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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3198.
Published online 2009 November 25. doi:  10.1107/S1600536809049423
PMCID: PMC2971820

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

Abstract

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 [triangle]). d-p-hydroxy­phenyl­glycine is useful as a side chain in semi-synthetic penicillins or cephalosporins, see: Crast (1970 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3198-scheme1.jpg

Experimental

Crystal data

  • C17H20O4S2
  • M r = 352.45
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3198-efi1.jpg
  • 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 [triangle]) T min = 0.940, T max = 0.951
  • 45855 measured reflections
  • 6253 independent reflections
  • 5060 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 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 [triangle]); cell refinement: CrystalClear data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049423/fl2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049423/fl2264Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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..

Experimental

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

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).

Figures

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.

Crystal data

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

Rigaku Saturn CCD area-detector diffractometer6253 independent reflections
Radiation source: rotating anode5060 reflections with I > 2σ(I)
confocalRint = 0.052
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.1°
ω and [var phi] scansh = −19→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −22→22
Tmin = 0.940, Tmax = 0.951l = −26→26
45855 measured reflections

Refinement

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) = 0.155w = 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)

Special details

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)

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)
H8A0.3753−0.00130.73960.118*
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)
H180.7416−0.05300.49090.088*
C190.6381 (2)−0.0121 (2)0.52199 (19)0.0934 (12)
H190.6089−0.01800.48650.112*
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)
H240.8581−0.07480.54160.068*
C250.8621 (2)−0.10406 (19)0.63070 (16)0.0807 (10)
H25A0.8535−0.08230.66920.121*
H25B0.9166−0.12010.62820.121*
H25C0.8262−0.14270.62640.121*
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)

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, °)

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—C3−0.1 (7)C23—C18—C19—C201.1 (6)
C1—C2—C3—C4−0.3 (7)C18—C19—C20—C21−0.9 (7)
C2—C3—C4—C50.6 (7)C19—C20—C21—C22−0.3 (6)
C3—C4—C5—C6−0.5 (6)C20—C21—C22—C231.2 (5)
C4—C5—C6—C10.1 (5)C19—C18—C23—C22−0.2 (5)
C4—C5—C6—C7−178.6 (3)C19—C18—C23—C24178.3 (3)
C2—C1—C6—C50.2 (5)C21—C22—C23—C18−1.0 (5)
C2—C1—C6—C7178.9 (3)C21—C22—C23—C24−179.4 (3)
C5—C6—C7—C8132.9 (3)C18—C23—C24—C25−123.5 (3)
C1—C6—C7—C8−45.7 (4)C22—C23—C24—C2554.9 (4)
C5—C6—C7—S1−105.8 (3)C18—C23—C24—S3114.0 (3)
C1—C6—C7—S175.5 (3)C22—C23—C24—S3−67.6 (3)
O1—S1—C7—C6174.3 (2)O5—S3—C24—C23−172.48 (19)
O2—S1—C7—C6−55.4 (2)O6—S3—C24—C2357.0 (2)
C9—S1—C7—C657.4 (2)C26—S3—C24—C23−57.9 (2)
O1—S1—C7—C8−59.3 (2)O5—S3—C24—C2561.2 (2)
O2—S1—C7—C871.1 (2)O6—S3—C24—C25−69.4 (2)
C9—S1—C7—C8−176.2 (2)C26—S3—C24—C25175.8 (2)
O3—S2—C9—S1−67.0 (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—S3−77.6 (2)
O1—S1—C9—S2−41.5 (2)O5—S3—C26—S4−69.9 (2)
O2—S1—C9—S2−169.10 (16)O6—S3—C26—S458.95 (19)
C7—S1—C9—S275.01 (19)C24—S3—C26—S4175.96 (16)
O3—S2—C10—C12−67.9 (3)O7—S4—C27—C29−175.6 (2)
O4—S2—C10—C12161.6 (2)O8—S4—C27—C2954.3 (3)
C9—S2—C10—C1246.8 (3)C26—S4—C27—C29−59.1 (3)
O3—S2—C10—C1159.5 (3)O7—S4—C27—C2857.9 (3)
O4—S2—C10—C11−71.0 (3)O8—S4—C27—C28−72.2 (3)
C9—S2—C10—C11174.2 (3)C26—S4—C27—C28174.4 (3)
C11—C10—C12—C17−54.8 (4)C28—C27—C29—C30−134.8 (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—C13−110.4 (3)S4—C27—C29—C34−77.8 (4)
C17—C12—C13—C14−0.2 (5)C34—C29—C30—C31−1.0 (5)
C10—C12—C13—C14178.5 (3)C27—C29—C30—C31178.2 (3)
C12—C13—C14—C15−1.1 (7)C29—C30—C31—C321.0 (6)
C13—C14—C15—C162.5 (8)C30—C31—C32—C330.4 (7)
C14—C15—C16—C17−2.8 (9)C31—C32—C33—C34−1.8 (6)
C15—C16—C17—C121.5 (7)C32—C33—C34—C291.7 (6)
C13—C12—C17—C160.0 (5)C30—C29—C34—C33−0.3 (5)
C10—C12—C17—C16−178.6 (4)C27—C29—C34—C33−179.5 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2264).

References

  • Crast, L. B. Jr (1970). US Patent 3489750.
  • Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yoshioka, R., Tohyama, M., Yamada, S., Ohtsuki, O. & Chibata, I. (1987). Bull. Chem. Soc. Jpn, 60, 4321–4323.

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