#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/19/2221912.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_2221912
loop_
_publ_author_name
'Ren, Chun-Yan'
_publ_section_title
;
 (E)-N'-(4-Nitrobenzylidene)-2-(8-quinolyloxy)acetohydrazide
 methanol solvate
;
_journal_coeditor_code           BI2363
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1212
_journal_paper_doi               10.1107/S1600536809015992
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H14 N4 O4, C H4 O'
_chemical_formula_moiety         'C18 H14 N4 O4, C H4 O'
_chemical_formula_sum            'C19 H18 N4 O5'
_chemical_formula_weight         382.37
_chemical_name_systematic
;
(E)-N'-(4-Nitrobenzylidene)-2-(8-quinolyloxy)acetohydrazide
methanol solvate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 120.06(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.345(10)
_cell_length_b                   11.559(11)
_cell_length_c                   16.234(12)
_cell_measurement_reflns_used    1871
_cell_measurement_temperature    295
_cell_measurement_theta_max      22.76
_cell_measurement_theta_min      2.28
_cell_volume                     1843(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9196
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0561
_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)+(0.1106P)²+0.0143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1952
_reflns_number_gt                1872
_reflns_number_total             3258
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2363.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221912
_cod_database_fobs_code          2221912
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 0.1624(2) 0.23691(14) 1.11105(14) 0.0547(6) Uani d . 1 . .
O O2 0.1325(2) -0.07065(16) 1.10099(16) 0.0694(7) Uani d . 1 . .
O O3 0.4318(3) -0.4685(3) 0.7787(2) 0.1065(10) Uani d . 1 . .
O O4 0.5020(4) -0.3368(3) 0.7175(2) 0.1177(12) Uani d . 1 . .
O O5 0.2556(3) 0.27429(19) 0.9641(2) 0.0938(9) Uani d . 1 . .
H H5 0.2540 0.3180 1.0033 0.141 Uiso calc R 1 . .
N N1 0.2147(3) 0.45024(19) 1.06723(17) 0.0541(7) Uani d . 1 . .
N N2 0.2130(3) 0.05140(19) 1.02969(17) 0.0547(7) Uani d . 1 . .
H H2 0.2310 0.1214 1.0219 0.066 Uiso d R 1 . .
N N3 0.2403(3) -0.0398(2) 0.98661(17) 0.0538(7) Uani d . 1 . .
N N4 0.4508(3) -0.3671(3) 0.7651(2) 0.0834(9) Uani d . 1 . .
C C1 0.2366(3) 0.5556(3) 1.0457(2) 0.0621(9) Uani d . 1 . .
H H1 0.2848 0.5621 1.0135 0.075 Uiso calc R 1 . .
C C2 0.1921(4) 0.6582(2) 1.0679(2) 0.0652(9) Uani d . 1 . .
H H2A 0.2101 0.7298 1.0504 0.078 Uiso calc R 1 . .
C C3 0.1227(4) 0.6509(2) 1.1152(2) 0.0602(9) Uani d . 1 . .
H H3 0.0909 0.7176 1.1296 0.072 Uiso calc R 1 . .
C C4 0.0985(3) 0.5417(2) 1.14255(19) 0.0510(8) Uani d . 1 . .
C C5 0.0322(3) 0.5278(3) 1.1966(2) 0.0605(9) Uani d . 1 . .
H H5A -0.0014 0.5924 1.2123 0.073 Uiso calc R 1 . .
C C6 0.0173(3) 0.4215(3) 1.2255(2) 0.0618(9) Uani d . 1 . .
H H6 -0.0221 0.4141 1.2635 0.074 Uiso calc R 1 . .
C C7 0.0611(3) 0.3223(2) 1.1981(2) 0.0569(8) Uani d . 1 . .
H H7 0.0483 0.2498 1.2172 0.068 Uiso calc R 1 . .
C C8 0.1224(3) 0.3306(2) 1.14367(19) 0.0474(7) Uani d . 1 . .
C C9 0.1459(3) 0.4422(2) 1.11638(18) 0.0456(7) Uani d . 1 . .
C C10 0.1252(3) 0.1263(2) 1.1307(2) 0.0564(8) Uani d . 1 . .
H H10A 0.0283 0.1263 1.1084 0.068 Uiso calc R 1 . .
H H10B 0.1728 0.1145 1.1990 0.068 Uiso calc R 1 . .
C C11 0.1570(3) 0.0270(2) 1.0849(2) 0.0521(8) Uani d . 1 . .
C C12 0.2988(3) -0.0149(2) 0.9392(2) 0.0543(8) Uani d . 1 . .
H H12 0.3186 0.0619 0.9339 0.065 Uiso calc R 1 . .
C C13 0.3350(3) -0.1051(2) 0.89341(19) 0.0511(7) Uani d . 1 . .
C C14 0.2917(3) -0.2196(2) 0.8882(2) 0.0602(8) Uani d . 1 . .
H H14 0.2367 -0.2386 0.9135 0.072 Uiso calc R 1 . .
C C15 0.3289(3) -0.3049(3) 0.8461(2) 0.0630(9) Uani d . 1 . .
H H15 0.2996 -0.3808 0.8429 0.076 Uiso calc R 1 . .
C C16 0.4108(3) -0.2748(3) 0.8090(2) 0.0604(8) Uani d . 1 . .
C C17 0.4521(3) -0.1636(3) 0.8101(2) 0.0663(9) Uani d . 1 . .
H H17 0.5048 -0.1452 0.7828 0.080 Uiso calc R 1 . .
C C18 0.4146(3) -0.0785(3) 0.8526(2) 0.0610(9) Uani d . 1 . .
H H18 0.4427 -0.0026 0.8539 0.073 Uiso calc R 1 . .
C C19 0.3321(4) 0.3241(3) 0.9278(3) 0.0858(12) Uani d . 1 . .
H H19A 0.2805 0.3851 0.8845 0.129 Uiso calc R 1 . .
H H19B 0.3535 0.2664 0.8948 0.129 Uiso calc R 1 . .
H H19C 0.4149 0.3552 0.9791 0.129 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 . . 115.2(2) ?
C19 O5 H5 . . 109.5 ?
C1 N1 C9 . . 116.9(2) ?
C11 N2 N3 . . 118.1(2) ?
C11 N2 H2 . . 121.0 ?
N3 N2 H2 . . 120.9 ?
C12 N3 N2 . . 116.6(2) ?
O4 N4 O3 . . 124.4(3) ?
O4 N4 C16 . . 117.1(4) ?
O3 N4 C16 . . 118.5(3) ?
N1 C1 C2 . . 124.7(3) ?
N1 C1 H1 . . 117.6 ?
C2 C1 H1 . . 117.6 ?
C3 C2 C1 . . 118.7(3) ?
C3 C2 H2A . . 120.7 ?
C1 C2 H2A . . 120.7 ?
C2 C3 C4 . . 119.8(3) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C4 C9 . . 117.9(3) ?
C3 C4 C5 . . 122.8(3) ?
C9 C4 C5 . . 119.3(3) ?
C6 C5 C4 . . 120.8(3) ?
C6 C5 H5A . . 119.6 ?
C4 C5 H5A . . 119.6 ?
C5 C6 C7 . . 120.3(3) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C8 C7 C6 . . 121.3(3) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C7 C8 O1 . . 124.2(2) ?
C7 C8 C9 . . 119.6(2) ?
O1 C8 C9 . . 116.2(2) ?
N1 C9 C4 . . 122.0(2) ?
N1 C9 C8 . . 119.3(2) ?
C4 C9 C8 . . 118.7(3) ?
O1 C10 C11 . . 113.6(2) ?
O1 C10 H10A . . 108.8 ?
C11 C10 H10A . . 108.8 ?
O1 C10 H10B . . 108.8 ?
C11 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
O2 C11 N2 . . 124.3(3) ?
O2 C11 C10 . . 117.5(3) ?
N2 C11 C10 . . 118.2(2) ?
N3 C12 C13 . . 120.8(3) ?
N3 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C18 C13 C14 . . 118.1(3) ?
C18 C13 C12 . . 120.0(3) ?
C14 C13 C12 . . 121.9(3) ?
C15 C14 C13 . . 121.4(3) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C16 . . 118.3(3) ?
C14 C15 H15 . . 120.8 ?
C16 C15 H15 . . 120.8 ?
C17 C16 C15 . . 122.3(3) ?
C17 C16 N4 . . 120.0(3) ?
C15 C16 N4 . . 117.8(3) ?
C16 C17 C18 . . 119.0(3) ?
C16 C17 H17 . . 120.5 ?
C18 C17 H17 . . 120.5 ?
C17 C18 C13 . . 120.9(3) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?
O5 C19 H19A . . 109.5 ?
O5 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O5 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 . 1.378(3) ?
O1 C10 . 1.431(3) ?
O2 C11 . 1.222(3) ?
O3 N4 . 1.232(4) ?
O4 N4 . 1.227(4) ?
O5 C19 . 1.394(4) ?
O5 H5 . 0.820 ?
N1 C1 . 1.324(4) ?
N1 C9 . 1.371(4) ?
N2 C11 . 1.362(4) ?
N2 N3 . 1.383(3) ?
N2 H2 . 0.860 ?
N3 C12 . 1.275(4) ?
N4 C16 . 1.476(4) ?
C1 C2 . 1.406(4) ?
C1 H1 . 0.930 ?
C2 C3 . 1.350(5) ?
C2 H2A . 0.930 ?
C3 C4 . 1.411(4) ?
C3 H3 . 0.930 ?
C4 C9 . 1.421(4) ?
C4 C5 . 1.422(4) ?
C5 C6 . 1.355(4) ?
C5 H5A . 0.930 ?
C6 C7 . 1.407(4) ?
C6 H6 . 0.930 ?
C7 C8 . 1.375(4) ?
C7 H7 . 0.930 ?
C8 C9 . 1.431(4) ?
C10 C11 . 1.506(4) ?
C10 H10A . 0.970 ?
C10 H10B . 0.970 ?
C12 C13 . 1.455(4) ?
C12 H12 . 0.930 ?
C13 C18 . 1.395(4) ?
C13 C14 . 1.399(4) ?
C14 C15 . 1.380(4) ?
C14 H14 . 0.930 ?
C15 C16 . 1.381(4) ?
C15 H15 . 0.930 ?
C16 C17 . 1.366(4) ?
C17 C18 . 1.385(4) ?
C17 H17 . 0.930 ?
C18 H18 . 0.930 ?
C19 H19A . 0.960 ?
C19 H19B . 0.960 ?
C19 H19C . 0.960 ?
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 H5 N1 . 0.82 2.02 2.817(4) 164.2
N2 H2 O5 . 0.86 2.08 2.919(4) 163.8
C17 H17 O3 2_656 0.93 2.53 3.287(5) 138.6
C18 H18 O4 2_656 0.93 2.48 3.329(5) 152.0
C3 H3 O2 1_565 0.93 2.58 3.233(5) 127.8
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 . . . . -176.7(3) ?
C9 N1 C1 C2 . . . . -1.3(5) ?
N1 C1 C2 C3 . . . . 0.4(5) ?
C1 C2 C3 C4 . . . . 1.1(5) ?
C2 C3 C4 C9 . . . . -1.7(5) ?
C2 C3 C4 C5 . . . . 176.8(3) ?
C3 C4 C5 C6 . . . . -176.6(3) ?
C9 C4 C5 C6 . . . . 1.9(5) ?
C4 C5 C6 C7 . . . . -3.3(5) ?
C5 C6 C7 C8 . . . . 1.5(5) ?
C6 C7 C8 O1 . . . . -177.1(3) ?
C6 C7 C8 C9 . . . . 1.8(5) ?
C10 O1 C8 C7 . . . . 5.2(4) ?
C10 O1 C8 C9 . . . . -173.7(3) ?
C1 N1 C9 C4 . . . . 0.6(4) ?
C1 N1 C9 C8 . . . . -178.4(3) ?
C3 C4 C9 N1 . . . . 0.9(4) ?
C5 C4 C9 N1 . . . . -177.7(3) ?
C3 C4 C9 C8 . . . . 179.9(3) ?
C5 C4 C9 C8 . . . . 1.4(4) ?
C7 C8 C9 N1 . . . . 175.9(3) ?
O1 C8 C9 N1 . . . . -5.1(4) ?
C7 C8 C9 C4 . . . . -3.2(4) ?
O1 C8 C9 C4 . . . . 175.8(3) ?
C8 O1 C10 C11 . . . . 173.7(3) ?
N3 N2 C11 O2 . . . . 2.0(5) ?
N3 N2 C11 C10 . . . . -179.0(3) ?
O1 C10 C11 O2 . . . . 177.6(3) ?
O1 C10 C11 N2 . . . . -1.4(4) ?
N2 N3 C12 C13 . . . . 178.4(3) ?
N3 C12 C13 C18 . . . . -171.6(3) ?
N3 C12 C13 C14 . . . . 8.8(5) ?
C18 C13 C14 C15 . . . . 1.6(5) ?
C12 C13 C14 C15 . . . . -178.7(3) ?
C13 C14 C15 C16 . . . . 0.1(5) ?
C14 C15 C16 C17 . . . . -2.0(5) ?
C14 C15 C16 N4 . . . . 179.4(3) ?
O4 N4 C16 C17 . . . . -11.5(5) ?
O3 N4 C16 C17 . . . . 168.2(4) ?
O4 N4 C16 C15 . . . . 167.1(3) ?
O3 N4 C16 C15 . . . . -13.2(5) ?
C15 C16 C17 C18 . . . . 2.1(5) ?
N4 C16 C17 C18 . . . . -179.3(3) ?
C16 C17 C18 C13 . . . . -0.3(5) ?
C14 C13 C18 C17 . . . . -1.5(5) ?
C12 C13 C18 C17 . . . . 178.8(3) ?
