#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/65/2226587.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_2226587
loop_
_publ_author_name
'Hao, Yu-Mei'
_publ_section_title
;
 N'-(5-Chloro-2-hydroxybenzylidene)-2-methoxybenzohydrazide
;
_journal_coeditor_code           LH5065
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1631
_journal_paper_doi               10.1107/S160053681002180X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 Cl N2 O3'
_chemical_formula_moiety         'C15 H13 Cl N2 O3'
_chemical_formula_sum            'C15 H13 Cl N2 O3'
_chemical_formula_weight         304.72
_chemical_name_systematic
;
N'-(5-Chloro-2-hydroxybenzylidene)-2-methoxybenzohydrazide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.392(3)
_cell_length_b                   9.110(2)
_cell_length_c                   20.128(3)
_cell_measurement_reflns_used    868
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.4
_cell_volume                     2822.4(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_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  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9958
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.9277
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                1463
_reflns_number_total             3051
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5065.cif
_cod_data_source_block           I
_cod_database_code               2226587
_cod_database_fobs_code          2226587
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 1.23358(6) 1.00596(10) 0.43870(5) 0.0931(4) Uani d . 1 . .
N N1 0.83185(15) 1.0819(2) 0.38838(11) 0.0491(6) Uani d . 1 . .
N N2 0.76629(15) 1.0034(2) 0.35851(13) 0.0532(7) Uani d D 1 . .
O O1 0.89608(14) 1.2927(2) 0.46463(12) 0.0713(7) Uani d . 1 . .
H H1 0.8575 1.2452 0.4466 0.107 Uiso calc R 1 . .
O O2 0.67478(12) 1.1960(2) 0.36350(11) 0.0626(6) Uani d . 1 . .
O O3 0.71657(13) 0.8451(2) 0.24964(11) 0.0675(6) Uani d . 1 . .
C C1 0.9728(2) 1.2226(3) 0.45691(15) 0.0547(8) Uani d . 1 . .
C C2 1.0460(2) 1.2825(3) 0.48644(16) 0.0670(9) Uani d . 1 . .
H H2 1.0410 1.3690 0.5107 0.080 Uiso calc R 1 . .
C C3 1.1255(2) 1.2168(4) 0.48063(16) 0.0710(10) Uani d . 1 . .
H H3 1.1741 1.2579 0.5007 0.085 Uiso calc R 1 . .
C C4 1.13245(19) 1.0896(4) 0.44478(16) 0.0600(8) Uani d . 1 . .
C C5 1.06147(18) 1.0276(3) 0.41535(16) 0.0557(8) Uani d . 1 . .
H H5 1.0676 0.9407 0.3916 0.067 Uiso calc R 1 . .
C C6 0.97993(17) 1.0929(3) 0.42047(14) 0.0477(7) Uani d . 1 . .
C C7 0.90686(18) 1.0219(3) 0.38947(14) 0.0487(7) Uani d . 1 . .
H H7 0.9144 0.9305 0.3698 0.058 Uiso calc R 1 . .
C C8 0.68942(18) 1.0680(3) 0.34816(13) 0.0467(7) Uani d . 1 . .
C C9 0.61993(17) 0.9746(3) 0.31858(15) 0.0494(7) Uani d . 1 . .
C C10 0.53588(19) 1.0005(3) 0.34012(16) 0.0573(8) Uani d . 1 . .
H H10 0.5259 1.0737 0.3714 0.069 Uiso calc R 1 . .
C C11 0.4666(2) 0.9204(4) 0.31633(18) 0.0675(9) Uani d . 1 . .
H H11 0.4108 0.9375 0.3322 0.081 Uiso calc R 1 . .
C C12 0.4811(2) 0.8159(4) 0.26919(19) 0.0721(10) Uani d . 1 . .
H H12 0.4346 0.7624 0.2524 0.086 Uiso calc R 1 . .
C C13 0.5630(2) 0.7886(3) 0.24629(17) 0.0654(9) Uani d . 1 . .
H H13 0.5716 0.7170 0.2140 0.078 Uiso calc R 1 . .
C C14 0.63371(19) 0.8664(3) 0.27054(15) 0.0519(8) Uani d . 1 . .
C C15 0.7318(2) 0.7299(4) 0.20290(18) 0.0821(11) Uani d . 1 . .
H H15A 0.7109 0.6388 0.2208 0.123 Uiso calc R 1 . .
H H15B 0.7930 0.7222 0.1943 0.123 Uiso calc R 1 . .
H H15C 0.7018 0.7513 0.1622 0.123 Uiso calc R 1 . .
H H2A 0.7748(19) 0.9090(14) 0.3487(15) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 N2 . . 116.6(2) ?
C8 N2 N1 . . 119.2(2) ?
C8 N2 H2A . . 121(2) ?
N1 N2 H2A . . 119(2) ?
C1 O1 H1 . . 109.5 ?
C14 O3 C15 . . 117.6(2) ?
O1 C1 C2 . . 118.4(3) ?
O1 C1 C6 . . 122.0(3) ?
C2 C1 C6 . . 119.6(3) ?
C3 C2 C1 . . 121.3(3) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
C2 C3 C4 . . 119.0(3) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C5 C4 C3 . . 121.1(3) ?
C5 C4 Cl1 . . 120.4(3) ?
C3 C4 Cl1 . . 118.6(3) ?
C4 C5 C6 . . 120.9(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 118.1(3) ?
C5 C6 C7 . . 118.7(3) ?
C1 C6 C7 . . 123.1(3) ?
N1 C7 C6 . . 121.4(3) ?
N1 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
O2 C8 N2 . . 122.8(2) ?
O2 C8 C9 . . 120.8(2) ?
N2 C8 C9 . . 116.5(2) ?
C10 C9 C14 . . 118.6(3) ?
C10 C9 C8 . . 116.6(3) ?
C14 C9 C8 . . 124.8(3) ?
C11 C10 C9 . . 121.6(3) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C12 C11 C10 . . 119.1(3) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C11 C12 C13 . . 120.9(3) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C14 . . 120.8(3) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
O3 C14 C13 . . 123.7(3) ?
O3 C14 C9 . . 117.3(2) ?
C13 C14 C9 . . 119.0(3) ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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 C4 . 1.737(3) ?
N1 C7 . 1.278(3) ?
N1 N2 . 1.375(3) ?
N2 C8 . 1.338(3) ?
N2 H2A . 0.892(10) ?
O1 C1 . 1.351(3) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.227(3) ?
O3 C14 . 1.357(3) ?
O3 C15 . 1.429(3) ?
C1 C2 . 1.386(4) ?
C1 C6 . 1.395(4) ?
C2 C3 . 1.367(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.369(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.365(4) ?
C5 C6 . 1.393(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.439(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.491(4) ?
C9 C10 . 1.385(4) ?
C9 C14 . 1.397(4) ?
C10 C11 . 1.377(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.363(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.365(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.387(4) ?
C13 H13 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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 H1 N1 . 0.82 1.93 2.649(3) 145.3
N2 H2A O2 8_755 0.892(10) 2.111(16) 2.946(3) 155(3)
N2 H2A O3 . 0.892(10) 2.26(3) 2.733(3) 113(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745271
