# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Z-FPhNaF
_database_code_depnum_ccdc_archive 'CCDC 2101699'
loop_
_audit_author_name
_audit_author_address
'cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-08-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 F2 N'
_chemical_formula_sum            'C19 H11 F2 N'
_chemical_formula_weight         291.29
_chemical_absolute_configuration ?
_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'

_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   26.343(3)
_cell_length_b                   3.8422(4)
_cell_length_c                   13.2780(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1343.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5591
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      3.07
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_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    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22957
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.641
_diffrn_reflns_theta_min         3.068
_diffrn_ambient_temperature      100.06
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2971
_reflns_number_total             3747
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 1057 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      1.117
_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+1.5214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1599
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_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
F1 F 0.49328(11) 0.4392(8) 0.6103(2) 0.0317(8) Uani 1 1 d . . . . .
F2 F 0.06564(10) 1.2340(8) 0.3793(2) 0.0273(7) Uani 1 1 d . . . . .
N1 N 0.24749(16) 0.5381(12) 0.7163(3) 0.0287(10) Uani 1 1 d . . . . .
C1 C 0.11102(17) 1.1278(12) 0.4180(4) 0.0196(10) Uani 1 1 d . . . . .
C2 C 0.11142(17) 0.9588(12) 0.5091(4) 0.0177(9) Uani 1 1 d . . . . .
H2 H 0.0808 0.9152 0.5448 0.021 Uiso 1 1 calc R U . . .
C3 C 0.15815(16) 0.8531(11) 0.5478(3) 0.0155(9) Uani 1 1 d . . . . .
H3 H 0.1592 0.7345 0.6105 0.019 Uiso 1 1 calc R U . . .
C4 C 0.20336(16) 0.9172(11) 0.4966(3) 0.0143(8) Uani 1 1 d . . . . .
C5 C 0.20075(17) 1.0970(12) 0.4037(3) 0.0177(9) Uani 1 1 d . . . . .
H5 H 0.2311 1.1463 0.3677 0.021 Uiso 1 1 calc R U . . .
C6 C 0.15431(17) 1.2022(12) 0.3647(4) 0.0195(9) Uani 1 1 d . . . . .
H6 H 0.1526 1.3230 0.3023 0.023 Uiso 1 1 calc R U . . .
C7 C 0.25274(17) 0.7925(11) 0.5362(3) 0.0148(8) Uani 1 1 d . . . . .
C8 C 0.25137(18) 0.6506(12) 0.6369(4) 0.0182(9) Uani 1 1 d . . . . .
C9 C 0.29661(16) 0.7936(11) 0.4830(3) 0.0147(8) Uani 1 1 d . . . . .
H9 H 0.2944 0.8717 0.4153 0.018 Uiso 1 1 calc R U . . .
C10 C 0.34762(16) 0.6867(11) 0.5185(3) 0.0148(9) Uani 1 1 d . . . . .
C11 C 0.36400(17) 0.7631(12) 0.6146(3) 0.0195(10) Uani 1 1 d . . . . .
H11 H 0.3414 0.8747 0.6601 0.023 Uiso 1 1 calc R U . . .
C12 C 0.41335(18) 0.6796(12) 0.6470(3) 0.0201(10) Uani 1 1 d . . . . .
H12 H 0.4241 0.7303 0.7136 0.024 Uiso 1 1 calc R U . . .
C13 C 0.44538(17) 0.5230(12) 0.5795(4) 0.0208(10) Uani 1 1 d . . . . .
C14 C 0.43186(17) 0.4374(12) 0.4806(4) 0.0185(9) Uani 1 1 d . . . . .
C15 C 0.38136(16) 0.5194(12) 0.4480(3) 0.0151(8) Uani 1 1 d . . . . .
C16 C 0.36749(18) 0.4344(12) 0.3474(4) 0.0191(9) Uani 1 1 d . . . . .
H16 H 0.3343 0.4868 0.3241 0.023 Uiso 1 1 calc R U . . .
C17 C 0.40149(19) 0.2780(13) 0.2841(4) 0.0227(10) Uani 1 1 d . . . . .
H17 H 0.3915 0.2236 0.2171 0.027 Uiso 1 1 calc R U . . .
C18 C 0.45104(19) 0.1961(13) 0.3164(4) 0.0224(10) Uani 1 1 d . . . . .
H18 H 0.4742 0.0880 0.2714 0.027 Uiso 1 1 calc R U . . .
C19 C 0.46568(18) 0.2722(12) 0.4124(4) 0.0209(10) Uani 1 1 d . . . . .
H19 H 0.4990 0.2138 0.4340 0.025 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 C13 1.365(5) . ?
F2 C1 1.364(5) . ?
N1 C8 1.144(6) . ?
C1 C2 1.373(7) . ?
C1 C6 1.373(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(6) . ?
C4 C5 1.415(6) . ?
C4 C7 1.483(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.444(6) . ?
C7 C9 1.355(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.482(6) . ?
C10 C11 1.378(6) . ?
C10 C15 1.442(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.406(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.370(7) . ?
C13 C14 1.400(7) . ?
C14 C15 1.434(6) . ?
C14 C19 1.420(6) . ?
C15 C16 1.423(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.368(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.410(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.364(7) . ?
C19 H19 0.9500 . ?

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
F2 C1 C2 118.7(4) . . ?
F2 C1 C6 118.1(4) . . ?
C6 C1 C2 123.1(4) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.0(4) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 118.0(4) . . ?
C3 C4 C7 121.3(4) . . ?
C5 C4 C7 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C4 115.4(4) . . ?
C9 C7 C4 124.2(4) . . ?
C9 C7 C8 120.4(4) . . ?
N1 C8 C7 176.3(5) . . ?
C7 C9 H9 116.3 . . ?
C7 C9 C10 127.3(4) . . ?
C10 C9 H9 116.3 . . ?
C11 C10 C9 121.3(4) . . ?
C11 C10 C15 120.2(4) . . ?
C15 C10 C9 118.4(4) . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(4) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.0(4) . . ?
C13 C12 H12 121.0 . . ?
F1 C13 C12 118.5(4) . . ?
F1 C13 C14 117.5(4) . . ?
C12 C13 C14 124.0(4) . . ?
C13 C14 C15 117.9(4) . . ?
C13 C14 C19 122.9(4) . . ?
C19 C14 C15 119.2(4) . . ?
C14 C15 C10 118.3(4) . . ?
C16 C15 C10 123.6(4) . . ?
C16 C15 C14 118.1(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(5) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.0(4) . . ?
C18 C19 H19 119.5 . . ?

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
F1 C13 C14 C15 179.0(4) . . . . ?
F1 C13 C14 C19 -0.5(7) . . . . ?
F2 C1 C2 C3 -179.8(4) . . . . ?
F2 C1 C6 C5 179.6(4) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C2 C3 C4 C7 -177.7(4) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C3 C4 C7 C8 -9.0(6) . . . . ?
C3 C4 C7 C9 168.4(4) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C4 C7 C9 C10 177.4(4) . . . . ?
C5 C4 C7 C8 172.8(4) . . . . ?
C5 C4 C7 C9 -9.8(6) . . . . ?
C6 C1 C2 C3 -1.2(7) . . . . ?
C7 C4 C5 C6 177.5(4) . . . . ?
C7 C9 C10 C11 -38.7(7) . . . . ?
C7 C9 C10 C15 145.2(5) . . . . ?
C8 C7 C9 C10 -5.3(7) . . . . ?
C9 C10 C11 C12 -176.4(4) . . . . ?
C9 C10 C15 C14 175.9(4) . . . . ?
C9 C10 C15 C16 -3.4(6) . . . . ?
C10 C11 C12 C13 0.9(7) . . . . ?
C10 C15 C16 C17 179.5(5) . . . . ?
C11 C10 C15 C14 -0.2(6) . . . . ?
C11 C10 C15 C16 -179.5(4) . . . . ?
C11 C12 C13 F1 -179.7(4) . . . . ?
C11 C12 C13 C14 -0.7(7) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C12 C13 C14 C19 -179.4(5) . . . . ?
C13 C14 C15 C10 0.4(6) . . . . ?
C13 C14 C15 C16 179.7(4) . . . . ?
C13 C14 C19 C18 -179.5(5) . . . . ?
C14 C15 C16 C17 0.2(7) . . . . ?
C15 C10 C11 C12 -0.4(7) . . . . ?
C15 C14 C19 C18 1.1(7) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C16 C17 C18 C19 0.2(8) . . . . ?
C17 C18 C19 C14 -0.8(7) . . . . ?
C19 C14 C15 C10 179.9(4) . . . . ?
C19 C14 C15 C16 -0.8(6) . . . . ?

_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_Z-FPhNaOMe
_database_code_depnum_ccdc_archive 'CCDC 2101707'
loop_
_audit_author_name
_audit_author_address
'cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-08-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F N O'
_chemical_formula_sum            'C20 H14 F N O'
_chemical_formula_weight         303.32
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.8720(3)
_cell_length_b                   28.953(2)
_cell_length_c                   13.1938(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.852(3)
_cell_angle_gamma                90
_cell_volume                     1479.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6705
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29308
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.615
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                2234
_reflns_number_total             3355
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.025
_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)+(0.0458P)²+1.8569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1563
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13-C14 \\sim C19-C14
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C13)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C12(H12), C6(H6), C16(H16), C2(H2), C17(H17), C11(H11),
 C9(H9), C19(H19), C18(H18)
4.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
F1 F -0.1210(5) 0.92644(5) 0.52345(12) 0.0521(5) Uani 1 1 d . . . . .
O1 O 0.4901(5) 0.52743(6) 0.73385(14) 0.0422(5) Uani 1 1 d . . . . .
N1 N 0.5317(7) 0.75068(8) 0.84629(18) 0.0494(6) Uani 1 1 d . . . . .
C4 C 0.1505(6) 0.79674(8) 0.62922(17) 0.0286(5) Uani 1 1 d . . . . .
C14 C 0.5319(6) 0.58578(8) 0.60969(18) 0.0316(4) Uani 1 1 d D . . . .
C5 C -0.0303(6) 0.80231(9) 0.53661(18) 0.0328(5) Uani 1 1 d . . . . .
H5 H -0.0904 0.7758 0.4977 0.039 Uiso 1 1 calc R U . . .
C3 C 0.2291(6) 0.83618(8) 0.68544(18) 0.0318(5) Uani 1 1 d . . . . .
H3 H 0.3468 0.8332 0.7488 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2586(6) 0.75065(8) 0.66544(17) 0.0308(5) Uani 1 1 d . . . . .
C10 C 0.3237(6) 0.66454(8) 0.64546(18) 0.0314(5) Uani 1 1 d . . . . .
C15 C 0.4781(6) 0.63196(8) 0.57764(18) 0.0308(5) Uani 1 1 d . . . . .
C12 C 0.2832(6) 0.60401(8) 0.77385(19) 0.0334(5) Uani 1 1 d . . . . .
H12 H 0.2180 0.5951 0.8402 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4311(6) 0.57254(8) 0.70936(18) 0.0316(4) Uani 1 1 d D . . . .
C6 C -0.1218(7) 0.84559(9) 0.5012(2) 0.0369(6) Uani 1 1 d . . . . .
H6 H -0.2435 0.8491 0.4387 0.044 Uiso 1 1 calc R U . . .
C16 C 0.5849(6) 0.64414(9) 0.47829(18) 0.0333(6) Uani 1 1 d . . . . .
H16 H 0.5582 0.6751 0.4555 0.040 Uiso 1 1 calc R U . . .
C2 C 0.1378(7) 0.88001(9) 0.6502(2) 0.0365(6) Uani 1 1 d . . . . .
H2 H 0.1924 0.9068 0.6887 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4074(7) 0.74928(8) 0.7665(2) 0.0356(6) Uani 1 1 d . . . . .
C17 C 0.7251(7) 0.61196(9) 0.4154(2) 0.0367(6) Uani 1 1 d . . . . .
H17 H 0.7923 0.6207 0.3491 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2302(6) 0.64951(8) 0.73980(19) 0.0337(6) Uani 1 1 d . . . . .
H11 H 0.1245 0.6709 0.7843 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2445(6) 0.71140(8) 0.61051(19) 0.0333(5) Uani 1 1 d . . . . .
H9 H 0.1755 0.7145 0.5414 0.040 Uiso 1 1 calc R U . . .
C1 C -0.0329(7) 0.88343(9) 0.5586(2) 0.0377(6) Uani 1 1 d . . . . .
C19 C 0.6810(7) 0.55334(9) 0.5421(2) 0.0383(6) Uani 1 1 d D . . . .
H19 H 0.7176 0.5224 0.5636 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7712(7) 0.56613(9) 0.4473(2) 0.0396(6) Uani 1 1 d . . . . .
H18 H 0.8658 0.5440 0.4024 0.048 Uiso 1 1 calc R U . . .
C20 C 0.3654(8) 0.51154(10) 0.8284(2) 0.0494(7) Uani 1 1 d . . . . .
H20A H 0.1155 0.5166 0.8312 0.074 Uiso 1 1 calc R U . . .
H20B H 0.4800 0.5286 0.8835 0.074 Uiso 1 1 calc R U . . .
H20C H 0.4148 0.4785 0.8356 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 C1 1.370(3) . ?
O1 C13 1.364(3) . ?
O1 C20 1.420(3) . ?
N1 C8 1.152(3) . ?
C4 C5 1.408(3) . ?
C4 C3 1.393(3) . ?
C4 C7 1.476(3) . ?
C14 C15 1.417(3) . ?
C14 C13 1.430(3) . ?
C14 C19 1.423(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.395(3) . ?
C7 C8 1.445(3) . ?
C7 C9 1.349(3) . ?
C10 C15 1.436(3) . ?
C10 C11 1.372(3) . ?
C10 C9 1.464(3) . ?
C15 C16 1.425(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(3) . ?
C12 C11 1.406(3) . ?
C6 H6 0.9500 . ?
C6 C1 1.372(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.366(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.373(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.403(4) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.355(4) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C13 O1 C20 117.4(2) . . ?
C5 C4 C7 121.3(2) . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 C7 120.7(2) . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 C19 119.7(2) . . ?
C19 C14 C13 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C8 C7 C4 115.5(2) . . ?
C9 C7 C4 125.4(2) . . ?
C9 C7 C8 119.0(2) . . ?
C15 C10 C9 120.0(2) . . ?
C11 C10 C15 118.3(2) . . ?
C11 C10 C9 121.5(2) . . ?
C14 C15 C10 119.6(2) . . ?
C14 C15 C16 117.7(2) . . ?
C16 C15 C10 122.7(2) . . ?
C13 C12 H12 120.6 . . ?
C13 C12 C11 118.9(2) . . ?
C11 C12 H12 120.6 . . ?
O1 C13 C14 115.3(2) . . ?
O1 C13 C12 123.8(2) . . ?
C12 C13 C14 120.8(2) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 H6 120.8 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.5 . . ?
C3 C2 H2 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
N1 C8 C7 176.2(3) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C10 C11 C12 123.2(2) . . ?
C10 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
C7 C9 C10 127.2(2) . . ?
C7 C9 H9 116.4 . . ?
C10 C9 H9 116.4 . . ?
F1 C1 C6 118.7(2) . . ?
F1 C1 C2 118.5(2) . . ?
C6 C1 C2 122.8(2) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C3 C2 C1 0.2(4) . . . . ?
C4 C7 C9 C10 -175.0(2) . . . . ?
C14 C15 C16 C17 1.8(3) . . . . ?
C14 C19 C18 C17 1.4(4) . . . . ?
C5 C4 C3 C2 -1.3(3) . . . . ?
C5 C4 C7 C8 -173.4(2) . . . . ?
C5 C4 C7 C9 10.1(4) . . . . ?
C5 C6 C1 F1 179.6(2) . . . . ?
C5 C6 C1 C2 -1.1(4) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C3 C4 C7 C8 7.5(3) . . . . ?
C3 C4 C7 C9 -169.1(2) . . . . ?
C3 C2 C1 F1 -179.6(2) . . . . ?
C3 C2 C1 C6 1.1(4) . . . . ?
C7 C4 C5 C6 -177.9(2) . . . . ?
C7 C4 C3 C2 177.9(2) . . . . ?
C10 C15 C16 C17 -178.8(2) . . . . ?
C15 C14 C13 O1 179.6(2) . . . . ?
C15 C14 C13 C12 0.1(3) . . . . ?
C15 C14 C19 C18 -0.2(4) . . . . ?
C15 C10 C11 C12 1.1(4) . . . . ?
C15 C10 C9 C7 -146.0(3) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C13 C14 C15 C16 179.3(2) . . . . ?
C13 C14 C19 C18 179.1(2) . . . . ?
C13 C12 C11 C10 -1.0(4) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C8 C7 C9 C10 8.6(4) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C11 C10 C15 C16 -179.8(2) . . . . ?
C11 C10 C9 C7 39.0(4) . . . . ?
C11 C12 C13 O1 -179.1(2) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C9 C10 C15 C14 -175.6(2) . . . . ?
C9 C10 C15 C16 5.0(4) . . . . ?
C9 C10 C11 C12 176.1(2) . . . . ?
C19 C14 C15 C10 179.2(2) . . . . ?
C19 C14 C15 C16 -1.4(3) . . . . ?
C19 C14 C13 O1 0.3(3) . . . . ?
C19 C14 C13 C12 -179.2(2) . . . . ?
C20 O1 C13 C14 -174.3(2) . . . . ?
C20 O1 C13 C12 5.2(4) . . . . ?

_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_E-FPhNaF
_database_code_depnum_ccdc_archive 'CCDC 2101680'
loop_
_audit_author_name
_audit_author_address
'cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-08-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        Z-FPFNA
_chemical_formula_moiety         'C19 H11 F2 N'
_chemical_formula_sum            'C19 H11 F2 N'
_chemical_formula_weight         291.29
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0153(2)
_cell_length_b                   21.7501(6)
_cell_length_c                   8.4639(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.2200(10)
_cell_angle_gamma                90
_cell_volume                     1466.86(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9367
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.659
_cell_measurement_theta_min      2.556
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32703
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2032
_reflns_number_total             3363
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.038
_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)+(0.0580P)²+0.2661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1439
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_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
F1 F 0.6657(2) 0.15585(6) 0.80843(19) 0.1216(6) Uani 1 1 d . . . . .
F2 F 0.08070(18) 0.44118(7) 0.4671(2) 0.1250(6) Uani 1 1 d . . . . .
N1 N 0.8087(3) 0.56346(9) 0.9111(3) 0.1065(7) Uani 1 1 d . . . . .
C1 C 0.2341(3) 0.44616(10) 0.5514(3) 0.0810(6) Uani 1 1 d . . . . .
C2 C 0.2541(3) 0.48656(10) 0.6758(3) 0.0856(6) Uani 1 1 d . . . . .
H2 H 0.1635 0.5114 0.7019 0.103 Uiso 1 1 calc R U . . .
C3 C 0.4103(2) 0.49020(9) 0.7624(2) 0.0749(5) Uani 1 1 d . . . . .
H3 H 0.4283 0.5188 0.8474 0.090 Uiso 1 1 calc R U . . .
C4 C 0.5404(2) 0.45282(7) 0.7268(2) 0.0604(4) Uani 1 1 d . . . . .
C5 C 0.5145(2) 0.41401(8) 0.5970(2) 0.0696(5) Uani 1 1 d . . . . .
H5 H 0.6044 0.3893 0.5686 0.084 Uiso 1 1 calc R U . . .
C6 C 0.3606(3) 0.41069(9) 0.5084(2) 0.0798(6) Uani 1 1 d . . . . .
H6 H 0.3433 0.3841 0.4191 0.096 Uiso 1 1 calc R U . . .
C7 C 0.7060(2) 0.45502(8) 0.8233(2) 0.0662(5) Uani 1 1 d . . . . .
C8 C 0.7653(3) 0.51539(9) 0.8715(3) 0.0786(6) Uani 1 1 d . . . . .
C9 C 0.8051(2) 0.40725(9) 0.8694(2) 0.0727(5) Uani 1 1 d . . . . .
H9 H 0.9127 0.4170 0.9217 0.087 Uiso 1 1 calc R U . . .
C10 C 0.7665(2) 0.34147(8) 0.8485(2) 0.0672(5) Uani 1 1 d . . . . .
C11 C 0.6187(2) 0.31794(10) 0.8895(3) 0.0797(6) Uani 1 1 d . . . . .
H11 H 0.5381 0.3447 0.9272 0.096 Uiso 1 1 calc R U . . .
C12 C 0.5845(3) 0.25433(11) 0.8765(3) 0.0887(7) Uani 1 1 d . . . . .
H12 H 0.4815 0.2383 0.9044 0.106 Uiso 1 1 calc R U . . .
C13 C 0.7002(3) 0.21679(10) 0.8240(3) 0.0837(6) Uani 1 1 d . . . . .
C14 C 0.8552(2) 0.23685(9) 0.7813(2) 0.0718(5) Uani 1 1 d . . . . .
C15 C 0.8884(2) 0.30101(8) 0.7937(2) 0.0656(5) Uani 1 1 d . . . . .
C16 C 1.0427(2) 0.32159(9) 0.7476(3) 0.0786(6) Uani 1 1 d . . . . .
H16 H 1.0687 0.3642 0.7529 0.094 Uiso 1 1 calc R U . . .
C17 C 1.1556(3) 0.28143(11) 0.6956(3) 0.0915(7) Uani 1 1 d . . . . .
H17 H 1.2587 0.2966 0.6655 0.110 Uiso 1 1 calc R U . . .
C18 C 1.1224(3) 0.21880(11) 0.6857(3) 0.0929(7) Uani 1 1 d . . . . .
H18 H 1.2026 0.1916 0.6493 0.112 Uiso 1 1 calc R U . . .
C19 C 0.9764(3) 0.19659(9) 0.7277(3) 0.0852(6) Uani 1 1 d . . . . .
H19 H 0.9546 0.1537 0.7214 0.102 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 C13 1.357(2) . ?
F2 C1 1.357(2) . ?
N1 C8 1.141(2) . ?
C1 C2 1.368(3) . ?
C1 C6 1.355(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 C5 1.383(2) . ?
C4 C7 1.482(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.440(3) . ?
C7 C9 1.340(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.471(3) . ?
C10 C11 1.370(3) . ?
C10 C15 1.429(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.412(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.346(3) . ?
C13 C14 1.401(3) . ?
C14 C15 1.422(2) . ?
C14 C19 1.418(3) . ?
C15 C16 1.410(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.364(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.349(3) . ?
C19 H19 0.9500 . ?

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
F2 C1 C2 118.7(2) . . ?
C6 C1 F2 118.40(19) . . ?
C6 C1 C2 122.92(18) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.84(19) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.71(16) . . ?
C3 C4 C7 120.89(16) . . ?
C5 C4 C7 120.39(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.92(18) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.53(19) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C4 115.69(16) . . ?
C9 C7 C4 127.05(16) . . ?
C9 C7 C8 117.26(17) . . ?
N1 C8 C7 178.4(3) . . ?
C7 C9 H9 116.2 . . ?
C7 C9 C10 127.54(16) . . ?
C10 C9 H9 116.2 . . ?
C11 C10 C9 120.61(19) . . ?
C11 C10 C15 119.53(17) . . ?
C15 C10 C9 119.76(16) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.5 . . ?
F1 C13 C14 117.1(2) . . ?
C12 C13 F1 119.0(2) . . ?
C12 C13 C14 123.90(19) . . ?
C13 C14 C15 116.8(2) . . ?
C13 C14 C19 123.20(19) . . ?
C19 C14 C15 120.02(18) . . ?
C14 C15 C10 119.95(17) . . ?
C16 C15 C10 123.05(17) . . ?
C16 C15 C14 116.99(18) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.21(19) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.8 . . ?

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
F1 C13 C14 C15 178.29(16) . . . . ?
F1 C13 C14 C19 -1.7(3) . . . . ?
F2 C1 C2 C3 178.74(19) . . . . ?
F2 C1 C6 C5 -177.72(18) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
C2 C3 C4 C5 3.6(3) . . . . ?
C2 C3 C4 C7 -177.68(18) . . . . ?
C3 C4 C5 C6 -2.6(3) . . . . ?
C3 C4 C7 C8 -40.6(2) . . . . ?
C3 C4 C7 C9 139.6(2) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C7 C9 C10 -6.3(3) . . . . ?
C5 C4 C7 C8 138.08(19) . . . . ?
C5 C4 C7 C9 -41.8(3) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C7 C4 C5 C6 178.71(17) . . . . ?
C7 C9 C10 C11 -48.9(3) . . . . ?
C7 C9 C10 C15 134.8(2) . . . . ?
C8 C7 C9 C10 173.9(2) . . . . ?
C9 C10 C11 C12 -177.05(18) . . . . ?
C9 C10 C15 C14 176.67(16) . . . . ?
C9 C10 C15 C16 -4.4(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C10 C15 C16 C17 -179.80(19) . . . . ?
C11 C10 C15 C14 0.4(3) . . . . ?
C11 C10 C15 C16 179.32(17) . . . . ?
C11 C12 C13 F1 -178.65(18) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C12 C13 C14 C19 179.3(2) . . . . ?
C13 C14 C15 C10 0.3(2) . . . . ?
C13 C14 C15 C16 -178.66(17) . . . . ?
C13 C14 C19 C18 178.8(2) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C10 C11 C12 -0.8(3) . . . . ?
C15 C14 C19 C18 -1.1(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 C14 0.4(3) . . . . ?
C19 C14 C15 C10 -179.69(16) . . . . ?
C19 C14 C15 C16 1.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
