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In the title mol­ecule, C26H27ClN2O2S, the fused pyrrolidine rings adopt twist conformations. C—H...O and C—H...π inter­actions link the mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000657/is2140sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000657/is2140Isup2.hkl
Contains datablock I

CCDC reference: 636715

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.037
  • wR factor = 0.094
  • Data-to-parameter ratio = 48.9

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.310 From the CIF: _refine_ls_abs_structure_Flack_su 0.030 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.31 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 40.00 From the CIF: _reflns_number_total 14228 Count of symmetry unique reflns 7975 Completeness (_total/calc) 178.41% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 6253 Fraction of Friedel pairs measured 0.784 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 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).

(3aR,6S,6aR)-cis-6-Benzyl-1-(4-chlorophenyl)-5- tosylperhydropyrrolo[3,4-b]pyrrole top
Crystal data top
C26H27ClN2O2SF(000) = 984
Mr = 467.01Dx = 1.322 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 8749 reflections
a = 10.3604 (2) Åθ = 2.7–43.3°
b = 10.7859 (2) ŵ = 0.28 mm1
c = 21.0024 (4) ÅT = 100 K
V = 2346.94 (8) Å3Block, colourless
Z = 40.65 × 0.64 × 0.45 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
14228 independent reflections
Radiation source: fine-focus sealed tube12745 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 8.33 pixels mm-1θmax = 40.0°, θmin = 1.9°
ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1719
Tmin = 0.797, Tmax = 0.885l = 3735
58953 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)] = 0.037H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1841P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
14228 reflectionsΔρmax = 0.55 e Å3
291 parametersΔρmin = 0.35 e Å3
0 restraintsAbsolute structure: Flack (1983), with 6271 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.31 (3)
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
Cl10.67565 (3)0.66484 (2)0.255031 (16)0.03637 (7)
O10.95707 (7)0.04397 (6)0.01476 (3)0.02109 (11)
O21.07423 (6)0.03326 (6)0.11054 (3)0.01936 (10)
S10.959132 (19)0.027921 (18)0.072465 (9)0.01514 (3)
N10.84597 (7)0.02876 (7)0.11783 (3)0.01588 (10)
N20.62380 (8)0.15786 (8)0.14924 (4)0.02165 (13)
C10.72566 (9)0.07412 (9)0.08790 (4)0.02152 (15)
H1A0.73420.16220.07540.026*
H1B0.70410.02450.04970.026*
C20.62213 (9)0.05854 (9)0.13949 (4)0.02242 (16)
H20.60890.13660.16430.027*
C30.67268 (8)0.04719 (8)0.18156 (4)0.01827 (13)
H30.63910.04090.22610.022*
C40.82087 (7)0.03490 (7)0.17940 (3)0.01479 (11)
H40.86090.11920.17870.018*
C50.49548 (9)0.00889 (12)0.11229 (5)0.0285 (2)
H5A0.47460.04930.07120.034*
H5B0.42330.02230.14240.034*
C60.52198 (9)0.12921 (11)0.10314 (5)0.02652 (18)
H6A0.55140.14640.05920.032*
H6B0.44350.17870.11180.032*
C70.63625 (8)0.27537 (9)0.17420 (4)0.02076 (15)
C80.57921 (10)0.37818 (10)0.14343 (5)0.02610 (18)
H80.53210.36590.10510.031*
C90.59098 (10)0.49652 (10)0.16821 (5)0.0286 (2)
H90.55070.56460.14750.034*
C100.66178 (10)0.51555 (9)0.22338 (5)0.02633 (18)
C110.72054 (9)0.41699 (8)0.25455 (5)0.02315 (15)
H110.77040.43110.29180.028*
C120.70571 (9)0.29743 (8)0.23073 (4)0.02062 (14)
H120.74300.22960.25300.025*
C130.91428 (8)0.18140 (7)0.05469 (4)0.01550 (12)
C140.96505 (9)0.27838 (8)0.09073 (4)0.01910 (13)
H141.02840.26240.12240.023*
C150.92212 (9)0.39861 (8)0.07995 (4)0.02051 (14)
H150.95690.46480.10430.025*
C160.82858 (9)0.42359 (8)0.03381 (4)0.01893 (13)
C170.77992 (8)0.32556 (8)0.00228 (4)0.01910 (13)
H170.71690.34160.03410.023*
C180.82214 (8)0.20475 (8)0.00761 (4)0.01730 (12)
H180.78870.13870.01740.021*
C190.78075 (10)0.55400 (8)0.02348 (5)0.02537 (17)
H19A0.76080.56610.02170.038*
H19B0.84760.61300.03650.038*
H19C0.70270.56770.04890.038*
C200.87723 (8)0.04074 (7)0.23485 (4)0.01706 (12)
H20A0.82700.11810.24010.020*
H20B0.96750.06370.22490.020*
C210.87379 (7)0.03215 (7)0.29605 (3)0.01522 (11)
C220.77823 (9)0.01359 (8)0.34187 (4)0.02030 (14)
H220.71680.05090.33620.024*
C230.77171 (11)0.08873 (10)0.39597 (4)0.02595 (18)
H230.70600.07530.42670.031*
C240.86127 (12)0.18293 (9)0.40475 (5)0.02767 (19)
H240.85640.23460.44130.033*
C250.95847 (11)0.20160 (8)0.35973 (4)0.02374 (16)
H251.02060.26530.36590.028*
C260.96419 (9)0.12681 (7)0.30587 (4)0.01782 (12)
H261.03030.14010.27530.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.03755 (14)0.01834 (9)0.05322 (17)0.00325 (8)0.01405 (13)0.00559 (10)
O10.0256 (3)0.0214 (3)0.0163 (2)0.0035 (2)0.0012 (2)0.00410 (19)
O20.0160 (2)0.0225 (3)0.0197 (2)0.0016 (2)0.00214 (19)0.0020 (2)
S10.01578 (7)0.01541 (7)0.01424 (7)0.00111 (6)0.00003 (6)0.00026 (6)
N10.0173 (3)0.0157 (2)0.0146 (2)0.0018 (2)0.0007 (2)0.0002 (2)
N20.0187 (3)0.0272 (3)0.0190 (3)0.0048 (3)0.0037 (2)0.0033 (3)
C10.0215 (4)0.0224 (4)0.0207 (3)0.0056 (3)0.0026 (3)0.0024 (3)
C20.0192 (3)0.0280 (4)0.0200 (3)0.0074 (3)0.0022 (3)0.0042 (3)
C30.0153 (3)0.0241 (3)0.0154 (3)0.0007 (2)0.0005 (2)0.0032 (2)
C40.0154 (3)0.0149 (3)0.0141 (3)0.0000 (2)0.0010 (2)0.0007 (2)
C50.0172 (3)0.0447 (6)0.0236 (4)0.0070 (3)0.0033 (3)0.0035 (4)
C60.0184 (4)0.0404 (5)0.0208 (4)0.0031 (3)0.0036 (3)0.0044 (4)
C70.0162 (3)0.0253 (4)0.0208 (3)0.0059 (3)0.0030 (3)0.0057 (3)
C80.0209 (4)0.0329 (5)0.0244 (4)0.0097 (3)0.0035 (3)0.0106 (3)
C90.0242 (4)0.0278 (4)0.0336 (5)0.0093 (3)0.0089 (4)0.0139 (4)
C100.0234 (4)0.0207 (4)0.0349 (5)0.0048 (3)0.0111 (3)0.0068 (3)
C110.0208 (4)0.0212 (3)0.0275 (4)0.0040 (3)0.0054 (3)0.0030 (3)
C120.0199 (3)0.0212 (3)0.0207 (3)0.0061 (3)0.0023 (3)0.0032 (3)
C130.0166 (3)0.0153 (3)0.0147 (3)0.0007 (2)0.0004 (2)0.0017 (2)
C140.0217 (3)0.0176 (3)0.0181 (3)0.0018 (3)0.0034 (3)0.0006 (2)
C150.0243 (4)0.0159 (3)0.0214 (4)0.0019 (2)0.0018 (3)0.0002 (2)
C160.0186 (3)0.0163 (3)0.0219 (3)0.0003 (2)0.0028 (3)0.0035 (2)
C170.0172 (3)0.0192 (3)0.0209 (3)0.0002 (2)0.0018 (3)0.0040 (3)
C180.0174 (3)0.0183 (3)0.0162 (3)0.0011 (2)0.0016 (2)0.0019 (2)
C190.0244 (4)0.0182 (3)0.0335 (5)0.0034 (3)0.0042 (3)0.0046 (3)
C200.0201 (3)0.0148 (3)0.0163 (3)0.0005 (2)0.0032 (2)0.0007 (2)
C210.0167 (3)0.0143 (3)0.0146 (3)0.0002 (2)0.0009 (2)0.0018 (2)
C220.0190 (3)0.0229 (4)0.0190 (3)0.0009 (3)0.0018 (3)0.0057 (3)
C230.0296 (5)0.0292 (4)0.0190 (3)0.0072 (3)0.0065 (3)0.0042 (3)
C240.0435 (6)0.0210 (4)0.0185 (4)0.0076 (4)0.0017 (4)0.0019 (3)
C250.0344 (4)0.0152 (3)0.0216 (3)0.0025 (3)0.0042 (3)0.0006 (3)
C260.0207 (3)0.0159 (3)0.0169 (3)0.0026 (3)0.0014 (3)0.0015 (2)
Geometric parameters (Å, º) top
Cl1—C101.7480 (11)C11—C121.3916 (13)
O1—S11.4390 (6)C11—H110.95
O2—S11.4369 (6)C12—H120.95
S1—N11.6298 (7)C13—C141.3942 (11)
S1—C131.7595 (8)C13—C181.3971 (11)
N1—C11.4793 (11)C14—C151.3895 (12)
N1—C41.4868 (10)C14—H140.95
N2—C71.3775 (13)C15—C161.3966 (13)
N2—C31.4637 (11)C15—H150.95
N2—C61.4649 (12)C16—C171.3953 (12)
C1—C21.5338 (13)C16—C191.5070 (12)
C1—H1A0.99C17—C181.3901 (12)
C1—H1B0.99C17—H170.95
C2—C51.5280 (14)C18—H180.95
C2—C31.5348 (13)C19—H19A0.98
C2—H21.00C19—H19B0.98
C3—C41.5417 (11)C19—H19C0.98
C3—H31.00C20—C211.5072 (11)
C4—C201.5372 (10)C20—H20A0.99
C4—H41.00C20—H20B0.99
C5—C61.5267 (17)C21—C221.3951 (11)
C5—H5A0.99C21—C261.4008 (11)
C5—H5B0.99C22—C231.3972 (13)
C6—H6A0.99C22—H220.95
C6—H6B0.99C23—C241.3882 (17)
C7—C121.4087 (13)C23—H230.95
C7—C81.4130 (12)C24—C251.3960 (16)
C8—C91.3838 (17)C24—H240.95
C8—H80.95C25—C261.3907 (12)
C9—C101.3865 (17)C25—H250.95
C9—H90.95C26—H260.95
C10—C111.3890 (13)
O2—S1—O1120.17 (4)C9—C10—C11120.83 (10)
O2—S1—N1106.66 (4)C9—C10—Cl1119.84 (8)
O1—S1—N1106.24 (4)C11—C10—Cl1119.32 (9)
O2—S1—C13107.43 (4)C10—C11—C12119.42 (10)
O1—S1—C13108.93 (4)C10—C11—H11120.3
N1—S1—C13106.68 (4)C12—C11—H11120.3
C1—N1—C4112.02 (6)C11—C12—C7121.06 (8)
C1—N1—S1118.80 (6)C11—C12—H12119.5
C4—N1—S1117.45 (5)C7—C12—H12119.5
C7—N2—C3122.78 (7)C14—C13—C18120.45 (7)
C7—N2—C6120.86 (8)C14—C13—S1119.41 (6)
C3—N2—C6112.56 (8)C18—C13—S1120.02 (6)
N1—C1—C2104.64 (7)C15—C14—C13119.40 (8)
N1—C1—H1A110.8C15—C14—H14120.3
C2—C1—H1A110.8C13—C14—H14120.3
N1—C1—H1B110.8C14—C15—C16121.01 (8)
C2—C1—H1B110.8C14—C15—H15119.5
H1A—C1—H1B108.9C16—C15—H15119.5
C5—C2—C1112.01 (8)C17—C16—C15118.78 (8)
C5—C2—C3104.35 (8)C17—C16—C19120.68 (8)
C1—C2—C3104.45 (7)C15—C16—C19120.54 (8)
C5—C2—H2111.9C18—C17—C16121.03 (8)
C1—C2—H2111.9C18—C17—H17119.5
C3—C2—H2111.9C16—C17—H17119.5
N2—C3—C2102.76 (7)C17—C18—C13119.32 (8)
N2—C3—C4113.64 (7)C17—C18—H18120.3
C2—C3—C4105.00 (7)C13—C18—H18120.3
N2—C3—H3111.6C16—C19—H19A109.5
C2—C3—H3111.6C16—C19—H19B109.5
C4—C3—H3111.6H19A—C19—H19B109.5
N1—C4—C20110.33 (6)C16—C19—H19C109.5
N1—C4—C3103.86 (6)H19A—C19—H19C109.5
C20—C4—C3113.67 (6)H19B—C19—H19C109.5
N1—C4—H4109.6C21—C20—C4111.12 (6)
C20—C4—H4109.6C21—C20—H20A109.4
C3—C4—H4109.6C4—C20—H20A109.4
C6—C5—C2103.57 (8)C21—C20—H20B109.4
C6—C5—H5A111.0C4—C20—H20B109.4
C2—C5—H5A111.0H20A—C20—H20B108.0
C6—C5—H5B111.0C22—C21—C26118.53 (7)
C2—C5—H5B111.0C22—C21—C20122.02 (7)
H5A—C5—H5B109.0C26—C21—C20119.33 (7)
N2—C6—C5104.60 (8)C21—C22—C23120.80 (8)
N2—C6—H6A110.8C21—C22—H22119.6
C5—C6—H6A110.8C23—C22—H22119.6
N2—C6—H6B110.8C24—C23—C22120.02 (9)
C5—C6—H6B110.8C24—C23—H23120.0
H6A—C6—H6B108.9C22—C23—H23120.0
N2—C7—C12121.60 (8)C23—C24—C25119.85 (9)
N2—C7—C8120.59 (9)C23—C24—H24120.1
C12—C7—C8117.81 (9)C25—C24—H24120.1
C9—C8—C7121.00 (10)C26—C25—C24119.87 (9)
C9—C8—H8119.5C26—C25—H25120.1
C7—C8—H8119.5C24—C25—H25120.1
C8—C9—C10119.83 (9)C25—C26—C21120.93 (8)
C8—C9—H9120.1C25—C26—H26119.5
C10—C9—H9120.1C21—C26—H26119.5
O2—S1—N1—C1165.00 (7)C7—C8—C9—C101.27 (15)
O1—S1—N1—C135.68 (8)C8—C9—C10—C110.49 (14)
C13—S1—N1—C180.42 (7)C8—C9—C10—Cl1179.52 (8)
O2—S1—N1—C454.85 (7)C9—C10—C11—C121.36 (14)
O1—S1—N1—C4175.84 (6)Cl1—C10—C11—C12177.68 (7)
C13—S1—N1—C459.74 (6)C10—C11—C12—C72.45 (14)
C4—N1—C1—C210.49 (9)N2—C7—C12—C11178.25 (9)
S1—N1—C1—C2152.66 (6)C8—C7—C12—C111.67 (13)
N1—C1—C2—C5138.50 (8)O2—S1—C13—C1417.56 (8)
N1—C1—C2—C326.15 (9)O1—S1—C13—C14149.21 (7)
C7—N2—C3—C2173.71 (8)N1—S1—C13—C1496.50 (7)
C6—N2—C3—C215.53 (9)O2—S1—C13—C18166.62 (7)
C7—N2—C3—C473.41 (11)O1—S1—C13—C1834.97 (8)
C6—N2—C3—C4128.42 (8)N1—S1—C13—C1879.32 (7)
C5—C2—C3—N230.86 (9)C18—C13—C14—C150.74 (13)
C1—C2—C3—N286.88 (8)S1—C13—C14—C15175.07 (7)
C5—C2—C3—C4149.96 (7)C13—C14—C15—C160.29 (14)
C1—C2—C3—C432.22 (9)C14—C15—C16—C170.99 (13)
C1—N1—C4—C20112.75 (8)C14—C15—C16—C19178.73 (9)
S1—N1—C4—C20104.52 (7)C15—C16—C17—C180.67 (13)
C1—N1—C4—C39.42 (9)C19—C16—C17—C18179.04 (8)
S1—N1—C4—C3133.31 (6)C16—C17—C18—C130.33 (13)
N2—C3—C4—N185.98 (8)C14—C13—C18—C171.04 (12)
C2—C3—C4—N125.55 (8)S1—C13—C18—C17174.74 (6)
N2—C3—C4—C20154.09 (7)N1—C4—C20—C21170.01 (6)
C2—C3—C4—C2094.38 (8)C3—C4—C20—C2173.81 (9)
C1—C2—C5—C677.46 (10)C4—C20—C21—C22100.06 (9)
C3—C2—C5—C634.95 (9)C4—C20—C21—C2675.91 (9)
C7—N2—C6—C5152.55 (9)C26—C21—C22—C230.81 (12)
C3—N2—C6—C56.09 (10)C20—C21—C22—C23175.18 (8)
C2—C5—C6—N225.26 (10)C21—C22—C23—C240.23 (14)
C3—N2—C7—C124.71 (14)C22—C23—C24—C250.60 (15)
C6—N2—C7—C12161.14 (8)C23—C24—C25—C260.83 (15)
C3—N2—C7—C8175.36 (8)C24—C25—C26—C210.24 (14)
C6—N2—C7—C818.94 (13)C22—C21—C26—C250.58 (12)
N2—C7—C8—C9179.87 (9)C20—C21—C26—C25175.53 (8)
C12—C7—C8—C90.20 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O2i0.952.573.4684 (11)159
C23—H23···O1ii0.952.533.4750 (12)176
C12—H12···Cg10.952.763.6558 (9)157
C15—H15···Cg1iii0.952.563.4547 (10)157
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+3/2, y, z+1/2; (iii) x+2, y+1/2, z+1/2.
 

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