Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The non-bonded S...O intramolecular interactions in the title compounds 2-(phenyl­thio)­aceto­phenone {IUPAC: 2-[2-(phenylsulfanyl)phenyl]ethanone}, C14H12OS, and 2-(benzyl­thio)­aceto­phenone {IUPAC: 2-[2-(benzylsulfanyl)phenyl]­ethanone}, C15H14OS, are unusually short, indicating the contribution of heterocyclic oxa­thiole-type resonance structures to the overall bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101008216/bm1449sup1.cif
Contains datablocks II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101008216/bm1449IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101008216/bm1449IIIsup3.hkl
Contains datablock III

CCDC references: 174810; 174811

Comment top

The crystal structure of 2-(phenylmethylthio)benzaldehyde, (I), was recently reported (Wong & Lee, 1995). In connection with the study of iminyl and thiophenoxyl radical cyclization reactions (Creed et al., 2001) we required the acetophenone derivatives (II) and (III) as starting materials. There is structural interest in related systems (Wong & Lee, 1995; Kucsman et al., 1984; Kucsman et al., 1986) because of the presence of a short S···O intramolecular distance which is suggestive of a weak interaction between the two heteroatoms. This can be represented by a contribution of the heterocyclic resonance form (Ia). Structural data on benzene derivatives containing ortho-disposed carbonyl and sulfur-containing substituents are rare; apart from aldehyde (I) the only relevant data available concern esters (IV)-(VII) and the diazo compound (VIII). We now report the crystal structures of the two related acetophenone derivatives. \sch

In (I)-(III), the CO group is aligned s-Z to the ortho substituent. The angle between the best plane of the acetyl group and that of the aryl group to which it is attached is only 6.2 (4)° in (II), whereas it is 25.87 (16)° in (III); these compare with a corresponding angle of 4.4° in aldehyde (I). In (II) the phenyl rings are almost orthogonal to each other [88.29 (7)°], whereas in (I) and (III) the corresponding angles are 78.3 and 62.21 (5)°, respectively. The two Ar—S bonds in (II) are significantly different. The shorter [1.7694 (18) Å] is associated with the ring bearing the acetyl group; that associated with the unsubstituted phenyl group [1.781 (2) Å] is longer because the group is twisted out of the plane. Therefore even in the diarylsulfide (II), the lone pair of the sulfur atom interacts preferentially with the aryl ring carrying the acetyl group. These features would be expected if the cyclic resonance (###AUTHOR: OK to add this ?) form, e.g. (Ia), contributes to the overall structure.

The non-bonded S···O distance in (I) was reported to be unusually short at 2.804 (2) Å, and this was interpreted as indicating a weak interaction. The related distances in (II) and (III) are even shorter, at 2.6578 (18) and 2.7125 (17) Å, respectively. These are of a similar order of magnitude to related distances in structures (IV)–(VIII). However, these interactions are substantially weaker than in the 6,6a-dithiafurophthenes, where S···O distances can be as short as 2.287 Å (Saethre & Hordvik, 1975, CSD refcode: MAPTFU10).

The geometries of the disubstituted aryl rings in (I)-(III) are substantially distorted. The bond between the two substituents is the longest in each case: 1.408 (4), 1.414 (3) and 1.415 (3) Å, respectively, which may, in part, be rationalized by a contribution of resonance (###AUTHOR: OK to add this ?) structures of type (Ia). Similarly the shortest bond - differing from the largest by over 6σ in all three structures - is C5—C6 [1.361 (4), 1.367 (3) and 1.375 (3) Å in (I)-(III), respectively]. In (I)-(III) the bonds C3—C4 and C4—C5 are shorter than average, whereas C2—C3 and C1—C6 are longer than average. Intra-ring bond angles at the substituted sites in (II) and (III) are 118–119°, whereas the angles at C6 are around 122° in each case. The geometries of the S-phenyl group in (II) and the benzyl group in (III) are very regular.

Experimental top

Compounds (II) and (III) were made by displacement of halide by the appropriate thiol from the corresponding 2-halogenoacetophenone. Crystals of (II) were obtained directly from the reaction mixture and those of (III) were obtained by slow evaporation from an acetone solution.

Refinement top

For (II), the H atoms attached to C12 were located in a circular difference synthesis, the methyl group was thereafter treated as a rotating rigid group with Uiso(H) = 1.5Ueq(C12). Other H atoms were placed in calculated positions and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).

Computing details top

For both compounds, data collection: DIF4 (Stoe & Cie, 1990a); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1990b); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of (II) and (III) with atom-numbering schemes. Displacement ellipsoids enclose 50% probability surfaces.
(II) 1-[(2-phenylsulfanyl)phenyl]ethanone top
Crystal data top
C14H12OSF(000) = 480
Mr = 228.30Dx = 1.284 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 9.0151 (7) ÅCell parameters from 48 reflections
b = 12.7805 (14) Åθ = 20–22°
c = 10.6400 (12) ŵ = 2.22 mm1
β = 105.497 (7)°T = 293 K
V = 1181.3 (2) Å3Block, colourless
Z = 40.58 × 0.47 × 0.39 mm
Data collection top
Stoe Stadi-4 four-circle
diffractometer
1754 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 70.0°, θmin = 5.1°
ω/θ scansh = 1010
Absorption correction: ψ scans
(North et al., 1968)
k = 415
Tmin = 0.331, Tmax = 0.420l = 612
3137 measured reflections3 standard reflections every 60 min
2070 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: see text
R[F2 > 2σ(F2)] = 0.039See text
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0571P)2 + 0.297P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2070 reflectionsΔρmax = 0.30 e Å3
147 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0107 (9)
Crystal data top
C14H12OSV = 1181.3 (2) Å3
Mr = 228.30Z = 4
Monoclinic, P21/cCu Kα radiation
a = 9.0151 (7) ŵ = 2.22 mm1
b = 12.7805 (14) ÅT = 293 K
c = 10.6400 (12) Å0.58 × 0.47 × 0.39 mm
β = 105.497 (7)°
Data collection top
Stoe Stadi-4 four-circle
diffractometer
1754 reflections with I > 2σ(I)
Absorption correction: ψ scans
(North et al., 1968)
Rint = 0.033
Tmin = 0.331, Tmax = 0.4203 standard reflections every 60 min
3137 measured reflections intensity decay: none
2070 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.110See text
S = 1.07Δρmax = 0.30 e Å3
2070 reflectionsΔρmin = 0.19 e Å3
147 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.9941 (2)0.37915 (15)0.10751 (17)0.0437 (4)
C110.9209 (2)0.28736 (16)0.02984 (19)0.0518 (5)
O110.79066 (19)0.26176 (13)0.02729 (18)0.0729 (5)
C121.0095 (3)0.2247 (2)0.0446 (3)0.0801 (8)
H12A1.09900.19510.01510.120*
H12B1.04080.26930.10550.120*
H12C0.94560.16950.09100.120*
C20.9116 (2)0.44574 (15)0.17073 (17)0.0430 (4)
S210.71436 (5)0.42206 (4)0.15644 (5)0.0572 (2)
C220.6611 (2)0.52844 (16)0.24334 (19)0.0487 (5)
C230.5953 (3)0.61685 (19)0.1771 (2)0.0625 (6)
H230.59230.62520.08960.075*
C240.5339 (3)0.6931 (2)0.2403 (3)0.0743 (7)
H240.48930.75240.19500.089*
C250.5384 (3)0.6819 (2)0.3695 (3)0.0670 (6)
H250.49640.73310.41180.080*
C260.6055 (3)0.5944 (2)0.4358 (2)0.0663 (6)
H260.61050.58720.52390.080*
C270.6653 (2)0.51726 (19)0.3734 (2)0.0576 (5)
H270.70850.45760.41880.069*
C30.9885 (2)0.52901 (17)0.24371 (19)0.0512 (5)
H30.93540.57310.28600.061*
C41.1424 (2)0.54780 (19)0.2548 (2)0.0596 (6)
H41.19160.60390.30440.072*
C51.2232 (2)0.4838 (2)0.1927 (2)0.0635 (6)
H51.32660.49660.19950.076*
C61.1497 (2)0.40116 (18)0.1208 (2)0.0554 (5)
H61.20500.35800.07930.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0437 (10)0.0464 (10)0.0400 (9)0.0013 (8)0.0096 (8)0.0057 (8)
C110.0579 (12)0.0464 (11)0.0507 (10)0.0017 (9)0.0142 (9)0.0030 (9)
O110.0691 (10)0.0651 (10)0.0878 (11)0.0200 (8)0.0268 (9)0.0218 (9)
C120.0855 (18)0.0669 (15)0.0932 (19)0.0034 (13)0.0332 (15)0.0246 (14)
C20.0408 (9)0.0482 (10)0.0389 (9)0.0024 (8)0.0087 (7)0.0041 (8)
S210.0431 (3)0.0636 (4)0.0671 (4)0.0118 (2)0.0187 (2)0.0156 (3)
C220.0361 (9)0.0565 (12)0.0542 (11)0.0042 (8)0.0133 (8)0.0007 (9)
C230.0619 (13)0.0664 (14)0.0573 (12)0.0016 (11)0.0124 (10)0.0078 (11)
C240.0686 (15)0.0582 (14)0.0894 (18)0.0085 (12)0.0094 (13)0.0072 (13)
C250.0522 (12)0.0635 (14)0.0865 (17)0.0006 (11)0.0204 (12)0.0158 (13)
C260.0649 (14)0.0795 (17)0.0602 (13)0.0020 (12)0.0266 (11)0.0056 (12)
C270.0542 (12)0.0624 (13)0.0579 (12)0.0046 (10)0.0177 (10)0.0074 (10)
C30.0470 (10)0.0589 (12)0.0479 (10)0.0054 (9)0.0129 (8)0.0079 (9)
C40.0456 (11)0.0707 (14)0.0578 (12)0.0146 (10)0.0056 (9)0.0113 (11)
C50.0386 (10)0.0817 (16)0.0691 (13)0.0076 (10)0.0125 (10)0.0061 (12)
C60.0457 (11)0.0649 (13)0.0568 (11)0.0054 (9)0.0160 (9)0.0009 (10)
Geometric parameters (Å, º) top
C1—C61.400 (3)C4—C51.376 (3)
C1—C21.414 (3)C5—C61.367 (3)
C1—C111.484 (3)C3—H30.93
C11—O111.213 (2)C4—H40.93
C11—C121.498 (3)C5—H50.93
C2—C31.389 (3)C6—H60.93
C2—S211.7694 (18)C12—H12A0.96
S21—C221.781 (2)C12—H12B0.96
C22—C231.379 (3)C12—H12C0.96
C22—C271.382 (3)C23—H230.93
C23—C241.381 (3)C24—H240.93
C24—C251.372 (4)C25—H250.93
C25—C261.374 (4)C26—H260.93
C26—C271.376 (3)C27—H270.93
C3—C41.381 (3)
C6—C1—C2118.13 (18)C2—C3—H3118.7
C6—C1—C11119.97 (17)C5—C4—H4119.8
C2—C1—C11121.90 (17)C3—C4—H4119.5
O11—C11—C1120.64 (18)C6—C5—H5120.4
O11—C11—C12119.6 (2)C4—C5—H5120.4
C1—C11—C12119.76 (19)C5—C6—H6118.9
C3—C2—C1118.64 (17)C1—C6—H6118.1
C3—C2—S21121.30 (15)C11—C12—H12A108.9
C1—C2—S21120.06 (14)C11—C12—H12B110.0
C2—S21—C22103.24 (9)H12A—C12—H12B109.5
C23—C22—C27119.3 (2)C11—C12—H12C109.5
C23—C22—S21119.92 (16)H12A—C12—H12C109.5
C27—C22—S21120.14 (17)H12B—C12—H12C109.5
C22—C23—C24120.2 (2)C22—C23—H23119.9
C25—C24—C23120.4 (2)C24—C23—H23120.0
C24—C25—C26119.4 (2)C25—C24—H24119.8
C25—C26—C27120.7 (2)C23—C24—H24119.6
C26—C27—C22120.0 (2)C24—C25—H25121.3
C4—C3—C2121.42 (19)C26—C25—H25120.8
C5—C4—C3120.2 (2)C25—C26—H26119.1
C6—C5—C4119.25 (19)C27—C26—H26119.7
C5—C6—C1122.32 (19)C26—C27—H27120.0
C4—C3—H3119.6C22—C27—H27120.0
(III) 1-[(2-phenylmethylsulfanyl)phenyl]ethanone top
Crystal data top
C15H14OSDx = 1.304 Mg m3
Mr = 242.32Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, PbcaCell parameters from 150 reflections
a = 7.8838 (18) Åθ = 20–22°
b = 14.719 (3) ŵ = 2.15 mm1
c = 21.277 (4) ÅT = 150 K
V = 2469.1 (9) Å3Block, colourless
Z = 80.54 × 0.18 × 0.12 mm
F(000) = 1024
Data collection top
Stoe Stadi-4 four-circle
diffractometer
1520 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.011
Graphite monochromatorθmax = 59.9°, θmin = 4.2°
ω/θ scansh = 86
Absorption correction: ψ scans
(North et al., 1968)
k = 1516
Tmin = 0.429, Tmax = 0.581l = 2317
2272 measured reflections3 standard reflections every 60 min
1790 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033All H-atom parameters refined
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.689P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
1790 reflectionsΔρmax = 0.19 e Å3
211 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0026 (2)
Crystal data top
C15H14OSV = 2469.1 (9) Å3
Mr = 242.32Z = 8
Orthorhombic, PbcaCu Kα radiation
a = 7.8838 (18) ŵ = 2.15 mm1
b = 14.719 (3) ÅT = 150 K
c = 21.277 (4) Å0.54 × 0.18 × 0.12 mm
Data collection top
Stoe Stadi-4 four-circle
diffractometer
1520 reflections with I > 2σ(I)
Absorption correction: ψ scans
(North et al., 1968)
Rint = 0.011
Tmin = 0.429, Tmax = 0.581θmax = 59.9°
2272 measured reflections3 standard reflections every 60 min
1790 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.087All H-atom parameters refined
S = 1.02Δρmax = 0.19 e Å3
1790 reflectionsΔρmin = 0.30 e Å3
211 parameters
Special details top

Experimental. Data were collected to 2θmax = 120° because of the presence of a low-temperature unit.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1098 (2)0.54262 (13)0.21073 (9)0.0250 (5)
C110.0473 (3)0.45532 (13)0.23716 (9)0.0289 (5)
O110.0116 (2)0.39745 (10)0.20286 (7)0.0433 (4)
C120.0611 (3)0.43843 (19)0.30664 (11)0.0378 (6)
H12A0.028 (5)0.379 (3)0.3148 (15)0.098 (12)*
H12B0.003 (4)0.479 (2)0.3301 (14)0.086 (11)*
H12C0.179 (4)0.4493 (19)0.3216 (14)0.073 (10)*
C20.1637 (2)0.54871 (12)0.14744 (9)0.0235 (5)
C30.2257 (3)0.63192 (13)0.12562 (10)0.0287 (5)
H3A0.261 (3)0.6370 (13)0.0833 (10)0.022 (5)*
C40.2301 (3)0.70738 (14)0.16445 (11)0.0337 (5)
H4A0.274 (3)0.7627 (17)0.1489 (11)0.047 (7)*
C50.1723 (3)0.70216 (15)0.22569 (11)0.0358 (6)
H5A0.176 (3)0.7521 (16)0.2519 (12)0.042 (6)*
C60.1152 (3)0.62014 (14)0.24819 (11)0.0319 (5)
H6A0.080 (3)0.6146 (14)0.2894 (10)0.029 (6)*
S210.15434 (6)0.45227 (3)0.09782 (2)0.0243 (2)
C210.2889 (3)0.48540 (15)0.03213 (10)0.0298 (5)
H21A0.397 (3)0.5042 (16)0.0495 (10)0.036 (6)*
H21B0.237 (3)0.5364 (15)0.0090 (11)0.037 (6)*
C220.3101 (2)0.40234 (13)0.00845 (9)0.0246 (5)
C230.4131 (3)0.33112 (14)0.01019 (10)0.0310 (5)
H23A0.468 (3)0.3350 (15)0.0476 (11)0.043 (7)*
C240.4301 (3)0.25422 (16)0.02655 (10)0.0361 (5)
H24A0.508 (3)0.2056 (16)0.0124 (11)0.052 (7)*
C250.3421 (3)0.24734 (16)0.08266 (10)0.0348 (5)
H25A0.353 (3)0.1945 (18)0.1078 (12)0.057 (8)*
C260.2370 (3)0.31730 (16)0.10132 (10)0.0338 (5)
H26A0.177 (3)0.3141 (15)0.1394 (11)0.035 (6)*
C270.2221 (3)0.39448 (15)0.06478 (9)0.0291 (5)
H27A0.148 (3)0.4426 (16)0.0750 (12)0.044 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0223 (10)0.0263 (11)0.0264 (11)0.0025 (8)0.0011 (8)0.0039 (8)
C110.0255 (10)0.0320 (11)0.0292 (11)0.0005 (9)0.0063 (9)0.0010 (9)
O110.0592 (10)0.0367 (9)0.0341 (8)0.0190 (8)0.0076 (8)0.0053 (7)
C120.0410 (14)0.0414 (14)0.0311 (12)0.0008 (12)0.0053 (11)0.0039 (11)
C20.0214 (10)0.0207 (10)0.0284 (11)0.0033 (8)0.0034 (8)0.0012 (8)
C30.0331 (11)0.0248 (11)0.0282 (12)0.0001 (9)0.0008 (10)0.0005 (9)
C40.0391 (13)0.0224 (11)0.0395 (13)0.0000 (10)0.0085 (10)0.0004 (10)
C50.0438 (13)0.0255 (12)0.0380 (13)0.0034 (10)0.0070 (10)0.0095 (10)
C60.0341 (11)0.0346 (12)0.0270 (11)0.0030 (10)0.0004 (9)0.0063 (10)
S210.0278 (3)0.0212 (3)0.0240 (3)0.0011 (2)0.0030 (2)0.00262 (19)
C210.0349 (12)0.0271 (11)0.0272 (11)0.0049 (10)0.0059 (9)0.0011 (9)
C220.0253 (10)0.0261 (10)0.0223 (10)0.0014 (9)0.0060 (8)0.0010 (8)
C230.0311 (11)0.0382 (13)0.0238 (11)0.0022 (10)0.0003 (9)0.0001 (10)
C240.0375 (12)0.0355 (12)0.0353 (11)0.0099 (11)0.0042 (10)0.0000 (10)
C250.0371 (12)0.0354 (12)0.0320 (11)0.0011 (11)0.0099 (10)0.0086 (10)
C260.0311 (11)0.0467 (13)0.0238 (11)0.0042 (11)0.0014 (10)0.0042 (10)
C270.0275 (11)0.0340 (12)0.0257 (11)0.0046 (10)0.0030 (9)0.0026 (9)
Geometric parameters (Å, º) top
C1—C61.393 (3)C6—H6A0.92 (2)
C1—C21.415 (3)S21—C211.821 (2)
C1—C111.487 (3)C21—C221.506 (3)
C11—O111.214 (2)C21—H21A0.97 (2)
C11—C121.503 (3)C21—H21B0.99 (2)
C12—H12A0.93 (4)C22—C231.384 (3)
C12—H12B0.90 (3)C22—C271.389 (3)
C12—H12C1.00 (3)C23—C241.382 (3)
C2—C31.398 (3)C23—H23A0.91 (2)
C2—S211.7706 (19)C24—C251.384 (3)
C3—C41.385 (3)C24—H24A0.99 (2)
C3—H3A0.95 (2)C25—C261.380 (3)
C4—C51.382 (3)C25—H25A0.95 (3)
C4—H4A0.94 (2)C26—C271.382 (3)
C5—C61.375 (3)C26—H26A0.94 (2)
C5—H5A0.92 (3)C27—H27A0.94 (2)
C6—C1—C2118.92 (18)C1—C6—H6A117.6 (13)
C6—C1—C11120.13 (18)C2—S21—C21102.62 (10)
C2—C1—C11120.95 (17)C22—C21—S21106.68 (14)
O11—C11—C1120.40 (18)C22—C21—H21A110.6 (13)
O11—C11—C12120.2 (2)S21—C21—H21A107.3 (12)
C1—C11—C12119.40 (19)C22—C21—H21B112.2 (13)
C11—C12—H12A109 (2)S21—C21—H21B110.1 (14)
C11—C12—H12B113 (2)H21A—C21—H21B109.8 (19)
H12A—C12—H12B112 (3)C23—C22—C27118.49 (19)
C11—C12—H12C110.7 (18)C23—C22—C21121.02 (18)
H12A—C12—H12C111 (3)C27—C22—C21120.46 (19)
H12B—C12—H12C101 (3)C24—C23—C22120.98 (19)
C3—C2—C1118.46 (17)C24—C23—H23A120.2 (15)
C3—C2—S21121.27 (15)C22—C23—H23A118.8 (15)
C1—C2—S21120.27 (14)C23—C24—C25120.0 (2)
C4—C3—C2120.90 (19)C23—C24—H24A118.6 (14)
C4—C3—H3A119.8 (12)C25—C24—H24A121.4 (14)
C2—C3—H3A119.3 (12)C26—C25—C24119.6 (2)
C5—C4—C3120.6 (2)C26—C25—H25A120.4 (16)
C5—C4—H4A119.9 (15)C24—C25—H25A120.0 (16)
C3—C4—H4A119.5 (15)C25—C26—C27120.2 (2)
C6—C5—C4119.0 (2)C25—C26—H26A120.8 (13)
C6—C5—H5A119.8 (15)C27—C26—H26A119.0 (14)
C4—C5—H5A121.1 (15)C26—C27—C22120.8 (2)
C5—C6—C1122.0 (2)C26—C27—H27A122.7 (15)
C5—C6—H6A120.4 (13)C22—C27—H27A116.4 (15)

Experimental details

(II)(III)
Crystal data
Chemical formulaC14H12OSC15H14OS
Mr228.30242.32
Crystal system, space groupMonoclinic, P21/cOrthorhombic, Pbca
Temperature (K)293150
a, b, c (Å)9.0151 (7), 12.7805 (14), 10.6400 (12)7.8838 (18), 14.719 (3), 21.277 (4)
α, β, γ (°)90, 105.497 (7), 9090, 90, 90
V3)1181.3 (2)2469.1 (9)
Z48
Radiation typeCu KαCu Kα
µ (mm1)2.222.15
Crystal size (mm)0.58 × 0.47 × 0.390.54 × 0.18 × 0.12
Data collection
DiffractometerStoe Stadi-4 four-circle
diffractometer
Stoe Stadi-4 four-circle
diffractometer
Absorption correctionψ scans
(North et al., 1968)
ψ scans
(North et al., 1968)
Tmin, Tmax0.331, 0.4200.429, 0.581
No. of measured, independent and
observed [I > 2σ(I)] reflections
3137, 2070, 1754 2272, 1790, 1520
Rint0.0330.011
θmax (°)70.059.9
(sin θ/λ)max1)0.6100.561
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.110, 1.07 0.033, 0.087, 1.02
No. of reflections20701790
No. of parameters147211
H-atom treatmentSee textAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.30, 0.190.19, 0.30

Computer programs: DIF4 (Stoe & Cie, 1990a), DIF4, REDU4 (Stoe & Cie, 1990b), SHELXTL (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) for (II) top
C1—C61.400 (3)C2—S211.7694 (18)
C1—C21.414 (3)S21—C221.781 (2)
C1—C111.484 (3)C3—C41.381 (3)
C11—O111.213 (2)C4—C51.376 (3)
C11—C121.498 (3)C5—C61.367 (3)
C2—C31.389 (3)
C6—C1—C2118.13 (18)C3—C2—S21121.30 (15)
C6—C1—C11119.97 (17)C1—C2—S21120.06 (14)
C2—C1—C11121.90 (17)C2—S21—C22103.24 (9)
O11—C11—C1120.64 (18)C4—C3—C2121.42 (19)
O11—C11—C12119.6 (2)C5—C4—C3120.2 (2)
C1—C11—C12119.76 (19)C6—C5—C4119.25 (19)
C3—C2—C1118.64 (17)C5—C6—C1122.32 (19)
Selected geometric parameters (Å, º) for (III) top
C1—C61.393 (3)C2—S211.7706 (19)
C1—C21.415 (3)C3—C41.385 (3)
C1—C111.487 (3)C4—C51.382 (3)
C11—O111.214 (2)C5—C61.375 (3)
C11—C121.503 (3)S21—C211.821 (2)
C2—C31.398 (3)
C6—C1—C2118.92 (18)C3—C2—S21121.27 (15)
C6—C1—C11120.13 (18)C1—C2—S21120.27 (14)
C2—C1—C11120.95 (17)C4—C3—C2120.90 (19)
O11—C11—C1120.40 (18)C5—C4—C3120.6 (2)
O11—C11—C12120.2 (2)C6—C5—C4119.0 (2)
C1—C11—C12119.40 (19)C5—C6—C1122.0 (2)
C3—C2—C1118.46 (17)C2—S21—C21102.62 (10)
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds