#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220750.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_2220750
loop_
_publ_author_name
'Sun, Yuying'
'Li, Hong-Gang'
'Wang, Xiao'
'Fu, Shizhou'
'Wang, Daqi'
_publ_section_title
2-Hydroxy-N'-[(E)-(3-hydroxy-2-naphthyl)methylene]benzohydrazide
_journal_coeditor_code           CV2501
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o262
_journal_paper_doi               10.1107/S1600536808044073
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H14 N2 O3'
_chemical_formula_moiety         'C18 H14 N2 O3'
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.31
_chemical_name_systematic
2-Hydroxy-N'-[(E)-(3-hydroxy-2-naphthyl)methylene]benzohydrazide
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   21.124(2)
_cell_length_b                   11.6212(13)
_cell_length_c                   5.9826(8)
_cell_measurement_reflns_used    1119
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.349
_cell_measurement_theta_min      2.606
_cell_volume                     1468.6(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6099
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1422
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0398
_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)+(0.0012P)²+0.7621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                896
_reflns_number_total             1422
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2501.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220750
_cod_database_fobs_code          2220750
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'
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 0.22373(16) 0.9395(3) 0.7320(6) 0.0514(10) Uani d . 1 . .
H H1 0.2172 0.8713 0.7828 0.062 Uiso calc R 1 . .
N N2 0.19138(18) 0.9753(3) 0.5434(6) 0.0536(11) Uani d . 1 . .
O O1 0.27673(14) 1.1075(2) 0.7748(6) 0.0703(10) Uani d . 1 . .
O O2 0.25278(12) 0.7725(2) 1.0077(6) 0.0574(9) Uani d . 1 . .
H H2 0.2526 0.7107 1.0739 0.086 Uiso calc R 1 . .
O O3 0.16012(13) 1.1067(3) 0.2045(6) 0.0664(10) Uani d . 1 . .
H H3 0.1787 1.0892 0.3199 0.100 Uiso calc R 1 . .
C C1 0.2649(2) 1.0079(4) 0.8375(8) 0.0504(12) Uani d . 1 . .
C C2 0.2955(2) 0.9611(3) 1.0404(8) 0.0447(11) Uani d . 1 . .
C C3 0.2891(2) 0.8497(3) 1.1229(7) 0.0441(12) Uani d . 1 . .
C C4 0.3185(2) 0.8179(4) 1.3196(8) 0.0544(13) Uani d . 1 . .
H H4 0.3135 0.7435 1.3740 0.065 Uiso calc R 1 . .
C C5 0.3548(2) 0.8948(5) 1.4348(9) 0.0672(15) Uani d . 1 . .
H H5 0.3750 0.8718 1.5655 0.081 Uiso calc R 1 . .
C C6 0.3618(2) 1.0054(5) 1.3596(10) 0.0718(16) Uani d . 1 . .
H H6 0.3863 1.0578 1.4392 0.086 Uiso calc R 1 . .
C C7 0.3321(2) 1.0378(4) 1.1646(10) 0.0614(14) Uani d . 1 . .
H H7 0.3366 1.1130 1.1142 0.074 Uiso calc R 1 . .
C C8 0.1536(2) 0.8994(4) 0.4641(8) 0.0546(13) Uani d . 1 . .
H H8 0.1507 0.8288 0.5363 0.066 Uiso calc R 1 . .
C C9 0.1152(2) 0.9189(4) 0.2659(8) 0.0493(12) Uani d . 1 . .
C C10 0.1211(2) 1.0193(4) 0.1429(8) 0.0495(12) Uani d . 1 . .
C C11 0.0868(2) 1.0370(4) -0.0549(8) 0.0560(13) Uani d . 1 . .
H H11 0.0914 1.1054 -0.1339 0.067 Uiso calc R 1 . .
C C12 0.0468(2) 0.9542(4) -0.1312(9) 0.0607(14) Uani d . 1 . .
H H12 0.0255 0.9653 -0.2656 0.073 Uiso calc R 1 . .
C C13 0.0369(2) 0.8510(4) -0.0089(9) 0.0548(13) Uani d . 1 . .
C C14 0.07102(19) 0.8331(4) 0.1920(8) 0.0511(12) Uani d . 1 . .
C C15 0.0568(2) 0.7320(4) 0.3138(9) 0.0656(15) Uani d . 1 . .
H H15 0.0780 0.7173 0.4470 0.079 Uiso calc R 1 . .
C C16 0.0128(2) 0.6564(5) 0.2396(11) 0.0790(19) Uani d . 1 . .
H H16 0.0044 0.5909 0.3239 0.095 Uiso calc R 1 . .
C C17 -0.0202(2) 0.6734(5) 0.0415(12) 0.0771(17) Uani d . 1 . .
H H17 -0.0500 0.6199 -0.0067 0.093 Uiso calc R 1 . .
C C18 -0.0082(2) 0.7700(4) -0.0809(9) 0.0686(16) Uani d . 1 . .
H H18 -0.0301 0.7825 -0.2136 0.082 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 . . 121.8(4) ?
C1 N1 H1 . . 119.1 ?
N2 N1 H1 . . 119.1 ?
C8 N2 N1 . . 113.8(4) ?
C3 O2 H2 . . 109.5 ?
C10 O3 H3 . . 109.5 ?
O1 C1 N1 . . 122.9(4) ?
O1 C1 C2 . . 120.2(5) ?
N1 C1 C2 . . 116.9(4) ?
C3 C2 C7 . . 117.3(4) ?
C3 C2 C1 . . 126.2(4) ?
C7 C2 C1 . . 116.4(4) ?
O2 C3 C4 . . 120.5(4) ?
O2 C3 C2 . . 119.1(4) ?
C4 C3 C2 . . 120.5(4) ?
C5 C4 C3 . . 120.6(5) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.6(5) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C7 . . 119.0(5) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
C6 C7 C2 . . 122.0(5) ?
C6 C7 H7 . . 119.0 ?
C2 C7 H7 . . 119.0 ?
N2 C8 C9 . . 122.9(4) ?
N2 C8 H8 . . 118.6 ?
C9 C8 H8 . . 118.6 ?
C10 C9 C14 . . 118.7(4) ?
C10 C9 C8 . . 120.9(4) ?
C14 C9 C8 . . 120.4(4) ?
O3 C10 C9 . . 122.7(4) ?
O3 C10 C11 . . 115.7(4) ?
C9 C10 C11 . . 121.6(5) ?
C12 C11 C10 . . 120.1(5) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C11 C12 C13 . . 121.1(5) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C18 C13 C14 . . 120.4(5) ?
C18 C13 C12 . . 120.4(5) ?
C14 C13 C12 . . 119.1(5) ?
C15 C14 C13 . . 116.8(5) ?
C15 C14 C9 . . 123.8(5) ?
C13 C14 C9 . . 119.4(4) ?
C16 C15 C14 . . 121.1(5) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
C15 C16 C17 . . 122.1(6) ?
C15 C16 H16 . . 118.9 ?
C17 C16 H16 . . 118.9 ?
C18 C17 C16 . . 118.8(6) ?
C18 C17 H17 . . 120.6 ?
C16 C17 H17 . . 120.6 ?
C17 C18 C13 . . 120.8(6) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?
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 C1 . 1.336(5) ?
N1 N2 . 1.383(5) ?
N1 H1 . 0.8600 ?
N2 C8 . 1.280(5) ?
O1 C1 . 1.242(5) ?
O2 C3 . 1.366(5) ?
O2 H2 . 0.8200 ?
O3 C10 . 1.359(5) ?
O3 H3 . 0.8200 ?
C1 C2 . 1.479(6) ?
C2 C3 . 1.392(5) ?
C2 C7 . 1.395(6) ?
C3 C4 . 1.381(6) ?
C4 C5 . 1.364(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.370(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.377(7) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.455(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.386(5) ?
C9 C14 . 1.435(5) ?
C10 C11 . 1.403(6) ?
C11 C12 . 1.360(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.420(6) ?
C12 H12 . 0.9300 ?
C13 C18 . 1.407(6) ?
C13 C14 . 1.417(6) ?
C14 C15 . 1.415(6) ?
C15 C16 . 1.354(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.389(7) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.364(6) ?
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
O3 H3 N2 . 0.82 1.90 2.623(5) 146.4
N1 H1 O2 . 0.86 1.92 2.620(4) 137.3
O2 H2 O1 4_545 0.82 1.81 2.573(4) 154.7
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12230748
