#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227334.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227334
loop_
_publ_author_name
'Tang, Chun-Bao'
_publ_section_title
;
 N'-(4-Hydroxybenzylidene)-2-methylbenzohydrazide
;
_journal_coeditor_code           CI5176
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2482
_journal_paper_doi               10.1107/S1600536810035063
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H14 N2 O2'
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_systematic
;
N'-(4-Hydroxybenzylidene)-2-methylbenzohydrazide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   7.6900(15)
_cell_length_b                   11.701(2)
_cell_length_c                   14.471(3)
_cell_measurement_reflns_used    4917
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.2
_cell_volume                     1302.1(4)
_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  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10755
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1634
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0604P)²+0.1042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                1502
_reflns_number_total             1634
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5176.cif
_cod_data_source_block           I
_cod_database_code               2227334
_cod_database_fobs_code          2227334
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'
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
N N1 0.1045(2) 0.76789(13) 0.47260(10) 0.0442(4) Uani d . 1 . .
N N2 0.1260(2) 0.70443(13) 0.55210(10) 0.0433(4) Uani d D 1 . .
O O1 0.1276(2) 1.15917(11) 0.16838(8) 0.0439(3) Uani d . 1 . .
H H1 0.0660 1.1323 0.1275 0.066 Uiso calc R 1 . .
O O2 0.0277(2) 0.54745(11) 0.47842(8) 0.0480(4) Uani d . 1 . .
C C1 0.1310(2) 0.94736(15) 0.39752(11) 0.0369(4) Uani d . 1 . .
C C2 0.0694(2) 0.90743(16) 0.31255(12) 0.0397(4) Uani d . 1 . .
H H2A 0.0288 0.8328 0.3080 0.048 Uiso calc R 1 . .
C C3 0.0675(2) 0.97611(15) 0.23590(12) 0.0391(4) Uani d . 1 . .
H H3 0.0264 0.9482 0.1799 0.047 Uiso calc R 1 . .
C C4 0.1276(2) 1.08777(15) 0.24249(11) 0.0345(4) Uani d . 1 . .
C C5 0.1884(3) 1.12934(16) 0.32573(13) 0.0416(4) Uani d . 1 . .
H H5 0.2283 1.2042 0.3300 0.050 Uiso calc R 1 . .
C C6 0.1899(3) 1.05962(16) 0.40250(12) 0.0427(4) Uani d . 1 . .
H H6 0.2309 1.0880 0.4584 0.051 Uiso calc R 1 . .
C C7 0.1410(3) 0.87360(15) 0.47796(12) 0.0402(4) Uani d . 1 . .
H H7 0.1747 0.9043 0.5345 0.048 Uiso calc R 1 . .
C C8 0.0859(2) 0.59215(15) 0.54852(11) 0.0375(4) Uani d . 1 . .
C C9 0.1113(2) 0.52835(15) 0.63685(12) 0.0389(4) Uani d . 1 . .
C C10 0.1715(3) 0.41533(17) 0.63644(15) 0.0483(5) Uani d . 1 . .
C C11 0.1871(3) 0.3609(2) 0.7213(2) 0.0631(7) Uani d . 1 . .
H H11 0.2286 0.2863 0.7229 0.076 Uiso calc R 1 . .
C C12 0.1439(3) 0.4126(3) 0.80218(18) 0.0703(8) Uani d . 1 . .
H H12 0.1559 0.3732 0.8576 0.084 Uiso calc R 1 . .
C C13 0.0828(3) 0.5227(2) 0.80235(14) 0.0649(7) Uani d . 1 . .
H H13 0.0519 0.5579 0.8576 0.078 Uiso calc R 1 . .
C C14 0.0678(3) 0.5808(2) 0.71959(13) 0.0498(5) Uani d . 1 . .
H H14 0.0280 0.6559 0.7194 0.060 Uiso calc R 1 . .
C C15 0.2224(4) 0.3530(2) 0.5498(2) 0.0763(8) Uani d . 1 . .
H H15A 0.1196 0.3306 0.5167 0.114 Uiso calc R 1 . .
H H15B 0.2886 0.2863 0.5656 0.114 Uiso calc R 1 . .
H H15C 0.2915 0.4024 0.5116 0.114 Uiso calc R 1 . .
H H2 0.190(3) 0.733(2) 0.5994(13) 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'
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 . . 116.54(15) ?
C8 N2 N1 . . 117.68(14) ?
C8 N2 H2 . . 120.6(17) ?
N1 N2 H2 . . 119.9(17) ?
C4 O1 H1 . . 109.5 ?
C6 C1 C2 . . 118.12(15) ?
C6 C1 C7 . . 120.18(16) ?
C2 C1 C7 . . 121.65(16) ?
C3 C2 C1 . . 121.31(16) ?
C3 C2 H2A . . 119.3 ?
C1 C2 H2A . . 119.3 ?
C2 C3 C4 . . 119.52(16) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
O1 C4 C5 . . 118.15(16) ?
O1 C4 C3 . . 121.59(15) ?
C5 C4 C3 . . 120.26(15) ?
C6 C5 C4 . . 119.83(16) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 120.96(16) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
N1 C7 C1 . . 121.21(16) ?
N1 C7 H7 . . 119.4 ?
C1 C7 H7 . . 119.4 ?
O2 C8 N2 . . 122.01(15) ?
O2 C8 C9 . . 122.87(16) ?
N2 C8 C9 . . 115.07(15) ?
C14 C9 C10 . . 120.08(17) ?
C14 C9 C8 . . 119.10(17) ?
C10 C9 C8 . . 120.77(17) ?
C11 C10 C9 . . 117.2(2) ?
C11 C10 C15 . . 119.6(2) ?
C9 C10 C15 . . 123.19(19) ?
C12 C11 C10 . . 122.5(2) ?
C12 C11 H11 . . 118.8 ?
C10 C11 H11 . . 118.8 ?
C11 C12 C13 . . 120.2(2) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C14 . . 119.3(2) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C13 C14 C9 . . 120.7(2) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
C10 C15 H15A . . 109.5 ?
C10 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C10 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
N1 C7 . 1.271(2) ?
N1 N2 . 1.379(2) ?
N2 C8 . 1.350(2) ?
N2 H2 . 0.907(10) ?
O1 C4 . 1.3594(19) ?
O1 H1 . 0.82 ?
O2 C8 . 1.226(2) ?
C1 C6 . 1.391(3) ?
C1 C2 . 1.398(2) ?
C1 C7 . 1.451(2) ?
C2 C3 . 1.370(2) ?
C2 H2A . 0.93 ?
C3 C4 . 1.389(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.381(2) ?
C5 C6 . 1.378(2) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 H7 . 0.93 ?
C8 C9 . 1.493(2) ?
C9 C14 . 1.387(3) ?
C9 C10 . 1.401(3) ?
C10 C11 . 1.389(3) ?
C10 C15 . 1.503(3) ?
C11 C12 . 1.358(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.371(4) ?
C12 H12 . 0.93 ?
C13 C14 . 1.382(3) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
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 O2 3 0.82 1.96 2.7657(18) 166
O1 H1 N1 3 0.82 2.52 2.995(2) 118
N2 H2 O1 2_575 0.910(10) 2.140(10) 2.995(2) 158(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11013958
