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The thia­zolidine ring and the two pyrrolidine rings in the title compound, C20H21ClN2O2S2, adopt twisted conformations. In the crystal structure, the mol­ecules translated by a unit cell along the a axis are linked by inter­molecular C—H...O hydrogen bonds into a chain and inversion-related mol­ecules in adjacent chains are inter­connected via C—H...π inter­actions to form a double-stranded chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031072/fl2042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031072/fl2042Isup2.hkl
Contains datablock I

CCDC reference: 621307

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.030
  • wR factor = 0.080
  • Data-to-parameter ratio = 23.0

checkCIF/PLATON results

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Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-(4-Chlorophenyl)-5-(phenylsulfonyl)perhydro-1,3-thiazolo[3,4-a]pyrrolo[4,5-c]pyrrole top
Crystal data top
C20H21ClN2O2S2F(000) = 880
Mr = 420.96Dx = 1.446 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6984 reflections
a = 10.4869 (2) Åθ = 2.2–39.9°
b = 11.2536 (2) ŵ = 0.43 mm1
c = 16.4220 (2) ÅT = 100 K
β = 94.052 (1)°Block, colourless
V = 1933.20 (6) Å30.56 × 0.33 × 0.32 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5600 independent reflections
Radiation source: fine-focus sealed tube5046 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.2°
ω scansh = 1414
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1415
Tmin = 0.795, Tmax = 0.874l = 2321
25474 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0399P)2 + 0.9249P]
where P = (Fo2 + 2Fc2)/3
5600 reflections(Δ/σ)max = 0.001
244 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.33 e Å3
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
Cl10.68991 (3)0.11596 (3)0.560686 (19)0.02566 (8)
S10.60424 (3)0.63900 (3)0.323836 (19)0.01870 (7)
S20.01335 (2)0.44920 (2)0.309088 (16)0.01395 (7)
O10.09718 (8)0.39438 (8)0.24706 (5)0.01916 (17)
O20.06026 (8)0.53955 (8)0.36113 (5)0.01923 (17)
N10.10187 (9)0.50999 (9)0.26344 (6)0.01423 (18)
N20.40379 (9)0.49905 (8)0.29302 (6)0.01260 (17)
C10.16481 (11)0.44670 (10)0.19861 (7)0.0163 (2)
H1A0.10430.43110.15080.020*
H1B0.20240.37060.21880.020*
C20.26892 (11)0.53519 (10)0.17769 (7)0.0157 (2)
H20.23480.59730.13840.019*
C30.31052 (10)0.58864 (10)0.26132 (7)0.0142 (2)
H30.34980.66910.25670.017*
C40.19211 (11)0.59096 (10)0.31008 (7)0.0160 (2)
H4A0.21190.56150.36640.019*
H4B0.15660.67230.31250.019*
C50.39048 (11)0.47567 (11)0.14873 (7)0.0169 (2)
H5A0.37150.39440.12820.020*
H5B0.42620.52270.10480.020*
C60.48443 (11)0.47220 (10)0.22531 (7)0.0158 (2)
H60.52100.39050.23240.019*
C70.59493 (12)0.56467 (14)0.22537 (8)0.0264 (3)
H7A0.57750.62320.18090.032*
H7B0.67680.52430.21680.032*
C80.48545 (10)0.53583 (10)0.36318 (7)0.0142 (2)
H80.43250.58080.40110.017*
C90.54285 (10)0.42808 (10)0.40846 (7)0.0140 (2)
C100.45867 (11)0.34035 (10)0.43266 (7)0.0161 (2)
H100.36980.34740.41760.019*
C110.50330 (11)0.24317 (10)0.47833 (7)0.0172 (2)
H110.44580.18410.49480.021*
C120.63370 (11)0.23389 (10)0.49950 (7)0.0170 (2)
C130.71936 (11)0.31755 (11)0.47471 (7)0.0185 (2)
H130.80840.30860.48830.022*
C140.67308 (11)0.41545 (11)0.42932 (7)0.0172 (2)
H140.73110.47390.41260.021*
C150.05182 (10)0.33467 (10)0.37292 (7)0.0142 (2)
C160.08712 (11)0.35873 (11)0.45466 (7)0.0167 (2)
H160.07850.43670.47570.020*
C170.13526 (11)0.26737 (11)0.50528 (7)0.0189 (2)
H170.15930.28260.56120.023*
C180.14790 (12)0.15363 (11)0.47350 (7)0.0193 (2)
H180.18000.09120.50810.023*
C190.11388 (12)0.13048 (11)0.39150 (7)0.0188 (2)
H190.12360.05270.37030.023*
C200.06571 (11)0.22108 (10)0.34062 (7)0.0171 (2)
H200.04260.20590.28460.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02864 (16)0.02373 (15)0.02426 (15)0.00870 (12)0.00070 (12)0.00804 (11)
S10.01745 (13)0.01476 (13)0.02357 (15)0.00338 (10)0.00084 (10)0.00138 (10)
S20.01176 (12)0.01493 (13)0.01494 (13)0.00128 (9)0.00044 (9)0.00025 (9)
O10.0156 (4)0.0211 (4)0.0199 (4)0.0017 (3)0.0050 (3)0.0016 (3)
O20.0171 (4)0.0188 (4)0.0221 (4)0.0051 (3)0.0042 (3)0.0014 (3)
N10.0138 (4)0.0145 (4)0.0144 (4)0.0007 (3)0.0007 (3)0.0015 (3)
N20.0126 (4)0.0130 (4)0.0121 (4)0.0012 (3)0.0001 (3)0.0005 (3)
C10.0162 (5)0.0184 (5)0.0142 (5)0.0007 (4)0.0011 (4)0.0032 (4)
C20.0160 (5)0.0173 (5)0.0138 (5)0.0009 (4)0.0002 (4)0.0017 (4)
C30.0138 (5)0.0126 (5)0.0158 (5)0.0009 (4)0.0006 (4)0.0006 (4)
C40.0142 (5)0.0153 (5)0.0181 (5)0.0002 (4)0.0013 (4)0.0037 (4)
C50.0173 (5)0.0205 (5)0.0129 (5)0.0000 (4)0.0017 (4)0.0006 (4)
C60.0155 (5)0.0175 (5)0.0146 (5)0.0010 (4)0.0024 (4)0.0000 (4)
C70.0196 (6)0.0405 (8)0.0195 (6)0.0116 (5)0.0041 (5)0.0020 (5)
C80.0135 (5)0.0136 (5)0.0152 (5)0.0005 (4)0.0002 (4)0.0014 (4)
C90.0146 (5)0.0154 (5)0.0119 (5)0.0016 (4)0.0001 (4)0.0016 (4)
C100.0142 (5)0.0171 (5)0.0167 (5)0.0008 (4)0.0006 (4)0.0005 (4)
C110.0191 (5)0.0163 (5)0.0162 (5)0.0006 (4)0.0009 (4)0.0013 (4)
C120.0216 (5)0.0159 (5)0.0132 (5)0.0064 (4)0.0005 (4)0.0000 (4)
C130.0150 (5)0.0219 (6)0.0183 (5)0.0045 (4)0.0006 (4)0.0000 (4)
C140.0144 (5)0.0198 (5)0.0175 (5)0.0004 (4)0.0013 (4)0.0011 (4)
C150.0121 (5)0.0157 (5)0.0148 (5)0.0001 (4)0.0000 (4)0.0009 (4)
C160.0171 (5)0.0179 (5)0.0150 (5)0.0020 (4)0.0009 (4)0.0028 (4)
C170.0206 (5)0.0221 (6)0.0138 (5)0.0031 (4)0.0007 (4)0.0013 (4)
C180.0212 (6)0.0193 (5)0.0171 (5)0.0035 (4)0.0002 (4)0.0020 (4)
C190.0216 (5)0.0158 (5)0.0187 (5)0.0016 (4)0.0011 (4)0.0013 (4)
C200.0190 (5)0.0176 (5)0.0146 (5)0.0003 (4)0.0009 (4)0.0022 (4)
Geometric parameters (Å, º) top
Cl1—C121.7420 (12)C6—H61.00
S1—C71.8171 (14)C7—H7A0.99
S1—C81.8523 (11)C7—H7B0.99
S2—O11.4368 (9)C8—C91.5239 (15)
S2—O21.4373 (9)C8—H81.00
S2—N11.6180 (10)C9—C141.3916 (15)
S2—C151.7680 (12)C9—C101.4006 (16)
N1—C11.4750 (14)C10—C111.3885 (16)
N1—C41.4866 (14)C10—H100.95
N2—C81.4466 (14)C11—C121.3910 (16)
N2—C31.4739 (14)C11—H110.95
N2—C61.4751 (14)C12—C131.3823 (17)
C1—C21.5346 (16)C13—C141.3978 (16)
C1—H1A0.99C13—H130.95
C1—H1B0.99C14—H140.95
C2—C31.5342 (16)C15—C161.3936 (15)
C2—C51.5445 (16)C15—C201.3955 (16)
C2—H21.00C16—C171.3942 (16)
C3—C41.5246 (16)C16—H160.95
C3—H31.00C17—C181.3922 (17)
C4—H4A0.99C17—H170.95
C4—H4B0.99C18—C191.3931 (17)
C5—C61.5424 (16)C18—H180.95
C5—H5A0.99C19—C201.3904 (16)
C5—H5B0.99C19—H190.95
C6—C71.5574 (17)C20—H200.95
C7—S1—C891.53 (5)C6—C7—S1107.53 (8)
O1—S2—O2120.48 (5)C6—C7—H7A110.2
O1—S2—N1107.02 (5)S1—C7—H7A110.2
O2—S2—N1105.94 (5)C6—C7—H7B110.2
O1—S2—C15107.39 (5)S1—C7—H7B110.2
O2—S2—C15107.30 (5)H7A—C7—H7B108.5
N1—S2—C15108.23 (5)N2—C8—C9110.62 (9)
C1—N1—C4111.52 (9)N2—C8—S1106.05 (7)
C1—N1—S2121.14 (8)C9—C8—S1114.63 (8)
C4—N1—S2119.30 (8)N2—C8—H8108.5
C8—N2—C3115.23 (9)C9—C8—H8108.5
C8—N2—C6108.68 (8)S1—C8—H8108.5
C3—N2—C6105.98 (8)C14—C9—C10119.04 (10)
N1—C1—C2102.12 (9)C14—C9—C8123.25 (10)
N1—C1—H1A111.3C10—C9—C8117.66 (10)
C2—C1—H1A111.3C11—C10—C9120.88 (11)
N1—C1—H1B111.3C11—C10—H10119.6
C2—C1—H1B111.3C9—C10—H10119.6
H1A—C1—H1B109.2C10—C11—C12118.82 (11)
C3—C2—C1102.46 (9)C10—C11—H11120.6
C3—C2—C5104.89 (9)C12—C11—H11120.6
C1—C2—C5113.78 (10)C13—C12—C11121.54 (11)
C3—C2—H2111.7C13—C12—Cl1119.23 (9)
C1—C2—H2111.7C11—C12—Cl1119.21 (9)
C5—C2—H2111.7C12—C13—C14119.05 (11)
N2—C3—C4111.78 (9)C12—C13—H13120.5
N2—C3—C2100.82 (8)C14—C13—H13120.5
C4—C3—C2106.64 (9)C9—C14—C13120.63 (11)
N2—C3—H3112.3C9—C14—H14119.7
C4—C3—H3112.3C13—C14—H14119.7
C2—C3—H3112.3C16—C15—C20121.09 (10)
N1—C4—C3103.37 (9)C16—C15—S2119.65 (9)
N1—C4—H4A111.1C20—C15—S2119.26 (9)
C3—C4—H4A111.1C15—C16—C17119.43 (11)
N1—C4—H4B111.1C15—C16—H16120.3
C3—C4—H4B111.1C17—C16—H16120.3
H4A—C4—H4B109.1C18—C17—C16119.64 (11)
C6—C5—C2104.69 (9)C18—C17—H17120.2
C6—C5—H5A110.8C16—C17—H17120.2
C2—C5—H5A110.8C17—C18—C19120.64 (11)
C6—C5—H5B110.8C17—C18—H18119.7
C2—C5—H5B110.8C19—C18—H18119.7
H5A—C5—H5B108.9C20—C19—C18120.08 (11)
N2—C6—C5104.02 (9)C20—C19—H19120.0
N2—C6—C7109.21 (9)C18—C19—H19120.0
C5—C6—C7114.58 (10)C19—C20—C15119.11 (11)
N2—C6—H6109.6C19—C20—H20120.4
C5—C6—H6109.6C15—C20—H20120.4
C7—C6—H6109.6
O1—S2—N1—C144.10 (10)C6—N2—C8—C981.20 (11)
O2—S2—N1—C1173.83 (9)C3—N2—C8—S175.07 (10)
C15—S2—N1—C171.36 (10)C6—N2—C8—S143.66 (10)
O1—S2—N1—C4169.74 (8)C7—S1—C8—N229.10 (8)
O2—S2—N1—C440.01 (10)C7—S1—C8—C993.24 (9)
C15—S2—N1—C474.80 (9)N2—C8—C9—C14128.68 (11)
C4—N1—C1—C228.87 (12)S1—C8—C9—C148.85 (14)
S2—N1—C1—C2177.41 (7)N2—C8—C9—C1053.87 (13)
N1—C1—C2—C336.51 (11)S1—C8—C9—C10173.71 (8)
N1—C1—C2—C5149.15 (9)C14—C9—C10—C111.38 (17)
C8—N2—C3—C481.58 (11)C8—C9—C10—C11176.18 (10)
C6—N2—C3—C4158.20 (9)C9—C10—C11—C120.29 (17)
C8—N2—C3—C2165.45 (9)C10—C11—C12—C131.37 (17)
C6—N2—C3—C245.24 (10)C10—C11—C12—Cl1177.10 (9)
C1—C2—C3—N284.10 (10)C11—C12—C13—C141.89 (18)
C5—C2—C3—N234.98 (10)Cl1—C12—C13—C14176.58 (9)
C1—C2—C3—C432.73 (11)C10—C9—C14—C130.85 (17)
C5—C2—C3—C4151.81 (9)C8—C9—C14—C13176.56 (11)
C1—N1—C4—C38.62 (12)C12—C13—C14—C90.75 (17)
S2—N1—C4—C3157.80 (8)O1—S2—C15—C16151.10 (9)
N2—C3—C4—N193.76 (10)O2—S2—C15—C1620.23 (11)
C2—C3—C4—N115.53 (11)N1—S2—C15—C1693.69 (10)
C3—C2—C5—C613.22 (11)O1—S2—C15—C2028.20 (10)
C1—C2—C5—C697.94 (11)O2—S2—C15—C20159.07 (9)
C8—N2—C6—C5161.71 (9)N1—S2—C15—C2087.01 (10)
C3—N2—C6—C537.32 (11)C20—C15—C16—C171.00 (17)
C8—N2—C6—C738.96 (12)S2—C15—C16—C17178.28 (9)
C3—N2—C6—C785.43 (11)C15—C16—C17—C180.26 (17)
C2—C5—C6—N213.66 (11)C16—C17—C18—C190.52 (18)
C2—C5—C6—C7105.49 (11)C17—C18—C19—C200.57 (19)
N2—C6—C7—S115.76 (12)C18—C19—C20—C150.16 (18)
C5—C6—C7—S1131.96 (9)C16—C15—C20—C190.95 (17)
C8—S1—C7—C67.35 (10)S2—C15—C20—C19178.33 (9)
C3—N2—C8—C9160.07 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···S11.002.833.2274 (11)104
C14—H14···S10.952.663.1103 (13)110
C14—H14···O2i0.952.513.3863 (14)153
C16—H16···O20.952.572.9246 (15)102
C8—H8···Cg1ii1.002.613.4999 (12)148
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1.
 

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