# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_190415xjf08_0m
_database_code_depnum_ccdc_archive 'CCDC 1958968'
loop_
_audit_author_name
_audit_author_address
dd
;dd
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2019-04-18
_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         'C17 H12 Br F3 N2 O2'
_chemical_formula_sum            'C17 H12 Br F3 N2 O2'
_chemical_formula_weight         413.20
_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'
N N 0.0061 0.0033 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   15.949(2)
_cell_length_b                   9.0933(12)
_cell_length_c                   25.010(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.421(2)
_cell_angle_gamma                90
_cell_volume                     3328.3(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2138
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.129
_cell_measurement_theta_min      2.600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.515
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0592 before and 0.0324 after correction. The Ratio of minimum to maximum transmission is 0.8058. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9770
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.620
_diffrn_reflns_theta_min         2.600
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2267
_reflns_number_total             3779
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.540
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00040(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.013
_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)+(0.0494P)²+4.0563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1197
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_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 0.05183(3) 0.33531(6) 0.18277(2) 0.0778(2) Uani 1 1 d . . . . .
F1 F 0.3236(3) 0.7173(3) 0.63067(15) 0.1187(11) Uani 1 1 d . . . . .
F2 F 0.3733(2) 0.5920(3) 0.71051(12) 0.1159(11) Uani 1 1 d . . . . .
F3 F 0.4622(2) 0.6656(4) 0.67296(13) 0.1341(14) Uani 1 1 d . . . . .
O1 O 0.39577(17) 0.5427(2) 0.47604(10) 0.0537(6) Uani 1 1 d . . . . .
O2 O 0.37843(15) 0.4977(2) 0.57602(9) 0.0460(5) Uani 1 1 d . . . . .
N1 N 0.39489(16) 0.2961(2) 0.45842(10) 0.0337(6) Uani 1 1 d . . . . .
N2 N 0.36703(16) 0.2480(3) 0.56079(10) 0.0381(6) Uani 1 1 d . . . . .
C1 C 0.1608(2) 0.3297(4) 0.25159(14) 0.0489(8) Uani 1 1 d . . . . .
C2 C 0.1720(2) 0.4261(4) 0.29605(15) 0.0581(10) Uani 1 1 d . . . . .
H2 H 0.125970 0.492487 0.293111 0.070 Uiso 1 1 calc R . . . .
C3 C 0.2529(2) 0.4232(4) 0.34558(14) 0.0508(9) Uani 1 1 d . . . . .
H3 H 0.261000 0.489096 0.375685 0.061 Uiso 1 1 calc R . . . .
C4 C 0.3218(2) 0.3243(3) 0.35099(12) 0.0355(7) Uani 1 1 d . . . . .
C5 C 0.4093(2) 0.3256(3) 0.40455(12) 0.0387(7) Uani 1 1 d . . . . .
H5A H 0.450318 0.251880 0.400439 0.046 Uiso 1 1 calc R . . . .
H5B H 0.438436 0.420804 0.407859 0.046 Uiso 1 1 calc R . . . .
C6 C 0.3905(2) 0.4152(3) 0.49056(13) 0.0376(7) Uani 1 1 d . . . . .
C7 C 0.3779(2) 0.3769(3) 0.54423(13) 0.0374(7) Uani 1 1 d . . . . .
C8 C 0.3647(2) 0.4707(4) 0.62813(14) 0.0508(9) Uani 1 1 d . . . . .
H8A H 0.406408 0.395301 0.651246 0.061 Uiso 1 1 calc R . . . .
H8B H 0.302590 0.438065 0.618902 0.061 Uiso 1 1 calc R . . . .
C9 C 0.3824(3) 0.6121(5) 0.66066(18) 0.0711(12) Uani 1 1 d . . . . .
C10 C 0.37022(19) 0.1309(3) 0.52574(13) 0.0355(7) Uani 1 1 d . . . . .
C11 C 0.38454(18) 0.1517(3) 0.47458(12) 0.0326(6) Uani 1 1 d . . . . .
C12 C 0.38872(19) 0.0289(3) 0.44216(13) 0.0409(7) Uani 1 1 d . . . . .
H12 H 0.398141 0.041084 0.408045 0.049 Uiso 1 1 calc R . . . .
C13 C 0.3790(2) -0.1096(3) 0.46056(15) 0.0463(8) Uani 1 1 d . . . . .
H13 H 0.382437 -0.190634 0.438837 0.056 Uiso 1 1 calc R . . . .
C14 C 0.3641(2) -0.1311(4) 0.51086(16) 0.0494(9) Uani 1 1 d . . . . .
H14 H 0.356747 -0.225562 0.522624 0.059 Uiso 1 1 calc R . . . .
C15 C 0.3602(2) -0.0114(3) 0.54314(14) 0.0456(8) Uani 1 1 d . . . . .
H15 H 0.350749 -0.025277 0.577166 0.055 Uiso 1 1 calc R . . . .
C16 C 0.3081(2) 0.2292(4) 0.30541(15) 0.0557(9) Uani 1 1 d . . . . .
H16 H 0.353670 0.162218 0.308059 0.067 Uiso 1 1 calc R . . . .
C17 C 0.2279(3) 0.2315(5) 0.25571(16) 0.0638(11) Uani 1 1 d . . . . .
H17 H 0.219760 0.166595 0.225314 0.077 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
Br1 C1 1.899(3) . ?
F1 C9 1.341(5) . ?
F2 C9 1.324(5) . ?
F3 C9 1.281(5) . ?
O1 C6 1.228(4) . ?
O2 C7 1.354(3) . ?
O2 C8 1.426(4) . ?
N1 C5 1.479(4) . ?
N1 C6 1.367(4) . ?
N1 C11 1.403(4) . ?
N2 C7 1.278(4) . ?
N2 C10 1.393(4) . ?
C1 C2 1.371(5) . ?
C1 C17 1.366(5) . ?
C2 C3 1.390(5) . ?
C3 C4 1.384(4) . ?
C4 C5 1.502(4) . ?
C4 C16 1.377(4) . ?
C6 C7 1.476(4) . ?
C8 C9 1.487(5) . ?
C10 C11 1.399(4) . ?
C10 C15 1.394(4) . ?
C11 C12 1.398(4) . ?
C12 C13 1.371(4) . ?
C13 C14 1.384(5) . ?
C14 C15 1.371(5) . ?
C16 C17 1.385(5) . ?

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 O2 C8 115.4(2) . . ?
C6 N1 C5 117.1(2) . . ?
C6 N1 C11 122.2(2) . . ?
C11 N1 C5 120.7(2) . . ?
C7 N2 C10 117.0(3) . . ?
C2 C1 Br1 119.7(3) . . ?
C17 C1 Br1 119.5(3) . . ?
C17 C1 C2 120.8(3) . . ?
C1 C2 C3 119.1(3) . . ?
C4 C3 C2 121.3(3) . . ?
C3 C4 C5 120.1(3) . . ?
C16 C4 C3 118.0(3) . . ?
C16 C4 C5 121.9(3) . . ?
N1 C5 C4 112.6(2) . . ?
O1 C6 N1 123.3(3) . . ?
O1 C6 C7 122.8(3) . . ?
N1 C6 C7 113.9(3) . . ?
O2 C7 C6 111.8(3) . . ?
N2 C7 O2 121.6(3) . . ?
N2 C7 C6 126.6(3) . . ?
O2 C8 C9 106.6(3) . . ?
F1 C9 C8 111.8(3) . . ?
F2 C9 F1 108.1(4) . . ?
F2 C9 C8 109.1(4) . . ?
F3 C9 F1 105.7(4) . . ?
F3 C9 F2 107.3(4) . . ?
F3 C9 C8 114.5(4) . . ?
N2 C10 C11 122.2(3) . . ?
N2 C10 C15 118.4(3) . . ?
C15 C10 C11 119.5(3) . . ?
C10 C11 N1 118.1(2) . . ?
C12 C11 N1 122.9(3) . . ?
C12 C11 C10 119.0(3) . . ?
C13 C12 C11 120.1(3) . . ?
C12 C13 C14 121.2(3) . . ?
C15 C14 C13 119.1(3) . . ?
C14 C15 C10 121.0(3) . . ?
C4 C16 C17 121.3(3) . . ?
C1 C17 C16 119.6(3) . . ?

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 -178.5(3) . . . . ?
Br1 C1 C17 C16 178.8(3) . . . . ?
O1 C6 C7 O2 -3.5(4) . . . . ?
O1 C6 C7 N2 176.1(3) . . . . ?
O2 C8 C9 F1 62.4(4) . . . . ?
O2 C8 C9 F2 -178.1(3) . . . . ?
O2 C8 C9 F3 -57.9(5) . . . . ?
N1 C6 C7 O2 177.0(2) . . . . ?
N1 C6 C7 N2 -3.4(4) . . . . ?
N1 C11 C12 C13 179.4(3) . . . . ?
N2 C10 C11 N1 -0.7(4) . . . . ?
N2 C10 C11 C12 178.8(3) . . . . ?
N2 C10 C15 C14 -179.1(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C1 C17 C16 0.1(6) . . . . ?
C2 C3 C4 C5 178.8(3) . . . . ?
C2 C3 C4 C16 0.7(5) . . . . ?
C3 C4 C5 N1 60.7(4) . . . . ?
C3 C4 C16 C17 -0.3(5) . . . . ?
C4 C16 C17 C1 0.0(6) . . . . ?
C5 N1 C6 O1 1.7(4) . . . . ?
C5 N1 C6 C7 -178.8(2) . . . . ?
C5 N1 C11 C10 -179.4(2) . . . . ?
C5 N1 C11 C12 1.2(4) . . . . ?
C5 C4 C16 C17 -178.5(3) . . . . ?
C6 N1 C5 C4 -97.6(3) . . . . ?
C6 N1 C11 C10 -0.7(4) . . . . ?
C6 N1 C11 C12 179.9(3) . . . . ?
C7 O2 C8 C9 171.2(3) . . . . ?
C7 N2 C10 C11 -0.1(4) . . . . ?
C7 N2 C10 C15 178.9(3) . . . . ?
C8 O2 C7 N2 -0.9(4) . . . . ?
C8 O2 C7 C6 178.7(3) . . . . ?
C10 N2 C7 O2 -178.2(2) . . . . ?
C10 N2 C7 C6 2.2(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 N1 C5 C4 81.2(3) . . . . ?
C11 N1 C6 O1 -177.1(3) . . . . ?
C11 N1 C6 C7 2.4(4) . . . . ?
C11 C10 C15 C14 -0.1(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
C15 C10 C11 N1 -179.6(3) . . . . ?
C15 C10 C11 C12 -0.2(4) . . . . ?
C16 C4 C5 N1 -121.2(3) . . . . ?
C17 C1 C2 C3 0.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
