# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1965821'
loop_
_audit_author_name
_audit_author_address
'Suman Pradhan'
;Indian Institute of Technology Ropar
India
;
_audit_update_record             
;
2019-11-14 deposited with the CCDC.	2020-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cl N O S'
_chemical_formula_sum            'C14 H10 Cl N O S'
_chemical_formula_weight         275.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.0173(7)
_cell_length_b                   9.8035(10)
_cell_length_c                   14.1588(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.552(3)
_cell_angle_gamma                90
_cell_volume                     1245.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2558
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26.4

_exptl_crystal_description       'BLOCK TYPE'
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_meas      1.5
_exptl_crystal_density_method    'NOT MEASURED'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   0.5257
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.219
_exptl_absorpt_coefficient_mu    0.459
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'FINE FOCUS SEALED TUBE'
_diffrn_measurement_device_type  'BRUKER D8 VENTURE, PHOTON 200'
_diffrn_measurement_method       'PHI AND OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11179
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.269
_diffrn_reflns_theta_max         26.449
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2558
_reflns_number_gt                1892
_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       'APEX3.INC.BRUKER SOFTWARE PACKAGE'
_computing_cell_refinement       'SAINT V8.38A (BRUKER AXS INC.,2017)'
_computing_data_reduction        'SAINT V8.38A (BRUKER AXS INC.,2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3, MERCURY,AND PLATON'
_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)+(0.0417P)²+0.4302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2558
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.67609(7) -0.47725(7) 0.58782(5) 0.0476(2) Uani 1 1 d . . . . .
Cl Cl 0.76635(9) -0.48088(9) 1.11116(5) 0.0672(3) Uani 1 1 d . . . . .
O1 O 0.6103(2) -0.6171(2) 0.57553(14) 0.0659(6) Uani 1 1 d . . . . .
C1 C 0.7302(3) -0.4705(3) 0.9886(2) 0.0487(7) Uani 1 1 d . . . . .
C2 C 0.6035(2) -0.3742(2) 0.85240(19) 0.0428(6) Uani 1 1 d . . . . .
N1 N 0.5108(2) -0.2900(2) 0.79567(18) 0.0529(6) Uani 1 1 d . . . . .
H1 H 0.450494 -0.231204 0.815806 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6835(2) -0.4554(2) 0.79262(18) 0.0393(6) Uani 1 1 d . . . . .
C4 C 0.9676(3) -0.3970(3) 0.6347(2) 0.0540(7) Uani 1 1 d . . . . .
H4 H 0.930804 -0.308568 0.636904 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6343(2) -0.4142(3) 0.69732(18) 0.0425(6) Uani 1 1 d . . . . .
C6 C 0.8730(3) -0.5049(3) 0.61498(17) 0.0403(6) Uani 1 1 d . . . . .
C7 C 0.6246(3) -0.3802(3) 0.95040(19) 0.0471(6) Uani 1 1 d . . . . .
H7 H 0.570081 -0.325887 0.988383 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7895(3) -0.5462(3) 0.83503(19) 0.0468(6) Uani 1 1 d . . . . .
H8 H 0.843833 -0.601765 0.797772 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8126(3) -0.5525(3) 0.9323(2) 0.0503(7) Uani 1 1 d . . . . .
H9 H 0.883748 -0.611980 0.960901 0.060 Uiso 1 1 calc R U . . .
C10 C 0.9263(3) -0.6362(3) 0.6114(2) 0.0571(7) Uani 1 1 d . . . . .
H10 H 0.861320 -0.708671 0.597464 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5290(3) -0.3139(3) 0.7038(2) 0.0532(7) Uani 1 1 d . . . . .
H11 H 0.478072 -0.269256 0.652451 0.064 Uiso 1 1 calc R U . . .
C12 C 1.1726(3) -0.5518(4) 0.6477(2) 0.0628(8) Uani 1 1 d . . . . .
H12 H 1.274647 -0.567288 0.658231 0.075 Uiso 1 1 calc R U . . .
C13 C 1.0771(3) -0.6588(3) 0.6287(2) 0.0668(9) Uani 1 1 d . . . . .
H13 H 1.114213 -0.747198 0.627399 0.080 Uiso 1 1 calc R U . . .
C14 C 1.1179(3) -0.4221(3) 0.6513(2) 0.0644(8) Uani 1 1 d . . . . .
H14 H 1.183233 -0.349822 0.665199 0.077 Uiso 1 1 calc R 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
S1 O1 1.497(2) . ?
S1 C5 1.744(3) . ?
S1 C6 1.800(2) . ?
Cl C1 1.738(3) . ?
C1 C7 1.372(4) . ?
C1 C9 1.396(4) . ?
C2 N1 1.376(3) . ?
C2 C7 1.383(4) . ?
C2 C3 1.411(3) . ?
N1 C11 1.348(4) . ?
N1 H1 0.8600 . ?
C3 C8 1.398(3) . ?
C3 C5 1.437(3) . ?
C4 C6 1.371(3) . ?
C4 C14 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C11 1.376(3) . ?
C6 C10 1.377(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C13 1.376(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C14 1.367(4) . ?
C12 C13 1.367(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C5 108.11(11) . . ?
O1 S1 C6 104.96(12) . . ?
C5 S1 C6 99.04(11) . . ?
C7 C1 C9 122.3(3) . . ?
C7 C1 Cl 119.2(2) . . ?
C9 C1 Cl 118.5(2) . . ?
N1 C2 C7 128.9(2) . . ?
N1 C2 C3 107.8(2) . . ?
C7 C2 C3 123.3(2) . . ?
C11 N1 C2 109.6(2) . . ?
C11 N1 H1 125.2 . . ?
C2 N1 H1 125.2 . . ?
C8 C3 C2 118.0(2) . . ?
C8 C3 C5 135.9(2) . . ?
C2 C3 C5 106.0(2) . . ?
C6 C4 C14 118.7(3) . . ?
C6 C4 H4 120.6 . . ?
C14 C4 H4 120.6 . . ?
C11 C5 C3 106.9(2) . . ?
C11 C5 S1 121.5(2) . . ?
C3 C5 S1 131.40(19) . . ?
C4 C6 C10 121.1(2) . . ?
C4 C6 S1 120.58(19) . . ?
C10 C6 S1 118.3(2) . . ?
C1 C7 C2 116.4(2) . . ?
C1 C7 H7 121.8 . . ?
C2 C7 H7 121.8 . . ?
C9 C8 C3 119.3(2) . . ?
C9 C8 H8 120.3 . . ?
C3 C8 H8 120.3 . . ?
C8 C9 C1 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C1 C9 H9 119.7 . . ?
C13 C10 C6 119.1(3) . . ?
C13 C10 H10 120.4 . . ?
C6 C10 H10 120.4 . . ?
N1 C11 C5 109.7(2) . . ?
N1 C11 H11 125.2 . . ?
C5 C11 H11 125.2 . . ?
C14 C12 C13 119.9(3) . . ?
C14 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C10 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C10 C13 H13 119.8 . . ?
C12 C14 C4 120.9(3) . . ?
C12 C14 H14 119.6 . . ?
C4 C14 H14 119.6 . . ?

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
C7 C2 N1 C11 177.4(2) . . . . ?
C3 C2 N1 C11 -0.2(3) . . . . ?
N1 C2 C3 C8 177.7(2) . . . . ?
C7 C2 C3 C8 0.0(3) . . . . ?
N1 C2 C3 C5 0.4(3) . . . . ?
C7 C2 C3 C5 -177.3(2) . . . . ?
C8 C3 C5 C11 -177.1(3) . . . . ?
C2 C3 C5 C11 -0.5(3) . . . . ?
C8 C3 C5 S1 8.0(4) . . . . ?
C2 C3 C5 S1 -175.40(19) . . . . ?
O1 S1 C5 C11 -106.6(2) . . . . ?
C6 S1 C5 C11 144.3(2) . . . . ?
O1 S1 C5 C3 67.7(3) . . . . ?
C6 S1 C5 C3 -41.4(2) . . . . ?
C14 C4 C6 C10 -0.2(4) . . . . ?
C14 C4 C6 S1 -177.4(2) . . . . ?
O1 S1 C6 C4 -177.2(2) . . . . ?
C5 S1 C6 C4 -65.6(2) . . . . ?
O1 S1 C6 C10 5.5(2) . . . . ?
C5 S1 C6 C10 117.1(2) . . . . ?
C9 C1 C7 C2 0.0(4) . . . . ?
Cl C1 C7 C2 178.45(18) . . . . ?
N1 C2 C7 C1 -177.0(2) . . . . ?
C3 C2 C7 C1 0.3(4) . . . . ?
C2 C3 C8 C9 -0.5(4) . . . . ?
C5 C3 C8 C9 175.8(3) . . . . ?
C3 C8 C9 C1 0.7(4) . . . . ?
C7 C1 C9 C8 -0.5(4) . . . . ?
Cl C1 C9 C8 -179.0(2) . . . . ?
C4 C6 C10 C13 0.5(4) . . . . ?
S1 C6 C10 C13 177.8(2) . . . . ?
C2 N1 C11 C5 -0.1(3) . . . . ?
C3 C5 C11 N1 0.4(3) . . . . ?
S1 C5 C11 N1 175.90(17) . . . . ?
C14 C12 C13 C10 1.2(5) . . . . ?
C6 C10 C13 C12 -1.0(4) . . . . ?
C13 C12 C14 C4 -0.9(5) . . . . ?
C6 C4 C14 C12 0.4(5) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1965825'
loop_
_audit_author_name
_audit_author_address
'Suman Pradhan'
;Indian Institute of Technology Ropar
India
;
_audit_update_record             
;
2019-11-14 deposited with the CCDC.	2020-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O S'
_chemical_formula_sum            'C14 H15 N O S'
_chemical_formula_weight         245.33

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 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                   14.275(2)
_cell_length_b                   7.6981(10)
_cell_length_c                   11.6398(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.250(5)
_cell_angle_gamma                90
_cell_volume                     1254.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2569
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      26.4

_exptl_crystal_description       'BLOCK TYPE'
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_meas      1.3
_exptl_crystal_density_method    'NOT MEASURED'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   0.3593
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.298
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'FINE FOCUS SEALED TUBE'
_diffrn_measurement_device_type  'BRUKER D8 VENTURE, PHOTON 200'
_diffrn_measurement_method       'PHI AND OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12433
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.910
_diffrn_reflns_theta_max         26.425
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2569
_reflns_number_gt                1718
_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       'APEX3 INC.BRUKER SOFTWARE PACKAGE'
_computing_cell_refinement       'SAINT V8.38A (BRUKER AXS INC.,2017)'
_computing_data_reduction        'SAINT V8.38A (BRUKER AXS INC.,2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY,ORTEP3 AND PLATON'
_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)+(0.1200P)²+0.5317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2569
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.2260
_refine_ls_wR_factor_gt          0.1939
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.32177(7) 0.18180(11) 0.36049(8) 0.0645(4) Uani 1 1 d . . . . .
O1 O 0.3292(2) 0.1343(4) 0.2397(2) 0.0904(10) Uani 1 1 d . . . . .
N3 N -0.0922(2) 0.1663(3) 0.3795(2) 0.0594(7) Uani 1 1 d . . . . .
C9 C 0.3605(2) -0.0021(4) 0.4512(3) 0.0508(7) Uani 1 1 d . . . . .
C5 C 0.0702(3) 0.2477(4) 0.4645(3) 0.0557(8) Uani 1 1 d . . . . .
H5 H 0.049786 0.300200 0.527265 0.067 Uiso 1 1 calc R U . . .
C7 C 0.1978(3) 0.1726(4) 0.3678(3) 0.0512(8) Uani 1 1 d . . . . .
C3 C 0.0022(2) 0.1666(3) 0.3766(2) 0.0486(8) Uani 1 1 d . . . . .
C14 C 0.3595(3) -0.1643(4) 0.4017(3) 0.0641(9) Uani 1 1 d . . . . .
H14 H 0.339554 -0.178636 0.321309 0.077 Uiso 1 1 calc R U . . .
C8 C 0.1337(3) 0.0893(4) 0.2815(2) 0.0579(9) Uani 1 1 d . . . . .
H8 H 0.155406 0.035303 0.220203 0.070 Uiso 1 1 calc R U . . .
C4 C 0.0386(3) 0.0851(4) 0.2850(2) 0.0551(8) Uani 1 1 d . . . . .
H4 H -0.003264 0.027508 0.226079 0.066 Uiso 1 1 calc R U . . .
C1 C -0.1281(3) 0.2425(5) 0.4753(3) 0.0699(10) Uani 1 1 d . . . . .
H1A H -0.196236 0.229729 0.461759 0.105 Uiso 1 1 calc R U . . .
H1B H -0.099994 0.184913 0.546907 0.105 Uiso 1 1 calc R U . . .
H1C H -0.111890 0.363653 0.481128 0.105 Uiso 1 1 calc R U . . .
C6 C 0.1655(3) 0.2515(4) 0.4600(3) 0.0573(8) Uani 1 1 d . . . . .
H6 H 0.208468 0.306983 0.518887 0.069 Uiso 1 1 calc R U . . .
C10 C 0.3933(3) 0.0213(5) 0.5708(3) 0.0646(9) Uani 1 1 d . . . . .
H10 H 0.395532 0.131676 0.603628 0.078 Uiso 1 1 calc R U . . .
C2 C -0.1595(3) 0.0711(5) 0.2933(3) 0.0757(11) Uani 1 1 d . . . . .
H2A H -0.222730 0.085524 0.308766 0.114 Uiso 1 1 calc R U . . .
H2B H -0.157602 0.114549 0.216489 0.114 Uiso 1 1 calc R U . . .
H2C H -0.143010 -0.049894 0.297462 0.114 Uiso 1 1 calc R U . . .
C13 C 0.3883(3) -0.3055(5) 0.4728(4) 0.0844(13) Uani 1 1 d . . . . .
H13 H 0.386652 -0.416099 0.440362 0.101 Uiso 1 1 calc R U . . .
C11 C 0.4221(3) -0.1207(7) 0.6394(3) 0.0841(13) Uani 1 1 d . . . . .
H11 H 0.443754 -0.106947 0.719556 0.101 Uiso 1 1 calc R U . . .
C12 C 0.4192(3) -0.2838(7) 0.5903(5) 0.0898(14) Uani 1 1 d . . . . .
H12 H 0.438354 -0.379728 0.637555 0.108 Uiso 1 1 calc R 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
S1 O1 1.477(3) . ?
S1 C9 1.788(3) . ?
S1 C7 1.789(4) . ?
N3 C3 1.355(4) . ?
N3 C1 1.440(4) . ?
N3 C2 1.446(4) . ?
C9 C14 1.374(5) . ?
C9 C10 1.390(5) . ?
C5 C6 1.371(5) . ?
C5 C3 1.411(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.378(5) . ?
C7 C6 1.388(4) . ?
C3 C4 1.420(4) . ?
C14 C13 1.380(5) . ?
C14 H14 0.9300 . ?
C8 C4 1.367(5) . ?
C8 H8 0.9300 . ?
C4 H4 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6 0.9300 . ?
C10 C11 1.369(6) . ?
C10 H10 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C13 C12 1.363(7) . ?
C13 H13 0.9300 . ?
C11 C12 1.377(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C9 107.15(16) . . ?
O1 S1 C7 106.92(17) . . ?
C9 S1 C7 97.79(14) . . ?
C3 N3 C1 121.6(3) . . ?
C3 N3 C2 120.9(3) . . ?
C1 N3 C2 117.1(3) . . ?
C14 C9 C10 120.8(3) . . ?
C14 C9 S1 119.6(2) . . ?
C10 C9 S1 119.6(3) . . ?
C6 C5 C3 121.9(3) . . ?
C6 C5 H5 119.0 . . ?
C3 C5 H5 119.0 . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 S1 120.4(2) . . ?
C6 C7 S1 120.1(3) . . ?
N3 C3 C5 122.0(3) . . ?
N3 C3 C4 122.0(3) . . ?
C5 C3 C4 116.0(3) . . ?
C9 C14 C13 119.1(3) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C4 C8 C7 120.8(3) . . ?
C4 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C4 C3 121.5(3) . . ?
C8 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C10 C11 C12 120.3(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?

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
O1 S1 C9 C14 -21.3(3) . . . . ?
C7 S1 C9 C14 89.1(3) . . . . ?
O1 S1 C9 C10 157.4(3) . . . . ?
C7 S1 C9 C10 -92.2(3) . . . . ?
O1 S1 C7 C8 15.4(3) . . . . ?
C9 S1 C7 C8 -95.3(3) . . . . ?
O1 S1 C7 C6 -163.8(3) . . . . ?
C9 S1 C7 C6 85.5(3) . . . . ?
C1 N3 C3 C5 -2.7(5) . . . . ?
C2 N3 C3 C5 -175.2(3) . . . . ?
C1 N3 C3 C4 177.2(3) . . . . ?
C2 N3 C3 C4 4.7(5) . . . . ?
C6 C5 C3 N3 -178.4(3) . . . . ?
C6 C5 C3 C4 1.7(4) . . . . ?
C10 C9 C14 C13 2.2(5) . . . . ?
S1 C9 C14 C13 -179.1(3) . . . . ?
C6 C7 C8 C4 0.7(4) . . . . ?
S1 C7 C8 C4 -178.5(2) . . . . ?
C7 C8 C4 C3 0.4(5) . . . . ?
N3 C3 C4 C8 178.6(3) . . . . ?
C5 C3 C4 C8 -1.5(4) . . . . ?
C3 C5 C6 C7 -0.6(5) . . . . ?
C8 C7 C6 C5 -0.6(4) . . . . ?
S1 C7 C6 C5 178.6(2) . . . . ?
C14 C9 C10 C11 -1.8(5) . . . . ?
S1 C9 C10 C11 179.5(3) . . . . ?
C9 C14 C13 C12 -1.3(6) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C14 C13 C12 C11 -0.1(7) . . . . ?
C10 C11 C12 C13 0.5(7) . . . . ?

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.065

