#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/16/2221639.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_2221639
loop_
_publ_author_name
'Wang, Shou-Yu'
'Yuan, Liang'
'Xu, Liang'
'Zhang, Zhen'
'Diao, Yun-Peng'
'Lv, De-Cheng'
_publ_section_title
;(E)-N'-(2,5-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide
 methanol solvate
;
_journal_coeditor_code           CV2552
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1154
_journal_paper_doi               10.1107/S1600536809015165
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H19 N3 O4, C H4 O'
_chemical_formula_moiety         'C20 H19 N3 O4, C H4 O'
_chemical_formula_sum            'C21 H23 N3 O5'
_chemical_formula_weight         397.42
_chemical_name_systematic
;(E)-N'-(2,5-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide
methanol
 solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.2680(10)
_cell_angle_beta                 112.816(2)
_cell_angle_gamma                107.859(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4199(12)
_cell_length_b                   10.8652(14)
_cell_length_c                   11.1721(14)
_cell_measurement_reflns_used    1903
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      2.46
_cell_volume                     982.8(2)
_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      295
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5196
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.334
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0498
_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)+(0.0685P)²+0.304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1492
_reflns_number_gt                2363
_reflns_number_total             3456
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2552.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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               2221639
_cod_database_fobs_code          2221639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.24162(17) 0.13371(15) 0.32912(13) 0.0535(4) Uani d . 1 . .
O O2 0.0642(2) 0.1461(2) 0.64429(16) 0.0858(6) Uani d . 1 . .
O O3 0.4628(2) 0.39500(19) 0.28395(18) 0.0788(5) Uani d . 1 . .
O O4 0.8736(2) 0.3699(2) 0.7849(2) 0.0949(7) Uani d . 1 . .
O O5 -0.0293(3) 0.2135(3) 0.1843(2) 0.1266(11) Uani d . 1 . .
H H5A -0.1081 0.2324 0.1818 0.190 Uiso calc R 1 . .
N N1 -0.3582(2) 0.19146(18) 0.08689(17) 0.0528(5) Uani d . 1 . .
N N2 0.0876(2) 0.19807(18) 0.45814(17) 0.0560(5) Uani d . 1 . .
H H2 0.0371 0.2020 0.3766 0.067 Uiso calc R 1 . .
N N3 0.2580(2) 0.23818(18) 0.51768(18) 0.0558(5) Uani d . 1 . .
C C1 -0.4175(3) 0.2184(2) -0.0328(2) 0.0601(6) Uani d . 1 . .
H H1 -0.3428 0.2594 -0.0664 0.072 Uiso calc R 1 . .
C C2 -0.5851(3) 0.1892(2) -0.1121(2) 0.0643(7) Uani d . 1 . .
H H2A -0.6203 0.2104 -0.1956 0.077 Uiso calc R 1 . .
C C3 -0.6951(3) 0.1293(2) -0.0644(2) 0.0627(6) Uani d . 1 . .
H H3 -0.8073 0.1086 -0.1154 0.075 Uiso calc R 1 . .
C C4 -0.6394(3) 0.0981(2) 0.0630(2) 0.0536(6) Uani d . 1 . .
C C5 -0.7479(3) 0.0345(3) 0.1181(3) 0.0662(7) Uani d . 1 . .
H H5 -0.8608 0.0141 0.0709 0.079 Uiso calc R 1 . .
C C6 -0.6890(3) 0.0033(3) 0.2383(3) 0.0693(7) Uani d . 1 . .
H H6 -0.7616 -0.0393 0.2731 0.083 Uiso calc R 1 . .
C C7 -0.5183(3) 0.0346(2) 0.3117(2) 0.0575(6) Uani d . 1 . .
H H7 -0.4796 0.0116 0.3941 0.069 Uiso calc R 1 . .
C C8 -0.4090(2) 0.0981(2) 0.2636(2) 0.0474(5) Uani d . 1 . .
C C9 -0.4680(3) 0.1308(2) 0.1355(2) 0.0473(5) Uani d . 1 . .
C C10 -0.1828(3) 0.1048(2) 0.4579(2) 0.0543(6) Uani d . 1 . .
H H10A -0.2262 0.0101 0.4509 0.065 Uiso calc R 1 . .
H H10B -0.2240 0.1450 0.5106 0.065 Uiso calc R 1 . .
C C11 0.0023(3) 0.1532(2) 0.5280(2) 0.0549(6) Uani d . 1 . .
C C12 0.3277(3) 0.2839(2) 0.4443(2) 0.0603(6) Uani d . 1 . .
H H12 0.2622 0.2859 0.3576 0.072 Uiso calc R 1 . .
C C13 0.5061(3) 0.3334(2) 0.4906(2) 0.0568(6) Uani d . 1 . .
C C14 0.5723(3) 0.3921(2) 0.4061(3) 0.0625(6) Uani d . 1 . .
C C15 0.7399(4) 0.4419(3) 0.4488(3) 0.0800(8) Uani d . 1 . .
H H15 0.7843 0.4798 0.3926 0.096 Uiso calc R 1 . .
C C16 0.8436(4) 0.4366(3) 0.5739(3) 0.0842(9) Uani d . 1 . .
H H16 0.9572 0.4722 0.6020 0.101 Uiso calc R 1 . .
C C17 0.7807(3) 0.3791(3) 0.6577(3) 0.0701(7) Uani d . 1 . .
C C18 0.6115(3) 0.3272(2) 0.6158(3) 0.0637(6) Uani d . 1 . .
H H18 0.5682 0.2879 0.6720 0.076 Uiso calc R 1 . .
C C19 0.5240(4) 0.4653(3) 0.2014(3) 0.0892(9) Uani d . 1 . .
H H19A 0.5871 0.5557 0.2460 0.134 Uiso calc R 1 . .
H H19B 0.4335 0.4616 0.1206 0.134 Uiso calc R 1 . .
H H19C 0.5931 0.4265 0.1814 0.134 Uiso calc R 1 . .
C C20 1.0484(4) 0.4126(4) 0.8254(4) 0.1123(12) Uani d . 1 . .
H H20A 1.0716 0.3572 0.7710 0.168 Uiso calc R 1 . .
H H20B 1.1020 0.4068 0.9164 0.168 Uiso calc R 1 . .
H H20C 1.0885 0.5023 0.8159 0.168 Uiso calc R 1 . .
C C21 0.0330(4) 0.2797(4) 0.1045(3) 0.0957(10) Uani d . 1 . .
H H21A 0.0494 0.3715 0.1245 0.144 Uiso calc R 1 . .
H H21B -0.0432 0.2434 0.0133 0.144 Uiso calc R 1 . .
H H21C 0.1365 0.2705 0.1197 0.144 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 0.0016 '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
C8 O1 C10 . . 115.50(17) ?
C14 O3 C19 . . 118.6(2) ?
C17 O4 C20 . . 116.1(2) ?
C21 O5 H5A . . 109.5 ?
C1 N1 C9 . . 117.75(19) ?
C11 N2 N3 . . 119.67(17) ?
C11 N2 H2 . . 120.2 ?
N3 N2 H2 . . 120.2 ?
C12 N3 N2 . . 114.67(19) ?
N1 C1 C2 . . 124.2(2) ?
N1 C1 H1 . . 117.9 ?
C2 C1 H1 . . 117.9 ?
C3 C2 C1 . . 118.4(2) ?
C3 C2 H2A . . 120.8 ?
C1 C2 H2A . . 120.8 ?
C2 C3 C4 . . 120.1(2) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C9 C4 C3 . . 117.5(2) ?
C9 C4 C5 . . 119.7(2) ?
C3 C4 C5 . . 122.8(2) ?
C6 C5 C4 . . 120.5(2) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C7 . . 120.5(2) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 121.0(2) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C7 C8 O1 . . 124.68(19) ?
C7 C8 C9 . . 119.8(2) ?
O1 C8 C9 . . 115.50(18) ?
N1 C9 C4 . . 122.07(19) ?
N1 C9 C8 . . 119.45(18) ?
C4 C9 C8 . . 118.5(2) ?
O1 C10 C11 . . 113.06(18) ?
O1 C10 H10A . . 109.0 ?
C11 C10 H10A . . 109.0 ?
O1 C10 H10B . . 109.0 ?
C11 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
O2 C11 N2 . . 124.4(2) ?
O2 C11 C10 . . 117.6(2) ?
N2 C11 C10 . . 117.96(18) ?
N3 C12 C13 . . 122.5(2) ?
N3 C12 H12 . . 118.7 ?
C13 C12 H12 . . 118.7 ?
C18 C13 C14 . . 119.4(2) ?
C18 C13 C12 . . 122.2(2) ?
C14 C13 C12 . . 118.4(2) ?
O3 C14 C15 . . 123.8(2) ?
O3 C14 C13 . . 116.8(2) ?
C15 C14 C13 . . 119.3(3) ?
C14 C15 C16 . . 120.8(3) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C17 C16 C15 . . 120.6(3) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 O4 . . 125.0(2) ?
C16 C17 C18 . . 119.4(3) ?
O4 C17 C18 . . 115.5(2) ?
C17 C18 C13 . . 120.4(2) ?
C17 C18 H18 . . 119.8 ?
C13 C18 H18 . . 119.8 ?
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 ?
O4 C20 H20A . . 109.5 ?
O4 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O4 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
O5 C21 H21A . . 109.5 ?
O5 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O5 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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
O1 C8 . 1.367(2) ?
O1 C10 . 1.420(2) ?
O2 C11 . 1.219(3) ?
O3 C14 . 1.364(3) ?
O3 C19 . 1.410(3) ?
O4 C17 . 1.378(3) ?
O4 C20 . 1.435(3) ?
O5 C21 . 1.371(3) ?
O5 H5A . 0.8200 ?
N1 C1 . 1.324(3) ?
N1 C9 . 1.363(3) ?
N2 C11 . 1.335(3) ?
N2 N3 . 1.385(2) ?
N2 H2 . 0.8600 ?
N3 C12 . 1.271(3) ?
C1 C2 . 1.398(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.355(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.414(3) ?
C3 H3 . 0.9300 ?
C4 C9 . 1.411(3) ?
C4 C5 . 1.415(3) ?
C5 C6 . 1.348(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.408(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.364(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.430(3) ?
C10 C11 . 1.504(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 C13 . 1.456(3) ?
C12 H12 . 0.9300 ?
C13 C18 . 1.386(3) ?
C13 C14 . 1.403(3) ?
C14 C15 . 1.369(4) ?
C15 C16 . 1.378(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.374(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.385(3) ?
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 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 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
O5 H5A O1 . 0.82 2.53 2.996(3) 116.9
O5 H5A N1 . 0.82 2.06 2.782(3) 147.0
N2 H2 O5 . 0.86 2.01 2.856(3) 166.1
C12 H12 O5 . 0.93 2.51 3.305(3) 143.9
C3 H3 O2 1_454 0.93 2.60 3.220(3) 124.8
C20 H20A O2 1_655 0.96 2.59 3.511(5) 160.2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N2 N3 C12 . . . . -177.4(2) ?
C9 N1 C1 C2 . . . . 0.3(3) ?
N1 C1 C2 C3 . . . . -0.1(4) ?
C1 C2 C3 C4 . . . . 0.2(4) ?
C2 C3 C4 C9 . . . . -0.6(3) ?
C2 C3 C4 C5 . . . . -179.4(2) ?
C9 C4 C5 C6 . . . . -0.9(4) ?
C3 C4 C5 C6 . . . . 177.9(2) ?
C4 C5 C6 C7 . . . . 0.6(4) ?
C5 C6 C7 C8 . . . . 0.7(4) ?
C6 C7 C8 O1 . . . . 179.0(2) ?
C6 C7 C8 C9 . . . . -1.6(3) ?
C10 O1 C8 C7 . . . . -2.3(3) ?
C10 O1 C8 C9 . . . . 178.19(18) ?
C1 N1 C9 C4 . . . . -0.7(3) ?
C1 N1 C9 C8 . . . . 179.0(2) ?
C3 C4 C9 N1 . . . . 0.8(3) ?
C5 C4 C9 N1 . . . . 179.7(2) ?
C3 C4 C9 C8 . . . . -178.88(19) ?
C5 C4 C9 C8 . . . . 0.0(3) ?
C7 C8 C9 N1 . . . . -178.5(2) ?
O1 C8 C9 N1 . . . . 1.0(3) ?
C7 C8 C9 C4 . . . . 1.2(3) ?
O1 C8 C9 C4 . . . . -179.29(18) ?
C8 O1 C10 C11 . . . . -176.68(18) ?
N3 N2 C11 O2 . . . . 1.0(4) ?
N3 N2 C11 C10 . . . . -177.22(19) ?
O1 C10 C11 O2 . . . . 172.0(2) ?
O1 C10 C11 N2 . . . . -9.6(3) ?
N2 N3 C12 C13 . . . . 178.7(2) ?
N3 C12 C13 C18 . . . . 3.6(4) ?
N3 C12 C13 C14 . . . . -174.8(2) ?
C19 O3 C14 C15 . . . . -7.1(4) ?
C19 O3 C14 C13 . . . . 173.3(2) ?
C18 C13 C14 O3 . . . . 179.8(2) ?
C12 C13 C14 O3 . . . . -1.8(3) ?
C18 C13 C14 C15 . . . . 0.2(4) ?
C12 C13 C14 C15 . . . . 178.6(2) ?
O3 C14 C15 C16 . . . . 179.5(3) ?
C13 C14 C15 C16 . . . . -0.9(4) ?
C14 C15 C16 C17 . . . . 1.1(5) ?
C15 C16 C17 O4 . . . . -179.3(3) ?
C15 C16 C17 C18 . . . . -0.5(4) ?
C20 O4 C17 C16 . . . . -6.5(4) ?
C20 O4 C17 C18 . . . . 174.7(3) ?
C16 C17 C18 C13 . . . . -0.2(4) ?
O4 C17 C18 C13 . . . . 178.7(2) ?
C14 C13 C18 C17 . . . . 0.4(4) ?
C12 C13 C18 C17 . . . . -178.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655761
