#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220703.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_2220703
loop_
_publ_author_name
'Li, Man-Lin'
'Huang, Xianqiang'
'Feng, Ruo-Kun'
_publ_section_title
;
 (E)-N'-[1-(4-Chlorophenyl)ethylidene]-2-hydroxybenzohydrazide
;
_journal_coeditor_code           BI2333
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o369
_journal_paper_doi               10.1107/S1600536809002311
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 Cl N2 O2'
_chemical_formula_moiety         'C15 H13 Cl N2 O2'
_chemical_formula_sum            'C15 H13 Cl N2 O2'
_chemical_formula_weight         288.72
_chemical_name_systematic
;
(E)-N'-[1-(4-Chlorophenyl)ethylidene]-2-hydroxybenzohydrazide
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.530(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.900(3)
_cell_length_b                   7.8800(10)
_cell_length_c                   13.4899(15)
_cell_measurement_reflns_used    951
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.100
_cell_measurement_theta_min      2.709
_cell_volume                     2719.2(5)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and 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  0.0816
_diffrn_reflns_av_sigmaI/netI    0.1041
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4744
_diffrn_reflns_theta_full        21.96
_diffrn_reflns_theta_max         21.96
_diffrn_reflns_theta_min         1.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.370
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0648
_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)+(0.1726P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.2657
_reflns_number_gt                901
_reflns_number_total             1663
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2333.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220703
_cod_database_fobs_code          2220703
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.16974(8) 0.5453(3) -0.40292(16) 0.0745(9) Uani d . 1 . .
N N1 0.07264(19) 0.1148(7) 0.0780(4) 0.0390(15) Uani d . 1 . .
H H1 0.0712 0.1193 0.1404 0.047 Uiso calc R 1 . .
N N2 0.0332(2) 0.1842(7) -0.0112(4) 0.0372(15) Uani d . 1 . .
O O1 0.11636(19) 0.0271(8) -0.0221(4) 0.0714(19) Uani d . 1 . .
O O2 0.11905(18) 0.0618(6) 0.2888(3) 0.0531(15) Uani d . 1 . .
H H2 0.1252 0.0612 0.3535 0.080 Uiso calc R 1 . .
C C1 0.1133(2) 0.0401(10) 0.0666(5) 0.0422(19) Uani d . 1 . .
C C2 0.1557(2) -0.0358(9) 0.1654(5) 0.0400(18) Uani d . 1 . .
C C3 0.1585(2) -0.0201(9) 0.2719(5) 0.0405(19) Uani d . 1 . .
C C4 0.2007(3) -0.0898(10) 0.3581(5) 0.050(2) Uani d . 1 . .
H H4 0.2027 -0.0789 0.4283 0.060 Uiso calc R 1 . .
C C5 0.2391(3) -0.1741(11) 0.3394(6) 0.063(2) Uani d . 1 . .
H H5 0.2671 -0.2198 0.3975 0.075 Uiso calc R 1 . .
C C6 0.2372(3) -0.1928(11) 0.2365(6) 0.060(2) Uani d . 1 . .
H H6 0.2627 -0.2543 0.2242 0.071 Uiso calc R 1 . .
C C7 0.1960(3) -0.1174(9) 0.1511(6) 0.0457(19) Uani d . 1 . .
H H7 0.1958 -0.1225 0.0820 0.055 Uiso calc R 1 . .
C C8 -0.0107(3) 0.2598(11) 0.1122(5) 0.056(2) Uani d . 1 . .
H H8A -0.0043 0.1505 0.1465 0.084 Uiso calc R 1 . .
H H8B -0.0452 0.2971 0.1005 0.084 Uiso calc R 1 . .
H H8C 0.0145 0.3397 0.1578 0.084 Uiso calc R 1 . .
C C9 -0.0057(2) 0.2471(9) 0.0044(5) 0.0405(18) Uani d . 1 . .
C C10 -0.0473(3) 0.3259(9) -0.0938(5) 0.0387(18) Uani d . 1 . .
C C11 -0.0867(3) 0.4294(9) -0.0915(5) 0.046(2) Uani d . 1 . .
H H11 -0.0883 0.4545 -0.0254 0.055 Uiso calc R 1 . .
C C12 -0.1242(3) 0.4970(10) -0.1857(6) 0.052(2) Uani d . 1 . .
H H12 -0.1503 0.5674 -0.1824 0.063 Uiso calc R 1 . .
C C13 -0.1227(3) 0.4592(9) -0.2842(5) 0.0430(19) Uani d . 1 . .
C C14 -0.0845(3) 0.3575(10) -0.2901(5) 0.052(2) Uani d . 1 . .
H H14 -0.0827 0.3366 -0.3563 0.062 Uiso calc R 1 . .
C C15 -0.0479(3) 0.2847(9) -0.1954(5) 0.0450(19) Uani d . 1 . .
H H15 -0.0236 0.2077 -0.2001 0.054 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 N2 . . 119.4(5) ?
C1 N1 H1 . . 120.3 ?
N2 N1 H1 . . 120.3 ?
C9 N2 N1 . . 116.2(5) ?
C3 O2 H2 . . 109.5 ?
O1 C1 N1 . . 122.4(6) ?
O1 C1 C2 . . 119.3(6) ?
N1 C1 C2 . . 118.3(5) ?
C7 C2 C3 . . 117.8(6) ?
C7 C2 C1 . . 117.3(5) ?
C3 C2 C1 . . 124.8(6) ?
O2 C3 C4 . . 120.8(6) ?
O2 C3 C2 . . 119.2(6) ?
C4 C3 C2 . . 120.0(6) ?
C5 C4 C3 . . 120.0(6) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 121.3(7) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C5 C6 C7 . . 118.4(7) ?
C5 C6 H6 . . 120.8 ?
C7 C6 H6 . . 120.8 ?
C2 C7 C6 . . 122.3(6) ?
C2 C7 H7 . . 118.8 ?
C6 C7 H7 . . 118.8 ?
C9 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C9 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N2 C9 C10 . . 114.8(5) ?
N2 C9 C8 . . 126.1(6) ?
C10 C9 C8 . . 118.9(6) ?
C11 C10 C15 . . 117.4(6) ?
C11 C10 C9 . . 124.5(5) ?
C15 C10 C9 . . 118.0(6) ?
C10 C11 C12 . . 121.4(6) ?
C10 C11 H11 . . 119.3 ?
C12 C11 H11 . . 119.3 ?
C13 C12 C11 . . 119.8(7) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C14 C13 C12 . . 120.7(6) ?
C14 C13 Cl1 . . 119.6(5) ?
C12 C13 Cl1 . . 119.8(6) ?
C13 C14 C15 . . 119.4(6) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C14 C15 C10 . . 121.1(7) ?
C14 C15 H15 . . 119.4 ?
C10 C15 H15 . . 119.4 ?
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
Cl1 C13 . 1.752(7) ?
N1 C1 . 1.340(8) ?
N1 N2 . 1.379(7) ?
N1 H1 . 0.860 ?
N2 C9 . 1.284(8) ?
O1 C1 . 1.237(7) ?
O2 C3 . 1.372(8) ?
O2 H2 . 0.820 ?
C1 C2 . 1.508(9) ?
C2 C7 . 1.374(9) ?
C2 C3 . 1.412(9) ?
C3 C4 . 1.395(9) ?
C4 C5 . 1.367(10) ?
C4 H4 . 0.930 ?
C5 C6 . 1.375(10) ?
C5 H5 . 0.930 ?
C6 C7 . 1.395(9) ?
C6 H6 . 0.930 ?
C7 H7 . 0.930 ?
C8 C9 . 1.518(8) ?
C8 H8A . 0.960 ?
C8 H8B . 0.960 ?
C8 H8C . 0.960 ?
C9 C10 . 1.503(9) ?
C10 C11 . 1.380(9) ?
C10 C15 . 1.403(8) ?
C11 C12 . 1.390(9) ?
C11 H11 . 0.930 ?
C12 C13 . 1.379(10) ?
C12 H12 . 0.930 ?
C13 C14 . 1.361(10) ?
C14 C15 . 1.400(9) ?
C14 H14 . 0.930 ?
C15 H15 . 0.930 ?
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
N1 H1 O2 . 0.86 1.96 2.645(6) 135.2
O2 H2 O1 6_556 0.82 1.92 2.676(6) 152.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7890392
