# Electronic Supplementary Material (ESI) for RSC Medicinal 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_db-3-273
_database_code_depnum_ccdc_archive 'CCDC 2068073'
loop_
_audit_author_name
_audit_author_address
'Benjamin Gelfand'
;University of Calgary
Canada
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_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         'C10 H18 F3 N O S, H2 O'
_chemical_formula_sum            'C10 H20 F3 N O2 S'
_chemical_formula_weight         275.33
_chemical_absolute_configuration syn
_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'
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      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                   6.0280(5)
_cell_length_b                   12.5634(8)
_cell_length_c                   18.7272(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1418.25(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3931
_cell_measurement_temperature    173
_cell_measurement_theta_max      65.192
_cell_measurement_theta_min      4.723
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.470
_exptl_absorpt_coefficient_mu    2.301
_exptl_absorpt_correction_T_max  0.8641
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1091 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.8162. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6416
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        65.188
_diffrn_reflns_theta_max         65.188
_diffrn_reflns_theta_min         4.237
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2080
_reflns_number_total             2391
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 741 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+0.2652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1104
_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,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.52634(14) 0.49946(8) 0.50563(5) 0.0362(3) Uani 1 1 d . . . . .
F1 F 0.3785(6) 0.3262(2) 0.38117(17) 0.0647(9) Uani 1 1 d . . . . .
F2 F 0.2205(6) 0.3896(3) 0.28756(16) 0.0692(9) Uani 1 1 d . . . . .
F3 F 0.0423(5) 0.3818(2) 0.38671(16) 0.0595(8) Uani 1 1 d . . . . .
O1 O 0.6335(5) 0.6017(2) 0.52932(17) 0.0437(7) Uani 1 1 d . . . . .
N1 N 0.3142(6) 0.5262(3) 0.4544(2) 0.0370(8) Uani 1 1 d . . . . .
C1 C 0.2726(12) 0.7744(5) 0.2950(4) 0.0726(17) Uani 1 1 d . . . . .
H1A H 0.239281 0.794023 0.342850 0.087 Uiso 1 1 calc R . . . .
H1B H 0.187443 0.802638 0.256779 0.087 Uiso 1 1 calc R . . . .
C2 C 0.4354(10) 0.7087(4) 0.2819(3) 0.0577(14) Uani 1 1 d . . . . .
H2 H 0.462625 0.691369 0.233334 0.069 Uiso 1 1 calc R . . . .
C3 C 0.5820(9) 0.6585(4) 0.3363(3) 0.0556(13) Uani 1 1 d . . . . .
H3A H 0.553181 0.691574 0.383359 0.067 Uiso 1 1 calc R . . . .
H3B H 0.738722 0.672545 0.323585 0.067 Uiso 1 1 calc R . . . .
C4 C 0.5460(8) 0.5385(4) 0.3419(2) 0.0483(11) Uani 1 1 d . . . . .
H4A H 0.667065 0.506665 0.370547 0.058 Uiso 1 1 calc R . . . .
H4B H 0.551103 0.506633 0.293584 0.058 Uiso 1 1 calc R . . . .
C5 C 0.3234(7) 0.5129(4) 0.3767(2) 0.0388(9) Uani 1 1 d . . . . .
H5 H 0.213600 0.564143 0.356162 0.047 Uiso 1 1 calc R . . . .
C6 C 0.2411(9) 0.4024(4) 0.3577(3) 0.0516(12) Uani 1 1 d . . . . .
C7 C 0.3788(8) 0.4515(3) 0.5862(3) 0.0430(10) Uani 1 1 d . . . . .
C8 C 0.2595(10) 0.3495(4) 0.5649(3) 0.0610(14) Uani 1 1 d . . . . .
H8A H 0.135436 0.366796 0.533120 0.092 Uiso 1 1 calc GR . . . .
H8B H 0.203094 0.313914 0.607751 0.092 Uiso 1 1 calc GR . . . .
H8C H 0.363255 0.302216 0.540051 0.092 Uiso 1 1 calc GR . . . .
C9 C 0.5642(9) 0.4287(4) 0.6396(3) 0.0571(13) Uani 1 1 d . . . . .
H9A H 0.669839 0.378327 0.618640 0.086 Uiso 1 1 calc GR . . . .
H9B H 0.500750 0.397987 0.683187 0.086 Uiso 1 1 calc GR . . . .
H9C H 0.641089 0.495172 0.651388 0.086 Uiso 1 1 calc GR . . . .
C10 C 0.2233(9) 0.5363(4) 0.6136(3) 0.0539(13) Uani 1 1 d . . . . .
H10A H 0.304221 0.603464 0.618869 0.081 Uiso 1 1 calc GR . . . .
H10B H 0.163430 0.514537 0.659975 0.081 Uiso 1 1 calc GR . . . .
H10C H 0.101216 0.545901 0.579608 0.081 Uiso 1 1 calc GR . . . .
O2 O 0.0031(6) 0.6859(3) 0.4626(2) 0.0540(9) Uani 1 1 d . . . . .
H1 H 0.234(11) 0.577(5) 0.469(3) 0.081 Uiso 1 1 d R . . . .
H2A H -0.104(11) 0.673(5) 0.486(3) 0.081 Uiso 1 1 d R . . . .
H2B H 0.021(11) 0.745(5) 0.467(3) 0.081 Uiso 1 1 d 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 O1 1.505(3) . ?
S1 N1 1.634(4) . ?
S1 C7 1.852(4) . ?
F1 C6 1.341(6) . ?
F2 C6 1.329(5) . ?
F3 C6 1.341(6) . ?
N1 C5 1.466(5) . ?
C1 C2 1.306(8) . ?
C2 C3 1.488(7) . ?
C3 C4 1.527(6) . ?
C4 C5 1.526(6) . ?
C5 C6 1.516(7) . ?
C7 C8 1.522(6) . ?
C7 C9 1.527(7) . ?
C7 C10 1.509(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 109.48(17) . . ?
O1 S1 C7 104.12(19) . . ?
N1 S1 C7 99.8(2) . . ?
C5 N1 S1 122.0(3) . . ?
C1 C2 C3 125.8(5) . . ?
C2 C3 C4 112.4(4) . . ?
C3 C4 C5 111.3(4) . . ?
N1 C5 C4 115.6(4) . . ?
N1 C5 C6 109.0(3) . . ?
C6 C5 C4 112.4(4) . . ?
F1 C6 C5 112.0(4) . . ?
F2 C6 F1 107.1(4) . . ?
F2 C6 F3 107.1(4) . . ?
F2 C6 C5 111.9(4) . . ?
F3 C6 F1 106.3(4) . . ?
F3 C6 C5 112.0(4) . . ?
C8 C7 S1 106.7(3) . . ?
C8 C7 C9 111.1(4) . . ?
C9 C7 S1 104.1(3) . . ?
C10 C7 S1 110.2(3) . . ?
C10 C7 C8 112.9(4) . . ?
C10 C7 C9 111.4(4) . . ?

_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_db-3-267_2nd
_database_code_depnum_ccdc_archive 'CCDC 2068076'
loop_
_audit_author_name
_audit_author_address
'Benjamin Gelfand'
;University of Calgary
Canada
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT987_db-3-267_2nd        
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: using BASF/TWIN provided marginal improvement; this 2nd collection was primarily as confirmation of the chirality
;
# Added during the CSD deposition process: Thursday 04 March 2021 09:26 PM
# end Validation Reply Form

_audit_creation_date             2021-01-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11 H8 Br N O3)'
_chemical_formula_sum            'C22 H16 Br2 N2 O6'
_chemical_formula_weight         564.19
_chemical_absolute_configuration ad
_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'

_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                   8.1112(2)
_cell_length_b                   8.1755(3)
_cell_length_c                   32.6852(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2167.46(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    173
_cell_measurement_theta_max      72.150
_cell_measurement_theta_min      2.704
_shelx_estimated_absorpt_T_max   0.829
_shelx_estimated_absorpt_T_min   0.281
_exptl_absorpt_coefficient_mu    5.123
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1024 before and 0.0673 after correction.
The Ratio of minimum to maximum transmission is 0.7509.
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    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 1.00 0.0960
1.00 -1.00 -1.00 0.1080
0.00 1.00 -1.00 0.1730
0.00 -1.00 -1.00 0.1060
0.00 0.00 -1.00 0.0150
0.00 0.00 1.00 0.0190
1.00 1.00 0.00 0.1590
-1.00 -1.00 0.00 0.1660

_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.038
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            14513
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         2.704
_diffrn_ambient_temperature      173
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.64
_diffrn_source_power             0.0285824
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           44.66
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3774
_reflns_number_total             3939
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 
;
 Flack x determined using 1430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.069(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     210
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0132P)²+7.0937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C6-C4 \\sim C4A-C6 \\sim C18-C15 \\sim C18-C15A
 with sigma of 0.04
 C6-C5A \\sim C6-C5 \\sim C17-C16A \\sim C17-C16
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A \\sim C16-C15 \\sim C16A-C15A
 with sigma of 0.02
 C4A-C3 \\sim C4-C3 \\sim C15-C14 \\sim C15A-C14
 with sigma of 0.02
 C14-C16A \\sim C14-C16 \\sim C3-C5 \\sim C3-C5A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C14 \\sim C15 \\sim C15A \\sim C16 \\sim C16A \\sim C17: within 3A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 3A
C3 \\sim C4 \\sim C4A \\sim C5 \\sim C5A \\sim C6: within 3A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 3A
4. Others
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=FVAR(1)
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=1-FVAR(2)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4A(H4AA,H4AB), C5(H5A,H5B), C5A(H5AA,H5AB), C15(H15A,H15B),
 C15A(H15C,H15D), C16(H16A,H16B), C16A(H16C,H16D)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C9(H9), C11(H11), N2(H2), C19(H19), C20(H20), C22(H22)
;
_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
Br1 Br 0.61849(14) 0.79131(19) 0.72731(3) 0.0623(4) Uani 1 1 d . . . . .
O1 O 0.2895(8) 0.9556(8) 0.48441(18) 0.0382(14) Uani 1 1 d . . . . .
O2 O 0.1255(7) 0.5016(7) 0.55462(16) 0.0287(12) Uani 1 1 d . . . . .
O3 O 0.2293(7) 0.9181(7) 0.55103(17) 0.0295(12) Uani 1 1 d . . . . .
N1 N 0.1992(8) 0.7067(8) 0.5097(2) 0.0284(14) Uani 1 1 d . . . . .
H1 H 0.195866 0.650285 0.486769 0.034 Uiso 1 1 calc R U . . .
C1 C 0.2424(10) 0.8693(11) 0.5119(3) 0.0317(18) Uani 1 1 d . . . . .
C2 C 0.1626(10) 0.6440(11) 0.5465(2) 0.0280(18) Uani 1 1 d . . . . .
C3 C 0.1709(10) 0.7824(11) 0.5770(2) 0.0295(16) Uani 1 1 d D U . . .
C4 C 0.0066(13) 0.827(3) 0.5973(3) 0.033(3) Uani 0.83(9) 1 d D U P A 1
H4A H -0.068956 0.731948 0.597079 0.040 Uiso 0.83(9) 1 calc R U P A 1
H4B H -0.046802 0.918415 0.582445 0.040 Uiso 0.83(9) 1 calc R U P A 1
C4A C 0.003(3) 0.796(13) 0.5982(11) 0.032(4) Uani 0.17(9) 1 d D U P A 2
H4AA H -0.060569 0.889183 0.586761 0.038 Uiso 0.17(9) 1 calc R U P A 2
H4AB H -0.061908 0.694760 0.594020 0.038 Uiso 0.17(9) 1 calc R U P A 2
C5 C 0.0462(16) 0.878(4) 0.6415(3) 0.032(3) Uani 0.83(9) 1 d D U P A 1
H5A H 0.040442 0.998119 0.644673 0.039 Uiso 0.83(9) 1 calc R U P A 1
H5B H -0.031117 0.826144 0.660995 0.039 Uiso 0.83(9) 1 calc R U P A 1
C5A C 0.035(3) 0.823(17) 0.6438(12) 0.032(4) Uani 0.17(9) 1 d D U P A 2
H5AA H -0.007641 0.930839 0.652780 0.039 Uiso 0.17(9) 1 calc R U P A 2
H5AB H -0.017649 0.736462 0.660418 0.039 Uiso 0.17(9) 1 calc R U P A 2
C6 C 0.2203(10) 0.8164(11) 0.6480(3) 0.0331(17) Uani 1 1 d D U . . .
C7 C 0.2904(10) 0.7634(9) 0.6121(2) 0.0257(17) Uani 1 1 d . . . . .
C8 C 0.4520(10) 0.7147(10) 0.6095(2) 0.0267(16) Uani 1 1 d . . . . .
H8 H 0.496340 0.676733 0.584336 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5494(10) 0.7222(10) 0.6444(2) 0.0316(18) Uani 1 1 d . . . . .
H9 H 0.662102 0.690959 0.643487 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4797(11) 0.7758(12) 0.6805(2) 0.040(2) Uani 1 1 d . . . . .
C11 C 0.3157(11) 0.8224(12) 0.6832(3) 0.037(2) Uani 1 1 d . . . . .
H11 H 0.269834 0.857494 0.708466 0.044 Uiso 1 1 calc R U . . .
Br2 Br 0.52031(13) 0.04249(16) 0.27959(3) 0.0561(3) Uani 1 1 d . . . . .
O4 O -0.0609(7) 0.0752(7) 0.50680(19) 0.0328(13) Uani 1 1 d . . . . .
O5 O 0.1472(7) 0.5131(7) 0.43885(16) 0.0281(12) Uani 1 1 d . . . . .
O6 O -0.0152(7) 0.1180(6) 0.43961(16) 0.0293(12) Uani 1 1 d . . . . .
N2 N 0.0603(8) 0.3115(8) 0.48292(19) 0.0287(15) Uani 1 1 d . . . . .
H2 H 0.083034 0.359854 0.506315 0.034 Uiso 1 1 calc R U . . .
C12 C -0.0095(9) 0.1593(10) 0.4798(2) 0.0293(17) Uani 1 1 d . . . . .
C13 C 0.0902(9) 0.3788(10) 0.4458(2) 0.0246(16) Uani 1 1 d . . . . .
C14 C 0.0401(10) 0.2529(9) 0.4138(2) 0.0272(16) Uani 1 1 d D U . . .
C15 C -0.094(3) 0.325(5) 0.3854(6) 0.027(3) Uani 0.58(16) 1 d D U P B 1
H15A H -0.205388 0.299010 0.395881 0.033 Uiso 0.58(16) 1 calc R U P B 1
H15B H -0.082411 0.445317 0.383403 0.033 Uiso 0.58(16) 1 calc R U P B 1
C15A C -0.106(4) 0.299(7) 0.3862(8) 0.027(4) Uani 0.42(16) 1 d D U P B 2
H15C H -0.109430 0.418707 0.381815 0.032 Uiso 0.42(16) 1 calc R U P B 2
H15D H -0.211006 0.263450 0.398599 0.032 Uiso 0.42(16) 1 calc R U P B 2
C16 C -0.065(3) 0.244(6) 0.3436(7) 0.029(3) Uani 0.58(16) 1 d D U P B 1
H16A H -0.140378 0.150301 0.339529 0.034 Uiso 0.58(16) 1 calc R U P B 1
H16B H -0.080913 0.323408 0.321093 0.034 Uiso 0.58(16) 1 calc R U P B 1
C16A C -0.075(3) 0.209(8) 0.3456(9) 0.027(3) Uani 0.42(16) 1 d D U P B 2
H16C H -0.131962 0.102028 0.345019 0.032 Uiso 0.42(16) 1 calc R U P B 2
H16D H -0.111640 0.275405 0.321952 0.032 Uiso 0.42(16) 1 calc R U P B 2
C17 C 0.1122(10) 0.1877(10) 0.3457(2) 0.0293(16) Uani 1 1 d D U . . .
C18 C 0.1728(10) 0.2017(11) 0.3850(2) 0.0294(17) Uani 1 1 d D . . . .
C19 C 0.3334(10) 0.1627(10) 0.3942(3) 0.0295(18) Uani 1 1 d . . . . .
H19 H 0.372383 0.167782 0.421539 0.035 Uiso 1 1 calc R U . . .
C20 C 0.4389(10) 0.1152(11) 0.3622(3) 0.0331(19) Uani 1 1 d . . . . .
H20 H 0.551407 0.090845 0.367511 0.040 Uiso 1 1 calc R U . . .
C21 C 0.3759(12) 0.1045(11) 0.3226(3) 0.037(2) Uani 1 1 d . . . . .
C22 C 0.2153(11) 0.1449(11) 0.3137(3) 0.0341(19) Uani 1 1 d . . . . .
H22 H 0.176216 0.143497 0.286298 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.904(8) . ?
O1 C1 1.203(11) . ?
O2 C2 1.231(10) . ?
O3 C1 1.345(10) . ?
O3 C3 1.475(10) . ?
N1 H1 0.8800 . ?
N1 C1 1.377(11) . ?
N1 C2 1.342(11) . ?
C2 C3 1.508(11) . ?
C3 C4 1.533(12) . ?
C3 C4A 1.54(2) . ?
C3 C7 1.511(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.536(12) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.53(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.514(12) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6 1.51(2) . ?
C6 C7 1.373(12) . ?
C6 C11 1.387(12) . ?
C7 C8 1.372(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(12) . ?
C10 C11 1.387(13) . ?
C11 H11 0.9500 . ?
Br2 C21 1.899(9) . ?
O4 C12 1.195(10) . ?
O5 C13 1.213(9) . ?
O6 C12 1.356(9) . ?
O6 C14 1.458(9) . ?
N2 H2 0.8800 . ?
N2 C12 1.372(10) . ?
N2 C13 1.354(10) . ?
C13 C14 1.522(10) . ?
C14 C15 1.546(15) . ?
C14 C15A 1.534(18) . ?
C14 C18 1.490(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.537(16) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.538(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.510(16) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A C17 1.528(19) . ?
C17 C18 1.380(11) . ?
C17 C22 1.384(12) . ?
C18 C19 1.374(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.404(12) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(12) . ?
C21 C22 1.375(13) . ?
C22 H22 0.9500 . ?

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
C1 O3 C3 110.5(6) . . ?
C1 N1 H1 123.9 . . ?
C2 N1 H1 123.9 . . ?
C2 N1 C1 112.3(7) . . ?
O1 C1 O3 124.1(8) . . ?
O1 C1 N1 127.5(9) . . ?
O3 C1 N1 108.4(7) . . ?
O2 C2 N1 127.4(8) . . ?
O2 C2 C3 125.4(7) . . ?
N1 C2 C3 107.2(7) . . ?
O3 C3 C2 101.5(6) . . ?
O3 C3 C4 110.4(10) . . ?
O3 C3 C4A 119(4) . . ?
O3 C3 C7 108.0(6) . . ?
C2 C3 C4 115.2(9) . . ?
C2 C3 C4A 108(3) . . ?
C2 C3 C7 116.9(7) . . ?
C7 C3 C4 104.7(7) . . ?
C7 C3 C4A 103.6(16) . . ?
C3 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
C3 C4 C5 106.8(8) . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C3 C4A H4AA 110.3 . . ?
C3 C4A H4AB 110.3 . . ?
H4AA C4A H4AB 108.5 . . ?
C5A C4A C3 107(2) . . ?
C5A C4A H4AA 110.3 . . ?
C5A C4A H4AB 110.3 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C6 C5 C4 103.8(8) . . ?
C6 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
C4A C5A H5AA 110.8 . . ?
C4A C5A H5AB 110.8 . . ?
H5AA C5A H5AB 108.9 . . ?
C6 C5A C4A 105(2) . . ?
C6 C5A H5AA 110.8 . . ?
C6 C5A H5AB 110.8 . . ?
C7 C6 C5 111.8(8) . . ?
C7 C6 C5A 110.3(18) . . ?
C7 C6 C11 119.3(8) . . ?
C11 C6 C5 128.7(8) . . ?
C11 C6 C5A 128.9(15) . . ?
C6 C7 C3 110.5(7) . . ?
C8 C7 C3 126.5(7) . . ?
C8 C7 C6 122.7(8) . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.6(7) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 118.9(8) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 Br1 117.8(7) . . ?
C9 C10 C11 122.4(8) . . ?
C11 C10 Br1 119.8(7) . . ?
C6 C11 H11 120.9 . . ?
C10 C11 C6 118.2(8) . . ?
C10 C11 H11 120.9 . . ?
C12 O6 C14 111.1(6) . . ?
C12 N2 H2 124.0 . . ?
C13 N2 H2 124.0 . . ?
C13 N2 C12 112.0(7) . . ?
O4 C12 O6 124.1(7) . . ?
O4 C12 N2 127.7(8) . . ?
O6 C12 N2 108.2(7) . . ?
O5 C13 N2 127.1(7) . . ?
O5 C13 C14 125.9(7) . . ?
N2 C13 C14 107.0(7) . . ?
O6 C14 C13 101.4(6) . . ?
O6 C14 C15 114.8(18) . . ?
O6 C14 C15A 107(2) . . ?
O6 C14 C18 112.0(6) . . ?
C13 C14 C15 110.0(14) . . ?
C13 C14 C15A 116.3(18) . . ?
C18 C14 C13 115.5(7) . . ?
C18 C14 C15 103.6(10) . . ?
C18 C14 C15A 104.6(12) . . ?
C14 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C16 C15 C14 105.2(13) . . ?
C16 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C14 C15A H15C 110.6 . . ?
C14 C15A H15D 110.6 . . ?
C14 C15A C16A 105.5(17) . . ?
H15C C15A H15D 108.8 . . ?
C16A C15A H15C 110.6 . . ?
C16A C15A H15D 110.6 . . ?
C15 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C17 C16 C15 103.7(12) . . ?
C17 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
C15A C16A H16C 111.3 . . ?
C15A C16A H16D 111.3 . . ?
H16C C16A H16D 109.2 . . ?
C17 C16A C15A 102.3(17) . . ?
C17 C16A H16C 111.3 . . ?
C17 C16A H16D 111.3 . . ?
C18 C17 C16 110.8(10) . . ?
C18 C17 C16A 110.3(12) . . ?
C18 C17 C22 120.6(8) . . ?
C22 C17 C16 128.1(11) . . ?
C22 C17 C16A 128.9(12) . . ?
C17 C18 C14 110.8(7) . . ?
C19 C18 C14 127.8(7) . . ?
C19 C18 C17 121.4(8) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(8) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.0(8) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 Br2 118.6(7) . . ?
C22 C21 Br2 119.4(7) . . ?
C22 C21 C20 121.9(8) . . ?
C17 C22 H22 120.9 . . ?
C21 C22 C17 118.2(8) . . ?
C21 C22 H22 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C10 C11 C6 177.1(7) . . . . ?
O2 C2 C3 O3 177.0(7) . . . . ?
O2 C2 C3 C4 -63.8(13) . . . . ?
O2 C2 C3 C4A -57(3) . . . . ?
O2 C2 C3 C7 59.8(11) . . . . ?
O3 C3 C4 C5 -100.9(10) . . . . ?
O3 C3 C4A C5A -108(6) . . . . ?
O3 C3 C7 C6 108.2(7) . . . . ?
O3 C3 C7 C8 -66.2(10) . . . . ?
N1 C2 C3 O3 -4.4(8) . . . . ?
N1 C2 C3 C4 114.9(10) . . . . ?
N1 C2 C3 C4A 122(3) . . . . ?
N1 C2 C3 C7 -121.6(8) . . . . ?
C1 O3 C3 C2 3.3(8) . . . . ?
C1 O3 C3 C4 -119.3(8) . . . . ?
C1 O3 C3 C4A -115(2) . . . . ?
C1 O3 C3 C7 126.8(7) . . . . ?
C1 N1 C2 O2 -177.2(8) . . . . ?
C1 N1 C2 C3 4.1(9) . . . . ?
C2 N1 C1 O1 175.8(9) . . . . ?
C2 N1 C1 O3 -2.0(10) . . . . ?
C2 C3 C4 C5 144.9(10) . . . . ?
C2 C3 C4A C5A 137(6) . . . . ?
C2 C3 C7 C6 -138.2(8) . . . . ?
C2 C3 C7 C8 47.3(11) . . . . ?
C3 O3 C1 O1 -179.0(8) . . . . ?
C3 O3 C1 N1 -1.1(9) . . . . ?
C3 C4 C5 C6 -15.0(14) . . . . ?
C3 C4A C5A C6 -3(8) . . . . ?
C3 C7 C8 C9 172.6(7) . . . . ?
C4 C3 C7 C6 -9.5(12) . . . . ?
C4 C3 C7 C8 176.1(11) . . . . ?
C4 C5 C6 C7 9.7(17) . . . . ?
C4 C5 C6 C11 -176.8(10) . . . . ?
C4A C3 C7 C6 -19(4) . . . . ?
C4A C3 C7 C8 166(4) . . . . ?
C4A C5A C6 C7 -10(8) . . . . ?
C4A C5A C6 C11 -175(4) . . . . ?
C5 C6 C7 C3 -0.2(16) . . . . ?
C5 C6 C7 C8 174.5(15) . . . . ?
C5 C6 C11 C10 -172.4(18) . . . . ?
C5A C6 C7 C3 19(6) . . . . ?
C5A C6 C7 C8 -167(6) . . . . ?
C5A C6 C11 C10 165(7) . . . . ?
C6 C7 C8 C9 -1.2(12) . . . . ?
C7 C3 C4 C5 15.1(12) . . . . ?
C7 C3 C4A C5A 12(7) . . . . ?
C7 C6 C11 C10 0.7(13) . . . . ?
C7 C8 C9 C10 1.0(12) . . . . ?
C8 C9 C10 Br1 -178.0(6) . . . . ?
C8 C9 C10 C11 0.0(14) . . . . ?
C9 C10 C11 C6 -0.9(15) . . . . ?
C11 C6 C7 C3 -174.4(8) . . . . ?
C11 C6 C7 C8 0.3(13) . . . . ?
Br2 C21 C22 C17 179.2(7) . . . . ?
O5 C13 C14 O6 178.9(7) . . . . ?
O5 C13 C14 C15 -59.2(18) . . . . ?
O5 C13 C14 C15A -66(2) . . . . ?
O5 C13 C14 C18 57.6(11) . . . . ?
O6 C14 C15 C16 -98.2(15) . . . . ?
O6 C14 C15A C16A -97(2) . . . . ?
O6 C14 C18 C17 105.5(8) . . . . ?
O6 C14 C18 C19 -71.0(11) . . . . ?
N2 C13 C14 O6 -0.5(8) . . . . ?
N2 C13 C14 C15 121.3(16) . . . . ?
N2 C13 C14 C15A 115(2) . . . . ?
N2 C13 C14 C18 -121.9(7) . . . . ?
C12 O6 C14 C13 3.4(8) . . . . ?
C12 O6 C14 C15 -115.1(12) . . . . ?
C12 O6 C14 C15A -118.9(15) . . . . ?
C12 O6 C14 C18 127.1(7) . . . . ?
C12 N2 C13 O5 178.1(8) . . . . ?
C12 N2 C13 C14 -2.4(9) . . . . ?
C13 N2 C12 O4 -173.9(8) . . . . ?
C13 N2 C12 O6 4.6(9) . . . . ?
C13 C14 C15 C16 148.3(13) . . . . ?
C13 C14 C15A C16A 150.9(18) . . . . ?
C13 C14 C18 C17 -139.0(8) . . . . ?
C13 C14 C18 C19 44.4(12) . . . . ?
C14 O6 C12 O4 173.6(8) . . . . ?
C14 O6 C12 N2 -5.0(8) . . . . ?
C14 C15 C16 C17 -21.2(19) . . . . ?
C14 C15A C16A C17 -25(3) . . . . ?
C14 C18 C19 C20 179.2(8) . . . . ?
C15 C14 C18 C17 -19(2) . . . . ?
C15 C14 C18 C19 164.8(19) . . . . ?
C15 C16 C17 C18 10(2) . . . . ?
C15 C16 C17 C22 -162.1(14) . . . . ?
C15A C14 C18 C17 -10(2) . . . . ?
C15A C14 C18 C19 174(2) . . . . ?
C15A C16A C17 C18 20(3) . . . . ?
C15A C16A C17 C22 -165.7(17) . . . . ?
C16 C17 C18 C14 5(2) . . . . ?
C16 C17 C18 C19 -178(2) . . . . ?
C16 C17 C22 C21 177(3) . . . . ?
C16A C17 C18 C14 -7(3) . . . . ?
C16A C17 C18 C19 170(3) . . . . ?
C16A C17 C22 C21 -168(4) . . . . ?
C17 C18 C19 C20 3.0(13) . . . . ?
C18 C14 C15 C16 24.2(17) . . . . ?
C18 C14 C15A C16A 22(2) . . . . ?
C18 C17 C22 C21 5.0(13) . . . . ?
C18 C19 C20 C21 -1.9(13) . . . . ?
C19 C20 C21 Br2 179.3(7) . . . . ?
C19 C20 C21 C22 2.5(14) . . . . ?
C20 C21 C22 C17 -4.0(14) . . . . ?
C22 C17 C18 C14 178.6(8) . . . . ?
C22 C17 C18 C19 -4.7(14) . . . . ?

_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_db-3-267
_database_code_depnum_ccdc_archive 'CCDC 2068075'
loop_
_audit_author_name
_audit_author_address
'Benjamin Gelfand'
;University of Calgary
Canada
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-01-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 Br N O3'
_chemical_formula_sum            'C11 H8 Br N O3'
_chemical_formula_weight         282.09
_chemical_absolute_configuration ad
_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'

_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                   8.1072(2)
_cell_length_b                   8.1810(2)
_cell_length_c                   32.6881(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2168.04(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.449
_cell_measurement_theta_min      5.413
_shelx_estimated_absorpt_T_max   0.777
_shelx_estimated_absorpt_T_min   0.257
_exptl_absorpt_coefficient_mu    5.121
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1040 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.7710.
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    1.728
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 -1.00 0.1810
1.00 1.00 0.00 0.1710
-1.00 -1.00 1.00 0.1770
1.00 -1.00 0.00 0.0550
1.00 -1.00 -1.00 0.0520
-1.00 1.00 1.00 0.0530
0.00 0.00 1.00 0.0130
0.00 0.00 -1.00 0.0260
0.00 1.00 -1.00 0.1290

_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            15161
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.233
_diffrn_reflns_theta_min         2.703
_diffrn_ambient_temperature      173
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.64
_diffrn_source_power             0.0285696
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           44.64
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3826
_reflns_number_total             3947
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.078
_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)+(0.0276P)²+2.1900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0838
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C15-C14 \\sim C15A-C14 \\sim C4-C3 \\sim C4A-C3
 with sigma of 0.02
 C4A-C5A \\sim C4-C5 \\sim C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C6-C5A \\sim C6-C5 \\sim C17-C16 \\sim C17-C16A
 with sigma of 0.02
 C14-C16A \\sim C3-C5A \\sim C3-C5 \\sim C14-C16
 with sigma of 0.04
 C17-C15A \\sim C6-C4 \\sim C17-C15 \\sim C6-C4A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C16A \\sim C15 \\sim C15A \\sim C16 \\sim C14 \\sim C17: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
C4 \\sim C5 \\sim C5A \\sim C4A \\sim C3 \\sim C6: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C15A)=Sof(H15C)=Sof(H15D)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16C)=Sof(H16D)=FVAR(1)
 Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=1-FVAR(2)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C16A(H16A,H16B), C15(H15A,H15B), C5(H5A,H5B), C15A(H15C,H15D),
 C16(H16C,H16D), C5A(H5AA,H5AB), C4A(H4AA,H4AB)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C20(H20), C19(H19), C9(H9), C8(H8), C11(H11), C22(H22)
;
_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
Br1 Br 0.52041(7) 0.95748(10) 0.72043(2) 0.0529(2) Uani 1 1 d . . . . .
Br2 Br 0.61846(7) 0.20853(12) 0.27271(2) 0.0590(2) Uani 1 1 d . . . . .
O6 O 0.2294(4) 0.0813(4) 0.44898(10) 0.0272(7) Uani 1 1 d . . . . .
O5 O 0.1254(4) 0.4976(4) 0.44535(9) 0.0255(7) Uani 1 1 d . . . . .
O2 O 0.1474(4) 0.4866(4) 0.56115(9) 0.0252(7) Uani 1 1 d . . . . .
O1 O -0.0605(4) 0.9249(4) 0.49331(11) 0.0314(7) Uani 1 1 d . . . . .
O3 O -0.0169(4) 0.8825(4) 0.56032(9) 0.0262(7) Uani 1 1 d . . . . .
O4 O 0.2890(4) 0.0459(5) 0.51564(11) 0.0331(8) Uani 1 1 d . . . . .
N2 N 0.1993(5) 0.2935(5) 0.49036(12) 0.0260(8) Uani 1 1 d . . . . .
H2 H 0.196183 0.349620 0.513319 0.031 Uiso 1 1 calc R U . . .
N1 N 0.0600(4) 0.6883(5) 0.51721(11) 0.0243(8) Uani 1 1 d . . . . .
H1 H 0.081695 0.639889 0.493772 0.029 Uiso 1 1 calc R U . . .
C20 C 0.5505(6) 0.2782(6) 0.35549(14) 0.0290(10) Uani 1 1 d . . . . .
H20 H 0.663338 0.309489 0.356191 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4539(6) 0.2866(6) 0.39057(13) 0.0250(9) Uani 1 1 d . . . . .
H19 H 0.498658 0.324922 0.415656 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1725(5) 0.2166(6) 0.42311(13) 0.0246(9) Uani 1 1 d D U . . .
C2 C 0.0920(5) 0.6206(6) 0.55419(13) 0.0208(9) Uani 1 1 d . . . . .
C3 C 0.0393(5) 0.7474(5) 0.58581(13) 0.0222(9) Uani 1 1 d D U . . .
C1 C -0.0097(5) 0.8397(6) 0.52027(14) 0.0245(9) Uani 1 1 d . . . . .
C18 C 0.2910(6) 0.2375(5) 0.38798(14) 0.0226(9) Uani 1 1 d . . . . .
C7 C 0.1731(6) 0.7991(6) 0.61504(13) 0.0245(9) Uani 1 1 d . . . . .
C4 C -0.092(3) 0.674(4) 0.6149(5) 0.024(3) Uani 0.54(10) 1 d D U P A 1
H4A H -0.204248 0.696836 0.604698 0.029 Uiso 0.54(10) 1 calc R U P A 1
H4B H -0.077691 0.553637 0.617002 0.029 Uiso 0.54(10) 1 calc R U P A 1
C12 C 0.2430(6) 0.1312(6) 0.48813(15) 0.0264(10) Uani 1 1 d . . . . .
C9 C 0.4392(6) 0.8845(7) 0.63757(16) 0.0312(11) Uani 1 1 d . . . . .
H9 H 0.551304 0.910663 0.632194 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1618(5) 0.3572(6) 0.45337(14) 0.0228(9) Uani 1 1 d . . . . .
C10 C 0.3771(7) 0.8927(7) 0.67730(15) 0.0328(11) Uani 1 1 d . . . . .
C8 C 0.3350(6) 0.8374(6) 0.60601(15) 0.0280(10) Uani 1 1 d . . . . .
H8 H 0.374304 0.831713 0.578664 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1122(6) 0.8111(6) 0.65445(14) 0.0275(10) Uani 1 1 d D U . . .
C17 C 0.2211(6) 0.1830(6) 0.35191(15) 0.0292(10) Uani 1 1 d D U . . .
C11 C 0.2150(6) 0.8559(7) 0.68654(15) 0.0316(11) Uani 1 1 d . . . . .
H11 H 0.175266 0.861039 0.713851 0.038 Uiso 1 1 calc R U . . .
C22 C 0.3163(6) 0.1771(8) 0.31648(15) 0.0356(12) Uani 1 1 d . . . . .
H22 H 0.270818 0.142241 0.291160 0.043 Uiso 1 1 calc R U . . .
C21 C 0.4794(6) 0.2237(8) 0.31960(14) 0.0356(11) Uani 1 1 d . . . . .
C16A C 0.0485(17) 0.115(4) 0.3588(4) 0.030(3) Uani 0.69(9) 1 d D U P B 2
H16A H 0.047307 -0.005310 0.356149 0.036 Uiso 0.69(9) 1 calc R U P B 2
H16B H -0.030845 0.162460 0.339004 0.036 Uiso 0.69(9) 1 calc R U P B 2
C15 C 0.004(3) 0.198(7) 0.4016(8) 0.028(4) Uani 0.31(9) 1 d D U P B 1
H15A H -0.061020 0.109883 0.414599 0.034 Uiso 0.31(9) 1 calc R U P B 1
H15B H -0.059741 0.301531 0.403860 0.034 Uiso 0.31(9) 1 calc R U P B 1
C5 C -0.065(2) 0.755(4) 0.6570(6) 0.027(3) Uani 0.54(10) 1 d D U P A 1
H5A H -0.140532 0.848213 0.661024 0.032 Uiso 0.54(10) 1 calc R U P A 1
H5B H -0.080165 0.675434 0.679531 0.032 Uiso 0.54(10) 1 calc R U P A 1
C15A C 0.0073(13) 0.168(3) 0.4029(4) 0.028(3) Uani 0.69(9) 1 d D U P B 2
H15C H -0.045008 0.077350 0.418058 0.034 Uiso 0.69(9) 1 calc R U P B 2
H15D H -0.069456 0.262512 0.402688 0.034 Uiso 0.69(9) 1 calc R U P B 2
C16 C 0.037(2) 0.158(7) 0.3564(9) 0.028(4) Uani 0.31(9) 1 d D U P B 1
H16C H 0.005726 0.043503 0.350152 0.033 Uiso 0.31(9) 1 calc R U P B 1
H16D H -0.025312 0.232121 0.338130 0.033 Uiso 0.31(9) 1 calc R U P B 1
C5A C -0.0746(19) 0.791(5) 0.6542(7) 0.024(3) Uani 0.46(10) 1 d D U P A 2
H5AA H -0.130602 0.898813 0.654820 0.029 Uiso 0.46(10) 1 calc R U P A 2
H5AB H -0.112343 0.725262 0.677791 0.029 Uiso 0.46(10) 1 calc R U P A 2
C4A C -0.107(3) 0.702(4) 0.6134(6) 0.023(3) Uani 0.46(10) 1 d D U P A 2
H4AA H -0.112019 0.582060 0.617701 0.028 Uiso 0.46(10) 1 calc R U P A 2
H4AB H -0.212414 0.738425 0.601121 0.028 Uiso 0.46(10) 1 calc R U P A 2


_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 C10 1.902(5) . ?
Br2 C21 1.907(4) . ?
O6 C14 1.467(6) . ?
O6 C12 1.348(6) . ?
O5 C13 1.214(6) . ?
O2 C2 1.206(6) . ?
O1 C1 1.197(6) . ?
O3 C3 1.457(5) . ?
O3 C1 1.356(5) . ?
O4 C12 1.198(6) . ?
N2 H2 0.8800 . ?
N2 C12 1.376(7) . ?
N2 C13 1.351(6) . ?
N1 H1 0.8800 . ?
N1 C2 1.355(6) . ?
N1 C1 1.365(6) . ?
C20 H20 0.9500 . ?
C20 C19 1.390(6) . ?
C20 C21 1.381(7) . ?
C19 H19 0.9500 . ?
C19 C18 1.383(6) . ?
C14 C18 1.507(6) . ?
C14 C13 1.519(6) . ?
C14 C15 1.545(19) . ?
C14 C15A 1.545(10) . ?
C2 C3 1.525(6) . ?
C3 C7 1.506(6) . ?
C3 C4 1.549(14) . ?
C3 C4A 1.537(15) . ?
C18 C17 1.382(7) . ?
C7 C8 1.382(7) . ?
C7 C6 1.383(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.543(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(7) . ?
C9 C8 1.388(7) . ?
C10 C11 1.381(8) . ?
C8 H8 0.9500 . ?
C6 C11 1.389(7) . ?
C6 C5 1.508(14) . ?
C6 C5A 1.524(15) . ?
C17 C22 1.393(7) . ?
C17 C16A 1.522(10) . ?
C17 C16 1.516(18) . ?
C11 H11 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.379(8) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16A C15A 1.543(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.539(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C4A 1.544(15) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?

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
C12 O6 C14 110.1(4) . . ?
C1 O3 C3 110.0(3) . . ?
C12 N2 H2 123.8 . . ?
C13 N2 H2 123.8 . . ?
C13 N2 C12 112.5(4) . . ?
C2 N1 H1 123.7 . . ?
C2 N1 C1 112.6(4) . . ?
C1 N1 H1 123.7 . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C21 C20 C19 118.8(4) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 C20 118.3(4) . . ?
C18 C19 H19 120.9 . . ?
O6 C14 C18 108.9(4) . . ?
O6 C14 C13 102.4(3) . . ?
O6 C14 C15 118(2) . . ?
O6 C14 C15A 109.1(10) . . ?
C18 C14 C13 116.5(4) . . ?
C18 C14 C15 103.3(11) . . ?
C18 C14 C15A 104.8(6) . . ?
C13 C14 C15 108.5(16) . . ?
C13 C14 C15A 115.0(8) . . ?
O2 C2 N1 127.7(4) . . ?
O2 C2 C3 126.5(4) . . ?
N1 C2 C3 105.8(4) . . ?
O3 C3 C2 102.5(3) . . ?
O3 C3 C7 112.0(4) . . ?
O3 C3 C4 115.6(14) . . ?
O3 C3 C4A 106.2(15) . . ?
C2 C3 C4 110.1(11) . . ?
C2 C3 C4A 116.7(12) . . ?
C7 C3 C2 114.8(4) . . ?
C7 C3 C4 102.3(8) . . ?
C7 C3 C4A 104.6(9) . . ?
O1 C1 O3 123.1(4) . . ?
O1 C1 N1 128.1(4) . . ?
O3 C1 N1 108.8(4) . . ?
C19 C18 C14 126.5(4) . . ?
C17 C18 C19 122.5(4) . . ?
C17 C18 C14 110.6(4) . . ?
C8 C7 C3 127.8(4) . . ?
C8 C7 C6 121.4(4) . . ?
C6 C7 C3 110.8(4) . . ?
C3 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 C3 106.4(11) . . ?
C5 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
O6 C12 N2 108.8(4) . . ?
O4 C12 O6 124.2(5) . . ?
O4 C12 N2 127.1(5) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.1(4) . . ?
O5 C13 N2 127.8(4) . . ?
O5 C13 C14 126.1(4) . . ?
N2 C13 C14 106.1(4) . . ?
C9 C10 Br1 118.9(4) . . ?
C11 C10 Br1 118.7(4) . . ?
C11 C10 C9 122.5(5) . . ?
C7 C8 C9 118.8(4) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C7 C6 C11 120.6(4) . . ?
C7 C6 C5 111.6(8) . . ?
C7 C6 C5A 110.0(9) . . ?
C11 C6 C5 127.5(8) . . ?
C11 C6 C5A 129.0(9) . . ?
C18 C17 C22 119.6(5) . . ?
C18 C17 C16A 111.6(6) . . ?
C18 C17 C16 111.4(10) . . ?
C22 C17 C16A 128.3(6) . . ?
C22 C17 C16 128.5(11) . . ?
C10 C11 C6 117.6(4) . . ?
C10 C11 H11 121.2 . . ?
C6 C11 H11 121.2 . . ?
C17 C22 H22 121.3 . . ?
C21 C22 C17 117.4(5) . . ?
C21 C22 H22 121.3 . . ?
C20 C21 Br2 117.2(4) . . ?
C22 C21 Br2 119.3(4) . . ?
C22 C21 C20 123.5(4) . . ?
C17 C16A H16A 111.1 . . ?
C17 C16A H16B 111.1 . . ?
C17 C16A C15A 103.5(7) . . ?
H16A C16A H16B 109.0 . . ?
C15A C16A H16A 111.1 . . ?
C15A C16A H16B 111.1 . . ?
C14 C15 H15A 110.2 . . ?
C14 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 C14 107.6(17) . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C4 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
C6 C5 C4 102.6(11) . . ?
C6 C5 H5A 111.2 . . ?
C6 C5 H5B 111.2 . . ?
H5A C5 H5B 109.2 . . ?
C14 C15A H15C 110.4 . . ?
C14 C15A H15D 110.4 . . ?
C16A C15A C14 106.5(8) . . ?
C16A C15A H15C 110.4 . . ?
C16A C15A H15D 110.4 . . ?
H15C C15A H15D 108.6 . . ?
C17 C16 C15 103.6(16) . . ?
C17 C16 H16C 111.0 . . ?
C17 C16 H16D 111.0 . . ?
C15 C16 H16C 111.0 . . ?
C15 C16 H16D 111.0 . . ?
H16C C16 H16D 109.0 . . ?
C6 C5A H5AA 111.2 . . ?
C6 C5A H5AB 111.2 . . ?
C6 C5A C4A 103.0(12) . . ?
H5AA C5A H5AB 109.1 . . ?
C4A C5A H5AA 111.2 . . ?
C4A C5A H5AB 111.2 . . ?
C3 C4A C5A 105.1(13) . . ?
C3 C4A H4AA 110.7 . . ?
C3 C4A H4AB 110.7 . . ?
C5A C4A H4AA 110.7 . . ?
C5A C4A H4AB 110.7 . . ?
H4AA C4A H4AB 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C10 C11 C6 179.1(4) . . . . ?
O6 C14 C18 C19 -66.0(6) . . . . ?
O6 C14 C18 C17 107.3(4) . . . . ?
O6 C14 C13 O5 177.0(4) . . . . ?
O6 C14 C13 N2 -3.5(4) . . . . ?
O6 C14 C15 C16 -103(2) . . . . ?
O6 C14 C15A C16A -100.5(8) . . . . ?
O2 C2 C3 O3 -179.9(4) . . . . ?
O2 C2 C3 C7 58.4(6) . . . . ?
O2 C2 C3 C4 -56.3(13) . . . . ?
O2 C2 C3 C4A -64.4(15) . . . . ?
O3 C3 C7 C8 -72.0(6) . . . . ?
O3 C3 C7 C6 105.7(5) . . . . ?
O3 C3 C4 C5 -97.0(11) . . . . ?
O3 C3 C4A C5A -97.1(13) . . . . ?
N1 C2 C3 O3 -1.3(4) . . . . ?
N1 C2 C3 C7 -123.0(4) . . . . ?
N1 C2 C3 C4 122.3(12) . . . . ?
N1 C2 C3 C4A 114.2(15) . . . . ?
C20 C19 C18 C14 171.6(5) . . . . ?
C20 C19 C18 C17 -0.9(7) . . . . ?
C19 C20 C21 Br2 -178.2(4) . . . . ?
C19 C20 C21 C22 0.2(9) . . . . ?
C19 C18 C17 C22 -0.3(8) . . . . ?
C19 C18 C17 C16A 172.2(14) . . . . ?
C19 C18 C17 C16 -173(3) . . . . ?
C14 O6 C12 O4 -179.0(4) . . . . ?
C14 O6 C12 N2 -0.3(5) . . . . ?
C14 C18 C17 C22 -173.8(5) . . . . ?
C14 C18 C17 C16A -1.3(14) . . . . ?
C14 C18 C17 C16 14(3) . . . . ?
C14 C15 C16 C17 -9(3) . . . . ?
C2 N1 C1 O1 -175.1(5) . . . . ?
C2 N1 C1 O3 3.8(5) . . . . ?
C2 C3 C7 C8 44.4(7) . . . . ?
C2 C3 C7 C6 -138.0(4) . . . . ?
C2 C3 C4 C5 147.5(10) . . . . ?
C2 C3 C4A C5A 149.5(11) . . . . ?
C3 O3 C1 O1 174.4(4) . . . . ?
C3 O3 C1 N1 -4.6(5) . . . . ?
C3 C7 C8 C9 179.3(5) . . . . ?
C3 C7 C6 C11 179.5(5) . . . . ?
C3 C7 C6 C5 5.1(18) . . . . ?
C3 C7 C6 C5A -7.9(18) . . . . ?
C3 C4 C5 C6 -22.3(14) . . . . ?
C1 O3 C3 C2 3.6(4) . . . . ?
C1 O3 C3 C7 127.1(4) . . . . ?
C1 O3 C3 C4 -116.2(9) . . . . ?
C1 O3 C3 C4A -119.3(9) . . . . ?
C1 N1 C2 O2 177.2(4) . . . . ?
C1 N1 C2 C3 -1.4(5) . . . . ?
C18 C14 C13 O5 58.3(6) . . . . ?
C18 C14 C13 N2 -122.2(4) . . . . ?
C18 C14 C15 C16 17(3) . . . . ?
C18 C14 C15A C16A 16.0(10) . . . . ?
C18 C17 C22 C21 1.3(8) . . . . ?
C18 C17 C16A C15A 11.4(14) . . . . ?
C18 C17 C16 C15 -2(3) . . . . ?
C7 C3 C4 C5 25.0(13) . . . . ?
C7 C3 C4A C5A 21.5(16) . . . . ?
C7 C6 C11 C10 2.1(8) . . . . ?
C7 C6 C5 C4 11.1(17) . . . . ?
C7 C6 C5A C4A 21.1(18) . . . . ?
C4 C3 C7 C8 163.6(14) . . . . ?
C4 C3 C7 C6 -18.8(15) . . . . ?
C12 O6 C14 C18 126.3(4) . . . . ?
C12 O6 C14 C13 2.3(5) . . . . ?
C12 O6 C14 C15 -116.6(13) . . . . ?
C12 O6 C14 C15A -119.9(7) . . . . ?
C12 N2 C13 O5 -176.9(4) . . . . ?
C12 N2 C13 C14 3.6(5) . . . . ?
C9 C10 C11 C6 -0.7(8) . . . . ?
C13 N2 C12 O6 -2.2(5) . . . . ?
C13 N2 C12 O4 176.5(5) . . . . ?
C13 C14 C18 C19 49.1(6) . . . . ?
C13 C14 C18 C17 -137.6(4) . . . . ?
C13 C14 C15 C16 141(2) . . . . ?
C13 C14 C15A C16A 145.2(8) . . . . ?
C10 C9 C8 C7 -0.5(8) . . . . ?
C8 C7 C6 C11 -2.8(8) . . . . ?
C8 C7 C6 C5 -177.1(17) . . . . ?
C8 C7 C6 C5A 169.9(17) . . . . ?
C8 C9 C10 Br1 -179.9(4) . . . . ?
C8 C9 C10 C11 -0.1(9) . . . . ?
C6 C7 C8 C9 1.9(8) . . . . ?
C6 C5A C4A C3 -25.5(17) . . . . ?
C17 C22 C21 Br2 177.1(4) . . . . ?
C17 C22 C21 C20 -1.3(9) . . . . ?
C17 C16A C15A C14 -16.5(11) . . . . ?
C11 C6 C5 C4 -162.8(11) . . . . ?
C11 C6 C5A C4A -167.0(11) . . . . ?
C22 C17 C16A C15A -177.0(8) . . . . ?
C22 C17 C16 C15 -173.9(18) . . . . ?
C21 C20 C19 C18 0.9(8) . . . . ?
C16A C17 C22 C21 -169.8(16) . . . . ?
C15 C14 C18 C19 168(2) . . . . ?
C15 C14 C18 C17 -19(2) . . . . ?
C15 C14 C13 O5 -57.6(18) . . . . ?
C15 C14 C13 N2 121.9(18) . . . . ?
C5 C6 C11 C10 176(2) . . . . ?
C15A C14 C18 C19 177.4(11) . . . . ?
C15A C14 C18 C17 -9.3(11) . . . . ?
C15A C14 C13 O5 -64.9(10) . . . . ?
C15A C14 C13 N2 114.6(9) . . . . ?
C16 C17 C22 C21 172(3) . . . . ?
C5A C6 C11 C10 -169(2) . . . . ?
C4A C3 C7 C8 173.5(16) . . . . ?
C4A C3 C7 C6 -8.9(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
