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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/71/7217150.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_7217150
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       401
_chemical_melting_point_lt       403
_chemical_name_systematic
;
N,N'-bis[(3-fluorophenyl)methylene]-1,4-benzenediamine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 92.710(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.2826(17)
_cell_length_b                   6.1796(6)
_cell_length_c                   7.0765(7)
_cell_measurement_reflns_used    2344
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.36
_cell_volume                     754.92(13)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_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 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4277
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.2221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                1421
_reflns_number_total             1692
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ce42540a1.cif
_cod_data_source_block           5
_cod_database_code               7217150
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'
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 0.25151(7) 0.0968(2) 0.41074(17) 0.0268(3) Uani 1 1 d .
C2 C 0.31238(7) 0.2439(2) 0.43508(18) 0.0298(3) Uani 1 1 d .
H2 H 0.3032 0.3883 0.4743 0.036 Uiso 1 1 calc R
C3 C 0.38591(7) 0.1743(2) 0.4008(2) 0.0345(3) Uani 1 1 d .
C4 C 0.40231(8) -0.0324(3) 0.3426(2) 0.0378(3) Uani 1 1 d .
H4 H 0.4538 -0.0740 0.3182 0.045 Uiso 1 1 calc R
C5 C 0.34176(8) -0.1781(2) 0.3205(2) 0.0366(3) Uani 1 1 d .
H5 H 0.3516 -0.3217 0.2803 0.044 Uiso 1 1 calc R
C6 C 0.26658(8) -0.1157(2) 0.35675(19) 0.0320(3) Uani 1 1 d .
H6 H 0.2255 -0.2177 0.3448 0.038 Uiso 1 1 calc R
C7 C 0.17167(7) 0.1668(2) 0.43934(17) 0.0266(3) Uani 1 1 d .
H7 H 0.1326 0.0606 0.4528 0.032 Uiso 1 1 calc R
C8 C 0.07545(7) 0.4255(2) 0.47087(16) 0.0233(3) Uani 1 1 d .
C9 C 0.06307(7) 0.6229(2) 0.56181(17) 0.0240(3) Uani 1 1 d .
H9 H 0.1063 0.7083 0.6033 0.029 Uiso 1 1 calc R
C10 C -0.01111(7) 0.6959(2) 0.59243(16) 0.0240(3) Uani 1 1 d .
H10 H -0.0182 0.8289 0.6567 0.029 Uiso 1 1 calc R
F1 F 0.44518(5) 0.31740(16) 0.42372(15) 0.0529(3) Uani 1 1 d .
N1 N 0.15353(6) 0.36598(17) 0.44659(15) 0.0258(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
C2 C1 C6 119.85(12) . .
C2 C1 C7 119.90(12) . .
C6 C1 C7 120.24(12) . .
C3 C2 C1 118.18(13) . .
C3 C2 H2 120. . .
C1 C2 H2 120. . .
F1 C3 C2 118.28(13) . .
F1 C3 C4 118.42(12) . .
C2 C3 C4 123.30(13) . .
C3 C4 C5 118.19(12) . .
C3 C4 H4 120. . .
C5 C4 H4 120. . .
C4 C5 C6 120.47(13) . .
C4 C5 H5 120 . .
C6 C5 H5 120 . .
C5 C6 C1 119.96(13) . .
C5 C6 H6 120. . .
C1 C6 H6 120. . .
N1 C7 C1 121.71(12) . .
N1 C7 H7 120 . .
C1 C7 H7 120 . .
C10 C8 C9 118.59(11) 3_566 .
C10 C8 N1 124.74(11) 3_566 .
C9 C8 N1 116.66(11) . .
C10 C9 C8 121.20(11) . .
C10 C9 H9 120 . .
C8 C9 H9 120 . .
C9 C10 C8 120.21(11) . 3_566
C9 C10 H10 120 . .
C8 C10 H10 120 3_566 .
C7 N1 C8 119.61(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3949(18) .
C1 C6 1.3954(18) .
C1 C7 1.4693(16) .
C2 C3 1.3743(17) .
C2 H2 0.95 .
C3 F1 1.3573(16) .
C3 C4 1.375(2) .
C4 C5 1.384(2) .
C4 H4 0.95 .
C5 C6 1.3907(18) .
C5 H5 0.95 .
C6 H6 0.95 .
C7 N1 1.2718(17) .
C7 H7 0.95 .
C8 C10 1.3973(17) 3_566
C8 C9 1.4005(17) .
C8 N1 1.4169(15) .
C9 C10 1.3858(16) .
C9 H9 0.95 .
C10 C8 1.3973(17) 3_566
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_1
C2 C1 C7 N1 15.10(18) .
C6 C1 C7 N1 -164.02(13) .
C10 C8 N1 C7 -29.80(18) 3_566
C9 C8 N1 C7 151.56(12) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198909
