#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/84/2218424.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_2218424
loop_
_publ_author_name
'Liang, Qi-Feng'
'Feng, Hai-Mei'
'Li, Feng-Qing'
_publ_section_title
;
 N'-Benzoyl-3-hydroxy-2-naphthohydrazide
;
_journal_coeditor_code           HG2387
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1008
_journal_paper_doi               10.1107/S1600536808012919
_journal_volume                  64
_journal_year                    2008
_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_melting_point_gt       219
_chemical_melting_point_lt       223
_chemical_name_systematic
;
N'-Benzoyl-3-hydroxy-2-naphthohydrazide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8049(10)
_cell_length_b                   5.0231(10)
_cell_length_c                   29.398(6)
_cell_measurement_reflns_used    4889
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.47
_cell_volume                     709.3(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2002)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2002)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            6959
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi,1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1798
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0471
_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)+(0.0467P)²+0.1714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                1397
_reflns_number_total             1798
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2387.cif
_cod_data_source_block           I
_cod_original_cell_volume        709.3(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2218424
_cod_database_fobs_code          2218424
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C C1 0.8504(7) -0.1340(8) 0.04316(11) 0.0580(10) Uani d . 1
H H1A 0.9337 -0.1095 0.0153 0.070 Uiso calc R 1
C C2 0.9282(8) 0.0197(9) 0.07930(11) 0.0644(11) Uani d . 1
H H2A 1.0645 0.1491 0.0759 0.077 Uiso calc R 1
C C3 0.5261(8) -0.3656(8) 0.08826(12) 0.0646(11) Uani d . 1
H H3A 0.3923 -0.4981 0.0909 0.078 Uiso calc R 1
C C4 0.6474(8) -0.3272(9) 0.04768(12) 0.0607(10) Uani d . 1
H H4A 0.5941 -0.4312 0.0228 0.073 Uiso calc R 1
C C5 0.5989(6) -0.2081(7) 0.12670(10) 0.0426(7) Uani d . 1
C C6 0.8049(6) -0.0137(7) 0.12216(10) 0.0438(7) Uani d . 1
C C7 0.8769(7) 0.1425(7) 0.16055(10) 0.0491(8) Uani d . 1
H H7A 1.0142 0.2715 0.1578 0.059 Uiso calc R 1
C C8 0.4731(7) -0.2387(8) 0.16918(11) 0.0512(8) Uani d . 1
H H8A 0.3369 -0.3684 0.1724 0.061 Uiso calc R 1
C C9 0.5449(5) -0.0842(6) 0.20558(9) 0.0362(6) Uani d . 1
C C10 0.7539(6) 0.1128(6) 0.20171(10) 0.0368(7) Uani d . 1
C C11 0.8542(5) 0.2972(6) 0.23870(9) 0.0371(6) Uani d . 1
C C12 0.6027(5) 0.5289(6) 0.34255(9) 0.0366(7) Uani d . 1
C C13 0.6956(6) 0.7103(6) 0.38002(9) 0.0355(7) Uani d . 1
C C14 0.5666(7) 0.6932(7) 0.42123(10) 0.0474(8) Uani d . 1
H H14A 0.4253 0.5694 0.4251 0.057 Uiso calc R 1
C C15 0.9033(6) 0.8972(7) 0.37430(10) 0.0432(7) Uani d . 1
H H15A 0.9915 0.9099 0.3466 0.052 Uiso calc R 1
C C16 0.9798(7) 1.0656(7) 0.40988(12) 0.0536(9) Uani d . 1
H H16A 1.1171 1.1933 0.4058 0.064 Uiso calc R 1
C C17 0.8531(7) 1.0442(7) 0.45115(11) 0.0530(9) Uani d . 1
H H17A 0.9074 1.1549 0.4752 0.064 Uiso calc R 1
C C18 0.6461(7) 0.8593(8) 0.45684(11) 0.0526(9) Uani d . 1
H H18A 0.5595 0.8457 0.4846 0.063 Uiso calc R 1
N N1 0.7200(5) 0.2895(6) 0.27768(8) 0.0417(6) Uani d . 1
H H1B 0.5876 0.1768 0.2812 0.050 Uiso calc R 1
N N2 0.7938(4) 0.4635(6) 0.31267(7) 0.0410(6) Uani d . 1
H H2B 0.9596 0.5276 0.3150 0.049 Uiso calc R 1
O O1 0.4183(4) -0.1167(5) 0.24650(6) 0.0469(6) Uani d . 1
H H1C 0.3089 -0.2417 0.2447 0.070 Uiso calc R 1
O O2 1.0522(4) 0.4497(5) 0.23390(7) 0.0525(6) Uani d . 1
O O3 0.3630(4) 0.4405(6) 0.33929(7) 0.0533(6) Uani 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 0.0000 '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
C2 C1 C4 120.2(3)
C2 C1 H1A 119.9
C4 C1 H1A 119.9
C1 C2 C6 121.1(3)
C1 C2 H2A 119.5
C6 C2 H2A 119.5
C4 C3 C5 121.3(4)
C4 C3 H3A 119.3
C5 C3 H3A 119.3
C3 C4 C1 120.3(3)
C3 C4 H4A 119.8
C1 C4 H4A 119.8
C6 C5 C8 118.8(3)
C6 C5 C3 118.3(3)
C8 C5 C3 122.9(3)
C5 C6 C7 118.1(3)
C5 C6 C2 118.8(3)
C7 C6 C2 123.1(3)
C10 C7 C6 123.0(3)
C10 C7 H7A 118.5
C6 C7 H7A 118.5
C9 C8 C5 122.0(3)
C9 C8 H8A 119.0
C5 C8 H8A 119.0
C8 C9 O1 120.9(3)
C8 C9 C10 120.0(3)
O1 C9 C10 119.1(2)
C7 C10 C9 118.1(3)
C7 C10 C11 115.9(3)
C9 C10 C11 126.0(2)
O2 C11 N1 120.7(3)
O2 C11 C10 122.4(3)
N1 C11 C10 117.0(2)
O3 C12 N2 121.3(3)
O3 C12 C13 122.5(3)
N2 C12 C13 116.2(2)
C14 C13 C15 119.5(3)
C14 C13 C12 118.6(3)
C15 C13 C12 121.9(3)
C13 C14 C18 120.4(3)
C13 C14 H14A 119.8
C18 C14 H14A 119.8
C13 C15 C16 119.9(3)
C13 C15 H15A 120.0
C16 C15 H15A 120.0
C17 C16 C15 120.2(3)
C17 C16 H16A 119.9
C15 C16 H16A 119.9
C18 C17 C16 119.9(3)
C18 C17 H17A 120.0
C16 C17 H17A 120.0
C17 C18 C14 120.1(3)
C17 C18 H18A 120.0
C14 C18 H18A 120.0
C11 N1 N2 120.0(2)
C11 N1 H1B 120.0
N2 N1 H1B 120.0
C12 N2 N1 118.5(2)
C12 N2 H2B 120.7
N1 N2 H2B 120.7
C9 O1 H1C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.357(5)
C1 C4 1.385(5)
C1 H1A 0.9300
C2 C6 1.417(4)
C2 H2A 0.9300
C3 C4 1.356(5)
C3 C5 1.415(5)
C3 H3A 0.9300
C4 H4A 0.9300
C5 C6 1.399(5)
C5 C8 1.411(4)
C6 C7 1.410(4)
C7 C10 1.369(4)
C7 H7A 0.9300
C8 C9 1.359(4)
C8 H8A 0.9300
C9 O1 1.373(3)
C9 C10 1.417(4)
C10 C11 1.497(4)
C11 O2 1.233(3)
C11 N1 1.331(4)
C12 O3 1.235(3)
C12 N2 1.330(3)
C12 C13 1.489(4)
C13 C14 1.379(4)
C13 C15 1.384(4)
C14 C18 1.384(4)
C14 H14A 0.9300
C15 C16 1.387(4)
C15 H15A 0.9300
C16 C17 1.377(5)
C16 H16A 0.9300
C17 C18 1.374(5)
C17 H17A 0.9300
C18 H18A 0.9300
N1 N2 1.388(3)
N1 H1B 0.8600
N2 H2B 0.8600
O1 H1C 0.8200
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
_geom_hbond_publ_flag
O1 H1C O2 1_445 0.8196 2.0008 2.818(3) 174.36 y
N1 H1B O1 1_555 0.8600 1.9570 2.652(4) 137.00 y
N2 H2B O3 1_655 0.8602 2.0932 2.826(3) 142.72 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13478691
