#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/71/7217146.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_7217146
loop_
_publ_author_name
'Ojala, William H.'
'Balidemaj, Barjeta'
'Johnson, Jenna A.'
'Larson, Sarah N.'
'Ojala, Charles R.'
_publ_section_title
;
 Molecular symmetry and fluorine-containing supramolecular synthons as
 structure-differentiating agents in some “bridge-flipped”
 isomeric bis-benzylideneanilines
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              7226
_journal_paper_doi               10.1039/C3CE42540A
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33
_chemical_melting_point_gt       421
_chemical_melting_point_lt       422
_chemical_name_systematic
;
N,N'-(1,4-phenylenedimethylidyne)bis[2-fluorobenzenamine]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-09-17 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 107.509(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8090(7)
_cell_length_b                   20.942(3)
_cell_length_c                   6.6746(8)
_cell_measurement_reflns_used    3431
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.384
_cell_measurement_theta_min      3.345
_cell_volume                     774.36(17)
_computing_cell_refinement       'SAINTPLUS, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8930
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0401P)²+0.2341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                1348
_reflns_number_total             1781
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ce42540a1.cif
_cod_data_source_block           1
_cod_original_cell_volume        774.35(16)
_cod_database_code               7217146
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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.8943(2) 0.63095(6) 0.6469(2) 0.0239(3) Uani 1 1 d .
C2 C 1.0938(2) 0.67096(7) 0.6809(2) 0.0266(3) Uani 1 1 d .
C3 C 1.1755(3) 0.70950(7) 0.8544(2) 0.0307(3) Uani 1 1 d .
H3 H 1.3116 0.7364 0.8711 0.037 Uiso 1 1 calc R
C4 C 1.0547(3) 0.70811(7) 1.0045(2) 0.0320(3) Uani 1 1 d .
H4 H 1.1087 0.7340 1.1266 0.038 Uiso 1 1 calc R
C5 C 0.8551(3) 0.66899(7) 0.9764(2) 0.0315(3) Uani 1 1 d .
H5 H 0.7722 0.6684 1.0793 0.038 Uiso 1 1 calc R
C6 C 0.7753(3) 0.63063(6) 0.7991(2) 0.0274(3) Uani 1 1 d .
H6 H 0.6384 0.6040 0.7818 0.033 Uiso 1 1 calc R
C7 C 0.6211(2) 0.58058(6) 0.3642(2) 0.0265(3) Uani 1 1 d .
H7 H 0.4958 0.6009 0.4046 0.032 Uiso 1 1 calc R
C8 C 0.5597(2) 0.53817(6) 0.1804(2) 0.0238(3) Uani 1 1 d .
C9 C 0.3253(2) 0.53841(7) 0.0417(2) 0.0271(3) Uani 1 1 d .
H9 H 0.2054 0.5645 0.0707 0.033 Uiso 1 1 calc R
C10 C 0.2661(2) 0.50095(6) -0.1374(2) 0.0268(3) Uani 1 1 d .
H10 H 0.1066 0.5018 -0.2313 0.032 Uiso 1 1 calc R
F1 F 1.21019(16) 0.67254(5) 0.53281(14) 0.0402(3) Uani 1 1 d .
N1 N 0.8398(2) 0.59034(5) 0.46980(17) 0.0266(3) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C6 C1 C2 117.14(12) . .
C6 C1 N1 124.97(12) . .
C2 C1 N1 117.70(12) . .
F1 C2 C3 118.60(12) . .
F1 C2 C1 117.98(12) . .
C3 C2 C1 123.41(13) . .
C2 C3 C4 118.39(13) . .
C2 C3 H3 120. . .
C4 C3 H3 120. . .
C3 C4 C5 119.99(13) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C4 C5 C6 120.54(14) . .
C4 C5 H5 120 . .
C6 C5 H5 120 . .
C5 C6 C1 120.52(13) . .
C5 C6 H6 120 . .
C1 C6 H6 120 . .
N1 C7 C8 120.77(13) . .
N1 C7 H7 120 . .
C8 C7 H7 120 . .
C10 C8 C9 119.19(12) 3_665 .
C10 C8 C7 121.15(12) 3_665 .
C9 C8 C7 119.62(12) . .
C10 C9 C8 120.63(12) . .
C10 C9 H9 120 . .
C8 C9 H9 120 . .
C9 C10 C8 120.18(12) . 3_665
C9 C10 H10 120 . .
C8 C10 H10 120 3_665 .
C7 N1 C1 119.74(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.3903(19) .
C1 C2 1.3920(19) .
C1 N1 1.4126(17) .
C2 F1 1.3555(15) .
C2 C3 1.3738(19) .
C3 C4 1.386(2) .
C3 H3 0.95 .
C4 C5 1.386(2) .
C4 H4 0.95 .
C5 C6 1.3895(19) .
C5 H5 0.95 .
C6 H6 0.95 .
C7 N1 1.2706(18) .
C7 C8 1.4691(19) .
C7 H7 0.95 .
C8 C10 1.3970(19) 3_665
C8 C9 1.3973(18) .
C9 C10 1.3838(19) .
C9 H9 0.95 .
C10 C8 1.3970(19) 3_665
C10 H10 0.95 .
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_4
N1 C7 C8 C10 11.2(2) 3_665
N1 C7 C8 C9 -166.62(13) .
C6 C1 N1 C7 43.8(2) .
C2 C1 N1 C7 -141.44(14) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 340897
