# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_comp5
_audit_block_doi                 10.5517/cc50f9w
_database_code_depnum_ccdc_archive 'CCDC 149367'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/S0022-2860(01)00759-1 2002
_audit_update_record             
;
2000-09-06 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;

_audit_creation_method           Xtal3.6
_audit_creation_date             00-09-05

_chemical_formula_sum            'C19 H13 N1 O1'
_chemical_formula_moiety         ?
_chemical_formula_weight         271.32
_chemical_melting_point          ?

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P_21_21_21
_symmetry_space_group_name_Hall  p_2ac_2ab

loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z

_cell_length_a                   17.214(2)
_cell_length_b                   14.4042(16)
_cell_length_c                   5.5668(7)
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_volume                     1380.3(3)
_cell_formula_units_Z            4

_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_diffrn_radiation_type           'Cu K\\a'
_diffrn_radiation_wavelength     1.54178

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    293

_exptl_absorpt_coefficient_mu    .636
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_diffrn_reflns_number            1360
_reflns_number_total             1292
_reflns_Friedel_coverage         0
_reflns_number_gt                909
_reflns_threshold_expression     'I    > 1.00 sig(1   )'

_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_full        ?
_diffrn_measured_fraction_theta_max ?
_diffrn_measured_fraction_theta_full ?
_diffrn_reflns_av_R_equivalents  .004
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       5
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ? #<< do not append units
_diffrn_standards_decay_%        ? #<< do not append %


_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           .051
_refine_ls_wR_factor_ref         .059
_refine_ls_goodness_of_fit_ref   .968
_refine_ls_number_reflns         909
_refine_ls_number_parameters     243
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_shift/su_max          .06
_refine_diff_density_min         -.276
_refine_diff_density_max         .226

_refine_ls_extinction_method     Zachariasen
_refine_ls_extinction_coef       652(125)
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   0


# 3. Information for the "methods" section
#-----------------------------------------

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'xtal DIFDAT SORTRF ADDREF'
_computing_structure_solution    xtal
_computing_structure_refinement  'xtal CRYLSQ'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'


# 4. Supplementary data for validation and tables
#------------------------------------------------

loop_
_atom_type_symbol
_atom_type_description
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C ? 0 76 .017 .009 'INTERNATIONAL TABLES FOR X-RAY='
H ? 0 52 0 0 'INTERNATIONAL TABLES FOR X-RAY='
N ? 0 4 .029 .018 'INTERNATIONAL TABLES FOR X-RAY='
O ? 0 4 .047 .032 'INTERNATIONAL TABLES FOR X-RAY='

loop_
_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_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 .1603(2) .2806(3) .3034(9) .054(2) Uani ? ? 1.00000 ? ?
C2 .1300(3) .3327(4) .4977(11) .053(3) Uani ? ? 1.00000 ? ?
C3 .1626(4) .4073(4) .6224(14) .064(4) Uani ? ? 1.00000 ? ?
C4 .1211(4) .4418(4) .8117(14) .072(4) Uani ? ? 1.00000 ? ?
C5 .0490(4) .4054(4) .8802(14) .068(4) Uani ? ? 1.00000 ? ?
C6 .0169(3) .3322(4) .7546(12) .059(3) Uani ? ? 1.00000 ? ?
C7 .0573(3) .2953(3) .5623(10) .048(3) Uani ? ? 1.00000 ? ?
C8 .0411(3) .2205(3) .3976(10) .049(3) Uani ? ? 1.00000 ? ?
C9 -.0235(3) .1619(4) .3699(13) .063(4) Uani ? ? 1.00000 ? ?
C10 -.0245(4) .1021(4) .1785(14) .065(4) Uani ? ? 1.00000 ? ?
C11 .0358(4) .0980(4) .0127(14) .068(4) Uani ? ? 1.00000 ? ?
C12 .1011(3) .1550(4) .0384(12) .058(3) Uani ? ? 1.00000 ? ?
C13 .1032(3) .2132(3) .2369(11) .050(3) Uani ? ? 1.00000 ? ?
C14 .2347(3) .2924(4) .2063(13) .066(3) Uani ? ? 1.00000 ? ?
O15 .2677(3) .3661(3) .2318(13) .105(4) Uani ? ? 1.00000 ? ?
C16 .2729(3) .2108(4) .0989(12) .058(3) Uani ? ? 1.00000 ? ?
C17 .2722(3) .1265(4) .2182(14) .060(4) Uani ? ? 1.00000 ? ?
C18 .3144(4) .0521(4) .1262(16) .073(4) Uani ? ? 1.00000 ? ?
C19 .3530(4) .0624(6) -.0838(17) .081(5) Uani ? ? 1.00000 ? ?
C20 .3543(4) .1454(7) -.2052(16) .086(5) Uani ? ? 1.00000 ? ?
C21 .3143(3) .2218(5) -.1113(12) .070(4) Uani ? ? 1.00000 ? ?
H3 .212(4) .428(4) .562(14) .06(2) Uiso ? ? 1.00000 ? ?
H4 .143(3) .497(4) .894(12) .045(18) Uiso ? ? 1.00000 ? ?
H5 .025(3) .429(4) 1.032(11) .031(16) Uiso ? ? 1.00000 ? ?
H6 -.032(4) .309(4) .787(13) .047(19) Uiso ? ? 1.00000 ? ?
H9 -.065(3) .167(3) .515(10) .020(13) Uiso ? ? 1.00000 ? ?
H10 -.070(3) .066(4) .154(12) .039(17) Uiso ? ? 1.00000 ? ?
H11 .027(4) .059(5) -.150(16) .08(3) Uiso ? ? 1.00000 ? ?
H12 .142(3) .152(4) -.103(12) .038(17) Uiso ? ? 1.00000 ? ?
H17 .248(4) .126(5) .393(15) .06(2) Uiso ? ? 1.00000 ? ?
H18 .318(4) -.012(5) .232(15) .09(3) Uiso ? ? 1.00000 ? ?
H19 .383(4) .010(5) -.164(15) .07(2) Uiso ? ? 1.00000 ? ?
H20 .377(3) .152(4) -.374(12) .028(15) Uiso ? ? 1.00000 ? ?
H21 .310(4) .286(5) -.201(14) .07(2) Uiso ? ? 1.00000 ? ?



# 5. Molecular Geometry
#----------------------

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag #<< enter YES for value to be published
N1 C14 . . 1.400(7) ?
N1 C2 . . 1.416(7) ?
N1 C13 . . 1.431(6) ?
C2 C3 . . 1.397(8) ?
C2 C7 . . 1.410(7) ?
C3 H3 . . .96(7) ?
C3 C4 . . 1.367(10) ?
C4 H4 . . .99(6) ?
C4 C5 . . 1.400(9) ?
C5 H5 . . 1.00(6) ?
C5 C6 . . 1.380(9) ?
C6 H6 . . .92(6) ?
C6 C7 . . 1.383(8) ?
C7 C8 . . 1.441(7) ?
C8 C13 . . 1.398(7) ?
C8 C9 . . 1.406(7) ?
C9 H9 . . 1.08(5) ?
C9 C10 . . 1.371(10) ?
C10 H10 . . .95(6) ?
C10 C11 . . 1.390(10) ?
C11 H11 . . 1.08(9) ?
C11 C12 . . 1.400(9) ?
C12 H12 . . 1.06(6) ?
C12 C13 . . 1.387(9) ?
C14 O15 . . 1.212(7) ?
C14 C16 . . 1.474(8) ?
C16 C21 . . 1.380(9) ?
C16 C17 . . 1.383(9) ?
C17 H17 . . 1.06(8) ?
C17 C18 . . 1.393(9) ?
C18 H18 . . 1.10(8) ?
C18 C19 . . 1.353(12) ?
C19 H19 . . 1.01(7) ?
C19 C20 . . 1.374(13) ?
C20 H20 . . 1.02(6) ?
C20 C21 . . 1.400(11) ?
C21 H21 . . 1.06(7) ?

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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag #<< enter YES for value to be published
C14 N1 C2 . . . 124.6(4) ?
C14 N1 C13 . . . 127.6(5) ?
C2 N1 C13 . . . 107.7(4) ?
C3 C2 C7 . . . 121.7(5) ?
C3 C2 N1 . . . 129.7(5) ?
C7 C2 N1 . . . 108.6(4) ?
H3 C3 C4 . . . 128(4) ?
H3 C3 C2 . . . 115(4) ?
C4 C3 C2 . . . 116.9(6) ?
H4 C4 C3 . . . 117(4) ?
H4 C4 C5 . . . 121(4) ?
C3 C4 C5 . . . 122.5(6) ?
H5 C5 C6 . . . 121(3) ?
H5 C5 C4 . . . 118(3) ?
C6 C5 C4 . . . 120.2(6) ?
H6 C6 C5 . . . 123(4) ?
H6 C6 C7 . . . 118(4) ?
C5 C6 C7 . . . 119.0(5) ?
C6 C7 C2 . . . 119.7(5) ?
C6 C7 C8 . . . 133.1(5) ?
C2 C7 C8 . . . 107.2(5) ?
C13 C8 C9 . . . 119.3(5) ?
C13 C8 C7 . . . 108.4(4) ?
C9 C8 C7 . . . 132.2(5) ?
H9 C9 C10 . . . 128(3) ?
H9 C9 C8 . . . 113(3) ?
C10 C9 C8 . . . 118.2(6) ?
H10 C10 C9 . . . 117(4) ?
H10 C10 C11 . . . 120(4) ?
C9 C10 C11 . . . 122.2(6) ?
H11 C11 C10 . . . 118(4) ?
H11 C11 C12 . . . 120(4) ?
C10 C11 C12 . . . 120.5(6) ?
H12 C12 C13 . . . 127(3) ?
H12 C12 C11 . . . 116(3) ?
C13 C12 C11 . . . 117.1(6) ?
C12 C13 C8 . . . 122.4(5) ?
C12 C13 N1 . . . 129.3(5) ?
C8 C13 N1 . . . 107.9(5) ?
O15 C14 N1 . . . 119.3(6) ?
O15 C14 C16 . . . 122.5(5) ?
N1 C14 C16 . . . 117.9(5) ?
C21 C16 C17 . . . 120.9(6) ?
C21 C16 C14 . . . 118.8(6) ?
C17 C16 C14 . . . 120.1(6) ?
H17 C17 C16 . . . 117(4) ?
H17 C17 C18 . . . 123(4) ?
C16 C17 C18 . . . 119.6(7) ?
H18 C18 C19 . . . 122(4) ?
H18 C18 C17 . . . 119(4) ?
C19 C18 C17 . . . 119.3(7) ?
H19 C19 C18 . . . 123(5) ?
H19 C19 C20 . . . 115(5) ?
C18 C19 C20 . . . 121.9(7) ?
H20 C20 C19 . . . 123(3) ?
H20 C20 C21 . . . 117(3) ?
C19 C20 C21 . . . 119.5(8) ?
H21 C21 C16 . . . 118(4) ?
H21 C21 C20 . . . 123(4) ?
C16 C21 C20 . . . 118.7(7) ?

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 #<< enter YES for value to be published
C2 N1 C14 O15 . . . . -23.5(9) ?
N1 C14 C16 C17 . . . . -45.7(8) ?
C13 N1 C2 C3 . . . . -178.6(6) ?
C13 N1 C2 C7 . . . . 3.5(6) ?
C14 N1 C2 C3 . . . . 4.1(9) ?
C14 N1 C2 C7 . . . . -173.8(5) ?
C2 N1 C13 C8 . . . . -3.5(6) ?
C2 N1 C13 C12 . . . . 170.3(6) ?
C14 N1 C13 C8 . . . . 173.8(5) ?
C14 N1 C13 C12 . . . . -12.5(9) ?
C2 N1 C14 O15 . . . . -23.5(9) ?
C2 N1 C14 C16 . . . . 150.2(6) ?
C13 N1 C14 O15 . . . . 159.7(6) ?
C13 N1 C14 C16 . . . . -26.6(9) ?
N1 C2 C3 C4 . . . . -177.1(6) ?
N1 C2 C3 H3 . . . . 3(5) ?
C7 C2 C3 C4 . . . . .6(9) ?
C7 C2 C3 H3 . . . . -179(5) ?
N1 C2 C7 C6 . . . . 177.7(5) ?
N1 C2 C7 C8 . . . . -2.2(6) ?
C3 C2 C7 C6 . . . . -.5(8) ?
C3 C2 C7 C8 . . . . 179.7(5) ?
C2 C3 C4 C5 . . . . -.1(10) ?
C2 C3 C4 H4 . . . . -177(4) ?
H3 C3 C4 C5 . . . . 180(5) ?
H3 C3 C4 H4 . . . . 3(7) ?
C3 C4 C5 C6 . . . . -.5(10) ?
C3 C4 C5 H5 . . . . 173(4) ?
H4 C4 C5 C6 . . . . 176(4) ?
H4 C4 C5 H5 . . . . -11(6) ?
C4 C5 C6 C7 . . . . .6(9) ?
C4 C5 C6 H6 . . . . -176(5) ?
H5 C5 C6 C7 . . . . -173(4) ?
H5 C5 C6 H6 . . . . 11(6) ?
C5 C6 C7 C2 . . . . -.1(8) ?
C5 C6 C7 C8 . . . . 179.7(6) ?
H6 C6 C7 C2 . . . . 177(5) ?
H6 C6 C7 C8 . . . . -4(5) ?
C2 C7 C8 C9 . . . . -176.8(6) ?
C2 C7 C8 C13 . . . . .0(6) ?
C6 C7 C8 C9 . . . . 3.3(11) ?
C6 C7 C8 C13 . . . . -179.8(6) ?
C7 C8 C9 C10 . . . . 173.8(6) ?
C7 C8 C9 H9 . . . . -11(3) ?
C13 C8 C9 C10 . . . . -2.8(8) ?
C13 C8 C9 H9 . . . . 173(3) ?
C7 C8 C13 N1 . . . . 2.1(6) ?
C7 C8 C13 C12 . . . . -172.1(5) ?
C9 C8 C13 N1 . . . . 179.4(5) ?
C9 C8 C13 C12 . . . . 5.2(8) ?
C8 C9 C10 C11 . . . . -.2(9) ?
C8 C9 C10 H10 . . . . -175(4) ?
H9 C9 C10 C11 . . . . -175(3) ?
H9 C9 C10 H10 . . . . 10(5) ?
C9 C10 C11 C12 . . . . 1.0(10) ?
C9 C10 C11 H11 . . . . -169(5) ?
H10 C10 C11 C12 . . . . 176(4) ?
H10 C10 C11 H11 . . . . 5(6) ?
C10 C11 C12 C13 . . . . 1.3(9) ?
C10 C11 C12 H12 . . . . -175(4) ?
H11 C11 C12 C13 . . . . 171(5) ?
H11 C11 C12 H12 . . . . -5(6) ?
C11 C12 C13 N1 . . . . -177.3(5) ?
C11 C12 C13 C8 . . . . -4.4(8) ?
H12 C12 C13 N1 . . . . -2(4) ?
H12 C12 C13 C8 . . . . 171(4) ?
N1 C14 C16 C17 . . . . -45.7(8) ?
N1 C14 C16 C21 . . . . 139.5(6) ?
O15 C14 C16 C17 . . . . 127.8(7) ?
O15 C14 C16 C21 . . . . -47.1(10) ?
C14 C16 C17 C18 . . . . -174.1(6) ?
C14 C16 C17 H17 . . . . -5(4) ?
C21 C16 C17 C18 . . . . .7(9) ?
C21 C16 C17 H17 . . . . 169(4) ?
C14 C16 C21 C20 . . . . 176.3(6) ?
C14 C16 C21 H21 . . . . -9(5) ?
C17 C16 C21 C20 . . . . 1.5(9) ?
C17 C16 C21 H21 . . . . 177(4) ?
C16 C17 C18 C19 . . . . -2.7(10) ?
C16 C17 C18 H18 . . . . 174(5) ?
H17 C17 C18 C19 . . . . -171(5) ?
H17 C17 C18 H18 . . . . 7(6) ?
C17 C18 C19 C20 . . . . 2.6(11) ?
C17 C18 C19 H19 . . . . -177(5) ?
H18 C18 C19 C20 . . . . -174(5) ?
H18 C18 C19 H19 . . . . 6(7) ?
C18 C19 C20 C21 . . . . -.5(11) ?
C18 C19 C20 H20 . . . . -171(4) ?
H19 C19 C20 C21 . . . . 179(5) ?
H19 C19 C20 H20 . . . . 8(6) ?
C19 C20 C21 C16 . . . . -1.6(10) ?
C19 C20 C21 H21 . . . . -176(5) ?
H20 C20 C21 C16 . . . . 170(4) ?
H20 C20 C21 H21 . . . . -5(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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 #<< enter YES for value to be published
? ? ? ? ? ? ? ? ? ? ?

#--------------------------------------------------------------------------
#       Items which are non-mandatory for Acta C submissions
#--------------------------------------------------------------------------

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   ?

_geom_special_details            ?


_cell_special_details            
;      ?
;

_exptl_special_details           
;      ?
;

_diffrn_special_details          
;      ?
;

_chemical_compound_source        ?
_chemical_name_systematic        9-benzoylcarbazole
_chemical_name_common            ?
_chemical_formula_analytical     ?
_chemical_formula_structural     ?

_exptl_crystal_F_000             568

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_diffrn_attenuator_code
_diffrn_attenuator_scale
? ?

_reflns_limit_h_min              0
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              5
_reflns_number_observed          ?
_reflns_d_resolution_high        .84
_reflns_d_resolution_low         11.047

_diffrn_reflns_av_sigmaI/netI    .035
_diffrn_reflns_theta_min         4.
_diffrn_reflns_reduction_process 'equatorial monochr Lp'

_diffrn_ambient_temperature      293
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_diffrn_radiation_detector       ?

_refine_ls_extinction_expression 'Eq22 p292 "Cryst. Comp." Munksgaard 1970'
_refine_ls_matrix_type           full
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          .085
_refine_ls_wR_factor_all         .074
_refine_ls_goodness_of_fit_all   .972
_refine_ls_shift/su_mean         .011



#==========================================================================
#       Structure Factor lists should be submitted as separate files
#==========================================================================

#data_<structure> # but for xtal use the refln data is needed in same block

####################################################################### 
# 
# 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_111a
_database_code_depnum_ccdc_archive 'CCDC 1975648'
loop_
_audit_author_name
_audit_author_address
lihui
;Nanjing University Of Posts And Telecommunications
China
;
_audit_update_record             
;
2020-01-06 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 F N O'
_chemical_formula_sum            'C19 H12 F N O'
_chemical_formula_weight         289.30
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.8585(9)
_cell_length_b                   10.3783(7)
_cell_length_c                   22.8559(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2812.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2041
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.737
_cell_measurement_theta_min      1.746
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23843
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.206
_diffrn_reflns_theta_min         2.475
_diffrn_ambient_temperature      296.23
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  CCD?area?detector
_diffrn_measurement_method       CCD?area?detector
_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                2382
_reflns_number_total             3455
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.041
_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)+(0.0514P)²+0.6312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1179
_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:
 C8(H8), C5(H5), C11(H11), C2(H2), C15(H15), C4(H4), C9(H9), C3(H3), C10(H10),
 C16(H16), C18(H18), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.29697(9) 0.74864(11) 0.35852(5) 0.0725(3) Uani 1 1 d . . . . .
N1 N 0.51467(10) 0.61099(11) 0.38728(5) 0.0357(3) Uani 1 1 d . . . . .
O1 O 0.48538(10) 0.66518(14) 0.48164(5) 0.0650(4) Uani 1 1 d . . . . .
C12 C 0.58670(12) 0.54819(13) 0.29898(6) 0.0355(3) Uani 1 1 d . . . . .
C7 C 0.49302(12) 0.53779(12) 0.33566(6) 0.0335(3) Uani 1 1 d . . . . .
C1 C 0.62466(12) 0.66424(13) 0.38197(6) 0.0361(3) Uani 1 1 d . . . . .
C6 C 0.66967(12) 0.62719(13) 0.32828(6) 0.0364(3) Uani 1 1 d . . . . .
C8 C 0.40305(12) 0.45923(14) 0.32072(7) 0.0416(3) Uani 1 1 d . . . . .
H8 H 0.3417 0.4493 0.3457 0.050 Uiso 1 1 calc R . . . .
C14 C 0.32518(12) 0.59333(15) 0.43150(6) 0.0401(3) Uani 1 1 d . . . . .
C13 C 0.44706(13) 0.62567(14) 0.43599(6) 0.0411(3) Uani 1 1 d . . . . .
C5 C 0.77711(13) 0.66727(15) 0.31214(7) 0.0459(4) Uani 1 1 d . . . . .
H5 H 0.8081 0.6422 0.2765 0.055 Uiso 1 1 calc R . . . .
C11 C 0.58846(14) 0.48389(16) 0.24569(7) 0.0478(4) Uani 1 1 d . . . . .
H11 H 0.6502 0.4916 0.2208 0.057 Uiso 1 1 calc R . . . .
C2 C 0.68368(14) 0.74426(16) 0.41972(7) 0.0491(4) Uani 1 1 d . . . . .
H2 H 0.6529 0.7707 0.4552 0.059 Uiso 1 1 calc R . . . .
C15 C 0.27900(15) 0.50082(17) 0.46788(7) 0.0518(4) Uani 1 1 d . . . . .
H15 H 0.3252 0.4565 0.4939 0.062 Uiso 1 1 calc R . . . .
C19 C 0.25296(14) 0.65861(16) 0.39475(7) 0.0489(4) Uani 1 1 d . . . . .
C4 C 0.83659(14) 0.74467(16) 0.34991(8) 0.0540(4) Uani 1 1 d . . . . .
H4 H 0.9089 0.7715 0.3400 0.065 Uiso 1 1 calc R . . . .
C9 C 0.40732(14) 0.39629(16) 0.26775(7) 0.0505(4) Uani 1 1 d . . . . .
H9 H 0.3473 0.3437 0.2569 0.061 Uiso 1 1 calc R . . . .
C3 C 0.79009(15) 0.78309(17) 0.40252(8) 0.0573(5) Uani 1 1 d . . . . .
H3 H 0.8316 0.8366 0.4270 0.069 Uiso 1 1 calc R . . . .
C10 C 0.49777(15) 0.40866(17) 0.23014(7) 0.0545(4) Uani 1 1 d . . . . .
H10 H 0.4974 0.3662 0.1943 0.065 Uiso 1 1 calc R . . . .
C16 C 0.16508(16) 0.4735(2) 0.46609(8) 0.0645(5) Uani 1 1 d . . . . .
H16 H 0.1351 0.4095 0.4900 0.077 Uiso 1 1 calc R . . . .
C18 C 0.13976(16) 0.6351(2) 0.39307(9) 0.0642(5) Uani 1 1 d . . . . .
H18 H 0.0930 0.6816 0.3681 0.077 Uiso 1 1 calc R . . . .
C17 C 0.09627(16) 0.5414(2) 0.42885(9) 0.0704(6) Uani 1 1 d . . . . .
H17 H 0.0194 0.5236 0.4279 0.084 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C19 1.3532(19) . ?
N1 C7 1.4266(17) . ?
N1 C1 1.4217(18) . ?
N1 C13 1.3804(18) . ?
O1 C13 1.2096(17) . ?
C12 C7 1.3959(19) . ?
C12 C6 1.4452(19) . ?
C12 C11 1.389(2) . ?
C7 C8 1.3855(19) . ?
C1 C6 1.393(2) . ?
C1 C2 1.387(2) . ?
C6 C5 1.390(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(2) . ?
C14 C13 1.487(2) . ?
C14 C15 1.383(2) . ?
C14 C19 1.378(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.374(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.376(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C19 C18 1.365(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(2) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.373(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.371(3) . ?
C17 H17 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
C1 N1 C7 107.55(11) . . ?
C13 N1 C7 128.41(12) . . ?
C13 N1 C1 123.97(12) . . ?
C7 C12 C6 107.90(12) . . ?
C11 C12 C7 120.09(13) . . ?
C11 C12 C6 131.96(14) . . ?
C12 C7 N1 108.20(11) . . ?
C8 C7 N1 130.98(13) . . ?
C8 C7 C12 120.69(13) . . ?
C6 C1 N1 108.63(12) . . ?
C2 C1 N1 129.99(14) . . ?
C2 C1 C6 121.34(14) . . ?
C1 C6 C12 107.70(12) . . ?
C5 C6 C12 132.13(14) . . ?
C5 C6 C1 120.17(14) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 C7 117.88(14) . . ?
C9 C8 H8 121.1 . . ?
C15 C14 C13 119.99(14) . . ?
C19 C14 C13 122.36(14) . . ?
C19 C14 C15 117.51(15) . . ?
N1 C13 C14 118.94(12) . . ?
O1 C13 N1 120.99(14) . . ?
O1 C13 C14 120.07(13) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.60(15) . . ?
C4 C5 H5 120.7 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.18(15) . . ?
C10 C11 H11 120.4 . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.28(15) . . ?
C3 C2 H2 121.4 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.79(17) . . ?
C16 C15 H15 119.6 . . ?
F1 C19 C14 118.22(15) . . ?
F1 C19 C18 119.06(15) . . ?
C18 C19 C14 122.71(17) . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.71(16) . . ?
C3 C4 H4 119.6 . . ?
C8 C9 H9 118.9 . . ?
C8 C9 C10 122.15(15) . . ?
C10 C9 H9 118.9 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.87(16) . . ?
C4 C3 H3 119.1 . . ?
C11 C10 C9 119.95(15) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.63(18) . . ?
C17 C16 H16 120.2 . . ?
C19 C18 H18 120.7 . . ?
C19 C18 C17 118.69(18) . . ?
C17 C18 H18 120.7 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.65(18) . . ?
C18 C17 H17 119.7 . . ?

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 C19 C18 C17 178.35(16) . . . . ?
N1 C7 C8 C9 -177.70(14) . . . . ?
N1 C1 C6 C12 -0.28(15) . . . . ?
N1 C1 C6 C5 179.77(12) . . . . ?
N1 C1 C2 C3 -178.99(15) . . . . ?
C12 C7 C8 C9 -2.5(2) . . . . ?
C12 C6 C5 C4 179.40(15) . . . . ?
C12 C11 C10 C9 -1.0(3) . . . . ?
C7 N1 C1 C6 0.91(15) . . . . ?
C7 N1 C1 C2 178.59(15) . . . . ?
C7 N1 C13 O1 162.77(15) . . . . ?
C7 N1 C13 C14 -17.8(2) . . . . ?
C7 C12 C6 C1 -0.48(15) . . . . ?
C7 C12 C6 C5 179.46(15) . . . . ?
C7 C12 C11 C10 -1.0(2) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C1 N1 C7 C12 -1.21(14) . . . . ?
C1 N1 C7 C8 174.43(14) . . . . ?
C1 N1 C13 O1 -13.8(2) . . . . ?
C1 N1 C13 C14 165.59(13) . . . . ?
C1 C6 C5 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C6 C12 C7 N1 1.04(15) . . . . ?
C6 C12 C7 C8 -175.13(12) . . . . ?
C6 C12 C11 C10 176.36(15) . . . . ?
C6 C1 C2 C3 -1.6(2) . . . . ?
C6 C5 C4 C3 -0.7(2) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C14 C15 C16 C17 -1.7(3) . . . . ?
C14 C19 C18 C17 -0.9(3) . . . . ?
C13 N1 C7 C12 -178.23(13) . . . . ?
C13 N1 C7 C8 -2.6(2) . . . . ?
C13 N1 C1 C6 178.10(13) . . . . ?
C13 N1 C1 C2 -4.2(2) . . . . ?
C13 C14 C15 C16 177.17(15) . . . . ?
C13 C14 C19 F1 5.0(2) . . . . ?
C13 C14 C19 C18 -175.73(16) . . . . ?
C5 C4 C3 C2 1.0(3) . . . . ?
C11 C12 C7 N1 178.99(13) . . . . ?
C11 C12 C7 C8 2.8(2) . . . . ?
C11 C12 C6 C1 -178.09(15) . . . . ?
C11 C12 C6 C5 1.9(3) . . . . ?
C2 C1 C6 C12 -178.19(13) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
C15 C14 C13 N1 121.52(15) . . . . ?
C15 C14 C13 O1 -59.1(2) . . . . ?
C15 C14 C19 F1 -179.44(14) . . . . ?
C15 C14 C19 C18 -0.2(2) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C19 C14 C13 N1 -63.0(2) . . . . ?
C19 C14 C13 O1 116.36(18) . . . . ?
C19 C14 C15 C16 1.5(2) . . . . ?
C19 C18 C17 C16 0.7(3) . . . . ?

_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_1111
_database_code_depnum_ccdc_archive 'CCDC 1975612'
loop_
_audit_author_name
_audit_author_address
LiHui
;Nanjing University Of Posts And Telecommunications
China
;
_audit_update_record             
;
2020-01-06 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 F N O'
_chemical_formula_sum            'C19 H12 F N O'
_chemical_formula_weight         289.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.608(3)
_cell_length_b                   5.4287(11)
_cell_length_c                   18.371(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.996(5)
_cell_angle_gamma                90
_cell_volume                     1385.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2041
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.737
_cell_measurement_theta_min      1.746
_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   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11920
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.206
_diffrn_reflns_theta_min         1.566
_diffrn_ambient_temperature      293.57
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CCD?area?detector
_diffrn_measurement_method       CCD?area?detector
_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                1755
_reflns_number_total             3415
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.035
_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)+(0.0781P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1624
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.12207(10) 0.6115(3) 0.50446(8) 0.0783(5) Uani 1 1 d . . . . .
O1 O 0.53512(12) 0.6541(3) 0.57932(10) 0.0621(5) Uani 1 1 d . . . . .
N003 N 0.47683(12) 0.5455(3) 0.67580(10) 0.0410(5) Uani 1 1 d . . . . .
C12 C 0.42964(14) 0.6093(4) 0.73012(11) 0.0373(5) Uani 1 1 d . . . . .
C7 C 0.46093(14) 0.4466(4) 0.79220(12) 0.0394(5) Uani 1 1 d . . . . .
C1 C 0.54185(14) 0.3502(4) 0.70708(12) 0.0397(5) Uani 1 1 d . . . . .
C6 C 0.53086(14) 0.2828(4) 0.77706(12) 0.0399(5) Uani 1 1 d . . . . .
C14 C 0.37378(16) 0.7654(4) 0.56209(12) 0.0451(6) Uani 1 1 d . . . . .
C11 C 0.36831(16) 0.8024(4) 0.73134(14) 0.0450(6) Uani 1 1 d . . . . .
C15 C 0.28909(16) 0.6419(5) 0.55757(13) 0.0471(6) Uani 1 1 d . . . . .
C13 C 0.46874(16) 0.6578(4) 0.60599(13) 0.0455(6) Uani 1 1 d . . . . .
C8 C 0.42735(17) 0.4722(5) 0.85446(14) 0.0516(6) Uani 1 1 d . . . . .
C5 C 0.58362(17) 0.0858(5) 0.81800(15) 0.0500(6) Uani 1 1 d . . . . .
C2 C 0.60384(16) 0.2247(5) 0.67598(15) 0.0498(6) Uani 1 1 d . . . . .
C10 C 0.33668(17) 0.8260(5) 0.79433(14) 0.0517(6) Uani 1 1 d . . . . .
C16 C 0.20503(16) 0.7338(5) 0.50978(13) 0.0543(7) Uani 1 1 d . . . . .
C19 C 0.3718(2) 0.9776(5) 0.51920(14) 0.0534(6) Uani 1 1 d . . . . .
C4 C 0.64600(18) -0.0376(5) 0.78776(16) 0.0558(7) Uani 1 1 d . . . . .
C9 C 0.36506(18) 0.6625(5) 0.85497(15) 0.0557(7) Uani 1 1 d . . . . .
C3 C 0.65588(18) 0.0311(5) 0.71769(16) 0.0550(7) Uani 1 1 d . . . . .
C17 C 0.2004(2) 0.9419(6) 0.46644(14) 0.0627(8) Uani 1 1 d . . . . .
C18 C 0.2846(2) 1.0632(6) 0.47183(15) 0.0616(8) Uani 1 1 d . . . . .
H15 H 0.2891(15) 0.493(5) 0.5876(13) 0.052(7) Uiso 1 1 d . . . . .
H8 H 0.4488(18) 0.360(5) 0.8971(15) 0.062(7) Uiso 1 1 d . . . . .
H10 H 0.2941(15) 0.968(4) 0.7963(12) 0.048(6) Uiso 1 1 d . . . . .
H9 H 0.3412(17) 0.676(4) 0.8970(15) 0.063(7) Uiso 1 1 d . . . . .
H4 H 0.6845(19) -0.174(5) 0.8184(16) 0.076(8) Uiso 1 1 d . . . . .
H11 H 0.3483(15) 0.921(4) 0.6906(13) 0.046(6) Uiso 1 1 d . . . . .
H19 H 0.4324(18) 1.064(5) 0.5228(14) 0.060(7) Uiso 1 1 d . . . . .
H18 H 0.2822(18) 1.205(5) 0.4454(16) 0.070(8) Uiso 1 1 d . . . . .
H2 H 0.6108(16) 0.267(4) 0.6264(15) 0.056(7) Uiso 1 1 d . . . . .
H3 H 0.6994(17) -0.062(5) 0.6974(14) 0.064(7) Uiso 1 1 d . . . . .
H5 H 0.5743(17) 0.044(5) 0.8662(16) 0.068(8) Uiso 1 1 d . . . . .
H17 H 0.134(2) 0.996(5) 0.4350(17) 0.084(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C16 1.359(3) . ?
O1 C13 1.214(3) . ?
N003 C12 1.420(3) . ?
N003 C1 1.421(3) . ?
N003 C13 1.392(3) . ?
C12 C7 1.403(3) . ?
C12 C11 1.384(3) . ?
C7 C6 1.444(3) . ?
C7 C8 1.384(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.389(3) . ?
C6 C5 1.395(3) . ?
C14 C15 1.387(3) . ?
C14 C13 1.491(3) . ?
C14 C19 1.391(3) . ?
C11 C10 1.378(3) . ?
C11 H11 0.96(2) . ?
C15 C16 1.364(3) . ?
C15 H15 0.98(2) . ?
C8 C9 1.379(4) . ?
C8 H8 0.97(3) . ?
C5 C4 1.379(4) . ?
C5 H5 0.96(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.98(2) . ?
C10 C9 1.384(4) . ?
C10 H10 1.00(2) . ?
C16 C17 1.372(4) . ?
C19 C18 1.382(4) . ?
C19 H19 0.99(2) . ?
C4 C3 1.390(4) . ?
C4 H4 0.99(3) . ?
C9 H9 0.94(3) . ?
C3 H3 0.97(3) . ?
C17 C18 1.372(4) . ?
C17 H17 1.01(3) . ?
C18 H18 0.90(3) . ?

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
C12 N003 C1 107.87(17) . . ?
C13 N003 C12 128.26(18) . . ?
C13 N003 C1 123.75(18) . . ?
C7 C12 N003 108.10(18) . . ?
C11 C12 N003 130.82(19) . . ?
C11 C12 C7 120.9(2) . . ?
C12 C7 C6 107.65(18) . . ?
C8 C7 C12 119.9(2) . . ?
C8 C7 C6 132.3(2) . . ?
C6 C1 N003 108.41(18) . . ?
C2 C1 N003 129.7(2) . . ?
C2 C1 C6 121.8(2) . . ?
C1 C6 C7 107.83(18) . . ?
C1 C6 C5 119.8(2) . . ?
C5 C6 C7 132.4(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 C19 120.3(2) . . ?
C19 C14 C13 118.9(2) . . ?
C12 C11 H11 122.5(13) . . ?
C10 C11 C12 118.1(2) . . ?
C10 C11 H11 119.4(13) . . ?
C14 C15 H15 121.4(13) . . ?
C16 C15 C14 118.1(2) . . ?
C16 C15 H15 120.5(13) . . ?
O1 C13 N003 120.9(2) . . ?
O1 C13 C14 120.9(2) . . ?
N003 C13 C14 118.03(19) . . ?
C7 C8 H8 119.9(15) . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 121.1(15) . . ?
C6 C5 H5 117.8(15) . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 123.6(15) . . ?
C1 C2 H2 122.5(14) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2 120.0(14) . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10 118.5(13) . . ?
C9 C10 H10 120.0(13) . . ?
F1 C16 C15 118.2(2) . . ?
F1 C16 C17 118.5(2) . . ?
C15 C16 C17 123.2(3) . . ?
C14 C19 H19 119.6(15) . . ?
C18 C19 C14 119.3(3) . . ?
C18 C19 H19 121.1(15) . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 117.6(15) . . ?
C3 C4 H4 121.5(15) . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 118.5(15) . . ?
C10 C9 H9 120.9(15) . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.7(15) . . ?
C4 C3 H3 118.9(15) . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 H17 116.0(17) . . ?
C18 C17 H17 125.8(17) . . ?
C19 C18 H18 120.0(17) . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 118.9(16) . . ?

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 C16 C17 C18 -179.6(2) . . . . ?
N003 C12 C7 C6 1.6(2) . . . . ?
N003 C12 C7 C8 178.52(19) . . . . ?
N003 C12 C11 C10 -176.7(2) . . . . ?
N003 C1 C6 C7 -2.8(2) . . . . ?
N003 C1 C6 C5 176.96(18) . . . . ?
N003 C1 C2 C3 -176.5(2) . . . . ?
C12 N003 C1 C6 3.8(2) . . . . ?
C12 N003 C1 C2 179.8(2) . . . . ?
C12 N003 C13 O1 151.3(2) . . . . ?
C12 N003 C13 C14 -33.4(3) . . . . ?
C12 C7 C6 C1 0.8(2) . . . . ?
C12 C7 C6 C5 -179.0(2) . . . . ?
C12 C7 C8 C9 -1.5(3) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
C7 C12 C11 C10 -1.8(3) . . . . ?
C7 C6 C5 C4 179.9(2) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C1 N003 C12 C7 -3.3(2) . . . . ?
C1 N003 C12 C11 172.1(2) . . . . ?
C1 N003 C13 O1 -24.0(3) . . . . ?
C1 N003 C13 C14 151.3(2) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C6 C7 C8 C9 174.5(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C5 C4 C3 -0.4(4) . . . . ?
C14 C15 C16 F1 179.2(2) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C14 C19 C18 C17 -0.1(4) . . . . ?
C11 C12 C7 C6 -174.36(18) . . . . ?
C11 C12 C7 C8 2.6(3) . . . . ?
C11 C10 C9 C8 1.0(4) . . . . ?
C15 C14 C13 O1 134.3(2) . . . . ?
C15 C14 C13 N003 -41.0(3) . . . . ?
C15 C14 C19 C18 -0.3(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C13 N003 C12 C7 -179.24(19) . . . . ?
C13 N003 C12 C11 -3.9(4) . . . . ?
C13 N003 C1 C6 179.97(18) . . . . ?
C13 N003 C1 C2 -4.0(3) . . . . ?
C13 C14 C15 C16 -172.7(2) . . . . ?
C13 C14 C19 C18 173.0(2) . . . . ?
C8 C7 C6 C1 -175.7(2) . . . . ?
C8 C7 C6 C5 4.6(4) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?
C2 C1 C6 C7 -179.23(19) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C19 C14 C13 O1 -39.0(3) . . . . ?
C19 C14 C13 N003 145.7(2) . . . . ?

_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_1111a
_database_code_depnum_ccdc_archive 'CCDC 1975625'
loop_
_audit_author_name
_audit_author_address
LiHui
;Nanjing University Of Posts And Telecommunications
China
;
_audit_update_record             
;
2020-01-06 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 F N O'
_chemical_formula_sum            'C19 H12 F N O'
_chemical_formula_weight         289.30
_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                   8.9406(17)
_cell_length_b                   22.597(4)
_cell_length_c                   7.0302(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.313(5)
_cell_angle_gamma                90
_cell_volume                     1419.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2041
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.737
_cell_measurement_theta_min      1.746
_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   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12326
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.217
_diffrn_reflns_theta_min         1.802
_diffrn_ambient_temperature      297.79
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD?area?detector
_diffrn_measurement_method       CCD?area?detector
_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                2410
_reflns_number_total             3491
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.6496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1499
_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:
 C15(H15), C16(H16), C2(H2), C8(H8), C18(H18), C19(H19), C5(H5), C4(H4),
 C3(H3), C9(H9), C11(H11), C10(H10)
;
_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 0.4125(2) 0.57883(7) 1.0333(3) 0.0963(6) Uani 1 1 d . . . . .
N1 N 0.16789(18) 0.37925(7) 0.4602(2) 0.0449(4) Uani 1 1 d . . . . .
O1 O -0.04115(18) 0.41328(9) 0.6018(2) 0.0718(5) Uani 1 1 d . . . . .
C13 C 0.0942(2) 0.41504(10) 0.5917(3) 0.0485(5) Uani 1 1 d . . . . .
C14 C 0.1860(2) 0.45675(9) 0.7079(3) 0.0443(5) Uani 1 1 d . . . . .
C1 C 0.3201(2) 0.36016(8) 0.4660(3) 0.0446(5) Uani 1 1 d . . . . .
C7 C 0.0986(2) 0.35576(8) 0.2925(3) 0.0458(5) Uani 1 1 d . . . . .
C6 C 0.3476(2) 0.32886(8) 0.2977(3) 0.0475(5) Uani 1 1 d . . . . .
C15 C 0.2942(2) 0.49280(9) 0.6281(3) 0.0510(5) Uani 1 1 d . . . . .
H15 H 0.3146 0.4891 0.4995 0.061 Uiso 1 1 calc R . . . .
C12 C 0.2090(3) 0.32618(8) 0.1883(3) 0.0491(5) Uani 1 1 d . . . . .
C16 C 0.3713(3) 0.53386(10) 0.7371(4) 0.0593(6) Uani 1 1 d . . . . .
H16 H 0.4437 0.5579 0.6843 0.071 Uiso 1 1 calc R . . . .
C17 C 0.3377(3) 0.53802(10) 0.9258(4) 0.0623(6) Uani 1 1 d . . . . .
C2 C 0.4286(2) 0.36498(9) 0.6092(3) 0.0542(5) Uani 1 1 d . . . . .
H2 H 0.4088 0.3841 0.7231 0.065 Uiso 1 1 calc R . . . .
C8 C -0.0479(3) 0.35961(10) 0.2273(3) 0.0550(5) Uani 1 1 d . . . . .
H8 H -0.1198 0.3795 0.2965 0.066 Uiso 1 1 calc R . . . .
C18 C 0.2318(3) 0.50376(12) 1.0103(3) 0.0648(7) Uani 1 1 d . . . . .
H18 H 0.2127 0.5078 1.1392 0.078 Uiso 1 1 calc R . . . .
C19 C 0.1538(3) 0.46295(10) 0.8992(3) 0.0543(6) Uani 1 1 d . . . . .
H19 H 0.0799 0.4397 0.9528 0.065 Uiso 1 1 calc R . . . .
C5 C 0.4890(3) 0.30439(9) 0.2699(4) 0.0612(6) Uani 1 1 d . . . . .
H5 H 0.5090 0.2841 0.1582 0.073 Uiso 1 1 calc R . . . .
C4 C 0.5982(3) 0.31060(10) 0.4095(4) 0.0676(7) Uani 1 1 d . . . . .
H4 H 0.6928 0.2948 0.3915 0.081 Uiso 1 1 calc R . . . .
C3 C 0.5680(3) 0.34028(10) 0.5766(4) 0.0627(6) Uani 1 1 d . . . . .
H3 H 0.6432 0.3438 0.6696 0.075 Uiso 1 1 calc R . . . .
C9 C -0.0839(3) 0.33286(11) 0.0551(4) 0.0676(7) Uani 1 1 d . . . . .
H9 H -0.1819 0.3347 0.0082 0.081 Uiso 1 1 calc R . . . .
C11 C 0.1694(3) 0.29991(10) 0.0148(3) 0.0645(7) Uani 1 1 d . . . . .
H11 H 0.2408 0.2805 -0.0563 0.077 Uiso 1 1 calc R . . . .
C10 C 0.0235(4) 0.30326(11) -0.0493(4) 0.0728(8) Uani 1 1 d . . . . .
H10 H -0.0041 0.2855 -0.1642 0.087 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.358(3) . ?
N1 C13 1.403(3) . ?
N1 C1 1.427(3) . ?
N1 C7 1.422(3) . ?
O1 C13 1.215(3) . ?
C13 C14 1.482(3) . ?
C14 C15 1.392(3) . ?
C14 C19 1.389(3) . ?
C1 C6 1.405(3) . ?
C1 C2 1.386(3) . ?
C7 C12 1.410(3) . ?
C7 C8 1.381(3) . ?
C6 C12 1.445(3) . ?
C6 C5 1.397(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C12 C11 1.395(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(3) . ?
C17 C18 1.369(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.393(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.373(4) . ?
C10 H10 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
C13 N1 C1 128.08(18) . . ?
C13 N1 C7 124.00(18) . . ?
C7 N1 C1 107.91(16) . . ?
N1 C13 C14 117.85(18) . . ?
O1 C13 N1 120.2(2) . . ?
O1 C13 C14 121.86(19) . . ?
C15 C14 C13 122.05(18) . . ?
C19 C14 C13 118.26(19) . . ?
C19 C14 C15 119.5(2) . . ?
C6 C1 N1 108.27(18) . . ?
C2 C1 N1 130.40(19) . . ?
C2 C1 C6 121.2(2) . . ?
C12 C7 N1 108.13(19) . . ?
C8 C7 N1 130.06(19) . . ?
C8 C7 C12 121.8(2) . . ?
C1 C6 C12 107.72(18) . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C12 132.6(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C7 C12 C6 107.78(18) . . ?
C11 C12 C7 119.3(2) . . ?
C11 C12 C6 132.9(2) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 C15 117.8(2) . . ?
C17 C16 H16 121.1 . . ?
F1 C17 C16 118.0(3) . . ?
F1 C17 C18 118.6(2) . . ?
C18 C17 C16 123.4(2) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.7(2) . . ?
C3 C2 H2 121.2 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.6(2) . . ?
C9 C8 H8 121.2 . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.4(2) . . ?
C19 C18 H18 120.8 . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5 120.4 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 H11 120.5 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 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 C17 C18 C19 178.8(2) . . . . ?
N1 C13 C14 C15 46.4(3) . . . . ?
N1 C13 C14 C19 -138.7(2) . . . . ?
N1 C1 C6 C12 -2.4(2) . . . . ?
N1 C1 C6 C5 -178.85(17) . . . . ?
N1 C1 C2 C3 178.0(2) . . . . ?
N1 C7 C12 C6 2.8(2) . . . . ?
N1 C7 C12 C11 -178.93(18) . . . . ?
N1 C7 C8 C9 179.0(2) . . . . ?
O1 C13 C14 C15 -130.2(2) . . . . ?
O1 C13 C14 C19 44.6(3) . . . . ?
C13 N1 C1 C6 -175.53(18) . . . . ?
C13 N1 C1 C2 9.1(3) . . . . ?
C13 N1 C7 C12 175.40(18) . . . . ?
C13 N1 C7 C8 -3.3(3) . . . . ?
C13 C14 C15 C16 175.8(2) . . . . ?
C13 C14 C19 C18 -176.6(2) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C1 N1 C13 O1 -157.6(2) . . . . ?
C1 N1 C13 C14 25.7(3) . . . . ?
C1 N1 C7 C12 -4.3(2) . . . . ?
C1 N1 C7 C8 177.1(2) . . . . ?
C1 C6 C12 C7 -0.3(2) . . . . ?
C1 C6 C12 C11 -178.2(2) . . . . ?
C1 C6 C5 C4 1.0(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C7 N1 C13 O1 22.9(3) . . . . ?
C7 N1 C13 C14 -153.84(18) . . . . ?
C7 N1 C1 C6 4.1(2) . . . . ?
C7 N1 C1 C2 -171.3(2) . . . . ?
C7 C12 C11 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C6 C1 C2 C3 3.1(3) . . . . ?
C6 C12 C11 C10 177.3(2) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C15 C14 C19 C18 -1.6(3) . . . . ?
C15 C16 C17 F1 -179.4(2) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C12 C6 C5 C4 -174.4(2) . . . . ?
C12 C11 C10 C9 0.7(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C14 1.3(3) . . . . ?
C2 C1 C6 C12 173.52(18) . . . . ?
C2 C1 C6 C5 -3.0(3) . . . . ?
C8 C7 C12 C6 -178.42(19) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C19 C14 C15 C16 1.0(3) . . . . ?
C5 C6 C12 C7 175.6(2) . . . . ?
C5 C6 C12 C11 -2.4(4) . . . . ?
C5 C4 C3 C2 -0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
