# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_11955
_database_code_depnum_ccdc_archive 'CCDC 2155801'
loop_
_audit_author_name
_audit_author_address
'Biao Wang'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2022-03-02 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 Cl F O3'
_chemical_formula_weight         495.00

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4244(8)
_cell_length_b                   9.7735(8)
_cell_length_c                   16.0599(13)
_cell_angle_alpha                105.511(7)
_cell_angle_beta                 106.708(7)
_cell_angle_gamma                93.809(7)
_cell_volume                     1348.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2383
_cell_measurement_theta_min      4.7330
_cell_measurement_theta_max      69.8700

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.538
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.849
_exptl_absorpt_correction_T_min  0.85807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8428
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.011
_diffrn_reflns_theta_max         67.250
_diffrn_reflns_theta_full        67.250
_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             4832
_reflns_number_gt                3041
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0566P)²+0.0198P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0126(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4832
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Cl1 Cl 0.83564(8) 0.26550(10) 0.30405(5) 0.0790(3) Uani 1 1 d . . . . .
O1 O 0.2848(2) 0.3957(3) 0.21988(13) 0.0784(7) Uani 1 1 d . . . . .
O2 O 0.4722(2) 0.4115(3) 0.34324(12) 0.0762(7) Uani 1 1 d . . . . .
H2 H 0.403750 0.407045 0.364933 0.114 Uiso 1 1 calc R U . . .
O3 O 0.2647(3) 0.4078(3) 0.43024(15) 0.0936(8) Uani 1 1 d . . . . .
F1 F 0.6878(3) 1.0569(2) 0.41979(14) 0.1207(9) Uani 1 1 d . . . . .
C1 C 0.8162(3) 0.2450(3) 0.18928(18) 0.0528(7) Uani 1 1 d . . . . .
C2 C 0.9483(3) 0.2406(3) 0.1694(2) 0.0654(8) Uani 1 1 d . . . . .
H2A H 1.038519 0.252827 0.215679 0.078 Uiso 1 1 calc R U . . .
C3 C 0.9469(4) 0.2179(3) 0.0808(3) 0.0731(9) Uani 1 1 d . . . . .
H3 H 1.036049 0.214595 0.066809 0.088 Uiso 1 1 calc R U . . .
C4 C 0.8134(4) 0.2004(3) 0.0135(2) 0.0675(8) Uani 1 1 d . . . . .
H4A H 0.811468 0.181901 -0.046750 0.081 Uiso 1 1 calc R U . . .
C5 C 0.6807(3) 0.2100(3) 0.03457(19) 0.0545(7) Uani 1 1 d . . . . .
H5 H 0.591705 0.201249 -0.011924 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6770(3) 0.2326(3) 0.12374(17) 0.0467(6) Uani 1 1 d . . . . .
C7 C 0.5262(3) 0.2434(3) 0.14312(17) 0.0444(6) Uani 1 1 d . . . . .
C8 C 0.3982(3) 0.2230(3) 0.05664(17) 0.0480(6) Uani 1 1 d . . . . .
H8 H 0.362805 0.128959 0.019379 0.058 Uiso 1 1 calc R U . . .
C9 C 0.3307(3) 0.3246(3) 0.02792(16) 0.0434(6) Uani 1 1 d . . . . .
C10 C 0.1967(3) 0.2896(3) -0.05517(16) 0.0464(6) Uani 1 1 d . . . . .
C11 C 0.1460(3) 0.1503(3) -0.11333(19) 0.0638(8) Uani 1 1 d . . . . .
H11 H 0.198008 0.076798 -0.100720 0.077 Uiso 1 1 calc R U . . .
C12 C 0.0203(4) 0.1183(3) -0.1894(2) 0.0733(9) Uani 1 1 d . . . . .
H12 H -0.011313 0.023892 -0.226904 0.088 Uiso 1 1 calc R U . . .
C13 C -0.0583(3) 0.2244(3) -0.2102(2) 0.0656(8) Uani 1 1 d . . . . .
H13 H -0.142212 0.202860 -0.261883 0.079 Uiso 1 1 calc R U . . .
C14 C -0.0114(3) 0.3624(3) -0.1540(2) 0.0626(8) Uani 1 1 d . . . . .
H14 H -0.064269 0.435156 -0.167087 0.075 Uiso 1 1 calc R U . . .
C15 C 0.1142(3) 0.3943(3) -0.07756(19) 0.0560(7) Uani 1 1 d . . . . .
H15 H 0.144152 0.488839 -0.040129 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3824(3) 0.4813(3) 0.08079(16) 0.0498(6) Uani 1 1 d . . . . .
H16A H 0.305020 0.518091 0.105352 0.060 Uiso 1 1 calc R U . . .
H16B H 0.395186 0.533917 0.039430 0.060 Uiso 1 1 calc R U . . .
C17 C 0.5288(3) 0.5091(3) 0.15870(16) 0.0454(6) Uani 1 1 d . . . . .
H17 H 0.608595 0.497927 0.130625 0.054 Uiso 1 1 calc R U . . .
C18 C 0.5355(3) 0.3949(3) 0.20988(16) 0.0442(6) Uani 1 1 d . . . . .
H18 H 0.633144 0.417233 0.257581 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5681(3) 0.6594(3) 0.22599(17) 0.0506(6) Uani 1 1 d . . . . .
C20 C 0.4629(4) 0.7381(3) 0.2488(2) 0.0813(10) Uani 1 1 d . . . . .
H20 H 0.361831 0.701425 0.219243 0.098 Uiso 1 1 calc R U . . .
C21 C 0.5027(5) 0.8714(4) 0.3148(3) 0.0967(13) Uani 1 1 d . . . . .
H21 H 0.429801 0.922159 0.331027 0.116 Uiso 1 1 calc R U . . .
C22 C 0.6471(5) 0.9245(3) 0.3542(2) 0.0796(10) Uani 1 1 d . . . . .
C23 C 0.7566(5) 0.8534(4) 0.3344(2) 0.0940(12) Uani 1 1 d . . . . .
H23 H 0.857060 0.892912 0.363618 0.113 Uiso 1 1 calc R U . . .
C24 C 0.7149(4) 0.7189(3) 0.2686(2) 0.0754(9) Uani 1 1 d . . . . .
H24 H 0.788977 0.668740 0.253583 0.090 Uiso 1 1 calc R U . . .
C25 C 0.4909(3) 0.1220(3) 0.18325(19) 0.0577(7) Uani 1 1 d . . . . .
H25A H 0.390131 0.118864 0.185588 0.087 Uiso 1 1 calc R U . . .
H25B H 0.559586 0.140629 0.243640 0.087 Uiso 1 1 calc R U . . .
H25C H 0.501177 0.031341 0.145310 0.087 Uiso 1 1 calc R U . . .
C26 C 0.4157(3) 0.3997(3) 0.25574(17) 0.0489(6) Uani 1 1 d . . . . .
C27 C 0.1884(8) 0.6232(6) 0.4107(4) 0.168(2) Uani 1 1 d . . . . .
H27A H 0.284593 0.669916 0.415625 0.252 Uiso 1 1 calc R U . . .
H27B H 0.129586 0.694353 0.430128 0.252 Uiso 1 1 calc R U . . .
H27C H 0.137727 0.567709 0.348547 0.252 Uiso 1 1 calc R U . . .
C28 C 0.2078(5) 0.5318(6) 0.4665(3) 0.1192(17) Uani 1 1 d . . . . .
H28A H 0.276170 0.583926 0.526484 0.143 Uiso 1 1 calc R U . . .
H28B H 0.112128 0.503366 0.473223 0.143 Uiso 1 1 calc R U . . .
C29 C 0.2591(6) 0.3016(6) 0.4732(3) 0.1231(16) Uani 1 1 d . . . . .
H29A H 0.159209 0.284320 0.477351 0.148 Uiso 1 1 calc R U . . .
H29B H 0.328995 0.335738 0.534637 0.148 Uiso 1 1 calc R U . . .
C30 C 0.2951(7) 0.1696(6) 0.4256(4) 0.169(2) Uani 1 1 d . . . . .
H30A H 0.252931 0.153084 0.361129 0.254 Uiso 1 1 calc R U . . .
H30B H 0.254607 0.091974 0.442203 0.254 Uiso 1 1 calc R U . . .
H30C H 0.402115 0.175238 0.441549 0.254 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
Cl1 C1 1.753(3) . ?
O1 C26 1.195(3) . ?
O2 C26 1.321(3) . ?
O3 C29 1.396(5) . ?
O3 C28 1.408(4) . ?
F1 C22 1.380(3) . ?
C1 C2 1.372(4) . ?
C1 C6 1.400(3) . ?
C2 C3 1.377(4) . ?
C3 C4 1.368(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.401(3) . ?
C6 C7 1.543(3) . ?
C7 C8 1.510(3) . ?
C7 C25 1.554(3) . ?
C7 C18 1.559(3) . ?
C8 C9 1.328(3) . ?
C9 C10 1.491(3) . ?
C9 C16 1.507(3) . ?
C10 C15 1.387(4) . ?
C10 C11 1.389(3) . ?
C11 C12 1.382(4) . ?
C12 C13 1.372(4) . ?
C13 C14 1.368(4) . ?
C14 C15 1.384(4) . ?
C16 C17 1.523(3) . ?
C17 C19 1.520(3) . ?
C17 C18 1.548(3) . ?
C18 C26 1.511(3) . ?
C19 C24 1.363(4) . ?
C19 C20 1.367(4) . ?
C20 C21 1.389(4) . ?
C21 C22 1.326(5) . ?
C22 C23 1.347(5) . ?
C23 C24 1.396(4) . ?
C27 C28 1.410(6) . ?
C29 C30 1.429(6) . ?

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
C29 O3 C28 114.2(3) . . ?
C2 C1 C6 123.2(3) . . ?
C2 C1 Cl1 114.3(2) . . ?
C6 C1 Cl1 122.5(2) . . ?
C1 C2 C3 119.8(3) . . ?
C4 C3 C2 119.4(3) . . ?
C3 C4 C5 120.4(3) . . ?
C4 C5 C6 122.0(3) . . ?
C1 C6 C5 115.1(2) . . ?
C1 C6 C7 125.3(2) . . ?
C5 C6 C7 119.7(2) . . ?
C8 C7 C6 111.3(2) . . ?
C8 C7 C25 106.7(2) . . ?
C6 C7 C25 109.8(2) . . ?
C8 C7 C18 108.7(2) . . ?
C6 C7 C18 108.96(19) . . ?
C25 C7 C18 111.4(2) . . ?
C9 C8 C7 127.2(2) . . ?
C8 C9 C10 122.0(2) . . ?
C8 C9 C16 121.1(2) . . ?
C10 C9 C16 116.8(2) . . ?
C15 C10 C11 116.4(2) . . ?
C15 C10 C9 121.6(2) . . ?
C11 C10 C9 122.0(2) . . ?
C12 C11 C10 121.7(3) . . ?
C13 C12 C11 120.6(3) . . ?
C14 C13 C12 119.0(3) . . ?
C13 C14 C15 120.4(3) . . ?
C14 C15 C10 121.9(3) . . ?
C9 C16 C17 113.5(2) . . ?
C19 C17 C16 115.3(2) . . ?
C19 C17 C18 110.2(2) . . ?
C16 C17 C18 111.9(2) . . ?
C26 C18 C17 111.6(2) . . ?
C26 C18 C7 112.3(2) . . ?
C17 C18 C7 109.64(19) . . ?
C24 C19 C20 117.3(3) . . ?
C24 C19 C17 119.4(3) . . ?
C20 C19 C17 123.3(3) . . ?
C19 C20 C21 121.9(3) . . ?
C22 C21 C20 118.4(3) . . ?
C21 C22 C23 122.9(3) . . ?
C21 C22 F1 118.8(4) . . ?
C23 C22 F1 118.3(4) . . ?
C22 C23 C24 118.1(3) . . ?
C19 C24 C23 121.5(3) . . ?
O1 C26 O2 122.1(3) . . ?
O1 C26 C18 125.8(2) . . ?
O2 C26 C18 112.1(2) . . ?
O3 C28 C27 112.2(4) . . ?
O3 C29 C30 112.4(4) . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_210825tx_0m
_database_code_depnum_ccdc_archive 'CCDC 2155802'
loop_
_audit_author_name
_audit_author_address
'Biao Wang'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2022-03-02 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2021-08-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 Br Cl O2'
_chemical_formula_sum            'C26 H22 Br Cl O2'
_chemical_formula_weight         481.79
_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'
Cl Cl 0.1484 0.1585 '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                   7.0573(7)
_cell_length_b                   18.127(2)
_cell_length_c                   33.894(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4336.0(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.69
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.822
_shelx_estimated_absorpt_T_min   0.686
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0980 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.6756.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_colour_lustre     .
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26041
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.453
_diffrn_reflns_theta_min         1.274
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                6697
_reflns_number_total             9783
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 2215 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         9783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.1079
_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:
 C009(H009), C00D(H00F), C00F(H00G), C00L(H00L), C00O(H00O), C01D(H01L)
2.b Secondary CH2 refined with riding coordinates:
 C00U(H00D,H00E), C013(H01D,H01F)
2.c Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00N(H00N), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V),
 C00W(H00W), C00Y(H00Y), C00Z(H00Z), C012(H012), C014(H014), C015(H015),
 C016(H016), C019(H019), C01A(H01G), C01B(H01I), C01C(H01J), C01E(H01E),
 C01F(H01M), C01G(H01N), C01H(H01H), C01I(H01O), C01J(H01P), C01K(H01K),
 C01L(H01Q), C01M(H01R), C01N(H01S), C01O(H01T)
2.d Idealised Me refined as rotating group:
 C00B(H00A,H00B,H00C), C010(H01A,H01B,H01C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.03880(10) 0.08361(3) 0.28078(2) 0.04056(18) Uani 1 1 d . . . . .
Br02 Br 0.46300(10) 0.65840(3) 0.38925(2) 0.04187(19) Uani 1 1 d . . . . .
Cl03 Cl 0.1936(2) 0.16714(9) 0.19779(4) 0.0424(4) Uani 1 1 d . . . . .
Cl04 Cl 0.3030(3) 0.57370(9) 0.30468(5) 0.0508(5) Uani 1 1 d . . . . .
O005 O 0.5612(5) 0.11442(18) 0.33509(11) 0.0259(9) Uani 1 1 d . . . . .
O006 O -0.0559(6) 0.61936(19) 0.44386(11) 0.0318(9) Uani 1 1 d . . . . .
O007 O 0.7083(6) 0.2182(2) 0.34998(12) 0.0366(11) Uani 1 1 d . . . . .
O008 O -0.1897(6) 0.5126(2) 0.45849(14) 0.0456(12) Uani 1 1 d . . . . .
C009 C 0.2187(8) 0.1967(3) 0.35660(15) 0.0238(13) Uani 1 1 d . . . . .
H009 H 0.098233 0.204655 0.342865 0.029 Uiso 1 1 calc R U . . .
C00A C 0.3697(7) 0.0841(3) 0.32740(16) 0.0228(12) Uani 1 1 d . . . . .
C00B C 0.5228(8) 0.2170(3) 0.26118(16) 0.0287(13) Uani 1 1 d . . . . .
H00A H 0.621608 0.184748 0.270229 0.043 Uiso 1 1 calc R U . . .
H00B H 0.561332 0.267328 0.264644 0.043 Uiso 1 1 calc R U . . .
H00C H 0.498572 0.207794 0.233745 0.043 Uiso 1 1 calc R U . . .
C00C C 0.5640(9) 0.1893(3) 0.33967(15) 0.0254(13) Uani 1 1 d . . . . .
C00D C 0.2925(8) 0.5410(3) 0.46513(16) 0.0253(13) Uani 1 1 d . . . . .
H00F H 0.415276 0.534711 0.452030 0.030 Uiso 1 1 calc R U . . .
C00E C 0.2073(8) 0.2365(3) 0.39570(16) 0.0239(12) Uani 1 1 d . . . . .
C00F C 0.1367(8) 0.5122(3) 0.43654(16) 0.0253(13) Uani 1 1 d . . . . .
H00G H 0.129749 0.458230 0.437996 0.030 Uiso 1 1 calc R U . . .
C00G C 0.3383(7) 0.2023(3) 0.28551(15) 0.0200(12) Uani 1 1 d . . . . .
C00H C 0.1755(8) 0.5367(3) 0.39292(16) 0.0239(12) Uani 1 1 d . . . . .
C00I C 0.4059(8) 0.0009(3) 0.32699(16) 0.0233(13) Uani 1 1 d . . . . .
C00J C 0.3383(8) 0.4943(3) 0.37390(16) 0.0238(12) Uani 1 1 d . . . . .
C00K C 0.0472(10) 0.2771(3) 0.40486(16) 0.0315(13) Uani 1 1 d . . . . .
H00K H -0.050029 0.280742 0.386435 0.038 Uiso 1 1 calc R U . . .
C00L C 0.3034(7) 0.1158(3) 0.28727(16) 0.0230(12) Uani 1 1 d . . . . .
H00L H 0.379148 0.092750 0.266415 0.028 Uiso 1 1 calc R U . . .
C00M C 0.2977(8) 0.4971(3) 0.50329(16) 0.0263(13) Uani 1 1 d . . . . .
C00N C 0.1153(8) 0.3133(3) 0.28535(18) 0.0304(14) Uani 1 1 d . . . . .
H00N H 0.155527 0.323455 0.310915 0.036 Uiso 1 1 calc R U . . .
C00O C 0.3790(8) 0.2244(3) 0.32911(16) 0.0227(12) Uani 1 1 d . . . . .
H00O H 0.389927 0.278195 0.331157 0.027 Uiso 1 1 calc R U . . .
C00P C -0.0506(9) 0.5450(3) 0.44781(16) 0.0305(13) Uani 1 1 d . . . . .
C00Q C 0.1825(7) 0.2493(3) 0.26671(15) 0.0229(12) Uani 1 1 d . . . . .
C00R C 0.4551(10) 0.4068(3) 0.54408(18) 0.0417(15) Uani 1 1 d . . . . .
H00R H 0.556336 0.374861 0.548153 0.050 Uiso 1 1 calc R U . . .
C00S C 0.4481(9) 0.4494(3) 0.51010(16) 0.0289(13) Uani 1 1 d . . . . .
H00S H 0.545239 0.445862 0.491656 0.035 Uiso 1 1 calc R U . . .
C00T C 0.1717(10) 0.3088(3) 0.46812(18) 0.0395(16) Uani 1 1 d . . . . .
H00T H 0.160207 0.333109 0.492173 0.047 Uiso 1 1 calc R U . . .
C00U C 0.2455(8) 0.1122(3) 0.36130(15) 0.0252(13) Uani 1 1 d . . . . .
H00D H 0.305541 0.101508 0.386399 0.030 Uiso 1 1 calc R U . . .
H00E H 0.123307 0.087749 0.360721 0.030 Uiso 1 1 calc R U . . .
C00V C 0.3223(9) -0.0462(3) 0.35343(18) 0.0330(14) Uani 1 1 d . . . . .
H00V H 0.230814 -0.028421 0.370757 0.040 Uiso 1 1 calc R U . . .
C00W C 0.0286(10) 0.3124(3) 0.44089(17) 0.0385(15) Uani 1 1 d . . . . .
H00W H -0.081421 0.338517 0.446621 0.046 Uiso 1 1 calc R U . . .
C00X C 0.1339(8) 0.6524(3) 0.43617(17) 0.0263(13) Uani 1 1 d . . . . .
C00Y C 0.3507(9) 0.2336(3) 0.42400(17) 0.0336(14) Uani 1 1 d . . . . .
H00Y H 0.460574 0.207062 0.418632 0.040 Uiso 1 1 calc R U . . .
C00Z C 0.3729(10) -0.1198(3) 0.35451(19) 0.0387(16) Uani 1 1 d . . . . .
H00Z H 0.317824 -0.150894 0.373073 0.046 Uiso 1 1 calc R U . . .
C010 C -0.0076(8) 0.5194(3) 0.36895(17) 0.0356(15) Uani 1 1 d . . . . .
H01A H -0.043287 0.468895 0.373106 0.053 Uiso 1 1 calc R U . . .
H01B H 0.015917 0.527467 0.341388 0.053 Uiso 1 1 calc R U . . .
H01C H -0.108194 0.551177 0.377591 0.053 Uiso 1 1 calc R U . . .
C011 C 0.0957(8) 0.7356(3) 0.43580(17) 0.0299(14) Uani 1 1 d . . . . .
C012 C 0.5040(9) -0.1474(3) 0.32836(18) 0.0391(16) Uani 1 1 d . . . . .
H012 H 0.537747 -0.196973 0.329193 0.047 Uiso 1 1 calc R U . . .
C013 C 0.2585(9) 0.6249(3) 0.47036(16) 0.0288(14) Uani 1 1 d . . . . .
H01D H 0.195860 0.634222 0.495341 0.035 Uiso 1 1 calc R U . . .
H01F H 0.378589 0.650922 0.470321 0.035 Uiso 1 1 calc R U . . .
C014 C 0.5375(10) -0.0266(3) 0.30071(17) 0.0334(14) Uani 1 1 d . . . . .
H014 H 0.595158 0.004855 0.282664 0.040 Uiso 1 1 calc R U . . .
C015 C 0.5843(9) -0.1012(3) 0.30110(19) 0.0428(17) Uani 1 1 d . . . . .
H015 H 0.670284 -0.119752 0.282817 0.051 Uiso 1 1 calc R U . . .
C016 C 0.3142(10) 0.4115(4) 0.57158(19) 0.0470(18) Uani 1 1 d . . . . .
H016 H 0.318370 0.382518 0.594201 0.056 Uiso 1 1 calc R U . . .
C017 C 0.3977(9) 0.5039(3) 0.33477(17) 0.0325(14) Uani 1 1 d . . . . .
C018 C 0.1141(8) 0.2391(3) 0.22805(17) 0.0305(14) Uani 1 1 d . . . . .
C019 C -0.0067(8) 0.3614(3) 0.26749(18) 0.0371(16) Uani 1 1 d . . . . .
H019 H -0.044503 0.403620 0.280983 0.044 Uiso 1 1 calc R U . . .
C01A C 0.4263(8) 0.4351(3) 0.39368(17) 0.0303(14) Uani 1 1 d . . . . .
H01G H 0.390165 0.425069 0.419516 0.036 Uiso 1 1 calc R U . . .
C01B C 0.5641(8) 0.3910(3) 0.37647(18) 0.0321(14) Uani 1 1 d . . . . .
H01I H 0.619399 0.353119 0.390938 0.039 Uiso 1 1 calc R U . . .
C01C C 0.0189(11) 0.8865(3) 0.4321(2) 0.0475(19) Uani 1 1 d . . . . .
H01J H -0.006416 0.936761 0.430903 0.057 Uiso 1 1 calc R U . . .
C01D C 0.2018(8) 0.6234(3) 0.39599(16) 0.0266(13) Uani 1 1 d . . . . .
H01L H 0.123666 0.646323 0.375477 0.032 Uiso 1 1 calc R U . . .
C01E C 0.3329(10) 0.2690(3) 0.45955(19) 0.0436(17) Uani 1 1 d . . . . .
H01E H 0.430237 0.266119 0.477989 0.052 Uiso 1 1 calc R U . . .
C01F C 0.1585(9) 0.5012(4) 0.53144(18) 0.0412(16) Uani 1 1 d . . . . .
H01M H 0.056557 0.532775 0.527419 0.049 Uiso 1 1 calc R U . . .
C01G C 0.1653(10) 0.4597(4) 0.5655(2) 0.0503(19) Uani 1 1 d . . . . .
H01N H 0.070175 0.464221 0.584373 0.060 Uiso 1 1 calc R U . . .
C01H C -0.0742(9) 0.3492(4) 0.2306(2) 0.0460(18) Uani 1 1 d . . . . .
H01H H -0.158780 0.382044 0.218940 0.055 Uiso 1 1 calc R U . . .
C01I C 0.5357(10) 0.4604(3) 0.31738(18) 0.0419(16) Uani 1 1 d . . . . .
H01O H 0.572996 0.469550 0.291519 0.050 Uiso 1 1 calc R U . . .
C01J C 0.6188(9) 0.4030(3) 0.3385(2) 0.0400(17) Uani 1 1 d . . . . .
H01P H 0.710344 0.373266 0.326853 0.048 Uiso 1 1 calc R U . . .
C01K C -0.0146(9) 0.2871(3) 0.21074(18) 0.0415(17) Uani 1 1 d . . . . .
H01K H -0.060807 0.277323 0.185589 0.050 Uiso 1 1 calc R U . . .
C01L C -0.0413(11) 0.7627(3) 0.41072(18) 0.0431(16) Uani 1 1 d . . . . .
H01Q H -0.108832 0.730291 0.394783 0.052 Uiso 1 1 calc R U . . .
C01M C 0.1548(11) 0.8603(3) 0.4571(2) 0.0488(19) Uani 1 1 d . . . . .
H01R H 0.222337 0.893230 0.472801 0.059 Uiso 1 1 calc R U . . .
C01N C -0.0803(10) 0.8380(3) 0.4089(2) 0.0487(18) Uani 1 1 d . . . . .
H01S H -0.173477 0.855460 0.391832 0.058 Uiso 1 1 calc R U . . .
C01O C 0.1942(10) 0.7849(3) 0.45950(19) 0.0388(16) Uani 1 1 d . . . . .
H01T H 0.286137 0.767745 0.476904 0.047 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
Br01 C00L 1.969(5) . ?
Br02 C01D 1.963(5) . ?
Cl03 C018 1.752(6) . ?
Cl04 C017 1.757(6) . ?
O005 C00A 1.482(6) . ?
O005 C00C 1.366(6) . ?
O006 C00P 1.355(6) . ?
O006 C00X 1.491(6) . ?
O007 C00C 1.198(7) . ?
O008 C00P 1.200(7) . ?
C009 H009 0.9800 . ?
C009 C00E 1.511(7) . ?
C009 C00O 1.549(8) . ?
C009 C00U 1.551(7) . ?
C00A C00I 1.530(7) . ?
C00A C00L 1.549(7) . ?
C00A C00U 1.533(7) . ?
C00B H00A 0.9600 . ?
C00B H00B 0.9600 . ?
C00B H00C 0.9600 . ?
C00B C00G 1.564(7) . ?
C00C C00O 1.496(8) . ?
C00D H00F 0.9800 . ?
C00D C00F 1.556(8) . ?
C00D C00M 1.519(7) . ?
C00D C013 1.550(7) . ?
C00E C00K 1.384(8) . ?
C00E C00Y 1.396(8) . ?
C00F H00G 0.9800 . ?
C00F C00H 1.568(8) . ?
C00F C00P 1.499(8) . ?
C00G C00L 1.588(6) . ?
C00G C00O 1.558(7) . ?
C00G C00Q 1.529(7) . ?
C00H C00J 1.526(8) . ?
C00H C010 1.558(8) . ?
C00H C01D 1.585(7) . ?
C00I C00V 1.371(7) . ?
C00I C014 1.380(8) . ?
C00J C017 1.402(8) . ?
C00J C01A 1.409(7) . ?
C00K H00K 0.9300 . ?
C00K C00W 1.385(8) . ?
C00L H00L 0.9800 . ?
C00M C00S 1.389(8) . ?
C00M C01F 1.371(8) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.405(7) . ?
C00N C019 1.367(7) . ?
C00O H00O 0.9800 . ?
C00Q C018 1.409(8) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.387(8) . ?
C00R C016 1.366(9) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00T C00W 1.370(9) . ?
C00T C01E 1.379(9) . ?
C00U H00D 0.9700 . ?
C00U H00E 0.9700 . ?
C00V H00V 0.9300 . ?
C00V C00Z 1.382(8) . ?
C00W H00W 0.9300 . ?
C00X C011 1.533(7) . ?
C00X C013 1.537(7) . ?
C00X C01D 1.536(8) . ?
C00Y H00Y 0.9300 . ?
C00Y C01E 1.371(8) . ?
C00Z H00Z 0.9300 . ?
C00Z C012 1.376(8) . ?
C010 H01A 0.9600 . ?
C010 H01B 0.9600 . ?
C010 H01C 0.9600 . ?
C011 C01L 1.378(8) . ?
C011 C01O 1.388(8) . ?
C012 H012 0.9300 . ?
C012 C015 1.370(8) . ?
C013 H01D 0.9700 . ?
C013 H01F 0.9700 . ?
C014 H014 0.9300 . ?
C014 C015 1.393(7) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C01G 1.382(9) . ?
C017 C01I 1.385(8) . ?
C018 C01K 1.388(8) . ?
C019 H019 0.9300 . ?
C019 C01H 1.357(8) . ?
C01A H01G 0.9300 . ?
C01A C01B 1.387(8) . ?
C01B H01I 0.9300 . ?
C01B C01J 1.360(8) . ?
C01C H01J 0.9300 . ?
C01C C01M 1.364(10) . ?
C01C C01N 1.372(9) . ?
C01D H01L 0.9800 . ?
C01E H01E 0.9300 . ?
C01F H01M 0.9300 . ?
C01F C01G 1.379(8) . ?
C01G H01N 0.9300 . ?
C01H H01H 0.9300 . ?
C01H C01K 1.377(9) . ?
C01I H01O 0.9300 . ?
C01I C01J 1.393(8) . ?
C01J H01P 0.9300 . ?
C01K H01K 0.9300 . ?
C01L H01Q 0.9300 . ?
C01L C01N 1.394(8) . ?
C01M H01R 0.9300 . ?
C01M C01O 1.398(8) . ?
C01N H01S 0.9300 . ?
C01O H01T 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C O005 C00A 113.7(4) . . ?
C00P O006 C00X 113.1(5) . . ?
C00E C009 H009 107.5 . . ?
C00E C009 C00O 114.3(4) . . ?
C00E C009 C00U 112.8(4) . . ?
C00O C009 H009 107.5 . . ?
C00O C009 C00U 107.0(5) . . ?
C00U C009 H009 107.5 . . ?
O005 C00A C00I 102.4(4) . . ?
O005 C00A C00L 107.0(4) . . ?
O005 C00A C00U 105.4(4) . . ?
C00I C00A C00L 114.1(5) . . ?
C00I C00A C00U 115.5(4) . . ?
C00U C00A C00L 111.2(4) . . ?
H00A C00B H00B 109.5 . . ?
H00A C00B H00C 109.5 . . ?
H00B C00B H00C 109.5 . . ?
C00G C00B H00A 109.5 . . ?
C00G C00B H00B 109.5 . . ?
C00G C00B H00C 109.5 . . ?
O005 C00C C00O 112.5(5) . . ?
O007 C00C O005 118.7(5) . . ?
O007 C00C C00O 128.7(5) . . ?
C00F C00D H00F 107.7 . . ?
C00M C00D H00F 107.7 . . ?
C00M C00D C00F 111.8(4) . . ?
C00M C00D C013 114.8(5) . . ?
C013 C00D H00F 107.7 . . ?
C013 C00D C00F 106.9(5) . . ?
C00K C00E C009 119.6(5) . . ?
C00K C00E C00Y 117.3(5) . . ?
C00Y C00E C009 123.1(5) . . ?
C00D C00F H00G 109.8 . . ?
C00D C00F C00H 111.6(4) . . ?
C00H C00F H00G 109.8 . . ?
C00P C00F C00D 109.3(5) . . ?
C00P C00F H00G 109.8 . . ?
C00P C00F C00H 106.3(5) . . ?
C00B C00G C00L 108.5(4) . . ?
C00O C00G C00B 107.6(4) . . ?
C00O C00G C00L 104.3(4) . . ?
C00Q C00G C00B 106.5(4) . . ?
C00Q C00G C00L 117.0(4) . . ?
C00Q C00G C00O 112.6(4) . . ?
C00F C00H C01D 103.9(4) . . ?
C00J C00H C00F 112.7(4) . . ?
C00J C00H C010 107.6(4) . . ?
C00J C00H C01D 116.1(4) . . ?
C010 C00H C00F 106.8(4) . . ?
C010 C00H C01D 109.3(4) . . ?
C00V C00I C00A 122.4(5) . . ?
C00V C00I C014 119.2(5) . . ?
C014 C00I C00A 118.3(5) . . ?
C017 C00J C00H 124.2(5) . . ?
C017 C00J C01A 114.4(5) . . ?
C01A C00J C00H 121.0(5) . . ?
C00E C00K H00K 119.3 . . ?
C00E C00K C00W 121.4(6) . . ?
C00W C00K H00K 119.3 . . ?
Br01 C00L H00L 108.1 . . ?
C00A C00L Br01 105.9(3) . . ?
C00A C00L C00G 110.7(4) . . ?
C00A C00L H00L 108.1 . . ?
C00G C00L Br01 115.8(4) . . ?
C00G C00L H00L 108.1 . . ?
C00S C00M C00D 119.1(5) . . ?
C01F C00M C00D 123.2(5) . . ?
C01F C00M C00S 117.7(5) . . ?
C00Q C00N H00N 118.6 . . ?
C019 C00N H00N 118.6 . . ?
C019 C00N C00Q 122.7(6) . . ?
C009 C00O C00G 110.6(4) . . ?
C009 C00O H00O 109.7 . . ?
C00C C00O C009 110.8(4) . . ?
C00C C00O C00G 106.1(4) . . ?
C00C C00O H00O 109.7 . . ?
C00G C00O H00O 109.7 . . ?
O006 C00P C00F 113.2(5) . . ?
O008 C00P O006 119.6(6) . . ?
O008 C00P C00F 127.2(5) . . ?
C00N C00Q C00G 121.0(5) . . ?
C00N C00Q C018 114.2(5) . . ?
C018 C00Q C00G 124.2(5) . . ?
C00S C00R H00R 119.8 . . ?
C016 C00R H00R 119.8 . . ?
C016 C00R C00S 120.4(6) . . ?
C00M C00S H00S 119.6 . . ?
C00R C00S C00M 120.8(6) . . ?
C00R C00S H00S 119.6 . . ?
C00W C00T H00T 120.3 . . ?
C00W C00T C01E 119.4(6) . . ?
C01E C00T H00T 120.3 . . ?
C009 C00U H00D 109.9 . . ?
C009 C00U H00E 109.9 . . ?
C00A C00U C009 108.7(4) . . ?
C00A C00U H00D 109.9 . . ?
C00A C00U H00E 109.9 . . ?
H00D C00U H00E 108.3 . . ?
C00I C00V H00V 119.8 . . ?
C00I C00V C00Z 120.5(6) . . ?
C00Z C00V H00V 119.8 . . ?
C00K C00W H00W 119.9 . . ?
C00T C00W C00K 120.2(6) . . ?
C00T C00W H00W 119.9 . . ?
O006 C00X C011 103.8(4) . . ?
O006 C00X C013 104.6(4) . . ?
O006 C00X C01D 107.3(4) . . ?
C011 C00X C013 115.2(5) . . ?
C011 C00X C01D 112.6(5) . . ?
C01D C00X C013 112.3(4) . . ?
C00E C00Y H00Y 119.3 . . ?
C01E C00Y C00E 121.3(6) . . ?
C01E C00Y H00Y 119.3 . . ?
C00V C00Z H00Z 119.7 . . ?
C012 C00Z C00V 120.6(6) . . ?
C012 C00Z H00Z 119.7 . . ?
C00H C010 H01A 109.5 . . ?
C00H C010 H01B 109.5 . . ?
C00H C010 H01C 109.5 . . ?
H01A C010 H01B 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 109.5 . . ?
C01L C011 C00X 118.7(5) . . ?
C01L C011 C01O 118.6(5) . . ?
C01O C011 C00X 122.7(5) . . ?
C00Z C012 H012 120.3 . . ?
C015 C012 C00Z 119.4(5) . . ?
C015 C012 H012 120.3 . . ?
C00D C013 H01D 110.0 . . ?
C00D C013 H01F 110.0 . . ?
C00X C013 C00D 108.7(5) . . ?
C00X C013 H01D 110.0 . . ?
C00X C013 H01F 110.0 . . ?
H01D C013 H01F 108.3 . . ?
C00I C014 H014 119.9 . . ?
C00I C014 C015 120.3(5) . . ?
C015 C014 H014 119.9 . . ?
C012 C015 C014 120.1(6) . . ?
C012 C015 H015 119.9 . . ?
C014 C015 H015 119.9 . . ?
C00R C016 H016 120.3 . . ?
C00R C016 C01G 119.5(6) . . ?
C01G C016 H016 120.3 . . ?
C00J C017 Cl04 121.7(5) . . ?
C01I C017 Cl04 115.5(5) . . ?
C01I C017 C00J 122.8(5) . . ?
C00Q C018 Cl03 122.1(4) . . ?
C01K C018 Cl03 115.4(5) . . ?
C01K C018 C00Q 122.4(5) . . ?
C00N C019 H019 119.1 . . ?
C01H C019 C00N 121.7(6) . . ?
C01H C019 H019 119.1 . . ?
C00J C01A H01G 118.4 . . ?
C01B C01A C00J 123.2(5) . . ?
C01B C01A H01G 118.4 . . ?
C01A C01B H01I 119.9 . . ?
C01J C01B C01A 120.3(6) . . ?
C01J C01B H01I 119.9 . . ?
C01M C01C H01J 120.2 . . ?
C01M C01C C01N 119.6(6) . . ?
C01N C01C H01J 120.2 . . ?
Br02 C01D H01L 108.0 . . ?
C00H C01D Br02 115.0(4) . . ?
C00H C01D H01L 108.0 . . ?
C00X C01D Br02 106.6(4) . . ?
C00X C01D C00H 111.2(4) . . ?
C00X C01D H01L 108.0 . . ?
C00T C01E H01E 119.8 . . ?
C00Y C01E C00T 120.4(6) . . ?
C00Y C01E H01E 119.8 . . ?
C00M C01F H01M 119.0 . . ?
C00M C01F C01G 122.0(6) . . ?
C01G C01F H01M 119.0 . . ?
C016 C01G H01N 120.2 . . ?
C01F C01G C016 119.7(6) . . ?
C01F C01G H01N 120.2 . . ?
C019 C01H H01H 120.8 . . ?
C019 C01H C01K 118.4(6) . . ?
C01K C01H H01H 120.8 . . ?
C017 C01I H01O 119.9 . . ?
C017 C01I C01J 120.2(6) . . ?
C01J C01I H01O 119.9 . . ?
C01B C01J C01I 119.1(6) . . ?
C01B C01J H01P 120.4 . . ?
C01I C01J H01P 120.4 . . ?
C018 C01K H01K 119.8 . . ?
C01H C01K C018 120.4(6) . . ?
C01H C01K H01K 119.8 . . ?
C011 C01L H01Q 119.5 . . ?
C011 C01L C01N 121.0(6) . . ?
C01N C01L H01Q 119.5 . . ?
C01C C01M H01R 119.5 . . ?
C01C C01M C01O 121.0(7) . . ?
C01O C01M H01R 119.5 . . ?
C01C C01N C01L 120.0(6) . . ?
C01C C01N H01S 120.0 . . ?
C01L C01N H01S 120.0 . . ?
C011 C01O C01M 119.7(6) . . ?
C011 C01O H01T 120.1 . . ?
C01M C01O H01T 120.1 . . ?

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
Cl03 C018 C01K C01H -174.4(5) . . . . ?
Cl04 C017 C01I C01J -179.3(5) . . . . ?
O005 C00A C00I C00V 118.5(5) . . . . ?
O005 C00A C00I C014 -57.0(6) . . . . ?
O005 C00A C00L Br01 -173.8(3) . . . . ?
O005 C00A C00L C00G -47.6(5) . . . . ?
O005 C00A C00U C009 69.3(5) . . . . ?
O005 C00C C00O C009 62.3(6) . . . . ?
O005 C00C C00O C00G -57.8(5) . . . . ?
O006 C00X C011 C01L -54.6(7) . . . . ?
O006 C00X C011 C01O 125.9(6) . . . . ?
O006 C00X C013 C00D 69.9(5) . . . . ?
O006 C00X C01D Br02 -173.7(3) . . . . ?
O006 C00X C01D C00H -47.7(6) . . . . ?
O007 C00C C00O C009 -120.0(6) . . . . ?
O007 C00C C00O C00G 119.8(6) . . . . ?
C009 C00E C00K C00W 177.9(5) . . . . ?
C009 C00E C00Y C01E -178.3(5) . . . . ?
C00A O005 C00C O007 172.4(5) . . . . ?
C00A O005 C00C C00O -9.7(6) . . . . ?
C00A C00I C00V C00Z -173.7(5) . . . . ?
C00A C00I C014 C015 175.7(6) . . . . ?
C00B C00G C00L Br01 -138.9(4) . . . . ?
C00B C00G C00L C00A 100.6(5) . . . . ?
C00B C00G C00O C009 -168.3(4) . . . . ?
C00B C00G C00O C00C -48.0(5) . . . . ?
C00B C00G C00Q C00N -106.3(5) . . . . ?
C00B C00G C00Q C018 64.4(6) . . . . ?
C00C O005 C00A C00I -175.6(4) . . . . ?
C00C O005 C00A C00L 64.1(5) . . . . ?
C00C O005 C00A C00U -54.4(5) . . . . ?
C00D C00F C00H C00J 73.6(5) . . . . ?
C00D C00F C00H C010 -168.4(4) . . . . ?
C00D C00F C00H C01D -52.9(6) . . . . ?
C00D C00F C00P O006 63.7(6) . . . . ?
C00D C00F C00P O008 -118.2(6) . . . . ?
C00D C00M C00S C00R -178.2(5) . . . . ?
C00D C00M C01F C01G 178.9(6) . . . . ?
C00E C009 C00O C00C 82.9(5) . . . . ?
C00E C009 C00O C00G -159.7(4) . . . . ?
C00E C009 C00U C00A -145.9(5) . . . . ?
C00E C00K C00W C00T 1.3(9) . . . . ?
C00E C00Y C01E C00T -0.2(9) . . . . ?
C00F C00D C00M C00S 108.2(6) . . . . ?
C00F C00D C00M C01F -70.6(7) . . . . ?
C00F C00D C013 C00X -18.8(6) . . . . ?
C00F C00H C00J C017 177.9(5) . . . . ?
C00F C00H C00J C01A 5.7(7) . . . . ?
C00F C00H C01D Br02 107.5(4) . . . . ?
C00F C00H C01D C00X -13.7(6) . . . . ?
C00G C00Q C018 Cl03 3.4(8) . . . . ?
C00G C00Q C018 C01K -173.8(5) . . . . ?
C00H C00F C00P O006 -56.9(6) . . . . ?
C00H C00F C00P O008 121.2(7) . . . . ?
C00H C00J C017 Cl04 6.3(8) . . . . ?
C00H C00J C017 C01I -174.6(5) . . . . ?
C00H C00J C01A C01B 174.6(5) . . . . ?
C00I C00A C00L Br01 73.6(5) . . . . ?
C00I C00A C00L C00G -160.1(4) . . . . ?
C00I C00A C00U C009 -178.4(5) . . . . ?
C00I C00V C00Z C012 -1.8(10) . . . . ?
C00I C014 C015 C012 -1.9(10) . . . . ?
C00J C00H C01D Br02 -16.9(6) . . . . ?
C00J C00H C01D C00X -138.1(5) . . . . ?
C00J C017 C01I C01J 1.6(9) . . . . ?
C00J C01A C01B C01J -1.1(9) . . . . ?
C00K C00E C00Y C01E 0.5(8) . . . . ?
C00L C00A C00I C00V -126.3(6) . . . . ?
C00L C00A C00I C014 58.2(7) . . . . ?
C00L C00A C00U C009 -46.3(6) . . . . ?
C00L C00G C00O C009 -53.2(5) . . . . ?
C00L C00G C00O C00C 67.1(5) . . . . ?
C00L C00G C00Q C00N 132.2(5) . . . . ?
C00L C00G C00Q C018 -57.0(7) . . . . ?
C00M C00D C00F C00H -159.9(5) . . . . ?
C00M C00D C00F C00P 82.7(5) . . . . ?
C00M C00D C013 C00X -143.5(5) . . . . ?
C00M C01F C01G C016 -1.2(10) . . . . ?
C00N C00Q C018 Cl03 174.8(4) . . . . ?
C00N C00Q C018 C01K -2.4(8) . . . . ?
C00N C019 C01H C01K -1.0(9) . . . . ?
C00O C009 C00E C00K 116.6(6) . . . . ?
C00O C009 C00E C00Y -64.5(7) . . . . ?
C00O C009 C00U C00A -19.3(6) . . . . ?
C00O C00G C00L Br01 106.6(4) . . . . ?
C00O C00G C00L C00A -13.9(6) . . . . ?
C00O C00G C00Q C00N 11.4(7) . . . . ?
C00O C00G C00Q C018 -177.8(5) . . . . ?
C00P O006 C00X C011 -176.1(4) . . . . ?
C00P O006 C00X C013 -55.0(6) . . . . ?
C00P O006 C00X C01D 64.5(5) . . . . ?
C00P C00F C00H C00J -167.2(4) . . . . ?
C00P C00F C00H C010 -49.2(5) . . . . ?
C00P C00F C00H C01D 66.3(5) . . . . ?
C00Q C00G C00L Br01 -18.5(6) . . . . ?
C00Q C00G C00L C00A -139.0(5) . . . . ?
C00Q C00G C00O C009 74.6(5) . . . . ?
C00Q C00G C00O C00C -165.1(4) . . . . ?
C00Q C00N C019 C01H 1.4(9) . . . . ?
C00Q C018 C01K C01H 2.9(9) . . . . ?
C00R C016 C01G C01F 1.5(11) . . . . ?
C00S C00M C01F C01G 0.1(9) . . . . ?
C00S C00R C016 C01G -0.8(10) . . . . ?
C00U C009 C00E C00K -120.7(5) . . . . ?
C00U C009 C00E C00Y 58.1(7) . . . . ?
C00U C009 C00O C00C -42.8(6) . . . . ?
C00U C009 C00O C00G 74.6(5) . . . . ?
C00U C00A C00I C00V 4.5(8) . . . . ?
C00U C00A C00I C014 -171.0(5) . . . . ?
C00U C00A C00L Br01 -59.2(5) . . . . ?
C00U C00A C00L C00G 67.1(5) . . . . ?
C00V C00I C014 C015 0.1(9) . . . . ?
C00V C00Z C012 C015 0.0(10) . . . . ?
C00W C00T C01E C00Y 0.4(10) . . . . ?
C00X O006 C00P O008 171.6(5) . . . . ?
C00X O006 C00P C00F -10.2(7) . . . . ?
C00X C011 C01L C01N -179.2(6) . . . . ?
C00X C011 C01O C01M 178.7(6) . . . . ?
C00Y C00E C00K C00W -1.0(8) . . . . ?
C00Z C012 C015 C014 1.9(10) . . . . ?
C010 C00H C00J C017 60.4(6) . . . . ?
C010 C00H C00J C01A -111.9(5) . . . . ?
C010 C00H C01D Br02 -138.8(4) . . . . ?
C010 C00H C01D C00X 100.0(5) . . . . ?
C011 C00X C013 C00D -176.9(5) . . . . ?
C011 C00X C01D Br02 72.7(5) . . . . ?
C011 C00X C01D C00H -161.3(5) . . . . ?
C011 C01L C01N C01C 0.2(11) . . . . ?
C013 C00D C00F C00H 73.6(6) . . . . ?
C013 C00D C00F C00P -43.8(6) . . . . ?
C013 C00D C00M C00S -129.7(6) . . . . ?
C013 C00D C00M C01F 51.5(8) . . . . ?
C013 C00X C011 C01L -168.3(5) . . . . ?
C013 C00X C011 C01O 12.1(8) . . . . ?
C013 C00X C01D Br02 -59.3(5) . . . . ?
C013 C00X C01D C00H 66.7(6) . . . . ?
C014 C00I C00V C00Z 1.8(9) . . . . ?
C016 C00R C00S C00M -0.4(9) . . . . ?
C017 C00J C01A C01B 1.7(8) . . . . ?
C017 C01I C01J C01B -0.8(9) . . . . ?
C019 C00N C00Q C00G 171.9(5) . . . . ?
C019 C00N C00Q C018 0.3(8) . . . . ?
C019 C01H C01K C018 -1.1(9) . . . . ?
C01A C00J C017 Cl04 179.0(4) . . . . ?
C01A C00J C017 C01I -1.9(8) . . . . ?
C01A C01B C01J C01I 0.6(9) . . . . ?
C01C C01M C01O C011 0.8(11) . . . . ?
C01D C00H C00J C017 -62.4(7) . . . . ?
C01D C00H C00J C01A 125.3(5) . . . . ?
C01D C00X C011 C01L 61.2(7) . . . . ?
C01D C00X C011 C01O -118.4(6) . . . . ?
C01D C00X C013 C00D -46.2(6) . . . . ?
C01E C00T C00W C00K -1.0(9) . . . . ?
C01F C00M C00S C00R 0.7(8) . . . . ?
C01L C011 C01O C01M -0.9(9) . . . . ?
C01M C01C C01N C01L -0.2(11) . . . . ?
C01N C01C C01M C01O -0.3(11) . . . . ?
C01O C011 C01L C01N 0.3(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
