#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225992.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_2225992
loop_
_publ_author_name
'Hao, Yu-Mei'
_publ_section_title
;
 N'-[(2-Hydroxy-1-naphthyl)methylidene]-2-nitrobenzohydrazide
;
_journal_coeditor_code           SU2174
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1177
_journal_paper_doi               10.1107/S160053681001490X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H13 N3 O4'
_chemical_formula_moiety         'C18 H13 N3 O4'
_chemical_formula_sum            'C18 H13 N3 O4'
_chemical_formula_weight         335.31
_chemical_name_systematic
;
N'-[(2-Hydroxy-1-naphthyl)methylidene]-2-nitrobenzohydrazide
;
_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                 113.963(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4473(6)
_cell_length_b                   29.068(2)
_cell_length_c                   7.8504(6)
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.6
_cell_volume                     1553.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8499
_diffrn_reflns_theta_full        25.88
_diffrn_reflns_theta_max         25.88
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9725
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0436
_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)+(0.0464P)²+0.0232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                1856
_reflns_number_total             2972
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2174.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2225992
_cod_database_fobs_code          2225992
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.9372(2) 0.21679(5) 0.1587(2) 0.0397(4) Uani d . 1 . .
N N2 0.8992(2) 0.24623(5) 0.0095(2) 0.0391(4) Uani d D 1 . .
N N3 0.8947(3) 0.38594(6) 0.0264(2) 0.0484(5) Uani d . 1 . .
O O1 0.9712(2) 0.20162(5) 0.49534(18) 0.0565(4) Uani d . 1 . .
H H1 0.9752 0.2167 0.4087 0.085 Uiso calc R 1 . .
O O2 1.1317(2) 0.29693(4) 0.18479(17) 0.0468(4) Uani d . 1 . .
O O3 0.8562(2) 0.36371(5) 0.1378(2) 0.0621(5) Uani d . 1 . .
O O4 0.9318(3) 0.42719(5) 0.0425(2) 0.0876(6) Uani d . 1 . .
C C1 0.8835(3) 0.14285(6) 0.2610(3) 0.0380(5) Uani d . 1 . .
C C2 0.9240(3) 0.15757(6) 0.4402(3) 0.0411(5) Uani d . 1 . .
C C3 0.9145(3) 0.12727(7) 0.5760(3) 0.0517(6) Uani d . 1 . .
H H3 0.9385 0.1380 0.6949 0.062 Uiso calc R 1 . .
C C4 0.8703(3) 0.08250(8) 0.5329(3) 0.0570(6) Uani d . 1 . .
H H4 0.8643 0.0628 0.6236 0.068 Uiso calc R 1 . .
C C5 0.8329(3) 0.06477(7) 0.3541(3) 0.0506(6) Uani d . 1 . .
C C6 0.7861(4) 0.01817(8) 0.3104(4) 0.0742(8) Uani d . 1 . .
H H6 0.7802 -0.0016 0.4012 0.089 Uiso calc R 1 . .
C C7 0.7492(5) 0.00153(8) 0.1374(4) 0.0952(10) Uani d . 1 . .
H H7 0.7182 -0.0294 0.1101 0.114 Uiso calc R 1 . .
C C8 0.7582(4) 0.03098(8) 0.0022(4) 0.0897(9) Uani d . 1 . .
H H8 0.7343 0.0195 -0.1156 0.108 Uiso calc R 1 . .
C C9 0.8014(4) 0.07638(7) 0.0383(3) 0.0661(7) Uani d . 1 . .
H H9 0.8057 0.0954 -0.0553 0.079 Uiso calc R 1 . .
C C10 0.8398(3) 0.09508(6) 0.2155(3) 0.0439(5) Uani d . 1 . .
C C11 0.8723(3) 0.17566(6) 0.1180(3) 0.0402(5) Uani d . 1 . .
H H11 0.8167 0.1666 -0.0063 0.048 Uiso calc R 1 . .
C C12 0.9971(3) 0.28614(6) 0.0366(2) 0.0348(4) Uani d . 1 . .
C C13 0.9339(3) 0.31554(6) -0.1353(2) 0.0331(4) Uani d . 1 . .
C C14 0.8952(3) 0.36234(6) -0.1387(2) 0.0352(5) Uani d . 1 . .
C C15 0.8493(3) 0.38854(7) -0.2967(3) 0.0479(5) Uani d . 1 . .
H H15 0.8260 0.4199 -0.2947 0.057 Uiso calc R 1 . .
C C16 0.8383(3) 0.36763(7) -0.4579(3) 0.0528(6) Uani d . 1 . .
H H16 0.8061 0.3849 -0.5660 0.063 Uiso calc R 1 . .
C C17 0.8747(3) 0.32149(7) -0.4602(3) 0.0487(6) Uani d . 1 . .
H H17 0.8671 0.3076 -0.5696 0.058 Uiso calc R 1 . .
C C18 0.9226(3) 0.29568(6) -0.3002(2) 0.0406(5) Uani d . 1 . .
H H18 0.9478 0.2644 -0.3029 0.049 Uiso calc R 1 . .
H H2 0.808(3) 0.2378(7) -0.1025(18) 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
C11 N1 N2 . . 116.07(15) ?
C12 N2 N1 . . 119.34(15) ?
C12 N2 H2 . . 122.4(14) ?
N1 N2 H2 . . 118.3(14) ?
O3 N3 O4 . . 123.87(18) ?
O3 N3 C14 . . 118.30(17) ?
O4 N3 C14 . . 117.83(18) ?
C2 O1 H1 . . 109.5 ?
C2 C1 C10 . . 119.08(17) ?
C2 C1 C11 . . 120.32(17) ?
C10 C1 C11 . . 120.47(17) ?
O1 C2 C1 . . 122.73(17) ?
O1 C2 C3 . . 115.90(17) ?
C1 C2 C3 . . 121.36(18) ?
C4 C3 C2 . . 119.7(2) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 122.0(2) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C6 C5 C4 . . 121.5(2) ?
C6 C5 C10 . . 119.6(2) ?
C4 C5 C10 . . 118.81(19) ?
C7 C6 C5 . . 121.0(2) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 119.5(2) ?
C6 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
C9 C8 C7 . . 121.4(3) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
C8 C9 C10 . . 121.0(2) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C9 C10 C5 . . 117.49(19) ?
C9 C10 C1 . . 123.50(18) ?
C5 C10 C1 . . 119.01(18) ?
N1 C11 C1 . . 121.60(17) ?
N1 C11 H11 . . 119.2 ?
C1 C11 H11 . . 119.2 ?
O2 C12 N2 . . 123.57(16) ?
O2 C12 C13 . . 122.88(16) ?
N2 C12 C13 . . 113.46(16) ?
C18 C13 C14 . . 117.16(16) ?
C18 C13 C12 . . 118.64(16) ?
C14 C13 C12 . . 124.12(16) ?
C15 C14 C13 . . 122.20(17) ?
C15 C14 N3 . . 116.68(17) ?
C13 C14 N3 . . 121.09(16) ?
C14 C15 C16 . . 119.03(19) ?
C14 C15 H15 . . 120.5 ?
C16 C15 H15 . . 120.5 ?
C17 C16 C15 . . 120.40(19) ?
C17 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
C16 C17 C18 . . 120.01(19) ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C17 C18 C13 . . 121.19(18) ?
C17 C18 H18 . . 119.4 ?
C13 C18 H18 . . 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
N1 C11 . 1.281(2) ?
N1 N2 . 1.3838(19) ?
N2 C12 . 1.341(2) ?
N2 H2 . 0.899(9) ?
N3 O3 . 1.212(2) ?
N3 O4 . 1.225(2) ?
N3 C14 . 1.468(2) ?
O1 C2 . 1.352(2) ?
O1 H1 . 0.8200 ?
O2 C12 . 1.229(2) ?
C1 C2 . 1.381(2) ?
C1 C10 . 1.438(2) ?
C1 C11 . 1.449(2) ?
C2 C3 . 1.407(3) ?
C3 C4 . 1.351(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.413(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.406(3) ?
C5 C10 . 1.417(3) ?
C6 C7 . 1.360(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.386(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.360(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.411(3) ?
C9 H9 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.502(2) ?
C13 C18 . 1.388(2) ?
C13 C14 . 1.389(2) ?
C14 C15 . 1.375(2) ?
C15 C16 . 1.376(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.370(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.380(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 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
O1 H1 N1 . 0.82 1.87 2.5881(18) 146
N2 H2 O2 4_565 0.899(9) 1.938(11) 2.8133(19) 164(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12974008
