# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_T
_database_code_depnum_ccdc_archive 'CCDC 2059983'
loop_
_audit_author_name
_audit_author_address
'Wenjie Zhang'
;Huaibei Normal University
China
;
_audit_update_record             
;
2021-02-01 deposited with the CCDC.	2021-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 F N2'
_chemical_formula_sum            'C18 H13 F N2'
_chemical_formula_weight         276.30

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.661(2)
_cell_length_b                   11.744(2)
_cell_length_c                   10.481(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.40(3)
_cell_angle_gamma                90
_cell_volume                     1401.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7005
_cell_measurement_theta_min      2.491
_cell_measurement_theta_max      25.048

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.9995
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7005
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.491
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2477
_reflns_number_gt                1702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1484P)²+0.1823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.2034
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.9453(3) 0.9978(2) 0.6475(3) 0.1277(10) Uani 1 1 d . . . . .
N1 N 0.6694(2) 0.53129(19) 0.5651(2) 0.0576(7) Uani 1 1 d . . . . .
N2 N 0.6428(2) 0.6375(2) 0.5105(2) 0.0611(7) Uani 1 1 d . . . . .
H2A H 0.5775 0.6494 0.4558 0.073 Uiso 1 1 calc R U . . .
C1 C 0.8223(3) 0.4654(3) 0.4457(3) 0.0636(8) Uani 1 1 d . . . . .
H1 H 0.8242 0.5320 0.3981 0.076 Uiso 1 1 calc R U . . .
C2 C 0.8924(3) 0.3731(3) 0.4325(3) 0.0699(9) Uani 1 1 d . . . . .
H2 H 0.9429 0.3780 0.3751 0.084 Uiso 1 1 calc R U . . .
C3 C 0.8895(3) 0.2737(3) 0.5024(3) 0.0723(10) Uani 1 1 d . . . . .
H3 H 0.9374 0.2130 0.4907 0.087 Uiso 1 1 calc R U . . .
C4 C 0.8162(3) 0.2633(3) 0.5896(3) 0.0585(8) Uani 1 1 d . . . . .
H4 H 0.8140 0.1959 0.6356 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7465(2) 0.3545(2) 0.6073(2) 0.0488(7) Uani 1 1 d . . . . .
C6 C 0.7492(2) 0.4543(2) 0.5330(3) 0.0515(7) Uani 1 1 d . . . . .
C7 C 0.6608(2) 0.3731(2) 0.6863(2) 0.0467(7) Uani 1 1 d . . . . .
C8 C 0.6207(3) 0.3093(3) 0.7791(3) 0.0594(8) Uani 1 1 d . . . . .
H8 H 0.6509 0.2371 0.8018 0.071 Uiso 1 1 calc R U . . .
C9 C 0.5355(3) 0.3543(3) 0.8374(3) 0.0685(9) Uani 1 1 d . . . . .
H9 H 0.5095 0.3121 0.9007 0.082 Uiso 1 1 calc R U . . .
C10 C 0.4881(3) 0.4603(3) 0.8037(3) 0.0673(9) Uani 1 1 d . . . . .
H10 H 0.4289 0.4875 0.8426 0.081 Uiso 1 1 calc R U . . .
C11 C 0.5272(3) 0.5264(3) 0.7134(3) 0.0599(8) Uani 1 1 d . . . . .
H11 H 0.4959 0.5984 0.6915 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6140(2) 0.4832(2) 0.6560(3) 0.0486(7) Uani 1 1 d . . . . .
C13 C 0.7246(2) 0.7257(2) 0.5463(3) 0.0479(7) Uani 1 1 d . . . . .
C14 C 0.8110(3) 0.7227(3) 0.6592(3) 0.0585(8) Uani 1 1 d . . . . .
H14 H 0.8202 0.6585 0.7123 0.070 Uiso 1 1 calc R U . . .
C15 C 0.8840(3) 0.8160(3) 0.6929(3) 0.0702(9) Uani 1 1 d . . . . .
H15 H 0.9418 0.8148 0.7694 0.084 Uiso 1 1 calc R U . . .
C16 C 0.8710(3) 0.9103(3) 0.6132(4) 0.0673(9) Uani 1 1 d . . . . .
C17 C 0.7860(3) 0.9139(3) 0.5018(3) 0.0713(9) Uani 1 1 d . . . . .
H17 H 0.7774 0.9781 0.4486 0.086 Uiso 1 1 calc R U . . .
C18 C 0.7131(3) 0.8216(2) 0.4688(3) 0.0618(8) Uani 1 1 d . . . . .
H18 H 0.6549 0.8239 0.3927 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C16 1.342(4) . ?
N1 N2 1.380(3) . ?
N1 C12 1.382(3) . ?
N1 C6 1.390(4) . ?
N2 C13 1.403(4) . ?
N2 H2A 0.8600 . ?
C1 C2 1.382(5) . ?
C1 C6 1.384(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(4) . ?
C5 C7 1.445(4) . ?
C7 C8 1.385(4) . ?
C7 C12 1.413(4) . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C13 C18 1.378(4) . ?
C13 C14 1.381(4) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(5) . ?
C17 C18 1.376(4) . ?
C17 H17 0.9300 . ?
C18 H18 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
N2 N1 C12 123.9(2) . . ?
N2 N1 C6 126.2(2) . . ?
C12 N1 C6 109.7(2) . . ?
N1 N2 C13 118.5(2) . . ?
N1 N2 H2A 120.8 . . ?
C13 N2 H2A 120.8 . . ?
C2 C1 C6 116.9(3) . . ?
C2 C1 H1 121.5 . . ?
C6 C1 H1 121.5 . . ?
C1 C2 C3 121.8(3) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 C7 133.9(3) . . ?
C6 C5 C7 106.9(2) . . ?
C1 C6 N1 129.6(3) . . ?
C1 C6 C5 122.2(3) . . ?
N1 C6 C5 108.1(2) . . ?
C8 C7 C12 118.7(3) . . ?
C8 C7 C5 134.4(3) . . ?
C12 C7 C5 106.9(2) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 118.3(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 N1 130.2(3) . . ?
C11 C12 C7 121.5(3) . . ?
N1 C12 C7 108.3(2) . . ?
C18 C13 C14 119.2(3) . . ?
C18 C13 N2 118.1(2) . . ?
C14 C13 N2 122.6(2) . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
F1 C16 C17 121.0(3) . . ?
F1 C16 C15 118.2(3) . . ?
C17 C16 C15 120.8(3) . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C13 121.3(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.060

