# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_to3_2019
_database_code_depnum_ccdc_archive 'CCDC 2224267'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2022-12-21
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
phenanthridin-6(5H)-one -- perfluorobenzoic acid
;
_chemical_formula_moiety         ' C13 H9 N O, C7 H F5 O2'
_chemical_formula_sum            'C20 H10 F5 N O3'
_chemical_formula_weight         407.29


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2840(13)
_cell_length_b                   8.5719(13)
_cell_length_c                   13.363(2)
_cell_angle_alpha                93.005(13)
_cell_angle_beta                 102.411(13)
_cell_angle_gamma                92.991(13)
_cell_volume                     812.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2109
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      29.38
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.15
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_number            8160
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.936
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             3008
_reflns_number_gt                2559
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1211P)²+0.4701P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1907
_refine_ls_wR_factor_gt          0.1813
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.2381(3) 0.6269(3) 0.74692(17) 0.0289(5) Uani 1 1 d . . . . .
C2 C 0.1691(3) 0.4819(3) 0.77172(19) 0.0335(5) Uani 1 1 d . . . . .
H2A H 0.137607 0.3973 0.721013 0.045(8) Uiso 1 1 calc R . . . .
C3 C 0.1471(4) 0.4629(3) 0.87062(19) 0.0375(6) Uani 1 1 d . . . . .
H3 H 0.100873 0.364661 0.888153 0.049(8) Uiso 1 1 calc R . . . .
C4 C 0.1926(3) 0.5878(3) 0.94482(19) 0.0376(5) Uani 1 1 d . . . . .
H4 H 0.178978 0.574074 1.01299 0.053(8) Uiso 1 1 calc R . . . .
C5 C 0.2574(3) 0.7313(3) 0.91919(17) 0.0324(5) Uani 1 1 d . . . . .
H5 H 0.286425 0.8159 0.970044 0.036(7) Uiso 1 1 calc R . . . .
C6 C 0.2814(3) 0.7548(3) 0.81952(17) 0.0289(5) Uani 1 1 d . . . . .
C7 C 0.3466(3) 0.9040(3) 0.78688(17) 0.0280(5) Uani 1 1 d . . . . .
C8 C 0.3888(3) 1.0410(3) 0.85254(17) 0.0312(5) Uani 1 1 d . . . . .
H8 H 0.37328 1.038379 0.921238 0.037(7) Uiso 1 1 calc R . . . .
C9 C 0.4522(3) 1.1788(3) 0.81883(18) 0.0329(5) Uani 1 1 d . . . . .
H9 H 0.480613 1.269514 0.8647 0.043(7) Uiso 1 1 calc R . . . .
C10 C 0.4751(3) 1.1866(3) 0.71791(18) 0.0340(5) Uani 1 1 d . . . . .
H10 H 0.518899 1.282083 0.695326 0.049(8) Uiso 1 1 calc R . . . .
C11 C 0.4337(3) 1.0545(3) 0.65133(18) 0.0321(5) Uani 1 1 d . . . . .
H11 H 0.447821 1.059227 0.582487 0.036(7) Uiso 1 1 calc R . . . .
C12 C 0.3711(3) 0.9142(3) 0.68514(17) 0.0283(5) Uani 1 1 d . . . . .
C13 C 0.3310(3) 0.7746(3) 0.61278(17) 0.0285(5) Uani 1 1 d . . . . .
C14 C 0.2371(3) 0.3036(3) 0.23502(18) 0.0315(5) Uani 1 1 d . . . . .
C15 C 0.2012(3) 0.1831(3) 0.15884(17) 0.0330(5) Uani 1 1 d . . . . .
C16 C 0.1367(3) 0.0370(3) 0.17991(19) 0.0357(6) Uani 1 1 d . . . . .
C17 C 0.1075(3) 0.0111(3) 0.27648(19) 0.0341(5) Uani 1 1 d . . . . .
C18 C 0.1415(3) 0.1322(3) 0.35166(17) 0.0316(5) Uani 1 1 d . . . . .
C19 C 0.2069(3) 0.2825(3) 0.33315(17) 0.0295(5) Uani 1 1 d . . . . .
C20 C 0.2370(3) 0.4119(3) 0.41644(17) 0.0310(5) Uani 1 1 d . . . . .
F1 F 0.2999(2) 0.44174(16) 0.20832(10) 0.0375(4) Uani 1 1 d . . . . .
F2 F 0.2309(2) 0.20729(18) 0.06515(10) 0.0419(4) Uani 1 1 d . . . . .
F3 F 0.0995(2) -0.07916(17) 0.10599(11) 0.0447(4) Uani 1 1 d . . . . .
F4 F 0.0461(2) -0.13094(16) 0.29645(12) 0.0447(4) Uani 1 1 d . . . . .
F5 F 0.1094(2) 0.09989(17) 0.44270(11) 0.0404(4) Uani 1 1 d . . . . .
N1 N 0.2636(3) 0.6429(2) 0.64776(14) 0.0301(4) Uani 1 1 d . . . . .
H1 H 0.233411 0.560486 0.604048 0.040(7) Uiso 1 1 calc R . . . .
O1 O 0.3588(2) 0.77496(19) 0.52383(12) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.3250(4) 0.5352(2) 0.39715(16) 0.0639(7) Uani 1 1 d . . . . .
H2 H 0.318043 0.608208 0.440336 0.108(16) Uiso 1 1 calc R . . . .
O3 O 0.1780(4) 0.3974(2) 0.49244(17) 0.0719(8) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.390(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.382(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.381(3) . ?
C5 C6 1.403(3) . ?
C6 C7 1.461(3) . ?
C7 C8 1.408(3) . ?
C7 C12 1.415(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.399(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.474(3) . ?
C13 O1 1.248(3) . ?
C13 N1 1.353(3) . ?
C14 F1 1.340(3) . ?
C14 C15 1.385(3) . ?
C14 C19 1.395(3) . ?
C15 F2 1.340(3) . ?
C15 C16 1.379(4) . ?
C16 F3 1.340(3) . ?
C16 C17 1.379(4) . ?
C17 F4 1.335(3) . ?
C17 C18 1.380(3) . ?
C18 F5 1.327(3) . ?
C18 C19 1.403(3) . ?
C19 C20 1.503(3) . ?
C20 O3 1.195(3) . ?
C20 O2 1.273(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
N1 C1 C2 118.7(2) . . ?
N1 C1 C6 119.8(2) . . ?
C2 C1 C6 121.5(2) . . ?
C3 C2 C1 119.4(2) . . ?
C2 C3 C4 120.1(2) . . ?
C5 C4 C3 120.1(2) . . ?
C4 C5 C6 121.3(2) . . ?
C1 C6 C5 117.6(2) . . ?
C1 C6 C7 118.3(2) . . ?
C5 C6 C7 124.1(2) . . ?
C8 C7 C12 117.2(2) . . ?
C8 C7 C6 123.1(2) . . ?
C12 C7 C6 119.70(19) . . ?
C9 C8 C7 121.1(2) . . ?
C8 C9 C10 120.8(2) . . ?
C11 C10 C9 119.5(2) . . ?
C10 C11 C12 120.0(2) . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 C13 118.8(2) . . ?
C7 C12 C13 119.9(2) . . ?
O1 C13 N1 120.73(19) . . ?
O1 C13 C12 122.6(2) . . ?
N1 C13 C12 116.62(19) . . ?
F1 C14 C15 116.0(2) . . ?
F1 C14 C19 122.2(2) . . ?
C15 C14 C19 121.8(2) . . ?
F2 C15 C16 119.8(2) . . ?
F2 C15 C14 120.4(2) . . ?
C16 C15 C14 119.8(2) . . ?
F3 C16 C15 119.9(2) . . ?
F3 C16 C17 120.0(2) . . ?
C15 C16 C17 120.1(2) . . ?
F4 C17 C16 119.7(2) . . ?
F4 C17 C18 120.5(2) . . ?
C16 C17 C18 119.8(2) . . ?
F5 C18 C17 116.8(2) . . ?
F5 C18 C19 121.4(2) . . ?
C17 C18 C19 121.8(2) . . ?
C14 C19 C18 116.7(2) . . ?
C14 C19 C20 123.3(2) . . ?
C18 C19 C20 120.0(2) . . ?
O3 C20 O2 124.5(2) . . ?
O3 C20 C19 121.1(2) . . ?
O2 C20 C19 114.3(2) . . ?
C13 N1 C1 125.51(19) . . ?

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
N1 C1 C2 C3 178.5(2) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
N1 C1 C6 C5 -178.49(19) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
N1 C1 C6 C7 2.1(3) . . . . ?
C2 C1 C6 C7 -177.88(19) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C7 179.0(2) . . . . ?
C1 C6 C7 C8 178.12(19) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C1 C6 C7 C12 -2.4(3) . . . . ?
C5 C6 C7 C12 178.2(2) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C6 C7 C8 C9 179.19(19) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C6 C7 C12 C11 -179.81(19) . . . . ?
C8 C7 C12 C13 179.48(18) . . . . ?
C6 C7 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 O1 3.3(3) . . . . ?
C7 C12 C13 O1 -176.4(2) . . . . ?
C11 C12 C13 N1 -177.47(19) . . . . ?
C7 C12 C13 N1 2.8(3) . . . . ?
F1 C14 C15 F2 0.6(3) . . . . ?
C19 C14 C15 F2 179.70(19) . . . . ?
F1 C14 C15 C16 179.83(19) . . . . ?
C19 C14 C15 C16 -1.1(4) . . . . ?
F2 C15 C16 F3 -1.7(3) . . . . ?
C14 C15 C16 F3 179.11(19) . . . . ?
F2 C15 C16 C17 179.43(19) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
F3 C16 C17 F4 1.5(3) . . . . ?
C15 C16 C17 F4 -179.59(19) . . . . ?
F3 C16 C17 C18 -178.36(19) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
F4 C17 C18 F5 -0.3(3) . . . . ?
C16 C17 C18 F5 179.55(19) . . . . ?
F4 C17 C18 C19 179.68(19) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
F1 C14 C19 C18 -179.82(18) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
F1 C14 C19 C20 1.5(3) . . . . ?
C15 C14 C19 C20 -177.5(2) . . . . ?
F5 C18 C19 C14 179.62(19) . . . . ?
C17 C18 C19 C14 -0.4(3) . . . . ?
F5 C18 C19 C20 -1.7(3) . . . . ?
C17 C18 C19 C20 178.3(2) . . . . ?
C14 C19 C20 O3 166.2(3) . . . . ?
C18 C19 C20 O3 -12.4(4) . . . . ?
C14 C19 C20 O2 -12.4(3) . . . . ?
C18 C19 C20 O2 169.0(2) . . . . ?
O1 C13 N1 C1 175.9(2) . . . . ?
C12 C13 N1 C1 -3.3(3) . . . . ?
C2 C1 N1 C13 -179.2(2) . . . . ?
C6 C1 N1 C13 0.9(3) . . . . ?

_vrf_PLAT097_to3_2019            
;
PROBLEM:  Large Reported Max. (Positive) Residual Density 0.94 eA-3
RESPONSE: The residual density of 0.94 eA-3 is due to disorder resulting from 
the presence of minute population of the second tautomer. The determination 
position of the all molecul of the tautomer would not be reliable.
;
# END of CIF

# END of CIF
####################################################################### 
# 
# 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_to13_2021
_database_code_depnum_ccdc_archive 'CCDC 2224270'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-12-04 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2021-07-27
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic



#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
pyridin-2(1H)-one -- perfluorophenol 
;
_chemical_formula_moiety         'C6 H F5 O, C5 H5 N O'
_chemical_formula_sum            'C11 H6 F5 N O2'
_chemical_formula_weight         279.17
_chemical_absolute_configuration unk


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   5.6381(10)
_cell_length_b                   8.0585(14)
_cell_length_c                   23.653(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.658(14)
_cell_angle_gamma                90
_cell_volume                     1069.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2922
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      24.80
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.032
_diffrn_reflns_number            11382
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.672
_diffrn_reflns_theta_max         29.264
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_Friedel_coverage         0
_reflns_number_total             2873
_reflns_number_gt                2253
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0828P)²+0.3499P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.092

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 1.0678(3) 0.8654(2) 0.62580(7) 0.0295(4) Uani 1 1 d . . . . .
H1A H 1.211949 0.911578 0.643214 0.035 Uiso 1 1 calc R U . . .
C2 C 0.9319(3) 0.7692(2) 0.65664(8) 0.0325(4) Uani 1 1 d . . . . .
H2A H 0.977934 0.747354 0.695645 0.039 Uiso 1 1 calc R U . . .
C3 C 0.7199(3) 0.7023(2) 0.62919(8) 0.0324(4) Uani 1 1 d . . . . .
H3 H 0.621606 0.634728 0.650099 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6535(3) 0.7328(2) 0.57323(8) 0.0304(4) Uani 1 1 d . . . . .
H4 H 0.512052 0.684243 0.555283 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7952(3) 0.8373(2) 0.54150(7) 0.0280(3) Uani 1 1 d . . . . .
C6 C 0.1527(3) 0.6982(2) 0.41089(7) 0.0287(3) Uani 1 1 d . . . . .
C7 C -0.0577(3) 0.6243(2) 0.38906(8) 0.0296(4) Uani 1 1 d . . . . .
C8 C -0.1318(3) 0.6381(2) 0.33195(8) 0.0298(4) Uani 1 1 d . . . . .
C9 C 0.0051(3) 0.7256(2) 0.29702(7) 0.0297(4) Uani 1 1 d . . . . .
C10 C 0.2140(3) 0.7994(2) 0.31923(7) 0.0281(3) Uani 1 1 d . . . . .
C11 C 0.2938(3) 0.78762(19) 0.37666(7) 0.0271(3) Uani 1 1 d . . . . .
F1 F 0.2239(2) 0.68355(14) 0.46647(5) 0.0374(3) Uani 1 1 d . . . . .
F2 F -0.1876(2) 0.53769(14) 0.42297(5) 0.0395(3) Uani 1 1 d . . . . .
F3 F -0.3361(2) 0.56730(14) 0.31007(5) 0.0395(3) Uani 1 1 d . . . . .
F4 F -0.0663(2) 0.73824(15) 0.24130(5) 0.0397(3) Uani 1 1 d . . . . .
F5 F 0.3440(2) 0.88606(14) 0.28462(5) 0.0367(3) Uani 1 1 d . . . . .
N1 N 0.9996(3) 0.89656(17) 0.57011(6) 0.0274(3) Uani 1 1 d . . . . .
H1 H 1.093163 0.958884 0.551319 0.033 Uiso 1 1 calc R U . . .
O1 O 0.7461(2) 0.87816(17) 0.49007(5) 0.0353(3) Uani 1 1 d . . . . .
O2 O 0.4982(2) 0.86331(16) 0.39533(6) 0.0326(3) Uani 1 1 d . . . . .
H2 H 0.532506 0.841375 0.429887 0.049 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.353(2) . ?
C1 N1 1.359(2) . ?
C1 H1A 0.95 . ?
C2 C3 1.410(3) . ?
C2 H2A 0.95 . ?
C3 C4 1.362(3) . ?
C3 H3 0.95 . ?
C4 C5 1.424(2) . ?
C4 H4 0.95 . ?
C5 O1 1.264(2) . ?
C5 N1 1.364(2) . ?
C6 F1 1.341(2) . ?
C6 C7 1.381(2) . ?
C6 C11 1.391(2) . ?
C7 F2 1.335(2) . ?
C7 C8 1.378(2) . ?
C8 F3 1.343(2) . ?
C8 C9 1.379(3) . ?
C9 F4 1.344(2) . ?
C9 C10 1.377(2) . ?
C10 F5 1.3467(19) . ?
C10 C11 1.391(2) . ?
C11 O2 1.340(2) . ?
N1 H1 0.88 . ?
O2 H2 0.84 . ?

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
C2 C1 N1 120.48(16) . . ?
C2 C1 H1A 119.8 . . ?
N1 C1 H1A 119.8 . . ?
C1 C2 C3 118.05(17) . . ?
C1 C2 H2A 121 . . ?
C3 C2 H2A 121 . . ?
C4 C3 C2 121.20(16) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.27(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
O1 C5 N1 118.68(15) . . ?
O1 C5 C4 125.47(16) . . ?
N1 C5 C4 115.85(15) . . ?
F1 C6 C7 119.44(15) . . ?
F1 C6 C11 118.89(15) . . ?
C7 C6 C11 121.67(16) . . ?
F2 C7 C8 119.99(16) . . ?
F2 C7 C6 120.17(16) . . ?
C8 C7 C6 119.84(16) . . ?
F3 C8 C7 120.59(16) . . ?
F3 C8 C9 119.73(16) . . ?
C7 C8 C9 119.68(16) . . ?
F4 C9 C10 120.27(16) . . ?
F4 C9 C8 119.69(16) . . ?
C10 C9 C8 120.04(16) . . ?
F5 C10 C9 119.25(16) . . ?
F5 C10 C11 119.08(15) . . ?
C9 C10 C11 121.68(16) . . ?
O2 C11 C6 124.51(16) . . ?
O2 C11 C10 118.39(15) . . ?
C6 C11 C10 117.10(16) . . ?
C1 N1 C5 124.11(15) . . ?
C1 N1 H1 117.9 . . ?
C5 N1 H1 117.9 . . ?
C11 O2 H2 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
N1 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C3 C4 C5 O1 -177.50(18) . . . . ?
C3 C4 C5 N1 2.4(3) . . . . ?
F1 C6 C7 F2 -0.7(2) . . . . ?
C11 C6 C7 F2 179.20(15) . . . . ?
F1 C6 C7 C8 -179.72(15) . . . . ?
C11 C6 C7 C8 0.2(3) . . . . ?
F2 C7 C8 F3 1.1(3) . . . . ?
C6 C7 C8 F3 -179.89(15) . . . . ?
F2 C7 C8 C9 -178.97(15) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
F3 C8 C9 F4 -0.4(2) . . . . ?
C7 C8 C9 F4 179.62(15) . . . . ?
F3 C8 C9 C10 179.57(15) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
F4 C9 C10 F5 0.8(2) . . . . ?
C8 C9 C10 F5 -179.19(15) . . . . ?
F4 C9 C10 C11 -179.53(14) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
F1 C6 C11 O2 -0.8(2) . . . . ?
C7 C6 C11 O2 179.35(16) . . . . ?
F1 C6 C11 C10 179.80(14) . . . . ?
C7 C6 C11 C10 -0.1(2) . . . . ?
F5 C10 C11 O2 0.0(2) . . . . ?
C9 C10 C11 O2 -179.71(15) . . . . ?
F5 C10 C11 C6 179.44(14) . . . . ?
C9 C10 C11 C6 -0.2(2) . . . . ?
C2 C1 N1 C5 0.6(3) . . . . ?
O1 C5 N1 C1 177.98(16) . . . . ?
C4 C5 N1 C1 -1.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A F5 0.95 2.54 3.357(2) 143.8 4_676 yes
C4 H4 F1 0.95 2.53 3.346(2) 144.6 . yes
N1 H1 O1 0.88 1.92 2.7892(19) 170.2 3_776 yes
O2 H2 F1 0.84 2.39 2.7989(17) 111 . yes
O2 H2 O1 0.84 1.8 2.5245(19) 144 . yes

# END of CIF

####################################################################### 
# 
# 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_to5_2022
_database_code_depnum_ccdc_archive 'CCDC 2224268'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2022-12-21
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
benzo[cd]indol-2(1H)-one -- perfluorobenzoic acid 
;
_chemical_formula_moiety         'C7 H F5 O2, C11 H7 N O'
_chemical_formula_sum            'C18 H8 F5 N O3'
_chemical_formula_weight         381.25
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   7.9484(9)
_cell_length_b                   7.1832(5)
_cell_length_c                   26.471(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.279(9)
_cell_angle_gamma                90
_cell_volume                     1508.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9680
_cell_measurement_theta_min      1.61
_cell_measurement_theta_max      29.37

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_number            17470
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.637
_diffrn_reflns_theta_max         29.3
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             4067
_reflns_number_gt                3502
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#


_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²+0.4808P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4067
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.13
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.81191(16) 0.89355(19) 0.63148(5) 0.0285(3) Uani 1 1 d . . . . .
C2 C 0.72299(16) 1.06083(19) 0.62267(5) 0.0293(3) Uani 1 1 d . . . . .
C3 C 0.72262(18) 1.1931(2) 0.65980(6) 0.0345(3) Uani 1 1 d . . . . .
H3 H 0.662589 1.306673 0.655036 0.041 Uiso 1 1 calc R U . . .
C4 C 0.81694(19) 1.1524(2) 0.70623(6) 0.0378(3) Uani 1 1 d . . . . .
H4 H 0.819454 1.24315 0.732382 0.045 Uiso 1 1 calc R U . . .
C5 C 0.90395(18) 0.9892(2) 0.71494(5) 0.0368(3) Uani 1 1 d . . . . .
H5 H 0.964642 0.969312 0.746443 0.044 Uiso 1 1 calc R U . . .
C6 C 0.90294(17) 0.8499(2) 0.67661(5) 0.0323(3) Uani 1 1 d . . . . .
C7 C 0.98136(18) 0.6728(2) 0.67730(6) 0.0360(3) Uani 1 1 d . . . . .
H7 H 1.045113 0.633147 0.706798 0.043 Uiso 1 1 calc R U . . .
C8 C 0.96630(18) 0.5568(2) 0.63551(6) 0.0362(3) Uani 1 1 d . . . . .
H8 H 1.021504 0.439465 0.637184 0.043 Uiso 1 1 calc R U . . .
C9 C 0.87207(17) 0.6054(2) 0.59032(6) 0.0331(3) Uani 1 1 d . . . . .
H9 H 0.86243 0.523162 0.562204 0.04 Uiso 1 1 calc R U . . .
C10 C 0.79491(16) 0.77788(19) 0.58904(5) 0.0287(3) Uani 1 1 d . . . . .
C11 C 0.68614(16) 0.88119(19) 0.55127(5) 0.0293(3) Uani 1 1 d . . . . .
C12 C 0.76612(16) 0.1576(2) 0.43106(5) 0.0300(3) Uani 1 1 d . . . . .
C13 C 0.79758(17) -0.0078(2) 0.40654(5) 0.0324(3) Uani 1 1 d . . . . .
C14 C 0.72773(17) -0.0387(2) 0.35822(6) 0.0326(3) Uani 1 1 d . . . . .
C15 C 0.62944(17) 0.0970(2) 0.33453(5) 0.0323(3) Uani 1 1 d . . . . .
C16 C 0.59814(16) 0.2615(2) 0.35956(5) 0.0297(3) Uani 1 1 d . . . . .
C17 C 0.66477(16) 0.29731(19) 0.40864(5) 0.0286(3) Uani 1 1 d . . . . .
C18 C 0.62769(16) 0.47879(19) 0.43385(5) 0.0303(3) Uani 1 1 d . . . . .
F1 F 0.83801(11) 0.17789(13) 0.47756(3) 0.0379(2) Uani 1 1 d . . . . .
F2 F 0.89762(12) -0.13708(13) 0.42883(4) 0.0410(2) Uani 1 1 d . . . . .
F3 F 0.75701(12) -0.19775(13) 0.33419(4) 0.0426(2) Uani 1 1 d . . . . .
F4 F 0.56695(12) 0.07070(14) 0.28707(3) 0.0422(2) Uani 1 1 d . . . . .
F5 F 0.50417(12) 0.38744(13) 0.33370(3) 0.0383(2) Uani 1 1 d . . . . .
N1 N 0.64774(14) 1.04810(16) 0.57318(4) 0.0303(2) Uani 1 1 d . . . . .
H1 H 0.584752 1.135305 0.558366 0.036 Uiso 1 1 calc R U . . .
O1 O 0.63412(14) 0.83208(15) 0.50832(4) 0.0366(2) Uani 1 1 d . . . . .
O2 O 0.72967(17) 0.51697(18) 0.47249(5) 0.0514(3) Uani 1 1 d . . . . .
H2 H 0.702887 0.619663 0.484914 0.087(9) Uiso 1 1 calc R . . . .
O3 O 0.51472(18) 0.57915(19) 0.41891(5) 0.0587(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C6 1.3967(18) . ?
C1 C10 1.3976(18) . ?
C1 C2 1.4067(19) . ?
C2 C3 1.3672(19) . ?
C2 N1 1.4115(16) . ?
C3 C4 1.433(2) . ?
C3 H3 0.95 . ?
C4 C5 1.374(2) . ?
C4 H4 0.95 . ?
C5 C6 1.425(2) . ?
C5 H5 0.95 . ?
C6 C7 1.416(2) . ?
C7 C8 1.385(2) . ?
C7 H7 0.95 . ?
C8 C9 1.418(2) . ?
C8 H8 0.95 . ?
C9 C10 1.3818(19) . ?
C9 H9 0.95 . ?
C10 C11 1.4829(18) . ?
C11 O1 1.2388(16) . ?
C11 N1 1.3738(17) . ?
C12 F1 1.3352(15) . ?
C12 C13 1.383(2) . ?
C12 C17 1.3977(18) . ?
C13 F2 1.3377(15) . ?
C13 C14 1.383(2) . ?
C14 F3 1.3343(16) . ?
C14 C15 1.378(2) . ?
C15 F4 1.3378(15) . ?
C15 C16 1.384(2) . ?
C16 F5 1.3366(15) . ?
C16 C17 1.3987(18) . ?
C17 C18 1.5013(19) . ?
C18 O3 1.2007(18) . ?
C18 O2 1.2976(17) . ?
N1 H1 0.88 . ?
O2 H2 0.84 . ?

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
C6 C1 C10 125.15(13) . . ?
C6 C1 C2 124.36(13) . . ?
C10 C1 C2 110.49(12) . . ?
C3 C2 C1 119.74(12) . . ?
C3 C2 N1 133.95(13) . . ?
C1 C2 N1 106.30(11) . . ?
C2 C3 C4 116.92(14) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C5 C4 C3 123.47(14) . . ?
C5 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C4 C5 C6 119.84(13) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 114.76(13) . . ?
C1 C6 C5 115.66(13) . . ?
C7 C6 C5 129.59(13) . . ?
C8 C7 C6 120.83(13) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 122.88(14) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
C10 C9 C8 116.99(13) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C9 C10 C1 119.40(13) . . ?
C9 C10 C11 134.91(13) . . ?
C1 C10 C11 105.68(11) . . ?
O1 C11 N1 124.44(12) . . ?
O1 C11 C10 128.86(13) . . ?
N1 C11 C10 106.69(11) . . ?
F1 C12 C13 116.55(12) . . ?
F1 C12 C17 121.25(12) . . ?
C13 C12 C17 122.19(12) . . ?
F2 C13 C14 119.58(13) . . ?
F2 C13 C12 120.53(12) . . ?
C14 C13 C12 119.88(12) . . ?
F3 C14 C15 119.93(13) . . ?
F3 C14 C13 120.44(13) . . ?
C15 C14 C13 119.63(13) . . ?
F4 C15 C14 119.84(13) . . ?
F4 C15 C16 120.20(13) . . ?
C14 C15 C16 119.95(13) . . ?
F5 C16 C15 116.30(12) . . ?
F5 C16 C17 121.47(12) . . ?
C15 C16 C17 122.20(12) . . ?
C12 C17 C16 116.14(12) . . ?
C12 C17 C18 123.91(12) . . ?
C16 C17 C18 119.94(12) . . ?
O3 C18 O2 123.67(14) . . ?
O3 C18 C17 122.49(13) . . ?
O2 C18 C17 113.84(12) . . ?
C11 N1 C2 110.84(11) . . ?
C11 N1 H1 124.6 . . ?
C2 N1 H1 124.6 . . ?
C18 O2 H2 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
C6 C1 C2 C3 0.0(2) . . . . ?
C10 C1 C2 C3 179.55(12) . . . . ?
C6 C1 C2 N1 -179.26(12) . . . . ?
C10 C1 C2 N1 0.25(15) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
N1 C2 C3 C4 179.81(14) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C10 C1 C6 C7 0.0(2) . . . . ?
C2 C1 C6 C7 179.40(12) . . . . ?
C10 C1 C6 C5 179.73(13) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C7 -179.46(14) . . . . ?
C1 C6 C7 C8 0.3(2) . . . . ?
C5 C6 C7 C8 -179.45(14) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C1 -0.39(19) . . . . ?
C8 C9 C10 C11 -179.00(14) . . . . ?
C6 C1 C10 C9 0.1(2) . . . . ?
C2 C1 C10 C9 -179.40(12) . . . . ?
C6 C1 C10 C11 179.09(13) . . . . ?
C2 C1 C10 C11 -0.42(15) . . . . ?
C9 C10 C11 O1 0.3(3) . . . . ?
C1 C10 C11 O1 -178.45(14) . . . . ?
C9 C10 C11 N1 179.18(15) . . . . ?
C1 C10 C11 N1 0.43(14) . . . . ?
F1 C12 C13 F2 -1.06(19) . . . . ?
C17 C12 C13 F2 178.84(12) . . . . ?
F1 C12 C13 C14 -179.87(12) . . . . ?
C17 C12 C13 C14 0.0(2) . . . . ?
F2 C13 C14 F3 1.2(2) . . . . ?
C12 C13 C14 F3 -179.94(12) . . . . ?
F2 C13 C14 C15 -177.75(12) . . . . ?
C12 C13 C14 C15 1.1(2) . . . . ?
F3 C14 C15 F4 -1.6(2) . . . . ?
C13 C14 C15 F4 177.43(13) . . . . ?
F3 C14 C15 C16 179.58(13) . . . . ?
C13 C14 C15 C16 -1.4(2) . . . . ?
F4 C15 C16 F5 0.0(2) . . . . ?
C14 C15 C16 F5 178.87(12) . . . . ?
F4 C15 C16 C17 -178.15(12) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
F1 C12 C17 C16 179.15(12) . . . . ?
C13 C12 C17 C16 -0.7(2) . . . . ?
F1 C12 C17 C18 0.0(2) . . . . ?
C13 C12 C17 C18 -179.88(13) . . . . ?
F5 C16 C17 C12 -177.70(12) . . . . ?
C15 C16 C17 C12 0.4(2) . . . . ?
F5 C16 C17 C18 1.5(2) . . . . ?
C15 C16 C17 C18 179.56(13) . . . . ?
C12 C17 C18 O3 -164.10(16) . . . . ?
C16 C17 C18 O3 16.8(2) . . . . ?
C12 C17 C18 O2 16.7(2) . . . . ?
C16 C17 C18 O2 -162.46(14) . . . . ?
O1 C11 N1 C2 178.65(13) . . . . ?
C10 C11 N1 C2 -0.29(15) . . . . ?
C3 C2 N1 C11 -179.12(15) . . . . ?
C1 C2 N1 C11 0.04(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 F5 0.95 2.59 3.5205(17) 165.7 3_676 yes
C3 H3 O3 0.95 2.48 3.182(2) 130.2 3_676 yes
N1 H1 O1 0.88 2.42 3.1403(15) 139.6 3_676 yes
N1 H1 O3 0.88 2.29 2.9852(17) 135.8 3_676 yes
O2 H2 O1 0.84 1.75 2.5849(16) 176.1 . yes
C3 H3 F5 0.95 2.59 3.5205(17) 165.7 3_676 yes
C3 H3 O3 0.95 2.48 3.182(2) 130.2 3_676 yes
N1 H1 O1 0.88 2.42 3.1403(15) 139.6 3_676 yes
N1 H1 O3 0.88 2.29 2.9852(17) 135.8 3_676 yes
O2 H2 O1 0.84 1.75 2.5849(16) 176.1 . yes


# END of CIF

####################################################################### 
# 
# 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_to14_2021
_database_code_depnum_ccdc_archive 'CCDC 2224271'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-12-04 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2022-11-20
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
pyridin-2(1H)-one -- perfluorobenzoic acid 
;
_chemical_formula_moiety         'C7 H F5 O2, C5 H5 N O'
_chemical_formula_sum            'C12 H6 F5 N O3'
_chemical_formula_weight         307.18
_chemical_absolute_configuration unk
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.275(2)
_cell_length_b                   5.3902(5)
_cell_length_c                   16.953(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.829(11)
_cell_angle_gamma                90
_cell_volume                     1182.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7029
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      25.01
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             616

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_number            14218
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.464
_diffrn_reflns_theta_max         29.235
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_coverage         0
_reflns_number_total             3196
_reflns_number_gt                2889
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+0.3622P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3196
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.039
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.02824(8) -0.30857(19) 0.34951(6) 0.0220(2) Uani 1 1 d . . . . .
H1A H -0.020209 -0.440784 0.343227 0.026 Uiso 1 1 calc R U . . .
C2 C 0.09321(8) -0.2878(2) 0.29786(6) 0.0247(2) Uani 1 1 d . . . . .
H2A H 0.090347 -0.403307 0.255078 0.03 Uiso 1 1 calc R U . . .
C3 C 0.16471(8) -0.0907(2) 0.30956(7) 0.0251(2) Uani 1 1 d . . . . .
H3A H 0.210865 -0.073724 0.274347 0.03 Uiso 1 1 calc R U . . .
C4 C 0.16868(8) 0.0765(2) 0.37080(6) 0.0229(2) Uani 1 1 d . . . . .
H4 H 0.217146 0.20872 0.377754 0.027 Uiso 1 1 calc R U . . .
C5 C 0.10030(7) 0.05247(19) 0.42409(6) 0.01959(19) Uani 1 1 d . . . . .
C6 C 0.30175(8) 1.06183(19) 0.64804(6) 0.0212(2) Uani 1 1 d . . . . .
C7 C 0.38263(8) 1.22550(19) 0.67421(6) 0.0233(2) Uani 1 1 d . . . . .
C8 C 0.47559(8) 1.1904(2) 0.65221(6) 0.0241(2) Uani 1 1 d . . . . .
C9 C 0.48768(8) 0.9899(2) 0.60480(6) 0.0242(2) Uani 1 1 d . . . . .
C10 C 0.40583(8) 0.82819(19) 0.57828(6) 0.0217(2) Uani 1 1 d . . . . .
C11 C 0.31049(8) 0.85899(19) 0.59899(6) 0.01992(19) Uani 1 1 d . . . . .
C12 C 0.22222(8) 0.67870(19) 0.57474(6) 0.0212(2) Uani 1 1 d . . . . .
F1 F 0.21442(5) 1.10955(14) 0.67184(4) 0.02985(17) Uani 1 1 d . . . . .
F2 F 0.37119(6) 1.41857(14) 0.72134(5) 0.03286(18) Uani 1 1 d . . . . .
F3 F 0.55350(6) 1.34836(14) 0.67773(5) 0.03330(18) Uani 1 1 d . . . . .
F4 F 0.57824(5) 0.95027(15) 0.58505(5) 0.03352(18) Uani 1 1 d . . . . .
F5 F 0.42441(5) 0.63651(13) 0.53377(4) 0.03003(17) Uani 1 1 d . . . . .
N1 N 0.03260(7) -0.14077(16) 0.40991(5) 0.02002(18) Uani 1 1 d . . . . .
H1 H -0.01095 -0.157923 0.441824 0.024 Uiso 1 1 calc R U . . .
O1 O 0.09884(6) 0.19608(15) 0.48355(5) 0.02528(18) Uani 1 1 d . . . . .
O2 O 0.22824(6) 0.54726(16) 0.51113(5) 0.02792(18) Uani 1 1 d . . . . .
H2 H 0.180233 0.442439 0.502021 0.042 Uiso 1 1 calc R U . . .
O3 O 0.15520(7) 0.66149(18) 0.61231(5) 0.0333(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.3579(13) . ?
C1 C2 1.3632(14) . ?
C1 H1A 0.95 . ?
C2 C3 1.4093(15) . ?
C2 H2A 0.95 . ?
C3 C4 1.3668(15) . ?
C3 H3A 0.95 . ?
C4 C5 1.4216(14) . ?
C4 H4 0.95 . ?
C5 O1 1.2746(12) . ?
C5 N1 1.3617(13) . ?
C6 F1 1.3344(12) . ?
C6 C7 1.3844(15) . ?
C6 C11 1.3941(14) . ?
C7 F2 1.3411(12) . ?
C7 C8 1.3791(15) . ?
C8 F3 1.3353(12) . ?
C8 C9 1.3775(16) . ?
C9 F4 1.3348(12) . ?
C9 C10 1.3876(15) . ?
C10 F5 1.3343(12) . ?
C10 C11 1.3964(14) . ?
C11 C12 1.5075(14) . ?
C12 O3 1.2072(13) . ?
C12 O2 1.3075(13) . ?
N1 H1 0.88 . ?
O2 H2 0.84 . ?

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
N1 C1 C2 120.18(9) . . ?
N1 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 C3 118.28(10) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C4 C3 C2 121.01(9) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 120.03(9) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
O1 C5 N1 118.61(9) . . ?
O1 C5 C4 124.85(9) . . ?
N1 C5 C4 116.54(9) . . ?
F1 C6 C7 116.38(9) . . ?
F1 C6 C11 121.64(9) . . ?
C7 C6 C11 121.97(10) . . ?
F2 C7 C8 119.61(10) . . ?
F2 C7 C6 120.20(10) . . ?
C8 C7 C6 120.19(10) . . ?
F3 C8 C9 120.47(10) . . ?
F3 C8 C7 120.02(10) . . ?
C9 C8 C7 119.51(10) . . ?
F4 C9 C8 120.00(10) . . ?
F4 C9 C10 120.15(10) . . ?
C8 C9 C10 119.84(10) . . ?
F5 C10 C9 116.10(9) . . ?
F5 C10 C11 121.72(9) . . ?
C9 C10 C11 122.15(10) . . ?
C6 C11 C10 116.32(9) . . ?
C6 C11 C12 120.37(9) . . ?
C10 C11 C12 123.22(9) . . ?
O3 C12 O2 125.49(10) . . ?
O3 C12 C11 121.67(10) . . ?
O2 C12 C11 112.83(9) . . ?
C1 N1 C5 123.96(9) . . ?
C1 N1 H1 118 . . ?
C5 N1 H1 118 . . ?
C12 O2 H2 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
N1 C1 C2 C3 0.61(16) . . . . ?
C1 C2 C3 C4 -0.33(17) . . . . ?
C2 C3 C4 C5 0.25(17) . . . . ?
C3 C4 C5 O1 178.96(10) . . . . ?
C3 C4 C5 N1 -0.44(15) . . . . ?
F1 C6 C7 F2 0.44(15) . . . . ?
C11 C6 C7 F2 179.98(9) . . . . ?
F1 C6 C7 C8 -179.81(9) . . . . ?
C11 C6 C7 C8 -0.27(16) . . . . ?
F2 C7 C8 F3 -0.09(15) . . . . ?
C6 C7 C8 F3 -179.84(9) . . . . ?
F2 C7 C8 C9 179.03(9) . . . . ?
C6 C7 C8 C9 -0.72(16) . . . . ?
F3 C8 C9 F4 1.00(16) . . . . ?
C7 C8 C9 F4 -178.12(10) . . . . ?
F3 C8 C9 C10 -179.58(9) . . . . ?
C7 C8 C9 C10 1.31(16) . . . . ?
F4 C9 C10 F5 0.49(15) . . . . ?
C8 C9 C10 F5 -178.93(9) . . . . ?
F4 C9 C10 C11 178.48(9) . . . . ?
C8 C9 C10 C11 -0.94(16) . . . . ?
F1 C6 C11 C10 -179.85(9) . . . . ?
C7 C6 C11 C10 0.64(15) . . . . ?
F1 C6 C11 C12 -3.16(15) . . . . ?
C7 C6 C11 C12 177.33(9) . . . . ?
F5 C10 C11 C6 177.85(9) . . . . ?
C9 C10 C11 C6 -0.04(15) . . . . ?
F5 C10 C11 C12 1.26(15) . . . . ?
C9 C10 C11 C12 -176.62(9) . . . . ?
C6 C11 C12 O3 -20.32(15) . . . . ?
C10 C11 C12 O3 156.14(11) . . . . ?
C6 C11 C12 O2 160.43(9) . . . . ?
C10 C11 C12 O2 -23.11(14) . . . . ?
C2 C1 N1 C5 -0.87(16) . . . . ?
O1 C5 N1 C1 -178.68(10) . . . . ?
C4 C5 N1 C1 0.75(15) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_to15a_2021
_database_code_depnum_ccdc_archive 'CCDC 2224272'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2022-11-20
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic



#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
phenanthridin-6(5H)-one -- perfluorophenol
;
_chemical_formula_moiety         '2(C13 H8.83 N O), C6 H F5 O'
_chemical_formula_sum            'C32 H18.67 F5 N2 O3'
_chemical_formula_weight         574.15
_chemical_absolute_configuration unk
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'

_cell_length_a                   8.6150(8)
_cell_length_b                   15.9915(14)
_cell_length_c                   9.1239(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.072(8)
_cell_angle_gamma                90
_cell_volume                     1224.40(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2750
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      21.60

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             587


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_number            12715
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.459
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             2153
_reflns_number_gt                1807
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0827P)²+0.8267P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2153
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.3167(3) 0.07972(15) 0.2351(3) 0.0412(6) Uani 1 1 d . . . . .
C2 C 0.2704(3) 0.15913(17) 0.1837(3) 0.0504(6) Uani 1 1 d . . . . .
H2 H 0.305873 0.181756 0.100694 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1739(3) 0.20497(16) 0.2523(3) 0.0556(7) Uani 1 1 d . . . . .
H3 H 0.143052 0.25984 0.217572 0.067 Uiso 1 1 calc R U . . .
C4 C 0.1192(3) 0.17120(16) 0.3750(3) 0.0509(7) Uani 1 1 d . . . . .
H4 H 0.051252 0.203133 0.422133 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1652(3) 0.09167(15) 0.4260(3) 0.0414(6) Uani 1 1 d . . . . .
H5 H 0.128899 0.069154 0.508581 0.05 Uiso 1 1 calc R U . . .
C6 C 0.2654(2) 0.04364(14) 0.3566(2) 0.0360(5) Uani 1 1 d . . . . .
C7 C 0.3160(2) -0.04115(14) 0.4008(3) 0.0363(5) Uani 1 1 d . . . . .
C8 C 0.2705(3) -0.08377(15) 0.5193(3) 0.0414(6) Uani 1 1 d . . . . .
H8 H 0.205311 -0.056076 0.575242 0.05 Uiso 1 1 calc R U . . .
C9 C 0.3187(3) -0.16514(16) 0.5562(3) 0.0487(6) Uani 1 1 d . . . . .
H9 H 0.286907 -0.192094 0.637446 0.058 Uiso 1 1 calc R U . . .
C10 C 0.4125(3) -0.20783(16) 0.4762(3) 0.0514(7) Uani 1 1 d . . . . .
H10 H 0.443303 -0.264057 0.500886 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4604(3) -0.16794(16) 0.3613(3) 0.0496(7) Uani 1 1 d . . . . .
H11 H 0.526178 -0.196605 0.307103 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4136(3) -0.08508(16) 0.3221(3) 0.0408(6) Uani 1 1 d . . . . .
C13 C 0.4643(3) -0.04515(17) 0.1979(3) 0.0469(6) Uani 0.833(5) 1 d . . P . .
C13A C 0.4165(2) 0.03188(14) 0.1618(2) 0.0446(5) Uani 0.167(5) 1 d . . P . .
C14 C 0.0503(3) -0.07946(14) 0.0455(3) 0.0408(6) Uani 1 1 d . . . . .
C15 C -0.0579(3) -0.03938(16) 0.1127(3) 0.0413(6) Uani 1 1 d . . . . .
C16 C -0.1064(3) 0.04002(15) 0.0662(3) 0.0402(6) Uani 1 1 d . . . . .
F1 F 0.09916(17) -0.15737(9) 0.08754(18) 0.0509(4) Uani 1 1 d . . . . .
F2 F -0.1123(12) -0.0805(6) 0.2207(12) 0.039(2) Uani 0.5 1 d . . P . .
F3 F -0.21269(16) 0.07985(9) 0.13033(17) 0.0514(4) Uani 1 1 d . . . . .
N1 N 0.4165(2) 0.03188(14) 0.1618(2) 0.0446(5) Uani 0.833(5) 1 d . . P . .
H1 H 0.449791 0.056437 0.085507 0.054 Uiso 0.833(5) 1 d R U P . .
N1A N 0.4643(3) -0.04515(17) 0.1979(3) 0.0469(6) Uani 0.167(5) 1 d . . P . .
O1 O 0.5537(3) -0.08616(13) 0.1260(2) 0.0474(7) Uani 0.833(5) 1 d . . P . .
O1A O 0.4213(11) 0.0942(6) 0.0350(10) 0.038(3) Uiso 0.167(5) 1 d . . P . .
O2 O -0.109(2) -0.0753(10) 0.2279(19) 0.074(5) Uani 0.5 1 d . . P . .
H2A H -0.216529 -0.077078 0.204369 0.12(4) Uiso 0.5 1 d R . P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.381(4) . ?
C1 C6 1.407(3) . ?
C1 N1 1.426(3) . ?
C2 C3 1.362(4) . ?
C2 H2 0.95 . ?
C3 C4 1.416(4) . ?
C3 H3 0.95 . ?
C4 C5 1.381(4) . ?
C4 H4 0.95 . ?
C5 C6 1.408(3) . ?
C5 H5 0.95 . ?
C6 C7 1.453(3) . ?
C7 C8 1.406(3) . ?
C7 C12 1.411(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.95 . ?
C9 C10 1.385(4) . ?
C9 H9 0.95 . ?
C10 C11 1.368(4) . ?
C10 H10 0.95 . ?
C11 C12 1.407(4) . ?
C11 H11 0.95 . ?
C12 C13 1.451(3) . ?
C13 O1 1.297(3) . ?
C13 N1 1.317(3) . ?
C14 F1 1.343(3) . ?
C14 C16 1.376(3) 3 ?
C14 C15 1.384(3) . ?
C15 F2 1.353(11) . ?
C15 O2 1.357(16) . ?
C15 C16 1.374(4) . ?
C16 F3 1.352(3) . ?
F2 H2A 0.8776 . ?
N1 O1A 1.534(9) . ?
N1 H1 0.9002 . ?
O1 O1A 1.538(9) 3_655 ?
O1A H1 0.7655 . ?
O2 H2A 0.9 . ?

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
C2 C1 C6 121.8(2) . . ?
C2 C1 N1 119.5(2) . . ?
C6 C1 N1 118.7(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.7(2) . . ?
C1 C6 C7 118.2(2) . . ?
C5 C6 C7 124.1(2) . . ?
C8 C7 C12 116.9(2) . . ?
C8 C7 C6 123.2(2) . . ?
C12 C7 C6 120.0(2) . . ?
C9 C8 C7 121.5(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 120.6(2) . . ?
C11 C12 C13 119.6(2) . . ?
C7 C12 C13 119.9(2) . . ?
O1 C13 N1 122.3(2) . . ?
O1 C13 C12 119.4(2) . . ?
N1 C13 C12 118.4(2) . . ?
F1 C14 C16 119.8(2) . 3 ?
F1 C14 C15 120.1(2) . . ?
C16 C14 C15 120.1(2) 3 . ?
F2 C15 O2 4.5(12) . . ?
F2 C15 C16 122.8(4) . . ?
O2 C15 C16 120.0(7) . . ?
F2 C15 C14 118.5(4) . . ?
O2 C15 C14 121.2(7) . . ?
C16 C15 C14 118.7(2) . . ?
F3 C16 C15 119.4(2) . . ?
F3 C16 C14 119.4(2) . 3 ?
C15 C16 C14 121.3(2) . 3 ?
C15 F2 H2A 110.9 . . ?
C13 N1 C1 124.9(2) . . ?
C13 N1 O1A 137.4(4) . . ?
C1 N1 O1A 97.3(4) . . ?
C13 N1 H1 117.8 . . ?
C1 N1 H1 117.4 . . ?
O1A N1 H1 21 . . ?
C13 O1 O1A 138.8(4) . 3_655 ?
N1 O1A O1 134.4(6) . 3_655 ?
N1 O1A H1 25 . . ?
O1 O1A H1 114.5 3_655 . ?
C15 O2 H2A 109 . . ?

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
C6 C1 C2 C3 0.7(4) . . . . ?
N1 C1 C2 C3 179.4(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
N1 C1 C6 C5 -179.21(19) . . . . ?
C2 C1 C6 C7 178.3(2) . . . . ?
N1 C1 C6 C7 -0.5(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
C1 C6 C7 C8 -179.2(2) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C1 C6 C7 C12 -0.2(3) . . . . ?
C5 C6 C7 C12 178.5(2) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C6 C7 C8 C9 178.7(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C7 0.0(4) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C8 C7 C12 C11 0.6(3) . . . . ?
C6 C7 C12 C11 -178.5(2) . . . . ?
C8 C7 C12 C13 179.6(2) . . . . ?
C6 C7 C12 C13 0.5(3) . . . . ?
C11 C12 C13 O1 -0.8(3) . . . . ?
C7 C12 C13 O1 -179.8(2) . . . . ?
C11 C12 C13 N1 178.8(2) . . . . ?
C7 C12 C13 N1 -0.2(3) . . . . ?
F1 C14 C15 F2 -0.1(6) . . . . ?
C16 C14 C15 F2 179.1(6) 3 . . . ?
F1 C14 C15 O2 4.0(10) . . . . ?
C16 C14 C15 O2 -176.9(9) 3 . . . ?
F1 C14 C15 C16 -179.5(2) . . . . ?
C16 C14 C15 C16 -0.4(4) 3 . . . ?
F2 C15 C16 F3 0.3(7) . . . . ?
O2 C15 C16 F3 -3.8(9) . . . . ?
C14 C15 C16 F3 179.7(2) . . . . ?
F2 C15 C16 C14 -179.0(6) . . . 3 ?
O2 C15 C16 C14 176.9(9) . . . 3 ?
C14 C15 C16 C14 0.4(4) . . . 3 ?
O1 C13 N1 C1 179.1(2) . . . . ?
C12 C13 N1 C1 -0.5(3) . . . . ?
O1 C13 N1 O1A 8.3(7) . . . . ?
C12 C13 N1 O1A -171.3(5) . . . . ?
C2 C1 N1 C13 -177.9(2) . . . . ?
C6 C1 N1 C13 0.8(3) . . . . ?
C2 C1 N1 O1A -4.2(4) . . . . ?
C6 C1 N1 O1A 174.6(4) . . . . ?
N1 C13 O1 O1A -34.3(7) . . . 3_655 ?
C12 C13 O1 O1A 145.4(6) . . . 3_655 ?
C13 N1 O1A O1 19.0(12) . . . 3_655 ?
C1 N1 O1A O1 -153.4(8) . . . 3_655 ?

_vrf_PLAT230_to15a_2021          
;
PROBLEM:  Hirshfeld Test Diff for C2 --C3 . 9.5 s.u.
RESPONSE: The disorder model is limited only to carbon C13 and nitrogen N1 atoms 
and does not include carbon atoms in rings, which creates distoreted elipsoids 
carbon at C2-C3.
;
# END of CIF

####################################################################### 
# 
# 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_to9_2022
_database_code_depnum_ccdc_archive 'CCDC 2224269'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-03 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2023-02-03
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
benzo[cd]indol-2(1H)-one -- perfluorophenol  
;

_chemical_formula_moiety         'C11 H7 N O, C6 H F5 O '
_chemical_formula_sum            'C17 H8 F5 N O2'
_chemical_formula_weight         353.24
_chemical_absolute_configuration unk
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0463(9)
_cell_length_b                   11.6765(12)
_cell_length_c                   13.7306(14)
_cell_angle_alpha                98.454(8)
_cell_angle_beta                 97.155(8)
_cell_angle_gamma                100.557(8)
_cell_volume                     1393.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    13839
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      29.40
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_number            22130
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.318
_diffrn_reflns_theta_max         29.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             7482
_reflns_number_gt                6231
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²+2.1247P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7482
_refine_ls_number_parameters     515
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1837
_refine_ls_wR_factor_gt          0.177
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.076

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.6706(3) 0.94382(19) 0.58266(17) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.7721(2) 0.91442(18) 0.66520(16) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.8909(3) 0.8554(2) 0.67140(19) 0.0268(4) Uani 1 1 d . . . . .
H3 H 0.92645 0.822611 0.61348 0.032 Uiso 1 1 calc R U . . .
C4 C 0.9577(3) 0.8461(2) 0.7686(2) 0.0286(5) Uani 1 1 d . . . . .
H4 H 1.039942 0.806083 0.774747 0.034 Uiso 1 1 calc R U . . .
C5 C 0.9087(3) 0.8923(2) 0.85444(19) 0.0282(5) Uani 1 1 d . . . . .
H5 H 0.957226 0.883211 0.917495 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7865(2) 0.95317(19) 0.84928(16) 0.0231(4) Uani 1 1 d . . . . .
C7 C 0.7236(2) 0.96028(18) 0.75281(15) 0.0201(4) Uani 1 1 d . . . . .
C8 C 0.6000(2) 1.01413(18) 0.73094(16) 0.0210(4) Uani 1 1 d . . . . .
C9 C 0.5339(3) 1.0651(2) 0.80588(17) 0.0256(4) Uani 1 1 d . . . . .
H9 H 0.449897 1.101793 0.792519 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5982(3) 1.0601(2) 0.90549(18) 0.0280(5) Uani 1 1 d . . . . .
H10 H 0.555332 1.095546 0.959007 0.034 Uiso 1 1 calc R U . . .
C11 C 0.7181(3) 1.0069(2) 0.92790(17) 0.0278(5) Uani 1 1 d . . . . .
H11 H 0.755803 1.005769 0.995409 0.033 Uiso 1 1 calc R U . . .
C12 C 0.9556(4) 0.4814(4) 0.3476(2) 0.0251(6) Uani 0.907(6) 1 d D . P A 1
C13 C 0.8901(2) 0.48342(19) 0.24360(17) 0.0235(4) Uani 1 1 d D . . . .
C14 C 0.9231(3) 0.4409(2) 0.15109(19) 0.0285(5) Uani 1 1 d . . . . .
H14 H 1.003048 0.399075 0.144603 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8328(3) 0.4622(2) 0.06658(18) 0.0306(5) Uani 1 1 d . . . . .
H15 H 0.853328 0.433256 0.002341 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7162(3) 0.5230(2) 0.07321(18) 0.0283(5) Uani 1 1 d . . . . .
H16 H 0.659589 0.535677 0.014092 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6802(2) 0.56681(19) 0.16707(16) 0.0224(4) Uani 1 1 d . . . . .
C18 C 0.7704(2) 0.54432(17) 0.24934(16) 0.0201(4) Uani 1 1 d . . . . .
C19 C 0.7540(3) 0.57907(19) 0.34864(17) 0.0242(4) Uani 1 1 d D . . . .
C20 C 0.6439(3) 0.6389(2) 0.37110(19) 0.0291(5) Uani 1 1 d . . . . .
H20 H 0.630573 0.663006 0.438042 0.035 Uiso 1 1 calc R U . . .
C21 C 0.5492(3) 0.6639(2) 0.2889(2) 0.0309(5) Uani 1 1 d . . . . .
H21 H 0.471443 0.705755 0.302668 0.037 Uiso 1 1 calc R U . . .
C22 C 0.5644(3) 0.6305(2) 0.19047(19) 0.0279(5) Uani 1 1 d . . . . .
H22 H 0.498416 0.64964 0.138629 0.033 Uiso 1 1 calc R U . . .
C23 C 0.9011(2) 0.86476(19) 0.29364(17) 0.0243(4) Uani 1 1 d . . . . .
C24 C 1.0085(3) 0.8266(2) 0.35584(17) 0.0262(4) Uani 1 1 d . . . . .
C25 C 1.1108(3) 0.7640(2) 0.31886(18) 0.0264(4) Uani 1 1 d . . . . .
C26 C 1.1082(2) 0.73800(19) 0.21728(18) 0.0250(4) Uani 1 1 d . . . . .
C27 C 1.0038(3) 0.77536(19) 0.15402(16) 0.0244(4) Uani 1 1 d . . . . .
C28 C 0.9014(2) 0.83764(19) 0.19169(17) 0.0237(4) Uani 1 1 d . . . . .
C29 C 0.5731(3) 0.6424(2) 0.6756(2) 0.0222(5) Uani 0.897(4) 1 d D . P B 1
C30 C 0.4522(3) 0.6900(2) 0.6379(2) 0.0230(5) Uani 0.897(4) 1 d D . P B 1
C31 C 0.3693(4) 0.7466(3) 0.69984(19) 0.0222(6) Uani 0.897(4) 1 d D . P B 1
C32 C 0.4051(5) 0.7582(6) 0.8023(2) 0.0218(10) Uani 0.897(4) 1 d D . P B 1
C33 C 0.5230(5) 0.7104(5) 0.8410(3) 0.0246(7) Uani 0.897(4) 1 d D U P B 1
C34 C 0.6057(3) 0.6534(2) 0.7785(3) 0.0232(5) Uani 0.897(4) 1 d D . P B 1
F1 F 1.01358(19) 0.85173(15) 0.45527(11) 0.0370(4) Uani 1 1 d . . . . .
F2 F 1.21223(18) 0.72805(15) 0.38077(12) 0.0376(4) Uani 1 1 d . . . . .
F3 F 1.20610(17) 0.67596(13) 0.18056(13) 0.0359(4) Uani 1 1 d . . . . .
F4 F 1.00022(18) 0.74971(14) 0.05505(11) 0.0339(3) Uani 1 1 d . . . . .
F5 F 0.80028(17) 0.87136(14) 0.12805(11) 0.0336(3) Uani 1 1 d . . . . .
F6 F 0.41619(19) 0.68165(16) 0.53914(12) 0.0325(4) Uani 0.897(4) 1 d D . P B 1
F7 F 0.2543(2) 0.79201(19) 0.66102(14) 0.0313(4) Uani 0.897(4) 1 d D . P B 1
F8 F 0.3228(5) 0.8120(4) 0.8628(3) 0.0293(7) Uani 0.897(4) 1 d D . P B 1
F9 F 0.5589(3) 0.7194(2) 0.94050(17) 0.0322(5) Uani 0.897(4) 1 d D . P B 1
F10 F 0.72009(17) 0.60715(14) 0.81779(14) 0.0297(4) Uani 0.897(4) 1 d D . P B 1
N1 N 0.5699(2) 1.00206(17) 0.62648(14) 0.0238(4) Uani 1 1 d . . . . .
H1 H 0.496677 1.028149 0.593639 0.029 Uiso 1 1 calc R U . . .
N2 N 0.8687(4) 0.5379(4) 0.4065(3) 0.0246(7) Uani 0.907(6) 1 d D . P A 1
H2 H 0.882539 0.547489 0.471976 0.03 Uiso 0.907(6) 1 calc R U P A 1
O2 O 1.0630(2) 0.43823(16) 0.37866(14) 0.0265(5) Uani 0.907(6) 1 d D . P A 1
O1 O 0.6709(2) 0.92250(16) 0.49146(12) 0.0290(4) Uani 1 1 d . . . . .
O3 O 0.8017(2) 0.92797(16) 0.32677(14) 0.0306(4) Uani 1 1 d . . . . .
H3A H 0.793246 0.919905 0.385743 0.046 Uiso 1 1 calc R U . . .
O4 O 0.6497(2) 0.58852(18) 0.61061(14) 0.0280(5) Uani 0.897(4) 1 d D . P B 1
H4A H 0.740268 0.595204 0.637447 0.042 Uiso 0.897(4) 1 calc R U P B 1
C31A C 0.399(4) 0.730(4) 0.7006(16) 0.038(13) Uiso 0.103(4) 1 d D . P B 2
F7A F 0.289(2) 0.7672(18) 0.6475(15) 0.038(5) Uiso 0.103(4) 1 d D . P B 2
C32A C 0.398(4) 0.738(4) 0.8028(15) 0.025(13) Uiso 0.103(4) 1 d D . P B 2
F8A F 0.315(5) 0.811(4) 0.845(2) 0.028(8) Uiso 0.103(4) 1 d D . P B 2
C33A C 0.521(4) 0.714(4) 0.8611(15) 0.012(4) Uiso 0.103(4) 1 d D U P B 2
F9A F 0.534(3) 0.734(2) 0.9607(14) 0.031(6) Uiso 0.103(4) 1 d D . P B 2
C34A C 0.619(3) 0.653(3) 0.8167(14) 0.032(7) Uiso 0.103(4) 1 d D . P B 2
F10A F 0.7274(16) 0.6199(13) 0.8755(13) 0.032(4) Uiso 0.103(4) 1 d D . P B 2
C29A C 0.613(2) 0.6337(18) 0.7149(14) 0.022(5) Uiso 0.103(4) 1 d D . P B 2
O4A O 0.7077(19) 0.5718(14) 0.6709(13) 0.030(4) Uiso 0.103(4) 1 d D . P B 2
H4AA H 0.656026 0.510795 0.632976 0.045 Uiso 0.103(4) 1 calc R U P B 2
C30A C 0.500(2) 0.6704(15) 0.6582(11) 0.011(4) Uiso 0.103(4) 1 d D . P B 2
F6A F 0.4825(19) 0.6488(13) 0.5583(10) 0.032(4) Uiso 0.103(4) 1 d D . P B 2
N2A N 0.927(4) 0.492(3) 0.3543(14) 0.02 Uiso 0.093(6) 1 d D U P A 2
H2A H 0.996185 0.453052 0.375538 0.024 Uiso 0.093(6) 1 calc R U P A 2
C12A C 0.864(5) 0.552(6) 0.4256(14) 0.037(16) Uiso 0.093(6) 1 d D . P A 2
O2A O 0.8375(19) 0.5758(15) 0.5122(12) 0.025(5) Uiso 0.093(6) 1 d D . P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.241(3) . ?
C1 N1 1.378(3) . ?
C1 C2 1.488(3) . ?
C2 C3 1.379(3) . ?
C2 C7 1.398(3) . ?
C3 C4 1.423(3) . ?
C3 H3 0.95 . ?
C4 C5 1.381(4) . ?
C4 H4 0.95 . ?
C5 C6 1.420(3) . ?
C5 H5 0.95 . ?
C6 C7 1.395(3) . ?
C6 C11 1.432(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.369(3) . ?
C8 N1 1.407(3) . ?
C9 C10 1.432(3) . ?
C9 H9 0.95 . ?
C10 C11 1.369(3) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 O2 1.234(3) . ?
C12 N2 1.378(5) . ?
C12 C13 1.481(4) . ?
C13 C14 1.383(3) . ?
C13 C18 1.405(3) . ?
C13 N2A 1.500(19) . ?
C14 C15 1.413(4) . ?
C14 H14 0.95 . ?
C15 C16 1.381(4) . ?
C15 H15 0.95 . ?
C16 C17 1.414(3) . ?
C16 H16 0.95 . ?
C17 C18 1.395(3) . ?
C17 C22 1.433(3) . ?
C18 C19 1.398(3) . ?
C19 C20 1.358(3) . ?
C19 N2 1.424(3) . ?
C19 C12A 1.47(2) . ?
C20 C21 1.428(4) . ?
C20 H20 0.95 . ?
C21 C22 1.381(4) . ?
C21 H21 0.95 . ?
C22 H22 0.95 . ?
C23 O3 1.344(3) . ?
C23 C28 1.390(3) . ?
C23 C24 1.391(3) . ?
C24 F1 1.347(3) . ?
C24 C25 1.380(3) . ?
C25 F2 1.339(3) . ?
C25 C26 1.379(3) . ?
C26 F3 1.343(2) . ?
C26 C27 1.377(3) . ?
C27 F4 1.343(3) . ?
C27 C28 1.382(3) . ?
C28 F5 1.338(2) . ?
C29 O4 1.350(3) . ?
C29 C34 1.388(4) . ?
C29 C30 1.393(3) . ?
C30 F6 1.339(3) . ?
C30 C31 1.378(4) . ?
C31 F7 1.340(4) . ?
C31 C32 1.384(4) . ?
C32 F8 1.346(3) . ?
C32 C33 1.376(4) . ?
C33 F9 1.348(4) . ?
C33 C34 1.383(4) . ?
C34 F10 1.344(3) . ?
N1 H1 0.88 . ?
N2 H2 0.88 . ?
O3 H3A 0.84 . ?
O4 H4A 0.84 . ?
C31A F7A 1.335(17) . ?
C31A C30A 1.377(17) . ?
C31A C32A 1.394(17) . ?
C32A F8A 1.352(18) . ?
C32A C33A 1.382(17) . ?
C33A F9A 1.340(16) . ?
C33A C34A 1.377(16) . ?
C34A F10A 1.341(16) . ?
C34A C29A 1.375(17) . ?
C29A O4A 1.360(16) . ?
C29A C30A 1.377(16) . ?
O4A H4AA 0.84 . ?
C30A F6A 1.341(15) . ?
N2A C12A 1.366(18) . ?
N2A H2A 0.88 . ?
C12A O2A 1.244(19) . ?

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
O1 C1 N1 124.2(2) . . ?
O1 C1 C2 129.2(2) . . ?
N1 C1 C2 106.51(18) . . ?
C3 C2 C7 119.2(2) . . ?
C3 C2 C1 135.3(2) . . ?
C7 C2 C1 105.48(18) . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 123.2(2) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 114.6(2) . . ?
C7 C6 C11 115.7(2) . . ?
C5 C6 C11 129.7(2) . . ?
C6 C7 C2 125.6(2) . . ?
C6 C7 C8 123.8(2) . . ?
C2 C7 C8 110.60(19) . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 N1 132.7(2) . . ?
C7 C8 N1 106.68(18) . . ?
C8 C9 C10 116.4(2) . . ?
C8 C9 H9 121.8 . . ?
C10 C9 H9 121.8 . . ?
C11 C10 C9 123.6(2) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C10 C11 C6 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
O2 C12 N2 125.2(3) . . ?
O2 C12 C13 129.4(3) . . ?
N2 C12 C13 105.5(2) . . ?
C14 C13 C18 119.3(2) . . ?
C14 C13 C12 134.3(2) . . ?
C18 C13 C12 106.5(2) . . ?
C14 C13 N2A 146.4(11) . . ?
C18 C13 N2A 94.3(11) . . ?
C13 C14 C15 117.3(2) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C16 C15 C14 122.9(2) . . ?
C16 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 115.3(2) . . ?
C18 C17 C22 115.0(2) . . ?
C16 C17 C22 129.7(2) . . ?
C17 C18 C19 124.8(2) . . ?
C17 C18 C13 124.5(2) . . ?
C19 C18 C13 110.70(19) . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 N2 134.1(3) . . ?
C18 C19 N2 105.5(3) . . ?
C20 C19 C12A 122.5(10) . . ?
C18 C19 C12A 117.1(9) . . ?
C19 C20 C21 116.5(2) . . ?
C19 C20 H20 121.7 . . ?
C21 C20 H20 121.7 . . ?
C22 C21 C20 123.7(2) . . ?
C22 C21 H21 118.1 . . ?
C20 C21 H21 118.1 . . ?
C21 C22 C17 119.6(2) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
O3 C23 C28 119.1(2) . . ?
O3 C23 C24 123.8(2) . . ?
C28 C23 C24 117.0(2) . . ?
F1 C24 C25 118.8(2) . . ?
F1 C24 C23 119.2(2) . . ?
C25 C24 C23 122.0(2) . . ?
F2 C25 C26 119.8(2) . . ?
F2 C25 C24 120.5(2) . . ?
C26 C25 C24 119.7(2) . . ?
F3 C26 C27 120.4(2) . . ?
F3 C26 C25 120.1(2) . . ?
C27 C26 C25 119.5(2) . . ?
F4 C27 C26 119.7(2) . . ?
F4 C27 C28 119.9(2) . . ?
C26 C27 C28 120.4(2) . . ?
F5 C28 C27 118.9(2) . . ?
F5 C28 C23 119.8(2) . . ?
C27 C28 C23 121.3(2) . . ?
O4 C29 C34 124.5(2) . . ?
O4 C29 C30 118.4(2) . . ?
C34 C29 C30 117.1(2) . . ?
F6 C30 C31 119.0(3) . . ?
F6 C30 C29 119.4(2) . . ?
C31 C30 C29 121.6(3) . . ?
F7 C31 C30 120.0(2) . . ?
F7 C31 C32 119.6(3) . . ?
C30 C31 C32 120.4(3) . . ?
F8 C32 C33 120.7(3) . . ?
F8 C32 C31 120.4(4) . . ?
C33 C32 C31 118.9(3) . . ?
F9 C33 C32 120.0(3) . . ?
F9 C33 C34 119.6(3) . . ?
C32 C33 C34 120.5(3) . . ?
F10 C34 C33 119.5(3) . . ?
F10 C34 C29 118.9(2) . . ?
C33 C34 C29 121.6(2) . . ?
C1 N1 C8 110.72(18) . . ?
C1 N1 H1 124.6 . . ?
C8 N1 H1 124.6 . . ?
C12 N2 C19 111.9(3) . . ?
C12 N2 H2 124.1 . . ?
C19 N2 H2 124.1 . . ?
C23 O3 H3A 109.5 . . ?
C29 O4 H4A 109.5 . . ?
F7A C31A C30A 123.3(18) . . ?
F7A C31A C32A 117.6(17) . . ?
C30A C31A C32A 118.5(17) . . ?
F8A C32A C33A 119(2) . . ?
F8A C32A C31A 117(2) . . ?
C33A C32A C31A 119(2) . . ?
F9A C33A C34A 119.3(16) . . ?
F9A C33A C32A 120.5(17) . . ?
C34A C33A C32A 119.6(17) . . ?
F10A C34A C29A 120.4(16) . . ?
F10A C34A C33A 118.3(16) . . ?
C29A C34A C33A 121.1(15) . . ?
O4A C29A C34A 121.2(16) . . ?
O4A C29A C30A 120.7(15) . . ?
C34A C29A C30A 117.9(14) . . ?
C29A O4A H4AA 109.5 . . ?
F6A C30A C31A 116.8(16) . . ?
F6A C30A C29A 121.2(14) . . ?
C31A C30A C29A 122.0(14) . . ?
C12A N2A C13 127(2) . . ?
C12A N2A H2A 116.6 . . ?
C13 N2A H2A 116.6 . . ?
O2A C12A N2A 152(3) . . ?
O2A C12A C19 115(2) . . ?
N2A C12A C19 90.8(18) . . ?

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
O1 C1 C2 C3 -1.9(4) . . . . ?
N1 C1 C2 C3 178.1(2) . . . . ?
O1 C1 C2 C7 179.1(2) . . . . ?
N1 C1 C2 C7 -0.9(2) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 -179.3(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C11 179.8(2) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C11 C6 C7 C2 179.9(2) . . . . ?
C5 C6 C7 C8 178.5(2) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
C3 C2 C7 C6 0.7(3) . . . . ?
C1 C2 C7 C6 179.9(2) . . . . ?
C3 C2 C7 C8 -178.55(19) . . . . ?
C1 C2 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C2 C7 C8 C9 179.9(2) . . . . ?
C6 C7 C8 N1 -179.37(19) . . . . ?
C2 C7 C8 N1 -0.1(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
N1 C8 C9 C10 -179.8(2) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C7 C6 C11 C10 0.4(3) . . . . ?
C5 C6 C11 C10 -179.0(2) . . . . ?
O2 C12 C13 C14 0.1(6) . . . . ?
N2 C12 C13 C14 -179.0(3) . . . . ?
O2 C12 C13 C18 -179.5(4) . . . . ?
N2 C12 C13 C18 1.4(4) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C12 C13 C14 C15 -179.3(3) . . . . ?
N2A C13 C14 C15 177(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C17 C22 -179.4(2) . . . . ?
C16 C17 C18 C19 -179.7(2) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C22 C17 C18 C13 180.0(2) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C12 C13 C18 C17 179.1(2) . . . . ?
N2A C13 C18 C17 -178.8(15) . . . . ?
C14 C13 C18 C19 179.4(2) . . . . ?
C12 C13 C18 C19 -0.9(3) . . . . ?
N2A C13 C18 C19 1.1(15) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C13 C18 C19 C20 -179.7(2) . . . . ?
C17 C18 C19 N2 -180.0(3) . . . . ?
C13 C18 C19 N2 0.1(3) . . . . ?
C17 C18 C19 C12A -177(3) . . . . ?
C13 C18 C19 C12A 3(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
N2 C19 C20 C21 180.0(3) . . . . ?
C12A C19 C20 C21 177(3) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C17 0.2(4) . . . . ?
C18 C17 C22 C21 -0.3(3) . . . . ?
C16 C17 C22 C21 179.4(2) . . . . ?
O3 C23 C24 F1 1.2(3) . . . . ?
C28 C23 C24 F1 179.4(2) . . . . ?
O3 C23 C24 C25 -178.6(2) . . . . ?
C28 C23 C24 C25 -0.4(3) . . . . ?
F1 C24 C25 F2 0.6(3) . . . . ?
C23 C24 C25 F2 -179.6(2) . . . . ?
F1 C24 C25 C26 -179.6(2) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
F2 C25 C26 F3 0.5(3) . . . . ?
C24 C25 C26 F3 -179.2(2) . . . . ?
F2 C25 C26 C27 -179.9(2) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
F3 C26 C27 F4 -0.1(3) . . . . ?
C25 C26 C27 F4 -179.7(2) . . . . ?
F3 C26 C27 C28 179.0(2) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
F4 C27 C28 F5 -0.1(3) . . . . ?
C26 C27 C28 F5 -179.2(2) . . . . ?
F4 C27 C28 C23 179.4(2) . . . . ?
C26 C27 C28 C23 0.3(3) . . . . ?
O3 C23 C28 F5 -2.1(3) . . . . ?
C24 C23 C28 F5 179.6(2) . . . . ?
O3 C23 C28 C27 178.4(2) . . . . ?
C24 C23 C28 C27 0.1(3) . . . . ?
O4 C29 C30 F6 -0.3(4) . . . . ?
C34 C29 C30 F6 -180.0(2) . . . . ?
O4 C29 C30 C31 -179.8(3) . . . . ?
C34 C29 C30 C31 0.6(4) . . . . ?
F6 C30 C31 F7 0.1(4) . . . . ?
C29 C30 C31 F7 179.6(3) . . . . ?
F6 C30 C31 C32 -179.1(4) . . . . ?
C29 C30 C31 C32 0.4(5) . . . . ?
F7 C31 C32 F8 1.7(8) . . . . ?
C30 C31 C32 F8 -179.1(5) . . . . ?
F7 C31 C32 C33 179.6(4) . . . . ?
C30 C31 C32 C33 -1.2(7) . . . . ?
F8 C32 C33 F9 -1.4(9) . . . . ?
C31 C32 C33 F9 -179.3(5) . . . . ?
F8 C32 C33 C34 178.9(5) . . . . ?
C31 C32 C33 C34 1.0(8) . . . . ?
F9 C33 C34 F10 0.4(6) . . . . ?
C32 C33 C34 F10 -179.9(4) . . . . ?
F9 C33 C34 C29 -179.8(3) . . . . ?
C32 C33 C34 C29 -0.1(7) . . . . ?
O4 C29 C34 F10 -0.5(4) . . . . ?
C30 C29 C34 F10 179.1(2) . . . . ?
O4 C29 C34 C33 179.7(3) . . . . ?
C30 C29 C34 C33 -0.7(4) . . . . ?
O1 C1 N1 C8 -179.1(2) . . . . ?
C2 C1 N1 C8 0.9(2) . . . . ?
C9 C8 N1 C1 179.4(2) . . . . ?
C7 C8 N1 C1 -0.5(2) . . . . ?
O2 C12 N2 C19 179.5(4) . . . . ?
C13 C12 N2 C19 -1.4(4) . . . . ?
C20 C19 N2 C12 -179.4(3) . . . . ?
C18 C19 N2 C12 0.9(4) . . . . ?
F7A C31A C32A F8A -18(7) . . . . ?
C30A C31A C32A F8A 171(4) . . . . ?
F7A C31A C32A C33A -172(4) . . . . ?
C30A C31A C32A C33A 16(7) . . . . ?
F8A C32A C33A F9A 18(7) . . . . ?
C31A C32A C33A F9A 172(4) . . . . ?
F8A C32A C33A C34A -171(5) . . . . ?
C31A C32A C33A C34A -17(7) . . . . ?
F9A C33A C34A F10A -2(6) . . . . ?
C32A C33A C34A F10A -173(4) . . . . ?
F9A C33A C34A C29A -178(3) . . . . ?
C32A C33A C34A C29A 11(6) . . . . ?
F10A C34A C29A O4A 6(4) . . . . ?
C33A C34A C29A O4A -179(3) . . . . ?
F10A C34A C29A C30A -180(2) . . . . ?
C33A C34A C29A C30A -4(5) . . . . ?
F7A C31A C30A F6A -1(5) . . . . ?
C32A C31A C30A F6A 170(4) . . . . ?
F7A C31A C30A C29A 180(3) . . . . ?
C32A C31A C30A C29A -9(6) . . . . ?
O4A C29A C30A F6A -2(3) . . . . ?
C34A C29A C30A F6A -177(2) . . . . ?
O4A C29A C30A C31A 178(3) . . . . ?
C34A C29A C30A C31A 3(4) . . . . ?
C14 C13 N2A C12A 177(4) . . . . ?
C18 C13 N2A C12A -6(5) . . . . ?
C13 N2A C12A O2A 165(10) . . . . ?
C13 N2A C12A C19 7(6) . . . . ?
C20 C19 C12A O2A 9(7) . . . . ?
C18 C19 C12A O2A -174(4) . . . . ?
C20 C19 C12A N2A 177(2) . . . . ?
C18 C19 C12A N2A -5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.88 2.02 2.896(2) 175.2 2_676 yes
N2^a H2^a O2^a 0.88 2.02 2.899(4) 173.2 2_766 yes
O3 H3A O1 0.84 1.93 2.683(2) 148.3 . yes

# END of CIF
