#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228544.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228544
loop_
_publ_author_name
'Ban, Hong-Yan'
_publ_section_title
;
 (E)-4-Methoxy-N'-(4-nitrobenzylidene)benzohydrazide
 methanol monosolvate
;
_journal_coeditor_code           RZ2522
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3240
_journal_paper_doi               10.1107/S160053681004701X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 N3 O4, C H4 O'
_chemical_formula_moiety         'C15 H13 N3 O4, C H4 O'
_chemical_formula_sum            'C16 H17 N3 O5'
_chemical_formula_weight         331.33
_chemical_name_systematic
;
(E)-4-Methoxy-N'-(4-nitrobenzylidene)benzohydrazide methanol
monosolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.004(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6482(14)
_cell_length_b                   17.730(3)
_cell_length_c                   13.898(2)
_cell_measurement_reflns_used    794
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.7
_cell_volume                     1631.9(5)
_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.1147
_diffrn_reflns_av_sigmaI/netI    0.1391
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12876
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.2347
_refine_ls_R_factor_gt           0.0805
_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)+(0.0757P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.2040
_reflns_number_gt                1184
_reflns_number_total             3466
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2522.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228544
_cod_database_fobs_code          2228544
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.4536(7) -0.3135(2) 0.1424(3) 0.0634(12) Uani d . 1 . .
N N2 0.1193(5) 0.0260(2) 0.1132(2) 0.0453(9) Uani d . 1 . .
N N3 0.0063(5) 0.0908(2) 0.1112(3) 0.0460(9) Uani d D 1 . .
O O1 0.3670(6) -0.3698(2) 0.1665(3) 0.0923(13) Uani d . 1 . .
O O2 0.6283(6) -0.3132(2) 0.1217(3) 0.0930(13) Uani d . 1 . .
O O3 0.2843(4) 0.15868(16) 0.0864(2) 0.0650(10) Uani d . 1 . .
O O4 -0.3188(4) 0.43167(16) 0.0795(2) 0.0709(10) Uani d . 1 . .
O O5 0.5933(4) 0.05685(17) 0.1482(3) 0.0642(10) Uani d . 1 . .
H H5 0.4898 0.0767 0.1237 0.096 Uiso calc R 1 . .
C C1 0.1378(6) -0.1068(2) 0.1293(3) 0.0424(11) Uani d . 1 . .
C C2 0.3344(6) -0.1112(2) 0.1018(3) 0.0529(12) Uani d . 1 . .
H H2 0.3964 -0.0682 0.0801 0.063 Uiso calc R 1 . .
C C3 0.4373(6) -0.1786(3) 0.1064(3) 0.0549(13) Uani d . 1 . .
H H3 0.5680 -0.1817 0.0876 0.066 Uiso calc R 1 . .
C C4 0.3437(7) -0.2407(2) 0.1391(3) 0.0493(12) Uani d . 1 . .
C C5 0.1521(7) -0.2403(3) 0.1657(3) 0.0586(13) Uani d . 1 . .
H H5A 0.0922 -0.2840 0.1866 0.070 Uiso calc R 1 . .
C C6 0.0480(6) -0.1719(3) 0.1607(3) 0.0563(13) Uani d . 1 . .
H H6 -0.0834 -0.1699 0.1786 0.068 Uiso calc R 1 . .
C C7 0.0276(6) -0.0354(3) 0.1262(3) 0.0495(12) Uani d . 1 . .
H H7 -0.1100 -0.0350 0.1338 0.059 Uiso calc R 1 . .
C C8 0.1041(7) 0.1569(2) 0.0971(3) 0.0461(11) Uani d . 1 . .
C C9 -0.0195(6) 0.2263(2) 0.0959(3) 0.0449(11) Uani d . 1 . .
C C10 -0.2157(6) 0.2311(2) 0.1201(3) 0.0508(12) Uani d . 1 . .
H H10 -0.2785 0.1877 0.1403 0.061 Uiso calc R 1 . .
C C11 -0.3223(6) 0.2981(2) 0.1153(3) 0.0535(12) Uani d . 1 . .
H H11 -0.4551 0.2998 0.1314 0.064 Uiso calc R 1 . .
C C12 -0.2287(7) 0.3619(2) 0.0864(3) 0.0540(12) Uani d . 1 . .
C C13 -0.0345(7) 0.3593(3) 0.0605(4) 0.0829(18) Uani d . 1 . .
H H13 0.0277 0.4028 0.0402 0.100 Uiso calc R 1 . .
C C14 0.0666(7) 0.2920(3) 0.0649(4) 0.0745(16) Uani d . 1 . .
H H14 0.1977 0.2904 0.0465 0.089 Uiso calc R 1 . .
C C15 -0.5263(8) 0.4384(3) 0.0967(4) 0.0833(17) Uani d . 1 . .
H H15A -0.6078 0.4115 0.0477 0.125 Uiso calc R 1 . .
H H15B -0.5642 0.4907 0.0951 0.125 Uiso calc R 1 . .
H H15C -0.5467 0.4177 0.1589 0.125 Uiso calc R 1 . .
C C16 0.5721(7) 0.0414(3) 0.2467(4) 0.0823(17) Uani d . 1 . .
H H16A 0.6181 -0.0089 0.2617 0.123 Uiso calc R 1 . .
H H16B 0.4327 0.0459 0.2588 0.123 Uiso calc R 1 . .
H H16C 0.6512 0.0767 0.2863 0.123 Uiso calc R 1 . .
H H3A -0.128(2) 0.087(2) 0.116(3) 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
O1 N1 O2 . . 123.5(4) ?
O1 N1 C4 . . 118.7(4) ?
O2 N1 C4 . . 117.7(5) ?
C7 N2 N3 . . 116.9(3) ?
C8 N3 N2 . . 117.2(3) ?
C8 N3 H3A . . 124(3) ?
N2 N3 H3A . . 119(3) ?
C12 O4 C15 . . 119.1(4) ?
C16 O5 H5 . . 109.5 ?
C6 C1 C2 . . 118.6(4) ?
C6 C1 C7 . . 120.1(4) ?
C2 C1 C7 . . 121.3(4) ?
C3 C2 C1 . . 120.6(4) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 118.5(4) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C5 C4 C3 . . 123.6(4) ?
C5 C4 N1 . . 118.0(4) ?
C3 C4 N1 . . 118.4(4) ?
C4 C5 C6 . . 117.7(4) ?
C4 C5 H5A . . 121.2 ?
C6 C5 H5A . . 121.2 ?
C1 C6 C5 . . 120.9(4) ?
C1 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
N2 C7 C1 . . 120.1(4) ?
N2 C7 H7 . . 120.0 ?
C1 C7 H7 . . 120.0 ?
O3 C8 N3 . . 121.7(4) ?
O3 C8 C9 . . 121.8(4) ?
N3 C8 C9 . . 116.5(4) ?
C10 C9 C14 . . 116.8(4) ?
C10 C9 C8 . . 125.8(4) ?
C14 C9 C8 . . 117.4(4) ?
C9 C10 C11 . . 122.2(4) ?
C9 C10 H10 . . 118.9 ?
C11 C10 H10 . . 118.9 ?
C12 C11 C10 . . 118.7(4) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.6 ?
C11 C12 C13 . . 120.9(4) ?
C11 C12 O4 . . 123.9(4) ?
C13 C12 O4 . . 115.2(4) ?
C14 C13 C12 . . 119.2(5) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C13 C14 C9 . . 122.2(4) ?
C13 C14 H14 . . 118.9 ?
C9 C14 H14 . . 118.9 ?
O4 C15 H15A . . 109.5 ?
O4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O5 C16 H16A . . 109.5 ?
O5 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O5 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 O1 . 1.214(4) ?
N1 O2 . 1.221(5) ?
N1 C4 . 1.482(5) ?
N2 C7 . 1.269(5) ?
N2 N3 . 1.372(4) ?
N3 C8 . 1.363(5) ?
N3 H3A . 0.902(10) ?
O3 C8 . 1.221(4) ?
O4 C12 . 1.374(5) ?
O4 C15 . 1.426(5) ?
O5 C16 . 1.415(5) ?
O5 H5 . 0.8200 ?
C1 C6 . 1.386(5) ?
C1 C2 . 1.395(5) ?
C1 C7 . 1.461(5) ?
C2 C3 . 1.376(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.362(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.357(5) ?
C5 C6 . 1.395(5) ?
C5 H5A . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.479(5) ?
C9 C10 . 1.377(5) ?
C9 C14 . 1.383(5) ?
C10 C11 . 1.383(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.367(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.371(6) ?
C13 C14 . 1.369(6) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 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
O5 H5 O3 . 0.82 2.03 2.812(4) 159.2
O5 H5 N2 . 0.82 2.61 3.194(4) 128.9
N3 H3A O5 1_455 0.902(10) 2.018(15) 2.900(4) 166(4)
