# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smk-164

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 N S'
_chemical_formula_weight         164.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.9271(15)
_cell_length_b                   12.790(3)
_cell_length_c                   12.361(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.163(13)
_cell_angle_gamma                90.00
_cell_volume                     922.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8365
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         28.58
_reflns_number_total             2267
_reflns_number_gt                1606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2267
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.755
_refine_ls_shift/su_mean         0.029

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.12244(7) 0.31720(3) 0.61691(4) 0.0620(2) Uani 1 1 d . . .
N1 N 0.7236(2) 0.27270(12) 0.48971(12) 0.0579(4) Uani 1 1 d . . .
C4 C 0.8664(2) 0.14272(11) 0.62666(12) 0.0413(3) Uani 1 1 d . . .
C3 C 0.8906(2) 0.24433(11) 0.57057(13) 0.0447(4) Uani 1 1 d . . .
C5 C 0.6884(3) 0.12599(13) 0.68358(14) 0.0533(4) Uani 1 1 d . . .
H5 H 0.5775 0.1773 0.6842 0.064 Uiso 1 1 calc R . .
C2 C 0.5364(3) 0.20376(15) 0.43882(16) 0.0660(5) Uani 1 1 d . . .
H2A H 0.5654 0.1339 0.4661 0.099 Uiso 1 1 calc R . .
H2B H 0.5271 0.2041 0.3605 0.099 Uiso 1 1 calc R . .
H2C H 0.3942 0.2282 0.4566 0.099 Uiso 1 1 calc R . .
C9 C 1.0289(3) 0.06444(12) 0.62618(14) 0.0509(4) Uani 1 1 d . . .
H9 H 1.1499 0.0746 0.5886 0.061 Uiso 1 1 calc R . .
C7 C 0.8366(3) -0.04334(13) 0.73829(16) 0.0625(5) Uani 1 1 d . . .
H7 H 0.8272 -0.1055 0.7763 0.075 Uiso 1 1 calc R . .
C8 C 1.0115(3) -0.02805(13) 0.68117(16) 0.0616(5) Uani 1 1 d . . .
H8 H 1.1195 -0.0805 0.6794 0.074 Uiso 1 1 calc R . .
C6 C 0.6751(3) 0.03320(13) 0.73948(16) 0.0627(5) Uani 1 1 d . . .
H6 H 0.5559 0.0226 0.7781 0.075 Uiso 1 1 calc R . .
C1 C 0.7248(5) 0.37569(19) 0.4374(2) 0.0972(8) Uani 1 1 d . . .
H1A H 0.8086 0.4243 0.4885 0.146 Uiso 1 1 calc R . .
H1B H 0.5701 0.3998 0.4157 0.146 Uiso 1 1 calc R . .
H1C H 0.7965 0.3703 0.3738 0.146 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0587(3) 0.0547(3) 0.0708(4) -0.00493(19) 0.0064(2) -0.01110(18)
N1 0.0628(8) 0.0590(8) 0.0481(9) 0.0101(6) -0.0003(7) 0.0006(6)
C4 0.0422(7) 0.0426(7) 0.0371(9) -0.0041(6) 0.0014(6) 0.0007(5)
C3 0.0486(8) 0.0467(8) 0.0394(9) -0.0037(6) 0.0095(7) 0.0028(6)
C5 0.0452(8) 0.0532(9) 0.0626(12) 0.0021(8) 0.0123(7) 0.0033(6)
C2 0.0568(10) 0.0869(13) 0.0495(12) -0.0030(9) -0.0040(8) 0.0000(9)
C9 0.0511(8) 0.0551(9) 0.0467(10) -0.0032(7) 0.0091(7) 0.0068(7)
C7 0.0727(12) 0.0472(9) 0.0626(12) 0.0077(8) -0.0020(9) -0.0053(7)
C8 0.0646(11) 0.0520(9) 0.0645(12) -0.0034(8) 0.0017(9) 0.0143(8)
C6 0.0578(10) 0.0632(10) 0.0692(13) 0.0080(9) 0.0167(9) -0.0075(8)
C1 0.1135(18) 0.0828(14) 0.0864(16) 0.0414(13) -0.0069(14) 0.0000(13)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.6754(15) . ?
N1 C3 1.327(2) . ?
N1 C1 1.468(3) . ?
N1 C2 1.469(2) . ?
C4 C5 1.384(2) . ?
C4 C9 1.390(2) . ?
C4 C3 1.492(2) . ?
C5 C6 1.383(2) . ?
C9 C8 1.377(2) . ?
C7 C8 1.367(3) . ?
C7 C6 1.371(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C1 121.07(16) . . ?
C3 N1 C2 124.40(15) . . ?
C1 N1 C2 114.33(16) . . ?
C5 C4 C9 118.79(14) . . ?
C5 C4 C3 121.02(13) . . ?
C9 C4 C3 120.15(13) . . ?
N1 C3 C4 117.91(13) . . ?
N1 C3 S1 124.27(12) . . ?
C4 C3 S1 117.78(11) . . ?
C6 C5 C4 120.18(15) . . ?
C8 C9 C4 120.29(16) . . ?
C8 C7 C6 119.84(16) . . ?
C7 C8 C9 120.49(15) . . ?
C7 C6 C5 120.41(17) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        28.58
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 994136'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smk-170

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N S'
_chemical_formula_weight         199.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1194(3)
_cell_length_b                   14.4115(4)
_cell_length_c                   7.3274(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.198(2)
_cell_angle_gamma                90.00
_cell_volume                     1026.18(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12072
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         28.46
_reflns_number_total             2559
_reflns_number_gt                1546
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 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 > 2sigma(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2559
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0648(2) 0.13846(14) 0.9550(3) 0.0750(6) Uani 1 1 d . . .
H1A H 1.0711 0.1714 1.0709 0.113 Uiso 1 1 calc R . .
H1B H 1.1113 0.1729 0.8792 0.113 Uiso 1 1 calc R . .
H1C H 1.1071 0.0786 0.9840 0.113 Uiso 1 1 calc R . .
C2 C 0.8954(2) 0.12255(14) 0.6441(3) 0.0675(5) Uani 1 1 d . . .
H2A H 0.8019 0.1043 0.5859 0.101 Uiso 1 1 calc R . .
H2B H 0.9566 0.0780 0.6138 0.101 Uiso 1 1 calc R . .
H2C H 0.9117 0.1825 0.5974 0.101 Uiso 1 1 calc R . .
C3 C 0.82325(18) 0.11726(10) 0.9392(3) 0.0522(5) Uani 1 1 d . . .
C4 C 0.67709(18) 0.11684(12) 0.8229(2) 0.0507(4) Uani 1 1 d . . .
C5 C 0.61991(19) 0.19443(14) 0.7181(3) 0.0670(5) Uani 1 1 d . . .
H5 H 0.6746 0.2462 0.7175 0.080 Uiso 1 1 calc R . .
C6 C 0.4834(2) 0.19578(15) 0.6150(3) 0.0714(6) Uani 1 1 d . . .
H6 H 0.4463 0.2480 0.5448 0.086 Uiso 1 1 calc R . .
C7 C 0.4023(2) 0.11919(14) 0.6167(3) 0.0631(5) Uani 1 1 d . . .
C8 C 0.45600(18) 0.04164(14) 0.7186(3) 0.0713(6) Uani 1 1 d . . .
H8 H 0.4011 -0.0102 0.7178 0.086 Uiso 1 1 calc R . .
C9 C 0.5926(2) 0.04131(13) 0.8223(3) 0.0654(5) Uani 1 1 d . . .
H9 H 0.6287 -0.0109 0.8934 0.078 Uiso 1 1 calc R . .
N1 N 0.91987(15) 0.12689(9) 0.8493(2) 0.0547(4) Uani 1 1 d . . .
S1 S 0.85795(5) 0.10716(4) 1.17517(7) 0.0680(2) Uani 1 1 d . . .
Cl1 Cl 0.23012(6) 0.12029(4) 0.48319(10) 0.0917(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0538(12) 0.0841(14) 0.0835(16) -0.0128(12) 0.0131(10) -0.0005(10)
C2 0.0692(13) 0.0761(14) 0.0600(13) -0.0024(10) 0.0226(10) -0.0016(10)
C3 0.0590(11) 0.0436(9) 0.0512(11) -0.0007(7) 0.0108(8) 0.0015(7)
C4 0.0511(10) 0.0554(11) 0.0456(10) 0.0031(7) 0.0137(8) 0.0008(8)
C5 0.0618(12) 0.0596(12) 0.0750(13) 0.0098(10) 0.0115(10) -0.0029(9)
C6 0.0627(12) 0.0721(14) 0.0735(13) 0.0173(11) 0.0093(10) 0.0106(10)
C7 0.0486(11) 0.0779(14) 0.0595(12) 0.0006(10) 0.0097(9) 0.0014(9)
C8 0.0607(13) 0.0678(14) 0.0813(15) 0.0079(11) 0.0130(10) -0.0122(10)
C9 0.0620(12) 0.0598(12) 0.0710(13) 0.0138(9) 0.0130(9) -0.0021(10)
N1 0.0500(9) 0.0598(9) 0.0540(9) -0.0023(7) 0.0138(7) -0.0017(6)
S1 0.0716(4) 0.0815(4) 0.0479(3) 0.0026(2) 0.0114(2) 0.0089(2)
Cl1 0.0522(4) 0.1136(6) 0.0983(5) 0.0019(3) 0.0031(3) 0.0034(3)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.464(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.455(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.330(2) . ?
C3 C4 1.487(2) . ?
C3 S1 1.6722(18) . ?
C4 C9 1.384(2) . ?
C4 C5 1.388(2) . ?
C5 C6 1.377(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(3) . ?
C7 Cl1 1.744(2) . ?
C8 C9 1.379(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 117.92(16) . . ?
N1 C3 S1 123.36(14) . . ?
C4 C3 S1 118.72(13) . . ?
C9 C4 C5 118.03(17) . . ?
C9 C4 C3 121.36(16) . . ?
C5 C4 C3 120.55(15) . . ?
C6 C5 C4 120.96(18) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.53(18) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.76(18) . . ?
C8 C7 Cl1 119.72(15) . . ?
C6 C7 Cl1 119.50(15) . . ?
C7 C8 C9 119.19(17) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C4 121.52(17) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
C3 N1 C2 124.78(15) . . ?
C3 N1 C1 121.11(16) . . ?
C2 N1 C1 114.05(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 C9 119.89(19) . . . . ?
S1 C3 C4 C9 -60.9(2) . . . . ?
N1 C3 C4 C5 -63.0(2) . . . . ?
S1 C3 C4 C5 116.16(16) . . . . ?
C9 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 -177.84(18) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 Cl1 -179.02(15) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
Cl1 C7 C8 C9 179.45(15) . . . . ?
C7 C8 C9 C4 -1.2(3) . . . . ?
C5 C4 C9 C8 1.1(3) . . . . ?
C3 C4 C9 C8 178.26(17) . . . . ?
C4 C3 N1 C2 -10.1(2) . . . . ?
S1 C3 N1 C2 170.75(13) . . . . ?
C4 C3 N1 C1 173.03(14) . . . . ?
S1 C3 N1 C1 -6.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 994137'
