#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:20:42 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246246.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246246
loop_
_publ_author_name
'Alfuth, Jan'
'Kazimierczuk, Katarzyna'
'Połoński, Tadeusz'
'Olszewska, Teresa'
_publ_section_title
;
 Self-assembly of secondary aryl amides in cocrystals with perfluoroaryl
 coformers: structural analysis and synthon preferences
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1403
_journal_page_last               1410
_journal_paper_doi               10.1039/D2CE01710E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         ' C13 H9 N O, C7 H F5 O2'
_chemical_formula_sum            'C20 H10 F5 N O3'
_chemical_formula_weight         407.29
_chemical_name_systematic
;
phenanthridin-6(5H)-one -- perfluorobenzoic acid
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2022-12-21
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-02-01 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                93.005(13)
_cell_angle_beta                 102.411(13)
_cell_angle_gamma                92.991(13)
_cell_formula_units_Z            2
_cell_length_a                   7.2840(13)
_cell_length_b                   8.5719(13)
_cell_length_c                   13.363(2)
_cell_measurement_reflns_used    2109
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.38
_cell_measurement_theta_min      2.43
_cell_measurement_wavelength     0.71073
_cell_volume                     812.0(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8160
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.936
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.15
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1211P)²+0.4701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.1907
_reflns_Friedel_coverage         0
_reflns_number_gt                2559
_reflns_number_total             3008
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01710e2.cif
_cod_data_source_block           to3_2019
_cod_depositor_comments
'Adding full bibliography for 7246246--7246251.cif.'
_cod_database_code               7246246
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . . . . .
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_
_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_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_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) . . . . ?
