# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_t
_audit_block_doi                 10.5517/ccdc.csd.cc27fbrs
_database_code_depnum_ccdc_archive 'CCDC 2068405'
loop_
_audit_author_name
_audit_author_address
JNQ
;Soochow University
China
;
_audit_update_record             
;
2021-03-06 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 Br2 O'
_chemical_formula_sum            'C22 H16 Br2 O'
_chemical_formula_weight         456.17

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.7279(9)
_cell_length_b                   9.0758(14)
_cell_length_c                   17.852(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.135(5)
_cell_angle_gamma                90
_cell_volume                     925.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   0.2803
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.385
_shelx_estimated_absorpt_T_min   0.178
_shelx_estimated_absorpt_T_max   0.474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20721
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3332
_reflns_number_gt                3101
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.989

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.6918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1330 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.162(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3332
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002

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 0.69098(19) 0.51848(12) 1.15598(5) 0.0472(3) Uani 1 1 d . . . . .
Br2 Br 0.51935(17) 0.88969(13) 0.50174(5) 0.0402(3) Uani 1 1 d . . . . .
O1 O -0.1870(13) 0.7479(8) 0.8011(4) 0.0454(18) Uani 1 1 d . . . . .
C1 C 0.5326(17) 0.4995(10) 1.0588(5) 0.0325(19) Uani 1 1 d . . . . .
C4 C 0.3110(17) 0.4675(9) 0.9171(5) 0.0302(19) Uani 1 1 d . . . . .
C2 C 0.674(3) 0.468(2) 1.0023(11) 0.035(4) Uani 0.5 1 d . . P A 1
H2 H 0.8351 0.4558 1.0108 0.042 Uiso 0.5 1 calc R U P A 1
C3 C 0.558(4) 0.4548(19) 0.9303(10) 0.030(4) Uani 0.5 1 d . . P A 1
H3 H 0.6471 0.4371 0.8896 0.036 Uiso 0.5 1 calc R U P A 1
C5 C 0.192(3) 0.501(2) 0.9805(10) 0.031(4) Uani 0.5 1 d . . P A 1
H5 H 0.0319 0.5184 0.9741 0.037 Uiso 0.5 1 calc R U P A 1
C6 C 0.299(3) 0.509(2) 1.0524(9) 0.033(4) Uani 0.5 1 d . . P A 1
H6 H 0.2129 0.5200 1.0942 0.039 Uiso 0.5 1 calc R U P A 1
C2A C 0.551(3) 0.6074(18) 1.0007(11) 0.036(4) Uani 0.5 1 d . . P A 2
H2A H 0.6415 0.6912 1.0110 0.043 Uiso 0.5 1 calc R U P A 2
C3A C 0.441(4) 0.591(2) 0.9307(11) 0.035(4) Uani 0.5 1 d . . P A 2
H3A H 0.4536 0.6620 0.8937 0.042 Uiso 0.5 1 calc R U P A 2
C5A C 0.289(4) 0.357(2) 0.9715(11) 0.032(4) Uani 0.5 1 d . . P A 2
H5A H 0.2006 0.2728 0.9606 0.038 Uiso 0.5 1 calc R U P A 2
C6A C 0.402(4) 0.378(3) 1.0413(10) 0.038(4) Uani 0.5 1 d . . P A 2
H6A H 0.3880 0.3057 1.0778 0.046 Uiso 0.5 1 calc R U P A 2
C7 C 0.2032(18) 0.4476(11) 0.8402(5) 0.035(2) Uani 1 1 d . . . . .
H7 H 0.2445 0.3612 0.8165 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0544(14) 0.5354(9) 0.7994(4) 0.0265(17) Uani 1 1 d . . . . .
C9 C -0.0376(16) 0.6716(9) 0.8326(5) 0.033(2) Uani 1 1 d . . . . .
H9 H 0.0231 0.6997 0.8801 0.040 Uiso 1 1 calc R U . . .
C10 C -0.0256(14) 0.5065(10) 0.7181(5) 0.0262(16) Uani 1 1 d . . . . .
H10 H -0.1903 0.5360 0.7111 0.031 Uiso 1 1 calc R U . . .
C11 C -0.0131(15) 0.3433(9) 0.6987(5) 0.0255(18) Uani 1 1 d . . . . .
C12 C -0.1905(17) 0.2506(10) 0.7216(7) 0.037(2) Uani 1 1 d . . . . .
H12 H -0.3130 0.2903 0.7465 0.044 Uiso 1 1 calc R U . . .
C13 C -0.1852(17) 0.0991(10) 0.7074(6) 0.039(2) Uani 1 1 d . . . . .
H13 H -0.3048 0.0384 0.7219 0.046 Uiso 1 1 calc R U . . .
C14 C -0.0006(17) 0.0408(9) 0.6717(5) 0.034(2) Uani 1 1 d . . . . .
H14 H 0.0045 -0.0598 0.6621 0.041 Uiso 1 1 calc R U . . .
C15 C 0.1778(17) 0.1316(12) 0.6500(5) 0.0348(19) Uani 1 1 d . . . . .
H15 H 0.3033 0.0921 0.6265 0.042 Uiso 1 1 calc R U . . .
C16 C 0.1669(16) 0.2812(9) 0.6637(5) 0.0286(19) Uani 1 1 d . . . . .
H16 H 0.2861 0.3416 0.6486 0.034 Uiso 1 1 calc R U . . .
C17 C 0.1111(15) 0.6023(8) 0.6661(5) 0.0256(18) Uani 1 1 d . . . . .
C18 C 0.3253(15) 0.6654(9) 0.6891(5) 0.0277(18) Uani 1 1 d . . . . .
H18 H 0.3891 0.6506 0.7379 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4447(16) 0.7502(9) 0.6400(5) 0.0263(18) Uani 1 1 d . . . . .
H19 H 0.5870 0.7930 0.6562 0.032 Uiso 1 1 calc R U . . .
C20 C 0.3551(15) 0.7714(8) 0.5681(5) 0.0257(18) Uani 1 1 d . . . . .
C21 C 0.1394(16) 0.7091(10) 0.5423(5) 0.0296(18) Uani 1 1 d . . . . .
H21 H 0.0777 0.7237 0.4933 0.036 Uiso 1 1 calc R U . . .
C22 C 0.0205(15) 0.6246(10) 0.5927(5) 0.0305(18) Uani 1 1 d . . . . .
H22 H -0.1224 0.5823 0.5768 0.037 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 1.906(9) . ?
Br2 C20 1.897(8) . ?
O1 C9 1.208(12) . ?
C1 C6 1.34(2) . ?
C1 C6A 1.36(2) . ?
C1 C2 1.37(2) . ?
C1 C2A 1.44(2) . ?
C4 C3A 1.36(2) . ?
C4 C5 1.396(19) . ?
C4 C5A 1.41(2) . ?
C4 C3 1.42(2) . ?
C4 C7 1.475(14) . ?
C2 C3 1.41(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C5 C6 1.38(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2A C3A 1.37(3) . ?
C2A H2A 0.9300 . ?
C3A H3A 0.9300 . ?
C5A C6A 1.37(3) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7 C8 1.343(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.483(12) . ?
C8 C10 1.512(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.524(12) . ?
C10 C17 1.529(12) . ?
C10 H10 0.9800 . ?
C11 C16 1.366(13) . ?
C11 C12 1.402(13) . ?
C12 C13 1.399(14) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(14) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(13) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.389(12) . ?
C17 C22 1.389(12) . ?
C18 C19 1.385(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.361(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.406(13) . ?
C21 C22 1.396(13) . ?
C21 H21 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
C6 C1 C2 126.2(13) . . ?
C6A C1 C2A 117.2(12) . . ?
C6 C1 Br1 118.7(9) . . ?
C6A C1 Br1 120.1(10) . . ?
C2 C1 Br1 114.9(10) . . ?
C2A C1 Br1 122.7(10) . . ?
C3A C4 C5A 122.7(14) . . ?
C5 C4 C3 114.9(12) . . ?
C3A C4 C7 117.0(11) . . ?
C5 C4 C7 125.8(11) . . ?
C5A C4 C7 120.2(11) . . ?
C3 C4 C7 119.2(10) . . ?
C1 C2 C3 115.2(16) . . ?
C1 C2 H2 122.4 . . ?
C3 C2 H2 122.4 . . ?
C4 C3 C2 122.8(15) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C6 C5 C4 123.6(15) . . ?
C6 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C1 C6 C5 116.8(14) . . ?
C1 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
C3A C2A C1 122.1(16) . . ?
C3A C2A H2A 118.9 . . ?
C1 C2A H2A 118.9 . . ?
C4 C3A C2A 117.7(17) . . ?
C4 C3A H3A 121.1 . . ?
C2A C3A H3A 121.1 . . ?
C6A C5A C4 118.0(17) . . ?
C6A C5A H5A 121.0 . . ?
C4 C5A H5A 121.0 . . ?
C1 C6A C5A 122.3(17) . . ?
C1 C6A H6A 118.8 . . ?
C5A C6A H6A 118.8 . . ?
C8 C7 C4 129.7(8) . . ?
C8 C7 H7 115.1 . . ?
C4 C7 H7 115.1 . . ?
C7 C8 C9 120.5(8) . . ?
C7 C8 C10 123.6(8) . . ?
C9 C8 C10 115.8(7) . . ?
O1 C9 C8 123.5(9) . . ?
O1 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
C8 C10 C11 111.8(7) . . ?
C8 C10 C17 110.5(7) . . ?
C11 C10 C17 112.4(6) . . ?
C8 C10 H10 107.3 . . ?
C11 C10 H10 107.3 . . ?
C17 C10 H10 107.3 . . ?
C16 C11 C12 118.2(8) . . ?
C16 C11 C10 123.7(7) . . ?
C12 C11 C10 118.0(8) . . ?
C13 C12 C11 120.8(9) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 119.2(9) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.4(8) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.3(9) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C11 C16 C15 122.1(8) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C18 C17 C22 118.7(8) . . ?
C18 C17 C10 122.4(7) . . ?
C22 C17 C10 118.9(8) . . ?
C17 C18 C19 120.5(8) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 120.4(8) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.9(8) . . ?
C19 C20 Br2 119.9(7) . . ?
C21 C20 Br2 119.2(7) . . ?
C22 C21 C20 118.0(8) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
C17 C22 C21 121.4(8) . . ?
C17 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?

_refine_diff_density_max         1.261
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.120

