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

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

data_exp_10214
_database_code_depnum_ccdc_archive 'CCDC 1959362'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2019-10-15 deposited with the CCDC.	2019-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H10 Br F O4'
_chemical_formula_weight         389.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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'

_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'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.2599(2)
_cell_length_b                   12.5261(3)
_cell_length_c                   12.6868(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1471.54(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4381
_cell_measurement_theta_min      3.4650
_cell_measurement_theta_max      70.8340

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.115
_shelx_estimated_absorpt_T_min   0.638
_shelx_estimated_absorpt_T_max   0.660
_exptl_absorpt_correction_T_min  0.68841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9322
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.962
_diffrn_reflns_theta_max         67.195
_diffrn_reflns_theta_full        67.195
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2633
_reflns_number_gt                2427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0400P)²+0.1935P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.047(14)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2633
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.98947(6) 0.27003(4) 0.32186(5) 0.0555(2) Uani 1 1 d . . . . .
F1 F 0.6378(3) 0.9615(2) 0.6496(2) 0.0548(8) Uani 1 1 d . . . . .
O1 O 0.4948(4) 0.6409(2) 0.4830(2) 0.0365(7) Uani 1 1 d . . . . .
O2 O 0.4853(4) 0.8130(2) 0.5523(2) 0.0392(7) Uani 1 1 d . . . . .
O3 O 0.6328(4) 0.7628(3) 0.1445(3) 0.0468(8) Uani 1 1 d . . . . .
O4 O 0.7323(3) 0.6175(2) 0.2089(2) 0.0360(7) Uani 1 1 d . . . . .
C1 C 0.8529(5) 0.3805(4) 0.3436(4) 0.0367(10) Uani 1 1 d . . . . .
C2 C 0.7700(6) 0.3796(4) 0.4339(4) 0.0442(12) Uani 1 1 d . . . . .
H2 H 0.779059 0.324656 0.482703 0.053 Uiso 1 1 calc R U . . .
C3 C 0.6735(6) 0.4616(4) 0.4504(4) 0.0409(11) Uani 1 1 d . . . . .
H3 H 0.617112 0.462029 0.511089 0.049 Uiso 1 1 calc R U . . .
C4 C 0.6594(5) 0.5442(3) 0.3769(3) 0.0312(9) Uani 1 1 d . . . . .
C5 C 0.5664(4) 0.6354(3) 0.3890(3) 0.0292(9) Uani 1 1 d . . . . .
C6 C 0.4033(4) 0.7325(4) 0.5015(4) 0.0360(10) Uani 1 1 d . . . . .
H6 H 0.326082 0.710539 0.549724 0.043 Uiso 1 1 calc R U . . .
C7 C 0.5483(4) 0.8903(4) 0.4909(4) 0.0333(10) Uani 1 1 d . . . . .
C8 C 0.6282(5) 0.9677(4) 0.5429(4) 0.0403(11) Uani 1 1 d . . . . .
C9 C 0.6980(6) 1.0470(4) 0.4902(5) 0.0518(14) Uani 1 1 d . . . . .
H9 H 0.750636 1.098099 0.526934 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6897(6) 1.0506(4) 0.3813(5) 0.0558(14) Uani 1 1 d . . . . .
H10 H 0.736836 1.104315 0.344169 0.067 Uiso 1 1 calc R U . . .
C11 C 0.6117(5) 0.9745(4) 0.3286(4) 0.0406(11) Uani 1 1 d . . . . .
H11 H 0.606747 0.977044 0.255451 0.049 Uiso 1 1 calc R U . . .
C12 C 0.5400(4) 0.8939(3) 0.3817(3) 0.0305(9) Uani 1 1 d . . . . .
C13 C 0.4566(4) 0.8055(3) 0.3284(3) 0.0315(9) Uani 1 1 d . . . . .
H13 H 0.418386 0.829770 0.260458 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5539(4) 0.7096(3) 0.3133(3) 0.0284(9) Uani 1 1 d . . . . .
C15 C 0.6376(5) 0.7016(3) 0.2170(3) 0.0328(10) Uani 1 1 d . . . . .
C16 C 0.7437(5) 0.5404(3) 0.2859(3) 0.0309(9) Uani 1 1 d . . . . .
C17 C 0.8421(5) 0.4592(4) 0.2691(4) 0.0350(10) Uani 1 1 d . . . . .
H17 H 0.899332 0.458108 0.208893 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3339(4) 0.7710(4) 0.4010(3) 0.0374(10) Uani 1 1 d . . . . .
H18A H 0.269999 0.830588 0.415239 0.045 Uiso 1 1 calc R U . . .
H18B H 0.278233 0.714110 0.368721 0.045 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 1.895(4) . ?
F1 C8 1.359(5) . ?
O1 C5 1.366(5) . ?
O1 C6 1.445(5) . ?
O2 C7 1.373(5) . ?
O2 C6 1.418(5) . ?
O3 C15 1.199(5) . ?
O4 C15 1.374(5) . ?
O4 C16 1.378(5) . ?
C1 C17 1.370(6) . ?
C1 C2 1.379(7) . ?
C2 C3 1.377(7) . ?
C3 C4 1.400(6) . ?
C4 C16 1.394(6) . ?
C4 C5 1.439(6) . ?
C5 C14 1.341(6) . ?
C6 C18 1.507(6) . ?
C7 C8 1.386(6) . ?
C7 C12 1.388(6) . ?
C8 C9 1.359(7) . ?
C9 C10 1.385(8) . ?
C10 C11 1.371(7) . ?
C11 C12 1.383(6) . ?
C12 C13 1.511(6) . ?
C13 C14 1.513(6) . ?
C13 C18 1.525(6) . ?
C14 C15 1.450(6) . ?
C16 C17 1.381(7) . ?

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
C5 O1 C6 117.8(3) . . ?
C7 O2 C6 118.2(3) . . ?
C15 O4 C16 122.2(3) . . ?
C17 C1 C2 122.5(4) . . ?
C17 C1 Br1 118.3(3) . . ?
C2 C1 Br1 119.1(4) . . ?
C3 C2 C1 118.8(5) . . ?
C2 C3 C4 120.7(5) . . ?
C16 C4 C3 118.3(4) . . ?
C16 C4 C5 116.8(4) . . ?
C3 C4 C5 124.9(4) . . ?
C14 C5 O1 123.3(4) . . ?
C14 C5 C4 121.7(4) . . ?
O1 C5 C4 115.1(4) . . ?
O2 C6 O1 108.9(3) . . ?
O2 C6 C18 112.6(4) . . ?
O1 C6 C18 111.5(4) . . ?
O2 C7 C8 116.8(4) . . ?
O2 C7 C12 124.4(4) . . ?
C8 C7 C12 118.8(4) . . ?
F1 C8 C9 120.0(4) . . ?
F1 C8 C7 117.9(4) . . ?
C9 C8 C7 122.1(5) . . ?
C8 C9 C10 119.2(5) . . ?
C11 C10 C9 119.5(5) . . ?
C10 C11 C12 121.5(5) . . ?
C11 C12 C7 118.9(4) . . ?
C11 C12 C13 124.2(4) . . ?
C7 C12 C13 116.8(4) . . ?
C12 C13 C14 109.5(3) . . ?
C12 C13 C18 108.5(4) . . ?
C14 C13 C18 107.2(3) . . ?
C5 C14 C15 120.6(4) . . ?
C5 C14 C13 120.7(4) . . ?
C15 C14 C13 118.7(4) . . ?
O3 C15 O4 117.1(4) . . ?
O3 C15 C14 125.7(4) . . ?
O4 C15 C14 117.2(4) . . ?
O4 C16 C17 117.2(4) . . ?
O4 C16 C4 121.3(4) . . ?
C17 C16 C4 121.5(4) . . ?
C1 C17 C16 118.1(4) . . ?
C6 C18 C13 106.5(3) . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.051


