#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/98/2229839.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_2229839
loop_
_publ_author_name
'Zhu, Hai-Yun'
_publ_section_title
;
 N'-(2-Methoxybenzylidene)-4-nitrobenzohydrazide
;
_journal_coeditor_code           SJ5112
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o812
_journal_paper_doi               10.1107/S1600536811008014
_journal_volume                  67
_journal_year                    2011
_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
;
N'-(2-Methoxybenzylidene)-4-nitrobenzohydrazide
;
_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                 93.572(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.737(2)
_cell_length_b                   14.728(2)
_cell_length_c                   9.1320(10)
_cell_measurement_reflns_used    864
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.3
_cell_volume                     1441.3(4)
_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  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.0765
_diffrn_reflns_av_sigmaI/netI    0.1038
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9434
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut from needle'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.0577
_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)+(0.0427P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                1426
_reflns_number_total             3129
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5112.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229839
_cod_database_fobs_code          2229839
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 0.30611(19) 0.83021(15) 1.0924(2) 0.0485(6) Uani d . 1 . .
N N2 0.2592(2) 0.75864(15) 1.0066(2) 0.0494(6) Uani d D 1 . .
N N3 0.0510(2) 0.38411(19) 0.7154(3) 0.0661(7) Uani d . 1 . .
O O1 0.27693(19) 1.07382(12) 0.9099(2) 0.0761(7) Uani d . 1 . .
O O2 0.22796(17) 0.67342(11) 1.2070(2) 0.0597(6) Uani d . 1 . .
O O3 0.0703(2) 0.30882(15) 0.7635(3) 0.1087(10) Uani d . 1 . .
O O4 -0.0029(2) 0.39878(16) 0.5963(3) 0.0971(8) Uani d . 1 . .
C C1 0.3456(2) 1.07183(19) 1.0414(3) 0.0539(7) Uani d . 1 . .
C C2 0.3634(2) 0.98652(18) 1.1036(3) 0.0469(7) Uani d . 1 . .
C C3 0.4307(2) 0.9800(2) 1.2379(3) 0.0612(8) Uani d . 1 . .
H H3 0.4428 0.9234 1.2817 0.073 Uiso calc R 1 . .
C C4 0.4799(3) 1.0566(2) 1.3077(4) 0.0776(10) Uani d . 1 . .
H H4 0.5248 1.0516 1.3977 0.093 Uiso calc R 1 . .
C C5 0.4618(3) 1.1399(2) 1.2431(4) 0.0752(10) Uani d . 1 . .
H H5 0.4958 1.1912 1.2896 0.090 Uiso calc R 1 . .
C C6 0.3947(3) 1.1492(2) 1.1112(4) 0.0695(9) Uani d . 1 . .
H H6 0.3821 1.2062 1.0691 0.083 Uiso calc R 1 . .
C C7 0.2470(4) 1.1582(2) 0.8462(4) 0.1186(16) Uani d . 1 . .
H H7A 0.2078 1.1957 0.9160 0.178 Uiso calc R 1 . .
H H7B 0.1908 1.1496 0.7614 0.178 Uiso calc R 1 . .
H H7C 0.3218 1.1872 0.8176 0.178 Uiso calc R 1 . .
C C8 0.3139(2) 0.90618(17) 1.0267(3) 0.0476(7) Uani d . 1 . .
H H8 0.2874 0.9105 0.9280 0.057 Uiso calc R 1 . .
C C9 0.2221(2) 0.68303(17) 1.0733(3) 0.0439(6) Uani d . 1 . .
C C10 0.1746(2) 0.60759(16) 0.9749(3) 0.0408(6) Uani d . 1 . .
C C11 0.1895(2) 0.51927(17) 1.0271(3) 0.0498(7) Uani d . 1 . .
H H11 0.2268 0.5096 1.1204 0.060 Uiso calc R 1 . .
C C12 0.1499(2) 0.44613(18) 0.9432(3) 0.0524(7) Uani d . 1 . .
H H12 0.1615 0.3871 0.9775 0.063 Uiso calc R 1 . .
C C13 0.0927(2) 0.46272(17) 0.8069(3) 0.0467(7) Uani d . 1 . .
C C14 0.0734(2) 0.54826(19) 0.7530(3) 0.0507(7) Uani d . 1 . .
H H14 0.0332 0.5573 0.6610 0.061 Uiso calc R 1 . .
C C15 0.1148(2) 0.62158(18) 0.8380(3) 0.0492(7) Uani d . 1 . .
H H15 0.1023 0.6804 0.8029 0.059 Uiso calc R 1 . .
H H2 0.251(2) 0.7686(17) 0.9092(12) 0.059 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
C8 N1 N2 . . 115.6(2) ?
C9 N2 N1 . . 118.7(2) ?
C9 N2 H2 . . 124.7(16) ?
N1 N2 H2 . . 116.4(17) ?
O3 N3 O4 . . 123.3(3) ?
O3 N3 C13 . . 118.3(3) ?
O4 N3 C13 . . 118.3(3) ?
C1 O1 C7 . . 118.7(2) ?
O1 C1 C2 . . 115.5(2) ?
O1 C1 C6 . . 123.4(3) ?
C2 C1 C6 . . 121.0(3) ?
C1 C2 C3 . . 118.4(3) ?
C1 C2 C8 . . 120.0(3) ?
C3 C2 C8 . . 121.6(3) ?
C4 C3 C2 . . 120.9(3) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C5 C4 C3 . . 119.5(3) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 121.4(3) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C5 C6 C1 . . 118.9(3) ?
C5 C6 H6 . . 120.6 ?
C1 C6 H6 . . 120.6 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 C2 . . 121.1(2) ?
N1 C8 H8 . . 119.4 ?
C2 C8 H8 . . 119.4 ?
O2 C9 N2 . . 123.3(2) ?
O2 C9 C10 . . 120.4(2) ?
N2 C9 C10 . . 116.3(2) ?
C15 C10 C11 . . 119.0(2) ?
C15 C10 C9 . . 123.5(2) ?
C11 C10 C9 . . 117.4(2) ?
C12 C11 C10 . . 121.2(3) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C13 . . 118.1(3) ?
C11 C12 H12 . . 121.0 ?
C13 C12 H12 . . 121.0 ?
C14 C13 C12 . . 122.7(2) ?
C14 C13 N3 . . 119.0(3) ?
C12 C13 N3 . . 118.3(3) ?
C13 C14 C15 . . 118.8(2) ?
C13 C14 H14 . . 120.6 ?
C15 C14 H14 . . 120.6 ?
C10 C15 C14 . . 120.3(2) ?
C10 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
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 C8 . 1.275(3) ?
N1 N2 . 1.389(3) ?
N2 C9 . 1.342(3) ?
N2 H2 . 0.900(10) ?
N3 O3 . 1.206(3) ?
N3 O4 . 1.219(3) ?
N3 C13 . 1.480(3) ?
O1 C1 . 1.370(3) ?
O1 C7 . 1.402(3) ?
O2 C9 . 1.227(3) ?
C1 C2 . 1.387(4) ?
C1 C6 . 1.393(4) ?
C2 C3 . 1.387(4) ?
C2 C8 . 1.460(3) ?
C3 C4 . 1.384(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.371(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.499(3) ?
C10 C15 . 1.385(3) ?
C10 C11 . 1.391(3) ?
C11 C12 . 1.374(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.364(3) ?
C14 C15 . 1.387(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 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 H2 O2 4_575 0.900(10) 2.035(12) 2.913(3) 165(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7835219
