#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229013.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_2229013
loop_
_publ_author_name
'Li, Tian-Yi'
'Ge, Yan-Xia'
_publ_section_title
;
 3-Chloro-N'-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide
;
_journal_coeditor_code           CV5034
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o374
_journal_paper_doi               10.1107/S1600536811000924
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H15 Cl N2 O2'
_chemical_formula_moiety         'C19 H15 Cl N2 O2'
_chemical_formula_sum            'C19 H15 Cl N2 O2'
_chemical_formula_weight         338.78
_chemical_name_systematic
;
3-Chloro-N'-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.446(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.181(2)
_cell_length_b                   16.953(4)
_cell_length_c                   8.5482(15)
_cell_measurement_reflns_used    762
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      2.5
_cell_volume                     1664.5(6)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (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 APEXII CCD area-detector
;
_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  0.0670
_diffrn_reflns_av_sigmaI/netI    0.1093
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8964
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0597
_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)+(0.0386P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                1624
_reflns_number_total             3586
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5034.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229013
_cod_database_fobs_code          2229013
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl Cl1 0.57105(8) 0.10288(6) 1.03193(12) 0.0793(4) Uani d . 1 . .
N N1 0.8646(2) 0.28050(15) 0.6055(3) 0.0469(7) Uani d . 1 . .
N N2 0.7753(2) 0.24546(15) 0.6487(3) 0.0467(7) Uani d D 1 . .
O O1 0.9252(2) 0.49223(13) 0.7763(3) 0.0709(7) Uani d . 1 . .
O O2 0.71701(19) 0.17210(12) 0.4129(3) 0.0619(7) Uani d . 1 . .
C C1 1.0045(3) 0.38640(17) 0.6734(4) 0.0453(8) Uani d . 1 . .
C C2 1.0122(3) 0.46507(19) 0.7236(4) 0.0540(9) Uani d . 1 . .
C C3 1.1046(3) 0.5131(2) 0.7182(4) 0.0707(11) Uani d . 1 . .
H H3 1.1088 0.5653 0.7527 0.085 Uiso calc R 1 . .
C C4 1.1874(3) 0.4831(2) 0.6626(5) 0.0753(11) Uani d . 1 . .
H H4 1.2479 0.5157 0.6589 0.090 Uiso calc R 1 . .
C C5 1.1857(3) 0.4049(2) 0.6107(4) 0.0563(9) Uani d . 1 . .
C C6 1.2739(3) 0.3739(2) 0.5573(5) 0.0737(11) Uani d . 1 . .
H H6 1.3347 0.4067 0.5556 0.088 Uiso calc R 1 . .
C C7 1.2739(3) 0.2977(3) 0.5082(5) 0.0751(11) Uani d . 1 . .
H H7 1.3337 0.2785 0.4739 0.090 Uiso calc R 1 . .
C C8 1.1819(3) 0.2489(2) 0.5103(4) 0.0676(10) Uani d . 1 . .
H H8 1.1807 0.1965 0.4773 0.081 Uiso calc R 1 . .
C C9 1.0942(3) 0.27685(19) 0.5598(4) 0.0549(9) Uani d . 1 . .
H H9 1.0337 0.2431 0.5582 0.066 Uiso calc R 1 . .
C C10 1.0917(3) 0.35562(17) 0.6136(4) 0.0458(8) Uani d . 1 . .
C C11 0.9075(3) 0.34138(18) 0.6916(4) 0.0488(8) Uani d . 1 . .
H H11 0.8752 0.3580 0.7703 0.059 Uiso calc R 1 . .
C C12 0.7072(3) 0.19108(18) 0.5452(4) 0.0463(8) Uani d . 1 . .
C C13 0.6157(3) 0.15628(16) 0.6049(4) 0.0418(7) Uani d . 1 . .
C C14 0.6300(2) 0.14888(16) 0.7713(4) 0.0433(8) Uani d . 1 . .
H H14 0.6972 0.1682 0.8504 0.052 Uiso calc R 1 . .
C C15 0.5463(3) 0.11327(18) 0.8211(4) 0.0506(8) Uani d . 1 . .
C C16 0.4458(3) 0.0859(2) 0.7070(5) 0.0752(11) Uani d . 1 . .
H H16 0.3886 0.0626 0.7417 0.090 Uiso calc R 1 . .
C C17 0.4298(3) 0.0930(2) 0.5414(5) 0.0840(12) Uani d . 1 . .
H H17 0.3618 0.0743 0.4633 0.101 Uiso calc R 1 . .
C C18 0.5144(3) 0.1278(2) 0.4901(4) 0.0670(10) Uani d . 1 . .
H H18 0.5031 0.1322 0.3774 0.080 Uiso calc R 1 . .
C C19 0.9307(4) 0.5719(2) 0.8359(5) 0.0905(13) Uani d . 1 . .
H H19A 1.0029 0.5798 0.9245 0.136 Uiso calc R 1 . .
H H19B 0.8669 0.5812 0.8758 0.136 Uiso calc R 1 . .
H H19C 0.9260 0.6079 0.7471 0.136 Uiso calc R 1 . .
H H2 0.757(3) 0.265(2) 0.736(3) 0.109 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'
Cl Cl 0.1484 0.1585 '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 . . 113.5(2) ?
C12 N2 N1 . . 118.7(2) ?
C12 N2 H2 . . 121(2) ?
N1 N2 H2 . . 119(2) ?
C2 O1 C19 . . 119.1(3) ?
C2 C1 C10 . . 118.7(3) ?
C2 C1 C11 . . 116.2(3) ?
C10 C1 C11 . . 125.1(3) ?
O1 C2 C1 . . 116.4(3) ?
O1 C2 C3 . . 122.4(3) ?
C1 C2 C3 . . 121.1(3) ?
C4 C3 C2 . . 119.7(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 122.4(3) ?
C3 C4 H4 . . 118.8 ?
C5 C4 H4 . . 118.8 ?
C4 C5 C6 . . 121.9(3) ?
C4 C5 C10 . . 118.6(3) ?
C6 C5 C10 . . 119.5(3) ?
C7 C6 C5 . . 122.4(3) ?
C7 C6 H6 . . 118.8 ?
C5 C6 H6 . . 118.8 ?
C6 C7 C8 . . 118.4(3) ?
C6 C7 H7 . . 120.8 ?
C8 C7 H7 . . 120.8 ?
C9 C8 C7 . . 121.0(3) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 122.3(3) ?
C8 C9 H9 . . 118.9 ?
C10 C9 H9 . . 118.9 ?
C9 C10 C1 . . 124.2(3) ?
C9 C10 C5 . . 116.3(3) ?
C1 C10 C5 . . 119.5(3) ?
N1 C11 C1 . . 123.7(3) ?
N1 C11 H11 . . 118.2 ?
C1 C11 H11 . . 118.2 ?
O2 C12 N2 . . 123.9(3) ?
O2 C12 C13 . . 121.8(3) ?
N2 C12 C13 . . 114.2(3) ?
C14 C13 C18 . . 118.5(3) ?
C14 C13 C12 . . 122.4(3) ?
C18 C13 C12 . . 119.1(3) ?
C15 C14 C13 . . 120.6(3) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C14 . . 120.7(3) ?
C16 C15 Cl1 . . 120.8(2) ?
C14 C15 Cl1 . . 118.5(3) ?
C15 C16 C17 . . 119.5(3) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C16 C17 C18 . . 120.2(3) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C17 C18 C13 . . 120.5(3) ?
C17 C18 H18 . . 119.7 ?
C13 C18 H18 . . 119.7 ?
O1 C19 H19A . . 109.5 ?
O1 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O1 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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
Cl1 C15 . 1.735(3) ?
N1 C11 . 1.274(3) ?
N1 N2 . 1.392(3) ?
N2 C12 . 1.354(4) ?
N2 H2 . 0.91(3) ?
O1 C2 . 1.362(4) ?
O1 C19 . 1.437(4) ?
O2 C12 . 1.219(3) ?
C1 C2 . 1.394(4) ?
C1 C10 . 1.422(4) ?
C1 C11 . 1.458(4) ?
C2 C3 . 1.402(4) ?
C3 C4 . 1.349(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.395(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.402(5) ?
C5 C10 . 1.425(4) ?
C6 C7 . 1.358(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.399(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.358(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.416(4) ?
C9 H9 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.494(4) ?
C13 C14 . 1.380(4) ?
C13 C18 . 1.383(4) ?
C14 C15 . 1.370(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.367(4) ?
C16 C17 . 1.368(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.379(5) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
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
N2 H2 O2 4_566 0.91(3) 2.04(3) 2.937(3) 170(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4495714
