#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226481.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_2226481
loop_
_publ_author_name
'Zeng, Li'
'Zhou, Xiao-Si'
'Lv, Li-Hua'
'Li, Geng-Xi'
_publ_section_title
;
 (E)-N'-(3-Nitrobenzylidene)-4-(8-quinolyloxy)butanohydrazide
;
_journal_coeditor_code           HB5488
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1659
_journal_paper_doi               10.1107/S1600536810022257
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H18 N4 O4'
_chemical_formula_moiety         'C20 H18 N4 O4'
_chemical_formula_sum            'C20 H18 N4 O4'
_chemical_formula_weight         378.38
_chemical_name_systematic
;
(E)-N'-(3-Nitrobenzylidene)-4-(8-quinolyloxy)butanohydrazide
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.595(3)
_cell_angle_beta                 91.968(3)
_cell_angle_gamma                101.898(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3664(12)
_cell_length_b                   10.4882(15)
_cell_length_c                   11.5855(16)
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.43
_cell_volume                     975.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (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      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5434
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0647
_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)+(0.1425P)²+0.1889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1910
_refine_ls_wR_factor_ref         0.2675
_reflns_number_gt                1926
_reflns_number_total             3409
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5488.cif
_cod_data_source_block           I
_cod_database_code               2226481
_cod_database_fobs_code          2226481
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 0.2886(3) -0.1013(3) 0.68540(19) 0.0613(8) Uani d . 1 . .
O O2 0.2305(4) -0.0360(3) 1.0959(2) 0.0740(9) Uani d . 1 . .
O O3 0.8883(6) 0.6809(5) 0.8111(4) 0.1341(17) Uani d . 1 . .
O O4 0.6888(6) 0.5092(4) 0.7739(3) 0.1053(12) Uani d . 1 . .
N N1 0.5334(4) -0.2125(3) 0.6100(2) 0.0625(9) Uani d . 1 . .
N N2 0.4230(4) 0.1503(3) 1.1241(3) 0.0642(9) Uani d . 1 . .
H H2A 0.4367 0.1491 1.1978 0.077 Uiso calc R 1 . .
N N3 0.5149(4) 0.2515(3) 1.0792(3) 0.0566(8) Uani d . 1 . .
C C1 0.6550(6) -0.2666(5) 0.5723(4) 0.0872(15) Uani d . 1 . .
H H1 0.7215 -0.2894 0.6277 0.105 Uiso calc R 1 . .
C C2 0.6912(7) -0.2923(6) 0.4538(4) 0.0991(17) Uani d . 1 . .
H H2 0.7791 -0.3306 0.4316 0.119 Uiso calc R 1 . .
C C3 0.5935(6) -0.2595(5) 0.3724(4) 0.0786(13) Uani d . 1 . .
H H3 0.6141 -0.2765 0.2933 0.094 Uiso calc R 1 . .
C C4 0.4625(5) -0.2005(4) 0.4064(3) 0.0592(10) Uani d . 1 . .
C C5 0.3618(6) -0.1590(4) 0.3276(3) 0.0685(12) Uani d . 1 . .
H H5 0.3790 -0.1723 0.2478 0.082 Uiso calc R 1 . .
C C6 0.2416(6) -0.1004(4) 0.3671(3) 0.0711(12) Uani d . 1 . .
H H6 0.1778 -0.0709 0.3147 0.085 Uiso calc R 1 . .
C C7 0.2099(5) -0.0826(4) 0.4869(3) 0.0670(11) Uani d . 1 . .
H H7 0.1221 -0.0456 0.5119 0.080 Uiso calc R 1 . .
C C8 0.3055(5) -0.1187(4) 0.5660(3) 0.0558(10) Uani d . 1 . .
C C9 0.4356(5) -0.1781(4) 0.5281(3) 0.0524(9) Uani d . 1 . .
C C10 0.1507(5) -0.0514(5) 0.7282(3) 0.0621(10) Uani d . 1 . .
H H10A 0.0496 -0.1098 0.6910 0.074 Uiso calc R 1 . .
H H10B 0.1552 0.0363 0.7112 0.074 Uiso calc R 1 . .
C C11 0.1582(5) -0.0454(4) 0.8588(3) 0.0617(11) Uani d . 1 . .
H H11A 0.0553 -0.0295 0.8878 0.074 Uiso calc R 1 . .
H H11B 0.1703 -0.1309 0.8740 0.074 Uiso calc R 1 . .
C C12 0.2951(5) 0.0599(4) 0.9259(3) 0.0560(10) Uani d . 1 . .
H H12A 0.2762 0.1465 0.9191 0.067 Uiso calc R 1 . .
H H12B 0.3971 0.0506 0.8913 0.067 Uiso calc R 1 . .
C C13 0.3110(5) 0.0523(4) 1.0542(3) 0.0507(9) Uani d . 1 . .
C C14 0.6227(5) 0.3359(4) 1.1503(3) 0.0624(10) Uani d . 1 . .
H H14 0.6351 0.3263 1.2282 0.075 Uiso calc R 1 . .
C C15 0.7263(5) 0.4469(4) 1.1114(3) 0.0629(11) Uani d . 1 . .
C C16 0.7079(5) 0.4681(4) 0.9964(3) 0.0597(10) Uani d . 1 . .
H H16 0.6269 0.4117 0.9428 0.072 Uiso calc R 1 . .
C C17 0.8108(5) 0.5730(4) 0.9636(4) 0.0637(11) Uani d . 1 . .
C C18 0.9289(6) 0.6604(4) 1.0400(5) 0.0755(13) Uani d . 1 . .
H H18 0.9950 0.7321 1.0160 0.091 Uiso calc R 1 . .
C C19 0.9478(6) 0.6398(5) 1.1533(5) 0.0840(14) Uani d . 1 . .
H H19 1.0292 0.6964 1.2064 0.101 Uiso calc R 1 . .
C C20 0.8451(6) 0.5343(5) 1.1875(4) 0.0761(13) Uani d . 1 . .
H H20 0.8571 0.5224 1.2646 0.091 Uiso calc R 1 . .
N N4 0.7921(6) 0.5887(4) 0.8403(4) 0.0813(11) 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 0.0016 '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 . . 117.5(3) ?
C1 N1 C9 . . 117.9(3) ?
C13 N2 N3 . . 120.9(3) ?
C13 N2 H2A . . 119.5 ?
N3 N2 H2A . . 119.5 ?
C14 N3 N2 . . 116.6(3) ?
N1 C1 C2 . . 124.3(4) ?
N1 C1 H1 . . 117.9 ?
C2 C1 H1 . . 117.9 ?
C3 C2 C1 . . 118.0(4) ?
C3 C2 H2 . . 121.0 ?
C1 C2 H2 . . 121.0 ?
C2 C3 C4 . . 120.8(4) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C3 C4 C5 . . 123.5(3) ?
C3 C4 C9 . . 117.2(3) ?
C5 C4 C9 . . 119.2(4) ?
C6 C5 C4 . . 120.1(3) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 121.0(4) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 120.8(4) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 O1 . . 125.3(3) ?
C7 C8 C9 . . 119.8(3) ?
O1 C8 C9 . . 114.9(3) ?
N1 C9 C8 . . 119.1(3) ?
N1 C9 C4 . . 121.9(3) ?
C8 C9 C4 . . 119.0(3) ?
O1 C10 C11 . . 107.0(3) ?
O1 C10 H10A . . 110.3 ?
C11 C10 H10A . . 110.3 ?
O1 C10 H10B . . 110.3 ?
C11 C10 H10B . . 110.3 ?
H10A C10 H10B . . 108.6 ?
C12 C11 C10 . . 114.0(3) ?
C12 C11 H11A . . 108.8 ?
C10 C11 H11A . . 108.8 ?
C12 C11 H11B . . 108.8 ?
C10 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C11 C12 C13 . . 112.4(3) ?
C11 C12 H12A . . 109.1 ?
C13 C12 H12A . . 109.1 ?
C11 C12 H12B . . 109.1 ?
C13 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.9 ?
O2 C13 N2 . . 119.8(3) ?
O2 C13 C12 . . 123.5(4) ?
N2 C13 C12 . . 116.6(3) ?
N3 C14 C15 . . 120.9(4) ?
N3 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C20 C15 C16 . . 118.1(4) ?
C20 C15 C14 . . 120.4(4) ?
C16 C15 C14 . . 121.5(4) ?
C17 C16 C15 . . 119.2(4) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C18 C17 C16 . . 122.5(4) ?
C18 C17 N4 . . 119.9(4) ?
C16 C17 N4 . . 117.6(4) ?
C17 C18 C19 . . 118.5(5) ?
C17 C18 H18 . . 120.7 ?
C19 C18 H18 . . 120.7 ?
C18 C19 C20 . . 119.6(4) ?
C18 C19 H19 . . 120.2 ?
C20 C19 H19 . . 120.2 ?
C15 C20 C19 . . 122.1(4) ?
C15 C20 H20 . . 118.9 ?
C19 C20 H20 . . 118.9 ?
O4 N4 O3 . . 124.2(4) ?
O4 N4 C17 . . 118.8(4) ?
O3 N4 C17 . . 116.9(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 . 1.378(4) ?
O1 C10 . 1.429(4) ?
O2 C13 . 1.214(4) ?
O3 N4 . 1.231(5) ?
O4 N4 . 1.207(5) ?
N1 C1 . 1.313(5) ?
N1 C9 . 1.377(4) ?
N2 C13 . 1.355(5) ?
N2 N3 . 1.372(4) ?
N2 H2A . 0.8600 ?
N3 C14 . 1.276(5) ?
C1 C2 . 1.406(6) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.363(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.399(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.407(5) ?
C4 C9 . 1.419(5) ?
C5 C6 . 1.334(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.408(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.350(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.406(5) ?
C10 C11 . 1.501(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.495(5) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.505(5) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C14 C15 . 1.454(6) ?
C14 H14 . 0.9300 ?
C15 C20 . 1.368(6) ?
C15 C16 . 1.399(5) ?
C16 C17 . 1.372(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.367(6) ?
C17 N4 . 1.474(6) ?
C18 C19 . 1.379(7) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.382(6) ?
C19 H19 . 0.9300 ?
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 H2A N1 2_657 0.86 2.19 3.022(4) 162
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
C13 N2 N3 C14 . . . . -176.8(3) ?
C9 N1 C1 C2 . . . . -0.4(8) ?
N1 C1 C2 C3 . . . . -0.3(9) ?
C1 C2 C3 C4 . . . . 0.8(8) ?
C2 C3 C4 C5 . . . . 177.1(5) ?
C2 C3 C4 C9 . . . . -0.7(7) ?
C3 C4 C5 C6 . . . . -178.3(4) ?
C9 C4 C5 C6 . . . . -0.7(6) ?
C4 C5 C6 C7 . . . . -1.9(7) ?
C5 C6 C7 C8 . . . . 3.2(7) ?
C6 C7 C8 O1 . . . . 177.6(4) ?
C6 C7 C8 C9 . . . . -1.8(6) ?
C10 O1 C8 C7 . . . . 5.6(6) ?
C10 O1 C8 C9 . . . . -175.0(3) ?
C1 N1 C9 C8 . . . . -179.3(4) ?
C1 N1 C9 C4 . . . . 0.5(6) ?
C7 C8 C9 N1 . . . . 179.0(4) ?
O1 C8 C9 N1 . . . . -0.3(5) ?
C7 C8 C9 C4 . . . . -0.8(6) ?
O1 C8 C9 C4 . . . . 179.8(3) ?
C3 C4 C9 N1 . . . . 0.0(6) ?
C5 C4 C9 N1 . . . . -177.8(4) ?
C3 C4 C9 C8 . . . . 179.8(4) ?
C5 C4 C9 C8 . . . . 2.0(6) ?
C8 O1 C10 C11 . . . . 178.5(3) ?
O1 C10 C11 C12 . . . . 70.1(4) ?
C10 C11 C12 C13 . . . . -173.2(3) ?
N3 N2 C13 O2 . . . . -179.7(3) ?
N3 N2 C13 C12 . . . . 0.8(5) ?
C11 C12 C13 O2 . . . . 5.7(5) ?
C11 C12 C13 N2 . . . . -174.8(3) ?
N2 N3 C14 C15 . . . . -180.0(3) ?
N3 C14 C15 C20 . . . . -177.9(3) ?
N3 C14 C15 C16 . . . . 2.4(5) ?
C20 C15 C16 C17 . . . . 1.4(5) ?
C14 C15 C16 C17 . . . . -178.9(3) ?
C15 C16 C17 C18 . . . . -1.7(5) ?
C15 C16 C17 N4 . . . . 177.5(3) ?
C16 C17 C18 C19 . . . . 1.8(6) ?
N4 C17 C18 C19 . . . . -177.3(4) ?
C17 C18 C19 C20 . . . . -1.7(6) ?
C16 C15 C20 C19 . . . . -1.3(6) ?
C14 C15 C20 C19 . . . . 178.9(4) ?
C18 C19 C20 C15 . . . . 1.5(6) ?
C18 C17 N4 O4 . . . . 178.7(4) ?
C16 C17 N4 O4 . . . . -0.4(6) ?
C18 C17 N4 O3 . . . . 1.3(6) ?
C16 C17 N4 O3 . . . . -177.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745295
