# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 2120636'
loop_
_audit_author_name
_audit_author_address
'haipeng hu'
;sichuan normal university
China
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H6 Br F O2)'
_chemical_formula_sum            'C16 H12 Br2 F2 O4'
_chemical_formula_weight         466.08
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   18.9959(7)
_cell_length_b                   6.0086(3)
_cell_length_c                   7.7051(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.911(4)
_cell_angle_gamma                90
_cell_volume                     878.96(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4011
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      75.7340
_cell_measurement_theta_min      7.0050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          .
_exptl_crystal_size_mid          .
_exptl_crystal_size_min          .
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2780
_diffrn_reflns_point_group_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.879
_diffrn_reflns_theta_min         2.327
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.551
_reflns_Friedel_fraction_full    0.589
_reflns_Friedel_fraction_max     0.540
_reflns_number_gt                2288
_reflns_number_total             2780
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (version 2014/5)'
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Flack x determined using 687 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.107
_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)+(0.1311P)²+0.1999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1894
_refine_ls_wR_factor_ref         0.2036
_refine_special_details          
;
 Refined as a 2-component twin.
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Br1A Br 0.93230(8) 0.1950(5) 0.6190(3) 0.1593(11) Uani 1 1 d . . . . .
F1A F 0.6001(3) 0.2786(7) 0.2806(6) 0.0591(11) Uani 1 1 d . . . . .
O1A O 0.5363(3) 0.0196(8) 0.4995(7) 0.0511(11) Uani 1 1 d . . . . .
O2A O 0.5781(3) 0.2144(8) 0.7278(7) 0.0531(13) Uani 1 1 d D . . . .
H2OA H 0.558(7) 0.154(19) 0.816(5) 0.13(6) Uiso 1 1 d D . . . .
C1A C 0.5721(4) 0.1686(9) 0.5619(10) 0.0422(14) Uani 1 1 d D . . . .
C2A C 0.6159(4) 0.3225(10) 0.4563(10) 0.0481(16) Uani 1 1 d . . . . .
H2A H 0.602844 0.476534 0.481854 0.058 Uiso 1 1 calc R U . . .
C3A C 0.6934(4) 0.2937(11) 0.4929(10) 0.0487(15) Uani 1 1 d . . . . .
C4A C 0.7321(5) 0.4550(14) 0.5783(11) 0.063(2) Uani 1 1 d . . . . .
H4A H 0.710118 0.586341 0.610449 0.076 Uiso 1 1 calc R U . . .
C5A C 0.8037(5) 0.426(2) 0.6179(15) 0.079(3) Uani 1 1 d . . . . .
H5A H 0.829398 0.534983 0.678283 0.094 Uiso 1 1 calc R U . . .
C6A C 0.8352(6) 0.234(2) 0.5655(17) 0.084(3) Uani 1 1 d . . . . .
C7A C 0.7982(6) 0.0709(19) 0.4767(17) 0.080(3) Uani 1 1 d . . . . .
H7A H 0.820928 -0.057338 0.440659 0.096 Uiso 1 1 calc R U . . .
C8A C 0.7272(5) 0.0990(14) 0.4416(13) 0.065(2) Uani 1 1 d . . . . .
H8A H 0.701671 -0.011862 0.383625 0.078 Uiso 1 1 calc R U . . .
Br1B Br 0.06811(7) 0.6902(4) 0.5434(3) 0.1565(11) Uani 1 1 d . . . . .
F1B F 0.4004(3) 0.7789(7) 0.2655(7) 0.0582(11) Uani 1 1 d . . . . .
O1B O 0.4644(3) 0.5201(8) 0.4947(8) 0.0546(12) Uani 1 1 d . . . . .
O2B O 0.4222(3) 0.7142(9) 0.7136(7) 0.0517(12) Uani 1 1 d D . . . .
H2OB H 0.451(7) 0.61(2) 0.75(2) 0.14(6) Uiso 1 1 d D . . . .
C1B C 0.4286(4) 0.6693(10) 0.5505(10) 0.0423(14) Uani 1 1 d . . . . .
C2B C 0.3854(4) 0.8236(10) 0.4358(9) 0.0468(16) Uani 1 1 d . . . . .
H2B H 0.398368 0.977872 0.463040 0.056 Uiso 1 1 calc R U . . .
C3B C 0.3073(4) 0.7925(11) 0.4600(10) 0.0501(16) Uani 1 1 d . . . . .
C4B C 0.2683(5) 0.9557(15) 0.5406(13) 0.066(2) Uani 1 1 d . . . . .
H4B H 0.290313 1.086177 0.578128 0.079 Uiso 1 1 calc R U . . .
C5B C 0.1969(6) 0.927(2) 0.5660(15) 0.079(3) Uani 1 1 d . . . . .
H5B H 0.170656 1.035746 0.620625 0.094 Uiso 1 1 calc R U . . .
C6B C 0.1658(6) 0.730(2) 0.5068(18) 0.082(3) Uani 1 1 d . . . . .
C7B C 0.2029(6) 0.5688(18) 0.4251(18) 0.083(3) Uani 1 1 d . . . . .
H7B H 0.180541 0.440532 0.384299 0.100 Uiso 1 1 calc R U . . .
C8B C 0.2732(5) 0.5980(13) 0.4041(12) 0.064(2) Uani 1 1 d . . . . .
H8B H 0.298992 0.486584 0.351555 0.077 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
Br1A C6A 1.892(11) . ?
F1A C2A 1.402(9) . ?
O1A C1A 1.213(9) . ?
O2A H2OA 0.87(3) . ?
O2A C1A 1.309(9) . ?
C1A C2A 1.502(9) . ?
C2A H2A 0.9800 . ?
C2A C3A 1.500(12) . ?
C3A C4A 1.371(11) . ?
C3A C8A 1.398(11) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.396(14) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.367(18) . ?
C6A C7A 1.375(19) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.377(14) . ?
C8A H8A 0.9300 . ?
Br1B C6B 1.901(11) . ?
F1B C2B 1.379(9) . ?
O1B C1B 1.213(9) . ?
O2B H2OB 0.86(3) . ?
O2B C1B 1.295(9) . ?
C1B C2B 1.504(9) . ?
C2B H2B 0.9800 . ?
C2B C3B 1.514(11) . ?
C3B C4B 1.389(11) . ?
C3B C8B 1.397(11) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.388(14) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.395(18) . ?
C6B C7B 1.364(18) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.362(14) . ?
C8B H8B 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
C1A O2A H2OA 130(4) . . ?
O1A C1A O2A 124.9(6) . . ?
O1A C1A C2A 123.5(6) . . ?
O2A C1A C2A 111.6(6) . . ?
F1A C2A C1A 107.6(6) . . ?
F1A C2A H2A 108.9 . . ?
F1A C2A C3A 109.7(6) . . ?
C1A C2A H2A 108.9 . . ?
C3A C2A C1A 112.7(6) . . ?
C3A C2A H2A 108.9 . . ?
C4A C3A C2A 121.1(7) . . ?
C4A C3A C8A 118.9(8) . . ?
C8A C3A C2A 120.0(7) . . ?
C3A C4A H4A 119.3 . . ?
C3A C4A C5A 121.4(9) . . ?
C5A C4A H4A 119.3 . . ?
C4A C5A H5A 120.9 . . ?
C6A C5A C4A 118.2(9) . . ?
C6A C5A H5A 120.9 . . ?
C5A C6A Br1A 118.2(9) . . ?
C5A C6A C7A 121.9(10) . . ?
C7A C6A Br1A 119.8(9) . . ?
C6A C7A H7A 120.3 . . ?
C6A C7A C8A 119.4(9) . . ?
C8A C7A H7A 120.3 . . ?
C3A C8A H8A 119.9 . . ?
C7A C8A C3A 120.2(8) . . ?
C7A C8A H8A 119.9 . . ?
C1B O2B H2OB 96(10) . . ?
O1B C1B O2B 124.7(6) . . ?
O1B C1B C2B 123.3(6) . . ?
O2B C1B C2B 112.0(6) . . ?
F1B C2B C1B 108.3(6) . . ?
F1B C2B H2B 109.3 . . ?
F1B C2B C3B 109.1(6) . . ?
C1B C2B H2B 109.3 . . ?
C1B C2B C3B 111.6(6) . . ?
C3B C2B H2B 109.3 . . ?
C4B C3B C2B 120.6(7) . . ?
C4B C3B C8B 118.7(8) . . ?
C8B C3B C2B 120.7(7) . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B C3B 121.0(8) . . ?
C5B C4B H4B 119.5 . . ?
C4B C5B H5B 121.2 . . ?
C4B C5B C6B 117.7(9) . . ?
C6B C5B H5B 121.2 . . ?
C5B C6B Br1B 117.5(9) . . ?
C7B C6B Br1B 120.2(9) . . ?
C7B C6B C5B 122.3(10) . . ?
C6B C7B H7B 120.4 . . ?
C8B C7B C6B 119.2(10) . . ?
C8B C7B H7B 120.4 . . ?
C3B C8B H8B 119.4 . . ?
C7B C8B C3B 121.1(8) . . ?
C7B C8B H8B 119.4 . . ?

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
Br1A C6A C7A C8A 178.7(9) . . . . ?
F1A C2A C3A C4A 129.8(7) . . . . ?
F1A C2A C3A C8A -50.9(9) . . . . ?
O1A C1A C2A F1A 7.3(10) . . . . ?
O1A C1A C2A C3A -113.7(8) . . . . ?
O2A C1A C2A F1A -173.3(6) . . . . ?
O2A C1A C2A C3A 65.6(8) . . . . ?
C1A C2A C3A C4A -110.3(8) . . . . ?
C1A C2A C3A C8A 69.0(9) . . . . ?
C2A C3A C4A C5A 177.9(8) . . . . ?
C2A C3A C8A C7A -179.3(9) . . . . ?
C3A C4A C5A C6A 1.5(15) . . . . ?
C4A C3A C8A C7A 0.0(14) . . . . ?
C4A C5A C6A Br1A 180.0(8) . . . . ?
C4A C5A C6A C7A -0.2(18) . . . . ?
C5A C6A C7A C8A -1.1(19) . . . . ?
C6A C7A C8A C3A 1.2(16) . . . . ?
C8A C3A C4A C5A -1.4(13) . . . . ?
Br1B C6B C7B C8B -178.4(9) . . . . ?
F1B C2B C3B C4B -130.4(8) . . . . ?
F1B C2B C3B C8B 50.5(9) . . . . ?
O1B C1B C2B F1B -6.2(9) . . . . ?
O1B C1B C2B C3B 113.9(8) . . . . ?
O2B C1B C2B F1B 174.2(6) . . . . ?
O2B C1B C2B C3B -65.7(7) . . . . ?
C1B C2B C3B C4B 110.0(8) . . . . ?
C1B C2B C3B C8B -69.1(9) . . . . ?
C2B C3B C4B C5B -178.9(8) . . . . ?
C2B C3B C8B C7B -179.9(9) . . . . ?
C3B C4B C5B C6B -0.4(15) . . . . ?
C4B C3B C8B C7B 1.0(14) . . . . ?
C4B C5B C6B Br1B 179.5(8) . . . . ?
C4B C5B C6B C7B -0.5(18) . . . . ?
C5B C6B C7B C8B 1.7(19) . . . . ?
C6B C7B C8B C3B -1.9(17) . . . . ?
C8B C3B C4B C5B 0.2(14) . . . . ?

