# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_3
_database_code_depnum_ccdc_archive 'CCDC 1941798'
loop_
_audit_author_name
_audit_author_address
'Jing Li'
;The cambridge crystallographic data centre
China
;
_audit_update_record             
;
2019-07-19 deposited with the CCDC.	2021-03-23 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         ?
_chemical_formula_sum            'C9 H10 Br2 O2'
_chemical_formula_weight         309.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   5.9149(2)
_cell_length_b                   8.0004(2)
_cell_length_c                   11.2008(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.679(3)
_cell_angle_gamma                90
_cell_volume                     519.07(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    179.99(10)
_cell_measurement_reflns_used    6208
_cell_measurement_theta_min      3.1450
_cell_measurement_theta_max      28.5490

_exptl_crystal_description       rod-like
_exptl_crystal_colour            'white solid'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    7.773
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.47158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      179.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11171
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.152
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2382
_reflns_number_gt                2251
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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)+(0.0379P)²+0.3209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2382
_refine_ls_number_parameters     120
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.05215(11) 0.88387(9) 0.51927(6) 0.0404(2) Uani 1 1 d . . . . .
Br2 Br 0.60640(9) 0.11638(6) 0.71441(5) 0.03001(16) Uani 1 1 d . . . . .
O1 O 0.7843(5) 0.3799(5) 0.9235(3) 0.0235(7) Uani 1 1 d . . . . .
H1 H 0.8195 0.4647 0.9641 0.035 Uiso 1 1 calc R U . . .
O2 O 0.1448(6) 0.1610(5) 0.9407(3) 0.0269(9) Uani 1 1 d . . . . .
H2 H 0.0210 0.2106 0.9273 0.040 Uiso 1 1 calc R U . . .
C1 C 0.4271(9) 0.4942(7) 0.8026(5) 0.0196(10) Uani 1 1 d . . . . .
C2 C 0.5227(10) 0.5434(7) 0.7034(5) 0.0233(11) Uani 1 1 d . . . . .
H2A H 0.6610 0.4959 0.6931 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4175(10) 0.6594(7) 0.6218(5) 0.0285(12) Uani 1 1 d . . . . .
H3 H 0.4852 0.6920 0.5574 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2083(9) 0.7289(7) 0.6350(5) 0.0260(12) Uani 1 1 d . . . . .
C5 C 0.1104(9) 0.6843(7) 0.7332(5) 0.0257(12) Uani 1 1 d . . . . .
H5 H -0.0281 0.7319 0.7430 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2210(9) 0.5691(7) 0.8158(5) 0.0236(12) Uani 1 1 d . . . . .
H6 H 0.1565 0.5403 0.8822 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5387(8) 0.3646(7) 0.8936(4) 0.0202(10) Uani 1 1 d . . . . .
H7 H 0.4820 0.3839 0.9688 0.024 Uiso 1 1 calc R U . . .
C8 C 0.4831(8) 0.1839(7) 0.8562(5) 0.0203(10) Uani 1 1 d . . . . .
H8 H 0.5565 0.1132 0.9246 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2263(9) 0.1432(8) 0.8295(5) 0.0239(12) Uani 1 1 d . . . . .
H9A H 0.1438 0.2190 0.7683 0.029 Uiso 1 1 calc R U . . .
H9B H 0.2012 0.0298 0.7991 0.029 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 C4 1.894(5) . ?
Br2 C8 1.954(5) . ?
O1 C7 1.429(5) . ?
O1 H1 0.8200 . ?
O2 C9 1.431(6) . ?
O2 H2 0.8200 . ?
C1 C6 1.393(7) . ?
C1 C2 1.402(7) . ?
C1 C7 1.509(7) . ?
C2 C3 1.362(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.392(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(8) . ?
C5 C6 1.374(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.522(7) . ?
C7 H7 0.9800 . ?
C8 C9 1.523(7) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 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
C7 O1 H1 109.5 . . ?
C9 O2 H2 109.5 . . ?
C6 C1 C2 117.7(5) . . ?
C6 C1 C7 119.8(5) . . ?
C2 C1 C7 122.5(5) . . ?
C3 C2 C1 121.4(5) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 119.7(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 Br1 119.1(4) . . ?
C3 C4 Br1 120.6(4) . . ?
C6 C5 C4 119.2(5) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.6(5) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O1 C7 C1 112.6(4) . . ?
O1 C7 C8 107.4(4) . . ?
C1 C7 C8 115.3(4) . . ?
O1 C7 H7 107.1 . . ?
C1 C7 H7 107.1 . . ?
C8 C7 H7 107.1 . . ?
C7 C8 C9 114.1(4) . . ?
C7 C8 Br2 113.0(3) . . ?
C9 C8 Br2 107.6(4) . . ?
C7 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
Br2 C8 H8 107.3 . . ?
O2 C9 C8 107.8(4) . . ?
O2 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
O2 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(8) . . . . ?
C7 C1 C2 C3 179.3(5) . . . . ?
C1 C2 C3 C4 -1.2(8) . . . . ?
C2 C3 C4 C5 2.0(8) . . . . ?
C2 C3 C4 Br1 -177.5(4) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
Br1 C4 C5 C6 178.5(4) . . . . ?
C4 C5 C6 C1 -0.9(8) . . . . ?
C2 C1 C6 C5 1.6(8) . . . . ?
C7 C1 C6 C5 -178.2(5) . . . . ?
C6 C1 C7 O1 -140.4(5) . . . . ?
C2 C1 C7 O1 39.7(7) . . . . ?
C6 C1 C7 C8 95.9(6) . . . . ?
C2 C1 C7 C8 -84.0(6) . . . . ?
O1 C7 C8 C9 176.0(4) . . . . ?
C1 C7 C8 C9 -57.6(6) . . . . ?
O1 C7 C8 Br2 -60.6(4) . . . . ?
C1 C7 C8 Br2 65.8(5) . . . . ?
C7 C8 C9 O2 -65.1(6) . . . . ?
Br2 C8 C9 O2 168.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.89 2.699(6) 171.7 2_657
O2 H2 O1 0.82 1.94 2.736(5) 162.7 1_455

_refine_diff_density_max         0.735
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_3_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1963482'
loop_
_audit_author_name
_audit_author_address
'Li Jing'
;Changzhou University
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2021-03-23 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         ?
_chemical_formula_sum            'C10 H13 Br O2'
_chemical_formula_weight         245.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.30480(10)
_cell_length_b                   9.2603(2)
_cell_length_c                   27.0823(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2082.76(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    19942
_cell_measurement_theta_min      2.3190
_cell_measurement_theta_max      28.4190

_exptl_crystal_description       rod-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    3.913
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.75718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48490
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4767
_reflns_number_gt                4521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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)+(0.0298P)²+0.3454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4767
_refine_ls_number_parameters     249
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0507
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.06004(3) 0.14505(3) 0.45919(2) 0.02365(8) Uani 1 1 d . . . . .
O1 O 0.1555(2) 0.4480(2) 0.45241(10) 0.0307(5) Uani 1 1 d D . . . .
H1 H 0.064(3) 0.467(4) 0.4579(14) 0.046 Uiso 1 1 d D U . . .
O2 O 0.2170(3) -0.0656(2) 0.43495(8) 0.0252(5) Uani 1 1 d D . . . .
H2 H 0.269(4) -0.126(3) 0.4215(12) 0.038 Uiso 1 1 d D U . . .
C1 C 0.1735(4) 0.3347(3) 0.41733(12) 0.0277(7) Uani 1 1 d . . . . .
H1A H 0.2767 0.3448 0.4009 0.033 Uiso 1 1 calc R U . . .
H1B H 0.0899 0.3433 0.3925 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1638(3) 0.1867(3) 0.44072(11) 0.0193(6) Uani 1 1 d . . . . .
H2A H 0.2269 0.1899 0.4713 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2352(3) 0.0671(3) 0.40847(11) 0.0219(6) Uani 1 1 d . . . . .
H3A H 0.3510 0.0859 0.4058 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1700(3) 0.0586(3) 0.35662(11) 0.0215(6) Uani 1 1 d . . . . .
C5 C 0.0325(4) -0.0198(3) 0.34495(11) 0.0266(7) Uani 1 1 d . . . . .
H5 H -0.0215 -0.0705 0.3695 0.032 Uiso 1 1 calc R U . . .
C6 C -0.0250(4) -0.0230(4) 0.29674(12) 0.0328(8) Uani 1 1 d . . . . .
H6 H -0.1175 -0.0759 0.2898 0.039 Uiso 1 1 calc R U . . .
C7 C 0.0506(4) 0.0496(4) 0.25901(11) 0.0337(7) Uani 1 1 d . . . . .
C8 C 0.1884(4) 0.1274(4) 0.27071(12) 0.0350(7) Uani 1 1 d . . . . .
H8 H 0.2422 0.1772 0.2459 0.042 Uiso 1 1 calc R U . . .
C9 C 0.2474(4) 0.1326(4) 0.31843(11) 0.0298(7) Uani 1 1 d . . . . .
H9 H 0.3397 0.1859 0.3252 0.036 Uiso 1 1 calc R U . . .
C10 C -0.0108(5) 0.0426(5) 0.20645(13) 0.0494(10) Uani 1 1 d . . . . .
H10A H 0.0569 -0.0203 0.1874 0.074 Uiso 1 1 calc R U . . .
H10B H -0.0094 0.1376 0.1922 0.074 Uiso 1 1 calc R U . . .
H10C H -0.1190 0.0061 0.2063 0.074 Uiso 1 1 calc R U . . .
Br2 Br 0.61797(4) 0.88088(3) 0.39073(2) 0.03303(9) Uani 1 1 d . . . . .
O3 O 0.8608(3) 0.5726(2) 0.47234(8) 0.0284(5) Uani 1 1 d D . . . .
H3 H 0.831(5) 0.586(4) 0.4998(9) 0.043 Uiso 1 1 d D U . . .
O4 O 0.3708(2) 0.6716(2) 0.43867(8) 0.0270(5) Uani 1 1 d D . . . .
H4 H 0.308(4) 0.606(3) 0.4451(13) 0.041 Uiso 1 1 d D U . . .
C11 C 0.8247(3) 0.6911(3) 0.44053(12) 0.0242(6) Uani 1 1 d . . . . .
H11A H 0.8524 0.6653 0.4069 0.029 Uiso 1 1 calc R U . . .
H11B H 0.8902 0.7734 0.4499 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6479(3) 0.7335(3) 0.44269(11) 0.0223(6) Uani 1 1 d . . . . .
H12 H 0.6277 0.7792 0.4747 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5285(3) 0.6104(3) 0.43645(10) 0.0210(6) Uani 1 1 d . . . . .
H13 H 0.5402 0.5474 0.4653 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5546(3) 0.5176(3) 0.39114(11) 0.0199(5) Uani 1 1 d . . . . .
C15 C 0.6551(4) 0.3975(3) 0.39390(12) 0.0268(7) Uani 1 1 d . . . . .
H15 H 0.7015 0.3728 0.4240 0.032 Uiso 1 1 calc R U . . .
C16 C 0.6871(4) 0.3142(3) 0.35253(13) 0.0311(7) Uani 1 1 d . . . . .
H16 H 0.7555 0.2350 0.3551 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6183(4) 0.3478(3) 0.30735(11) 0.0290(6) Uani 1 1 d . . . . .
C18 C 0.5144(4) 0.4644(3) 0.30518(12) 0.0305(7) Uani 1 1 d . . . . .
H18 H 0.4646 0.4865 0.2754 0.037 Uiso 1 1 calc R U . . .
C19 C 0.4826(4) 0.5491(3) 0.34614(12) 0.0276(7) Uani 1 1 d . . . . .
H19 H 0.4128 0.6273 0.3435 0.033 Uiso 1 1 calc R U . . .
C20 C 0.6562(5) 0.2614(4) 0.26147(14) 0.0434(9) Uani 1 1 d . . . . .
H20A H 0.7460 0.3043 0.2446 0.065 Uiso 1 1 calc R U . . .
H20B H 0.5641 0.2609 0.2400 0.065 Uiso 1 1 calc R U . . .
H20C H 0.6826 0.1640 0.2706 0.065 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 C2 1.963(3) . ?
O1 C1 1.424(4) . ?
O1 H1 0.80(2) . ?
O2 C3 1.431(3) . ?
O2 H2 0.79(2) . ?
C1 C2 1.512(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.530(4) . ?
C2 H2A 0.9800 . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9800 . ?
C4 C5 1.390(4) . ?
C4 C9 1.397(4) . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(5) . ?
C7 C10 1.514(5) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Br2 C12 1.976(3) . ?
O3 C11 1.427(4) . ?
O3 H3 0.79(2) . ?
O4 C13 1.429(3) . ?
O4 H4 0.82(2) . ?
C11 C12 1.521(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(4) . ?
C12 H12 0.9800 . ?
C13 C14 1.514(4) . ?
C13 H13 0.9800 . ?
C14 C19 1.389(4) . ?
C14 C15 1.392(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(4) . ?
C17 C20 1.511(4) . ?
C18 C19 1.384(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 O1 H1 113(3) . . ?
C3 O2 H2 109(3) . . ?
O1 C1 C2 112.5(3) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 113.3(2) . . ?
C1 C2 Br1 109.58(19) . . ?
C3 C2 Br1 111.75(19) . . ?
C1 C2 H2A 107.3 . . ?
C3 C2 H2A 107.3 . . ?
Br1 C2 H2A 107.3 . . ?
O2 C3 C4 112.6(2) . . ?
O2 C3 C2 107.1(2) . . ?
C4 C3 C2 115.5(2) . . ?
O2 C3 H3A 107.1 . . ?
C4 C3 H3A 107.1 . . ?
C2 C3 H3A 107.1 . . ?
C5 C4 C9 117.8(3) . . ?
C5 C4 C3 122.3(3) . . ?
C9 C4 C3 119.9(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 117.4(3) . . ?
C6 C7 C10 121.6(3) . . ?
C8 C7 C10 121.0(3) . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 O3 H3 112(3) . . ?
C13 O4 H4 107(3) . . ?
O3 C11 C12 112.2(2) . . ?
O3 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
O3 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 115.6(2) . . ?
C13 C12 Br2 110.9(2) . . ?
C11 C12 Br2 105.8(2) . . ?
C13 C12 H12 108.1 . . ?
C11 C12 H12 108.1 . . ?
Br2 C12 H12 108.1 . . ?
O4 C13 C14 113.0(2) . . ?
O4 C13 C12 107.2(2) . . ?
C14 C13 C12 115.0(2) . . ?
O4 C13 H13 107.1 . . ?
C14 C13 H13 107.1 . . ?
C12 C13 H13 107.1 . . ?
C19 C14 C15 118.2(3) . . ?
C19 C14 C13 122.0(2) . . ?
C15 C14 C13 119.7(3) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C20 120.6(3) . . ?
C16 C17 C20 121.4(3) . . ?
C17 C18 C19 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C14 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C1 C2 C3 -161.3(2) . . . . ?
O1 C1 C2 Br1 73.1(3) . . . . ?
C1 C2 C3 O2 -179.7(2) . . . . ?
Br1 C2 C3 O2 -55.3(3) . . . . ?
C1 C2 C3 C4 -53.4(3) . . . . ?
Br1 C2 C3 C4 71.0(3) . . . . ?
O2 C3 C4 C5 36.5(4) . . . . ?
C2 C3 C4 C5 -87.0(3) . . . . ?
O2 C3 C4 C9 -144.2(3) . . . . ?
C2 C3 C4 C9 92.4(3) . . . . ?
C9 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C5 C6 C7 C10 178.6(3) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C10 C7 C8 C9 -178.8(3) . . . . ?
C7 C8 C9 C4 0.2(5) . . . . ?
C5 C4 C9 C8 0.0(5) . . . . ?
C3 C4 C9 C8 -179.3(3) . . . . ?
O3 C11 C12 C13 -50.1(4) . . . . ?
O3 C11 C12 Br2 -173.2(2) . . . . ?
C11 C12 C13 O4 -179.0(2) . . . . ?
Br2 C12 C13 O4 -58.6(2) . . . . ?
C11 C12 C13 C14 -52.4(4) . . . . ?
Br2 C12 C13 C14 68.0(3) . . . . ?
O4 C13 C14 C19 33.7(4) . . . . ?
C12 C13 C14 C19 -89.8(3) . . . . ?
O4 C13 C14 C15 -147.0(3) . . . . ?
C12 C13 C14 C15 89.4(3) . . . . ?
C19 C14 C15 C16 2.2(4) . . . . ?
C13 C14 C15 C16 -177.1(3) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 -1.4(5) . . . . ?
C15 C16 C17 C20 177.9(3) . . . . ?
C16 C17 C18 C19 2.0(5) . . . . ?
C20 C17 C18 C19 -177.3(3) . . . . ?
C17 C18 C19 C14 -0.5(5) . . . . ?
C15 C14 C19 C18 -1.6(4) . . . . ?
C13 C14 C19 C18 177.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.80(2) 1.99(2) 2.759(3) 163(4) 1_455
O2 H2 O4 0.79(2) 2.11(3) 2.750(3) 138(3) 1_545
O3 H3 O2 0.79(2) 2.01(2) 2.781(3) 163(4) 4_556
O4 H4 O1 0.82(2) 1.94(2) 2.760(3) 174(4) .

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_00
_database_code_depnum_ccdc_archive 'CCDC 2027431'
loop_
_audit_author_name
_audit_author_address
lj
;Changzhou University
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_audit_creation_date             2020-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C11 H14 Br Cl O2)'
_chemical_formula_sum            'C22 H28 Br2 Cl2 O4'
_chemical_formula_weight         587.16
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C O H Cl Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   10.45924(4)
_cell_length_b                   10.51707(4)
_cell_length_c                   22.10012(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2431.027(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    54415
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3440
_cell_measurement_theta_min      3.9930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.465
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            58808
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.528
_diffrn_reflns_theta_min         4.001
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  65.00   0.50    0.05    --   42.30  77.00 -60.00  104
  2  ω     17.00  49.00   0.50    0.05    --   42.30  77.00-120.00   64
  3  ω     71.00  97.00   0.50    0.05    --   42.30  77.00 -60.00   52
  4  ω     86.00 113.00   0.50    0.05    --   42.30  77.00   0.00   54
  5  ω     14.00  72.00   0.50    0.05    --   42.30  77.00   0.00  116
  6  ω     13.00  73.00   0.50    0.05    --   42.30  77.00  90.00  120
  7  ω     83.00 116.00   0.50    0.05    --   42.30  77.00  90.00   66
  8  ω     20.00 117.00   0.50    0.05    --   42.30  57.00  60.00  194
  9  ω     50.00  76.00   0.50    0.05    --   42.30  77.00-120.00   52
 10  ω     20.00  50.00   0.50    0.05    --   42.30  37.00-180.00   60
 11  ω     21.00  73.00   0.50    0.05    --   42.30  57.00-180.00  104
 12  ω     83.00 115.00   0.50    0.05    --   42.30  57.00-180.00   64
 13  ω     13.00 117.00   0.50    0.05    --   42.30  77.00-180.00  208
 14  ω     23.00  94.00   0.50    0.05    --   42.30  37.00 -60.00  142
 15  ω     21.00  86.00   0.50    0.05    --   42.30  37.00   0.00  130
 16  ω    -83.00 -36.00   0.50    0.05    --  -42.30 125.00  90.00   94
 17  ω    -76.00 -50.00   0.50    0.05    -- -102.00 111.00  44.00   52
 18  ω   -108.00 -77.00   0.50    0.05    -- -102.00 111.00  44.00   62
 19  ω    -78.00  -4.00   0.50    0.05    --  -42.30 111.00  44.00  148
 20  ω    108.00 133.00   0.50    0.05    --  107.38 111.00  44.00   50
 21  ω     34.00 106.00   0.50    0.05    --  107.38 -77.00  90.00  144
 22  ω     48.00  77.00   0.50    0.05    --  107.38-125.00  60.00   58
 23  ω     82.00 111.00   0.50    0.05    --  107.38-125.00  60.00   58
 24  ω     42.00  73.00   0.50    0.05    --  107.38 -61.00 -60.00   62
 25  ω     37.00 108.00   0.50    0.05    --  107.38-111.00 -49.00  142
 26  ω     37.00 108.00   0.50    0.05    --  107.38-125.00 -60.00  142
 27  ω     39.00  95.00   0.50    0.05    --  107.38 -94.00   0.00  112
 28  ω     37.00  62.00   0.50    0.05    --  107.38-125.00-180.00   50
 29  ω     76.00 111.00   0.50    0.05    --  107.38-125.00-180.00   70
 30  ω     58.00  96.00   0.50    0.05    --  107.38 -94.00-180.00   76
 31  ω     36.00 102.00   0.50    0.05    --  107.38 -94.00-150.00  132
 32  ω     35.00 103.00   0.50    0.05    --  107.38 -94.00  60.00  136
 33  ω      8.00  73.00   0.50    0.05    --   42.30-111.00 -49.00  130
 34  ω     18.00  59.00   0.50    0.05    --   42.30-125.00-120.00   82
 35  ω     64.00  95.00   0.50    0.05    --   42.30-125.00-120.00   62
 36  ω   -175.00 -72.00   0.50    0.05    -- -102.00 -78.00-166.24  206
 37  ω   -108.00 -72.00   0.50    0.05    -- -102.00 -80.00 -18.44   72
 38  ω    -99.00 -73.00   0.50    0.05    -- -102.00 -80.00  30.59   52
 39  ω   -175.00-123.00   0.50    0.05    -- -102.00 -80.00  30.59  104
 40  ω   -169.00 -73.00   0.50    0.05    -- -102.00 -77.00  82.03  192
 41  ω    -98.00 -72.00   0.50    0.05    -- -102.00 -78.00  97.16   52
 42  ω   -175.00-122.00   0.50    0.05    -- -102.00 -78.00  97.16  106
 43  ω   -171.00-116.00   0.50    0.05    -- -102.00 -77.00   0.00  110
 44  ω   -172.00 -73.00   0.50    0.05    -- -102.00 -77.00 120.00  198
 45  ω   -108.00 -73.00   0.50    0.05    -- -102.00 -77.00   0.00   70
 46  ω    -99.00 -73.00   0.50    0.05    -- -102.00 -77.00  60.00   52
 47  ω   -101.00 -73.00   0.50    0.05    -- -102.00 -77.00 -60.00   56
 48  ω   -108.00 -73.00   0.50    0.05    -- -102.00 -77.00 -90.00   70
 49  ω   -106.00 -73.00   0.50    0.05    -- -102.00 -77.00-113.57   66
 50  ω   -173.00 -73.00   0.50    0.05    -- -102.00 -77.00-180.00  200
 51  ω   -174.00 -74.00   0.50    0.05    -- -102.00 -77.00 -30.00  200
 52  ω   -145.00 -74.00   0.50    0.05    -- -102.00 -75.00-135.71  142
 53  ω   -140.00 -74.00   0.50    0.05    -- -102.00 -75.00-158.42  132
 54  ω    -99.00 -74.00   0.50    0.05    -- -102.00 -74.00 -51.81   50
 55  ω   -152.00-126.00   0.50    0.05    -- -102.00 -74.00 -51.81   52
 56  ω   -168.00-127.00   0.50    0.05    -- -102.00 -73.00-129.19   82
 57  ω   -157.00 -74.00   0.50    0.05    -- -102.00 -74.00-147.76  166
 58  ω   -105.00 -75.00   0.50    0.05    -- -102.00 -73.00-129.19   60
 59  ω   -175.00 -75.00   0.50    0.05    -- -102.00 -73.00-104.20  200
 60  ω   -127.00 -75.00   0.50    0.05    -- -102.00 -71.00  26.51  104
 61  ω   -169.00 -73.00   0.50    0.05    -- -102.00 -76.00  42.22  192
 62  ω   -139.00-113.00   0.50    0.05    -- -102.00 -71.00   2.51   52
 63  ω   -166.00-140.00   0.50    0.05    -- -102.00 -71.00  26.51   52
 64  ω   -153.00-117.00   0.50    0.05    -- -102.00 -77.00  60.00   72
 65  ω   -100.00 -75.00   0.50    0.05    -- -102.00 -71.00   2.51   50
 66  ω   -101.00 -76.00   0.50    0.05    -- -102.00 -70.00   9.45   50
 67  ω   -126.00 -77.00   0.50    0.05    -- -102.00 -68.00  95.36   98
 68  ω   -101.00 -76.00   0.50    0.05    -- -102.00 -69.00 125.41   50
 69  ω   -100.00 -75.00   0.50    0.05    -- -102.00 -72.00 146.95   50
 70  ω   -158.00 -73.00   0.50    0.05    -- -102.00 -76.00 164.10  170
 71  ω   -108.00 -79.00   0.50    0.05    -- -102.00 -63.00  57.60   58
 72  ω   -167.00 -77.00   0.50    0.05    -- -102.00 -66.00 -23.53  180
 73  ω   -108.00 -77.00   0.50    0.05    -- -102.00 -66.00 -94.18   62
 74  ω   -175.00 -78.00   0.50    0.05    -- -102.00 -61.00 -60.00  194
 75  ω   -175.00-117.00   0.50    0.05    -- -102.00 -66.00 -94.18  116
 76  ω   -156.00-131.00   0.50    0.05    -- -102.00 -61.00 -90.00   50
 77  ω   -103.00 -78.00   0.50    0.05    -- -102.00 -61.00 120.00   50
 78  ω   -138.00-111.00   0.50    0.05    -- -102.00 -61.00 120.00   54
 79  ω   -103.00 -78.00   0.50    0.05    -- -102.00 -61.00 -90.00   50
 80  ω   -149.00-124.00   0.50    0.05    -- -102.00-111.00 -49.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0171154000
_diffrn_orient_matrix_UB_12      -0.0249465000
_diffrn_orient_matrix_UB_13      0.0682126000
_diffrn_orient_matrix_UB_21      -0.1374414000
_diffrn_orient_matrix_UB_22      0.0521096000
_diffrn_orient_matrix_UB_23      -0.0033950000
_diffrn_orient_matrix_UB_31      -0.0500872000
_diffrn_orient_matrix_UB_32      -0.1346194000
_diffrn_orient_matrix_UB_33      -0.0139550000
_diffrn_oxdiff_digest_frames     
;
01f71722cfc85792020b0e6fd2bef88742000847760
;
_diffrn_oxdiff_digest_hkl        
;
01a3b6ceda650ae42a978efd001ee6840f5c82
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4919
_reflns_number_total             4930
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_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    ?
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 2095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.015(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0174
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0191P)²+1.2153P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0432
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C8(H8), C23(H23), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C17(H17), C2(H2), C18(H18), C3(H3), C6(H6)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C29(H29A,H29B,H29C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O27(H27), O12(H12)
;
_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
Br7 Br 0.95651(3) 0.80090(2) 0.78535(2) 0.02628(7) Uani 1 1 d . . . . .
Br22 Br 0.91702(3) -0.28192(3) 0.57093(2) 0.03095(7) Uani 1 1 d . . . . .
Cl26 Cl 0.35073(6) 0.35431(7) 0.56865(3) 0.03389(15) Uani 1 1 d . . . . .
Cl11 Cl 0.46458(7) 0.14231(6) 0.91572(3) 0.03270(14) Uani 1 1 d . . . . .
O28 O 0.69391(15) 0.31487(16) 0.63458(7) 0.0183(3) Uani 1 1 d . . . . .
O27 O 0.52550(16) 0.14694(16) 0.69383(7) 0.0190(3) Uani 1 1 d . . . . .
H27 H 0.5680 0.1978 0.7135 0.028 Uiso 1 1 calc GR . . . .
O13 O 0.67852(15) 0.20832(16) 0.79089(7) 0.0199(3) Uani 1 1 d . . . . .
O12 O 0.47939(17) 0.38939(17) 0.78054(8) 0.0224(3) Uani 1 1 d . . . . .
H12 H 0.4716 0.4666 0.7842 0.034 Uiso 1 1 calc GR . . . .
C24 C 0.5001(2) 0.1983(2) 0.63556(10) 0.0184(4) Uani 1 1 d . . . . .
H24 H 0.4512 0.1346 0.6129 0.022 Uiso 1 1 calc R . . . .
C19 C 0.6985(2) 0.1025(2) 0.58990(10) 0.0166(5) Uani 1 1 d . . . . .
C8 C 0.6605(2) 0.3029(2) 0.83637(10) 0.0184(5) Uani 1 1 d . . . . .
H8 H 0.6835 0.2667 0.8758 0.022 Uiso 1 1 calc R . . . .
C21 C 0.7390(2) -0.0909(2) 0.53519(11) 0.0217(5) Uani 1 1 d . . . . .
H21 H 0.7227 -0.1450 0.5028 0.026 Uiso 1 1 calc R . . . .
C17 C 0.8583(2) -0.0455(2) 0.62654(11) 0.0219(5) Uani 1 1 d . . . . .
H17 H 0.9202 -0.0684 0.6548 0.026 Uiso 1 1 calc R . . . .
C4 C 0.7416(2) 0.4200(2) 0.82509(11) 0.0175(5) Uani 1 1 d . . . . .
C2 C 0.8269(2) 0.5726(2) 0.75314(11) 0.0203(5) Uani 1 1 d . . . . .
H2 H 0.8405 0.5985 0.7134 0.024 Uiso 1 1 calc R . . . .
C20 C 0.6719(2) 0.0226(2) 0.54051(10) 0.0196(5) Uani 1 1 d . . . . .
C18 C 0.7919(2) 0.0678(2) 0.63181(11) 0.0197(5) Uani 1 1 d . . . . .
H18 H 0.8099 0.1219 0.6640 0.024 Uiso 1 1 calc R . . . .
C16 C 0.8299(2) -0.1237(2) 0.57789(11) 0.0216(5) Uani 1 1 d . . . . .
C5 C 0.7898(2) 0.4929(2) 0.87317(11) 0.0187(5) Uani 1 1 d . . . . .
C3 C 0.7616(2) 0.4607(2) 0.76581(11) 0.0193(5) Uani 1 1 d . . . . .
H3 H 0.7306 0.4117 0.7340 0.023 Uiso 1 1 calc R . . . .
C23 C 0.6233(2) 0.2244(2) 0.60011(10) 0.0173(4) Uani 1 1 d . . . . .
H23 H 0.6013 0.2617 0.5608 0.021 Uiso 1 1 calc R . . . .
C1 C 0.8709(2) 0.6446(2) 0.80111(11) 0.0191(5) Uani 1 1 d . . . . .
C9 C 0.5170(2) 0.3361(2) 0.83672(11) 0.0190(5) Uani 1 1 d . . . . .
H9 H 0.5003 0.3977 0.8691 0.023 Uiso 1 1 calc R . . . .
C30 C 0.5732(2) 0.0566(3) 0.49351(11) 0.0242(5) Uani 1 1 d . . . . .
H30A H 0.4893 0.0489 0.5107 0.036 Uiso 1 1 calc GR . . . .
H30B H 0.5809 0.0000 0.4596 0.036 Uiso 1 1 calc GR . . . .
H30C H 0.5865 0.1425 0.4803 0.036 Uiso 1 1 calc GR . . . .
C29 C 0.7891(2) 0.3776(2) 0.59931(11) 0.0219(5) Uani 1 1 d . . . . .
H29A H 0.7486 0.4267 0.5681 0.033 Uiso 1 1 calc GR . . . .
H29B H 0.8445 0.3154 0.5813 0.033 Uiso 1 1 calc GR . . . .
H29C H 0.8383 0.4329 0.6248 0.033 Uiso 1 1 calc GR . . . .
C6 C 0.8544(2) 0.6056(2) 0.86045(11) 0.0198(5) Uani 1 1 d . . . . .
H6 H 0.8866 0.6548 0.8919 0.024 Uiso 1 1 calc R . . . .
C25 C 0.4167(2) 0.3162(2) 0.64134(12) 0.0242(5) Uani 1 1 d . . . . .
H25A H 0.4674 0.3869 0.6561 0.029 Uiso 1 1 calc R . . . .
H25B H 0.3483 0.3006 0.6700 0.029 Uiso 1 1 calc R . . . .
C14 C 0.7780(3) 0.1214(3) 0.80445(12) 0.0265(6) Uani 1 1 d . . . . .
H14A H 0.7845 0.0596 0.7726 0.040 Uiso 1 1 calc GR . . . .
H14B H 0.7594 0.0790 0.8419 0.040 Uiso 1 1 calc GR . . . .
H14C H 0.8574 0.1665 0.8080 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.4315(2) 0.2212(2) 0.84549(11) 0.0240(5) Uani 1 1 d . . . . .
H10A H 0.4444 0.1621 0.8123 0.029 Uiso 1 1 calc R . . . .
H10B H 0.3427 0.2479 0.8449 0.029 Uiso 1 1 calc R . . . .
C15 C 0.7776(3) 0.4519(3) 0.93844(11) 0.0264(5) Uani 1 1 d . . . . .
H15A H 0.6898 0.4325 0.9472 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.8060 0.5194 0.9644 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.8291 0.3777 0.9452 0.040 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br7 C1 1.904(2) . ?
Br22 C16 1.904(2) . ?
Cl26 C25 1.793(3) . ?
Cl11 C10 1.793(3) . ?
O28 C23 1.425(3) . ?
O28 C29 1.426(3) . ?
O27 H27 0.8200 . ?
O27 C24 1.421(3) . ?
O13 C8 1.426(3) . ?
O13 C14 1.417(3) . ?
O12 H12 0.8200 . ?
O12 C9 1.418(3) . ?
C24 H24 0.9800 . ?
C24 C23 1.533(3) . ?
C24 C25 1.522(4) . ?
C19 C20 1.406(3) . ?
C19 C18 1.395(3) . ?
C19 C23 1.520(3) . ?
C8 H8 0.9800 . ?
C8 C4 1.516(3) . ?
C8 C9 1.541(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(4) . ?
C21 C16 1.383(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(4) . ?
C17 C16 1.386(4) . ?
C4 C5 1.404(3) . ?
C4 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C2 C1 1.381(3) . ?
C20 C30 1.507(3) . ?
C18 H18 0.9300 . ?
C5 C6 1.393(4) . ?
C5 C15 1.511(3) . ?
C3 H3 0.9300 . ?
C23 H23 0.9800 . ?
C1 C6 1.385(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.516(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C6 H6 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C23 O28 C29 112.24(18) . . ?
C24 O27 H27 109.5 . . ?
C14 O13 C8 113.45(18) . . ?
C9 O12 H12 109.5 . . ?
O27 C24 H24 107.5 . . ?
O27 C24 C23 111.96(18) . . ?
O27 C24 C25 109.91(19) . . ?
C23 C24 H24 107.5 . . ?
C25 C24 H24 107.5 . . ?
C25 C24 C23 112.3(2) . . ?
C20 C19 C23 121.1(2) . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 C23 119.0(2) . . ?
O13 C8 H8 108.9 . . ?
O13 C8 C4 112.10(18) . . ?
O13 C8 C9 106.91(18) . . ?
C4 C8 H8 108.9 . . ?
C4 C8 C9 111.2(2) . . ?
C9 C8 H8 108.9 . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C16 C21 C20 120.2(2) . . ?
C18 C17 H17 121.0 . . ?
C18 C17 C16 117.9(2) . . ?
C16 C17 H17 121.0 . . ?
C5 C4 C8 121.3(2) . . ?
C3 C4 C8 119.2(2) . . ?
C3 C4 C5 119.3(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(2) . . ?
C19 C20 C30 121.9(2) . . ?
C21 C20 C19 118.7(2) . . ?
C21 C20 C30 119.4(2) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 C19 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C21 C16 Br22 119.46(19) . . ?
C21 C16 C17 121.9(2) . . ?
C17 C16 Br22 118.60(19) . . ?
C4 C5 C15 122.4(2) . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 C15 118.5(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
O28 C23 C24 106.38(18) . . ?
O28 C23 C19 111.98(18) . . ?
O28 C23 H23 109.1 . . ?
C24 C23 H23 109.1 . . ?
C19 C23 C24 111.1(2) . . ?
C19 C23 H23 109.1 . . ?
C2 C1 Br7 119.28(18) . . ?
C2 C1 C6 121.5(2) . . ?
C6 C1 Br7 119.17(18) . . ?
O12 C9 C8 110.83(19) . . ?
O12 C9 H9 109.1 . . ?
O12 C9 C10 105.26(19) . . ?
C8 C9 H9 109.1 . . ?
C10 C9 C8 113.2(2) . . ?
C10 C9 H9 109.1 . . ?
C20 C30 H30A 109.5 . . ?
C20 C30 H30B 109.5 . . ?
C20 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O28 C29 H29A 109.5 . . ?
O28 C29 H29B 109.5 . . ?
O28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.2(2) . . ?
C1 C6 H6 119.9 . . ?
Cl26 C25 H25A 109.9 . . ?
Cl26 C25 H25B 109.9 . . ?
C24 C25 Cl26 109.11(17) . . ?
C24 C25 H25A 109.9 . . ?
C24 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Cl11 C10 H10A 109.3 . . ?
Cl11 C10 H10B 109.3 . . ?
C9 C10 Cl11 111.43(17) . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Br7 C1 C6 C5 178.70(18) . . . . ?
O27 C24 C23 O28 -60.9(2) . . . . ?
O27 C24 C23 C19 61.2(2) . . . . ?
O27 C24 C25 Cl26 -164.65(15) . . . . ?
O13 C8 C4 C5 -147.9(2) . . . . ?
O13 C8 C4 C3 36.3(3) . . . . ?
O13 C8 C9 O12 -62.8(2) . . . . ?
O13 C8 C9 C10 55.2(2) . . . . ?
O12 C9 C10 Cl11 -179.18(15) . . . . ?
C8 C4 C5 C6 -174.5(2) . . . . ?
C8 C4 C5 C15 7.2(4) . . . . ?
C8 C4 C3 C2 175.0(2) . . . . ?
C8 C9 C10 Cl11 59.6(2) . . . . ?
C4 C8 C9 O12 59.8(2) . . . . ?
C4 C8 C9 C10 177.82(19) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
C20 C19 C18 C17 -1.1(4) . . . . ?
C20 C19 C23 O28 -155.7(2) . . . . ?
C20 C19 C23 C24 85.5(3) . . . . ?
C20 C21 C16 Br22 178.19(17) . . . . ?
C20 C21 C16 C17 -0.7(4) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C18 C19 C20 C30 -179.2(2) . . . . ?
C18 C19 C23 O28 26.8(3) . . . . ?
C18 C19 C23 C24 -92.0(2) . . . . ?
C18 C17 C16 Br22 -178.40(18) . . . . ?
C18 C17 C16 C21 0.5(4) . . . . ?
C16 C21 C20 C19 0.0(3) . . . . ?
C16 C21 C20 C30 180.0(2) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C5 C4 C3 C2 -0.8(4) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C3 C4 C5 C15 -177.0(2) . . . . ?
C3 C2 C1 Br7 -178.28(18) . . . . ?
C3 C2 C1 C6 1.8(4) . . . . ?
C23 C24 C25 Cl26 70.0(2) . . . . ?
C23 C19 C20 C21 -176.6(2) . . . . ?
C23 C19 C20 C30 3.4(3) . . . . ?
C23 C19 C18 C17 176.5(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C9 C8 C4 C5 92.5(3) . . . . ?
C9 C8 C4 C3 -83.3(3) . . . . ?
C29 O28 C23 C24 -161.54(19) . . . . ?
C29 O28 C23 C19 76.9(2) . . . . ?
C25 C24 C23 O28 63.3(2) . . . . ?
C25 C24 C23 C19 -174.59(19) . . . . ?
C14 O13 C8 C4 89.9(2) . . . . ?
C14 O13 C8 C9 -148.0(2) . . . . ?
C15 C5 C6 C1 178.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.359
_oxdiff_exptl_absorpt_empirical_full_min 0.843
