# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_745
_database_code_depnum_ccdc_archive 'CCDC 1909456'
loop_
_audit_author_name
_audit_author_address
'Xiao-Li Zhao'
;East China Normal University
China
;
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-10-16 downloaded from the CCDC.
;
_audit_creation_date             2019-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Br N2 O4, C H Cl3'
_chemical_formula_sum            'C22 H18 Br Cl3 N2 O4'
_chemical_formula_weight         560.64
_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'
Cl Cl 0.3639 0.7018 '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                   13.3229(3)
_cell_length_b                   6.20240(10)
_cell_length_c                   15.4655(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.145(3)
_cell_angle_gamma                90
_cell_volume                     1156.87(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14508
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2650
_cell_measurement_theta_min      5.7210
_shelx_estimated_absorpt_T_max   0.799
_shelx_estimated_absorpt_T_min   0.226
_exptl_absorpt_coefficient_mu    5.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23138
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.806
_diffrn_reflns_theta_min         3.665
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  27.00   1.00    4.00    --    0.00  82.00-180.00   58
  2  ω    -19.00  28.00   1.00    4.00    --    0.00  38.00 -30.00   47
  3  ω    -49.00  19.00   1.00    4.00    --    0.00 -38.00-180.00   68
  4  ω    -15.00  11.00   1.00    4.00    --    0.00 -77.00-180.00   26
  5  ω    -14.00  31.00   1.00    4.00    --    0.00  38.00 -90.00   45
  6  ω     31.00  67.00   1.00    4.00    --    0.00  38.00 -30.00   36
  7  ω     46.00  89.00   1.00    4.00    --    0.00  38.00 -90.00   43
  8  ω     33.00  82.00   1.00    4.00    --    0.00  82.00-180.00   49
  9  ω    -85.00 -60.00   1.00    4.00    --    0.00 -77.00-180.00   25
 10  ω    -23.00  80.00   1.00    4.00    --    0.00  57.00  60.00  103
 11  ω    -86.00 -54.00   1.00    4.00    --    0.00 -38.00-180.00   32
 12  ω     47.00  86.00   1.00    4.00    --    0.00  38.00 120.00   39
 13  ω     64.00  89.00   1.00    4.00    --   95.80  82.00 -30.00   25
 14  ω    134.00 185.00   1.00    4.00    --   95.80  76.00 133.88   51
 15  ω    154.00 182.00   1.00    4.00    --   95.80  69.00-122.22   28
 16  ω     65.00  94.00   1.00    4.00    --   95.80  76.00 133.88   29
 17  ω    153.00 184.00   1.00    4.00    --   95.80  67.00 -35.23   31
 18  ω    104.00 130.00   1.00    4.00    --   95.80  69.00-122.22   26
 19  ω    122.00 183.00   1.00    4.00    --   95.80  58.00  17.89   61
 20  ω    160.00 185.00   1.00    4.00    --   95.80  82.00-150.00   25
 21  ω     65.00  91.00   1.00    4.00    --   95.80  77.00 120.00   26
 22  ω     70.00  95.00   1.00    4.00    --   95.80  67.00 -35.23   25
 23  ω     63.00  89.00   1.00    4.00    --   95.80  82.00  60.00   26
 24  ω     65.00  91.00   1.00    4.00    --   95.80  77.00-150.00   26
 25  ω      7.00  55.00   1.00    4.00    --   95.80 -82.00-120.00   48
 26  ω     58.00 118.00   1.00    4.00    --   95.80 -82.00-120.00   60
 27  ω    129.00 185.00   1.00    4.00    --   95.80  82.00  90.00   56
 28  ω     63.00  89.00   1.00    4.00    --   95.80  82.00  30.00   26
 29  ω    154.00 180.00   1.00    4.00    --   95.80  82.00  30.00   26
 30  ω     66.00  91.00   1.00    4.00    --   95.80  77.00-180.00   25
 31  ω     63.00  95.00   1.00    4.00    --   95.80  82.00  90.00   32
 32  ω     72.00 110.00   1.00    4.00    --   95.80  55.00 -31.18   38
 33  ω     68.00  95.00   1.00    4.00    --   95.80  69.00-122.22   27
 34  ω     95.00 126.00   1.00    4.00    --   95.80 -77.00  30.00   31
 35  ω     15.00 101.00   1.00    4.00    --   95.80 -82.00-180.00   86
 36  ω     13.00  80.00   1.00    4.00    --   95.80 -77.00  30.00   67
 37  ω     64.00  90.00   1.00    4.00    --   95.80  80.00   5.55   26
 38  ω     77.00 170.00   1.00    4.00    --   95.80  45.00  60.00   93
 39  ω     65.00  91.00   1.00    4.00    --   95.80  77.00 -90.00   26
 40  ω    134.00 183.00   1.00    4.00    --   95.80  77.00 -90.00   49
 41  ω     66.00 108.00   1.00    4.00    --   95.80  77.00 -30.00   42
 42  ω     65.00  91.00   1.00    4.00    --   95.80  77.00  90.00   26
 43  ω    141.00 166.00   1.00    4.00    --   95.80  77.00  90.00   25
 44  ω     63.00  89.00   1.00    4.00    --   95.80  82.00-150.00   26
 45  ω     76.00 139.00   1.00    4.00    --   95.80  45.00 120.00   63
 46  ω     88.00 127.00   1.00    4.00    --   95.80 -82.00  90.00   39
 47  ω     65.00  91.00   1.00    4.00    --   95.80  77.00 -60.00   26
 48  ω     65.00  91.00   1.00    4.00    --   95.80  77.00 150.00   26
 49  ω     76.00 117.00   1.00    4.00    --   95.80  30.00  60.00   41
 50  ω     79.00 131.00   1.00    4.00    --   95.80  45.00-180.00   52
 51  ω     75.00 183.00   1.00    4.00    --   95.80  45.00-150.00  108
 52  ω     76.00 150.00   1.00    4.00    --   95.80  45.00 -30.00   74
 53  ω     77.00 137.00   1.00    4.00    --   95.80  45.00 150.00   60
 54  ω     63.00  90.00   1.00    4.00    --   95.80  82.00 150.00   27
 55  ω      8.00 126.00   1.00    4.00    --   95.80 -82.00   0.00  118
 56  ω     64.00  89.00   1.00    4.00    --   95.80  79.00-109.85   25
 57  ω     84.00 125.00   1.00    4.00    --   95.80  30.00  30.00   41
 58  ω     76.00 165.00   1.00    4.00    --   95.80  45.00-120.00   89
 59  ω     72.00  97.00   1.00    4.00    --   95.80  61.00 -60.00   25
 60  ω     69.00 184.00   1.00    4.00    --   95.80  66.00  67.50  115
 61  ω     72.00  99.00   1.00    4.00    --   95.80  58.00  17.89   27
 62  ω     66.00  93.00   1.00    4.00    --   95.80  82.00-180.00   27
 63  ω     75.00 168.00   1.00    4.00    --   95.80  57.00 -96.89   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0237878000
_diffrn_orient_matrix_UB_12      -0.0969476000
_diffrn_orient_matrix_UB_13      0.0985229000
_diffrn_orient_matrix_UB_21      0.1099946000
_diffrn_orient_matrix_UB_22      0.1259675000
_diffrn_orient_matrix_UB_23      0.0443841000
_diffrn_orient_matrix_UB_31      -0.0604892000
_diffrn_orient_matrix_UB_32      0.1908409000
_diffrn_orient_matrix_UB_33      0.0207054000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.799
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                4428
_reflns_number_total             4644
_reflns_odcompleteness_completeness 99.91
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.232
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.093
_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)+(0.0592P)²+1.1260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1112
_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:
 C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.07944(4) 0.14912(14) 0.73280(3) 0.0385(2) Uani 1 1 d . . . . .
O1 O 0.5634(3) 0.0497(6) 0.3561(3) 0.0231(8) Uani 1 1 d . . . . .
O2 O 0.5342(3) 0.3790(6) 0.4017(3) 0.0236(8) Uani 1 1 d . . . . .
O3 O 0.4260(3) 0.4282(6) 0.1850(2) 0.0204(7) Uani 1 1 d . . . . .
O4 O 0.5041(3) 0.9838(6) 0.0311(2) 0.0227(7) Uani 1 1 d . . . . .
N1 N 0.6818(3) 0.2123(7) 0.2670(3) 0.0173(8) Uani 1 1 d . . . . .
N2 N 0.4405(3) 0.7315(7) 0.1051(3) 0.0163(8) Uani 1 1 d . . . . .
C1 C 0.8146(4) 0.4438(9) 0.5141(3) 0.0222(10) Uani 1 1 d . . . . .
H1 H 0.773517 0.569307 0.506369 0.027 Uiso 1 1 calc R . . . .
C2 C 0.9054(4) 0.4053(9) 0.6011(3) 0.0242(11) Uani 1 1 d . . . . .
H2 H 0.925853 0.504581 0.650755 0.029 Uiso 1 1 calc R . . . .
C3 C 0.9640(4) 0.2161(10) 0.6115(3) 0.0262(12) Uani 1 1 d . . . . .
C4 C 0.9387(4) 0.0701(9) 0.5374(4) 0.0226(11) Uani 1 1 d . . . . .
H4 H 0.981145 -0.053558 0.545013 0.027 Uiso 1 1 calc R . . . .
C5 C 0.8475(4) 0.1135(9) 0.4506(3) 0.0202(10) Uani 1 1 d . . . . .
H5 H 0.828964 0.017070 0.400055 0.024 Uiso 1 1 calc R . . . .
C6 C 0.7844(4) 0.2987(9) 0.4390(3) 0.0187(10) Uani 1 1 d . . . . .
C7 C 0.6792(4) 0.3364(8) 0.3478(3) 0.0173(9) Uani 1 1 d . . . . .
C8 C 0.6623(4) 0.5758(8) 0.3149(3) 0.0174(9) Uani 1 1 d . . . . .
H8A H 0.613722 0.649788 0.337399 0.021 Uiso 1 1 calc R . . . .
H8B H 0.732517 0.651657 0.337749 0.021 Uiso 1 1 calc R . . . .
C9 C 0.6082(4) 0.5573(8) 0.2044(3) 0.0173(9) Uani 1 1 d . . . . .
C10 C 0.6456(4) 0.3321(8) 0.1934(3) 0.0166(9) Uani 1 1 d . . . . .
H10 H 0.642214 0.283832 0.135258 0.020 Uiso 1 1 calc R . . . .
C11 C 0.6324(4) 0.7399(8) 0.1499(3) 0.0187(9) Uani 1 1 d . . . . .
H11A H 0.681064 0.845851 0.194024 0.022 Uiso 1 1 calc R . . . .
H11B H 0.667812 0.684346 0.111185 0.022 Uiso 1 1 calc R . . . .
C12 C 0.5225(4) 0.8396(8) 0.0879(3) 0.0164(9) Uani 1 1 d . . . . .
C13 C 0.4815(4) 0.5578(8) 0.1656(3) 0.0176(10) Uani 1 1 d . . . . .
C14 C 0.3242(4) 0.7802(9) 0.0531(3) 0.0200(10) Uani 1 1 d . . . . .
C15 C 0.2859(4) 0.9822(10) 0.0612(4) 0.0259(11) Uani 1 1 d . . . . .
H15 H 0.334348 1.086145 0.100125 0.031 Uiso 1 1 calc R . . . .
C16 C 0.1732(5) 1.0284(10) 0.0101(4) 0.0308(13) Uani 1 1 d . . . . .
H16 H 0.146120 1.163855 0.015051 0.037 Uiso 1 1 calc R . . . .
C17 C 0.1020(5) 0.8726(11) -0.0477(4) 0.0349(14) Uani 1 1 d . . . . .
H17 H 0.027095 0.903918 -0.081721 0.042 Uiso 1 1 calc R . . . .
C18 C 0.1413(4) 0.6714(12) -0.0554(4) 0.0328(12) Uani 1 1 d . . . . .
H18 H 0.092799 0.567373 -0.094176 0.039 Uiso 1 1 calc R . . . .
C19 C 0.2538(4) 0.6234(10) -0.0049(3) 0.0254(11) Uani 1 1 d . . . . .
H19 H 0.281015 0.488396 -0.010262 0.031 Uiso 1 1 calc R . . . .
C20 C 0.5825(4) 0.2605(8) 0.3702(3) 0.0173(10) Uani 1 1 d . . . . .
C21 C 0.4749(5) -0.0356(10) 0.3770(4) 0.0293(12) Uani 1 1 d . . . . .
H21A H 0.404598 0.004085 0.326931 0.044 Uiso 1 1 calc GR . . . .
H21B H 0.480923 0.022427 0.436590 0.044 Uiso 1 1 calc GR . . . .
H21C H 0.480549 -0.189900 0.381464 0.044 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.28416(13) 0.4907(4) 0.40284(11) 0.0484(5) Uani 1 1 d . . . . .
Cl2 Cl 0.18719(13) 0.2187(2) 0.23790(13) 0.0447(4) Uani 1 1 d . . . . .
Cl3 Cl 0.19202(13) 0.6771(3) 0.21273(12) 0.0428(4) Uani 1 1 d . . . . .
C22 C 0.2626(4) 0.4574(10) 0.2841(4) 0.0276(11) Uani 1 1 d . . . . .
H22 H 0.334909 0.444320 0.282178 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.899(5) . ?
O1 C20 1.332(6) . ?
O1 C21 1.449(6) . ?
O2 C20 1.209(6) . ?
O3 C13 1.213(6) . ?
O4 C12 1.203(6) . ?
N1 C7 1.480(6) . ?
N1 C10 1.270(6) . ?
N2 C12 1.399(6) . ?
N2 C13 1.379(6) . ?
N2 C14 1.443(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.395(7) . ?
C1 C6 1.387(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(8) . ?
C3 C4 1.386(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(7) . ?
C6 C7 1.526(6) . ?
C7 C8 1.554(7) . ?
C7 C20 1.543(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.552(6) . ?
C9 C10 1.517(7) . ?
C9 C11 1.526(7) . ?
C9 C13 1.532(6) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.502(7) . ?
C14 C15 1.378(8) . ?
C14 C19 1.384(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.397(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.397(7) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cl1 C22 1.746(6) . ?
Cl2 C22 1.761(6) . ?
Cl3 C22 1.754(6) . ?
C22 H22 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 C21 116.1(4) . . ?
C10 N1 C7 108.4(4) . . ?
C12 N2 C14 122.3(4) . . ?
C13 N2 C12 112.8(4) . . ?
C13 N2 C14 124.3(4) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C6 C1 C2 121.4(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 Br1 118.8(4) . . ?
C2 C3 C4 122.2(5) . . ?
C4 C3 Br1 119.0(4) . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.3(5) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 120.0(4) . . ?
C5 C6 C7 120.9(4) . . ?
N1 C7 C6 111.0(4) . . ?
N1 C7 C8 105.8(4) . . ?
N1 C7 C20 110.6(4) . . ?
C6 C7 C8 113.4(4) . . ?
C6 C7 C20 105.8(4) . . ?
C20 C7 C8 110.3(4) . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 C7 103.0(4) . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C10 C9 C8 99.9(4) . . ?
C10 C9 C11 117.7(4) . . ?
C10 C9 C13 108.5(4) . . ?
C11 C9 C8 116.4(4) . . ?
C11 C9 C13 103.8(4) . . ?
C13 C9 C8 110.5(4) . . ?
N1 C10 C9 117.1(4) . . ?
N1 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
C9 C11 H11A 110.5 . . ?
C9 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C12 C11 C9 106.3(4) . . ?
C12 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
O4 C12 N2 124.2(4) . . ?
O4 C12 C11 127.8(4) . . ?
N2 C12 C11 108.0(4) . . ?
O3 C13 N2 125.4(4) . . ?
O3 C13 C9 126.0(4) . . ?
N2 C13 C9 108.6(4) . . ?
C15 C14 N2 119.4(5) . . ?
C15 C14 C19 121.5(5) . . ?
C19 C14 N2 119.0(5) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.1(5) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(6) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.1(6) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 118.9(6) . . ?
C14 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
O1 C20 C7 112.5(4) . . ?
O2 C20 O1 124.4(5) . . ?
O2 C20 C7 123.0(5) . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl1 C22 Cl2 109.7(3) . . ?
Cl1 C22 Cl3 112.0(3) . . ?
Cl1 C22 H22 108.5 . . ?
Cl2 C22 H22 108.5 . . ?
Cl3 C22 Cl2 109.7(3) . . ?
Cl3 C22 H22 108.5 . . ?

_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 3.648
_oxdiff_exptl_absorpt_empirical_full_min 0.384
