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The compound 2-[(4-phen­oxy­phenyl)­sulfonyl­meth­yl]thiirane, C15H14O3S2, a selective gelatinase inhibitor, was synthesized and structurally characterized. Two crystals were analyzed, one each for the R and S enantio­mers, and the results were compared with the previously reported structure of the racemate. The enantio­merically pure compounds both crystallize with Z' = 2 in the space group P21, while the racemic mixture crystallizes with Z' = 1 in the space group P21/c, with disorder in the position of the thiirane group. This disorder accommodates both mol­ecules for each of the enantio­merically pure crystals, showing good overlap of the mol­ecules of the pure enanti­omorphs with the components of the centrosymmetric structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614021214/fa3348sup1.cif
Contains datablocks R-II, S-III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614021214/fa3348R-IIsup2.hkl
Contains datablock R-II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614021214/fa3348S-IIIsup3.hkl
Contains datablock S-III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614021214/fa3348R-IIsup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614021214/fa3348S-IIIsup5.cml
Supplementary material

CCDC references: 1025708; 1025709

Introduction top

Matrix metalloproteinases (MMPs) are a group of 23 enzymes in humans that are involved in a number of physiological and pathological processes (Gialeli et al., 2011; Sekhon, 2010; Lee et al., 2004; Stamenkovic, 2003; Sternlicht et al. 2001; Nagase et al., 1999; Massova et al., 1998). Two members of this family, MMP-2 and MMP-9, are known as gelatinases A and B, respectively. These two enzymes have emerged as important targets for inhibition, in the light of their involvement in a number of diseases affecting extracellular matrix remodeling, such as cancer metastasis and stroke. Compound (I) is a potent and selective gelatinase inhibitor (Brown et al., 2000). It is active in rodent models for cancer and stroke, and is a useful tool for the elucidation of the functional properties of these enzymes in in vivo models (Hadass et al., 2013; Cui et al., 2012; Gu et al., 2005; Krüger et al., 2005; Bonfil et al., 2006, 2007).

The optically active (R)- and (S)-enanti­omers of (I), starting from commercially available (R)- and (S)-epi­chloro­hydrin (97% ee), were synthesized and both (R)-(II) and (S)-(III) were equally active towards gelatinase inhibition (Lee et al., 2005). In a previous study, we have shown that the optical purity of the compounds (R)-(II) and (S)-(III) was >90%, based on the fact that no trace of the other enanti­omer was dete­cta­ble in the 1H NMR spectra in the presence of the chiral shift reagent, europium tris­[3-(hepta­fluoro­propyl­hydroxy­methyl­ene)-(+)-camphorate], Eu(hfc)3. A key reaction, the epoxide ring-opening reaction by 4-phen­oxy­phenyl­thiol­ate, occurred exclusively at atom C3 of epi­chloro­hydrin, not at atom C1, and the stereocenter was not scrambled during this step. In the final thiirane, the epi­chloro­hydrin C atoms become C13, C14 and C15. Throughout the remainder of the synthetic route, involving the formation of the epoxide ring, sulfide oxidation and thiirane ring formation, the stereocenter was intact. Although we can expect (R)-epi­chloro­hydrin to give the R-enanti­omer, (R)-(II), and (S)-epi­chloro­hydrin to give the S-enanti­omer, (S)-(III), their respective absolute stereochemistries need to be established experimentally. To determine the absolute stereochemistry of compounds (R)-(II) and (S)-(III), crystals were grown and their X-ray crystal structures were determined. We have reported the structure of the racemic (I) previously (Lee et al., 2008).

Experimental top

Synthesis and crystallization top

Compounds (R)-(II) and (S)-(III) were synthesized according to the literature procedure developed in our laboratory (Lee et al., 2005). Crystals of suitable size for single-crystal X-ray diffraction analysis were obtained by diffusion of hexanes (or di­ethyl ether) into a CH2Cl2 solution at room temperature overnight.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. Examination of the structures of (R)-(II) and (S)-(III) suggests the possibility of inversion symmetry relating the two independent molecules of the asymmetric unit. The intensity data show a number of systematic absence violations for a c-glide, and no solution could be obtained for space group P21/m. In addition, 8% of the atoms of the structure do not fit the proposed inversion symmetry. These atoms are located at the stereocenter.

From the synthesis, the stereochemistry of the parent epi­chloro­hydrin was expected to be retained. This was one purpose of the study and was confirmed by comparison of the intensities of Friedel pairs of reflections and a Bayesian analysis of the Friedel pairs. For (R)-(II), the Flack x parameter is 0.055 (9) (Parsons et al., 2013) and the Hooft y parameter is 0.053 (11) (Hooft et al., 2008). (S)-(III) yields a Flack x parameter of 0.02 (2) and a Hooft y parameter of 0.010 (12). For both structures these analyses are in agreement and strongly indicate the correct absolute stereochemistry. Further support for this hypothesis is provided by the |E2-1| statistics for both compounds (0.835 and 0.826, respectively). While these |E2-1| values deviate from the expected value of 0.736 for an acentric space group, they tend towards this value. Based on these analyses, the space group P21 was retained.

H atoms were included in geometrically calculated positions and refined with C—H = 0.95 Å for aromatic C—H, 0.99 Å for methyl­ene C—H and 1.00 Å for methyne C—H, and with Uiso(H) = 1.2Ueq(C).

Results and discussion top

X-ray analysis of (R)-(II) and (S)-(III) reveals that their respective stereochemistries were (R) and (S), as anti­cipated. The unit-cell dimensions for (I), (R)-(II) and (S)-(III) are all identical. Clearly, (R)-(II) and (S)-(III) are related by inversion (stereoisomers), but they are not perfectly superimposed upon inversion. Compound (I) crystallizes in space group P21/c, with disorder in the orientation of the thiirane at the stereocenter located at C14 (Lee et al., 2008). In the chosen asymmetric unit for (I), the S-enanti­omer is present with a site occupancy of 0.701 (7); the R-enanti­omer is present as disorder at a site occupancy of 0.299 (7). Upon inversion, the primary component becomes the R-enanti­omer. It would be equally valid to use a reference asymmetric unit in which the R-enanti­omer was the majority component. In (R)-(II) and (S)-(III), the space group is P21. Two independent molecules (molecule 1, indicated with a suffix A on the atom labels, and molecule 2, with a suffix B) (Fig. 1), are present in the unit cell: Z' = 2 and Z = 4. The two molecules within the asymmetric unit are not superimposable, differing in the orientation of the sulfonyl­methyl­thiirane group and the terminal phenyl group (Fig. 2).

The sulfonyl­methyl­thiirane groups are oriented in different directions within the two independent molecules in both (R)-(II) and (S)-(III), demonstrated by the differing C10—S1—C13—C14 torsion angles (Tables 2 and 3). The terminal phenyl groups are also pivoted and do not overlay each other (Fig. 2; C1—O1—C7—C8 torsion angles, Tables 2 and 3). The overlay of the two independent molecules in each compound reveals that the molecules adopt a pseudo-mirror symmetry, differing primarily in the orientation of the thiirane ring; the pseudo-mirror plane accounts for the orientation of the terminal phenyl group. The thiirane ring breaks the mirror symmetry due to the chiral center at C14. It is a known phenomenon that chiral molecules often adopt pseudo-symmetry in structures with Z' > 1 (Collins et al., 2006).

The orientation of the thiirane ring is such that it allows nesting of atom S2 of one molecule into the center of the middle phenyl ring of the second molecule related by an a-axis translation (Table 4). For (R)-(II), the average contact distance is 3.557 Å, and in (S)-(III) the contact between S2 and the ring centroid is 3.506 Å. The molecules otherwise pack in a herringbone-type fashion (Fig. 3), mimicking the glide plane present in the racemate. Again, this is a common feature of chiral structures with Z' > 1 (Collins et al., 2006).

Comparison of the structures of (R)-(II) and (S)-(III) with the parent racemate (I) shows significant overlap of all three structures (Fig. 4). The disorder present in racemate (I) is a result of the two orientations of the independent molecules in both (R)-(II) and (S)-(III) (Figs. 2 and 4). Since (R)-(II) and (S)-(III) are related by inversion and adopt a unit cell with parameters close to that of racemate (I), it appears that the two orientations of the phenyl and thiirane rings found in the enanti­opure compounds (R)-(II) and (S)-(III) are retained to some degree in the racemate upon crystallization. While the percentages vary, this provides the rationalization for the disorder observed in (I).

In summary, we report the structures of the two enanti­omerically pure thiirane compounds that comprise the structure of the previously reported 2-(4-phen­oxy­phenyl­sulfonyl­methyl)­thiirane, and discuss their role in the observed disorder in the racemate.

Related literature top

For related literature, see: Bonfil et al. (2006, 2007); Brown et al. (2000); Collins et al. (2006); Cui et al. (2012); Gialeli et al. (2011); Gu et al. (2005); Hadass et al. (2013); Hooft et al. (2008); Krüger et al. (2005); Lee et al. (2004, 2005, 2008); Massova et al. (1998); Nagase et al. (1999); Parsons et al. (2013); Sekhon (2010); Stamenkovic (2003); Sternlicht et al. (2001).

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2007). Cell refinement: APEX2 and SAINT (Bruker, 2007) for R-II; SAINT (Bruker, 2014) for S-III. Data reduction: SAINT (Bruker, 2007) and XPREP (Sheldrick, 2008) for R-II; SAINT (Bruker, 2014) for S-III. For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014); molecular graphics: CrystalMaker (Palmer, 2008), Mercury (Macrae et al., 2008), pyMOL (Schrödinger, 2011) and POVRay (Cason, 2003); software used to prepare material for publication: XCIF (Sheldrick, 2008), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (R)-(II), showing the atom-numbering scheme and the interaction between atom S2 and the ring centroid. Displacement ellipsoids are drawn at the 50% probability level. The structure of (S)-(III) is identical, except for the opposite chirality at C14.
[Figure 2] Fig. 2. Overlays of the independent molecules in (a) (R)-(II) and (b) (S)-(III). Fit made at C7 to C12. Molecule A is shown in red, molecule B in light green.
[Figure 3] Fig. 3. A packing diagram of (R)-(II). Molecule B is shown in gray.
[Figure 4] Fig. 4. An overlay of (I) (red), (R)-(II) (green and light green) and (S)-(III) (blue and light blue), demonstrating the disorder. Disorder in (I) is indicated by red stars. (R)-(II)A (green) and (S)-(III)B (light blue) are the mirror images of the reference unit of (I). Note the high degree of structural overlap.
(R-II) (R)-2-(4-Phenoxyphenylsulfonylmethyl)thiirane top
Crystal data top
C15H14O3S2F(000) = 640
Mr = 306.38Dx = 1.448 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 5.3891 (3) ÅCell parameters from 3913 reflections
b = 28.3231 (13) Åθ = 3.1–67.3°
c = 9.2503 (4) ŵ = 3.48 mm1
β = 95.434 (3)°T = 100 K
V = 1405.58 (12) Å3Needle, clear colourless
Z = 40.23 × 0.01 × 0.01 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4353 independent reflections
Radiation source: fine-focus sealed tube, Siemens KFFCU2K-903926 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 8.33 pixels mm-1θmax = 69.3°, θmin = 3.1°
ϕ and ω scansh = 64
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
k = 3333
Tmin = 0.50, Tmax = 0.97l = 1110
11717 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0625P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
4353 reflectionsΔρmax = 0.43 e Å3
361 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack x parameter determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.055 (9)
Crystal data top
C15H14O3S2V = 1405.58 (12) Å3
Mr = 306.38Z = 4
Monoclinic, P21Cu Kα radiation
a = 5.3891 (3) ŵ = 3.48 mm1
b = 28.3231 (13) ÅT = 100 K
c = 9.2503 (4) Å0.23 × 0.01 × 0.01 mm
β = 95.434 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4353 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
3926 reflections with I > 2σ(I)
Tmin = 0.50, Tmax = 0.97Rint = 0.035
11717 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.097Δρmax = 0.43 e Å3
S = 1.07Δρmin = 0.23 e Å3
4353 reflectionsAbsolute structure: Flack x parameter determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
361 parametersAbsolute structure parameter: 0.055 (9)
1 restraint
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. Examination of the structure suggests the possibility of inversion symmetry relating the two independent molecules of the asymmetric unit. The intensity data show a number of systematic absence violations for P21/c and no solution could be obtained for P21/m. In addition, 8% of the atoms of the structure do not fit the proposed inversion symmetry. Based on these analyses, the space group P21 was retained.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.70704 (19)0.56561 (4)0.13832 (11)0.0173 (3)
S2A0.8468 (2)0.43844 (4)0.13205 (13)0.0270 (3)
O1A0.9356 (6)0.71950 (13)0.2825 (3)0.0238 (8)
O2A0.4423 (6)0.55669 (13)0.1384 (3)0.0230 (7)
O3A0.8054 (6)0.57784 (12)0.2718 (3)0.0233 (7)
C1A1.0894 (9)0.75743 (17)0.2500 (5)0.0199 (10)
C2A1.3181 (9)0.76229 (19)0.3292 (5)0.0246 (11)
H2A1.37780.73890.39730.029*
C3A1.4589 (10)0.8023 (2)0.3069 (6)0.0305 (13)
H3A1.61610.80640.36130.037*
C4A1.3749 (11)0.8358 (2)0.2082 (6)0.0320 (13)
H4A1.47230.86310.19450.038*
C5A1.1445 (10)0.82964 (19)0.1273 (6)0.0290 (12)
H5A1.08700.85260.05710.035*
C6A1.0002 (9)0.7904 (2)0.1487 (5)0.0250 (10)
H6A0.84270.78630.09480.030*
C7A0.8926 (9)0.68441 (17)0.1816 (5)0.0180 (10)
C8A1.0465 (9)0.67601 (18)0.0714 (5)0.0187 (10)
H8A1.18750.69550.06220.022*
C9A0.9928 (8)0.63910 (17)0.0247 (5)0.0188 (10)
H9A1.09680.63300.09990.023*
C10A0.7846 (8)0.61091 (17)0.0099 (5)0.0179 (9)
C11A0.6323 (8)0.61891 (17)0.1010 (5)0.0192 (10)
H11A0.49220.59920.11090.023*
C12A0.6864 (8)0.65558 (19)0.1962 (5)0.0203 (10)
H12A0.58330.66130.27220.024*
C13A0.8710 (8)0.51414 (16)0.0693 (5)0.0191 (9)
H13A0.84330.48800.14010.023*
H13B1.05200.52090.05620.023*
C14A0.7824 (8)0.49931 (16)0.0749 (5)0.0212 (9)
H14A0.80420.52350.15390.025*
C15A0.5567 (9)0.46964 (19)0.0749 (6)0.0280 (12)
H15A0.47050.46110.02080.034*
H15B0.44310.47630.15050.034*
S1B0.3123 (2)0.45368 (4)0.60609 (13)0.0214 (3)
S2B0.1707 (2)0.58472 (5)0.35736 (13)0.0290 (3)
O1B0.0601 (6)0.29480 (13)0.2112 (3)0.0263 (8)
O2B0.5729 (6)0.46423 (12)0.6017 (4)0.0276 (8)
O3B0.2197 (6)0.44597 (13)0.7444 (4)0.0288 (8)
C1B0.0977 (9)0.25807 (18)0.2458 (5)0.0223 (11)
C2B0.3246 (9)0.25306 (18)0.1644 (5)0.0248 (11)
H2B0.37710.27560.09170.030*
C3B0.4750 (10)0.2148 (2)0.1900 (6)0.0294 (12)
H3B0.63100.21090.13430.035*
C4B0.3982 (11)0.1822 (2)0.2963 (6)0.0334 (14)
H4B0.50240.15620.31360.040*
C5B0.1714 (11)0.1873 (2)0.3778 (6)0.0323 (13)
H5B0.11930.16460.45010.039*
C6B0.0176 (9)0.2261 (2)0.3531 (5)0.0265 (11)
H6B0.13800.23020.40910.032*
C7B0.1147 (9)0.32956 (18)0.3115 (5)0.0216 (11)
C8B0.0297 (9)0.33920 (19)0.4247 (5)0.0190 (10)
H8B0.17020.32010.43880.023*
C9B0.0321 (8)0.37667 (17)0.5166 (5)0.0188 (10)
H9B0.06700.38380.59340.023*
C10B0.2416 (9)0.40400 (18)0.4956 (5)0.0195 (10)
C11B0.3848 (9)0.39436 (17)0.3826 (5)0.0222 (10)
H11B0.52600.41340.36910.027*
C12B0.3236 (9)0.35762 (18)0.2906 (5)0.0210 (10)
H12B0.42160.35100.21290.025*
C13B0.1288 (8)0.49897 (19)0.5035 (6)0.0303 (11)
H13C0.10350.48940.40020.036*
H13D0.03710.50120.54060.036*
C14B0.2505 (9)0.54610 (17)0.5137 (5)0.0272 (11)
H14B0.26080.56160.61120.033*
C15B0.4595 (9)0.5555 (2)0.4257 (5)0.0297 (12)
H15C0.51650.52900.36750.036*
H15D0.59590.57580.46960.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0147 (6)0.0172 (6)0.0199 (6)0.0006 (4)0.0009 (4)0.0001 (5)
S2A0.0318 (7)0.0210 (7)0.0284 (6)0.0023 (5)0.0026 (5)0.0042 (5)
O1A0.027 (2)0.025 (2)0.0201 (16)0.0105 (14)0.0060 (14)0.0037 (14)
O2A0.0154 (17)0.026 (2)0.0266 (16)0.0020 (13)0.0015 (12)0.0030 (14)
O3A0.0256 (19)0.025 (2)0.0196 (16)0.0009 (12)0.0009 (13)0.0007 (13)
C1A0.021 (3)0.019 (3)0.021 (2)0.0018 (18)0.0084 (19)0.006 (2)
C2A0.023 (3)0.027 (3)0.024 (2)0.002 (2)0.006 (2)0.006 (2)
C3A0.026 (3)0.035 (3)0.031 (3)0.008 (2)0.009 (2)0.014 (3)
C4A0.040 (3)0.027 (3)0.032 (3)0.012 (2)0.019 (3)0.012 (2)
C5A0.039 (3)0.023 (3)0.027 (3)0.002 (2)0.012 (2)0.000 (2)
C6A0.024 (3)0.027 (3)0.024 (2)0.001 (2)0.0050 (18)0.004 (2)
C7A0.017 (3)0.016 (3)0.020 (2)0.0004 (17)0.0027 (17)0.000 (2)
C8A0.016 (3)0.019 (3)0.020 (2)0.0006 (18)0.0005 (18)0.002 (2)
C9A0.016 (2)0.022 (3)0.018 (2)0.0016 (17)0.0022 (17)0.0017 (19)
C10A0.016 (2)0.017 (2)0.020 (2)0.0036 (17)0.0006 (18)0.0026 (19)
C11A0.014 (2)0.019 (3)0.025 (2)0.0020 (17)0.0002 (17)0.0020 (19)
C12A0.014 (2)0.028 (3)0.020 (2)0.0003 (18)0.0066 (18)0.002 (2)
C13A0.019 (2)0.011 (2)0.027 (2)0.0018 (15)0.0019 (18)0.0013 (19)
C14A0.023 (2)0.017 (2)0.024 (2)0.0029 (17)0.0001 (17)0.0003 (19)
C15A0.024 (3)0.032 (3)0.029 (3)0.001 (2)0.005 (2)0.009 (2)
S1B0.0159 (6)0.0169 (6)0.0314 (6)0.0008 (4)0.0015 (4)0.0006 (5)
S2B0.0311 (7)0.0280 (7)0.0271 (6)0.0009 (5)0.0022 (5)0.0046 (5)
O1B0.025 (2)0.033 (2)0.0208 (16)0.0076 (14)0.0047 (13)0.0036 (15)
O2B0.0169 (18)0.022 (2)0.0436 (19)0.0001 (12)0.0010 (14)0.0052 (15)
O3B0.029 (2)0.026 (2)0.0305 (18)0.0023 (14)0.0012 (14)0.0060 (15)
C1B0.022 (3)0.021 (3)0.025 (2)0.0044 (18)0.009 (2)0.007 (2)
C2B0.024 (3)0.027 (3)0.024 (3)0.001 (2)0.006 (2)0.007 (2)
C3B0.020 (3)0.037 (3)0.032 (3)0.007 (2)0.008 (2)0.012 (3)
C4B0.038 (3)0.028 (3)0.037 (3)0.012 (2)0.021 (3)0.015 (3)
C5B0.046 (4)0.023 (3)0.030 (3)0.002 (2)0.013 (2)0.002 (2)
C6B0.026 (3)0.031 (3)0.023 (2)0.000 (2)0.005 (2)0.004 (2)
C7B0.020 (3)0.022 (3)0.022 (2)0.0006 (19)0.0033 (19)0.004 (2)
C8B0.012 (2)0.026 (3)0.019 (2)0.0016 (17)0.0007 (18)0.003 (2)
C9B0.013 (2)0.021 (3)0.023 (2)0.0006 (17)0.0052 (17)0.0038 (19)
C10B0.014 (2)0.021 (3)0.023 (2)0.0006 (17)0.0019 (18)0.0007 (19)
C11B0.015 (2)0.020 (3)0.032 (3)0.0003 (18)0.0052 (19)0.009 (2)
C12B0.017 (3)0.024 (3)0.022 (2)0.0032 (18)0.0053 (18)0.004 (2)
C13B0.017 (3)0.023 (3)0.050 (3)0.0018 (19)0.000 (2)0.006 (2)
C14B0.030 (3)0.026 (3)0.024 (2)0.0013 (18)0.0053 (19)0.008 (2)
C15B0.021 (3)0.036 (3)0.033 (3)0.005 (2)0.003 (2)0.013 (2)
Geometric parameters (Å, º) top
S1A—O3A1.432 (3)S1B—O3B1.433 (4)
S1A—O2A1.449 (3)S1B—O2B1.440 (4)
S1A—C10A1.771 (5)S1B—C10B1.760 (5)
S1A—C13A1.791 (5)S1B—C13B1.829 (5)
S2A—C14A1.827 (5)S2B—C15B1.822 (5)
S2A—C15A1.830 (5)S2B—C14B1.832 (5)
O1A—C7A1.368 (6)O1B—C7B1.366 (6)
O1A—C1A1.407 (6)O1B—C1B1.400 (6)
C1A—C6A1.378 (8)C1B—C2B1.382 (8)
C1A—C2A1.380 (7)C1B—C6B1.382 (8)
C2A—C3A1.390 (8)C2B—C3B1.388 (8)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.363 (9)C3B—C4B1.382 (9)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.399 (8)C4B—C5B1.381 (9)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.381 (8)C5B—C6B1.408 (8)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.394 (7)C7B—C8B1.389 (7)
C7A—C12A1.396 (7)C7B—C12B1.406 (7)
C8A—C9A1.385 (7)C8B—C9B1.380 (8)
C8A—H8A0.9500C8B—H8B0.9500
C9A—C10A1.394 (7)C9B—C10B1.398 (7)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.392 (6)C10B—C11B1.384 (7)
C11A—C12A1.375 (7)C11B—C12B1.365 (8)
C11A—H11A0.9500C11B—H11B0.9500
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.518 (6)C13B—C14B1.486 (7)
C13A—H13A0.9900C13B—H13C0.9900
C13A—H13B0.9900C13B—H13D0.9900
C14A—C15A1.479 (7)C14B—C15B1.475 (6)
C14A—H14A1.0000C14B—H14B1.0000
C15A—H15A0.9900C15B—H15C0.9900
C15A—H15B0.9900C15B—H15D0.9900
O3A—S1A—O2A119.12 (19)O3B—S1B—O2B118.7 (2)
O3A—S1A—C10A108.7 (2)O3B—S1B—C10B108.8 (2)
O2A—S1A—C10A107.2 (2)O2B—S1B—C10B107.9 (2)
O3A—S1A—C13A107.1 (2)O3B—S1B—C13B110.7 (2)
O2A—S1A—C13A108.1 (2)O2B—S1B—C13B108.7 (2)
C10A—S1A—C13A105.9 (2)C10B—S1B—C13B100.5 (2)
C14A—S2A—C15A47.7 (2)C15B—S2B—C14B47.6 (2)
C7A—O1A—C1A118.3 (3)C7B—O1B—C1B118.5 (4)
C6A—C1A—C2A122.0 (5)C2B—C1B—C6B121.6 (5)
C6A—C1A—O1A119.3 (4)C2B—C1B—O1B118.5 (4)
C2A—C1A—O1A118.5 (4)C6B—C1B—O1B119.7 (5)
C1A—C2A—C3A118.4 (5)C1B—C2B—C3B119.2 (5)
C1A—C2A—H2A120.8C1B—C2B—H2B120.4
C3A—C2A—H2A120.8C3B—C2B—H2B120.4
C4A—C3A—C2A121.0 (5)C4B—C3B—C2B120.2 (5)
C4A—C3A—H3A119.5C4B—C3B—H3B119.9
C2A—C3A—H3A119.5C2B—C3B—H3B119.9
C3A—C4A—C5A119.6 (5)C5B—C4B—C3B120.6 (5)
C3A—C4A—H4A120.2C5B—C4B—H4B119.7
C5A—C4A—H4A120.2C3B—C4B—H4B119.7
C6A—C5A—C4A120.5 (5)C4B—C5B—C6B119.8 (5)
C6A—C5A—H5A119.8C4B—C5B—H5B120.1
C4A—C5A—H5A119.8C6B—C5B—H5B120.1
C1A—C6A—C5A118.6 (5)C1B—C6B—C5B118.6 (5)
C1A—C6A—H6A120.7C1B—C6B—H6B120.7
C5A—C6A—H6A120.7C5B—C6B—H6B120.7
O1A—C7A—C8A123.3 (4)O1B—C7B—C8B123.6 (5)
O1A—C7A—C12A116.3 (4)O1B—C7B—C12B116.0 (4)
C8A—C7A—C12A120.4 (4)C8B—C7B—C12B120.3 (5)
C9A—C8A—C7A119.7 (4)C9B—C8B—C7B119.7 (4)
C9A—C8A—H8A120.2C9B—C8B—H8B120.1
C7A—C8A—H8A120.2C7B—C8B—H8B120.1
C8A—C9A—C10A119.4 (4)C8B—C9B—C10B119.4 (4)
C8A—C9A—H9A120.3C8B—C9B—H9B120.3
C10A—C9A—H9A120.3C10B—C9B—H9B120.3
C11A—C10A—C9A121.0 (4)C11B—C10B—C9B120.8 (5)
C11A—C10A—S1A119.6 (4)C11B—C10B—S1B119.4 (4)
C9A—C10A—S1A119.3 (3)C9B—C10B—S1B119.7 (4)
C12A—C11A—C10A119.4 (4)C12B—C11B—C10B120.1 (4)
C12A—C11A—H11A120.3C12B—C11B—H11B119.9
C10A—C11A—H11A120.3C10B—C11B—H11B119.9
C11A—C12A—C7A120.1 (4)C11B—C12B—C7B119.6 (4)
C11A—C12A—H12A119.9C11B—C12B—H12B120.2
C7A—C12A—H12A119.9C7B—C12B—H12B120.2
C14A—C13A—S1A110.7 (3)C14B—C13B—S1B112.5 (4)
C14A—C13A—H13A109.5C14B—C13B—H13C109.1
S1A—C13A—H13A109.5S1B—C13B—H13C109.1
C14A—C13A—H13B109.5C14B—C13B—H13D109.1
S1A—C13A—H13B109.5S1B—C13B—H13D109.1
H13A—C13A—H13B108.1H13C—C13B—H13D107.8
C15A—C14A—C13A119.0 (4)C15B—C14B—C13B118.9 (5)
C15A—C14A—S2A66.3 (3)C15B—C14B—S2B65.9 (3)
C13A—C14A—S2A116.7 (3)C13B—C14B—S2B114.6 (4)
C15A—C14A—H14A115.3C15B—C14B—H14B116.0
C13A—C14A—H14A115.3C13B—C14B—H14B116.0
S2A—C14A—H14A115.3S2B—C14B—H14B116.0
C14A—C15A—S2A66.0 (3)C14B—C15B—S2B66.5 (3)
C14A—C15A—H15A117.1C14B—C15B—H15C117.1
S2A—C15A—H15A117.1S2B—C15B—H15C117.1
C14A—C15A—H15B117.1C14B—C15B—H15D117.1
S2A—C15A—H15B117.1S2B—C15B—H15D117.1
H15A—C15A—H15B114.1H15C—C15B—H15D114.1
C7A—O1A—C1A—C6A72.7 (6)C7B—O1B—C1B—C2B116.1 (5)
C7A—O1A—C1A—C2A112.3 (5)C7B—O1B—C1B—C6B68.1 (6)
C6A—C1A—C2A—C3A1.1 (7)C6B—C1B—C2B—C3B0.6 (7)
O1A—C1A—C2A—C3A173.7 (4)O1B—C1B—C2B—C3B175.1 (4)
C1A—C2A—C3A—C4A0.7 (7)C1B—C2B—C3B—C4B0.3 (7)
C2A—C3A—C4A—C5A0.5 (8)C2B—C3B—C4B—C5B0.3 (8)
C3A—C4A—C5A—C6A1.2 (8)C3B—C4B—C5B—C6B0.5 (8)
C2A—C1A—C6A—C5A0.5 (7)C2B—C1B—C6B—C5B0.8 (7)
O1A—C1A—C6A—C5A174.4 (4)O1B—C1B—C6B—C5B174.9 (4)
C4A—C5A—C6A—C1A0.7 (7)C4B—C5B—C6B—C1B0.7 (7)
C1A—O1A—C7A—C8A20.5 (7)C1B—O1B—C7B—C8B20.4 (7)
C1A—O1A—C7A—C12A161.4 (4)C1B—O1B—C7B—C12B162.6 (4)
O1A—C7A—C8A—C9A178.6 (4)O1B—C7B—C8B—C9B176.5 (4)
C12A—C7A—C8A—C9A0.6 (7)C12B—C7B—C8B—C9B0.3 (7)
C7A—C8A—C9A—C10A0.2 (7)C7B—C8B—C9B—C10B0.9 (7)
C8A—C9A—C10A—C11A0.9 (7)C8B—C9B—C10B—C11B1.1 (7)
C8A—C9A—C10A—S1A176.8 (4)C8B—C9B—C10B—S1B176.7 (4)
O3A—S1A—C10A—C11A152.5 (4)O3B—S1B—C10B—C11B155.8 (4)
O2A—S1A—C10A—C11A22.5 (4)O2B—S1B—C10B—C11B25.8 (5)
C13A—S1A—C10A—C11A92.8 (4)C13B—S1B—C10B—C11B88.0 (4)
O3A—S1A—C10A—C9A25.3 (4)O3B—S1B—C10B—C9B28.6 (5)
O2A—S1A—C10A—C9A155.2 (4)O2B—S1B—C10B—C9B158.6 (4)
C13A—S1A—C10A—C9A89.5 (4)C13B—S1B—C10B—C9B87.7 (4)
C9A—C10A—C11A—C12A0.9 (7)C9B—C10B—C11B—C12B0.5 (7)
S1A—C10A—C11A—C12A176.9 (4)S1B—C10B—C11B—C12B176.1 (4)
C10A—C11A—C12A—C7A0.1 (7)C10B—C11B—C12B—C7B0.2 (8)
O1A—C7A—C12A—C11A178.8 (4)O1B—C7B—C12B—C11B177.3 (4)
C8A—C7A—C12A—C11A0.6 (7)C8B—C7B—C12B—C11B0.3 (8)
O3A—S1A—C13A—C14A178.6 (3)O3B—S1B—C13B—C14B98.9 (4)
O2A—S1A—C13A—C14A51.9 (4)O2B—S1B—C13B—C14B33.1 (5)
C10A—S1A—C13A—C14A62.8 (4)C10B—S1B—C13B—C14B146.2 (4)
S1A—C13A—C14A—C15A83.9 (4)S1B—C13B—C14B—C15B77.5 (5)
S1A—C13A—C14A—S2A160.2 (2)S1B—C13B—C14B—S2B152.4 (3)
C15A—S2A—C14A—C13A111.8 (4)C15B—S2B—C14B—C13B112.1 (5)
C13A—C14A—C15A—S2A108.5 (4)C13B—C14B—C15B—S2B105.9 (4)
(S-III) (S)-2-(4-Phenoxyphenylsulfonylmethyl)thiirane top
Crystal data top
C15H14O3S2F(000) = 640
Mr = 306.38Dx = 1.447 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 5.3887 (3) ÅCell parameters from 5268 reflections
b = 28.3506 (12) Åθ = 4.8–68.0°
c = 9.2463 (4) ŵ = 3.47 mm1
β = 95.463 (3)°T = 100 K
V = 1406.17 (12) Å3Needle, clear colourless
Z = 40.22 × 0.07 × 0.01 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4473 independent reflections
Radiation source: fine-focus sealed tube, Siemens KFFCU2K-903968 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 8.33 pixels mm-1θmax = 68.5°, θmin = 3.1°
ϕ and ω scansh = 66
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2012)
k = 3333
Tmin = 0.789, Tmax = 0.971l = 1111
25587 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0721P)2 + 3.2676P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
4473 reflectionsΔρmax = 0.66 e Å3
361 parametersΔρmin = 0.44 e Å3
1 restraintAbsolute structure: Flack x parameter determined using 1669 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (2)
Crystal data top
C15H14O3S2V = 1406.17 (12) Å3
Mr = 306.38Z = 4
Monoclinic, P21Cu Kα radiation
a = 5.3887 (3) ŵ = 3.47 mm1
b = 28.3506 (12) ÅT = 100 K
c = 9.2463 (4) Å0.22 × 0.07 × 0.01 mm
β = 95.463 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4473 independent reflections
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2012)
3968 reflections with I > 2σ(I)
Tmin = 0.789, Tmax = 0.971Rint = 0.053
25587 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.143Δρmax = 0.66 e Å3
S = 1.02Δρmin = 0.44 e Å3
4473 reflectionsAbsolute structure: Flack x parameter determined using 1669 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
361 parametersAbsolute structure parameter: 0.02 (2)
1 restraint
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.2929 (4)0.59141 (6)0.63875 (18)0.0157 (4)
S2A0.1530 (5)0.71863 (7)0.3688 (2)0.0266 (5)
O1A0.0645 (12)0.4375 (2)0.2178 (6)0.0236 (14)
O2A0.1926 (11)0.57904 (19)0.7715 (5)0.0225 (13)
O3A0.5569 (11)0.6001 (2)0.6394 (5)0.0214 (12)
C1A0.0901 (17)0.3997 (3)0.2493 (8)0.0200 (18)
C2A0.3188 (17)0.3946 (3)0.1712 (8)0.0221 (19)
H2A0.37820.41800.10290.027*
C3A0.463 (2)0.3548 (3)0.1930 (10)0.034 (2)
H3A0.62110.35110.13930.041*
C4A0.377 (2)0.3213 (3)0.2914 (10)0.032 (2)
H4A0.47410.29400.30550.039*
C5A0.144 (2)0.3274 (3)0.3721 (9)0.029 (2)
H5A0.08560.30430.44160.035*
C6A0.0006 (17)0.3667 (3)0.3511 (9)0.0242 (18)
H6A0.15790.37090.40520.029*
C7A0.1061 (17)0.4729 (3)0.3187 (8)0.0170 (17)
C8A0.0456 (16)0.4808 (3)0.4291 (8)0.0175 (17)
H8A0.18500.46090.43870.021*
C9A0.0062 (17)0.5179 (3)0.5262 (8)0.0194 (18)
H9A0.09870.52400.60100.023*
C10A0.2155 (16)0.5461 (3)0.5113 (8)0.0160 (17)
C11A0.3675 (17)0.5383 (3)0.3992 (8)0.0190 (17)
H11A0.50680.55810.38840.023*
C12A0.3113 (16)0.5011 (3)0.3036 (8)0.0182 (17)
H12A0.41430.49500.22780.022*
C13A0.1292 (15)0.6428 (3)0.5695 (8)0.0186 (16)
H13A0.05180.63610.55650.022*
H13B0.15710.66890.64030.022*
C14A0.2181 (15)0.6578 (3)0.4242 (8)0.0216 (16)
H14A0.19780.63370.34490.026*
C15A0.4445 (17)0.6874 (3)0.4274 (10)0.030 (2)
H15A0.56000.68120.35250.036*
H15B0.52840.69570.52400.036*
S1B0.6873 (4)0.70339 (6)0.1052 (2)0.0212 (5)
S2B0.8290 (4)0.57240 (8)0.1433 (2)0.0282 (5)
O1B0.9399 (12)0.8624 (2)0.2891 (5)0.0250 (14)
O2B0.7782 (12)0.7110 (2)0.2438 (6)0.0276 (14)
O3B0.4263 (11)0.69272 (19)0.1006 (6)0.0253 (13)
C1B1.0972 (17)0.8993 (3)0.2529 (8)0.0212 (18)
C2B1.3235 (18)0.9040 (3)0.3363 (9)0.025 (2)
H2B1.37520.88170.40990.030*
C3B1.4721 (18)0.9424 (3)0.3087 (9)0.028 (2)
H3B1.62890.94610.36370.034*
C4B1.398 (2)0.9750 (3)0.2038 (10)0.032 (2)
H4B1.50121.00120.18820.038*
C5B1.173 (2)0.9698 (3)0.1215 (10)0.030 (2)
H5B1.12300.99210.04780.036*
C6B1.0176 (18)0.9311 (3)0.1468 (9)0.025 (2)
H6B0.86120.92720.09140.030*
C7B0.8843 (17)0.8275 (3)0.1882 (9)0.0202 (18)
C8B1.0289 (17)0.8178 (3)0.0748 (9)0.0186 (18)
H8B1.16870.83700.06010.022*
C9B0.9678 (15)0.7801 (3)0.0161 (9)0.0179 (17)
H9B1.06750.77250.09220.021*
C10B0.7575 (15)0.7534 (3)0.0055 (8)0.0160 (17)
C11B0.6141 (16)0.7631 (3)0.1174 (8)0.0192 (17)
H11B0.47190.74420.12990.023*
C12B0.6751 (17)0.7997 (3)0.2108 (8)0.0193 (18)
H12B0.57820.80620.28910.023*
C13B0.8703 (16)0.6580 (3)0.0042 (9)0.0278 (19)
H13C1.03490.65550.04290.033*
H13D0.89890.66760.09890.033*
C14B0.7487 (17)0.6112 (3)0.0125 (9)0.030 (2)
H14B0.73710.59570.10990.036*
C15B0.5399 (17)0.6018 (3)0.0756 (9)0.028 (2)
H15C0.40300.58170.03160.034*
H15D0.48360.62830.13430.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0148 (10)0.0170 (10)0.0151 (9)0.0003 (7)0.0000 (7)0.0009 (7)
S2A0.0347 (14)0.0198 (11)0.0249 (10)0.0022 (9)0.0014 (9)0.0041 (8)
O1A0.029 (4)0.024 (3)0.018 (3)0.011 (3)0.006 (2)0.004 (2)
O2A0.020 (3)0.027 (3)0.020 (3)0.001 (2)0.001 (2)0.000 (2)
O3A0.020 (3)0.023 (3)0.020 (3)0.002 (2)0.002 (2)0.002 (2)
C1A0.027 (5)0.017 (4)0.018 (4)0.002 (3)0.012 (4)0.006 (3)
C2A0.019 (5)0.032 (5)0.015 (4)0.001 (4)0.004 (3)0.007 (3)
C3A0.033 (6)0.037 (6)0.035 (5)0.008 (4)0.010 (4)0.016 (4)
C4A0.051 (7)0.020 (5)0.030 (5)0.013 (4)0.022 (5)0.010 (4)
C5A0.047 (7)0.021 (5)0.022 (4)0.003 (4)0.014 (4)0.000 (3)
C6A0.023 (5)0.027 (5)0.023 (4)0.004 (4)0.004 (3)0.004 (3)
C7A0.020 (5)0.020 (4)0.010 (4)0.002 (3)0.002 (3)0.001 (3)
C8A0.013 (5)0.021 (4)0.016 (4)0.000 (3)0.008 (3)0.000 (3)
C9A0.027 (5)0.016 (4)0.015 (4)0.004 (3)0.002 (3)0.004 (3)
C10A0.020 (5)0.015 (4)0.013 (4)0.001 (3)0.000 (3)0.002 (3)
C11A0.020 (5)0.015 (4)0.022 (4)0.003 (3)0.001 (3)0.001 (3)
C12A0.015 (5)0.026 (4)0.015 (4)0.001 (3)0.006 (3)0.000 (3)
C13A0.014 (4)0.017 (4)0.023 (4)0.005 (3)0.009 (3)0.001 (3)
C14A0.027 (5)0.013 (4)0.024 (4)0.003 (3)0.005 (3)0.002 (3)
C15A0.020 (6)0.042 (5)0.028 (4)0.002 (4)0.006 (4)0.008 (4)
S1B0.0190 (12)0.0173 (10)0.0272 (10)0.0007 (8)0.0010 (8)0.0002 (8)
S2B0.0314 (14)0.0272 (12)0.0251 (11)0.0018 (9)0.0014 (9)0.0039 (8)
O1B0.033 (4)0.029 (3)0.013 (3)0.008 (3)0.005 (2)0.002 (2)
O2B0.030 (4)0.027 (3)0.026 (3)0.005 (3)0.002 (3)0.008 (2)
O3B0.012 (3)0.024 (3)0.039 (3)0.002 (2)0.004 (2)0.001 (2)
C1B0.019 (5)0.021 (4)0.025 (4)0.006 (3)0.008 (3)0.007 (3)
C2B0.023 (5)0.028 (5)0.022 (4)0.005 (4)0.001 (4)0.006 (3)
C3B0.019 (5)0.036 (5)0.030 (5)0.010 (4)0.002 (4)0.011 (4)
C4B0.035 (6)0.031 (5)0.032 (5)0.011 (4)0.018 (5)0.012 (4)
C5B0.046 (7)0.020 (5)0.028 (5)0.002 (4)0.012 (4)0.001 (4)
C6B0.030 (6)0.026 (5)0.020 (4)0.004 (4)0.006 (4)0.004 (3)
C7B0.020 (5)0.019 (4)0.021 (4)0.001 (3)0.004 (3)0.004 (3)
C8B0.015 (5)0.022 (4)0.020 (4)0.002 (3)0.005 (3)0.006 (3)
C9B0.009 (4)0.022 (4)0.023 (4)0.001 (3)0.003 (3)0.006 (3)
C10B0.007 (4)0.024 (4)0.017 (4)0.001 (3)0.000 (3)0.000 (3)
C11B0.014 (5)0.020 (4)0.023 (4)0.000 (3)0.001 (3)0.006 (3)
C12B0.020 (5)0.023 (4)0.016 (4)0.001 (3)0.004 (3)0.004 (3)
C13B0.020 (5)0.027 (5)0.035 (5)0.001 (4)0.003 (4)0.009 (4)
C14B0.035 (6)0.031 (5)0.021 (4)0.002 (4)0.006 (3)0.007 (3)
C15B0.022 (5)0.033 (5)0.031 (5)0.008 (4)0.003 (4)0.013 (4)
Geometric parameters (Å, º) top
S1A—O2A1.431 (5)S1B—O2B1.431 (6)
S1A—O3A1.443 (6)S1B—O3B1.443 (6)
S1A—C10A1.766 (8)S1B—C10B1.769 (8)
S1A—C13A1.791 (7)S1B—C13B1.824 (9)
S2A—C14A1.824 (7)S2B—C15B1.825 (10)
S2A—C15A1.839 (10)S2B—C14B1.832 (8)
O1A—C7A1.374 (10)O1B—C7B1.375 (10)
O1A—C1A1.404 (10)O1B—C1B1.406 (10)
C1A—C2A1.376 (13)C1B—C6B1.371 (13)
C1A—C6A1.383 (12)C1B—C2B1.386 (13)
C2A—C3A1.395 (13)C2B—C3B1.390 (13)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.366 (15)C3B—C4B1.372 (15)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.409 (16)C4B—C5B1.373 (15)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.384 (13)C5B—C6B1.414 (13)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
C7A—C12A1.382 (12)C7B—C8B1.392 (12)
C7A—C8A1.386 (12)C7B—C12B1.407 (12)
C8A—C9A1.393 (11)C8B—C9B1.380 (12)
C8A—H8A0.9500C8B—H8B0.9500
C9A—C10A1.400 (12)C9B—C10B1.393 (11)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.399 (11)C10B—C11B1.376 (11)
C11A—C12A1.392 (12)C11B—C12B1.370 (12)
C11A—H11A0.9500C11B—H11B0.9500
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.528 (10)C13B—C14B1.477 (12)
C13A—H13A0.9900C13B—H13C0.9900
C13A—H13B0.9900C13B—H13D0.9900
C14A—C15A1.480 (12)C14B—C15B1.475 (11)
C14A—H14A1.0000C14B—H14B1.0000
C15A—H15A0.9900C15B—H15C0.9900
C15A—H15B0.9900C15B—H15D0.9900
O2A—S1A—O3A119.4 (3)O2B—S1B—O3B118.4 (4)
O2A—S1A—C10A108.0 (3)O2B—S1B—C10B109.0 (4)
O3A—S1A—C10A107.3 (4)O3B—S1B—C10B107.8 (4)
O2A—S1A—C13A107.0 (4)O2B—S1B—C13B110.5 (4)
O3A—S1A—C13A108.3 (4)O3B—S1B—C13B108.5 (4)
C10A—S1A—C13A106.1 (4)C10B—S1B—C13B101.2 (4)
C14A—S2A—C15A47.7 (4)C15B—S2B—C14B47.6 (4)
C7A—O1A—C1A118.5 (6)C7B—O1B—C1B118.1 (6)
C2A—C1A—C6A121.8 (8)C6B—C1B—C2B122.3 (8)
C2A—C1A—O1A119.4 (7)C6B—C1B—O1B120.3 (8)
C6A—C1A—O1A118.6 (8)C2B—C1B—O1B117.2 (7)
C1A—C2A—C3A119.6 (8)C1B—C2B—C3B117.7 (8)
C1A—C2A—H2A120.2C1B—C2B—H2B121.2
C3A—C2A—H2A120.2C3B—C2B—H2B121.2
C4A—C3A—C2A120.0 (10)C4B—C3B—C2B121.5 (10)
C4A—C3A—H3A120.0C4B—C3B—H3B119.2
C2A—C3A—H3A120.0C2B—C3B—H3B119.2
C3A—C4A—C5A119.7 (8)C3B—C4B—C5B120.2 (9)
C3A—C4A—H4A120.1C3B—C4B—H4B119.9
C5A—C4A—H4A120.1C5B—C4B—H4B119.9
C6A—C5A—C4A120.7 (9)C4B—C5B—C6B119.7 (9)
C6A—C5A—H5A119.7C4B—C5B—H5B120.1
C4A—C5A—H5A119.7C6B—C5B—H5B120.1
C1A—C6A—C5A118.2 (9)C1B—C6B—C5B118.6 (9)
C1A—C6A—H6A120.9C1B—C6B—H6B120.7
C5A—C6A—H6A120.9C5B—C6B—H6B120.7
O1A—C7A—C12A115.7 (7)O1B—C7B—C8B123.5 (8)
O1A—C7A—C8A123.3 (7)O1B—C7B—C12B115.4 (7)
C12A—C7A—C8A121.0 (7)C8B—C7B—C12B121.0 (8)
C7A—C8A—C9A120.0 (8)C9B—C8B—C7B119.5 (8)
C7A—C8A—H8A120.0C9B—C8B—H8B120.2
C9A—C8A—H8A120.0C7B—C8B—H8B120.2
C8A—C9A—C10A118.8 (7)C8B—C9B—C10B118.9 (7)
C8A—C9A—H9A120.6C8B—C9B—H9B120.5
C10A—C9A—H9A120.6C10B—C9B—H9B120.5
C11A—C10A—C9A121.1 (7)C11B—C10B—C9B121.5 (8)
C11A—C10A—S1A119.4 (6)C11B—C10B—S1B119.3 (6)
C9A—C10A—S1A119.4 (6)C9B—C10B—S1B119.0 (6)
C12A—C11A—C10A118.9 (8)C12B—C11B—C10B120.4 (8)
C12A—C11A—H11A120.6C12B—C11B—H11B119.8
C10A—C11A—H11A120.6C10B—C11B—H11B119.8
C7A—C12A—C11A120.1 (7)C11B—C12B—C7B118.6 (7)
C7A—C12A—H12A119.9C11B—C12B—H12B120.7
C11A—C12A—H12A119.9C7B—C12B—H12B120.7
C14A—C13A—S1A110.8 (5)C14B—C13B—S1B113.0 (6)
C14A—C13A—H13A109.5C14B—C13B—H13C109.0
S1A—C13A—H13A109.5S1B—C13B—H13C109.0
C14A—C13A—H13B109.5C14B—C13B—H13D109.0
S1A—C13A—H13B109.5S1B—C13B—H13D109.0
H13A—C13A—H13B108.1H13C—C13B—H13D107.8
C15A—C14A—C13A117.8 (7)C15B—C14B—C13B119.4 (8)
C15A—C14A—S2A66.7 (5)C15B—C14B—S2B66.0 (5)
C13A—C14A—S2A116.2 (5)C13B—C14B—S2B115.4 (6)
C15A—C14A—H14A115.7C15B—C14B—H14B115.6
C13A—C14A—H14A115.7C13B—C14B—H14B115.6
S2A—C14A—H14A115.7S2B—C14B—H14B115.6
C14A—C15A—S2A65.7 (5)C14B—C15B—S2B66.5 (5)
C14A—C15A—H15A117.2C14B—C15B—H15C117.1
S2A—C15A—H15A117.2S2B—C15B—H15C117.1
C14A—C15A—H15B117.2C14B—C15B—H15D117.1
S2A—C15A—H15B117.2S2B—C15B—H15D117.1
H15A—C15A—H15B114.2H15C—C15B—H15D114.1
C7A—O1A—C1A—C2A111.4 (8)C7B—O1B—C1B—C6B68.2 (10)
C7A—O1A—C1A—C6A73.3 (10)C7B—O1B—C1B—C2B116.9 (8)
C6A—C1A—C2A—C3A1.0 (11)C6B—C1B—C2B—C3B0.4 (11)
O1A—C1A—C2A—C3A174.1 (7)O1B—C1B—C2B—C3B175.2 (7)
C1A—C2A—C3A—C4A0.1 (12)C1B—C2B—C3B—C4B0.8 (12)
C2A—C3A—C4A—C5A0.8 (13)C2B—C3B—C4B—C5B1.1 (13)
C3A—C4A—C5A—C6A0.9 (13)C3B—C4B—C5B—C6B1.0 (13)
C2A—C1A—C6A—C5A0.8 (11)C2B—C1B—C6B—C5B0.4 (12)
O1A—C1A—C6A—C5A174.3 (7)O1B—C1B—C6B—C5B175.0 (7)
C4A—C5A—C6A—C1A0.1 (12)C4B—C5B—C6B—C1B0.7 (12)
C1A—O1A—C7A—C12A161.5 (8)C1B—O1B—C7B—C8B21.0 (12)
C1A—O1A—C7A—C8A18.8 (12)C1B—O1B—C7B—C12B162.3 (8)
O1A—C7A—C8A—C9A179.0 (7)O1B—C7B—C8B—C9B175.9 (7)
C12A—C7A—C8A—C9A0.7 (12)C12B—C7B—C8B—C9B0.6 (13)
C7A—C8A—C9A—C10A1.2 (12)C7B—C8B—C9B—C10B1.9 (12)
C8A—C9A—C10A—C11A1.7 (12)C8B—C9B—C10B—C11B1.7 (12)
C8A—C9A—C10A—S1A176.8 (6)C8B—C9B—C10B—S1B177.0 (6)
O2A—S1A—C10A—C11A153.4 (6)O2B—S1B—C10B—C11B155.2 (7)
O3A—S1A—C10A—C11A23.5 (7)O3B—S1B—C10B—C11B25.5 (8)
C13A—S1A—C10A—C11A92.1 (7)C13B—S1B—C10B—C11B88.4 (7)
O2A—S1A—C10A—C9A25.1 (8)O2B—S1B—C10B—C9B29.4 (8)
O3A—S1A—C10A—C9A155.1 (6)O3B—S1B—C10B—C9B159.1 (6)
C13A—S1A—C10A—C9A89.3 (7)C13B—S1B—C10B—C9B87.0 (7)
C9A—C10A—C11A—C12A1.6 (12)C9B—C10B—C11B—C12B0.2 (13)
S1A—C10A—C11A—C12A176.9 (6)S1B—C10B—C11B—C12B175.5 (6)
O1A—C7A—C12A—C11A179.1 (7)C10B—C11B—C12B—C7B1.0 (12)
C8A—C7A—C12A—C11A0.6 (13)O1B—C7B—C12B—C11B177.6 (7)
C10A—C11A—C12A—C7A1.0 (12)C8B—C7B—C12B—C11B0.8 (13)
O2A—S1A—C13A—C14A178.0 (5)O2B—S1B—C13B—C14B99.3 (7)
O3A—S1A—C13A—C14A52.0 (6)O3B—S1B—C13B—C14B32.0 (8)
C10A—S1A—C13A—C14A62.9 (6)C10B—S1B—C13B—C14B145.3 (6)
S1A—C13A—C14A—C15A83.9 (7)S1B—C13B—C14B—C15B76.6 (9)
S1A—C13A—C14A—S2A160.1 (4)S1B—C13B—C14B—S2B152.1 (5)
C15A—S2A—C14A—C13A110.8 (8)C15B—S2B—C14B—C13B112.6 (9)
C13A—C14A—C15A—S2A108.4 (6)C13B—C14B—C15B—S2B106.7 (8)

Experimental details

(R-II)(S-III)
Crystal data
Chemical formulaC15H14O3S2C15H14O3S2
Mr306.38306.38
Crystal system, space groupMonoclinic, P21Monoclinic, P21
Temperature (K)100100
a, b, c (Å)5.3891 (3), 28.3231 (13), 9.2503 (4)5.3887 (3), 28.3506 (12), 9.2463 (4)
β (°) 95.434 (3) 95.463 (3)
V3)1405.58 (12)1406.17 (12)
Z44
Radiation typeCu KαCu Kα
µ (mm1)3.483.47
Crystal size (mm)0.23 × 0.01 × 0.010.22 × 0.07 × 0.01
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Bruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Multi-scan
(TWINABS; Sheldrick, 2012)
Tmin, Tmax0.50, 0.970.789, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
11717, 4353, 3926 25587, 4473, 3968
Rint0.0350.053
(sin θ/λ)max1)0.6070.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.097, 1.07 0.054, 0.143, 1.02
No. of reflections43534473
No. of parameters361361
No. of restraints11
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.230.66, 0.44
Absolute structureFlack x parameter determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).Flack x parameter determined using 1669 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter0.055 (9)0.02 (2)

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2014), SAINT (Bruker, 2007) and XPREP (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2014), CrystalMaker (Palmer, 2008), Mercury (Macrae et al., 2008), pyMOL (Schrödinger, 2011) and POVRay (Cason, 2003), XCIF (Sheldrick, 2008), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).

Selected torsion angles (º) for (R-II) top
C1A—O1A—C7A—C8A20.5 (7)C1B—O1B—C7B—C8B20.4 (7)
C10A—S1A—C13A—C14A62.8 (4)C10B—S1B—C13B—C14B146.2 (4)
Selected torsion angles (º) for (S-III) top
C1A—O1A—C7A—C8A18.8 (12)C1B—O1B—C7B—C8B21.0 (12)
C10A—S1A—C13A—C14A62.9 (6)C10B—S1B—C13B—C14B145.3 (6)
Thiirane sulfur to phenyl ring centroid contacts (Å) top
(R)-(II)(S)-(III)
S2A···CgB3.571i3.576ii
S2B···CgA3.543ii3.436i
CgA/B denotes the centroid of the C7–C12 phenyl ring of molecule A or B.

Symmetry codes: (i) 1 + x, y, z; (ii) 1 - x, y, z.
 

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