# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1052404'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_chemical_name_systematic        
2-methyl-6-(phenylthio)-N-(quinolin-8-yl)benzamide
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         370.45

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2600(6)
_cell_length_b                   8.0578(3)
_cell_length_c                   16.7298(7)
_cell_angle_alpha                90
_cell_angle_beta                 118.216(1)
_cell_angle_gamma                90
_cell_volume                     1931.46(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      3.4906
_cell_measurement_theta_max      29.0105
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       paralellopiped
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_size_max          0.623
_exptl_crystal_size_mid          0.435
_exptl_crystal_size_min          0.304
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776

_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Triumph

_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            15986
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             4423
_reflns_number_gt                3405
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1265
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_number_reflns         4423
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.9520P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 '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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.26690(4) 0.41082(7) 1.03971(4) 0.0647(2) Uani d . . . 1 . .
O O1 0.22416(12) 0.45723(19) 0.81527(13) 0.0750(5) Uani d . . . 1 . .
N N1 0.27461(11) 0.1957(2) 0.86306(11) 0.0441(4) Uani d . . . 1 . .
H H1N 0.2634(15) 0.107(3) 0.8832(14) 0.053(6) Uiso d . . . 1 . .
N N2 0.35986(11) -0.09515(19) 0.90311(11) 0.0454(4) Uani d . . . 1 . .
C C1 0.21675(13) 0.3260(2) 0.84671(13) 0.0448(4) Uani d . . . 1 . .
C C2 0.14006(12) 0.2976(2) 0.87108(13) 0.0426(4) Uani d . . . 1 . .
C C3 0.05402(15) 0.2334(3) 0.80678(16) 0.0594(6) Uani d . . . 1 . .
C C4 -0.01557(16) 0.2174(3) 0.8317(2) 0.0787(8) Uani d . . . 1 . .
H H4 -0.073 0.1731 0.7905 0.094 Uiso calc U . R 1 . .
C C5 -0.00168(19) 0.2655(4) 0.9158(2) 0.0825(8) Uani d . . . 1 . .
H H5 -0.0501 0.2559 0.9303 0.099 Uiso calc U . R 1 . .
C C6 0.08256(17) 0.3275(3) 0.97851(18) 0.0676(6) Uani d . . . 1 . .
H H6 0.0916 0.3591 1.0356 0.081 Uiso calc U . R 1 . .
C C7 0.15420(13) 0.3429(2) 0.95666(14) 0.0460(4) Uani d . . . 1 . .
C C8 0.24392(12) 0.6148(2) 1.06322(12) 0.0429(4) Uani d . . . 1 . .
C C9 0.26360(14) 0.6540(3) 1.15083(13) 0.0538(5) Uani d . . . 1 . .
H H9 0.2859 0.5725 1.1955 0.065 Uiso calc U . R 1 . .
C C10 0.25035(16) 0.8128(3) 1.17219(16) 0.0637(6) Uani d . . . 1 . .
H H10 0.2642 0.839 1.2314 0.076 Uiso calc U . R 1 . .
C C11 0.21705(16) 0.9316(3) 1.1071(2) 0.0692(7) Uani d . . . 1 . .
H H11 0.208 1.039 1.1218 0.083 Uiso calc U . R 1 . .
C C12 0.19655(18) 0.8942(3) 1.01921(19) 0.0696(6) Uani d . . . 1 . .
H H12 0.1731 0.976 0.9747 0.083 Uiso calc U . R 1 . .
C C13 0.21082(15) 0.7354(3) 0.99702(14) 0.0555(5) Uani d . . . 1 . .
H H13 0.1982 0.7102 0.9381 0.067 Uiso calc U . R 1 . .
C C14 0.35532(12) 0.1834(2) 0.85317(11) 0.0392(4) Uani d . . . 1 . .
C C15 0.39246(14) 0.3086(3) 0.82507(13) 0.0494(5) Uani d . . . 1 . .
H H15 0.3625 0.4108 0.8086 0.059 Uiso calc U . R 1 . .
C C16 0.47608(15) 0.2825(3) 0.82110(15) 0.0573(5) Uani d . . . 1 . .
H H16 0.5011 0.3687 0.8025 0.069 Uiso calc U . R 1 . .
C C17 0.52067(14) 0.1347(3) 0.84376(14) 0.0561(5) Uani d . . . 1 . .
H H17 0.576 0.1205 0.8409 0.067 Uiso calc U . R 1 . .
C C18 0.48374(13) 0.0022(2) 0.87168(12) 0.0448(4) Uani d . . . 1 . .
C C19 0.52566(15) -0.1557(3) 0.89651(14) 0.0565(5) Uani d . . . 1 . .
H H19 0.5808 -0.1777 0.8946 0.068 Uiso calc U . R 1 . .
C C20 0.48539(16) -0.2747(3) 0.92308(15) 0.0595(6) Uani d . . . 1 . .
H H20 0.5127 -0.3791 0.9398 0.071 Uiso calc U . R 1 . .
C C21 0.40237(15) -0.2399(2) 0.92532(14) 0.0544(5) Uani d . . . 1 . .
H H21 0.3756 -0.3237 0.9436 0.065 Uiso calc U . R 1 . .
C C22 0.40020(12) 0.0256(2) 0.87656(11) 0.0381(4) Uani d . . . 1 . .
C C23 0.0377(2) 0.1876(4) 0.71306(19) 0.0952(10) Uani d . . . 1 . .
H H23A -0.0218 0.1338 0.6806 0.143 Uiso calc U . R 1 . .
H H23B 0.0861 0.1136 0.7177 0.143 Uiso calc U . R 1 . .
H H23C 0.0385 0.2861 0.6812 0.143 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.7705(19) ?
S1 C7 . 1.783(2) ?
O1 C1 . 1.212(2) ?
N1 C1 . 1.349(2) ?
N1 C14 . 1.402(2) ?
N2 C21 . 1.316(2) ?
N2 C22 . 1.360(2) ?
C1 C2 . 1.501(3) ?
C2 C7 . 1.387(3) ?
C2 C3 . 1.400(3) ?
C3 C4 . 1.384(3) ?
C3 C23 . 1.507(4) ?
C4 C5 . 1.372(4) ?
C5 C6 . 1.366(4) ?
C6 C7 . 1.382(3) ?
C8 C13 . 1.377(3) ?
C8 C9 . 1.381(3) ?
C9 C10 . 1.373(3) ?
C10 C11 . 1.356(4) ?
C11 C12 . 1.378(4) ?
C12 C13 . 1.382(3) ?
C14 C15 . 1.368(3) ?
C14 C22 . 1.426(2) ?
C15 C16 . 1.408(3) ?
C16 C17 . 1.352(3) ?
C17 C18 . 1.409(3) ?
C18 C19 . 1.410(3) ?
C18 C22 . 1.412(3) ?
C19 C20 . 1.350(3) ?
C20 C21 . 1.397(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C7 . . 102.18(8) ?
C1 N1 C14 . . 129.27(17) ?
C21 N2 C22 . . 117.14(17) ?
O1 C1 N1 . . 124.35(18) ?
O1 C1 C2 . . 121.11(17) ?
N1 C1 C2 . . 114.54(16) ?
C7 C2 C3 . . 120.53(18) ?
C7 C2 C1 . . 119.11(17) ?
C3 C2 C1 . . 120.29(18) ?
C4 C3 C2 . . 117.7(2) ?
C4 C3 C23 . . 121.6(2) ?
C2 C3 C23 . . 120.7(2) ?
C5 C4 C3 . . 121.4(2) ?
C6 C5 C4 . . 120.7(2) ?
C5 C6 C7 . . 119.6(2) ?
C6 C7 C2 . . 120.0(2) ?
C6 C7 S1 . . 120.38(18) ?
C2 C7 S1 . . 119.51(14) ?
C13 C8 C9 . . 119.91(19) ?
C13 C8 S1 . . 121.30(15) ?
C9 C8 S1 . . 118.73(16) ?
C10 C9 C8 . . 120.2(2) ?
C11 C10 C9 . . 120.1(2) ?
C10 C11 C12 . . 120.4(2) ?
C11 C12 C13 . . 120.1(2) ?
C8 C13 C12 . . 119.2(2) ?
C15 C14 N1 . . 125.37(17) ?
C15 C14 C22 . . 120.00(16) ?
N1 C14 C22 . . 114.62(16) ?
C14 C15 C16 . . 119.94(19) ?
C17 C16 C15 . . 121.4(2) ?
C16 C17 C18 . . 120.29(18) ?
C17 C18 C19 . . 124.00(19) ?
C17 C18 C22 . . 119.38(18) ?
C19 C18 C22 . . 116.62(19) ?
C20 C19 C18 . . 119.73(19) ?
C19 C20 C21 . . 119.45(19) ?
N2 C21 C20 . . 123.8(2) ?
N2 C22 C18 . . 123.29(17) ?
N2 C22 C14 . . 117.68(15) ?
C18 C22 C14 . . 119.02(17) ?


_exptl_crystal_recrystallization_method 'Vapour Deposition'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1052405'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_chemical_name_systematic        
3-chloro-2-(phenylthio)-N-(quinolin-8-yl)benzamide
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 Cl N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         390.87

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   12.0459(5)
_cell_length_b                   10.3781(5)
_cell_length_c                   15.4051(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.3945(12)
_cell_angle_gamma                90
_cell_volume                     1837.78(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      3.2223
_cell_measurement_theta_max      32.5824
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.607
_exptl_crystal_size_min          0.526
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.84

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)

_diffrn_source                   ?
_diffrn_source_type              fine-focus

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Triumph

_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed-chi'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            28740
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             4214
_reflns_number_gt                3444
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1676
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         4214
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    riding
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0835P)²+1.1019P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.380
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 '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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.33168(7) 0.52839(8) 0.11672(5) 0.0787(3) Uani d . . . 1 . .
S S1 0.59522(5) 0.48751(6) 0.23561(4) 0.0533(2) Uani d . . . 1 . .
O O1 0.67933(18) 0.13640(19) 0.32607(14) 0.0748(6) Uani d . . . 1 . .
N N1 0.69058(17) 0.31069(19) 0.41662(13) 0.0507(4) Uani d . . . 1 . .
H H1 0.6483 0.3698 0.4299 0.061 Uiso calc U . R 1 . .
N N2 0.75732(17) 0.49700(18) 0.53759(13) 0.0505(4) Uani d . . . 1 . .
C C1 0.6362(2) 0.2325(2) 0.34750(15) 0.0478(5) Uani d . . . 1 . .
C C2 0.51317(19) 0.2684(2) 0.29605(14) 0.0453(5) Uani d . . . 1 . .
C C3 0.4261(2) 0.1793(3) 0.29601(17) 0.0580(6) Uani d . . . 1 . .
H H3 0.444 0.105 0.3312 0.07 Uiso calc U . R 1 . .
C C4 0.3126(2) 0.2025(3) 0.24305(19) 0.0681(8) Uani d . . . 1 . .
H H4 0.2546 0.1439 0.2439 0.082 Uiso calc U . R 1 . .
C C5 0.2845(2) 0.3098(3) 0.18969(18) 0.0647(7) Uani d . . . 1 . .
H H5 0.2081 0.3241 0.1545 0.078 Uiso calc U . R 1 . .
C C6 0.3705(2) 0.3964(2) 0.18859(16) 0.0540(5) Uani d . . . 1 . .
C C7 0.48536(19) 0.3786(2) 0.24198(14) 0.0450(5) Uani d . . . 1 . .
C C8 0.58105(18) 0.6120(2) 0.31105(15) 0.0451(5) Uani d . . . 1 . .
C C9 0.6468(2) 0.7222(2) 0.31205(18) 0.0560(6) Uani d . . . 1 . .
H H9 0.6924 0.7288 0.2731 0.067 Uiso calc U . R 1 . .
C C10 0.6445(2) 0.8216(3) 0.3706(2) 0.0700(8) Uani d . . . 1 . .
H H10 0.6888 0.8951 0.3712 0.084 Uiso calc U . R 1 . .
C C11 0.5769(3) 0.8130(3) 0.4284(2) 0.0752(9) Uani d . . . 1 . .
H H11 0.576 0.88 0.4682 0.09 Uiso calc U . R 1 . .
C C12 0.5109(2) 0.7043(3) 0.42684(19) 0.0657(7) Uani d . . . 1 . .
H H12 0.4649 0.6985 0.4656 0.079 Uiso calc U . R 1 . .
C C13 0.5122(2) 0.6038(2) 0.36840(17) 0.0538(5) Uani d . . . 1 . .
H H13 0.467 0.5309 0.3676 0.065 Uiso calc U . R 1 . .
C C14 0.80788(19) 0.3082(2) 0.47011(14) 0.0454(5) Uani d . . . 1 . .
C C15 0.8889(2) 0.2174(3) 0.46488(16) 0.0582(6) Uani d . . . 1 . .
H H15 0.8674 0.1483 0.4249 0.07 Uiso calc U . R 1 . .
C C16 1.0041(2) 0.2301(3) 0.52041(18) 0.0683(8) Uani d . . . 1 . .
H H16 1.0584 0.1683 0.5165 0.082 Uiso calc U . R 1 . .
C C17 1.0392(2) 0.3291(3) 0.57955(16) 0.0618(7) Uani d . . . 1 . .
H H17 1.1165 0.3351 0.6149 0.074 Uiso calc U . R 1 . .
C C18 0.95850(19) 0.4227(2) 0.58741(14) 0.0489(5) Uani d . . . 1 . .
C C19 0.9862(2) 0.5283(3) 0.64795(17) 0.0587(6) Uani d . . . 1 . .
H H19 1.0621 0.5397 0.6851 0.07 Uiso calc U . R 1 . .
C C20 0.9026(2) 0.6126(3) 0.65187(18) 0.0639(7) Uani d . . . 1 . .
H H20 0.9201 0.6823 0.6916 0.077 Uiso calc U . R 1 . .
C C21 0.7883(2) 0.5935(3) 0.59484(18) 0.0627(7) Uani d . . . 1 . .
H H21 0.7316 0.6526 0.5979 0.075 Uiso calc U . R 1 . .
C C22 0.84156(18) 0.4121(2) 0.53288(13) 0.0436(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C6 . 1.735(3) ?
S1 C7 . 1.765(2) ?
S1 C8 . 1.780(2) ?
O1 C1 . 1.215(3) ?
N1 C1 . 1.344(3) ?
N1 C14 . 1.407(3) ?
N2 C21 . 1.313(3) ?
N2 C22 . 1.362(3) ?
C1 C2 . 1.504(3) ?
C2 C7 . 1.396(3) ?
C2 C3 . 1.399(3) ?
C3 C4 . 1.387(4) ?
C4 C5 . 1.365(4) ?
C5 C6 . 1.376(4) ?
C6 C7 . 1.394(3) ?
C8 C13 . 1.384(3) ?
C8 C9 . 1.389(3) ?
C9 C10 . 1.377(4) ?
C10 C11 . 1.377(5) ?
C11 C12 . 1.376(4) ?
C12 C13 . 1.381(4) ?
C14 C15 . 1.376(3) ?
C14 C22 . 1.424(3) ?
C15 C16 . 1.402(4) ?
C16 C17 . 1.355(4) ?
C17 C18 . 1.405(3) ?
C18 C22 . 1.412(3) ?
C18 C19 . 1.413(4) ?
C19 C20 . 1.349(4) ?
C20 C21 . 1.408(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 S1 C8 . . 102.03(10) ?
C1 N1 C14 . . 128.3(2) ?
C21 N2 C22 . . 117.5(2) ?
O1 C1 N1 . . 124.4(2) ?
O1 C1 C2 . . 119.7(2) ?
N1 C1 C2 . . 116.0(2) ?
C7 C2 C3 . . 119.7(2) ?
C7 C2 C1 . . 122.75(19) ?
C3 C2 C1 . . 117.2(2) ?
C4 C3 C2 . . 119.5(2) ?
C5 C4 C3 . . 121.3(2) ?
C4 C5 C6 . . 119.2(2) ?
C5 C6 C7 . . 121.6(2) ?
C5 C6 Cl1 . . 117.6(2) ?
C7 C6 Cl1 . . 120.76(19) ?
C6 C7 C2 . . 118.6(2) ?
C6 C7 S1 . . 120.71(18) ?
C2 C7 S1 . . 120.51(17) ?
C13 C8 C9 . . 119.5(2) ?
C13 C8 S1 . . 124.42(18) ?
C9 C8 S1 . . 116.07(18) ?
C10 C9 C8 . . 120.1(3) ?
C9 C10 C11 . . 120.5(3) ?
C12 C11 C10 . . 119.5(3) ?
C11 C12 C13 . . 120.8(3) ?
C12 C13 C8 . . 119.7(2) ?
C15 C14 N1 . . 125.7(2) ?
C15 C14 C22 . . 119.7(2) ?
N1 C14 C22 . . 114.57(18) ?
C14 C15 C16 . . 119.4(2) ?
C17 C16 C15 . . 122.3(2) ?
C16 C17 C18 . . 119.9(2) ?
C17 C18 C22 . . 119.2(2) ?
C17 C18 C19 . . 124.1(2) ?
C22 C18 C19 . . 116.7(2) ?
C20 C19 C18 . . 120.0(2) ?
C19 C20 C21 . . 119.0(2) ?
N2 C21 C20 . . 123.7(2) ?
N2 C22 C18 . . 123.0(2) ?
N2 C22 C14 . . 117.41(18) ?
C18 C22 C14 . . 119.6(2) ?


_exptl_crystal_recrystallization_method 'Vapour Deposition'
