# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_20230216_hg_1
_database_code_depnum_ccdc_archive 'CCDC 2293956'
loop_
_audit_author_name
_audit_author_address
'Jianquan Hong'
;Jiangnan University
China
;
_audit_update_record             
;
2023-09-09 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H9 Br F3 N'
_chemical_formula_sum            'C15 H9 Br F3 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         340.14

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1764(6)
_cell_length_b                   10.5249(7)
_cell_length_c                   15.2713(10)
_cell_angle_alpha                86.542(2)
_cell_angle_beta                 88.533(2)
_cell_angle_gamma                89.967(2)
_cell_volume                     1311.36(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.8999
_cell_measurement_theta_max      68.2555
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    4.521
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.5333
_exptl_absorpt_correction_T_max  0.7531

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           Cuk\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            17835
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         68.32
_diffrn_reflns_theta_full        68.32
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             4791
_reflns_number_gt                4551
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0810
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.097
_refine_ls_number_reflns         4791
_refine_ls_number_parameters     361
_refine_ls_number_restraints     24
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0291P)²+1.8159P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.805
_refine_diff_density_min         -0.535
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.48502(3) 0.17126(2) 0.44070(2) 0.02413(9) Uani d . . . 1 . .
F F1 0.8891(4) 0.07694(17) 0.56060(13) 0.0662(8) Uani d . . . 1 . .
N N1 0.8252(2) 0.28375(19) 0.53910(13) 0.0178(4) Uani d . . . 1 . .
C C1 0.7554(3) 0.5117(3) 0.70141(18) 0.0245(5) Uani d . . . 1 . .
H H1 0.707164 0.593783 0.70248 0.029 Uiso calc U . R 1 . .
Br Br2 0.99425(3) 0.67245(2) -0.03573(2) 0.02458(9) Uani d . . . 1 . .
F F2 1.0791(2) 0.2044(3) 0.51796(16) 0.0619(7) Uani d . . . 1 . .
N N2 0.6498(2) 0.77609(19) 0.07516(13) 0.0194(4) Uani d . . . 1 . .
C C2 0.8183(3) 0.4529(3) 0.77676(17) 0.0259(5) Uani d . . . 1 . .
H H2 0.81143 0.494688 0.830166 0.031 Uiso calc U . R 1 . .
F F3 0.8964(2) 0.15720(15) 0.42919(10) 0.0303(4) Uani d . . . 1 . .
C C3 0.8922(3) 0.3325(3) 0.77556(17) 0.0259(5) Uani d . . . 1 . .
H H3 0.93567 0.294713 0.828018 0.031 Uiso calc U . R 1 . .
F F4 0.5545(4) 0.57675(19) 0.08327(15) 0.0787(9) Uani d U . . 1 . .
C C4 0.9027(3) 0.2678(2) 0.69926(17) 0.0220(5) Uani d . . . 1 . .
H H4 0.953197 0.186555 0.698223 0.026 Uiso calc U . R 1 . .
C C5 0.8365(3) 0.3264(2) 0.62435(16) 0.0183(5) Uani d . . . 1 . .
F F5 0.3915(2) 0.7213(3) 0.04548(18) 0.0734(8) Uani d U . . 1 . .
C C6 0.7487(3) 0.3804(2) 0.48558(16) 0.0175(5) Uani d . . . 1 . .
F F6 0.5790(2) 0.67020(17) -0.04293(11) 0.0388(4) Uani d U . . 1 . .
C C7 0.7115(3) 0.4789(2) 0.53575(17) 0.0200(5) Uani d . . . 1 . .
H H7 0.659343 0.55571 0.516068 0.024 Uiso calc U . R 1 . .
C C8 0.7641(3) 0.4481(2) 0.62380(17) 0.0195(5) Uani d . . . 1 . .
C C9 0.7165(3) 0.3697(2) 0.39145(16) 0.0182(5) Uani d . . . 1 . .
C C10 0.7946(3) 0.4535(2) 0.32984(17) 0.0208(5) Uani d . . . 1 . .
H H10 0.866543 0.516282 0.34915 0.025 Uiso calc U . R 1 . .
C C11 0.7692(3) 0.4468(2) 0.24089(17) 0.0232(5) Uani d . . . 1 . .
H H11 0.822389 0.505403 0.199805 0.028 Uiso calc U . R 1 . .
C C12 0.6661(3) 0.3544(3) 0.21187(17) 0.0230(5) Uani d . . . 1 . .
H H12 0.651565 0.347975 0.150772 0.028 Uiso calc U . R 1 . .
C C13 0.5841(3) 0.2713(2) 0.27174(17) 0.0212(5) Uani d . . . 1 . .
H H13 0.512445 0.208543 0.252182 0.025 Uiso calc U . R 1 . .
C C14 0.6083(3) 0.2813(2) 0.36050(16) 0.0189(5) Uani d . . . 1 . .
C C15 0.7478(3) 0.9626(2) 0.25570(17) 0.0229(5) Uani d . . . 1 . .
H H15 0.807338 1.038614 0.262707 0.027 Uiso calc U . R 1 . .
C C16 0.6757(3) 0.8969(3) 0.32747(17) 0.0239(5) Uani d . . . 1 . .
H H16 0.686349 0.927808 0.384221 0.029 Uiso calc U . R 1 . .
C C17 0.5869(3) 0.7850(2) 0.31760(17) 0.0234(5) Uani d . . . 1 . .
H H17 0.537875 0.74163 0.367971 0.028 Uiso calc U . R 1 . .
C C18 0.5688(3) 0.7361(2) 0.23616(17) 0.0215(5) Uani d . . . 1 . .
H H18 0.507749 0.660639 0.229533 0.026 Uiso calc U . R 1 . .
C C19 0.6440(3) 0.8025(2) 0.16443(16) 0.0182(5) Uani d . . . 1 . .
C C20 0.7380(3) 0.8747(2) 0.02789(16) 0.0187(5) Uani d . . . 1 . .
C C21 0.7881(3) 0.9589(2) 0.08575(17) 0.0214(5) Uani d . . . 1 . .
H H21 0.850048 1.033926 0.071263 0.026 Uiso calc U . R 1 . .
C C22 0.7321(3) 0.9158(2) 0.17240(17) 0.0197(5) Uani d . . . 1 . .
C C23 0.7705(3) 0.8784(2) -0.06783(16) 0.0188(5) Uani d . . . 1 . .
C C24 0.6936(3) 0.9701(2) -0.12233(18) 0.0229(5) Uani d . . . 1 . .
H H24 0.620523 1.028823 -0.097191 0.027 Uiso calc U . R 1 . .
C C25 0.7218(3) 0.9773(2) -0.21233(18) 0.0250(5) Uani d . . . 1 . .
H H25 0.668225 1.040371 -0.248344 0.03 Uiso calc U . R 1 . .
C C26 0.8288(3) 0.8919(2) -0.24985(17) 0.0228(5) Uani d . . . 1 . .
H H26 0.847375 0.896049 -0.311615 0.027 Uiso calc U . R 1 . .
C C27 0.9086(3) 0.8004(2) -0.19693(16) 0.0210(5) Uani d . . . 1 . .
H H27 0.982044 0.741953 -0.222042 0.025 Uiso calc U . R 1 . .
C C28 0.8791(3) 0.7959(2) -0.10724(16) 0.0189(5) Uani d . . . 1 . .
C C29 0.5460(3) 0.6871(2) 0.03981(17) 0.0236(5) Uani d U . . 1 . .
C C30 0.9204(3) 0.1826(2) 0.51120(17) 0.0238(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C14 . 1.904(2) ?
F1 C30 . 1.327(3) ?
N1 C30 . 1.399(3) ?
N1 C5 . 1.408(3) ?
N1 C6 . 1.421(3) ?
C1 C2 . 1.384(4) ?
C1 C8 . 1.396(4) ?
C1 H1 . 0.95 ?
Br2 C28 . 1.910(2) ?
F2 C30 . 1.326(3) ?
N2 C29 . 1.405(3) ?
N2 C19 . 1.407(3) ?
N2 C20 . 1.415(3) ?
C2 C3 . 1.405(4) ?
C2 H2 . 0.95 ?
F3 C30 . 1.316(3) ?
C3 C4 . 1.385(4) ?
C3 H3 . 0.95 ?
F4 C29 . 1.306(3) ?
C4 C5 . 1.389(4) ?
C4 H4 . 0.95 ?
C5 C8 . 1.410(3) ?
F5 C29 . 1.315(4) ?
C6 C7 . 1.356(3) ?
C6 C9 . 1.479(3) ?
F6 C29 . 1.308(3) ?
C7 C8 . 1.441(4) ?
C7 H7 . 0.95 ?
C9 C10 . 1.393(4) ?
C9 C14 . 1.396(3) ?
C10 C11 . 1.385(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.388(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.386(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.385(4) ?
C13 H13 . 0.95 ?
C15 C16 . 1.379(4) ?
C15 C22 . 1.400(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.402(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.386(4) ?
C17 H17 . 0.95 ?
C18 C19 . 1.393(4) ?
C18 H18 . 0.95 ?
C19 C22 . 1.407(3) ?
C20 C21 . 1.359(4) ?
C20 C23 . 1.477(3) ?
C21 C22 . 1.436(4) ?
C21 H21 . 0.95 ?
C23 C28 . 1.393(4) ?
C23 C24 . 1.396(4) ?
C24 C25 . 1.385(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.392(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.393(4) ?
C26 H26 . 0.95 ?
C27 C28 . 1.383(4) ?
C27 H27 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C30 N1 C5 . . 121.6(2) ?
C30 N1 C6 . . 127.3(2) ?
C5 N1 C6 . . 108.36(19) ?
C2 C1 C8 . . 118.7(2) ?
C2 C1 H1 . . 120.6 ?
C8 C1 H1 . . 120.6 ?
C29 N2 C19 . . 122.8(2) ?
C29 N2 C20 . . 126.5(2) ?
C19 N2 C20 . . 108.46(19) ?
C1 C2 C3 . . 121.1(2) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C4 C3 C2 . . 121.2(2) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C5 . . 117.3(2) ?
C3 C4 H4 . . 121.3 ?
C5 C4 H4 . . 121.3 ?
C4 C5 N1 . . 130.3(2) ?
C4 C5 C8 . . 122.4(2) ?
N1 C5 C8 . . 107.3(2) ?
C7 C6 N1 . . 108.4(2) ?
C7 C6 C9 . . 127.7(2) ?
N1 C6 C9 . . 123.9(2) ?
C6 C7 C8 . . 108.8(2) ?
C6 C7 H7 . . 125.6 ?
C8 C7 H7 . . 125.6 ?
C1 C8 C5 . . 119.3(2) ?
C1 C8 C7 . . 133.6(2) ?
C5 C8 C7 . . 107.1(2) ?
C10 C9 C14 . . 117.6(2) ?
C10 C9 C6 . . 119.0(2) ?
C14 C9 C6 . . 123.4(2) ?
C11 C10 C9 . . 121.1(2) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C10 C11 C12 . . 119.9(2) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C13 C12 C11 . . 120.2(2) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C14 C13 C12 . . 119.0(2) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C13 C14 C9 . . 122.0(2) ?
C13 C14 Br1 . . 117.65(18) ?
C9 C14 Br1 . . 120.29(19) ?
C16 C15 C22 . . 119.2(2) ?
C16 C15 H15 . . 120.4 ?
C22 C15 H15 . . 120.4 ?
C15 C16 C17 . . 120.7(2) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C18 C17 C16 . . 121.6(2) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C17 C18 C19 . . 117.0(2) ?
C17 C18 H18 . . 121.5 ?
C19 C18 H18 . . 121.5 ?
C18 C19 C22 . . 122.5(2) ?
C18 C19 N2 . . 130.2(2) ?
C22 C19 N2 . . 107.3(2) ?
C21 C20 N2 . . 108.3(2) ?
C21 C20 C23 . . 127.9(2) ?
N2 C20 C23 . . 123.8(2) ?
C20 C21 C22 . . 108.8(2) ?
C20 C21 H21 . . 125.6 ?
C22 C21 H21 . . 125.6 ?
C15 C22 C19 . . 118.9(2) ?
C15 C22 C21 . . 133.9(2) ?
C19 C22 C21 . . 107.1(2) ?
C28 C23 C24 . . 117.4(2) ?
C28 C23 C20 . . 122.9(2) ?
C24 C23 C20 . . 119.6(2) ?
C25 C24 C23 . . 121.3(2) ?
C25 C24 H24 . . 119.3 ?
C23 C24 H24 . . 119.3 ?
C24 C25 C26 . . 119.8(2) ?
C24 C25 H25 . . 120.1 ?
C26 C25 H25 . . 120.1 ?
C25 C26 C27 . . 120.1(2) ?
C25 C26 H26 . . 120.0 ?
C27 C26 H26 . . 120.0 ?
C28 C27 C26 . . 118.9(2) ?
C28 C27 H27 . . 120.5 ?
C26 C27 H27 . . 120.5 ?
C27 C28 C23 . . 122.4(2) ?
C27 C28 Br2 . . 118.16(18) ?
C23 C28 Br2 . . 119.42(18) ?
F4 C29 F6 . . 108.0(2) ?
F4 C29 F5 . . 105.5(3) ?
F6 C29 F5 . . 106.9(2) ?
F4 C29 N2 . . 111.0(2) ?
F6 C29 N2 . . 113.1(2) ?
F5 C29 N2 . . 111.9(2) ?
F3 C30 F2 . . 106.9(2) ?
F3 C30 F1 . . 107.3(2) ?
F2 C30 F1 . . 105.9(3) ?
F3 C30 N1 . . 113.4(2) ?
F2 C30 N1 . . 112.1(2) ?
F1 C30 N1 . . 110.9(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C1 C2 C3 . . . . 1.0(4) ?
C1 C2 C3 C4 . . . . -0.8(4) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C3 C4 C5 N1 . . . . -178.3(2) ?
C3 C4 C5 C8 . . . . 1.4(4) ?
C30 N1 C5 C4 . . . . -16.8(4) ?
C6 N1 C5 C4 . . . . -179.1(2) ?
C30 N1 C5 C8 . . . . 163.5(2) ?
C6 N1 C5 C8 . . . . 1.1(2) ?
C30 N1 C6 C7 . . . . -161.8(2) ?
C5 N1 C6 C7 . . . . -0.8(3) ?
C30 N1 C6 C9 . . . . 18.7(4) ?
C5 N1 C6 C9 . . . . 179.8(2) ?
N1 C6 C7 C8 . . . . 0.2(3) ?
C9 C6 C7 C8 . . . . 179.5(2) ?
C2 C1 C8 C5 . . . . 0.0(4) ?
C2 C1 C8 C7 . . . . 179.4(3) ?
C4 C5 C8 C1 . . . . -1.2(4) ?
N1 C5 C8 C1 . . . . 178.6(2) ?
C4 C5 C8 C7 . . . . 179.2(2) ?
N1 C5 C8 C7 . . . . -1.0(3) ?
C6 C7 C8 C1 . . . . -179.0(3) ?
C6 C7 C8 C5 . . . . 0.5(3) ?
C7 C6 C9 C10 . . . . 64.6(3) ?
N1 C6 C9 C10 . . . . -116.1(3) ?
C7 C6 C9 C14 . . . . -113.9(3) ?
N1 C6 C9 C14 . . . . 65.3(3) ?
C14 C9 C10 C11 . . . . -1.8(3) ?
C6 C9 C10 C11 . . . . 179.6(2) ?
C9 C10 C11 C12 . . . . -0.8(4) ?
C10 C11 C12 C13 . . . . 2.1(4) ?
C11 C12 C13 C14 . . . . -0.7(4) ?
C12 C13 C14 C9 . . . . -2.0(4) ?
C12 C13 C14 Br1 . . . . 176.88(18) ?
C10 C9 C14 C13 . . . . 3.2(3) ?
C6 C9 C14 C13 . . . . -178.2(2) ?
C10 C9 C14 Br1 . . . . -175.65(17) ?
C6 C9 C14 Br1 . . . . 2.9(3) ?
C22 C15 C16 C17 . . . . -0.4(4) ?
C15 C16 C17 C18 . . . . 0.3(4) ?
C16 C17 C18 C19 . . . . 0.5(4) ?
C17 C18 C19 C22 . . . . -1.3(4) ?
C17 C18 C19 N2 . . . . 178.9(2) ?
C29 N2 C19 C18 . . . . 14.4(4) ?
C20 N2 C19 C18 . . . . 178.4(2) ?
C29 N2 C19 C22 . . . . -165.4(2) ?
C20 N2 C19 C22 . . . . -1.4(3) ?
C29 N2 C20 C21 . . . . 164.2(2) ?
C19 N2 C20 C21 . . . . 1.0(3) ?
C29 N2 C20 C23 . . . . -17.5(4) ?
C19 N2 C20 C23 . . . . 179.3(2) ?
N2 C20 C21 C22 . . . . -0.2(3) ?
C23 C20 C21 C22 . . . . -178.4(2) ?
C16 C15 C22 C19 . . . . -0.4(4) ?
C16 C15 C22 C21 . . . . 179.3(3) ?
C18 C19 C22 C15 . . . . 1.3(4) ?
N2 C19 C22 C15 . . . . -178.9(2) ?
C18 C19 C22 C21 . . . . -178.5(2) ?
N2 C19 C22 C21 . . . . 1.3(3) ?
C20 C21 C22 C15 . . . . 179.5(3) ?
C20 C21 C22 C19 . . . . -0.7(3) ?
C21 C20 C23 C28 . . . . 107.1(3) ?
N2 C20 C23 C28 . . . . -70.9(3) ?
C21 C20 C23 C24 . . . . -71.1(3) ?
N2 C20 C23 C24 . . . . 110.9(3) ?
C28 C23 C24 C25 . . . . 1.2(3) ?
C20 C23 C24 C25 . . . . 179.5(2) ?
C23 C24 C25 C26 . . . . -0.1(4) ?
C24 C25 C26 C27 . . . . -0.7(4) ?
C25 C26 C27 C28 . . . . 0.2(4) ?
C26 C27 C28 C23 . . . . 1.0(4) ?
C26 C27 C28 Br2 . . . . -178.40(18) ?
C24 C23 C28 C27 . . . . -1.7(3) ?
C20 C23 C28 C27 . . . . -180.0(2) ?
C24 C23 C28 Br2 . . . . 177.69(17) ?
C20 C23 C28 Br2 . . . . -0.6(3) ?
C19 N2 C29 F4 . . . . -53.8(4) ?
C20 N2 C29 F4 . . . . 145.2(3) ?
C19 N2 C29 F6 . . . . -175.4(2) ?
C20 N2 C29 F6 . . . . 23.6(4) ?
C19 N2 C29 F5 . . . . 63.8(3) ?
C20 N2 C29 F5 . . . . -97.2(3) ?
C5 N1 C30 F3 . . . . -178.8(2) ?
C6 N1 C30 F3 . . . . -20.0(4) ?
C5 N1 C30 F2 . . . . -57.7(3) ?
C6 N1 C30 F2 . . . . 101.1(3) ?
C5 N1 C30 F1 . . . . 60.4(3) ?
C6 N1 C30 F1 . . . . -140.8(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 F1 . 0.95 2.52 3.009(3) 111.8 ?
C18 H18 F4 . 0.95 2.47 2.961(3) 111.9 ?



####################################################################### 
# 
# 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_20230905_zcg
_database_code_depnum_ccdc_archive 'CCDC 2293958'
loop_
_audit_author_name
_audit_author_address
'Jianquan Hong'
;Jiangnan University
China
;
_audit_update_record             
;
2023-09-09 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H10 F3 N O2'
_chemical_formula_sum            'C18 H10 F3 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         329.27

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6165(5)
_cell_length_b                   10.3211(8)
_cell_length_c                   10.9424(8)
_cell_angle_alpha                96.542(3)
_cell_angle_beta                 96.293(3)
_cell_angle_gamma                102.766(3)
_cell_volume                     716.99(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6953
_cell_measurement_theta_min      4.1065
_cell_measurement_theta_max      68.2947
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.028
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336

_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_T_max  0.7531

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           Cuk\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            8757
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_full        68.36
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2627
_reflns_number_gt                2361
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1303
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0733P)²+0.2208P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.13268(18) 0.42509(11) 0.26559(11) 0.0385(3) Uani d . . . 1 . .
N N1 0.4062(2) 0.60903(13) 0.32641(12) 0.0186(3) Uani d . . . 1 . .
O O1 -0.16996(17) 0.89080(11) 0.66945(10) 0.0193(3) Uani d . . . 1 . .
C C1 0.6502(3) 0.74448(17) 0.07445(15) 0.0247(4) Uani d . . . 1 . .
H H1 0.652742 0.822049 0.034953 0.03 Uiso calc U . R 1 . .
F F2 0.40609(18) 0.40315(10) 0.37606(11) 0.0347(3) Uani d . . . 1 . .
O O2 -0.23569(19) 0.94244(12) 0.85940(11) 0.0251(3) Uani d . . . 1 . .
C C2 0.7654(3) 0.65329(19) 0.03855(16) 0.0284(4) Uani d . . . 1 . .
H H2 0.847275 0.668382 -0.026847 0.034 Uiso calc U . R 1 . .
C C3 0.7633(3) 0.53955(18) 0.09689(17) 0.0279(4) Uani d . . . 1 . .
H H3 0.84394 0.478843 0.070187 0.033 Uiso calc U . R 1 . .
F F3 0.19774(18) 0.50783(10) 0.45721(10) 0.0318(3) Uani d . . . 1 . .
C C4 0.6464(3) 0.51299(17) 0.19290(16) 0.0245(4) Uani d . . . 1 . .
H H4 0.645761 0.435707 0.232576 0.029 Uiso calc U . R 1 . .
C C5 0.5298(2) 0.60486(16) 0.22863(14) 0.0195(3) Uani d . . . 1 . .
C C6 0.5295(2) 0.71912(16) 0.17088(14) 0.0203(3) Uani d . . . 1 . .
C C7 0.3994(2) 0.79266(16) 0.23222(15) 0.0205(3) Uani d . . . 1 . .
H H7 0.370392 0.874335 0.211822 0.025 Uiso calc U . R 1 . .
C C8 0.3254(2) 0.72641(15) 0.32364(15) 0.0184(3) Uani d . . . 1 . .
C C9 0.1990(2) 0.76902(15) 0.41703(15) 0.0185(3) Uani d . . . 1 . .
C C10 0.0014(2) 0.78985(15) 0.37752(15) 0.0191(3) Uani d . . . 1 . .
H H10 -0.050021 0.775169 0.291327 0.023 Uiso calc U . R 1 . .
C C11 -0.1201(2) 0.83154(15) 0.46242(15) 0.0195(3) Uani d . . . 1 . .
H H11 -0.253969 0.845516 0.435255 0.023 Uiso calc U . R 1 . .
C C12 -0.0425(2) 0.85244(14) 0.58759(15) 0.0175(3) Uani d . . . 1 . .
C C13 0.1562(2) 0.83630(15) 0.63006(15) 0.0187(3) Uani d . . . 1 . .
C C14 0.2762(2) 0.79415(15) 0.54248(15) 0.0196(3) Uani d . . . 1 . .
H H14 0.411779 0.782676 0.569374 0.024 Uiso calc U . R 1 . .
C C15 0.2264(2) 0.86512(16) 0.76235(15) 0.0212(4) Uani d . . . 1 . .
H H15 0.362705 0.858413 0.793867 0.025 Uiso calc U . R 1 . .
C C16 0.0994(3) 0.90135(16) 0.84086(15) 0.0224(4) Uani d . . . 1 . .
H H16 0.147382 0.919414 0.927539 0.027 Uiso calc U . R 1 . .
C C17 -0.1092(3) 0.91341(15) 0.79594(15) 0.0201(3) Uani d . . . 1 . .
C C18 0.2864(3) 0.48874(16) 0.35662(15) 0.0207(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C18 . 1.339(2) ?
N1 C18 . 1.412(2) ?
N1 C5 . 1.419(2) ?
N1 C8 . 1.4299(19) ?
O1 C17 . 1.377(2) ?
O1 C12 . 1.3795(19) ?
C1 C2 . 1.386(3) ?
C1 C6 . 1.406(2) ?
C1 H1 . 0.95 ?
F2 C18 . 1.3294(19) ?
O2 C17 . 1.209(2) ?
C2 C3 . 1.397(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.388(2) ?
C3 H3 . 0.95 ?
F3 C18 . 1.3183(19) ?
C4 C5 . 1.397(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.400(2) ?
C6 C7 . 1.437(2) ?
C7 C8 . 1.350(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.478(2) ?
C9 C14 . 1.385(2) ?
C9 C10 . 1.402(2) ?
C10 C11 . 1.385(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.95 ?
C12 C13 . 1.397(2) ?
C13 C14 . 1.401(2) ?
C13 C15 . 1.447(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.344(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.451(2) ?
C16 H16 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C18 N1 C5 . . 120.06(13) ?
C18 N1 C8 . . 121.61(13) ?
C5 N1 C8 . . 107.01(13) ?
C17 O1 C12 . . 121.92(12) ?
C2 C1 C6 . . 118.21(16) ?
C2 C1 H1 . . 120.9 ?
C6 C1 H1 . . 120.9 ?
C1 C2 C3 . . 121.12(16) ?
C1 C2 H2 . . 119.4 ?
C3 C2 H2 . . 119.4 ?
C4 C3 C2 . . 121.67(16) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C3 C4 C5 . . 117.10(16) ?
C3 C4 H4 . . 121.4 ?
C5 C4 H4 . . 121.4 ?
C4 C5 C6 . . 122.00(15) ?
C4 C5 N1 . . 130.12(15) ?
C6 C5 N1 . . 107.80(13) ?
C5 C6 C1 . . 119.90(15) ?
C5 C6 C7 . . 107.42(14) ?
C1 C6 C7 . . 132.63(15) ?
C8 C7 C6 . . 108.69(14) ?
C8 C7 H7 . . 125.7 ?
C6 C7 H7 . . 125.7 ?
C7 C8 N1 . . 109.05(14) ?
C7 C8 C9 . . 127.98(14) ?
N1 C8 C9 . . 122.71(14) ?
C14 C9 C10 . . 119.44(15) ?
C14 C9 C8 . . 121.11(14) ?
C10 C9 C8 . . 119.39(14) ?
C11 C10 C9 . . 120.92(14) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C12 C11 C10 . . 118.69(14) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.7 ?
O1 C12 C11 . . 117.00(13) ?
O1 C12 C13 . . 121.07(14) ?
C11 C12 C13 . . 121.93(15) ?
C12 C13 C14 . . 118.32(15) ?
C12 C13 C15 . . 117.81(15) ?
C14 C13 C15 . . 123.86(14) ?
C9 C14 C13 . . 120.65(14) ?
C9 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C13 . . 120.30(15) ?
C16 C15 H15 . . 119.9 ?
C13 C15 H15 . . 119.9 ?
C15 C16 C17 . . 121.34(15) ?
C15 C16 H16 . . 119.3 ?
C17 C16 H16 . . 119.3 ?
O2 C17 O1 . . 116.48(14) ?
O2 C17 C16 . . 126.05(15) ?
O1 C17 C16 . . 117.47(14) ?
F3 C18 F2 . . 107.58(13) ?
F3 C18 F1 . . 106.67(14) ?
F2 C18 F1 . . 106.14(13) ?
F3 C18 N1 . . 112.84(13) ?
F2 C18 N1 . . 110.44(14) ?
F1 C18 N1 . . 112.79(14) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.4(3) ?
C1 C2 C3 C4 . . . . 0.0(3) ?
C2 C3 C4 C5 . . . . 0.2(3) ?
C3 C4 C5 C6 . . . . 0.0(2) ?
C3 C4 C5 N1 . . . . -176.17(15) ?
C18 N1 C5 C4 . . . . -37.4(2) ?
C8 N1 C5 C4 . . . . 178.48(16) ?
C18 N1 C5 C6 . . . . 146.01(14) ?
C8 N1 C5 C6 . . . . 1.88(16) ?
C4 C5 C6 C1 . . . . -0.5(2) ?
N1 C5 C6 C1 . . . . 176.47(13) ?
C4 C5 C6 C7 . . . . -178.36(14) ?
N1 C5 C6 C7 . . . . -1.42(17) ?
C2 C1 C6 C5 . . . . 0.7(2) ?
C2 C1 C6 C7 . . . . 177.93(16) ?
C5 C6 C7 C8 . . . . 0.40(18) ?
C1 C6 C7 C8 . . . . -177.12(17) ?
C6 C7 C8 N1 . . . . 0.79(18) ?
C6 C7 C8 C9 . . . . 174.96(15) ?
C18 N1 C8 C7 . . . . -145.11(15) ?
C5 N1 C8 C7 . . . . -1.66(17) ?
C18 N1 C8 C9 . . . . 40.4(2) ?
C5 N1 C8 C9 . . . . -176.20(13) ?
C7 C8 C9 C14 . . . . -115.90(19) ?
N1 C8 C9 C14 . . . . 57.5(2) ?
C7 C8 C9 C10 . . . . 61.4(2) ?
N1 C8 C9 C10 . . . . -125.19(16) ?
C14 C9 C10 C11 . . . . -1.8(2) ?
C8 C9 C10 C11 . . . . -179.13(14) ?
C9 C10 C11 C12 . . . . 0.0(2) ?
C17 O1 C12 C11 . . . . 179.56(13) ?
C17 O1 C12 C13 . . . . -0.7(2) ?
C10 C11 C12 O1 . . . . -178.49(12) ?
C10 C11 C12 C13 . . . . 1.8(2) ?
O1 C12 C13 C14 . . . . 178.53(13) ?
C11 C12 C13 C14 . . . . -1.8(2) ?
O1 C12 C13 C15 . . . . -1.9(2) ?
C11 C12 C13 C15 . . . . 177.83(14) ?
C10 C9 C14 C13 . . . . 1.8(2) ?
C8 C9 C14 C13 . . . . 179.10(13) ?
C12 C13 C14 C9 . . . . -0.1(2) ?
C15 C13 C14 C9 . . . . -179.67(14) ?
C12 C13 C15 C16 . . . . 2.4(2) ?
C14 C13 C15 C16 . . . . -178.03(15) ?
C13 C15 C16 C17 . . . . -0.4(2) ?
C12 O1 C17 O2 . . . . -177.70(13) ?
C12 O1 C17 C16 . . . . 2.7(2) ?
C15 C16 C17 O2 . . . . 178.31(16) ?
C15 C16 C17 O1 . . . . -2.2(2) ?
C5 N1 C18 F3 . . . . 173.36(13) ?
C8 N1 C18 F3 . . . . -47.8(2) ?
C5 N1 C18 F2 . . . . 52.92(19) ?
C8 N1 C18 F2 . . . . -168.24(14) ?
C5 N1 C18 F1 . . . . -65.66(19) ?
C8 N1 C18 F1 . . . . 73.18(19) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 F2 . 0.95 2.35 2.872(2) 114.1 ?
C7 H7 O2 2_576 0.95 2.43 3.3689(19) 169.6 ?
C16 H16 O2 2_577 0.95 2.53 3.417(2) 156.0 ?



####################################################################### 
# 
# 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_20230217_hg_2
_database_code_depnum_ccdc_archive 'CCDC 2293957'
loop_
_audit_author_name
_audit_author_address
'Jianquan Hong'
;Jiangnan University
China
;
_audit_update_record             
;
2023-09-09 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H9 Cl F3 N'
_chemical_formula_sum            'C15 H9 Cl F3 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         295.68
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   5.9221(4)
_cell_length_b                   21.7851(16)
_cell_length_c                   10.0601(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.563(4)
_cell_angle_gamma                90
_cell_volume                     1275.90(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6011
_cell_measurement_theta_min      4.0585
_cell_measurement_theta_max      68.2289
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

_exptl_absorpt_coefficient_mu    2.903
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.5326
_exptl_absorpt_correction_T_max  0.7531

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           Cuk\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            6340
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_full        68.25
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             1822
_reflns_number_gt                1699
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0829
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.100
_refine_ls_number_reflns         1822
_refine_ls_number_parameters     181
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+0.4436P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 516 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(19)

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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.23899(13) 0.34793(4) 0.10884(9) 0.0355(2) Uani d . . . 1 . .
N N1 0.6949(5) 0.41128(12) 0.6196(3) 0.0282(6) Uani d . . . 1 . .
F F1 0.7184(5) 0.50754(10) 0.7032(2) 0.0476(6) Uani d . . . 1 . .
C C1 1.0002(6) 0.29324(16) 0.8268(3) 0.0289(7) Uani d . . . 1 . .
H H1 0.974386 0.251127 0.843481 0.035 Uiso calc U . R 1 . .
C C2 1.1978(7) 0.32186(17) 0.8904(4) 0.0323(8) Uani d . . . 1 . .
H H2 1.310194 0.29914 0.95014 0.039 Uiso calc U . R 1 . .
F F2 0.7673(6) 0.49521(11) 0.5013(3) 0.0581(8) Uani d . . . 1 . .
F F3 0.4330(5) 0.48596(10) 0.5486(3) 0.0542(7) Uani d . . . 1 . .
C C3 1.2346(7) 0.38436(19) 0.8678(4) 0.0347(8) Uani d . . . 1 . .
H H3 1.372561 0.403081 0.912744 0.042 Uiso calc U . R 1 . .
C C4 1.0768(7) 0.41940(17) 0.7823(4) 0.0324(8) Uani d . . . 1 . .
H H4 1.102325 0.461763 0.768216 0.039 Uiso calc U . R 1 . .
C C5 0.8780(6) 0.38982(15) 0.7174(3) 0.0269(7) Uani d . . . 1 . .
C C6 0.8371(6) 0.32704(15) 0.7371(3) 0.0252(7) Uani d . . . 1 . .
C C7 0.6281(6) 0.31126(15) 0.6487(3) 0.0257(7) Uani d . . . 1 . .
H H7 0.558443 0.271828 0.641311 0.031 Uiso calc U . R 1 . .
C C8 0.5448(6) 0.36181(15) 0.5769(3) 0.0262(7) Uani d . . . 1 . .
C C9 0.3474(6) 0.36393(15) 0.4639(3) 0.0251(7) Uani d . . . 1 . .
C C10 0.1487(6) 0.33185(16) 0.4757(4) 0.0293(7) Uani d . . . 1 . .
H H10 0.13755 0.312489 0.558818 0.035 Uiso calc U . R 1 . .
C C11 -0.0324(6) 0.32784(16) 0.3678(4) 0.0327(8) Uani d . . . 1 . .
H H11 -0.168216 0.306322 0.377011 0.039 Uiso calc U . R 1 . .
C C12 -0.0146(6) 0.35545(16) 0.2459(4) 0.0269(7) Uani d . . . 1 . .
C C13 0.1803(6) 0.38768(16) 0.2312(3) 0.0287(7) Uani d . . . 1 . .
H H13 0.189969 0.406844 0.147645 0.034 Uiso calc U . R 1 . .
C C14 0.3625(6) 0.39178(16) 0.3404(4) 0.0281(7) Uani d . . . 1 . .
H H14 0.497652 0.413567 0.330931 0.034 Uiso calc U . R 1 . .
C C15 0.6539(7) 0.47409(16) 0.5926(3) 0.0335(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C12 . 1.739(4) ?
N1 C5 . 1.404(4) ?
N1 C15 . 1.408(5) ?
N1 C8 . 1.413(5) ?
F1 C15 . 1.326(4) ?
C1 C2 . 1.376(5) ?
C1 C6 . 1.404(5) ?
C1 H1 . 0.95 ?
C2 C3 . 1.404(6) ?
C2 H2 . 0.95 ?
F2 C15 . 1.316(5) ?
F3 C15 . 1.328(5) ?
C3 C4 . 1.379(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.395(5) ?
C4 H4 . 0.95 ?
C5 C6 . 1.409(5) ?
C6 C7 . 1.427(5) ?
C7 C8 . 1.359(5) ?
C7 H7 . 0.95 ?
C8 C9 . 1.475(5) ?
C9 C10 . 1.392(5) ?
C9 C14 . 1.400(5) ?
C10 C11 . 1.382(6) ?
C10 H10 . 0.95 ?
C11 C12 . 1.387(5) ?
C11 H11 . 0.95 ?
C12 C13 . 1.382(5) ?
C13 C14 . 1.394(5) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C15 . . 122.9(3) ?
C5 N1 C8 . . 108.7(3) ?
C15 N1 C8 . . 127.3(3) ?
C2 C1 C6 . . 119.2(3) ?
C2 C1 H1 . . 120.4 ?
C6 C1 H1 . . 120.4 ?
C1 C2 C3 . . 120.5(3) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C4 C3 C2 . . 122.0(4) ?
C4 C3 H3 . . 119.0 ?
C2 C3 H3 . . 119.0 ?
C3 C4 C5 . . 117.0(3) ?
C3 C4 H4 . . 121.5 ?
C5 C4 H4 . . 121.5 ?
C4 C5 N1 . . 130.6(3) ?
C4 C5 C6 . . 122.3(3) ?
N1 C5 C6 . . 106.9(3) ?
C1 C6 C5 . . 118.9(3) ?
C1 C6 C7 . . 133.6(3) ?
C5 C6 C7 . . 107.3(3) ?
C8 C7 C6 . . 108.9(3) ?
C8 C7 H7 . . 125.5 ?
C6 C7 H7 . . 125.5 ?
C7 C8 N1 . . 108.0(3) ?
C7 C8 C9 . . 126.5(3) ?
N1 C8 C9 . . 125.2(3) ?
C10 C9 C14 . . 119.1(3) ?
C10 C9 C8 . . 118.8(3) ?
C14 C9 C8 . . 121.8(3) ?
C11 C10 C9 . . 120.8(3) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 119.5(3) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C13 C12 C11 . . 121.0(3) ?
C13 C12 Cl1 . . 119.7(3) ?
C11 C12 Cl1 . . 119.3(3) ?
C12 C13 C14 . . 119.3(3) ?
C12 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C13 C14 C9 . . 120.3(3) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
F2 C15 F1 . . 106.7(3) ?
F2 C15 F3 . . 107.3(3) ?
F1 C15 F3 . . 106.7(3) ?
F2 C15 N1 . . 112.5(3) ?
F1 C15 N1 . . 111.1(3) ?
F3 C15 N1 . . 112.2(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.1(5) ?
C1 C2 C3 C4 . . . . 0.1(6) ?
C2 C3 C4 C5 . . . . -0.7(6) ?
C3 C4 C5 N1 . . . . -175.5(3) ?
C3 C4 C5 C6 . . . . 0.0(5) ?
C15 N1 C5 C4 . . . . -16.4(6) ?
C8 N1 C5 C4 . . . . 174.7(3) ?
C15 N1 C5 C6 . . . . 167.6(3) ?
C8 N1 C5 C6 . . . . -1.3(3) ?
C2 C1 C6 C5 . . . . -1.6(5) ?
C2 C1 C6 C7 . . . . 174.4(4) ?
C4 C5 C6 C1 . . . . 1.1(5) ?
N1 C5 C6 C1 . . . . 177.5(3) ?
C4 C5 C6 C7 . . . . -175.9(3) ?
N1 C5 C6 C7 . . . . 0.5(3) ?
C1 C6 C7 C8 . . . . -175.9(3) ?
C5 C6 C7 C8 . . . . 0.5(4) ?
C6 C7 C8 N1 . . . . -1.4(4) ?
C6 C7 C8 C9 . . . . 172.6(3) ?
C5 N1 C8 C7 . . . . 1.7(4) ?
C15 N1 C8 C7 . . . . -166.6(3) ?
C5 N1 C8 C9 . . . . -172.3(3) ?
C15 N1 C8 C9 . . . . 19.4(5) ?
C7 C8 C9 C10 . . . . 43.8(5) ?
N1 C8 C9 C10 . . . . -143.2(3) ?
C7 C8 C9 C14 . . . . -129.4(4) ?
N1 C8 C9 C14 . . . . 43.6(5) ?
C14 C9 C10 C11 . . . . -0.6(5) ?
C8 C9 C10 C11 . . . . -174.0(3) ?
C9 C10 C11 C12 . . . . 0.8(5) ?
C10 C11 C12 C13 . . . . -0.9(5) ?
C10 C11 C12 Cl1 . . . . 177.7(3) ?
C11 C12 C13 C14 . . . . 0.8(5) ?
Cl1 C12 C13 C14 . . . . -177.9(3) ?
C12 C13 C14 C9 . . . . -0.5(5) ?
C10 C9 C14 C13 . . . . 0.4(5) ?
C8 C9 C14 C13 . . . . 173.6(3) ?
C5 N1 C15 F2 . . . . 87.8(4) ?
C8 N1 C15 F2 . . . . -105.4(4) ?
C5 N1 C15 F1 . . . . -31.7(5) ?
C8 N1 C15 F1 . . . . 135.0(3) ?
C5 N1 C15 F3 . . . . -151.1(3) ?
C8 N1 C15 F3 . . . . 15.6(5) ?



