organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-Phenyl-1-[(1-phenyl­ethyl)sulfonyl­methyl­sulfon­yl]ethane

aCollege of Chemical Engineering, Hebei University of Technology, Tianjin 300130, People's Republic of China, bCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China, and cGraduate School, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China
*Correspondence e-mail: fxsun001@163.com

(Received 24 August 2009; accepted 19 November 2009; online 25 November 2009)

There are two mol­ecules in the asymmetric unit of the title compound, C17H20O4S2. There are slight differences in the twist of the two rings relative to the S–C–S chain [dihedral angles of 48.41 (18) and 87.58 (16)° in the first mol­ecule and 45.98 (18) and 87.02 (18)° in the second] and the difference in the C—S—C—S torsion angles [176.68 (17) and −77.6 (2)° for the two independent mol­ecules].

Related literature

The title compound is a by-product from the synthesis of 1-phenyl­ethanesulfonic acid. 1-Phenyl-ethanesulfonic acid is a favorable resolving agent for the diastereomeric resolution of DL-p-hydroxy­phenyl­glycine, see: Yoshioka, et al. (1987[Yoshioka, R., Tohyama, M., Yamada, S., Ohtsuki, O. & Chibata, I. (1987). Bull. Chem. Soc. Jpn, 60, 4321-4323.]). D-p-hydroxy­phenyl­glycine is useful as a side chain in semi-synthetic penicillins or cephalosporins, see: Crast (1970[Crast, L. B. Jr (1970). US Patent 3489750.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20O4S2

  • Mr = 352.45

  • Orthorhombic, P b c a

  • a = 16.662 (3) Å

  • b = 19.270 (4) Å

  • c = 22.094 (4) Å

  • V = 7094 (2) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 293 K

  • 0.20 × 0.18 × 0.16 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.940, Tmax = 0.951

  • 45855 measured reflections

  • 6253 independent reflections

  • 5060 reflections with I > 2σ(I)

  • Rint = 0.052

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.155

  • S = 1.11

  • 6253 reflections

  • 420 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

It is well known that D-p-hydroxyphenylglycine is useful as a side chain of semisynthetic penicillins or cephalosporins (Crast, 1970). 1-Phenyl-ethanesulfonic acid is a favorable resolving agent for the diastereomeric resolution of DL-p-hydroxyphenylglycine ( Yoshioka, et al.,1987). The title compound (Fig. 1) is a byproduct from the synthesis of 1-phenyl- ethanesulfonic acid. The compound crystallized with two molecules per asymmetric unit. The formula is symmetric about the central carbon but there is no physical symmetry relating the two halves of the molecule. The dihedral angle between the two aromatic rings is essentially the same in each molecule. The crystallographic symmetry was lost due to the small differences in the twist of the two rings related to the CSCSC chain and also the difference in the two CSCS torsion angles in the chain itself (176.68 (17) and -77.6 (2) for the two independent molecules). The dihedral angle between the C10-C12-C13-C14-C15-C16-C17 plane and the plane formed by atoms S2-C9-S1 is 87.58 (16), while the dihedral angle between the C1-C2-C3-C4-C5-C6-C7 plane and the plane formed by atoms S2-C9-S1 is 48.41 (18). The dihedral angle between C27-C29-C30-C31-C32-C33-C34 plane and the plane formed by atoms S4-C26-S3 is 45.98 (18), while the dihedral angle between C18-C19-C20-C21-C22-C23-C24 plane and the plane formed by atoms S4-C26-S3 is 87.02 (18). C10 and C7 are displaced from the plane formed by atoms S2-C9-S1 by 0.102 (1) Å and 1.668 (1) Å respectively while in the second molecule, C27 and C24 are displaced from the plane formed by atoms S4-C26-S3 by 1.695 (1) Å and 0.123 (1) Å respectively..

Related literature top

The title compound is a by-product from the synthesis of 1-phenylethanesulfonic acid. 1-Phenyl-ethanesulfonic acid is a favorable resolving agent for the diastereomeric resolution of DL-p-hydroxyphenylglycine, see: Yoshioka, et al. (1987). D-p-hydroxyphenylglycine is useful as a side chain in semi-synthetic penicillins or cephalosporins, see: Crast (1970);

Experimental top

The title compound was found by chance during the synthesis of 1-phenyl- ethanesulfonic acid. In order to clarify the structure, we prepared the compound as following. 1-Phenyl-ethanethiol (10 g), paraformaldehyde(1.5 g) and water(4 mL) were placed in a 50 mL three-necked flask.The mixture was cooled to 283 K.To this suspension, hydrochloric acid (30%,10 g)was added at 283 K. After the addition was completed, the solution was stirred until all the thiol had reacted (according to TLC, 7 h). The solution was then extracted with petroleum ether(80 mL). The combined organic layers was dried over anhydrous magnesium sulfate, and concentrated in vacuo to yield a brown liquid (8.9 g). Hydrogen peroxide(30%, 28.0 g) was added to the solution of the brown liquid (8.9 g) and acetic acid(11.1 g) at 283 K. The solution was stirred at 283 K for 4 h to obtain the title compound. Ethyl acetate was used to extract and light yellow block crystals were obtained by slow evaporation of the solution.

Refinement top

H atoms on C atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H = 0.93–0.98 A ° and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title compound (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
1-Phenyl-1-[(1-phenylethyl)sulfonylmethylsulfonyl]ethane top
Crystal data top
C17H20O4S2Dx = 1.320 Mg m3
Mr = 352.45Melting point = 443.0–442.0 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 16.662 (3) ÅCell parameters from 12971 reflections
b = 19.270 (4) Åθ = 2.1–27.1°
c = 22.094 (4) ŵ = 0.32 mm1
V = 7094 (2) Å3T = 293 K
Z = 16Block, light yellow
F(000) = 29760.20 × 0.18 × 0.16 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
6253 independent reflections
Radiation source: rotating anode5060 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.052
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.1°
ω and ϕ scansh = 1918
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 2222
Tmin = 0.940, Tmax = 0.951l = 2626
45855 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)] = 0.058H-atom parameters constrained
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0766P)2 + 2.0257P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.002
6253 reflectionsΔρmax = 0.26 e Å3
420 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0035 (4)
Crystal data top
C17H20O4S2V = 7094 (2) Å3
Mr = 352.45Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 16.662 (3) ŵ = 0.32 mm1
b = 19.270 (4) ÅT = 293 K
c = 22.094 (4) Å0.20 × 0.18 × 0.16 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
6253 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
5060 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 0.951Rint = 0.052
45855 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.11Δρmax = 0.26 e Å3
6253 reflectionsΔρmin = 0.31 e Å3
420 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
S10.42601 (4)0.14356 (4)0.65021 (3)0.0548 (2)
S20.43044 (5)0.28236 (4)0.71302 (4)0.0658 (3)
S30.91769 (4)0.01716 (4)0.58927 (3)0.0549 (2)
S40.95474 (4)0.14921 (4)0.52137 (3)0.0595 (2)
O10.50929 (13)0.14107 (13)0.66501 (12)0.0812 (7)
O20.40126 (15)0.11824 (12)0.59213 (9)0.0745 (6)
O30.39709 (17)0.25589 (12)0.76788 (9)0.0842 (7)
O40.51574 (14)0.28768 (13)0.70805 (14)0.0964 (8)
O50.99638 (12)0.01180 (13)0.58338 (9)0.0716 (6)
O60.90029 (12)0.05709 (11)0.64260 (8)0.0626 (5)
O71.03467 (12)0.13461 (14)0.54114 (11)0.0783 (7)
O80.94424 (13)0.17500 (12)0.46090 (9)0.0680 (6)
C10.2418 (2)0.0672 (2)0.65607 (16)0.0807 (10)
H10.27060.03760.63090.097*
C20.1600 (3)0.0728 (3)0.6496 (2)0.1075 (15)
H20.13400.04690.62000.129*
C30.1172 (3)0.1152 (3)0.6855 (3)0.1045 (15)
H30.06190.11860.68050.125*
C40.1543 (2)0.1535 (2)0.7294 (2)0.0925 (12)
H40.12440.18250.75440.111*
C50.2375 (2)0.14881 (17)0.73661 (16)0.0702 (9)
H50.26310.17500.76620.084*
C60.28160 (17)0.10547 (14)0.69983 (12)0.0520 (7)
C70.37104 (17)0.09921 (14)0.70854 (12)0.0516 (7)
H70.38460.12100.74730.062*
C80.4035 (2)0.02521 (17)0.70958 (16)0.0789 (10)
H8A0.37530.00130.73960.118*
H8B0.45970.02610.71920.118*
H8C0.39600.00420.67060.118*
C90.39327 (17)0.23133 (14)0.65224 (12)0.0521 (7)
H9A0.40880.25340.61450.063*
H9B0.33510.23160.65410.063*
C100.3892 (2)0.36687 (17)0.69637 (16)0.0721 (9)
H100.41760.38480.66080.086*
C110.4098 (3)0.4138 (2)0.7492 (2)0.1226 (18)
H11A0.39170.46010.74070.184*
H11B0.46690.41410.75510.184*
H11C0.38400.39700.78510.184*
C120.30164 (19)0.36350 (15)0.68054 (15)0.0607 (8)
C130.2783 (2)0.3767 (2)0.62202 (18)0.0861 (11)
H130.31680.38850.59330.103*
C140.1986 (4)0.3726 (3)0.6053 (3)0.133 (2)
H140.18250.38220.56590.160*
C150.1430 (3)0.3535 (3)0.6495 (5)0.149 (3)
H150.08920.34850.63930.179*
C160.1663 (4)0.3425 (3)0.7057 (4)0.133 (2)
H160.12790.33180.73480.160*
C170.2446 (3)0.34631 (19)0.7224 (2)0.0892 (12)
H170.25940.33720.76220.107*
C180.7175 (2)0.03355 (18)0.52485 (15)0.0732 (9)
H180.74160.05300.49090.088*
C190.6381 (2)0.0121 (2)0.52199 (19)0.0934 (12)
H190.60890.01800.48650.112*
C200.6028 (2)0.0175 (2)0.5712 (2)0.0885 (11)
H200.54980.03240.56910.106*
C210.6446 (2)0.02539 (19)0.62323 (18)0.0764 (10)
H210.62020.04590.65660.092*
C220.72306 (19)0.00328 (17)0.62717 (14)0.0654 (8)
H220.75090.00810.66340.078*
C230.76090 (17)0.02629 (15)0.57724 (13)0.0536 (7)
C240.84634 (17)0.05169 (15)0.58011 (13)0.0570 (7)
H240.85810.07480.54160.068*
C250.8621 (2)0.10406 (19)0.63070 (16)0.0807 (10)
H25A0.85350.08230.66920.121*
H25B0.91660.12010.62820.121*
H25C0.82620.14270.62640.121*
C260.89830 (16)0.07083 (16)0.52489 (11)0.0534 (7)
H26A0.90920.04410.48860.064*
H26B0.84170.08250.52460.064*
C270.90765 (19)0.20848 (18)0.57385 (14)0.0671 (9)
H270.90890.18690.61400.081*
C280.9598 (3)0.2734 (3)0.5763 (2)0.1152 (16)
H28A0.96490.29250.53640.173*
H28B1.01200.26150.59160.173*
H28C0.93540.30700.60260.173*
C290.82128 (19)0.22151 (16)0.55802 (14)0.0611 (8)
C300.7612 (2)0.18929 (19)0.59077 (16)0.0771 (10)
H300.77480.15870.62170.093*
C310.6814 (2)0.2018 (2)0.5783 (2)0.0978 (13)
H310.64190.18020.60130.117*
C320.6603 (3)0.2448 (2)0.5333 (2)0.1013 (14)
H320.60630.25300.52560.122*
C330.7169 (3)0.2765 (2)0.4991 (2)0.0950 (13)
H330.70160.30520.46740.114*
C340.7977 (3)0.26611 (18)0.51137 (16)0.0802 (10)
H340.83640.28890.48840.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0510 (4)0.0588 (5)0.0545 (4)0.0056 (3)0.0035 (3)0.0007 (3)
S20.0669 (5)0.0562 (5)0.0742 (6)0.0133 (4)0.0189 (4)0.0005 (4)
S30.0473 (4)0.0713 (5)0.0460 (4)0.0054 (3)0.0008 (3)0.0045 (3)
S40.0458 (4)0.0806 (6)0.0522 (4)0.0071 (4)0.0008 (3)0.0088 (4)
O10.0452 (12)0.0881 (17)0.1104 (18)0.0122 (11)0.0044 (12)0.0007 (14)
O20.1017 (18)0.0751 (15)0.0467 (12)0.0035 (13)0.0062 (11)0.0084 (10)
O30.125 (2)0.0704 (15)0.0570 (13)0.0155 (14)0.0186 (13)0.0040 (11)
O40.0565 (14)0.0835 (17)0.149 (2)0.0166 (13)0.0312 (14)0.0037 (16)
O50.0459 (12)0.0994 (17)0.0696 (13)0.0169 (11)0.0043 (10)0.0080 (12)
O60.0709 (14)0.0757 (14)0.0413 (10)0.0014 (11)0.0021 (9)0.0015 (9)
O70.0431 (12)0.1102 (19)0.0816 (15)0.0108 (12)0.0066 (10)0.0171 (13)
O80.0707 (14)0.0814 (15)0.0518 (12)0.0013 (11)0.0071 (10)0.0163 (10)
C10.071 (2)0.091 (3)0.081 (2)0.0129 (19)0.0115 (18)0.009 (2)
C20.073 (3)0.129 (4)0.120 (4)0.028 (3)0.027 (3)0.003 (3)
C30.058 (2)0.115 (4)0.140 (4)0.012 (3)0.007 (3)0.032 (3)
C40.069 (2)0.090 (3)0.119 (3)0.001 (2)0.033 (2)0.012 (2)
C50.061 (2)0.069 (2)0.080 (2)0.0048 (16)0.0154 (17)0.0030 (17)
C60.0534 (16)0.0508 (16)0.0517 (16)0.0087 (13)0.0000 (13)0.0073 (12)
C70.0582 (17)0.0513 (16)0.0453 (15)0.0014 (13)0.0045 (12)0.0034 (12)
C80.101 (3)0.0556 (19)0.080 (2)0.0167 (18)0.0067 (19)0.0087 (16)
C90.0525 (16)0.0547 (16)0.0492 (15)0.0053 (13)0.0019 (12)0.0091 (12)
C100.073 (2)0.0572 (19)0.086 (2)0.0122 (17)0.0067 (18)0.0010 (16)
C110.143 (4)0.065 (2)0.160 (4)0.013 (3)0.052 (3)0.033 (3)
C120.0620 (19)0.0499 (16)0.070 (2)0.0009 (14)0.0113 (15)0.0139 (14)
C130.087 (3)0.092 (3)0.079 (3)0.019 (2)0.000 (2)0.015 (2)
C140.119 (4)0.134 (4)0.147 (5)0.058 (4)0.058 (4)0.071 (4)
C150.065 (3)0.116 (4)0.267 (9)0.003 (3)0.021 (5)0.110 (6)
C160.085 (4)0.085 (3)0.229 (7)0.012 (3)0.061 (4)0.036 (4)
C170.086 (3)0.073 (2)0.108 (3)0.008 (2)0.037 (2)0.010 (2)
C180.065 (2)0.084 (2)0.070 (2)0.0042 (18)0.0046 (16)0.0184 (17)
C190.069 (2)0.111 (3)0.100 (3)0.003 (2)0.023 (2)0.027 (2)
C200.053 (2)0.092 (3)0.121 (3)0.0045 (19)0.004 (2)0.018 (2)
C210.061 (2)0.078 (2)0.090 (3)0.0038 (18)0.0190 (19)0.0103 (19)
C220.066 (2)0.070 (2)0.0601 (18)0.0020 (16)0.0102 (15)0.0033 (15)
C230.0514 (16)0.0561 (17)0.0535 (16)0.0020 (13)0.0050 (13)0.0014 (13)
C240.0564 (18)0.0613 (18)0.0534 (16)0.0067 (14)0.0012 (13)0.0014 (13)
C250.090 (3)0.068 (2)0.084 (2)0.0091 (19)0.0015 (19)0.0184 (18)
C260.0425 (15)0.0736 (19)0.0442 (15)0.0020 (14)0.0010 (11)0.0033 (13)
C270.068 (2)0.082 (2)0.0521 (17)0.0144 (17)0.0001 (15)0.0049 (15)
C280.099 (3)0.120 (4)0.126 (4)0.050 (3)0.006 (3)0.042 (3)
C290.0656 (19)0.0579 (17)0.0597 (18)0.0021 (15)0.0042 (15)0.0043 (14)
C300.071 (2)0.070 (2)0.090 (2)0.0053 (18)0.0155 (18)0.0123 (18)
C310.070 (3)0.077 (3)0.146 (4)0.005 (2)0.023 (2)0.003 (3)
C320.081 (3)0.085 (3)0.138 (4)0.025 (2)0.011 (3)0.019 (3)
C330.117 (4)0.078 (3)0.091 (3)0.041 (3)0.015 (3)0.002 (2)
C340.106 (3)0.065 (2)0.069 (2)0.008 (2)0.014 (2)0.0018 (17)
Geometric parameters (Å, º) top
S1—O11.426 (2)C13—H130.9300
S1—O21.433 (2)C14—C151.396 (9)
S1—C91.778 (3)C14—H140.9300
S1—C71.797 (3)C15—C161.318 (9)
S2—O31.428 (2)C15—H150.9300
S2—O41.429 (2)C16—C171.358 (7)
S2—C91.776 (3)C16—H160.9300
S2—C101.805 (3)C17—H170.9300
S3—O51.431 (2)C18—C231.372 (4)
S3—O61.437 (2)C18—C191.388 (5)
S3—C261.788 (3)C18—H180.9300
S3—C241.793 (3)C19—C201.362 (5)
S4—O71.430 (2)C19—H190.9300
S4—O81.436 (2)C20—C211.352 (5)
S4—C261.781 (3)C20—H200.9300
S4—C271.807 (3)C21—C221.377 (4)
C1—C21.374 (5)C21—H210.9300
C1—C61.385 (4)C22—C231.392 (4)
C1—H10.9300C22—H220.9300
C2—C31.345 (6)C23—C241.507 (4)
C2—H20.9300C24—C251.529 (4)
C3—C41.366 (6)C24—H240.9800
C3—H30.9300C25—H25A0.9600
C4—C51.398 (5)C25—H25B0.9600
C4—H40.9300C25—H25C0.9600
C5—C61.377 (4)C26—H26A0.9700
C5—H50.9300C26—H26B0.9700
C6—C71.507 (4)C27—C291.502 (4)
C7—C81.526 (4)C27—C281.524 (5)
C7—H70.9800C27—H270.9800
C8—H8A0.9600C28—H28A0.9600
C8—H8B0.9600C28—H28B0.9600
C8—H8C0.9600C28—H28C0.9600
C9—H9A0.9700C29—C301.383 (4)
C9—H9B0.9700C29—C341.398 (5)
C10—C121.501 (4)C30—C311.379 (5)
C10—C111.517 (5)C30—H300.9300
C10—H100.9800C31—C321.341 (6)
C11—H11A0.9600C31—H310.9300
C11—H11B0.9600C32—C331.353 (6)
C11—H11C0.9600C32—H320.9300
C12—C171.367 (5)C33—C341.388 (5)
C12—C131.374 (5)C33—H330.9300
C13—C141.382 (6)C34—H340.9300
O1—S1—O2118.26 (15)C13—C14—C15117.8 (6)
O1—S1—C9108.95 (14)C13—C14—H14121.1
O2—S1—C9104.96 (13)C15—C14—H14121.1
O1—S1—C7108.39 (14)C16—C15—C14120.5 (6)
O2—S1—C7109.48 (14)C16—C15—H15119.8
C9—S1—C7106.14 (13)C14—C15—H15119.8
O3—S2—O4118.55 (16)C15—C16—C17122.0 (6)
O3—S2—C9107.97 (13)C15—C16—H16119.0
O4—S2—C9109.17 (16)C17—C16—H16119.0
O3—S2—C10110.31 (17)C16—C17—C12119.9 (5)
O4—S2—C10107.35 (16)C16—C17—H17120.1
C9—S2—C10102.27 (14)C12—C17—H17120.1
O5—S3—O6117.93 (13)C23—C18—C19120.7 (3)
O5—S3—C26108.59 (13)C23—C18—H18119.6
O6—S3—C26107.82 (13)C19—C18—H18119.6
O5—S3—C24107.99 (14)C20—C19—C18120.0 (3)
O6—S3—C24110.80 (13)C20—C19—H19120.0
C26—S3—C24102.61 (13)C18—C19—H19120.0
O7—S4—O8117.77 (13)C21—C20—C19120.2 (3)
O7—S4—C26108.16 (14)C21—C20—H20119.9
O8—S4—C26105.66 (13)C19—C20—H20119.9
O7—S4—C27109.44 (15)C20—C21—C22120.5 (3)
O8—S4—C27108.98 (15)C20—C21—H21119.7
C26—S4—C27106.18 (14)C22—C21—H21119.7
C2—C1—C6120.4 (4)C21—C22—C23120.4 (3)
C2—C1—H1119.8C21—C22—H22119.8
C6—C1—H1119.8C23—C22—H22119.8
C3—C2—C1120.8 (4)C18—C23—C22118.1 (3)
C3—C2—H2119.6C18—C23—C24120.0 (3)
C1—C2—H2119.6C22—C23—C24121.8 (3)
C2—C3—C4120.4 (4)C23—C24—C25114.1 (3)
C2—C3—H3119.8C23—C24—S3113.0 (2)
C4—C3—H3119.8C25—C24—S3107.0 (2)
C3—C4—C5119.7 (4)C23—C24—H24107.5
C3—C4—H4120.2C25—C24—H24107.5
C5—C4—H4120.2S3—C24—H24107.5
C6—C5—C4120.0 (3)C24—C25—H25A109.5
C6—C5—H5120.0C24—C25—H25B109.5
C4—C5—H5120.0H25A—C25—H25B109.5
C5—C6—C1118.6 (3)C24—C25—H25C109.5
C5—C6—C7120.0 (3)H25A—C25—H25C109.5
C1—C6—C7121.3 (3)H25B—C25—H25C109.5
C6—C7—C8115.3 (3)S4—C26—S3115.46 (15)
C6—C7—S1111.98 (18)S4—C26—H26A108.4
C8—C7—S1105.9 (2)S3—C26—H26A108.4
C6—C7—H7107.8S4—C26—H26B108.4
C8—C7—H7107.8S3—C26—H26B108.4
S1—C7—H7107.8H26A—C26—H26B107.5
C7—C8—H8A109.5C29—C27—C28114.7 (3)
C7—C8—H8B109.5C29—C27—S4111.9 (2)
H8A—C8—H8B109.5C28—C27—S4107.1 (2)
C7—C8—H8C109.5C29—C27—H27107.6
H8A—C8—H8C109.5C28—C27—H27107.6
H8B—C8—H8C109.5S4—C27—H27107.6
S2—C9—S1116.03 (15)C27—C28—H28A109.5
S2—C9—H9A108.3C27—C28—H28B109.5
S1—C9—H9A108.3H28A—C28—H28B109.5
S2—C9—H9B108.3C27—C28—H28C109.5
S1—C9—H9B108.3H28A—C28—H28C109.5
H9A—C9—H9B107.4H28B—C28—H28C109.5
C12—C10—C11115.2 (3)C30—C29—C34117.3 (3)
C12—C10—S2112.2 (2)C30—C29—C27119.8 (3)
C11—C10—S2107.2 (3)C34—C29—C27122.9 (3)
C12—C10—H10107.3C31—C30—C29121.0 (4)
C11—C10—H10107.3C31—C30—H30119.5
S2—C10—H10107.3C29—C30—H30119.5
C10—C11—H11A109.5C32—C31—C30120.6 (4)
C10—C11—H11B109.5C32—C31—H31119.7
H11A—C11—H11B109.5C30—C31—H31119.7
C10—C11—H11C109.5C31—C32—C33120.6 (4)
H11A—C11—H11C109.5C31—C32—H32119.7
H11B—C11—H11C109.5C33—C32—H32119.7
C17—C12—C13119.0 (4)C32—C33—C34120.2 (4)
C17—C12—C10121.9 (3)C32—C33—H33119.9
C13—C12—C10119.1 (3)C34—C33—H33119.9
C12—C13—C14120.9 (4)C33—C34—C29120.3 (4)
C12—C13—H13119.6C33—C34—H34119.9
C14—C13—H13119.6C29—C34—H34119.9
C6—C1—C2—C30.1 (7)C23—C18—C19—C201.1 (6)
C1—C2—C3—C40.3 (7)C18—C19—C20—C210.9 (7)
C2—C3—C4—C50.6 (7)C19—C20—C21—C220.3 (6)
C3—C4—C5—C60.5 (6)C20—C21—C22—C231.2 (5)
C4—C5—C6—C10.1 (5)C19—C18—C23—C220.2 (5)
C4—C5—C6—C7178.6 (3)C19—C18—C23—C24178.3 (3)
C2—C1—C6—C50.2 (5)C21—C22—C23—C181.0 (5)
C2—C1—C6—C7178.9 (3)C21—C22—C23—C24179.4 (3)
C5—C6—C7—C8132.9 (3)C18—C23—C24—C25123.5 (3)
C1—C6—C7—C845.7 (4)C22—C23—C24—C2554.9 (4)
C5—C6—C7—S1105.8 (3)C18—C23—C24—S3114.0 (3)
C1—C6—C7—S175.5 (3)C22—C23—C24—S367.6 (3)
O1—S1—C7—C6174.3 (2)O5—S3—C24—C23172.48 (19)
O2—S1—C7—C655.4 (2)O6—S3—C24—C2357.0 (2)
C9—S1—C7—C657.4 (2)C26—S3—C24—C2357.9 (2)
O1—S1—C7—C859.3 (2)O5—S3—C24—C2561.2 (2)
O2—S1—C7—C871.1 (2)O6—S3—C24—C2569.4 (2)
C9—S1—C7—C8176.2 (2)C26—S3—C24—C25175.8 (2)
O3—S2—C9—S167.0 (2)O7—S4—C26—S339.8 (2)
O4—S2—C9—S163.2 (2)O8—S4—C26—S3166.74 (15)
C10—S2—C9—S1176.68 (17)C27—S4—C26—S377.6 (2)
O1—S1—C9—S241.5 (2)O5—S3—C26—S469.9 (2)
O2—S1—C9—S2169.10 (16)O6—S3—C26—S458.95 (19)
C7—S1—C9—S275.01 (19)C24—S3—C26—S4175.96 (16)
O3—S2—C10—C1267.9 (3)O7—S4—C27—C29175.6 (2)
O4—S2—C10—C12161.6 (2)O8—S4—C27—C2954.3 (3)
C9—S2—C10—C1246.8 (3)C26—S4—C27—C2959.1 (3)
O3—S2—C10—C1159.5 (3)O7—S4—C27—C2857.9 (3)
O4—S2—C10—C1171.0 (3)O8—S4—C27—C2872.2 (3)
C9—S2—C10—C11174.2 (3)C26—S4—C27—C28174.4 (3)
C11—C10—C12—C1754.8 (4)C28—C27—C29—C30134.8 (3)
S2—C10—C12—C1768.2 (4)S4—C27—C29—C30103.0 (3)
C11—C10—C12—C13126.6 (4)C28—C27—C29—C3444.4 (4)
S2—C10—C12—C13110.4 (3)S4—C27—C29—C3477.8 (4)
C17—C12—C13—C140.2 (5)C34—C29—C30—C311.0 (5)
C10—C12—C13—C14178.5 (3)C27—C29—C30—C31178.2 (3)
C12—C13—C14—C151.1 (7)C29—C30—C31—C321.0 (6)
C13—C14—C15—C162.5 (8)C30—C31—C32—C330.4 (7)
C14—C15—C16—C172.8 (9)C31—C32—C33—C341.8 (6)
C15—C16—C17—C121.5 (7)C32—C33—C34—C291.7 (6)
C13—C12—C17—C160.0 (5)C30—C29—C34—C330.3 (5)
C10—C12—C17—C16178.6 (4)C27—C29—C34—C33179.5 (3)

Experimental details

Crystal data
Chemical formulaC17H20O4S2
Mr352.45
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)16.662 (3), 19.270 (4), 22.094 (4)
V3)7094 (2)
Z16
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.20 × 0.18 × 0.16
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.940, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections
45855, 6253, 5060
Rint0.052
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.155, 1.11
No. of reflections6253
No. of parameters420
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.31

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors gratefully acknowledge support from Nankai University and Hebei University of Science and Technology.

References

First citationCrast, L. B. Jr (1970). US Patent 3489750.  Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYoshioka, R., Tohyama, M., Yamada, S., Ohtsuki, O. & Chibata, I. (1987). Bull. Chem. Soc. Jpn, 60, 4321–4323.  CrossRef CAS Web of Science Google Scholar

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