# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_try
_database_code_depnum_ccdc_archive 'CCDC 2262771'
loop_
_audit_author_name
_audit_author_address
'Yaxing Wu'
;Tsinghua University
China
;
_audit_update_record             
;
2023-05-13 deposited with the CCDC.	2023-11-23 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         'C18 H12 Br F7 O'
_chemical_formula_sum            'C18 H12 Br F7 O'
_chemical_formula_weight         457.19

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   28.7901(4)
_cell_length_b                   11.39160(10)
_cell_length_c                   11.1231(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.1140(10)
_cell_angle_gamma                90
_cell_volume                     3486.46(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    109(2)
_cell_measurement_reflns_used    7515
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      66.7

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    3.950
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      109(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12043
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.200
_diffrn_reflns_theta_max         66.566
_diffrn_reflns_theta_full        66.566
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             2981
_reflns_number_gt                2715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0784P)²+28.3095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_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_number_reflns         2981
_refine_ls_number_parameters     244
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1757
_refine_ls_wR_factor_gt          0.1726
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.138
_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 0.05964(2) 0.54794(5) 0.63703(7) 0.0541(3) Uani 1 1 d . . . . .
F1 F 0.24003(11) 0.2560(3) 0.7063(5) 0.0764(14) Uani 1 1 d . . . . .
F2 F 0.28410(16) 0.2199(7) 0.9539(6) 0.141(3) Uani 1 1 d . U . . .
F3 F 0.33392(12) 0.2334(3) 0.8461(4) 0.0637(10) Uani 1 1 d . . . . .
F4 F 0.31854(14) 0.0719(5) 0.9182(4) 0.0931(17) Uani 1 1 d . . . . .
F5 F 0.30965(13) 0.1453(5) 0.6219(4) 0.0789(13) Uani 1 1 d . . . . .
F6 F 0.23907(16) 0.0871(9) 0.5432(4) 0.155(3) Uani 1 1 d . U . . .
F7 F 0.2895(3) -0.0163(5) 0.6797(8) 0.147(3) Uani 1 1 d . . . . .
O1 O 0.14749(11) -0.0524(3) 0.8378(3) 0.0251(7) Uani 1 1 d . . . . .
C1 C 0.13609(14) -0.0214(4) 0.7284(4) 0.0188(8) Uani 1 1 d . . . . .
C2 C 0.16678(14) 0.0712(4) 0.6858(4) 0.0200(8) Uani 1 1 d . . . . .
H2 H 0.1706 0.0479 0.6026 0.024 Uiso 1 1 calc R U . . .
C3 C 0.21707(14) 0.0763(4) 0.7841(4) 0.0225(9) Uani 1 1 d . . . . .
H3A H 0.2131 0.1101 0.8624 0.027 Uiso 1 1 calc R U . . .
H3B H 0.2289 -0.0051 0.8032 0.027 Uiso 1 1 calc R U . . .
C4 C 0.25631(15) 0.1462(4) 0.7488(4) 0.0274(9) Uani 1 1 d . . . . .
C5 C 0.29926(18) 0.1685(6) 0.8672(6) 0.0478(15) Uani 1 1 d . . . . .
C6 C 0.2741(2) 0.0881(7) 0.6480(5) 0.0566(18) Uani 1 1 d . . . . .
C7 C 0.09127(14) -0.0674(3) 0.6362(4) 0.0195(8) Uani 1 1 d . . . . .
C8 C 0.08121(15) -0.0501(4) 0.5067(4) 0.0240(9) Uani 1 1 d . . . . .
H8 H 0.1028 -0.0047 0.4752 0.029 Uiso 1 1 calc R U . . .
C9 C 0.04015(15) -0.0987(4) 0.4240(4) 0.0283(10) Uani 1 1 d . . . . .
H9 H 0.0338 -0.0874 0.3361 0.034 Uiso 1 1 calc R U . . .
C10 C 0.00825(15) -0.1637(4) 0.4691(4) 0.0285(10) Uani 1 1 d . . . . .
H10 H -0.0200 -0.1969 0.4122 0.034 Uiso 1 1 calc R U . . .
C11 C 0.01748(15) -0.1803(4) 0.5969(4) 0.0272(9) Uani 1 1 d . . . . .
H11 H -0.0046 -0.2244 0.6278 0.033 Uiso 1 1 calc R U . . .
C12 C 0.05872(15) -0.1332(4) 0.6801(4) 0.0234(9) Uani 1 1 d . . . . .
H12 H 0.0650 -0.1456 0.7679 0.028 Uiso 1 1 calc R U . . .
C13 C 0.13899(14) 0.1870(4) 0.6717(4) 0.0215(8) Uani 1 1 d . . . . .
C14 C 0.12559(15) 0.2324(4) 0.7722(4) 0.0268(9) Uani 1 1 d . . . . .
H14 H 0.1333 0.1900 0.8491 0.032 Uiso 1 1 calc R U . . .
C15 C 0.10113(17) 0.3388(4) 0.7625(5) 0.0344(11) Uani 1 1 d . . . . .
H15 H 0.0921 0.3697 0.8317 0.041 Uiso 1 1 calc R U . . .
C16 C 0.09039(17) 0.3984(4) 0.6500(5) 0.0361(11) Uani 1 1 d . . . . .
C17 C 0.10231(17) 0.3549(4) 0.5475(5) 0.0340(11) Uani 1 1 d . . . . .
H17 H 0.0941 0.3972 0.4705 0.041 Uiso 1 1 calc R U . . .
C18 C 0.12657(15) 0.2484(4) 0.5584(4) 0.0267(9) Uani 1 1 d . . . . .
H18 H 0.1348 0.2171 0.4881 0.032 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 C16 1.906(5) . ?
F1 C4 1.370(6) . ?
F2 C5 1.308(7) . ?
F3 C5 1.317(6) . ?
F4 C5 1.287(8) . ?
F5 C6 1.315(7) . ?
F6 C6 1.297(7) . ?
F7 C6 1.282(10) . ?
O1 C1 1.216(5) . ?
C1 C7 1.488(5) . ?
C1 C2 1.538(5) . ?
C2 C13 1.527(6) . ?
C2 C3 1.537(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.524(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.516(8) . ?
C4 C5 1.539(7) . ?
C7 C8 1.397(6) . ?
C7 C12 1.396(6) . ?
C8 C9 1.381(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.386(6) . ?
C13 C18 1.392(6) . ?
C14 C15 1.390(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(7) . ?
C17 C18 1.387(7) . ?
C17 H17 0.9500 . ?
C18 H18 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
O1 C1 C7 120.8(4) . . ?
O1 C1 C2 119.8(4) . . ?
C7 C1 C2 119.3(3) . . ?
C13 C2 C3 113.3(3) . . ?
C13 C2 C1 107.1(3) . . ?
C3 C2 C1 108.3(3) . . ?
C13 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C4 C3 C2 116.8(3) . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C2 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
F1 C4 C6 107.3(5) . . ?
F1 C4 C3 111.2(4) . . ?
C6 C4 C3 113.6(4) . . ?
F1 C4 C5 104.6(4) . . ?
C6 C4 C5 110.1(4) . . ?
C3 C4 C5 109.6(4) . . ?
F4 C5 F2 104.6(7) . . ?
F4 C5 F3 107.9(5) . . ?
F2 C5 F3 108.3(5) . . ?
F4 C5 C4 111.7(5) . . ?
F2 C5 C4 110.3(5) . . ?
F3 C5 C4 113.6(5) . . ?
F7 C6 F6 110.7(8) . . ?
F7 C6 F5 106.9(6) . . ?
F6 C6 F5 104.9(5) . . ?
F7 C6 C4 111.5(5) . . ?
F6 C6 C4 109.0(5) . . ?
F5 C6 C4 113.7(6) . . ?
C8 C7 C12 118.7(4) . . ?
C8 C7 C1 122.4(4) . . ?
C12 C7 C1 118.9(4) . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.2(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 120.5(4) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 119.0(4) . . ?
C14 C13 C2 120.0(4) . . ?
C18 C13 C2 121.0(4) . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 118.3(4) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C17 C16 C15 122.1(4) . . ?
C17 C16 Br1 118.9(4) . . ?
C15 C16 Br1 119.0(4) . . ?
C16 C17 C18 119.0(4) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?

_refine_diff_density_max         1.207
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.113



