# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1468845'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,6-dimethoxy-N-methylbenzothioamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N O2 S'
_chemical_formula_weight         211.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.1567(2)
_cell_length_b                   8.34180(10)
_cell_length_c                   8.61660(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1089.43(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    7167
_cell_measurement_theta_min      6.0520
_cell_measurement_theta_max      76.9920

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.723
_exptl_crystal_size_mid          0.431
_exptl_crystal_size_min          0.358
_exptl_absorpt_coefficient_mu    2.445
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.57275
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130.00(10)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8872
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         6.055
_diffrn_reflns_theta_max         77.001
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2220
_reflns_number_gt                2209
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.959

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.0311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2220
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61332(2) 0.60397(4) 0.74235(5) 0.02069(14) Uani 1 1 d . . . . .
O1 O 0.62871(8) 0.80037(18) 0.37974(18) 0.0303(3) Uani 1 1 d . . . . .
O2 O 0.38594(7) 0.59223(16) 0.63869(19) 0.0264(3) Uani 1 1 d . . . . .
N1 N 0.56450(10) 0.44574(17) 0.48899(18) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.50402(10) 0.70560(17) 0.50652(18) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.41379(11) 0.70968(19) 0.54018(19) 0.0199(3) Uani 1 1 d . . . . .
C5 C 0.35997(11) 0.8278(2) 0.4758(2) 0.0249(4) Uani 1 1 d . . . . .
C2 C 0.54062(11) 0.81869(19) 0.4069(2) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.56075(10) 0.57642(18) 0.57371(19) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.48781(13) 0.9393(2) 0.3429(2) 0.0289(4) Uani 1 1 d . . . . .
C4 C 0.39898(13) 0.9420(2) 0.3792(3) 0.0286(4) Uani 1 1 d . . . . .
C7 C 0.29365(13) 0.5652(3) 0.6516(3) 0.0386(5) Uani 1 1 d . . . . .
C1 C 0.66620(15) 0.8927(3) 0.2573(3) 0.0402(5) Uani 1 1 d . . . . .
C10 C 0.61475(15) 0.3035(3) 0.5304(3) 0.0347(5) Uani 1 1 d . . . . .
H4 H 0.5135(17) 1.022(3) 0.273(3) 0.037(6) Uiso 1 1 d . . . . .
H1 H 0.731(2) 0.854(4) 0.259(4) 0.049(7) Uiso 1 1 d . . . . .
H6 H 0.3013(16) 0.838(3) 0.489(3) 0.025(6) Uiso 1 1 d . . . . .
H5 H 0.3626(19) 1.029(3) 0.334(3) 0.037(7) Uiso 1 1 d . . . . .
H9 H 0.2886(17) 0.468(3) 0.712(4) 0.034(6) Uiso 1 1 d . . . . .
H10 H 0.532(2) 0.438(4) 0.403(4) 0.050(8) Uiso 1 1 d . . . . .
H3 H 0.642(2) 0.862(4) 0.163(4) 0.045(8) Uiso 1 1 d . . . . .
H2 H 0.662(2) 1.013(4) 0.275(4) 0.057(9) Uiso 1 1 d . . . . .
H7 H 0.257(3) 0.664(4) 0.693(5) 0.074(11) Uiso 1 1 d . . . . .
H13 H 0.607(2) 0.278(4) 0.638(5) 0.052(9) Uiso 1 1 d . . . . .
H8 H 0.270(2) 0.544(4) 0.549(5) 0.062(9) Uiso 1 1 d . . . . .
H11 H 0.672(2) 0.320(4) 0.504(5) 0.065(10) Uiso 1 1 d . . . . .
H12 H 0.590(2) 0.210(5) 0.492(5) 0.067(11) Uiso 1 1 d . . . . .


_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 C9 1.6731(17) . ?
O1 C2 1.364(2) . ?
O1 C1 1.424(3) . ?
O2 C6 1.363(2) . ?
O2 C7 1.421(2) . ?
N1 C9 1.313(2) . ?
N1 C10 1.454(2) . ?
N1 H10 0.90(4) . ?
C8 C2 1.391(2) . ?
C8 C6 1.398(2) . ?
C8 C9 1.495(2) . ?
C6 C5 1.394(2) . ?
C5 C4 1.396(3) . ?
C5 H6 0.90(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.382(3) . ?
C3 H4 0.99(3) . ?
C4 H5 0.99(3) . ?
C7 H9 0.96(3) . ?
C7 H7 1.05(4) . ?
C7 H8 0.97(4) . ?
C1 H1 1.03(3) . ?
C1 H3 0.93(4) . ?
C1 H2 1.02(3) . ?
C10 H13 0.95(4) . ?
C10 H11 0.91(4) . ?
C10 H12 0.93(4) . ?

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
C2 O1 C1 117.18(15) . . ?
C6 O2 C7 117.87(15) . . ?
C9 N1 C10 124.30(16) . . ?
C9 N1 H10 119.7(19) . . ?
C10 N1 H10 115.9(19) . . ?
C2 C8 C6 120.10(15) . . ?
C2 C8 C9 119.90(14) . . ?
C6 C8 C9 119.97(14) . . ?
O2 C6 C5 125.06(15) . . ?
O2 C6 C8 114.49(14) . . ?
C5 C6 C8 120.45(16) . . ?
C6 C5 C4 118.13(17) . . ?
C6 C5 H6 126.4(15) . . ?
C4 C5 H6 115.4(15) . . ?
O1 C2 C8 114.84(14) . . ?
O1 C2 C3 124.98(16) . . ?
C8 C2 C3 120.18(16) . . ?
N1 C9 C8 114.07(14) . . ?
N1 C9 S1 125.19(12) . . ?
C8 C9 S1 120.74(12) . . ?
C4 C3 C2 118.67(17) . . ?
C4 C3 H4 120.4(16) . . ?
C2 C3 H4 120.9(16) . . ?
C3 C4 C5 122.43(16) . . ?
C3 C4 H5 117.8(17) . . ?
C5 C4 H5 119.8(17) . . ?
O2 C7 H9 104.7(15) . . ?
O2 C7 H7 115(2) . . ?
H9 C7 H7 116(3) . . ?
O2 C7 H8 109(2) . . ?
H9 C7 H8 108(3) . . ?
H7 C7 H8 104(3) . . ?
O1 C1 H1 101.6(18) . . ?
O1 C1 H3 110(2) . . ?
H1 C1 H3 107(3) . . ?
O1 C1 H2 113(2) . . ?
H1 C1 H2 112(2) . . ?
H3 C1 H2 112(3) . . ?
N1 C10 H13 111(2) . . ?
N1 C10 H11 109(2) . . ?
H13 C10 H11 113(3) . . ?
N1 C10 H12 113(2) . . ?
H13 C10 H12 96(3) . . ?
H11 C10 H12 115(3) . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.054



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Slow evaporation of dichloromethane and pentane mixtures'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1468846'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-ethyl-2,6-dimethoxybenzothioamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H15 N O2 S'
_chemical_formula_weight         225.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   7.0891(2)
_cell_length_b                   17.2751(3)
_cell_length_c                   10.1191(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.161(2)
_cell_angle_gamma                90
_cell_volume                     1190.26(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    6413
_cell_measurement_theta_min      5.1270
_cell_measurement_theta_max      76.8570

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.932
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    2.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.48261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            10054
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.121
_diffrn_reflns_theta_max         77.096
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2503
_reflns_number_gt                2398
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+0.3547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.45242(5) 0.17823(2) 0.16977(3) 0.02180(13) Uani 1 1 d . . . . .
O1 O 0.73518(14) 0.32129(5) 0.41902(10) 0.0240(2) Uani 1 1 d . . . . .
O2 O 0.07014(13) 0.29706(6) 0.19162(11) 0.0269(2) Uani 1 1 d . . . . .
N1 N 0.40850(15) 0.19409(6) 0.42029(11) 0.0170(2) Uani 1 1 d . . . . .
C8 C 0.40285(18) 0.31314(7) 0.30193(12) 0.0156(2) Uani 1 1 d . . . . .
C6 C 0.22062(18) 0.34758(7) 0.24105(12) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.56540(18) 0.36013(7) 0.36035(12) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.42105(18) 0.11086(7) 0.44669(13) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.42047(16) 0.22664(7) 0.30533(11) 0.0160(2) Uani 1 1 d . . . . .
C3 C 0.54792(19) 0.44051(7) 0.35531(13) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.3664(2) 0.47309(7) 0.29278(14) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.20202(19) 0.42793(7) 0.23557(13) 0.0216(3) Uani 1 1 d . . . . .
C7 C -0.1195(2) 0.32856(9) 0.12680(17) 0.0285(3) Uani 1 1 d . . . . .
C11 C 0.2279(2) 0.06969(8) 0.38244(15) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.8998(2) 0.36542(10) 0.49647(17) 0.0332(3) Uani 1 1 d . . . . .
H6 H 0.082(2) 0.4512(10) 0.1942(17) 0.026(4) Uiso 1 1 d . . . . .
H12 H 0.455(2) 0.1049(9) 0.5454(17) 0.020(4) Uiso 1 1 d . . . . .
H11 H 0.521(2) 0.0899(10) 0.4102(17) 0.023(4) Uiso 1 1 d . . . . .
H8 H -0.159(3) 0.3644(11) 0.1884(19) 0.031(4) Uiso 1 1 d . . . . .
H4 H 0.656(3) 0.4722(11) 0.3967(17) 0.028(4) Uiso 1 1 d . . . . .
H9 H -0.119(3) 0.3551(12) 0.041(2) 0.041(5) Uiso 1 1 d . . . . .
H14 H 0.125(3) 0.0898(12) 0.418(2) 0.040(5) Uiso 1 1 d . . . . .
H1 H 0.945(3) 0.4031(12) 0.436(2) 0.040(5) Uiso 1 1 d . . . . .
H15 H 0.247(3) 0.0152(13) 0.411(2) 0.046(5) Uiso 1 1 d . . . . .
H13 H 0.189(3) 0.0736(12) 0.284(2) 0.037(5) Uiso 1 1 d . . . . .
H5 H 0.358(3) 0.5252(11) 0.2915(17) 0.027(4) Uiso 1 1 d . . . . .
H2 H 0.860(3) 0.3953(12) 0.570(2) 0.044(5) Uiso 1 1 d . . . . .
H3 H 0.994(3) 0.3302(12) 0.531(2) 0.045(6) Uiso 1 1 d . . . . .
H10 H 0.398(3) 0.2250(11) 0.4870(18) 0.028(4) Uiso 1 1 d . . . . .
H7 H -0.203(3) 0.2855(12) 0.1054(19) 0.037(5) Uiso 1 1 d . . . . .


_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 C9 1.6749(12) . ?
O1 C2 1.3614(15) . ?
O1 C1 1.4312(16) . ?
O2 C6 1.3611(15) . ?
O2 C7 1.4293(16) . ?
N1 C9 1.3159(16) . ?
N1 C10 1.4605(15) . ?
N1 H10 0.880(19) . ?
C8 C2 1.3990(16) . ?
C8 C6 1.3998(17) . ?
C8 C9 1.4990(16) . ?
C6 C5 1.3940(17) . ?
C2 C3 1.3936(18) . ?
C10 C11 1.5194(17) . ?
C10 H12 0.965(16) . ?
C10 H11 0.954(17) . ?
C3 C4 1.3857(19) . ?
C3 H4 0.941(18) . ?
C4 C5 1.3878(19) . ?
C4 H5 0.902(19) . ?
C5 H6 0.927(17) . ?
C7 H8 0.973(19) . ?
C7 H9 0.98(2) . ?
C7 H7 0.94(2) . ?
C11 H14 0.96(2) . ?
C11 H15 0.98(2) . ?
C11 H13 0.96(2) . ?
C1 H1 1.00(2) . ?
C1 H2 1.01(2) . ?
C1 H3 0.90(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
C2 O1 C1 117.61(11) . . ?
C6 O2 C7 117.74(11) . . ?
C9 N1 C10 124.53(10) . . ?
C9 N1 H10 117.3(12) . . ?
C10 N1 H10 118.1(12) . . ?
C2 C8 C6 119.34(11) . . ?
C2 C8 C9 121.01(10) . . ?
C6 C8 C9 119.64(10) . . ?
O2 C6 C5 124.61(11) . . ?
O2 C6 C8 114.97(10) . . ?
C5 C6 C8 120.41(11) . . ?
O1 C2 C3 124.46(11) . . ?
O1 C2 C8 114.99(11) . . ?
C3 C2 C8 120.55(11) . . ?
N1 C10 C11 112.38(10) . . ?
N1 C10 H12 106.2(9) . . ?
C11 C10 H12 109.2(9) . . ?
N1 C10 H11 108.4(10) . . ?
C11 C10 H11 109.5(10) . . ?
H12 C10 H11 111.1(14) . . ?
N1 C9 C8 114.89(10) . . ?
N1 C9 S1 124.56(9) . . ?
C8 C9 S1 120.55(9) . . ?
C4 C3 C2 118.90(11) . . ?
C4 C3 H4 120.4(11) . . ?
C2 C3 H4 120.6(11) . . ?
C3 C4 C5 121.82(12) . . ?
C3 C4 H5 117.6(11) . . ?
C5 C4 H5 120.5(11) . . ?
C4 C5 C6 118.95(12) . . ?
C4 C5 H6 120.1(11) . . ?
C6 C5 H6 121.0(11) . . ?
O2 C7 H8 110.4(11) . . ?
O2 C7 H9 110.5(12) . . ?
H8 C7 H9 109.9(16) . . ?
O2 C7 H7 105.0(12) . . ?
H8 C7 H7 112.1(16) . . ?
H9 C7 H7 108.8(16) . . ?
C10 C11 H14 110.9(12) . . ?
C10 C11 H15 106.9(12) . . ?
H14 C11 H15 106.9(17) . . ?
C10 C11 H13 112.1(12) . . ?
H14 C11 H13 109.4(16) . . ?
H15 C11 H13 110.4(17) . . ?
O1 C1 H1 111.3(11) . . ?
O1 C1 H2 108.8(12) . . ?
H1 C1 H2 108.6(16) . . ?
O1 C1 H3 104.7(14) . . ?
H1 C1 H3 110.1(18) . . ?
H2 C1 H3 113.3(18) . . ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.067


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Slow evaporation of dichloromethane and pentane mixtures'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1468847'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(tert-butyl)-2,6-dimethoxybenzothioamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 N O2 S'
_chemical_formula_weight         253.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1980(4)
_cell_length_b                   10.3995(6)
_cell_length_c                   14.5146(7)
_cell_angle_alpha                73.111(5)
_cell_angle_beta                 81.002(4)
_cell_angle_gamma                73.607(4)
_cell_volume                     1408.41(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    130
_cell_measurement_reflns_used    5808
_cell_measurement_theta_min      4.5380
_cell_measurement_theta_max      76.6410

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.142
_exptl_absorpt_coefficient_mu    1.969
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.90488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      130
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            12929
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         76.988
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5879
_reflns_number_gt                5045
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.4058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5879
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.75699(3) 0.23560(4) 0.16964(3) 0.02727(10) Uani 1 1 d . . . . .
S1 S 0.21435(3) 0.26549(4) 0.33009(3) 0.03161(11) Uani 1 1 d . . . . .
O2 O 0.13495(13) 0.34268(12) 0.08067(8) 0.0398(3) Uani 1 1 d . . . . .
O3 O 0.60141(14) 0.15721(13) 0.41909(8) 0.0425(3) Uani 1 1 d . . . . .
N2 N 0.53004(12) 0.13951(12) 0.22184(8) 0.0235(2) Uani 1 1 d . . . . .
O4 O 0.45552(12) 0.48663(13) 0.13740(9) 0.0417(3) Uani 1 1 d . . . . .
O1 O 0.04055(13) 0.01219(14) 0.35922(8) 0.0412(3) Uani 1 1 d . . . . .
N1 N -0.04474(12) 0.35722(13) 0.27948(9) 0.0262(3) Uani 1 1 d . . . . .
C20 C 0.52754(13) 0.32896(15) 0.28078(10) 0.0238(3) Uani 1 1 d . . . . .
C7 C 0.09005(13) 0.17145(15) 0.21752(10) 0.0247(3) Uani 1 1 d . . . . .
C9 C 0.07869(14) 0.27155(15) 0.27669(10) 0.0252(3) Uani 1 1 d . . . . .
C22 C 0.60100(13) 0.22780(14) 0.22314(9) 0.0224(3) Uani 1 1 d . . . . .
C6 C 0.11724(14) 0.21135(16) 0.11717(11) 0.0295(3) Uani 1 1 d . . . . .
C19 C 0.52936(16) 0.28951(17) 0.38152(11) 0.0313(3) Uani 1 1 d . . . . .
C23 C 0.56924(14) 0.02361(15) 0.17436(11) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.06910(14) 0.04061(16) 0.26169(11) 0.0284(3) Uani 1 1 d . . . . .
C15 C 0.45466(14) 0.46069(16) 0.23487(11) 0.0298(3) Uani 1 1 d . . . . .
C10 C -0.09603(15) 0.47143(16) 0.32826(12) 0.0307(3) Uani 1 1 d . . . . .
C3 C 0.07789(15) -0.05268(17) 0.20689(13) 0.0333(3) Uani 1 1 d . . . . .
C5 C 0.12332(16) 0.11992(18) 0.06211(12) 0.0344(3) Uani 1 1 d . . . . .
C4 C 0.10425(15) -0.01074(18) 0.10780(13) 0.0352(3) Uani 1 1 d . . . . .
C25 C 0.58421(18) 0.08242(19) 0.06546(12) 0.0353(3) Uani 1 1 d . . . . .
C24 C 0.45182(17) -0.04808(18) 0.20197(13) 0.0343(3) Uani 1 1 d . . . . .
C16 C 0.38672(16) 0.55621(19) 0.28791(15) 0.0394(4) Uani 1 1 d . . . . .
C13 C -0.01322(18) 0.58083(19) 0.28863(15) 0.0392(4) Uani 1 1 d . . . . .
C11 C -0.24495(16) 0.53570(18) 0.30350(15) 0.0383(4) Uani 1 1 d . . . . .
C18 C 0.46019(19) 0.3846(2) 0.43451(13) 0.0423(4) Uani 1 1 d . . . . .
C26 C 0.70142(17) -0.07900(18) 0.21149(16) 0.0396(4) Uani 1 1 d . . . . .
C17 C 0.39134(18) 0.5156(2) 0.38654(15) 0.0447(5) Uani 1 1 d . . . . .
C12 C -0.0909(2) 0.4133(2) 0.43683(13) 0.0428(4) Uani 1 1 d . . . . .
C8 C 0.1686(3) 0.3871(2) -0.02095(15) 0.0533(5) Uani 1 1 d . . . . .
C21 C 0.6049(3) 0.1102(3) 0.52194(15) 0.0634(6) Uani 1 1 d . . . . .
C1 C -0.0399(3) -0.0787(3) 0.40250(15) 0.0788(9) Uani 1 1 d . . . . .
H1 H -0.0512 -0.0886 0.4709 0.118 Uiso 1 1 calc R U . . .
H2 H -0.1280 -0.0435 0.3767 0.118 Uiso 1 1 calc R U . . .
H3 H 0.0034 -0.1675 0.3901 0.118 Uiso 1 1 calc R U . . .
C14 C 0.3517(3) 0.5947(3) 0.09057(18) 0.0718(7) Uani 1 1 d . . . . .
H27 H 0.3644 0.6016 0.0225 0.108 Uiso 1 1 calc R U . . .
H28 H 0.2641 0.5762 0.1157 0.108 Uiso 1 1 calc R U . . .
H26 H 0.3552 0.6804 0.1014 0.108 Uiso 1 1 calc R U . . .
H29 H 0.447(2) 0.154(2) 0.2506(13) 0.034(5) Uiso 1 1 d . . . . .
H10 H -0.1055(19) 0.3444(19) 0.2510(13) 0.032(5) Uiso 1 1 d . . . . .
H38 H 0.365(2) 0.014(2) 0.1804(14) 0.041(5) Uiso 1 1 d . . . . .
H32 H 0.657(2) 0.132(2) 0.0447(14) 0.043(5) Uiso 1 1 d . . . . .
H18 H 0.081(2) 0.541(2) 0.3035(14) 0.044(5) Uiso 1 1 d . . . . .
H16 H 0.003(2) 0.367(2) 0.4532(14) 0.039(5) Uiso 1 1 d . . . . .
H35 H 0.720(2) -0.161(2) 0.1849(15) 0.048(6) Uiso 1 1 d . . . . .
H36 H 0.471(2) -0.130(2) 0.1739(14) 0.039(5) Uiso 1 1 d . . . . .
H5 H 0.112(2) -0.076(2) 0.0686(15) 0.042(5) Uiso 1 1 d . . . . .
H30 H 0.606(2) 0.009(2) 0.0321(16) 0.051(6) Uiso 1 1 d . . . . .
H17 H -0.015(2) 0.618(2) 0.2167(16) 0.044(5) Uiso 1 1 d . . . . .
H11 H -0.296(2) 0.466(2) 0.3294(15) 0.048(6) Uiso 1 1 d . . . . .
H23 H 0.463(2) 0.359(2) 0.5005(16) 0.049(6) Uiso 1 1 d . . . . .
H19 H -0.051(2) 0.659(3) 0.3191(17) 0.065(7) Uiso 1 1 d . . . . .
H13 H -0.284(2) 0.613(2) 0.3333(15) 0.044(5) Uiso 1 1 d . . . . .
H33 H 0.780(2) -0.038(2) 0.1904(17) 0.058(6) Uiso 1 1 d . . . . .
H6 H 0.141(2) 0.146(2) -0.0036(16) 0.047(6) Uiso 1 1 d . . . . .
H15 H -0.133(2) 0.490(3) 0.4694(17) 0.059(6) Uiso 1 1 d . . . . .
H37 H 0.438(2) -0.084(2) 0.2703(16) 0.045(5) Uiso 1 1 d . . . . .
H31 H 0.498(2) 0.147(2) 0.0430(15) 0.045(5) Uiso 1 1 d . . . . .
H12 H -0.251(2) 0.575(2) 0.2271(17) 0.054(6) Uiso 1 1 d . . . . .
H8 H 0.255(2) 0.325(2) -0.0405(16) 0.057(6) Uiso 1 1 d . . . . .
H14 H -0.143(2) 0.340(2) 0.4626(16) 0.053(6) Uiso 1 1 d . . . . .
H7 H 0.089(3) 0.389(3) -0.0560(18) 0.062(7) Uiso 1 1 d . . . . .
H9 H 0.178(2) 0.480(3) -0.0318(17) 0.061(7) Uiso 1 1 d . . . . .
H22 H 0.650(3) 0.167(3) 0.5471(19) 0.076(8) Uiso 1 1 d . . . . .
H21 H 0.655(3) 0.014(3) 0.5351(18) 0.069(8) Uiso 1 1 d . . . . .
H20 H 0.507(3) 0.114(3) 0.552(2) 0.080(8) Uiso 1 1 d . . . . .
H4 H 0.061(2) -0.142(2) 0.2380(15) 0.043(5) Uiso 1 1 d . . . . .
H25 H 0.339(2) 0.649(2) 0.2550(15) 0.048(6) Uiso 1 1 d . . . . .
H24 H 0.342(2) 0.584(2) 0.4228(16) 0.053(6) Uiso 1 1 d . . . . .
H34 H 0.691(2) -0.109(2) 0.2809(17) 0.052(6) Uiso 1 1 d . . . . .


_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
S2 C22 1.6704(13) . ?
S1 C9 1.6663(14) . ?
O2 C6 1.3666(19) . ?
O2 C8 1.429(2) . ?
O3 C19 1.360(2) . ?
O3 C21 1.432(2) . ?
N2 C22 1.3253(18) . ?
N2 C23 1.4873(17) . ?
N2 H29 0.876(19) . ?
O4 C15 1.3601(19) . ?
O4 C14 1.399(2) . ?
O1 C2 1.3611(18) . ?
O1 C1 1.376(2) . ?
N1 C9 1.3236(18) . ?
N1 C10 1.4859(17) . ?
N1 H10 0.86(2) . ?
C20 C15 1.387(2) . ?
C20 C19 1.401(2) . ?
C20 C22 1.4962(18) . ?
C7 C2 1.387(2) . ?
C7 C6 1.399(2) . ?
C7 C9 1.5017(18) . ?
C6 C5 1.393(2) . ?
C19 C18 1.394(2) . ?
C23 C25 1.520(2) . ?
C23 C26 1.526(2) . ?
C23 C24 1.527(2) . ?
C2 C3 1.400(2) . ?
C15 C16 1.396(2) . ?
C10 C12 1.519(2) . ?
C10 C11 1.530(2) . ?
C10 C13 1.532(2) . ?
C3 C4 1.383(2) . ?
C3 H4 0.96(2) . ?
C5 C4 1.382(3) . ?
C5 H6 0.92(2) . ?
C4 H5 0.99(2) . ?
C25 H32 0.99(2) . ?
C25 H30 0.98(2) . ?
C25 H31 0.98(2) . ?
C24 H38 0.97(2) . ?
C24 H36 1.00(2) . ?
C24 H37 0.96(2) . ?
C16 C17 1.374(3) . ?
C16 H25 0.96(2) . ?
C13 H18 0.97(2) . ?
C13 H17 1.00(2) . ?
C13 H19 0.99(3) . ?
C11 H11 0.97(2) . ?
C11 H13 0.98(2) . ?
C11 H12 1.07(2) . ?
C18 C17 1.377(3) . ?
C18 H23 0.92(2) . ?
C26 H35 0.99(2) . ?
C26 H33 0.98(2) . ?
C26 H34 0.96(2) . ?
C17 H24 0.98(2) . ?
C12 H16 0.98(2) . ?
C12 H15 1.00(3) . ?
C12 H14 1.00(2) . ?
C8 H8 0.99(2) . ?
C8 H7 1.02(3) . ?
C8 H9 0.96(3) . ?
C21 H22 1.01(3) . ?
C21 H21 0.96(3) . ?
C21 H20 1.02(3) . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C1 H3 0.9600 . ?
C14 H27 0.9600 . ?
C14 H28 0.9600 . ?
C14 H26 0.9600 . ?

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
C6 O2 C8 117.58(14) . . ?
C19 O3 C21 117.46(17) . . ?
C22 N2 C23 128.99(12) . . ?
C22 N2 H29 115.2(13) . . ?
C23 N2 H29 115.7(13) . . ?
C15 O4 C14 118.10(15) . . ?
C2 O1 C1 118.76(14) . . ?
C9 N1 C10 129.32(12) . . ?
C9 N1 H10 116.5(12) . . ?
C10 N1 H10 114.1(12) . . ?
C15 C20 C19 119.88(13) . . ?
C15 C20 C22 120.09(12) . . ?
C19 C20 C22 120.01(13) . . ?
C2 C7 C6 119.65(13) . . ?
C2 C7 C9 120.13(13) . . ?
C6 C7 C9 120.18(13) . . ?
N1 C9 C7 112.91(12) . . ?
N1 C9 S1 127.41(11) . . ?
C7 C9 S1 119.68(10) . . ?
N2 C22 C20 113.22(11) . . ?
N2 C22 S2 127.57(10) . . ?
C20 C22 S2 119.20(10) . . ?
O2 C6 C5 124.84(14) . . ?
O2 C6 C7 115.08(13) . . ?
C5 C6 C7 120.08(15) . . ?
O3 C19 C18 125.55(15) . . ?
O3 C19 C20 114.95(13) . . ?
C18 C19 C20 119.50(16) . . ?
N2 C23 C25 109.27(12) . . ?
N2 C23 C26 110.33(12) . . ?
C25 C23 C26 111.41(14) . . ?
N2 C23 C24 106.11(11) . . ?
C25 C23 C24 109.95(12) . . ?
C26 C23 C24 109.64(14) . . ?
O1 C2 C7 115.43(13) . . ?
O1 C2 C3 124.09(14) . . ?
C7 C2 C3 120.48(14) . . ?
O4 C15 C20 115.13(13) . . ?
O4 C15 C16 124.34(16) . . ?
C20 C15 C16 120.53(15) . . ?
N1 C10 C12 110.03(14) . . ?
N1 C10 C11 105.32(12) . . ?
C12 C10 C11 109.84(14) . . ?
N1 C10 C13 110.40(12) . . ?
C12 C10 C13 111.50(14) . . ?
C11 C10 C13 109.57(14) . . ?
C4 C3 C2 118.83(15) . . ?
C4 C3 H4 121.2(12) . . ?
C2 C3 H4 119.8(12) . . ?
C4 C5 C6 119.29(15) . . ?
C4 C5 H6 120.8(14) . . ?
C6 C5 H6 119.9(14) . . ?
C5 C4 C3 121.65(14) . . ?
C5 C4 H5 118.9(12) . . ?
C3 C4 H5 119.5(12) . . ?
C23 C25 H32 112.6(12) . . ?
C23 C25 H30 111.1(13) . . ?
H32 C25 H30 107.4(17) . . ?
C23 C25 H31 110.1(12) . . ?
H32 C25 H31 108.4(17) . . ?
H30 C25 H31 107.1(18) . . ?
C23 C24 H38 112.5(12) . . ?
C23 C24 H36 111.2(11) . . ?
H38 C24 H36 107.9(16) . . ?
C23 C24 H37 112.1(13) . . ?
H38 C24 H37 107.0(17) . . ?
H36 C24 H37 105.8(17) . . ?
C17 C16 C15 118.50(17) . . ?
C17 C16 H25 121.6(13) . . ?
C15 C16 H25 119.8(13) . . ?
C10 C13 H18 110.2(12) . . ?
C10 C13 H17 111.5(12) . . ?
H18 C13 H17 108.0(16) . . ?
C10 C13 H19 110.0(14) . . ?
H18 C13 H19 107.9(18) . . ?
H17 C13 H19 109.1(18) . . ?
C10 C11 H11 108.4(12) . . ?
C10 C11 H13 108.9(12) . . ?
H11 C11 H13 109.5(17) . . ?
C10 C11 H12 111.2(12) . . ?
H11 C11 H12 110.5(18) . . ?
H13 C11 H12 108.2(17) . . ?
C17 C18 C19 119.20(16) . . ?
C17 C18 H23 121.6(14) . . ?
C19 C18 H23 119.2(14) . . ?
C23 C26 H35 109.2(12) . . ?
C23 C26 H33 111.5(14) . . ?
H35 C26 H33 107.5(18) . . ?
C23 C26 H34 109.3(13) . . ?
H35 C26 H34 109.1(18) . . ?
H33 C26 H34 110.3(19) . . ?
C16 C17 C18 122.36(15) . . ?
C16 C17 H24 117.4(13) . . ?
C18 C17 H24 120.2(13) . . ?
C10 C12 H16 110.6(12) . . ?
C10 C12 H15 109.5(13) . . ?
H16 C12 H15 111.5(18) . . ?
C10 C12 H14 111.6(13) . . ?
H16 C12 H14 105.2(17) . . ?
H15 C12 H14 108.4(18) . . ?
O2 C8 H8 110.5(13) . . ?
O2 C8 H7 108.3(14) . . ?
H8 C8 H7 111(2) . . ?
O2 C8 H9 104.8(14) . . ?
H8 C8 H9 111.8(19) . . ?
H7 C8 H9 110(2) . . ?
O3 C21 H22 111.4(15) . . ?
O3 C21 H21 105.6(16) . . ?
H22 C21 H21 112(2) . . ?
O3 C21 H20 108.0(16) . . ?
H22 C21 H20 112(2) . . ?
H21 C21 H20 108(2) . . ?
O1 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
O4 C14 H27 109.5 . . ?
O4 C14 H28 109.5 . . ?
H27 C14 H28 109.5 . . ?
O4 C14 H26 109.5 . . ?
H27 C14 H26 109.5 . . ?
H28 C14 H26 109.5 . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Slow evaporation of dichloromethane and pentane mixtures'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1468848'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N-(4-chlorophenyl)-2,6-dimethoxybenzothioamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Cl N O2 S'
_chemical_formula_weight         307.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7838(2)
_cell_length_b                   13.8454(5)
_cell_length_c                   14.3496(5)
_cell_angle_alpha                76.510(3)
_cell_angle_beta                 76.082(3)
_cell_angle_gamma                83.060(2)
_cell_volume                     1456.20(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    130
_cell_measurement_reflns_used    8936
_cell_measurement_theta_min      4.1210
_cell_measurement_theta_max      76.8050

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    3.667
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      130
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13965
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.247
_diffrn_reflns_theta_max         76.953
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6079
_reflns_number_gt                5782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.6152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6079
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.14829(5) -0.07092(2) 0.38321(2) 0.02095(9) Uani 1 1 d . . . . .
S2 S 0.91608(4) 0.65681(2) -0.03091(2) 0.01997(9) Uani 1 1 d . . . . .
Cl1 Cl 0.54720(6) 0.30236(3) 0.53644(3) 0.03550(10) Uani 1 1 d . . . . .
Cl2 Cl 0.20396(6) 0.54798(3) 0.33181(3) 0.03402(10) Uani 1 1 d . . . . .
O1 O 0.15882(13) 0.07071(8) 0.15630(7) 0.0214(2) Uani 1 1 d . . . . .
O3 O 0.47178(13) 0.59546(8) 0.07373(8) 0.0223(2) Uani 1 1 d . . . . .
O4 O 0.85381(13) 0.75158(8) 0.18795(8) 0.0240(2) Uani 1 1 d . . . . .
O2 O 0.51782(13) 0.07688(8) 0.37166(7) 0.0243(2) Uani 1 1 d . . . . .
N1 N 0.11458(15) 0.11711(9) 0.39539(8) 0.0175(2) Uani 1 1 d . . . . .
N2 N 0.83139(15) 0.52056(9) 0.13141(8) 0.0187(2) Uani 1 1 d . . . . .
C21 C 0.48663(17) 0.67218(10) 0.11557(9) 0.0169(2) Uani 1 1 d . . . . .
C2 C 0.51113(18) 0.08849(10) 0.27543(10) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.34583(17) 0.07663(9) 0.25948(9) 0.0161(2) Uani 1 1 d . . . . .
C23 C 0.65625(17) 0.67898(10) 0.12892(9) 0.0165(2) Uani 1 1 d . . . . .
C6 C 0.32448(18) 0.08553(10) 0.16366(10) 0.0176(3) Uani 1 1 d . . . . .
C24 C 0.80313(17) 0.61300(10) 0.08348(10) 0.0165(2) Uani 1 1 d . . . . .
C11 C 0.13978(17) 0.22031(10) 0.37573(10) 0.0175(3) Uani 1 1 d . . . . .
C19 C 0.38132(19) 0.81459(10) 0.18569(10) 0.0203(3) Uani 1 1 d . . . . .
C20 C 0.34782(17) 0.74050(10) 0.14326(10) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.19751(17) 0.04805(10) 0.34625(9) 0.0163(2) Uani 1 1 d . . . . .
C25 C 0.74791(17) 0.47437(10) 0.22927(10) 0.0187(3) Uani 1 1 d . . . . .
C4 C 0.62886(19) 0.12218(11) 0.10186(10) 0.0232(3) Uani 1 1 d . . . . .
C18 C 0.54738(19) 0.82130(10) 0.20275(10) 0.0206(3) Uani 1 1 d . . . . .
C17 C 0.68525(18) 0.75290(10) 0.17439(10) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.65544(18) 0.11113(11) 0.19636(11) 0.0225(3) Uani 1 1 d . . . . .
C10 C 0.1681(2) 0.27983(11) 0.28158(10) 0.0222(3) Uani 1 1 d . . . . .
C14 C 0.17541(19) 0.42187(11) 0.34909(11) 0.0232(3) Uani 1 1 d . . . . .
C5 C 0.46657(19) 0.10949(11) 0.08415(10) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.1406(2) 0.36435(11) 0.44326(11) 0.0250(3) Uani 1 1 d . . . . .
C26 C 0.75135(19) 0.51454(11) 0.30882(11) 0.0231(3) Uani 1 1 d . . . . .
C12 C 0.1241(2) 0.26322(11) 0.45656(10) 0.0227(3) Uani 1 1 d . . . . .
C27 C 0.6856(2) 0.46214(12) 0.40364(11) 0.0257(3) Uani 1 1 d . . . . .
C30 C 0.6755(2) 0.38359(11) 0.24374(11) 0.0254(3) Uani 1 1 d . . . . .
C15 C 0.1888(2) 0.38053(11) 0.26796(11) 0.0251(3) Uani 1 1 d . . . . .
C28 C 0.6180(2) 0.37079(11) 0.41730(11) 0.0246(3) Uani 1 1 d . . . . .
C22 C 0.31129(19) 0.59587(12) 0.04162(11) 0.0238(3) Uani 1 1 d . . . . .
C7 C 0.1373(2) 0.06549(12) 0.06130(10) 0.0248(3) Uani 1 1 d . . . . .
C29 C 0.6087(2) 0.33118(12) 0.33851(12) 0.0288(3) Uani 1 1 d . . . . .
C16 C 0.8798(2) 0.81487(15) 0.24851(14) 0.0355(4) Uani 1 1 d . . . . .
C1 C 0.6886(2) 0.06006(16) 0.39492(13) 0.0365(4) Uani 1 1 d . . . . .
170 H 0.867(3) 0.8866(19) 0.2119(18) 0.049(6) Uiso 1 1 d . . . . .
H12 H 0.209(3) 0.4206(16) 0.2043(16) 0.038(5) Uiso 1 1 d . . . . .
H5 H 0.727(3) 0.1407(15) 0.0483(15) 0.032(5) Uiso 1 1 d . . . . .
H56 H 0.207(2) 0.5890(14) 0.0985(14) 0.026(5) Uiso 1 1 d . . . . .
H57 H 0.327(3) 0.5369(15) 0.0121(14) 0.030(5) Uiso 1 1 d . . . . .
H53 H 0.286(2) 0.8623(14) 0.2040(13) 0.021(4) Uiso 1 1 d . . . . .
H8 H 0.224(3) 0.0153(15) 0.0355(15) 0.032(5) Uiso 1 1 d . . . . .
H6 H 0.453(3) 0.1202(15) 0.0167(16) 0.034(5) Uiso 1 1 d . . . . .
H7 H 0.150(3) 0.1289(16) 0.0140(15) 0.033(5) Uiso 1 1 d . . . . .
H13 H 0.128(3) 0.3932(16) 0.5036(16) 0.037(5) Uiso 1 1 d . . . . .
H3 H 0.758(3) 0.004(2) 0.3709(19) 0.056(7) Uiso 1 1 d . . . . .
H14 H 0.103(2) 0.2187(15) 0.5207(15) 0.028(5) Uiso 1 1 d . . . . .
H59 H 0.806(2) 0.5771(15) 0.2979(14) 0.026(5) Uiso 1 1 d . . . . .
H4 H 0.768(3) 0.1214(15) 0.2062(14) 0.030(5) Uiso 1 1 d . . . . .
H62 H 0.690(3) 0.4875(18) 0.4572(18) 0.047(6) Uiso 1 1 d . . . . .
H2 H 0.762(3) 0.1215(18) 0.3696(17) 0.047(6) Uiso 1 1 d . . . . .
H51 H 0.995(3) 0.7977(17) 0.2600(16) 0.039(6) Uiso 1 1 d . . . . .
H11 H 0.171(3) 0.2523(16) 0.2254(16) 0.039(6) Uiso 1 1 d . . . . .
H54 H 0.232(2) 0.7355(13) 0.1329(13) 0.020(4) Uiso 1 1 d . . . . .
H52 H 0.561(2) 0.8731(15) 0.2322(14) 0.028(5) Uiso 1 1 d . . . . .
H10 H 0.042(3) 0.0921(15) 0.4559(15) 0.028(5) Uiso 1 1 d . . . . .
H55 H 0.295(3) 0.6585(16) -0.0067(15) 0.030(5) Uiso 1 1 d . . . . .
H1 H 0.666(3) 0.0457(19) 0.4662(19) 0.052(7) Uiso 1 1 d . . . . .
H9 H 0.012(3) 0.0460(16) 0.0705(16) 0.038(5) Uiso 1 1 d . . . . .
H60 H 0.672(3) 0.3569(16) 0.1886(15) 0.034(5) Uiso 1 1 d . . . . .
H61 H 0.558(3) 0.2701(17) 0.3474(16) 0.041(6) Uiso 1 1 d . . . . .
H50 H 0.790(3) 0.8063(17) 0.3135(17) 0.045(6) Uiso 1 1 d . . . . .
H58 H 0.908(3) 0.4807(15) 0.0950(15) 0.032(5) Uiso 1 1 d . . . . .


_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 C9 1.6699(14) . ?
S2 C24 1.6749(14) . ?
Cl1 C28 1.7439(15) . ?
Cl2 C14 1.7392(15) . ?
O1 C6 1.3623(16) . ?
O1 C7 1.4319(16) . ?
O3 C21 1.3648(15) . ?
O3 C22 1.4308(16) . ?
O4 C17 1.3693(16) . ?
O4 C16 1.4307(17) . ?
O2 C2 1.3654(16) . ?
O2 C1 1.4266(18) . ?
N1 C9 1.3321(17) . ?
N1 C11 1.4188(17) . ?
N1 H10 0.93(2) . ?
N2 C24 1.3243(18) . ?
N2 C25 1.4303(18) . ?
N2 H58 0.92(2) . ?
C21 C20 1.3934(18) . ?
C21 C23 1.3960(18) . ?
C2 C8 1.3947(18) . ?
C2 C3 1.3978(19) . ?
C8 C6 1.3996(18) . ?
C8 C9 1.4929(17) . ?
C23 C17 1.4010(18) . ?
C23 C24 1.4945(17) . ?
C6 C5 1.3929(19) . ?
C11 C10 1.3908(19) . ?
C11 C12 1.3960(18) . ?
C19 C20 1.3869(19) . ?
C19 C18 1.390(2) . ?
C19 H53 0.961(18) . ?
C20 H54 0.962(18) . ?
C25 C26 1.3883(19) . ?
C25 C30 1.391(2) . ?
C4 C5 1.386(2) . ?
C4 C3 1.391(2) . ?
C4 H5 0.96(2) . ?
C18 C17 1.3922(19) . ?
C18 H52 0.94(2) . ?
C3 H4 0.95(2) . ?
C10 C15 1.386(2) . ?
C10 H11 0.96(2) . ?
C14 C13 1.381(2) . ?
C14 C15 1.390(2) . ?
C5 H6 0.97(2) . ?
C13 C12 1.386(2) . ?
C13 H13 1.01(2) . ?
C26 C27 1.391(2) . ?
C26 H59 0.976(19) . ?
C12 H14 0.97(2) . ?
C27 C28 1.382(2) . ?
C27 H62 0.93(2) . ?
C30 C29 1.392(2) . ?
C30 H60 0.95(2) . ?
C15 H12 0.94(2) . ?
C28 C29 1.386(2) . ?
C22 H56 0.999(19) . ?
C22 H57 0.99(2) . ?
C22 H55 0.99(2) . ?
C7 H8 0.98(2) . ?
C7 H7 0.98(2) . ?
C7 H9 1.01(2) . ?
C29 H61 0.94(2) . ?
C16 170 1.01(3) . ?
C16 H51 0.94(2) . ?
C16 H50 1.01(2) . ?
C1 H3 0.97(3) . ?
C1 H2 1.03(2) . ?
C1 H1 0.97(3) . ?

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
C6 O1 C7 116.97(11) . . ?
C21 O3 C22 116.85(11) . . ?
C17 O4 C16 116.58(11) . . ?
C2 O2 C1 117.47(12) . . ?
C9 N1 C11 129.46(11) . . ?
C9 N1 H10 114.5(12) . . ?
C11 N1 H10 115.4(12) . . ?
C24 N2 C25 128.14(11) . . ?
C24 N2 H58 114.8(13) . . ?
C25 N2 H58 116.8(13) . . ?
O3 C21 C20 124.56(12) . . ?
O3 C21 C23 114.66(11) . . ?
C20 C21 C23 120.78(12) . . ?
O2 C2 C8 115.09(12) . . ?
O2 C2 C3 124.33(12) . . ?
C8 C2 C3 120.59(12) . . ?
C2 C8 C6 119.91(12) . . ?
C2 C8 C9 118.75(11) . . ?
C6 C8 C9 121.23(12) . . ?
C21 C23 C17 119.49(12) . . ?
C21 C23 C24 117.29(11) . . ?
C17 C23 C24 122.88(12) . . ?
O1 C6 C5 124.71(12) . . ?
O1 C6 C8 115.23(11) . . ?
C5 C6 C8 120.05(13) . . ?
N2 C24 C23 119.48(12) . . ?
N2 C24 S2 122.32(10) . . ?
C23 C24 S2 118.03(10) . . ?
C10 C11 C12 119.77(13) . . ?
C10 C11 N1 123.05(12) . . ?
C12 C11 N1 117.07(12) . . ?
C20 C19 C18 121.99(13) . . ?
C20 C19 H53 118.7(11) . . ?
C18 C19 H53 119.3(11) . . ?
C19 C20 C21 118.51(12) . . ?
C19 C20 H54 121.5(11) . . ?
C21 C20 H54 120.0(11) . . ?
N1 C9 C8 119.05(12) . . ?
N1 C9 S1 121.72(10) . . ?
C8 C9 S1 119.12(10) . . ?
C26 C25 C30 120.52(13) . . ?
C26 C25 N2 121.13(13) . . ?
C30 C25 N2 118.15(12) . . ?
C5 C4 C3 122.34(13) . . ?
C5 C4 H5 120.4(12) . . ?
C3 C4 H5 117.3(12) . . ?
C19 C18 C17 118.98(12) . . ?
C19 C18 H52 117.9(12) . . ?
C17 C18 H52 123.1(12) . . ?
O4 C17 C18 124.30(12) . . ?
O4 C17 C23 115.51(12) . . ?
C18 C17 C23 120.19(12) . . ?
C4 C3 C2 118.15(13) . . ?
C4 C3 H4 120.4(12) . . ?
C2 C3 H4 121.4(12) . . ?
C15 C10 C11 119.94(13) . . ?
C15 C10 H11 119.2(13) . . ?
C11 C10 H11 120.8(13) . . ?
C13 C14 C15 121.10(14) . . ?
C13 C14 Cl2 119.40(11) . . ?
C15 C14 Cl2 119.50(12) . . ?
C4 C5 C6 118.92(13) . . ?
C4 C5 H6 119.6(12) . . ?
C6 C5 H6 121.4(12) . . ?
C14 C13 C12 119.24(13) . . ?
C14 C13 H13 122.4(12) . . ?
C12 C13 H13 118.3(12) . . ?
C25 C26 C27 119.51(14) . . ?
C25 C26 H59 119.8(11) . . ?
C27 C26 H59 120.6(11) . . ?
C13 C12 C11 120.34(13) . . ?
C13 C12 H14 123.0(11) . . ?
C11 C12 H14 116.6(11) . . ?
C28 C27 C26 119.52(14) . . ?
C28 C27 H62 120.3(15) . . ?
C26 C27 H62 120.2(15) . . ?
C25 C30 C29 120.13(14) . . ?
C25 C30 H60 120.0(13) . . ?
C29 C30 H60 119.8(13) . . ?
C10 C15 C14 119.55(14) . . ?
C10 C15 H12 119.9(13) . . ?
C14 C15 H12 120.5(13) . . ?
C27 C28 C29 121.59(14) . . ?
C27 C28 Cl1 119.25(12) . . ?
C29 C28 Cl1 119.15(12) . . ?
O3 C22 H56 110.8(11) . . ?
O3 C22 H57 104.6(11) . . ?
H56 C22 H57 109.6(16) . . ?
O3 C22 H55 109.6(11) . . ?
H56 C22 H55 110.1(16) . . ?
H57 C22 H55 112.0(16) . . ?
O1 C7 H8 109.6(12) . . ?
O1 C7 H7 113.4(12) . . ?
H8 C7 H7 109.2(17) . . ?
O1 C7 H9 106.6(12) . . ?
H8 C7 H9 110.6(17) . . ?
H7 C7 H9 107.4(17) . . ?
C28 C29 C30 118.70(14) . . ?
C28 C29 H61 121.9(13) . . ?
C30 C29 H61 119.4(13) . . ?
O4 C16 170 108.3(14) . . ?
O4 C16 H51 106.6(14) . . ?
170 C16 H51 111.4(19) . . ?
O4 C16 H50 112.5(13) . . ?
170 C16 H50 108.5(18) . . ?
H51 C16 H50 109.6(18) . . ?
O2 C1 H3 112.9(15) . . ?
O2 C1 H2 113.0(13) . . ?
H3 C1 H2 109(2) . . ?
O2 C1 H1 105.6(14) . . ?
H3 C1 H1 109(2) . . ?
H2 C1 H1 107.3(19) . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Slow evaporation of dichloromethane and pentane mixtures'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1468849'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,6-dimethoxy-N-phenylbenzothioamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N O2 S'
_chemical_formula_weight         273.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.0843(2)
_cell_length_b                   12.4311(2)
_cell_length_c                   17.6208(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2866.06(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    129.95(11)
_cell_measurement_reflns_used    10589
_cell_measurement_theta_min      5.0160
_cell_measurement_theta_max      76.4120

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    1.984
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      129.95(11)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            29121
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         5.020
_diffrn_reflns_theta_max         76.924
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3026
_reflns_number_gt                2672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.7558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3026
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.54342(2) 0.50001(2) 0.38492(2) 0.02376(10) Uani 1 1 d . . . . .
O1 O 0.25727(7) 0.49615(7) 0.32551(5) 0.0286(2) Uani 1 1 d . . . . .
O2 O 0.53607(7) 0.26273(8) 0.30760(5) 0.0316(2) Uani 1 1 d . . . . .
N1 N 0.38416(7) 0.41176(8) 0.44926(5) 0.0229(2) Uani 1 1 d . . . . .
C1 C 0.39781(8) 0.38178(9) 0.31217(6) 0.0225(2) Uani 1 1 d . . . . .
C9 C 0.43659(8) 0.42586(9) 0.38538(6) 0.0212(2) Uani 1 1 d . . . . .
C10 C 0.29002(9) 0.35687(10) 0.46121(6) 0.0260(2) Uani 1 1 d . . . . .
C6 C 0.30746(9) 0.42283(9) 0.28119(6) 0.0251(2) Uani 1 1 d . . . . .
C2 C 0.45369(9) 0.30497(10) 0.27097(7) 0.0255(2) Uani 1 1 d . . . . .
C5 C 0.27427(10) 0.39102(11) 0.20939(7) 0.0312(3) Uani 1 1 d . . . . .
C3 C 0.42184(10) 0.27387(11) 0.19869(7) 0.0308(3) Uani 1 1 d . . . . .
C4 C 0.33277(11) 0.31788(11) 0.16909(7) 0.0341(3) Uani 1 1 d . . . . .
C15 C 0.27076(12) 0.25607(11) 0.43033(8) 0.0366(3) Uani 1 1 d . . . . .
C11 C 0.21881(10) 0.40592(12) 0.50809(8) 0.0354(3) Uani 1 1 d . . . . .
C8 C 0.59556(11) 0.18397(12) 0.26787(8) 0.0369(3) Uani 1 1 d . . . . .
C14 C 0.17786(14) 0.20600(13) 0.44503(9) 0.0480(4) Uani 1 1 d . . . . .
C12 C 0.12647(12) 0.35430(15) 0.52279(9) 0.0489(4) Uani 1 1 d . . . . .
C7 C 0.15204(12) 0.51509(15) 0.30917(11) 0.0468(4) Uani 1 1 d . . . . .
C13 C 0.10624(13) 0.25483(16) 0.49056(10) 0.0539(4) Uani 1 1 d . . . . .
H10 H 0.4151(13) 0.4458(14) 0.4912(9) 0.038(4) Uiso 1 1 d . . . . .
H11 H 0.3246(14) 0.2225(15) 0.3989(11) 0.045(5) Uiso 1 1 d . . . . .
H3 H 0.4613(12) 0.2227(14) 0.1720(10) 0.037(4) Uiso 1 1 d . . . . .
H1 H 0.2122(13) 0.4197(14) 0.1883(10) 0.043(4) Uiso 1 1 d . . . . .
H6 H 0.6488(13) 0.1628(14) 0.3033(10) 0.041(4) Uiso 1 1 d . . . . .
H4 H 0.6241(12) 0.2156(14) 0.2200(10) 0.039(4) Uiso 1 1 d . . . . .
H5 H 0.5542(13) 0.1196(14) 0.2543(10) 0.043(5) Uiso 1 1 d . . . . .
H2 H 0.3113(13) 0.2952(15) 0.1179(10) 0.044(5) Uiso 1 1 d . . . . .
H15 H 0.2313(13) 0.4761(14) 0.5297(10) 0.040(4) Uiso 1 1 d . . . . .
H12 H 0.1661(15) 0.1351(17) 0.4225(12) 0.060(6) Uiso 1 1 d . . . . .
H13 H 0.0402(16) 0.218(2) 0.5026(14) 0.075(7) Uiso 1 1 d . . . . .
H14 H 0.0746(16) 0.3933(17) 0.5523(12) 0.064(6) Uiso 1 1 d . . . . .
H9 H 0.1244(14) 0.5550(16) 0.3537(11) 0.048(5) Uiso 1 1 d . . . . .
H8 H 0.1159(16) 0.4506(19) 0.3050(12) 0.061(6) Uiso 1 1 d . . . . .
H7 H 0.1477(18) 0.5591(19) 0.2618(15) 0.076(7) Uiso 1 1 d . . . . .


_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 C9 1.6744(12) . ?
O1 C6 1.3682(14) . ?
O1 C7 1.4263(16) . ?
O2 C2 1.3617(14) . ?
O2 C8 1.4333(15) . ?
N1 C9 1.3298(14) . ?
N1 C10 1.4238(14) . ?
N1 H10 0.943(17) . ?
C1 C6 1.3985(16) . ?
C1 C2 1.4048(16) . ?
C1 C9 1.4906(14) . ?
C10 C11 1.3865(18) . ?
C10 C15 1.3892(18) . ?
C6 C5 1.3948(16) . ?
C2 C3 1.3946(16) . ?
C5 C4 1.3845(19) . ?
C5 H1 0.961(17) . ?
C3 C4 1.3891(19) . ?
C3 H3 0.945(17) . ?
C4 H2 0.986(17) . ?
C15 C14 1.390(2) . ?
C15 H11 0.989(19) . ?
C11 C12 1.3924(19) . ?
C11 H15 0.966(18) . ?
C8 H6 0.972(18) . ?
C8 H4 1.003(18) . ?
C8 H5 0.995(18) . ?
C14 C13 1.375(3) . ?
C14 H12 0.98(2) . ?
C12 C13 1.386(3) . ?
C12 H14 0.98(2) . ?
C7 H9 0.997(19) . ?
C7 H8 0.93(2) . ?
C7 H7 1.00(3) . ?
C13 H13 1.00(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
C6 O1 C7 117.26(10) . . ?
C2 O2 C8 117.50(10) . . ?
C9 N1 C10 129.40(10) . . ?
C9 N1 H10 112.5(10) . . ?
C10 N1 H10 118.1(10) . . ?
C6 C1 C2 119.10(10) . . ?
C6 C1 C9 119.44(10) . . ?
C2 C1 C9 121.33(10) . . ?
N1 C9 C1 120.57(10) . . ?
N1 C9 S1 120.48(8) . . ?
C1 C9 S1 118.84(8) . . ?
C11 C10 C15 120.54(12) . . ?
C11 C10 N1 117.31(11) . . ?
C15 C10 N1 122.09(11) . . ?
O1 C6 C5 123.86(11) . . ?
O1 C6 C1 115.21(10) . . ?
C5 C6 C1 120.91(11) . . ?
O2 C2 C3 124.23(11) . . ?
O2 C2 C1 115.42(10) . . ?
C3 C2 C1 120.32(11) . . ?
C4 C5 C6 118.64(12) . . ?
C4 C5 H1 120.9(11) . . ?
C6 C5 H1 120.5(11) . . ?
C4 C3 C2 118.98(12) . . ?
C4 C3 H3 122.4(10) . . ?
C2 C3 H3 118.6(10) . . ?
C5 C4 C3 122.00(11) . . ?
C5 C4 H2 119.9(11) . . ?
C3 C4 H2 118.1(11) . . ?
C10 C15 C14 119.31(14) . . ?
C10 C15 H11 118.1(11) . . ?
C14 C15 H11 122.6(11) . . ?
C10 C11 C12 119.43(14) . . ?
C10 C11 H15 121.2(10) . . ?
C12 C11 H15 119.3(10) . . ?
O2 C8 H6 105.1(10) . . ?
O2 C8 H4 110.2(10) . . ?
H6 C8 H4 112.3(14) . . ?
O2 C8 H5 111.8(10) . . ?
H6 C8 H5 109.0(14) . . ?
H4 C8 H5 108.4(14) . . ?
C13 C14 C15 120.47(14) . . ?
C13 C14 H12 121.8(12) . . ?
C15 C14 H12 117.7(12) . . ?
C13 C12 C11 120.04(15) . . ?
C13 C12 H14 121.6(12) . . ?
C11 C12 H14 118.1(12) . . ?
O1 C7 H9 105.9(11) . . ?
O1 C7 H8 111.2(13) . . ?
H9 C7 H8 107.7(17) . . ?
O1 C7 H7 108.3(14) . . ?
H9 C7 H7 111.4(17) . . ?
H8 C7 H7 112.1(19) . . ?
C14 C13 C12 120.19(14) . . ?
C14 C13 H13 120.8(14) . . ?
C12 C13 H13 118.9(14) . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Slow evaporation of dichloromethane and pentane mixtures'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1468850'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,6-dimethoxy-N-(4-(trifluoromethyl)phenyl)benzothioamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 F3 N O2 S'
_chemical_formula_weight         341.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   11.2091(2)
_cell_length_b                   7.59230(10)
_cell_length_c                   18.4855(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.543(2)
_cell_angle_gamma                90
_cell_volume                     1573.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    8004
_cell_measurement_theta_min      3.9550
_cell_measurement_theta_max      76.1590

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.226
_exptl_absorpt_coefficient_mu    2.210
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.80174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.2273

_diffrn_reflns_number            14080
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.594
_diffrn_reflns_theta_max         76.906
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3294
_reflns_number_gt                3099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.8479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3294
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.09775(3) 0.97859(4) 0.39875(2) 0.02848(11) Uani 1 1 d . . . . .
F1 F 0.14195(9) 1.86794(14) 0.71392(6) 0.0500(3) Uani 1 1 d . . . . .
O2 O 0.12734(9) 1.33945(14) 0.30264(5) 0.0319(2) Uani 1 1 d . . . . .
O1 O 0.36392(9) 1.17178(14) 0.49953(5) 0.0334(2) Uani 1 1 d . . . . .
F3 F 0.32455(10) 1.80708(17) 0.69931(7) 0.0725(4) Uani 1 1 d . . . . .
N1 N 0.10206(10) 1.23432(15) 0.49405(6) 0.0241(2) Uani 1 1 d . . . . .
F2 F 0.23593(15) 1.98295(14) 0.62683(7) 0.0742(4) Uani 1 1 d . . . . .
C8 C 0.25075(11) 1.25873(16) 0.39944(7) 0.0231(3) Uani 1 1 d . . . . .
C10 C 0.13508(11) 1.38816(16) 0.53293(6) 0.0217(2) Uani 1 1 d . . . . .
C11 C 0.16748(12) 1.54516(17) 0.49969(7) 0.0244(3) Uani 1 1 d . . . . .
C12 C 0.19633(12) 1.69091(17) 0.54195(7) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.23897(12) 1.34215(17) 0.33213(7) 0.0257(3) Uani 1 1 d . . . . .
C9 C 0.14816(11) 1.16728(17) 0.43376(6) 0.0226(2) Uani 1 1 d . . . . .
C13 C 0.18966(12) 1.68090(17) 0.61663(7) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.36175(12) 1.25748(18) 0.43454(7) 0.0277(3) Uani 1 1 d . . . . .
C15 C 0.12724(14) 1.37967(19) 0.60811(7) 0.0305(3) Uani 1 1 d . . . . .
C3 C 0.33717(14) 1.42385(19) 0.30063(8) 0.0321(3) Uani 1 1 d . . . . .
C14 C 0.15427(14) 1.52603(19) 0.64960(7) 0.0311(3) Uani 1 1 d . . . . .
C16 C 0.22214(13) 1.8342(2) 0.66353(8) 0.0339(3) Uani 1 1 d . . . . .
C4 C 0.44585(14) 1.4189(2) 0.33643(9) 0.0375(3) Uani 1 1 d . . . . .
C5 C 0.46013(13) 1.3366(2) 0.40293(9) 0.0355(3) Uani 1 1 d . . . . .
C1 C 0.11140(17) 1.4179(3) 0.23295(9) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.46764(18) 1.1948(3) 0.54445(11) 0.0500(4) Uani 1 1 d . . . . .
H11 H 0.1657(15) 1.552(2) 0.4483(10) 0.034(4) Uiso 1 1 d . . . . .
H12 H 0.2174(15) 1.798(2) 0.5185(9) 0.033(4) Uiso 1 1 d . . . . .
H10 H 0.0509(17) 1.170(3) 0.5156(10) 0.039(5) Uiso 1 1 d . . . . .
H4 H 0.3302(16) 1.478(2) 0.2564(10) 0.036(5) Uiso 1 1 d . . . . .
H13 H 0.1050(17) 1.273(3) 0.6297(10) 0.043(5) Uiso 1 1 d . . . . .
H14 H 0.1497(17) 1.520(3) 0.7003(11) 0.044(5) Uiso 1 1 d . . . . .
H1 H 0.0263(18) 1.392(3) 0.2194(10) 0.045(5) Uiso 1 1 d . . . . .
H3 H 0.1234(17) 1.546(3) 0.2372(10) 0.046(5) Uiso 1 1 d . . . . .
H5 H 0.5151(19) 1.471(3) 0.3149(11) 0.046(5) Uiso 1 1 d . . . . .
H6 H 0.5336(18) 1.337(3) 0.4266(10) 0.042(5) Uiso 1 1 d . . . . .
H2 H 0.1686(19) 1.364(3) 0.1961(11) 0.051(6) Uiso 1 1 d . . . . .
H7 H 0.545(2) 1.142(3) 0.5194(13) 0.074(7) Uiso 1 1 d . . . . .
H8 H 0.4814(19) 1.318(3) 0.5536(12) 0.058(6) Uiso 1 1 d . . . . .
H9 H 0.448(2) 1.135(3) 0.5894(13) 0.065(7) Uiso 1 1 d . . . . .


_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 C9 1.6684(13) . ?
F1 C16 1.3255(17) . ?
O2 C2 1.3603(17) . ?
O2 C1 1.4290(17) . ?
O1 C6 1.3662(17) . ?
O1 C7 1.4331(19) . ?
F3 C16 1.3354(18) . ?
N1 C9 1.3338(16) . ?
N1 C10 1.4187(16) . ?
N1 H10 0.85(2) . ?
F2 C16 1.3272(19) . ?
C8 C6 1.3978(19) . ?
C8 C2 1.4013(17) . ?
C8 C9 1.4903(17) . ?
C10 C11 1.3908(18) . ?
C10 C15 1.3949(17) . ?
C11 C12 1.3910(18) . ?
C11 H11 0.952(18) . ?
C12 C13 1.3852(18) . ?
C12 H12 0.954(18) . ?
C2 C3 1.3956(19) . ?
C13 C14 1.3842(19) . ?
C13 C16 1.4944(18) . ?
C6 C5 1.389(2) . ?
C15 C14 1.3822(19) . ?
C15 H13 0.94(2) . ?
C3 C4 1.381(2) . ?
C3 H4 0.918(19) . ?
C14 H14 0.94(2) . ?
C4 C5 1.387(2) . ?
C4 H5 0.96(2) . ?
C5 H6 0.93(2) . ?
C1 H1 1.00(2) . ?
C1 H3 0.99(2) . ?
C1 H2 1.03(2) . ?
C7 H7 1.06(3) . ?
C7 H8 0.96(2) . ?
C7 H9 0.97(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
C2 O2 C1 117.49(12) . . ?
C6 O1 C7 117.32(13) . . ?
C9 N1 C10 129.51(11) . . ?
C9 N1 H10 116.0(13) . . ?
C10 N1 H10 114.0(12) . . ?
C6 C8 C2 119.42(12) . . ?
C6 C8 C9 119.09(11) . . ?
C2 C8 C9 121.47(12) . . ?
C11 C10 C15 119.93(12) . . ?
C11 C10 N1 123.35(11) . . ?
C15 C10 N1 116.62(11) . . ?
C10 C11 C12 119.60(12) . . ?
C10 C11 H11 119.1(11) . . ?
C12 C11 H11 121.2(11) . . ?
C13 C12 C11 120.11(12) . . ?
C13 C12 H12 121.1(10) . . ?
C11 C12 H12 118.7(10) . . ?
O2 C2 C3 124.45(12) . . ?
O2 C2 C8 115.32(11) . . ?
C3 C2 C8 120.22(13) . . ?
N1 C9 C8 118.98(11) . . ?
N1 C9 S1 121.29(10) . . ?
C8 C9 S1 119.65(9) . . ?
C14 C13 C12 120.25(12) . . ?
C14 C13 C16 118.39(12) . . ?
C12 C13 C16 121.35(13) . . ?
O1 C6 C5 124.62(13) . . ?
O1 C6 C8 114.82(11) . . ?
C5 C6 C8 120.56(13) . . ?
C14 C15 C10 120.01(13) . . ?
C14 C15 H13 121.1(12) . . ?
C10 C15 H13 118.9(12) . . ?
C4 C3 C2 118.91(13) . . ?
C4 C3 H4 120.4(12) . . ?
C2 C3 H4 120.6(12) . . ?
C15 C14 C13 120.05(12) . . ?
C15 C14 H14 119.8(12) . . ?
C13 C14 H14 120.1(12) . . ?
F1 C16 F2 106.13(13) . . ?
F1 C16 F3 105.49(13) . . ?
F2 C16 F3 106.30(14) . . ?
F1 C16 C13 113.28(12) . . ?
F2 C16 C13 113.27(13) . . ?
F3 C16 C13 111.76(12) . . ?
C3 C4 C5 122.06(13) . . ?
C3 C4 H5 120.2(12) . . ?
C5 C4 H5 117.7(12) . . ?
C4 C5 C6 118.82(14) . . ?
C4 C5 H6 120.8(12) . . ?
C6 C5 H6 120.4(12) . . ?
O2 C1 H1 104.6(11) . . ?
O2 C1 H3 109.0(11) . . ?
H1 C1 H3 110.1(16) . . ?
O2 C1 H2 111.0(11) . . ?
H1 C1 H2 110.7(16) . . ?
H3 C1 H2 111.1(17) . . ?
O1 C7 H7 111.1(13) . . ?
O1 C7 H8 110.4(13) . . ?
H7 C7 H8 108.3(19) . . ?
O1 C7 H9 104.6(14) . . ?
H7 C7 H9 112.8(19) . . ?
H8 C7 H9 109.8(19) . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Slow evaporation of dichloromethane and pentane mixtures'
