# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2168916'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 Br N O2 S2'
_chemical_formula_sum            'C16 H12 Br N O2 S2'
_chemical_formula_weight         394.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8787(3)
_cell_length_b                   8.2497(4)
_cell_length_c                   13.2573(6)
_cell_angle_alpha                91.0830(10)
_cell_angle_beta                 93.0320(10)
_cell_angle_gamma                116.6810(10)
_cell_volume                     767.97(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.32
_cell_measurement_theta_min      3.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.242
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5566
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.7396.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16708
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        65.317
_diffrn_reflns_theta_max         65.317
_diffrn_reflns_theta_min         3.342
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2587
_reflns_number_total             2587
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+1.0817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00M(H00A,H00D,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br01 Br -0.20278(4) 0.71650(4) 1.00744(2) 0.02924(13) Uani 1 1 d . . . . .
S002 S 0.26727(9) 0.29213(8) 0.54840(4) 0.02161(16) Uani 1 1 d . . . . .
S003 S 0.40462(9) 0.24515(8) 0.75466(5) 0.02308(16) Uani 1 1 d . . . . .
O004 O 0.7390(2) 0.7710(2) 0.72874(14) 0.0257(4) Uani 1 1 d . . . . .
O005 O 0.6483(3) 0.9637(2) 0.80228(14) 0.0279(4) Uani 1 1 d . . . . .
N006 N 0.3652(3) 0.5373(3) 0.68937(15) 0.0179(4) Uani 1 1 d . . . . .
C007 C 0.3507(3) 0.3677(3) 0.67363(18) 0.0185(5) Uani 1 1 d . . . . .
C008 C 0.2593(3) 0.4934(3) 0.51873(19) 0.0204(5) Uani 1 1 d . . . . .
C009 C 0.6167(3) 0.8126(3) 0.77424(18) 0.0192(5) Uani 1 1 d . . . . .
C00A C 0.3161(3) 0.6123(3) 0.60530(18) 0.0176(5) Uani 1 1 d . . . . .
C00B C 0.4323(3) 0.6373(3) 0.78745(18) 0.0185(5) Uani 1 1 d . . . . .
H00B H 0.469183 0.560384 0.832114 0.022 Uiso 1 1 calc R . . . .
C00C C 0.2746(4) 0.8323(3) 0.5074(2) 0.0238(5) Uani 1 1 d . . . . .
H00C H 0.276416 0.947810 0.502459 0.029 Uiso 1 1 calc R . . . .
C00D C 0.2771(3) 0.6624(3) 0.83852(18) 0.0195(5) Uani 1 1 d . . . . .
C00E C 0.2149(4) 0.5450(3) 0.42738(19) 0.0235(5) Uani 1 1 d . . . . .
H00E H 0.177792 0.464855 0.369139 0.028 Uiso 1 1 calc R . . . .
C00F C -0.0578(4) 0.5671(4) 0.85790(19) 0.0230(5) Uani 1 1 d . . . . .
H00F H -0.187618 0.492480 0.836453 0.028 Uiso 1 1 calc R . . . .
C00G C 0.0865(4) 0.5538(3) 0.80886(19) 0.0221(5) Uani 1 1 d . . . . .
H00G H 0.054291 0.468275 0.753438 0.026 Uiso 1 1 calc R . . . .
C00H C -0.0087(4) 0.6914(3) 0.93886(18) 0.0216(5) Uani 1 1 d . . . . .
C00I C 0.3214(4) 0.7821(3) 0.60066(19) 0.0225(5) Uani 1 1 d . . . . .
H00I H 0.355823 0.861701 0.659046 0.027 Uiso 1 1 calc R . . . .
C00J C 0.2254(4) 0.7172(4) 0.4219(2) 0.0251(5) Uani 1 1 d . . . . .
H00J H 0.198509 0.756458 0.358765 0.030 Uiso 1 1 calc R . . . .
C00K C 0.1781(4) 0.7961(4) 0.9730(2) 0.0284(6) Uani 1 1 d . . . . .
H00K H 0.208901 0.877879 1.030129 0.034 Uiso 1 1 calc R . . . .
C00L C 0.3210(4) 0.7811(4) 0.9232(2) 0.0274(6) Uani 1 1 d . . . . .
H00L H 0.450246 0.852278 0.946932 0.033 Uiso 1 1 calc R . . . .
C00M C 0.9275(4) 0.9216(4) 0.7211(2) 0.0305(6) Uani 1 1 d . . . . .
H00A H 0.918684 1.008618 0.674379 0.046 Uiso 1 1 calc GR . . . .
H00D H 1.012925 0.875451 0.695827 0.046 Uiso 1 1 calc GR . . . .
H00H H 0.977528 0.982125 0.787995 0.046 Uiso 1 1 calc GR . . . .


_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
Br01 C00H 1.906(2) . ?
S002 C007 1.748(2) . ?
S002 C008 1.741(2) . ?
S003 C007 1.654(3) . ?
O004 C009 1.327(3) . ?
O004 C00M 1.457(3) . ?
O005 C009 1.204(3) . ?
N006 C007 1.363(3) . ?
N006 C00A 1.403(3) . ?
N006 C00B 1.465(3) . ?
C008 C00A 1.410(3) . ?
C008 C00E 1.371(4) . ?
C009 C00B 1.543(3) . ?
C00A C00I 1.386(3) . ?
C00B C00D 1.518(3) . ?
C00C C00I 1.394(4) . ?
C00C C00J 1.386(4) . ?
C00D C00G 1.389(4) . ?
C00D C00L 1.398(4) . ?
C00E C00J 1.389(4) . ?
C00F C00G 1.383(4) . ?
C00F C00H 1.383(4) . ?
C00H C00K 1.375(4) . ?
C00K C00L 1.385(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
C008 S002 C007 93.03(12) . . ?
C009 O004 C00M 115.2(2) . . ?
C007 N006 C00A 115.98(19) . . ?
C007 N006 C00B 122.1(2) . . ?
C00A N006 C00B 121.92(19) . . ?
S003 C007 S002 122.60(14) . . ?
N006 C007 S002 109.24(17) . . ?
N006 C007 S003 128.15(19) . . ?
C00A C008 S002 109.69(18) . . ?
C00E C008 S002 129.2(2) . . ?
C00E C008 C00A 121.0(2) . . ?
O004 C009 C00B 109.38(19) . . ?
O005 C009 O004 124.6(2) . . ?
O005 C009 C00B 126.0(2) . . ?
N006 C00A C008 112.0(2) . . ?
C00I C00A N006 127.4(2) . . ?
C00I C00A C008 120.5(2) . . ?
N006 C00B C009 108.66(19) . . ?
N006 C00B C00D 112.72(19) . . ?
C00D C00B C009 115.77(19) . . ?
C00J C00C C00I 121.4(2) . . ?
C00G C00D C00B 120.6(2) . . ?
C00G C00D C00L 118.1(2) . . ?
C00L C00D C00B 120.9(2) . . ?
C008 C00E C00J 118.5(2) . . ?
C00H C00F C00G 118.4(2) . . ?
C00F C00G C00D 121.7(2) . . ?
C00F C00H Br01 119.84(19) . . ?
C00K C00H Br01 118.62(19) . . ?
C00K C00H C00F 121.5(2) . . ?
C00A C00I C00C 117.8(2) . . ?
C00C C00J C00E 120.7(2) . . ?
C00H C00K C00L 119.3(2) . . ?
C00K C00L C00D 120.7(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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2168920'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 Br N O3 S'
_chemical_formula_sum            'C16 H12 Br N O3 S'
_chemical_formula_weight         378.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8174(2)
_cell_length_b                   8.2527(3)
_cell_length_c                   31.1764(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1496.76(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.34
_cell_measurement_theta_min      5.55
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.425
_exptl_absorpt_coefficient_mu    5.158
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.7389.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            18325
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.356
_diffrn_reflns_theta_min         2.835
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2678
_reflns_number_total             2710
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+0.8394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0609
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C16(H16), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br1 Br -0.02956(7) 0.87261(6) 0.81934(2) 0.04394(14) Uani 1 1 d . . . . .
S1 S -0.09691(15) 0.67738(10) 0.53064(3) 0.0340(2) Uani 1 1 d . . . . .
O2 O 0.7812(4) 0.9436(3) 0.60802(9) 0.0396(6) Uani 1 1 d . . . . .
O3 O 0.4766(5) 1.0725(3) 0.63353(9) 0.0455(7) Uani 1 1 d . . . . .
O1 O -0.2262(5) 0.4232(3) 0.48401(9) 0.0453(7) Uani 1 1 d . . . . .
N1 N 0.0753(5) 0.3911(3) 0.53085(9) 0.0328(6) Uani 1 1 d . . . . .
H1 H 0.104218 0.288952 0.524793 0.039 Uiso 1 1 calc R . . . .
C9 C 0.5905(5) 0.9524(4) 0.63108(10) 0.0250(7) Uani 1 1 d . . . . .
C8 C 0.5369(6) 0.7900(4) 0.65227(9) 0.0271(7) Uani 1 1 d . . . . .
H8 H 0.686287 0.738060 0.660154 0.033 Uiso 1 1 calc R . . . .
C11 C 0.3984(6) 0.8113(4) 0.69311(10) 0.0259(7) Uani 1 1 d . . . . .
C3 C 0.1328(5) 0.6362(4) 0.56521(10) 0.0262(6) Uani 1 1 d . . . . .
C4 C 0.2425(6) 0.7404(4) 0.59362(10) 0.0272(7) Uani 1 1 d . . . . .
H4 H 0.197662 0.850869 0.595467 0.033 Uiso 1 1 calc R . . . .
C5 C 0.4183(6) 0.6811(4) 0.61926(10) 0.0245(7) Uani 1 1 d . . . . .
C16 C 0.4800(6) 0.7493(4) 0.73179(10) 0.0282(7) Uani 1 1 d . . . . .
H16 H 0.623119 0.693819 0.732246 0.034 Uiso 1 1 calc R . . . .
C2 C 0.2025(6) 0.4763(4) 0.56143(10) 0.0269(7) Uani 1 1 d . . . . .
C6 C 0.4833(7) 0.5188(4) 0.61580(10) 0.0298(7) Uani 1 1 d . . . . .
H6 H 0.602950 0.478452 0.633582 0.036 Uiso 1 1 calc R . . . .
C1 C -0.0944(7) 0.4741(4) 0.51107(11) 0.0328(8) Uani 1 1 d . . . . .
C14 C 0.1490(6) 0.8469(4) 0.76833(10) 0.0294(7) Uani 1 1 d . . . . .
C7 C 0.3770(6) 0.4154(4) 0.58700(11) 0.0335(8) Uani 1 1 d . . . . .
H7 H 0.422815 0.305238 0.584818 0.040 Uiso 1 1 calc R . . . .
C12 C 0.1873(6) 0.8925(5) 0.69336(10) 0.0318(7) Uani 1 1 d . . . . .
H12 H 0.128889 0.936041 0.667347 0.038 Uiso 1 1 calc R . . . .
C13 C 0.0619(6) 0.9105(4) 0.73084(10) 0.0320(7) Uani 1 1 d . . . . .
H13 H -0.081396 0.965720 0.730687 0.038 Uiso 1 1 calc R . . . .
C15 C 0.3571(6) 0.7667(4) 0.76969(11) 0.0319(8) Uani 1 1 d . . . . .
H15 H 0.414754 0.724401 0.795913 0.038 Uiso 1 1 calc R . . . .
C10 C 0.8380(7) 1.0870(5) 0.58350(13) 0.0431(9) Uani 1 1 d . . . . .
H10A H 0.711881 1.112028 0.563744 0.065 Uiso 1 1 calc GR . . . .
H10B H 0.979067 1.067640 0.567098 0.065 Uiso 1 1 calc GR . . . .
H10C H 0.861556 1.178519 0.603052 0.065 Uiso 1 1 calc GR . . . .


_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
Br1 C14 1.911(3) . ?
S1 C3 1.750(3) . ?
S1 C1 1.785(3) . ?
O2 C9 1.324(4) . ?
O2 C10 1.447(4) . ?
O3 C9 1.195(4) . ?
O1 C1 1.215(4) . ?
N1 C2 1.396(4) . ?
N1 C1 1.351(5) . ?
C9 C8 1.526(4) . ?
C8 C11 1.517(4) . ?
C8 C5 1.531(5) . ?
C11 C16 1.394(4) . ?
C11 C12 1.399(5) . ?
C3 C4 1.390(5) . ?
C3 C2 1.385(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.396(5) . ?
C16 C15 1.389(5) . ?
C2 C7 1.385(5) . ?
C6 C7 1.384(5) . ?
C14 C13 1.378(5) . ?
C14 C15 1.380(5) . ?
C12 C13 1.386(5) . ?

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
C3 S1 C1 91.24(17) . . ?
C9 O2 C10 115.7(3) . . ?
C1 N1 C2 116.3(3) . . ?
O2 C9 C8 111.0(3) . . ?
O3 C9 O2 123.0(3) . . ?
O3 C9 C8 126.0(3) . . ?
C9 C8 C5 108.5(2) . . ?
C11 C8 C9 111.7(3) . . ?
C11 C8 C5 113.2(3) . . ?
C16 C11 C8 120.2(3) . . ?
C16 C11 C12 118.1(3) . . ?
C12 C11 C8 121.8(3) . . ?
C4 C3 S1 128.5(3) . . ?
C2 C3 S1 110.9(3) . . ?
C2 C3 C4 120.6(3) . . ?
C5 C4 C3 119.2(3) . . ?
C4 C5 C8 120.8(3) . . ?
C4 C5 C6 119.6(3) . . ?
C6 C5 C8 119.6(3) . . ?
C15 C16 C11 121.5(3) . . ?
C3 C2 N1 112.5(3) . . ?
C7 C2 N1 126.8(3) . . ?
C7 C2 C3 120.7(3) . . ?
C7 C6 C5 121.4(3) . . ?
O1 C1 S1 123.9(3) . . ?
O1 C1 N1 127.1(3) . . ?
N1 C1 S1 109.1(2) . . ?
C13 C14 Br1 117.6(3) . . ?
C13 C14 C15 122.1(3) . . ?
C15 C14 Br1 120.3(3) . . ?
C6 C7 C2 118.5(3) . . ?
C13 C12 C11 121.2(3) . . ?
C14 C13 C12 118.7(3) . . ?
C14 C15 C16 118.4(3) . . ?

_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_11_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2168918'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 Br N O3 S'
_chemical_formula_sum            'C16 H12 Br N O3 S'
_chemical_formula_weight         378.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   17.2756(7)
_cell_length_b                   5.8934(3)
_cell_length_c                   15.8085(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.614(2)
_cell_angle_gamma                90
_cell_volume                     1534.04(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9129
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.17
_cell_measurement_theta_min      5.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.033
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1133 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.8396.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.160
_diffrn_reflns_theta_min         2.683
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2771
_reflns_number_total             3024
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+1.1439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0793
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00M(H00A,H00C,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br01 Br 0.62995(2) 0.27451(5) 1.00222(2) 0.03787(10) Uani 1 1 d . . . . .
S002 S 0.19582(4) 0.18153(10) 0.50696(4) 0.03498(15) Uani 1 1 d . . . . .
O003 O 0.29360(9) 0.3693(3) 0.65050(10) 0.0310(3) Uani 1 1 d . . . . .
O004 O 0.25631(10) 0.8415(3) 0.76954(12) 0.0329(4) Uani 1 1 d . . . . .
O005 O 0.21003(10) 0.4859(3) 0.77236(11) 0.0334(4) Uani 1 1 d . . . . .
N006 N 0.18254(11) 0.5853(3) 0.56991(12) 0.0276(4) Uani 1 1 d . . . . .
C007 C 0.39574(13) 0.4899(4) 0.77987(14) 0.0251(4) Uani 1 1 d . . . . .
C008 C 0.11644(13) 0.5577(4) 0.49361(14) 0.0273(4) Uani 1 1 d . . . . .
C009 C 0.31915(13) 0.5603(4) 0.70940(14) 0.0267(4) Uani 1 1 d . . . . .
H009 H 0.330221 0.694046 0.675856 0.032 Uiso 1 1 calc R . . . .
C00A C 0.25358(12) 0.6198(4) 0.75274(14) 0.0262(4) Uani 1 1 d . . . . .
C00B C 0.39931(14) 0.2816(4) 0.82259(16) 0.0291(5) Uani 1 1 d . . . . .
H00B H 0.353914 0.182182 0.805827 0.035 Uiso 1 1 calc R . . . .
C00C C 0.53404(13) 0.3657(4) 0.91255(14) 0.0280(4) Uani 1 1 d . . . . .
C00D C 0.53201(13) 0.5738(4) 0.87181(15) 0.0299(5) Uani 1 1 d . . . . .
H00D H 0.577433 0.673006 0.889174 0.036 Uiso 1 1 calc R . . . .
C00E C 0.46215(13) 0.6354(4) 0.80483(14) 0.0281(4) Uani 1 1 d . . . . .
H00E H 0.459809 0.777773 0.775975 0.034 Uiso 1 1 calc R . . . .
C00F C 0.46866(14) 0.2183(4) 0.88940(15) 0.0296(5) Uani 1 1 d . . . . .
H00F H 0.471212 0.076442 0.918685 0.035 Uiso 1 1 calc R . . . .
C00G C 0.11343(14) 0.3493(4) 0.44980(15) 0.0298(5) Uani 1 1 d . . . . .
C00H C 0.05122(15) 0.2975(4) 0.37272(16) 0.0346(5) Uani 1 1 d . . . . .
H00H H 0.049992 0.156401 0.343312 0.041 Uiso 1 1 calc R . . . .
C00I C 0.22597(13) 0.4043(4) 0.58271(14) 0.0282(4) Uani 1 1 d . . . . .
C00J C 0.05537(14) 0.7173(4) 0.45975(16) 0.0312(5) Uani 1 1 d . . . . .
H00J H 0.056293 0.859172 0.488586 0.037 Uiso 1 1 calc R . . . .
C00K C -0.00678(14) 0.6654(4) 0.38322(17) 0.0358(5) Uani 1 1 d . . . . .
H00K H -0.048710 0.773065 0.359671 0.043 Uiso 1 1 calc R . . . .
C00L C -0.00871(15) 0.4587(5) 0.34046(16) 0.0377(6) Uani 1 1 d . . . . .
H00L H -0.051948 0.427310 0.288129 0.045 Uiso 1 1 calc R . . . .
C00M C 0.19887(16) 0.9240(5) 0.8127(2) 0.0424(6) Uani 1 1 d . . . . .
H00A H 0.143468 0.903623 0.773064 0.064 Uiso 1 1 calc GR . . . .
H00C H 0.208806 1.085481 0.826613 0.064 Uiso 1 1 calc GR . . . .
H00G H 0.205477 0.838789 0.867680 0.064 Uiso 1 1 calc GR . . . .


_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
Br01 C00C 1.903(2) . ?
S002 C00G 1.744(2) . ?
S002 C00I 1.747(2) . ?
O003 C009 1.442(3) . ?
O003 C00I 1.341(3) . ?
O004 C00A 1.331(3) . ?
O004 C00M 1.448(3) . ?
O005 C00A 1.194(3) . ?
N006 C008 1.397(3) . ?
N006 C00I 1.284(3) . ?
C007 C009 1.507(3) . ?
C007 C00B 1.393(3) . ?
C007 C00E 1.390(3) . ?
C008 C00G 1.403(3) . ?
C008 C00J 1.394(3) . ?
C009 C00A 1.531(3) . ?
C00B C00F 1.387(3) . ?
C00C C00D 1.381(3) . ?
C00C C00F 1.384(3) . ?
C00D C00E 1.391(3) . ?
C00G C00H 1.393(3) . ?
C00H C00L 1.383(4) . ?
C00J C00K 1.387(4) . ?
C00K C00L 1.389(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
C00G S002 C00I 87.50(11) . . ?
C00I O003 C009 114.74(17) . . ?
C00A O004 C00M 115.83(18) . . ?
C00I N006 C008 108.99(19) . . ?
C00B C007 C009 120.07(19) . . ?
C00E C007 C009 120.28(19) . . ?
C00E C007 C00B 119.6(2) . . ?
N006 C008 C00G 115.2(2) . . ?
C00J C008 N006 125.4(2) . . ?
C00J C008 C00G 119.4(2) . . ?
O003 C009 C007 106.91(17) . . ?
O003 C009 C00A 110.13(17) . . ?
C007 C009 C00A 109.57(17) . . ?
O004 C00A C009 109.12(17) . . ?
O005 C00A O004 125.7(2) . . ?
O005 C00A C009 125.1(2) . . ?
C00F C00B C007 120.5(2) . . ?
C00D C00C Br01 119.45(17) . . ?
C00D C00C C00F 122.1(2) . . ?
C00F C00C Br01 118.48(18) . . ?
C00C C00D C00E 118.7(2) . . ?
C007 C00E C00D 120.4(2) . . ?
C00C C00F C00B 118.7(2) . . ?
C008 C00G S002 109.75(17) . . ?
C00H C00G S002 128.44(19) . . ?
C00H C00G C008 121.8(2) . . ?
C00L C00H C00G 117.7(2) . . ?
O003 C00I S002 116.07(16) . . ?
N006 C00I S002 118.51(17) . . ?
N006 C00I O003 125.4(2) . . ?
C00K C00J C008 118.8(2) . . ?
C00J C00K C00L 121.1(2) . . ?
C00H C00L C00K 121.2(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_11_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2168917'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Br Cl N O3 S'
_chemical_formula_sum            'C16 H11 Br Cl N O3 S'
_chemical_formula_weight         412.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.1958(3)
_cell_length_b                   15.7734(5)
_cell_length_c                   9.1550(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.1360(10)
_cell_angle_gamma                90
_cell_volume                     1607.47(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.57
_cell_measurement_theta_min      3.97
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.355
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6268
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8317.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29115
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.561
_diffrn_reflns_theta_min         3.971
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2894
_reflns_number_total             3180
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+0.6734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0607
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C13(H13), C12(H12), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br1 Br 0.27928(2) 0.75492(2) 1.14519(2) 0.02219(7) Uani 1 1 d . . . . .
Cl1 Cl 0.13321(4) 0.56051(3) 0.42301(5) 0.02221(11) Uani 1 1 d . . . . .
S1 S 0.47322(4) 0.32975(3) 0.58425(5) 0.02044(11) Uani 1 1 d . . . . .
O1 O 0.38566(11) 0.35622(9) 0.83865(13) 0.0194(3) Uani 1 1 d . . . . .
O3 O 0.14150(12) 0.30801(8) 0.71190(14) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.11625(12) 0.37990(8) 0.91904(14) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.29613(13) 0.42755(10) 0.63702(15) 0.0152(3) Uani 1 1 d . . . . .
C6 C 0.30140(15) 0.43348(11) 0.48452(19) 0.0148(3) Uani 1 1 d . . . . .
C14 C 0.25547(16) 0.66411(11) 1.00855(18) 0.0161(3) Uani 1 1 d . . . . .
C15 C 0.35415(16) 0.62351(11) 0.96184(19) 0.0168(3) Uani 1 1 d . . . . .
H15 H 0.433343 0.641585 0.995099 0.020 Uiso 1 1 calc R . . . .
C16 C 0.33490(16) 0.55563(11) 0.86513(19) 0.0157(3) Uani 1 1 d . . . . .
H16 H 0.401812 0.527272 0.831926 0.019 Uiso 1 1 calc R . . . .
C9 C 0.14870(15) 0.37659(11) 0.79908(19) 0.0164(3) Uani 1 1 d . . . . .
C13 C 0.13915(16) 0.63974(12) 0.95993(19) 0.0174(4) Uani 1 1 d . . . . .
H13 H 0.072495 0.669140 0.991648 0.021 Uiso 1 1 calc R . . . .
C11 C 0.21926(16) 0.52867(11) 0.81633(18) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.19478(15) 0.45298(11) 0.71616(18) 0.0148(3) Uani 1 1 d . . . . .
H8 H 0.128231 0.469779 0.640047 0.018 Uiso 1 1 calc R . . . .
C12 C 0.12167(16) 0.57179(11) 0.86429(19) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.042257 0.554251 0.830844 0.021 Uiso 1 1 calc R . . . .
C7 C 0.37987(16) 0.37297(11) 0.70876(19) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.25163(17) 0.47409(12) 0.2313(2) 0.0196(4) Uani 1 1 d . . . . .
H2 H 0.204294 0.506790 0.159652 0.024 Uiso 1 1 calc R . . . .
C4 C 0.40881(17) 0.37208(12) 0.2904(2) 0.0209(4) Uani 1 1 d . . . . .
H4 H 0.469326 0.335339 0.261555 0.025 Uiso 1 1 calc R . . . .
C5 C 0.39060(16) 0.38081(12) 0.4372(2) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.33649(18) 0.41831(13) 0.1867(2) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.345040 0.411798 0.085231 0.027 Uiso 1 1 calc R . . . .
C1 C 0.23460(16) 0.48301(11) 0.3785(2) 0.0167(3) Uani 1 1 d . . . . .
C10 C 0.1017(2) 0.23137(13) 0.7790(3) 0.0276(4) Uani 1 1 d . . . . .
H10A H 0.109964 0.183180 0.713289 0.041 Uiso 1 1 calc GR . . . .
H10B H 0.017277 0.237488 0.796568 0.041 Uiso 1 1 calc GR . . . .
H10C H 0.150827 0.221559 0.872628 0.041 Uiso 1 1 calc GR . . . .


_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
Br1 C14 1.9017(17) . ?
Cl1 C1 1.7457(19) . ?
S1 C7 1.7638(18) . ?
S1 C5 1.7467(18) . ?
O1 C7 1.213(2) . ?
O3 C9 1.342(2) . ?
O3 C10 1.448(2) . ?
O2 C9 1.194(2) . ?
N1 C6 1.407(2) . ?
N1 C8 1.466(2) . ?
N1 C7 1.386(2) . ?
C6 C5 1.403(3) . ?
C6 C1 1.399(2) . ?
C14 C15 1.384(3) . ?
C14 C13 1.385(3) . ?
C15 C16 1.391(3) . ?
C16 C11 1.390(2) . ?
C9 C8 1.542(2) . ?
C13 C12 1.385(3) . ?
C11 C8 1.513(2) . ?
C11 C12 1.397(2) . ?
C2 C3 1.388(3) . ?
C2 C1 1.389(3) . ?
C4 C5 1.388(3) . ?
C4 C3 1.387(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
C5 S1 C7 91.06(8) . . ?
C9 O3 C10 114.99(15) . . ?
C6 N1 C8 126.09(14) . . ?
C7 N1 C6 114.44(14) . . ?
C7 N1 C8 117.12(14) . . ?
C5 C6 N1 111.96(15) . . ?
C1 C6 N1 130.51(16) . . ?
C1 C6 C5 117.52(16) . . ?
C15 C14 Br1 119.44(13) . . ?
C15 C14 C13 121.78(16) . . ?
C13 C14 Br1 118.78(13) . . ?
C14 C15 C16 118.58(16) . . ?
C11 C16 C15 121.03(16) . . ?
O3 C9 C8 109.83(14) . . ?
O2 C9 O3 125.28(17) . . ?
O2 C9 C8 124.70(16) . . ?
C12 C13 C14 118.85(17) . . ?
C16 C11 C8 122.58(16) . . ?
C16 C11 C12 118.86(16) . . ?
C12 C11 C8 118.54(15) . . ?
N1 C8 C9 110.30(14) . . ?
N1 C8 C11 114.58(14) . . ?
C11 C8 C9 111.52(14) . . ?
C13 C12 C11 120.88(16) . . ?
O1 C7 S1 125.17(14) . . ?
O1 C7 N1 124.23(16) . . ?
N1 C7 S1 110.58(12) . . ?
C3 C2 C1 121.25(17) . . ?
C3 C4 C5 118.35(17) . . ?
C6 C5 S1 111.75(13) . . ?
C4 C5 S1 125.48(15) . . ?
C4 C5 C6 122.77(17) . . ?
C4 C3 C2 120.04(17) . . ?
C6 C1 Cl1 122.83(14) . . ?
C2 C1 Cl1 117.23(14) . . ?
C2 C1 C6 119.87(17) . . ?

_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_11_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2168921'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O6 S'
_chemical_formula_sum            'C18 H15 N O6 S'
_chemical_formula_weight         373.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3619(3)
_cell_length_b                   8.0345(3)
_cell_length_c                   13.9973(5)
_cell_angle_alpha                90.6280(10)
_cell_angle_beta                 94.4890(10)
_cell_angle_gamma                101.8900(10)
_cell_volume                     807.37(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.09
_cell_measurement_theta_min      3.17
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6477
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1238 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8606.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24386
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        65.125
_diffrn_reflns_theta_max         65.125
_diffrn_reflns_theta_min         3.168
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2655
_reflns_number_total             2752
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+0.5059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C2(H2), C7(H7), C13(H13), C17(H17), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72825(5) 0.55194(5) 0.81143(3) 0.02410(13) Uani 1 1 d . . . . .
O1 O 0.16506(15) 0.15970(14) 0.95871(8) 0.0244(3) Uani 1 1 d . . . . .
O4 O 0.97168(15) 0.92548(14) 0.81239(8) 0.0258(3) Uani 1 1 d . . . . .
H4 H 0.963043 1.010325 0.845999 0.039 Uiso 1 1 calc GR . . . .
O2 O 0.61811(16) 1.03688(14) 0.65311(8) 0.0275(3) Uani 1 1 d . . . . .
O3 O 0.76197(17) 1.15646(14) 0.79201(8) 0.0290(3) Uani 1 1 d . . . . .
O6 O 0.73081(18) 0.57784(17) 0.42547(9) 0.0375(3) Uani 1 1 d . . . . .
O5 O 1.0402(2) 0.66937(19) 0.39655(9) 0.0425(3) Uani 1 1 d . . . . .
N1 N 0.50575(18) 0.76488(16) 0.80379(9) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.4115(2) 0.61711(19) 0.84416(11) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.6698(2) 0.74662(19) 0.78417(11) 0.0202(3) Uani 1 1 d . . . . .
C5 C 0.5114(2) 0.4864(2) 0.85454(11) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.4376(2) 0.3299(2) 0.89332(11) 0.0214(3) Uani 1 1 d . . . . .
H4A H 0.507552 0.243129 0.900389 0.026 Uiso 1 1 calc R . . . .
C2 C 0.1552(2) 0.4361(2) 0.91081(11) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.031828 0.416494 0.930042 0.028 Uiso 1 1 calc R . . . .
C7 C 0.2302(2) 0.5902(2) 0.87352(11) 0.0238(3) Uani 1 1 d . . . . .
H7 H 0.160299 0.677221 0.867723 0.029 Uiso 1 1 calc R . . . .
C11 C 0.8158(2) 0.88496(19) 0.74389(11) 0.0217(3) Uani 1 1 d . . . . .
C13 C 0.7547(2) 0.7233(2) 0.58316(11) 0.0244(3) Uani 1 1 d . . . . .
H13 H 0.627274 0.685759 0.594222 0.029 Uiso 1 1 calc R . . . .
C3 C 0.2578(2) 0.3070(2) 0.92100(11) 0.0210(3) Uani 1 1 d . . . . .
C12 C 0.8812(2) 0.82674(19) 0.65075(11) 0.0216(3) Uani 1 1 d . . . . .
C10 C 0.7290(2) 1.0435(2) 0.73243(11) 0.0224(3) Uani 1 1 d . . . . .
C14 C 0.8235(2) 0.6792(2) 0.50104(12) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.2676(2) 0.0288(2) 0.97609(12) 0.0258(4) Uani 1 1 d . . . . .
H1A H 0.311164 -0.004811 0.915811 0.039 Uiso 1 1 calc GR . . . .
H1B H 0.187147 -0.069909 1.002251 0.039 Uiso 1 1 calc GR . . . .
H1C H 0.374954 0.071173 1.022146 0.039 Uiso 1 1 calc GR . . . .
C15 C 1.0083(3) 0.7335(2) 0.48369(12) 0.0304(4) Uani 1 1 d . . . . .
C17 C 1.0670(2) 0.8780(2) 0.63352(13) 0.0302(4) Uani 1 1 d . . . . .
H17 H 1.150723 0.946563 0.680374 0.036 Uiso 1 1 calc R . . . .
C9 C 0.5269(2) 1.1798(2) 0.64072(13) 0.0305(4) Uani 1 1 d . . . . .
H9A H 0.446152 1.163342 0.580858 0.046 Uiso 1 1 calc GR . . . .
H9B H 0.621175 1.285006 0.638158 0.046 Uiso 1 1 calc GR . . . .
H9C H 0.451850 1.187527 0.694767 0.046 Uiso 1 1 calc GR . . . .
C18 C 0.8635(3) 0.5854(3) 0.35465(13) 0.0380(4) Uani 1 1 d . . . . .
H18A H 0.868532 0.469000 0.332726 0.046 Uiso 1 1 calc R . . . .
H18B H 0.826169 0.648286 0.298518 0.046 Uiso 1 1 calc R . . . .
C16 C 1.1340(3) 0.8308(2) 0.54861(14) 0.0363(4) Uani 1 1 d . . . . .
H16 H 1.261487 0.865242 0.536861 0.044 Uiso 1 1 calc R . . . .


_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 C8 1.7442(15) . ?
S1 C5 1.7325(16) . ?
O1 C3 1.3719(19) . ?
O1 C1 1.4284(19) . ?
O4 C11 1.4172(19) . ?
O2 C10 1.319(2) . ?
O2 C9 1.4499(19) . ?
O3 C10 1.199(2) . ?
O6 C14 1.374(2) . ?
O6 C18 1.438(2) . ?
O5 C15 1.374(2) . ?
O5 C18 1.414(2) . ?
N1 C6 1.395(2) . ?
N1 C8 1.296(2) . ?
C6 C5 1.403(2) . ?
C6 C7 1.402(2) . ?
C8 C11 1.525(2) . ?
C5 C4 1.397(2) . ?
C4 C3 1.385(2) . ?
C2 C7 1.374(2) . ?
C2 C3 1.406(2) . ?
C11 C12 1.526(2) . ?
C11 C10 1.543(2) . ?
C13 C12 1.407(2) . ?
C13 C14 1.363(2) . ?
C12 C17 1.386(2) . ?
C14 C15 1.381(3) . ?
C15 C16 1.360(3) . ?
C17 C16 1.399(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
C5 S1 C8 88.83(7) . . ?
C3 O1 C1 116.86(12) . . ?
C10 O2 C9 115.02(13) . . ?
C14 O6 C18 105.39(14) . . ?
C15 O5 C18 105.71(14) . . ?
C8 N1 C6 109.90(13) . . ?
N1 C6 C5 115.15(13) . . ?
N1 C6 C7 125.82(14) . . ?
C7 C6 C5 119.02(14) . . ?
N1 C8 S1 116.70(12) . . ?
N1 C8 C11 124.70(14) . . ?
C11 C8 S1 118.53(11) . . ?
C6 C5 S1 109.42(12) . . ?
C4 C5 S1 127.97(12) . . ?
C4 C5 C6 122.61(14) . . ?
C3 C4 C5 116.93(14) . . ?
C7 C2 C3 121.19(14) . . ?
C2 C7 C6 118.95(14) . . ?
O4 C11 C8 108.35(12) . . ?
O4 C11 C12 108.37(12) . . ?
O4 C11 C10 108.15(12) . . ?
C8 C11 C12 111.95(12) . . ?
C8 C11 C10 106.76(12) . . ?
C12 C11 C10 113.11(12) . . ?
C14 C13 C12 116.93(15) . . ?
O1 C3 C4 123.85(14) . . ?
O1 C3 C2 114.85(13) . . ?
C4 C3 C2 121.29(14) . . ?
C13 C12 C11 120.57(14) . . ?
C17 C12 C11 118.98(14) . . ?
C17 C12 C13 120.46(15) . . ?
O2 C10 C11 112.79(13) . . ?
O3 C10 O2 126.07(15) . . ?
O3 C10 C11 121.14(14) . . ?
O6 C14 C15 109.53(14) . . ?
C13 C14 O6 128.25(16) . . ?
C13 C14 C15 122.22(16) . . ?
O5 C15 C14 110.11(16) . . ?
C16 C15 O5 127.84(17) . . ?
C16 C15 C14 122.00(16) . . ?
C12 C17 C16 121.43(16) . . ?
O5 C18 O6 108.37(14) . . ?
C15 C16 C17 116.94(16) . . ?

_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_11_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2168919'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Br N2 O5 S'
_chemical_formula_sum            'C16 H11 Br N2 O5 S'
_chemical_formula_weight         423.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.6509(6)
_cell_length_b                   18.0112(13)
_cell_length_c                   10.3592(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.201(2)
_cell_angle_gamma                90
_cell_volume                     1604.66(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9494
_cell_measurement_temperature    227(2)
_cell_measurement_theta_max      72.73
_cell_measurement_theta_min      4.91
_shelx_estimated_absorpt_T_max   0.690
_shelx_estimated_absorpt_T_min   0.434
_exptl_absorpt_coefficient_mu    5.006
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6292
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1082 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.8349.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35227
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.723
_diffrn_reflns_theta_min         4.911
_diffrn_ambient_temperature      227.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3110
_reflns_number_total             3183
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.385
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+2.5869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00L(H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00I(H00I), C00K(H00K), C00M(H00M), C00N(H00N),
 C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br01 Br 0.89267(3) 0.22100(2) 0.83489(3) 0.04330(12) Uani 1 1 d . . . . .
S002 S 0.21646(7) 0.52293(3) 0.40214(6) 0.02866(15) Uani 1 1 d . . . . .
O003 O 0.2979(2) 0.42758(12) 0.97060(18) 0.0395(4) Uani 1 1 d . . . . .
O004 O 0.4148(2) 0.57499(10) 0.59460(19) 0.0384(4) Uani 1 1 d . . . . .
O005 O -0.2111(2) 0.23780(11) 0.3901(2) 0.0415(5) Uani 1 1 d . . . . .
O006 O 0.1083(2) 0.46903(13) 0.8268(2) 0.0462(5) Uani 1 1 d . . . . .
N007 N 0.2932(2) 0.46381(11) 0.62829(19) 0.0252(4) Uani 1 1 d . . . . .
O008 O -0.2005(3) 0.31391(13) 0.2302(2) 0.0499(5) Uani 1 1 d . . . . .
N009 N -0.1574(3) 0.29273(13) 0.3401(2) 0.0339(5) Uani 1 1 d . . . . .
C00A C 0.1292(3) 0.43988(13) 0.4409(2) 0.0242(5) Uani 1 1 d . . . . .
C00B C 0.2406(3) 0.45097(13) 0.8547(2) 0.0281(5) Uani 1 1 d . . . . .
C00C C 0.3260(3) 0.52591(14) 0.5568(2) 0.0285(5) Uani 1 1 d . . . . .
C00D C 0.0178(3) 0.39980(14) 0.3644(2) 0.0268(5) Uani 1 1 d . . . . .
H00D H -0.020426 0.415789 0.280647 0.032 Uiso 1 1 calc R . . . .
C00E C 0.1841(3) 0.41509(13) 0.5658(2) 0.0239(5) Uani 1 1 d . . . . .
C00F C -0.0351(3) 0.33486(14) 0.4171(2) 0.0273(5) Uani 1 1 d . . . . .
C00G C 0.1318(3) 0.34901(13) 0.6146(2) 0.0272(5) Uani 1 1 d . . . . .
H00G H 0.171088 0.332081 0.697571 0.033 Uiso 1 1 calc R . . . .
C00H C 0.4952(3) 0.39786(13) 0.7767(2) 0.0258(5) Uani 1 1 d . . . . .
C00I C 0.6389(3) 0.29645(15) 0.6941(3) 0.0305(5) Uani 1 1 d . . . . .
H00I H 0.654315 0.263107 0.626847 0.037 Uiso 1 1 calc R . . . .
C00J C 0.7345(3) 0.29467(15) 0.8092(3) 0.0320(5) Uani 1 1 d . . . . .
C00K C 0.5193(3) 0.34825(14) 0.6787(2) 0.0266(5) Uani 1 1 d . . . . .
H00K H 0.453593 0.349652 0.600316 0.032 Uiso 1 1 calc R . . . .
C00L C 0.3670(3) 0.45663(13) 0.7610(2) 0.0269(5) Uani 1 1 d . . . . .
H00L H 0.419946 0.504619 0.781241 0.032 Uiso 1 1 calc R . . . .
C00M C 0.0206(3) 0.30861(14) 0.5385(2) 0.0284(5) Uani 1 1 d . . . . .
H00M H -0.016686 0.263641 0.569183 0.034 Uiso 1 1 calc R . . . .
C00N C 0.5971(3) 0.39591(17) 0.8908(3) 0.0351(6) Uani 1 1 d . . . . .
H00N H 0.584151 0.430064 0.957404 0.042 Uiso 1 1 calc R . . . .
C00O C 0.7164(3) 0.34475(18) 0.9076(3) 0.0384(6) Uani 1 1 d . . . . .
H00O H 0.784250 0.343968 0.984837 0.046 Uiso 1 1 calc R . . . .
C00P C 0.1881(4) 0.4219(2) 1.0665(3) 0.0541(9) Uani 1 1 d . . . . .
H00A H 0.107859 0.386208 1.037428 0.081 Uiso 1 1 calc GR . . . .
H00B H 0.140881 0.470046 1.077573 0.081 Uiso 1 1 calc GR . . . .
H00C H 0.241978 0.405752 1.148662 0.081 Uiso 1 1 calc GR . . . .


_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
Br01 C00J 1.904(3) . ?
S002 C00A 1.742(2) . ?
S002 C00C 1.772(3) . ?
O003 C00B 1.318(3) . ?
O003 C00P 1.451(3) . ?
O004 C00C 1.208(3) . ?
O005 N009 1.231(3) . ?
O006 C00B 1.195(3) . ?
N007 C00C 1.388(3) . ?
N007 C00E 1.395(3) . ?
N007 C00L 1.457(3) . ?
O008 N009 1.220(3) . ?
N009 C00F 1.465(3) . ?
C00A C00D 1.383(3) . ?
C00A C00E 1.403(3) . ?
C00B C00L 1.542(3) . ?
C00D C00F 1.389(4) . ?
C00E C00G 1.388(3) . ?
C00F C00M 1.381(4) . ?
C00G C00M 1.383(3) . ?
C00H C00K 1.385(3) . ?
C00H C00L 1.529(3) . ?
C00H C00N 1.397(3) . ?
C00I C00J 1.376(4) . ?
C00I C00K 1.389(4) . ?
C00J C00O 1.383(4) . ?
C00N C00O 1.380(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
C00A S002 C00C 91.19(11) . . ?
C00B O003 C00P 115.9(2) . . ?
C00C N007 C00E 115.3(2) . . ?
C00C N007 C00L 118.7(2) . . ?
C00E N007 C00L 125.9(2) . . ?
O005 N009 C00F 118.1(2) . . ?
O008 N009 O005 123.5(2) . . ?
O008 N009 C00F 118.4(2) . . ?
C00D C00A S002 127.53(18) . . ?
C00D C00A C00E 120.5(2) . . ?
C00E C00A S002 111.94(18) . . ?
O003 C00B C00L 111.8(2) . . ?
O006 C00B O003 124.4(2) . . ?
O006 C00B C00L 123.7(2) . . ?
O004 C00C S002 125.1(2) . . ?
O004 C00C N007 125.2(2) . . ?
N007 C00C S002 109.74(17) . . ?
C00A C00D C00F 117.0(2) . . ?
N007 C00E C00A 111.9(2) . . ?
C00G C00E N007 127.0(2) . . ?
C00G C00E C00A 121.2(2) . . ?
C00D C00F N009 118.1(2) . . ?
C00M C00F N009 118.6(2) . . ?
C00M C00F C00D 123.3(2) . . ?
C00M C00G C00E 118.5(2) . . ?
C00K C00H C00L 122.3(2) . . ?
C00K C00H C00N 118.2(2) . . ?
C00N C00H C00L 119.4(2) . . ?
C00J C00I C00K 119.0(2) . . ?
C00I C00J Br01 119.5(2) . . ?
C00I C00J C00O 121.2(2) . . ?
C00O C00J Br01 119.3(2) . . ?
C00H C00K C00I 121.2(2) . . ?
N007 C00L C00B 109.36(19) . . ?
N007 C00L C00H 113.59(19) . . ?
C00H C00L C00B 116.3(2) . . ?
C00F C00M C00G 119.5(2) . . ?
C00O C00N C00H 121.2(2) . . ?
C00N C00O C00J 119.0(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_11_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2168922'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H5 B F15 N O S)'
_chemical_formula_sum            'C50 H10 B2 F30 N2 O2 S2'
_chemical_formula_weight         1326.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.9957(5)
_cell_length_b                   20.7143(7)
_cell_length_c                   16.4103(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.911(2)
_cell_angle_gamma                90
_cell_volume                     4756.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9120
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.44
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.685
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5913
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0818 after correction.
The Ratio of minimum to maximum transmission is 0.7852.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            92990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.374
_diffrn_reflns_theta_min         3.436
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7336
_reflns_number_total             8693
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     793
_refine_ls_number_reflns         8693
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+1.3067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N00Z(H00Z), N1(H1), C01W(H01W), C024(H024), C22(H22), C24(H24), C21(H21),
 C23(H23), C02D(H02D), C02E(H02E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S001 S 0.60613(3) 0.35594(2) 0.81348(2) 0.03177(10) Uani 1 1 d . . . . .
S1 S 0.67238(3) 0.35134(2) 0.27424(2) 0.03345(11) Uani 1 1 d . . . . .
F7 F 0.47292(8) 0.48618(5) 0.13536(6) 0.0338(2) Uani 1 1 d . . . . .
F6 F 0.43322(8) 0.41238(5) 0.26437(6) 0.0333(2) Uani 1 1 d . . . . .
F1 F 0.39513(7) 0.24457(5) 0.44397(6) 0.0321(2) Uani 1 1 d . . . . .
F8 F 0.53977(8) 0.43103(5) -0.00341(6) 0.0356(2) Uani 1 1 d . . . . .
F10 F 0.53406(8) 0.22777(5) 0.11828(6) 0.0364(2) Uani 1 1 d . . . . .
F11 F 0.35271(8) 0.18945(5) 0.18115(6) 0.0382(2) Uani 1 1 d . . . . .
F009 F 0.29815(8) 0.25371(5) 0.67867(6) 0.0378(2) Uani 1 1 d . . . . .
F2 F 0.22911(8) 0.26869(5) 0.51150(6) 0.0359(2) Uani 1 1 d . . . . .
F00B F 0.36087(8) 0.47736(5) 0.75829(6) 0.0383(2) Uani 1 1 d . . . . .
F5 F 0.27681(8) 0.32799(6) 0.19282(6) 0.0371(2) Uani 1 1 d . . . . .
F00D F 0.41036(9) 0.25586(5) 0.81858(6) 0.0388(2) Uani 1 1 d . . . . .
F9 F 0.56589(8) 0.30229(5) -0.01044(6) 0.0367(2) Uani 1 1 d . . . . .
F00F F 0.21058(8) 0.38047(6) 0.69707(6) 0.0397(2) Uani 1 1 d . . . . .
F3 F 0.08226(7) 0.32160(6) 0.42136(7) 0.0403(2) Uani 1 1 d . . . . .
F00H F 0.61480(8) 0.31354(6) 0.61375(7) 0.0435(3) Uani 1 1 d . . . . .
F4 F 0.10932(8) 0.34925(6) 0.26130(7) 0.0421(3) Uani 1 1 d . . . . .
F15 F 0.60329(8) 0.19561(5) 0.37850(7) 0.0439(3) Uani 1 1 d . . . . .
F00K F 0.47636(9) 0.40209(6) 0.52317(6) 0.0430(3) Uani 1 1 d . . . . .
F12 F 0.37396(10) 0.06160(5) 0.16950(7) 0.0470(3) Uani 1 1 d . . . . .
O1 O 0.51621(8) 0.30764(6) 0.35276(6) 0.0265(2) Uani 1 1 d . . . . .
F00N F 0.34458(10) 0.27528(6) 0.96712(6) 0.0477(3) Uani 1 1 d . . . . .
F00O F 0.09712(8) 0.42518(6) 0.58017(8) 0.0480(3) Uani 1 1 d . . . . .
F00P F 0.30230(9) 0.49644(6) 0.90978(7) 0.0472(3) Uani 1 1 d . . . . .
F13 F 0.50460(10) -0.00099(5) 0.26606(8) 0.0507(3) Uani 1 1 d . . . . .
O00R O 0.51272(9) 0.40660(6) 0.68275(7) 0.0294(3) Uani 1 1 d . . . . .
F00S F 0.16981(10) 0.46058(6) 0.43332(7) 0.0530(3) Uani 1 1 d . . . . .
F00T F 0.29235(9) 0.39564(7) 1.01623(7) 0.0503(3) Uani 1 1 d . . . . .
F14 F 0.61524(9) 0.06793(6) 0.37202(9) 0.0539(3) Uani 1 1 d . . . . .
F00V F 0.32873(11) 0.13642(6) 0.61666(8) 0.0534(3) Uani 1 1 d . . . . .
F00W F 0.36052(11) 0.44976(7) 0.40805(7) 0.0566(4) Uani 1 1 d . . . . .
F00X F 0.64353(10) 0.19745(8) 0.55348(8) 0.0622(4) Uani 1 1 d . . . . .
F00Y F 0.50222(12) 0.10673(7) 0.55292(10) 0.0696(5) Uani 1 1 d . . . . .
N00Z N 0.64387(11) 0.45702(7) 0.73253(9) 0.0291(3) Uani 1 1 d . . . . .
H00Z H 0.643808 0.485909 0.693214 0.035 Uiso 1 1 calc R . . . .
N1 N 0.64341(11) 0.34172(8) 0.42613(8) 0.0312(3) Uani 1 1 d . . . . .
H1 H 0.615637 0.333727 0.472797 0.037 Uiso 1 1 calc R . . . .
C1 C 0.34736(12) 0.28740(8) 0.31532(9) 0.0239(3) Uani 1 1 d . . . . .
C9 C 0.48670(12) 0.42208(8) 0.13172(10) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.32716(12) 0.27178(8) 0.39601(10) 0.0253(3) Uani 1 1 d . . . . .
C13 C 0.47702(12) 0.19935(8) 0.27966(9) 0.0259(3) Uani 1 1 d . . . . .
C7 C 0.47977(12) 0.31612(8) 0.19848(9) 0.0249(3) Uani 1 1 d . . . . .
C10 C 0.52116(12) 0.39460(8) 0.06144(9) 0.0267(3) Uani 1 1 d . . . . .
C8 C 0.46695(12) 0.38265(8) 0.19668(9) 0.0252(3) Uani 1 1 d . . . . .
C12 C 0.51564(12) 0.29105(8) 0.12629(10) 0.0269(3) Uani 1 1 d . . . . .
C019 C 0.38582(12) 0.36521(8) 0.77907(10) 0.0267(3) Uani 1 1 d . . . . .
C01A C 0.58134(12) 0.40918(8) 0.73446(10) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.24028(13) 0.28259(8) 0.43230(10) 0.0279(3) Uani 1 1 d . . . . .
C25 C 0.73545(12) 0.36750(8) 0.42229(10) 0.0285(3) Uani 1 1 d . . . . .
C01D C 0.35074(13) 0.39093(8) 0.61802(10) 0.0282(3) Uani 1 1 d . . . . .
C4 C 0.16619(12) 0.30912(8) 0.38714(11) 0.0292(3) Uani 1 1 d . . . . .
C11 C 0.53470(12) 0.32899(9) 0.05900(9) 0.0281(3) Uani 1 1 d . . . . .
C01G C 0.70036(12) 0.40527(8) 0.84760(10) 0.0287(3) Uani 1 1 d . . . . .
C19 C 0.60043(12) 0.33001(8) 0.35483(9) 0.0248(3) Uani 1 1 d . . . . .
C14 C 0.42014(13) 0.16111(8) 0.22896(10) 0.0296(4) Uani 1 1 d . . . . .
C01J C 0.45504(13) 0.28884(9) 0.65322(9) 0.0293(4) Uani 1 1 d . . . . .
C01K C 0.70995(12) 0.45854(8) 0.79709(10) 0.0294(3) Uani 1 1 d . . . . .
C6 C 0.26940(13) 0.31228(8) 0.27203(10) 0.0283(3) Uani 1 1 d . . . . .
C01M C 0.38583(14) 0.24093(9) 0.65002(10) 0.0326(4) Uani 1 1 d . . . . .
C01N C 0.38047(13) 0.31613(9) 0.83636(10) 0.0301(4) Uani 1 1 d . . . . .
C5 C 0.18093(12) 0.32320(8) 0.30612(11) 0.0301(4) Uani 1 1 d . . . . .
C18 C 0.54281(12) 0.16490(9) 0.32662(11) 0.0303(4) Uani 1 1 d . . . . .
C20 C 0.76291(12) 0.37647(8) 0.34248(10) 0.0291(3) Uani 1 1 d . . . . .
C01R C 0.34826(13) 0.32530(10) 0.91498(10) 0.0348(4) Uani 1 1 d . . . . .
C01S C 0.38287(14) 0.40896(9) 0.54163(10) 0.0321(4) Uani 1 1 d . . . . .
C01T C 0.35825(12) 0.42541(8) 0.80820(10) 0.0294(3) Uani 1 1 d . . . . .
C01U C 0.25263(13) 0.39756(9) 0.62721(10) 0.0310(4) Uani 1 1 d . . . . .
C01V C 0.19147(14) 0.42083(9) 0.56703(12) 0.0361(4) Uani 1 1 d . . . . .
C01W C 0.75611(14) 0.39888(10) 0.91780(11) 0.0364(4) Uani 1 1 d . . . . .
H01W H 0.750123 0.362300 0.952269 0.044 Uiso 1 1 calc R . . . .
C15 C 0.42904(14) 0.09515(9) 0.22248(10) 0.0340(4) Uani 1 1 d . . . . .
C01Y C 0.54099(14) 0.27097(10) 0.61874(10) 0.0345(4) Uani 1 1 d . . . . .
C16 C 0.49510(14) 0.06344(9) 0.27058(12) 0.0364(4) Uani 1 1 d . . . . .
C17 C 0.55174(13) 0.09855(9) 0.32372(12) 0.0353(4) Uani 1 1 d . . . . .
C021 C 0.32407(16) 0.43333(9) 0.48083(10) 0.0388(4) Uani 1 1 d . . . . .
C022 C 0.32728(13) 0.43659(9) 0.88625(11) 0.0344(4) Uani 1 1 d . . . . .
C023 C 0.32191(13) 0.38581(10) 0.94012(10) 0.0360(4) Uani 1 1 d . . . . .
C024 C 0.77465(14) 0.50717(9) 0.81495(13) 0.0392(4) Uani 1 1 d . . . . .
H024 H 0.781212 0.543527 0.780200 0.047 Uiso 1 1 calc R . . . .
C025 C 0.22772(16) 0.43911(9) 0.49321(12) 0.0392(4) Uani 1 1 d . . . . .
C22 C 0.91181(13) 0.41796(9) 0.38878(12) 0.0364(4) Uani 1 1 d . . . . .
H22 H 0.972864 0.435891 0.378288 0.044 Uiso 1 1 calc R . . . .
C24 C 0.79570(14) 0.38300(10) 0.48719(11) 0.0389(4) Uani 1 1 d . . . . .
H24 H 0.776760 0.376856 0.541982 0.047 Uiso 1 1 calc R . . . .
C21 C 0.85157(13) 0.40242(10) 0.32429(12) 0.0371(4) Uani 1 1 d . . . . .
H21 H 0.870061 0.409229 0.269504 0.045 Uiso 1 1 calc R . . . .
C029 C 0.39964(17) 0.18026(9) 0.61788(11) 0.0408(5) Uani 1 1 d . . . . .
C02A C 0.55833(15) 0.21076(11) 0.58564(11) 0.0433(5) Uani 1 1 d . . . . .
C23 C 0.88447(14) 0.40775(10) 0.46889(12) 0.0389(4) Uani 1 1 d . . . . .
H23 H 0.927877 0.418050 0.512045 0.047 Uiso 1 1 calc R . . . .
C02C C 0.48734(18) 0.16507(10) 0.58537(12) 0.0462(5) Uani 1 1 d . . . . .
C02D C 0.82928(15) 0.50083(10) 0.88520(14) 0.0441(5) Uani 1 1 d . . . . .
H02D H 0.873917 0.533698 0.899267 0.053 Uiso 1 1 calc R . . . .
C02E C 0.82053(15) 0.44743(11) 0.93589(12) 0.0425(5) Uani 1 1 d . . . . .
H02E H 0.859480 0.444328 0.983667 0.051 Uiso 1 1 calc R . . . .
B1 B 0.45621(14) 0.27684(9) 0.28214(11) 0.0248(4) Uani 1 1 d . . . . .
B02G B 0.42501(14) 0.36037(10) 0.68611(11) 0.0274(4) 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
S001 C01A 1.7331(16) . ?
S001 C01G 1.7531(18) . ?
S1 C19 1.7322(17) . ?
S1 C20 1.7565(17) . ?
F7 C9 1.3432(19) . ?
F6 C8 1.3611(18) . ?
F1 C2 1.3484(19) . ?
F8 C10 1.3336(18) . ?
F10 C12 1.343(2) . ?
F11 C14 1.352(2) . ?
F009 C01M 1.347(2) . ?
F2 C3 1.3429(19) . ?
F00B C01T 1.353(2) . ?
F5 C6 1.3456(19) . ?
F00D C01N 1.350(2) . ?
F9 C11 1.3456(19) . ?
F00F C01U 1.344(2) . ?
F3 C4 1.335(2) . ?
F00H C01Y 1.362(2) . ?
F4 C5 1.347(2) . ?
F15 C18 1.350(2) . ?
F00K C01S 1.355(2) . ?
F12 C15 1.346(2) . ?
O1 C19 1.267(2) . ?
O1 B1 1.557(2) . ?
F00N C01R 1.345(2) . ?
F00O C01V 1.344(2) . ?
F00P C022 1.346(2) . ?
F13 C16 1.343(2) . ?
O00R C01A 1.273(2) . ?
O00R B02G 1.559(2) . ?
F00S C025 1.340(2) . ?
F00T C023 1.338(2) . ?
F14 C17 1.341(2) . ?
F00V C029 1.345(3) . ?
F00W C021 1.350(2) . ?
F00X C02A 1.340(2) . ?
F00Y C02C 1.338(2) . ?
N00Z C01A 1.323(2) . ?
N00Z C01K 1.396(2) . ?
N1 C25 1.397(2) . ?
N1 C19 1.329(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.391(2) . ?
C1 B1 1.641(2) . ?
C9 C10 1.380(2) . ?
C9 C8 1.374(2) . ?
C2 C3 1.381(2) . ?
C13 C14 1.390(2) . ?
C13 C18 1.389(2) . ?
C13 B1 1.632(2) . ?
C7 C8 1.390(2) . ?
C7 C12 1.394(2) . ?
C7 B1 1.634(2) . ?
C10 C11 1.373(2) . ?
C12 C11 1.385(2) . ?
C019 C01N 1.388(2) . ?
C019 C01T 1.392(2) . ?
C019 B02G 1.632(2) . ?
C3 C4 1.379(3) . ?
C25 C20 1.383(2) . ?
C25 C24 1.386(3) . ?
C01D C01S 1.390(2) . ?
C01D C01U 1.391(3) . ?
C01D B02G 1.641(2) . ?
C4 C5 1.380(3) . ?
C01G C01K 1.388(2) . ?
C01G C01W 1.387(3) . ?
C14 C15 1.376(3) . ?
C01J C01M 1.387(3) . ?
C01J C01Y 1.388(3) . ?
C01J B02G 1.634(3) . ?
C01K C024 1.383(3) . ?
C6 C5 1.385(3) . ?
C01M C029 1.378(3) . ?
C01N C01R 1.387(2) . ?
C18 C17 1.381(3) . ?
C20 C21 1.389(3) . ?
C01R C023 1.372(3) . ?
C01S C021 1.379(3) . ?
C01T C022 1.378(3) . ?
C01U C01V 1.383(3) . ?
C01V C025 1.374(3) . ?
C01W C02E 1.380(3) . ?
C15 C16 1.373(3) . ?
C01Y C02A 1.383(3) . ?
C16 C17 1.377(3) . ?
C021 C025 1.372(3) . ?
C022 C023 1.377(3) . ?
C024 C02D 1.379(3) . ?
C22 C21 1.381(3) . ?
C22 C23 1.391(3) . ?
C24 C23 1.381(3) . ?
C029 C02C 1.382(3) . ?
C02A C02C 1.372(3) . ?
C02D C02E 1.391(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
C01A S001 C01G 90.50(8) . . ?
C19 S1 C20 90.64(8) . . ?
C19 O1 B1 131.35(13) . . ?
C01A O00R B02G 126.07(13) . . ?
C01A N00Z C01K 115.43(14) . . ?
C19 N1 C25 115.77(14) . . ?
C2 C1 B1 119.14(14) . . ?
C6 C1 C2 113.64(15) . . ?
C6 C1 B1 127.20(14) . . ?
F7 C9 C10 119.82(14) . . ?
F7 C9 C8 121.47(15) . . ?
C8 C9 C10 118.71(15) . . ?
F1 C2 C1 119.91(15) . . ?
F1 C2 C3 115.72(14) . . ?
C3 C2 C1 124.36(15) . . ?
C14 C13 B1 118.33(15) . . ?
C18 C13 C14 114.07(16) . . ?
C18 C13 B1 127.48(15) . . ?
C8 C7 C12 113.54(14) . . ?
C8 C7 B1 118.94(14) . . ?
C12 C7 B1 127.48(15) . . ?
F8 C10 C9 120.58(15) . . ?
F8 C10 C11 120.54(15) . . ?
C11 C10 C9 118.87(15) . . ?
F6 C8 C9 116.16(14) . . ?
F6 C8 C7 118.53(14) . . ?
C9 C8 C7 125.31(15) . . ?
F10 C12 C7 121.28(14) . . ?
F10 C12 C11 115.86(14) . . ?
C11 C12 C7 122.86(16) . . ?
C01N C019 C01T 113.91(15) . . ?
C01N C019 B02G 127.65(16) . . ?
C01T C019 B02G 118.35(15) . . ?
O00R C01A S001 127.75(13) . . ?
O00R C01A N00Z 120.53(15) . . ?
N00Z C01A S001 111.71(12) . . ?
F2 C3 C2 119.97(15) . . ?
F2 C3 C4 120.49(16) . . ?
C4 C3 C2 119.52(15) . . ?
C20 C25 N1 111.37(15) . . ?
C20 C25 C24 121.45(17) . . ?
C24 C25 N1 127.18(16) . . ?
C01S C01D C01U 113.92(15) . . ?
C01S C01D B02G 120.48(16) . . ?
C01U C01D B02G 125.47(15) . . ?
F3 C4 C3 120.67(16) . . ?
F3 C4 C5 120.68(16) . . ?
C3 C4 C5 118.64(16) . . ?
F9 C11 C10 118.57(14) . . ?
F9 C11 C12 120.75(15) . . ?
C10 C11 C12 120.68(15) . . ?
C01K C01G S001 110.61(13) . . ?
C01W C01G S001 128.31(14) . . ?
C01W C01G C01K 120.89(17) . . ?
O1 C19 S1 128.67(12) . . ?
O1 C19 N1 119.89(15) . . ?
N1 C19 S1 111.41(12) . . ?
F11 C14 C13 119.20(15) . . ?
F11 C14 C15 116.72(15) . . ?
C15 C14 C13 124.07(17) . . ?
C01M C01J C01Y 113.76(17) . . ?
C01M C01J B02G 118.57(16) . . ?
C01Y C01J B02G 127.27(17) . . ?
C01G C01K N00Z 111.48(15) . . ?
C024 C01K N00Z 126.96(17) . . ?
C024 C01K C01G 121.45(17) . . ?
F5 C6 C1 120.73(16) . . ?
F5 C6 C5 115.70(15) . . ?
C5 C6 C1 123.57(15) . . ?
F009 C01M C01J 119.04(16) . . ?
F009 C01M C029 116.55(18) . . ?
C029 C01M C01J 124.40(19) . . ?
F00D C01N C019 120.72(15) . . ?
F00D C01N C01R 115.73(15) . . ?
C01R C01N C019 123.51(17) . . ?
F4 C5 C4 119.32(16) . . ?
F4 C5 C6 120.47(16) . . ?
C4 C5 C6 120.19(15) . . ?
F15 C18 C13 120.76(16) . . ?
F15 C18 C17 115.75(16) . . ?
C17 C18 C13 123.49(17) . . ?
C25 C20 S1 110.81(13) . . ?
C25 C20 C21 121.20(16) . . ?
C21 C20 S1 127.99(14) . . ?
F00N C01R C01N 120.18(18) . . ?
F00N C01R C023 119.95(16) . . ?
C023 C01R C01N 119.86(17) . . ?
F00K C01S C01D 120.06(15) . . ?
F00K C01S C021 116.35(16) . . ?
C021 C01S C01D 123.58(18) . . ?
F00B C01T C019 119.61(15) . . ?
F00B C01T C022 116.15(16) . . ?
C022 C01T C019 124.24(16) . . ?
F00F C01U C01D 120.85(15) . . ?
F00F C01U C01V 115.23(17) . . ?
C01V C01U C01D 123.91(17) . . ?
F00O C01V C01U 120.47(18) . . ?
F00O C01V C025 120.02(16) . . ?
C025 C01V C01U 119.50(19) . . ?
C02E C01W C01G 117.77(18) . . ?
F12 C15 C14 120.72(17) . . ?
F12 C15 C16 119.85(16) . . ?
C16 C15 C14 119.43(17) . . ?
F00H C01Y C01J 121.00(17) . . ?
F00H C01Y C02A 114.98(17) . . ?
C02A C01Y C01J 124.0(2) . . ?
F13 C16 C15 120.65(18) . . ?
F13 C16 C17 120.22(18) . . ?
C15 C16 C17 119.14(17) . . ?
F14 C17 C18 120.65(18) . . ?
F14 C17 C16 119.61(17) . . ?
C16 C17 C18 119.74(17) . . ?
F00W C021 C01S 120.19(19) . . ?
F00W C021 C025 119.68(17) . . ?
C025 C021 C01S 120.10(17) . . ?
F00P C022 C01T 120.55(17) . . ?
F00P C022 C023 120.16(16) . . ?
C023 C022 C01T 119.29(17) . . ?
F00T C023 C01R 120.56(18) . . ?
F00T C023 C022 120.26(18) . . ?
C01R C023 C022 119.17(16) . . ?
C02D C024 C01K 117.40(19) . . ?
F00S C025 C01V 120.7(2) . . ?
F00S C025 C021 120.32(19) . . ?
C021 C025 C01V 118.95(16) . . ?
C21 C22 C23 121.01(18) . . ?
C23 C24 C25 117.21(18) . . ?
C22 C21 C20 117.53(17) . . ?
F00V C029 C01M 120.9(2) . . ?
F00V C029 C02C 120.00(18) . . ?
C01M C029 C02C 119.1(2) . . ?
F00X C02A C01Y 120.2(2) . . ?
F00X C02A C02C 120.37(19) . . ?
C02C C02A C01Y 119.44(19) . . ?
C24 C23 C22 121.58(17) . . ?
F00Y C02C C029 120.3(2) . . ?
F00Y C02C C02A 120.5(2) . . ?
C02A C02C C029 119.28(18) . . ?
C024 C02D C02E 121.51(19) . . ?
C01W C02E C02D 120.97(18) . . ?
O1 B1 C1 101.01(12) . . ?
O1 B1 C13 109.10(13) . . ?
O1 B1 C7 107.92(13) . . ?
C13 B1 C1 107.84(13) . . ?
C13 B1 C7 115.49(14) . . ?
C7 B1 C1 114.42(13) . . ?
O00R B02G C019 105.78(13) . . ?
O00R B02G C01D 103.28(13) . . ?
O00R B02G C01J 109.79(14) . . ?
C019 B02G C01D 113.20(14) . . ?
C019 B02G C01J 117.14(14) . . ?
C01J B02G C01D 106.76(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
