Related literature   {#sec1}
====================

For the medicinal properties of pyrrolidine compounds, see: Yang *et al.* (1997[@bb5]). For related structures, see: Köhn *et al.* (2004[@bb2]); Li (2011[@bb3]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~11~H~20~N~2~S*M* *~r~* = 212.35Orthorhombic,*a* = 9.3808 (19) Å*b* = 10.925 (2) Å*c* = 23.540 (5) Å*V* = 2412.6 (8) Å^3^*Z* = 8Mo *K*α radiationμ = 0.24 mm^−1^*T* = 293 K0.22 × 0.20 × 0.18 mm

### Data collection   {#sec2.1.2}

Bruker SMART CCD diffractometer22078 measured reflections2766 independent reflections1700 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.046

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.053*wR*(*F* ^2^) = 0.190*S* = 1.182766 reflections127 parametersH-atom parameters constrainedΔρ~max~ = 0.25 e Å^−3^Δρ~min~ = −0.35 e Å^−3^

 {#d5e285}

Data collection: *SMART* (Bruker, 1997[@bb1]); cell refinement: *SAINT* (Bruker, 1997[@bb1]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb4]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb4]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb4]); software used to prepare material for publication: *SHELXTL*.

Supplementary Material
======================

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S1600536812012627/lh5439sup1.cif](http://dx.doi.org/10.1107/S1600536812012627/lh5439sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536812012627/lh5439Isup2.hkl](http://dx.doi.org/10.1107/S1600536812012627/lh5439Isup2.hkl)

Supplementary material file. DOI: [10.1107/S1600536812012627/lh5439Isup3.cml](http://dx.doi.org/10.1107/S1600536812012627/lh5439Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?lh5439&file=lh5439sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?lh5439sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?lh5439&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [LH5439](http://scripts.iucr.org/cgi-bin/sendsup?lh5439)).

The authors would like to thank the Natural Science Foundation of Shandong Province (No. ZR2010BL025).

Comment
=======

Pyrrolidine compounds have been shown to have medicinal properties (Yang *et al.*, 1997). The molecular structure of the title compound is shown in Fig. 1. The five-membered ring has an envelope conformation with atom C2 forming the flap. The structures related compounds have been determined (Köhn *et al.*, 2004; Li, 2011).

Experimental {#experimental}
============

A mixture of pyrrolidine (0.6 mol), and *N*-cyclohexylmethanethioamide (0.6 mol) was stirred in refluxing ethanol (14 ml) for 4 h to afford the title compound (0.51 mol, yield 85%). Colourless blocks of the title compound were obtained by recrystallization of a solution of the title compound ethanol at room temperature.

Refinement {#refinement}
==========

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C---H distances = 0.93--0.97 Å; N---H = 0.86 Å and with *U*~iso~(H) = 1.2*U*~eq~(C,*N*).

Figures
=======

![The molecular structure of the title compound showing 30% probability displacement ellipsoids.](e-68-o1220-fig1){#Fap1}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------- ---------------------------------------
  C~11~H~20~N~2~S           *F*(000) = 928
  *M~r~* = 212.35           *D*~x~ = 1.169 Mg m^−3^
  Orthorhombic, *Pbca*      Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ac 2ab   Cell parameters from 1700 reflections
  *a* = 9.3808 (19) Å       θ = 3.4--27.5°
  *b* = 10.925 (2) Å        µ = 0.24 mm^−1^
  *c* = 23.540 (5) Å        *T* = 293 K
  *V* = 2412.6 (8) Å^3^     Block, colorless
  *Z* = 8                   0.22 × 0.20 × 0.18 mm
  ------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------ --------------------------------------
  Bruker SMART CCD diffractometer            1700 reflections with *I* \> 2σ(*I*)
  Radiation source: fine-focus sealed tube   *R*~int~ = 0.046
  Graphite monochromator                     θ~max~ = 27.5°, θ~min~ = 3.4°
  φ and ω scans                              *h* = −12→12
  22078 measured reflections                 *k* = −13→14
  2766 independent reflections               *l* = −30→30
  ------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.053   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.190                  H-atom parameters constrained
  *S* = 1.18                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.1021*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  2766 reflections                      (Δ/σ)~max~ \< 0.001
  127 parameters                        Δρ~max~ = 0.25 e Å^−3^
  0 restraints                          Δρ~min~ = −0.35 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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 *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ ------------- -------------- -------------- -------------------- --
         *x*           *y*            *z*            *U*~iso~\*/*U*~eq~   
  S1     0.07717 (8)   0.34275 (5)    0.16033 (2)    0.0727 (3)           
  N2     0.1756 (2)    0.57053 (15)   0.14966 (7)    0.0649 (5)           
  H2A    0.2105        0.6354         0.1650         0.078\*              
  N1     0.1569 (2)    0.49963 (16)   0.24023 (7)    0.0625 (5)           
  C5     0.1402 (2)    0.47798 (18)   0.18465 (8)    0.0533 (5)           
  C6     0.1600 (2)    0.57042 (18)   0.08782 (8)    0.0565 (6)           
  H6A    0.0941        0.5046         0.0773         0.068\*              
  C7     0.3007 (3)    0.54772 (19)   0.05863 (8)    0.0604 (6)           
  H7A    0.3378        0.4686         0.0701         0.072\*              
  H7B    0.3687        0.6098         0.0702         0.072\*              
  C9     0.2197 (3)    0.6700 (2)     −0.02522 (9)   0.0637 (6)           
  H9A    0.2865        0.7359         −0.0179        0.076\*              
  H9B    0.2032        0.6664         −0.0659        0.076\*              
  C10    0.0817 (2)    0.6969 (2)     0.00449 (10)   0.0647 (6)           
  H10A   0.0103        0.6382         −0.0076        0.078\*              
  H10B   0.0490        0.7778         −0.0064        0.078\*              
  C11    0.0964 (2)    0.6912 (2)     0.06890 (10)   0.0657 (6)           
  H11A   0.1569        0.7578         0.0817         0.079\*              
  H11B   0.0034        0.7015         0.0862         0.079\*              
  C8     0.2838 (3)    0.5505 (2)     −0.00562 (8)   0.0655 (6)           
  H8A    0.3763        0.5396         −0.0233        0.079\*              
  H8B    0.2230        0.4834         −0.0175        0.079\*              
  C4     0.2130 (3)    0.6141 (2)     0.26409 (9)    0.0751 (7)           
  H4A    0.1503        0.6824         0.2557         0.090\*              
  H4B    0.3073        0.6319         0.2493         0.090\*              
  C3     0.2184 (4)    0.5887 (3)     0.32761 (10)   0.0947 (10)          
  H3A    0.3120        0.5596         0.3388         0.114\*              
  H3B    0.1960        0.6619         0.3492         0.114\*              
  C2     0.1095 (5)    0.4934 (3)     0.33665 (10)   0.1053 (11)          
  H2B    0.0163        0.5302         0.3418         0.126\*              
  H2C    0.1320        0.4451         0.3700         0.126\*              
  C1     0.1110 (4)    0.4151 (3)     0.28475 (9)    0.0917 (9)           
  H1A    0.1776        0.3477         0.2888         0.110\*              
  H1B    0.0169        0.3826         0.2768         0.110\*              
  ------ ------------- -------------- -------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  S1    0.1120 (6)    0.0526 (4)    0.0536 (4)    −0.0127 (3)    −0.0018 (3)    −0.0005 (2)
  N2    0.0950 (14)   0.0592 (11)   0.0406 (9)    −0.0187 (10)   0.0007 (8)     −0.0041 (7)
  N1    0.0922 (14)   0.0560 (10)   0.0393 (9)    0.0013 (9)     0.0052 (9)     −0.0024 (7)
  C5    0.0651 (13)   0.0519 (11)   0.0429 (10)   0.0033 (9)     0.0023 (9)     −0.0004 (8)
  C6    0.0732 (14)   0.0557 (12)   0.0408 (10)   −0.0137 (10)   −0.0010 (9)    −0.0014 (8)
  C7    0.0765 (14)   0.0565 (12)   0.0482 (11)   0.0150 (10)    −0.0002 (10)   0.0070 (9)
  C9    0.0625 (14)   0.0741 (14)   0.0545 (12)   −0.0005 (10)   −0.0019 (10)   0.0182 (10)
  C10   0.0600 (14)   0.0720 (14)   0.0620 (13)   0.0034 (11)    −0.0089 (10)   0.0097 (11)
  C11   0.0650 (14)   0.0706 (14)   0.0617 (13)   0.0093 (11)    0.0000 (10)    −0.0031 (11)
  C8    0.0774 (15)   0.0722 (14)   0.0468 (11)   0.0104 (12)    0.0073 (10)    0.0057 (10)
  C4    0.1016 (19)   0.0753 (14)   0.0484 (12)   −0.0030 (14)   −0.0013 (12)   −0.0143 (11)
  C3    0.139 (3)     0.096 (2)     0.0492 (13)   0.0122 (19)    −0.0130 (15)   −0.0142 (12)
  C2    0.155 (3)     0.119 (3)     0.0421 (14)   0.003 (2)      0.0090 (15)    0.0021 (14)
  C1    0.156 (3)     0.0742 (17)   0.0452 (13)   −0.0016 (16)   0.0119 (14)    0.0066 (11)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  ------------------- ------------- ------------------- -------------
  S1---C5             1.691 (2)     C10---H10A          0.9700
  N2---C5             1.346 (3)     C10---H10B          0.9700
  N2---C6             1.463 (2)     C11---H11A          0.9700
  N2---H2A            0.8600        C11---H11B          0.9700
  N1---C5             1.339 (3)     C8---H8A            0.9700
  N1---C1             1.462 (3)     C8---H8B            0.9700
  N1---C4             1.469 (3)     C4---C3             1.522 (3)
  C6---C7             1.509 (3)     C4---H4A            0.9700
  C6---C11            1.515 (3)     C4---H4B            0.9700
  C6---H6A            0.9800        C3---C2             1.475 (4)
  C7---C8             1.521 (3)     C3---H3A            0.9700
  C7---H7A            0.9700        C3---H3B            0.9700
  C7---H7B            0.9700        C2---C1             1.491 (4)
  C9---C10            1.500 (3)     C2---H2B            0.9700
  C9---C8             1.510 (3)     C2---H2C            0.9700
  C9---H9A            0.9700        C1---H1A            0.9700
  C9---H9B            0.9700        C1---H1B            0.9700
  C10---C11           1.524 (3)                         
                                                        
  C5---N2---C6        125.71 (17)   C10---C11---H11A    109.4
  C5---N2---H2A       117.1         C6---C11---H11B     109.4
  C6---N2---H2A       117.1         C10---C11---H11B    109.4
  C5---N1---C1        123.67 (19)   H11A---C11---H11B   108.0
  C5---N1---C4        124.49 (18)   C9---C8---C7        111.29 (18)
  C1---N1---C4        111.69 (18)   C9---C8---H8A       109.4
  N1---C5---N2        115.87 (18)   C7---C8---H8A       109.4
  N1---C5---S1        121.75 (16)   C9---C8---H8B       109.4
  N2---C5---S1        122.37 (15)   C7---C8---H8B       109.4
  N2---C6---C7        111.45 (17)   H8A---C8---H8B      108.0
  N2---C6---C11       109.34 (16)   N1---C4---C3        103.42 (19)
  C7---C6---C11       110.72 (16)   N1---C4---H4A       111.1
  N2---C6---H6A       108.4         C3---C4---H4A       111.1
  C7---C6---H6A       108.4         N1---C4---H4B       111.1
  C11---C6---H6A      108.4         C3---C4---H4B       111.1
  C6---C7---C8        110.99 (18)   H4A---C4---H4B      109.0
  C6---C7---H7A       109.4         C2---C3---C4        104.3 (2)
  C8---C7---H7A       109.4         C2---C3---H3A       110.9
  C6---C7---H7B       109.4         C4---C3---H3A       110.9
  C8---C7---H7B       109.4         C2---C3---H3B       110.9
  H7A---C7---H7B      108.0         C4---C3---H3B       110.9
  C10---C9---C8       111.75 (18)   H3A---C3---H3B      108.9
  C10---C9---H9A      109.3         C3---C2---C1        106.3 (2)
  C8---C9---H9A       109.3         C3---C2---H2B       110.5
  C10---C9---H9B      109.3         C1---C2---H2B       110.5
  C8---C9---H9B       109.3         C3---C2---H2C       110.5
  H9A---C9---H9B      107.9         C1---C2---H2C       110.5
  C9---C10---C11      112.17 (18)   H2B---C2---H2C      108.7
  C9---C10---H10A     109.2         N1---C1---C2        103.2 (2)
  C11---C10---H10A    109.2         N1---C1---H1A       111.1
  C9---C10---H10B     109.2         C2---C1---H1A       111.1
  C11---C10---H10B    109.2         N1---C1---H1B       111.1
  H10A---C10---H10B   107.9         C2---C1---H1B       111.1
  C6---C11---C10      111.34 (18)   H1A---C1---H1B      109.1
  C6---C11---H11A     109.4                             
  ------------------- ------------- ------------------- -------------
