# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_songxh_210301
_database_code_depnum_ccdc_archive 'CCDC 2082642'
loop_
_audit_author_name
_audit_author_address
sxh
;SYSU
China
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Br2 O2'
_chemical_formula_sum            'C16 H14 Br2 O2'
_chemical_formula_weight         398.09
_chemical_absolute_configuration ?
_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'
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                   7.96300(10)
_cell_length_b                   6.03520(10)
_cell_length_c                   16.0210(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.6370(10)
_cell_angle_gamma                90
_cell_volume                     768.391(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11898
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9870
_cell_measurement_theta_min      2.7460
_shelx_estimated_absorpt_T_max   0.731
_shelx_estimated_absorpt_T_min   0.555
_exptl_absorpt_coefficient_mu    6.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15800
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.041
_diffrn_reflns_theta_min         2.764
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    113.00 139.00   0.50    0.20    --  105.44  30.00-101.00   52
  2  ω     48.00  97.00   0.50    0.05    --   46.62  30.00-101.00   98
  3  ω      4.00  29.00   0.50    0.05    --   46.62 -30.00  98.00   50
  4  ω     33.00  70.00   0.50    0.20    --  105.44-125.00  30.00   74
  5  ω     77.00 107.00   0.50    0.20    --  105.44-125.00  30.00   60
  6  ω     79.00 105.00   0.50    0.20    --  105.44 -94.00-150.00   52
  7  ω     44.00  70.00   0.50    0.20    --  105.44 -94.00-150.00   52
  8  ω     33.00  69.00   0.50    0.20    --  105.44 -61.00  60.00   72
  9  ω     35.00  72.00   0.50    0.20    --  105.44 -61.00 120.00   74
 10  ω     35.00  68.00   0.50    0.20    --  105.44 -61.00  90.00   66
 11  ω     36.00  65.00   0.50    0.20    --  105.44 -61.00 150.00   58
 12  ω     36.00  62.00   0.50    0.20    --  105.44 -61.00  30.00   52
 13  ω     35.00  63.00   0.50    0.20    --  105.44 -61.00-150.00   56
 14  ω     34.00  70.00   0.50    0.20    --  105.44 -61.00-180.00   72
 15  ω    -40.00  20.00   0.50    0.05    --  -46.62  38.00  30.00  120
 16  ω    -23.00  29.00   0.50    0.05    --  -46.62  19.00 -30.00  104
 17  ω    -33.00  27.00   0.50    0.05    --  -46.62  30.00-101.00  120
 18  ω    -66.00 -30.00   0.50    0.20    -- -100.00  61.00 -30.00   72
 19  ω    -58.00 -33.00   0.50    0.20    -- -100.00  61.00-120.00   50
 20  ω    -64.00 -38.00   0.50    0.20    -- -100.00  61.00   0.00   52
 21  ω    -55.00 -29.00   0.50    0.20    -- -100.00  61.00  30.00   52
 22  ω    -60.00 -35.00   0.50    0.20    -- -100.00  61.00  60.00   50
 23  ω    -69.00 -43.00   0.50    0.20    -- -100.00  61.00  90.00   52
 24  ω    -71.00 -33.00   0.50    0.05    --  -46.62 -30.00  98.00   76
 25  ω   -175.00 -86.00   0.50    0.20    -- -100.00 -30.00  98.00  178
 26  ω     52.00  77.00   0.50    0.05    --   46.37  30.00-101.00   50
 27  ω     23.00  80.00   0.50    0.05    --   46.37  77.00 -30.00  114
 28  ω     56.00  95.00   0.50    0.05    --   46.37  38.00 -60.00   78
 29  ω     31.00  74.00   0.50    0.05    --   46.37  57.00  60.00   86
 30  ω   -161.00-135.00   0.50    0.20    -- -100.00 -73.00   7.50   52
 31  ω   -105.00 -79.00   0.50    0.20    -- -100.00 -77.00   0.00   52
 32  ω   -105.00 -78.00   0.50    0.20    -- -100.00 -73.00   7.50   54
 33  ω   -128.00 -79.00   0.50    0.20    -- -100.00 -73.00 -22.52   98
 34  ω   -167.00 -88.00   0.50    0.20    -- -100.00 -15.00   0.00  158
 35  ω   -103.00 -77.00   0.50    0.20    -- -100.00 -77.00 -60.00   52
 36  ω   -111.00 -77.00   0.50    0.20    -- -100.00 -77.00  23.80   68
 37  ω   -111.00 -85.00   0.50    0.20    -- -100.00 -53.00  52.65   52
 38  ω   -109.00 -76.00   0.50    0.20    -- -100.00 -77.00  60.00   66
 39  ω   -111.00 -85.00   0.50    0.20    -- -100.00 -61.00  30.00   52
 40  ω   -102.00 -76.00   0.50    0.20    -- -100.00 -77.00  30.00   52
 41  ω   -144.00 -79.00   0.50    0.20    -- -100.00 -71.00  -0.31  130
 42  ω   -164.00-138.00   0.50    0.20    -- -100.00 -72.00 -12.33   52
 43  ω   -109.00 -78.00   0.50    0.20    -- -100.00 -72.00 -12.33   62
 44  ω   -171.00-145.00   0.50    0.20    -- -100.00 -54.00 -54.65   52
 45  ω   -117.00 -77.00   0.50    0.20    -- -100.00 -75.00 -25.56   80
 46  ω   -112.00 -77.00   0.50    0.20    -- -100.00 -76.00  16.00   70
 47  ω   -106.00 -81.00   0.50    0.20    -- -100.00 -67.00  64.68   50
 48  ω   -122.00 -85.00   0.50    0.20    -- -100.00 -54.00 -54.65   74
 49  ω   -154.00-128.00   0.50    0.20    -- -100.00 -77.00  60.00   52
 50  ω   -165.00 -86.00   0.50    0.20    -- -100.00 -58.00  17.24  158
 51  ω   -136.00 -82.00   0.50    0.20    -- -100.00 -61.00 -60.00  108
 52  ω   -103.00 -77.00   0.50    0.20    -- -100.00 -77.00 -30.00   52
 53  ω   -164.00-139.00   0.50    0.20    -- -100.00 -77.00  30.00   50
 54  ω     97.00 143.00   0.50    0.20    --  107.00  30.00-120.00   92
 55  ω     66.00 104.00   0.50    0.20    --  107.00 -77.00 -60.00   76
 56  ω     73.00  99.00   0.50    0.20    --  107.00 -77.00-180.00   52
 57  ω     35.00  60.00   0.50    0.20    --  107.00 -77.00-180.00   50
 58  ω     62.00  99.00   0.50    0.20    --  107.00-125.00  60.00   74
 59  ω     82.00 107.00   0.50    0.20    --  107.00 -77.00 120.00   50
 60  ω     39.00  69.00   0.50    0.20    --  107.00 -77.00 120.00   60
 61  ω     36.00  72.00   0.50    0.20    --  107.00 -61.00-120.00   72
 62  ω   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00 -60.00  176
 63  ω   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00  60.00  176
 64  ω   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00  30.00  190
 65  ω   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00-120.00  176
 66  ω   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00-180.00  190
 67  ω     18.00  95.00   0.50    0.05    --   46.37-125.00  60.00  154
 68  ω     30.00  74.00   0.50    0.05    --   46.37  57.00 120.00   88
 69  ω     23.00 118.00   0.50    0.05    --   46.37  77.00-120.00  190
 70  ω     18.00  95.00   0.50    0.05    --   46.37-125.00 120.00  154
 71  ω     23.00 118.00   0.50    0.05    --   46.37  77.00 150.00  190
 72  ω    -20.00   5.00   0.50    0.05    --   46.37 -30.00  98.00   50
 73  ω   -103.00 -77.00   0.50    0.20    -- -100.00 -74.00 -16.96   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0304032000
_diffrn_orient_matrix_UB_12      -0.0982294000
_diffrn_orient_matrix_UB_13      0.0865203000
_diffrn_orient_matrix_UB_21      -0.1912696000
_diffrn_orient_matrix_UB_22      0.0033820000
_diffrn_orient_matrix_UB_23      -0.0218939000
_diffrn_orient_matrix_UB_31      0.0104596000
_diffrn_orient_matrix_UB_32      -0.2355930000
_diffrn_orient_matrix_UB_33      -0.0361734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                2989
_reflns_number_total             3060
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Flack x determined using 1260 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.112
_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)+(0.0184P)²+1.1540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0676
_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.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C2(H2), C15(H15), C5(H5), C3(H3), C14(H14), C6(H6)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C12(H12A,H12B,H12C)
;
_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
Br10 Br 1.07213(7) 0.70832(9) 0.90430(3) 0.02814(14) Uani 1 1 d . . . . .
Br9 Br 1.17197(7) 0.90858(10) 0.73036(3) 0.03012(15) Uani 1 1 d . . . . .
O19 O 0.4639(5) 0.0913(7) 0.9315(2) 0.0297(8) Uani 1 1 d . . . . .
O11 O 0.6916(5) 0.7053(9) 0.4054(2) 0.0355(9) Uani 1 1 d . . . . .
C16 C 0.5569(6) 0.2301(10) 0.8863(3) 0.0254(11) Uani 1 1 d . . . . .
C17 C 0.7172(7) 0.1520(9) 0.8687(3) 0.0284(12) Uani 1 1 d . . . . .
H17 H 0.752641 0.012214 0.886699 0.034 Uiso 1 1 calc R U . . .
C18 C 0.8217(7) 0.2844(9) 0.8243(3) 0.0269(12) Uani 1 1 d . . . . .
H18 H 0.927458 0.231814 0.812575 0.032 Uiso 1 1 calc R U . . .
C8 C 1.0201(6) 0.7310(10) 0.7870(3) 0.0264(11) Uani 1 1 d . . . . .
C2 C 0.8880(7) 0.5062(11) 0.6010(3) 0.0280(11) Uani 1 1 d . . . . .
H2 H 0.953068 0.385818 0.619499 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8858(6) 0.6372(9) 0.7493(3) 0.0226(10) Uani 1 1 d . . . . .
C4 C 0.7383(6) 0.7048(12) 0.4887(3) 0.0271(10) Uani 1 1 d . . . . .
C13 C 0.7722(6) 0.4940(10) 0.7969(3) 0.0226(10) Uani 1 1 d . . . . .
C1 C 0.8414(6) 0.6659(9) 0.6580(3) 0.0245(11) Uani 1 1 d . . . . .
C15 C 0.5046(7) 0.4387(10) 0.8581(3) 0.0259(12) Uani 1 1 d . . . . .
H15 H 0.398578 0.491151 0.869433 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6924(7) 0.8650(10) 0.5453(3) 0.0294(12) Uani 1 1 d . . . . .
H5 H 0.627351 0.985737 0.527051 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8380(7) 0.5260(11) 0.5169(3) 0.0309(12) Uani 1 1 d . . . . .
H3 H 0.870890 0.419973 0.479052 0.037 Uiso 1 1 calc R U . . .
C20 C 0.3109(7) 0.1792(11) 0.9604(3) 0.0303(12) Uani 1 1 d . . . . .
H20A H 0.230620 0.199091 0.913745 0.045 Uiso 1 1 calc R U . . .
H20B H 0.333306 0.319279 0.987200 0.045 Uiso 1 1 calc R U . . .
H20C H 0.266364 0.077994 0.999604 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6110(6) 0.5683(9) 0.8130(3) 0.0245(11) Uani 1 1 d . . . . .
H14 H 0.574598 0.706181 0.793210 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7445(8) 0.8433(10) 0.6293(4) 0.0326(13) Uani 1 1 d . . . . .
H6 H 0.713383 0.950553 0.667091 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5908(9) 0.8871(15) 0.3738(4) 0.0491(18) Uani 1 1 d . . . . .
H12A H 0.564243 0.866858 0.315003 0.074 Uiso 1 1 calc R U . . .
H12B H 0.652084 1.022912 0.382737 0.074 Uiso 1 1 calc R U . . .
H12C H 0.488683 0.893229 0.402461 0.074 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
Br10 C8 1.904(5) . ?
Br9 C8 1.890(6) . ?
O19 C16 1.357(7) . ?
O19 C20 1.432(6) . ?
O11 C4 1.362(6) . ?
O11 C12 1.433(8) . ?
C16 C17 1.406(8) . ?
C16 C15 1.393(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(8) . ?
C18 H18 0.9300 . ?
C18 C13 1.388(8) . ?
C8 C7 1.322(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.395(8) . ?
C2 C3 1.386(7) . ?
C7 C13 1.495(8) . ?
C7 C1 1.492(7) . ?
C4 C5 1.391(8) . ?
C4 C3 1.397(9) . ?
C13 C14 1.399(7) . ?
C1 C6 1.381(8) . ?
C15 H15 0.9300 . ?
C15 C14 1.389(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(8) . ?
C3 H3 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O19 C20 116.6(5) . . ?
C4 O11 C12 117.4(5) . . ?
O19 C16 C17 115.7(5) . . ?
O19 C16 C15 124.7(5) . . ?
C15 C16 C17 119.6(5) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(5) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C13 121.4(5) . . ?
C13 C18 H18 119.3 . . ?
Br9 C8 Br10 114.1(3) . . ?
C7 C8 Br10 122.6(4) . . ?
C7 C8 Br9 123.2(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.4(5) . . ?
C8 C7 C13 120.8(5) . . ?
C8 C7 C1 122.1(5) . . ?
C1 C7 C13 117.0(4) . . ?
O11 C4 C5 124.8(6) . . ?
O11 C4 C3 115.6(5) . . ?
C5 C4 C3 119.6(5) . . ?
C18 C13 C7 121.3(5) . . ?
C18 C13 C14 118.7(5) . . ?
C14 C13 C7 120.0(5) . . ?
C2 C1 C7 120.3(5) . . ?
C6 C1 C2 118.9(5) . . ?
C6 C1 C7 120.6(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 C16 119.9(5) . . ?
C14 C15 H15 120.1 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(5) . . ?
C6 C5 H5 120.3 . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C1 C6 C5 121.4(5) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O11 C12 H12A 109.5 . . ?
O11 C12 H12B 109.5 . . ?
O11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br10 C8 C7 C13 -4.0(8) . . . . ?
Br10 C8 C7 C1 176.7(4) . . . . ?
Br9 C8 C7 C13 178.6(4) . . . . ?
Br9 C8 C7 C1 -0.7(8) . . . . ?
O19 C16 C17 C18 -178.8(5) . . . . ?
O19 C16 C15 C14 179.3(5) . . . . ?
O11 C4 C5 C6 178.4(6) . . . . ?
O11 C4 C3 C2 -178.0(5) . . . . ?
C16 C17 C18 C13 0.3(8) . . . . ?
C16 C15 C14 C13 -1.4(8) . . . . ?
C17 C16 C15 C14 -0.2(7) . . . . ?
C17 C18 C13 C7 179.8(5) . . . . ?
C17 C18 C13 C14 -1.8(8) . . . . ?
C18 C13 C14 C15 2.4(7) . . . . ?
C8 C7 C13 C18 -72.1(7) . . . . ?
C8 C7 C13 C14 109.5(6) . . . . ?
C8 C7 C1 C2 96.7(7) . . . . ?
C8 C7 C1 C6 -87.5(7) . . . . ?
C2 C1 C6 C5 0.2(9) . . . . ?
C7 C13 C14 C15 -179.2(5) . . . . ?
C7 C1 C6 C5 -175.6(5) . . . . ?
C4 C5 C6 C1 0.1(9) . . . . ?
C13 C7 C1 C2 -82.6(6) . . . . ?
C13 C7 C1 C6 93.3(6) . . . . ?
C1 C2 C3 C4 -0.9(9) . . . . ?
C1 C7 C13 C18 107.1(6) . . . . ?
C1 C7 C13 C14 -71.3(6) . . . . ?
C15 C16 C17 C18 0.8(8) . . . . ?
C5 C4 C3 C2 1.3(9) . . . . ?
C3 C2 C1 C7 176.0(5) . . . . ?
C3 C2 C1 C6 0.1(9) . . . . ?
C3 C4 C5 C6 -0.9(9) . . . . ?
C20 O19 C16 C17 171.4(4) . . . . ?
C20 O19 C16 C15 -8.1(7) . . . . ?
C12 O11 C4 C5 1.4(9) . . . . ?
C12 O11 C4 C3 -179.3(6) . . . . ?

_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 2.032
_oxdiff_exptl_absorpt_empirical_full_min 0.583
####################################################################### 
# 
# 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_songxh_cl_210208_2
_database_code_depnum_ccdc_archive 'CCDC 2082644'
loop_
_audit_author_name
_audit_author_address
sxh
;SYSU
China
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2021-02-09
_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         'C16 H13 Br3 O2'
_chemical_formula_sum            'C16 H13 Br3 O2'
_chemical_formula_weight         476.99
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONClBr
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'
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                   5.5472(2)
_cell_length_b                   7.8195(4)
_cell_length_c                   18.3327(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.308(4)
_cell_angle_gamma                90
_cell_volume                     792.96(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.5100
_cell_measurement_theta_min      2.4020
_shelx_estimated_absorpt_T_max   0.452
_shelx_estimated_absorpt_T_min   0.201
_exptl_absorpt_coefficient_mu    9.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.998
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1869
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16382
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.846
_diffrn_reflns_theta_min         2.417
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    127.00 157.00   0.50    0.05    --  105.44  62.00 132.00   60
  2  ω    147.00 176.00   0.50    0.05    --  105.44  45.00  60.00   58
  3  ω     98.00 143.00   0.50    0.05    --  105.44  45.00  60.00   90
  4  ω     88.00 142.00   0.50    0.05    --  105.44  15.00-120.00  108
  5  ω     44.00 106.00   0.50    0.05    --  105.44 -77.00  60.00  124
  6  ω    -10.00  28.00   0.50    0.05    --   46.62 -62.00  -5.00   76
  7  ω     33.00  73.00   0.50    0.05    --  105.44 -61.00 150.00   80
  8  ω     33.00  74.00   0.50    0.05    --  105.44 -62.00  -5.00   82
  9  ω     55.00  90.00   0.50    0.05    --  105.44 -77.00-120.00   70
 10  ω     40.00  70.00   0.50    0.05    --  105.44 -61.00 -90.00   60
 11  ω     43.00  69.00   0.50    0.05    --  105.44-125.00-150.00   52
 12  ω    -63.00 -34.00   0.50    0.05    -- -100.00  62.00 132.00   58
 13  ω    -64.00  23.00   0.50    0.05    --  -46.62  62.00 132.00  174
 14  ω    -58.00 -33.00   0.50    0.05    -- -100.00  61.00  90.00   50
 15  ω    -66.00 -30.00   0.50    0.05    -- -100.00  61.00 -90.00   72
 16  ω     75.00 101.00   0.50    0.05    --  105.44-125.00-150.00   52
 17  ω    -94.00 -34.00   0.50    0.05    --  -46.62 -62.00  -5.00  120
 18  ω   -106.00 -76.00   0.50    0.05    --  -46.62-125.00  60.00   60
 19  ω   -118.00 -77.00   0.50    0.05    --  -46.62-125.00 150.00   82
 20  ω   -170.00-107.00   0.50    0.05    -- -100.00 -94.00  90.00  126
 21  ω   -172.00 -82.00   0.50    0.05    -- -100.00 -62.00  -5.00  180
 22  ω   -118.00 -91.00   0.50    0.05    --  -46.37 -62.00  -5.00   54
 23  ω     33.00 114.00   0.50    0.05    --   46.37  57.00-120.00  162
 24  ω   -170.00-145.00   0.50    0.05    -- -100.00 -61.00-120.00   50
 25  ω   -163.00 -85.00   0.50    0.05    -- -100.00 -15.00 -90.00  156
 26  ω   -101.00 -76.00   0.50    0.05    -- -100.00 -77.00 -30.00   50
 27  ω   -112.00 -86.00   0.50    0.05    -- -100.00 -61.00-120.00   52
 28  ω    140.00 166.00   0.50    0.05    --  107.00  77.00-120.00   52
 29  ω    100.00 136.00   0.50    0.05    --  107.00  45.00  30.00   72
 30  ω    106.00 134.00   0.50    0.05    --  107.00  77.00-120.00   56
 31  ω    126.00 153.00   0.50    0.05    --  107.00  77.00-180.00   54
 32  ω     83.00 109.00   0.50    0.05    --  107.00  77.00-180.00   52
 33  ω     94.00 166.00   0.50    0.05    --  107.00  30.00 -90.00  144
 34  ω    149.00 177.00   0.50    0.05    --  107.00  45.00  30.00   56
 35  ω     38.00  64.00   0.50    0.05    --  107.00 -61.00 120.00   52
 36  ω     42.00  68.00   0.50    0.05    --  107.00 -94.00 -60.00   52
 37  ω     81.00 106.00   0.50    0.05    --  107.00 -94.00  60.00   50
 38  ω    122.00 150.00   0.50    0.05    --  107.00  45.00  90.00   56
 39  ω     69.00  94.00   0.50    0.05    --  107.00 -94.00 -60.00   50
 40  ω     35.00  62.00   0.50    0.05    --  107.00 -94.00  60.00   54
 41  ω     35.00  61.00   0.50    0.05    --  107.00 -61.00-150.00   52
 42  ω     94.00 160.00   0.50    0.05    --  107.00  77.00 120.00  132
 43  ω     77.00 104.00   0.50    0.05    --  107.00 -94.00  30.00   54
 44  ω     96.00 125.00   0.50    0.05    --  107.00  45.00 -90.00   58
 45  ω     38.00  83.00   0.50    0.05    --  107.00 -94.00 -30.00   90
 46  ω     83.00 174.00   0.50    0.05    --  107.00  77.00-150.00  182
 47  ω     29.00 118.00   0.50    0.05    --   46.37  62.00 132.00  178
 48  ω     23.00 118.00   0.50    0.05    --   46.37  77.00  30.00  190
 49  ω     30.00 118.00   0.50    0.05    --   46.37  57.00-150.00  176
 50  ω     23.00 118.00   0.50    0.05    --   46.37  77.00 -30.00  190
 51  ω     18.00  95.00   0.50    0.05    --   46.37-125.00   0.00  154
 52  ω     23.00 118.00   0.50    0.05    --   46.37  77.00-150.00  190
 53  ω     30.00 118.00   0.50    0.05    --   46.37  57.00 -60.00  176
 54  ω   -173.00 -80.00   0.50    0.05    -- -100.00 -77.00 150.00  186
 55  ω   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00 -90.00  174
 56  ω   -173.00 -82.00   0.50    0.05    -- -100.00 -61.00-180.00  182
 57  ω   -173.00 -76.00   0.50    0.05    -- -100.00 -77.00  60.00  194
 58  ω     34.00 112.00   0.50    0.05    --  107.00-125.00  30.00  156
 59  ω     92.00 178.00   0.50    0.05    --  107.00  30.00 120.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2172560000
_diffrn_orient_matrix_UB_12      -0.0633704000
_diffrn_orient_matrix_UB_13      -0.0500641000
_diffrn_orient_matrix_UB_21      -0.0640660000
_diffrn_orient_matrix_UB_22      -0.1280248000
_diffrn_orient_matrix_UB_23      0.0593796000
_diffrn_orient_matrix_UB_31      -0.1620416000
_diffrn_orient_matrix_UB_32      0.1356504000
_diffrn_orient_matrix_UB_33      0.0327307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                2401
_reflns_number_total             3232
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         1.009
_refine_diff_density_min         -1.626
_refine_diff_density_rms         0.190
_refine_ls_abs_structure_details 
;
 Flack x determined using 726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0697
_refine_ls_restrained_S_all      1.109
_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)+(0.0675P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1783
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C18(H18), C16(H16), C5(H5), C19(H19), C15(H15), C3(H3)
2.c 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
Br13 Br 1.0550(3) 0.4067(3) 1.09215(9) 0.0344(5) Uani 1 1 d . . . . .
Br12 Br 0.4586(3) 0.7898(2) 0.77804(10) 0.0371(5) Uani 1 1 d . . . . .
Br11 Br 0.3181(4) 0.2084(3) 0.77944(11) 0.0408(5) Uani 1 1 d . . . . .
O20 O 0.293(2) 0.441(2) 0.3930(6) 0.043(4) Uani 1 1 d . . . . .
O10 O -0.025(2) 0.5297(18) 0.7146(6) 0.039(3) Uani 1 1 d . . . . .
C4 C 0.843(3) 0.455(2) 1.0068(9) 0.028(4) Uani 1 1 d . . . . .
C2 C 0.481(3) 0.570(3) 0.9502(9) 0.035(4) Uani 1 1 d . . . . .
H2 H 0.337432 0.629027 0.953763 0.042 Uiso 1 1 calc R U . . .
C6 C 0.759(3) 0.428(3) 0.8785(9) 0.037(4) Uani 1 1 d . . . . .
H6 H 0.802460 0.391044 0.833073 0.044 Uiso 1 1 calc R U . . .
C18 C 0.434(3) 0.387(3) 0.5134(9) 0.034(4) Uani 1 1 d . . . . .
H18 H 0.567185 0.333329 0.495796 0.041 Uiso 1 1 calc R U . . .
C16 C 0.052(3) 0.541(2) 0.4905(9) 0.031(4) Uani 1 1 d . . . . .
H16 H -0.067435 0.589745 0.458586 0.037 Uiso 1 1 calc R U . . .
C9 C 0.168(3) 0.488(3) 0.6939(10) 0.033(4) Uani 1 1 d . . . . .
C5 C 0.909(3) 0.395(2) 0.9403(9) 0.029(4) Uani 1 1 d . . . . .
H5 H 1.052067 0.334562 0.937243 0.034 Uiso 1 1 calc R U . . .
C1 C 0.539(3) 0.515(2) 0.8835(9) 0.030(4) Uani 1 1 d . . . . .
C17 C 0.255(3) 0.458(2) 0.4647(9) 0.033(4) Uani 1 1 d . . . . .
C19 C 0.410(3) 0.397(3) 0.5884(9) 0.034(4) Uani 1 1 d . . . . .
H19 H 0.528701 0.349678 0.621007 0.041 Uiso 1 1 calc R U . . .
C7 C 0.374(3) 0.555(2) 0.8180(9) 0.033(4) Uani 1 1 d . . . . .
H7 H 0.207775 0.557780 0.832308 0.040 Uiso 1 1 calc R U . . .
C15 C 0.038(3) 0.547(2) 0.5659(9) 0.033(4) Uani 1 1 d . . . . .
H15 H -0.093505 0.601618 0.584147 0.039 Uiso 1 1 calc R U . . .
C3 C 0.631(3) 0.539(2) 1.0142(10) 0.028(4) Uiso 1 1 d . . . . .
H3 H 0.586288 0.574156 1.059793 0.034 Uiso 1 1 calc R U . . .
C8 C 0.384(3) 0.451(2) 0.7505(10) 0.035(4) Uiso 1 1 d . . . . .
H8 H 0.539489 0.461749 0.728960 0.042 Uiso 1 1 calc R U . . .
C14 C 0.210(3) 0.477(3) 0.6145(9) 0.032(4) Uani 1 1 d . . . . .
C21 C 0.108(4) 0.509(3) 0.3416(10) 0.047(6) Uani 1 1 d . . . . .
H21A H -0.045060 0.458590 0.350565 0.070 Uiso 1 1 calc R U . . .
H21B H 0.146281 0.482126 0.292637 0.070 Uiso 1 1 calc R U . . .
H21C H 0.099090 0.630514 0.347275 0.070 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
Br13 C4 1.923(15) . ?
Br12 C7 2.041(19) . ?
Br11 C8 2.008(19) . ?
O20 C17 1.35(2) . ?
O20 C21 1.44(2) . ?
O10 C9 1.21(2) . ?
C4 C5 1.38(2) . ?
C4 C3 1.37(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.36(3) . ?
C2 C3 1.40(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.38(2) . ?
C6 C1 1.40(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.40(2) . ?
C18 C19 1.39(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.41(2) . ?
C16 C15 1.39(2) . ?
C9 C8 1.55(2) . ?
C9 C14 1.49(2) . ?
C5 H5 0.9300 . ?
C1 C7 1.49(2) . ?
C19 H19 0.9300 . ?
C19 C14 1.39(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.49(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.37(2) . ?
C3 H3 0.9300 . ?
C8 H8 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O20 C21 116.2(14) . . ?
C5 C4 Br13 117.8(12) . . ?
C3 C4 Br13 119.5(13) . . ?
C3 C4 C5 122.6(15) . . ?
C1 C2 H2 118.8 . . ?
C1 C2 C3 122.3(18) . . ?
C3 C2 H2 118.8 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C1 120.6(16) . . ?
C1 C6 H6 119.7 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C19 C18 C17 119.6(17) . . ?
C17 C16 H16 121.6 . . ?
C15 C16 H16 121.6 . . ?
C15 C16 C17 116.8(16) . . ?
O10 C9 C8 119.9(16) . . ?
O10 C9 C14 122.0(16) . . ?
C14 C9 C8 118.1(16) . . ?
C4 C5 C6 118.6(15) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C2 C1 C6 118.5(16) . . ?
C2 C1 C7 119.2(16) . . ?
C6 C1 C7 122.2(16) . . ?
O20 C17 C18 115.1(16) . . ?
O20 C17 C16 123.9(15) . . ?
C18 C17 C16 121.0(16) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C14 120.0(16) . . ?
C14 C19 H19 120.0 . . ?
Br12 C7 H7 108.9 . . ?
C1 C7 Br12 109.6(13) . . ?
C1 C7 H7 108.9 . . ?
C1 C7 C8 119.8(15) . . ?
C8 C7 Br12 99.9(12) . . ?
C8 C7 H7 108.9 . . ?
C16 C15 H15 118.4 . . ?
C14 C15 C16 123.3(17) . . ?
C14 C15 H15 118.4 . . ?
C4 C3 C2 117.2(17) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
Br11 C8 H8 111.9 . . ?
C9 C8 Br11 102.0(12) . . ?
C9 C8 H8 111.9 . . ?
C7 C8 Br11 106.3(12) . . ?
C7 C8 C9 112.3(15) . . ?
C7 C8 H8 111.9 . . ?
C19 C14 C9 123.2(16) . . ?
C15 C14 C9 117.4(17) . . ?
C15 C14 C19 119.3(16) . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br13 C4 C5 C6 179.5(14) . . . . ?
Br13 C4 C3 C2 -179.3(13) . . . . ?
Br12 C7 C8 Br11 177.7(8) . . . . ?
Br12 C7 C8 C9 -71.6(16) . . . . ?
O10 C9 C8 Br11 82(2) . . . . ?
O10 C9 C8 C7 -31(3) . . . . ?
O10 C9 C14 C19 -166(2) . . . . ?
O10 C9 C14 C15 12(3) . . . . ?
C2 C1 C7 Br12 87.0(19) . . . . ?
C2 C1 C7 C8 -158.5(18) . . . . ?
C6 C1 C7 Br12 -91(2) . . . . ?
C6 C1 C7 C8 24(3) . . . . ?
C18 C19 C14 C9 177.8(19) . . . . ?
C18 C19 C14 C15 -1(3) . . . . ?
C16 C15 C14 C9 -177.8(17) . . . . ?
C16 C15 C14 C19 1(3) . . . . ?
C5 C4 C3 C2 -3(3) . . . . ?
C5 C6 C1 C2 1(3) . . . . ?
C5 C6 C1 C7 178.9(19) . . . . ?
C1 C2 C3 C4 2(3) . . . . ?
C1 C6 C5 C4 -2(3) . . . . ?
C1 C7 C8 Br11 58(2) . . . . ?
C1 C7 C8 C9 168.9(17) . . . . ?
C17 C18 C19 C14 0(3) . . . . ?
C17 C16 C15 C14 0(3) . . . . ?
C19 C18 C17 O20 -179.7(18) . . . . ?
C19 C18 C17 C16 1(3) . . . . ?
C15 C16 C17 O20 179.8(17) . . . . ?
C15 C16 C17 C18 -1(3) . . . . ?
C3 C4 C5 C6 3(3) . . . . ?
C3 C2 C1 C6 -1(3) . . . . ?
C3 C2 C1 C7 -178.9(17) . . . . ?
C8 C9 C14 C19 16(3) . . . . ?
C8 C9 C14 C15 -165.3(18) . . . . ?
C14 C9 C8 Br11 -100.2(18) . . . . ?
C14 C9 C8 C7 146.4(18) . . . . ?
C21 O20 C17 C18 178.3(19) . . . . ?
C21 O20 C17 C16 -2(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 3.400
_oxdiff_exptl_absorpt_empirical_full_min 0.414
