#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102363.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102363
loop_
_publ_author_name
'Xiao-Yang Qiu'
_publ_section_title
;
 Crystal structure of
 4-hydroxy-3-methoxy-N'-(2-hydroxynaphthylidene)benzohydrazide methanol
 solvate, C19H16N2O4 · CH3OH
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              473
_journal_volume                  223
_journal_year                    2008
_chemical_formula_sum            'C20 H20 N2 O5'
_chemical_formula_weight         368.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.633(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.307(3)
_cell_length_b                   15.775(5)
_cell_length_c                   12.642(4)
_cell_measurement_reflns_used    2706
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.6
_cell_volume                     1787.4(10)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 [11]'
_computing_structure_solution    'SHELXS-97 [10]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10033
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9833
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0425
_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)+(0.0563P)²+0.1835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                2429
_reflns_number_total             3847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2439.cff
_cod_data_source_block           2
_cod_original_cell_volume        1787.4(9)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               8102363
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.21009(13) 0.53549(9) 0.76699(11) 0.0568(4) Uani 1 1 d . . .
H1 H 1.1798 0.5020 0.7163 0.085 Uiso 1 1 calc R . .
O2 O 1.21563(13) 0.39590(8) 0.53542(10) 0.0497(3) Uani 1 1 d . . .
O3 O 1.24547(13) 0.21562(8) 0.21321(10) 0.0543(4) Uani 1 1 d . . .
O4 O 0.98685(13) 0.14907(9) 0.13722(11) 0.0566(4) Uani 1 1 d . . .
H4 H 0.8984 0.1373 0.1117 0.085 Uiso 1 1 calc R . .
O5 O 0.16677(14) 0.15267(9) 0.98358(11) 0.0589(4) Uani 1 1 d . . .
H5 H 0.1353 0.1627 1.0369 0.088 Uiso 1 1 calc R . .
N1 N 1.02000(15) 0.44050(9) 0.63727(11) 0.0430(4) Uani 1 1 d . . .
N2 N 0.98098(15) 0.38716(9) 0.54795(11) 0.0434(4) Uani 1 1 d D . .
C1 C 0.95947(17) 0.51575(10) 0.78086(13) 0.0361(4) Uani 1 1 d . . .
C2 C 1.10099(18) 0.55083(11) 0.81630(14) 0.0421(4) Uani 1 1 d . . .
C3 C 1.1384(2) 0.60535(12) 0.90714(15) 0.0520(5) Uani 1 1 d . . .
H3 H 1.2335 0.6289 0.9293 0.062 Uiso 1 1 calc R . .
C4 C 1.0372(2) 0.62383(12) 0.96251(15) 0.0526(5) Uani 1 1 d . . .
H4A H 1.0643 0.6601 1.0226 0.063 Uiso 1 1 calc R . .
C5 C 0.89220(19) 0.59017(11) 0.93232(14) 0.0433(4) Uani 1 1 d . . .
C6 C 0.7874(2) 0.60890(12) 0.99081(16) 0.0548(5) Uani 1 1 d . . .
H6 H 0.8144 0.6450 1.0511 0.066 Uiso 1 1 calc R . .
C7 C 0.6480(2) 0.57580(13) 0.96171(17) 0.0586(5) Uani 1 1 d . . .
H7 H 0.5803 0.5890 1.0015 0.070 Uiso 1 1 calc R . .
C8 C 0.6072(2) 0.52180(12) 0.87160(16) 0.0538(5) Uani 1 1 d . . .
H8 H 0.5115 0.4990 0.8513 0.065 Uiso 1 1 calc R . .
C9 C 0.70512(18) 0.50174(11) 0.81254(15) 0.0445(4) Uani 1 1 d . . .
H9 H 0.6751 0.4653 0.7528 0.053 Uiso 1 1 calc R . .
C10 C 0.85127(18) 0.53505(10) 0.84013(13) 0.0364(4) Uani 1 1 d . . .
C11 C 0.92137(19) 0.46071(10) 0.68629(13) 0.0400(4) Uani 1 1 d . . .
H11 H 0.8247 0.4399 0.6609 0.048 Uiso 1 1 calc R . .
C12 C 1.08927(18) 0.36576(10) 0.50056(13) 0.0381(4) Uani 1 1 d . . .
C13 C 1.05268(17) 0.30655(10) 0.40703(13) 0.0371(4) Uani 1 1 d . . .
C14 C 1.16620(18) 0.28932(10) 0.35710(14) 0.0396(4) Uani 1 1 d . . .
H14 H 1.2593 0.3144 0.3844 0.047 Uiso 1 1 calc R . .
C15 C 1.14253(18) 0.23618(10) 0.26868(14) 0.0401(4) Uani 1 1 d . . .
C16 C 1.00293(19) 0.19877(11) 0.22697(14) 0.0422(4) Uani 1 1 d . . .
C17 C 0.89116(19) 0.21433(11) 0.27691(15) 0.0478(5) Uani 1 1 d . . .
H17 H 0.7986 0.1885 0.2502 0.057 Uiso 1 1 calc R . .
C18 C 0.91504(19) 0.26787(11) 0.36627(15) 0.0461(4) Uani 1 1 d . . .
H18 H 0.8387 0.2780 0.3993 0.055 Uiso 1 1 calc R . .
C19 C 1.38384(19) 0.25920(12) 0.24259(16) 0.0520(5) Uani 1 1 d . . .
H19A H 1.3662 0.3192 0.2366 0.078 Uiso 1 1 calc R . .
H19B H 1.4425 0.2426 0.1942 0.078 Uiso 1 1 calc R . .
H19C H 1.4364 0.2453 0.3169 0.078 Uiso 1 1 calc R . .
C20 C 0.0898(2) 0.08308(14) 0.92581(19) 0.0669(6) Uani 1 1 d . . .
H20A H 0.1268 0.0317 0.9643 0.100 Uiso 1 1 calc R . .
H20B H 0.1048 0.0813 0.8536 0.100 Uiso 1 1 calc R . .
H20C H -0.0147 0.0886 0.9200 0.100 Uiso 1 1 calc R . .
H2 H 0.8840(12) 0.3713(13) 0.5239(17) 0.080 Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C15 O3 C19 117.53(13) . . ?
C16 O4 H4 109.5 . . ?
C20 O5 H5 109.5 . . ?
C11 N1 N2 119.01(14) . . ?
C12 N2 N1 117.04(14) . . ?
C12 N2 H2 125.3(14) . . ?
N1 N2 H2 117.5(14) . . ?
C2 C1 C10 118.93(15) . . ?
C2 C1 C11 120.52(15) . . ?
C10 C1 C11 120.54(15) . . ?
O1 C2 C1 123.14(16) . . ?
O1 C2 C3 115.90(15) . . ?
C1 C2 C3 120.96(16) . . ?
C4 C3 C2 120.24(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 122.15(17) . . ?
C3 C4 H4A 118.9 . . ?
C5 C4 H4A 118.9 . . ?
C4 C5 C6 122.03(17) . . ?
C4 C5 C10 118.67(16) . . ?
C6 C5 C10 119.30(17) . . ?
C7 C6 C5 121.75(18) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 119.28(18) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 121.05(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.38(17) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 117.25(16) . . ?
C9 C10 C1 123.71(15) . . ?
C5 C10 C1 119.04(15) . . ?
N1 C11 C1 120.23(16) . . ?
N1 C11 H11 119.9 . . ?
C1 C11 H11 119.9 . . ?
O2 C12 N2 119.98(15) . . ?
O2 C12 C13 121.52(15) . . ?
N2 C12 C13 118.50(15) . . ?
C18 C13 C14 118.83(15) . . ?
C18 C13 C12 124.61(15) . . ?
C14 C13 C12 116.56(15) . . ?
C15 C14 C13 120.96(15) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 O3 125.65(15) . . ?
C14 C15 C16 119.81(15) . . ?
O3 C15 C16 114.53(15) . . ?
O4 C16 C17 124.13(16) . . ?
O4 C16 C15 116.31(15) . . ?
C17 C16 C15 119.56(16) . . ?
C16 C17 C18 120.64(16) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.17(16) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.349(2) . ?
O1 H1 0.8200 . ?
O2 C12 1.2346(18) . ?
O3 C15 1.3701(19) . ?
O3 C19 1.418(2) . ?
O4 C16 1.354(2) . ?
O4 H4 0.8200 . ?
O5 C20 1.404(2) . ?
O5 H5 0.8200 . ?
N1 C11 1.279(2) . ?
N1 N2 1.3762(19) . ?
N2 C12 1.347(2) . ?
N2 H2 0.907(9) . ?
C1 C2 1.387(2) . ?
C1 C10 1.440(2) . ?
C1 C11 1.442(2) . ?
C2 C3 1.401(2) . ?
C3 C4 1.348(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.405(3) . ?
C5 C10 1.421(2) . ?
C6 C7 1.354(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.362(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(2) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.473(2) . ?
C13 C18 1.387(2) . ?
C13 C14 1.396(2) . ?
C14 C15 1.367(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.395(2) . ?
C16 C17 1.377(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.83 2.5497(19) 145.7 .
O4 H4 O2 0.82 1.79 2.6040(18) 169.7 4_565
O5 H5 O4 0.82 2.12 2.8867(18) 155.0 1_456
O5 H5 O3 0.82 2.34 2.967(2) 133.6 1_456
N2 H2 O5 0.907(9) 1.983(10) 2.886(2) 173(2) 4_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653954
