#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/67/2226755.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_2226755
loop_
_publ_author_name
'XiaHou, Guo-Lun'
'Ding, Ye-Chun'
'Fan, Xiao-Na'
_publ_section_title
;
 (E)-N'-(4-Nitrobenzylidene)-4-(8-quinolyloxy)butanohydrazide
;
_journal_coeditor_code           ZS2040
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1522
_journal_paper_doi               10.1107/S1600536810020039
_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'-(4-Nitrobenzylidene)-4-(8-quinolyloxy)butanohydrazide
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.365(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.836(3)
_cell_length_b                   10.633(3)
_cell_length_c                   17.566(5)
_cell_measurement_reflns_used    3279
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.24
_cell_volume                     1835.6(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker SMART CCD area-detector diffractometer'
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9957
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0435
_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)+(0.0719P)²+0.3873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2345
_reflns_number_total             3256
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2040.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226755
_cod_database_fobs_code          2226755
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 0.75513(15) 0.53054(15) 0.16112(8) 0.0599(4) Uani d . 1 . .
O O2 1.05475(15) 0.89991(18) 0.07985(10) 0.0749(5) Uani d . 1 . .
O O3 0.0388(2) 0.8161(3) -0.16156(15) 0.1302(10) Uani d . 1 . .
O O4 0.04918(18) 0.6940(2) -0.06516(13) 0.0903(6) Uani d . 1 . .
N N1 0.50202(18) 0.48897(16) 0.10959(10) 0.0542(5) Uani d . 1 . .
N N2 0.85327(17) 0.90258(17) 0.01739(10) 0.0499(4) Uani d . 1 . .
H H2A 0.8844 0.9544 -0.0152 0.060 Uiso calc R 1 . .
N N3 0.71999(16) 0.86354(16) 0.00912(10) 0.0466(4) Uani d . 1 . .
N N4 0.0993(2) 0.7717(2) -0.10668(13) 0.0710(6) Uani d . 1 . .
C C1 0.3767(2) 0.4663(2) 0.08357(15) 0.0651(7) Uani d . 1 . .
H H1 0.3479 0.5042 0.0380 0.078 Uiso calc R 1 . .
C C2 0.2845(2) 0.3894(2) 0.11982(17) 0.0685(7) Uani d . 1 . .
H H2 0.1962 0.3793 0.0998 0.082 Uiso calc R 1 . .
C C3 0.3263(2) 0.3297(2) 0.18475(15) 0.0642(7) Uani d . 1 . .
H H3 0.2665 0.2777 0.2097 0.077 Uiso calc R 1 . .
C C4 0.4606(2) 0.34635(18) 0.21447(11) 0.0472(5) Uani d . 1 . .
C C5 0.5148(3) 0.2828(2) 0.28008(12) 0.0601(6) Uani d . 1 . .
H H5 0.4608 0.2271 0.3063 0.072 Uiso calc R 1 . .
C C6 0.6447(3) 0.3036(2) 0.30424(12) 0.0605(6) Uani d . 1 . .
H H6 0.6793 0.2610 0.3471 0.073 Uiso calc R 1 . .
C C7 0.7296(2) 0.3877(2) 0.26657(11) 0.0521(5) Uani d . 1 . .
H H7 0.8184 0.4012 0.2851 0.063 Uiso calc R 1 . .
C C8 0.6817(2) 0.44914(18) 0.20301(11) 0.0444(5) Uani d . 1 . .
C C9 0.5446(2) 0.42934(17) 0.17467(10) 0.0410(5) Uani d . 1 . .
C C10 0.8940(2) 0.5533(2) 0.18444(13) 0.0587(6) Uani d . 1 . .
H H10A 0.9454 0.4755 0.1842 0.070 Uiso calc R 1 . .
H H10B 0.8996 0.5879 0.2356 0.070 Uiso calc R 1 . .
C C11 0.9503(2) 0.6450(2) 0.12900(15) 0.0663(7) Uani d . 1 . .
H H11A 0.9384 0.6113 0.0779 0.080 Uiso calc R 1 . .
H H11B 1.0472 0.6550 0.1401 0.080 Uiso calc R 1 . .
C C12 0.8825(2) 0.7721(2) 0.13204(13) 0.0615(6) Uani d . 1 . .
H H12A 0.7853 0.7618 0.1225 0.074 Uiso calc R 1 . .
H H12B 0.8969 0.8070 0.1827 0.074 Uiso calc R 1 . .
C C13 0.9360(2) 0.8621(2) 0.07498(13) 0.0561(6) Uani d . 1 . .
C C14 0.6530(2) 0.90707(19) -0.04826(11) 0.0451(5) Uani d . 1 . .
H H14 0.6949 0.9608 -0.0818 0.054 Uiso calc R 1 . .
C C15 0.5098(2) 0.87299(17) -0.06186(10) 0.0422(5) Uani d . 1 . .
C C16 0.4388(2) 0.9199(2) -0.12587(12) 0.0528(5) Uani d . 1 . .
H H16 0.4825 0.9730 -0.1591 0.063 Uiso calc R 1 . .
C C17 0.3046(2) 0.8885(2) -0.14041(13) 0.0581(6) Uani d . 1 . .
H H17 0.2572 0.9203 -0.1831 0.070 Uiso calc R 1 . .
C C18 0.2416(2) 0.8095(2) -0.09103(12) 0.0503(5) Uani d . 1 . .
C C19 0.3084(2) 0.7626(2) -0.02718(12) 0.0518(5) Uani d . 1 . .
H H19 0.2635 0.7104 0.0060 0.062 Uiso calc R 1 . .
C C20 0.4429(2) 0.79389(19) -0.01275(11) 0.0475(5) Uani d . 1 . .
H H20 0.4892 0.7618 0.0302 0.057 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 . . 118.32(16) ?
C1 N1 C9 . . 117.24(19) ?
C13 N2 N3 . . 121.83(18) ?
C13 N2 H2A . . 119.1 ?
N3 N2 H2A . . 119.1 ?
C14 N3 N2 . . 115.79(18) ?
O3 N4 O4 . . 123.0(2) ?
O3 N4 C18 . . 118.4(3) ?
O4 N4 C18 . . 118.6(2) ?
N1 C1 C2 . . 124.4(2) ?
N1 C1 H1 . . 117.8 ?
C2 C1 H1 . . 117.8 ?
C3 C2 C1 . . 118.6(2) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 120.0(2) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C9 . . 116.9(2) ?
C3 C4 C5 . . 123.6(2) ?
C9 C4 C5 . . 119.41(19) ?
C6 C5 C4 . . 119.8(2) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C7 . . 121.9(2) ?
C5 C6 H6 . . 119.0 ?
C7 C6 H6 . . 119.0 ?
C8 C7 C6 . . 119.9(2) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 O1 . . 125.06(19) ?
C7 C8 C9 . . 120.23(19) ?
O1 C8 C9 . . 114.71(16) ?
N1 C9 C4 . . 122.77(18) ?
N1 C9 C8 . . 118.49(17) ?
C4 C9 C8 . . 118.73(17) ?
O1 C10 C11 . . 107.34(19) ?
O1 C10 H10A . . 110.2 ?
C11 C10 H10A . . 110.2 ?
O1 C10 H10B . . 110.2 ?
C11 C10 H10B . . 110.2 ?
H10A C10 H10B . . 108.5 ?
C10 C11 C12 . . 112.5(2) ?
C10 C11 H11A . . 109.1 ?
C12 C11 H11A . . 109.1 ?
C10 C11 H11B . . 109.1 ?
C12 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.8 ?
C13 C12 C11 . . 112.35(19) ?
C13 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
C13 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.9 ?
O2 C13 N2 . . 119.3(2) ?
O2 C13 C12 . . 121.3(2) ?
N2 C13 C12 . . 119.38(19) ?
N3 C14 C15 . . 120.28(19) ?
N3 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C20 C15 C16 . . 118.90(19) ?
C20 C15 C14 . . 121.72(18) ?
C16 C15 C14 . . 119.38(19) ?
C17 C16 C15 . . 120.6(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C18 C17 C16 . . 119.1(2) ?
C18 C17 H17 . . 120.5 ?
C16 C17 H17 . . 120.5 ?
C19 C18 C17 . . 121.7(2) ?
C19 C18 N4 . . 118.3(2) ?
C17 C18 N4 . . 120.0(2) ?
C18 C19 C20 . . 119.2(2) ?
C18 C19 H19 . . 120.4 ?
C20 C19 H19 . . 120.4 ?
C19 C20 C15 . . 120.53(19) ?
C19 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
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 . 1.363(2) ?
O1 C10 . 1.430(2) ?
O2 C13 . 1.235(2) ?
O3 N4 . 1.208(3) ?
O4 N4 . 1.220(3) ?
N1 C1 . 1.319(3) ?
N1 C9 . 1.358(2) ?
N2 C13 . 1.343(3) ?
N2 N3 . 1.377(2) ?
N2 H2A . 0.8600 ?
N3 C14 . 1.269(3) ?
N4 C18 . 1.471(3) ?
C1 C2 . 1.394(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.354(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.412(3) ?
C3 H3 . 0.9300 ?
C4 C9 . 1.413(3) ?
C4 C5 . 1.421(3) ?
C5 C6 . 1.348(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.407(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.361(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.433(3) ?
C10 C11 . 1.500(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.508(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.497(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C14 C15 . 1.464(3) ?
C14 H14 . 0.9300 ?
C15 C20 . 1.390(3) ?
C15 C16 . 1.392(3) ?
C16 C17 . 1.375(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.374(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.370(3) ?
C19 C20 . 1.377(3) ?
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 O2 3_775 0.86 2.03 2.876(3) 169.9
C12 H12A O1 . 0.97 2.57 2.912(3) 101
C12 H12A N3 . 0.97 2.33 2.807(3) 109.3
C10 H10B O3 4_676 0.97 2.45 3.311(3) 148.4
C2 H2 O4 3_565 0.93 2.58 3.496(3) 166.6
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 . . . . -178.96(19) ?
C9 N1 C1 C2 . . . . 2.4(3) ?
N1 C1 C2 C3 . . . . -2.5(4) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C9 . . . . 1.7(3) ?
C2 C3 C4 C5 . . . . -176.9(2) ?
C3 C4 C5 C6 . . . . 179.5(2) ?
C9 C4 C5 C6 . . . . 0.9(3) ?
C4 C5 C6 C7 . . . . 0.4(3) ?
C5 C6 C7 C8 . . . . -1.1(3) ?
C6 C7 C8 O1 . . . . -178.65(19) ?
C6 C7 C8 C9 . . . . 0.5(3) ?
C10 O1 C8 C7 . . . . 0.7(3) ?
C10 O1 C8 C9 . . . . -178.53(17) ?
C1 N1 C9 C4 . . . . -0.3(3) ?
C1 N1 C9 C8 . . . . 178.11(19) ?
C3 C4 C9 N1 . . . . -1.7(3) ?
C5 C4 C9 N1 . . . . 176.92(18) ?
C3 C4 C9 C8 . . . . 179.88(18) ?
C5 C4 C9 C8 . . . . -1.5(3) ?
C7 C8 C9 N1 . . . . -177.70(18) ?
O1 C8 C9 N1 . . . . 1.6(3) ?
C7 C8 C9 C4 . . . . 0.8(3) ?
O1 C8 C9 C4 . . . . -179.99(16) ?
C8 O1 C10 C11 . . . . 179.83(18) ?
O1 C10 C11 C12 . . . . 65.1(3) ?
C10 C11 C12 C13 . . . . -178.24(19) ?
N3 N2 C13 O2 . . . . 180.00(19) ?
N3 N2 C13 C12 . . . . -0.1(3) ?
C11 C12 C13 O2 . . . . -66.0(3) ?
C11 C12 C13 N2 . . . . 114.1(2) ?
N2 N3 C14 C15 . . . . -179.17(16) ?
N3 C14 C15 C20 . . . . 0.6(3) ?
N3 C14 C15 C16 . . . . -178.84(18) ?
C20 C15 C16 C17 . . . . -0.1(3) ?
C14 C15 C16 C17 . . . . 179.41(18) ?
C15 C16 C17 C18 . . . . -0.3(3) ?
C16 C17 C18 C19 . . . . 0.9(3) ?
C16 C17 C18 N4 . . . . -178.20(19) ?
O3 N4 C18 C19 . . . . 177.6(2) ?
O4 N4 C18 C19 . . . . -4.7(3) ?
O3 N4 C18 C17 . . . . -3.2(3) ?
O4 N4 C18 C17 . . . . 174.4(2) ?
C17 C18 C19 C20 . . . . -1.1(3) ?
N4 C18 C19 C20 . . . . 178.07(18) ?
C18 C19 C20 C15 . . . . 0.6(3) ?
C16 C15 C20 C19 . . . . -0.1(3) ?
C14 C15 C20 C19 . . . . -179.55(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745190
