#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224493.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_2224493
loop_
_publ_author_name
'Ban, Hong-Yan'
'Li, Cong-Ming'
_publ_section_title
;
 (E)-2-Methoxy-N'-(4-nitrobenzylidene)benzohydrazide
;
_journal_coeditor_code           WN2369
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3272
_journal_paper_doi               10.1107/S160053680905079X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 N3 O4'
_chemical_formula_moiety         'C15 H13 N3 O4'
_chemical_formula_sum            'C15 H13 N3 O4'
_chemical_formula_weight         299.28
_chemical_name_systematic
;
(E)-2-Methoxy-N'-(4-nitrobenzylidene)benzohydrazide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.792(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1843(2)
_cell_length_b                   11.3718(3)
_cell_length_c                   13.0519(2)
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      2.6
_cell_volume                     1410.96(6)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART 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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8270
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0467
_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)+(0.0691P)²+0.1341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                1964
_reflns_number_total             3048
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2369.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224493
_cod_database_fobs_code          2224493
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
N N1 0.02468(14) 0.74628(13) 0.11097(11) 0.0533(4) Uani d . 1 . .
N N2 0.10276(15) 0.75892(13) 0.23349(11) 0.0542(4) Uani d D 1 . .
N N3 -0.37828(15) 0.80034(14) -0.46112(12) 0.0584(4) Uani d . 1 . .
O O1 0.18128(13) 0.87506(11) 0.43486(10) 0.0632(4) Uani d . 1 . .
O O2 0.16350(19) 0.56837(12) 0.25823(12) 0.0989(6) Uani d . 1 . .
O O3 -0.36814(16) 0.71210(14) -0.50895(11) 0.0841(5) Uani d . 1 . .
O O4 -0.45977(16) 0.87945(13) -0.51687(11) 0.0874(5) Uani d . 1 . .
C C1 -0.12755(16) 0.82699(14) -0.08248(13) 0.0477(4) Uani d . 1 . .
C C2 -0.13227(17) 0.72335(14) -0.14102(14) 0.0513(4) Uani d . 1 . .
H H2 -0.0804 0.6587 -0.0958 0.062 Uiso calc R 1 . .
C C3 -0.21222(17) 0.71486(15) -0.26456(14) 0.0518(4) Uani d . 1 . .
H H3 -0.2148 0.6454 -0.3032 0.062 Uiso calc R 1 . .
C C4 -0.28832(16) 0.81139(14) -0.32966(13) 0.0477(4) Uani d . 1 . .
C C5 -0.28638(18) 0.91571(15) -0.27587(15) 0.0572(4) Uani d . 1 . .
H H5 -0.3389 0.9798 -0.3219 0.069 Uiso calc R 1 . .
C C6 -0.20458(18) 0.92326(15) -0.15175(15) 0.0559(4) Uani d . 1 . .
H H6 -0.2009 0.9936 -0.1139 0.067 Uiso calc R 1 . .
C C7 -0.04485(17) 0.83471(15) 0.04892(14) 0.0523(4) Uani d . 1 . .
H H7 -0.0432 0.9044 0.0870 0.063 Uiso calc R 1 . .
C C8 0.17233(18) 0.66437(16) 0.30264(14) 0.0571(4) Uani d . 1 . .
C C9 0.26280(16) 0.68339(15) 0.43602(13) 0.0507(4) Uani d . 1 . .
C C10 0.26528(17) 0.78298(15) 0.49941(13) 0.0514(4) Uani d . 1 . .
C C11 0.35310(19) 0.78490(18) 0.62478(15) 0.0643(5) Uani d . 1 . .
H H11 0.3528 0.8500 0.6678 0.077 Uiso calc R 1 . .
C C12 0.4398(2) 0.6917(2) 0.68511(16) 0.0730(6) Uani d . 1 . .
H H12 0.4982 0.6944 0.7686 0.088 Uiso calc R 1 . .
C C13 0.4412(2) 0.5949(2) 0.62399(16) 0.0720(6) Uani d . 1 . .
H H13 0.5015 0.5326 0.6653 0.086 Uiso calc R 1 . .
C C14 0.35239(19) 0.59045(17) 0.50043(15) 0.0621(5) Uani d . 1 . .
H H14 0.3523 0.5238 0.4591 0.075 Uiso calc R 1 . .
C C15 0.1754(2) 0.97515(17) 0.49824(18) 0.0720(6) Uani d . 1 . .
H H15A 0.1474 0.9507 0.5530 0.108 Uiso calc R 1 . .
H H15B 0.1083 1.0306 0.4417 0.108 Uiso calc R 1 . .
H H15C 0.2665 1.0114 0.5426 0.108 Uiso calc R 1 . .
H H2A 0.102(2) 0.8277(12) 0.2684(17) 0.080 Uiso d 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
C7 N1 N2 . . 117.55(14) ?
C8 N2 N1 . . 118.97(14) ?
C8 N2 H2A . . 120.2(13) ?
N1 N2 H2A . . 120.6(13) ?
O4 N3 O3 . . 123.15(15) ?
O4 N3 C4 . . 118.28(15) ?
O3 N3 C4 . . 118.56(14) ?
C10 O1 C15 . . 118.79(13) ?
C2 C1 C6 . . 118.59(14) ?
C2 C1 C7 . . 120.89(14) ?
C6 C1 C7 . . 120.52(15) ?
C3 C2 C1 . . 121.13(14) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
C4 C3 C2 . . 118.51(15) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C5 C4 C3 . . 122.42(14) ?
C5 C4 N3 . . 119.23(14) ?
C3 C4 N3 . . 118.31(15) ?
C4 C5 C6 . . 118.42(15) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C5 C6 C1 . . 120.92(16) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
N1 C7 C1 . . 119.88(16) ?
N1 C7 H7 . . 120.1 ?
C1 C7 H7 . . 120.1 ?
O2 C8 N2 . . 121.41(15) ?
O2 C8 C9 . . 121.28(15) ?
N2 C8 C9 . . 117.30(15) ?
C14 C9 C10 . . 118.37(14) ?
C14 C9 C8 . . 114.99(15) ?
C10 C9 C8 . . 126.64(15) ?
O1 C10 C9 . . 117.77(13) ?
O1 C10 C11 . . 122.89(16) ?
C9 C10 C11 . . 119.34(16) ?
C12 C11 C10 . . 120.60(18) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.70(16) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C14 . . 119.37(18) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C13 C14 C9 . . 121.58(18) ?
C13 C14 H14 . . 119.2 ?
C9 C14 H14 . . 119.2 ?
O1 C15 H15A . . 109.5 ?
O1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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
N1 C7 . 1.268(2) ?
N1 N2 . 1.3672(17) ?
N2 C8 . 1.355(2) ?
N2 H2A . 0.908(9) ?
N3 O4 . 1.2127(18) ?
N3 O3 . 1.2183(18) ?
N3 C4 . 1.467(2) ?
O1 C10 . 1.3619(19) ?
O1 C15 . 1.429(2) ?
O2 C8 . 1.215(2) ?
C1 C2 . 1.390(2) ?
C1 C6 . 1.392(2) ?
C1 C7 . 1.460(2) ?
C2 C3 . 1.375(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(2) ?
C5 C6 . 1.381(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.498(2) ?
C9 C14 . 1.393(2) ?
C9 C10 . 1.394(2) ?
C10 C11 . 1.396(2) ?
C11 C12 . 1.371(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.364(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.379(2) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
N2 H2A O1 . 0.908(9) 1.940(16) 2.644(2) 133.0(15)
C3 H3 O2 3_565 0.93 2.50 3.260(2) 140
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7932830
