# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_s1
_database_code_depnum_ccdc_archive 'CCDC 2170084'
loop_
_audit_author_name
_audit_author_address
'fang zheng'
;Fuzhou University, Fuzhou City, Fujian Province
China
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;
_audit_creation_date             2022-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H17 Br F3 N'
_chemical_formula_sum            'C25 H17 Br F3 N'
_chemical_formula_weight         468.31
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9303(7)
_cell_length_b                   16.2965(11)
_cell_length_c                   12.8568(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.523(2)
_cell_angle_gamma                90.00
_cell_volume                     2057.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7158
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.861
_cell_measurement_theta_min      2.421
_exptl_absorpt_coefficient_mu    2.036
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0945 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.8831.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33763
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.03
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2614
_reflns_number_total             3657
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       lb20201022
_computing_data_collection       ?
_computing_data_reduction        lb20201022
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.054
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0692P)²+3.7456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1640
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C12(H12), C15(H15), C14(H14),
 C42(H42), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24),
  C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.17858(6) 0.65256(5) 0.58899(4) 0.0811(3) Uani 1 d . . . .
N3 N -0.0286(4) 0.6599(2) 0.1206(3) 0.0562(11) Uani 1 d . . . .
H3 H -0.0086 0.7037 0.0889 0.067 Uiso 1 calc . . R .
C2 C 0.1162(5) 0.6539(3) 0.4421(4) 0.0511(12) Uani 1 d . . . .
C8 C -0.3914(4) 0.6378(2) -0.5570(3) 0.0391(10) Uani 1 d . . . .
C4 C -0.3910(5) 0.5588(3) -0.2810(3) 0.0452(10) Uani 1 d . . . .
H4 H -0.4488 0.5290 -0.2445 0.054 Uiso 1 calc . . R .
C5 C -0.2244(4) 0.5660(3) -0.1154(3) 0.0416(10) Uani 1 d . . . .
C6 C -0.1831(5) 0.6303(3) -0.2860(4) 0.0456(11) Uani 1 d . . . .
H6 H -0.0990 0.6491 -0.2531 0.055 Uiso 1 calc . . R .
C7 C -0.2231(5) 0.6471(3) -0.3909(4) 0.0460(11) Uani 1 d . . . .
H7 H -0.1656 0.6772 -0.4272 0.055 Uiso 1 calc . . R .
C13 C -0.5275(5) 0.6524(3) -0.5952(4) 0.0469(11) Uani 1 d . . . .
H13 H -0.5914 0.6510 -0.5492 0.056 Uiso 1 calc . . R .
C9 C -0.1060(5) 0.6020(3) 0.0586(3) 0.0456(11) Uani 1 d . . . .
C10 C -0.2659(4) 0.5859(2) -0.2281(3) 0.0395(10) Uani 1 d . . . .
C11 C 0.0211(4) 0.6558(3) 0.2285(4) 0.0459(11) Uani 1 d . . . .
C12 C 0.1149(5) 0.5830(3) 0.3851(4) 0.0528(12) Uani 1 d . . . .
H12 H 0.1450 0.5342 0.4180 0.063 Uiso 1 calc . . R .
C15 C -0.3420(6) 0.6572(3) -0.7328(4) 0.0622(14) Uani 1 d . . . .
H15 H -0.2786 0.6590 -0.7792 0.075 Uiso 1 calc . . R .
C14 C -0.1528(5) 0.5297(3) 0.0981(3) 0.0482(11) Uani 1 d . . . .
H14 H -0.1325 0.5177 0.1695 0.058 Uiso 1 calc . . R .
C42 C -0.4778(5) 0.6714(3) -0.7693(4) 0.0572(13) Uani 1 d . . . .
H42 H -0.5062 0.6826 -0.8401 0.069 Uiso 1 calc . . R .
C16 C 0.0685(5) 0.5845(3) 0.2785(4) 0.0495(11) Uani 1 d . . . .
H16 H 0.0692 0.5364 0.2397 0.059 Uiso 1 calc . . R .
C17 C -0.4302(4) 0.5753(3) -0.3859(3) 0.0437(10) Uani 1 d . . . .
H17 H -0.5139 0.5560 -0.4188 0.052 Uiso 1 calc . . R .
C18 C -0.2994(5) 0.6404(3) -0.6279(4) 0.0549(12) Uani 1 d . . . .
H18 H -0.2076 0.6308 -0.6045 0.066 Uiso 1 calc . . R .
C19 C -0.5698(5) 0.6689(3) -0.7006(4) 0.0524(12) Uani 1 d . . . .
H19 H -0.6615 0.6784 -0.7246 0.063 Uiso 1 calc . . R .
C20 C 0.0748(5) 0.7264(3) 0.3937(4) 0.0578(13) Uani 1 d . . . .
H20 H 0.0798 0.7748 0.4324 0.069 Uiso 1 calc . . R .
C21 C -0.1429(5) 0.6194(3) -0.0484(3) 0.0444(10) Uani 1 d . . . .
H21 H -0.1124 0.6677 -0.0755 0.053 Uiso 1 calc . . R .
C22 C -0.2294(5) 0.4757(3) 0.0311(3) 0.0495(11) Uani 1 d . . . .
C23 C -0.2723(7) 0.3972(4) 0.0738(4) 0.0771(19) Uani 1 d . . . .
C24 C -0.2656(5) 0.4926(3) -0.0746(3) 0.0481(11) Uani 1 d . . . .
H24 H -0.3171 0.4551 -0.1183 0.058 Uiso 1 calc . . R .
C25 C -0.3484(4) 0.6200(3) -0.4442(3) 0.0401(10) Uani 1 d . . . .
C27 C 0.0254(5) 0.7277(3) 0.2867(4) 0.0535(12) Uani 1 d . . . .
H27 H -0.0048 0.7767 0.2542 0.064 Uiso 1 calc . . R .
F3 F -0.2961(8) 0.3391(3) 0.0121(4) 0.171(3) Uani 1 d . . . .
F4 F -0.3839(9) 0.4034(4) 0.1064(9) 0.256(5) Uani 1 d . . . U
F5 F -0.2013(11) 0.3709(4) 0.1523(5) 0.266(6) Uani 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 C2 1.898(5) . ?
N3 H3 0.8600 . ?
N3 C9 1.392(6) . ?
N3 C11 1.403(6) . ?
C2 C12 1.367(7) . ?
C2 C20 1.370(7) . ?
C8 C13 1.388(6) . ?
C8 C18 1.383(6) . ?
C8 C25 1.479(6) . ?
C4 H4 0.9300 . ?
C4 C10 1.396(6) . ?
C4 C17 1.373(6) . ?
C5 C10 1.482(6) . ?
C5 C21 1.395(6) . ?
C5 C24 1.392(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(6) . ?
C6 C10 1.391(6) . ?
C7 H7 0.9300 . ?
C7 C25 1.400(6) . ?
C13 H13 0.9300 . ?
C13 C19 1.384(6) . ?
C9 C14 1.391(6) . ?
C9 C21 1.399(6) . ?
C11 C16 1.376(6) . ?
C11 C27 1.389(6) . ?
C12 H12 0.9300 . ?
C12 C16 1.380(6) . ?
C15 H15 0.9300 . ?
C15 C42 1.381(7) . ?
C15 C18 1.380(7) . ?
C14 H14 0.9300 . ?
C14 C22 1.379(6) . ?
C42 H42 0.9300 . ?
C42 C19 1.363(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C25 1.390(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C27 1.390(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.479(7) . ?
C22 C24 1.381(6) . ?
C23 F3 1.235(7) . ?
C23 F4 1.246(9) . ?
C23 F5 1.220(8) . ?
C24 H24 0.9300 . ?
C27 H27 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
C9 N3 H3 115.9 . . ?
C9 N3 C11 128.1(4) . . ?
C11 N3 H3 115.9 . . ?
C12 C2 Br1 119.9(4) . . ?
C12 C2 C20 120.5(4) . . ?
C20 C2 Br1 119.6(4) . . ?
C13 C8 C25 120.4(4) . . ?
C18 C8 C13 117.7(4) . . ?
C18 C8 C25 121.9(4) . . ?
C10 C4 H4 119.4 . . ?
C17 C4 H4 119.4 . . ?
C17 C4 C10 121.3(4) . . ?
C21 C5 C10 121.3(4) . . ?
C24 C5 C10 120.2(4) . . ?
C24 C5 C21 118.6(4) . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C10 121.4(4) . . ?
C10 C6 H6 119.3 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C25 121.6(4) . . ?
C25 C7 H7 119.2 . . ?
C8 C13 H13 119.4 . . ?
C19 C13 C8 121.2(4) . . ?
C19 C13 H13 119.4 . . ?
N3 C9 C21 117.9(4) . . ?
C14 C9 N3 123.5(4) . . ?
C14 C9 C21 118.5(4) . . ?
C4 C10 C5 120.4(4) . . ?
C6 C10 C4 117.2(4) . . ?
C6 C10 C5 122.4(4) . . ?
C16 C11 N3 123.3(4) . . ?
C16 C11 C27 118.6(4) . . ?
C27 C11 N3 118.1(4) . . ?
C2 C12 H12 120.2 . . ?
C2 C12 C16 119.5(5) . . ?
C16 C12 H12 120.2 . . ?
C42 C15 H15 119.7 . . ?
C18 C15 H15 119.7 . . ?
C18 C15 C42 120.6(5) . . ?
C9 C14 H14 120.1 . . ?
C22 C14 C9 119.7(4) . . ?
C22 C14 H14 120.1 . . ?
C15 C42 H42 120.4 . . ?
C19 C42 C15 119.3(5) . . ?
C19 C42 H42 120.4 . . ?
C11 C16 C12 121.3(4) . . ?
C11 C16 H16 119.3 . . ?
C12 C16 H16 119.3 . . ?
C4 C17 H17 119.0 . . ?
C4 C17 C25 121.9(4) . . ?
C25 C17 H17 119.0 . . ?
C8 C18 H18 119.6 . . ?
C15 C18 C8 120.9(5) . . ?
C15 C18 H18 119.6 . . ?
C13 C19 H19 119.8 . . ?
C42 C19 C13 120.4(4) . . ?
C42 C19 H19 119.8 . . ?
C2 C20 H20 120.0 . . ?
C2 C20 C27 120.1(4) . . ?
C27 C20 H20 120.0 . . ?
C5 C21 C9 121.6(4) . . ?
C5 C21 H21 119.2 . . ?
C9 C21 H21 119.2 . . ?
C14 C22 C23 118.8(4) . . ?
C14 C22 C24 121.8(4) . . ?
C24 C22 C23 119.4(4) . . ?
F3 C23 C22 117.6(5) . . ?
F3 C23 F4 100.5(7) . . ?
F4 C23 C22 112.0(7) . . ?
F5 C23 C22 116.6(5) . . ?
F5 C23 F3 107.1(8) . . ?
F5 C23 F4 100.6(7) . . ?
C5 C24 H24 120.2 . . ?
C22 C24 C5 119.7(4) . . ?
C22 C24 H24 120.2 . . ?
C7 C25 C8 121.7(4) . . ?
C17 C25 C8 121.6(4) . . ?
C17 C25 C7 116.7(4) . . ?
C11 C27 C20 119.9(5) . . ?
C11 C27 H27 120.0 . . ?
C20 C27 H27 120.0 . . ?

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 C12 C16 179.6(4) . . . . ?
Br1 C2 C20 C27 -178.2(4) . . . . ?
N3 C9 C14 C22 179.8(5) . . . . ?
N3 C9 C21 C5 -177.8(4) . . . . ?
N3 C11 C16 C12 -179.2(4) . . . . ?
N3 C11 C27 C20 -179.5(4) . . . . ?
C2 C12 C16 C11 -1.2(7) . . . . ?
C2 C20 C27 C11 -1.6(7) . . . . ?
C8 C13 C19 C42 -0.2(7) . . . . ?
C4 C17 C25 C8 -179.8(4) . . . . ?
C4 C17 C25 C7 0.3(6) . . . . ?
C6 C7 C25 C8 -179.9(4) . . . . ?
C6 C7 C25 C17 0.1(6) . . . . ?
C7 C6 C10 C4 0.3(6) . . . . ?
C7 C6 C10 C5 179.1(4) . . . . ?
C13 C8 C18 C15 0.1(7) . . . . ?
C13 C8 C25 C7 -144.9(4) . . . . ?
C13 C8 C25 C17 35.1(6) . . . . ?
C9 N3 C11 C16 37.6(8) . . . . ?
C9 N3 C11 C27 -144.0(5) . . . . ?
C9 C14 C22 C23 177.0(5) . . . . ?
C9 C14 C22 C24 -2.3(7) . . . . ?
C10 C4 C17 C25 -0.4(7) . . . . ?
C10 C5 C21 C9 178.4(4) . . . . ?
C10 C5 C24 C22 -178.2(4) . . . . ?
C10 C6 C7 C25 -0.4(7) . . . . ?
C11 N3 C9 C14 3.3(8) . . . . ?
C11 N3 C9 C21 -179.4(4) . . . . ?
C12 C2 C20 C27 2.8(7) . . . . ?
C15 C42 C19 C13 0.0(7) . . . . ?
C14 C9 C21 C5 -0.3(7) . . . . ?
C14 C22 C23 F3 -154.8(7) . . . . ?
C14 C22 C23 F4 89.6(9) . . . . ?
C14 C22 C23 F5 -25.6(11) . . . . ?
C14 C22 C24 C5 -0.1(7) . . . . ?
C42 C15 C18 C8 -0.3(8) . . . . ?
C16 C11 C27 C20 -1.0(7) . . . . ?
C17 C4 C10 C5 -178.7(4) . . . . ?
C17 C4 C10 C6 0.1(6) . . . . ?
C18 C8 C13 C19 0.1(7) . . . . ?
C18 C8 C25 C7 35.1(6) . . . . ?
C18 C8 C25 C17 -144.8(5) . . . . ?
C18 C15 C42 C19 0.2(8) . . . . ?
C20 C2 C12 C16 -1.5(7) . . . . ?
C21 C5 C10 C4 -148.4(4) . . . . ?
C21 C5 C10 C6 32.9(6) . . . . ?
C21 C5 C24 C22 2.3(7) . . . . ?
C21 C9 C14 C22 2.4(7) . . . . ?
C23 C22 C24 C5 -179.4(5) . . . . ?
C24 C5 C10 C4 32.1(6) . . . . ?
C24 C5 C10 C6 -146.6(4) . . . . ?
C24 C5 C21 C9 -2.1(7) . . . . ?
C24 C22 C23 F3 24.4(10) . . . . ?
C24 C22 C23 F4 -91.2(9) . . . . ?
C24 C22 C23 F5 153.7(9) . . . . ?
C25 C8 C13 C19 -179.8(4) . . . . ?
C25 C8 C18 C15 -179.9(5) . . . . ?
C27 C11 C16 C12 2.4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_s1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2180121'
loop_
_audit_author_name
_audit_author_address
'fang zheng'
;Fuzhou University
China
;
_audit_update_record             
;
2022-06-18 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_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         'C16 H11 F3 N2 O'
_chemical_formula_sum            'C16 H11 F3 N2 O'
_chemical_formula_weight         304.27
_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'
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           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                   12.9125(12)
_cell_length_b                   7.5482(8)
_cell_length_c                   15.0653(17)
_cell_angle_alpha                90
_cell_angle_beta                 104.114(4)
_cell_angle_gamma                90
_cell_volume                     1424.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3393
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.894
_cell_measurement_theta_min      2.386
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1447 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8732.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13918
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.092
_diffrn_reflns_theta_max         25.092
_diffrn_reflns_theta_min         2.386
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1792
_reflns_number_total             2514
_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       lb20201022
_computing_data_collection       ?
_computing_data_reduction        lb20201022
_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    ?
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.027
_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)+(0.0583P)²+0.5641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C002(H002), C006(H006), N007(H007), C008(H008), C009(H009), C011(H011),
 C013(H013), C016(H016)
2.b Idealised Me refined as rotating group:
 C021(H02A,H02B,H02C)
;
_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
F F 0.45923(11) 0.6946(2) 0.02381(10) 0.0781(5) Uani 1 1 d . . . . .
C002 C 0.32502(15) 0.4629(3) 0.28218(14) 0.0368(5) Uani 1 1 d . . . . .
H002 H 0.316798 0.426210 0.338996 0.044 Uiso 1 1 calc R . . . .
O003 O 0.45854(11) 0.3149(2) 0.44909(10) 0.0505(4) Uani 1 1 d . . . . .
C004 C 0.23536(15) 0.5034(3) 0.21248(14) 0.0353(5) Uani 1 1 d . . . . .
C005 C 0.12612(15) 0.4906(3) 0.22856(14) 0.0367(5) Uani 1 1 d . . . . .
C006 C 0.04166(15) 0.4225(3) 0.16220(15) 0.0435(5) Uani 1 1 d . . . . .
H006 H 0.053885 0.380097 0.107692 0.052 Uiso 1 1 calc R . . . .
N007 N 0.52084(13) 0.4352(3) 0.33340(12) 0.0423(5) Uani 1 1 d . . . . .
H007 H 0.579373 0.461852 0.318935 0.051 Uiso 1 1 calc R . . . .
C008 C 0.43879(15) 0.5365(3) 0.18255(14) 0.0383(5) Uani 1 1 d . . . . .
H008 H 0.506644 0.547943 0.172302 0.046 Uiso 1 1 calc R . . . .
C009 C 0.24776(15) 0.5603(3) 0.12805(15) 0.0386(5) Uani 1 1 d . . . . .
H009 H 0.188262 0.586367 0.081053 0.046 Uiso 1 1 calc R . . . .
C010 C 0.42680(15) 0.4773(3) 0.26704(14) 0.0357(5) Uani 1 1 d . . . . .
C011 C 0.00410(17) 0.5484(3) 0.32353(17) 0.0505(6) Uani 1 1 d . . . . .
H011 H -0.008508 0.590659 0.377932 0.061 Uiso 1 1 calc R . . . .
C012 C -0.07892(16) 0.4819(3) 0.25592(16) 0.0466(6) Uani 1 1 d . . . . .
C013 C 0.10612(16) 0.5518(3) 0.30979(16) 0.0451(6) Uani 1 1 d . . . . .
H013 H 0.162151 0.595635 0.355551 0.054 Uiso 1 1 calc R . . . .
C014 C 0.35023(16) 0.5781(3) 0.11434(14) 0.0383(5) Uani 1 1 d . . . . .
F015 F 0.29735(14) 0.7774(3) -0.00801(12) 0.0935(6) Uani 1 1 d . . . . .
C016 C -0.05990(16) 0.4167(3) 0.17556(16) 0.0490(6) Uani 1 1 d . . . . .
H016 H -0.115564 0.368994 0.130765 0.059 Uiso 1 1 calc R . . . .
C017 C 0.36187(17) 0.6429(4) 0.02398(16) 0.0500(6) Uani 1 1 d . . . . .
C018 C -0.18652(19) 0.4835(4) 0.26829(18) 0.0616(7) Uani 1 1 d . . . . .
C019 C 0.53270(16) 0.3588(3) 0.41685(15) 0.0397(5) Uani 1 1 d . . . . .
F020 F 0.33632(15) 0.5197(3) -0.04130(11) 0.0902(6) Uani 1 1 d . . . . .
C021 C 0.64715(16) 0.3320(4) 0.46752(16) 0.0543(6) Uani 1 1 d . . . . .
H02A H 0.649830 0.276730 0.525437 0.081 Uiso 1 1 calc GR . . . .
H02B H 0.682701 0.444529 0.477412 0.081 Uiso 1 1 calc GR . . . .
H02C H 0.682047 0.257454 0.432082 0.081 Uiso 1 1 calc GR . . . .
N022 N -0.27105(17) 0.4872(4) 0.27766(18) 0.0859(9) 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
F C017 1.317(2) . ?
C002 H002 0.9300 . ?
C002 C004 1.394(3) . ?
C002 C010 1.392(3) . ?
O003 C019 1.220(2) . ?
C004 C005 1.491(3) . ?
C004 C009 1.388(3) . ?
C005 C006 1.386(3) . ?
C005 C013 1.390(3) . ?
C006 H006 0.9300 . ?
C006 C016 1.375(3) . ?
N007 H007 0.8600 . ?
N007 C010 1.408(3) . ?
N007 C019 1.357(3) . ?
C008 H008 0.9300 . ?
C008 C010 1.393(3) . ?
C008 C014 1.374(3) . ?
C009 H009 0.9300 . ?
C009 C014 1.394(3) . ?
C011 H011 0.9300 . ?
C011 C012 1.381(3) . ?
C011 C013 1.383(3) . ?
C012 C016 1.383(3) . ?
C012 C018 1.446(3) . ?
C013 H013 0.9300 . ?
C014 C017 1.488(3) . ?
F015 C017 1.327(3) . ?
C016 H016 0.9300 . ?
C017 F020 1.335(3) . ?
C018 N022 1.135(3) . ?
C019 C021 1.503(3) . ?
C021 H02A 0.9600 . ?
C021 H02B 0.9600 . ?
C021 H02C 0.9600 . ?

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
C004 C002 H002 119.9 . . ?
C010 C002 H002 119.9 . . ?
C010 C002 C004 120.22(19) . . ?
C002 C004 C005 120.53(18) . . ?
C009 C004 C002 119.86(18) . . ?
C009 C004 C005 119.59(18) . . ?
C006 C005 C004 121.05(19) . . ?
C006 C005 C013 118.42(19) . . ?
C013 C005 C004 120.50(19) . . ?
C005 C006 H006 119.4 . . ?
C016 C006 C005 121.1(2) . . ?
C016 C006 H006 119.4 . . ?
C010 N007 H007 115.2 . . ?
C019 N007 H007 115.2 . . ?
C019 N007 C010 129.53(17) . . ?
C010 C008 H008 120.0 . . ?
C014 C008 H008 120.0 . . ?
C014 C008 C010 119.93(18) . . ?
C004 C009 H009 120.3 . . ?
C004 C009 C014 119.41(19) . . ?
C014 C009 H009 120.3 . . ?
C002 C010 N007 123.45(19) . . ?
C002 C010 C008 119.64(18) . . ?
C008 C010 N007 116.91(17) . . ?
C012 C011 H011 120.2 . . ?
C012 C011 C013 119.5(2) . . ?
C013 C011 H011 120.2 . . ?
C011 C012 C016 120.24(19) . . ?
C011 C012 C018 120.0(2) . . ?
C016 C012 C018 119.8(2) . . ?
C005 C013 H013 119.5 . . ?
C011 C013 C005 120.9(2) . . ?
C011 C013 H013 119.5 . . ?
C008 C014 C009 120.92(19) . . ?
C008 C014 C017 120.51(18) . . ?
C009 C014 C017 118.57(19) . . ?
C006 C016 C012 119.7(2) . . ?
C006 C016 H016 120.1 . . ?
C012 C016 H016 120.1 . . ?
F C017 C014 114.12(19) . . ?
F C017 F015 106.7(2) . . ?
F C017 F020 105.64(19) . . ?
F015 C017 C014 112.90(18) . . ?
F015 C017 F020 104.2(2) . . ?
F020 C017 C014 112.5(2) . . ?
N022 C018 C012 179.0(3) . . ?
O003 C019 N007 124.16(19) . . ?
O003 C019 C021 122.1(2) . . ?
N007 C019 C021 113.75(18) . . ?
C019 C021 H02A 109.5 . . ?
C019 C021 H02B 109.5 . . ?
C019 C021 H02C 109.5 . . ?
H02A C021 H02B 109.5 . . ?
H02A C021 H02C 109.5 . . ?
H02B C021 H02C 109.5 . . ?

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
C002 C004 C005 C006 -139.7(2) . . . . ?
C002 C004 C005 C013 42.2(3) . . . . ?
C002 C004 C009 C014 -0.7(3) . . . . ?
C004 C002 C010 N007 -178.6(2) . . . . ?
C004 C002 C010 C008 1.6(3) . . . . ?
C004 C005 C006 C016 -177.6(2) . . . . ?
C004 C005 C013 C011 176.8(2) . . . . ?
C004 C009 C014 C008 1.4(3) . . . . ?
C004 C009 C014 C017 -178.8(2) . . . . ?
C005 C004 C009 C014 177.73(19) . . . . ?
C005 C006 C016 C012 1.0(4) . . . . ?
C006 C005 C013 C011 -1.3(3) . . . . ?
C008 C014 C017 F -15.2(3) . . . . ?
C008 C014 C017 F015 -137.3(2) . . . . ?
C008 C014 C017 F020 105.2(2) . . . . ?
C009 C004 C005 C006 41.9(3) . . . . ?
C009 C004 C005 C013 -136.2(2) . . . . ?
C009 C014 C017 F 165.0(2) . . . . ?
C009 C014 C017 F015 42.9(3) . . . . ?
C009 C014 C017 F020 -74.7(3) . . . . ?
C010 C002 C004 C005 -179.20(19) . . . . ?
C010 C002 C004 C009 -0.8(3) . . . . ?
C010 N007 C019 O003 -1.2(4) . . . . ?
C010 N007 C019 C021 178.8(2) . . . . ?
C010 C008 C014 C009 -0.6(3) . . . . ?
C010 C008 C014 C017 179.5(2) . . . . ?
C011 C012 C016 C006 -1.7(4) . . . . ?
C012 C011 C013 C005 0.6(4) . . . . ?
C013 C005 C006 C016 0.5(3) . . . . ?
C013 C011 C012 C016 1.0(4) . . . . ?
C013 C011 C012 C018 -177.9(2) . . . . ?
C014 C008 C010 C002 -0.9(3) . . . . ?
C014 C008 C010 N007 179.3(2) . . . . ?
C018 C012 C016 C006 177.1(2) . . . . ?
C019 N007 C010 C002 7.6(4) . . . . ?
C019 N007 C010 C008 -172.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
