#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/02/2210271.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_2210271
loop_
_publ_author_name
'De-Suo Yang'
_publ_section_title
;
 N'-[1-(5-Chloro-2-hydroxyphenyl)methylidene]isonicotinohydrazide
;
_journal_coeditor_code           HG2090
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3755
_journal_page_last               o3756
_journal_paper_doi               10.1107/S1600536806030777
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H10 Cl N3 O2'
_chemical_formula_moiety         'C13 H10 Cl N3 O2'
_chemical_formula_sum            'C13 H10 Cl N3 O2'
_chemical_formula_weight         275.69
_chemical_name_systematic
;
N'-[1-(5-Chloro-2-hydroxyphenyl)methylidene]isonicotinohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.219(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6170(10)
_cell_length_b                   15.730(2)
_cell_length_c                   9.2850(10)
_cell_measurement_reflns_used    1852
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1234.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 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  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10471
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9209
_exptl_absorpt_correction_T_min  0.9045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0445
_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)+(0.0507P)²+0.1995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2007
_reflns_number_total             2812
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2090.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210271
_cod_database_fobs_code          2210271
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl Cl1 1.19673(7) 1.10126(4) 0.95543(6) 0.0635(2) Uani d . 1
O O1 0.78260(18) 1.13617(9) 0.37912(15) 0.0542(4) Uani d . 1
H H1 0.7210 1.0961 0.3613 0.081 Uiso calc R 1
O O2 0.45278(19) 1.00917(9) 0.18787(16) 0.0643(5) Uani d . 1
N N1 0.67266(18) 0.98771(10) 0.42011(16) 0.0390(4) Uani d . 1
N N2 0.57479(18) 0.92182(10) 0.36601(17) 0.0382(4) Uani d D 1
N N3 0.16236(18) 0.73965(10) 0.03802(16) 0.0410(4) Uani d . 1
C C1 0.8753(2) 1.04950(11) 0.59381(19) 0.0338(4) Uani d . 1
C C2 0.8776(2) 1.12462(12) 0.51217(19) 0.0371(4) Uani d . 1
C C3 0.9787(2) 1.19012(12) 0.5679(2) 0.0434(5) Uani d . 1
H H3 0.9814 1.2392 0.5127 0.052 Uiso calc R 1
C C4 1.0751(2) 1.18353(13) 0.7040(2) 0.0429(5) Uani d . 1
H H4 1.1411 1.2284 0.7414 0.052 Uiso calc R 1
C C5 1.0734(2) 1.11030(12) 0.7845(2) 0.0401(5) Uani d . 1
C C6 0.9753(2) 1.04366(12) 0.7309(2) 0.0383(4) Uani d . 1
H H6 0.9758 0.9945 0.7866 0.046 Uiso calc R 1
C C7 0.7713(2) 0.97949(12) 0.53980(19) 0.0371(4) Uani d . 1
H H7 0.7767 0.9289 0.5924 0.044 Uiso calc R 1
C C8 0.4671(2) 0.93926(12) 0.2423(2) 0.0404(5) Uani d . 1
C C9 0.3655(2) 0.86642(12) 0.17577(19) 0.0357(4) Uani d . 1
C C10 0.2926(2) 0.87317(12) 0.0292(2) 0.0410(5) Uani d . 1
H H10 0.3105 0.9203 -0.0258 0.049 Uiso calc R 1
C C11 0.1936(2) 0.80898(13) -0.0336(2) 0.0419(5) Uani d . 1
H H11 0.1457 0.8143 -0.1320 0.050 Uiso calc R 1
C C12 0.2319(2) 0.73444(13) 0.1797(2) 0.0409(5) Uani d . 1
H H12 0.2099 0.6872 0.2325 0.049 Uiso calc R 1
C C13 0.3341(2) 0.79478(12) 0.25237(19) 0.0371(4) Uani d . 1
H H13 0.3809 0.7876 0.3506 0.045 Uiso calc R 1
H H2 0.596(3) 0.8709(9) 0.409(2) 0.080 Uiso d 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'
Cl Cl 0.1484 0.1585 '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 O1 H1 109.5
C7 N1 N2 120.31(16)
C8 N2 N1 115.39(15)
C8 N2 H2 127.1(17)
N1 N2 H2 117.1(17)
C11 N3 C12 116.48(16)
C6 C1 C2 118.47(16)
C6 C1 C7 119.83(16)
C2 C1 C7 121.69(16)
O1 C2 C3 117.77(17)
O1 C2 C1 122.36(16)
C3 C2 C1 119.87(17)
C4 C3 C2 120.79(18)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 119.65(17)
C3 C4 H4 120.2
C5 C4 H4 120.2
C4 C5 C6 120.79(17)
C4 C5 Cl1 119.77(15)
C6 C5 Cl1 119.44(15)
C5 C6 C1 120.42(18)
C5 C6 H6 119.8
C1 C6 H6 119.8
N1 C7 C1 119.40(17)
N1 C7 H7 120.3
C1 C7 H7 120.3
O2 C8 N2 122.40(18)
O2 C8 C9 121.34(17)
N2 C8 C9 116.26(17)
C13 C9 C10 117.97(17)
C13 C9 C8 124.47(16)
C10 C9 C8 117.50(17)
C11 C10 C9 118.97(18)
C11 C10 H10 120.5
C9 C10 H10 120.5
N3 C11 C10 123.92(17)
N3 C11 H11 118.0
C10 C11 H11 118.0
N3 C12 C13 124.06(18)
N3 C12 H12 118.0
C13 C12 H12 118.0
C12 C13 C9 118.58(17)
C12 C13 H13 120.7
C9 C13 H13 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.7356(19)
O1 C2 1.355(2)
O1 H1 0.8200
O2 C8 1.206(2)
N1 C7 1.267(2)
N1 N2 1.369(2)
N2 C8 1.357(2)
N2 H2 0.897(10)
N3 C11 1.332(2)
N3 C12 1.338(2)
C1 C6 1.395(2)
C1 C2 1.406(2)
C1 C7 1.447(2)
C2 C3 1.383(3)
C3 C4 1.374(3)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C6 1.377(3)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.500(3)
C9 C13 1.387(3)
C9 C10 1.388(2)
C10 C11 1.376(3)
C10 H10 0.9300
C11 H11 0.9300
C12 C13 1.379(3)
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
N2 H2 N3 4_676 0.897(10) 2.127(10) 3.017(2) 172(2)
O1 H1 N1 . 0.82 1.86 2.576(2) 145
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655036
