# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_KB606_0m
_database_code_depnum_ccdc_archive 'CCDC 2352135'
loop_
_audit_author_name
_audit_author_address
'B. Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-04-30 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H7 F3 O2'
_chemical_formula_sum            'C10 H7 F3 O2'
_chemical_formula_weight         216.16

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.510(8)
_cell_length_b                   4.956(4)
_cell_length_c                   11.481(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.91(3)
_cell_angle_gamma                90
_cell_volume                     463.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2581
_cell_measurement_theta_min      2.5015
_cell_measurement_theta_max      23.733

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9200
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         30.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2488
_reflns_number_gt                1483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.862
_reflns_Friedel_fraction_full    0.997

_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 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1051P)²+0.0255P] 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_abs_structure_details 
;
 Flack x determined using 497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2488
_refine_ls_number_parameters     140
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1962
_refine_ls_wR_factor_gt          0.1661
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.9690(6) 0.9782(10) 0.6152(4) 0.0630(12) Uani 1 1 d . . . . .
H1 H 1.052034 1.076631 0.597133 0.076 Uiso 1 1 calc R U . . .
C2 C 1.0084(5) 0.7986(9) 0.7110(4) 0.0562(11) Uani 1 1 d . . . . .
H2 H 1.116808 0.774145 0.757632 0.067 Uiso 1 1 calc R U . . .
C3 C 0.8829(5) 0.6566(8) 0.7356(3) 0.0461(9) Uani 1 1 d . . . . .
C4 C 0.7247(5) 0.6966(8) 0.6659(3) 0.0496(9) Uani 1 1 d . . . . .
C5 C 0.6822(6) 0.8761(9) 0.5694(3) 0.0617(12) Uani 1 1 d . . . . .
H5 H 0.573719 0.901822 0.523236 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8094(6) 1.0138(10) 0.5460(3) 0.0614(11) Uani 1 1 d . . . . .
H6 H 0.786806 1.134936 0.481385 0.074 Uiso 1 1 calc R U . . .
C7 C 0.8804(5) 0.4472(7) 0.8289(3) 0.0461(9) Uani 1 1 d . . . . .
H7 H 0.935821 0.283864 0.813025 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6983(5) 0.3927(8) 0.8010(3) 0.0481(9) Uani 1 1 d . . . . .
C9 C 0.6221(6) 0.2281(10) 0.8582(4) 0.0620(12) Uani 1 1 d . . . . .
H9 H 0.686999 0.134893 0.925324 0.074 Uiso 1 1 calc R U . . .
C10 C 0.4450(6) 0.1808(12) 0.8248(4) 0.0694(13) Uani 1 1 d . . . . .
F1 F 0.3620(6) 0.3895(12) 0.8299(8) 0.210(4) Uani 1 1 d . . . . .
F2 F 0.3820(5) 0.0898(15) 0.7154(3) 0.153(2) Uani 1 1 d . . . . .
F3 F 0.4033(5) 0.0050(16) 0.8923(5) 0.175(3) Uani 1 1 d . . . . .
O1 O 0.6119(3) 0.5403(6) 0.7014(2) 0.0605(8) Uani 1 1 d . . . . .
O2 O 0.9544(4) 0.5335(6) 0.9502(2) 0.0580(8) Uani 1 1 d D . . . .
H2O H 1.002(5) 0.380(6) 0.984(4) 0.049(11) Uiso 1 1 d 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
C1 C6 1.371(7) . ?
C1 C2 1.378(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(5) . ?
C3 C7 1.496(5) . ?
C4 C5 1.384(5) . ?
C4 O1 1.385(5) . ?
C5 C6 1.371(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.418(4) . ?
C7 C8 1.513(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.329(6) . ?
C8 O1 1.376(4) . ?
C9 C10 1.462(7) . ?
C9 H9 0.9300 . ?
C10 F1 1.264(8) . ?
C10 F3 1.283(7) . ?
C10 F2 1.294(6) . ?
O2 H2O 0.89(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 C1 C2 121.0(4) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 118.1(4) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 C7 107.7(3) . . ?
C2 C3 C7 132.5(4) . . ?
C3 C4 C5 123.1(4) . . ?
C3 C4 O1 113.3(3) . . ?
C5 C4 O1 123.6(4) . . ?
C6 C5 C4 116.0(4) . . ?
C6 C5 H5 122.0 . . ?
C4 C5 H5 122.0 . . ?
C1 C6 C5 121.9(4) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
O2 C7 C3 113.5(3) . . ?
O2 C7 C8 113.4(3) . . ?
C3 C7 C8 101.5(3) . . ?
O2 C7 H7 109.4 . . ?
C3 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C9 C8 O1 121.1(4) . . ?
C9 C8 C7 128.5(4) . . ?
O1 C8 C7 110.4(3) . . ?
C8 C9 C10 125.7(4) . . ?
C8 C9 H9 117.2 . . ?
C10 C9 H9 117.2 . . ?
F1 C10 F3 105.8(6) . . ?
F1 C10 F2 104.5(6) . . ?
F3 C10 F2 103.9(5) . . ?
F1 C10 C9 113.8(5) . . ?
F3 C10 C9 113.3(5) . . ?
F2 C10 C9 114.5(4) . . ?
C8 O1 C4 107.0(3) . . ?
C7 O2 H2O 100(3) . . ?

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 -0.2(6) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C1 C2 C3 C7 178.9(4) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C7 C3 C4 C5 -179.3(3) . . . . ?
C2 C3 C4 O1 -179.9(3) . . . . ?
C7 C3 C4 O1 0.8(4) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
O1 C4 C5 C6 -179.6(4) . . . . ?
C2 C1 C6 C5 0.7(7) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
C4 C3 C7 O2 -124.2(4) . . . . ?
C2 C3 C7 O2 56.6(5) . . . . ?
C4 C3 C7 C8 -2.2(4) . . . . ?
C2 C3 C7 C8 178.6(4) . . . . ?
O2 C7 C8 C9 -55.6(6) . . . . ?
C3 C7 C8 C9 -177.7(4) . . . . ?
O2 C7 C8 O1 125.1(3) . . . . ?
C3 C7 C8 O1 3.0(4) . . . . ?
O1 C8 C9 C10 0.5(7) . . . . ?
C7 C8 C9 C10 -178.7(4) . . . . ?
C8 C9 C10 F1 -61.4(8) . . . . ?
C8 C9 C10 F3 177.7(6) . . . . ?
C8 C9 C10 F2 58.7(8) . . . . ?
C9 C8 O1 C4 178.0(4) . . . . ?
C7 C8 O1 C4 -2.7(4) . . . . ?
C3 C4 O1 C8 1.2(4) . . . . ?
C5 C4 O1 C8 -178.7(4) . . . . ?

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
_geom_hbond_publ_flag
O2 H2O O2 0.89(2) 1.87(3) 2.745(3) 165(4) 2_747 yes

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_KB1537_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2366081'
loop_
_audit_author_name
_audit_author_address
'Sridhar B'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-07-24 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         'C11 H9 Br F3 N O3 S'
_chemical_formula_sum            'C11 H9 Br F3 N O3 S'
_chemical_formula_weight         372.16

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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           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                   5.4629(7)
_cell_length_b                   21.481(3)
_cell_length_c                   11.2799(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1323.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8395
_cell_measurement_theta_min      2.3435
_cell_measurement_theta_max      28.312

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    3.305
_shelx_estimated_absorpt_T_min   0.480
_shelx_estimated_absorpt_T_max   0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5666
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9707
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.370
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             2982
_reflns_number_gt                2460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.808
_reflns_Friedel_fraction_full    0.855

_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 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.3468P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 882 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.061(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2982
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.4817(7) 0.66267(19) 0.2307(3) 0.0381(9) Uani 1 1 d . . . . .
C2 C 0.5986(6) 0.67889(16) 0.3343(4) 0.0343(8) Uani 1 1 d . . . . .
H2 H 0.737485 0.703924 0.333178 0.041 Uiso 1 1 calc R U . . .
C3 C 0.5043(6) 0.65701(16) 0.4397(3) 0.0284(7) Uani 1 1 d . . . . .
C4 C 0.2966(6) 0.62025(16) 0.4400(3) 0.0299(8) Uani 1 1 d . . . . .
C5 C 0.1765(7) 0.60456(19) 0.3363(4) 0.0431(10) Uani 1 1 d . . . . .
H5 H 0.035464 0.580318 0.337396 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2727(8) 0.62600(19) 0.2316(4) 0.0454(10) Uani 1 1 d . . . . .
H6 H 0.196920 0.615826 0.160367 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6010(6) 0.66326(15) 0.5638(4) 0.0288(9) Uani 1 1 d . . . . .
H7 H 0.744351 0.636186 0.572134 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3939(6) 0.63633(16) 0.6372(3) 0.0281(7) Uani 1 1 d . . . . .
C9 C 0.3585(7) 0.65059(18) 0.7498(3) 0.0335(8) Uani 1 1 d . . . . .
H9 H 0.490391 0.669845 0.786886 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1409(7) 0.6407(2) 0.8265(4) 0.0411(10) Uani 1 1 d . . . . .
C11 C 0.3497(8) 0.4829(2) 0.4955(5) 0.0602(14) Uani 1 1 d . . . . .
H11A H 0.308053 0.489782 0.413907 0.090 Uiso 1 1 calc R U . . .
H11B H 0.329743 0.439608 0.514283 0.090 Uiso 1 1 calc R U . . .
H11C H 0.516842 0.494868 0.508758 0.090 Uiso 1 1 calc R U . . .
Br1 Br 0.62363(8) 0.68953(2) 0.08541(5) 0.05507(14) Uani 1 1 d . . . . .
S1 S 0.15759(15) 0.52748(4) 0.58608(16) 0.0436(2) Uani 1 1 d . . . . .
F1 F 0.0789(5) 0.69521(13) 0.8772(3) 0.0717(9) Uani 1 1 d . . . . .
F2 F 0.1784(5) 0.60165(14) 0.9153(2) 0.0617(8) Uani 1 1 d . . . . .
F3 F -0.0571(4) 0.62074(14) 0.7698(2) 0.0576(7) Uani 1 1 d . . . . .
O1 O 0.6680(4) 0.72459(11) 0.5985(3) 0.0393(7) Uani 1 1 d . . . . .
H1 H 0.556(6) 0.7431(12) 0.610(5) 0.059 Uiso 1 1 calc R U . . .
O2 O -0.0846(5) 0.52141(13) 0.5441(3) 0.0633(11) Uani 1 1 d . . . . .
O3 O 0.2127(7) 0.51511(14) 0.7067(3) 0.0686(10) Uani 1 1 d . . . . .
N1 N 0.2355(5) 0.60249(13) 0.5600(3) 0.0314(7) Uani 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
C1 C2 1.376(5) . ?
C1 C6 1.387(6) . ?
C1 Br1 1.903(4) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(5) . ?
C3 C7 1.502(5) . ?
C4 C5 1.384(5) . ?
C4 N1 1.445(5) . ?
C5 C6 1.372(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.423(4) . ?
C7 C8 1.517(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.321(5) . ?
C8 N1 1.427(4) . ?
C9 C10 1.486(5) . ?
C9 H9 0.9300 . ?
C10 F2 1.322(5) . ?
C10 F3 1.327(4) . ?
C10 F1 1.347(5) . ?
C11 S1 1.750(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
S1 O2 1.411(3) . ?
S1 O3 1.419(4) . ?
S1 N1 1.692(3) . ?
O1 H1 0.74(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 C1 C6 121.3(4) . . ?
C2 C1 Br1 117.7(3) . . ?
C6 C1 Br1 120.9(3) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 C7 129.9(3) . . ?
C4 C3 C7 109.7(3) . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 N1 110.1(3) . . ?
C5 C4 N1 128.2(3) . . ?
C6 C5 C4 117.7(3) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C1 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 C3 115.5(3) . . ?
O1 C7 C8 113.3(3) . . ?
C3 C7 C8 102.3(3) . . ?
O1 C7 H7 108.5 . . ?
C3 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C9 C8 N1 128.1(3) . . ?
C9 C8 C7 123.1(3) . . ?
N1 C8 C7 108.3(3) . . ?
C8 C9 C10 130.1(3) . . ?
C8 C9 H9 115.0 . . ?
C10 C9 H9 115.0 . . ?
F2 C10 F3 106.6(3) . . ?
F2 C10 F1 105.6(4) . . ?
F3 C10 F1 106.3(3) . . ?
F2 C10 C9 114.1(3) . . ?
F3 C10 C9 114.7(3) . . ?
F1 C10 C9 108.9(3) . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 S1 O3 120.2(2) . . ?
O2 S1 N1 105.39(17) . . ?
O3 S1 N1 106.96(18) . . ?
O2 S1 C11 108.4(2) . . ?
O3 S1 C11 109.3(3) . . ?
N1 S1 C11 105.6(2) . . ?
C7 O1 H1 109.5 . . ?
C8 N1 C4 107.3(3) . . ?
C8 N1 S1 122.1(2) . . ?
C4 N1 S1 118.2(2) . . ?

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 0.8(6) . . . . ?
Br1 C1 C2 C3 -176.8(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C7 175.3(4) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C7 C3 C4 C5 -177.0(3) . . . . ?
C2 C3 C4 N1 179.2(3) . . . . ?
C7 C3 C4 N1 2.6(4) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
N1 C4 C5 C6 -178.5(4) . . . . ?
C4 C5 C6 C1 -0.7(6) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
Br1 C1 C6 C5 177.3(3) . . . . ?
C2 C3 C7 O1 49.4(5) . . . . ?
C4 C3 C7 O1 -134.4(3) . . . . ?
C2 C3 C7 C8 172.9(4) . . . . ?
C4 C3 C7 C8 -10.9(4) . . . . ?
O1 C7 C8 C9 -31.3(5) . . . . ?
C3 C7 C8 C9 -156.2(3) . . . . ?
O1 C7 C8 N1 140.4(3) . . . . ?
C3 C7 C8 N1 15.5(3) . . . . ?
N1 C8 C9 C10 -5.4(7) . . . . ?
C7 C8 C9 C10 164.6(4) . . . . ?
C8 C9 C10 F2 115.1(5) . . . . ?
C8 C9 C10 F3 -8.4(6) . . . . ?
C8 C9 C10 F1 -127.3(5) . . . . ?
C9 C8 N1 C4 156.6(4) . . . . ?
C7 C8 N1 C4 -14.6(3) . . . . ?
C9 C8 N1 S1 -62.2(5) . . . . ?
C7 C8 N1 S1 126.6(3) . . . . ?
C3 C4 N1 C8 7.6(4) . . . . ?
C5 C4 N1 C8 -172.8(4) . . . . ?
C3 C4 N1 S1 -135.3(3) . . . . ?
C5 C4 N1 S1 44.2(5) . . . . ?
O2 S1 N1 C8 146.3(3) . . . . ?
O3 S1 N1 C8 17.3(3) . . . . ?
C11 S1 N1 C8 -99.1(3) . . . . ?
O2 S1 N1 C4 -76.5(3) . . . . ?
O3 S1 N1 C4 154.5(3) . . . . ?
C11 S1 N1 C4 38.2(3) . . . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.053



