#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222436.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_2222436
loop_
_publ_author_name
'Liu, Ting'
_publ_section_title
;
 (E)-2-(2,4-Dihydroxybenzylideneamino)benzonitrile
;
_journal_coeditor_code           RZ2327
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1502
_journal_paper_doi               10.1107/S1600536809020182
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 N2 O2'
_chemical_formula_moiety         'C14 H10 N2 O2'
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24
_chemical_name_systematic
;
(E)-2-(2,4-Dihydroxybenzylideneamino)benzonitrile
;
_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                90.00
_cell_angle_beta                 108.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.322(3)
_cell_length_b                   5.7505(12)
_cell_length_c                   16.132(3)
_cell_measurement_reflns_used    8059
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      3.07
_cell_volume                     1168.7(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCXmini'
_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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11536
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0585
_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)+(0.0648P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1528
_reflns_number_gt                1394
_reflns_number_total             2683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2327.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222436
_cod_database_fobs_code          2222436
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O2 0.79346(11) 0.8933(3) 0.08149(11) 0.0566(5) Uani d . 1 . .
H H2A 0.7911 0.7663 0.0578 0.085 Uiso calc R 1 . .
N N2 0.33856(14) 0.9483(3) 0.12987(11) 0.0458(5) Uani d . 1 . .
O O1 0.45029(14) 0.6553(3) 0.07575(12) 0.0620(5) Uani d . 1 . .
C C8 0.41862(18) 1.0886(4) 0.14982(14) 0.0467(6) Uani d . 1 . .
H H8A 0.4127 1.2327 0.1740 0.056 Uiso calc R 1 . .
C C9 0.51588(16) 1.0290(4) 0.13590(13) 0.0413(5) Uani d . 1 . .
C C12 0.70129(17) 0.9304(4) 0.09842(14) 0.0430(6) Uani d . 1 . .
C C5 0.1263(2) 1.2217(5) 0.20046(18) 0.0709(8) Uani d . 1 . .
H H5A 0.1164 1.3435 0.2349 0.085 Uiso calc R 1 . .
C C3 0.05604(19) 0.8978(5) 0.10712(18) 0.0643(7) Uani d . 1 . .
H H3A -0.0004 0.8009 0.0784 0.077 Uiso calc R 1 . .
C C1 0.24136(18) 1.0047(4) 0.14176(14) 0.0466(6) Uani d . 1 . .
C C10 0.52810(17) 0.8164(4) 0.09675(14) 0.0434(6) Uani d . 1 . .
C C14 0.60082(18) 1.1854(4) 0.15679(15) 0.0506(6) Uani d . 1 . .
H H14A 0.5947 1.3258 0.1834 0.061 Uiso calc R 1 . .
C C11 0.61972(16) 0.7695(4) 0.07767(14) 0.0447(6) Uani d . 1 . .
H H11A 0.6266 0.6300 0.0509 0.054 Uiso calc R 1 . .
C C13 0.69260(18) 1.1384(4) 0.13929(15) 0.0514(6) Uani d . 1 . .
H H13A 0.7484 1.2443 0.1545 0.062 Uiso calc R 1 . .
C C2 0.15547(18) 0.8609(4) 0.09949(15) 0.0500(6) Uani d . 1 . .
C C7 0.17047(19) 0.6737(5) 0.04576(18) 0.0575(7) Uani d . 1 . .
N N1 0.18114(18) 0.5237(4) 0.00325(17) 0.0777(8) Uani d . 1 . .
C C6 0.22459(19) 1.1855(5) 0.19264(16) 0.0598(7) Uani d . 1 . .
H H6A 0.2806 1.2832 0.2218 0.072 Uiso calc R 1 . .
C C4 0.0418(2) 1.0796(5) 0.15775(18) 0.0707(8) Uani d . 1 . .
H H4A -0.0247 1.1065 0.1632 0.085 Uiso calc R 1 . .
H H1A 0.392(2) 0.729(5) 0.0876(17) 0.090(10) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O2 H2A . . 109.5 ?
C8 N2 C1 . . 123.0(2) ?
C10 O1 H1A . . 104.5(17) ?
N2 C8 C9 . . 122.0(2) ?
N2 C8 H8A . . 119.0 ?
C9 C8 H8A . . 119.0 ?
C14 C9 C10 . . 117.6(2) ?
C14 C9 C8 . . 120.9(2) ?
C10 C9 C8 . . 121.5(2) ?
O2 C12 C11 . . 122.5(2) ?
O2 C12 C13 . . 116.8(2) ?
C11 C12 C13 . . 120.7(2) ?
C6 C5 C4 . . 120.8(3) ?
C6 C5 H5A . . 119.6 ?
C4 C5 H5A . . 119.6 ?
C4 C3 C2 . . 119.3(2) ?
C4 C3 H3A . . 120.4 ?
C2 C3 H3A . . 120.4 ?
C6 C1 C2 . . 117.9(2) ?
C6 C1 N2 . . 125.9(2) ?
C2 C1 N2 . . 116.2(2) ?
O1 C10 C11 . . 118.2(2) ?
O1 C10 C9 . . 121.1(2) ?
C11 C10 C9 . . 120.6(2) ?
C13 C14 C9 . . 122.0(2) ?
C13 C14 H14A . . 119.0 ?
C9 C14 H14A . . 119.0 ?
C12 C11 C10 . . 119.9(2) ?
C12 C11 H11A . . 120.1 ?
C10 C11 H11A . . 120.1 ?
C14 C13 C12 . . 119.1(2) ?
C14 C13 H13A . . 120.5 ?
C12 C13 H13A . . 120.5 ?
C3 C2 C1 . . 121.4(2) ?
C3 C2 C7 . . 119.5(2) ?
C1 C2 C7 . . 119.1(2) ?
N1 C7 C2 . . 179.0(3) ?
C5 C6 C1 . . 120.7(2) ?
C5 C6 H6A . . 119.7 ?
C1 C6 H6A . . 119.7 ?
C3 C4 C5 . . 119.9(2) ?
C3 C4 H4A . . 120.1 ?
C5 C4 H4A . . 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C12 . 1.359(2) ?
O2 H2A . 0.8200 ?
N2 C8 . 1.292(3) ?
N2 C1 . 1.407(3) ?
O1 C10 . 1.349(3) ?
O1 H1A . 0.95(3) ?
C8 C9 . 1.427(3) ?
C8 H8A . 0.9300 ?
C9 C14 . 1.398(3) ?
C9 C10 . 1.409(3) ?
C12 C11 . 1.383(3) ?
C12 C13 . 1.389(3) ?
C5 C6 . 1.372(3) ?
C5 C4 . 1.380(4) ?
C5 H5A . 0.9300 ?
C3 C4 . 1.377(3) ?
C3 C2 . 1.386(3) ?
C3 H3A . 0.9300 ?
C1 C6 . 1.387(3) ?
C1 C2 . 1.397(3) ?
C10 C11 . 1.379(3) ?
C14 C13 . 1.368(3) ?
C14 H14A . 0.9300 ?
C11 H11A . 0.9300 ?
C13 H13A . 0.9300 ?
C2 C7 . 1.436(3) ?
C7 N1 . 1.139(3) ?
C6 H6A . 0.9300 ?
C4 H4A . 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
O1 H1A N2 . 0.95(3) 1.70(3) 2.581(2) 152(3)
O2 H2A N1 3_665 0.82 2.03 2.835(3) 166.3
C11 H11A O1 3_665 0.93 2.56 3.386(3) 148
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742499
