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In the title mol­ecule, C21H24N2O2S2, the two pyrrolidine rings adopt twisted conformations, while the thia­zolidine ring is in an envelope conformation with the N atom at the flap position. In the crystal structure, mol­ecules translated by a unit cell along the a axis are linked by inter­molecular O—H...O hydrogen bonds into chains. Adjacent chains are inter­connected via π–π and C—H...π inter­actions to form sheets parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031060/fl2045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031060/fl2045Isup2.hkl
Contains datablock I

CCDC reference: 621309

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.031
  • wR factor = 0.091
  • Data-to-parameter ratio = 33.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.69 mm PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C6 .. 2.98 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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-Methylphenyl)-5-(phenylsulfonyl)perhydro-1,3-thiazolo[3,4-a]pyrrolo[4,5-c]pyrrole top
Crystal data top
C21H24N2O2S2Z = 2
Mr = 400.54F(000) = 424
Triclinic, P1Dx = 1.408 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9672 (1) ÅCell parameters from 8023 reflections
b = 10.4040 (1) Åθ = 2.8–40.9°
c = 10.6794 (1) ŵ = 0.30 mm1
α = 88.311 (1)°T = 100 K
β = 72.555 (1)°Block, colourless
γ = 83.761 (1)°0.69 × 0.63 × 0.43 mm
V = 944.87 (2) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
8275 independent reflections
Radiation source: fine-focus sealed tube7477 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 8.33 pixels mm-1θmax = 35.0°, θmin = 2.6°
ω scansh = 1414
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1616
Tmin = 0.782, Tmax = 0.881l = 1717
23928 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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0473P)2 + 0.2769P]
where P = (Fo2 + 2Fc2)/3
8275 reflections(Δ/σ)max = 0.001
245 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.43 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
S10.63394 (3)0.03156 (2)0.285620 (19)0.01952 (5)
S20.02279 (2)0.433074 (19)0.284891 (18)0.01423 (4)
O10.00373 (8)0.56638 (6)0.32439 (6)0.02027 (12)
O20.10658 (7)0.35609 (7)0.31051 (7)0.02208 (12)
N10.14375 (8)0.36155 (6)0.35707 (6)0.01376 (11)
N20.48516 (7)0.19893 (6)0.26025 (6)0.01207 (10)
C10.26927 (9)0.42780 (7)0.38125 (7)0.01421 (12)
H1A0.22560.50330.44010.017*
H1B0.34190.45650.29820.017*
C20.35146 (9)0.32172 (7)0.44716 (7)0.01373 (12)
H20.29620.31620.54330.016*
C30.34258 (8)0.19897 (7)0.37383 (7)0.01277 (11)
H30.34450.11960.42860.015*
C40.19240 (9)0.22157 (7)0.33319 (7)0.01426 (12)
H4A0.21330.19980.23950.017*
H4B0.11070.16930.38720.017*
C50.52855 (9)0.33236 (8)0.42032 (8)0.01639 (13)
H5A0.55520.41960.38780.020*
H5B0.56010.31470.50090.020*
C60.61007 (8)0.22874 (7)0.31459 (7)0.01372 (12)
H60.69720.26420.24470.016*
C70.67242 (10)0.10293 (8)0.37237 (8)0.01913 (14)
H7A0.61780.09750.46750.023*
H7B0.78660.10150.35970.023*
C80.53380 (9)0.07889 (7)0.18744 (7)0.01401 (12)
H80.43730.04090.18400.017*
C90.63425 (9)0.10008 (7)0.04709 (7)0.01372 (12)
C100.78370 (10)0.03672 (9)0.00837 (8)0.01935 (14)
H100.83030.02040.04370.023*
C110.86590 (10)0.05634 (9)0.14007 (8)0.02116 (15)
H110.96840.01310.17570.025*
C120.80089 (10)0.13769 (8)0.21987 (7)0.01772 (14)
C130.65061 (10)0.20115 (8)0.16353 (8)0.01755 (13)
H130.60360.25750.21590.021*
C140.56865 (9)0.18329 (8)0.03232 (7)0.01584 (12)
H140.46710.22800.00380.019*
C150.12062 (9)0.42454 (7)0.11467 (7)0.01424 (12)
C160.08860 (10)0.33158 (8)0.03785 (8)0.01768 (13)
H160.01240.27380.07590.021*
C170.17007 (12)0.32463 (9)0.09568 (8)0.02177 (16)
H170.14840.26260.14960.026*
C180.28294 (11)0.40844 (9)0.14991 (8)0.02224 (16)
H180.33890.40260.24080.027*
C190.31497 (10)0.50087 (9)0.07258 (8)0.02081 (15)
H190.39260.55750.11050.025*
C200.23279 (10)0.50995 (8)0.06055 (8)0.01756 (13)
H200.25280.57340.11390.021*
C210.88898 (12)0.15497 (10)0.36255 (8)0.02512 (17)
H21A1.00150.15340.37280.038*
H21B0.85070.23810.39340.038*
H21C0.87200.08470.41420.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02571 (10)0.01434 (8)0.01500 (8)0.00316 (7)0.00273 (7)0.00127 (6)
S20.01041 (7)0.01847 (9)0.01286 (7)0.00014 (6)0.00246 (5)0.00152 (6)
O10.0207 (3)0.0199 (3)0.0182 (3)0.0061 (2)0.0052 (2)0.0052 (2)
O20.0125 (2)0.0329 (3)0.0214 (3)0.0069 (2)0.0046 (2)0.0027 (2)
N10.0123 (2)0.0149 (3)0.0142 (2)0.0011 (2)0.0043 (2)0.0013 (2)
N20.0112 (2)0.0130 (2)0.0109 (2)0.00136 (19)0.00131 (19)0.00158 (19)
C10.0129 (3)0.0151 (3)0.0147 (3)0.0015 (2)0.0040 (2)0.0021 (2)
C20.0129 (3)0.0166 (3)0.0111 (3)0.0004 (2)0.0029 (2)0.0021 (2)
C30.0120 (3)0.0142 (3)0.0109 (2)0.0016 (2)0.0013 (2)0.0002 (2)
C40.0127 (3)0.0144 (3)0.0153 (3)0.0031 (2)0.0028 (2)0.0002 (2)
C50.0141 (3)0.0192 (3)0.0166 (3)0.0002 (2)0.0058 (2)0.0051 (2)
C60.0113 (3)0.0160 (3)0.0135 (3)0.0006 (2)0.0033 (2)0.0010 (2)
C70.0191 (3)0.0206 (3)0.0173 (3)0.0027 (3)0.0065 (3)0.0002 (3)
C80.0157 (3)0.0124 (3)0.0122 (3)0.0009 (2)0.0017 (2)0.0010 (2)
C90.0143 (3)0.0139 (3)0.0118 (3)0.0017 (2)0.0018 (2)0.0018 (2)
C100.0167 (3)0.0232 (4)0.0148 (3)0.0027 (3)0.0014 (2)0.0003 (3)
C110.0168 (3)0.0266 (4)0.0157 (3)0.0007 (3)0.0009 (3)0.0020 (3)
C120.0209 (3)0.0180 (3)0.0127 (3)0.0064 (3)0.0009 (2)0.0021 (2)
C130.0221 (3)0.0165 (3)0.0136 (3)0.0033 (3)0.0043 (3)0.0003 (2)
C140.0167 (3)0.0157 (3)0.0141 (3)0.0008 (2)0.0032 (2)0.0008 (2)
C150.0137 (3)0.0159 (3)0.0128 (3)0.0000 (2)0.0041 (2)0.0007 (2)
C160.0213 (3)0.0161 (3)0.0168 (3)0.0007 (3)0.0079 (3)0.0018 (2)
C170.0294 (4)0.0200 (3)0.0163 (3)0.0046 (3)0.0095 (3)0.0042 (3)
C180.0241 (4)0.0258 (4)0.0134 (3)0.0068 (3)0.0036 (3)0.0002 (3)
C190.0181 (3)0.0253 (4)0.0166 (3)0.0006 (3)0.0026 (3)0.0047 (3)
C200.0170 (3)0.0191 (3)0.0162 (3)0.0027 (3)0.0043 (2)0.0010 (2)
C210.0316 (4)0.0264 (4)0.0133 (3)0.0083 (4)0.0013 (3)0.0015 (3)
Geometric parameters (Å, º) top
S1—C71.8189 (9)C8—C91.5234 (10)
S1—C81.8697 (8)C8—H81.00
S2—O11.4355 (7)C9—C101.3916 (11)
S2—O21.4356 (7)C9—C141.3999 (11)
S2—N11.6176 (7)C10—C111.3991 (12)
S2—C151.7659 (7)C10—H100.95
N1—C11.4704 (10)C11—C121.3894 (13)
N1—C41.4811 (10)C11—H110.95
N2—C81.4457 (9)C12—C131.3992 (12)
N2—C61.4709 (10)C12—C211.5070 (12)
N2—C31.4751 (9)C13—C141.3910 (11)
C1—C21.5314 (11)C13—H130.95
C1—H1A0.99C14—H140.95
C1—H1B0.99C15—C161.3926 (11)
C2—C31.5392 (10)C15—C201.3967 (11)
C2—C51.5425 (11)C16—C171.3937 (12)
C2—H21.00C16—H160.95
C3—C41.5273 (10)C17—C181.3895 (14)
C3—H31.00C17—H170.95
C4—H4A0.99C18—C191.3922 (13)
C4—H4B0.99C18—H180.95
C5—C61.5418 (10)C19—C201.3921 (12)
C5—H5A0.99C19—H190.95
C5—H5B0.99C20—H200.95
C6—C71.5514 (11)C21—H21A0.98
C6—H61.00C21—H21B0.98
C7—H7A0.99C21—H21C0.98
C7—H7B0.99
C7—S1—C892.30 (4)C6—C7—H7B110.3
O1—S2—O2120.27 (4)S1—C7—H7B110.3
O1—S2—N1106.97 (4)H7A—C7—H7B108.6
O2—S2—N1106.39 (4)N2—C8—C9111.73 (6)
O1—S2—C15108.37 (4)N2—C8—S1106.13 (5)
O2—S2—C15107.51 (4)C9—C8—S1114.25 (5)
N1—S2—C15106.59 (3)N2—C8—H8108.2
C1—N1—C4111.35 (6)C9—C8—H8108.2
C1—N1—S2121.74 (5)S1—C8—H8108.2
C4—N1—S2118.52 (5)C10—C9—C14118.29 (7)
C8—N2—C6109.25 (6)C10—C9—C8123.83 (7)
C8—N2—C3115.43 (6)C14—C9—C8117.79 (6)
C6—N2—C3105.37 (5)C9—C10—C11120.60 (8)
N1—C1—C2102.08 (6)C9—C10—H10119.7
N1—C1—H1A111.4C11—C10—H10119.7
C2—C1—H1A111.4C12—C11—C10121.44 (8)
N1—C1—H1B111.4C12—C11—H11119.3
C2—C1—H1B111.4C10—C11—H11119.3
H1A—C1—H1B109.2C11—C12—C13117.69 (7)
C1—C2—C3102.64 (6)C11—C12—C21120.84 (8)
C1—C2—C5113.66 (6)C13—C12—C21121.46 (8)
C3—C2—C5105.20 (6)C14—C13—C12121.28 (8)
C1—C2—H2111.6C14—C13—H13119.4
C3—C2—H2111.6C12—C13—H13119.4
C5—C2—H2111.6C13—C14—C9120.69 (7)
N2—C3—C4112.10 (6)C13—C14—H14119.7
N2—C3—C2101.32 (6)C9—C14—H14119.7
C4—C3—C2106.54 (6)C16—C15—C20121.29 (7)
N2—C3—H3112.1C16—C15—S2120.03 (6)
C4—C3—H3112.1C20—C15—S2118.66 (6)
C2—C3—H3112.1C15—C16—C17119.00 (8)
N1—C4—C3103.60 (6)C15—C16—H16120.5
N1—C4—H4A111.0C17—C16—H16120.5
C3—C4—H4A111.0C18—C17—C16120.01 (8)
N1—C4—H4B111.0C18—C17—H17120.0
C3—C4—H4B111.0C16—C17—H17120.0
H4A—C4—H4B109.0C17—C18—C19120.76 (8)
C6—C5—C2104.44 (6)C17—C18—H18119.6
C6—C5—H5A110.9C19—C18—H18119.6
C2—C5—H5A110.9C20—C19—C18119.76 (8)
C6—C5—H5B110.9C20—C19—H19120.1
C2—C5—H5B110.9C18—C19—H19120.1
H5A—C5—H5B108.9C19—C20—C15119.17 (8)
N2—C6—C5104.25 (6)C19—C20—H20120.4
N2—C6—C7108.54 (6)C15—C20—H20120.4
C5—C6—C7112.71 (6)C12—C21—H21A109.5
N2—C6—H6110.4C12—C21—H21B109.5
C5—C6—H6110.4H21A—C21—H21B109.5
C7—C6—H6110.4C12—C21—H21C109.5
C6—C7—S1106.94 (5)H21A—C21—H21C109.5
C6—C7—H7A110.3H21B—C21—H21C109.5
S1—C7—H7A110.3
O1—S2—N1—C134.42 (7)C3—N2—C8—C9156.82 (6)
O2—S2—N1—C1164.15 (6)C6—N2—C8—S140.44 (7)
C15—S2—N1—C181.34 (6)C3—N2—C8—S178.05 (6)
O1—S2—N1—C4179.84 (5)C7—S1—C8—N221.24 (5)
O2—S2—N1—C450.44 (6)C7—S1—C8—C9102.33 (6)
C15—S2—N1—C464.07 (6)N2—C8—C9—C10124.87 (8)
C4—N1—C1—C231.20 (7)S1—C8—C9—C104.38 (10)
S2—N1—C1—C2178.82 (5)N2—C8—C9—C1458.50 (9)
N1—C1—C2—C336.58 (7)S1—C8—C9—C14178.99 (6)
N1—C1—C2—C5149.64 (6)C14—C9—C10—C110.18 (12)
C8—N2—C3—C481.44 (8)C8—C9—C10—C11176.80 (8)
C6—N2—C3—C4157.94 (6)C9—C10—C11—C120.89 (14)
C8—N2—C3—C2165.31 (6)C10—C11—C12—C130.88 (13)
C6—N2—C3—C244.70 (7)C10—C11—C12—C21178.26 (8)
C1—C2—C3—N286.81 (6)C11—C12—C13—C140.19 (12)
C5—C2—C3—N232.35 (7)C21—C12—C13—C14178.93 (8)
C1—C2—C3—C430.56 (7)C12—C13—C14—C90.49 (12)
C5—C2—C3—C4149.72 (6)C10—C9—C14—C130.49 (12)
C1—N1—C4—C312.11 (8)C8—C9—C14—C13176.33 (7)
S2—N1—C4—C3160.89 (5)O1—S2—C15—C16145.01 (7)
N2—C3—C4—N197.82 (7)O2—S2—C15—C1613.58 (8)
C2—C3—C4—N112.16 (7)N1—S2—C15—C16100.17 (7)
C1—C2—C5—C6102.20 (7)O1—S2—C15—C2036.80 (7)
C3—C2—C5—C69.31 (8)O2—S2—C15—C20168.23 (6)
C8—N2—C6—C5163.96 (6)N1—S2—C15—C2078.02 (7)
C3—N2—C6—C539.37 (7)C20—C15—C16—C170.29 (12)
C8—N2—C6—C743.61 (8)S2—C15—C16—C17178.44 (6)
C3—N2—C6—C780.98 (7)C15—C16—C17—C180.93 (13)
C2—C5—C6—N217.40 (8)C16—C17—C18—C190.69 (13)
C2—C5—C6—C7100.11 (7)C17—C18—C19—C200.21 (13)
N2—C6—C7—S125.42 (7)C18—C19—C20—C150.84 (13)
C5—C6—C7—S1140.37 (6)C16—C15—C20—C190.60 (12)
C8—S1—C7—C62.37 (6)S2—C15—C20—C19177.57 (6)
C6—N2—C8—C984.70 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···S10.952.663.1166 (8)110
C16—H16···O20.952.542.9152 (11)103
C14—H14···Cg10.952.983.8372 (9)152
C6—H6···O2i1.002.382.9791 (10)118
C8—H8···Cg2ii1.002.693.6178 (9)154
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z.
 

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