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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/16/4501688.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_4501688
loop_
_publ_author_name
'Long, Sihui'
'Li, Tonglei'
_publ_section_title
;
 Enforcing Molecule’s π-Conjugation and Consequent Formation of
 the Acid−Acid Homosynthon over the Acid−Pyridine
 Heterosynthon in 2-Anilinonicotinic Acids
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2465
_journal_paper_doi               10.1021/cg100227s
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C12 H8 F2 N2 O2'
_chemical_formula_sum            'C12 H8 F2 N2 O2'
_chemical_formula_weight         250.20
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.6379(15)
_cell_angle_beta                 105.2924(15)
_cell_angle_gamma                94.5914(16)
_cell_formula_units_Z            2
_cell_length_a                   6.8233(2)
_cell_length_b                   7.6420(3)
_cell_length_c                   10.9371(4)
_cell_measurement_reflns_used    2367
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     525.64(3)
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4728
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0579
_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)+(0.0950P)²+0.0970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1760
_reflns_number_gt                1483
_reflns_number_total             2392
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg100227s_si_006.cif
_cod_data_source_block           4c
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4501688
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F -0.1202(2) 0.5433(2) 0.85456(14) 0.0375(4) Uani 1 1 d .
N1 N 0.2602(3) 0.3911(3) 0.53601(19) 0.0266(5) Uani 1 1 d .
F2 F 0.0787(2) 0.8033(2) 1.07893(16) 0.0476(5) Uani 1 1 d .
C2 C 0.0878(3) 0.3218(3) 0.5552(2) 0.0251(5) Uani 1 1 d .
C3 C -0.0634(3) 0.1860(3) 0.4527(2) 0.0248(5) Uani 1 1 d .
C4 C -0.0227(3) 0.1192(3) 0.3327(2) 0.0275(6) Uani 1 1 d .
H4 H -0.1201 0.0269 0.2634 0.033 Uiso 1 1 calc R
C5 C 0.1573(4) 0.1852(3) 0.3131(3) 0.0314(6) Uani 1 1 d .
H5 H 0.1878 0.1391 0.2321 0.038 Uiso 1 1 calc R
C6 C 0.2915(4) 0.3223(3) 0.4172(2) 0.0304(6) Uani 1 1 d .
H6 H 0.4143 0.3713 0.4041 0.037 Uiso 1 1 calc R
N7 N 0.0587(3) 0.3858(3) 0.67613(19) 0.0284(5) Uani 1 1 d .
H7 H -0.0564 0.3360 0.6841 0.034 Uiso 1 1 calc R
C8 C 0.1830(3) 0.5182(3) 0.7895(2) 0.0267(5) Uani 1 1 d .
C9 C 0.0844(3) 0.5989(3) 0.8811(2) 0.0295(6) Uani 1 1 d .
C10 C 0.1875(4) 0.7306(4) 0.9963(3) 0.0349(6) Uani 1 1 d .
C11 C 0.3954(4) 0.7878(4) 1.0282(3) 0.0400(7) Uani 1 1 d .
H11 H 0.4672 0.8787 1.1084 0.048 Uiso 1 1 calc R
C12 C 0.4967(4) 0.7075(4) 0.9386(3) 0.0399(7) Uani 1 1 d .
H12 H 0.6405 0.7446 0.9584 0.048 Uiso 1 1 calc R
C13 C 0.3942(4) 0.5756(4) 0.8216(2) 0.0316(6) Uani 1 1 d .
H13 H 0.4680 0.5234 0.7626 0.038 Uiso 1 1 calc R
C14 C -0.2562(3) 0.1125(3) 0.4720(2) 0.0259(5) Uani 1 1 d .
O15 O -0.3057(2) 0.1676(2) 0.57379(16) 0.0294(4) Uani 1 1 d .
O16 O -0.3740(2) -0.0208(2) 0.36859(16) 0.0318(4) Uani 1 1 d .
H16 H -0.4748 -0.0642 0.3881 0.048 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C6 117.9(2)
N1 C2 N7 118.2(2)
N1 C2 C3 121.7(2)
N7 C2 C3 120.1(2)
C4 C3 C2 118.0(2)
C4 C3 C14 120.0(2)
C2 C3 C14 122.0(2)
C5 C4 C3 120.9(2)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C6 116.8(2)
C4 C5 H5 121.6
C6 C5 H5 121.6
N1 C6 C5 124.7(2)
N1 C6 H6 117.6
C5 C6 H6 117.6
C2 N7 C8 130.12(19)
C2 N7 H7 114.9
C8 N7 H7 114.9
C9 C8 C13 116.9(2)
C9 C8 N7 116.0(2)
C13 C8 N7 127.1(2)
F1 C9 C10 119.4(2)
F1 C9 C8 118.5(2)
C10 C9 C8 122.1(2)
F2 C10 C9 118.1(2)
F2 C10 C11 120.6(2)
C9 C10 C11 121.3(2)
C10 C11 C12 117.4(2)
C10 C11 H11 121.3
C12 C11 H11 121.3
C13 C12 C11 121.9(2)
C13 C12 H12 119.1
C11 C12 H12 119.1
C12 C13 C8 120.5(2)
C12 C13 H13 119.8
C8 C13 H13 119.8
O15 C14 O16 122.27(19)
O15 C14 C3 123.9(2)
O16 C14 C3 113.8(2)
C14 O16 H16 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.357(3)
N1 C2 1.340(3)
N1 C6 1.353(3)
F2 C10 1.358(3)
C2 N7 1.363(3)
C2 C3 1.424(3)
C3 C4 1.391(3)
C3 C14 1.476(3)
C4 C5 1.379(3)
C4 H4 0.9500
C5 C6 1.388(4)
C5 H5 0.9500
C6 H6 0.9500
N7 C8 1.398(3)
N7 H7 0.8800
C8 C9 1.395(3)
C8 C13 1.395(3)
C9 C10 1.369(4)
C10 C11 1.374(4)
C11 C12 1.392(4)
C11 H11 0.9500
C12 C13 1.380(4)
C12 H12 0.9500
C13 H13 0.9500
C14 O15 1.231(3)
C14 O16 1.331(3)
O16 H16 0.8400
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
C6 N1 C2 N7 177.7(2)
C6 N1 C2 C3 -2.9(3)
N1 C2 C3 C4 3.3(3)
N7 C2 C3 C4 -177.28(19)
N1 C2 C3 C14 -178.33(19)
N7 C2 C3 C14 1.1(3)
C2 C3 C4 C5 -1.2(3)
C14 C3 C4 C5 -179.6(2)
C3 C4 C5 C6 -1.1(3)
C2 N1 C6 C5 0.3(3)
C4 C5 C6 N1 1.7(4)
N1 C2 N7 C8 0.2(3)
C3 C2 N7 C8 -179.2(2)
C2 N7 C8 C9 158.7(2)
C2 N7 C8 C13 -22.5(4)
C13 C8 C9 F1 -178.5(2)
N7 C8 C9 F1 0.5(3)
C13 C8 C9 C10 1.1(4)
N7 C8 C9 C10 -179.9(2)
F1 C9 C10 F2 -1.2(4)
C8 C9 C10 F2 179.2(2)
F1 C9 C10 C11 178.6(2)
C8 C9 C10 C11 -1.0(4)
F2 C10 C11 C12 -179.8(2)
C9 C10 C11 C12 0.4(4)
C10 C11 C12 C13 0.1(4)
C11 C12 C13 C8 0.0(4)
C9 C8 C13 C12 -0.6(4)
N7 C8 C13 C12 -179.4(2)
C4 C3 C14 O15 -178.1(2)
C2 C3 C14 O15 3.6(3)
C4 C3 C14 O16 2.1(3)
C2 C3 C14 O16 -176.25(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661345
2 PubChem 61075238
