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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/4/50/16/4501690.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_4501690
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, C3 H7 N O'
_chemical_formula_sum            'C15 H15 F2 N3 O3'
_chemical_formula_weight         323.30
_space_group_IT_number           61
_space_group_name_Hall           '-P 2bc 2ac'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.1189(2)
_cell_length_b                   13.6856(5)
_cell_length_c                   36.8482(15)
_cell_measurement_reflns_used    2973
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     3085.7(2)
_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 0.960
_diffrn_measured_fraction_theta_max 0.960
_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  0.0931
_diffrn_reflns_av_sigmaI/netI    0.1206
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            4700
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.876
_refine_ls_R_factor_all          0.1868
_refine_ls_R_factor_gt           0.0600
_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)+(0.1042P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1977
_reflns_number_gt                970
_reflns_number_total             2610
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg100227s_si_008.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      Pcab
_cod_database_code               4501690
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, 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 0.5944(5) 0.4240(2) 0.34928(6) 0.1081(10) Uani 1 1 d .
N1 N 0.9308(6) 0.5678(2) 0.45761(9) 0.0720(10) Uani 1 1 d .
F2 F 0.2563(5) 0.3061(2) 0.36173(8) 0.1297(11) Uani 1 1 d .
C2 C 0.9560(7) 0.5694(3) 0.42161(12) 0.0691(12) Uani 1 1 d .
C3 C 1.1309(7) 0.6180(3) 0.40420(12) 0.0678(11) Uani 1 1 d .
C4 C 1.2803(7) 0.6664(3) 0.42588(13) 0.0788(13) Uani 1 1 d .
H4 H 1.3997 0.7000 0.4151 0.095 Uiso 1 1 calc R
C5 C 1.2562(8) 0.6658(3) 0.46312(13) 0.0817(13) Uani 1 1 d .
H5 H 1.3571 0.6989 0.4784 0.098 Uiso 1 1 calc R
C6 C 1.0811(8) 0.6158(3) 0.47738(12) 0.0789(13) Uani 1 1 d .
H6 H 1.0653 0.6150 0.5030 0.095 Uiso 1 1 calc R
N7 N 0.8050(6) 0.5194(3) 0.40104(9) 0.0781(11) Uani 1 1 d .
H7 H 0.8212 0.5256 0.3774 0.094 Uiso 1 1 calc R
C8 C 0.6301(7) 0.4604(3) 0.41170(11) 0.0658(11) Uani 1 1 d .
C9 C 0.5233(8) 0.4122(4) 0.38391(12) 0.0798(13) Uani 1 1 d .
C10 C 0.3509(9) 0.3522(4) 0.39050(14) 0.0870(14) Uani 1 1 d .
C11 C 0.2714(8) 0.3373(3) 0.42462(15) 0.0892(14) Uani 1 1 d .
H11 H 0.1494 0.2960 0.4290 0.107 Uiso 1 1 calc R
C12 C 0.3774(8) 0.3854(3) 0.45261(13) 0.0810(13) Uani 1 1 d .
H12 H 0.3264 0.3766 0.4767 0.097 Uiso 1 1 calc R
C13 C 0.5533(7) 0.4450(3) 0.44667(11) 0.0758(12) Uani 1 1 d .
H13 H 0.6232 0.4761 0.4666 0.091 Uiso 1 1 calc R
C14 C 1.1557(9) 0.6184(3) 0.36413(14) 0.0804(13) Uani 1 1 d .
O15 O 1.0306(6) 0.5795(3) 0.34328(8) 0.1002(11) Uani 1 1 d .
O16 O 1.3314(6) 0.6676(3) 0.35373(8) 0.1056(12) Uani 1 1 d .
H16 H 1.3481 0.6614 0.3312 0.158 Uiso 1 1 calc R
N17 N 0.6779(7) 0.6263(3) 0.24473(11) 0.0915(13) Uani 1 1 d .
C18 C 0.6048(9) 0.6448(3) 0.27754(15) 0.0889(14) Uani 1 1 d .
H18 H 0.7089 0.6503 0.2965 0.107 Uiso 1 1 calc R
O19 O 0.4107(6) 0.6555(2) 0.28535(8) 0.1041(12) Uani 1 1 d .
C20 C 0.5270(9) 0.6176(5) 0.21427(15) 0.130(2) Uani 1 1 d .
H20A H 0.6092 0.6033 0.1921 0.196 Uiso 1 1 calc R
H20B H 0.4471 0.6791 0.2113 0.196 Uiso 1 1 calc R
H20C H 0.4232 0.5646 0.2190 0.196 Uiso 1 1 calc R
C21 C 0.9098(9) 0.6164(4) 0.23814(17) 0.132(2) Uani 1 1 d .
H21A H 0.9346 0.6022 0.2124 0.198 Uiso 1 1 calc R
H21B H 0.9680 0.5628 0.2529 0.198 Uiso 1 1 calc R
H21C H 0.9839 0.6774 0.2446 0.198 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 116.8(4)
N1 C2 N7 117.4(4)
N1 C2 C3 123.1(4)
N7 C2 C3 119.5(4)
C4 C3 C2 117.6(4)
C4 C3 C14 120.3(4)
C2 C3 C14 122.1(4)
C5 C4 C3 120.1(4)
C5 C4 H4 120.0
C3 C4 H4 120.0
C6 C5 C4 117.8(4)
C6 C5 H5 121.1
C4 C5 H5 121.1
N1 C6 C5 124.7(4)
N1 C6 H6 117.7
C5 C6 H6 117.7
C2 N7 C8 130.3(4)
C2 N7 H7 114.9
C8 N7 H7 114.9
C9 C8 C13 117.1(4)
C9 C8 N7 115.4(4)
C13 C8 N7 127.4(4)
F1 C9 C10 119.2(4)
F1 C9 C8 119.2(4)
C10 C9 C8 121.5(4)
C9 C10 F2 118.1(5)
C9 C10 C11 122.2(4)
F2 C10 C11 119.7(5)
C10 C11 C12 116.6(4)
C10 C11 H11 121.7
C12 C11 H11 121.7
C13 C12 C11 122.2(4)
C13 C12 H12 118.9
C11 C12 H12 118.9
C12 C13 C8 120.3(4)
C12 C13 H13 119.8
C8 C13 H13 119.8
O15 C14 O16 123.6(4)
O15 C14 C3 124.5(5)
O16 C14 C3 111.9(5)
C14 O16 H16 109.5
C18 N17 C21 120.5(5)
C18 N17 C20 120.5(4)
C21 N17 C20 119.0(4)
O19 C18 N17 124.5(5)
O19 C18 H18 117.7
N17 C18 H18 117.7
N17 C20 H20A 109.5
N17 C20 H20B 109.5
H20A C20 H20B 109.5
N17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
N17 C21 H21A 109.5
N17 C21 H21B 109.5
H21A C21 H21B 109.5
N17 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.357(5)
N1 C2 1.336(5)
N1 C6 1.344(5)
F2 C10 1.363(5)
C2 N7 1.378(5)
C2 C3 1.413(5)
C3 C4 1.383(5)
C3 C14 1.484(6)
C4 C5 1.380(5)
C4 H4 0.9500
C5 C6 1.376(6)
C5 H5 0.9500
C6 H6 0.9500
N7 C8 1.397(5)
N7 H7 0.8800
C8 C9 1.382(6)
C8 C13 1.388(5)
C9 C10 1.359(6)
C10 C11 1.364(6)
C11 C12 1.385(6)
C11 H11 0.9500
C12 C13 1.368(5)
C12 H12 0.9500
C13 H13 0.9500
C14 O15 1.208(5)
C14 O16 1.325(5)
O16 H16 0.8400
N17 C18 1.313(6)
N17 C21 1.446(6)
N17 C20 1.458(6)
C18 O19 1.231(5)
C18 H18 0.9500
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
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 179.1(3)
C6 N1 C2 C3 0.3(6)
N1 C2 C3 C4 -0.5(6)
N7 C2 C3 C4 -179.2(4)
N1 C2 C3 C14 179.8(4)
N7 C2 C3 C14 1.1(6)
C2 C3 C4 C5 0.2(6)
C14 C3 C4 C5 179.9(4)
C3 C4 C5 C6 0.2(6)
C2 N1 C6 C5 0.2(6)
C4 C5 C6 N1 -0.5(7)
N1 C2 N7 C8 -4.2(6)
C3 C2 N7 C8 174.5(4)
C2 N7 C8 C9 -173.3(4)
C2 N7 C8 C13 6.6(7)
C13 C8 C9 F1 -179.1(4)
N7 C8 C9 F1 0.8(6)
C13 C8 C9 C10 -0.1(6)
N7 C8 C9 C10 179.8(4)
F1 C9 C10 F2 0.1(6)
C8 C9 C10 F2 -179.0(4)
F1 C9 C10 C11 -179.9(4)
C8 C9 C10 C11 1.0(7)
C9 C10 C11 C12 -0.9(7)
F2 C10 C11 C12 179.0(4)
C10 C11 C12 C13 0.0(7)
C11 C12 C13 C8 0.9(6)
C9 C8 C13 C12 -0.8(6)
N7 C8 C13 C12 179.3(4)
C4 C3 C14 O15 -178.6(4)
C2 C3 C14 O15 1.0(7)
C4 C3 C14 O16 0.8(6)
C2 C3 C14 O16 -179.6(4)
C21 N17 C18 O19 179.0(5)
C20 N17 C18 O19 0.4(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661347
2 PubChem 139144736
