# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_GM037_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2451030'
loop_
_audit_author_name
_audit_author_address
'Balasubramani Alagesan'
;University of Hyderabad
India
;
_audit_update_record             
;
2025-05-14 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_audit_creation_date             2024-08-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C23 H15 N S'
_chemical_formula_sum            'C23 H15 N S'
_chemical_formula_weight         337.448
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   9.755(2)
_cell_length_b                   17.605(4)
_cell_length_c                   19.937(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3423.6(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.31
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5471
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             1409.487
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9922
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28725
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9922
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         2.04
_diffrn_ambient_temperature      102.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9922
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                3262
_reflns_number_total             3962
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5856
_refine_diff_density_min         -0.3366
_refine_diff_density_rms         0.1079
_refine_ls_d_res_high            0.7660
_refine_ls_d_res_low             9.9684
_refine_ls_goodness_of_fit_ref   1.0124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.0124
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0780P)²+1.1849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1296
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00P(H00P), C00O(H00O), C00N(H00N), C00L(H00L), C00E(H00E),
 C00G(H00G), C00I(H00I), C00B(H00B), C00H(H00H), C00K(H00K), C00J(H00J),
 C00F(H00F), C00C(H00C), C009(H009)
;
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_refinement_flags_posn
S1 S 0.34051(4) 0.46217(2) 0.36739(2) 0.02525(14) Uani 1.000000 .
N002 N 0.33903(13) 0.56383(8) 0.46487(7) 0.0245(3) Uani 1.000000 .
C003 C 0.55372(15) 0.55635(8) 0.41219(7) 0.0203(3) Uani 1.000000 .
C004 C 0.56124(16) 0.61576(8) 0.46322(7) 0.0219(3) Uani 1.000000 .
C005 C 0.41209(16) 0.53051(8) 0.41844(7) 0.0215(3) Uani 1.000000 .
C006 C 0.64357(16) 0.52661(9) 0.36603(7) 0.0215(3) Uani 1.000000 .
C007 C 0.78882(16) 0.55143(8) 0.36254(8) 0.0222(3) Uani 1.000000 .
C008 C 0.42942(16) 0.61723(9) 0.49312(8) 0.0233(3) Uani 1.000000 .
C009 C 0.60159(17) 0.46933(9) 0.31946(8) 0.0245(3) Uani 1.000000 .
C00A C 0.47463(16) 0.43758(9) 0.31515(7) 0.0237(3) Uani 1.000000 .
C00B C 0.66069(17) 0.66781(9) 0.48462(8) 0.0261(3) Uani 1.000000 .
C00C C 0.84322(16) 0.57869(9) 0.30250(8) 0.0254(3) Uani 1.000000 .
C00D C 0.43702(17) 0.37899(9) 0.26508(8) 0.0277(4) Uani 1.000000 .
C00E C 0.39730(18) 0.66789(9) 0.54420(8) 0.0282(3) Uani 1.000000 .
C00F C 0.97870(18) 0.60277(9) 0.29916(9) 0.0309(4) Uani 1.000000 .
C00G C 0.49649(19) 0.71924(9) 0.56420(8) 0.0318(4) Uani 1.000000 .
C00H C 0.87369(17) 0.54628(10) 0.41907(9) 0.0290(4) Uani 1.000000 .
C00I C 0.62650(19) 0.71975(10) 0.53440(8) 0.0318(4) Uani 1.000000 .
C00J C 1.06153(17) 0.59818(10) 0.35557(9) 0.0326(4) Uani 1.000000 .
C00K C 1.00933(18) 0.56931(10) 0.41506(9) 0.0334(4) Uani 1.000000 .
C00L C 0.34358(19) 0.32189(10) 0.28090(9) 0.0346(4) Uani 1.000000 .
C00M C 0.4932(2) 0.38128(11) 0.20053(9) 0.0383(4) Uani 1.000000 .
C00N C 0.3075(2) 0.26768(11) 0.23346(11) 0.0480(5) Uani 1.000000 .
C00O C 0.3668(3) 0.26885(12) 0.17076(11) 0.0523(6) Uani 1.000000 .
C00P C 0.4588(2) 0.32572(14) 0.15392(10) 0.0527(6) Uani 1.000000 .
H00M H 0.5548(2) 0.42081(11) 0.18855(9) 0.0460(5) Uiso 1.000000 R
H00P H 0.4985(2) 0.32674(14) 0.11041(10) 0.0633(7) Uiso 1.000000 R
H00O H 0.3445(3) 0.23058(12) 0.13898(11) 0.0628(7) Uiso 1.000000 R
H00N H 0.2419(2) 0.22973(11) 0.24427(11) 0.0576(6) Uiso 1.000000 R
H00L H 0.30423(19) 0.32002(10) 0.32446(9) 0.0416(5) Uiso 1.000000 R
H00E H 0.30953(18) 0.66727(9) 0.56484(8) 0.0338(4) Uiso 1.000000 R
H00G H 0.47612(19) 0.75472(9) 0.59869(8) 0.0381(5) Uiso 1.000000 R
H00I H 0.69238(19) 0.75618(10) 0.54843(8) 0.0382(5) Uiso 1.000000 R
H00B H 0.74987(17) 0.66761(9) 0.46546(8) 0.0313(4) Uiso 1.000000 R
H00H H 0.83831(17) 0.52703(10) 0.46008(9) 0.0347(4) Uiso 1.000000 R
H00K H 1.06693(18) 0.56530(10) 0.45332(9) 0.0401(5) Uiso 1.000000 R
H00J H 1.15408(17) 0.61482(10) 0.35346(9) 0.0391(5) Uiso 1.000000 R
H00F H 1.01451(18) 0.62232(9) 0.25835(9) 0.0371(4) Uiso 1.000000 R
H00C H 0.78720(16) 0.58082(9) 0.26357(8) 0.0305(4) Uiso 1.000000 R
H009 H 0.66869(17) 0.45178(9) 0.28859(8) 0.0294(4) Uiso 1.000000 R


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 C005 1.7237(15) . ?
S1 C00A 1.7273(16) . ?
N002 C005 1.307(2) . ?
N002 C008 1.407(2) . ?
C003 C004 1.461(2) . ?
C003 C005 1.460(2) . ?
C003 C006 1.375(2) . ?
C004 C008 1.418(2) . ?
C004 C00B 1.401(2) . ?
C006 C007 1.484(2) . ?
C006 C009 1.431(2) . ?
C007 C00C 1.395(2) . ?
C007 C00H 1.401(2) . ?
C008 C00E 1.389(2) . ?
C009 C00A 1.361(2) . ?
C00A C00D 1.482(2) . ?
C00B C00I 1.390(2) . ?
C00C C00F 1.389(2) . ?
C00D C00L 1.393(2) . ?
C00D C00M 1.399(2) . ?
C00E C00G 1.383(2) . ?
C00F C00J 1.387(3) . ?
C00G C00I 1.400(3) . ?
C00H C00K 1.386(2) . ?
C00J C00K 1.387(3) . ?
C00L C00N 1.389(2) . ?
C00M C00P 1.390(3) . ?
C00N C00O 1.377(3) . ?
C00O C00P 1.386(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A S1 C005 102.95(8) . . ?
C008 N002 C005 103.99(13) . . ?
C005 C003 C004 102.19(12) . . ?
C006 C003 C004 134.99(14) . . ?
C006 C003 C005 122.81(14) . . ?
C008 C004 C003 105.09(13) . . ?
C00B C004 C003 135.65(14) . . ?
C00B C004 C008 119.21(14) . . ?
N002 C005 S1 120.69(12) . . ?
C003 C005 S1 123.40(12) . . ?
C003 C005 N002 115.89(13) . . ?
C007 C006 C003 121.86(14) . . ?
C009 C006 C003 121.36(14) . . ?
C009 C006 C007 116.77(13) . . ?
C00C C007 C006 120.31(14) . . ?
C00H C007 C006 120.48(14) . . ?
C00H C007 C00C 119.19(15) . . ?
C004 C008 N002 112.83(13) . . ?
C00E C008 N002 125.53(15) . . ?
C00E C008 C004 121.63(15) . . ?
C00A C009 C006 126.21(14) . . ?
C009 C00A S1 123.23(12) . . ?
C00D C00A S1 113.15(12) . . ?
C00D C00A C009 123.62(15) . . ?
C00I C00B C004 118.79(15) . . ?
C00F C00C C007 120.53(15) . . ?
C00L C00D C00A 120.79(15) . . ?
C00M C00D C00A 120.17(16) . . ?
C00M C00D C00L 119.03(16) . . ?
C00G C00E C008 118.24(16) . . ?
C00J C00F C00C 119.83(16) . . ?
C00I C00G C00E 121.03(15) . . ?
C00K C00H C007 119.91(16) . . ?
C00G C00I C00B 121.05(15) . . ?
C00K C00J C00F 120.05(16) . . ?
C00J C00K C00H 120.45(16) . . ?
C00N C00L C00D 120.48(19) . . ?
C00P C00M C00D 120.0(2) . . ?
C00O C00N C00L 120.1(2) . . ?
C00P C00O C00N 120.16(18) . . ?
C00O C00P C00M 120.2(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_KB1654_0m
_database_code_depnum_ccdc_archive 'CCDC 2451031'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-08-25 deposited with the CCDC.	2025-09-22 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         'C23 H13 Br F N S'
_chemical_formula_sum            'C23 H13 Br F N S'
_chemical_formula_weight         434.31

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'
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'
F F 0.0171 0.0103 '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                   9.555(6)
_cell_length_b                   10.663(6)
_cell_length_c                   11.118(6)
_cell_angle_alpha                115.183(8)
_cell_angle_beta                 110.520(10)
_cell_angle_gamma                95.253(10)
_cell_volume                     920.4(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2765
_cell_measurement_theta_min      2.244
_cell_measurement_theta_max      28.360

_exptl_crystal_description       'metallic brownish brown'
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             436
_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    2.363
_shelx_estimated_absorpt_T_min   0.649
_shelx_estimated_absorpt_T_max   0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6176
_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                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13731
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0427
_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       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.244
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3182
_reflns_number_gt                2406
_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       'APEX5 (Bruker, 2023)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_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)+(0.1521P)²+0.3925P] 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         3182
_refine_ls_number_parameters     263
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.2199
_refine_ls_wR_factor_gt          0.2006
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.104
_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 1.0587(6) 0.3129(5) 0.8723(5) 0.0432(11) Uani 1 1 d . . . . .
C2 C 1.0986(7) 0.3608(6) 1.0214(6) 0.0501(12) Uani 1 1 d . . . . .
C3 C 1.2487(8) 0.3983(6) 1.1252(6) 0.0625(16) Uani 1 1 d . . . . .
H3 H 1.269418 0.430019 1.223278 0.075 Uiso 1 1 calc R U . . .
C4 C 1.3672(8) 0.3883(7) 1.0826(7) 0.0688(17) Uani 1 1 d . . . . .
H4 H 1.469159 0.414138 1.152252 0.083 Uiso 1 1 calc R U . . .
C5 C 1.3361(7) 0.3401(8) 0.9372(7) 0.0718(17) Uani 1 1 d . . . . .
H5 H 1.416432 0.333410 0.907994 0.086 Uiso 1 1 calc R U . . .
C6 C 1.1848(6) 0.3020(7) 0.8357(6) 0.0605(15) Uani 1 1 d . . . . .
H6 H 1.165056 0.267042 0.737425 0.073 Uiso 1 1 calc R U . . .
C7 C 0.8975(5) 0.2778(5) 0.7592(5) 0.0396(10) Uani 1 1 d . . . . .
C8 C 0.5816(5) 0.2020(5) 0.6461(5) 0.0378(10) Uani 1 1 d . . . . .
C9 C 0.5883(5) 0.2088(5) 0.5194(5) 0.0379(10) Uani 1 1 d . . . . .
C10 C 0.7252(5) 0.2409(5) 0.5129(5) 0.0391(10) Uani 1 1 d . . . . .
C11 C 0.8720(5) 0.2785(5) 0.6290(5) 0.0414(11) Uani 1 1 d . . . . .
H11 H 0.959342 0.306064 0.617210 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3412(6) 0.1416(5) 0.4938(6) 0.0461(12) Uani 1 1 d . . . . .
C13 C 0.4247(5) 0.1683(5) 0.4190(5) 0.0413(11) Uani 1 1 d . . . . .
C14 C 0.7227(5) 0.2150(5) 0.3643(5) 0.0429(11) Uani 1 1 d D U . . .
C16 C 0.6872(6) 0.0493(7) 0.1205(5) 0.0552(13) Uani 1 1 d D U . . .
H16 H 0.660977 -0.042436 0.040985 0.066 Uiso 1 1 calc R U . A 1
C17 C 0.7221(7) 0.1657(7) 0.0993(6) 0.0574(13) Uani 1 1 d . U . . .
H17 H 0.723095 0.149216 0.010510 0.069 Uiso 1 1 calc R U . . .
C18 C 0.7540(7) 0.3000(7) 0.2047(6) 0.0589(13) Uani 1 1 d . U . . .
H18 H 0.775339 0.376259 0.187756 0.071 Uiso 1 1 calc R U . . .
C19 C 0.7562(6) 0.3298(6) 0.3408(6) 0.0517(12) Uani 1 1 d . U . . .
C20 C 0.1787(6) 0.1010(6) 0.4272(7) 0.0540(13) Uani 1 1 d . . . . .
H20 H 0.122662 0.083379 0.474721 0.065 Uiso 1 1 calc R U . . .
C21 C 0.1035(6) 0.0876(6) 0.2911(8) 0.0649(17) Uani 1 1 d . . . . .
H21 H -0.004840 0.058464 0.245138 0.078 Uiso 1 1 calc R U . . .
C22 C 0.1843(6) 0.1162(6) 0.2199(7) 0.0589(15) Uani 1 1 d . . . . .
H22 H 0.129165 0.106688 0.127565 0.071 Uiso 1 1 calc R U . . .
C23 C 0.3459(6) 0.1588(6) 0.2833(6) 0.0499(12) Uani 1 1 d . . . . .
H23 H 0.399701 0.180278 0.235910 0.060 Uiso 1 1 calc R U . . .
N1 N 0.4408(5) 0.1628(4) 0.6336(5) 0.0476(10) Uani 1 1 d . . . . .
S1 S 0.74497(14) 0.23382(14) 0.79776(13) 0.0462(4) Uani 1 1 d . . . . .
C15 C 0.6876(4) 0.0561(6) 0.2479(4) 0.0385(12) Uani 0.936(6) 1 d D U P B 1
H15 H 0.669484 -0.023128 0.261281 0.046 Uiso 0.936(6) 1 calc R U P B 1
Br1 Br 0.7948(2) 0.52560(9) 0.48518(10) 0.0710(6) Uani 0.936(6) 1 d . . P B 1
C15D C 0.6917(6) 0.0733(15) 0.2549(10) 0.044(6) Uani 0.064(6) 1 d D U P B 2
H15D H 0.674325 -0.003647 0.271784 0.053 Uiso 0.064(6) 1 calc R U P B 2
Br1D Br 0.703(4) 0.501(3) 0.469(3) 0.133(9) Uani 0.064(6) 1 d . . P B 2
F1 F 0.9885(4) 0.3733(5) 1.0692(4) 0.0809(11) 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 1.399(7) . ?
C1 C6 1.399(8) . ?
C1 C7 1.493(7) . ?
C2 F1 1.328(7) . ?
C2 C3 1.375(8) . ?
C3 C4 1.368(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.384(6) . ?
C7 S1 1.735(5) . ?
C8 N1 1.312(6) . ?
C8 C9 1.464(6) . ?
C8 S1 1.722(5) . ?
C9 C10 1.356(6) . ?
C9 C13 1.455(6) . ?
C10 C11 1.407(6) . ?
C10 C14 1.546(6) . ?
C11 H11 0.9300 . ?
C12 C20 1.394(7) . ?
C12 N1 1.413(7) . ?
C12 C13 1.426(7) . ?
C13 C23 1.383(7) . ?
C14 C19 1.388(7) . ?
C14 C15D 1.397(10) . ?
C14 C15 1.544(6) . ?
C16 C15 1.386(6) . ?
C16 C15D 1.389(10) . ?
C16 C17 1.390(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.326(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.400(8) . ?
C18 H18 0.9300 . ?
C19 Br1 1.914(6) . ?
C19 Br1D 2.02(3) . ?
C20 C21 1.365(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C15 H15 0.9300 . ?
C15D H15D 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
C2 C1 C6 114.2(5) . . ?
C2 C1 C7 124.3(5) . . ?
C6 C1 C7 121.5(4) . . ?
F1 C2 C3 116.6(5) . . ?
F1 C2 C1 119.8(5) . . ?
C3 C2 C1 123.5(5) . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.1(7) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 123.6(6) . . ?
C5 C6 H6 118.2 . . ?
C1 C6 H6 118.2 . . ?
C11 C7 C1 121.2(4) . . ?
C11 C7 S1 121.9(4) . . ?
C1 C7 S1 116.9(3) . . ?
N1 C8 C9 115.2(4) . . ?
N1 C8 S1 121.6(3) . . ?
C9 C8 S1 123.2(3) . . ?
C10 C9 C13 134.8(4) . . ?
C10 C9 C8 122.1(4) . . ?
C13 C9 C8 103.1(4) . . ?
C9 C10 C11 123.5(4) . . ?
C9 C10 C14 119.0(4) . . ?
C11 C10 C14 116.9(4) . . ?
C7 C11 C10 125.6(4) . . ?
C7 C11 H11 117.2 . . ?
C10 C11 H11 117.2 . . ?
C20 C12 N1 127.7(5) . . ?
C20 C12 C13 119.7(5) . . ?
N1 C12 C13 112.6(4) . . ?
C23 C13 C12 120.5(4) . . ?
C23 C13 C9 134.6(4) . . ?
C12 C13 C9 104.8(4) . . ?
C19 C14 C15D 120.1(7) . . ?
C19 C14 C15 122.6(4) . . ?
C19 C14 C10 121.1(4) . . ?
C15D C14 C10 118.7(7) . . ?
C15 C14 C10 116.2(4) . . ?
C15 C16 C17 126.6(5) . . ?
C15D C16 C17 120.0(8) . . ?
C15 C16 H16 116.7 . . ?
C17 C16 H16 116.7 . . ?
C18 C17 C16 120.6(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.6(5) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C18 118.7(5) . . ?
C14 C19 Br1 121.8(4) . . ?
C18 C19 Br1 119.4(4) . . ?
C14 C19 Br1D 109.9(9) . . ?
C18 C19 Br1D 125.2(8) . . ?
C21 C20 C12 118.7(5) . . ?
C21 C20 H20 120.6 . . ?
C12 C20 H20 120.6 . . ?
C20 C21 C22 121.7(5) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C23 121.4(5) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C13 C23 C22 118.0(5) . . ?
C13 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?
C8 N1 C12 104.3(4) . . ?
C8 S1 C7 103.5(2) . . ?
C16 C15 C14 109.8(4) . . ?
C16 C15 H15 125.1 . . ?
C14 C15 H15 125.1 . . ?
C16 C15D C14 118.9(12) . . ?
C16 C15D H15D 120.5 . . ?
C14 C15D H15D 120.5 . . ?

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
C6 C1 C2 F1 -178.9(5) . . . . ?
C7 C1 C2 F1 2.0(8) . . . . ?
C6 C1 C2 C3 1.8(8) . . . . ?
C7 C1 C2 C3 -177.3(5) . . . . ?
F1 C2 C3 C4 -179.7(5) . . . . ?
C1 C2 C3 C4 -0.3(9) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C4 C5 C6 C1 1.8(10) . . . . ?
C2 C1 C6 C5 -2.5(8) . . . . ?
C7 C1 C6 C5 176.6(5) . . . . ?
C2 C1 C7 C11 158.0(5) . . . . ?
C6 C1 C7 C11 -21.0(7) . . . . ?
C2 C1 C7 S1 -22.9(6) . . . . ?
C6 C1 C7 S1 158.1(4) . . . . ?
N1 C8 C9 C10 -176.8(4) . . . . ?
S1 C8 C9 C10 0.1(6) . . . . ?
N1 C8 C9 C13 0.6(5) . . . . ?
S1 C8 C9 C13 177.5(3) . . . . ?
C13 C9 C10 C11 179.7(5) . . . . ?
C8 C9 C10 C11 -3.8(7) . . . . ?
C13 C9 C10 C14 -9.2(8) . . . . ?
C8 C9 C10 C14 167.3(4) . . . . ?
C1 C7 C11 C10 177.0(4) . . . . ?
S1 C7 C11 C10 -2.0(7) . . . . ?
C9 C10 C11 C7 5.0(8) . . . . ?
C14 C10 C11 C7 -166.3(5) . . . . ?
C20 C12 C13 C23 2.1(7) . . . . ?
N1 C12 C13 C23 -177.2(4) . . . . ?
C20 C12 C13 C9 179.4(4) . . . . ?
N1 C12 C13 C9 0.1(5) . . . . ?
C10 C9 C13 C23 -6.7(10) . . . . ?
C8 C9 C13 C23 176.4(5) . . . . ?
C10 C9 C13 C12 176.5(5) . . . . ?
C8 C9 C13 C12 -0.4(5) . . . . ?
C9 C10 C14 C19 107.8(5) . . . . ?
C11 C10 C14 C19 -80.5(6) . . . . ?
C9 C10 C14 C15D -74.6(6) . . . . ?
C11 C10 C14 C15D 97.1(5) . . . . ?
C9 C10 C14 C15 -74.6(5) . . . . ?
C11 C10 C14 C15 97.1(5) . . . . ?
C15 C16 C17 C18 -3.0(9) . . . . ?
C15D C16 C17 C18 -2.6(8) . . . . ?
C16 C17 C18 C19 1.0(9) . . . . ?
C15D C14 C19 C18 1.7(7) . . . . ?
C15 C14 C19 C18 1.8(7) . . . . ?
C10 C14 C19 C18 179.2(4) . . . . ?
C15 C14 C19 Br1 178.6(3) . . . . ?
C10 C14 C19 Br1 -3.9(6) . . . . ?
C15D C14 C19 Br1D 155.4(9) . . . . ?
C10 C14 C19 Br1D -27.1(10) . . . . ?
C17 C18 C19 C14 -0.6(8) . . . . ?
C17 C18 C19 Br1 -177.5(4) . . . . ?
C17 C18 C19 Br1D -149.9(12) . . . . ?
N1 C12 C20 C21 179.3(5) . . . . ?
C13 C12 C20 C21 0.1(7) . . . . ?
C12 C20 C21 C22 -1.4(8) . . . . ?
C20 C21 C22 C23 0.5(9) . . . . ?
C12 C13 C23 C22 -2.9(8) . . . . ?
C9 C13 C23 C22 -179.3(5) . . . . ?
C21 C22 C23 C13 1.7(8) . . . . ?
C9 C8 N1 C12 -0.6(5) . . . . ?
S1 C8 N1 C12 -177.5(3) . . . . ?
C20 C12 N1 C8 -179.0(5) . . . . ?
C13 C12 N1 C8 0.3(5) . . . . ?
N1 C8 S1 C7 178.9(4) . . . . ?
C9 C8 S1 C7 2.2(4) . . . . ?
C11 C7 S1 C8 -1.3(5) . . . . ?
C1 C7 S1 C8 179.7(3) . . . . ?
C17 C16 C15 C14 3.8(7) . . . . ?
C19 C14 C15 C16 -3.2(6) . . . . ?
C10 C14 C15 C16 179.3(4) . . . . ?
C17 C16 C15D C14 3.7(7) . . . . ?
C19 C14 C15D C16 -3.3(7) . . . . ?
C10 C14 C15D C16 179.2(4) . . . . ?

_refine_diff_density_max         1.411
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.104

