# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_2bg-c_zzx-913-new
_database_code_depnum_ccdc_archive 'CCDC 2151449'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2022-02-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_weight         316.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'C1 H1 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.48375(11)
_cell_length_b                   23.7768(5)
_cell_length_c                   8.95801(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.0554(14)
_cell_angle_gamma                90
_cell_volume                     1589.99(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10596
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      71.6240
_cell_measurement_theta_min      4.9430
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.37
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15193
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.700
_diffrn_reflns_theta_min         4.949
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    1.00    --  -35.97 -38.00 -60.00   88
  2  ω    -90.00  -3.00   1.00    1.00    --  -35.97 126.00 -90.00   87
  3  ω    -33.00  55.00   1.00    1.00    --   35.97 -38.00-150.00   88
  4  ω      1.00  75.00   1.00    1.00    --   35.97 -99.00-180.00   74
  5  ω     19.00 103.00   1.00    1.00    --   35.97  57.00  30.00   84
  6  ω     87.00 178.00   1.00    1.00    --  107.97  30.00 -60.00   91
  7  ω     38.00 129.00   1.00    1.00    --  107.97 -30.00 -60.00   91
  8  ω     91.00 176.00   1.00    1.00    --  107.97  45.00  30.00   85
  9  ω     39.00 110.00   1.00    1.00    --  107.97 -95.00 -90.00   71
 10  ω     41.00 126.00   1.00    1.00    --  107.97 -61.00 120.00   85
 11  ω     39.00 110.00   1.00    1.00    --  107.97 -95.00  90.00   71
 12  ω     40.00 125.00   1.00    1.00    --  107.97 -45.00-150.00   85
 13  ω     39.00 110.00   1.00    1.00    --  107.97 -95.00  30.00   71
 14  ω   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00-150.00   95
 15  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  90.00   84
 16  ω   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00 -60.00   95
 17  ω    -31.00  53.00   1.00    1.00    --   35.97 -57.00  60.00   84
 18  ω     87.00 178.00   1.00    1.00    --  107.97  30.00-120.00   91
 19  ω     81.00 176.00   1.00    1.00    --  107.97  77.00 -30.00   95
 20  ω     70.00 178.00   1.00    1.00    --  107.97  15.00 150.00  108
 21  ω     91.00 176.00   1.00    1.00    --  107.97  45.00  60.00   85
 22  ω     91.00 176.00   1.00    1.00    --  107.97  45.00-180.00   85
 23  ω     81.00 141.00   1.00    1.00    --  107.97  77.00 -60.00   60
 24  ω     81.00 176.00   1.00    1.00    --  107.97  77.00-120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0093427000
_diffrn_orient_matrix_UB_12      0.0054691000
_diffrn_orient_matrix_UB_13      0.1717989000
_diffrn_orient_matrix_UB_21      -0.2050703000
_diffrn_orient_matrix_UB_22      -0.0062043000
_diffrn_orient_matrix_UB_23      -0.0029191000
_diffrn_orient_matrix_UB_31      0.0205045000
_diffrn_orient_matrix_UB_32      -0.0642601000
_diffrn_orient_matrix_UB_33      0.0148865000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.668
_reflns_Friedel_fraction_max     0.651
_reflns_number_gt                5051
_reflns_number_total             5126
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1854 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.057
_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)+(0.0487P)²+0.3349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0924
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C33(H33A,H33B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
  C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
 C37(H37), C38(H38), C39(H39), C40(H40)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5A)
;
_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
O1 O -0.4213(2) -0.45881(9) -0.87354(19) 0.0356(5) Uani 1 1 d . . . . .
O2 O 0.1077(2) -0.42664(9) -0.7534(2) 0.0379(5) Uani 1 1 d . . . . .
H2 H 0.154246 -0.417686 -0.671247 0.057 Uiso 1 1 calc R U . . .
O3 O 0.1047(2) -0.49103(10) -0.5163(2) 0.0415(5) Uani 1 1 d . . . . .
C1 C 0.0140(3) -0.52346(10) -0.9481(2) 0.0223(5) Uani 1 1 d . . . . .
C2 C 0.1871(3) -0.53577(12) -0.8829(3) 0.0309(6) Uani 1 1 d . . . . .
H2A H 0.223648 -0.520748 -0.789823 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3016(4) -0.56960(14) -0.9551(3) 0.0406(7) Uani 1 1 d . . . . .
H3 H 0.414359 -0.577574 -0.909791 0.049 Uiso 1 1 calc R U . . .
C4 C 0.2516(4) -0.59227(15) -1.0957(3) 0.0446(7) Uani 1 1 d . . . . .
H4 H 0.331815 -0.614346 -1.144599 0.054 Uiso 1 1 calc R U . . .
C5 C 0.0849(4) -0.58192(13) -1.1609(3) 0.0364(6) Uani 1 1 d . . . . .
H5 H 0.051797 -0.597319 -1.254256 0.044 Uiso 1 1 calc R U . . .
C6 C -0.0384(3) -0.54815(11) -1.0891(2) 0.0264(5) Uani 1 1 d . . . . .
C7 C -0.2137(4) -0.53895(12) -1.1531(3) 0.0324(6) Uani 1 1 d . . . . .
H7 H -0.247296 -0.553636 -1.247122 0.039 Uiso 1 1 calc R U . . .
C8 C -0.3334(3) -0.50911(13) -1.0795(3) 0.0342(6) Uani 1 1 d . . . . .
H8 H -0.449541 -0.504397 -1.121693 0.041 Uiso 1 1 calc R U . . .
C9 C -0.2828(3) -0.48500(11) -0.9385(3) 0.0268(5) Uani 1 1 d . . . . .
C10 C -0.1102(3) -0.48817(10) -0.8758(2) 0.0219(5) Uani 1 1 d . . . . .
C11 C -0.0564(3) -0.45548(11) -0.7347(3) 0.0252(5) Uani 1 1 d . . . . .
C12 C -0.1993(4) -0.41107(12) -0.7104(3) 0.0337(6) Uani 1 1 d . . . . .
H12A H -0.177740 -0.395223 -0.610951 0.040 Uiso 1 1 calc R U . . .
H12B H -0.188874 -0.380917 -0.782171 0.040 Uiso 1 1 calc R U . . .
C13 C -0.3859(3) -0.43429(13) -0.7267(3) 0.0337(6) Uani 1 1 d . . . . .
H13 H -0.466504 -0.401922 -0.722394 0.040 Uiso 1 1 calc R U . . .
C14 C -0.4335(3) -0.47353(14) -0.6027(3) 0.0370(7) Uani 1 1 d . . . . .
H14A H -0.405564 -0.454190 -0.508567 0.044 Uiso 1 1 calc R U . . .
H14B H -0.562318 -0.478821 -0.612368 0.044 Uiso 1 1 calc R U . . .
C15 C -0.3491(3) -0.53091(13) -0.5895(3) 0.0345(6) Uani 1 1 d . . . . .
C16 C -0.4576(5) -0.57767(18) -0.5724(4) 0.0555(10) Uani 1 1 d . . . . .
H16 H -0.580961 -0.572733 -0.574034 0.067 Uiso 1 1 calc R U . . .
C17 C -0.3879(7) -0.63125(19) -0.5531(4) 0.0719(13) Uani 1 1 d . . . . .
H17 H -0.464664 -0.661631 -0.544261 0.086 Uiso 1 1 calc R U . . .
C18 C -0.2063(7) -0.63990(16) -0.5468(4) 0.0629(11) Uani 1 1 d . . . . .
H18 H -0.159253 -0.675921 -0.534164 0.076 Uiso 1 1 calc R U . . .
C19 C -0.0950(5) -0.59437(14) -0.5597(3) 0.0437(7) Uani 1 1 d . . . . .
H19 H 0.028363 -0.599805 -0.553148 0.052 Uiso 1 1 calc R U . . .
C20 C -0.1629(3) -0.54064(12) -0.5821(2) 0.0294(5) Uani 1 1 d . . . . .
C21 C -0.0296(3) -0.49515(12) -0.6000(2) 0.0260(5) Uani 1 1 d . . . . .
O4 O -0.6377(3) -0.38403(10) -0.2753(2) 0.0438(5) Uani 1 1 d . . . . .
O5 O -1.1859(3) -0.38459(11) -0.3225(2) 0.0512(6) Uani 1 1 d . . . . .
H5A H -1.264098 -0.380631 -0.263684 0.077 Uiso 1 1 calc R U . . .
O6 O -1.2107(3) -0.31290(14) -0.1014(3) 0.0659(8) Uani 1 1 d . . . . .
C22 C -0.9870(3) -0.30169(10) -0.4916(2) 0.0222(5) Uani 1 1 d . . . . .
C23 C -1.1635(3) -0.27921(13) -0.4907(3) 0.0338(6) Uani 1 1 d . . . . .
H23 H -1.233346 -0.287914 -0.411989 0.041 Uiso 1 1 calc R U . . .
C24 C -1.2320(4) -0.24504(15) -0.6036(4) 0.0450(7) Uani 1 1 d . . . . .
H24 H -1.348089 -0.231308 -0.600880 0.054 Uiso 1 1 calc R U . . .
C25 C -1.1304(5) -0.23037(14) -0.7230(3) 0.0467(8) Uani 1 1 d . . . . .
H25 H -1.179925 -0.208096 -0.800664 0.056 Uiso 1 1 calc R U . . .
C26 C -0.9591(4) -0.24894(13) -0.7246(3) 0.0380(6) Uani 1 1 d . . . . .
H26 H -0.890570 -0.238279 -0.802498 0.046 Uiso 1 1 calc R U . . .
C27 C -0.8832(3) -0.28403(11) -0.6106(2) 0.0255(5) Uani 1 1 d . . . . .
C28 C -0.7031(3) -0.30188(13) -0.6107(3) 0.0335(6) Uani 1 1 d . . . . .
H28 H -0.634783 -0.291252 -0.688738 0.040 Uiso 1 1 calc R U . . .
C29 C -0.6288(3) -0.33426(13) -0.4986(3) 0.0349(6) Uani 1 1 d . . . . .
H29 H -0.508839 -0.344477 -0.498459 0.042 Uiso 1 1 calc R U . . .
C30 C -0.7321(3) -0.35272(11) -0.3815(3) 0.0282(5) Uani 1 1 d . . . . .
C31 C -0.9116(3) -0.33918(10) -0.3804(2) 0.0230(5) Uani 1 1 d . . . . .
C32 C -1.0212(4) -0.36223(12) -0.2581(3) 0.0317(6) Uani 1 1 d . . . . .
C33 C -0.9186(5) -0.40976(13) -0.1757(3) 0.0455(8) Uani 1 1 d . . . . .
H33A H -0.973968 -0.417701 -0.083276 0.055 Uiso 1 1 calc R U . . .
H33B H -0.927311 -0.443435 -0.236861 0.055 Uiso 1 1 calc R U . . .
C34 C -0.7252(4) -0.39604(13) -0.1401(3) 0.0426(7) Uani 1 1 d . . . . .
H34 H -0.669388 -0.430414 -0.098229 0.051 Uiso 1 1 calc R U . . .
C35 C -0.6832(4) -0.34995(14) -0.0248(3) 0.0368(6) Uani 1 1 d . . . . .
H35A H -0.735983 -0.361041 0.066562 0.044 Uiso 1 1 calc R U . . .
H35B H -0.554437 -0.349416 -0.003041 0.044 Uiso 1 1 calc R U . . .
C36 C -0.7419(3) -0.29047(13) -0.0596(2) 0.0299(5) Uani 1 1 d . . . . .
C37 C -0.6172(5) -0.24773(16) -0.0328(3) 0.0476(8) Uani 1 1 d . . . . .
H37 H -0.498747 -0.256974 -0.005141 0.057 Uiso 1 1 calc R U . . .
C38 C -0.6653(7) -0.19189(17) -0.0463(4) 0.0681(13) Uani 1 1 d . . . . .
H38 H -0.578942 -0.164141 -0.027887 0.082 Uiso 1 1 calc R U . . .
C39 C -0.8397(8) -0.17671(15) -0.0867(4) 0.0682(13) Uani 1 1 d . . . . .
H39 H -0.871503 -0.138988 -0.095635 0.082 Uiso 1 1 calc R U . . .
C40 C -0.9666(5) -0.21836(14) -0.1139(3) 0.0468(8) Uani 1 1 d . . . . .
H40 H -1.084968 -0.208580 -0.140291 0.056 Uiso 1 1 calc R U . . .
C41 C -0.9186(3) -0.27497(12) -0.1020(2) 0.0292(5) Uani 1 1 d . . . . .
C42 C -1.0614(3) -0.31617(13) -0.1457(3) 0.0336(6) 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
O1 C9 1.373(3) . ?
O1 C13 1.446(3) . ?
O2 H2 0.8200 . ?
O2 C11 1.427(3) . ?
O3 C21 1.214(3) . ?
C1 C2 1.413(3) . ?
C1 C6 1.422(3) . ?
C1 C10 1.440(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.371(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.413(4) . ?
C6 C7 1.411(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.350(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.414(3) . ?
C9 C10 1.374(3) . ?
C10 C11 1.514(3) . ?
C11 C12 1.529(4) . ?
C11 C21 1.534(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.499(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.512(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.505(4) . ?
C15 C16 1.392(4) . ?
C15 C20 1.410(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(4) . ?
C20 C21 1.488(4) . ?
O4 C30 1.365(3) . ?
O4 C34 1.446(4) . ?
O5 H5A 0.8200 . ?
O5 C32 1.426(3) . ?
O6 C42 1.215(3) . ?
C22 C23 1.426(3) . ?
C22 C27 1.426(3) . ?
C22 C31 1.424(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.368(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.400(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.357(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.407(4) . ?
C27 C28 1.413(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.353(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.416(4) . ?
C30 C31 1.382(3) . ?
C31 C32 1.517(3) . ?
C32 C33 1.527(4) . ?
C32 C42 1.532(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.496(5) . ?
C34 H34 0.9800 . ?
C34 C35 1.523(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.507(4) . ?
C36 C37 1.389(4) . ?
C36 C41 1.400(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.378(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.378(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.382(6) . ?
C40 H40 0.9300 . ?
C40 C41 1.395(4) . ?
C41 C42 1.481(4) . ?

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
C9 O1 C13 118.25(18) . . ?
C11 O2 H2 109.5 . . ?
C2 C1 C6 118.0(2) . . ?
C2 C1 C10 122.5(2) . . ?
C6 C1 C10 119.6(2) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.4(2) . . ?
C7 C6 C1 119.1(2) . . ?
C7 C6 C5 121.4(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
O1 C9 C8 113.6(2) . . ?
O1 C9 C10 124.6(2) . . ?
C10 C9 C8 121.8(2) . . ?
C1 C10 C11 122.21(19) . . ?
C9 C10 C1 117.8(2) . . ?
C9 C10 C11 120.0(2) . . ?
O2 C11 C10 109.16(18) . . ?
O2 C11 C12 107.5(2) . . ?
O2 C11 C21 108.81(19) . . ?
C10 C11 C12 109.03(19) . . ?
C10 C11 C21 110.7(2) . . ?
C12 C11 C21 111.5(2) . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 112.8(2) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
O1 C13 C12 110.3(2) . . ?
O1 C13 H13 106.2 . . ?
O1 C13 C14 112.5(2) . . ?
C12 C13 H13 106.2 . . ?
C12 C13 C14 114.9(2) . . ?
C14 C13 H13 106.2 . . ?
C13 C14 H14A 107.4 . . ?
C13 C14 H14B 107.4 . . ?
H14A C14 H14B 106.9 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14A 107.4 . . ?
C15 C14 H14B 107.4 . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 C20 116.5(3) . . ?
C20 C15 C14 124.1(3) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 C15 122.1(3) . . ?
C17 C16 H16 118.9 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(4) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.9(4) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.3(3) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C21 122.9(3) . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 C21 116.4(2) . . ?
O3 C21 C11 119.5(2) . . ?
O3 C21 C20 121.6(2) . . ?
C20 C21 C11 118.71(18) . . ?
C30 O4 C34 116.7(2) . . ?
C32 O5 H5A 109.5 . . ?
C27 C22 C23 116.6(2) . . ?
C31 C22 C23 123.5(2) . . ?
C31 C22 C27 119.8(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.2(3) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.4(3) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.2(3) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C22 120.3(2) . . ?
C26 C27 C28 120.9(2) . . ?
C28 C27 C22 118.8(2) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
O4 C30 C29 113.7(2) . . ?
O4 C30 C31 125.3(2) . . ?
C31 C30 C29 121.0(2) . . ?
C22 C31 C32 121.6(2) . . ?
C30 C31 C22 118.6(2) . . ?
C30 C31 C32 119.7(2) . . ?
O5 C32 C31 109.79(19) . . ?
O5 C32 C33 108.1(2) . . ?
O5 C32 C42 109.1(2) . . ?
C31 C32 C33 109.7(2) . . ?
C31 C32 C42 111.0(2) . . ?
C33 C32 C42 109.1(2) . . ?
C32 C33 H33A 109.0 . . ?
C32 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C34 C33 C32 112.8(2) . . ?
C34 C33 H33A 109.0 . . ?
C34 C33 H33B 109.0 . . ?
O4 C34 C33 110.7(2) . . ?
O4 C34 H34 106.2 . . ?
O4 C34 C35 110.0(3) . . ?
C33 C34 H34 106.2 . . ?
C33 C34 C35 116.8(3) . . ?
C35 C34 H34 106.2 . . ?
C34 C35 H35A 107.4 . . ?
C34 C35 H35B 107.4 . . ?
H35A C35 H35B 107.0 . . ?
C36 C35 C34 119.5(2) . . ?
C36 C35 H35A 107.4 . . ?
C36 C35 H35B 107.4 . . ?
C37 C36 C35 118.0(3) . . ?
C37 C36 C41 117.7(3) . . ?
C41 C36 C35 124.0(2) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 C36 121.5(4) . . ?
C38 C37 H37 119.3 . . ?
C37 C38 H38 119.6 . . ?
C39 C38 C37 120.8(4) . . ?
C39 C38 H38 119.6 . . ?
C38 C39 H39 120.5 . . ?
C38 C39 C40 119.0(3) . . ?
C40 C39 H39 120.5 . . ?
C39 C40 H40 119.7 . . ?
C39 C40 C41 120.5(3) . . ?
C41 C40 H40 119.7 . . ?
C36 C41 C42 123.2(3) . . ?
C40 C41 C36 120.5(3) . . ?
C40 C41 C42 116.2(3) . . ?
O6 C42 C32 119.2(3) . . ?
O6 C42 C41 122.3(3) . . ?
C41 C42 C32 118.3(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
O1 C9 C10 C1 171.8(2) . . . . ?
O1 C9 C10 C11 -7.8(4) . . . . ?
O1 C13 C14 C15 57.1(3) . . . . ?
O2 C11 C12 C13 165.9(2) . . . . ?
O2 C11 C21 O3 11.8(3) . . . . ?
O2 C11 C21 C20 -163.6(2) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C1 C6 C7 C8 -2.7(4) . . . . ?
C1 C10 C11 O2 47.9(3) . . . . ?
C1 C10 C11 C12 165.1(2) . . . . ?
C1 C10 C11 C21 -71.9(3) . . . . ?
C2 C1 C6 C5 -2.4(4) . . . . ?
C2 C1 C6 C7 176.7(2) . . . . ?
C2 C1 C10 C9 -171.3(2) . . . . ?
C2 C1 C10 C11 8.3(4) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C4 C5 C6 C7 -177.5(3) . . . . ?
C5 C6 C7 C8 176.4(3) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
C6 C1 C10 C9 7.4(3) . . . . ?
C6 C1 C10 C11 -173.1(2) . . . . ?
C6 C7 C8 C9 2.0(4) . . . . ?
C7 C8 C9 O1 -176.4(3) . . . . ?
C7 C8 C9 C10 3.8(4) . . . . ?
C8 C9 C10 C1 -8.3(4) . . . . ?
C8 C9 C10 C11 172.1(2) . . . . ?
C9 O1 C13 C12 34.5(3) . . . . ?
C9 O1 C13 C14 -95.3(3) . . . . ?
C9 C10 C11 O2 -132.6(2) . . . . ?
C9 C10 C11 C12 -15.4(3) . . . . ?
C9 C10 C11 C21 107.6(3) . . . . ?
C10 C1 C2 C3 180.0(3) . . . . ?
C10 C1 C6 C5 178.9(2) . . . . ?
C10 C1 C6 C7 -2.0(3) . . . . ?
C10 C11 C12 C13 47.6(3) . . . . ?
C10 C11 C21 O3 131.7(2) . . . . ?
C10 C11 C21 C20 -43.6(3) . . . . ?
C11 C12 C13 O1 -58.1(3) . . . . ?
C11 C12 C13 C14 70.3(3) . . . . ?
C12 C11 C21 O3 -106.7(3) . . . . ?
C12 C11 C21 C20 77.9(3) . . . . ?
C12 C13 C14 C15 -70.2(3) . . . . ?
C13 O1 C9 C8 178.0(3) . . . . ?
C13 O1 C9 C10 -2.1(4) . . . . ?
C13 C14 C15 C16 -131.4(3) . . . . ?
C13 C14 C15 C20 53.6(3) . . . . ?
C14 C15 C16 C17 -177.1(3) . . . . ?
C14 C15 C20 C19 175.5(2) . . . . ?
C14 C15 C20 C21 -5.6(4) . . . . ?
C15 C16 C17 C18 1.4(6) . . . . ?
C15 C20 C21 O3 134.8(3) . . . . ?
C15 C20 C21 C11 -49.9(3) . . . . ?
C16 C15 C20 C19 0.4(4) . . . . ?
C16 C15 C20 C21 179.3(2) . . . . ?
C16 C17 C18 C19 0.2(6) . . . . ?
C17 C18 C19 C20 -1.5(5) . . . . ?
C18 C19 C20 C15 1.2(4) . . . . ?
C18 C19 C20 C21 -177.8(2) . . . . ?
C19 C20 C21 O3 -46.3(3) . . . . ?
C19 C20 C21 C11 129.0(2) . . . . ?
C20 C15 C16 C17 -1.7(5) . . . . ?
C21 C11 C12 C13 -74.9(3) . . . . ?
O4 C30 C31 C22 174.1(2) . . . . ?
O4 C30 C31 C32 -3.2(4) . . . . ?
O4 C34 C35 C36 61.9(3) . . . . ?
O5 C32 C33 C34 164.1(2) . . . . ?
O5 C32 C42 O6 15.8(4) . . . . ?
O5 C32 C42 C41 -160.5(2) . . . . ?
C22 C23 C24 C25 -0.8(5) . . . . ?
C22 C27 C28 C29 -1.3(4) . . . . ?
C22 C31 C32 O5 49.9(3) . . . . ?
C22 C31 C32 C33 168.6(2) . . . . ?
C22 C31 C32 C42 -70.8(3) . . . . ?
C23 C22 C27 C26 -3.8(3) . . . . ?
C23 C22 C27 C28 175.5(2) . . . . ?
C23 C22 C31 C30 -171.8(2) . . . . ?
C23 C22 C31 C32 5.4(4) . . . . ?
C23 C24 C25 C26 -2.1(5) . . . . ?
C24 C25 C26 C27 1.9(5) . . . . ?
C25 C26 C27 C22 1.1(4) . . . . ?
C25 C26 C27 C28 -178.2(3) . . . . ?
C26 C27 C28 C29 178.0(3) . . . . ?
C27 C22 C23 C24 3.7(4) . . . . ?
C27 C22 C31 C30 7.0(3) . . . . ?
C27 C22 C31 C32 -175.7(2) . . . . ?
C27 C28 C29 C30 2.4(4) . . . . ?
C28 C29 C30 O4 -178.8(2) . . . . ?
C28 C29 C30 C31 1.4(4) . . . . ?
C29 C30 C31 C22 -6.0(4) . . . . ?
C29 C30 C31 C32 176.6(2) . . . . ?
C30 O4 C34 C33 40.7(3) . . . . ?
C30 O4 C34 C35 -89.9(3) . . . . ?
C30 C31 C32 O5 -132.8(3) . . . . ?
C30 C31 C32 C33 -14.2(3) . . . . ?
C30 C31 C32 C42 106.5(3) . . . . ?
C31 C22 C23 C24 -177.4(3) . . . . ?
C31 C22 C27 C26 177.2(2) . . . . ?
C31 C22 C27 C28 -3.4(3) . . . . ?
C31 C32 C33 C34 44.4(3) . . . . ?
C31 C32 C42 O6 136.9(3) . . . . ?
C31 C32 C42 C41 -39.4(3) . . . . ?
C32 C33 C34 O4 -58.8(3) . . . . ?
C32 C33 C34 C35 68.1(3) . . . . ?
C33 C32 C42 O6 -102.1(3) . . . . ?
C33 C32 C42 C41 81.6(3) . . . . ?
C33 C34 C35 C36 -65.3(4) . . . . ?
C34 O4 C30 C29 169.6(2) . . . . ?
C34 O4 C30 C31 -10.5(4) . . . . ?
C34 C35 C36 C37 -132.2(3) . . . . ?
C34 C35 C36 C41 54.9(4) . . . . ?
C35 C36 C37 C38 -172.9(3) . . . . ?
C35 C36 C41 C40 171.8(2) . . . . ?
C35 C36 C41 C42 -12.2(4) . . . . ?
C36 C37 C38 C39 0.1(5) . . . . ?
C36 C41 C42 O6 136.1(3) . . . . ?
C36 C41 C42 C32 -47.7(3) . . . . ?
C37 C36 C41 C40 -1.1(3) . . . . ?
C37 C36 C41 C42 174.9(2) . . . . ?
C37 C38 C39 C40 0.0(5) . . . . ?
C38 C39 C40 C41 -0.6(5) . . . . ?
C39 C40 C41 C36 1.2(4) . . . . ?
C39 C40 C41 C42 -175.1(3) . . . . ?
C40 C41 C42 O6 -47.7(4) . . . . ?
C40 C41 C42 C32 128.5(3) . . . . ?
C41 C36 C37 C38 0.4(4) . . . . ?
C42 C32 C33 C34 -77.4(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.312 0.314 0.288 17.9 0.1 ?
2 0.688 0.814 0.712 17.9 0.1 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.969
_oxdiff_exptl_absorpt_empirical_full_min 0.590
####################################################################### 
# 
# 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_20220114-lk-zzx-1474-up
_database_code_depnum_ccdc_archive 'CCDC 2151481'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2022-01-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H17 Br O2)'
_chemical_formula_sum            'C44 H34 Br2 O4'
_chemical_formula_weight         786.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   28.1188(8)
_cell_length_b                   7.6926(2)
_cell_length_c                   15.6637(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.223(3)
_cell_angle_gamma                90
_cell_volume                     3385.61(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8621
_cell_measurement_temperature    200.01(10)
_cell_measurement_theta_max      28.5290
_cell_measurement_theta_min      3.5940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27434
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.036
_diffrn_reflns_theta_min         3.327
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  48.00   1.00   27.50    --   18.58 -19.00 120.00   84
  2  ω    -50.00  27.00   1.00   27.50    --   18.58 -38.00  60.00   77
  3  ω    -44.00  34.00   1.00   27.50    --   18.58 -57.00-120.00   78
  4  ω    -42.00  11.00   1.00   27.50    --  -18.78 -77.00 -60.00   53
  5  ω    -39.00  11.00   1.00   27.50    --  -18.78 -77.00-150.00   50
  6  ω    -80.00  -4.00   1.00   27.50    --  -18.78 -57.00  30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0113368000
_diffrn_orient_matrix_UB_12      -0.0228455000
_diffrn_orient_matrix_UB_13      0.0396827000
_diffrn_orient_matrix_UB_21      0.0063130000
_diffrn_orient_matrix_UB_22      0.0882340000
_diffrn_orient_matrix_UB_23      0.0070328000
_diffrn_orient_matrix_UB_31      -0.0216608000
_diffrn_orient_matrix_UB_32      0.0137852000
_diffrn_orient_matrix_UB_33      0.0207320000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6205
_reflns_number_total             8072
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.652
_refine_diff_density_min         -1.488
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8072
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0781
_refine_ls_restrained_S_all      1.151
_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)+38.4785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1771
_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:
 C00R(H00R), C00T(H00T), C012(H012), C017(H017)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C010(H01F,H01G)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00F(H00F), C00G(H00G), C00M(H00M), C00N(H00N),
 C00O(H00O), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C013(H013), C015(H015), C018(H018), C019(H019), C01A(H01D), C01C(H01K),
 C01D(H01L), C01E(H01E)
2.d Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C), C016(H01H,H01I,H01J)
;
_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 0.62857(2) 0.12108(8) 0.27156(4) 0.02970(17) Uani 1 1 d . . . . .
Br02 Br 0.86748(2) 0.62029(9) 0.25140(5) 0.03035(18) Uani 1 1 d . . . . .
O003 O 0.62298(17) 0.5502(6) 0.0715(3) 0.0297(10) Uani 1 1 d . . . . .
O004 O 0.87798(19) 1.0438(6) 0.0521(3) 0.0352(12) Uani 1 1 d . . . . .
O005 O 0.67002(18) 0.7066(7) 0.1696(3) 0.0363(12) Uani 1 1 d . . . . .
O006 O 0.83123(19) 1.2050(7) 0.1412(3) 0.0394(12) Uani 1 1 d . . . . .
C007 C 0.9053(2) 0.8121(8) 0.2160(4) 0.0221(12) Uani 1 1 d . . . . .
C008 C 0.5922(2) 0.3169(8) 0.2300(4) 0.0192(12) Uani 1 1 d . . . . .
C009 C 0.5350(2) 0.1076(9) 0.1574(4) 0.0273(14) Uani 1 1 d . . . . .
H009 H 0.553774 0.012777 0.178068 0.033 Uiso 1 1 calc R U . . .
C00A C 0.5497(2) 0.2780(8) 0.1763(4) 0.0229(13) Uani 1 1 d . . . . .
C00B C 0.5226(2) 0.4170(9) 0.1426(4) 0.0262(14) Uani 1 1 d . . . . .
C00C C 0.8623(2) 0.9005(9) 0.4144(4) 0.0277(14) Uani 1 1 d . . . . .
H00C H 0.891418 0.852726 0.396340 0.033 Uiso 1 1 calc R U . . .
C00D C 0.9484(2) 0.7679(8) 0.1693(4) 0.0235(13) Uani 1 1 d . . . . .
C00E C 0.9764(2) 0.9054(9) 0.1385(4) 0.0267(14) Uani 1 1 d . . . . .
C00F C 0.6348(2) 0.3977(8) 0.4343(4) 0.0267(14) Uani 1 1 d . . . . .
H00F H 0.604993 0.356950 0.411930 0.032 Uiso 1 1 calc R U . . .
C00G C 0.6482(3) 0.3675(9) 0.5184(4) 0.0345(16) Uani 1 1 d . . . . .
H00G H 0.627301 0.305855 0.553744 0.041 Uiso 1 1 calc R U . . .
C00H C 0.6534(2) 0.5297(8) 0.2937(4) 0.0246(13) Uani 1 1 d . . . . .
C00I C 0.8903(2) 0.9731(8) 0.2297(4) 0.0240(13) Uani 1 1 d . . . . .
C00J C 0.8467(2) 1.0320(8) 0.2697(4) 0.0247(13) Uani 1 1 d . . . . .
C00K C 0.6087(2) 0.4781(8) 0.2469(4) 0.0227(13) Uani 1 1 d . . . . .
C00L C 0.6812(2) 0.6438(9) 0.2501(4) 0.0295(14) Uani 1 1 d . . . . .
C00M C 0.9626(2) 0.5963(9) 0.1546(5) 0.0316(15) Uani 1 1 d . . . . .
H00M H 0.943932 0.502808 0.174554 0.038 Uiso 1 1 calc R U . . .
C00N C 0.7766(3) 1.2178(10) 0.2502(5) 0.0382(18) Uani 1 1 d . . . . .
H00N H 0.757673 1.293156 0.214794 0.046 Uiso 1 1 calc R U . . .
C00O C 0.8498(3) 0.8746(10) 0.4957(5) 0.0345(16) Uani 1 1 d . . . . .
H00O H 0.870075 0.809886 0.533887 0.041 Uiso 1 1 calc R U . . .
C00P C 0.6658(2) 0.4899(8) 0.3815(4) 0.0248(13) Uani 1 1 d . . . . .
C00Q C 0.5365(2) 0.6027(9) 0.1597(4) 0.0289(14) Uani 1 1 d . . . . .
H00A H 0.513145 0.653953 0.198212 0.035 Uiso 1 1 calc R U . . .
H00B H 0.533926 0.667372 0.105088 0.035 Uiso 1 1 calc R U . . .
C00R C 0.6229(2) 0.6805(8) 0.1327(4) 0.0255(13) Uani 1 1 d . . . . .
H00R H 0.612285 0.790979 0.104282 0.031 Uiso 1 1 calc R U . . .
C00S C 0.7101(2) 0.5522(8) 0.4166(4) 0.0276(14) Uani 1 1 d . . . . .
C00T C 0.9135(2) 1.1252(8) 0.1845(4) 0.0264(13) Uani 1 1 d . . . . .
H00T H 0.915240 1.224483 0.225762 0.032 Uiso 1 1 calc R U . . .
C00U C 0.7902(2) 1.0699(9) 0.3841(5) 0.0316(15) Uani 1 1 d . . . . .
C00V C 0.8334(2) 0.9970(8) 0.3547(5) 0.0276(14) Uani 1 1 d . . . . .
C00W C 0.7393(3) 0.6538(9) 0.3659(5) 0.0357(17) Uani 1 1 d . . . . .
H00W H 0.769527 0.689402 0.388711 0.043 Uiso 1 1 calc R U . . .
C00X C 1.0038(2) 0.5615(10) 0.1108(5) 0.0351(16) Uani 1 1 d . . . . .
H00X H 1.012709 0.444590 0.100198 0.042 Uiso 1 1 calc R U . . .
C00Y C 0.7624(2) 1.1759(10) 0.3299(5) 0.0370(17) Uani 1 1 d . . . . .
H00Y H 0.733053 1.219705 0.348933 0.044 Uiso 1 1 calc R U . . .
C00Z C 0.7259(3) 0.7030(9) 0.2855(5) 0.0346(16) Uani 1 1 d . . . . .
H00Z H 0.745833 0.775496 0.253234 0.041 Uiso 1 1 calc R U . . .
C010 C 0.9637(2) 1.0934(9) 0.1549(5) 0.0314(15) Uani 1 1 d . . . . .
H01F H 0.967842 1.159998 0.101629 0.038 Uiso 1 1 calc R U . . .
H01G H 0.986558 1.140348 0.198657 0.038 Uiso 1 1 calc R U . . .
C011 C 0.7781(3) 1.0388(10) 0.4703(5) 0.0378(18) Uani 1 1 d . . . . .
H011 H 0.749418 1.086037 0.490323 0.045 Uiso 1 1 calc R U . . .
C012 C 0.8781(3) 1.1756(9) 0.1126(4) 0.0312(15) Uani 1 1 d . . . . .
H012 H 0.889492 1.284860 0.085534 0.037 Uiso 1 1 calc R U . . .
C013 C 0.7217(3) 0.5166(10) 0.5042(5) 0.0355(17) Uani 1 1 d . . . . .
H013 H 0.751035 0.557832 0.528742 0.043 Uiso 1 1 calc R U . . .
C014 C 0.6510(3) 0.5924(10) -0.0001(5) 0.0364(17) Uani 1 1 d . . . . .
H01A H 0.648763 0.497820 -0.041955 0.055 Uiso 1 1 calc R U . . .
H01B H 0.684258 0.608143 0.019244 0.055 Uiso 1 1 calc R U . . .
H01C H 0.639038 0.700159 -0.026524 0.055 Uiso 1 1 calc R U . . .
C015 C 0.4817(2) 0.3810(10) 0.0934(5) 0.0352(16) Uani 1 1 d . . . . .
H015 H 0.463163 0.474514 0.070525 0.042 Uiso 1 1 calc R U . . .
C016 C 0.8527(3) 1.0871(10) -0.0262(4) 0.0347(16) Uani 1 1 d . . . . .
H01H H 0.857086 0.994470 -0.068109 0.052 Uiso 1 1 calc R U . . .
H01I H 0.865005 1.196744 -0.048364 0.052 Uiso 1 1 calc R U . . .
H01J H 0.818759 1.099790 -0.015674 0.052 Uiso 1 1 calc R U . . .
C017 C 0.5867(2) 0.6319(8) 0.1997(4) 0.0257(13) Uani 1 1 d . . . . .
H017 H 0.585007 0.730648 0.241038 0.031 Uiso 1 1 calc R U . . .
C018 C 0.6920(3) 0.4256(10) 0.5532(5) 0.0389(18) Uani 1 1 d . . . . .
H018 H 0.700871 0.401050 0.611064 0.047 Uiso 1 1 calc R U . . .
C019 C 1.0172(3) 0.8662(11) 0.0956(5) 0.0364(17) Uani 1 1 d . . . . .
H019 H 1.036000 0.958183 0.074405 0.044 Uiso 1 1 calc R U . . .
C01A C 0.4939(2) 0.0748(10) 0.1093(5) 0.0350(16) Uani 1 1 d . . . . .
H01D H 0.484033 -0.041595 0.098733 0.042 Uiso 1 1 calc R U . . .
C01B C 0.8191(3) 1.1491(9) 0.2207(5) 0.0343(16) Uani 1 1 d . . . . .
C01C C 1.0314(3) 0.6951(11) 0.0829(5) 0.0401(18) Uani 1 1 d . . . . .
H01K H 1.060083 0.671067 0.055044 0.048 Uiso 1 1 calc R U . . .
C01D C 0.8064(3) 0.9439(10) 0.5244(5) 0.0393(18) Uani 1 1 d . . . . .
H01L H 0.797201 0.923649 0.581318 0.047 Uiso 1 1 calc R U . . .
C01E C 0.4672(3) 0.2111(11) 0.0767(5) 0.0398(18) Uani 1 1 d . . . . .
H01E H 0.439043 0.189229 0.043027 0.048 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 C008 1.919(6) . ?
Br02 C007 1.913(6) . ?
O003 C00R 1.386(8) . ?
O003 C014 1.432(8) . ?
O004 C012 1.388(8) . ?
O004 C016 1.432(8) . ?
O005 C00L 1.375(8) . ?
O005 C00R 1.438(8) . ?
O006 C012 1.425(9) . ?
O006 C01B 1.373(9) . ?
C007 C00D 1.481(9) . ?
C007 C00I 1.328(9) . ?
C008 C00A 1.466(8) . ?
C008 C00K 1.346(9) . ?
C009 H009 0.9500 . ?
C009 C00A 1.403(9) . ?
C009 C01A 1.377(9) . ?
C00A C00B 1.405(9) . ?
C00B C00Q 1.503(9) . ?
C00B C015 1.387(9) . ?
C00C H00C 0.9500 . ?
C00C C00O 1.350(10) . ?
C00C C00V 1.424(10) . ?
C00D C00E 1.414(9) . ?
C00D C00M 1.400(9) . ?
C00E C010 1.514(9) . ?
C00E C019 1.386(10) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.376(9) . ?
C00F C00P 1.415(9) . ?
C00G H00G 0.9500 . ?
C00G C018 1.400(11) . ?
C00H C00K 1.485(9) . ?
C00H C00L 1.374(9) . ?
C00H C00P 1.438(9) . ?
C00I C00J 1.468(9) . ?
C00I C00T 1.528(9) . ?
C00J C00V 1.422(9) . ?
C00J C01B 1.399(9) . ?
C00K C017 1.514(9) . ?
C00L C00Z 1.427(10) . ?
C00M H00M 0.9500 . ?
C00M C00X 1.395(10) . ?
C00N H00N 0.9500 . ?
C00N C00Y 1.364(11) . ?
C00N C01B 1.403(10) . ?
C00O H00O 0.9500 . ?
C00O C01D 1.422(11) . ?
C00P C00S 1.426(9) . ?
C00Q H00A 0.9900 . ?
C00Q H00B 0.9900 . ?
C00Q C017 1.540(9) . ?
C00R H00R 1.0000 . ?
C00R C017 1.537(9) . ?
C00S C00W 1.402(10) . ?
C00S C013 1.424(10) . ?
C00T H00T 1.0000 . ?
C00T C010 1.522(9) . ?
C00T C012 1.525(9) . ?
C00U C00V 1.432(9) . ?
C00U C00Y 1.394(11) . ?
C00U C011 1.425(10) . ?
C00W H00W 0.9500 . ?
C00W C00Z 1.354(10) . ?
C00X H00X 0.9500 . ?
C00X C01C 1.370(11) . ?
C00Y H00Y 0.9500 . ?
C00Z H00Z 0.9500 . ?
C010 H01F 0.9900 . ?
C010 H01G 0.9900 . ?
C011 H011 0.9500 . ?
C011 C01D 1.353(11) . ?
C012 H012 1.0000 . ?
C013 H013 0.9500 . ?
C013 C018 1.351(11) . ?
C014 H01A 0.9800 . ?
C014 H01B 0.9800 . ?
C014 H01C 0.9800 . ?
C015 H015 0.9500 . ?
C015 C01E 1.391(11) . ?
C016 H01H 0.9800 . ?
C016 H01I 0.9800 . ?
C016 H01J 0.9800 . ?
C017 H017 1.0000 . ?
C018 H018 0.9500 . ?
C019 H019 0.9500 . ?
C019 C01C 1.391(11) . ?
C01A H01D 0.9500 . ?
C01A C01E 1.376(11) . ?
C01C H01K 0.9500 . ?
C01D H01L 0.9500 . ?
C01E H01E 0.9500 . ?

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
C00R O003 C014 113.1(5) . . ?
C012 O004 C016 113.8(5) . . ?
C00L O005 C00R 119.6(5) . . ?
C01B O006 C012 120.0(5) . . ?
C00D C007 Br02 116.2(4) . . ?
C00I C007 Br02 119.3(5) . . ?
C00I C007 C00D 124.4(6) . . ?
C00A C008 Br01 116.5(4) . . ?
C00K C008 Br01 118.8(4) . . ?
C00K C008 C00A 124.5(6) . . ?
C00A C009 H009 119.3 . . ?
C01A C009 H009 119.3 . . ?
C01A C009 C00A 121.4(7) . . ?
C009 C00A C008 122.6(6) . . ?
C009 C00A C00B 118.7(6) . . ?
C00B C00A C008 118.6(6) . . ?
C00A C00B C00Q 121.5(6) . . ?
C015 C00B C00A 118.9(6) . . ?
C015 C00B C00Q 119.6(6) . . ?
C00O C00C H00C 118.8 . . ?
C00O C00C C00V 122.3(6) . . ?
C00V C00C H00C 118.8 . . ?
C00E C00D C007 118.3(6) . . ?
C00M C00D C007 122.7(6) . . ?
C00M C00D C00E 119.0(6) . . ?
C00D C00E C010 121.2(6) . . ?
C019 C00E C00D 119.0(6) . . ?
C019 C00E C010 119.7(6) . . ?
C00G C00F H00F 120.2 . . ?
C00G C00F C00P 119.6(7) . . ?
C00P C00F H00F 120.2 . . ?
C00F C00G H00G 119.3 . . ?
C00F C00G C018 121.5(7) . . ?
C018 C00G H00G 119.3 . . ?
C00L C00H C00K 114.4(6) . . ?
C00L C00H C00P 119.3(6) . . ?
C00P C00H C00K 125.7(6) . . ?
C007 C00I C00J 129.2(6) . . ?
C007 C00I C00T 119.7(6) . . ?
C00J C00I C00T 109.9(5) . . ?
C00V C00J C00I 126.5(6) . . ?
C01B C00J C00I 114.8(6) . . ?
C01B C00J C00V 118.3(6) . . ?
C008 C00K C00H 128.4(6) . . ?
C008 C00K C017 119.6(6) . . ?
C00H C00K C017 110.7(5) . . ?
O005 C00L C00Z 114.2(6) . . ?
C00H C00L O005 124.4(6) . . ?
C00H C00L C00Z 121.3(7) . . ?
C00D C00M H00M 119.7 . . ?
C00X C00M C00D 120.5(7) . . ?
C00X C00M H00M 119.7 . . ?
C00Y C00N H00N 120.2 . . ?
C00Y C00N C01B 119.7(7) . . ?
C01B C00N H00N 120.2 . . ?
C00C C00O H00O 120.0 . . ?
C00C C00O C01D 120.1(7) . . ?
C01D C00O H00O 120.0 . . ?
C00F C00P C00H 122.4(6) . . ?
C00F C00P C00S 119.4(6) . . ?
C00S C00P C00H 118.2(6) . . ?
C00B C00Q H00A 108.3 . . ?
C00B C00Q H00B 108.3 . . ?
C00B C00Q C017 116.1(5) . . ?
H00A C00Q H00B 107.4 . . ?
C017 C00Q H00A 108.3 . . ?
C017 C00Q H00B 108.3 . . ?
O003 C00R O005 110.7(5) . . ?
O003 C00R H00R 108.4 . . ?
O003 C00R C017 108.3(5) . . ?
O005 C00R H00R 108.4 . . ?
O005 C00R C017 112.5(5) . . ?
C017 C00R H00R 108.4 . . ?
C00W C00S C00P 119.3(6) . . ?
C00W C00S C013 122.4(6) . . ?
C013 C00S C00P 118.2(7) . . ?
C00I C00T H00T 107.3 . . ?
C010 C00T C00I 115.9(5) . . ?
C010 C00T H00T 107.3 . . ?
C010 C00T C012 113.7(6) . . ?
C012 C00T C00I 105.0(5) . . ?
C012 C00T H00T 107.3 . . ?
C00Y C00U C00V 119.8(7) . . ?
C00Y C00U C011 121.8(7) . . ?
C011 C00U C00V 118.4(7) . . ?
C00C C00V C00U 117.6(6) . . ?
C00J C00V C00C 123.3(6) . . ?
C00J C00V C00U 119.0(6) . . ?
C00S C00W H00W 118.8 . . ?
C00Z C00W C00S 122.4(7) . . ?
C00Z C00W H00W 118.8 . . ?
C00M C00X H00X 119.8 . . ?
C01C C00X C00M 120.3(7) . . ?
C01C C00X H00X 119.8 . . ?
C00N C00Y C00U 121.3(7) . . ?
C00N C00Y H00Y 119.4 . . ?
C00U C00Y H00Y 119.4 . . ?
C00L C00Z H00Z 120.6 . . ?
C00W C00Z C00L 118.7(7) . . ?
C00W C00Z H00Z 120.6 . . ?
C00E C010 C00T 115.7(6) . . ?
C00E C010 H01F 108.4 . . ?
C00E C010 H01G 108.4 . . ?
C00T C010 H01F 108.4 . . ?
C00T C010 H01G 108.4 . . ?
H01F C010 H01G 107.4 . . ?
C00U C011 H011 119.0 . . ?
C01D C011 C00U 122.0(7) . . ?
C01D C011 H011 119.0 . . ?
O004 C012 O006 110.7(6) . . ?
O004 C012 C00T 107.6(5) . . ?
O004 C012 H012 108.4 . . ?
O006 C012 C00T 113.2(6) . . ?
O006 C012 H012 108.4 . . ?
C00T C012 H012 108.4 . . ?
C00S C013 H013 119.3 . . ?
C018 C013 C00S 121.5(7) . . ?
C018 C013 H013 119.3 . . ?
O003 C014 H01A 109.5 . . ?
O003 C014 H01B 109.5 . . ?
O003 C014 H01C 109.5 . . ?
H01A C014 H01B 109.5 . . ?
H01A C014 H01C 109.5 . . ?
H01B C014 H01C 109.5 . . ?
C00B C015 H015 119.3 . . ?
C00B C015 C01E 121.5(7) . . ?
C01E C015 H015 119.3 . . ?
O004 C016 H01H 109.5 . . ?
O004 C016 H01I 109.5 . . ?
O004 C016 H01J 109.5 . . ?
H01H C016 H01I 109.5 . . ?
H01H C016 H01J 109.5 . . ?
H01I C016 H01J 109.5 . . ?
C00K C017 C00Q 115.8(5) . . ?
C00K C017 C00R 104.8(5) . . ?
C00K C017 H017 107.9 . . ?
C00Q C017 H017 107.9 . . ?
C00R C017 C00Q 112.3(5) . . ?
C00R C017 H017 107.9 . . ?
C00G C018 H018 120.0 . . ?
C013 C018 C00G 119.9(7) . . ?
C013 C018 H018 120.0 . . ?
C00E C019 H019 119.3 . . ?
C00E C019 C01C 121.5(7) . . ?
C01C C019 H019 119.3 . . ?
C009 C01A H01D 120.1 . . ?
C01E C01A C009 119.8(7) . . ?
C01E C01A H01D 120.1 . . ?
O006 C01B C00J 123.2(6) . . ?
O006 C01B C00N 115.2(6) . . ?
C00J C01B C00N 121.6(7) . . ?
C00X C01C C019 119.7(7) . . ?
C00X C01C H01K 120.2 . . ?
C019 C01C H01K 120.2 . . ?
C00O C01D H01L 120.2 . . ?
C011 C01D C00O 119.7(7) . . ?
C011 C01D H01L 120.2 . . ?
C015 C01E H01E 120.2 . . ?
C01A C01E C015 119.7(7) . . ?
C01A C01E H01E 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
Br01 C008 C00A C009 1.5(8) . . . . ?
Br01 C008 C00A C00B -178.4(4) . . . . ?
Br01 C008 C00K C00H 1.4(9) . . . . ?
Br01 C008 C00K C017 167.0(4) . . . . ?
Br02 C007 C00D C00E 177.3(5) . . . . ?
Br02 C007 C00D C00M -2.8(8) . . . . ?
Br02 C007 C00I C00J -0.3(10) . . . . ?
Br02 C007 C00I C00T -166.1(4) . . . . ?
O003 C00R C017 C00K 69.6(6) . . . . ?
O003 C00R C017 C00Q -56.8(7) . . . . ?
O005 C00L C00Z C00W 177.4(7) . . . . ?
O005 C00R C017 C00K -53.1(7) . . . . ?
O005 C00R C017 C00Q -179.5(5) . . . . ?
C007 C00D C00E C010 1.9(9) . . . . ?
C007 C00D C00E C019 179.2(6) . . . . ?
C007 C00D C00M C00X -179.5(6) . . . . ?
C007 C00I C00J C00V 60.8(10) . . . . ?
C007 C00I C00J C01B -126.6(8) . . . . ?
C007 C00I C00T C010 -23.1(9) . . . . ?
C007 C00I C00T C012 103.2(7) . . . . ?
C008 C00A C00B C00Q 0.5(9) . . . . ?
C008 C00A C00B C015 -178.6(6) . . . . ?
C008 C00K C017 C00Q 20.8(9) . . . . ?
C008 C00K C017 C00R -103.4(7) . . . . ?
C009 C00A C00B C00Q -179.5(6) . . . . ?
C009 C00A C00B C015 1.5(9) . . . . ?
C009 C01A C01E C015 -0.7(11) . . . . ?
C00A C008 C00K C00H -174.0(6) . . . . ?
C00A C008 C00K C017 -8.4(9) . . . . ?
C00A C009 C01A C01E 2.0(11) . . . . ?
C00A C00B C00Q C017 12.3(9) . . . . ?
C00A C00B C015 C01E -0.2(10) . . . . ?
C00B C00Q C017 C00K -22.2(8) . . . . ?
C00B C00Q C017 C00R 98.1(7) . . . . ?
C00B C015 C01E C01A -0.2(12) . . . . ?
C00C C00O C01D C011 -1.3(11) . . . . ?
C00D C007 C00I C00J 175.4(6) . . . . ?
C00D C007 C00I C00T 9.7(10) . . . . ?
C00D C00E C010 C00T -15.5(9) . . . . ?
C00D C00E C019 C01C -0.5(11) . . . . ?
C00D C00M C00X C01C 1.2(11) . . . . ?
C00E C00D C00M C00X 0.5(10) . . . . ?
C00E C019 C01C C00X 2.1(12) . . . . ?
C00F C00G C018 C013 1.4(11) . . . . ?
C00F C00P C00S C00W -175.6(6) . . . . ?
C00F C00P C00S C013 0.8(9) . . . . ?
C00G C00F C00P C00H -178.4(6) . . . . ?
C00G C00F C00P C00S -0.9(9) . . . . ?
C00H C00K C017 C00Q -171.2(5) . . . . ?
C00H C00K C017 C00R 64.5(6) . . . . ?
C00H C00L C00Z C00W -4.4(11) . . . . ?
C00H C00P C00S C00W 2.0(9) . . . . ?
C00H C00P C00S C013 178.4(6) . . . . ?
C00I C007 C00D C00E 1.4(9) . . . . ?
C00I C007 C00D C00M -178.7(7) . . . . ?
C00I C00J C00V C00C 1.6(10) . . . . ?
C00I C00J C00V C00U 178.0(6) . . . . ?
C00I C00J C01B O006 0.3(10) . . . . ?
C00I C00J C01B C00N -179.8(6) . . . . ?
C00I C00T C010 C00E 25.2(9) . . . . ?
C00I C00T C012 O004 -70.3(7) . . . . ?
C00I C00T C012 O006 52.3(7) . . . . ?
C00J C00I C00T C010 168.6(6) . . . . ?
C00J C00I C00T C012 -65.1(7) . . . . ?
C00K C008 C00A C009 177.1(6) . . . . ?
C00K C008 C00A C00B -2.8(9) . . . . ?
C00K C00H C00L O005 -0.6(10) . . . . ?
C00K C00H C00L C00Z -178.6(6) . . . . ?
C00K C00H C00P C00F -1.5(10) . . . . ?
C00K C00H C00P C00S -179.1(6) . . . . ?
C00L O005 C00R O003 -104.1(7) . . . . ?
C00L O005 C00R C017 17.3(8) . . . . ?
C00L C00H C00K C008 127.2(7) . . . . ?
C00L C00H C00K C017 -39.4(8) . . . . ?
C00L C00H C00P C00F 169.1(6) . . . . ?
C00L C00H C00P C00S -8.4(9) . . . . ?
C00M C00D C00E C010 -178.1(6) . . . . ?
C00M C00D C00E C019 -0.8(10) . . . . ?
C00M C00X C01C C019 -2.4(12) . . . . ?
C00O C00C C00V C00J 177.4(7) . . . . ?
C00O C00C C00V C00U 1.0(10) . . . . ?
C00P C00F C00G C018 -0.2(10) . . . . ?
C00P C00H C00K C008 -61.7(10) . . . . ?
C00P C00H C00K C017 131.7(6) . . . . ?
C00P C00H C00L O005 -172.3(6) . . . . ?
C00P C00H C00L C00Z 9.7(10) . . . . ?
C00P C00S C00W C00Z 3.4(10) . . . . ?
C00P C00S C013 C018 0.4(10) . . . . ?
C00Q C00B C015 C01E -179.3(7) . . . . ?
C00R O005 C00L C00H 12.1(10) . . . . ?
C00R O005 C00L C00Z -169.8(6) . . . . ?
C00S C00W C00Z C00L -2.4(11) . . . . ?
C00S C013 C018 C00G -1.5(11) . . . . ?
C00T C00I C00J C00V -132.3(7) . . . . ?
C00T C00I C00J C01B 40.2(8) . . . . ?
C00U C011 C01D C00O 1.0(11) . . . . ?
C00V C00C C00O C01D 0.3(11) . . . . ?
C00V C00J C01B O006 173.6(6) . . . . ?
C00V C00J C01B C00N -6.6(10) . . . . ?
C00V C00U C00Y C00N -2.7(11) . . . . ?
C00V C00U C011 C01D 0.4(10) . . . . ?
C00W C00S C013 C018 176.7(7) . . . . ?
C00Y C00N C01B O006 -177.3(7) . . . . ?
C00Y C00N C01B C00J 2.8(11) . . . . ?
C00Y C00U C00V C00C 175.4(6) . . . . ?
C00Y C00U C00V C00J -1.2(9) . . . . ?
C00Y C00U C011 C01D -176.3(7) . . . . ?
C010 C00E C019 C01C 176.8(7) . . . . ?
C010 C00T C012 O004 57.4(7) . . . . ?
C010 C00T C012 O006 180.0(6) . . . . ?
C011 C00U C00V C00C -1.3(9) . . . . ?
C011 C00U C00V C00J -177.9(6) . . . . ?
C011 C00U C00Y C00N 173.9(7) . . . . ?
C012 O006 C01B C00J -14.0(10) . . . . ?
C012 O006 C01B C00N 166.1(6) . . . . ?
C012 C00T C010 C00E -96.6(7) . . . . ?
C013 C00S C00W C00Z -172.8(7) . . . . ?
C014 O003 C00R O005 -63.8(7) . . . . ?
C014 O003 C00R C017 172.4(6) . . . . ?
C015 C00B C00Q C017 -168.7(6) . . . . ?
C016 O004 C012 O006 66.3(7) . . . . ?
C016 O004 C012 C00T -169.5(6) . . . . ?
C019 C00E C010 C00T 167.2(6) . . . . ?
C01A C009 C00A C008 177.6(6) . . . . ?
C01A C009 C00A C00B -2.4(10) . . . . ?
C01B O006 C012 O004 105.8(7) . . . . ?
C01B O006 C012 C00T -15.1(9) . . . . ?
C01B C00J C00V C00C -170.7(6) . . . . ?
C01B C00J C00V C00U 5.7(9) . . . . ?
C01B C00N C00Y C00U 2.0(11) . . . . ?

_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 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.807
####################################################################### 
# 
# 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_20210212-yanhl-zzx-577
_database_code_depnum_ccdc_archive 'CCDC 2151485'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2021-02-12
_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         'C20 H13 Br O2'
_chemical_formula_sum            'C20 H13 Br O2'
_chemical_formula_weight         365.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H13 Br O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0085(3)
_cell_length_b                   8.9848(6)
_cell_length_c                   21.0224(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1512.66(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1812
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.6000
_cell_measurement_theta_min      3.5270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6118
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.044
_diffrn_reflns_theta_min         3.408
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  49.00   1.00    5.14    --   18.58 -99.00 -90.00   43
  2  ω    -89.00 -52.00   1.00    5.14    --  -18.81 178.00  60.00   37
  3  ω    -91.00  26.00   1.00    5.14    --  -18.81   0.00 -30.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0091763000
_diffrn_orient_matrix_UB_12      0.0785198000
_diffrn_orient_matrix_UB_13      0.0002612000
_diffrn_orient_matrix_UB_21      0.0296660000
_diffrn_orient_matrix_UB_22      -0.0022020000
_diffrn_orient_matrix_UB_23      -0.0317638000
_diffrn_orient_matrix_UB_31      -0.0829495000
_diffrn_orient_matrix_UB_32      0.0079102000
_diffrn_orient_matrix_UB_33      -0.0113676000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                2759
_reflns_number_total             3463
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.384
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 868 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.035
_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)+(0.0247P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0823
_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:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C15(H15), C5(H5), C14(H14), C2(H2), C16(H16), C17(H17),
 C3(H3), C4(H4)
;
_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 0.38310(6) 0.70159(7) 0.33690(3) 0.04471(17) Uani 1 1 d . . . . .
O2 O 0.9440(4) 0.6681(4) 0.33892(19) 0.0509(10) Uani 1 1 d . . . . .
O1 O 0.9149(4) 0.6942(5) 0.23107(18) 0.0512(10) Uani 1 1 d . . . . .
C12 C 0.5900(5) 0.5973(5) 0.3342(3) 0.0339(11) Uani 1 1 d . . . . .
C6 C 0.4917(6) 0.6880(7) 0.1164(2) 0.0390(13) Uani 1 1 d . . . . .
C7 C 0.6384(7) 0.7644(6) 0.0994(3) 0.0471(14) Uani 1 1 d . . . . .
H7 H 0.641301 0.816602 0.061169 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6522(6) 0.5489(6) 0.2794(2) 0.0330(12) Uani 1 1 d . . . . .
C8 C 0.7764(7) 0.7639(6) 0.1374(3) 0.0451(15) Uani 1 1 d . . . . .
H8 H 0.873072 0.813343 0.125056 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7701(6) 0.6880(7) 0.1951(2) 0.0402(13) Uani 1 1 d . . . . .
C20 C 0.8168(6) 0.4666(6) 0.2808(3) 0.0413(14) Uani 1 1 d . . . . .
H20A H 0.826236 0.406077 0.318801 0.050 Uiso 1 1 calc R U . . .
H20B H 0.828634 0.403099 0.243703 0.050 Uiso 1 1 calc R U . . .
C10 C 0.6281(6) 0.6142(6) 0.2155(2) 0.0324(11) Uani 1 1 d . . . . .
C15 C 0.7061(8) 0.5692(7) 0.5093(3) 0.0547(16) Uani 1 1 d . . . . .
H15 H 0.654822 0.553858 0.548397 0.066 Uiso 1 1 calc R U . . .
C1 C 0.4868(5) 0.6088(6) 0.1746(2) 0.0307(12) Uani 1 1 d . . . . .
C5 C 0.3509(6) 0.6822(7) 0.0757(2) 0.0504(15) Uani 1 1 d . . . . .
H5 H 0.351448 0.735777 0.037827 0.060 Uiso 1 1 calc R U . . .
C19 C 0.9445(6) 0.5875(7) 0.2805(3) 0.0454(15) Uani 1 1 d . . . . .
H19 H 1.055144 0.543165 0.274224 0.054 Uiso 1 1 calc R U . . .
C14 C 0.6134(7) 0.5703(6) 0.4540(3) 0.0466(14) Uani 1 1 d . . . . .
H14 H 0.498741 0.555330 0.456533 0.056 Uiso 1 1 calc R U . . .
C18 C 0.8581(7) 0.6201(6) 0.3921(2) 0.0403(13) Uani 1 1 d . . . . .
C13 C 0.6850(6) 0.5929(6) 0.3946(2) 0.0373(13) Uani 1 1 d . . . . .
C2 C 0.3447(6) 0.5215(6) 0.1888(2) 0.0374(13) Uani 1 1 d . . . . .
H2 H 0.341268 0.466605 0.226327 0.045 Uiso 1 1 calc R U . . .
C16 C 0.8774(7) 0.5915(7) 0.5055(3) 0.0582(16) Uani 1 1 d . . . . .
H16 H 0.942067 0.588872 0.542191 0.070 Uiso 1 1 calc R U . . .
C17 C 0.9514(7) 0.6174(7) 0.4476(3) 0.0511(16) Uani 1 1 d . . . . .
H17 H 1.066012 0.633474 0.445592 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2125(6) 0.5173(7) 0.1478(3) 0.0456(15) Uani 1 1 d . . . . .
H3 H 0.119677 0.459287 0.157503 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2156(7) 0.5995(8) 0.0913(3) 0.0553(17) Uani 1 1 d . . . . .
H4 H 0.123859 0.597352 0.064163 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.904(4) . ?
O2 C19 1.426(6) . ?
O2 C18 1.383(6) . ?
O1 C9 1.385(5) . ?
O1 C19 1.433(7) . ?
C12 C11 1.328(6) . ?
C12 C13 1.482(7) . ?
C6 C7 1.407(7) . ?
C6 C1 1.416(7) . ?
C6 C5 1.417(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.365(7) . ?
C11 C20 1.512(6) . ?
C11 C10 1.478(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(7) . ?
C9 C10 1.384(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.492(7) . ?
C10 C1 1.422(6) . ?
C15 H15 0.9300 . ?
C15 C14 1.379(7) . ?
C15 C16 1.388(7) . ?
C1 C2 1.414(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.354(8) . ?
C19 H19 0.9800 . ?
C14 H14 0.9300 . ?
C14 C13 1.387(7) . ?
C18 C13 1.409(7) . ?
C18 C17 1.385(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(7) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.400(8) . ?
C4 H4 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
C18 O2 C19 122.7(4) . . ?
C9 O1 C19 120.5(4) . . ?
C11 C12 Br1 120.9(4) . . ?
C11 C12 C13 122.8(4) . . ?
C13 C12 Br1 115.7(4) . . ?
C7 C6 C1 119.3(4) . . ?
C7 C6 C5 121.8(5) . . ?
C1 C6 C5 118.8(5) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(5) . . ?
C8 C7 H7 119.2 . . ?
C12 C11 C20 118.1(4) . . ?
C12 C11 C10 127.5(5) . . ?
C10 C11 C20 109.0(4) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 118.9(5) . . ?
C9 C8 H8 120.5 . . ?
O1 C9 C8 115.2(5) . . ?
C10 C9 O1 122.6(5) . . ?
C10 C9 C8 122.3(5) . . ?
C11 C20 H20A 111.0 . . ?
C11 C20 H20B 111.0 . . ?
H20A C20 H20B 109.0 . . ?
C19 C20 C11 104.0(5) . . ?
C19 C20 H20A 111.0 . . ?
C19 C20 H20B 111.0 . . ?
C9 C10 C11 111.4(4) . . ?
C9 C10 C1 118.9(4) . . ?
C1 C10 C11 129.8(5) . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.8(6) . . ?
C16 C15 H15 120.6 . . ?
C6 C1 C10 118.9(4) . . ?
C2 C1 C6 118.9(4) . . ?
C2 C1 C10 122.1(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.7 . . ?
O2 C19 O1 106.5(5) . . ?
O2 C19 C20 111.4(4) . . ?
O2 C19 H19 108.9 . . ?
O1 C19 C20 112.1(4) . . ?
O1 C19 H19 108.9 . . ?
C20 C19 H19 108.9 . . ?
C15 C14 H14 118.8 . . ?
C15 C14 C13 122.4(6) . . ?
C13 C14 H14 118.8 . . ?
O2 C18 C13 125.0(5) . . ?
O2 C18 C17 114.7(5) . . ?
C17 C18 C13 119.8(5) . . ?
C14 C13 C12 124.2(5) . . ?
C14 C13 C18 117.7(5) . . ?
C18 C13 C12 118.0(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.1(5) . . ?
C17 C16 H16 119.9 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 121.0(5) . . ?
C16 C17 H17 119.5 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?

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
Br1 C12 C11 C20 -179.9(4) . . . . ?
Br1 C12 C11 C10 29.2(7) . . . . ?
Br1 C12 C13 C14 41.4(7) . . . . ?
Br1 C12 C13 C18 -135.6(4) . . . . ?
O2 C18 C13 C12 8.1(8) . . . . ?
O2 C18 C13 C14 -169.0(5) . . . . ?
O2 C18 C17 C16 171.2(6) . . . . ?
O1 C9 C10 C11 1.3(8) . . . . ?
O1 C9 C10 C1 -177.7(5) . . . . ?
C12 C11 C20 C19 -83.9(6) . . . . ?
C12 C11 C10 C9 105.5(6) . . . . ?
C12 C11 C10 C1 -75.5(8) . . . . ?
C6 C7 C8 C9 -1.3(9) . . . . ?
C6 C1 C2 C3 -1.9(7) . . . . ?
C6 C5 C4 C3 -0.4(10) . . . . ?
C7 C6 C1 C10 2.7(8) . . . . ?
C7 C6 C1 C2 -174.4(5) . . . . ?
C7 C6 C5 C4 175.4(5) . . . . ?
C7 C8 C9 O1 -179.5(5) . . . . ?
C7 C8 C9 C10 -0.6(9) . . . . ?
C11 C12 C13 C14 -146.8(5) . . . . ?
C11 C12 C13 C18 36.2(8) . . . . ?
C11 C20 C19 O2 69.1(5) . . . . ?
C11 C20 C19 O1 -50.1(5) . . . . ?
C11 C10 C1 C6 176.7(5) . . . . ?
C11 C10 C1 C2 -6.3(8) . . . . ?
C8 C9 C10 C11 -177.5(5) . . . . ?
C8 C9 C10 C1 3.4(8) . . . . ?
C9 O1 C19 O2 -114.6(5) . . . . ?
C9 O1 C19 C20 7.5(7) . . . . ?
C9 C10 C1 C6 -4.4(7) . . . . ?
C9 C10 C1 C2 172.6(5) . . . . ?
C20 C11 C10 C9 -47.5(6) . . . . ?
C20 C11 C10 C1 131.4(5) . . . . ?
C10 C11 C20 C19 72.1(5) . . . . ?
C10 C1 C2 C3 -178.9(5) . . . . ?
C15 C14 C13 C12 -179.0(5) . . . . ?
C15 C14 C13 C18 -2.0(9) . . . . ?
C15 C16 C17 C18 -0.8(10) . . . . ?
C1 C6 C7 C8 0.2(9) . . . . ?
C1 C6 C5 C4 -1.6(9) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C5 C6 C7 C8 -176.9(6) . . . . ?
C5 C6 C1 C10 179.8(5) . . . . ?
C5 C6 C1 C2 2.8(8) . . . . ?
C19 O2 C18 C13 -58.2(7) . . . . ?
C19 O2 C18 C17 129.8(5) . . . . ?
C19 O1 C9 C8 -160.9(5) . . . . ?
C19 O1 C9 C10 20.2(8) . . . . ?
C14 C15 C16 C17 1.5(9) . . . . ?
C18 O2 C19 O1 133.9(4) . . . . ?
C18 O2 C19 C20 11.4(7) . . . . ?
C13 C12 C11 C20 8.8(7) . . . . ?
C13 C12 C11 C10 -142.2(5) . . . . ?
C13 C18 C17 C16 -1.3(9) . . . . ?
C2 C3 C4 C5 1.3(9) . . . . ?
C16 C15 C14 C13 0.0(9) . . . . ?
C17 C18 C13 C12 179.8(5) . . . . ?
C17 C18 C13 C14 2.6(8) . . . . ?

_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_20220117-zzx-lk-467-r
_database_code_depnum_ccdc_archive 'CCDC 2151484'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Br O'
_chemical_formula_sum            'C21 H15 Br O'
_chemical_formula_weight         363.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   15.1076(5)
_cell_length_b                   10.0376(5)
_cell_length_c                   20.6682(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3134.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4960
_cell_measurement_theta_min      3.8080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11690
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.094
_diffrn_reflns_theta_min         3.375
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  86.00   1.00   12.50    --   18.74  19.00  30.00  103
  2  ω     45.00  83.00   1.00   12.50    --   18.74 178.00 -60.00   38
  3  ω    -47.00 -16.00   1.00   12.50    --  -18.85  77.00-180.00   31
  4  ω      8.00  33.00   1.00   12.50    --  -18.85  77.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0140502000
_diffrn_orient_matrix_UB_12      -0.0218395000
_diffrn_orient_matrix_UB_13      -0.0309670000
_diffrn_orient_matrix_UB_21      -0.0442929000
_diffrn_orient_matrix_UB_22      -0.0168731000
_diffrn_orient_matrix_UB_23      -0.0079161000
_diffrn_orient_matrix_UB_31      -0.0067470000
_diffrn_orient_matrix_UB_32      0.0650856000
_diffrn_orient_matrix_UB_33      -0.0124443000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2444
_reflns_number_total             3707
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.038
_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)+(0.0301P)²+1.0344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0899
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C13(H13), C1(H1), C16(H16), C17(H17), C14(H14), C4(H4),
 C2(H2), C3(H3)
;
_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 0.60912(2) 0.33335(3) 0.48450(2) 0.05109(12) Uani 1 1 d . . . . .
O1 O 0.86549(12) 0.25389(18) 0.62760(10) 0.0457(5) Uani 1 1 d . . . . .
C9 C 0.74532(15) 0.4246(2) 0.56961(13) 0.0308(6) Uani 1 1 d . . . . .
C11 C 0.77744(17) 0.4425(2) 0.45335(14) 0.0362(6) Uani 1 1 d . . . . .
C20 C 0.63060(17) 0.3495(2) 0.65620(13) 0.0331(6) Uani 1 1 d . . . . .
C21 C 0.71569(16) 0.3453(2) 0.62608(13) 0.0325(6) Uani 1 1 d . . . . .
C19 C 0.56391(17) 0.4394(3) 0.63615(14) 0.0379(6) Uani 1 1 d . . . . .
H19 H 0.575006 0.497448 0.602021 0.045 Uiso 1 1 calc R U . . .
C10 C 0.71718(17) 0.4185(2) 0.50871(14) 0.0341(6) Uani 1 1 d . . . . .
C5 C 0.85738(18) 0.3713(3) 0.45437(14) 0.0385(7) Uani 1 1 d . . . . .
C12 C 0.78059(18) 0.2629(3) 0.65121(13) 0.0365(6) Uani 1 1 d . . . . .
C6 C 0.87732(17) 0.2759(3) 0.50966(14) 0.0402(7) Uani 1 1 d . . . . .
H6A H 0.929791 0.224987 0.498726 0.048 Uiso 1 1 calc R U . . .
H6B H 0.828505 0.213703 0.513649 0.048 Uiso 1 1 calc R U . . .
C15 C 0.61255(19) 0.2648(3) 0.70979(14) 0.0378(6) Uani 1 1 d . . . . .
C8 C 0.83936(16) 0.4713(2) 0.58061(14) 0.0376(7) Uani 1 1 d . . . . .
H8A H 0.845893 0.511995 0.622912 0.045 Uiso 1 1 calc R U . . .
H8B H 0.857386 0.534647 0.547702 0.045 Uiso 1 1 calc R U . . .
C18 C 0.48342(18) 0.4422(3) 0.66629(15) 0.0451(7) Uani 1 1 d . . . . .
H18 H 0.440268 0.501586 0.652225 0.054 Uiso 1 1 calc R U . . .
C7 C 0.89225(17) 0.3435(3) 0.57585(15) 0.0408(7) Uani 1 1 d . . . . .
H7 H 0.955290 0.364223 0.580703 0.049 Uiso 1 1 calc R U . . .
C13 C 0.7627(2) 0.1804(3) 0.70520(14) 0.0440(7) Uani 1 1 d . . . . .
H13 H 0.806998 0.125966 0.721889 0.053 Uiso 1 1 calc R U . . .
C1 C 0.7577(2) 0.5277(3) 0.40242(15) 0.0469(7) Uani 1 1 d . . . . .
H1 H 0.704319 0.573872 0.401831 0.056 Uiso 1 1 calc R U . . .
C16 C 0.5279(2) 0.2708(3) 0.73930(15) 0.0492(8) Uani 1 1 d . . . . .
H16 H 0.515374 0.214653 0.773889 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4651(2) 0.3562(3) 0.71838(15) 0.0500(8) Uani 1 1 d . . . . .
H17 H 0.409883 0.358153 0.738295 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6812(2) 0.1808(3) 0.73260(14) 0.0455(7) Uani 1 1 d . . . . .
H14 H 0.670052 0.124307 0.767321 0.055 Uiso 1 1 calc R U . . .
C4 C 0.9165(2) 0.3880(3) 0.40347(16) 0.0509(8) Uani 1 1 d . . . . .
H4 H 0.969680 0.341311 0.403326 0.061 Uiso 1 1 calc R U . . .
C2 C 0.8180(2) 0.5435(3) 0.35246(16) 0.0576(9) Uani 1 1 d . . . . .
H2 H 0.805473 0.601276 0.318476 0.069 Uiso 1 1 calc R U . . .
C3 C 0.8969(2) 0.4734(3) 0.35317(17) 0.0584(9) Uani 1 1 d . . . . .
H3 H 0.936983 0.483931 0.319424 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
Br1 C10 1.909(3) . ?
O1 C12 1.375(3) . ?
O1 C7 1.455(3) . ?
C9 C21 1.482(3) . ?
C9 C10 1.330(4) . ?
C9 C8 1.513(3) . ?
C11 C10 1.482(4) . ?
C11 C5 1.403(4) . ?
C11 C1 1.389(4) . ?
C20 C21 1.429(3) . ?
C20 C19 1.415(3) . ?
C20 C15 1.422(4) . ?
C21 C12 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.367(4) . ?
C5 C6 1.521(4) . ?
C5 C4 1.390(4) . ?
C12 C13 1.415(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.543(4) . ?
C15 C16 1.418(4) . ?
C15 C14 1.418(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.515(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.407(4) . ?
C7 H7 0.9800 . ?
C13 H13 0.9300 . ?
C13 C14 1.355(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.350(4) . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 H3 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
C12 O1 C7 118.6(2) . . ?
C21 C9 C8 109.4(2) . . ?
C10 C9 C21 128.6(2) . . ?
C10 C9 C8 117.2(2) . . ?
C5 C11 C10 115.7(2) . . ?
C1 C11 C10 123.6(2) . . ?
C1 C11 C5 120.7(3) . . ?
C19 C20 C21 122.1(2) . . ?
C19 C20 C15 118.2(2) . . ?
C15 C20 C21 119.6(2) . . ?
C20 C21 C9 126.8(2) . . ?
C12 C21 C9 113.7(2) . . ?
C12 C21 C20 119.4(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C9 C10 Br1 122.8(2) . . ?
C9 C10 C11 121.8(2) . . ?
C11 C10 Br1 113.3(2) . . ?
C11 C5 C6 120.1(2) . . ?
C4 C5 C11 118.7(3) . . ?
C4 C5 C6 121.1(3) . . ?
O1 C12 C21 124.5(2) . . ?
O1 C12 C13 114.8(2) . . ?
C21 C12 C13 120.7(3) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C5 C6 C7 114.7(2) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C16 C15 C20 118.8(3) . . ?
C14 C15 C20 118.3(3) . . ?
C14 C15 C16 122.8(3) . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C9 C8 C7 102.88(19) . . ?
H8A C8 H8B 109.1 . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C19 C18 H18 119.6 . . ?
C19 C18 C17 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
O1 C7 C6 109.8(2) . . ?
O1 C7 C8 109.2(2) . . ?
O1 C7 H7 109.0 . . ?
C6 C7 H7 109.0 . . ?
C8 C7 C6 110.6(2) . . ?
C8 C7 H7 109.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C11 C1 H1 120.2 . . ?
C2 C1 C11 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.1 . . ?
C15 C14 H14 119.1 . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 H14 119.1 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C13 C14 -179.9(2) . . . . ?
C9 C21 C12 O1 0.6(4) . . . . ?
C9 C21 C12 C13 -179.9(2) . . . . ?
C9 C8 C7 O1 -63.2(3) . . . . ?
C9 C8 C7 C6 57.9(3) . . . . ?
C11 C5 C6 C7 -68.0(3) . . . . ?
C11 C5 C4 C3 0.3(4) . . . . ?
C11 C1 C2 C3 0.8(5) . . . . ?
C20 C21 C12 O1 -177.8(2) . . . . ?
C20 C21 C12 C13 1.7(4) . . . . ?
C20 C19 C18 C17 0.5(4) . . . . ?
C20 C15 C16 C17 -1.1(4) . . . . ?
C20 C15 C14 C13 0.7(4) . . . . ?
C21 C9 C10 Br1 16.2(4) . . . . ?
C21 C9 C10 C11 -146.3(3) . . . . ?
C21 C9 C8 C7 69.7(3) . . . . ?
C21 C20 C19 C18 -179.3(2) . . . . ?
C21 C20 C15 C16 179.7(2) . . . . ?
C21 C20 C15 C14 1.5(4) . . . . ?
C21 C12 C13 C14 0.5(4) . . . . ?
C19 C20 C21 C9 -3.5(4) . . . . ?
C19 C20 C21 C12 174.7(2) . . . . ?
C19 C20 C15 C16 2.2(4) . . . . ?
C19 C20 C15 C14 -176.0(2) . . . . ?
C19 C18 C17 C16 0.7(4) . . . . ?
C10 C9 C21 C20 -66.7(4) . . . . ?
C10 C9 C21 C12 115.1(3) . . . . ?
C10 C9 C8 C7 -87.8(3) . . . . ?
C10 C11 C5 C6 0.5(4) . . . . ?
C10 C11 C5 C4 179.2(2) . . . . ?
C10 C11 C1 C2 -179.7(3) . . . . ?
C5 C11 C10 Br1 -114.3(2) . . . . ?
C5 C11 C10 C9 49.7(4) . . . . ?
C5 C11 C1 C2 -0.7(4) . . . . ?
C5 C6 C7 O1 150.6(2) . . . . ?
C5 C6 C7 C8 30.0(3) . . . . ?
C5 C4 C3 C2 -0.1(5) . . . . ?
C12 O1 C7 C6 -93.1(3) . . . . ?
C12 O1 C7 C8 28.4(3) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C6 C5 C4 C3 179.0(3) . . . . ?
C15 C20 C21 C9 179.1(2) . . . . ?
C15 C20 C21 C12 -2.7(4) . . . . ?
C15 C20 C19 C18 -1.9(4) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C8 C9 C21 C20 139.1(2) . . . . ?
C8 C9 C21 C12 -39.1(3) . . . . ?
C8 C9 C10 Br1 168.75(17) . . . . ?
C8 C9 C10 C11 6.3(4) . . . . ?
C7 O1 C12 C21 5.0(4) . . . . ?
C7 O1 C12 C13 -174.6(2) . . . . ?
C1 C11 C10 Br1 64.8(3) . . . . ?
C1 C11 C10 C9 -131.2(3) . . . . ?
C1 C11 C5 C6 -178.6(3) . . . . ?
C1 C11 C5 C4 0.2(4) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C16 C15 C14 C13 -177.4(3) . . . . ?
C14 C15 C16 C17 176.9(3) . . . . ?
C4 C5 C6 C7 113.3(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 1.070
_oxdiff_exptl_absorpt_empirical_full_min 0.939
####################################################################### 
# 
# 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_20211117-zzx-968
_database_code_depnum_ccdc_archive 'CCDC 2151482'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2021-11-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Br O2'
_chemical_formula_sum            'C21 H15 Br O2'
_chemical_formula_weight         379.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H15 Br O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.8697(4)
_cell_length_b                   22.6968(7)
_cell_length_c                   8.9630(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.336(6)
_cell_angle_gamma                90
_cell_volume                     1644.05(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8520
_cell_measurement_theta_min      4.2130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13047
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.012
_diffrn_reflns_theta_min         3.591
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  95.00   1.00    4.00    --   18.74-178.00 -90.00   57
  2  ω    -12.00  91.00   1.00    4.00    --   18.74  19.00-120.00  103
  3  ω     48.00  83.00   1.00    4.00    --   18.74  57.00-120.00   35
  4  ω     46.00  72.00   1.00    4.00    --   18.74 178.00 -30.00   26
  5  ω    -64.00  25.00   1.00    4.00    --  -18.85 -19.00 -30.00   89
  6  ω    -41.00  36.00   1.00    4.00    --  -18.85  38.00 120.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0574829000
_diffrn_orient_matrix_UB_12      0.0048946000
_diffrn_orient_matrix_UB_13      -0.0819763000
_diffrn_orient_matrix_UB_21      0.0469931000
_diffrn_orient_matrix_UB_22      0.0245828000
_diffrn_orient_matrix_UB_23      -0.0051090000
_diffrn_orient_matrix_UB_31      0.0468252000
_diffrn_orient_matrix_UB_32      -0.0186635000
_diffrn_orient_matrix_UB_33      -0.0282931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                5045
_reflns_number_total             7480
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7480
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.010
_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)+(0.0257P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0867
_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:
 C13(H13), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C14(H14A,H14B), C35(H35A,H35B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C2(H2), C23(H23), C24(H24), C28(H28), C19(H19), C37(H37), C7(H7),
 C40(H40), C25(H25), C8(H8), C38(H38), C26(H26), C5(H5), C39(H39), C16(H16),
 C3(H3), C18(H18), C17(H17), C4(H4)
;
_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
Br2 Br 0.94095(9) 0.72651(3) 0.65062(9) 0.0649(2) Uani 1 1 d . . . . .
Br1 Br -0.15153(8) 0.36277(3) 0.74383(9) 0.0656(2) Uani 1 1 d . . . . .
O1 O 0.0977(6) 0.27525(18) 0.9404(6) 0.0635(13) Uani 1 1 d . . . . .
O2 O 0.2835(7) 0.4419(2) 0.6904(6) 0.0656(14) Uani 1 1 d . . . . .
O4 O 0.5786(6) 0.62980(18) 0.7940(6) 0.0557(12) Uani 1 1 d . . . . .
O3 O 1.0046(6) 0.6053(2) 0.5634(6) 0.0679(14) Uani 1 1 d . . . . .
C11 C 0.0904(6) 0.3685(3) 0.8086(6) 0.0376(12) Uani 1 1 d . . . . .
C22 C 0.5565(7) 0.6804(2) 0.3940(7) 0.0372(13) Uani 1 1 d . . . . .
C27 C 0.3845(8) 0.6917(2) 0.3174(8) 0.0466(16) Uani 1 1 d . . . . .
C29 C 0.3575(8) 0.6659(3) 0.5638(9) 0.0509(17) Uani 1 1 d . . . . .
H29 H 0.292086 0.660171 0.621223 0.061 Uiso 1 1 calc R U . . .
C30 C 0.5278(8) 0.6536(2) 0.6400(8) 0.0405(14) Uani 1 1 d . . . . .
C2 C 0.0629(8) 0.4209(3) 1.1075(7) 0.0483(16) Uani 1 1 d . . . . .
H2 H 0.026023 0.382608 1.076451 0.058 Uiso 1 1 calc R U . . .
C10 C 0.1525(7) 0.4289(2) 0.8781(7) 0.0374(14) Uani 1 1 d . . . . .
C32 C 0.8155(7) 0.6545(2) 0.6544(7) 0.0396(14) Uani 1 1 d . . . . .
C23 C 0.6448(9) 0.6822(2) 0.2932(8) 0.0492(16) Uani 1 1 d . . . . .
H23 H 0.758534 0.675816 0.340243 0.059 Uiso 1 1 calc R U . . .
C1 C 0.1343(7) 0.4524(2) 1.0184(7) 0.0405(14) Uani 1 1 d . . . . .
C41 C 0.7665(7) 0.5509(2) 0.5323(8) 0.0449(16) Uani 1 1 d . . . . .
C24 C 0.5672(11) 0.6930(3) 0.1286(9) 0.061(2) Uani 1 1 d . . . . .
H24 H 0.627582 0.692168 0.064929 0.073 Uiso 1 1 calc R U . . .
C28 C 0.2885(8) 0.6856(3) 0.4095(9) 0.0551(18) Uani 1 1 d . . . . .
H28 H 0.176748 0.695299 0.362417 0.066 Uiso 1 1 calc R U . . .
C33 C 0.8612(8) 0.6433(3) 0.8366(7) 0.0504(17) Uani 1 1 d . . . . .
H33A H 0.970756 0.625978 0.886264 0.060 Uiso 1 1 calc R U . . .
H33B H 0.864254 0.680575 0.890950 0.060 Uiso 1 1 calc R U . . .
C31 C 0.6312(7) 0.6643(2) 0.5634(7) 0.0336(13) Uani 1 1 d . . . . .
C13 C 0.2745(9) 0.3801(3) 0.6610(8) 0.0556(18) Uani 1 1 d . . . . .
H13 H 0.273436 0.374836 0.552087 0.067 Uiso 1 1 calc R U . . .
C9 C 0.2391(8) 0.4612(3) 0.8099(8) 0.0494(17) Uani 1 1 d . . . . .
C19 C 0.4104(10) 0.3088(2) 1.1892(8) 0.0553(18) Uani 1 1 d . . . . .
H19 H 0.336115 0.295546 1.230711 0.066 Uiso 1 1 calc R U . . .
C36 C 0.6872(8) 0.5269(2) 0.6233(9) 0.0460(16) Uani 1 1 d . . . . .
C15 C 0.4669(8) 0.3422(2) 0.9593(8) 0.0487(16) Uani 1 1 d . . . . .
C20 C 0.3554(7) 0.3234(2) 1.0238(8) 0.0413(14) Uani 1 1 d . . . . .
C37 C 0.5709(8) 0.4827(3) 0.5514(10) 0.061(2) Uani 1 1 d . . . . .
H37 H 0.515397 0.466282 0.609585 0.074 Uiso 1 1 calc R U . . .
C7 C 0.2644(9) 0.5430(3) 0.9861(11) 0.072(2) Uani 1 1 d . . . . .
H7 H 0.297149 0.581640 1.017964 0.086 Uiso 1 1 calc R U . . .
C40 C 0.7314(9) 0.5294(3) 0.3752(9) 0.0611(19) Uani 1 1 d . . . . .
H40 H 0.784935 0.545470 0.314766 0.073 Uiso 1 1 calc R U . . .
C25 C 0.3988(12) 0.7052(3) 0.0562(10) 0.071(2) Uani 1 1 d . . . . .
H25 H 0.347353 0.713203 -0.055401 0.086 Uiso 1 1 calc R U . . .
C21 C 0.1735(7) 0.3173(2) 0.9255(7) 0.0403(14) Uani 1 1 d . . . . .
C6 C 0.1896(8) 0.5110(3) 1.0698(9) 0.0518(17) Uani 1 1 d . . . . .
C8 C 0.2906(9) 0.5200(3) 0.8615(12) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.342115 0.542262 0.808832 0.085 Uiso 1 1 calc R U . . .
C38 C 0.5364(10) 0.4627(3) 0.3949(13) 0.081(3) Uani 1 1 d . . . . .
H38 H 0.456073 0.433938 0.347776 0.097 Uiso 1 1 calc R U . . .
C14 C 0.4279(9) 0.3482(3) 0.7806(9) 0.0618(19) Uani 1 1 d . . . . .
H14A H 0.423639 0.308593 0.738408 0.074 Uiso 1 1 calc R U . . .
H14B H 0.522472 0.367349 0.773379 0.074 Uiso 1 1 calc R U . . .
C34 C 0.7396(9) 0.6031(3) 0.8610(8) 0.0540(17) Uani 1 1 d . . . . .
H34 H 0.772804 0.600780 0.979501 0.065 Uiso 1 1 calc R U . . .
C26 C 0.3096(10) 0.7055(2) 0.1470(9) 0.064(2) Uani 1 1 d . . . . .
H26 H 0.197670 0.714965 0.097849 0.076 Uiso 1 1 calc R U . . .
C35 C 0.7328(9) 0.5399(3) 0.8016(9) 0.0593(19) Uani 1 1 d . . . . .
H35A H 0.840782 0.522540 0.863193 0.071 Uiso 1 1 calc R U . . .
H35B H 0.654948 0.518785 0.832564 0.071 Uiso 1 1 calc R U . . .
C42 C 0.8769(8) 0.6028(2) 0.5830(8) 0.0451(15) Uani 1 1 d . . . . .
C5 C 0.1691(10) 0.5343(3) 1.2068(10) 0.073(2) Uani 1 1 d . . . . .
H5 H 0.204297 0.572553 1.239961 0.088 Uiso 1 1 calc R U . . .
C12 C 0.1102(8) 0.3585(3) 0.6497(7) 0.0575(16) Uani 1 1 d . . . . .
H12A H 0.099973 0.316704 0.624292 0.069 Uiso 1 1 calc R U . . .
H12B H 0.022296 0.378822 0.561151 0.069 Uiso 1 1 calc R U . . .
C39 C 0.6195(11) 0.4851(3) 0.3096(11) 0.076(2) Uani 1 1 d . . . . .
H39 H 0.600144 0.470132 0.206675 0.091 Uiso 1 1 calc R U . . .
C16 C 0.6313(9) 0.3476(3) 1.0684(12) 0.073(2) Uani 1 1 d . . . . .
H16 H 0.707038 0.361258 1.029204 0.087 Uiso 1 1 calc R U . . .
C3 C 0.0461(8) 0.4458(3) 1.2411(9) 0.0634(19) Uani 1 1 d . . . . .
H3 H -0.001844 0.424306 1.298455 0.076 Uiso 1 1 calc R U . . .
C18 C 0.5775(12) 0.3142(3) 1.2910(10) 0.078(3) Uani 1 1 d . . . . .
H18 H 0.615083 0.304503 1.401262 0.093 Uiso 1 1 calc R U . . .
C17 C 0.6874(10) 0.3338(3) 1.2309(13) 0.085(3) Uani 1 1 d . . . . .
H17 H 0.799041 0.337673 1.299761 0.102 Uiso 1 1 calc R U . . .
C4 C 0.1015(10) 0.5035(4) 1.2900(11) 0.082(3) Uani 1 1 d . . . . .
H4 H 0.090939 0.520192 1.379999 0.099 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
Br2 C32 1.984(5) . ?
Br1 C11 1.983(5) . ?
O1 C21 1.206(6) . ?
O2 C13 1.424(7) . ?
O2 C9 1.356(7) . ?
O4 C30 1.374(7) . ?
O4 C34 1.436(8) . ?
O3 C42 1.217(7) . ?
C11 C10 1.513(8) . ?
C11 C21 1.535(8) . ?
C11 C12 1.523(7) . ?
C22 C27 1.414(8) . ?
C22 C23 1.420(8) . ?
C22 C31 1.432(7) . ?
C27 C28 1.416(9) . ?
C27 C26 1.428(9) . ?
C29 H29 0.9300 . ?
C29 C30 1.405(8) . ?
C29 C28 1.338(9) . ?
C30 C31 1.375(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.403(8) . ?
C2 C3 1.386(8) . ?
C10 C1 1.435(8) . ?
C10 C9 1.375(8) . ?
C32 C33 1.533(8) . ?
C32 C31 1.512(8) . ?
C32 C42 1.541(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.368(9) . ?
C1 C6 1.427(8) . ?
C41 C36 1.390(9) . ?
C41 C40 1.399(9) . ?
C41 C42 1.478(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(11) . ?
C28 H28 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.496(9) . ?
C13 H13 0.9800 . ?
C13 C14 1.524(9) . ?
C13 C12 1.501(8) . ?
C9 C8 1.424(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(9) . ?
C19 C18 1.389(10) . ?
C36 C37 1.392(9) . ?
C36 C35 1.507(9) . ?
C15 C20 1.401(8) . ?
C15 C14 1.500(9) . ?
C15 C16 1.386(9) . ?
C20 C21 1.492(8) . ?
C37 H37 0.9300 . ?
C37 C38 1.383(11) . ?
C7 H7 0.9300 . ?
C7 C6 1.394(10) . ?
C7 C8 1.338(10) . ?
C40 H40 0.9300 . ?
C40 C39 1.364(10) . ?
C25 H25 0.9300 . ?
C25 C26 1.349(10) . ?
C6 C5 1.415(10) . ?
C8 H8 0.9300 . ?
C38 H38 0.9300 . ?
C38 C39 1.360(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C34 H34 0.9800 . ?
C34 C35 1.524(9) . ?
C26 H26 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.331(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C39 H39 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.367(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.368(11) . ?
C17 H17 0.9300 . ?
C4 H4 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
C9 O2 C13 116.9(5) . . ?
C30 O4 C34 116.4(4) . . ?
C10 C11 Br1 110.3(4) . . ?
C10 C11 C21 114.5(5) . . ?
C10 C11 C12 111.0(5) . . ?
C21 C11 Br1 107.9(4) . . ?
C12 C11 Br1 104.1(4) . . ?
C12 C11 C21 108.5(5) . . ?
C27 C22 C23 117.0(6) . . ?
C27 C22 C31 119.8(5) . . ?
C23 C22 C31 123.1(5) . . ?
C22 C27 C28 119.1(6) . . ?
C22 C27 C26 119.5(7) . . ?
C28 C27 C26 121.2(7) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.7(6) . . ?
O4 C30 C29 114.1(5) . . ?
O4 C30 C31 124.1(6) . . ?
C31 C30 C29 121.8(6) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C3 C2 C1 121.2(6) . . ?
C1 C10 C11 123.0(5) . . ?
C9 C10 C11 118.4(5) . . ?
C9 C10 C1 118.5(5) . . ?
C33 C32 Br2 104.5(4) . . ?
C33 C32 C42 109.4(5) . . ?
C31 C32 Br2 111.1(4) . . ?
C31 C32 C33 110.5(5) . . ?
C31 C32 C42 112.1(5) . . ?
C42 C32 Br2 108.9(4) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.8(7) . . ?
C24 C23 H23 119.1 . . ?
C2 C1 C10 123.4(5) . . ?
C2 C1 C6 117.8(6) . . ?
C6 C1 C10 118.8(6) . . ?
C36 C41 C40 119.8(6) . . ?
C36 C41 C42 124.3(6) . . ?
C40 C41 C42 115.6(6) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.4(7) . . ?
C25 C24 H24 119.8 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(6) . . ?
C29 C28 H28 119.8 . . ?
C32 C33 H33A 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?
C34 C33 C32 111.5(5) . . ?
C34 C33 H33A 109.3 . . ?
C34 C33 H33B 109.3 . . ?
C22 C31 C32 122.3(5) . . ?
C30 C31 C22 117.5(5) . . ?
C30 C31 C32 120.0(5) . . ?
O2 C13 H13 106.4 . . ?
O2 C13 C14 111.9(6) . . ?
O2 C13 C12 108.3(5) . . ?
C14 C13 H13 106.4 . . ?
C12 C13 H13 106.4 . . ?
C12 C13 C14 116.9(5) . . ?
O2 C9 C10 125.2(6) . . ?
O2 C9 C8 113.6(6) . . ?
C10 C9 C8 121.2(6) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(7) . . ?
C41 C36 C37 117.9(7) . . ?
C41 C36 C35 124.5(6) . . ?
C37 C36 C35 117.2(6) . . ?
C20 C15 C14 125.2(6) . . ?
C16 C15 C20 116.9(7) . . ?
C16 C15 C14 117.3(7) . . ?
C19 C20 C15 120.9(6) . . ?
C19 C20 C21 115.1(6) . . ?
C15 C20 C21 124.0(6) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 C36 121.2(7) . . ?
C38 C37 H37 119.4 . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C8 C7 C6 122.0(7) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 C41 120.8(7) . . ?
C39 C40 H40 119.6 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.3(7) . . ?
C26 C25 H25 119.9 . . ?
O1 C21 C11 122.8(5) . . ?
O1 C21 C20 121.6(5) . . ?
C20 C21 C11 115.5(5) . . ?
C7 C6 C1 119.3(6) . . ?
C7 C6 C5 122.1(7) . . ?
C5 C6 C1 118.6(7) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 C9 119.7(7) . . ?
C7 C8 H8 120.2 . . ?
C37 C38 H38 119.9 . . ?
C39 C38 C37 120.2(7) . . ?
C39 C38 H38 119.9 . . ?
C13 C14 H14A 106.6 . . ?
C13 C14 H14B 106.6 . . ?
C15 C14 C13 122.7(5) . . ?
C15 C14 H14A 106.6 . . ?
C15 C14 H14B 106.6 . . ?
H14A C14 H14B 106.6 . . ?
O4 C34 C33 109.5(5) . . ?
O4 C34 H34 106.2 . . ?
O4 C34 C35 111.2(6) . . ?
C33 C34 H34 106.2 . . ?
C33 C34 C35 116.8(6) . . ?
C35 C34 H34 106.2 . . ?
C27 C26 H26 119.5 . . ?
C25 C26 C27 121.0(7) . . ?
C25 C26 H26 119.5 . . ?
C36 C35 C34 120.6(5) . . ?
C36 C35 H35A 107.2 . . ?
C36 C35 H35B 107.2 . . ?
C34 C35 H35A 107.2 . . ?
C34 C35 H35B 107.2 . . ?
H35A C35 H35B 106.8 . . ?
O3 C42 C32 122.2(6) . . ?
O3 C42 C41 122.1(6) . . ?
C41 C42 C32 115.6(5) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 C6 122.6(7) . . ?
C4 C5 H5 118.7 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 C11 111.7(5) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C40 C39 H39 120.0 . . ?
C38 C39 C40 119.9(8) . . ?
C38 C39 H39 120.0 . . ?
C15 C16 H16 118.4 . . ?
C17 C16 C15 123.1(8) . . ?
C17 C16 H16 118.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(7) . . ?
C4 C3 H3 119.9 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 C19 120.7(8) . . ?
C17 C18 H18 119.6 . . ?
C16 C17 C18 119.2(8) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C5 C4 C3 119.6(7) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 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
Br2 C32 C33 C34 161.8(4) . . . . ?
Br2 C32 C31 C22 59.3(6) . . . . ?
Br2 C32 C31 C30 -125.3(5) . . . . ?
Br2 C32 C42 O3 14.2(7) . . . . ?
Br2 C32 C42 C41 -162.9(4) . . . . ?
Br1 C11 C10 C1 58.9(6) . . . . ?
Br1 C11 C10 C9 -125.2(5) . . . . ?
Br1 C11 C21 O1 15.2(7) . . . . ?
Br1 C11 C21 C20 -163.4(4) . . . . ?
Br1 C11 C12 C13 161.5(5) . . . . ?
O2 C13 C14 C15 69.0(8) . . . . ?
O2 C13 C12 C11 -61.7(7) . . . . ?
O2 C9 C8 C7 -175.6(7) . . . . ?
O4 C30 C31 C22 170.2(5) . . . . ?
O4 C30 C31 C32 -5.4(8) . . . . ?
O4 C34 C35 C36 65.6(8) . . . . ?
C11 C10 C1 C2 2.3(9) . . . . ?
C11 C10 C1 C6 -176.9(5) . . . . ?
C11 C10 C9 O2 -4.4(9) . . . . ?
C11 C10 C9 C8 175.4(6) . . . . ?
C22 C27 C28 C29 -4.1(9) . . . . ?
C22 C27 C26 C25 3.3(8) . . . . ?
C22 C23 C24 C25 2.9(9) . . . . ?
C27 C22 C23 C24 -1.5(8) . . . . ?
C27 C22 C31 C30 7.6(7) . . . . ?
C27 C22 C31 C32 -176.9(5) . . . . ?
C29 C30 C31 C22 -8.7(8) . . . . ?
C29 C30 C31 C32 175.7(5) . . . . ?
C30 O4 C34 C33 46.8(7) . . . . ?
C30 O4 C34 C35 -83.8(6) . . . . ?
C30 C29 C28 C27 3.2(9) . . . . ?
C2 C1 C6 C7 178.6(6) . . . . ?
C2 C1 C6 C5 -0.2(8) . . . . ?
C2 C3 C4 C5 0.4(12) . . . . ?
C10 C11 C21 O1 138.4(6) . . . . ?
C10 C11 C21 C20 -40.2(6) . . . . ?
C10 C11 C12 C13 42.8(7) . . . . ?
C10 C1 C6 C7 -2.2(9) . . . . ?
C10 C1 C6 C5 179.0(6) . . . . ?
C10 C9 C8 C7 4.6(11) . . . . ?
C32 C33 C34 O4 -61.5(7) . . . . ?
C32 C33 C34 C35 66.1(7) . . . . ?
C23 C22 C27 C28 174.8(5) . . . . ?
C23 C22 C27 C26 -1.5(7) . . . . ?
C23 C22 C31 C30 -168.3(5) . . . . ?
C23 C22 C31 C32 7.2(8) . . . . ?
C23 C24 C25 C26 -1.1(10) . . . . ?
C1 C2 C3 C4 -0.2(10) . . . . ?
C1 C10 C9 O2 171.6(6) . . . . ?
C1 C10 C9 C8 -8.6(9) . . . . ?
C1 C6 C5 C4 0.4(10) . . . . ?
C41 C36 C37 C38 0.7(9) . . . . ?
C41 C36 C35 C34 54.7(9) . . . . ?
C41 C40 C39 C38 2.3(10) . . . . ?
C24 C25 C26 C27 -1.9(9) . . . . ?
C28 C27 C26 C25 -173.0(6) . . . . ?
C28 C29 C30 O4 -175.6(5) . . . . ?
C28 C29 C30 C31 3.5(9) . . . . ?
C33 C32 C31 C22 174.9(5) . . . . ?
C33 C32 C31 C30 -9.8(7) . . . . ?
C33 C32 C42 O3 -99.5(7) . . . . ?
C33 C32 C42 C41 83.4(6) . . . . ?
C33 C34 C35 C36 -61.2(9) . . . . ?
C31 C22 C27 C28 -1.4(8) . . . . ?
C31 C22 C27 C26 -177.7(5) . . . . ?
C31 C22 C23 C24 174.6(5) . . . . ?
C31 C32 C33 C34 42.3(7) . . . . ?
C31 C32 C42 O3 137.5(6) . . . . ?
C31 C32 C42 C41 -39.6(7) . . . . ?
C13 O2 C9 C10 -15.5(9) . . . . ?
C13 O2 C9 C8 164.6(6) . . . . ?
C9 O2 C13 C14 -82.7(7) . . . . ?
C9 O2 C13 C12 47.5(7) . . . . ?
C9 C10 C1 C2 -173.6(6) . . . . ?
C9 C10 C1 C6 7.3(8) . . . . ?
C19 C20 C21 O1 -43.3(8) . . . . ?
C19 C20 C21 C11 135.3(5) . . . . ?
C19 C18 C17 C16 -0.5(11) . . . . ?
C36 C41 C40 C39 0.2(9) . . . . ?
C36 C41 C42 O3 139.3(7) . . . . ?
C36 C41 C42 C32 -43.6(8) . . . . ?
C36 C37 C38 C39 1.8(11) . . . . ?
C15 C20 C21 O1 136.6(6) . . . . ?
C15 C20 C21 C11 -44.8(7) . . . . ?
C15 C16 C17 C18 -0.7(11) . . . . ?
C20 C19 C18 C17 0.1(10) . . . . ?
C20 C15 C14 C13 48.6(9) . . . . ?
C20 C15 C16 C17 2.1(9) . . . . ?
C37 C36 C35 C34 -133.1(6) . . . . ?
C37 C38 C39 C40 -3.3(11) . . . . ?
C7 C6 C5 C4 -178.3(8) . . . . ?
C40 C41 C36 C37 -1.7(8) . . . . ?
C40 C41 C36 C35 170.4(6) . . . . ?
C40 C41 C42 O3 -46.7(8) . . . . ?
C40 C41 C42 C32 130.4(6) . . . . ?
C21 C11 C10 C1 -63.0(7) . . . . ?
C21 C11 C10 C9 112.9(6) . . . . ?
C21 C11 C12 C13 -83.7(6) . . . . ?
C6 C7 C8 C9 0.8(11) . . . . ?
C6 C5 C4 C3 -0.6(12) . . . . ?
C8 C7 C6 C1 -1.9(11) . . . . ?
C8 C7 C6 C5 176.8(7) . . . . ?
C14 C13 C12 C11 65.7(7) . . . . ?
C14 C15 C20 C19 168.0(6) . . . . ?
C14 C15 C20 C21 -11.8(8) . . . . ?
C14 C15 C16 C17 -169.1(6) . . . . ?
C34 O4 C30 C29 165.0(5) . . . . ?
C34 O4 C30 C31 -14.0(8) . . . . ?
C26 C27 C28 C29 172.2(5) . . . . ?
C35 C36 C37 C38 -172.0(6) . . . . ?
C42 C32 C33 C34 -81.6(6) . . . . ?
C42 C32 C31 C22 -62.8(6) . . . . ?
C42 C32 C31 C30 112.6(6) . . . . ?
C42 C41 C36 C37 172.1(5) . . . . ?
C42 C41 C36 C35 -15.8(9) . . . . ?
C42 C41 C40 C39 -174.1(6) . . . . ?
C12 C11 C10 C1 173.8(5) . . . . ?
C12 C11 C10 C9 -10.3(7) . . . . ?
C12 C11 C21 O1 -97.0(6) . . . . ?
C12 C11 C21 C20 84.4(6) . . . . ?
C12 C13 C14 C15 -56.7(8) . . . . ?
C16 C15 C20 C19 -2.4(8) . . . . ?
C16 C15 C20 C21 177.7(5) . . . . ?
C16 C15 C14 C13 -141.0(6) . . . . ?
C3 C2 C1 C10 -179.1(6) . . . . ?
C3 C2 C1 C6 0.1(9) . . . . ?
C18 C19 C20 C15 1.4(8) . . . . ?
C18 C19 C20 C21 -178.7(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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.799
####################################################################### 
# 
# 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_20211117-zzx-934
_database_code_depnum_ccdc_archive 'CCDC 2151486'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2021-11-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Br O'
_chemical_formula_sum            'C22 H17 Br O'
_chemical_formula_weight         377.26
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H17 Br O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.5950(3)
_cell_length_b                   10.2307(4)
_cell_length_c                   29.7158(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1700.96(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2301
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5810
_cell_measurement_theta_min      3.9530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            6328
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.010
_diffrn_reflns_theta_min         3.706
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00   5.00   1.00    7.89    --  -18.78 -38.00 120.00   83
  2  ω    -91.00   6.00   1.00    7.89    --  -18.78 -38.00-150.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0091933000
_diffrn_orient_matrix_UB_12      -0.0566252000
_diffrn_orient_matrix_UB_13      0.0136688000
_diffrn_orient_matrix_UB_21      -0.0526910000
_diffrn_orient_matrix_UB_22      -0.0378812000
_diffrn_orient_matrix_UB_23      -0.0173429000
_diffrn_orient_matrix_UB_31      0.1149600000
_diffrn_orient_matrix_UB_32      -0.0128964000
_diffrn_orient_matrix_UB_33      -0.0090470000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                2981
_reflns_number_total             3859
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.065
_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)+(0.0192P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0772
_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:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C16(H16), C3(H3), C13(H13), C11(H11), C15(H15), C12(H12),
 C22(H22)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.44847(10) 0.72428(5) 0.62542(2) 0.05189(17) Uani 1 1 d . . . . .
O1 O 0.6792(5) 0.2685(3) 0.62496(10) 0.0445(7) Uani 1 1 d . . . . .
C5 C 0.2494(8) 0.5513(4) 0.69174(14) 0.0359(11) Uani 1 1 d . . . . .
C17 C 0.6549(8) 0.3367(4) 0.58504(15) 0.0351(11) Uani 1 1 d . . . . .
C9 C 0.4686(8) 0.4948(4) 0.53511(14) 0.0320(10) Uani 1 1 d . . . . .
C6 C 0.3137(8) 0.5608(4) 0.64309(14) 0.0355(11) Uani 1 1 d . . . . .
C4 C 0.0721(9) 0.6248(4) 0.71182(15) 0.0459(12) Uani 1 1 d . . . . .
H4 H -0.008547 0.687594 0.695021 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3281(7) 0.4544(4) 0.61759(14) 0.0330(10) Uani 1 1 d . . . . .
C19 C 0.2621(8) 0.3242(4) 0.63789(13) 0.0345(11) Uani 1 1 d . . . . .
H19A H 0.209918 0.263003 0.614972 0.041 Uiso 1 1 calc R U . . .
H19B H 0.136988 0.333647 0.660259 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2860(9) 0.5828(4) 0.52409(14) 0.0397(12) Uani 1 1 d . . . . .
H10 H 0.169653 0.602408 0.545406 0.048 Uiso 1 1 calc R U . . .
C16 C 0.8217(8) 0.3040(5) 0.55126(15) 0.0424(13) Uani 1 1 d . . . . .
H16 H 0.935482 0.239499 0.556500 0.051 Uiso 1 1 calc R U . . .
C18 C 0.4955(7) 0.2806(5) 0.65928(14) 0.0414(11) Uani 1 1 d . . . . .
H18 H 0.471005 0.194812 0.673209 0.050 Uiso 1 1 calc R U . . .
C8 C 0.4854(7) 0.4321(4) 0.57804(13) 0.0313(10) Uani 1 1 d . . . . .
C3 C 0.0126(10) 0.6065(4) 0.75662(15) 0.0503(14) Uani 1 1 d . . . . .
H3 H -0.109105 0.655777 0.769510 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6429(8) 0.4637(5) 0.50164(14) 0.0361(11) Uani 1 1 d . . . . .
C13 C 0.6290(9) 0.5281(5) 0.45921(15) 0.0478(14) Uani 1 1 d . . . . .
H13 H 0.743604 0.510792 0.437341 0.057 Uiso 1 1 calc R U . . .
C20 C 0.5771(9) 0.3781(4) 0.69612(15) 0.0452(12) Uani 1 1 d . . . . .
H20A H 0.657264 0.329593 0.719764 0.054 Uiso 1 1 calc R U . . .
H20B H 0.692929 0.437614 0.683079 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2753(10) 0.6406(5) 0.48261(15) 0.0460(13) Uani 1 1 d . . . . .
H11 H 0.151064 0.697721 0.475854 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1332(9) 0.5152(5) 0.78218(16) 0.0460(14) Uani 1 1 d . . . . .
C1 C 0.0638(11) 0.4935(5) 0.83128(14) 0.0638(16) Uani 1 1 d . . . . .
H1A H 0.087638 0.572845 0.847913 0.096 Uiso 1 1 calc R U . . .
H1B H 0.161414 0.425489 0.843863 0.096 Uiso 1 1 calc R U . . .
H1C H -0.101279 0.468353 0.832955 0.096 Uiso 1 1 calc R U . . .
C21 C 0.3767(8) 0.4580(5) 0.71709(15) 0.0406(12) Uani 1 1 d . . . . .
C15 C 0.8154(9) 0.3672(5) 0.51101(15) 0.0435(13) Uani 1 1 d . . . . .
H15 H 0.927783 0.346121 0.489118 0.052 Uiso 1 1 calc R U . . .
C12 C 0.4511(11) 0.6140(5) 0.45028(15) 0.0516(14) Uani 1 1 d . . . . .
H12 H 0.445614 0.655667 0.422481 0.062 Uiso 1 1 calc R U . . .
C22 C 0.3138(10) 0.4424(5) 0.76257(15) 0.0459(13) Uani 1 1 d . . . . .
H22 H 0.395658 0.381538 0.779958 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.908(5) . ?
O1 C17 1.383(5) . ?
O1 C18 1.453(5) . ?
C5 C6 1.493(5) . ?
C5 C4 1.380(6) . ?
C5 C21 1.410(6) . ?
C17 C16 1.411(6) . ?
C17 C8 1.376(6) . ?
C9 C10 1.401(6) . ?
C9 C8 1.431(5) . ?
C9 C14 1.429(6) . ?
C6 C7 1.329(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.385(6) . ?
C7 C19 1.508(5) . ?
C7 C8 1.486(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.520(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.360(6) . ?
C18 H18 0.9800 . ?
C18 C20 1.550(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.380(6) . ?
C14 C13 1.424(6) . ?
C14 C15 1.409(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.354(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.521(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(7) . ?
C2 C1 1.526(6) . ?
C2 C22 1.384(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C21 C22 1.406(6) . ?
C15 H15 0.9300 . ?
C12 H12 0.9300 . ?
C22 H22 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
C17 O1 C18 119.3(3) . . ?
C4 C5 C6 123.8(4) . . ?
C4 C5 C21 120.1(4) . . ?
C21 C5 C6 116.1(4) . . ?
O1 C17 C16 115.2(4) . . ?
C8 C17 O1 123.7(4) . . ?
C8 C17 C16 121.1(4) . . ?
C10 C9 C8 123.0(4) . . ?
C10 C9 C14 118.6(4) . . ?
C14 C9 C8 118.4(4) . . ?
C5 C6 Br1 114.8(3) . . ?
C7 C6 Br1 122.5(3) . . ?
C7 C6 C5 120.9(4) . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 120.9(5) . . ?
C3 C4 H4 119.5 . . ?
C6 C7 C19 118.7(4) . . ?
C6 C7 C8 127.8(4) . . ?
C8 C7 C19 109.0(4) . . ?
C7 C19 H19A 111.3 . . ?
C7 C19 H19B 111.3 . . ?
C7 C19 C18 102.5(4) . . ?
H19A C19 H19B 109.2 . . ?
C18 C19 H19A 111.3 . . ?
C18 C19 H19B 111.3 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H10 119.3 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.7(5) . . ?
C15 C16 H16 120.1 . . ?
O1 C18 C19 109.8(3) . . ?
O1 C18 H18 108.6 . . ?
O1 C18 C20 110.0(4) . . ?
C19 C18 H18 108.6 . . ?
C19 C18 C20 111.1(4) . . ?
C20 C18 H18 108.6 . . ?
C17 C8 C9 119.9(4) . . ?
C17 C8 C7 113.4(4) . . ?
C9 C8 C7 126.7(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C13 C14 C9 118.4(4) . . ?
C15 C14 C9 119.1(4) . . ?
C15 C14 C13 122.4(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H13 119.5 . . ?
C18 C20 H20A 108.6 . . ?
C18 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 C18 114.7(4) . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(5) . . ?
C12 C11 H11 119.9 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 C22 119.3(5) . . ?
C22 C2 C1 120.6(5) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C21 C20 121.2(4) . . ?
C22 C21 C5 117.6(4) . . ?
C22 C21 C20 121.2(4) . . ?
C16 C15 C14 121.7(4) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C2 C22 C21 121.8(5) . . ?
C2 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C6 C7 C19 167.7(3) . . . . ?
Br1 C6 C7 C8 14.2(7) . . . . ?
O1 C17 C16 C15 -178.9(4) . . . . ?
O1 C17 C8 C9 -178.1(4) . . . . ?
O1 C17 C8 C7 -0.5(6) . . . . ?
O1 C18 C20 C21 146.5(4) . . . . ?
C5 C6 C7 C19 4.1(7) . . . . ?
C5 C6 C7 C8 -149.5(4) . . . . ?
C5 C4 C3 C2 1.1(8) . . . . ?
C5 C21 C22 C2 0.1(7) . . . . ?
C17 O1 C18 C19 22.5(5) . . . . ?
C17 O1 C18 C20 -100.0(4) . . . . ?
C17 C16 C15 C14 -1.1(7) . . . . ?
C9 C10 C11 C12 -1.0(8) . . . . ?
C9 C14 C13 C12 -1.8(7) . . . . ?
C9 C14 C15 C16 -0.8(7) . . . . ?
C6 C5 C4 C3 176.6(5) . . . . ?
C6 C5 C21 C20 3.4(7) . . . . ?
C6 C5 C21 C22 -177.3(4) . . . . ?
C6 C7 C19 C18 -86.7(5) . . . . ?
C6 C7 C8 C17 113.8(5) . . . . ?
C6 C7 C8 C9 -68.8(7) . . . . ?
C4 C5 C6 Br1 65.9(5) . . . . ?
C4 C5 C6 C7 -129.2(5) . . . . ?
C4 C5 C21 C20 -178.4(4) . . . . ?
C4 C5 C21 C22 0.9(7) . . . . ?
C4 C3 C2 C1 -178.8(5) . . . . ?
C4 C3 C2 C22 -0.1(8) . . . . ?
C7 C19 C18 O1 -60.5(4) . . . . ?
C7 C19 C18 C20 61.4(4) . . . . ?
C19 C7 C8 C17 -41.8(5) . . . . ?
C19 C7 C8 C9 135.6(4) . . . . ?
C19 C18 C20 C21 24.6(6) . . . . ?
C10 C9 C8 C17 173.4(4) . . . . ?
C10 C9 C8 C7 -3.9(7) . . . . ?
C10 C9 C14 C13 2.7(6) . . . . ?
C10 C9 C14 C15 -174.7(4) . . . . ?
C10 C11 C12 C13 2.0(8) . . . . ?
C16 C17 C8 C9 3.3(6) . . . . ?
C16 C17 C8 C7 -179.1(4) . . . . ?
C18 O1 C17 C16 -170.8(4) . . . . ?
C18 O1 C17 C8 10.5(6) . . . . ?
C18 C20 C21 C5 -66.7(6) . . . . ?
C18 C20 C21 C22 114.0(5) . . . . ?
C8 C17 C16 C15 -0.2(7) . . . . ?
C8 C9 C10 C11 -179.8(4) . . . . ?
C8 C9 C14 C13 -178.8(4) . . . . ?
C8 C9 C14 C15 3.8(6) . . . . ?
C8 C7 C19 C18 71.4(4) . . . . ?
C3 C2 C22 C21 -0.5(7) . . . . ?
C14 C9 C10 C11 -1.3(7) . . . . ?
C14 C9 C8 C17 -5.1(6) . . . . ?
C14 C9 C8 C7 177.7(4) . . . . ?
C14 C13 C12 C11 -0.6(8) . . . . ?
C13 C14 C15 C16 -178.0(4) . . . . ?
C20 C21 C22 C2 179.4(5) . . . . ?
C1 C2 C22 C21 178.2(5) . . . . ?
C21 C5 C6 Br1 -115.9(4) . . . . ?
C21 C5 C6 C7 48.9(6) . . . . ?
C21 C5 C4 C3 -1.5(7) . . . . ?
C15 C14 C13 C12 175.5(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 1.091
_oxdiff_exptl_absorpt_empirical_full_min 0.901
####################################################################### 
# 
# 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_20220117-zzx-lk-671-c
_database_code_depnum_ccdc_archive 'CCDC 2151489'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 Br O Si'
_chemical_formula_sum            'C23 H21 Br O Si'
_chemical_formula_weight         421.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O Br Si'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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                   8.6383(3)
_cell_length_b                   12.6159(5)
_cell_length_c                   17.6123(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1919.39(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7660
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   0.529
_shelx_estimated_absorpt_T_min   0.487
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8032
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         3.431
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  83.00   1.00    6.95    --   18.58  38.00   0.00   89
  2  ω    -21.00  66.00   1.00    6.95    --   18.58  19.00 -60.00   87
  3  ω    -38.00  -9.00   1.00    6.95    --  -18.78 -77.00   0.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0094258000
_diffrn_orient_matrix_UB_12      -0.0203312000
_diffrn_orient_matrix_UB_13      -0.0372815000
_diffrn_orient_matrix_UB_21      0.0144679000
_diffrn_orient_matrix_UB_22      -0.0519480000
_diffrn_orient_matrix_UB_23      0.0136463000
_diffrn_orient_matrix_UB_31      -0.0802296000
_diffrn_orient_matrix_UB_32      -0.0069998000
_diffrn_orient_matrix_UB_33      0.0068964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                3532
_reflns_number_total             4349
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 1203 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.039
_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)+(0.0302P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0805
_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:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C21(H21), C3(H3), C20(H20), C18(H18), C7(H7), C19(H19), C8(H8),
 C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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 0.16630(5) 0.49596(4) 0.36026(2) 0.04223(15) Uani 1 1 d . . . . .
Si1 Si 0.47552(13) 0.60845(9) 0.55355(8) 0.0325(3) Uani 1 1 d . . . . .
O1 O 0.6971(3) 0.3590(2) 0.44049(18) 0.0390(8) Uani 1 1 d . . . . .
C11 C 0.3692(4) 0.3688(3) 0.4489(2) 0.0245(9) Uani 1 1 d . . . . .
C23 C 0.2557(4) 0.4407(3) 0.4520(2) 0.0234(9) Uani 1 1 d . . . . .
C2 C 0.2083(5) 0.2383(3) 0.3255(2) 0.0310(10) Uani 1 1 d . . . . .
H2 H 0.147081 0.269536 0.362690 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4466(4) 0.3202(3) 0.3826(2) 0.0250(9) Uani 1 1 d . . . . .
C22 C 0.1898(4) 0.4880(3) 0.5223(2) 0.0260(8) Uani 1 1 d . . . . .
C1 C 0.3698(5) 0.2590(3) 0.3246(2) 0.0276(9) Uani 1 1 d . . . . .
C21 C 0.0359(4) 0.4610(3) 0.5408(2) 0.0317(10) Uani 1 1 d . . . . .
H21 H -0.022416 0.420503 0.507157 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4657(5) 0.3484(3) 0.5188(2) 0.0271(9) Uani 1 1 d . . . . .
H12A H 0.483941 0.273109 0.525442 0.033 Uiso 1 1 calc R U . . .
H12B H 0.414574 0.375630 0.563831 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6070(5) 0.3187(4) 0.3830(3) 0.0337(11) Uani 1 1 d . . . . .
C14 C 0.5975(4) 0.5250(3) 0.4888(2) 0.0325(11) Uani 1 1 d . . . . .
H14A H 0.554956 0.531774 0.438087 0.039 Uiso 1 1 calc R U . . .
H14B H 0.700051 0.556243 0.487670 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2764(4) 0.5526(3) 0.5716(2) 0.0276(9) Uani 1 1 d . . . . .
C13 C 0.6174(4) 0.4069(3) 0.5047(2) 0.0317(10) Uani 1 1 d . . . . .
H13 H 0.682904 0.398867 0.549779 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1406(6) 0.1736(4) 0.2731(3) 0.0414(12) Uani 1 1 d . . . . .
H3 H 0.034735 0.160646 0.275431 0.050 Uiso 1 1 calc R U . . .
C20 C -0.0286(4) 0.4939(4) 0.6080(2) 0.0352(9) Uani 1 1 d . . . . .
H20 H -0.129627 0.474622 0.619855 0.042 Uiso 1 1 calc R U . . .
C18 C 0.2053(5) 0.5845(3) 0.6395(3) 0.0389(11) Uani 1 1 d . . . . .
H18 H 0.260546 0.626695 0.673306 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6214(5) 0.2217(4) 0.2665(3) 0.0429(12) Uani 1 1 d . . . . .
H7 H 0.679283 0.194052 0.226610 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4587(5) 0.2085(4) 0.2670(2) 0.0352(11) Uani 1 1 d . . . . .
C19 C 0.0549(5) 0.5552(4) 0.6578(3) 0.0422(13) Uani 1 1 d . . . . .
H19 H 0.011041 0.576761 0.703516 0.051 Uiso 1 1 calc R U . . .
C8 C 0.6938(5) 0.2741(4) 0.3233(3) 0.0416(12) Uani 1 1 d . . . . .
H8 H 0.801014 0.280641 0.322948 0.050 Uiso 1 1 calc R U . . .
C5 C 0.3854(6) 0.1445(4) 0.2131(3) 0.0489(14) Uani 1 1 d . . . . .
H5 H 0.444148 0.113478 0.174810 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2300(6) 0.1264(4) 0.2154(3) 0.0498(14) Uani 1 1 d . . . . .
H4 H 0.183338 0.083248 0.179192 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5792(5) 0.6241(5) 0.6461(3) 0.0605(17) Uani 1 1 d . . . . .
H15A H 0.589620 0.556057 0.670004 0.091 Uiso 1 1 calc R U . . .
H15B H 0.521297 0.670561 0.678522 0.091 Uiso 1 1 calc R U . . .
H15C H 0.680073 0.653547 0.637173 0.091 Uiso 1 1 calc R U . . .
C16 C 0.4515(7) 0.7393(4) 0.5068(4) 0.072(2) Uani 1 1 d . . . . .
H16A H 0.551452 0.770025 0.497632 0.109 Uiso 1 1 calc R U . . .
H16B H 0.392418 0.785250 0.539100 0.109 Uiso 1 1 calc R U . . .
H16C H 0.398287 0.730176 0.459362 0.109 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C23 1.922(4) . ?
Si1 C14 1.876(4) . ?
Si1 C17 1.886(4) . ?
Si1 C15 1.870(5) . ?
Si1 C16 1.856(5) . ?
O1 C9 1.374(5) . ?
O1 C13 1.455(5) . ?
C11 C23 1.337(5) . ?
C11 C10 1.480(5) . ?
C11 C12 1.509(5) . ?
C23 C22 1.487(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.420(6) . ?
C2 C3 1.363(6) . ?
C10 C1 1.442(5) . ?
C10 C9 1.386(5) . ?
C22 C21 1.411(5) . ?
C22 C17 1.407(5) . ?
C1 C6 1.424(6) . ?
C21 H21 0.9300 . ?
C21 C20 1.372(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.524(5) . ?
C9 C8 1.409(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.526(6) . ?
C17 C18 1.404(6) . ?
C13 H13 0.9800 . ?
C3 H3 0.9300 . ?
C3 C4 1.408(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.374(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(6) . ?
C7 H7 0.9300 . ?
C7 C6 1.416(7) . ?
C7 C8 1.352(7) . ?
C6 C5 1.398(6) . ?
C19 H19 0.9300 . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.363(7) . ?
C4 H4 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C14 Si1 C17 113.90(18) . . ?
C15 Si1 C14 108.6(2) . . ?
C15 Si1 C17 109.2(2) . . ?
C16 Si1 C14 107.0(2) . . ?
C16 Si1 C17 107.8(2) . . ?
C16 Si1 C15 110.3(3) . . ?
C9 O1 C13 117.3(3) . . ?
C23 C11 C10 130.1(4) . . ?
C23 C11 C12 119.2(4) . . ?
C10 C11 C12 108.9(3) . . ?
C11 C23 Br1 120.5(3) . . ?
C11 C23 C22 125.9(4) . . ?
C22 C23 Br1 113.6(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C3 C2 C1 121.6(4) . . ?
C1 C10 C11 124.9(3) . . ?
C9 C10 C11 117.0(4) . . ?
C9 C10 C1 117.2(4) . . ?
C21 C22 C23 117.1(3) . . ?
C17 C22 C23 122.9(3) . . ?
C17 C22 C21 119.9(4) . . ?
C2 C1 C10 123.0(4) . . ?
C2 C1 C6 117.1(4) . . ?
C6 C1 C10 119.7(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C11 C12 C13 105.0(3) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
O1 C9 C10 124.4(4) . . ?
O1 C9 C8 113.4(4) . . ?
C10 C9 C8 122.2(4) . . ?
Si1 C14 H14A 107.3 . . ?
Si1 C14 H14B 107.3 . . ?
H14A C14 H14B 106.9 . . ?
C13 C14 Si1 120.0(3) . . ?
C13 C14 H14A 107.3 . . ?
C13 C14 H14B 107.3 . . ?
C22 C17 Si1 126.7(3) . . ?
C18 C17 Si1 115.8(3) . . ?
C18 C17 C22 117.4(3) . . ?
O1 C13 C12 109.4(3) . . ?
O1 C13 C14 108.4(4) . . ?
O1 C13 H13 108.3 . . ?
C12 C13 C14 113.9(3) . . ?
C12 C13 H13 108.3 . . ?
C14 C13 H13 108.3 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C21 C20 H20 119.7 . . ?
C21 C20 C19 120.6(4) . . ?
C19 C20 H20 119.7 . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 122.1(4) . . ?
C19 C18 H18 119.0 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C8 C7 C6 120.8(4) . . ?
C7 C6 C1 119.2(4) . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 C7 120.9(4) . . ?
C20 C19 C18 119.5(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 119.9 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.5(5) . . ?
C4 C5 H5 119.2 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
Br1 C23 C22 C21 70.0(4) . . . . ?
Br1 C23 C22 C17 -113.4(4) . . . . ?
Si1 C14 C13 O1 171.7(2) . . . . ?
Si1 C14 C13 C12 49.6(5) . . . . ?
Si1 C17 C18 C19 175.8(4) . . . . ?
O1 C9 C8 C7 173.3(4) . . . . ?
C11 C23 C22 C21 -112.0(4) . . . . ?
C11 C23 C22 C17 64.7(6) . . . . ?
C11 C10 C1 C2 -0.2(6) . . . . ?
C11 C10 C1 C6 -174.6(4) . . . . ?
C11 C10 C9 O1 -0.1(7) . . . . ?
C11 C10 C9 C8 179.6(4) . . . . ?
C11 C12 C13 O1 -64.8(4) . . . . ?
C11 C12 C13 C14 56.8(5) . . . . ?
C23 C11 C10 C1 -59.8(6) . . . . ?
C23 C11 C10 C9 131.4(5) . . . . ?
C23 C11 C12 C13 -102.5(4) . . . . ?
C23 C22 C21 C20 174.3(4) . . . . ?
C23 C22 C17 Si1 9.7(6) . . . . ?
C23 C22 C17 C18 -174.3(4) . . . . ?
C2 C1 C6 C7 -176.3(4) . . . . ?
C2 C1 C6 C5 1.9(6) . . . . ?
C2 C3 C4 C5 1.1(8) . . . . ?
C10 C11 C23 Br1 0.6(6) . . . . ?
C10 C11 C23 C22 -177.3(4) . . . . ?
C10 C11 C12 C13 63.9(4) . . . . ?
C10 C1 C6 C7 -1.6(6) . . . . ?
C10 C1 C6 C5 176.6(4) . . . . ?
C10 C9 C8 C7 -6.4(7) . . . . ?
C22 C21 C20 C19 1.0(7) . . . . ?
C22 C17 C18 C19 -0.6(7) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C1 C10 C9 O1 -169.7(4) . . . . ?
C1 C10 C9 C8 10.0(7) . . . . ?
C1 C6 C5 C4 -1.8(8) . . . . ?
C21 C22 C17 Si1 -173.8(3) . . . . ?
C21 C22 C17 C18 2.2(6) . . . . ?
C21 C20 C19 C18 0.6(7) . . . . ?
C12 C11 C23 Br1 163.8(3) . . . . ?
C12 C11 C23 C22 -14.2(6) . . . . ?
C12 C11 C10 C1 135.7(4) . . . . ?
C12 C11 C10 C9 -33.1(5) . . . . ?
C9 O1 C13 C12 33.6(5) . . . . ?
C9 O1 C13 C14 -91.2(4) . . . . ?
C9 C10 C1 C2 168.5(4) . . . . ?
C9 C10 C1 C6 -5.8(6) . . . . ?
C14 Si1 C17 C22 -28.6(4) . . . . ?
C14 Si1 C17 C18 155.4(3) . . . . ?
C17 Si1 C14 C13 -51.3(4) . . . . ?
C17 C22 C21 C20 -2.4(6) . . . . ?
C17 C18 C19 C20 -0.8(7) . . . . ?
C13 O1 C9 C10 -0.3(6) . . . . ?
C13 O1 C9 C8 179.9(4) . . . . ?
C3 C2 C1 C10 -175.1(4) . . . . ?
C3 C2 C1 C6 -0.6(6) . . . . ?
C7 C6 C5 C4 176.4(5) . . . . ?
C6 C7 C8 C9 -1.6(8) . . . . ?
C6 C5 C4 C3 0.3(8) . . . . ?
C8 C7 C6 C1 5.5(7) . . . . ?
C8 C7 C6 C5 -172.7(5) . . . . ?
C15 Si1 C14 C13 70.7(4) . . . . ?
C15 Si1 C17 C22 -150.2(4) . . . . ?
C15 Si1 C17 C18 33.8(4) . . . . ?
C16 Si1 C14 C13 -170.2(3) . . . . ?
C16 Si1 C17 C22 90.0(4) . . . . ?
C16 Si1 C17 C18 -86.1(4) . . . . ?

_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 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.745
####################################################################### 
# 
# 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_20211228-lk-467-up
_database_code_depnum_ccdc_archive 'CCDC 2151483'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2021-12-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Br O'
_chemical_formula_sum            'C21 H15 Br O'
_chemical_formula_weight         363.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H Br O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8805(4)
_cell_length_b                   11.2373(4)
_cell_length_c                   17.8564(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1581.28(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3630
_cell_measurement_theta_min      3.8960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.33
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6083
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.096
_diffrn_reflns_theta_min         3.357
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  45.00   1.00    4.00    --   18.74 -77.00  60.00   77
  2  ω      0.00  84.00   1.00    4.00    --   18.74  38.00-120.00   84
  3  ω    -74.00 -48.00   1.00    4.00    --  -18.85 178.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0823196000
_diffrn_orient_matrix_UB_12      -0.0233225000
_diffrn_orient_matrix_UB_13      0.0063979000
_diffrn_orient_matrix_UB_21      -0.0187517000
_diffrn_orient_matrix_UB_22      -0.0488271000
_diffrn_orient_matrix_UB_23      -0.0237788000
_diffrn_orient_matrix_UB_31      0.0310413000
_diffrn_orient_matrix_UB_32      0.0324160000
_diffrn_orient_matrix_UB_33      -0.0312326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                2126
_reflns_number_total             3598
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 647 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      0.981
_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)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.1007
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C14(H14), C17(H17), C16(H16), C20(H20), C19(H19), C7(H7),
 C15(H15), C8(H8)
;
_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
Br2 Br 0.73281(9) 0.65207(5) 0.68054(4) 0.0765(3) Uani 1 1 d . . . . .
O1 O 0.8174(4) 0.1118(3) 0.7522(2) 0.0530(11) Uani 1 1 d . . . . .
C2 C 0.6502(7) 0.4032(4) 0.6953(3) 0.0426(14) Uani 1 1 d . . . . .
H2 H 0.575878 0.414705 0.651903 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5480(7) 0.4224(5) 0.7666(3) 0.0502(15) Uani 1 1 d . . . . .
H3A H 0.522905 0.506590 0.771415 0.060 Uiso 1 1 calc R U . . .
H3B H 0.440789 0.380616 0.761928 0.060 Uiso 1 1 calc R U . . .
C4 C 0.6352(7) 0.3812(4) 0.8366(3) 0.0451(15) Uani 1 1 d . . . . .
C12 C 0.7554(7) 0.1915(4) 0.6377(3) 0.0427(13) Uani 1 1 d . . . . .
C11 C 0.7157(6) 0.2769(4) 0.6951(3) 0.0405(14) Uani 1 1 d . . . . .
C13 C 0.7443(6) 0.1867(4) 0.5578(3) 0.0441(13) Uani 1 1 d . . . . .
C10 C 0.7557(7) 0.2258(4) 0.7611(3) 0.0434(12) Uani 1 1 d . . . . .
C1 C 0.8016(6) 0.4870(4) 0.6888(3) 0.0473(14) Uani 1 1 d . . . . .
H1A H 0.867888 0.465492 0.645123 0.057 Uiso 1 1 calc R U . . .
H1B H 0.873331 0.477705 0.732579 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7374(7) 0.2785(4) 0.8346(3) 0.0464(13) Uani 1 1 d . . . . .
C18 C 0.7919(6) 0.0783(5) 0.5223(4) 0.0502(15) Uani 1 1 d . . . . .
C6 C 0.6875(8) 0.3932(6) 0.9694(4) 0.0611(17) Uani 1 1 d . . . . .
H6 H 0.670165 0.431770 1.014820 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6116(8) 0.4377(5) 0.9047(4) 0.0562(17) Uani 1 1 d . . . . .
H5 H 0.544697 0.505710 0.907352 0.067 Uiso 1 1 calc R U . . .
C21 C 0.8153(6) 0.0927(5) 0.6757(4) 0.0475(14) Uani 1 1 d . . . . .
C14 C 0.6922(7) 0.2810(5) 0.5128(3) 0.0530(16) Uani 1 1 d . . . . .
H14 H 0.662426 0.352686 0.535324 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7804(7) 0.0711(5) 0.4432(4) 0.0604(18) Uani 1 1 d . . . . .
H17 H 0.809617 0.000496 0.419249 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7279(7) 0.1646(6) 0.4020(4) 0.0686(17) Uani 1 1 d . . . . .
H16 H 0.721310 0.157934 0.350169 0.082 Uiso 1 1 calc R U . . .
C20 C 0.8651(7) -0.0147(5) 0.6419(4) 0.0558(18) Uani 1 1 d . . . . .
H20 H 0.904482 -0.079004 0.669757 0.067 Uiso 1 1 calc R U . . .
C19 C 0.8524(7) -0.0190(5) 0.5668(4) 0.0600(19) Uani 1 1 d . . . . .
H19 H 0.884456 -0.088665 0.542476 0.072 Uiso 1 1 calc R U . . .
C7 C 0.7876(8) 0.2932(5) 0.9669(4) 0.0621(17) Uani 1 1 d . . . . .
H7 H 0.837491 0.264158 1.010422 0.075 Uiso 1 1 calc R U . . .
C15 C 0.6834(7) 0.2714(6) 0.4367(4) 0.0612(18) Uani 1 1 d . . . . .
H15 H 0.647851 0.335931 0.408111 0.073 Uiso 1 1 calc R U . . .
C8 C 0.8139(7) 0.2356(5) 0.8989(4) 0.0544(16) Uani 1 1 d . . . . .
H8 H 0.882727 0.168480 0.896640 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C1 1.938(4) . ?
O1 C10 1.379(5) . ?
O1 C21 1.381(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.522(7) . ?
C2 C11 1.511(6) . ?
C2 C1 1.525(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.500(7) . ?
C4 C9 1.408(7) . ?
C4 C5 1.385(7) . ?
C12 C11 1.438(7) . ?
C12 C13 1.430(7) . ?
C12 C21 1.385(7) . ?
C11 C10 1.348(6) . ?
C13 C18 1.424(7) . ?
C13 C14 1.391(7) . ?
C10 C9 1.447(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C9 C8 1.383(7) . ?
C18 C17 1.417(8) . ?
C18 C19 1.433(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.392(8) . ?
C6 C7 1.374(8) . ?
C5 H5 0.9300 . ?
C21 C20 1.406(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.347(8) . ?
C16 H16 0.9300 . ?
C16 C15 1.396(8) . ?
C20 H20 0.9300 . ?
C20 C19 1.347(8) . ?
C19 H19 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.392(8) . ?
C15 H15 0.9300 . ?
C8 H8 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
C10 O1 C21 104.7(4) . . ?
C3 C2 H2 109.0 . . ?
C3 C2 C1 113.0(5) . . ?
C11 C2 H2 109.0 . . ?
C11 C2 C3 108.4(4) . . ?
C11 C2 C1 108.3(4) . . ?
C1 C2 H2 109.0 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.2(5) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C9 C4 C3 119.6(5) . . ?
C5 C4 C3 121.9(5) . . ?
C5 C4 C9 118.4(5) . . ?
C13 C12 C11 136.3(5) . . ?
C21 C12 C11 105.0(5) . . ?
C21 C12 C13 118.7(5) . . ?
C12 C11 C2 134.6(5) . . ?
C10 C11 C2 118.5(5) . . ?
C10 C11 C12 106.8(4) . . ?
C18 C13 C12 117.4(5) . . ?
C14 C13 C12 124.4(5) . . ?
C14 C13 C18 118.2(5) . . ?
O1 C10 C9 121.3(5) . . ?
C11 C10 O1 112.1(4) . . ?
C11 C10 C9 126.5(4) . . ?
Br2 C1 H1A 109.2 . . ?
Br2 C1 H1B 109.2 . . ?
C2 C1 Br2 112.2(3) . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C4 C9 C10 114.6(5) . . ?
C8 C9 C4 120.9(5) . . ?
C8 C9 C10 124.5(5) . . ?
C13 C18 C19 119.5(6) . . ?
C17 C18 C13 118.4(5) . . ?
C17 C18 C19 122.0(6) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.9(6) . . ?
C4 C5 C6 120.4(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
O1 C21 C12 111.4(4) . . ?
O1 C21 C20 123.7(5) . . ?
C12 C21 C20 124.9(6) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.0(6) . . ?
C15 C14 H14 119.0 . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.2(5) . . ?
C16 C17 H17 119.4 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.3(6) . . ?
C15 C16 H16 119.8 . . ?
C21 C20 H20 122.0 . . ?
C19 C20 C21 116.0(6) . . ?
C19 C20 H20 122.0 . . ?
C18 C19 H19 118.3 . . ?
C20 C19 C18 123.4(6) . . ?
C20 C19 H19 118.3 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(6) . . ?
C8 C7 H7 120.2 . . ?
C14 C15 C16 119.8(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C9 C8 C7 119.8(6) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C9 C4 -164.8(4) . . . . ?
O1 C10 C9 C8 16.2(8) . . . . ?
O1 C21 C20 C19 178.9(5) . . . . ?
C2 C3 C4 C9 -35.7(7) . . . . ?
C2 C3 C4 C5 147.6(5) . . . . ?
C2 C11 C10 O1 -178.6(4) . . . . ?
C2 C11 C10 C9 2.2(8) . . . . ?
C3 C2 C11 C12 149.8(6) . . . . ?
C3 C2 C11 C10 -33.1(6) . . . . ?
C3 C2 C1 Br2 -64.5(5) . . . . ?
C3 C4 C9 C10 3.6(7) . . . . ?
C3 C4 C9 C8 -177.4(5) . . . . ?
C3 C4 C5 C6 176.6(5) . . . . ?
C4 C9 C8 C7 1.1(8) . . . . ?
C12 C11 C10 O1 -0.7(6) . . . . ?
C12 C11 C10 C9 180.0(5) . . . . ?
C12 C13 C18 C17 179.4(5) . . . . ?
C12 C13 C18 C19 -1.6(7) . . . . ?
C12 C13 C14 C15 -179.8(5) . . . . ?
C12 C21 C20 C19 0.1(8) . . . . ?
C11 C2 C3 C4 48.3(6) . . . . ?
C11 C2 C1 Br2 175.4(4) . . . . ?
C11 C12 C13 C18 -177.0(6) . . . . ?
C11 C12 C13 C14 3.8(10) . . . . ?
C11 C12 C21 O1 -0.8(6) . . . . ?
C11 C12 C21 C20 178.1(5) . . . . ?
C11 C10 C9 C4 14.4(8) . . . . ?
C11 C10 C9 C8 -164.6(5) . . . . ?
C13 C12 C11 C2 -3.1(11) . . . . ?
C13 C12 C11 C10 179.6(6) . . . . ?
C13 C12 C21 O1 -179.8(4) . . . . ?
C13 C12 C21 C20 -0.9(8) . . . . ?
C13 C18 C17 C16 0.9(9) . . . . ?
C13 C18 C19 C20 0.9(8) . . . . ?
C13 C14 C15 C16 -0.1(9) . . . . ?
C10 O1 C21 C12 0.4(6) . . . . ?
C10 O1 C21 C20 -178.5(5) . . . . ?
C10 C9 C8 C7 -179.9(5) . . . . ?
C1 C2 C3 C4 -71.6(6) . . . . ?
C1 C2 C11 C12 -87.3(7) . . . . ?
C1 C2 C11 C10 89.8(6) . . . . ?
C9 C4 C5 C6 -0.1(8) . . . . ?
C18 C13 C14 C15 1.0(8) . . . . ?
C18 C17 C16 C15 0.0(9) . . . . ?
C6 C7 C8 C9 -0.9(8) . . . . ?
C5 C4 C9 C10 -179.7(5) . . . . ?
C5 C4 C9 C8 -0.6(7) . . . . ?
C5 C6 C7 C8 0.1(8) . . . . ?
C21 O1 C10 C11 0.2(6) . . . . ?
C21 O1 C10 C9 179.6(5) . . . . ?
C21 C12 C11 C2 178.2(5) . . . . ?
C21 C12 C11 C10 0.9(6) . . . . ?
C21 C12 C13 C18 1.6(7) . . . . ?
C21 C12 C13 C14 -177.6(5) . . . . ?
C21 C20 C19 C18 -0.1(8) . . . . ?
C14 C13 C18 C17 -1.4(7) . . . . ?
C14 C13 C18 C19 177.6(5) . . . . ?
C17 C18 C19 C20 179.9(6) . . . . ?
C17 C16 C15 C14 -0.4(9) . . . . ?
C19 C18 C17 C16 -178.1(5) . . . . ?
C7 C6 C5 C4 0.3(8) . . . . ?

_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 1.239
_oxdiff_exptl_absorpt_empirical_full_min 0.800
####################################################################### 
# 
# 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_20211102-zzx-836
_database_code_depnum_ccdc_archive 'CCDC 2151487'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2021-11-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 Br O'
_chemical_formula_sum            'C27 H19 Br O'
_chemical_formula_weight         439.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H19 Br O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.7121(3)
_cell_length_b                   8.8820(4)
_cell_length_c                   13.2952(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.023(4)
_cell_angle_gamma                90
_cell_volume                     1018.72(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3242
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2690
_cell_measurement_theta_min      4.2810
_shelx_estimated_absorpt_T_max   0.512
_shelx_estimated_absorpt_T_min   0.482
_exptl_absorpt_coefficient_mu    2.033
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8304
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.047
_diffrn_reflns_theta_min         3.495
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  30.00   1.00    2.00    --   18.74  77.00-180.00   26
  2  ω    -42.00  40.00   1.00    2.00    --   18.74 -57.00  60.00   82
  3  ω    -42.00  11.00   1.00    2.00    --  -18.85 -77.00 -30.00   53
  4  ω    -91.00 -65.00   1.00    2.00    --  -18.85-178.00   0.00   26
  5  ω    -24.00   8.00   1.00    2.00    --  -18.85 -77.00-150.00   32
  6  ω    -39.00  50.00   1.00    2.00    --  -18.85  57.00-150.00   89
  7  ω    -88.00   3.00   1.00    2.00    --  -18.85 -57.00  60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0043716000
_diffrn_orient_matrix_UB_12      -0.0233048000
_diffrn_orient_matrix_UB_13      0.0505414000
_diffrn_orient_matrix_UB_21      0.0075803000
_diffrn_orient_matrix_UB_22      0.0759316000
_diffrn_orient_matrix_UB_23      0.0164401000
_diffrn_orient_matrix_UB_31      -0.0817802000
_diffrn_orient_matrix_UB_32      0.0082560000
_diffrn_orient_matrix_UB_33      -0.0087433000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                3735
_reflns_number_total             4625
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1379 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.053
_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)+(0.0271P)²+0.0254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0842
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C20(H20), C18(H18), C23(H23), C24(H24), C27(H27),
 C14(H14), C5(H5), C26(H26), C3(H3), C25(H25), C4(H4), C6(H6)
;
_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 0.21893(4) 0.70149(7) 0.79351(3) 0.04638(15) Uani 1 1 d . . . . .
O1 O 0.7265(4) 0.4436(5) 0.8601(3) 0.0576(12) Uani 1 1 d . . . . .
C21 C 0.4675(5) 0.5616(6) 0.6266(4) 0.0403(12) Uani 1 1 d . . . . .
C7 C 0.4035(7) 0.4504(7) 1.0201(5) 0.0454(15) Uani 1 1 d . . . . .
C11 C 0.4114(5) 0.4435(6) 0.7973(4) 0.0376(11) Uani 1 1 d . . . . .
C12 C 0.5126(5) 0.5059(5) 0.7269(4) 0.0400(12) Uani 1 1 d . . . . .
C16 C 0.5813(6) 0.6277(6) 0.5738(4) 0.0503(14) Uani 1 1 d . . . . .
C2 C 0.2733(6) 0.4710(6) 0.9453(4) 0.0445(12) Uani 1 1 d . . . . .
C19 C 0.2721(6) 0.6005(6) 0.4787(4) 0.0450(13) Uani 1 1 d . . . . .
C15 C 0.7383(6) 0.6295(6) 0.6206(5) 0.0579(15) Uani 1 1 d . . . . .
H15 H 0.813140 0.674297 0.586917 0.069 Uiso 1 1 calc R U . . .
C22 C 0.1119(6) 0.5843(6) 0.4248(4) 0.0457(13) Uani 1 1 d . . . . .
C17 C 0.5355(6) 0.6826(9) 0.4751(4) 0.0632(17) Uani 1 1 d . . . . .
H17 H 0.608378 0.728859 0.440495 0.076 Uiso 1 1 calc R U . . .
C1 C 0.3069(5) 0.5137(5) 0.8431(4) 0.0386(12) Uani 1 1 d . . . . .
C20 C 0.3138(6) 0.5505(6) 0.5764(4) 0.0418(12) Uani 1 1 d . . . . .
H20 H 0.238469 0.507834 0.610620 0.050 Uiso 1 1 calc R U . . .
C18 C 0.3871(6) 0.6692(7) 0.4293(4) 0.0620(19) Uani 1 1 d . . . . .
H18 H 0.360432 0.706254 0.363796 0.074 Uiso 1 1 calc R U . . .
C23 C 0.0105(7) 0.4749(7) 0.4512(4) 0.0541(14) Uani 1 1 d . . . . .
H23 H 0.043845 0.409574 0.504463 0.065 Uiso 1 1 calc R U . . .
C13 C 0.6687(6) 0.5039(6) 0.7669(4) 0.0480(14) Uani 1 1 d . . . . .
C24 C -0.1377(7) 0.4606(8) 0.4009(5) 0.0636(17) Uani 1 1 d . . . . .
H24 H -0.203382 0.387407 0.421062 0.076 Uiso 1 1 calc R U . . .
C27 C 0.0564(7) 0.6799(9) 0.3443(4) 0.0687(18) Uani 1 1 d . . . . .
H27 H 0.119697 0.755581 0.324684 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7805(6) 0.5678(7) 0.7125(5) 0.0580(16) Uani 1 1 d . . . . .
H14 H 0.884400 0.567239 0.740569 0.070 Uiso 1 1 calc R U . . .
C5 C 0.2299(10) 0.4053(9) 1.1432(6) 0.076(2) Uani 1 1 d . . . . .
H5 H 0.215507 0.382796 1.209511 0.091 Uiso 1 1 calc R U . . .
C26 C -0.0934(8) 0.6621(7) 0.2935(5) 0.075(2) Uani 1 1 d . . . . .
H26 H -0.128432 0.725850 0.239658 0.091 Uiso 1 1 calc R U . . .
C10 C 0.4851(6) 0.3037(6) 0.8477(4) 0.0467(13) Uani 1 1 d . . . . .
H10A H 0.413951 0.251403 0.885618 0.056 Uiso 1 1 calc R U . . .
H10B H 0.518424 0.235341 0.798127 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5674(7) 0.4731(8) 0.9960(5) 0.0485(16) Uani 1 1 d . . . . .
H8A H 0.638249 0.464010 1.058857 0.058 Uiso 1 1 calc R U . . .
H8B H 0.575789 0.575237 0.971605 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1250(6) 0.4624(8) 0.9713(5) 0.0650(17) Uani 1 1 d . . . . .
H3 H 0.039559 0.479468 0.922446 0.078 Uiso 1 1 calc R U . . .
C25 C -0.1890(8) 0.5541(8) 0.3207(5) 0.0692(18) Uani 1 1 d . . . . .
H25 H -0.288448 0.543167 0.285647 0.083 Uiso 1 1 calc R U . . .
C9 C 0.6222(6) 0.3654(7) 0.9178(5) 0.0539(15) Uani 1 1 d . . . . .
H9 H 0.677948 0.281293 0.954037 0.065 Uiso 1 1 calc R U . . .
C4 C 0.1040(8) 0.4283(9) 1.0705(5) 0.082(2) Uani 1 1 d . . . . .
H4 H 0.004349 0.421122 1.087652 0.098 Uiso 1 1 calc R U . . .
C6 C 0.3764(8) 0.4153(7) 1.1181(5) 0.0624(17) Uani 1 1 d . . . . .
H6 H 0.460536 0.398234 1.168079 0.075 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.914(5) . ?
O1 C13 1.379(7) . ?
O1 C9 1.446(7) . ?
C21 C12 1.425(7) . ?
C21 C16 1.419(7) . ?
C21 C20 1.414(7) . ?
C7 C2 1.412(8) . ?
C7 C8 1.520(7) . ?
C7 C6 1.392(9) . ?
C11 C12 1.480(7) . ?
C11 C1 1.321(6) . ?
C11 C10 1.512(7) . ?
C12 C13 1.389(7) . ?
C16 C15 1.421(7) . ?
C16 C17 1.405(7) . ?
C2 C1 1.479(7) . ?
C2 C3 1.385(7) . ?
C19 C22 1.484(7) . ?
C19 C20 1.372(7) . ?
C19 C18 1.411(7) . ?
C15 H15 0.9300 . ?
C15 C14 1.343(8) . ?
C22 C23 1.391(8) . ?
C22 C27 1.398(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.355(7) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.374(8) . ?
C13 C14 1.411(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.376(9) . ?
C27 H27 0.9300 . ?
C27 C26 1.392(8) . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.372(9) . ?
C5 C6 1.366(9) . ?
C26 H26 0.9300 . ?
C26 C25 1.353(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.511(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.537(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(8) . ?
C25 H25 0.9300 . ?
C9 H9 0.9800 . ?
C4 H4 0.9300 . ?
C6 H6 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
C13 O1 C9 119.0(4) . . ?
C16 C21 C12 119.1(5) . . ?
C20 C21 C12 122.5(4) . . ?
C20 C21 C16 118.4(5) . . ?
C2 C7 C8 121.4(5) . . ?
C6 C7 C2 117.6(6) . . ?
C6 C7 C8 120.9(5) . . ?
C12 C11 C10 109.6(4) . . ?
C1 C11 C12 128.6(5) . . ?
C1 C11 C10 117.4(4) . . ?
C21 C12 C11 127.7(4) . . ?
C13 C12 C21 119.3(5) . . ?
C13 C12 C11 113.0(5) . . ?
C21 C16 C15 119.0(5) . . ?
C17 C16 C21 118.6(5) . . ?
C17 C16 C15 122.4(5) . . ?
C7 C2 C1 116.0(5) . . ?
C3 C2 C7 120.2(5) . . ?
C3 C2 C1 123.7(5) . . ?
C20 C19 C22 122.1(5) . . ?
C20 C19 C18 118.0(5) . . ?
C18 C19 C22 119.9(5) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 H15 119.4 . . ?
C23 C22 C19 122.3(5) . . ?
C23 C22 C27 116.9(5) . . ?
C27 C22 C19 120.8(5) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(5) . . ?
C18 C17 H17 119.4 . . ?
C11 C1 Br1 121.4(4) . . ?
C11 C1 C2 122.7(4) . . ?
C2 C1 Br1 114.8(4) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 C21 122.1(5) . . ?
C19 C20 H20 118.9 . . ?
C19 C18 H18 119.2 . . ?
C17 C18 C19 121.6(5) . . ?
C17 C18 H18 119.2 . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.9(6) . . ?
C24 C23 H23 119.1 . . ?
O1 C13 C12 124.4(5) . . ?
O1 C13 C14 115.2(5) . . ?
C12 C13 C14 120.5(5) . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(7) . . ?
C25 C24 H24 119.9 . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.2(6) . . ?
C26 C27 H27 119.9 . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.1(6) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 C27 121.4(6) . . ?
C25 C26 H26 119.3 . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
C9 C10 C11 103.1(4) . . ?
C9 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C7 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C7 C8 C9 116.7(5) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(6) . . ?
C4 C3 H3 120.0 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.3(6) . . ?
C26 C25 H25 120.3 . . ?
O1 C9 C10 110.4(5) . . ?
O1 C9 C8 109.7(5) . . ?
O1 C9 H9 108.7 . . ?
C10 C9 C8 110.5(5) . . ?
C10 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C7 C6 H6 119.0 . . ?
C5 C6 C7 121.9(6) . . ?
C5 C6 H6 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C15 179.7(5) . . . . ?
C21 C12 C13 O1 -175.5(5) . . . . ?
C21 C12 C13 C14 5.3(8) . . . . ?
C21 C16 C15 C14 1.1(9) . . . . ?
C21 C16 C17 C18 -1.9(10) . . . . ?
C7 C2 C1 Br1 -120.6(5) . . . . ?
C7 C2 C1 C11 47.6(7) . . . . ?
C7 C2 C3 C4 -2.2(10) . . . . ?
C7 C8 C9 O1 146.6(4) . . . . ?
C7 C8 C9 C10 24.7(7) . . . . ?
C11 C12 C13 O1 3.1(7) . . . . ?
C11 C12 C13 C14 -176.0(5) . . . . ?
C11 C10 C9 O1 -60.5(5) . . . . ?
C11 C10 C9 C8 61.0(6) . . . . ?
C12 C21 C16 C15 3.1(8) . . . . ?
C12 C21 C16 C17 -179.8(5) . . . . ?
C12 C21 C20 C19 -178.1(5) . . . . ?
C12 C11 C1 Br1 20.4(7) . . . . ?
C12 C11 C1 C2 -147.0(5) . . . . ?
C12 C11 C10 C9 70.2(5) . . . . ?
C12 C13 C14 C15 -1.0(8) . . . . ?
C16 C21 C12 C11 175.3(5) . . . . ?
C16 C21 C12 C13 -6.3(8) . . . . ?
C16 C21 C20 C19 0.4(7) . . . . ?
C16 C15 C14 C13 -2.3(9) . . . . ?
C16 C17 C18 C19 0.3(11) . . . . ?
C2 C7 C8 C9 -63.9(7) . . . . ?
C2 C7 C6 C5 -2.0(10) . . . . ?
C2 C3 C4 C5 1.0(12) . . . . ?
C19 C22 C23 C24 -179.9(5) . . . . ?
C19 C22 C27 C26 179.1(5) . . . . ?
C15 C16 C17 C18 175.0(6) . . . . ?
C22 C19 C20 C21 178.0(5) . . . . ?
C22 C19 C18 C17 -178.3(6) . . . . ?
C22 C23 C24 C25 1.1(9) . . . . ?
C22 C27 C26 C25 0.6(10) . . . . ?
C17 C16 C15 C14 -175.8(6) . . . . ?
C1 C11 C12 C21 -68.0(8) . . . . ?
C1 C11 C12 C13 113.5(6) . . . . ?
C1 C11 C10 C9 -88.4(5) . . . . ?
C1 C2 C3 C4 -176.9(6) . . . . ?
C20 C21 C12 C11 -6.2(8) . . . . ?
C20 C21 C12 C13 172.2(5) . . . . ?
C20 C21 C16 C15 -175.4(5) . . . . ?
C20 C21 C16 C17 1.6(8) . . . . ?
C20 C19 C22 C23 -23.8(8) . . . . ?
C20 C19 C22 C27 156.3(5) . . . . ?
C20 C19 C18 C17 1.7(9) . . . . ?
C18 C19 C22 C23 156.2(6) . . . . ?
C18 C19 C22 C27 -23.8(8) . . . . ?
C18 C19 C20 C21 -2.0(8) . . . . ?
C23 C22 C27 C26 -0.9(9) . . . . ?
C23 C24 C25 C26 -1.4(10) . . . . ?
C13 O1 C9 C10 25.4(7) . . . . ?
C13 O1 C9 C8 -96.5(6) . . . . ?
C27 C22 C23 C24 0.0(9) . . . . ?
C27 C26 C25 C24 0.5(10) . . . . ?
C10 C11 C12 C21 136.4(5) . . . . ?
C10 C11 C12 C13 -42.1(6) . . . . ?
C10 C11 C1 Br1 174.3(3) . . . . ?
C10 C11 C1 C2 6.9(7) . . . . ?
C8 C7 C2 C1 0.7(8) . . . . ?
C8 C7 C2 C3 -174.4(5) . . . . ?
C8 C7 C6 C5 175.1(6) . . . . ?
C3 C2 C1 Br1 54.3(7) . . . . ?
C3 C2 C1 C11 -137.5(6) . . . . ?
C9 O1 C13 C12 5.5(8) . . . . ?
C9 O1 C13 C14 -175.3(5) . . . . ?
C4 C5 C6 C7 0.8(11) . . . . ?
C6 C7 C2 C1 177.8(6) . . . . ?
C6 C7 C2 C3 2.7(9) . . . . ?
C6 C7 C8 C9 119.1(7) . . . . ?
C6 C5 C4 C3 -0.2(12) . . . . ?

_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 1.066
_oxdiff_exptl_absorpt_empirical_full_min 0.929
####################################################################### 
# 
# 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_20220111-lk-zzx-483
_database_code_depnum_ccdc_archive 'CCDC 2151488'
loop_
_audit_author_name
_audit_author_address
'Mr. Xiangnan Gong'
;Analytical and Testing Center of Chongqing University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2022-01-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Br O'
_chemical_formula_sum            'C22 H17 Br O'
_chemical_formula_weight         377.26
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6693(2)
_cell_length_b                   13.0042(5)
_cell_length_c                   17.0867(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1704.11(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2396
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4730
_cell_measurement_theta_min      3.8920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6671
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.983
_diffrn_reflns_theta_min         3.352
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  25.00   1.00    6.70    --   18.74  77.00-150.00   36
  2  ω    -50.00  12.00   1.00    6.70    --   18.74 -57.00 -60.00   62
  3  ω     -2.00  91.00   1.00    6.70    --   18.74  38.00 -60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0770358000
_diffrn_orient_matrix_UB_12      -0.0020302000
_diffrn_orient_matrix_UB_13      0.0229426000
_diffrn_orient_matrix_UB_21      0.0511518000
_diffrn_orient_matrix_UB_22      -0.0064591000
_diffrn_orient_matrix_UB_23      0.0342314000
_diffrn_orient_matrix_UB_31      0.0031716000
_diffrn_orient_matrix_UB_32      0.0541095000
_diffrn_orient_matrix_UB_33      0.0049384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                2775
_reflns_number_total             3886
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 878 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.040
_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)+(0.0267P)²+0.2819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0841
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C20(H20), C3(H3), C17(H17), C15(H15), C4(H4), C18(H18), C16(H16),
 C1(H1), C2(H2)
;
_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 0.71057(6) 0.49154(4) 0.56831(3) 0.0606(2) Uani 1 1 d . . . . .
O1 O 0.3927(5) 0.7881(2) 0.6484(2) 0.0552(10) Uani 1 1 d . . . . .
C14 C 0.7235(6) 0.6305(3) 0.7492(3) 0.0395(11) Uani 1 1 d . . . . .
C8 C 0.4530(6) 0.5865(3) 0.6628(3) 0.0357(11) Uani 1 1 d . . . . .
C22 C 0.5367(7) 0.7591(4) 0.6905(3) 0.0445(12) Uani 1 1 d . . . . .
C7 C 0.4789(6) 0.5208(3) 0.6045(3) 0.0399(11) Uani 1 1 d . . . . .
C13 C 0.5801(6) 0.6569(3) 0.7000(3) 0.0393(11) Uani 1 1 d . . . . .
C19 C 0.8277(7) 0.7102(3) 0.7812(3) 0.0427(12) Uani 1 1 d . . . . .
C21 C 0.6449(8) 0.8376(4) 0.7194(3) 0.0513(14) Uani 1 1 d . . . . .
H21 H 0.618705 0.906023 0.708792 0.062 Uiso 1 1 calc R U . . .
C9 C 0.2725(6) 0.6177(3) 0.6873(3) 0.0469(12) Uani 1 1 d . . . . .
H9A H 0.264241 0.619265 0.743900 0.056 Uiso 1 1 calc R U . . .
H9B H 0.187798 0.568681 0.667586 0.056 Uiso 1 1 calc R U . . .
C20 C 0.7875(8) 0.8137(3) 0.7627(3) 0.0518(13) Uani 1 1 d . . . . .
H20 H 0.859880 0.866050 0.780578 0.062 Uiso 1 1 calc R U . . .
C3 C 0.0732(7) 0.3945(4) 0.4632(3) 0.0584(15) Uani 1 1 d . . . . .
H3 H -0.016273 0.367274 0.432908 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3391(6) 0.4768(3) 0.5548(3) 0.0406(11) Uani 1 1 d . . . . .
C5 C 0.2295(7) 0.5430(3) 0.5125(3) 0.0448(12) Uani 1 1 d . . . . .
C17 C 0.9950(7) 0.5847(4) 0.8540(3) 0.0532(14) Uani 1 1 d . . . . .
H17 H 1.083995 0.569343 0.889049 0.064 Uiso 1 1 calc R U . . .
C15 C 0.7621(6) 0.5278(3) 0.7711(3) 0.0487(13) Uani 1 1 d . . . . .
H15 H 0.697436 0.474080 0.749935 0.058 Uiso 1 1 calc R U . . .
C4 C 0.0958(6) 0.4998(4) 0.4679(3) 0.0536(13) Uani 1 1 d . . . . .
H4 H 0.020224 0.542879 0.440740 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2547(7) 0.6592(3) 0.5109(3) 0.0530(15) Uani 1 1 d . . . . .
H12A H 0.219473 0.683934 0.459682 0.064 Uiso 1 1 calc R U . . .
H12B H 0.378338 0.673366 0.516337 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2359(7) 0.7248(4) 0.6535(3) 0.0521(14) Uani 1 1 d . . . . .
H10 H 0.153231 0.759546 0.688347 0.063 Uiso 1 1 calc R U . . .
C18 C 0.9645(7) 0.6835(4) 0.8331(3) 0.0530(14) Uani 1 1 d . . . . .
H18 H 1.035178 0.735173 0.853369 0.064 Uiso 1 1 calc R U . . .
C16 C 0.8933(6) 0.5066(4) 0.8231(3) 0.0540(13) Uani 1 1 d . . . . .
H16 H 0.914396 0.438900 0.837811 0.065 Uiso 1 1 calc R U . . .
C1 C 0.3160(7) 0.3704(3) 0.5490(3) 0.0489(13) Uani 1 1 d . . . . .
H1 H 0.390582 0.326546 0.576036 0.059 Uiso 1 1 calc R U . . .
C2 C 0.1845(8) 0.3296(4) 0.5039(3) 0.0553(15) Uani 1 1 d . . . . .
H2 H 0.170332 0.258679 0.500604 0.066 Uiso 1 1 calc R U . . .
C11 C 0.1574(7) 0.7220(3) 0.5727(4) 0.0613(15) Uani 1 1 d . . . . .
H11A H 0.147679 0.792115 0.553879 0.074 Uiso 1 1 calc R U . . .
H11B H 0.039990 0.694722 0.576929 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
Br1 C7 1.920(4) . ?
O1 C22 1.371(6) . ?
O1 C10 1.460(6) . ?
C14 C13 1.427(6) . ?
C14 C19 1.418(6) . ?
C14 C15 1.419(6) . ?
C8 C7 1.327(6) . ?
C8 C13 1.480(6) . ?
C8 C9 1.502(6) . ?
C22 C13 1.380(6) . ?
C22 C21 1.405(7) . ?
C7 C6 1.481(6) . ?
C19 C20 1.417(6) . ?
C19 C18 1.417(7) . ?
C21 H21 0.9300 . ?
C21 C20 1.357(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.533(6) . ?
C20 H20 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.383(7) . ?
C3 C2 1.387(7) . ?
C6 C5 1.403(6) . ?
C6 C1 1.400(6) . ?
C5 C4 1.396(6) . ?
C5 C12 1.524(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.353(7) . ?
C17 C16 1.385(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(6) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.529(7) . ?
C10 H10 0.9800 . ?
C10 C11 1.508(7) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.376(7) . ?
C2 H2 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 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
C22 O1 C10 118.5(4) . . ?
C19 C14 C13 119.1(4) . . ?
C19 C14 C15 117.9(4) . . ?
C15 C14 C13 122.9(4) . . ?
C7 C8 C13 128.5(4) . . ?
C7 C8 C9 121.3(4) . . ?
C13 C8 C9 108.7(4) . . ?
O1 C22 C13 121.4(5) . . ?
O1 C22 C21 117.4(4) . . ?
C13 C22 C21 121.1(5) . . ?
C8 C7 Br1 120.5(4) . . ?
C8 C7 C6 124.8(4) . . ?
C6 C7 Br1 114.1(3) . . ?
C14 C13 C8 127.7(4) . . ?
C22 C13 C14 119.1(4) . . ?
C22 C13 C8 112.8(4) . . ?
C20 C19 C14 119.0(5) . . ?
C20 C19 C18 122.2(5) . . ?
C18 C19 C14 118.7(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.1(5) . . ?
C20 C21 H21 120.0 . . ?
C8 C9 H9A 110.1 . . ?
C8 C9 H9B 110.1 . . ?
C8 C9 C10 108.0(4) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C5 C6 C7 119.4(4) . . ?
C1 C6 C7 121.0(4) . . ?
C1 C6 C5 119.6(4) . . ?
C6 C5 C12 122.8(4) . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 C12 118.8(4) . . ?
C18 C17 H17 120.1 . . ?
C18 C17 C16 119.9(5) . . ?
C16 C17 H17 120.1 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(5) . . ?
C16 C15 H15 119.5 . . ?
C3 C4 C5 121.5(5) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C5 C12 H12A 108.0 . . ?
C5 C12 H12B 108.0 . . ?
C5 C12 C11 117.0(4) . . ?
H12A C12 H12B 107.3 . . ?
C11 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
O1 C10 C9 112.6(4) . . ?
O1 C10 H10 108.0 . . ?
O1 C10 C11 106.8(4) . . ?
C9 C10 H10 108.0 . . ?
C11 C10 C9 113.3(4) . . ?
C11 C10 H10 108.0 . . ?
C19 C18 H18 119.2 . . ?
C17 C18 C19 121.7(5) . . ?
C17 C18 H18 119.2 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.9(5) . . ?
C15 C16 H16 119.6 . . ?
C6 C1 H1 119.5 . . ?
C2 C1 C6 120.9(5) . . ?
C2 C1 H1 119.5 . . ?
C3 C2 H2 120.1 . . ?
C1 C2 C3 119.8(5) . . ?
C1 C2 H2 120.1 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C10 C11 C12 116.8(4) . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?

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
Br1 C7 C6 C5 -112.9(4) . . . . ?
Br1 C7 C6 C1 66.5(5) . . . . ?
O1 C22 C13 C14 -175.3(4) . . . . ?
O1 C22 C13 C8 -2.0(7) . . . . ?
O1 C22 C21 C20 178.8(4) . . . . ?
O1 C10 C11 C12 71.4(5) . . . . ?
C14 C19 C20 C21 4.4(7) . . . . ?
C14 C19 C18 C17 -1.5(7) . . . . ?
C14 C15 C16 C17 -1.8(7) . . . . ?
C8 C7 C6 C5 58.2(6) . . . . ?
C8 C7 C6 C1 -122.4(5) . . . . ?
C8 C9 C10 O1 -32.3(6) . . . . ?
C8 C9 C10 C11 89.0(5) . . . . ?
C22 O1 C10 C9 -16.6(6) . . . . ?
C22 O1 C10 C11 -141.5(4) . . . . ?
C22 C21 C20 C19 -1.5(7) . . . . ?
C7 C8 C13 C14 -70.5(7) . . . . ?
C7 C8 C13 C22 117.0(5) . . . . ?
C7 C8 C9 C10 -102.0(5) . . . . ?
C7 C6 C5 C4 -178.2(4) . . . . ?
C7 C6 C5 C12 4.2(7) . . . . ?
C7 C6 C1 C2 179.0(4) . . . . ?
C13 C14 C19 C20 -0.6(7) . . . . ?
C13 C14 C19 C18 177.0(4) . . . . ?
C13 C14 C15 C16 -175.2(4) . . . . ?
C13 C8 C7 Br1 10.2(7) . . . . ?
C13 C8 C7 C6 -160.4(4) . . . . ?
C13 C8 C9 C10 65.1(5) . . . . ?
C13 C22 C21 C20 -5.3(8) . . . . ?
C19 C14 C13 C8 -178.1(4) . . . . ?
C19 C14 C13 C22 -6.0(7) . . . . ?
C19 C14 C15 C16 1.6(7) . . . . ?
C21 C22 C13 C14 9.0(7) . . . . ?
C21 C22 C13 C8 -177.7(4) . . . . ?
C9 C8 C7 Br1 174.5(3) . . . . ?
C9 C8 C7 C6 4.0(7) . . . . ?
C9 C8 C13 C14 123.6(5) . . . . ?
C9 C8 C13 C22 -48.9(5) . . . . ?
C9 C10 C11 C12 -53.1(6) . . . . ?
C20 C19 C18 C17 176.0(5) . . . . ?
C6 C5 C4 C3 -1.8(7) . . . . ?
C6 C5 C12 C11 -91.4(6) . . . . ?
C6 C1 C2 C3 0.2(8) . . . . ?
C5 C6 C1 C2 -1.6(7) . . . . ?
C5 C12 C11 C10 79.4(6) . . . . ?
C15 C14 C13 C8 -1.3(7) . . . . ?
C15 C14 C13 C22 170.8(5) . . . . ?
C15 C14 C19 C20 -177.5(4) . . . . ?
C15 C14 C19 C18 0.0(7) . . . . ?
C4 C3 C2 C1 0.4(8) . . . . ?
C4 C5 C12 C11 91.0(5) . . . . ?
C12 C5 C4 C3 175.9(5) . . . . ?
C10 O1 C22 C13 36.9(7) . . . . ?
C10 O1 C22 C21 -147.2(4) . . . . ?
C18 C19 C20 C21 -173.1(5) . . . . ?
C18 C17 C16 C15 0.3(8) . . . . ?
C16 C17 C18 C19 1.4(8) . . . . ?
C1 C6 C5 C4 2.3(6) . . . . ?
C1 C6 C5 C12 -175.3(4) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?

_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 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.779
