Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004765/vj1103sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004765/vj1103Isup2.hkl |
CCDC reference: 147661
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: PLUTO (Motherwell & Clegg, 1978); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I) with the atom-numbering scheme and 50% probability displacement ellipsoids. |
C17H16OS | F(000) = 568 |
Mr = 268.36 | Dx = 1.245 Mg m−3 |
Orthorhombic, Pnma | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 25 reflections |
a = 10.867 (3) Å | θ = 8–16° |
b = 24.284 (4) Å | µ = 1.90 mm−1 |
c = 5.427 (2) Å | T = 293 K |
V = 1432.2 (7) Å3 | Plates, colourless |
Z = 4 | 0.20 × 0.12 × 0.08 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.007 |
Radiation source: fine-focus sealed tube | θmax = 71.9°, θmin = 3.6° |
Graphite monochromator | h = 0→13 |
ω–2θ scans | k = −29→11 |
1585 measured reflections | l = −6→0 |
1436 independent reflections | 2 standard reflections every 200 reflections |
1285 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | Only H-atom displacement parameters refined |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0432P)2 + 0.1515P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
1436 reflections | Δρmax = 0.35 e Å−3 |
124 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0126 (9) |
C17H16OS | V = 1432.2 (7) Å3 |
Mr = 268.36 | Z = 4 |
Orthorhombic, Pnma | Cu Kα radiation |
a = 10.867 (3) Å | µ = 1.90 mm−1 |
b = 24.284 (4) Å | T = 293 K |
c = 5.427 (2) Å | 0.20 × 0.12 × 0.08 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.007 |
1585 measured reflections | 2 standard reflections every 200 reflections |
1436 independent reflections | intensity decay: 1% |
1285 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.123 | Only H-atom displacement parameters refined |
S = 1.17 | Δρmax = 0.35 e Å−3 |
1436 reflections | Δρmin = −0.18 e Å−3 |
124 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 | ||
S1 | 0.28672 (5) | 0.2500 | 0.77840 (10) | 0.0600 (2) | |
O1 | 0.0090 (2) | 0.2500 | 0.2052 (3) | 0.0999 (7) | |
C2 | 0.23937 (14) | 0.19352 (7) | 0.5821 (3) | 0.0639 (4) | |
C3 | 0.10133 (15) | 0.19750 (8) | 0.5219 (4) | 0.0730 (5) | |
C4 | 0.0661 (2) | 0.2500 | 0.3963 (4) | 0.0739 (7) | |
C7 | 0.27358 (16) | 0.14107 (8) | 0.7105 (3) | 0.0677 (5) | |
C8 | 0.2127 (2) | 0.12431 (10) | 0.9227 (4) | 0.0870 (6) | |
C9 | 0.2452 (3) | 0.07676 (11) | 1.0424 (6) | 0.1048 (8) | |
C10 | 0.3391 (3) | 0.04492 (11) | 0.9537 (6) | 0.1127 (10) | |
C11 | 0.4009 (3) | 0.06105 (12) | 0.7482 (7) | 0.1186 (10) | |
C12 | 0.3688 (2) | 0.10896 (9) | 0.6252 (5) | 0.0898 (6) | |
H3A | 0.0779 (18) | 0.1652 (8) | 0.424 (4) | 0.084 (6)* | |
H2 | 0.2857 (18) | 0.1970 (8) | 0.430 (4) | 0.076 (6)* | |
H3B | 0.053 (2) | 0.1970 (8) | 0.684 (4) | 0.084 (6)* | |
H9 | 0.201 (3) | 0.0632 (12) | 1.195 (6) | 0.131 (11)* | |
H10 | 0.359 (3) | 0.0125 (13) | 1.032 (5) | 0.137 (10)* | |
H12 | 0.467 (3) | 0.0420 (11) | 0.689 (5) | 0.116 (9)* | |
H11 | 0.407 (2) | 0.1207 (9) | 0.476 (4) | 0.099 (7)* | |
H8 | 0.145 (3) | 0.1461 (10) | 0.983 (5) | 0.122 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0458 (3) | 0.0720 (4) | 0.0623 (4) | 0.000 | −0.0069 (2) | 0.000 |
O1 | 0.0717 (12) | 0.161 (2) | 0.0673 (11) | 0.000 | −0.0206 (9) | 0.000 |
C2 | 0.0486 (8) | 0.0856 (11) | 0.0576 (9) | −0.0016 (7) | 0.0015 (6) | −0.0090 (8) |
C3 | 0.0505 (9) | 0.0963 (13) | 0.0721 (10) | −0.0067 (8) | −0.0072 (8) | −0.0109 (9) |
C4 | 0.0414 (10) | 0.120 (2) | 0.0598 (13) | 0.000 | −0.0025 (9) | 0.000 |
C7 | 0.0575 (9) | 0.0746 (10) | 0.0709 (10) | −0.0046 (7) | −0.0077 (7) | −0.0155 (8) |
C8 | 0.0904 (14) | 0.0918 (14) | 0.0786 (13) | 0.0003 (11) | 0.0023 (10) | 0.0003 (11) |
C9 | 0.1215 (19) | 0.0927 (15) | 0.1002 (18) | −0.0073 (15) | −0.0128 (16) | 0.0088 (13) |
C10 | 0.136 (2) | 0.0730 (13) | 0.129 (2) | −0.0033 (14) | −0.034 (2) | 0.0031 (14) |
C11 | 0.114 (2) | 0.0905 (16) | 0.152 (3) | 0.0285 (16) | −0.0062 (18) | −0.0200 (17) |
C12 | 0.0759 (12) | 0.0894 (13) | 0.1042 (16) | 0.0069 (10) | 0.0018 (12) | −0.0162 (12) |
S1—C2 | 1.8114 (17) | C7—C8 | 1.389 (3) |
S1—C2i | 1.8114 (17) | C8—C9 | 1.371 (3) |
O1—C4 | 1.209 (3) | C8—H8 | 0.96 (3) |
C2—C7 | 1.499 (2) | C9—C10 | 1.367 (4) |
C2—C3 | 1.538 (2) | C9—H9 | 1.01 (3) |
C2—H2 | 0.97 (2) | C10—C11 | 1.359 (5) |
C3—C4 | 1.496 (2) | C10—H10 | 0.92 (3) |
C3—H3A | 0.98 (2) | C11—C12 | 1.386 (4) |
C3—H3B | 1.02 (2) | C11—H12 | 0.91 (3) |
C4—C3i | 1.495 (2) | C12—H11 | 0.95 (2) |
C7—C12 | 1.376 (3) | ||
C2—S1—C2i | 98.43 (12) | C12—C7—C2 | 120.78 (19) |
C7—C2—C3 | 113.20 (15) | C8—C7—C2 | 121.09 (18) |
C7—C2—S1 | 107.42 (11) | C9—C8—C7 | 121.1 (3) |
C3—C2—S1 | 110.74 (12) | C9—C8—H8 | 119.9 (15) |
C7—C2—H2 | 109.9 (11) | C7—C8—H8 | 119.0 (15) |
C3—C2—H2 | 108.7 (11) | C10—C9—C8 | 120.1 (3) |
S1—C2—H2 | 106.6 (11) | C10—C9—H9 | 117.2 (18) |
C4—C3—C2 | 113.57 (16) | C8—C9—H9 | 122.6 (18) |
C4—C3—H3A | 111.6 (11) | C11—C10—C9 | 119.6 (3) |
C2—C3—H3A | 108.5 (12) | C11—C10—H10 | 120.5 (18) |
C4—C3—H3B | 105.7 (11) | C9—C10—H10 | 119.9 (19) |
C2—C3—H3B | 108.4 (12) | C10—C11—C12 | 120.9 (3) |
H3A—C3—H3B | 108.9 (15) | C10—C11—H12 | 122.0 (18) |
O1—C4—C3i | 121.52 (10) | C12—C11—H12 | 117.1 (18) |
O1—C4—C3 | 121.51 (10) | C7—C12—C11 | 120.2 (3) |
C3i—C4—C3 | 116.9 (2) | C7—C12—H11 | 116.3 (15) |
C12—C7—C8 | 118.1 (2) | C11—C12—H11 | 123.4 (15) |
Symmetry code: (i) x, −y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C17H16OS |
Mr | 268.36 |
Crystal system, space group | Orthorhombic, Pnma |
Temperature (K) | 293 |
a, b, c (Å) | 10.867 (3), 24.284 (4), 5.427 (2) |
V (Å3) | 1432.2 (7) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.90 |
Crystal size (mm) | 0.20 × 0.12 × 0.08 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1585, 1436, 1285 |
Rint | 0.007 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.123, 1.17 |
No. of reflections | 1436 |
No. of parameters | 124 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.35, −0.18 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLUTO (Motherwell & Clegg, 1978), SHELXL97.
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The tendency of molecules to pack as closely as possible, usually, overrides that for retention of molecular symmetry upon crystallization and reduces the symmetry of a molecule in the solid state compared to that observed in the free state (Kitaigorodskii, 1973). Though inversion generally is the symmetry element which is carried over into the crystal, the tendency of molecules to possess mirror or twofold symmetry in the solid state seems to depend on the presence, nature and strength of the intermolecular interactions. An example of this is the crystal structure of 2,6-dibenzoyl-1,4-benzoquinone (Biradha et al., 1997), where interference from numerous C—H···O hydrogen bonds lowers the symmetry of the molecule.
In the present structure, (I), the molecule is bisected by a mirror plane passing through the atoms S1, C4 and O1 of the heterocyclic ring (Fig. 1). There are no C—H···X type interactions whose presence otherwise might have had a considerable influence on the molecular conformation. The absence of C—H···O hydrogen bonds is presumably due to the deficiency of acceptors compared to the donors (phenyl C—H). The crystal structure is stabilized by van der Waals interactions. The shortest S···O and C···O contacts observed are 3.567 (2) Å and 3.512 (3) Å, respectively. The strucutre provides a good example of the retention of mirror symmetry of a molecule in the crystals. \sch