#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/64/2216489.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2216489
loop_
_publ_author_name
'Qiang Wang'
'Yu-Ying Sun'
'Da-Qi Wang'
_publ_section_title
;
 3-(2-Pyridylmethyleneamino)benzoic acid
;
_journal_coeditor_code           HB2632
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4597
_journal_page_last               o4597
_journal_paper_doi               10.1107/S1600536807055754
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H10 N2 O2'
_chemical_formula_moiety         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23
_chemical_name_systematic
;
3-(2-Pyridylmethyleneamino)benzoic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 123.553(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.217(2)
_cell_length_b                   4.0536(17)
_cell_length_c                   23.767(2)
_cell_measurement_reflns_used    781
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.182
_cell_measurement_theta_min      3.007
_cell_volume                     2185.2(10)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_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  0.0923
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5079
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0617
_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)+(0.0411P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                896
_reflns_number_total             1926
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2632.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2216489
_cod_database_fobs_code          2216489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.10556(9) 0.7481(7) 0.34401(12) 0.0521(8) Uani d . 1
N N2 0.07264(9) 1.2019(7) 0.44507(12) 0.0514(8) Uani d . 1
O O1 0.35449(8) 0.8343(7) 0.41129(11) 0.0816(9) Uani d . 1
O O2 0.32303(8) 1.0085(7) 0.47445(10) 0.0703(8) Uani d . 1
H H2 0.3564 1.0856 0.4974 0.105 Uiso calc R 1
C C1 0.31601(12) 0.8605(9) 0.42142(16) 0.0561(10) Uani d . 1
C C2 0.25549(12) 0.7286(8) 0.37490(14) 0.0467(9) Uani d . 1
C C3 0.21148(11) 0.7944(8) 0.38571(14) 0.0466(9) Uani d . 1
H H3 0.2201 0.9108 0.4239 0.056 Uiso calc R 1
C C4 0.15450(11) 0.6866(8) 0.33956(14) 0.0431(8) Uani d . 1
C C5 0.14323(12) 0.5086(8) 0.28483(14) 0.0501(9) Uani d . 1
H H5 0.1053 0.4293 0.2545 0.060 Uiso calc R 1
C C6 0.18674(13) 0.4448(10) 0.27381(15) 0.0597(10) Uani d . 1
H H6 0.1782 0.3248 0.2361 0.072 Uiso calc R 1
C C7 0.24288(13) 0.5586(8) 0.31864(15) 0.0524(9) Uani d . 1
H H7 0.2723 0.5203 0.3108 0.063 Uiso calc R 1
C C8 0.10902(11) 0.9531(9) 0.38494(14) 0.0491(9) Uani d . 1
H H8 0.1443 1.0656 0.4125 0.059 Uiso calc R 1
C C9 0.05954(11) 1.0241(9) 0.39133(14) 0.0439(8) Uani d . 1
C C10 0.00358(11) 0.9087(9) 0.34624(14) 0.0538(10) Uani d . 1
H H10 -0.0049 0.7873 0.3087 0.065 Uiso calc R 1
C C11 -0.03951(12) 0.9758(9) 0.35763(15) 0.0568(10) Uani d . 1
H H11 -0.0778 0.9017 0.3273 0.068 Uiso calc R 1
C C12 -0.02658(13) 1.1499(9) 0.41295(16) 0.0581(10) Uani d . 1
H H12 -0.0552 1.1918 0.4219 0.070 Uiso calc R 1
C C13 0.03026(13) 1.2628(9) 0.45537(15) 0.0616(11) Uani d . 1
H H13 0.0394 1.3871 0.4929 0.074 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0372(14) 0.070(2) 0.0529(16) 0.0010(14) 0.0276(13) -0.0067(15)
N2 0.0346(14) 0.071(2) 0.0524(15) 0.0037(14) 0.0266(13) -0.0061(15)
O1 0.0428(13) 0.127(3) 0.0893(17) -0.0066(14) 0.0454(13) -0.0231(16)
O2 0.0356(12) 0.113(2) 0.0599(14) -0.0092(14) 0.0248(12) -0.0223(15)
C1 0.041(2) 0.074(3) 0.055(2) 0.0023(18) 0.0277(18) -0.0014(19)
C2 0.0362(17) 0.059(3) 0.0466(18) 0.0035(16) 0.0238(16) 0.0013(17)
C3 0.0352(17) 0.064(3) 0.0426(17) 0.0080(16) 0.0230(16) -0.0004(16)
C4 0.0315(16) 0.059(3) 0.0424(17) 0.0038(16) 0.0225(15) 0.0006(17)
C5 0.0401(17) 0.063(3) 0.0478(19) 0.0021(17) 0.0244(16) 0.0007(18)
C6 0.055(2) 0.076(3) 0.056(2) -0.001(2) 0.0359(19) -0.013(2)
C7 0.0442(19) 0.068(3) 0.059(2) 0.0016(18) 0.0369(18) -0.0017(19)
C8 0.0312(16) 0.068(3) 0.0505(19) -0.0021(17) 0.0240(16) 0.0008(19)
C9 0.0315(16) 0.058(2) 0.0456(18) 0.0012(16) 0.0234(15) -0.0017(17)
C10 0.0337(18) 0.073(3) 0.0525(19) -0.0016(16) 0.0223(17) -0.0095(18)
C11 0.0328(17) 0.073(3) 0.061(2) 0.0001(17) 0.0236(17) -0.004(2)
C12 0.0362(19) 0.080(3) 0.065(2) 0.0040(18) 0.0327(18) -0.003(2)
C13 0.0437(19) 0.087(3) 0.060(2) 0.0037(19) 0.0326(18) -0.012(2)
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'
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
C8 N1 C4 120.6(3)
C13 N2 C9 118.6(3)
C1 O2 H2 109.5
O1 C1 O2 123.6(3)
O1 C1 C2 123.3(3)
O2 C1 C2 113.1(2)
C7 C2 C3 120.2(3)
C7 C2 C1 119.0(3)
C3 C2 C1 120.7(3)
C2 C3 C4 119.9(3)
C2 C3 H3 120.1
C4 C3 H3 120.1
C5 C4 C3 119.0(2)
C5 C4 N1 116.0(3)
C3 C4 N1 125.0(3)
C4 C5 C6 121.2(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C7 119.8(3)
C5 C6 H6 120.1
C7 C6 H6 120.1
C2 C7 C6 119.9(3)
C2 C7 H7 120.1
C6 C7 H7 120.1
N1 C8 C9 122.4(3)
N1 C8 H8 118.8
C9 C8 H8 118.8
N2 C9 C10 121.8(2)
N2 C9 C8 115.6(3)
C10 C9 C8 122.6(3)
C11 C10 C9 118.7(3)
C11 C10 H10 120.6
C9 C10 H10 120.6
C12 C11 C10 120.2(3)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 117.9(3)
C11 C12 H12 121.1
C13 C12 H12 121.1
N2 C13 C12 122.8(3)
N2 C13 H13 118.6
C12 C13 H13 118.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.243(3)
N1 C4 1.415(3)
N2 C13 1.328(3)
N2 C9 1.332(3)
O1 C1 1.202(3)
O2 C1 1.311(3)
O2 H2 0.8200
C1 C2 1.486(4)
C2 C7 1.369(4)
C2 C3 1.383(3)
C3 C4 1.385(4)
C3 H3 0.9300
C4 C5 1.366(4)
C5 C6 1.371(3)
C5 H5 0.9300
C6 C7 1.372(4)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.465(3)
C8 H8 0.9300
C9 C10 1.372(4)
C10 C11 1.369(3)
C10 H10 0.9300
C11 C12 1.356(4)
C11 H11 0.9300
C12 C13 1.377(4)
C12 H12 0.9300
C13 H13 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12 O1 3_455 0.93 2.40 3.301(3) 164
O2 H2 N2 7_576 0.82 1.85 2.664(3) 172
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15454712
