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

For the synthesis, see: Mansuroğlu *et al.* ( 2008[@bb12]); Arslan *et al.* ( 2003*a* [@bb1],*b* [@bb4]); Binzet *et al.* ( 2006[@bb6]).  For general background, see: Arslan *et al.* ( 2006*a* [@bb3],*b* [@bb5], 2007[@bb2]); Kemp *et al.* ( 1997[@bb10]); Koch *et al.* ( 1995[@bb11]); Nencki (1873[@bb13]); Özpozan *et al.* ( 2000[@bb14]).  For related compounds, see: Arslan *et al.* ( 2003*a* [@bb1], 2006*b* [@bb5], 2007[@bb2]); Dong *et al.* ( 2008[@bb8]); Duque *et al.* ( 2008[@bb9]); Tutughamiarso & Bolte (2007[@bb16]); Yue *et al.* ( 2008[@bb19]); Yusof *et al.* ( 2008*a* [@bb20],*b* [@bb21]); Xian (2008[@bb18]); Thiam *et al.* ( 2008[@bb15]); Binzet *et al.* ( 2006[@bb6]); Uğur *et al.* ( 2006[@bb17]). 

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~14~H~12~ClN~3~OS*M* *~r~* = 305.78Triclinic,*a* = 8.255 (3) Å*b* = 9.030 (3) Å*c* = 9.957 (3) Åα = 80.810 (7)°β = 66.552 (7)°γ = 87.269 (7)°*V* = 672.1 (4) Å^3^*Z* = 2Mo *K*α radiationμ = 0.44 mm^−1^*T* = 120 (2) K0.20 × 0.14 × 0.10 mm

### Data collection {#sec2.1.2}

Bruker SMART CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2002[@bb7]) *T* ~min~ = 0.918, *T* ~max~ = 0.9583651 measured reflections2609 independent reflections1492 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.100

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.077*wR*(*F* ^2^) = 0.266*S* = 0.982609 reflections182 parametersH-atom parameters constrainedΔρ~max~ = 0.81 e Å^−3^Δρ~min~ = −0.50 e Å^−3^

 {#d5e571}

Data collection: *SMART* (Bruker, 2002[@bb7]); cell refinement: *SAINT* (Bruker, 2002[@bb7]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb22]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL*. 

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536808041123/hg2444sup1.cif](http://dx.doi.org/10.1107/S1600536808041123/hg2444sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536808041123/hg2444Isup2.hkl](http://dx.doi.org/10.1107/S1600536808041123/hg2444Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?hg2444&file=hg2444sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?hg2444sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?hg2444&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [HG2444](http://scripts.iucr.org/cgi-bin/sendsup?hg2444)). 

This work was supported by Mersin University Research Fund (Project Nos.  BAP-ECZ-F-TBB-(HA) 2004--3 and BAP-FEF-KB-(NK) 2006--3). 

Comment
=======

Thiourea derivatives, first synthesized by Nencki, 1873, are very flexible ligands and able to coordinate to a range of metal centers as neutral ligands, monoanions or dianions (Mansuroğlu *et al.*,  2008; Arslan *et al.*,  2003*b*, 2006*a*; Binzet *et al.*,  2006; Kemp *et al.*,  1997; Koch *et al.*,  1995).  In addition, the oxygen, nitrogen and sulfur donors provide a multitude of bonding possibilities.  The coordination chemistry of substituted thioureas has led to some interesting practical applications such as liquid--liquid extraction, pre-concentration and highly efficient chromatographic separation (Kemp *et al.*,  1997; Koch *et al.*,  1995). 

Our team focused on the synthesis, characterization, crystal structure, thermal behavior and antimicrobial activity of new thiourea derivatives (Mansuroğlu *et al.*,  2008; Arslan *et al.*,  2003*a*, 2003*b*, 2006*a*, 2006*b*, 2007; Uğur *et al.*,  2006; Özpozan *et al.*,  2000).  In this article, we report the preparation and characterization of a novel thiourea compound, 4-chloro-*N*-(6-methylpyridin-2-yl-carbamothioyl)benzamide (I), and its crystal structure.  The title compound was purified by re-crystallization from ethanol:dichloromethane mixture (1:2) and characterized by elemental analysis.  The analytical data is consistent with the proposed structure given in Scheme 1. 

The molecular structure and packing diagram are depicted in Figure 1 and 2, respectively.  The bond lengths and angles in the thiourea moiety are typical for thiourea derivatives; the C8---S1 and C7---O1 bonds both show a typical double-bond character with 1.655 (5) and 1.203 (6) Å, respectively.  The short bond lengths of the N1---C7, 1.395 (7); N1---C8, 1.376 (6) and N2---C8, 1.364 (6) Å bonds indicate partial double bond character.  These results can be explained by the existence of resonance in this part of the molecule.  The other C---N bond length is within the expected range. 

A lot of substitute benzoylthiourea derivatives have *cis*-*trans* configurations (Yusof, *et al.*,  2008*a*, 2008*b*; Thiam, *et al.*,  2008; Xian, 2008; Dong, *et al.*,  2008; Duque, *et al.*,  2008).  However, the title compound shows an intramolecular N---H···N hydrogen bond (Table 1) which results in the formation of a six membered ring (N3---C9---N2---C8---N1---H1) and leads to a *syn*-periplanar conformation between the thiocarbonyl group carbon atom and the pyridine group nitrogen atom (Tutughamiarso & Bolte, 2007; Yue *et al.*,  2008).  The torsion angles in this region, C8---N2---C9---N3, 14.9 (9)° and C9---N2---C8---N1, -7.2 (8)° confirm this conformation.  This formation forces the two amide hydrogen atoms to the opposite direction. 

The carbonyl and thiocarbonyl part is essentially planar, as reflected by the torsional angles O1---C7---N1---C8, C7---N1---C8---S1 and C7---N1---C8---N2 of 1.7 (9), 0.3 (8) and 179.3 (5) °, respectively.  O1, C7, N1, C8 and S1 fragment is also planar (maximum and mean deviations are 0.010 and 0.005 Å, respectively). 

The crystal packing is shown in Fig.  2.  There are two intermolecular, N---H···S and C---H···O, hydrogen bonds which connect molecules in chains parallel to \[100\]. 

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

The compound was prepared with a procedure similar to that reported in the literature (Arslan *et al.*,  2003*b*, 2006*a*).  A solution of 4-chloro-benzoyl chloride (0.01 mol) in acetone (50 cm^3^) was added dropwise to a suspension of potassium thiocyanate (0.01 mol) in acetone (30 cm^3^).  The reaction mixture was heated under reflux for 30 min, and then cooled to room temperature.  A solution of 6-methylpyridin-2-amine (0.01 mol) in acetone (10 cm^3^) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 cm^3^) was added to the solution, which was then filtered.  The solid product was washed with water and purifed by recrystalization from an ethanol:dichloromethane mixture (1:2).  Anal.  Calcd.  for C~14~H~12~ClN~3~OS: C, 55.0; H, 4.0; N, 13.7.  Found: C, 55.1; H, 3.9; N, 13.7%. 

Figures
=======

![ The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.](e-65-00o81-fig1){#Fap1}

![ Packing diagram for (I) viewed along a-direction.  Hydrogen bonds shown as dotted lines.](e-65-00o81-fig2){#Fap2}

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

  ---------------------- --------------------------------------
  C~14~H~12~ClN~3~OS     *Z* = 2
  *M~r~* = 305.78        *F*(000) = 316
  Triclinic, *P*1        *D*~x~ = 1.511 Mg m^−3^
  Hall symbol: -P 1      Mo *K*α radiation, λ = 0.71073 Å
  *a* = 8.255 (3) Å      Cell parameters from 716 reflections
  *b* = 9.030 (3) Å      θ = 2.3--26.3°
  *c* = 9.957 (3) Å      µ = 0.44 mm^−1^
  α = 80.810 (7)°        *T* = 120 K
  β = 66.552 (7)°        Prism, yellow
  γ = 87.269 (7)°        0.20 × 0.14 × 0.10 mm
  *V* = 672.1 (4) Å^3^   
  ---------------------- --------------------------------------

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

  ------------------------------------------------------------ --------------------------------------
  Bruker SMART CCD area-detector diffractometer                2609 independent reflections
  Radiation source: sealed tube                                1492 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.100
  φ and ω scans                                                θ~max~ = 26.4°, θ~min~ = 2.3°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2002)   *h* = −10→10
  *T*~min~ = 0.918, *T*~max~ = 0.958                           *k* = −11→5
  3651 measured reflections                                    *l* = −12→10
  ------------------------------------------------------------ --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.077   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.266                  H-atom parameters constrained
  *S* = 0.98                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.1601*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  2609 reflections                      (Δ/σ)~max~ \< 0.001
  182 parameters                        Δρ~max~ = 0.81 e Å^−3^
  0 restraints                          Δρ~min~ = −0.50 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~   
  Cl1    −0.0760 (2)   −0.08311 (16)   0.24521 (19)   0.0469 (5)           
  S1     0.4068 (2)    0.83271 (15)    0.20068 (15)   0.0316 (5)           
  O1     0.2334 (6)    0.5331 (4)      0.3623 (4)     0.0370 (10)          
  N1     0.2869 (6)    0.6040 (5)      0.1158 (5)     0.0296 (11)          
  H1B    0.2730        0.5725          0.0418         0.036\*              
  N2     0.4090 (6)    0.8104 (5)      −0.0583 (5)    0.0282 (11)          
  H2B    0.4462        0.9040          −0.0760        0.034\*              
  N3     0.3162 (6)    0.6306 (5)      −0.1620 (5)    0.0253 (10)          
  C1     0.0432 (8)    0.2777 (6)      0.3757 (6)     0.0347 (14)          
  H1A    0.0183        0.3141          0.4662         0.042\*              
  C2     −0.0314 (8)   0.1427 (6)      0.3760 (7)     0.0394 (15)          
  H2A    −0.1122       0.0888          0.4661         0.047\*              
  C3     0.0122 (8)    0.0878 (6)      0.2450 (6)     0.0322 (13)          
  C4     0.1259 (8)    0.1664 (6)      0.1110 (6)     0.0365 (15)          
  H4A    0.1537        0.1280          0.0211         0.044\*              
  C5     0.1987 (7)    0.3030 (6)      0.1107 (6)     0.0264 (12)          
  H5A    0.2783        0.3572          0.0201         0.032\*              
  C6     0.1558 (7)    0.3597 (5)      0.2407 (6)     0.0258 (12)          
  C7     0.2278 (7)    0.5061 (6)      0.2497 (6)     0.0272 (12)          
  C8     0.3644 (6)    0.7438 (5)      0.0850 (6)     0.0208 (11)          
  C9     0.4067 (7)    0.7576 (6)      −0.1828 (6)    0.0261 (12)          
  C10    0.5010 (7)    0.8375 (6)      −0.3213 (6)    0.0291 (13)          
  H10A   0.5701        0.9232          −0.3321        0.035\*              
  C11    0.4925 (8)    0.7902 (6)      −0.4435 (6)    0.0316 (13)          
  H11A   0.5503        0.8463          −0.5394        0.038\*              
  C12    0.3987 (7)    0.6598 (6)      −0.4245 (6)    0.0287 (13)          
  H12A   0.3913        0.6251          −0.5071        0.034\*              
  C13    0.3156 (7)    0.5806 (6)      −0.2823 (6)    0.0229 (12)          
  C14    0.2159 (8)    0.4360 (6)      −0.2553 (7)    0.0322 (13)          
  H14A   0.2846        0.3515          −0.2327        0.048\*              
  H14B   0.1965        0.4249          −0.3441        0.048\*              
  H14C   0.1018        0.4375          −0.1715        0.048\*              
  ------ ------------- --------------- -------------- -------------------- --

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

  ----- ------------- ------------ ------------- -------------- ------------- --------------
        *U*^11^       *U*^22^      *U*^33^       *U*^12^        *U*^13^       *U*^23^
  Cl1   0.0577 (11)   0.0250 (8)   0.0548 (11)   −0.0248 (7)    −0.0183 (9)   −0.0001 (7)
  S1    0.0473 (10)   0.0223 (7)   0.0274 (8)    −0.0173 (6)    −0.0164 (7)   −0.0004 (6)
  O1    0.053 (3)     0.030 (2)    0.029 (2)     −0.0182 (19)   −0.017 (2)    −0.0027 (17)
  N1    0.043 (3)     0.023 (2)    0.022 (2)     −0.019 (2)     −0.009 (2)    −0.0055 (19)
  N2    0.038 (3)     0.020 (2)    0.027 (2)     −0.0162 (19)   −0.013 (2)    −0.0017 (18)
  N3    0.024 (2)     0.022 (2)    0.034 (3)     −0.0071 (18)   −0.015 (2)    −0.0014 (19)
  C1    0.059 (4)     0.022 (3)    0.019 (3)     −0.015 (3)     −0.012 (3)    0.004 (2)
  C2    0.045 (4)     0.027 (3)    0.034 (3)     −0.022 (3)     −0.003 (3)    0.003 (3)
  C3    0.040 (3)     0.022 (3)    0.029 (3)     −0.019 (2)     −0.009 (3)    0.005 (2)
  C4    0.064 (4)     0.021 (3)    0.024 (3)     −0.014 (3)     −0.017 (3)    0.001 (2)
  C5    0.033 (3)     0.020 (3)    0.026 (3)     −0.013 (2)     −0.015 (2)    0.007 (2)
  C6    0.030 (3)     0.017 (3)    0.030 (3)     −0.008 (2)     −0.013 (3)    0.004 (2)
  C7    0.035 (3)     0.020 (3)    0.027 (3)     −0.009 (2)     −0.015 (3)    0.002 (2)
  C8    0.020 (3)     0.017 (2)    0.029 (3)     0.000 (2)      −0.016 (2)    0.004 (2)
  C9    0.043 (3)     0.017 (3)    0.020 (3)     −0.009 (2)     −0.016 (3)    0.004 (2)
  C10   0.036 (3)     0.020 (3)    0.032 (3)     −0.013 (2)     −0.015 (3)    0.003 (2)
  C11   0.047 (4)     0.020 (3)    0.024 (3)     −0.013 (2)     −0.011 (3)    0.001 (2)
  C12   0.036 (3)     0.025 (3)    0.024 (3)     −0.014 (2)     −0.010 (2)    −0.004 (2)
  C13   0.027 (3)     0.021 (3)    0.026 (3)     −0.004 (2)     −0.016 (2)    0.001 (2)
  C14   0.042 (3)     0.024 (3)    0.038 (3)     −0.011 (2)     −0.022 (3)    −0.006 (2)
  ----- ------------- ------------ ------------- -------------- ------------- --------------

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

  -------------------- ------------ ----------------------- ------------
  Cl1---C3             1.737 (5)    C4---C5                 1.396 (7)
  S1---C8              1.655 (5)    C4---H4A                0.9500
  O1---C7              1.203 (6)    C5---C6                 1.376 (7)
  N1---C8              1.376 (6)    C5---H5A                0.9500
  N1---C7              1.395 (7)    C6---C7                 1.504 (7)
  N1---H1B             0.8800       C9---C10                1.382 (7)
  N2---C8              1.364 (6)    C10---C11               1.379 (7)
  N2---C9              1.405 (6)    C10---H10A              0.9500
  N2---H2B             0.8800       C11---C12               1.386 (7)
  N3---C9              1.341 (6)    C11---H11A              0.9500
  N3---C13             1.347 (7)    C12---C13               1.392 (7)
  C1---C2              1.391 (7)    C12---H12A              0.9500
  C1---C6              1.405 (7)    C13---C14               1.506 (7)
  C1---H1A             0.9500       C14---H14A              0.9800
  C2---C3              1.375 (8)    C14---H14B              0.9800
  C2---H2A             0.9500       C14---H14C              0.9800
  C3---C4              1.390 (8)                            
                                                            
  C8---N1---C7         128.0 (4)    O1---C7---C6            122.3 (5)
  C8---N1---H1B        116.0        N1---C7---C6            113.2 (4)
  C7---N1---H1B        116.0        N2---C8---N1            113.5 (4)
  C8---N2---C9         132.1 (4)    N2---C8---S1            119.5 (4)
  C8---N2---H2B        113.9        N1---C8---S1            127.1 (4)
  C9---N2---H2B        113.9        N3---C9---C10           123.1 (5)
  C9---N3---C13        118.0 (5)    N3---C9---N2            118.5 (5)
  C2---C1---C6         119.5 (5)    C10---C9---N2           118.3 (5)
  C2---C1---H1A        120.2        C11---C10---C9          118.6 (5)
  C6---C1---H1A        120.2        C11---C10---H10A        120.7
  C3---C2---C1         119.7 (5)    C9---C10---H10A         120.7
  C3---C2---H2A        120.2        C10---C11---C12         119.2 (5)
  C1---C2---H2A        120.2        C10---C11---H11A        120.4
  C2---C3---C4         121.4 (5)    C12---C11---H11A        120.4
  C2---C3---Cl1        119.9 (4)    C11---C12---C13         118.8 (5)
  C4---C3---Cl1        118.7 (4)    C11---C12---H12A        120.6
  C3---C4---C5         118.8 (5)    C13---C12---H12A        120.6
  C3---C4---H4A        120.6        N3---C13---C12          122.1 (5)
  C5---C4---H4A        120.6        N3---C13---C14          116.7 (5)
  C6---C5---C4         120.5 (5)    C12---C13---C14         121.2 (5)
  C6---C5---H5A        119.8        C13---C14---H14A        109.5
  C4---C5---H5A        119.8        C13---C14---H14B        109.5
  C5---C6---C1         120.1 (5)    H14A---C14---H14B       109.5
  C5---C6---C7         123.7 (5)    C13---C14---H14C        109.5
  C1---C6---C7         116.2 (5)    H14A---C14---H14C       109.5
  O1---C7---N1         124.4 (5)    H14B---C14---H14C       109.5
                                                            
  C6---C1---C2---C3    3.0 (10)     C9---N2---C8---N1       −7.2 (8)
  C1---C2---C3---C4    −1.9 (10)    C9---N2---C8---S1       172.4 (5)
  C1---C2---C3---Cl1   178.3 (5)    C7---N1---C8---N2       179.3 (5)
  C2---C3---C4---C5    0.9 (10)     C7---N1---C8---S1       −0.3 (8)
  Cl1---C3---C4---C5   −179.3 (4)   C13---N3---C9---C10     −1.1 (8)
  C3---C4---C5---C6    −1.2 (9)     C13---N3---C9---N2      −179.7 (4)
  C4---C5---C6---C1    2.3 (9)      C8---N2---C9---N3       14.9 (9)
  C4---C5---C6---C7    −179.8 (5)   C8---N2---C9---C10      −163.8 (5)
  C2---C1---C6---C5    −3.3 (9)     N3---C9---C10---C11     4.4 (9)
  C2---C1---C6---C7    178.7 (5)    N2---C9---C10---C11     −177.0 (5)
  C8---N1---C7---O1    1.7 (9)      C9---C10---C11---C12    −3.7 (8)
  C8---N1---C7---C6    −177.9 (5)   C10---C11---C12---C13   0.1 (9)
  C5---C6---C7---O1    −157.3 (6)   C9---N3---C13---C12     −2.8 (8)
  C1---C6---C7---O1    20.7 (8)     C9---N3---C13---C14     178.7 (5)
  C5---C6---C7---N1    22.3 (8)     C11---C12---C13---N3    3.3 (8)
  C1---C6---C7---N1    −159.7 (5)   C11---C12---C13---C14   −178.3 (5)
  -------------------- ------------ ----------------------- ------------

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

  -------------------- --------- --------- ----------- ---------------
  *D*---H···*A*        *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C12---H12A···O1^i^   0.95      2.42      3.303 (7)   154
  N2---H2B···S1^ii^    0.88      2.61      3.464 (5)   165
  N1---H1B···N3        0.88      1.90      2.651 (7)   142
  -------------------- --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*          *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  -------------------- --------- ------- ----------- -------------
  C12---H12*A*⋯O1^i^   0.95      2.42    3.303 (7)   154
  N2---H2*B*⋯S1^ii^    0.88      2.61    3.464 (5)   165
  N1---H1*B*⋯N3        0.88      1.90    2.651 (7)   142

Symmetry codes: (i) ; (ii) .