# 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_b200723b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2059851'
loop_
_audit_author_name
_audit_author_address
'Chen Zhu'
;Soochow University
China
;
_audit_update_record             
;
2021-01-30 deposited with the CCDC.	2021-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-09-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 Br F2 O'
_chemical_formula_sum            'C18 H13 Br F2 O'
_chemical_formula_weight         363.19
_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 0.0033 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'
F F 0.0171 0.0103 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.2274(10)
_cell_length_b                   5.8081(6)
_cell_length_c                   26.071(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.283(3)
_cell_angle_gamma                90
_cell_volume                     1518.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8357
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.292
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1553 before and 0.0892 after correction.
The Ratio of minimum to maximum transmission is 0.4702.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22760
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.322
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2717
_reflns_number_total             3493
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.993
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.064
_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)+(0.0377P)²+3.0971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1192
_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:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00B,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.41776(4) 0.98267(7) 0.56503(2) 0.03938(15) Uani 1 1 d . . . . .
F002 F 0.5386(2) 0.3059(4) 0.72560(9) 0.0404(5) Uani 1 1 d . . . . .
F003 F 0.7080(2) 0.4852(4) 0.77211(8) 0.0427(6) Uani 1 1 d . . . . .
O004 O 0.7494(3) 0.4794(5) 0.66866(11) 0.0408(7) Uani 1 1 d . . . . .
C005 C 0.3094(3) 0.6559(6) 0.66474(12) 0.0228(7) Uani 1 1 d . . . . .
C006 C 0.5574(3) 0.7947(6) 0.60254(13) 0.0240(7) Uani 1 1 d . . . . .
C007 C 0.6678(3) 0.7628(6) 0.57434(12) 0.0243(7) Uani 1 1 d . . . . .
C008 C 0.5483(3) 0.7165(6) 0.64962(13) 0.0237(7) Uani 1 1 d . . . . .
C009 C 0.4435(3) 0.7741(6) 0.68167(13) 0.0246(7) Uani 1 1 d . . . . .
H009 H 0.429192 0.941023 0.680474 0.029 Uiso 1 1 calc R . . . .
C00A C 0.6724(4) 0.5734(7) 0.54255(15) 0.0342(8) Uani 1 1 d . . . . .
H00A H 0.606796 0.460587 0.539666 0.041 Uiso 1 1 calc R . . . .
C00B C 0.6507(3) 0.5628(6) 0.67982(14) 0.0281(7) Uani 1 1 d . . . . .
C00C C 0.2928(4) 0.4553(6) 0.63593(15) 0.0344(8) Uani 1 1 d . . . . .
H00C H 0.365406 0.390826 0.624590 0.041 Uiso 1 1 calc R . . . .
C00D C 0.5115(3) 0.7060(6) 0.73847(13) 0.0297(8) Uani 1 1 d . . . . .
H00B H 0.560511 0.834958 0.756475 0.036 Uiso 1 1 calc R . . . .
H00D H 0.445740 0.655211 0.758272 0.036 Uiso 1 1 calc R . . . .
C00E C 0.6035(3) 0.5141(6) 0.73159(14) 0.0312(8) Uani 1 1 d . . . . .
C00F C 0.8727(4) 0.7182(8) 0.52038(16) 0.0443(10) Uani 1 1 d . . . . .
H00F H 0.942546 0.702998 0.502507 0.053 Uiso 1 1 calc R . . . .
C00G C 0.1698(4) 0.3484(7) 0.62366(16) 0.0402(9) Uani 1 1 d . . . . .
H00G H 0.161022 0.211728 0.604713 0.048 Uiso 1 1 calc R . . . .
C00H C 0.1992(4) 0.7483(7) 0.68070(16) 0.0398(9) Uani 1 1 d . . . . .
H00H H 0.208036 0.882558 0.700518 0.048 Uiso 1 1 calc R . . . .
C00I C 0.7659(4) 0.9289(7) 0.57894(17) 0.0399(9) Uani 1 1 d . . . . .
H00I H 0.763188 1.056513 0.600250 0.048 Uiso 1 1 calc R . . . .
C00J C 0.0603(4) 0.4424(8) 0.63919(15) 0.0399(9) Uani 1 1 d . . . . .
H00J H -0.022549 0.371141 0.630652 0.048 Uiso 1 1 calc R . . . .
C00K C 0.7750(4) 0.5519(7) 0.51492(17) 0.0437(10) Uani 1 1 d . . . . .
H00K H 0.777693 0.426522 0.492974 0.052 Uiso 1 1 calc R . . . .
C00L C 0.0755(4) 0.6423(8) 0.66739(17) 0.0459(10) Uani 1 1 d . . . . .
H00L H 0.002014 0.708142 0.677810 0.055 Uiso 1 1 calc R . . . .
C00M C 0.8683(4) 0.9042(8) 0.55158(18) 0.0459(10) Uani 1 1 d . . . . .
H00M H 0.934554 1.015823 0.554608 0.055 Uiso 1 1 calc R . . . .


_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 C006 1.908(3) . ?
F002 C00E 1.374(4) . ?
F003 C00E 1.358(4) . ?
O004 C00B 1.206(4) . ?
C005 C009 1.520(4) . ?
C005 C00C 1.379(5) . ?
C005 C00H 1.384(5) . ?
C006 C007 1.475(4) . ?
C006 C008 1.329(5) . ?
C007 C00A 1.383(5) . ?
C007 C00I 1.380(5) . ?
C008 C009 1.520(4) . ?
C008 C00B 1.480(5) . ?
C009 H009 0.9800 . ?
C009 C00D 1.559(5) . ?
C00A H00A 0.9300 . ?
C00A C00K 1.390(5) . ?
C00B C00E 1.546(5) . ?
C00C H00C 0.9300 . ?
C00C C00G 1.383(5) . ?
C00D H00B 0.9700 . ?
C00D H00D 0.9700 . ?
C00D C00E 1.492(5) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.377(6) . ?
C00F C00M 1.358(6) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.376(5) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.389(6) . ?
C00I H00I 0.9300 . ?
C00I C00M 1.385(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.367(6) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 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
C00C C005 C009 123.2(3) . . ?
C00C C005 C00H 118.1(3) . . ?
C00H C005 C009 118.6(3) . . ?
C007 C006 Br01 112.7(2) . . ?
C008 C006 Br01 119.2(2) . . ?
C008 C006 C007 128.0(3) . . ?
C00A C007 C006 121.1(3) . . ?
C00I C007 C006 118.9(3) . . ?
C00I C007 C00A 119.9(3) . . ?
C006 C008 C009 128.1(3) . . ?
C006 C008 C00B 121.8(3) . . ?
C00B C008 C009 110.0(3) . . ?
C005 C009 H009 108.5 . . ?
C005 C009 C00D 111.7(3) . . ?
C008 C009 C005 115.8(3) . . ?
C008 C009 H009 108.5 . . ?
C008 C009 C00D 103.6(3) . . ?
C00D C009 H009 108.5 . . ?
C007 C00A H00A 120.0 . . ?
C007 C00A C00K 119.9(4) . . ?
C00K C00A H00A 120.0 . . ?
O004 C00B C008 130.8(3) . . ?
O004 C00B C00E 123.8(3) . . ?
C008 C00B C00E 105.4(3) . . ?
C005 C00C H00C 119.5 . . ?
C005 C00C C00G 121.0(3) . . ?
C00G C00C H00C 119.5 . . ?
C009 C00D H00B 110.9 . . ?
C009 C00D H00D 110.9 . . ?
H00B C00D H00D 108.9 . . ?
C00E C00D C009 104.5(3) . . ?
C00E C00D H00B 110.9 . . ?
C00E C00D H00D 110.9 . . ?
F002 C00E C00B 106.8(3) . . ?
F002 C00E C00D 111.6(3) . . ?
F003 C00E F002 105.6(3) . . ?
F003 C00E C00B 111.7(3) . . ?
F003 C00E C00D 114.7(3) . . ?
C00D C00E C00B 106.3(3) . . ?
C00K C00F H00F 119.6 . . ?
C00M C00F H00F 119.6 . . ?
C00M C00F C00K 120.7(4) . . ?
C00C C00G H00G 119.7 . . ?
C00J C00G C00C 120.6(4) . . ?
C00J C00G H00G 119.7 . . ?
C005 C00H H00H 119.7 . . ?
C005 C00H C00L 120.6(4) . . ?
C00L C00H H00H 119.7 . . ?
C007 C00I H00I 120.2 . . ?
C007 C00I C00M 119.5(4) . . ?
C00M C00I H00I 120.2 . . ?
C00G C00J H00J 120.6 . . ?
C00L C00J C00G 118.8(4) . . ?
C00L C00J H00J 120.6 . . ?
C00A C00K H00K 120.3 . . ?
C00F C00K C00A 119.3(4) . . ?
C00F C00K H00K 120.3 . . ?
C00H C00L H00L 119.6 . . ?
C00J C00L C00H 120.9(4) . . ?
C00J C00L H00L 119.6 . . ?
C00F C00M C00I 120.5(4) . . ?
C00F C00M H00M 119.7 . . ?
C00I C00M H00M 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
