# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_wang1
_database_code_depnum_ccdc_archive 'CCDC 2096474'
loop_
_audit_author_name
_audit_author_address
'Chun-Jiang Wang'
;Wuhan University
China
;
_audit_update_record             
;
2021-07-14 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-18
_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         'C25 H25 Br2 N O2'
_chemical_formula_sum            'C25 H25 Br2 N O2'
_chemical_formula_weight         531.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.982
_cell_length_b                   20.17050(10)
_cell_length_c                   9.655
_cell_angle_alpha                90
_cell_angle_beta                 104.4620(10)
_cell_angle_gamma                90
_cell_volume                     1128.058(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.495
_cell_measurement_theta_min      4.384
_shelx_estimated_absorpt_T_max   0.704
_shelx_estimated_absorpt_T_min   0.331
_exptl_absorpt_coefficient_mu    4.724
_exptl_absorpt_correction_T_max  0.685
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22395
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.495
_diffrn_reflns_theta_min         4.384
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2075
_reflns_number_total             2083
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0205
_refine_ls_restrained_S_all      1.074
_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)+(0.0236P)²+0.9886P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0514
_refine_ls_wR_factor_ref         0.0514
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H15A(0.5) H15B(0.5) H15C(0.5)
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42639(3) 0.55919(2) 0.16388(2) 0.02157(8) Uani 1 1 d . . . . .
O1 O 0.1201(3) 0.2500 0.16405(16) 0.0121(3) Uani 1 2 d S T P . .
O2 O 0.4845(3) 0.2500 0.30663(17) 0.0147(3) Uani 1 2 d S T P . .
N1 N 0.4627(4) 0.2500 0.6572(2) 0.0192(4) Uani 1 2 d S T P . .
C1 C 0.1544(4) 0.2500 0.4105(2) 0.0104(4) Uani 1 2 d S T P . .
C2 C 0.3317(4) 0.2500 0.5480(2) 0.0123(4) Uani 1 2 d S T P . .
C3 C 0.0032(3) 0.31550(8) 0.39729(16) 0.0113(3) Uani 1 1 d . . . . .
H3 H -0.1432 0.3063 0.3232 0.014 Uiso 1 1 calc R . . . .
C4 C -0.0661(3) 0.33179(8) 0.53416(18) 0.0164(3) Uani 1 1 d . . . . .
H4 H -0.169(4) 0.3025(11) 0.557(2) 0.029(6) Uiso 1 1 d . . . . .
C5 C -0.0054(3) 0.38440(10) 0.6145(2) 0.0221(4) Uani 1 1 d . . . . .
H5A H -0.058(4) 0.3900(11) 0.695(2) 0.025(5) Uiso 1 1 d . . . . .
H5B H 0.087(4) 0.4152(13) 0.590(3) 0.035(6) Uiso 1 1 d . . . . .
C6 C 0.1145(3) 0.37466(8) 0.34347(16) 0.0120(3) Uani 1 1 d . . . . .
C7 C 0.3443(3) 0.39284(8) 0.39907(17) 0.0145(3) Uani 1 1 d . . . . .
H7 H 0.4385 0.3674 0.4742 0.017 Uiso 1 1 calc R . . . .
C8 C 0.4379(3) 0.44759(8) 0.34621(18) 0.0159(3) Uani 1 1 d . . . . .
H8 H 0.5956 0.4590 0.3832 0.019 Uiso 1 1 calc R . . . .
C9 C 0.2980(3) 0.48507(8) 0.23909(17) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.0669(3) 0.46994(8) 0.18493(17) 0.0161(3) Uani 1 1 d . . . . .
H10 H -0.0287 0.4971 0.1138 0.019 Uiso 1 1 calc R . . . .
C11 C -0.0226(3) 0.41419(8) 0.23661(17) 0.0138(3) Uani 1 1 d . . . . .
H11 H -0.1801 0.4028 0.1985 0.017 Uiso 1 1 calc R . . . .
C12 C 0.2778(4) 0.2500 0.2877(2) 0.0113(4) Uani 1 2 d S T P . .
C13 C 0.1882(4) 0.2500 0.0248(2) 0.0145(5) Uani 1 2 d S T P . .
C14 C 0.3230(3) 0.31270(9) 0.01264(19) 0.0220(4) Uani 1 1 d . . . . .
H14A H 0.2345 0.3515 0.0292 0.033 Uiso 1 1 calc GR . . . .
H14B H 0.3497 0.3153 -0.0833 0.033 Uiso 1 1 calc GR . . . .
H14C H 0.4716 0.3117 0.0841 0.033 Uiso 1 1 calc GR . . . .
C15 C -0.0442(5) 0.2500 -0.0824(3) 0.0238(5) Uani 1 2 d S T P . .
H15A H -0.0219 0.2528 -0.1794 0.036 Uiso 0.5 1 calc GR . . A -1
H15B H -0.1346 0.2882 -0.0647 0.036 Uiso 0.5 1 calc GR . . A -1
H15C H -0.1267 0.2090 -0.0726 0.036 Uiso 0.5 1 calc GR . . A -1


_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 C9 1.9055(16) . ?
O1 C12 1.324(3) . ?
O1 C13 1.499(3) . ?
O2 C12 1.204(3) . ?
N1 C2 1.146(3) . ?
C1 C2 1.478(3) . ?
C1 C3 1.5879(19) . ?
C1 C3 1.5878(19) 4_565 ?
C1 C12 1.545(3) . ?
C3 C4 1.517(2) . ?
C3 C6 1.520(2) . ?
C4 C5 1.311(3) . ?
C6 C7 1.394(2) . ?
C6 C11 1.397(2) . ?
C7 C8 1.392(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.384(2) . ?
C10 C11 1.391(2) . ?
C13 C14 1.520(2) . ?
C13 C14 1.520(2) 4_565 ?
C13 C15 1.512(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C13 121.11(17) . . ?
C2 C1 C3 109.79(11) . 4_565 ?
C2 C1 C3 109.79(11) . . ?
C2 C1 C12 108.40(18) . . ?
C3 C1 C3 112.61(17) 4_565 . ?
C12 C1 C3 108.07(11) . . ?
C12 C1 C3 108.07(11) . 4_565 ?
N1 C2 C1 177.4(2) . . ?
C4 C3 C1 112.62(13) . . ?
C4 C3 C6 111.49(13) . . ?
C6 C3 C1 113.05(13) . . ?
C5 C4 C3 126.51(16) . . ?
C7 C6 C3 123.29(14) . . ?
C7 C6 C11 118.36(15) . . ?
C11 C6 C3 118.31(14) . . ?
C8 C7 C6 121.06(15) . . ?
C9 C8 C7 119.01(15) . . ?
C8 C9 Br1 119.23(12) . . ?
C8 C9 C10 121.54(15) . . ?
C10 C9 Br1 119.24(12) . . ?
C9 C10 C11 118.71(15) . . ?
C10 C11 C6 121.26(15) . . ?
O1 C12 C1 108.80(18) . . ?
O2 C12 O1 127.6(2) . . ?
O2 C12 C1 123.6(2) . . ?
O1 C13 C14 109.74(12) . 4_565 ?
O1 C13 C14 109.74(12) . . ?
O1 C13 C15 101.82(18) . . ?
C14 C13 C14 112.6(2) 4_565 . ?
C15 C13 C14 111.21(13) . . ?
C15 C13 C14 111.21(13) . 4_565 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20201124_sc-13-56a
_database_code_depnum_ccdc_archive 'CCDC 2096475'
loop_
_audit_author_name
_audit_author_address
'Chun-Jiang Wang'
;Wuhan University
China
;
_audit_update_record             
;
2021-07-14 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_audit_creation_date             2020-11-24
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H25 Br2 N O2'
_chemical_formula_sum            'C25 H25 Br2 N O2'
_chemical_formula_weight         531.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.68950(10)
_cell_length_b                   11.14220(10)
_cell_length_c                   10.92190(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.4700(10)
_cell_angle_gamma                90
_cell_volume                     1202.09(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    23537
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4640
_cell_measurement_theta_min      3.9590
_shelx_estimated_absorpt_T_max   0.666
_shelx_estimated_absorpt_T_min   0.350
_exptl_absorpt_coefficient_mu    4.433
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26178
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.796
_diffrn_reflns_theta_min         4.381
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  89.00   0.50    0.50    --    0.00  32.00-142.00  110
  2  ω    -12.00  20.00   0.50    0.50    --    0.00  32.00-142.00   64
  3  ω     32.00  58.00   0.50    0.50    --   94.60 -32.00  58.00   52
  4  ω    107.00 146.00   0.50    0.50    --   94.60  32.00-142.00   78
  5  ω    -54.00 -16.00   0.50    0.50    --    0.00 -32.00  58.00   76
  6  ω    -12.00  13.00   0.50    0.50    --    0.00 -32.00  58.00   50
  7  ω     73.00 120.00   0.50    0.50    --   32.00  72.00 -45.98   94
  8  ω      6.00  47.00   0.50    0.50    --   32.00  72.00 -45.98   82
  9  ω     10.00  61.00   0.50    0.50    --   36.00  72.00 170.83  102
 10  ω      1.00  61.00   0.50    0.50    --   44.00 -38.00 -16.74  120
 11  ω    -44.00  -3.00   0.50    0.50    --   44.00 -38.00 -16.74   82
 12  ω     29.00  54.00   0.50    0.50    --   52.00  73.00-118.99   50
 13  ω     25.00  83.00   0.50    0.50    --   52.00  72.00  24.57  116
 14  ω     32.00  79.00   0.50    0.50    --   60.00  75.00 -69.87   94
 15  ω     36.00  61.00   0.50    0.50    --   64.00  74.00 -35.59   50
 16  ω     37.00  73.00   0.50    0.50    --   64.00  75.00  69.04   72
 17  ω     36.00  67.00   0.50    0.50    --   64.00  75.00 178.18   62
 18  ω     41.00  75.00   0.50    0.50    --   68.00  75.00-114.22   68
 19  ω     40.00  65.00   0.50    0.50    --   68.00  74.00 135.23   50
 20  ω     40.00  77.00   0.50    0.50    --   68.00  74.00  35.97   74
 21  ω     41.00  69.00   0.50    0.50    --   68.00  75.00 -19.38   56
 22  ω     40.00  72.00   0.50    0.50    --   68.00  75.00-151.53   64
 23  ω     44.00  69.00   0.50    0.50    --   72.00  75.00  89.21   50
 24  ω     45.00  73.00   0.50    0.50    --   72.00  75.00 105.88   56
 25  ω    126.00 157.00   0.50    0.50    --   72.00  74.00 -41.94   62
 26  ω     46.00  71.00   0.50    0.50    --   72.00  74.00 -41.94   50
 27  ω    100.00 165.00   0.50    0.50    --   76.00  75.00   1.94  130
 28  ω     49.00  76.00   0.50    0.50    --   76.00  75.00   1.94   54
 29  ω     61.00 107.00   0.50    0.50    --   84.00  67.00 158.60   92
 30  ω    136.00 172.00   0.50    0.50    --   94.60  61.00 120.00   72
 31  ω     73.00  99.00   0.50    0.50    --   94.60 -77.00 -90.00   52
 32  ω      5.00  69.00   0.50    0.50    --   94.60 -77.00 -90.00  128
 33  ω     71.00 128.00   0.50    0.50    --   94.60  61.00 120.00  114
 34  ω      7.00  36.00   0.50    0.50    --   94.60 -82.00 150.00   58
 35  ω      5.00  39.00   0.50    0.50    --   94.60 -82.00-150.00   68
 36  ω     73.00 164.00   0.50    0.50    --   94.60  58.00 -59.67  182
 37  ω     67.00 183.00   0.50    0.50    --   94.60  72.00-104.35  232
 38  ω     98.00 126.00   0.50    0.50    --   94.60 -82.00   0.00   56
 39  ω     71.00 182.00   0.50    0.50    --   94.60  61.00  60.00  222
 40  ω      8.00 125.00   0.50    0.50    --   94.60 -82.00 -30.00  234
 41  ω     74.00 125.00   0.50    0.50    --   94.60 -82.00  60.00  102
 42  ω     72.00 115.00   0.50    0.50    --   94.60  61.00   0.00   86
 43  ω     63.00 109.00   0.50    0.50    --   94.60 -61.00 150.00   92
 44  ω     30.00  56.00   0.50    0.50    --   94.60 -61.00 150.00   52
 45  ω     71.00 169.00   0.50    0.50    --   94.60  59.00-123.34  196
 46  ω    127.00 152.00   0.50    0.50    --   94.60  61.00  90.00   50
 47  ω     74.00 112.00   0.50    0.50    --   94.60  61.00  90.00   76
 48  ω     78.00 154.00   0.50    0.50    --   94.60  30.00  30.00  152
 49  ω     71.00 168.00   0.50    0.50    --   94.60  61.00-150.00  194
 50  ω     42.00  68.00   0.50    0.50    --   94.60 -82.00  60.00   52
 51  ω     80.00 113.00   0.50    0.50    --   94.60  77.00 -60.00   66
 52  ω      5.00  94.00   0.50    0.50    --   94.60 -82.00   0.00  178
 53  ω     73.00 178.00   0.50    0.50    --   94.60  61.00-180.00  210
 54  ω     72.00 121.00   0.50    0.50    --   94.60  56.00 151.60   98
 55  ω     71.00 117.00   0.50    0.50    --   94.60  61.00  30.00   92
 56  ω     42.00 122.00   0.50    0.50    --   94.60 -82.00 150.00  160
 57  ω     93.00 120.00   0.50    0.50    --   94.60 -82.00-150.00   54
 58  ω    151.00 176.00   0.50    0.50    --   94.60  61.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1276797000
_diffrn_orient_matrix_UB_12      -0.0426494000
_diffrn_orient_matrix_UB_13      0.0205558000
_diffrn_orient_matrix_UB_21      -0.0880240000
_diffrn_orient_matrix_UB_22      0.0382976000
_diffrn_orient_matrix_UB_23      -0.1425905000
_diffrn_orient_matrix_UB_31      0.0165371000
_diffrn_orient_matrix_UB_32      -0.1258307000
_diffrn_orient_matrix_UB_33      -0.0503819000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                4759
_reflns_number_total             4773
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 2190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0192
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.5140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0498
_refine_ls_wR_factor_ref         0.0498
_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:
 C00G(H00G), C00H(H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00I(H00I), C00J(H00J), C00M(H00M),
 C00R(H00U), C00S(H00V), C00T(H00W), C00U(H00X)
2.c X=CH2 refined with riding coordinates:
 C006(H00A,H00B), C00Q(H00S,H00T)
2.d Idealised Me refined as rotating group:
 C00N(H00E,H00F,H00K), C00O(H00L,H00N,H00O), C00P(H00P,H00Q,H00R)
;
_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 0.89260(3) 0.85670(3) 0.37961(3) 0.02832(8) Uani 1 1 d . . . . .
Br02 Br -0.06464(3) 0.14327(3) 0.20618(3) 0.03181(9) Uani 1 1 d . . . . .
O003 O 0.41482(18) 0.43357(16) 0.13953(17) 0.0162(4) Uani 1 1 d . . . . .
O004 O 0.42139(19) 0.31684(16) 0.31250(18) 0.0178(4) Uani 1 1 d . . . . .
N005 N 0.3594(2) 0.7176(2) 0.1694(2) 0.0204(5) Uani 1 1 d . . . . .
C006 C 0.5783(3) 0.4998(3) 0.6836(3) 0.0257(6) Uani 1 1 d . . . . .
H00A H 0.573218 0.580056 0.704695 0.031 Uiso 1 1 calc R U . . .
H00B H 0.596501 0.441258 0.748876 0.031 Uiso 1 1 calc R U . . .
C007 C 0.1081(2) 0.3472(3) 0.2715(2) 0.0174(5) Uani 1 1 d . . . . .
H007 H 0.157506 0.303349 0.346945 0.021 Uiso 1 1 calc R U . . .
C008 C 0.3761(2) 0.6325(2) 0.2339(2) 0.0140(5) Uani 1 1 d . . . . .
C009 C -0.0072(3) 0.2984(3) 0.1753(3) 0.0211(5) Uani 1 1 d . . . . .
C00A C 0.6510(2) 0.5760(2) 0.4118(2) 0.0151(5) Uani 1 1 d . . . . .
C00B C 0.1492(2) 0.4623(2) 0.2542(2) 0.0166(5) Uani 1 1 d . . . . .
C00C C 0.5596(3) 0.4690(2) 0.5614(3) 0.0176(5) Uani 1 1 d . . . . .
H00C H 0.565031 0.388337 0.542253 0.021 Uiso 1 1 calc R U . . .
C00D C 0.2360(2) 0.6324(3) 0.4152(3) 0.0195(5) Uani 1 1 d . . . . .
H00D H 0.211349 0.697751 0.357969 0.023 Uiso 1 1 calc R U . . .
C00E C 0.4195(3) 0.3339(2) 0.0491(2) 0.0202(5) Uani 1 1 d . . . . .
C00F C 0.4135(2) 0.4123(2) 0.2588(2) 0.0137(5) Uani 1 1 d . . . . .
C00G C 0.2724(2) 0.5161(2) 0.3656(2) 0.0150(5) Uani 1 1 d . . . . .
H00G H 0.298656 0.459227 0.439659 0.018 Uiso 1 1 calc R U . . .
C00H C 0.5295(2) 0.5603(2) 0.4507(2) 0.0136(5) Uani 1 1 d . . . . .
H00H H 0.514000 0.637513 0.485462 0.016 Uiso 1 1 calc R U . . .
C00I C 0.7013(2) 0.6906(2) 0.4075(2) 0.0160(5) Uani 1 1 d . . . . .
H00I H 0.660280 0.757863 0.426378 0.019 Uiso 1 1 calc R U . . .
C00J C 0.7134(3) 0.4775(3) 0.3813(3) 0.0213(5) Uani 1 1 d . . . . .
H00J H 0.681065 0.400725 0.385481 0.026 Uiso 1 1 calc R U . . .
C00K C 0.8145(3) 0.7025(3) 0.3743(3) 0.0197(5) Uani 1 1 d . . . . .
C00L C 0.3981(2) 0.5303(2) 0.3252(2) 0.0133(5) Uani 1 1 d . . . . .
C00M C -0.0821(3) 0.3600(3) 0.0611(3) 0.0262(6) Uani 1 1 d . . . . .
H00M H -0.159098 0.326062 -0.002280 0.031 Uiso 1 1 calc R U . . .
C00N C 0.4219(3) 0.4046(3) -0.0692(3) 0.0276(6) Uani 1 1 d . . . . .
H00E H 0.342848 0.454471 -0.103506 0.041 Uiso 1 1 calc R U . . .
H00F H 0.422787 0.349890 -0.136791 0.041 Uiso 1 1 calc R U . . .
H00K H 0.501532 0.453863 -0.041919 0.041 Uiso 1 1 calc R U . . .
C00O C 0.5482(3) 0.2614(3) 0.1120(3) 0.0246(6) Uani 1 1 d . . . . .
H00L H 0.624821 0.314421 0.140143 0.037 Uiso 1 1 calc R U . . .
H00N H 0.555894 0.205378 0.048472 0.037 Uiso 1 1 calc R U . . .
H00O H 0.545439 0.218557 0.187152 0.037 Uiso 1 1 calc R U . . .
C00P C 0.2911(3) 0.2602(3) 0.0134(3) 0.0288(6) Uani 1 1 d . . . . .
H00P H 0.289991 0.221213 0.091423 0.043 Uiso 1 1 calc R U . . .
H00Q H 0.288233 0.200791 -0.051241 0.043 Uiso 1 1 calc R U . . .
H00R H 0.213733 0.311915 -0.022446 0.043 Uiso 1 1 calc R U . . .
C00Q C 0.2376(3) 0.6455(3) 0.5359(3) 0.0271(6) Uani 1 1 d . . . . .
H00S H 0.261946 0.581417 0.594937 0.032 Uiso 1 1 calc R U . . .
H00T H 0.214373 0.718897 0.561993 0.032 Uiso 1 1 calc R U . . .
C00R C 0.8744(3) 0.6051(3) 0.3413(3) 0.0258(6) Uani 1 1 d . . . . .
H00U H 0.948245 0.615264 0.317056 0.031 Uiso 1 1 calc R U . . .
C00S C 0.0753(3) 0.5252(3) 0.1394(3) 0.0223(6) Uani 1 1 d . . . . .
H00V H 0.102341 0.601902 0.126312 0.027 Uiso 1 1 calc R U . . .
C00T C -0.0396(3) 0.4734(3) 0.0434(3) 0.0282(6) Uani 1 1 d . . . . .
H00W H -0.088057 0.515966 -0.033460 0.034 Uiso 1 1 calc R U . . .
C00U C 0.8232(3) 0.4922(3) 0.3447(3) 0.0270(6) Uani 1 1 d . . . . .
H00X H 0.862507 0.425600 0.322357 0.032 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 C00K 1.901(3) . ?
Br02 C009 1.906(3) . ?
O003 C00E 1.499(3) . ?
O003 C00F 1.329(3) . ?
O004 C00F 1.202(3) . ?
N005 C008 1.154(4) . ?
C006 H00A 0.9300 . ?
C006 H00B 0.9300 . ?
C006 C00C 1.318(4) . ?
C007 H007 0.9300 . ?
C007 C009 1.389(4) . ?
C007 C00B 1.392(4) . ?
C008 C00L 1.473(3) . ?
C009 C00M 1.380(4) . ?
C00A C00H 1.523(3) . ?
C00A C00I 1.393(4) . ?
C00A C00J 1.390(4) . ?
C00B C00G 1.533(3) . ?
C00B C00S 1.389(4) . ?
C00C H00C 0.9300 . ?
C00C C00H 1.517(3) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.511(4) . ?
C00D C00Q 1.321(4) . ?
C00E C00N 1.522(4) . ?
C00E C00O 1.515(4) . ?
C00E C00P 1.517(4) . ?
C00F C00L 1.541(3) . ?
C00G H00G 0.9800 . ?
C00G C00L 1.574(3) . ?
C00H H00H 0.9800 . ?
C00H C00L 1.579(3) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.395(4) . ?
C00J H00J 0.9300 . ?
C00J C00U 1.388(4) . ?
C00K C00R 1.378(4) . ?
C00M H00M 0.9300 . ?
C00M C00T 1.381(5) . ?
C00N H00E 0.9600 . ?
C00N H00F 0.9600 . ?
C00N H00K 0.9600 . ?
C00O H00L 0.9600 . ?
C00O H00N 0.9600 . ?
C00O H00O 0.9600 . ?
C00P H00P 0.9600 . ?
C00P H00Q 0.9600 . ?
C00P H00R 0.9600 . ?
C00Q H00S 0.9300 . ?
C00Q H00T 0.9300 . ?
C00R H00U 0.9300 . ?
C00R C00U 1.377(5) . ?
C00S H00V 0.9300 . ?
C00S C00T 1.399(4) . ?
C00T H00W 0.9300 . ?
C00U H00X 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
C00F O003 C00E 121.9(2) . . ?
H00A C006 H00B 120.0 . . ?
C00C C006 H00A 120.0 . . ?
C00C C006 H00B 120.0 . . ?
C009 C007 H007 120.2 . . ?
C009 C007 C00B 119.6(2) . . ?
C00B C007 H007 120.2 . . ?
N005 C008 C00L 175.3(3) . . ?
C007 C009 Br02 118.3(2) . . ?
C00M C009 Br02 119.8(2) . . ?
C00M C009 C007 121.9(3) . . ?
C00I C00A C00H 119.8(2) . . ?
C00J C00A C00H 120.9(2) . . ?
C00J C00A C00I 119.3(2) . . ?
C007 C00B C00G 118.2(2) . . ?
C00S C00B C007 119.2(2) . . ?
C00S C00B C00G 122.6(2) . . ?
C006 C00C H00C 118.8 . . ?
C006 C00C C00H 122.5(3) . . ?
C00H C00C H00C 118.8 . . ?
C00G C00D H00D 118.5 . . ?
C00Q C00D H00D 118.5 . . ?
C00Q C00D C00G 123.1(3) . . ?
O003 C00E C00N 101.0(2) . . ?
O003 C00E C00O 110.5(2) . . ?
O003 C00E C00P 108.4(2) . . ?
C00O C00E C00N 110.7(2) . . ?
C00O C00E C00P 113.8(2) . . ?
C00P C00E C00N 111.7(2) . . ?
O003 C00F C00L 110.7(2) . . ?
O004 C00F O003 127.7(2) . . ?
O004 C00F C00L 121.7(2) . . ?
C00B C00G H00G 106.9 . . ?
C00B C00G C00L 112.50(19) . . ?
C00D C00G C00B 111.0(2) . . ?
C00D C00G H00G 106.9 . . ?
C00D C00G C00L 112.2(2) . . ?
C00L C00G H00G 106.9 . . ?
C00A C00H H00H 107.2 . . ?
C00A C00H C00L 110.67(19) . . ?
C00C C00H C00A 110.9(2) . . ?
C00C C00H H00H 107.2 . . ?
C00C C00H C00L 113.4(2) . . ?
C00L C00H H00H 107.2 . . ?
C00A C00I H00I 120.7 . . ?
C00A C00I C00K 118.7(2) . . ?
C00K C00I H00I 120.7 . . ?
C00A C00J H00J 119.6 . . ?
C00U C00J C00A 120.8(3) . . ?
C00U C00J H00J 119.6 . . ?
C00I C00K Br01 119.5(2) . . ?
C00R C00K Br01 118.5(2) . . ?
C00R C00K C00I 122.0(3) . . ?
C008 C00L C00F 111.0(2) . . ?
C008 C00L C00G 109.6(2) . . ?
C008 C00L C00H 106.44(19) . . ?
C00F C00L C00G 107.6(2) . . ?
C00F C00L C00H 111.69(19) . . ?
C00G C00L C00H 110.47(19) . . ?
C009 C00M H00M 120.9 . . ?
C009 C00M C00T 118.3(3) . . ?
C00T C00M H00M 120.9 . . ?
C00E C00N H00E 109.5 . . ?
C00E C00N H00F 109.5 . . ?
C00E C00N H00K 109.5 . . ?
H00E C00N H00F 109.5 . . ?
H00E C00N H00K 109.5 . . ?
H00F C00N H00K 109.5 . . ?
C00E C00O H00L 109.5 . . ?
C00E C00O H00N 109.5 . . ?
C00E C00O H00O 109.5 . . ?
H00L C00O H00N 109.5 . . ?
H00L C00O H00O 109.5 . . ?
H00N C00O H00O 109.5 . . ?
C00E C00P H00P 109.5 . . ?
C00E C00P H00Q 109.5 . . ?
C00E C00P H00R 109.5 . . ?
H00P C00P H00Q 109.5 . . ?
H00P C00P H00R 109.5 . . ?
H00Q C00P H00R 109.5 . . ?
C00D C00Q H00S 120.0 . . ?
C00D C00Q H00T 120.0 . . ?
H00S C00Q H00T 120.0 . . ?
C00K C00R H00U 120.6 . . ?
C00U C00R C00K 118.9(2) . . ?
C00U C00R H00U 120.6 . . ?
C00B C00S H00V 119.9 . . ?
C00B C00S C00T 120.1(3) . . ?
C00T C00S H00V 119.9 . . ?
C00M C00T C00S 120.9(3) . . ?
C00M C00T H00W 119.5 . . ?
C00S C00T H00W 119.5 . . ?
C00J C00U H00X 119.8 . . ?
C00R C00U C00J 120.3(3) . . ?
C00R C00U H00X 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br01 C00K C00R C00U 176.3(2) . . . . ?
Br02 C009 C00M C00T 178.4(2) . . . . ?
O003 C00F C00L C008 5.4(3) . . . . ?
O003 C00F C00L C00G 125.3(2) . . . . ?
O003 C00F C00L C00H -113.2(2) . . . . ?
O004 C00F C00L C008 -173.9(2) . . . . ?
O004 C00F C00L C00G -54.0(3) . . . . ?
O004 C00F C00L C00H 67.4(3) . . . . ?
C006 C00C C00H C00A 108.2(3) . . . . ?
C006 C00C C00H C00L -126.6(3) . . . . ?
C007 C009 C00M C00T 0.1(4) . . . . ?
C007 C00B C00G C00D -121.8(2) . . . . ?
C007 C00B C00G C00L 111.4(2) . . . . ?
C007 C00B C00S C00T 0.6(4) . . . . ?
C009 C007 C00B C00G 176.7(2) . . . . ?
C009 C007 C00B C00S -1.3(4) . . . . ?
C009 C00M C00T C00S -0.8(4) . . . . ?
C00A C00H C00L C008 -60.2(3) . . . . ?
C00A C00H C00L C00F 61.1(3) . . . . ?
C00A C00H C00L C00G -179.1(2) . . . . ?
C00A C00I C00K Br01 -175.70(18) . . . . ?
C00A C00I C00K C00R 2.4(4) . . . . ?
C00A C00J C00U C00R 1.6(4) . . . . ?
C00B C007 C009 Br02 -177.35(18) . . . . ?
C00B C007 C009 C00M 1.0(4) . . . . ?
C00B C00G C00L C008 74.6(3) . . . . ?
C00B C00G C00L C00F -46.2(3) . . . . ?
C00B C00G C00L C00H -168.4(2) . . . . ?
C00B C00S C00T C00M 0.5(5) . . . . ?
C00C C00H C00L C008 174.5(2) . . . . ?
C00C C00H C00L C00F -64.2(3) . . . . ?
C00C C00H C00L C00G 55.6(3) . . . . ?
C00D C00G C00L C008 -51.4(3) . . . . ?
C00D C00G C00L C00F -172.3(2) . . . . ?
C00D C00G C00L C00H 65.5(3) . . . . ?
C00E O003 C00F O004 3.4(4) . . . . ?
C00E O003 C00F C00L -175.9(2) . . . . ?
C00F O003 C00E C00N -179.0(2) . . . . ?
C00F O003 C00E C00O -61.8(3) . . . . ?
C00F O003 C00E C00P 63.5(3) . . . . ?
C00G C00B C00S C00T -177.3(2) . . . . ?
C00H C00A C00I C00K 178.6(2) . . . . ?
C00H C00A C00J C00U 179.4(2) . . . . ?
C00I C00A C00H C00C -127.8(2) . . . . ?
C00I C00A C00H C00L 105.5(3) . . . . ?
C00I C00A C00J C00U -1.1(4) . . . . ?
C00I C00K C00R C00U -1.8(4) . . . . ?
C00J C00A C00H C00C 51.7(3) . . . . ?
C00J C00A C00H C00L -75.0(3) . . . . ?
C00J C00A C00I C00K -0.9(4) . . . . ?
C00K C00R C00U C00J -0.2(4) . . . . ?
C00Q C00D C00G C00B 114.1(3) . . . . ?
C00Q C00D C00G C00L -119.0(3) . . . . ?
C00S C00B C00G C00D 56.1(3) . . . . ?
C00S C00B C00G C00L -70.6(3) . . . . ?

_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 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.700
####################################################################### 
# 
# 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_20210115_sc-14-148a
_database_code_depnum_ccdc_archive 'CCDC 2096476'
loop_
_audit_author_name
_audit_author_address
'Chun-Jiang Wang'
;Wuhan University
China
;
_audit_update_record             
;
2021-07-14 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H28 Br N O2'
_chemical_formula_sum            'C29 H28 Br N O2'
_chemical_formula_weight         502.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.53030(10)
_cell_length_b                   8.69550(10)
_cell_length_c                   39.2876(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2572.54(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15907
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5460
_cell_measurement_theta_min      4.5010
_shelx_estimated_absorpt_T_max   0.798
_shelx_estimated_absorpt_T_min   0.649
_exptl_absorpt_coefficient_mu    2.364
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_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  0.0390
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            26604
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.997
_diffrn_reflns_theta_min         4.502
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 -11.00   0.50    0.50    --    0.00 -19.00-180.00  118
  2  ω    -22.00  21.00   0.50    0.50    --    0.00  57.00-150.00   86
  3  ω     29.00  60.00   0.50    0.50    --    0.00  57.00-150.00   62
  4  ω    -33.00  30.00   0.50    0.50    --    0.00 -82.00  30.00  126
  5  ω    -33.00  31.00   0.50    0.50    --    0.00 -82.00 120.00  128
  6  ω     -3.00  28.00   0.50    0.50    --    0.00 -77.00-120.00   62
  7  ω     56.00 116.00   0.50    0.50    --   94.60 -82.00  90.00  120
  8  ω    136.00 183.00   0.50    0.50    --   94.60  30.00 -60.00   94
  9  ω      5.00 118.00   0.50    0.50    --   94.60 -61.00  90.00  226
 10  ω     92.00 127.00   0.50    0.50    --   94.60  30.00 -60.00   70
 11  ω     40.00 116.00   0.50    0.50    --   94.60 -82.00-120.00  152
 12  ω     81.00 184.00   0.50    0.50    --   94.60  77.00-150.00  206
 13  ω     33.00  79.00   0.50    0.50    --   94.60 -82.00 -90.00   92
 14  ω     19.00 116.00   0.50    0.50    --   94.60 -15.00-180.00  194
 15  ω     71.00 142.00   0.50    0.50    --   94.60  61.00-120.00  142
 16  ω     85.00 110.00   0.50    0.50    --   94.60 -45.00  30.00   50
 17  ω      6.00  49.00   0.50    0.50    --   94.60 -45.00  30.00   86
 18  ω     76.00 182.00   0.50    0.50    --   94.60  15.00   0.00  212
 19  ω     71.00 157.00   0.50    0.50    --   94.60  15.00  90.00  172
 20  ω     94.00 120.00   0.50    0.50    --   94.60  82.00-180.00   52
 21  ω     98.00 124.00   0.50    0.50    --   94.60  82.00 -90.00   52
 22  ω     15.00  91.00   0.50    0.50    --   94.60 -30.00 150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0668474000
_diffrn_orient_matrix_UB_12      0.1120738000
_diffrn_orient_matrix_UB_13      -0.0275460000
_diffrn_orient_matrix_UB_21      -0.0631331000
_diffrn_orient_matrix_UB_22      0.1117904000
_diffrn_orient_matrix_UB_23      0.0279044000
_diffrn_orient_matrix_UB_31      0.1827430000
_diffrn_orient_matrix_UB_32      0.0795849000
_diffrn_orient_matrix_UB_33      -0.0004335000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                5020
_reflns_number_total             5128
_reflns_odcompleteness_completeness 99.93
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 2035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(6)
_refine_ls_extinction_coef       0.00046(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.8187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0731
_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:
 C007(H007), C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00P(H00P), C00Q(H00Q), C00S(H00S), C00U(H00W), C00V(H00X), C00W(H00Y),
 C00X(H00Z)
2.c X=CH2 refined with riding coordinates:
 C00M(H00M,H00N), C00R(H00O,H00R)
2.d Idealised Me refined as rotating group:
 C00K(H00A,H00H,H00I), C00L(H00J,H00K,H00L), C00T(H00T,H00U,H00V)
;
_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 0.07592(5) 0.82455(4) 0.21313(2) 0.05528(13) Uani 1 1 d . . . . .
O002 O 0.3383(2) 0.59731(18) 0.36866(4) 0.0234(3) Uani 1 1 d . . . . .
O003 O 0.6315(2) 0.54574(19) 0.36343(5) 0.0293(4) Uani 1 1 d . . . . .
N004 N 0.2419(3) 0.9646(2) 0.37581(6) 0.0291(5) Uani 1 1 d . . . . .
C005 C 0.5086(3) 0.6331(2) 0.36586(6) 0.0222(5) Uani 1 1 d . . . . .
C006 C 0.4830(3) 0.8544(3) 0.30275(6) 0.0232(5) Uani 1 1 d . . . . .
C007 C 0.6165(3) 0.8673(3) 0.33181(6) 0.0244(5) Uani 1 1 d . . . . .
H007 H 0.641381 0.977102 0.334745 0.029 Uiso 1 1 calc R U . . .
C008 C 0.4054(3) 0.9863(3) 0.28927(6) 0.0273(5) Uani 1 1 d . . . . .
H008 H 0.435354 1.081645 0.298296 0.033 Uiso 1 1 calc R U . . .
C009 C 0.3655(3) 0.8906(3) 0.37159(6) 0.0229(5) Uani 1 1 d . . . . .
C00A C 0.5362(3) 0.8087(3) 0.36658(6) 0.0223(5) Uani 1 1 d . . . . .
C00B C 0.2843(4) 0.9789(3) 0.26269(7) 0.0317(6) Uani 1 1 d . . . . .
H00B H 0.233209 1.067889 0.253934 0.038 Uiso 1 1 calc R U . . .
C00C C 0.4363(3) 0.7124(3) 0.28873(6) 0.0272(5) Uani 1 1 d . . . . .
H00C H 0.487466 0.623071 0.297270 0.033 Uiso 1 1 calc R U . . .
C00D C 0.6641(3) 0.8459(3) 0.39719(6) 0.0248(5) Uani 1 1 d . . . . .
H00D H 0.784520 0.816772 0.390254 0.030 Uiso 1 1 calc R U . . .
C00E C 0.6658(4) 1.0156(3) 0.40489(6) 0.0273(5) Uani 1 1 d . . . . .
H00E H 0.562573 1.058935 0.413658 0.033 Uiso 1 1 calc R U . . .
C00F C 0.3147(4) 0.7026(3) 0.26221(6) 0.0299(5) Uani 1 1 d . . . . .
H00F H 0.283245 0.607592 0.253154 0.036 Uiso 1 1 calc R U . . .
C00G C 0.7901(3) 0.7921(3) 0.32256(6) 0.0307(5) Uani 1 1 d . . . . .
H00G H 0.790022 0.687118 0.318035 0.037 Uiso 1 1 calc R U . . .
C00H C 0.6178(4) 0.7524(3) 0.42890(6) 0.0281(5) Uani 1 1 d . . . . .
C00I C 0.2413(4) 0.8365(3) 0.24955(6) 0.0329(6) Uani 1 1 d . . . . .
C00J C 0.2813(4) 0.4338(3) 0.37138(7) 0.0277(5) Uani 1 1 d . . . . .
C00K C 0.3583(5) 0.3656(3) 0.40382(7) 0.0394(7) Uani 1 1 d . . . . .
H00A H 0.485296 0.360559 0.401950 0.059 Uiso 1 1 calc R U . . .
H00H H 0.311588 0.264020 0.407159 0.059 Uiso 1 1 calc R U . . .
H00I H 0.326679 0.429276 0.422845 0.059 Uiso 1 1 calc R U . . .
C00L C 0.3355(4) 0.3448(3) 0.33991(7) 0.0337(6) Uani 1 1 d . . . . .
H00J H 0.297337 0.399341 0.319963 0.051 Uiso 1 1 calc R U . . .
H00K H 0.281225 0.244934 0.340329 0.051 Uiso 1 1 calc R U . . .
H00L H 0.462344 0.333743 0.339487 0.051 Uiso 1 1 calc R U . . .
C00M C 0.8026(4) 1.1069(3) 0.40013(7) 0.0366(6) Uani 1 1 d . . . . .
H00M H 0.908061 1.067650 0.391406 0.044 Uiso 1 1 calc R U . . .
H00N H 0.793944 1.210852 0.405479 0.044 Uiso 1 1 calc R U . . .
C00N C 0.5363(4) 0.5782(3) 0.48748(7) 0.0357(6) Uani 1 1 d . . . . .
C00O C 0.6988(4) 0.5542(3) 0.47011(7) 0.0360(6) Uani 1 1 d . . . . .
C00P C 0.4554(4) 0.7736(3) 0.44636(7) 0.0327(6) Uani 1 1 d . . . . .
H00P H 0.374385 0.846157 0.438539 0.039 Uiso 1 1 calc R U . . .
C00Q C 0.7346(4) 0.6446(3) 0.44049(7) 0.0335(6) Uani 1 1 d . . . . .
H00Q H 0.840594 0.629430 0.428801 0.040 Uiso 1 1 calc R U . . .
C00R C 0.9422(4) 0.8667(4) 0.32053(7) 0.0405(7) Uani 1 1 d . . . . .
H00O H 0.946193 0.971761 0.324926 0.049 Uiso 1 1 calc R U . . .
H00R H 1.045473 0.814315 0.314700 0.049 Uiso 1 1 calc R U . . .
C00S C 0.4163(4) 0.6877(3) 0.47486(6) 0.0376(6) Uani 1 1 d . . . . .
H00S H 0.308483 0.702616 0.485926 0.045 Uiso 1 1 calc R U . . .
C00T C 0.0809(4) 0.4489(3) 0.37329(9) 0.0442(7) Uani 1 1 d . . . . .
H00T H 0.048941 0.502769 0.393714 0.066 Uiso 1 1 calc R U . . .
H00U H 0.028184 0.348350 0.373508 0.066 Uiso 1 1 calc R U . . .
H00V H 0.038800 0.505001 0.353862 0.066 Uiso 1 1 calc R U . . .
C00U C 0.6229(5) 0.3919(4) 0.52932(7) 0.0478(8) Uani 1 1 d . . . . .
H00W H 0.600593 0.339448 0.549507 0.057 Uiso 1 1 calc R U . . .
C00V C 0.5036(5) 0.4921(4) 0.51782(7) 0.0451(7) Uani 1 1 d . . . . .
H00X H 0.397892 0.506216 0.529650 0.054 Uiso 1 1 calc R U . . .
C00W C 0.8200(5) 0.4443(4) 0.48260(8) 0.0496(8) Uani 1 1 d . . . . .
H00Y H 0.926006 0.426907 0.471071 0.059 Uiso 1 1 calc R U . . .
C00X C 0.7829(6) 0.3633(4) 0.51153(8) 0.0567(10) Uani 1 1 d . . . . .
H00Z H 0.862323 0.289692 0.519490 0.068 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 C00I 1.900(3) . ?
O002 C005 1.324(3) . ?
O002 C00J 1.489(3) . ?
O003 C005 1.202(3) . ?
N004 C009 1.143(3) . ?
C005 C00A 1.541(3) . ?
C006 C007 1.525(3) . ?
C006 C008 1.392(3) . ?
C006 C00C 1.396(3) . ?
C007 H007 0.9800 . ?
C007 C00A 1.579(3) . ?
C007 C00G 1.506(3) . ?
C008 H008 0.9300 . ?
C008 C00B 1.388(4) . ?
C009 C00A 1.483(3) . ?
C00A C00D 1.574(3) . ?
C00B H00B 0.9300 . ?
C00B C00I 1.380(4) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.390(4) . ?
C00D H00D 0.9800 . ?
C00D C00E 1.507(3) . ?
C00D C00H 1.527(3) . ?
C00E H00E 0.9300 . ?
C00E C00M 1.314(4) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.381(4) . ?
C00G H00G 0.9300 . ?
C00G C00R 1.319(4) . ?
C00H C00P 1.414(4) . ?
C00H C00Q 1.364(4) . ?
C00J C00K 1.521(4) . ?
C00J C00L 1.514(4) . ?
C00J C00T 1.517(4) . ?
C00K H00A 0.9600 . ?
C00K H00H 0.9600 . ?
C00K H00I 0.9600 . ?
C00L H00J 0.9600 . ?
C00L H00K 0.9600 . ?
C00L H00L 0.9600 . ?
C00M H00M 0.9300 . ?
C00M H00N 0.9300 . ?
C00N C00O 1.417(4) . ?
C00N C00S 1.403(4) . ?
C00N C00V 1.429(4) . ?
C00O C00Q 1.430(4) . ?
C00O C00W 1.409(4) . ?
C00P H00P 0.9300 . ?
C00P C00S 1.378(4) . ?
C00Q H00Q 0.9300 . ?
C00R H00O 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9600 . ?
C00T H00U 0.9600 . ?
C00T H00V 0.9600 . ?
C00U H00W 0.9300 . ?
C00U C00V 1.330(5) . ?
C00U C00X 1.415(5) . ?
C00V H00X 0.9300 . ?
C00W H00Y 0.9300 . ?
C00W C00X 1.367(5) . ?
C00X H00Z 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
C005 O002 C00J 120.64(18) . . ?
O002 C005 C00A 111.23(19) . . ?
O003 C005 O002 127.2(2) . . ?
O003 C005 C00A 121.6(2) . . ?
C008 C006 C007 120.1(2) . . ?
C008 C006 C00C 118.2(2) . . ?
C00C C006 C007 121.7(2) . . ?
C006 C007 H007 106.6 . . ?
C006 C007 C00A 111.80(19) . . ?
C00A C007 H007 106.6 . . ?
C00G C007 C006 111.08(19) . . ?
C00G C007 H007 106.6 . . ?
C00G C007 C00A 113.65(19) . . ?
C006 C008 H008 119.2 . . ?
C00B C008 C006 121.6(2) . . ?
C00B C008 H008 119.2 . . ?
N004 C009 C00A 174.4(2) . . ?
C005 C00A C007 110.82(18) . . ?
C005 C00A C00D 107.46(18) . . ?
C009 C00A C005 111.20(19) . . ?
C009 C00A C007 106.98(18) . . ?
C009 C00A C00D 109.29(18) . . ?
C00D C00A C007 111.12(18) . . ?
C008 C00B H00B 120.8 . . ?
C00I C00B C008 118.5(2) . . ?
C00I C00B H00B 120.8 . . ?
C006 C00C H00C 119.5 . . ?
C00F C00C C006 121.1(2) . . ?
C00F C00C H00C 119.5 . . ?
C00A C00D H00D 107.5 . . ?
C00E C00D C00A 111.08(19) . . ?
C00E C00D H00D 107.5 . . ?
C00E C00D C00H 111.06(19) . . ?
C00H C00D C00A 112.0(2) . . ?
C00H C00D H00D 107.5 . . ?
C00D C00E H00E 117.6 . . ?
C00M C00E C00D 124.8(3) . . ?
C00M C00E H00E 117.6 . . ?
C00C C00F H00F 120.6 . . ?
C00I C00F C00C 118.8(2) . . ?
C00I C00F H00F 120.6 . . ?
C007 C00G H00G 118.2 . . ?
C00R C00G C007 123.7(3) . . ?
C00R C00G H00G 118.2 . . ?
C00P C00H C00D 121.6(2) . . ?
C00Q C00H C00D 119.4(2) . . ?
C00Q C00H C00P 119.0(2) . . ?
C00B C00I Br01 119.0(2) . . ?
C00B C00I C00F 121.9(2) . . ?
C00F C00I Br01 119.2(2) . . ?
O002 C00J C00K 108.8(2) . . ?
O002 C00J C00L 110.6(2) . . ?
O002 C00J C00T 101.98(19) . . ?
C00L C00J C00K 112.5(2) . . ?
C00L C00J C00T 110.7(2) . . ?
C00T C00J C00K 111.8(2) . . ?
C00J C00K H00A 109.5 . . ?
C00J C00K H00H 109.5 . . ?
C00J C00K H00I 109.5 . . ?
H00A C00K H00H 109.5 . . ?
H00A C00K H00I 109.5 . . ?
H00H C00K H00I 109.5 . . ?
C00J C00L H00J 109.5 . . ?
C00J C00L H00K 109.5 . . ?
C00J C00L H00L 109.5 . . ?
H00J C00L H00K 109.5 . . ?
H00J C00L H00L 109.5 . . ?
H00K C00L H00L 109.5 . . ?
C00E C00M H00M 120.0 . . ?
C00E C00M H00N 120.0 . . ?
H00M C00M H00N 120.0 . . ?
C00O C00N C00V 118.2(3) . . ?
C00S C00N C00O 119.1(2) . . ?
C00S C00N C00V 122.7(3) . . ?
C00N C00O C00Q 118.3(2) . . ?
C00W C00O C00N 119.5(3) . . ?
C00W C00O C00Q 122.3(3) . . ?
C00H C00P H00P 119.7 . . ?
C00S C00P C00H 120.6(3) . . ?
C00S C00P H00P 119.7 . . ?
C00H C00Q C00O 121.9(3) . . ?
C00H C00Q H00Q 119.1 . . ?
C00O C00Q H00Q 119.1 . . ?
C00G C00R H00O 120.0 . . ?
C00G C00R H00R 120.0 . . ?
H00O C00R H00R 120.0 . . ?
C00N C00S H00S 119.4 . . ?
C00P C00S C00N 121.2(3) . . ?
C00P C00S H00S 119.4 . . ?
C00J C00T H00T 109.5 . . ?
C00J C00T H00U 109.5 . . ?
C00J C00T H00V 109.5 . . ?
H00T C00T H00U 109.5 . . ?
H00T C00T H00V 109.5 . . ?
H00U C00T H00V 109.5 . . ?
C00V C00U H00W 119.3 . . ?
C00V C00U C00X 121.5(3) . . ?
C00X C00U H00W 119.3 . . ?
C00N C00V H00X 119.7 . . ?
C00U C00V C00N 120.7(3) . . ?
C00U C00V H00X 119.7 . . ?
C00O C00W H00Y 119.8 . . ?
C00X C00W C00O 120.4(3) . . ?
C00X C00W H00Y 119.8 . . ?
C00U C00X H00Z 120.2 . . ?
C00W C00X C00U 119.6(3) . . ?
C00W C00X H00Z 120.2 . . ?

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
O002 C005 C00A C007 -116.6(2) . . . . ?
O002 C005 C00A C009 2.2(3) . . . . ?
O002 C005 C00A C00D 121.8(2) . . . . ?
O003 C005 C00A C007 64.2(3) . . . . ?
O003 C005 C00A C009 -176.9(2) . . . . ?
O003 C005 C00A C00D -57.4(3) . . . . ?
C005 O002 C00J C00K 62.8(3) . . . . ?
C005 O002 C00J C00L -61.2(3) . . . . ?
C005 O002 C00J C00T -178.9(2) . . . . ?
C005 C00A C00D C00E -167.1(2) . . . . ?
C005 C00A C00D C00H -42.2(2) . . . . ?
C006 C007 C00A C005 69.2(2) . . . . ?
C006 C007 C00A C009 -52.1(2) . . . . ?
C006 C007 C00A C00D -171.36(19) . . . . ?
C006 C007 C00G C00R 117.9(3) . . . . ?
C006 C008 C00B C00I -0.1(4) . . . . ?
C006 C00C C00F C00I 0.7(4) . . . . ?
C007 C006 C008 C00B 179.6(2) . . . . ?
C007 C006 C00C C00F -179.9(2) . . . . ?
C007 C00A C00D C00E 71.6(2) . . . . ?
C007 C00A C00D C00H -163.63(19) . . . . ?
C008 C006 C007 C00A 108.0(2) . . . . ?
C008 C006 C007 C00G -123.9(2) . . . . ?
C008 C006 C00C C00F -0.5(3) . . . . ?
C008 C00B C00I Br01 -179.94(19) . . . . ?
C008 C00B C00I C00F 0.3(4) . . . . ?
C009 C00A C00D C00E -46.3(3) . . . . ?
C009 C00A C00D C00H 78.5(2) . . . . ?
C00A C007 C00G C00R -114.9(3) . . . . ?
C00A C00D C00E C00M -112.2(3) . . . . ?
C00A C00D C00H C00P -65.5(3) . . . . ?
C00A C00D C00H C00Q 113.7(3) . . . . ?
C00C C006 C007 C00A -72.6(3) . . . . ?
C00C C006 C007 C00G 55.5(3) . . . . ?
C00C C006 C008 C00B 0.2(4) . . . . ?
C00C C00F C00I Br01 179.64(18) . . . . ?
C00C C00F C00I C00B -0.6(4) . . . . ?
C00D C00H C00P C00S 179.8(2) . . . . ?
C00D C00H C00Q C00O 179.7(2) . . . . ?
C00E C00D C00H C00P 59.3(3) . . . . ?
C00E C00D C00H C00Q -121.5(3) . . . . ?
C00G C007 C00A C005 -57.5(3) . . . . ?
C00G C007 C00A C009 -178.9(2) . . . . ?
C00G C007 C00A C00D 61.9(3) . . . . ?
C00H C00D C00E C00M 122.5(3) . . . . ?
C00H C00P C00S C00N 0.5(4) . . . . ?
C00J O002 C005 O003 4.0(4) . . . . ?
C00J O002 C005 C00A -175.05(18) . . . . ?
C00N C00O C00Q C00H 0.4(4) . . . . ?
C00N C00O C00W C00X -1.1(5) . . . . ?
C00O C00N C00S C00P -1.2(4) . . . . ?
C00O C00N C00V C00U -0.1(4) . . . . ?
C00O C00W C00X C00U -1.0(5) . . . . ?
C00P C00H C00Q C00O -1.0(4) . . . . ?
C00Q C00H C00P C00S 0.6(4) . . . . ?
C00Q C00O C00W C00X 178.2(3) . . . . ?
C00S C00N C00O C00Q 0.7(4) . . . . ?
C00S C00N C00O C00W -180.0(3) . . . . ?
C00S C00N C00V C00U -178.4(3) . . . . ?
C00V C00N C00O C00Q -177.6(3) . . . . ?
C00V C00N C00O C00W 1.7(4) . . . . ?
C00V C00N C00S C00P 177.1(3) . . . . ?
C00V C00U C00X C00W 2.7(5) . . . . ?
C00W C00O C00Q C00H -178.9(3) . . . . ?
C00X C00U C00V C00N -2.0(5) . . . . ?

_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 1.934
_oxdiff_exptl_absorpt_empirical_full_min 0.695
####################################################################### 
# 
# 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_wcj-cx-15-72-20210223-rt
_database_code_depnum_ccdc_archive 'CCDC 2096478'
loop_
_audit_author_name
_audit_author_address
'Chun-Jiang Wang'
;Wuhan University
China
;
_audit_update_record             
;
2021-07-14 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 Cl4 I N O2'
_chemical_formula_sum            'C21 H14 Cl4 I N O2'
_chemical_formula_weight         581.03
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.2099(3)
_cell_length_b                   11.6051(4)
_cell_length_c                   12.1577(5)
_cell_angle_alpha                87.954(3)
_cell_angle_beta                 80.589(3)
_cell_angle_gamma                89.897(3)
_cell_volume                     1142.02(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15814
_cell_measurement_temperature    296.64(19)
_cell_measurement_theta_max      71.0010
_cell_measurement_theta_min      3.6270
_shelx_estimated_absorpt_T_max   0.747
_shelx_estimated_absorpt_T_min   0.577
_exptl_absorpt_coefficient_mu    15.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1302
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35246
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        64.983
_diffrn_reflns_theta_max         64.983
_diffrn_reflns_theta_min         3.688
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.64(19)
_diffrn_detector                 'Hybrid Pixel Counting (HPC) detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HyPix-6000HE'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  94.00   0.50    0.50    --    5.00  76.00 150.00  254
  2  ω    -84.00  42.00   0.50    0.50    --    5.00 -37.00  30.00  252
  3  ω    -32.00  94.00   0.50    0.50    --    5.00  37.00 -30.00  252
  4  ω   -136.00  -8.00   0.50    0.50    --  -46.70 -76.00 -30.00  256
  5  ω   -136.00  -8.00   0.50    0.50    --  -46.70 -76.00-150.00  256
  6  ω   -136.00  -8.00   0.50    0.50    --  -46.70 -76.00 -90.00  256
  7  ω   -136.00  -8.00   0.50    0.50    --  -46.70 -76.00  60.00  256
  8  ω   -136.00 -13.00   0.50    0.50    --  -46.70 -57.00  90.00  246
  9  ω    -80.00  43.00   0.50    0.50    --  -46.70  57.00-120.00  246
 10  ω   -187.00 -61.00   0.50    0.50    --  -97.30 -69.00 112.65  252
 11  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00  74.62  256
 12  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -74.00 148.90  256
 13  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -75.00 -53.72  256
 14  ω   -187.00 -60.00   0.50    0.50    --  -97.30 -72.00-147.21  254
 15  ω   -187.00 -60.00   0.50    0.50    --  -97.30 -73.00-111.00  254
 16  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -74.00 160.03  256
 17  ω   -136.00  -8.00   0.50    0.50    --  -97.30  76.00-120.00  256
 18  ω   -136.00  -8.00   0.50    0.50    --  -97.30  76.00-180.00  256
 19  ω   -136.00  -8.00   0.50    0.50    --  -97.30  76.00 -30.00  256
 20  ω   -136.00  -8.00   0.50    0.50    --  -97.30  76.00  30.00  256
 21  ω   -187.00 -60.00   0.50    0.50    --  -97.30 -73.00   8.34  254
 22  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00-180.00  256
 23  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00  51.47  256
 24  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00 -60.00  256
 25  ω   -187.00 -62.00   0.50    0.50    --  -97.30 -68.00 -92.67  250
 26  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00-120.00  256
 27  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -75.00  33.69  256
 28  ω   -187.00 -62.00   0.50    0.50    --  -97.30 -68.00  95.03  250
 29  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00 -90.00  256
 30  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00  90.00  256
 31  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00 -15.15  256
 32  ω   -187.00 -63.00   0.50    0.50    --  -97.30 -62.00 176.58  248
 33  ω   -136.00  -8.00   0.50    0.50    --  -97.30  76.00  90.00  256
 34  ω   -187.00 -59.00   0.50    0.50    --  -97.30 -76.00 -35.12  256
 35  ω   -136.00  -8.00   0.50    0.50    --  -46.70 -76.00-180.00  256
 36  ω   -136.00  43.00   0.50    0.50    --  -46.70   0.00-180.00  358
 37  ω   -136.00  43.00   0.50    0.50    --  -46.70   0.00-150.00  358
 38  ω   -136.00   3.00   0.50    0.50    --  -46.70   0.00-120.00  278
 39  ω   -136.00 -13.00   0.50    0.50    --  -46.70 -57.00 -60.00  246
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'profile data from ω-scans and φ-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0201039000
_diffrn_orient_matrix_UB_12      -0.1281241000
_diffrn_orient_matrix_UB_13      -0.0242738000
_diffrn_orient_matrix_UB_21      -0.0381454000
_diffrn_orient_matrix_UB_22      -0.0292280000
_diffrn_orient_matrix_UB_23      0.1262016000
_diffrn_orient_matrix_UB_31      -0.1852568000
_diffrn_orient_matrix_UB_32      0.0193635000
_diffrn_orient_matrix_UB_33      -0.0017680000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'VariMax VHF'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                6921
_reflns_number_total             7558
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     39.93
_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 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection       
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction        
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.982
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.001(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7558
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0738
_refine_ls_restrained_S_all      1.087
_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)+(0.1592P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2029
_refine_ls_wR_factor_ref         0.2072
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C33(H33), C13(H13), C32(H32), C28(H28), C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C4(H4), C27(H27), C42(H42), C38(H38), C40(H40), C8(H8),
 C21(H21), C29(H29), C17(H17), C25(H25), C19(H19), C23(H23)
2.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C30(H30A,H30B)
;
_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
I1 I 0.33465(10) 0.58369(7) 0.14829(7) 0.0864(3) Uani 1 1 d . . . . .
I2 I 0.67748(12) 0.41912(8) 0.86127(8) 0.0927(4) Uani 1 1 d . . . . .
Cl4 Cl 0.2092(7) 0.6390(3) 0.8121(4) 0.1021(13) Uani 1 1 d . . . . .
Cl3 Cl 0.1717(6) 0.2039(4) 0.9797(3) 0.0927(12) Uani 1 1 d . . . . .
Cl7 Cl 1.1576(5) 0.9280(3) 0.7936(4) 0.0942(11) Uani 1 1 d . . . . .
Cl6 Cl 0.8530(7) 0.7856(4) 0.0179(3) 0.1049(14) Uani 1 1 d . . . . .
Cl5 Cl 0.8701(7) 0.3545(4) 0.1898(5) 0.1065(14) Uani 1 1 d . . . . .
Cl2 Cl 0.7848(6) 0.0667(5) 0.1782(6) 0.1224(19) Uani 1 1 d . . . . .
Cl8 Cl 0.5464(7) 1.1005(5) 0.8701(5) 0.1195(17) Uani 1 1 d . . . . .
Cl1 Cl 0.1955(8) -0.0981(5) 0.1255(6) 0.1221(18) Uani 1 1 d . . . . .
C31 C 0.7551(15) 0.7281(12) 0.5151(10) 0.062(3) Uani 1 1 d . . . . .
O3 O 1.0016(12) 0.6028(11) 0.4687(9) 0.083(3) Uani 1 1 d . . . . .
C22 C 0.8199(19) 0.6907(13) 0.1310(11) 0.070(3) Uani 1 1 d . . . . .
O2 O 0.4936(12) 0.3861(11) 0.5319(8) 0.079(2) Uani 1 1 d . . . . .
C36 C 0.678(2) 0.5982(13) 0.8073(13) 0.073(3) Uani 1 1 d . . . . .
H36A H 0.5827 0.6363 0.8482 0.087 Uiso 1 1 calc R . . . .
H36B H 0.7765 0.6356 0.8232 0.087 Uiso 1 1 calc R . . . .
O1 O 0.3834(13) 0.4321(9) 0.3819(7) 0.075(2) Uani 1 1 d . . . . .
O4 O 0.8227(12) 0.5646(8) 0.6220(8) 0.073(2) Uani 1 1 d . . . . .
C16 C 0.3264(16) 0.1658(11) 0.2917(10) 0.062(3) Uani 1 1 d . . . . .
C18 C 0.310(2) -0.0009(12) 0.1833(12) 0.074(3) Uani 1 1 d . . . . .
C2 C 0.190(2) 0.4173(15) 0.8851(11) 0.072(3) Uani 1 1 d . . . . .
H2 H 0.2057 0.4434 0.9541 0.087 Uiso 1 1 calc R . . . .
C6 C 0.1514(17) 0.2602(11) 0.7657(9) 0.067(3) Uani 1 1 d . . . . .
H6 H 0.1439 0.1814 0.7560 0.080 Uiso 1 1 calc R . . . .
C34 C 0.8781(16) 0.6235(13) 0.5298(10) 0.068(3) Uani 1 1 d . . . . .
C11 C 0.3978(16) 0.3660(11) 0.4726(9) 0.065(3) Uani 1 1 d . . . . .
C41 C 0.9517(17) 0.9209(11) 0.7764(10) 0.067(3) Uani 1 1 d . . . . .
C4 C 0.1656(16) 0.4549(11) 0.6920(10) 0.066(3) Uani 1 1 d . . . . .
H4 H 0.1659 0.5083 0.6330 0.079 Uiso 1 1 calc R . . . .
C24 C 0.8232(17) 0.4977(12) 0.2088(13) 0.069(3) Uani 1 1 d . . . . .
C33 C 0.6728(18) 0.6095(14) 0.6854(11) 0.075(3) Uani 1 1 d . . . . .
H33 H 0.5782 0.5657 0.6690 0.090 Uiso 1 1 calc R . . . .
C13 C 0.2325(15) 0.2599(11) 0.3621(9) 0.062(2) Uani 1 1 d . . . . .
H13 H 0.1141 0.2443 0.3679 0.074 Uiso 1 1 calc R . . . .
C32 C 0.6630(16) 0.7372(12) 0.6384(9) 0.064(3) Uani 1 1 d . . . . .
H32 H 0.5469 0.7557 0.6365 0.076 Uiso 1 1 calc R . . . .
C28 C 0.6303(14) 0.6873(11) 0.4375(9) 0.061(2) Uani 1 1 d . . . . .
H28 H 0.5704 0.6202 0.4752 0.073 Uiso 1 1 calc R . . . .
C27 C 0.7489(17) 0.7288(11) 0.2339(10) 0.066(3) Uani 1 1 d . . . . .
H27 H 0.7234 0.8064 0.2426 0.080 Uiso 1 1 calc R . . . .
C35 C 0.8500(19) 0.8275(14) 0.4685(11) 0.076(3) Uani 1 1 d . . . . .
C42 C 0.8995(17) 0.8345(11) 0.7146(10) 0.066(3) Uani 1 1 d . . . . .
H42 H 0.9745 0.7811 0.6810 0.079 Uiso 1 1 calc R . . . .
C37 C 0.7343(15) 0.8283(10) 0.7032(10) 0.058(2) Uani 1 1 d . . . . .
C5 C 0.1435(15) 0.3392(10) 0.6756(9) 0.058(2) Uani 1 1 d . . . . .
N1 N 0.397(2) 0.0793(14) 0.5587(12) 0.102(5) Uani 1 1 d . . . . .
C38 C 0.6281(18) 0.9124(13) 0.7499(11) 0.073(3) Uani 1 1 d . . . . .
H38 H 0.5177 0.9101 0.7413 0.088 Uiso 1 1 calc R . . . .
C26 C 0.7148(15) 0.6500(10) 0.3262(9) 0.062(2) Uani 1 1 d . . . . .
C7 C 0.1069(15) 0.3012(12) 0.5638(9) 0.062(3) Uani 1 1 d . . . . .
H7 H 0.0595 0.3676 0.5284 0.074 Uiso 1 1 calc R . . . .
C20 C 0.5718(19) 0.0757(12) 0.2079(14) 0.077(3) Uani 1 1 d . . . . .
C3 C 0.1870(19) 0.4919(12) 0.7951(14) 0.072(3) Uani 1 1 d . . . . .
C40 C 0.8474(19) 1.0035(11) 0.8252(11) 0.072(3) Uani 1 1 d . . . . .
H40 H 0.8848 1.0600 0.8676 0.087 Uiso 1 1 calc R . . . .
C8 C -0.0174(16) 0.2045(13) 0.5740(11) 0.072(3) Uani 1 1 d . . . . .
H8 H 0.0170 0.1303 0.5902 0.086 Uiso 1 1 calc R . . . .
C9 C -0.171(2) 0.220(2) 0.5610(19) 0.108(6) Uani 1 1 d . . . . .
H9A H -0.2087 0.2930 0.5448 0.130 Uiso 1 1 calc R . . . .
H9B H -0.2434 0.1570 0.5682 0.130 Uiso 1 1 calc R . . . .
C21 C 0.4967(18) 0.1607(12) 0.2712(12) 0.071(3) Uani 1 1 d . . . . .
H21 H 0.5594 0.2150 0.3004 0.086 Uiso 1 1 calc R . . . .
C29 C 0.5050(19) 0.7826(15) 0.4309(12) 0.077(4) Uani 1 1 d . . . . .
H29 H 0.5452 0.8573 0.4154 0.093 Uiso 1 1 calc R . . . .
C17 C 0.2338(17) 0.0879(12) 0.2488(11) 0.069(3) Uani 1 1 d . . . . .
H17 H 0.1193 0.0931 0.2626 0.082 Uiso 1 1 calc R . . . .
N2 N 0.918(2) 0.9068(16) 0.4316(13) 0.104(4) Uani 1 1 d . . . . .
C12 C 0.2640(16) 0.3858(10) 0.3193(9) 0.062(3) Uani 1 1 d . . . . .
H12 H 0.1608 0.4288 0.3370 0.074 Uiso 1 1 calc R . . . .
C25 C 0.7544(18) 0.5336(12) 0.3109(11) 0.071(3) Uani 1 1 d . . . . .
H25 H 0.7335 0.4808 0.3709 0.085 Uiso 1 1 calc R . . . .
C19 C 0.483(2) -0.0058(13) 0.1587(12) 0.080(4) Uani 1 1 d . . . . .
H19 H 0.5358 -0.0606 0.1118 0.096 Uiso 1 1 calc R . . . .
C14 C 0.3445(18) 0.1607(13) 0.5257(11) 0.073(3) Uani 1 1 d . . . . .
C39 C 0.683(2) 1.0000(15) 0.8091(12) 0.081(4) Uani 1 1 d . . . . .
C23 C 0.8577(19) 0.5761(16) 0.1155(13) 0.078(4) Uani 1 1 d . . . . .
H23 H 0.9045 0.5507 0.0457 0.094 Uiso 1 1 calc R . . . .
C30 C 0.348(2) 0.768(2) 0.4450(19) 0.110(6) Uani 1 1 d . . . . .
H30A H 0.3029 0.6949 0.4606 0.132 Uiso 1 1 calc R . . . .
H30B H 0.2792 0.8313 0.4395 0.132 Uiso 1 1 calc R . . . .
C15 C 0.330(2) 0.4045(14) 0.1981(11) 0.078(4) Uani 1 1 d . . . . .
H15A H 0.2610 0.3630 0.1548 0.094 Uiso 1 1 calc R . . . .
H15B H 0.4405 0.3736 0.1822 0.094 Uiso 1 1 calc R . . . .
C10 C 0.2722(16) 0.2675(11) 0.4835(10) 0.062(3) Uani 1 1 d . . . . .
C1 C 0.1701(19) 0.3004(13) 0.8676(11) 0.072(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C15 2.143(17) . ?
I2 C36 2.157(15) . ?
Cl4 C3 1.740(15) . ?
Cl3 C1 1.734(14) . ?
Cl7 C41 1.739(14) . ?
Cl6 C22 1.717(15) . ?
Cl5 C24 1.720(14) . ?
Cl2 C20 1.731(16) . ?
Cl8 C39 1.717(14) . ?
Cl1 C18 1.712(15) . ?
C31 C34 1.601(18) . ?
C31 C32 1.572(15) . ?
C31 C28 1.586(16) . ?
C31 C35 1.44(2) . ?
O3 C34 1.185(16) . ?
C22 C27 1.379(19) . ?
C22 C23 1.38(2) . ?
O2 C11 1.180(16) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C33 1.49(2) . ?
O1 C11 1.342(16) . ?
O1 C12 1.451(16) . ?
O4 C34 1.308(17) . ?
O4 C33 1.448(17) . ?
C16 C13 1.539(15) . ?
C16 C21 1.38(2) . ?
C16 C17 1.354(19) . ?
C18 C17 1.408(19) . ?
C18 C19 1.40(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.37(2) . ?
C2 C1 1.39(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.413(16) . ?
C6 C1 1.371(19) . ?
C11 C10 1.529(19) . ?
C41 C42 1.38(2) . ?
C41 C40 1.37(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(18) . ?
C4 C3 1.38(2) . ?
C24 C25 1.36(2) . ?
C24 C23 1.42(3) . ?
C33 H33 0.9800 . ?
C33 C32 1.58(2) . ?
C13 H13 0.9800 . ?
C13 C12 1.541(18) . ?
C13 C10 1.568(15) . ?
C32 H32 0.9800 . ?
C32 C37 1.514(18) . ?
C28 H28 0.9800 . ?
C28 C26 1.495(16) . ?
C28 C29 1.519(19) . ?
C27 H27 0.9300 . ?
C27 C26 1.413(17) . ?
C35 N2 1.12(2) . ?
C42 H42 0.9300 . ?
C42 C37 1.388(19) . ?
C37 C38 1.383(17) . ?
C5 C7 1.520(15) . ?
N1 C14 1.13(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.38(2) . ?
C26 C25 1.401(19) . ?
C7 H7 0.9800 . ?
C7 C8 1.51(2) . ?
C7 C10 1.594(16) . ?
C20 C21 1.357(19) . ?
C20 C19 1.41(2) . ?
C40 H40 0.9300 . ?
C40 C39 1.40(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.31(3) . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C21 H21 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.28(3) . ?
C17 H17 0.9300 . ?
C12 H12 0.9800 . ?
C12 C15 1.493(18) . ?
C25 H25 0.9300 . ?
C19 H19 0.9300 . ?
C14 C10 1.484(19) . ?
C23 H23 0.9300 . ?
C30 H30A 0.9300 . ?
C30 H30B 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 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
C32 C31 C34 100.6(9) . . ?
C32 C31 C28 110.0(10) . . ?
C28 C31 C34 107.7(10) . . ?
C35 C31 C34 109.1(11) . . ?
C35 C31 C32 116.2(11) . . ?
C35 C31 C28 112.3(11) . . ?
C27 C22 Cl6 119.9(12) . . ?
C23 C22 Cl6 118.8(11) . . ?
C23 C22 C27 121.2(14) . . ?
I2 C36 H36A 109.5 . . ?
I2 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?
C33 C36 I2 110.7(10) . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C11 O1 C12 112.1(10) . . ?
C34 O4 C33 114.6(10) . . ?
C21 C16 C13 122.4(12) . . ?
C17 C16 C13 116.7(11) . . ?
C17 C16 C21 120.9(12) . . ?
C17 C18 Cl1 121.0(12) . . ?
C19 C18 Cl1 119.1(11) . . ?
C19 C18 C17 119.8(13) . . ?
C3 C2 H2 121.7 . . ?
C3 C2 C1 116.7(12) . . ?
C1 C2 H2 121.7 . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C1 C6 C5 119.6(12) . . ?
O3 C34 C31 126.1(12) . . ?
O3 C34 O4 124.7(13) . . ?
O4 C34 C31 109.2(10) . . ?
O2 C11 O1 122.6(13) . . ?
O2 C11 C10 128.3(12) . . ?
O1 C11 C10 109.1(11) . . ?
C42 C41 Cl7 119.9(10) . . ?
C40 C41 Cl7 117.4(11) . . ?
C40 C41 C42 122.7(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(12) . . ?
C25 C24 Cl5 120.2(13) . . ?
C25 C24 C23 121.4(13) . . ?
C23 C24 Cl5 118.4(10) . . ?
C36 C33 H33 109.0 . . ?
C36 C33 C32 114.8(12) . . ?
O4 C33 C36 110.5(13) . . ?
O4 C33 H33 109.0 . . ?
O4 C33 C32 104.3(10) . . ?
C32 C33 H33 109.0 . . ?
C16 C13 H13 107.8 . . ?
C16 C13 C12 116.9(10) . . ?
C16 C13 C10 115.2(10) . . ?
C12 C13 H13 107.8 . . ?
C12 C13 C10 100.6(9) . . ?
C10 C13 H13 107.8 . . ?
C31 C32 C33 102.0(10) . . ?
C31 C32 H32 108.5 . . ?
C33 C32 H32 108.5 . . ?
C37 C32 C31 113.6(11) . . ?
C37 C32 C33 115.4(10) . . ?
C37 C32 H32 108.5 . . ?
C31 C28 H28 107.3 . . ?
C26 C28 C31 113.1(9) . . ?
C26 C28 H28 107.3 . . ?
C26 C28 C29 113.7(10) . . ?
C29 C28 C31 107.9(10) . . ?
C29 C28 H28 107.3 . . ?
C22 C27 H27 120.0 . . ?
C22 C27 C26 120.1(12) . . ?
C26 C27 H27 120.0 . . ?
N2 C35 C31 177.3(18) . . ?
C41 C42 H42 120.3 . . ?
C41 C42 C37 119.4(11) . . ?
C37 C42 H42 120.3 . . ?
C42 C37 C32 124.1(10) . . ?
C38 C37 C32 117.3(12) . . ?
C38 C37 C42 118.6(12) . . ?
C6 C5 C7 122.2(11) . . ?
C4 C5 C6 118.2(10) . . ?
C4 C5 C7 119.6(10) . . ?
C37 C38 H38 119.3 . . ?
C39 C38 C37 121.3(14) . . ?
C39 C38 H38 119.3 . . ?
C27 C26 C28 121.5(11) . . ?
C25 C26 C28 119.6(11) . . ?
C25 C26 C27 118.8(11) . . ?
C5 C7 H7 107.2 . . ?
C5 C7 C10 111.1(9) . . ?
C8 C7 C5 113.4(10) . . ?
C8 C7 H7 107.2 . . ?
C8 C7 C10 110.5(10) . . ?
C10 C7 H7 107.2 . . ?
C21 C20 Cl2 121.2(12) . . ?
C21 C20 C19 122.4(14) . . ?
C19 C20 Cl2 116.4(11) . . ?
C2 C3 Cl4 118.8(12) . . ?
C2 C3 C4 122.6(14) . . ?
C4 C3 Cl4 118.6(12) . . ?
C41 C40 H40 121.2 . . ?
C41 C40 C39 117.6(13) . . ?
C39 C40 H40 121.2 . . ?
C7 C8 H8 118.4 . . ?
C9 C8 C7 123.3(16) . . ?
C9 C8 H8 118.4 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C16 C21 H21 120.3 . . ?
C20 C21 C16 119.4(13) . . ?
C20 C21 H21 120.3 . . ?
C28 C29 H29 117.4 . . ?
C30 C29 C28 125.2(19) . . ?
C30 C29 H29 117.4 . . ?
C16 C17 C18 120.2(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
O1 C12 C13 106.2(9) . . ?
O1 C12 H12 108.5 . . ?
O1 C12 C15 108.0(12) . . ?
C13 C12 H12 108.5 . . ?
C15 C12 C13 116.8(11) . . ?
C15 C12 H12 108.5 . . ?
C24 C25 C26 120.2(13) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C18 C19 C20 117.1(13) . . ?
C18 C19 H19 121.4 . . ?
C20 C19 H19 121.4 . . ?
N1 C14 C10 179.0(18) . . ?
C38 C39 Cl8 120.3(13) . . ?
C38 C39 C40 120.2(13) . . ?
C40 C39 Cl8 119.4(13) . . ?
C22 C23 C24 118.3(12) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C29 C30 H30A 120.0 . . ?
C29 C30 H30B 120.0 . . ?
H30A C30 H30B 120.0 . . ?
I1 C15 H15A 109.2 . . ?
I1 C15 H15B 109.2 . . ?
C12 C15 I1 111.9(9) . . ?
C12 C15 H15A 109.2 . . ?
C12 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C11 C10 C13 103.1(10) . . ?
C11 C10 C7 110.5(10) . . ?
C13 C10 C7 108.2(9) . . ?
C14 C10 C11 109.9(11) . . ?
C14 C10 C13 114.0(10) . . ?
C14 C10 C7 110.9(11) . . ?
C2 C1 Cl3 117.9(11) . . ?
C6 C1 Cl3 119.7(12) . . ?
C6 C1 C2 122.4(13) . . ?

_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 2.937
_oxdiff_exptl_absorpt_empirical_full_min 0.345
