#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/69/2216912.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_2216912
loop_
_publ_author_name
'Yun-Peng Diao'
'Yu-Hong Zhen'
'Xu Han'
'Sa Deng'
_publ_section_title
;
 3,5-Dihydroxy-N'-[(2-hydroxy-1-naphthyl)methylene]benzohydrazide
;
_journal_coeditor_code           BI2266
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o101
_journal_page_last               o101
_journal_paper_doi               10.1107/S1600536807062861
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H14 N2 O4'
_chemical_formula_moiety         'C18 H14 N2 O4'
_chemical_formula_sum            'C18 H14 N2 O4'
_chemical_formula_weight         322.31
_chemical_name_systematic
;
3,5-Dihydroxy-N'-[(2-hydroxy-1-naphthyl)methylene]benzohydrazide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.354(3)
_cell_length_b                   14.133(3)
_cell_length_c                   15.077(3)
_cell_measurement_reflns_used    5426
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.4
_cell_volume                     2845.5(10)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXTL (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15775
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9714
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0378
_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)+(0.0562P)²+0.7945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2433
_reflns_number_total             2949
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2266.cif
_cod_data_source_block           I
_cod_database_code               2216912
_cod_database_fobs_code          2216912
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
O O1 0.70957(9) -0.44067(6) 0.65672(7) 0.0446(3) Uani d . 1
H H1 0.6882 -0.4716 0.6987 0.067 Uiso calc R 1
O O2 0.64726(9) -0.17869(7) 0.84818(6) 0.0425(3) Uani d . 1
H H2 0.6418 -0.2214 0.8847 0.064 Uiso calc R 1
O O3 0.61626(10) -0.17124(7) 0.45805(7) 0.0468(3) Uani d . 1
O O4 0.61263(10) 0.02287(7) 0.29946(7) 0.0486(3) Uani d . 1
H H4 0.6170 -0.0031 0.3480 0.073 Uiso calc R 1
N N1 0.64522(10) -0.04149(8) 0.53870(8) 0.0359(3) Uani d D 1
N N2 0.62939(10) 0.01212(8) 0.46461(8) 0.0363(3) Uani d . 1
C C1 0.65842(10) -0.19422(9) 0.60952(9) 0.0308(3) Uani d . 1
C C2 0.67691(11) -0.28981(9) 0.59712(9) 0.0336(3) Uani d . 1
H H2A 0.6811 -0.3150 0.5402 0.040 Uiso calc R 1
C C3 0.68890(11) -0.34676(9) 0.67002(9) 0.0320(3) Uani d . 1
C C4 0.68089(11) -0.31096(9) 0.75469(9) 0.0317(3) Uani d . 1
H H4A 0.6893 -0.3504 0.8035 0.038 Uiso calc R 1
C C5 0.66031(10) -0.21629(9) 0.76661(9) 0.0308(3) Uani d . 1
C C6 0.65109(10) -0.15717(9) 0.69414(9) 0.0317(3) Uani d . 1
H H6 0.6400 -0.0928 0.7022 0.038 Uiso calc R 1
C C7 0.63939(11) -0.13645(9) 0.52904(9) 0.0330(3) Uani d . 1
C C8 0.62525(11) 0.10148(9) 0.47179(9) 0.0329(3) Uani d . 1
H H8 0.6324 0.1299 0.5271 0.040 Uiso calc R 1
C C9 0.60931(10) 0.15896(9) 0.39384(9) 0.0306(3) Uani d . 1
C C10 0.60344(11) 0.11717(10) 0.31095(9) 0.0350(3) Uani d . 1
C C11 0.58622(12) 0.17008(11) 0.23410(10) 0.0423(4) Uani d . 1
H H11 0.5823 0.1401 0.1793 0.051 Uiso calc R 1
C C12 0.57537(12) 0.26432(11) 0.23968(10) 0.0428(4) Uani d . 1
H H12 0.5621 0.2988 0.1885 0.051 Uiso calc R 1
C C13 0.58356(11) 0.31214(10) 0.32116(10) 0.0373(3) Uani d . 1
C C14 0.57676(13) 0.41122(11) 0.32600(12) 0.0503(4) Uani d . 1
H H14 0.5644 0.4457 0.2746 0.060 Uiso calc R 1
C C15 0.58771(15) 0.45740(11) 0.40359(14) 0.0577(5) Uani d . 1
H H15 0.5848 0.5231 0.4053 0.069 Uiso calc R 1
C C16 0.60341(14) 0.40619(11) 0.48111(13) 0.0540(5) Uani d . 1
H H16 0.6103 0.4380 0.5347 0.065 Uiso calc R 1
C C17 0.60877(12) 0.30993(10) 0.47952(11) 0.0433(4) Uani d . 1
H H17 0.6182 0.2770 0.5323 0.052 Uiso calc R 1
C C18 0.60030(10) 0.25964(9) 0.39969(10) 0.0325(3) Uani d . 1
H H1A 0.6770(14) -0.0170(14) 0.5862(10) 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
C3 O1 H1 109.5
C5 O2 H2 109.5
C10 O4 H4 109.5
C7 N1 N2 116.97(11)
C7 N1 H1A 119.6(14)
N2 N1 H1A 120.6(14)
C8 N2 N1 119.28(12)
C6 C1 C2 120.41(12)
C6 C1 C7 122.26(12)
C2 C1 C7 117.16(12)
C3 C2 C1 118.99(12)
C3 C2 H2A 120.5
C1 C2 H2A 120.5
O1 C3 C2 118.34(12)
O1 C3 C4 120.46(12)
C2 C3 C4 121.20(12)
C3 C4 C5 119.55(12)
C3 C4 H4A 120.2
C5 C4 H4A 120.2
O2 C5 C4 121.77(12)
O2 C5 C6 118.08(12)
C4 C5 C6 120.15(12)
C5 C6 C1 119.64(12)
C5 C6 H6 120.2
C1 C6 H6 120.2
O3 C7 N1 120.67(12)
O3 C7 C1 122.67(12)
N1 C7 C1 116.62(12)
N2 C8 C9 119.79(13)
N2 C8 H8 120.1
C9 C8 H8 120.1
C10 C9 C18 118.36(12)
C10 C9 C8 120.20(12)
C18 C9 C8 121.44(12)
O4 C10 C9 122.13(12)
O4 C10 C11 115.90(13)
C9 C10 C11 121.96(13)
C12 C11 C10 119.77(14)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C13 121.54(13)
C11 C12 H12 119.2
C13 C12 H12 119.2
C14 C13 C12 121.28(14)
C14 C13 C18 119.30(15)
C12 C13 C18 119.42(13)
C15 C14 C13 121.38(15)
C15 C14 H14 119.3
C13 C14 H14 119.3
C14 C15 C16 119.60(15)
C14 C15 H15 120.2
C16 C15 H15 120.2
C17 C16 C15 120.85(17)
C17 C16 H16 119.6
C15 C16 H16 119.6
C16 C17 C18 121.13(15)
C16 C17 H17 119.4
C18 C17 H17 119.4
C17 C18 C13 117.72(13)
C17 C18 C9 123.38(13)
C13 C18 C9 118.90(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.3704(15)
O1 H1 0.820
O2 C5 1.3511(15)
O2 H2 0.820
O3 C7 1.2177(17)
O4 C10 1.3496(17)
O4 H4 0.820
N1 C7 1.3521(17)
N1 N2 1.3661(16)
N1 H1A 0.903(9)
N2 C8 1.2688(17)
C1 C6 1.3826(19)
C1 C2 1.3859(18)
C1 C7 1.4845(18)
C2 C3 1.3716(19)
C2 H2A 0.930
C3 C4 1.3774(19)
C4 C5 1.3776(17)
C4 H4A 0.930
C5 C6 1.3810(18)
C6 H6 0.930
C8 C9 1.4445(18)
C8 H8 0.930
C9 C10 1.3845(19)
C9 C18 1.4307(18)
C10 C11 1.398(2)
C11 C12 1.342(2)
C11 H11 0.930
C12 C13 1.406(2)
C12 H12 0.930
C13 C14 1.405(2)
C13 C18 1.4150(19)
C14 C15 1.348(3)
C14 H14 0.930
C15 C16 1.391(3)
C15 H15 0.930
C16 C17 1.363(2)
C16 H16 0.930
C17 C18 1.402(2)
C17 H17 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
O1 H1 O4 7_556 0.82 1.96 2.7671(15) 166.6
O2 H2 O3 7_556 0.82 1.91 2.7227(15) 171.8
O4 H4 N2 . 0.82 1.78 2.5046(16) 146.5
N1 H1A O1 8_765 0.903(9) 2.141(12) 2.9929(16) 157.0(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21195892
