# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_210323_s1_xj
_database_code_depnum_ccdc_archive 'CCDC 2074740'
loop_
_audit_author_name
_audit_author_address
JIEJIE
;SiChuan University
China
;
_audit_update_record             
;
2021-04-01 deposited with the CCDC.	2022-04-21 downloaded from the CCDC.
;
_audit_creation_date             2021-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H6 Br F5'
_chemical_formula_sum            'C13 H6 Br F5'
_chemical_formula_weight         337.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3br1
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'

_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                   19.4671(16)
_cell_length_b                   5.8892(8)
_cell_length_c                   10.9041(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.106(11)
_cell_angle_gamma                90
_cell_volume                     1217.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    989
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2300
_cell_measurement_theta_min      3.9020
_shelx_estimated_absorpt_T_max   0.482
_shelx_estimated_absorpt_T_min   0.381
_exptl_absorpt_coefficient_mu    3.420
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5024
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.223
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   53.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336   38.0000  -60.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00  -31.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -57.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00   90.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  178.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega   42.00   85.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  178.0000   90.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0305306000
_diffrn_orient_matrix_UB_12      0.0577061000
_diffrn_orient_matrix_UB_13      0.0086685000
_diffrn_orient_matrix_UB_21      0.0057802000
_diffrn_orient_matrix_UB_22      0.0869094000
_diffrn_orient_matrix_UB_23      -0.0415253000
_diffrn_orient_matrix_UB_31      -0.0207759000
_diffrn_orient_matrix_UB_32      -0.0604735000
_diffrn_orient_matrix_UB_33      -0.0515636000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1053
_reflns_number_total             2488
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1767
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      0.988
_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)+(0.0767P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.2072
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9)
;
_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 0.05170(4) 0.23606(17) 0.09619(10) 0.0895(5) Uani 1 1 d . . . . .
F1 F 0.4762(2) 0.2746(8) 0.4427(5) 0.0816(16) Uani 1 1 d . . . . .
F2 F 0.4026(3) 0.0268(9) 0.3732(6) 0.114(2) Uani 1 1 d . . . . .
F3 F 0.3828(4) 0.2569(12) 0.5056(5) 0.150(3) Uani 1 1 d . . . . .
F4 F 0.4708(2) 0.5838(9) 0.2795(4) 0.0747(13) Uani 1 1 d . . . . .
F5 F 0.3722(2) 0.6789(7) 0.1610(4) 0.0665(13) Uani 1 1 d . . . . .
C1 C 0.1484(4) 0.2897(13) 0.1637(7) 0.054(2) Uani 1 1 d . . . . .
C2 C 0.1957(4) 0.1534(13) 0.1307(6) 0.054(2) Uani 1 1 d . . . . .
H2 H 0.180170 0.033280 0.076119 0.065 Uiso 1 1 calc R . . . .
C3 C 0.2681(4) 0.1867(12) 0.1763(6) 0.0454(17) Uani 1 1 d . . . . .
H3 H 0.300121 0.091075 0.150450 0.054 Uiso 1 1 calc R . . . .
C4 C 0.2921(3) 0.3607(12) 0.2593(6) 0.0419(16) Uani 1 1 d . . . . .
C5 C 0.2436(3) 0.5074(11) 0.2973(5) 0.0404(16) Uani 1 1 d . . . . .
C6 C 0.2650(4) 0.6888(12) 0.3838(6) 0.0491(19) Uani 1 1 d . . . . .
H6 H 0.312793 0.710574 0.418344 0.059 Uiso 1 1 calc R . . . .
C7 C 0.2176(4) 0.8304(14) 0.4171(7) 0.065(2) Uani 1 1 d . . . . .
H7 H 0.233053 0.948632 0.473064 0.078 Uiso 1 1 calc R . . . .
C8 C 0.1458(5) 0.7996(14) 0.3676(7) 0.065(2) Uani 1 1 d . . . . .
H8 H 0.113562 0.897618 0.391059 0.078 Uiso 1 1 calc R . . . .
C9 C 0.1222(4) 0.6285(15) 0.2858(7) 0.061(2) Uani 1 1 d . . . . .
H9 H 0.074063 0.612235 0.253017 0.073 Uiso 1 1 calc R . . . .
C10 C 0.1693(3) 0.4756(12) 0.2498(6) 0.0463(17) Uani 1 1 d . . . . .
C11 C 0.3695(3) 0.3906(12) 0.3046(6) 0.0424(16) Uani 1 1 d . . . . .
C12 C 0.4080(4) 0.2467(14) 0.4063(7) 0.059(2) Uani 1 1 d . . . . .
C13 C 0.4033(3) 0.5427(14) 0.2538(6) 0.0507(19) Uani 1 1 d . . . . .


_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 1.886(7) . ?
F1 C12 1.307(9) . ?
F2 C12 1.342(9) . ?
F3 C12 1.287(10) . ?
F4 C13 1.302(7) . ?
F5 C13 1.326(8) . ?
C1 C2 1.330(10) . ?
C1 C10 1.439(9) . ?
C2 C3 1.398(9) . ?
C3 C4 1.377(9) . ?
C4 C5 1.408(9) . ?
C4 C11 1.486(8) . ?
C5 C6 1.423(9) . ?
C5 C10 1.434(8) . ?
C6 C7 1.353(10) . ?
C7 C8 1.391(10) . ?
C8 C9 1.354(10) . ?
C9 C10 1.403(10) . ?
C11 C12 1.460(10) . ?
C11 C13 1.306(9) . ?

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
C2 C1 Br1 118.9(6) . . ?
C2 C1 C10 121.7(7) . . ?
C10 C1 Br1 119.4(6) . . ?
C1 C2 C3 121.5(7) . . ?
C4 C3 C2 120.1(7) . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 C11 118.3(6) . . ?
C5 C4 C11 121.7(6) . . ?
C4 C5 C6 122.7(6) . . ?
C4 C5 C10 120.1(6) . . ?
C6 C5 C10 117.2(6) . . ?
C7 C6 C5 121.7(7) . . ?
C6 C7 C8 120.1(7) . . ?
C9 C8 C7 120.8(8) . . ?
C8 C9 C10 121.1(7) . . ?
C5 C10 C1 116.6(6) . . ?
C9 C10 C1 124.4(7) . . ?
C9 C10 C5 119.0(6) . . ?
C12 C11 C4 119.4(6) . . ?
C13 C11 C4 120.7(6) . . ?
C13 C11 C12 119.9(6) . . ?
F1 C12 F2 102.4(7) . . ?
F1 C12 C11 117.9(7) . . ?
F2 C12 C11 111.1(6) . . ?
F3 C12 F1 107.0(7) . . ?
F3 C12 F2 104.5(8) . . ?
F3 C12 C11 112.6(7) . . ?
F4 C13 F5 108.3(6) . . ?
F4 C13 C11 128.1(7) . . ?
C11 C13 F5 123.5(6) . . ?

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 C1 C2 C3 179.1(5) . . . . ?
Br1 C1 C10 C5 -179.8(4) . . . . ?
Br1 C1 C10 C9 -2.0(9) . . . . ?
C1 C2 C3 C4 1.4(11) . . . . ?
C2 C1 C10 C5 0.5(10) . . . . ?
C2 C1 C10 C9 178.3(7) . . . . ?
C2 C3 C4 C5 -0.8(10) . . . . ?
C2 C3 C4 C11 -179.6(6) . . . . ?
C3 C4 C5 C6 179.3(6) . . . . ?
C3 C4 C5 C10 0.1(9) . . . . ?
C3 C4 C11 C12 -80.6(8) . . . . ?
C3 C4 C11 C13 99.0(8) . . . . ?
C4 C5 C6 C7 178.7(7) . . . . ?
C4 C5 C10 C1 0.1(9) . . . . ?
C4 C5 C10 C9 -177.9(6) . . . . ?
C4 C11 C12 F1 178.9(6) . . . . ?
C4 C11 C12 F2 61.2(9) . . . . ?
C4 C11 C12 F3 -55.6(10) . . . . ?
C4 C11 C13 F4 -177.3(6) . . . . ?
C4 C11 C13 F5 0.2(11) . . . . ?
C5 C4 C11 C12 100.7(8) . . . . ?
C5 C4 C11 C13 -79.8(8) . . . . ?
C5 C6 C7 C8 0.7(12) . . . . ?
C6 C5 C10 C1 -179.2(6) . . . . ?
C6 C5 C10 C9 2.8(9) . . . . ?
C6 C7 C8 C9 -0.1(12) . . . . ?
C7 C8 C9 C10 0.9(12) . . . . ?
C8 C9 C10 C1 179.9(7) . . . . ?
C8 C9 C10 C5 -2.3(10) . . . . ?
C10 C1 C2 C3 -1.2(11) . . . . ?
C10 C5 C6 C7 -2.1(10) . . . . ?
C11 C4 C5 C6 -1.9(9) . . . . ?
C11 C4 C5 C10 178.9(6) . . . . ?
C12 C11 C13 F4 2.2(11) . . . . ?
C12 C11 C13 F5 179.7(6) . . . . ?
C13 C11 C12 F1 -0.6(11) . . . . ?
C13 C11 C12 F2 -118.3(8) . . . . ?
C13 C11 C12 F3 124.8(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
