#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/52/2215236.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_2215236
loop_
_publ_author_name
'De-Suo Yang'
_publ_section_title
;
 6-Chloro-2'-(2-hydroxybenzylidene)nicotinohydrazide monohydrate
;
_journal_coeditor_code           OM2148
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3738
_journal_page_last               o3738
_journal_paper_doi               10.1107/S1600536807038500
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H10 Cl N3 O2 , H2 O1'
_chemical_formula_moiety         'C13 H10 Cl N3 O2 , H2 O1'
_chemical_formula_sum            'C13 H12 Cl N3 O3'
_chemical_formula_weight         293.71
_chemical_name_systematic
;
6-Chloro-2'-(2-hydroxybenzylidene)nicotinohydrazide monohydrate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 92.764(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.125(11)
_cell_length_b                   3.8193(15)
_cell_length_c                   12.281(5)
_cell_measurement_reflns_used    1313
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      2.5
_cell_volume                     1317.7(9)
_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'
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3648
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9232
_exptl_absorpt_correction_T_min  0.9099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.173
_refine_ls_abs_structure_details 'Flack (1983), 643 Friedel pairs'
_refine_ls_abs_structure_Flack   0.15(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0364
_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)+(0.0437P)²+0.2959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                1826
_reflns_number_total             2141
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2148.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2215236
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'
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 0.53442(3) 0.6124(2) 0.35665(6) 0.0658(3) Uani d . 1
O O1 0.22659(8) -0.2060(6) -0.05359(16) 0.0570(6) Uani d . 1
H H1 0.2498 -0.1108 -0.0233 0.086 Uiso calc R 1
O O2 0.36101(7) 0.0985(6) 0.00747(15) 0.0554(6) Uani d . 1
O O3 0.30098(9) 0.3904(7) 0.84650(17) 0.0631(6) Uani d D 1
N N1 0.27769(8) 0.0670(6) 0.10791(18) 0.0420(5) Uani d . 1
N N2 0.31879(8) 0.2013(7) 0.15714(18) 0.0435(5) Uani d D 1
C C1 0.19752(9) -0.1146(7) 0.1247(2) 0.0355(6) Uani d . 1
C C2 0.19157(10) -0.2361(7) 0.0176(2) 0.0396(6) Uani d . 1
C C3 0.14878(11) -0.3907(8) -0.0177(2) 0.0504(8) Uani d . 1
H H3 0.1446 -0.4695 -0.0892 0.060 Uiso calc R 1
C C4 0.11279(11) -0.4269(8) 0.0528(3) 0.0527(8) Uani d . 1
H H4 0.0844 -0.5320 0.0287 0.063 Uiso calc R 1
C C5 0.11802(11) -0.3107(8) 0.1582(3) 0.0524(7) Uani d . 1
H H5 0.0933 -0.3369 0.2053 0.063 Uiso calc R 1
C C6 0.16008(11) -0.1548(7) 0.1940(2) 0.0446(6) Uani d . 1
H H6 0.1636 -0.0752 0.2655 0.054 Uiso calc R 1
C C7 0.24163(9) 0.0418(7) 0.1670(2) 0.0399(6) Uani d . 1
H H7 0.2437 0.1251 0.2383 0.048 Uiso calc R 1
C C8 0.35906(10) 0.1958(7) 0.1026(2) 0.0410(6) Uani d . 1
C C9 0.40330(9) 0.3079(7) 0.16605(19) 0.0388(6) Uani d . 1
C C10 0.44136(11) 0.4366(8) 0.1104(2) 0.0480(7) Uani d . 1
H H10 0.4391 0.4588 0.0349 0.058 Uiso calc R 1
C C11 0.48227(11) 0.5306(9) 0.1682(2) 0.0525(8) Uani d . 1
H H11 0.5083 0.6190 0.1333 0.063 Uiso calc R 1
C C12 0.48349(10) 0.4898(8) 0.2797(2) 0.0449(7) Uani d . 1
N N3 0.44856(9) 0.3663(7) 0.33543(19) 0.0485(6) Uani d . 1
C C13 0.40865(10) 0.2742(8) 0.2784(2) 0.0459(7) Uani d . 1
H H13 0.3834 0.1838 0.3159 0.055 Uiso calc R 1
H H2 0.3168(13) 0.308(10) 0.2220(17) 0.080 Uiso d D 1
H H3B 0.2754(7) 0.427(11) 0.880(2) 0.080 Uiso d D 1
H H3A 0.3231(8) 0.362(10) 0.895(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
H3B O3 H3A 107(2)
C7 N1 N2 116.8(2)
C8 N2 N1 119.0(2)
C8 N2 H2 123(2)
N1 N2 H2 118(2)
C6 C1 C2 118.6(2)
C6 C1 C7 119.0(2)
C2 C1 C7 122.4(2)
O1 C2 C3 118.7(2)
O1 C2 C1 121.5(2)
C3 C2 C1 119.8(3)
C4 C3 C2 120.0(3)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 121.0(3)
C3 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C6 119.5(3)
C4 C5 H5 120.2
C6 C5 H5 120.2
C5 C6 C1 121.0(3)
C5 C6 H6 119.5
C1 C6 H6 119.5
N1 C7 C1 121.0(2)
N1 C7 H7 119.5
C1 C7 H7 119.5
O2 C8 N2 123.8(2)
O2 C8 C9 120.4(3)
N2 C8 C9 115.8(2)
C13 C9 C10 118.3(2)
C13 C9 C8 122.6(2)
C10 C9 C8 119.1(2)
C11 C10 C9 119.1(3)
C11 C10 H10 120.4
C9 C10 H10 120.4
C10 C11 C12 117.7(3)
C10 C11 H11 121.1
C12 C11 H11 121.1
N3 C12 C11 125.2(3)
N3 C12 Cl1 115.5(2)
C11 C12 Cl1 119.3(2)
C12 N3 C13 116.8(2)
N3 C13 C9 122.9(3)
N3 C13 H13 118.5
C9 C13 H13 118.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C12 1.742(3)
O1 C2 1.353(3)
O1 H1 0.8200
O2 C8 1.230(3)
O3 H3B 0.856(10)
O3 H3A 0.849(10)
N1 C7 1.279(3)
N1 N2 1.377(3)
N2 C8 1.343(4)
N2 H2 0.899(10)
C1 C6 1.394(4)
C1 C2 1.398(3)
C1 C7 1.451(3)
C2 C3 1.391(4)
C3 C4 1.370(4)
C3 H3 0.9300
C4 C5 1.370(5)
C4 H4 0.9300
C5 C6 1.377(4)
C5 H5 0.9300
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.498(3)
C9 C13 1.387(4)
C9 C10 1.387(4)
C10 C11 1.370(4)
C10 H10 0.9300
C11 C12 1.377(4)
C11 H11 0.9300
C12 N3 1.312(4)
N3 C13 1.341(3)
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
O3 H3A O2 1_556 0.849(10) 1.98(2) 2.771(3) 155(4)
O3 H3B O1 1_566 0.856(10) 2.15(2) 2.917(4) 149(4)
N2 H2 O3 2_564 0.899(10) 1.982(14) 2.864(3) 167(4)
O1 H1 N1 . 0.82 1.89 2.610(3) 147
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21184347
