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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o352.
Published online 2010 January 13. doi:  10.1107/S1600536810000991
PMCID: PMC2979862

(R)-2-(2-Methoxy­phen­yl)-2,5-dihydro­thio­phene-3-carbaldehyde

Abstract

In the title compound, C12H12O2S, the asymmetric unit contains two independent mol­ecules. The chiral C atoms of both mol­ecules were established to be in the R configuration. In both mol­ecules, the 2,5-dihydro­thio­phene rings adopt S-envelope conformations wherein the S atoms are displaced by 0.315 (5) and −0.249 (5) Å from the mean planes of the remaining ring atoms. In the crystal, the molecules are linked by weak C—H(...)O interactions.

Related literature

For background to the organocatalytic domino reaction, see: Enders et al. (2007 [triangle]); Yu & Wang (2008 [triangle]). For a related structure, see: Zhu et al. (2009 [triangle]).

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Object name is e-66-0o352-scheme1.jpg

Experimental

Crystal data

  • C12H12O2S
  • M r = 220.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o352-efi1.jpg
  • a = 6.8281 (6) Å
  • b = 7.7624 (9) Å
  • c = 11.8748 (12) Å
  • α = 71.733 (3)°
  • β = 79.051 (3)°
  • γ = 73.488 (3)°
  • V = 569.50 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.26 mm−1
  • T = 296 K
  • 0.46 × 0.42 × 0.38 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.886, T max = 0.905
  • 5623 measured reflections
  • 4243 independent reflections
  • 3098 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.116
  • S = 1.00
  • 4243 reflections
  • 274 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.31 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1657 Friedel pairs
  • Flack parameter: 0.02 (9)

Data collection: PROCESS-AUTO (Rigaku, 2006 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000991/pv2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000991/pv2254Isup2.hkl

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

Acknowledgments

The authors thank Professor Jian-Ming Gu of Zhejiang University.

supplementary crystallographic information

Comment

There has been growing interest in the study of domino or cascade reaction as it allows in principle the formation of multiple new bonds and stereocenters (Enders et al., 2007; Yu & Wang, 2008) in a one-pot system. Consequently, The title compound, (I), was synthesized as one of a series of thio-Michael-aldol products under investigation. In this paper, the absolute configuration and crystal structure of (I) has been presented.

The crystal structure of the title compoud (Fig. 1) contains two independent molecules (molecules A and B) in an asymmetric unit wherein C1A and C1B atoms have been established to exhibit R configuration. The main structure unit is a five-membered 2,5-dihydrothiophene ring with an aldehyde group and a 2-methoxyphenyl group. In molecule A, the atom S1A of the five-membered ring lies 0.315 (5)Å from the mean plane of C1A/C2A/C3A/C4A, the atoms O2A, C12A of the methoxy group lie -0.057 (5) and -0.213 (5) Å, respectively, from the benzene ring. The dihedral angel between the main planes of atoms CA1/C2A/C3A/C4A and the benzene ring is 75.45 (5)°. In molecule B, the atom S2B of the five-membered ring lies -0.249 (5)Å from the mean plane of C13B/C14B/C15B/C16B, the atoms O4B, C24B of the methoxy group lie 0.039 (5) and 0.001 (5) Å, respectively, from the benzene ring. The dihedral angel between the main plane formed by the atoms C13B/C14B/C15B/C16B and the benzene ring is 74.10 (5) °. The crystal structure is devoid of any classical hydrogen bonds. However, non-classical intermolecular interactions of the type C—H···O are present in the structure (Table 1).

The crystal structure of 2-morpholino-4-oxo-4,5-dihydrothiophene-3-carbonitrile which is closely related to the title compound has been reported recently (Zhu et al., 2009).

Experimental

The title compound was prepared by mixing a toluene (1 ml) solution of (E)-3-(2-methoxyphenyl)acrylaldehyde (1 mmol) and 1,4-dithiane-2,5-diol (0.6 mmol) in the presence of (S)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (0.2 mmol) as amine catalyst and 4-nitro-benzoic acid (0.1 mmol) as additive at room temperature with stirring. After completion of the reaction, the mixture was washed with water and extracted with ethyl acetate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: petroleum ether/diethyl ether). Single crystals were obtained by slow evaporation of an acetone solution.

Refinement

H atoms were placed in calculated position with C—H = 0.98, 0.97, 0.96 and 0.93 Å for sp, sp2, sp3 and aromatic H-atoms, respectively. All H atoms were included in the final cycles of refinement in riding mode, with Uiso(H)=1.2Ueq of the carrier atoms.

Figures

Fig. 1.
An ORTEP-3 view (Farrugia, 1997) of the two molecules A and B in the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 40% probability level.
Fig. 2.
The molecular packing of the title compound showing H-bridge interactions.

Crystal data

C12H12O2SZ = 2
Mr = 220.28F(000) = 232
Triclinic, P1Dx = 1.285 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8281 (6) ÅCell parameters from 4403 reflections
b = 7.7624 (9) Åθ = 3.1–27.4°
c = 11.8748 (12) ŵ = 0.26 mm1
α = 71.733 (3)°T = 296 K
β = 79.051 (3)°Chunk, yellow
γ = 73.488 (3)°0.46 × 0.42 × 0.38 mm
V = 569.50 (10) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer4243 independent reflections
Radiation source: rolling anode3098 reflections with I > 2σ(I)
graphiteRint = 0.031
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 3.1°
ω scansh = −7→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −10→10
Tmin = 0.886, Tmax = 0.905l = −14→15
5623 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039w = 1/[σ2(Fo2) + (0.0219P)2 + 0.3733P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.25 e Å3
4243 reflectionsΔρmin = −0.31 e Å3
274 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.053 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1657 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.02 (9)

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
S1B0.18231 (16)−0.06575 (15)0.81497 (10)0.0748 (4)
S1A0.48209 (17)1.01438 (17)0.33170 (10)0.0809 (4)
O2A0.9679 (4)1.0496 (4)0.2171 (2)0.0612 (7)
C11B0.5790 (6)0.0081 (5)0.9189 (3)0.0524 (9)
C6A0.8721 (5)0.7749 (5)0.3322 (3)0.0461 (8)
C11A1.0032 (5)0.8609 (5)0.2381 (3)0.0475 (8)
C1B0.3932 (5)0.0505 (5)0.7461 (3)0.0499 (8)
H1B0.5127−0.04230.72360.060*
C6B0.4530 (5)0.1295 (5)0.8313 (3)0.0470 (8)
O2B0.6306 (4)−0.1755 (4)0.9175 (3)0.0719 (8)
C1A0.7167 (5)0.8901 (5)0.4051 (3)0.0505 (8)
H1A0.77840.98210.41650.061*
C7A0.8916 (6)0.5850 (5)0.3545 (3)0.0570 (9)
H7A0.80340.52680.41450.068*
O1B0.6367 (5)0.2578 (6)0.5468 (3)0.0955 (11)
C9A1.1709 (7)0.5657 (7)0.2007 (4)0.0748 (13)
H9A1.27400.49440.15900.090*
C10A1.1518 (6)0.7556 (6)0.1729 (3)0.0617 (10)
H10A1.23800.81270.11090.074*
C8B0.4500 (7)0.3803 (7)0.9109 (4)0.0698 (12)
H8B0.40550.50600.90900.084*
O1A0.9507 (5)0.6890 (5)0.6125 (3)0.0903 (10)
C5A0.7736 (7)0.6832 (6)0.6196 (4)0.0682 (11)
H5A0.71840.61220.69080.082*
C9B0.5748 (7)0.2607 (7)0.9928 (4)0.0726 (12)
H9B0.61770.30581.04550.087*
C3B0.1198 (6)0.2121 (6)0.6214 (4)0.0707 (12)
H3B0.06110.29780.55500.085*
C2B0.3153 (5)0.1889 (5)0.6343 (3)0.0539 (9)
C10B0.6390 (6)0.0731 (6)0.9991 (3)0.0646 (11)
H10B0.7220−0.00871.05690.078*
C7B0.3878 (6)0.3165 (5)0.8297 (3)0.0584 (9)
H7B0.30200.39970.77380.070*
C2A0.6391 (6)0.7799 (5)0.5245 (3)0.0525 (9)
C3A0.4430 (6)0.7717 (6)0.5405 (4)0.0636 (11)
H3A0.38570.70420.61240.076*
C4B−0.0019 (7)0.0973 (8)0.7161 (4)0.0938 (17)
H4B1−0.06660.03120.68260.113*
H4B2−0.10760.17480.75850.113*
C8A1.0396 (7)0.4804 (6)0.2892 (4)0.0709 (12)
H8A1.05030.35300.30510.085*
C12A1.0829 (7)1.1464 (6)0.1151 (4)0.0725 (12)
H12A1.22581.10870.12700.109*
H12B1.03401.27870.10440.109*
H12C1.06611.11670.04540.109*
C5B0.4545 (8)0.2860 (6)0.5426 (4)0.0720 (12)
H5B0.39840.37570.47670.086*
C4A0.3209 (7)0.8746 (7)0.4393 (4)0.0794 (14)
H4A10.19320.95380.46470.095*
H4A20.28930.78860.40520.095*
C12B0.7650 (8)−0.3065 (7)1.0013 (5)0.0974 (18)
H12D0.8876−0.26440.99320.146*
H12E0.8005−0.42660.98610.146*
H12F0.6971−0.31621.08080.146*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1B0.0757 (7)0.0954 (8)0.0581 (6)−0.0439 (6)−0.0105 (5)−0.0051 (6)
S1A0.0595 (6)0.0968 (9)0.0570 (6)0.0082 (5)−0.0066 (5)−0.0044 (6)
O2A0.0662 (17)0.0593 (16)0.0527 (15)−0.0238 (13)0.0090 (12)−0.0094 (13)
C11B0.052 (2)0.059 (2)0.0457 (19)−0.0200 (17)−0.0097 (15)−0.0055 (16)
C6A0.0444 (18)0.0550 (19)0.0367 (16)−0.0105 (14)−0.0069 (13)−0.0094 (14)
C11A0.0433 (19)0.054 (2)0.0402 (17)−0.0074 (14)−0.0049 (13)−0.0092 (15)
C1B0.0415 (19)0.058 (2)0.0439 (18)−0.0088 (15)−0.0053 (14)−0.0082 (16)
C6B0.0435 (19)0.057 (2)0.0398 (17)−0.0143 (14)−0.0025 (13)−0.0124 (15)
O2B0.077 (2)0.0537 (16)0.082 (2)−0.0061 (13)−0.0380 (15)−0.0055 (14)
C1A0.0468 (19)0.055 (2)0.0415 (18)−0.0078 (15)0.0016 (14)−0.0100 (15)
C7A0.066 (2)0.056 (2)0.0419 (18)−0.0080 (17)−0.0076 (16)−0.0094 (16)
O1B0.081 (3)0.134 (3)0.072 (2)−0.059 (2)0.0003 (18)−0.006 (2)
C9A0.069 (3)0.084 (3)0.062 (3)0.010 (2)−0.003 (2)−0.034 (2)
C10A0.050 (2)0.083 (3)0.047 (2)−0.0103 (19)0.0017 (16)−0.021 (2)
C8B0.083 (3)0.067 (3)0.066 (3)−0.030 (2)0.010 (2)−0.026 (2)
O1A0.077 (2)0.115 (3)0.080 (2)−0.0127 (19)−0.0280 (18)−0.027 (2)
C5A0.074 (3)0.081 (3)0.045 (2)−0.016 (2)−0.0056 (19)−0.015 (2)
C9B0.080 (3)0.098 (4)0.057 (2)−0.046 (3)0.005 (2)−0.031 (2)
C3B0.057 (3)0.093 (3)0.048 (2)−0.001 (2)−0.0129 (18)−0.010 (2)
C2B0.052 (2)0.064 (2)0.0389 (18)−0.0054 (16)−0.0100 (15)−0.0095 (16)
C10B0.060 (2)0.093 (3)0.047 (2)−0.031 (2)−0.0098 (17)−0.013 (2)
C7B0.066 (2)0.058 (2)0.049 (2)−0.0163 (18)−0.0009 (17)−0.0139 (17)
C2A0.056 (2)0.058 (2)0.0421 (19)−0.0149 (16)0.0033 (15)−0.0157 (16)
C3A0.061 (3)0.079 (3)0.050 (2)−0.026 (2)0.0066 (18)−0.017 (2)
C4B0.056 (3)0.150 (5)0.068 (3)−0.029 (3)−0.007 (2)−0.015 (3)
C8A0.088 (3)0.061 (2)0.052 (2)0.005 (2)−0.008 (2)−0.019 (2)
C12A0.076 (3)0.087 (3)0.054 (2)−0.042 (2)0.007 (2)−0.007 (2)
C5B0.090 (4)0.078 (3)0.044 (2)−0.027 (2)−0.007 (2)−0.0043 (19)
C4A0.061 (3)0.107 (4)0.076 (3)−0.022 (2)−0.011 (2)−0.030 (3)
C12B0.091 (4)0.074 (3)0.116 (4)−0.021 (3)−0.058 (3)0.017 (3)

Geometric parameters (Å, °)

S1B—C4B1.813 (5)C8B—C7B1.389 (6)
S1B—C1B1.839 (4)C8B—H8B0.9300
S1A—C4A1.816 (5)O1A—C5A1.209 (5)
S1A—C1A1.839 (4)C5A—C2A1.468 (6)
O2A—C11A1.363 (4)C5A—H5A0.9300
O2A—C12A1.433 (4)C9B—C10B1.379 (6)
C11B—O2B1.372 (5)C9B—H9B0.9300
C11B—C10B1.377 (5)C3B—C2B1.327 (5)
C11B—C6B1.405 (5)C3B—C4B1.478 (6)
C6A—C7A1.385 (5)C3B—H3B0.9300
C6A—C11A1.410 (4)C2B—C5B1.469 (6)
C6A—C1A1.507 (5)C10B—H10B0.9300
C11A—C10A1.387 (5)C7B—H7B0.9300
C1B—C2B1.500 (4)C2A—C3A1.333 (5)
C1B—C6B1.502 (5)C3A—C4A1.476 (6)
C1B—H1B0.9800C3A—H3A0.9300
C6B—C7B1.387 (5)C4B—H4B10.9700
O2B—C12B1.431 (5)C4B—H4B20.9700
C1A—C2A1.495 (4)C8A—H8A0.9300
C1A—H1A0.9800C12A—H12A0.9600
C7A—C8A1.383 (5)C12A—H12B0.9600
C7A—H7A0.9300C12A—H12C0.9600
O1B—C5B1.208 (5)C5B—H5B0.9300
C9A—C8A1.375 (6)C4A—H4A10.9700
C9A—C10A1.379 (6)C4A—H4A20.9700
C9A—H9A0.9300C12B—H12D0.9600
C10A—H10A0.9300C12B—H12E0.9600
C8B—C9B1.354 (7)C12B—H12F0.9600
C4B—S1B—C1B95.1 (2)C2B—C3B—H3B121.1
C4A—S1A—C1A94.67 (19)C4B—C3B—H3B121.1
C11A—O2A—C12A117.2 (3)C3B—C2B—C5B122.7 (4)
O2B—C11B—C10B124.6 (3)C3B—C2B—C1B116.8 (3)
O2B—C11B—C6B114.3 (3)C5B—C2B—C1B120.4 (3)
C10B—C11B—C6B121.1 (3)C11B—C10B—C9B119.3 (4)
C7A—C6A—C11A118.2 (3)C11B—C10B—H10B120.3
C7A—C6A—C1A122.1 (3)C9B—C10B—H10B120.3
C11A—C6A—C1A119.7 (3)C6B—C7B—C8B120.4 (4)
O2A—C11A—C10A124.6 (3)C6B—C7B—H7B119.8
O2A—C11A—C6A115.0 (3)C8B—C7B—H7B119.8
C10A—C11A—C6A120.4 (3)C3A—C2A—C5A121.4 (4)
C2B—C1B—C6B116.1 (3)C3A—C2A—C1A117.2 (4)
C2B—C1B—S1B103.9 (3)C5A—C2A—C1A121.5 (3)
C6B—C1B—S1B111.5 (2)C2A—C3A—C4A117.0 (4)
C2B—C1B—H1B108.4C2A—C3A—H3A121.5
C6B—C1B—H1B108.4C4A—C3A—H3A121.5
S1B—C1B—H1B108.4C3B—C4B—S1B105.0 (3)
C7B—C6B—C11B117.8 (3)C3B—C4B—H4B1110.7
C7B—C6B—C1B123.5 (3)S1B—C4B—H4B1110.7
C11B—C6B—C1B118.7 (3)C3B—C4B—H4B2110.7
C11B—O2B—C12B117.5 (4)S1B—C4B—H4B2110.7
C2A—C1A—C6A114.7 (3)H4B1—C4B—H4B2108.8
C2A—C1A—S1A103.7 (2)C9A—C8A—C7A119.6 (4)
C6A—C1A—S1A112.1 (3)C9A—C8A—H8A120.2
C2A—C1A—H1A108.7C7A—C8A—H8A120.2
C6A—C1A—H1A108.7O2A—C12A—H12A109.5
S1A—C1A—H1A108.7O2A—C12A—H12B109.5
C8A—C7A—C6A121.3 (4)H12A—C12A—H12B109.5
C8A—C7A—H7A119.4O2A—C12A—H12C109.5
C6A—C7A—H7A119.4H12A—C12A—H12C109.5
C8A—C9A—C10A120.9 (4)H12B—C12A—H12C109.5
C8A—C9A—H9A119.6O1B—C5B—C2B124.7 (4)
C10A—C9A—H9A119.6O1B—C5B—H5B117.7
C9A—C10A—C11A119.6 (4)C2B—C5B—H5B117.7
C9A—C10A—H10A120.2C3A—C4A—S1A105.1 (3)
C11A—C10A—H10A120.2C3A—C4A—H4A1110.7
C9B—C8B—C7B120.4 (4)S1A—C4A—H4A1110.7
C9B—C8B—H8B119.8C3A—C4A—H4A2110.7
C7B—C8B—H8B119.8S1A—C4A—H4A2110.7
O1A—C5A—C2A124.9 (4)H4A1—C4A—H4A2108.8
O1A—C5A—H5A117.6O2B—C12B—H12D109.5
C2A—C5A—H5A117.6O2B—C12B—H12E109.5
C8B—C9B—C10B120.8 (4)H12D—C12B—H12E109.5
C8B—C9B—H9B119.6O2B—C12B—H12F109.5
C10B—C9B—H9B119.6H12D—C12B—H12F109.5
C2B—C3B—C4B117.9 (4)H12E—C12B—H12F109.5
C12A—O2A—C11A—C10A4.8 (5)C7B—C8B—C9B—C10B−1.4 (7)
C12A—O2A—C11A—C6A−174.0 (3)C4B—C3B—C2B—C5B176.0 (4)
C7A—C6A—C11A—O2A176.6 (3)C4B—C3B—C2B—C1B−1.4 (6)
C1A—C6A—C11A—O2A−3.4 (4)C6B—C1B—C2B—C3B−113.9 (4)
C7A—C6A—C11A—C10A−2.2 (5)S1B—C1B—C2B—C3B8.8 (4)
C1A—C6A—C11A—C10A177.7 (3)C6B—C1B—C2B—C5B68.6 (5)
C4B—S1B—C1B—C2B−10.7 (3)S1B—C1B—C2B—C5B−168.6 (3)
C4B—S1B—C1B—C6B115.0 (3)O2B—C11B—C10B—C9B−179.0 (4)
O2B—C11B—C6B—C7B177.7 (3)C6B—C11B—C10B—C9B−0.3 (5)
C10B—C11B—C6B—C7B−1.2 (5)C8B—C9B—C10B—C11B1.6 (6)
O2B—C11B—C6B—C1B−1.3 (4)C11B—C6B—C7B—C8B1.3 (5)
C10B—C11B—C6B—C1B179.8 (3)C1B—C6B—C7B—C8B−179.7 (3)
C2B—C1B—C6B—C7B18.9 (5)C9B—C8B—C7B—C6B−0.1 (6)
S1B—C1B—C6B—C7B−99.7 (3)O1A—C5A—C2A—C3A−177.7 (5)
C2B—C1B—C6B—C11B−162.2 (3)O1A—C5A—C2A—C1A2.9 (7)
S1B—C1B—C6B—C11B79.2 (3)C6A—C1A—C2A—C3A−111.8 (4)
C10B—C11B—O2B—C12B−3.4 (6)S1A—C1A—C2A—C3A10.7 (4)
C6B—C11B—O2B—C12B177.7 (4)C6A—C1A—C2A—C5A67.6 (5)
C7A—C6A—C1A—C2A20.1 (5)S1A—C1A—C2A—C5A−169.9 (3)
C11A—C6A—C1A—C2A−159.9 (3)C5A—C2A—C3A—C4A179.7 (4)
C7A—C6A—C1A—S1A−97.8 (3)C1A—C2A—C3A—C4A−0.8 (6)
C11A—C6A—C1A—S1A82.3 (4)C2B—C3B—C4B—S1B−6.9 (6)
C4A—S1A—C1A—C2A−13.5 (3)C1B—S1B—C4B—C3B10.1 (4)
C4A—S1A—C1A—C6A110.7 (3)C10A—C9A—C8A—C7A−2.6 (7)
C11A—C6A—C7A—C8A2.1 (5)C6A—C7A—C8A—C9A0.3 (6)
C1A—C6A—C7A—C8A−177.9 (4)C3B—C2B—C5B—O1B−173.9 (5)
C8A—C9A—C10A—C11A2.5 (7)C1B—C2B—C5B—O1B3.4 (7)
O2A—C11A—C10A—C9A−178.7 (4)C2A—C3A—C4A—S1A−9.7 (5)
C6A—C11A—C10A—C9A0.0 (5)C1A—S1A—C4A—C3A13.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7A—H7A···O1B0.932.603.473 (4)157
C4B—H4B1···O1Bi0.972.693.202 (4)113

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2254).

References

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