# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_kk3
_database_code_depnum_ccdc_archive 'CCDC 1543203'
_audit_update_record             
;
2017-04-10 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 Br N O5\"i?1/2\"i?1/2C H Cl3'
_chemical_formula_sum            'C23 H21 Br Cl3 N O5'
_chemical_formula_weight         577.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6151(4)
_cell_length_b                   14.8507(5)
_cell_length_c                   9.7033(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.7867(12)
_cell_angle_gamma                90
_cell_volume                     1214.32(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    5146
_cell_measurement_theta_min      0.604
_cell_measurement_theta_max      0.663

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             584.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.058
_shelx_estimated_absorpt_T_min   0.177
_shelx_estimated_absorpt_T_max   0.225
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_T_max  0.663
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19735
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.395
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             5578
_reflns_number_gt                5126
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.962

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+1.5177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2194 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5486
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002

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
C22 C 0.0559(9) 0.6329(5) 0.5200(10) 0.059(2) Uani 1 1 d . . . . .
H22A H 0.1025 0.6118 0.4555 0.089 Uiso 1 1 calc R U . . .
H22B H -0.0031 0.6887 0.4754 0.089 Uiso 1 1 calc R U . . .
H22C H -0.0163 0.5868 0.5217 0.089 Uiso 1 1 calc R U . . .
Br1 Br 1.06462(6) 0.38155(4) 1.47220(5) 0.03925(16) Uani 1 1 d . . . . .
C1 C 0.9731(5) 0.3720(3) 1.2502(5) 0.0216(8) Uani 1 1 d . . . . .
C6 C 1.0708(5) 0.3707(4) 1.1837(6) 0.0279(10) Uani 1 1 d . . . . .
H6 H 1.1821 0.3779 1.2478 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4783(5) 0.4213(3) 0.8398(5) 0.0184(8) Uani 1 1 d . . . . .
H13 H 0.5130 0.4737 0.8091 0.022 Uiso 1 1 calc R U . . .
O1 O 0.2905(4) 0.3579(2) 0.9065(4) 0.0221(7) Uani 1 1 d . . . . .
C12 C 0.3463(5) 0.4254(3) 0.8510(5) 0.0182(8) Uani 1 1 d . . . . .
C3 C 0.7449(5) 0.3505(3) 1.0025(5) 0.0175(8) Uani 1 1 d . . . . .
C11 C 0.4120(5) 0.2921(3) 1.0002(5) 0.0165(8) Uani 1 1 d . . . . .
H11 H 0.4954 0.3225 1.0966 0.020 Uiso 1 1 calc R U . . .
C4 C 0.8442(5) 0.3482(3) 0.9363(5) 0.0209(9) Uani 1 1 d . . . . .
C2 C 0.8080(5) 0.3648(3) 1.1620(5) 0.0208(9) Uani 1 1 d . . . . .
H2 H 0.7422 0.3695 1.2097 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3329(5) 0.2221(3) 1.0490(5) 0.0186(8) Uani 1 1 d . . . . .
C16 C 0.1512(7) 0.0965(4) 0.9906(8) 0.0381(13) Uani 1 1 d . . . . .
H16 H 0.0824 0.0528 0.9184 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2308(6) 0.1579(4) 0.9443(6) 0.0284(10) Uani 1 1 d . . . . .
H15 H 0.2150 0.1560 0.8399 0.034 Uiso 1 1 calc R U . . .
C5 C 1.0067(6) 0.3588(4) 1.0225(6) 0.0299(12) Uani 1 1 d . . . . .
H5 H 1.0718 0.3580 0.9736 0.036 Uiso 1 1 calc R U . . .
C19 C 0.3565(5) 0.2237(3) 1.2020(6) 0.0213(9) Uani 1 1 d . . . . .
C10 C 0.4874(5) 0.2580(3) 0.9039(5) 0.0181(8) Uani 1 1 d . . . . .
H10A H 0.4044 0.2339 0.8023 0.022 Uiso 1 1 calc R U . . .
H10B H 0.5629 0.2088 0.9612 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5756(5) 0.3360(3) 0.8744(5) 0.0174(8) Uani 1 1 d . . . . .
C18 C 0.2743(6) 0.1625(4) 1.2471(6) 0.0282(10) Uani 1 1 d . . . . .
H18 H 0.2883 0.1644 1.3509 0.034 Uiso 1 1 calc R U . . .
C17 C 0.1730(7) 0.0996(4) 1.1413(8) 0.0362(13) Uani 1 1 d . . . . .
H17 H 0.1183 0.0583 1.1730 0.043 Uiso 1 1 calc R U . . .
N1 N 0.7540(5) 0.3300(3) 0.7735(5) 0.0236(8) Uani 1 1 d . . . . .
C7 C 0.8232(7) 0.3195(5) 0.6703(7) 0.0396(14) Uani 1 1 d . . . . .
H7A H 0.7383 0.3141 0.5613 0.059 Uiso 1 1 calc R U . . .
H7B H 0.8891 0.2651 0.6998 0.059 Uiso 1 1 calc R U . . .
H7C H 0.8889 0.3721 0.6802 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5997(5) 0.3155(3) 0.7319(5) 0.0190(8) Uani 1 1 d . . . . .
O3 O 0.4962(4) 0.2901(2) 0.6026(4) 0.0265(7) Uani 1 1 d . . . . .
Cl1 Cl 0.4216(3) 0.51108(18) 0.4721(2) 0.0778(7) Uani 1 1 d . . . . .
Cl2 Cl 0.2875(4) 0.5780(2) 0.1627(3) 0.1169(14) Uani 1 1 d . . . . .
O5 O 0.1108(4) 0.5040(3) 0.7999(5) 0.0324(8) Uani 1 1 d . . . . .
O6 O 0.2901(4) 0.5718(2) 0.7485(5) 0.0332(8) Uani 1 1 d . . . . .
C20 C 0.2347(5) 0.5041(3) 0.7993(6) 0.0228(9) Uani 1 1 d . . . . .
Cl3 Cl 0.6117(5) 0.5254(2) 0.3196(7) 0.152(2) Uani 1 1 d . . . . .
C23 C 0.4623(9) 0.5688(5) 0.3418(9) 0.0553(18) Uani 1 1 d . . . . .
H23 H 0.4943 0.6312 0.3841 0.066 Uiso 1 1 calc R U . . .
O2 O 0.4566(5) 0.2853(3) 1.3033(4) 0.0322(8) Uani 1 1 d . . . . .
H2A H 0.4456 0.2868 1.3841 0.048 Uiso 1 1 calc R U . . .
C21 C 0.1866(7) 0.6503(4) 0.6859(8) 0.0431(14) Uani 1 1 d . . . . .
H21A H 0.2499 0.7029 0.6862 0.052 Uiso 1 1 calc R U . . .
H21B H 0.1391 0.6645 0.7540 0.052 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
C22 C21 1.512(10) . ?
Br1 C1 1.900(4) . ?
C1 C6 1.372(6) . ?
C1 C2 1.399(6) . ?
C6 C5 1.389(7) . ?
C13 C12 1.327(6) . ?
C13 C9 1.513(6) . ?
O1 C12 1.364(5) . ?
O1 C11 1.458(5) . ?
C12 C20 1.500(6) . ?
C3 C2 1.379(6) . ?
C3 C4 1.384(6) . ?
C3 C9 1.514(6) . ?
C11 C14 1.492(6) . ?
C11 C10 1.519(5) . ?
C4 C5 1.381(7) . ?
C4 N1 1.415(6) . ?
C14 C19 1.390(6) . ?
C14 C15 1.394(7) . ?
C16 C17 1.374(9) . ?
C16 C15 1.397(7) . ?
C19 O2 1.348(6) . ?
C19 C18 1.406(6) . ?
C10 C9 1.542(6) . ?
C9 C8 1.539(6) . ?
C18 C17 1.382(8) . ?
N1 C8 1.354(6) . ?
N1 C7 1.453(6) . ?
C8 O3 1.227(6) . ?
Cl1 C23 1.721(8) . ?
Cl2 C23 1.746(8) . ?
O5 C20 1.194(6) . ?
O6 C20 1.338(6) . ?
O6 C21 1.462(6) . ?
Cl3 C23 1.681(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.9(4) . . ?
C6 C1 Br1 119.1(3) . . ?
C2 C1 Br1 118.0(3) . . ?
C1 C6 C5 119.9(4) . . ?
C12 C13 C9 122.3(4) . . ?
C12 O1 C11 112.9(3) . . ?
C13 C12 O1 124.9(4) . . ?
C13 C12 C20 124.5(4) . . ?
O1 C12 C20 110.5(4) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 C9 131.4(4) . . ?
C4 C3 C9 108.9(4) . . ?
O1 C11 C14 106.7(3) . . ?
O1 C11 C10 108.5(3) . . ?
C14 C11 C10 115.5(4) . . ?
C5 C4 C3 123.3(4) . . ?
C5 C4 N1 127.1(4) . . ?
C3 C4 N1 109.5(4) . . ?
C3 C2 C1 117.1(4) . . ?
C19 C14 C15 119.0(4) . . ?
C19 C14 C11 118.8(4) . . ?
C15 C14 C11 122.2(4) . . ?
C17 C16 C15 119.6(5) . . ?
C14 C15 C16 121.0(5) . . ?
C4 C5 C6 117.1(4) . . ?
O2 C19 C14 118.9(4) . . ?
O2 C19 C18 121.5(5) . . ?
C14 C19 C18 119.7(5) . . ?
C11 C10 C9 109.4(3) . . ?
C3 C9 C13 111.6(4) . . ?
C3 C9 C8 101.5(3) . . ?
C13 C9 C8 108.2(3) . . ?
C3 C9 C10 115.1(4) . . ?
C13 C9 C10 109.5(3) . . ?
C8 C9 C10 110.6(4) . . ?
C17 C18 C19 120.4(5) . . ?
C16 C17 C18 120.3(5) . . ?
C8 N1 C4 111.0(4) . . ?
C8 N1 C7 125.2(4) . . ?
C4 N1 C7 123.5(4) . . ?
O3 C8 N1 126.0(4) . . ?
O3 C8 C9 125.5(4) . . ?
N1 C8 C9 108.5(4) . . ?
C20 O6 C21 116.1(4) . . ?
O5 C20 O6 125.3(5) . . ?
O5 C20 C12 123.5(5) . . ?
O6 C20 C12 111.2(4) . . ?
Cl3 C23 Cl1 114.4(5) . . ?
Cl3 C23 Cl2 112.0(5) . . ?
Cl1 C23 Cl2 108.6(4) . . ?
O6 C21 C22 110.9(5) . . ?

_refine_diff_density_max         0.968
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.074



####################################################################### 
# 
# 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_mo_20170509c_0m
_database_code_depnum_ccdc_archive 'CCDC 1549570'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Br N2 O4'
_chemical_formula_weight         443.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   16.2892(11)
_cell_length_b                   8.2430(5)
_cell_length_c                   15.3465(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.044(2)
_cell_angle_gamma                90.00
_cell_volume                     1959.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7486
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6183
_exptl_absorpt_correction_T_max  0.9011
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16441
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_sigmaI/netI    0.0734
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4468
_reflns_number_gt                3993
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration rm
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_number_reflns         4468
_refine_ls_number_parameters     260
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.535733(16) 0.57463(4) -0.112648(16) 0.02388(8) Uani 1 1 d . . .
N1 N 0.71310(15) 1.1283(2) 0.12679(15) 0.0191(5) Uani 1 1 d . . .
N2 N 0.93198(16) 0.4160(3) 0.32630(19) 0.0264(6) Uani 1 1 d . . .
O1 O 0.59321(13) 0.3737(2) 0.26745(13) 0.0225(4) Uani 1 1 d . . .
H1 H 0.5631 0.2925 0.2706 0.034 Uiso 1 1 calc R . .
O2 O 0.79475(10) 0.5788(3) 0.30847(11) 0.0202(4) Uani 1 1 d . . .
O3 O 0.99355(11) 0.6121(2) 0.26515(13) 0.0206(5) Uani 1 1 d . . .
O4 O 0.81401(13) 1.1248(2) 0.27007(13) 0.0217(4) Uani 1 1 d . . .
C1 C 0.67459(14) 0.5830(4) 0.36168(15) 0.0144(5) Uani 1 1 d . . .
C2 C 0.61908(17) 0.4506(3) 0.35051(19) 0.0162(6) Uani 1 1 d . . .
C3 C 0.59099(18) 0.3998(3) 0.42349(19) 0.0207(6) Uani 1 1 d . . .
H3 H 0.5521 0.3112 0.4155 0.025 Uiso 1 1 calc R . .
C4 C 0.61952(18) 0.4778(3) 0.5068(2) 0.0220(6) Uani 1 1 d . . .
H4 H 0.5998 0.4428 0.5559 0.026 Uiso 1 1 calc R . .
C5 C 0.67658(18) 0.6066(3) 0.51997(18) 0.0214(7) Uani 1 1 d . . .
H5 H 0.6970 0.6591 0.5778 0.026 Uiso 1 1 calc R . .
C6 C 0.70353(18) 0.6577(3) 0.44664(18) 0.0181(6) Uani 1 1 d . . .
H6 H 0.7427 0.7460 0.4551 0.022 Uiso 1 1 calc R . .
C7 C 0.70662(17) 0.6407(3) 0.28452(18) 0.0146(6) Uani 1 1 d . . .
H7 H 0.6713 0.5882 0.2262 0.018 Uiso 1 1 calc R . .
C8 C 0.70538(17) 0.8225(3) 0.27049(17) 0.0156(5) Uani 1 1 d . . .
H8A H 0.7370 0.8759 0.3290 0.019 Uiso 1 1 calc R . .
H8B H 0.6449 0.8615 0.2519 0.019 Uiso 1 1 calc R . .
C9 C 0.74728(17) 0.8703(3) 0.19608(17) 0.0139(5) Uani 1 1 d . . .
C10 C 0.82987(17) 0.7792(3) 0.21268(17) 0.0152(5) Uani 1 1 d . . .
H10 H 0.8709 0.8156 0.1845 0.018 Uiso 1 1 calc R . .
C11 C 0.84746(17) 0.6496(3) 0.26549(18) 0.0145(5) Uani 1 1 d . . .
C12 C 0.93113(15) 0.5577(4) 0.28604(16) 0.0170(5) Uani 1 1 d . . .
C13 C 1.0073(2) 0.3104(4) 0.3523(3) 0.0377(9) Uani 1 1 d . . .
H13A H 1.0134 0.2572 0.2975 0.056 Uiso 1 1 calc R . .
H13B H 1.0002 0.2279 0.3953 0.056 Uiso 1 1 calc R . .
H13C H 1.0591 0.3749 0.3814 0.056 Uiso 1 1 calc R . .
C14 C 0.76440(16) 1.0565(4) 0.20483(16) 0.0167(5) Uani 1 1 d . . .
C15 C 0.66568(18) 1.0149(3) 0.06344(18) 0.0171(6) Uani 1 1 d . . .
C16 C 0.68537(19) 0.8574(4) 0.0993(2) 0.0159(6) Uani 1 1 d . . .
C17 C 0.64851(17) 0.7263(3) 0.04705(18) 0.0161(6) Uani 1 1 d . . .
H17 H 0.6627 0.6190 0.0693 0.019 Uiso 1 1 calc R . .
C18 C 0.58976(17) 0.7535(3) -0.03940(18) 0.0177(6) Uani 1 1 d . . .
C19 C 0.56936(18) 0.9084(3) -0.07383(18) 0.0209(6) Uani 1 1 d . . .
H19 H 0.5288 0.9233 -0.1329 0.025 Uiso 1 1 calc R . .
C20 C 0.60801(17) 1.0426(3) -0.02220(18) 0.0189(6) Uani 1 1 d . . .
H20 H 0.5950 1.1497 -0.0453 0.023 Uiso 1 1 calc R . .
C21 C 0.7082(2) 1.3026(4) 0.1124(2) 0.0222(7) Uani 1 1 d . . .
H21A H 0.7475 1.3569 0.1659 0.033 Uiso 1 1 calc R . .
H21B H 0.6490 1.3394 0.1036 0.033 Uiso 1 1 calc R . .
H21C H 0.7247 1.3290 0.0578 0.033 Uiso 1 1 calc R . .
H22 H 0.887(2) 0.377(5) 0.328(3) 0.061(13) Uiso 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
Br1 C18 1.897(3) . ?
N1 C14 1.365(3) . ?
N1 C15 1.397(3) . ?
N1 C21 1.451(4) . ?
N2 C12 1.320(4) . ?
N2 C13 1.456(4) . ?
O1 C2 1.368(3) . ?
O2 C11 1.365(3) . ?
O2 C7 1.459(3) . ?
O3 C12 1.241(3) . ?
O4 C14 1.213(3) . ?
C1 C6 1.386(4) . ?
C1 C2 1.393(4) . ?
C1 C7 1.511(3) . ?
C2 C3 1.399(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.394(4) . ?
C7 C8 1.513(3) . ?
C8 C9 1.552(3) . ?
C9 C10 1.492(3) . ?
C9 C16 1.519(4) . ?
C9 C14 1.559(4) . ?
C10 C11 1.318(4) . ?
C11 C12 1.505(4) . ?
C15 C20 1.377(4) . ?
C15 C16 1.407(4) . ?
C16 C17 1.368(4) . ?
C17 C18 1.393(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.393(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
C14 N1 C15 112.1(2) . . ?
C14 N1 C21 123.6(2) . . ?
C15 N1 C21 124.3(2) . . ?
C12 N2 C13 122.9(2) . . ?
C11 O2 C7 116.5(2) . . ?
C6 C1 C2 118.8(2) . . ?
C6 C1 C7 119.9(3) . . ?
C2 C1 C7 121.2(2) . . ?
O1 C2 C1 118.6(2) . . ?
O1 C2 C3 121.6(2) . . ?
C1 C2 C3 119.8(2) . . ?
C4 C3 C2 120.3(3) . . ?
C3 C4 C5 120.7(3) . . ?
C4 C5 C6 118.7(3) . . ?
C1 C6 C5 121.6(3) . . ?
O2 C7 C1 104.14(19) . . ?
O2 C7 C8 110.5(2) . . ?
C1 C7 C8 115.5(2) . . ?
C7 C8 C9 111.5(2) . . ?
C10 C9 C16 115.0(2) . . ?
C10 C9 C8 109.0(2) . . ?
C16 C9 C8 113.1(2) . . ?
C10 C9 C14 110.7(2) . . ?
C16 C9 C14 101.5(2) . . ?
C8 C9 C14 107.12(19) . . ?
C11 C10 C9 121.7(2) . . ?
C10 C11 O2 126.5(2) . . ?
C10 C11 C12 123.2(2) . . ?
O2 C11 C12 110.4(2) . . ?
O3 C12 N2 123.4(3) . . ?
O3 C12 C11 121.7(3) . . ?
N2 C12 C11 114.9(2) . . ?
O4 C14 N1 126.4(3) . . ?
O4 C14 C9 125.7(2) . . ?
N1 C14 C9 107.9(2) . . ?
C20 C15 N1 128.3(2) . . ?
C20 C15 C16 122.1(3) . . ?
N1 C15 C16 109.6(2) . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 C9 131.7(3) . . ?
C15 C16 C9 108.6(2) . . ?
C16 C17 C18 118.5(2) . . ?
C19 C18 C17 121.7(2) . . ?
C19 C18 Br1 118.6(2) . . ?
C17 C18 Br1 119.7(2) . . ?
C18 C19 C20 120.2(3) . . ?
C15 C20 C19 117.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_b170515b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1550834'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Br N O5'
_chemical_formula_sum            'C18 H18 Br N O5'
_chemical_formula_weight         408.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.7193(6)
_cell_length_b                   17.0464(16)
_cell_length_c                   18.2530(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1779.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2282
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   0.3894
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.338
_shelx_estimated_absorpt_T_min   0.334
_shelx_estimated_absorpt_T_max   0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6271
_diffrn_reflns_av_unetI/netI     0.1392
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             3932
_reflns_number_gt                2286
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_fraction_full    0.917

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(19)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3932
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0898
_refine_ls_wR_factor_ref         0.2537
_refine_ls_wR_factor_gt          0.2169
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.3941(3) 0.29857(9) 0.59782(9) 0.0689(6) Uani 1 1 d . . . . .
C1 C 0.2749(17) 0.4831(7) 0.7272(5) 0.033(2) Uani 1 1 d . . . . .
C2 C 0.4519(17) 0.5330(7) 0.6852(6) 0.033(2) Uani 1 1 d . . . . .
C3 C 0.2139(19) 0.4770(7) 0.5997(6) 0.037(2) Uani 1 1 d . . . . .
C4 C 0.113(3) 0.4556(8) 0.5336(5) 0.054(4) Uani 1 1 d . . . . .
H4 H 0.1654 0.4772 0.4892 0.065 Uiso 1 1 calc R U . . .
C5 C -0.068(3) 0.4012(9) 0.5350(6) 0.055(4) Uani 1 1 d . . . . .
H5 H -0.1387 0.3854 0.4910 0.066 Uiso 1 1 calc R U . . .
C6 C -0.141(2) 0.3713(8) 0.5993(6) 0.050(3) Uani 1 1 d . . . . .
C7 C -0.0402(18) 0.3898(8) 0.6659(6) 0.044(3) Uani 1 1 d . . . . .
H7 H -0.0904 0.3663 0.7098 0.052 Uiso 1 1 calc R U . . .
C8 C 0.1347(18) 0.4437(7) 0.6650(5) 0.034(3) Uani 1 1 d . . . . .
C9 C 0.528(3) 0.5678(9) 0.5544(7) 0.058(4) Uani 1 1 d . . . . .
H9A H 0.6476 0.5325 0.5361 0.086 Uiso 1 1 calc R U . . .
H9B H 0.6009 0.6147 0.5738 0.086 Uiso 1 1 calc R U . . .
H9C H 0.4232 0.5820 0.5147 0.086 Uiso 1 1 calc R U . . .
C10 C 0.1204(19) 0.5368(6) 0.7753(5) 0.032(2) Uani 1 1 d . . . . .
H10 H -0.0009 0.5613 0.7441 0.039 Uiso 1 1 calc R U . . .
C11 C 0.001(2) 0.4918(7) 0.8369(6) 0.039(3) Uani 1 1 d . . . . .
H11 H -0.1270 0.4586 0.8174 0.047 Uiso 1 1 calc R U . . .
C12 C 0.3397(19) 0.4108(7) 0.8429(5) 0.036(3) Uani 1 1 d . . . . .
C13 C 0.3958(19) 0.4217(6) 0.7744(5) 0.032(2) Uani 1 1 d . . . . .
H13 H 0.5145 0.3908 0.7536 0.039 Uiso 1 1 calc R U . . .
C14 C 0.239(2) 0.6007(8) 0.8209(6) 0.049(3) Uani 1 1 d . . . . .
H14A H 0.3821 0.5816 0.8442 0.059 Uiso 1 1 calc R U . . .
H14B H 0.2742 0.6472 0.7914 0.059 Uiso 1 1 calc R U . . .
C15 C 0.052(3) 0.6166(9) 0.8756(7) 0.058(4) Uani 1 1 d . . . . .
H15A H 0.1227 0.6305 0.9227 0.070 Uiso 1 1 calc R U . . .
H15B H -0.0438 0.6609 0.8592 0.070 Uiso 1 1 calc R U . . .
C16 C 0.470(2) 0.3559(8) 0.8926(6) 0.047(3) Uani 1 1 d . . . . .
C17 C 0.789(3) 0.2699(11) 0.9034(8) 0.079(5) Uani 1 1 d . . . . .
H17A H 0.6880 0.2347 0.9316 0.095 Uiso 1 1 calc R U . . .
H17B H 0.8832 0.3006 0.9380 0.095 Uiso 1 1 calc R U . . .
C18 C 0.944(3) 0.2238(11) 0.8558(10) 0.090(6) Uani 1 1 d . . . . .
H18A H 0.8539 0.2028 0.8152 0.135 Uiso 1 1 calc R U . . .
H18B H 1.0114 0.1810 0.8837 0.135 Uiso 1 1 calc R U . . .
H18C H 1.0673 0.2572 0.8371 0.135 Uiso 1 1 calc R U . . .
N1 N 0.3954(18) 0.5287(6) 0.6123(4) 0.042(2) Uani 1 1 d . . . . .
O1 O 0.6097(15) 0.5716(6) 0.7099(4) 0.058(2) Uani 1 1 d . . . . .
O2 O 0.1641(15) 0.4452(5) 0.8793(4) 0.044(2) Uani 1 1 d . . . . .
O3 O -0.0884(15) 0.5497(5) 0.8837(4) 0.048(2) Uani 1 1 d . . . . .
O4 O 0.6490(16) 0.3217(6) 0.8591(4) 0.058(3) Uani 1 1 d . . . . .
O5 O 0.419(2) 0.3458(8) 0.9553(5) 0.089(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
Br1 C6 1.906(13) . ?
C1 C13 1.522(16) . ?
C1 C2 1.529(15) . ?
C1 C8 1.544(14) . ?
C1 C10 1.546(15) . ?
C2 O1 1.204(13) . ?
C2 N1 1.371(14) . ?
C3 N1 1.381(15) . ?
C3 C4 1.385(16) . ?
C3 C8 1.397(15) . ?
C4 C5 1.39(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.347(18) . ?
C5 H5 0.9400 . ?
C6 C7 1.383(16) . ?
C7 C8 1.358(17) . ?
C7 H7 0.9400 . ?
C9 N1 1.462(15) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.523(15) . ?
C10 C14 1.528(16) . ?
C10 H10 0.9900 . ?
C11 O3 1.402(14) . ?
C11 O2 1.451(14) . ?
C11 H11 0.9900 . ?
C12 C13 1.304(14) . ?
C12 O2 1.339(14) . ?
C12 C16 1.499(16) . ?
C13 H13 0.9400 . ?
C14 C15 1.486(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 O3 1.402(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 O5 1.192(14) . ?
C16 O4 1.330(16) . ?
C17 O4 1.441(16) . ?
C17 C18 1.47(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?

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
C13 C1 C2 111.5(8) . . ?
C13 C1 C8 110.7(9) . . ?
C2 C1 C8 102.6(8) . . ?
C13 C1 C10 110.2(8) . . ?
C2 C1 C10 109.5(9) . . ?
C8 C1 C10 112.2(8) . . ?
O1 C2 N1 124.7(10) . . ?
O1 C2 C1 127.7(10) . . ?
N1 C2 C1 107.5(9) . . ?
N1 C3 C4 128.8(10) . . ?
N1 C3 C8 111.2(9) . . ?
C4 C3 C8 120.0(11) . . ?
C3 C4 C5 118.1(11) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.0(11) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 123.4(12) . . ?
C5 C6 Br1 118.1(9) . . ?
C7 C6 Br1 118.5(9) . . ?
C8 C7 C6 116.8(11) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C7 C8 C3 121.7(9) . . ?
C7 C8 C1 131.9(9) . . ?
C3 C8 C1 106.4(9) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C14 98.9(8) . . ?
C11 C10 C1 112.2(9) . . ?
C14 C10 C1 118.6(9) . . ?
C11 C10 H10 108.8 . . ?
C14 C10 H10 108.8 . . ?
C1 C10 H10 108.8 . . ?
O3 C11 O2 107.2(8) . . ?
O3 C11 C10 105.0(9) . . ?
O2 C11 C10 112.4(9) . . ?
O3 C11 H11 110.7 . . ?
O2 C11 H11 110.7 . . ?
C10 C11 H11 110.7 . . ?
C13 C12 O2 126.7(11) . . ?
C13 C12 C16 123.2(11) . . ?
O2 C12 C16 110.1(9) . . ?
C12 C13 C1 122.0(10) . . ?
C12 C13 H13 119.0 . . ?
C1 C13 H13 119.0 . . ?
C15 C14 C10 100.3(10) . . ?
C15 C14 H14A 111.7 . . ?
C10 C14 H14A 111.7 . . ?
C15 C14 H14B 111.7 . . ?
C10 C14 H14B 111.7 . . ?
H14A C14 H14B 109.5 . . ?
O3 C15 C14 109.5(11) . . ?
O3 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
O3 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
O5 C16 O4 124.3(12) . . ?
O5 C16 C12 123.5(13) . . ?
O4 C16 C12 112.2(10) . . ?
O4 C17 C18 109.3(12) . . ?
O4 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O4 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 N1 C3 111.9(9) . . ?
C2 N1 C9 123.8(10) . . ?
C3 N1 C9 124.0(9) . . ?
C12 O2 C11 117.3(8) . . ?
C11 O3 C15 107.4(9) . . ?
C16 O4 C17 116.2(10) . . ?

_refine_diff_density_max         0.713
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.131



####################################################################### 
# 
# 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_mo_20201026e_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2040769'
loop_
_audit_author_name
_audit_author_address
yellow
;Soochow University
China
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 Br N O5'
_chemical_formula_sum            'C19 H20 Br N O5'
_chemical_formula_weight         422.27
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.12950(10)
_cell_length_b                   15.9652(4)
_cell_length_c                   18.5922(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1819.41(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    120.04
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.633
_shelx_estimated_absorpt_T_min   0.510
_exptl_absorpt_coefficient_mu    2.289
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0881 after correction.
The Ratio of minimum to maximum transmission is 0.6230.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28025
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         1.681
_diffrn_ambient_temperature      120.04
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3704
_reflns_number_total             4160
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.030
_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)+(0.0207P)²+0.4176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0652
_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
2.a Ternary CH refined with riding coordinates:
 C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C15(H15), C3(H3)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C1(H1A,H1B,H1C)
;
_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 0.95528(6) 0.28347(2) 0.79300(2) 0.02472(10) Uani 1 1 d . . . . .
O2 O 0.3816(4) 0.59917(16) 0.50859(12) 0.0223(6) Uani 1 1 d . . . . .
O5 O 0.0107(4) 0.35828(15) 0.46300(12) 0.0211(6) Uani 1 1 d . . . . .
O3 O 0.2046(4) 0.47997(16) 0.52610(12) 0.0236(6) Uani 1 1 d . . . . .
O4 O -0.1118(4) 0.30208(16) 0.56619(12) 0.0267(6) Uani 1 1 d . . . . .
O1 O -0.0129(3) 0.57240(15) 0.70440(13) 0.0237(5) Uani 1 1 d . . . . .
N1 N 0.1938(4) 0.52110(18) 0.79777(15) 0.0176(6) Uani 1 1 d . . . . .
C16 C 0.1297(6) 0.4184(2) 0.57106(18) 0.0179(7) Uani 1 1 d . . . . .
C6 C 0.6235(5) 0.3880(2) 0.73238(18) 0.0160(7) Uani 1 1 d . . . . .
H6 H 0.674206 0.369119 0.686892 0.019 Uiso 1 1 calc R U . . .
C17 C -0.0047(5) 0.3533(2) 0.53429(18) 0.0187(8) Uani 1 1 d . . . . .
C11 C 0.5089(5) 0.6171(2) 0.65652(18) 0.0185(7) Uani 1 1 d . . . . .
H11A H 0.620161 0.605680 0.693835 0.022 Uiso 1 1 calc R U . . .
H11B H 0.387305 0.648150 0.679313 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6552(6) 0.3916(2) 0.86293(18) 0.0201(8) Uani 1 1 d . . . . .
H4 H 0.730157 0.374555 0.905177 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4241(5) 0.5344(2) 0.62597(16) 0.0147(7) Uani 1 1 d . . . . .
H10 H 0.551459 0.501839 0.607362 0.018 Uiso 1 1 calc R U . . .
C5 C 0.7239(5) 0.3626(2) 0.79643(19) 0.0165(6) Uani 1 1 d . . . . .
C13 C 0.4479(7) 0.6795(2) 0.53526(18) 0.0227(7) Uani 1 1 d . . . . .
H13A H 0.318045 0.710694 0.552181 0.027 Uiso 1 1 calc R U . . .
H13B H 0.515788 0.712024 0.495848 0.027 Uiso 1 1 calc R U . . .
C15 C 0.1698(5) 0.4144(2) 0.64102(17) 0.0169(7) Uani 1 1 d . . . . .
H15 H 0.112752 0.368342 0.667399 0.020 Uiso 1 1 calc R U . . .
C12 C 0.6093(6) 0.6705(2) 0.59670(18) 0.0219(8) Uani 1 1 d . . . . .
H12A H 0.647244 0.726565 0.615767 0.026 Uiso 1 1 calc R U . . .
H12B H 0.744699 0.643728 0.579022 0.026 Uiso 1 1 calc R U . . .
C18 C -0.1109(6) 0.2955(2) 0.42291(18) 0.0247(8) Uani 1 1 d . . . . .
H18A H -0.269563 0.302624 0.430744 0.030 Uiso 1 1 calc R U . . .
H18B H -0.068746 0.238480 0.438652 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4474(6) 0.4417(2) 0.73819(16) 0.0145(6) Uani 1 1 d . . . . .
C8 C 0.3014(5) 0.4793(2) 0.68073(17) 0.0146(7) Uani 1 1 d . . . . .
C14 C 0.2734(6) 0.5540(2) 0.56274(17) 0.0176(7) Uani 1 1 d . . . . .
H14 H 0.143381 0.586109 0.579897 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4780(6) 0.4453(2) 0.86843(17) 0.0204(8) Uani 1 1 d . . . . .
H3 H 0.428481 0.464955 0.913824 0.024 Uiso 1 1 calc R U . . .
C19 C -0.0556(7) 0.3079(2) 0.34494(18) 0.0270(8) Uani 1 1 d . . . . .
H19A H -0.140976 0.268889 0.315560 0.040 Uiso 1 1 calc R U . . .
H19B H 0.100272 0.297448 0.337509 0.040 Uiso 1 1 calc R U . . .
H19C H -0.090169 0.365581 0.330871 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3766(5) 0.4692(2) 0.80537(17) 0.0163(7) Uani 1 1 d . . . . .
C9 C 0.1392(6) 0.5310(2) 0.72708(18) 0.0181(7) Uani 1 1 d . . . . .
C1 C 0.0697(6) 0.5572(2) 0.85690(18) 0.0250(8) Uani 1 1 d . . . . .
H1A H -0.000854 0.512252 0.884275 0.038 Uiso 1 1 calc R U . . .
H1B H -0.041763 0.595064 0.837689 0.038 Uiso 1 1 calc R U . . .
H1C H 0.168188 0.588482 0.888542 0.038 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 C5 1.901(3) . ?
O2 C13 1.434(4) . ?
O2 C14 1.405(4) . ?
O5 C17 1.331(4) . ?
O5 C18 1.455(4) . ?
O3 C16 1.370(4) . ?
O3 C14 1.428(4) . ?
O4 C17 1.205(4) . ?
O1 C9 1.218(4) . ?
N1 C2 1.401(4) . ?
N1 C9 1.365(4) . ?
N1 C1 1.456(4) . ?
C16 C17 1.492(5) . ?
C16 C15 1.325(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.400(5) . ?
C6 C7 1.383(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.529(4) . ?
C11 C12 1.531(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(5) . ?
C4 C3 1.387(5) . ?
C10 H10 1.0000 . ?
C10 C8 1.542(4) . ?
C10 C14 1.527(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.518(5) . ?
C15 H15 0.9500 . ?
C15 C8 1.507(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.502(5) . ?
C7 C8 1.517(4) . ?
C7 C2 1.393(4) . ?
C8 C9 1.553(5) . ?
C14 H14 1.0000 . ?
C3 H3 0.9500 . ?
C3 C2 1.381(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C14 O2 C13 110.2(3) . . ?
C17 O5 C18 115.6(3) . . ?
C16 O3 C14 113.7(2) . . ?
C2 N1 C1 125.2(3) . . ?
C9 N1 C2 111.2(3) . . ?
C9 N1 C1 123.6(3) . . ?
O3 C16 C17 113.9(3) . . ?
C15 C16 O3 124.9(3) . . ?
C15 C16 C17 121.2(3) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C7 C6 C5 117.1(3) . . ?
O5 C17 C16 112.1(3) . . ?
O4 C17 O5 124.7(3) . . ?
O4 C17 C16 123.2(3) . . ?
H11A C11 H11B 108.1 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C10 C11 C12 110.4(3) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C11 C10 H10 108.2 . . ?
C11 C10 C8 114.4(3) . . ?
C8 C10 H10 108.2 . . ?
C14 C10 C11 108.4(3) . . ?
C14 C10 H10 108.2 . . ?
C14 C10 C8 109.3(3) . . ?
C6 C5 Br1 119.5(3) . . ?
C4 C5 Br1 118.6(2) . . ?
C4 C5 C6 121.9(3) . . ?
O2 C13 H13A 109.4 . . ?
O2 C13 H13B 109.4 . . ?
O2 C13 C12 111.1(3) . . ?
H13A C13 H13B 108.0 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C16 C15 H15 118.4 . . ?
C16 C15 C8 123.1(3) . . ?
C8 C15 H15 118.4 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 C11 109.7(3) . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O5 C18 H18A 110.4 . . ?
O5 C18 H18B 110.4 . . ?
O5 C18 C19 106.7(3) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.4 . . ?
C19 C18 H18B 110.4 . . ?
C6 C7 C8 130.6(3) . . ?
C6 C7 C2 120.5(3) . . ?
C2 C7 C8 108.9(3) . . ?
C10 C8 C9 112.0(3) . . ?
C15 C8 C10 109.3(3) . . ?
C15 C8 C7 112.9(3) . . ?
C15 C8 C9 107.1(3) . . ?
C7 C8 C10 113.8(3) . . ?
C7 C8 C9 101.3(3) . . ?
O2 C14 O3 102.9(2) . . ?
O2 C14 C10 111.8(3) . . ?
O2 C14 H14 110.0 . . ?
O3 C14 C10 112.1(3) . . ?
O3 C14 H14 110.0 . . ?
C10 C14 H14 110.0 . . ?
C4 C3 H3 121.3 . . ?
C2 C3 C4 117.4(3) . . ?
C2 C3 H3 121.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 C2 N1 110.2(3) . . ?
C3 C2 N1 127.5(3) . . ?
C3 C2 C7 122.3(3) . . ?
O1 C9 N1 125.7(3) . . ?
O1 C9 C8 125.9(3) . . ?
N1 C9 C8 108.4(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C13 C12 C11 -56.7(4) . . . . ?
O3 C16 C17 O5 12.7(4) . . . . ?
O3 C16 C17 O4 -168.1(3) . . . . ?
O3 C16 C15 C8 1.3(6) . . . . ?
C16 O3 C14 O2 168.5(3) . . . . ?
C16 O3 C14 C10 48.2(4) . . . . ?
C16 C15 C8 C10 -14.2(4) . . . . ?
C16 C15 C8 C7 -141.9(3) . . . . ?
C16 C15 C8 C9 107.4(4) . . . . ?
C6 C7 C8 C10 -60.7(5) . . . . ?
C6 C7 C8 C15 64.6(5) . . . . ?
C6 C7 C8 C9 178.9(4) . . . . ?
C6 C7 C2 N1 -178.6(3) . . . . ?
C6 C7 C2 C3 0.7(5) . . . . ?
C17 O5 C18 C19 -175.2(3) . . . . ?
C17 C16 C15 C8 -179.0(3) . . . . ?
C11 C10 C8 C15 163.0(3) . . . . ?
C11 C10 C8 C7 -69.8(4) . . . . ?
C11 C10 C8 C9 44.4(4) . . . . ?
C11 C10 C14 O2 58.9(4) . . . . ?
C11 C10 C14 O3 173.8(3) . . . . ?
C4 C3 C2 N1 178.7(3) . . . . ?
C4 C3 C2 C7 -0.5(5) . . . . ?
C10 C11 C12 C13 52.5(4) . . . . ?
C10 C8 C9 O1 59.1(4) . . . . ?
C10 C8 C9 N1 -121.8(3) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C5 C6 C7 C2 0.5(5) . . . . ?
C5 C4 C3 C2 -0.9(5) . . . . ?
C13 O2 C14 O3 175.6(3) . . . . ?
C13 O2 C14 C10 -64.0(4) . . . . ?
C15 C16 C17 O5 -167.0(3) . . . . ?
C15 C16 C17 O4 12.2(5) . . . . ?
C15 C8 C9 O1 -60.7(4) . . . . ?
C15 C8 C9 N1 118.3(3) . . . . ?
C12 C11 C10 C8 -174.9(3) . . . . ?
C12 C11 C10 C14 -52.7(4) . . . . ?
C18 O5 C17 O4 -0.9(5) . . . . ?
C18 O5 C17 C16 178.4(3) . . . . ?
C7 C6 C5 Br1 176.2(2) . . . . ?
C7 C6 C5 C4 -1.9(5) . . . . ?
C7 C8 C9 O1 -179.2(3) . . . . ?
C7 C8 C9 N1 -0.2(4) . . . . ?
C8 C10 C14 O2 -175.8(3) . . . . ?
C8 C10 C14 O3 -60.9(4) . . . . ?
C8 C7 C2 N1 0.7(4) . . . . ?
C8 C7 C2 C3 -180.0(3) . . . . ?
C14 O2 C13 C12 62.5(4) . . . . ?
C14 O3 C16 C17 161.8(3) . . . . ?
C14 O3 C16 C15 -18.4(5) . . . . ?
C14 C10 C8 C15 41.3(4) . . . . ?
C14 C10 C8 C7 168.5(3) . . . . ?
C14 C10 C8 C9 -77.3(3) . . . . ?
C3 C4 C5 Br1 -175.9(3) . . . . ?
C3 C4 C5 C6 2.1(5) . . . . ?
C2 N1 C9 O1 179.6(3) . . . . ?
C2 N1 C9 C8 0.6(4) . . . . ?
C2 C7 C8 C10 120.1(3) . . . . ?
C2 C7 C8 C15 -114.6(3) . . . . ?
C2 C7 C8 C9 -0.3(3) . . . . ?
C9 N1 C2 C7 -0.9(4) . . . . ?
C9 N1 C2 C3 179.9(3) . . . . ?
C1 N1 C2 C7 176.4(3) . . . . ?
C1 N1 C2 C3 -2.9(6) . . . . ?
C1 N1 C9 O1 2.3(6) . . . . ?
C1 N1 C9 C8 -176.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
