# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_13559
_database_code_depnum_ccdc_archive 'CCDC 2295572'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;College of pharmacy, Gannan Medical University
China
;
_audit_update_record             
;
2023-10-30 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H7 Br F2 O3'
_chemical_formula_sum            'C11 H7 Br F2 O3'
_chemical_formula_weight         305.08
_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'
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'
O O 0.0492 0.0322 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4857(15)
_cell_length_b                   9.7788(14)
_cell_length_c                   9.6329(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.874(12)
_cell_angle_gamma                90
_cell_volume                     1058.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1177
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7230
_cell_measurement_theta_min      3.8650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.554
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3446
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.921
_diffrn_reflns_theta_min         3.933
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  23.00   1.00    1.50    --   36.10 -57.00   0.00   54
  2  ω     -3.00  22.00   1.00    1.50    --   36.10 -99.00  90.00   25
  3  ω     21.00  62.00   1.00    1.50    --   36.10-125.00 120.00   41
  4  ω     34.00  88.00   1.00    1.50    --   36.10-125.00  30.00   54
  5  ω    105.00 130.00   1.00    2.00    --  108.00 -38.00  90.00   25
  6  ω     78.00 177.00   1.00    2.00    --  108.00  25.00 120.00   99
  7  ω     68.00 127.00   1.00    2.00    --  108.00 -50.00 -60.00   59
  8  ω     89.00 151.00   1.00    2.00    --  108.00  38.00-150.00   62
  9  ω     69.00 105.00   1.00    1.50    --   36.10  77.00-120.00   36
 10  ω     24.00  94.00   1.00    1.50    --   36.10  57.00 -60.00   70
 11  ω     42.00  87.00   1.00    2.00    --  108.00 -38.00  90.00   45
 12  ω     43.00 129.00   1.00    2.00    --  108.00 -63.00 150.00   86
 13  ω     41.00  82.00   1.00    2.00    --  108.00 -63.00  60.00   41
 14  ω     50.00  85.00   1.00    2.00    --  108.00 -63.00 -60.00   35
 15  ω     16.00  58.00   1.00    1.50    --   36.10  77.00-120.00   42
 16  ω    -62.00 -24.00   1.00    1.50    --  -33.50  77.00-120.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0997433000
_diffrn_orient_matrix_UB_12      -0.0820733000
_diffrn_orient_matrix_UB_13      -0.0462545000
_diffrn_orient_matrix_UB_21      -0.0702706000
_diffrn_orient_matrix_UB_22      0.0021091000
_diffrn_orient_matrix_UB_23      -0.1546749000
_diffrn_orient_matrix_UB_31      0.0624767000
_diffrn_orient_matrix_UB_32      0.1344285000
_diffrn_orient_matrix_UB_33      -0.0257632000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1444
_reflns_number_total             1976
_reflns_odcompleteness_completeness 97.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.177
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1105P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.2021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3A), C4(H4), C7(H7)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 1.08520(6) 0.76547(8) 1.02374(7) 0.0557(3) Uani 1 1 d . . . . .
F1 F 0.3866(5) 0.7724(5) 0.4671(5) 0.0709(13) Uani 1 1 d . . . . .
F2 F 0.3247(4) 0.7175(6) 0.2479(5) 0.0791(15) Uani 1 1 d . . . . .
O1 O 0.7520(4) 0.9289(4) 0.6141(5) 0.0519(11) Uani 1 1 d . . . . .
O2 O 0.6562(4) 0.5465(5) 0.4608(5) 0.0530(11) Uani 1 1 d . . . . .
O3 O 0.4969(5) 0.9116(6) 0.2679(6) 0.0783(17) Uani 1 1 d . . . . .
H3 H 0.437174 0.910296 0.204364 0.118 Uiso 1 1 calc R U . . .
C1 C 0.8965(5) 0.8433(6) 0.7998(6) 0.0419(13) Uani 1 1 d . . . . .
H1 H 0.913462 0.932432 0.831156 0.050 Uiso 1 1 calc R U . . .
C2 C 0.9571(5) 0.7354(6) 0.8680(5) 0.0381(13) Uani 1 1 d . . . . .
C3 C 0.9301(6) 0.5996(7) 0.8244(6) 0.0482(14) Uani 1 1 d . . . . .
H3A H 0.972125 0.527117 0.873490 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8397(5) 0.5758(6) 0.7068(6) 0.0455(14) Uani 1 1 d . . . . .
H4 H 0.820727 0.486761 0.676416 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7776(5) 0.6857(6) 0.6346(6) 0.0392(12) Uani 1 1 d . . . . .
C6 C 0.8075(5) 0.8153(7) 0.6807(6) 0.0397(13) Uani 1 1 d . . . . .
C7 C 0.6647(6) 0.9081(7) 0.4979(7) 0.0531(16) Uani 1 1 d . . . . .
H7 H 0.628434 0.985240 0.451718 0.064 Uiso 1 1 calc R U . . .
C8 C 0.6262(5) 0.7865(6) 0.4438(6) 0.0396(12) Uani 1 1 d . . . . .
C9 C 0.6829(5) 0.6628(6) 0.5072(6) 0.0381(12) Uani 1 1 d . . . . .
C10 C 0.5248(6) 0.7762(7) 0.3177(6) 0.0476(15) Uani 1 1 d . . . . .
H10 H 0.549631 0.722237 0.243148 0.057 Uiso 1 1 calc R U . . .
C11 C 0.4192(5) 0.7112(7) 0.3572(6) 0.0457(14) Uani 1 1 d . . . . .
H11 H 0.437349 0.615069 0.381048 0.055 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 C2 1.896(5) . ?
F1 C11 1.335(7) . ?
F2 C11 1.349(8) . ?
O1 C6 1.373(7) . ?
O1 C7 1.355(8) . ?
O2 C9 1.237(7) . ?
O3 H3 0.8200 . ?
O3 C10 1.422(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.357(8) . ?
C1 C6 1.397(8) . ?
C2 C3 1.407(8) . ?
C3 H3A 0.9300 . ?
C3 C4 1.390(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(9) . ?
C5 C6 1.364(9) . ?
C5 C9 1.480(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.337(9) . ?
C8 C9 1.448(8) . ?
C8 C10 1.504(8) . ?
C10 H10 0.9800 . ?
C10 C11 1.486(9) . ?
C11 H11 0.9800 . ?

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
C7 O1 C6 117.2(5) . . ?
C10 O3 H3 109.5 . . ?
C2 C1 H1 121.3 . . ?
C2 C1 C6 117.4(6) . . ?
C6 C1 H1 121.3 . . ?
C1 C2 Br1 120.0(5) . . ?
C1 C2 C3 122.0(5) . . ?
C3 C2 Br1 118.0(4) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 C2 118.9(6) . . ?
C4 C3 H3A 120.6 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(6) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C9 120.7(6) . . ?
C6 C5 C4 119.0(6) . . ?
C6 C5 C9 120.2(6) . . ?
O1 C6 C1 114.6(6) . . ?
C5 C6 O1 122.6(5) . . ?
C5 C6 C1 122.8(6) . . ?
O1 C7 H7 117.1 . . ?
C8 C7 O1 125.8(6) . . ?
C8 C7 H7 117.1 . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 C10 120.9(6) . . ?
C9 C8 C10 119.4(6) . . ?
O2 C9 C5 121.6(6) . . ?
O2 C9 C8 124.0(6) . . ?
C8 C9 C5 114.4(5) . . ?
O3 C10 C8 107.1(5) . . ?
O3 C10 H10 109.5 . . ?
O3 C10 C11 110.2(6) . . ?
C8 C10 H10 109.5 . . ?
C11 C10 C8 111.1(5) . . ?
C11 C10 H10 109.5 . . ?
F1 C11 F2 106.7(6) . . ?
F1 C11 C10 112.8(6) . . ?
F1 C11 H11 109.0 . . ?
F2 C11 C10 110.4(5) . . ?
F2 C11 H11 109.0 . . ?
C10 C11 H11 109.0 . . ?

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
Br1 C2 C3 C4 -177.4(4) . . . . ?
O1 C7 C8 C9 -2.8(10) . . . . ?
O1 C7 C8 C10 177.2(6) . . . . ?
O3 C10 C11 F1 -65.1(7) . . . . ?
O3 C10 C11 F2 54.2(7) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
C2 C1 C6 O1 -178.2(5) . . . . ?
C2 C1 C6 C5 2.2(9) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
C3 C4 C5 C9 178.6(5) . . . . ?
C4 C5 C6 O1 178.9(5) . . . . ?
C4 C5 C6 C1 -1.5(8) . . . . ?
C4 C5 C9 O2 -0.2(8) . . . . ?
C4 C5 C9 C8 179.9(5) . . . . ?
C6 O1 C7 C8 1.4(10) . . . . ?
C6 C1 C2 Br1 176.4(4) . . . . ?
C6 C1 C2 C3 -1.9(9) . . . . ?
C6 C5 C9 O2 178.0(5) . . . . ?
C6 C5 C9 C8 -1.9(7) . . . . ?
C7 O1 C6 C1 -179.9(5) . . . . ?
C7 O1 C6 C5 -0.3(8) . . . . ?
C7 C8 C9 O2 -177.1(6) . . . . ?
C7 C8 C9 C5 2.8(8) . . . . ?
C7 C8 C10 O3 7.0(8) . . . . ?
C7 C8 C10 C11 -113.4(7) . . . . ?
C8 C10 C11 F1 53.4(8) . . . . ?
C8 C10 C11 F2 172.6(6) . . . . ?
C9 C5 C6 O1 0.7(8) . . . . ?
C9 C5 C6 C1 -179.7(5) . . . . ?
C9 C8 C10 O3 -173.0(5) . . . . ?
C9 C8 C10 C11 66.6(7) . . . . ?
C10 C8 C9 O2 2.9(8) . . . . ?
C10 C8 C9 C5 -177.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.268
_oxdiff_exptl_absorpt_empirical_full_min 0.430
