#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/64/2216415.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_2216415
loop_
_publ_author_name
'Yong-Ji Xu'
'Shuang Zhao'
'Sai Bi'
_publ_section_title
;
 (E)-N-(2-Hydroxybenzylidene)isonicotinohydrazide
;
_journal_coeditor_code           DN2264
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4633
_journal_page_last               o4633
_journal_paper_doi               10.1107/S1600536807055730
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H11 N3 O2'
_chemical_formula_moiety         'C13 H11 N3 O2'
_chemical_formula_sum            'C13 H11 N3 O2'
_chemical_formula_weight         241.25
_chemical_name_systematic
;
(E)-N-(2-Hydroxybenzylidene)isonicotinohydrazide
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.147(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1467(12)
_cell_length_b                   15.562(2)
_cell_length_c                   10.7457(12)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.57
_cell_volume                     1165.9(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2003)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_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  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6268
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         2.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0367
_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)+(0.0540P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                1908
_reflns_number_total             2212
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2264.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2216415
_cod_database_fobs_code          2216415
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
N N1 0.11674(17) 0.24122(7) 0.19619(12) 0.0453(3) Uani d . 1
N N2 0.19855(16) 0.43183(7) 0.60543(11) 0.0418(3) Uani d . 1
H H2 0.1578 0.3825 0.6140 0.050 Uiso calc R 1
N N3 0.24356(15) 0.49509(7) 0.70680(11) 0.0408(3) Uani d . 1
O O1 0.26941(17) 0.51914(6) 0.47109(12) 0.0610(3) Uani d . 1
O O2 0.39390(16) 0.64334(6) 0.82295(12) 0.0551(3) Uani d . 1
H H2B 0.3605 0.6042 0.7636 0.083 Uiso calc R 1
C C1 0.05708(19) 0.30830(8) 0.36987(14) 0.0423(3) Uani d . 1
H H1 -0.0065 0.3068 0.4210 0.051 Uiso calc R 1
C C2 0.0297(2) 0.24389(9) 0.27236(14) 0.0455(3) Uani d . 1
H H2A -0.0547 0.1997 0.2591 0.055 Uiso calc R 1
C C3 0.2340(2) 0.30658(9) 0.21573(15) 0.0467(3) Uani d . 1
H H3 0.2949 0.3067 0.1626 0.056 Uiso calc R 1
C C4 0.2702(2) 0.37406(8) 0.31032(14) 0.0440(3) Uani d . 1
H H4 0.3534 0.4181 0.3202 0.053 Uiso calc R 1
C C5 0.18043(18) 0.37496(8) 0.39010(13) 0.0379(3) Uani d . 1
C C6 0.22024(19) 0.44935(8) 0.49115(14) 0.0412(3) Uani d . 1
C C7 0.22300(19) 0.47889(8) 0.81433(14) 0.0404(3) Uani d . 1
H H7 0.1763 0.4256 0.8209 0.048 Uiso calc R 1
C C8 0.27183(17) 0.54288(8) 0.92658(13) 0.0373(3) Uani d . 1
C C9 0.35359(18) 0.62208(8) 0.92655(14) 0.0409(3) Uani d . 1
C C10 0.3940(2) 0.68162(9) 1.03475(16) 0.0537(4) Uani d . 1
H H10 0.4457 0.7347 1.0337 0.064 Uiso calc R 1
C C11 0.3581(2) 0.66285(10) 1.14385(17) 0.0567(4) Uani d . 1
H H11 0.3856 0.7034 1.2156 0.068 Uiso calc R 1
C C12 0.2820(2) 0.58455(10) 1.14758(16) 0.0533(4) Uani d . 1
H H12 0.2599 0.5717 1.2223 0.064 Uiso calc R 1
C C13 0.2388(2) 0.52549(9) 1.03945(15) 0.0459(3) Uani d . 1
H H13 0.1865 0.4728 1.0416 0.055 Uiso calc R 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
C2 N1 C3 116.40(11)
C6 N2 N3 117.97(11)
C6 N2 H2 121.0
N3 N2 H2 121.0
C7 N3 N2 118.14(11)
C9 O2 H2B 109.5
C5 C1 C2 118.88(12)
C5 C1 H1 120.6
C2 C1 H1 120.6
N1 C2 C1 124.04(12)
N1 C2 H2A 118.0
C1 C2 H2A 118.0
N1 C3 C4 123.84(12)
N1 C3 H3 118.1
C4 C3 H3 118.1
C3 C4 C5 118.84(12)
C3 C4 H4 120.6
C5 C4 H4 120.6
C1 C5 C4 117.98(12)
C1 C5 C6 124.03(11)
C4 C5 C6 117.97(12)
O1 C6 N2 123.36(12)
O1 C6 C5 121.87(12)
N2 C6 C5 114.76(11)
N3 C7 C8 120.60(12)
N3 C7 H7 119.7
C8 C7 H7 119.7
C13 C8 C9 118.38(12)
C13 C8 C7 119.66(12)
C9 C8 C7 121.95(11)
O2 C9 C10 118.20(12)
O2 C9 C8 122.17(12)
C10 C9 C8 119.63(13)
C11 C10 C9 120.58(14)
C11 C10 H10 119.7
C9 C10 H10 119.7
C12 C11 C10 120.61(13)
C12 C11 H11 119.7
C10 C11 H11 119.7
C13 C12 C11 119.22(14)
C13 C12 H12 120.4
C11 C12 H12 120.4
C12 C13 C8 121.55(13)
C12 C13 H13 119.2
C8 C13 H13 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3323(17)
N1 C3 1.3357(18)
N2 C6 1.3558(17)
N2 N3 1.3699(15)
N2 H2 0.8600
N3 C7 1.2756(16)
O1 C6 1.2148(16)
O2 C9 1.3546(16)
O2 H2B 0.8200
C1 C5 1.3809(19)
C1 C2 1.3822(18)
C1 H1 0.9300
C2 H2A 0.9300
C3 C4 1.3830(19)
C3 H3 0.9300
C4 C5 1.3853(18)
C4 H4 0.9300
C5 C6 1.5034(18)
C7 C8 1.4521(17)
C7 H7 0.9300
C8 C13 1.3978(18)
C8 C9 1.4009(18)
C9 C10 1.3867(19)
C10 C11 1.378(2)
C10 H10 0.9300
C11 C12 1.377(2)
C11 H11 0.9300
C12 C13 1.3770(19)
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
O2 H2B N3 . 0.82 1.89 2.6076(15) 146.0
N2 H2 N1 4_566 0.86 2.21 3.0530(15) 164.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10439927
