#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/16/4501687.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_4501687
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                106.3670(23)
_cell_angle_beta                 90.3310(23)
_cell_angle_gamma                96.5160(22)
_cell_formula_units_Z            2
_cell_length_a                   4.2521(2)
_cell_length_b                   9.4407(5)
_cell_length_c                   13.6969(8)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     523.73(5)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0756
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4690
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0664P)²+1.7429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2355
_refine_ls_wR_factor_ref         0.2489
_reflns_number_gt                1595
_reflns_number_total             2376
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg100227s_si_005.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4501687
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 0.3068(6) -0.0376(3) 0.23072(19) 0.0289(7) Uani 1 1 d .
O15 O -0.2231(7) 0.0738(3) 0.0872(2) 0.0256(7) Uani 1 1 d .
F2 F 0.6967(7) -0.0965(3) 0.3647(2) 0.0321(7) Uani 1 1 d .
O16 O -0.4816(8) 0.1959(4) 0.0004(2) 0.0299(8) Uani 1 1 d .
H16 H -0.5662 0.1092 -0.0285 0.045 Uiso 1 1 calc R
N7 N 0.1910(8) 0.2344(4) 0.2355(3) 0.0226(8) Uani 1 1 d .
H7 H 0.1058 0.1492 0.1942 0.027 Uiso 1 1 calc R
N1 N 0.2217(9) 0.4915(4) 0.2721(3) 0.0263(9) Uani 1 1 d .
C8 C 0.3975(10) 0.2213(5) 0.3109(3) 0.0221(9) Uani 1 1 d .
C12 C 0.7460(11) 0.3045(5) 0.4622(3) 0.0275(10) Uani 1 1 d .
H12 H 0.8447 0.3838 0.5166 0.033 Uiso 1 1 calc R
C9 C 0.4546(10) 0.0771(5) 0.3064(3) 0.0234(9) Uani 1 1 d .
C3 C -0.1207(10) 0.3392(5) 0.1316(3) 0.0235(9) Uani 1 1 d .
C11 C 0.7975(11) 0.1599(5) 0.4562(3) 0.0265(10) Uani 1 1 d .
H11 H 0.9298 0.1388 0.5052 0.032 Uiso 1 1 calc R
C14 C -0.2751(10) 0.1924(5) 0.0722(3) 0.0242(10) Uani 1 1 d .
C13 C 0.5544(10) 0.3367(5) 0.3908(3) 0.0241(9) Uani 1 1 d .
H13 H 0.5289 0.4372 0.3958 0.029 Uiso 1 1 calc R
C6 C 0.1400(12) 0.6107(5) 0.2480(4) 0.0303(11) Uani 1 1 d .
H6 H 0.2277 0.7059 0.2893 0.036 Uiso 1 1 calc R
C4 C -0.1957(12) 0.4664(5) 0.1093(4) 0.0291(10) Uani 1 1 d .
H4 H -0.3391 0.4578 0.0540 0.035 Uiso 1 1 calc R
C5 C -0.0630(12) 0.6051(5) 0.1672(4) 0.0309(11) Uani 1 1 d .
H5 H -0.1089 0.6931 0.1522 0.037 Uiso 1 1 calc R
C2 C 0.0984(10) 0.3569(5) 0.2148(3) 0.0224(9) Uani 1 1 d .
C10 C 0.6492(11) 0.0481(5) 0.3765(3) 0.0252(10) 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'
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
C14 O16 H16 109.5
C2 N7 C8 131.0(4)
C2 N7 H7 114.5
C8 N7 H7 114.5
C2 N1 C6 118.1(4)
N7 C8 C9 116.0(4)
N7 C8 C13 127.4(4)
C9 C8 C13 116.6(4)
C11 C12 C13 121.8(4)
C11 C12 H12 119.1
C13 C12 H12 119.1
F1 C9 C10 119.5(4)
F1 C9 C8 118.4(4)
C10 C9 C8 122.0(4)
C4 C3 C2 118.0(4)
C4 C3 C14 119.7(4)
C2 C3 C14 122.2(4)
C10 C11 C12 117.3(4)
C10 C11 H11 121.3
C12 C11 H11 121.3
O15 C14 O16 121.5(4)
O15 C14 C3 123.9(4)
O16 C14 C3 114.6(4)
C12 C13 C8 120.4(4)
C12 C13 H13 119.8
C8 C13 H13 119.8
N1 C6 C5 124.8(4)
N1 C6 H6 117.6
C5 C6 H6 117.6
C5 C4 C3 120.4(5)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 117.2(4)
C4 C5 H5 121.4
C6 C5 H5 121.4
N1 C2 N7 118.8(4)
N1 C2 C3 121.5(4)
N7 C2 C3 119.7(4)
F2 C10 C9 117.9(4)
F2 C10 C11 120.3(4)
C9 C10 C11 121.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.359(5)
O15 C14 1.237(5)
F2 C10 1.368(5)
O16 C14 1.324(5)
O16 H16 0.8400
N7 C2 1.363(6)
N7 C8 1.393(6)
N7 H7 0.8800
N1 C2 1.337(5)
N1 C6 1.339(6)
C8 C9 1.394(6)
C8 C13 1.408(6)
C12 C11 1.388(6)
C12 C13 1.388(7)
C12 H12 0.9500
C9 C10 1.368(7)
C3 C4 1.389(7)
C3 C2 1.428(6)
C3 C14 1.472(6)
C11 C10 1.377(6)
C11 H11 0.9500
C13 H13 0.9500
C6 C5 1.385(7)
C6 H6 0.9500
C4 C5 1.380(6)
C4 H4 0.9500
C5 H5 0.9500
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
C2 N7 C8 C9 -176.2(4)
C2 N7 C8 C13 3.8(7)
N7 C8 C9 F1 -0.3(6)
C13 C8 C9 F1 179.7(4)
N7 C8 C9 C10 -179.1(4)
C13 C8 C9 C10 0.9(6)
C13 C12 C11 C10 -0.3(7)
C4 C3 C14 O15 -179.7(4)
C2 C3 C14 O15 -1.9(7)
C4 C3 C14 O16 -0.5(6)
C2 C3 C14 O16 177.3(4)
C11 C12 C13 C8 1.9(7)
N7 C8 C13 C12 177.9(4)
C9 C8 C13 C12 -2.1(6)
C2 N1 C6 C5 -0.3(7)
C2 C3 C4 C5 -0.7(7)
C14 C3 C4 C5 177.2(4)
C3 C4 C5 C6 -1.1(7)
N1 C6 C5 C4 1.7(8)
C6 N1 C2 N7 176.9(4)
C6 N1 C2 C3 -1.6(6)
C8 N7 C2 N1 1.6(7)
C8 N7 C2 C3 -179.8(4)
C4 C3 C2 N1 2.1(6)
C14 C3 C2 N1 -175.8(4)
C4 C3 C2 N7 -176.4(4)
C14 C3 C2 N7 5.7(6)
F1 C9 C10 F2 2.6(6)
C8 C9 C10 F2 -178.6(4)
F1 C9 C10 C11 -178.2(4)
C8 C9 C10 C11 0.7(7)
C12 C11 C10 F2 178.2(4)
C12 C11 C10 C9 -1.0(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661345
2 PubChem 61075238
