# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_nadeem_17084
_database_code_depnum_ccdc_archive 'CCDC 1812914'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
; 
N-(naphthalen-1-yl)benzenesulfonamide
;
_chemical_name_common            
;
N-(naphthalen-1-yl)benzenesulfonamidee
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2 O2 S'
_chemical_formula_sum            'C17 H14 N2 O2 S'
_chemical_formula_weight         310.36

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'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.2556(14)
_cell_length_b                   9.1252(7)
_cell_length_c                   24.169(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3144.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3524
_cell_measurement_theta_min      2.8992
_cell_measurement_theta_max      29.0089

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_min  0.79440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26897
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.141
_diffrn_reflns_theta_max         29.078
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4013
_reflns_number_gt                1773
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0927P)²+0.0243P] 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         4013
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.2190
_refine_ls_wR_factor_gt          0.1718
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.7043(2) 0.1790(3) 0.75194(13) 0.0663(8) Uani 1 1 d . . . . .
C2 C 0.7576(3) 0.2662(4) 0.78573(15) 0.0863(10) Uani 1 1 d . . . . .
H2 H 0.811089 0.310431 0.771315 0.104 Uiso 1 1 calc R U . . .
C3 C 0.7346(3) 0.2905(4) 0.84071(18) 0.1062(13) Uani 1 1 d . . . . .
H3 H 0.771971 0.350642 0.862601 0.127 Uiso 1 1 calc R U . . .
C4 C 0.6574(4) 0.2264(5) 0.86221(16) 0.1083(13) Uani 1 1 d . . . . .
H4 H 0.642845 0.241815 0.899263 0.130 Uiso 1 1 calc R U . . .
C5 C 0.5982(3) 0.1364(3) 0.82991(15) 0.0824(10) Uani 1 1 d . . . . .
C6 C 0.6212(2) 0.1147(3) 0.77331(13) 0.0685(8) Uani 1 1 d . . . . .
C7 C 0.5572(2) 0.0313(3) 0.74132(15) 0.0820(10) Uani 1 1 d . . . . .
H7 H 0.568572 0.017923 0.703768 0.098 Uiso 1 1 calc R U . . .
C8 C 0.4796(3) -0.0294(4) 0.7644(2) 0.1060(13) Uani 1 1 d . . . . .
H8 H 0.438495 -0.082510 0.742238 0.127 Uiso 1 1 calc R U . . .
C9 C 0.4604(4) -0.0140(4) 0.8199(2) 0.1195(15) Uani 1 1 d . . . . .
H9 H 0.408323 -0.059930 0.835278 0.143 Uiso 1 1 calc R U . . .
C10 C 0.5172(4) 0.0677(5) 0.85162(19) 0.1095(14) Uani 1 1 d . . . . .
H10 H 0.502962 0.079590 0.888901 0.131 Uiso 1 1 calc R U . . .
C11 C 0.7396(2) 0.1608(3) 0.69564(13) 0.0683(8) Uani 1 1 d . . . . .
H11 H 0.787789 0.222256 0.684161 0.082 Uiso 1 1 calc R U . . .
C12 C 0.5898(3) 0.0857(3) 0.55480(11) 0.0674(8) Uani 1 1 d . . . . .
C13 C 0.5103(3) 0.0379(3) 0.58046(15) 0.0818(9) Uani 1 1 d . . . . .
H13 H 0.511465 -0.049030 0.600560 0.098 Uiso 1 1 calc R U . . .
C14 C 0.4284(3) 0.1170(5) 0.57687(18) 0.1029(12) Uani 1 1 d . . . . .
H14 H 0.374417 0.084689 0.594692 0.123 Uiso 1 1 calc R U . . .
C15 C 0.4276(4) 0.2434(5) 0.5468(2) 0.1194(16) Uani 1 1 d . . . . .
H15 H 0.372496 0.297567 0.543934 0.143 Uiso 1 1 calc R U . . .
C16 C 0.5073(5) 0.2913(4) 0.52076(18) 0.1161(16) Uani 1 1 d . . . . .
H16 H 0.505293 0.376482 0.499680 0.139 Uiso 1 1 calc R U . . .
C17 C 0.5905(3) 0.2149(3) 0.52537(14) 0.0903(11) Uani 1 1 d . . . . .
H17 H 0.645243 0.249536 0.509096 0.108 Uiso 1 1 calc R U . . .
N1 N 0.70910(18) 0.0669(3) 0.66121(10) 0.0661(7) Uani 1 1 d . . . . .
N2 N 0.75561(19) 0.0629(3) 0.61008(11) 0.0729(8) Uani 1 1 d . . . . .
O1 O 0.67116(17) -0.1563(2) 0.57842(9) 0.0848(7) Uani 1 1 d . . . . .
O2 O 0.75042(19) 0.0078(3) 0.51235(9) 0.0941(8) Uani 1 1 d . . . . .
S1 S 0.69480(6) -0.01231(8) 0.56053(3) 0.0718(3) Uani 1 1 d . . . . .
H1N H 0.779(3) 0.144(3) 0.6033(13) 0.086 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(4) . ?
C1 C6 1.419(4) . ?
C1 C11 1.460(4) . ?
C2 C3 1.387(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.413(5) . ?
C4 H4 0.9300 . ?
C5 C10 1.415(5) . ?
C5 C6 1.420(4) . ?
C6 C7 1.418(4) . ?
C7 C8 1.357(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.342(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N1 1.270(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(5) . ?
C12 C17 1.377(4) . ?
C12 S1 1.749(3) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N1 N2 1.403(3) . ?
N2 S1 1.630(3) . ?
N2 H1N 0.83(3) . ?
O1 S1 1.424(2) . ?
O2 S1 1.421(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 C1 C6 119.1(3) . . ?
C2 C1 C11 115.5(3) . . ?
C6 C1 C11 125.4(3) . . ?
C1 C2 C3 122.2(4) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.7(4) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C10 122.7(4) . . ?
C4 C5 C6 118.4(4) . . ?
C10 C5 C6 118.9(4) . . ?
C7 C6 C1 124.1(3) . . ?
C7 C6 C5 116.8(3) . . ?
C1 C6 C5 119.0(3) . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 121.8(4) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
N1 C11 C1 124.7(3) . . ?
N1 C11 H11 117.6 . . ?
C1 C11 H11 117.6 . . ?
C13 C12 C17 121.0(3) . . ?
C13 C12 S1 120.8(2) . . ?
C17 C12 S1 118.2(3) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C12 C17 C16 117.9(4) . . ?
C12 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C11 N1 N2 115.7(3) . . ?
N1 N2 S1 114.0(2) . . ?
N1 N2 H1N 110(2) . . ?
S1 N2 H1N 117(2) . . ?
O2 S1 O1 120.03(14) . . ?
O2 S1 N2 104.52(16) . . ?
O1 S1 N2 106.95(14) . . ?
O2 S1 C12 110.27(15) . . ?
O1 S1 C12 107.06(15) . . ?
N2 S1 C12 107.33(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.8(5) . . . . ?
C11 C1 C2 C3 -178.2(3) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C10 179.8(4) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C2 C1 C6 C7 175.4(3) . . . . ?
C11 C1 C6 C7 -4.6(4) . . . . ?
C2 C1 C6 C5 -3.2(4) . . . . ?
C11 C1 C6 C5 176.8(3) . . . . ?
C4 C5 C6 C7 -176.2(3) . . . . ?
C10 C5 C6 C7 3.6(4) . . . . ?
C4 C5 C6 C1 2.5(4) . . . . ?
C10 C5 C6 C1 -177.7(3) . . . . ?
C1 C6 C7 C8 179.0(3) . . . . ?
C5 C6 C7 C8 -2.5(5) . . . . ?
C6 C7 C8 C9 -0.8(6) . . . . ?
C7 C8 C9 C10 2.8(7) . . . . ?
C8 C9 C10 C5 -1.5(7) . . . . ?
C4 C5 C10 C9 178.0(4) . . . . ?
C6 C5 C10 C9 -1.7(6) . . . . ?
C2 C1 C11 N1 168.1(3) . . . . ?
C6 C1 C11 N1 -11.9(5) . . . . ?
C17 C12 C13 C14 0.8(5) . . . . ?
S1 C12 C13 C14 178.5(3) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C15 C16 C17 -1.5(7) . . . . ?
C13 C12 C17 C16 -2.6(5) . . . . ?
S1 C12 C17 C16 179.7(3) . . . . ?
C15 C16 C17 C12 2.9(6) . . . . ?
C1 C11 N1 N2 -177.1(3) . . . . ?
C11 N1 N2 S1 -159.4(2) . . . . ?
N1 N2 S1 O2 174.6(2) . . . . ?
N1 N2 S1 O1 -57.2(2) . . . . ?
N1 N2 S1 C12 57.5(2) . . . . ?
C13 C12 S1 O2 150.4(3) . . . . ?
C17 C12 S1 O2 -31.9(3) . . . . ?
C13 C12 S1 O1 18.2(3) . . . . ?
C17 C12 S1 O1 -164.0(2) . . . . ?
C13 C12 S1 N2 -96.3(3) . . . . ?
C17 C12 S1 N2 81.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O1 0.83(3) 2.04(3) 2.870(3) 173(3) 7_765

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_nadeem_17054
_database_code_depnum_ccdc_archive 'CCDC 1812915'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
; 
4-Methyl-N-(naphthalen-1-yl)benzenesulfonamide
;
_chemical_name_common            
;
4-Methyl-N-(naphthalen-1-yl)benzenesulfonamidee
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O2 S'
_chemical_formula_sum            'C18 H16 N2 O2 S'
_chemical_formula_weight         324.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'

_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'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   9.9621(9)
_cell_length_b                   11.8993(12)
_cell_length_c                   14.2532(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.480(8)
_cell_angle_gamma                90
_cell_volume                     1681.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2405
_cell_measurement_theta_min      3.1203
_cell_measurement_theta_max      29.1597

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_min  0.71218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8713
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.127
_diffrn_reflns_theta_max         29.224
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4010
_reflns_number_gt                2519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0596P)²+0.3335P] 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         4010
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.29412(19) 0.59249(17) 0.98701(14) 0.0551(5) Uani 1 1 d . . . . .
C2 C 0.1900(2) 0.52284(19) 1.00708(17) 0.0688(6) Uani 1 1 d . . . . .
H2 H 0.116756 0.513346 0.962185 0.083 Uiso 1 1 calc R U . . .
C3 C 0.1914(3) 0.4665(2) 1.09254(19) 0.0779(7) Uani 1 1 d . . . . .
H3 H 0.118394 0.421969 1.104948 0.094 Uiso 1 1 calc R U . . .
C4 C 0.2991(3) 0.4762(2) 1.15796(18) 0.0744(6) Uani 1 1 d . . . . .
H4 H 0.299527 0.437987 1.214910 0.089 Uiso 1 1 calc R U . . .
C5 C 0.4106(2) 0.54395(17) 1.14028(15) 0.0613(5) Uani 1 1 d . . . . .
C6 C 0.40769(19) 0.60530(16) 1.05482(14) 0.0538(5) Uani 1 1 d . . . . .
C7 C 0.5199(2) 0.67565(18) 1.04161(16) 0.0644(6) Uani 1 1 d . . . . .
H7 H 0.519897 0.718257 0.986905 0.077 Uiso 1 1 calc R U . . .
C8 C 0.6272(2) 0.6813(2) 1.10802(19) 0.0784(7) Uani 1 1 d . . . . .
H8 H 0.699180 0.728279 1.098419 0.094 Uiso 1 1 calc R U . . .
C9 C 0.6306(3) 0.6176(2) 1.19022(19) 0.0847(7) Uani 1 1 d . . . . .
H9 H 0.705924 0.620423 1.234078 0.102 Uiso 1 1 calc R U . . .
C10 C 0.5247(3) 0.5519(2) 1.20629(17) 0.0766(7) Uani 1 1 d . . . . .
H10 H 0.527248 0.511116 1.262067 0.092 Uiso 1 1 calc R U . . .
C11 C 0.2883(2) 0.65002(18) 0.89612(15) 0.0577(5) Uani 1 1 d . . . . .
H11 H 0.364998 0.685343 0.878046 0.069 Uiso 1 1 calc R U . . .
C12 C 0.07978(18) 0.5409(2) 0.64495(14) 0.0592(5) Uani 1 1 d . . . . .
C13 C 0.0079(2) 0.4617(2) 0.68898(17) 0.0736(7) Uani 1 1 d . . . . .
H13 H -0.050648 0.483667 0.732600 0.088 Uiso 1 1 calc R U . . .
C14 C 0.0226(2) 0.3497(2) 0.66854(19) 0.0818(7) Uani 1 1 d . . . . .
H14 H -0.026581 0.296920 0.699158 0.098 Uiso 1 1 calc R U . . .
C15 C 0.1073(2) 0.3131(2) 0.60443(17) 0.0756(7) Uani 1 1 d . . . . .
C16 C 0.1770(3) 0.3935(3) 0.56003(17) 0.0855(8) Uani 1 1 d . . . . .
H16 H 0.234201 0.371244 0.515614 0.103 Uiso 1 1 calc R U . . .
C17 C 0.1645(2) 0.5066(2) 0.57944(16) 0.0783(7) Uani 1 1 d . . . . .
H17 H 0.213041 0.559344 0.548423 0.094 Uiso 1 1 calc R U . . .
C18 C 0.1239(3) 0.1904(3) 0.5839(2) 0.1092(10) Uani 1 1 d . . . . .
H18A H 0.140772 0.149894 0.642117 0.164 Uiso 1 1 calc R U . . .
H18B H 0.198480 0.180367 0.546783 0.164 Uiso 1 1 calc R U . . .
H18C H 0.043053 0.162398 0.549770 0.164 Uiso 1 1 calc R U . . .
N1 N 0.17991(16) 0.65246(15) 0.84149(12) 0.0598(4) Uani 1 1 d . . . . .
N2 N 0.18720(18) 0.70918(16) 0.75728(13) 0.0642(5) Uani 1 1 d . . . . .
O1 O -0.05743(15) 0.69981(15) 0.71256(13) 0.0881(5) Uani 1 1 d . . . . .
O2 O 0.10419(17) 0.75036(16) 0.59698(12) 0.0893(5) Uani 1 1 d . . . . .
S1 S 0.06834(5) 0.68353(5) 0.67357(4) 0.0663(2) Uani 1 1 d . . . . .
H1N H 0.261(2) 0.723(2) 0.7370(17) 0.080 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(3) . ?
C1 C6 1.424(3) . ?
C1 C11 1.461(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.408(3) . ?
C5 C6 1.418(3) . ?
C6 C7 1.424(3) . ?
C7 C8 1.360(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.350(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N1 1.270(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 C17 1.379(3) . ?
C12 S1 1.752(2) . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(4) . ?
C15 C18 1.502(4) . ?
C16 C17 1.382(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 N2 1.385(2) . ?
N2 S1 1.6276(19) . ?
N2 H1N 0.83(2) . ?
O1 S1 1.4315(16) . ?
O2 S1 1.4234(17) . ?

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 C1 C6 119.22(19) . . ?
C2 C1 C11 119.9(2) . . ?
C6 C1 C11 120.88(18) . . ?
C1 C2 C3 121.8(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C10 C5 C4 121.1(2) . . ?
C10 C5 C6 119.2(2) . . ?
C4 C5 C6 119.6(2) . . ?
C5 C6 C7 117.7(2) . . ?
C5 C6 C1 118.53(18) . . ?
C7 C6 C1 123.80(19) . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 121.3(2) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
N1 C11 C1 120.92(19) . . ?
N1 C11 H11 119.5 . . ?
C1 C11 H11 119.5 . . ?
C13 C12 C17 119.1(2) . . ?
C13 C12 S1 120.73(17) . . ?
C17 C12 S1 120.14(18) . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 122.2(2) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C16 C15 C14 117.2(2) . . ?
C16 C15 C18 121.2(2) . . ?
C14 C15 C18 121.6(3) . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C12 C17 C16 119.8(2) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 N1 N2 115.52(17) . . ?
N1 N2 S1 116.70(14) . . ?
N1 N2 H1N 121.2(17) . . ?
S1 N2 H1N 112.8(17) . . ?
O2 S1 O1 121.00(11) . . ?
O2 S1 N2 103.84(10) . . ?
O1 S1 N2 107.00(10) . . ?
O2 S1 C12 109.64(11) . . ?
O1 S1 C12 107.47(10) . . ?
N2 S1 C12 107.06(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.3(3) . . . . ?
C11 C1 C2 C3 180.0(2) . . . . ?
C1 C2 C3 C4 -2.1(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C10 -178.0(2) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
C10 C5 C6 C7 -2.2(3) . . . . ?
C4 C5 C6 C7 177.68(19) . . . . ?
C10 C5 C6 C1 177.28(18) . . . . ?
C4 C5 C6 C1 -2.9(3) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C11 C1 C6 C5 -177.45(17) . . . . ?
C2 C1 C6 C7 -179.5(2) . . . . ?
C11 C1 C6 C7 1.9(3) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C1 C6 C7 C8 -177.9(2) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C10 -2.1(4) . . . . ?
C8 C9 C10 C5 1.5(4) . . . . ?
C4 C5 C10 C9 -179.1(2) . . . . ?
C6 C5 C10 C9 0.7(3) . . . . ?
C2 C1 C11 N1 12.0(3) . . . . ?
C6 C1 C11 N1 -169.44(18) . . . . ?
C17 C12 C13 C14 1.0(3) . . . . ?
S1 C12 C13 C14 -177.22(18) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C13 C14 C15 C18 179.0(3) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
C18 C15 C16 C17 -178.8(2) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
S1 C12 C17 C16 177.43(19) . . . . ?
C15 C16 C17 C12 -0.1(4) . . . . ?
C1 C11 N1 N2 -179.78(17) . . . . ?
C11 N1 N2 S1 162.33(16) . . . . ?
N1 N2 S1 O2 -178.62(15) . . . . ?
N1 N2 S1 O1 52.33(18) . . . . ?
N1 N2 S1 C12 -62.65(17) . . . . ?
C13 C12 S1 O2 -156.67(18) . . . . ?
C17 C12 S1 O2 25.1(2) . . . . ?
C13 C12 S1 O1 -23.4(2) . . . . ?
C17 C12 S1 O1 158.43(18) . . . . ?
C13 C12 S1 N2 91.29(19) . . . . ?
C17 C12 S1 N2 -86.90(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O1 0.83(2) 2.09(2) 2.892(2) 162(2) 4_675

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.033

