' | 121.1 (3) | C14—C13—H13 | 119.3 (19) |
C5'—C4'—H4' | 125.0 (17) | C14'—C13'—C12' | 119.3 (3) |
C3'—C4'—H4' | 113.9 (17) | C14'—C13'—H13' | 120.3 (19) |
C4—C5—C6 | 119.3 (3) | C12'—C13'—H13' | 120.3 (19) |
C4—C5—H5 | 120 (2) | C13—C14—C15 | 119.9 (3) |
C6—C5—H5 | 121 (2) | C13—C14—H14 | 120 (2) |
C4'—C5'—C6' | 119.5 (3) | C15—C14—H14 | 120 (2) |
C4'—C5'—H5' | 122.7 (18) | C13'—C14'—C15' | 120.9 (3) |
C6'—C5'—H5' | 117.8 (18) | C13'—C14'—H14' | 120 (2) |
C7—C6—C5 | 120.8 (3) | C15'—C14'—H14' | 119 (2) |
C7—C6—Cl1 | 119.1 (3) | C14—C15—C10 | 119.9 (3) |
C5—C6—Cl1 | 120.1 (2) | C14—C15—H15 | 121.4 (16) |
C5'—C6'—C7' | 120.9 (3) | C10—C15—H15 | 118.6 (16) |
C5'—C6'—Cl1' | 119.6 (2) | C14'—C15'—C10' | 120.5 (3) |
C7'—C6'—Cl1' | 119.4 (2) | C14'—C15'—H15' | 118.2 (17) |
C6—C7—C8 | 119.6 (3) | C10'—C15'—H15' | 121.2 (17) |
C6—C7—H7 | 119.8 (19) | ||
C2—O1—C1—C9 | 109.5 (3) | Cl1'—C6'—C7'—C8' | 177.9 (2) |
C2—O1—C1—S1 | −108.7 (2) | C6—C7—C8—C3 | 0.3 (5) |
C1'—S1—C1—O1 | −61.7 (2) | C4—C3—C8—C7 | −1.1 (5) |
C1'—S1—C1—C2 | −129.5 (2) | C2—C3—C8—C7 | −179.7 (3) |
C1'—S1—C1—C9 | 79.2 (2) | C6'—C7'—C8'—C3' | −0.4 (4) |
C2'—O1'—C1'—C9' | −110.3 (2) | C4'—C3'—C8'—C7' | 0.8 (4) |
C2'—O1'—C1'—S1 | 115.0 (2) | C2'—C3'—C8'—C7' | −179.7 (3) |
C1—S1—C1'—O1' | −159.95 (17) | O1—C1—C9—O2 | 22.9 (4) |
C1—S1—C1'—C2' | −91.9 (2) | C2—C1—C9—O2 | 89.6 (3) |
C1—S1—C1'—C9' | 67.1 (2) | S1—C1—C9—O2 | −119.0 (3) |
C1—O1—C2—C3 | 116.3 (3) | O1—C1—C9—C10 | −154.6 (2) |
C9—C1—C2—O1 | −103.1 (2) | C2—C1—C9—C10 | −87.8 (3) |
S1—C1—C2—O1 | 106.0 (2) | S1—C1—C9—C10 | 63.5 (3) |
O1—C1—C2—C3 | −104.4 (3) | O1'—C1'—C9'—O2' | 108.2 (3) |
C9—C1—C2—C3 | 152.5 (3) | C2'—C1'—C9'—O2' | 41.4 (4) |
S1—C1—C2—C3 | 1.6 (4) | S1—C1'—C9'—O2' | −118.5 (3) |
C1'—O1'—C2'—C3' | −116.7 (3) | O1'—C1'—C9'—C10' | −70.8 (3) |
C9'—C1'—C2'—O1' | 101.4 (2) | C2'—C1'—C9'—C10' | −137.7 (2) |
S1—C1'—C2'—O1' | −100.1 (2) | S1—C1'—C9'—C10' | 62.4 (3) |
O1'—C1'—C2'—C3' | 103.0 (3) | O2—C9—C10—C11 | 11.3 (4) |
C9'—C1'—C2'—C3' | −155.6 (2) | C1—C9—C10—C11 | −171.2 (2) |
S1—C1'—C2'—C3' | 3.0 (4) | O2—C9—C10—C15 | −165.6 (3) |
O1—C2—C3—C4 | −2.5 (4) | C1—C9—C10—C15 | 11.9 (4) |
C1—C2—C3—C4 | 67.1 (4) | O2'—C9'—C10'—C15' | −170.3 (3) |
O1—C2—C3—C8 | 175.9 (3) | C1'—C9'—C10'—C15' | 8.7 (4) |
C1—C2—C3—C8 | −114.4 (3) | O2'—C9'—C10'—C11' | 9.4 (4) |
O1'—C2'—C3'—C8' | −169.6 (2) | C1'—C9'—C10'—C11' | −171.5 (2) |
C1'—C2'—C3'—C8' | 121.1 (3) | C15—C10—C11—C12 | 0.3 (4) |
O1'—C2'—C3'—C4' | 9.8 (4) | C9—C10—C11—C12 | −176.7 (3) |
C1'—C2'—C3'—C4' | −59.4 (4) | C15'—C10'—C11'—C12' | −0.6 (5) |
C8—C3—C4—C5 | 0.9 (4) | C9'—C10'—C11'—C12' | 179.7 (3) |
C2—C3—C4—C5 | 179.3 (3) | C10—C11—C12—C13 | 0.6 (5) |
C8'—C3'—C4'—C5' | −0.7 (4) | C10'—C11'—C12'—C13' | 0.0 (6) |
C2'—C3'—C4'—C5' | 179.8 (3) | C11—C12—C13—C14 | −1.7 (5) |
C3—C4—C5—C6 | 0.2 (5) | C11'—C12'—C13'—C14' | 0.8 (6) |
C3'—C4'—C5'—C6' | 0.2 (5) | C12—C13—C14—C15 | 1.9 (5) |
C4—C5—C6—C7 | −1.0 (5) | C12'—C13'—C14'—C15' | −1.0 (6) |
C4—C5—C6—Cl1 | 178.8 (2) | C13—C14—C15—C10 | −0.9 (5) |
C4'—C5'—C6'—C7' | 0.3 (5) | C11—C10—C15—C14 | −0.2 (4) |
C4'—C5'—C6'—Cl1' | −177.9 (2) | C9—C10—C15—C14 | 176.7 (3) |
C5—C6—C7—C8 | 0.8 (5) | C13'—C14'—C15'—C10' | 0.4 (5) |
Cl1—C6—C7—C8 | −179.0 (3) | C11'—C10'—C15'—C14' | 0.4 (4) |
C5'—C6'—C7'—C8' | −0.2 (4) | C9'—C10'—C15'—C14' | −179.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.97 (3) | 2.45 (3) | 3.266 (4) | 142 (2) |
C8′—H8′···O2ii | 0.91 (3) | 2.58 (3) | 3.400 (3) | 151 (2) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C30H20Cl2O4S |
Mr | 547.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.0724 (17), 16.3184 (16), 11.768 (3) |
β (°) | 103.66 (2) |
V (Å3) | 2626.0 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.43 × 0.32 × 0.25 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.84, 0.91 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4835, 4587, 3241 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.116, 1.11 |
No. of reflections | 4587 |
No. of parameters | 414 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.24, −0.35 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.97 (3) | 2.45 (3) | 3.266 (4) | 142 (2) |
C8'—H8'···O2ii | 0.91 (3) | 2.58 (3) | 3.400 (3) | 151 (2) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z. |
Among heterocycles, small ring systems, such as oxiranes, assume much importance in organic synthesis. These strained heterocycles can undergo facile reaction with a host of nucleophiles affording novel products. Details of chemical synthesis, NMR studies and preliminary crystallographic data of the title compound, (I), have already been reported (Renuga et al., 1999). Interestingly, (I) exhibits stereoisomerism and the difficulty in ascertaining the configuration arises as one of the C atoms of each oxirane ring is quaternary as a result of which the molecule further exhibits diastereoisomerism with respect to the oxirane rings. The present X-ray study reports the complete structural details of (I).
This study points to the relative configuration between the aryl and aroyl groups (trans) on one hand and that between the two oxirane rings (trans) on the other. The molecular packing in the crystal is characterized by C—H···O hydrogen bonds and Cl···Cl short contacts. In the crystal, the molecules are linked by intermolecular C—H···O hydrogen bonds to form an infinite two-dimensional zigzag network parallel to the bc plane. The Cl···Cl short contacts observed in the structure are (a) Cl1···Cl1'i 3.746 (2) Å and (b) Cl1'···Cl1'ii 3.459 (1) Å [symmetry codes: (i) 1 - x, -y,-z; (ii) -x, -y, -z]. A study on the nature of Cl···Cl interactions on flat rigid molecules with moderately polar substituents (Sarma & Desiraju, 1986) suggests a range of 3.27–4.10 Å for the Cl···Cl short contacts in these group of structures. The value of 3.746 (2) Å in (I) is also significant. This may be due to the flexible nature of the molecule, in spite of being bulky. The configuration of (I) which is symmetrical in solution in the absence of intermolecular interactions, assumes an unsymmetrical configuration in the solid state. The absence of symmetry is probably necessitated by the optimum packing considerations which bring different oxirane molecules in proximity, unlike in solution.