# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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 1974744'
loop_
_audit_author_name
_audit_author_address
'Ramendra Pratap' 'University of Delhi'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O S2'
_chemical_formula_sum            'C15 H14 N2 O S2'
_chemical_formula_weight         302.40

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/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                   9.0969(8)
_cell_length_b                   11.7978(8)
_cell_length_c                   14.1107(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.790(8)
_cell_angle_gamma                90
_cell_volume                     1500.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6469
_cell_measurement_theta_min      3.7420
_cell_measurement_theta_max      28.6370

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.351
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22333
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.053
_diffrn_reflns_theta_max         29.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3815
_reflns_number_gt                3113
_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       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.,'
_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)+(0.1479P)²+7.2318P] 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         3815
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   0.425
_refine_ls_restrained_S_all      0.425
_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 0.11891(6) 0.37507(4) 0.60919(4) 0.04272(15) Uani 1 1 d . . . . .
S2 S 0.13615(7) 0.34703(5) 0.40425(4) 0.04792(17) Uani 1 1 d . . . . .
O1 O 0.3053(2) 0.45442(16) 0.96728(12) 0.0618(5) Uani 1 1 d . . . . .
C4 C 0.33514(19) 0.55416(14) 0.68887(13) 0.0313(3) Uani 1 1 d . . . . .
C9 C 0.2901(2) 0.51189(15) 0.51026(13) 0.0356(4) Uani 1 1 d . . . . .
H9 H 0.324272 0.527586 0.452444 0.043 Uiso 1 1 calc R U . . .
N2 N 0.4266(3) 0.75388(18) 0.39780(15) 0.0565(5) Uani 1 1 d . . . . .
C7 C 0.3450(2) 0.58463(15) 0.58797(13) 0.0321(4) Uani 1 1 d . . . . .
C5 C 0.4108(2) 0.45985(16) 0.73042(14) 0.0377(4) Uani 1 1 d . . . . .
H5 H 0.469108 0.416615 0.694906 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1941(2) 0.42212(15) 0.50904(13) 0.0333(4) Uani 1 1 d . . . . .
C3 C 0.2492(2) 0.61731(15) 0.74361(14) 0.0368(4) Uani 1 1 d . . . . .
H3 H 0.200464 0.681611 0.717343 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4109(2) 0.68641(16) 0.56929(13) 0.0357(4) Uani 1 1 d . . . . .
C6 C 0.3998(2) 0.43028(17) 0.82357(15) 0.0424(4) Uani 1 1 d . . . . .
H6 H 0.452603 0.368332 0.851083 0.051 Uiso 1 1 calc R U . . .
C1 C 0.3104(2) 0.49237(17) 0.87659(14) 0.0395(4) Uani 1 1 d . . . . .
C11 C 0.4196(2) 0.72406(16) 0.47403(15) 0.0399(4) Uani 1 1 d . . . . .
C2 C 0.2346(2) 0.58654(17) 0.83635(14) 0.0401(4) Uani 1 1 d . . . . .
H2 H 0.174454 0.628565 0.871516 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4796(2) 0.76017(17) 0.64300(15) 0.0424(4) Uani 1 1 d . . . . .
N1 N 0.5393(3) 0.8207(2) 0.69812(17) 0.0647(6) Uani 1 1 d . . . . .
C14 C -0.0164(2) 0.26990(19) 0.56469(17) 0.0478(5) Uani 1 1 d . . . . .
H14A H -0.062496 0.240236 0.616761 0.072 Uiso 1 1 calc R U . . .
H14B H -0.090502 0.303877 0.518442 0.072 Uiso 1 1 calc R U . . .
H14C H 0.031589 0.209510 0.535141 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2005(3) 0.4254(2) 0.30955(15) 0.0525(5) Uani 1 1 d . . . . .
H13A H 0.171151 0.387235 0.249879 0.079 Uiso 1 1 calc R U . . .
H13B H 0.158138 0.500015 0.306900 0.079 Uiso 1 1 calc R U . . .
H13C H 0.306684 0.430901 0.321015 0.079 Uiso 1 1 calc R U . . .
C15 C 0.2258(4) 0.5190(3) 1.02790(19) 0.0667(7) Uani 1 1 d . . . . .
H15A H 0.231431 0.482636 1.089128 0.100 Uiso 1 1 calc R U . . .
H15B H 0.268139 0.593537 1.035808 0.100 Uiso 1 1 calc R U . . .
H15C H 0.123833 0.524800 0.999871 0.100 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 C10 1.742(2) . ?
S1 C14 1.800(2) . ?
S2 C10 1.7431(18) . ?
S2 C13 1.787(2) . ?
O1 C1 1.363(2) . ?
O1 C15 1.416(3) . ?
C4 C3 1.388(3) . ?
C4 C5 1.395(2) . ?
C4 C7 1.483(2) . ?
C9 C10 1.371(3) . ?
C9 C7 1.428(2) . ?
C9 H9 0.9300 . ?
N2 C11 1.142(3) . ?
C7 C8 1.383(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C3 C2 1.382(3) . ?
C3 H3 0.9300 . ?
C8 C11 1.428(3) . ?
C8 C12 1.433(3) . ?
C6 C1 1.386(3) . ?
C6 H6 0.9300 . ?
C1 C2 1.388(3) . ?
C2 H2 0.9300 . ?
C12 N1 1.138(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C10 S1 C14 105.18(10) . . ?
C10 S2 C13 106.22(10) . . ?
C1 O1 C15 118.4(2) . . ?
C3 C4 C5 118.50(17) . . ?
C3 C4 C7 121.07(16) . . ?
C5 C4 C7 120.43(16) . . ?
C10 C9 C7 129.00(18) . . ?
C10 C9 H9 115.5 . . ?
C7 C9 H9 115.5 . . ?
C8 C7 C9 119.38(17) . . ?
C8 C7 C4 118.53(16) . . ?
C9 C7 C4 122.09(16) . . ?
C6 C5 C4 120.53(18) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C9 C10 S1 123.74(14) . . ?
C9 C10 S2 121.48(15) . . ?
S1 C10 S2 114.78(10) . . ?
C2 C3 C4 121.32(18) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C7 C8 C11 122.00(17) . . ?
C7 C8 C12 123.13(18) . . ?
C11 C8 C12 114.84(17) . . ?
C5 C6 C1 120.33(18) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C1 C2 124.7(2) . . ?
O1 C1 C6 115.49(19) . . ?
C2 C1 C6 119.84(18) . . ?
N2 C11 C8 179.8(3) . . ?
C1 C2 C3 119.44(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N1 C12 C8 176.2(2) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C10 C9 C7 C8 -164.0(2) . . . . ?
C10 C9 C7 C4 16.7(3) . . . . ?
C3 C4 C7 C8 65.3(2) . . . . ?
C5 C4 C7 C8 -115.7(2) . . . . ?
C3 C4 C7 C9 -115.4(2) . . . . ?
C5 C4 C7 C9 63.6(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C7 C4 C5 C6 -178.90(18) . . . . ?
C7 C9 C10 S1 -1.4(3) . . . . ?
C7 C9 C10 S2 177.72(16) . . . . ?
C14 S1 C10 C9 172.42(17) . . . . ?
C14 S1 C10 S2 -6.74(14) . . . . ?
C13 S2 C10 C9 -9.2(2) . . . . ?
C13 S2 C10 S1 169.99(12) . . . . ?
C5 C4 C3 C2 -1.8(3) . . . . ?
C7 C4 C3 C2 177.23(18) . . . . ?
C9 C7 C8 C11 3.2(3) . . . . ?
C4 C7 C8 C11 -177.49(17) . . . . ?
C9 C7 C8 C12 -174.78(19) . . . . ?
C4 C7 C8 C12 4.6(3) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C15 O1 C1 C2 -4.6(3) . . . . ?
C15 O1 C1 C6 175.0(2) . . . . ?
C5 C6 C1 O1 178.7(2) . . . . ?
C5 C6 C1 C2 -1.6(3) . . . . ?
O1 C1 C2 C3 179.6(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C4 C3 C2 C1 1.7(3) . . . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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 1974745'
loop_
_audit_author_name
_audit_author_address
'Ramendra Pratap' 'University of Delhi'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Br N3 O2 S'
_chemical_formula_sum            'C20 H14 Br N3 O2 S'
_chemical_formula_weight         440.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 '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                   8.4509(8)
_cell_length_b                   10.7362(9)
_cell_length_c                   11.5735(9)
_cell_angle_alpha                108.414(7)
_cell_angle_beta                 104.992(7)
_cell_angle_gamma                100.036(7)
_cell_volume                     924.09(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2361
_cell_measurement_theta_min      3.7460
_cell_measurement_theta_max      25.3840

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.358
_shelx_estimated_absorpt_T_min   0.650
_shelx_estimated_absorpt_T_max   0.704
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'xcalibur sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11237
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.366
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3255
_reflns_number_gt                2179
_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       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.,'
_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)+(0.2000P)²] 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         3248
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.2492
_refine_ls_wR_factor_gt          0.2086
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_restrained_S_all      0.864
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
Br Br 1.08518(13) 0.08775(9) 0.75330(7) 0.1163(5) Uani 1 1 d . . . . .
S S 0.16794(18) 0.44381(15) 0.47952(14) 0.0543(5) Uani 1 1 d . . . . .
O2 O -0.4244(7) 0.3370(6) -0.1177(6) 0.0998(17) Uani 1 1 d . . . . .
C19 C 0.5328(6) 0.0856(5) 0.2093(5) 0.0431(12) Uani 1 1 d . . . . .
O1 O -0.3067(7) 0.5506(6) -0.0035(6) 0.0904(16) Uani 1 1 d . . . . .
N1 N -0.3140(7) 0.4302(6) -0.0275(6) 0.0632(14) Uani 1 1 d . . . . .
N2 N 0.5862(6) 0.0136(5) 0.1442(4) 0.0574(12) Uani 1 1 d . . . . .
C6 C -0.1919(7) 0.2647(6) 0.0419(5) 0.0516(13) Uani 1 1 d . . . . .
H6 H -0.292139 0.197207 -0.013236 0.062 Uiso 1 1 calc R U . . .
C5 C -0.0600(7) 0.2319(5) 0.1127(5) 0.0504(13) Uani 1 1 d . . . . .
H5 H -0.071879 0.141598 0.105024 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2827(6) 0.3408(4) 0.4061(5) 0.0388(12) Uani 1 1 d . . . . .
C9 C 0.4521(6) 0.1762(4) 0.2802(4) 0.0365(11) Uani 1 1 d . . . . .
C11 C 0.4136(6) 0.3038(5) 0.4762(5) 0.0408(12) Uani 1 1 d . . . . .
H11 H 0.442553 0.334677 0.565597 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2361(6) 0.2940(5) 0.2705(4) 0.0366(11) Uani 1 1 d . . . . .
C14 C 0.7958(6) 0.1902(5) 0.4733(5) 0.0435(12) Uani 1 1 d . . . . .
H14 H 0.812447 0.213417 0.405502 0.052 Uiso 1 1 calc R U . . .
C4 C 0.0916(6) 0.3317(5) 0.1960(5) 0.0377(11) Uani 1 1 d . . . . .
C13 C 0.6405(7) 0.1881(5) 0.4955(5) 0.0412(12) Uani 1 1 d . . . . .
C3 C 0.1037(7) 0.4670(5) 0.2064(5) 0.0471(13) Uani 1 1 d . . . . .
H3 H 0.203396 0.535398 0.261144 0.056 Uiso 1 1 calc R U . . .
C2 C -0.0292(7) 0.4998(6) 0.1372(5) 0.0519(14) Uani 1 1 d . . . . .
H2 H -0.021182 0.590321 0.146899 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5020(6) 0.2224(5) 0.4165(4) 0.0379(11) Uani 1 1 d . . . . .
C1 C -0.1747(7) 0.3977(6) 0.0530(5) 0.0491(14) Uani 1 1 d . . . . .
C8 C 0.3224(6) 0.2133(5) 0.2080(4) 0.0378(11) Uani 1 1 d . . . . .
C15 C 0.9224(7) 0.1594(5) 0.5482(5) 0.0545(14) Uani 1 1 d . . . . .
H15 H 1.023123 0.159063 0.529739 0.065 Uiso 1 1 calc R U . . .
C18 C 0.6236(8) 0.1556(5) 0.6002(5) 0.0533(14) Uani 1 1 d . . . . .
H18 H 0.522336 0.153812 0.618192 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7545(9) 0.1261(6) 0.6780(5) 0.0631(17) Uani 1 1 d . . . . .
H17 H 0.741565 0.104842 0.747553 0.076 Uiso 1 1 calc R U . . .
C20 C 0.2682(8) 0.4879(6) 0.6474(6) 0.0624(17) Uani 1 1 d . . . . .
H20A H 0.212442 0.544890 0.695010 0.094 Uiso 1 1 calc R U . . .
H20B H 0.260490 0.406275 0.665659 0.094 Uiso 1 1 calc R U . . .
H20C H 0.386046 0.536530 0.672472 0.094 Uiso 1 1 calc R U . . .
C16 C 0.9039(9) 0.1287(5) 0.6505(5) 0.0607(16) Uani 1 1 d . . . . .
N3 N 0.2777(6) 0.1658(4) 0.0763(4) 0.0532(12) Uani 1 1 d . . . . .
H3A H 0.195100 0.186219 0.031713 0.064 Uiso 1 1 calc R U . . .
H3B H 0.332157 0.115611 0.038077 0.064 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
Br C16 1.891(6) . ?
S C20 1.773(6) . ?
S C12 1.759(4) . ?
O2 N1 1.214(7) . ?
C19 N2 1.140(6) . ?
C19 C9 1.450(7) . ?
O1 N1 1.220(7) . ?
N1 C1 1.468(8) . ?
C6 C1 1.370(8) . ?
C6 C5 1.373(8) . ?
C6 H6 0.9300 . ?
C5 C4 1.396(7) . ?
C5 H5 0.9300 . ?
C12 C11 1.390(7) . ?
C12 C7 1.408(7) . ?
C9 C10 1.415(7) . ?
C9 C8 1.395(7) . ?
C11 C10 1.382(7) . ?
C11 H11 0.9300 . ?
C7 C8 1.379(6) . ?
C7 C4 1.499(7) . ?
C14 C15 1.354(7) . ?
C14 C13 1.400(7) . ?
C14 H14 0.9300 . ?
C4 C3 1.401(7) . ?
C13 C10 1.467(7) . ?
C13 C18 1.396(7) . ?
C3 C2 1.371(8) . ?
C3 H3 0.9300 . ?
C2 C1 1.378(8) . ?
C2 H2 0.9300 . ?
C8 N3 1.368(6) . ?
C15 C16 1.363(8) . ?
C15 H15 0.9300 . ?
C18 C17 1.386(9) . ?
C18 H18 0.9300 . ?
C17 C16 1.378(9) . ?
C17 H17 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?

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
C20 S C12 104.2(3) . . ?
N2 C19 C9 174.1(6) . . ?
O2 N1 O1 123.7(6) . . ?
O2 N1 C1 118.5(5) . . ?
O1 N1 C1 117.6(6) . . ?
C1 C6 C5 119.6(5) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C11 C12 C7 119.9(4) . . ?
C11 C12 S 122.7(4) . . ?
C7 C12 S 117.4(4) . . ?
C10 C9 C8 122.0(4) . . ?
C10 C9 C19 120.9(5) . . ?
C8 C9 C19 117.1(4) . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C8 C7 C12 119.8(5) . . ?
C8 C7 C4 121.0(4) . . ?
C12 C7 C4 119.3(4) . . ?
C15 C14 C13 121.4(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C5 C4 C7 120.6(4) . . ?
C5 C4 C3 117.8(5) . . ?
C7 C4 C3 121.6(4) . . ?
C14 C13 C10 122.5(4) . . ?
C14 C13 C18 117.0(5) . . ?
C10 C13 C18 120.5(5) . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C13 C10 C9 123.4(4) . . ?
C13 C10 C11 119.4(4) . . ?
C9 C10 C11 117.2(5) . . ?
C2 C1 C6 121.0(5) . . ?
C2 C1 N1 120.1(5) . . ?
C6 C1 N1 118.9(5) . . ?
N3 C8 C7 120.6(5) . . ?
N3 C8 C9 120.1(4) . . ?
C7 C8 C9 119.3(4) . . ?
C16 C15 C14 120.7(6) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C18 C13 121.5(6) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C18 C17 C16 118.9(5) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
S C20 H20A 109.5 . . ?
S C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 C17 120.5(6) . . ?
C15 C16 Br 119.2(5) . . ?
C17 C16 Br 120.3(5) . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?

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
C1 C6 C5 C4 0.0(8) . . . . ?
C20 S C12 C11 3.4(5) . . . . ?
C20 S C12 C7 -177.4(4) . . . . ?
C7 C12 C11 C10 0.6(7) . . . . ?
S C12 C11 C10 179.8(3) . . . . ?
C11 C12 C7 C8 -1.0(7) . . . . ?
S C12 C7 C8 179.7(3) . . . . ?
C11 C12 C7 C4 178.4(4) . . . . ?
S C12 C7 C4 -0.8(6) . . . . ?
C6 C5 C4 C7 -178.6(5) . . . . ?
C6 C5 C4 C3 0.9(7) . . . . ?
C8 C7 C4 C5 66.3(6) . . . . ?
C12 C7 C4 C5 -113.1(5) . . . . ?
C8 C7 C4 C3 -113.2(5) . . . . ?
C12 C7 C4 C3 67.4(6) . . . . ?
C15 C14 C13 C10 179.4(4) . . . . ?
C15 C14 C13 C18 1.4(7) . . . . ?
C5 C4 C3 C2 0.1(7) . . . . ?
C7 C4 C3 C2 179.6(4) . . . . ?
C4 C3 C2 C1 -2.1(7) . . . . ?
C14 C13 C10 C9 42.9(7) . . . . ?
C18 C13 C10 C9 -139.1(5) . . . . ?
C14 C13 C10 C11 -137.2(5) . . . . ?
C18 C13 C10 C11 40.8(6) . . . . ?
C8 C9 C10 C13 -178.5(4) . . . . ?
C19 C9 C10 C13 2.6(7) . . . . ?
C8 C9 C10 C11 1.6(6) . . . . ?
C19 C9 C10 C11 -177.3(4) . . . . ?
C12 C11 C10 C13 179.2(4) . . . . ?
C12 C11 C10 C9 -0.9(7) . . . . ?
C3 C2 C1 C6 3.1(8) . . . . ?
C3 C2 C1 N1 -176.4(4) . . . . ?
C5 C6 C1 C2 -2.0(8) . . . . ?
C5 C6 C1 N1 177.4(5) . . . . ?
O2 N1 C1 C2 165.7(5) . . . . ?
O1 N1 C1 C2 -10.5(7) . . . . ?
O2 N1 C1 C6 -13.8(7) . . . . ?
O1 N1 C1 C6 170.1(5) . . . . ?
C12 C7 C8 N3 179.4(4) . . . . ?
C4 C7 C8 N3 -0.1(7) . . . . ?
C12 C7 C8 C9 1.8(7) . . . . ?
C4 C7 C8 C9 -177.7(4) . . . . ?
C10 C9 C8 N3 -179.7(4) . . . . ?
C19 C9 C8 N3 -0.7(7) . . . . ?
C10 C9 C8 C7 -2.1(7) . . . . ?
C19 C9 C8 C7 176.9(4) . . . . ?
C13 C14 C15 C16 -1.8(8) . . . . ?
C14 C13 C18 C17 -0.4(7) . . . . ?
C10 C13 C18 C17 -178.4(4) . . . . ?
C13 C18 C17 C16 -0.2(8) . . . . ?
C14 C15 C16 C17 1.2(8) . . . . ?
C14 C15 C16 Br -179.5(4) . . . . ?
C18 C17 C16 C15 -0.2(8) . . . . ?
C18 C17 C16 Br -179.5(4) . . . . ?

_refine_diff_density_max         0.660
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.075

