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

For related structures, see: Hökelek *et al.* (1998[@bb5]); Ianelli *et al.* (1994[@bb6]); Çaylak *et al.* (2007[@bb2]); Rodriguez *et al.* (1989[@bb9]). Hückel calculations were performed using *Chem3DPro* (Cambridgesoft, 2009[@bb1]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~12~H~11~NS*M* *~r~* = 201.28Monoclinic,*a* = 8.6353 (14) Å*b* = 12.1395 (15) Å*c* = 9.5808 (14) Åβ = 104.599 (10)°*V* = 971.9 (2) Å^3^*Z* = 4Mo *K*α radiationμ = 0.29 mm^−1^*T* = 90 K0.38 × 0.33 × 0.15 mm

### Data collection {#sec2.1.2}

Nonius KappaCCD diffractometerAbsorption correction: multi-scan (*SCALEPACK*; Otwinowski & Minor, 1997[@bb8]) *T* ~min~ = 0.900, *T* ~max~ = 0.9586145 measured reflections3305 independent reflections2915 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.018

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.033*wR*(*F* ^2^) = 0.087*S* = 1.043305 reflections128 parametersH-atom parameters constrainedΔρ~max~ = 0.42 e Å^−3^Δρ~min~ = −0.30 e Å^−3^

 {#d5e417}

Data collection: *COLLECT* (Nonius, 2000[@bb7]); cell refinement: *SCALEPACK* (Otwinowski & Minor, 1997[@bb8]); data reduction: *DENZO* (Otwinowski & Minor, 1997[@bb8]) and *SCALEPACK*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb10]); molecular graphics: *ORTEP-3 for Windows* (Farrugia, 1997[@bb3]); software used to prepare material for publication: *WinGX* (Farrugia, 1999[@bb4]).

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536811006623/fl2336sup1.cif](http://dx.doi.org/10.1107/S1600536811006623/fl2336sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536811006623/fl2336Isup2.hkl](http://dx.doi.org/10.1107/S1600536811006623/fl2336Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?fl2336&file=fl2336sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?fl2336sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?fl2336&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [FL2336](http://scripts.iucr.org/cgi-bin/sendsup?fl2336)).

The purchase of the diffractometer was made possible by grant No. LEQSF(1999--2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

Comment
=======

The title compound (1, Fig.1) is the sulfur analog of substituted carbazole 1,2,3-trihydrocarbazol-4(9*H*)-one (2) (Rodriguez *et al.*, 1989). Both 1 and 2 show the same molecular conformation (envelope, with flap angles 48.6 (1)° for 1 and 48.2 (1)° for 2) and similar H-bonded chains (Table 1) of alternating enantiomers (N···S = 3.319 (1) Å, N---H···S = 172.0 (1)°, and N···S═C = 98.0 (1)° for 1, N···O = 2.829 (1) Å, N---H···O = 162.3 (1)° and H···O═C = 117.5 (1)° for 2).

In 1, all H-bonded chains are parallel, extending along the \[101\] crystallographic direction, and adjacent chains 5.583 (1) Å apart are arranged in corrugated sheets parallel to the (010) crystallographic plane (Fig. 22)). The mean planes of adjacent sheets are 5.099 (1) Å apart, but enantiomers in adjacent sheets have parallel π-nodal planes and are only 3.466 (1) Å apart, indicative of a π-π\* interaction. Extended Hückel calculations (*Chem3DPro*, Cambridgesoft, 2009) suggest that the π-HOMO and π\*-LUMO orbitals in 1 are larger and closer in energy than those in 2. This may explain why molecules of 2 show no π-type interaction and are thus packed in a different pattern: H-bonded chains 5.359 (1) Å apart extend along the \[011\] and \[011\] directions in alternating sheets, so adjacent sheets are rotated by 76.5 (1)°. The distance between adjacent sheets is 4.979 (1) Å and the only interactions between them are C---H···C van der Waals and C---H···O contacts.

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

A solution of 1,2-dihydrocarbazol-4(3*H*)-one (5.4 mmol) in anhydrous 1,2-dimethoxyethane (30 ml) was stirred at room temperature for 15 min. Upon dissolution, the solution was chilled in an ice-water bath. Lawesson reagent, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, (2.9 mmol) was added to the vigorously stirred cold solution. The resulting mixture was stirred for 5 min and then allowed to warm to room temperature. After stirring for an additional 10 min, the white suspension dissolved, and the reaction mixture turned deep orange. The reaction mixture was poured into 150 ml of chilled water and the orange suspension was extracted with CHCl~3~ (3 *x* 80 ml). Evaporation under reduced pressure left a deep orange residue, which was purified on a silica column (100 g). The orange band was eluted with ethyl acetate. Evaporation of the solvent *in vacuo* gave the title compound as a yellow powder (92%). Recrystallization from dichloromethane yielded yellow needles, m.p. 173--175°C.

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

All H atoms were placed in calculated positions, guided by difference maps, with C---H bond distances 0.95--0.99 Å, N---H 0.88 Å, *U*~iso~=1.2*U*~eq~, and thereafter refined as riding.

Figures
=======

![View of 1 (50% probability displacement ellipsoids).](e-67-0o757-fig1){#Fap1}

![The unit cell, illustrating hydrogen bonds.](e-67-0o757-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~12~H~11~NS              *F*(000) = 424
  *M~r~* = 201.28           *D*~x~ = 1.376 Mg m^−3^
  Monoclinic, *P*2~1~/*n*   Melting point: 447(1) K
  Hall symbol: -P 2yn       Mo *K*α radiation, λ = 0.71073 Å
  *a* = 8.6353 (14) Å       Cell parameters from 3145 reflections
  *b* = 12.1395 (15) Å      θ = 2.8--31.8°
  *c* = 9.5808 (14) Å       µ = 0.29 mm^−1^
  β = 104.599 (10)°         *T* = 90 K
  *V* = 971.9 (2) Å^3^      Prism, yellow
  *Z* = 4                   0.38 × 0.33 × 0.15 mm
  ------------------------- ---------------------------------------

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

  --------------------------------------------------------------------------- --------------------------------------
  Nonius KappaCCD diffractometer                                              2915 reflections with *I* \> 2σ(*I*)
  ω and φ scans                                                               *R*~int~ = 0.018
  Absorption correction: multi-scan (*SCALEPACK*; Otwinowski & Minor, 1997)   θ~max~ = 31.8°, θ~min~ = 2.8°
  *T*~min~ = 0.900, *T*~max~ = 0.958                                          *h* = −12→12
  6145 measured reflections                                                   *k* = −17→15
  3305 independent reflections                                                *l* = −14→14
  --------------------------------------------------------------------------- --------------------------------------

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

  ------------------------------------- ----------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  H-atom parameters constrained
  Least-squares matrix: full            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0381*P*)^2^ + 0.4607*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.033   (Δ/σ)~max~ = 0.001
  *wR*(*F*^2^) = 0.087                  Δρ~max~ = 0.42 e Å^−3^
  *S* = 1.03                            Δρ~min~ = −0.30 e Å^−3^
  3305 reflections                      Extinction correction: *SHELXL97* (Sheldrick, 2008), Fc^\*^=kFc\[1+0.001xFc^2^λ^3^/sin(2θ)\]^-1/4^
  128 parameters                        Extinction coefficient: 0.007 (2)
  0 restraints                          
  ------------------------------------- ----------------------------------------------------------------------------------------------------

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.
  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ----- -------------- -------------- -------------- -------------------- --
        *x*            *y*            *z*            *U*~iso~\*/*U*~eq~   
  S1    0.73572 (3)    0.09251 (2)    0.17793 (3)    0.01632 (8)          
  N9    0.40190 (10)   0.23264 (7)    0.49231 (9)    0.01459 (16)         
  H9    0.3596         0.2739         0.5486         0.018\*              
  C1    0.64126 (13)   0.35282 (8)    0.50486 (11)   0.01640 (19)         
  H1A   0.6442         0.3693         0.6067         0.02\*               
  H1B   0.5975         0.4178         0.4456         0.02\*               
  C2    0.81014 (12)   0.32729 (9)    0.49014 (11)   0.01613 (19)         
  H2A   0.8612         0.2724         0.5639         0.019\*              
  H2B   0.8756         0.3953         0.5072         0.019\*              
  C3    0.80512 (12)   0.28219 (8)    0.33970 (11)   0.01504 (18)         
  H3A   0.766          0.3409         0.2677         0.018\*              
  H3B   0.9153         0.2631         0.3355         0.018\*              
  C4    0.69952 (12)   0.18152 (8)    0.29869 (10)   0.01239 (17)         
  C5    0.40380 (12)   −0.00895 (8)   0.27655 (10)   0.01451 (18)         
  H5    0.4724         −0.0398        0.2234         0.017\*              
  C6    0.26491 (13)   −0.06343 (9)   0.28577 (11)   0.0179 (2)           
  H6    0.2394         −0.1325        0.2389         0.021\*              
  C7    0.16174 (13)   −0.01841 (9)   0.36297 (12)   0.0196 (2)           
  H7    0.0665         −0.0567        0.3655         0.024\*              
  C8    0.19647 (13)   0.08102 (9)    0.43570 (11)   0.0181 (2)           
  H8    0.1273         0.1116         0.4885         0.022\*              
  C10   0.53890 (12)   0.25494 (8)    0.45510 (10)   0.01313 (17)         
  C11   0.56930 (11)   0.17216 (8)    0.36283 (10)   0.01191 (17)         
  C12   0.44039 (11)   0.09230 (8)    0.34726 (10)   0.01234 (17)         
  C13   0.33703 (12)   0.13394 (8)    0.42784 (10)   0.01382 (18)         
  ----- -------------- -------------- -------------- -------------------- --

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

  ----- -------------- -------------- -------------- -------------- ------------- --------------
        *U*^11^        *U*^22^        *U*^33^        *U*^12^        *U*^13^       *U*^23^
  S1    0.01819 (13)   0.01449 (12)   0.01981 (13)   −0.00184 (8)   0.01132 (9)   −0.00327 (8)
  N9    0.0156 (4)     0.0158 (4)     0.0144 (4)     0.0018 (3)     0.0077 (3)    −0.0002 (3)
  C1    0.0194 (5)     0.0149 (4)     0.0159 (4)     −0.0014 (4)    0.0063 (4)    −0.0029 (3)
  C2    0.0162 (4)     0.0168 (4)     0.0150 (4)     −0.0032 (4)    0.0031 (3)    −0.0016 (3)
  C3    0.0149 (4)     0.0145 (4)     0.0167 (4)     −0.0031 (3)    0.0059 (3)    −0.0012 (3)
  C4    0.0128 (4)     0.0125 (4)     0.0123 (4)     0.0008 (3)     0.0041 (3)    0.0011 (3)
  C5    0.0149 (4)     0.0145 (4)     0.0141 (4)     −0.0005 (3)    0.0035 (3)    0.0017 (3)
  C6    0.0182 (5)     0.0169 (5)     0.0175 (4)     −0.0039 (4)    0.0027 (4)    0.0026 (4)
  C7    0.0156 (5)     0.0230 (5)     0.0204 (5)     −0.0045 (4)    0.0049 (4)    0.0056 (4)
  C8    0.0140 (4)     0.0235 (5)     0.0182 (4)     0.0001 (4)     0.0068 (4)    0.0046 (4)
  C10   0.0140 (4)     0.0142 (4)     0.0115 (4)     0.0012 (3)     0.0039 (3)    0.0012 (3)
  C11   0.0120 (4)     0.0126 (4)     0.0115 (4)     0.0001 (3)     0.0037 (3)    0.0005 (3)
  C12   0.0117 (4)     0.0142 (4)     0.0115 (4)     0.0006 (3)     0.0035 (3)    0.0026 (3)
  C13   0.0136 (4)     0.0160 (4)     0.0126 (4)     0.0011 (3)     0.0046 (3)    0.0026 (3)
  ----- -------------- -------------- -------------- -------------- ------------- --------------

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

  ---------------------- ------------- ----------------------- --------------
  C1---C10               1.4860 (14)   C5---H5                 0.95
  C1---C2                1.5318 (14)   C6---C7                 1.4042 (16)
  C1---H1A               0.99          C6---H6                 0.95
  C1---H1B               0.99          C7---C8                 1.3882 (16)
  C2---C3                1.5322 (14)   C7---H7                 0.95
  C2---H2A               0.99          C8---C13                1.3920 (14)
  C2---H2B               0.99          C8---H8                 0.95
  C3---C4                1.5162 (14)   C10---N9                1.3463 (12)
  C3---H3A               0.99          C10---C11               1.4061 (13)
  C3---H3B               0.99          C11---C12               1.4553 (13)
  C4---C11               1.4154 (13)   C12---C13               1.4127 (13)
  C4---S1                1.6692 (10)   C13---N9                1.3988 (13)
  C5---C6                1.3917 (14)   N9---H9                 0.88
  C5---C12               1.4006 (13)                           
                                                               
  C10---C1---C2          108.17 (8)    C5---C6---C7            121.32 (10)
  C10---C1---H1A         110.1         C5---C6---H6            119.3
  C2---C1---H1A          110.1         C7---C6---H6            119.3
  C10---C1---H1B         110.1         C8---C7---C6            121.15 (10)
  C2---C1---H1B          110.1         C8---C7---H7            119.4
  H1A---C1---H1B         108.4         C6---C7---H7            119.4
  C1---C2---C3           110.92 (8)    C7---C8---C13           117.08 (10)
  C1---C2---H2A          109.5         C7---C8---H8            121.5
  C3---C2---H2A          109.5         C13---C8---H8           121.5
  C1---C2---H2B          109.5         N9---C10---C11          109.79 (9)
  C3---C2---H2B          109.5         N9---C10---C1           124.55 (9)
  H2A---C2---H2B         108           C11---C10---C1          125.66 (9)
  C4---C3---C2           113.85 (8)    C10---C11---C4          120.68 (9)
  C4---C3---H3A          108.8         C10---C11---C12         106.34 (8)
  C2---C3---H3A          108.8         C4---C11---C12          132.83 (9)
  C4---C3---H3B          108.8         C5---C12---C13          118.80 (9)
  C2---C3---H3B          108.8         C5---C12---C11          135.05 (9)
  H3A---C3---H3B         107.7         C13---C12---C11         106.14 (8)
  C11---C4---C3          116.35 (8)    C8---C13---N9           128.98 (9)
  C11---C4---S1          123.85 (7)    C8---C13---C12          122.96 (10)
  C3---C4---S1           119.73 (7)    N9---C13---C12          108.06 (8)
  C6---C5---C12          118.64 (9)    C10---N9---C13          109.64 (8)
  C6---C5---H5           120.7         C10---N9---H9           125.2
  C12---C5---H5          120.7         C13---N9---H9           125.2
                                                               
  C10---C1---C2---C3     49.84 (11)    C6---C5---C12---C13     1.45 (14)
  C1---C2---C3---C4      −55.67 (11)   C6---C5---C12---C11     −179.79 (10)
  C2---C3---C4---C11     28.23 (12)    C10---C11---C12---C5    −177.03 (10)
  C2---C3---C4---S1      −154.52 (8)   C4---C11---C12---C5     7.46 (19)
  C12---C5---C6---C7     0.52 (15)     C10---C11---C12---C13   1.84 (10)
  C5---C6---C7---C8      −1.47 (16)    C4---C11---C12---C13    −173.67 (10)
  C6---C7---C8---C13     0.35 (15)     C7---C8---C13---N9      −178.60 (10)
  C2---C1---C10---N9     158.35 (9)    C7---C8---C13---C12     1.70 (15)
  C2---C1---C10---C11    −21.72 (13)   C5---C12---C13---C8     −2.64 (14)
  N9---C10---C11---C4    174.61 (9)    C11---C12---C13---C8    178.27 (9)
  C1---C10---C11---C4    −5.33 (15)    C5---C12---C13---N9     177.61 (8)
  N9---C10---C11---C12   −1.56 (11)    C11---C12---C13---N9    −1.47 (10)
  C1---C10---C11---C12   178.50 (9)    C11---C10---N9---C13    0.66 (11)
  C3---C4---C11---C10    2.22 (13)     C1---C10---N9---C13     −179.40 (9)
  S1---C4---C11---C10    −174.91 (7)   C8---C13---N9---C10     −179.18 (10)
  C3---C4---C11---C12    177.20 (10)   C12---C13---N9---C10    0.55 (11)
  S1---C4---C11---C12    0.08 (16)                             
  ---------------------- ------------- ----------------------- --------------

Hydrogen-bond geometry (Å, °) {#tablewraphbondslong}
=============================

  ----------------- --------- --------- ------------ ---------------
  *D*---H···*A*     *D*---H   H···*A*   *D*···*A*    *D*---H···*A*
  N9---H9···S1^i^   0.88      2.45      3.3187 (9)   172
  ----------------- --------- --------- ------------ ---------------

Symmetry codes: (i) *x*−1/2, −*y*+1/2, *z*+1/2.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*     *D*---H   H⋯*A*   *D*⋯*A*      *D*---H⋯*A*
  --------------- --------- ------- ------------ -------------
  N9---H9⋯S1^i^   0.88      2.45    3.3187 (9)   172

Symmetry code: (i) .

[^1]: Current address: Winston-Salem State University, Winston-Salem, NC 27110, USA.

[^2]: Current address: University of South Florida, Tampa, Florida 33620, USA.
