#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/15/2221514.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_2221514
loop_
_publ_author_name
'Huang, Hai-Tao'
_publ_section_title
;
 N'-[4-(Dimethylamino)benzylidene]-3-hydroxy-2-naphthohydrazide
;
_journal_coeditor_code           SU2102
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o892
_journal_paper_doi               10.1107/S160053680900960X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H19 N3 O2'
_chemical_formula_moiety         'C20 H19 N3 O2'
_chemical_formula_sum            'C20 H19 N3 O2'
_chemical_formula_weight         333.38
_chemical_name_systematic
;
N'-[4-(Dimethylamino)benzylidene]-3-hydroxy-2-naphthohydrazide
;
_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                 98.978(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.090(2)
_cell_length_b                   15.798(3)
_cell_length_c                   13.428(3)
_cell_measurement_reflns_used    762
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      2.5
_cell_volume                     1695.2(7)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0749
_diffrn_reflns_av_sigmaI/netI    0.1333
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13922
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1664
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.001
_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)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1896
_reflns_number_gt                1629
_reflns_number_total             3670
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2102.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221514
_cod_database_fobs_code          2221514
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
O O1 -0.0121(3) 0.25089(12) 0.13318(14) 0.0832(7) Uani d . 1 . .
O O2 0.0653(3) 0.25424(12) -0.16764(12) 0.0674(6) Uani d . 1 . .
H H2 0.0589 0.2496 -0.2289 0.101 Uiso calc R 1 . .
N N1 0.1356(3) 0.39358(17) 0.07447(17) 0.0672(7) Uani d . 1 . .
N N2 0.0872(3) 0.32477(18) 0.01253(17) 0.0675(7) Uani d D 1 . .
N N3 0.4476(3) 0.76089(17) 0.2113(2) 0.0763(8) Uani d . 1 . .
C C1 0.2663(4) 0.5303(2) 0.0807(2) 0.0619(8) Uani d . 1 . .
C C2 0.2427(4) 0.5531(2) 0.1772(2) 0.0701(9) Uani d . 1 . .
H H2A 0.1870 0.5161 0.2144 0.084 Uiso calc R 1 . .
C C3 0.2992(4) 0.6282(2) 0.2186(2) 0.0726(9) Uani d . 1 . .
H H3 0.2785 0.6415 0.2830 0.087 Uiso calc R 1 . .
C C4 0.3873(4) 0.6862(2) 0.1683(2) 0.0615(8) Uani d . 1 . .
C C5 0.4095(4) 0.6637(2) 0.0710(2) 0.0756(10) Uani d . 1 . .
H H5 0.4645 0.7006 0.0333 0.091 Uiso calc R 1 . .
C C6 0.3512(5) 0.5876(2) 0.0302(2) 0.0825(10) Uani d . 1 . .
H H6 0.3699 0.5741 -0.0345 0.099 Uiso calc R 1 . .
C C7 0.4285(4) 0.7842(2) 0.3128(2) 0.0881(11) Uani d . 1 . .
H H7A 0.3154 0.7738 0.3228 0.132 Uiso calc R 1 . .
H H7B 0.4540 0.8432 0.3232 0.132 Uiso calc R 1 . .
H H7C 0.5036 0.7512 0.3599 0.132 Uiso calc R 1 . .
C C8 0.5351(4) 0.8210(2) 0.1573(3) 0.0897(11) Uani d . 1 . .
H H8A 0.6426 0.7985 0.1496 0.134 Uiso calc R 1 . .
H H8B 0.5496 0.8731 0.1944 0.134 Uiso calc R 1 . .
H H8C 0.4711 0.8312 0.0920 0.134 Uiso calc R 1 . .
C C9 0.2072(4) 0.4523(2) 0.0329(2) 0.0716(9) Uani d . 1 . .
H H9 0.2226 0.4443 -0.0336 0.086 Uiso calc R 1 . .
C C10 0.0123(4) 0.25726(19) 0.0455(2) 0.0588(8) Uani d . 1 . .
C C11 -0.0405(3) 0.18921(19) -0.02859(18) 0.0542(7) Uani d . 1 . .
C C12 -0.0109(3) 0.18591(18) -0.13032(18) 0.0524(7) Uani d . 1 . .
C C13 -0.0562(4) 0.11700(19) -0.18837(19) 0.0589(8) Uani d . 1 . .
H H13 -0.0304 0.1152 -0.2535 0.071 Uiso calc R 1 . .
C C14 -0.1407(3) 0.0483(2) -0.1533(2) 0.0580(8) Uani d . 1 . .
C C15 -0.1911(4) -0.0237(2) -0.2123(2) 0.0721(9) Uani d . 1 . .
H H15 -0.1660 -0.0273 -0.2774 0.087 Uiso calc R 1 . .
C C16 -0.2753(4) -0.0874(2) -0.1759(3) 0.0830(10) Uani d . 1 . .
H H16 -0.3073 -0.1344 -0.2161 0.100 Uiso calc R 1 . .
C C17 -0.3150(4) -0.0836(2) -0.0779(3) 0.0845(10) Uani d . 1 . .
H H17 -0.3747 -0.1274 -0.0540 0.101 Uiso calc R 1 . .
C C18 -0.2665(4) -0.0159(2) -0.0181(2) 0.0736(9) Uani d . 1 . .
H H18 -0.2927 -0.0138 0.0469 0.088 Uiso calc R 1 . .
C C19 -0.1767(3) 0.0512(2) -0.0534(2) 0.0567(8) Uani d . 1 . .
C C20 -0.1228(4) 0.12143(19) 0.00589(19) 0.0598(8) Uani d . 1 . .
H H20 -0.1434 0.1226 0.0721 0.072 Uiso calc R 1 . .
H H2B 0.104(3) 0.3251(17) -0.0520(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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O2 H2 . . 109.5 ?
C9 N1 N2 . . 114.5(2) ?
C10 N2 N1 . . 121.8(2) ?
C10 N2 H2B . . 117.9(18) ?
N1 N2 H2B . . 120.3(18) ?
C4 N3 C7 . . 122.3(3) ?
C4 N3 C8 . . 121.7(3) ?
C7 N3 C8 . . 116.0(3) ?
C6 C1 C2 . . 116.3(3) ?
C6 C1 C9 . . 120.0(3) ?
C2 C1 C9 . . 123.7(3) ?
C3 C2 C1 . . 121.5(3) ?
C3 C2 H2A . . 119.2 ?
C1 C2 H2A . . 119.2 ?
C2 C3 C4 . . 122.6(3) ?
C2 C3 H3 . . 118.7 ?
C4 C3 H3 . . 118.7 ?
N3 C4 C5 . . 121.7(3) ?
N3 C4 C3 . . 122.4(3) ?
C5 C4 C3 . . 115.9(3) ?
C6 C5 C4 . . 120.7(3) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 123.0(3) ?
C5 C6 H6 . . 118.5 ?
C1 C6 H6 . . 118.5 ?
N3 C7 H7A . . 109.5 ?
N3 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N3 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N3 C8 H8A . . 109.5 ?
N3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C1 . . 125.1(3) ?
N1 C9 H9 . . 117.5 ?
C1 C9 H9 . . 117.5 ?
O1 C10 N2 . . 122.1(3) ?
O1 C10 C11 . . 120.8(3) ?
N2 C10 C11 . . 117.1(2) ?
C20 C11 C12 . . 117.1(3) ?
C20 C11 C10 . . 116.2(2) ?
C12 C11 C10 . . 126.6(3) ?
C13 C12 O2 . . 121.1(2) ?
C13 C12 C11 . . 120.7(3) ?
O2 C12 C11 . . 118.2(3) ?
C12 C13 C14 . . 122.0(3) ?
C12 C13 H13 . . 119.0 ?
C14 C13 H13 . . 119.0 ?
C13 C14 C15 . . 123.3(3) ?
C13 C14 C19 . . 118.4(3) ?
C15 C14 C19 . . 118.3(3) ?
C16 C15 C14 . . 121.1(3) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
C15 C16 C17 . . 120.6(3) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C18 C17 C16 . . 120.1(3) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C19 . . 120.7(3) ?
C17 C18 H18 . . 119.7 ?
C19 C18 H18 . . 119.7 ?
C20 C19 C18 . . 122.6(3) ?
C20 C19 C14 . . 118.3(3) ?
C18 C19 C14 . . 119.1(3) ?
C11 C20 C19 . . 123.4(2) ?
C11 C20 H20 . . 118.3 ?
C19 C20 H20 . . 118.3 ?
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
O1 C10 . 1.228(3) ?
O2 C12 . 1.376(3) ?
O2 H2 . 0.8200 ?
N1 C9 . 1.268(3) ?
N1 N2 . 1.387(3) ?
N2 C10 . 1.336(3) ?
N2 H2B . 0.898(10) ?
N3 C4 . 1.370(4) ?
N3 C7 . 1.444(4) ?
N3 C8 . 1.444(4) ?
C1 C6 . 1.376(4) ?
C1 C2 . 1.386(4) ?
C1 C9 . 1.436(4) ?
C2 C3 . 1.359(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.399(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.392(4) ?
C5 C6 . 1.375(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.481(4) ?
C11 C20 . 1.379(4) ?
C11 C12 . 1.424(3) ?
C12 C13 . 1.356(4) ?
C13 C14 . 1.403(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.410(4) ?
C14 C19 . 1.417(3) ?
C15 C16 . 1.349(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.404(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.359(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.408(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.395(4) ?
C20 H20 . 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
N2 H2B O2 . 0.898(10) 1.90(2) 2.644(3) 139(2)
O2 H2 O1 4_565 0.82 1.85 2.651(3) 164.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5263703
