#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/21/2222152.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_2222152
loop_
_publ_author_name
'Zhang, Xinyou'
_publ_section_title
;
 4-Methoxy-N'-(2-methoxybenzylidene)benzohydrazide
;
_journal_coeditor_code           SU2114
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1388
_journal_paper_doi               10.1107/S1600536809019102
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H16 N2 O3'
_chemical_formula_moiety         'C16 H16 N2 O3'
_chemical_formula_sum            'C16 H16 N2 O3'
_chemical_formula_weight         284.31
_chemical_name_systematic
;
4-Methoxy-N'-(2-methoxybenzylidene)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                 107.233(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7050(10)
_cell_length_b                   16.053(2)
_cell_length_c                   7.7180(10)
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      2.5
_cell_volume                     1503.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8570
_diffrn_reflns_theta_full        26.23
_diffrn_reflns_theta_max         26.23
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0489
_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)+(0.0515P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                1574
_reflns_number_total             3007
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2114.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1503.5(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222152
_cod_database_fobs_code          2222152
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 0.11626(13) 0.25479(11) 0.8800(2) 0.0459(5) Uani d . 1 . .
N N2 0.20751(14) 0.23123(11) 0.8290(2) 0.0464(5) Uani d D 1 . .
O O1 -0.00123(13) 0.47737(10) 0.7280(2) 0.0698(5) Uani d . 1 . .
O O2 0.27806(12) 0.16021(9) 1.0915(2) 0.0572(4) Uani d . 1 . .
O O3 0.62405(13) 0.06696(12) 0.6746(2) 0.0832(6) Uani d . 1 . .
C C1 -0.03802(17) 0.34548(14) 0.8236(3) 0.0484(6) Uani d . 1 . .
C C2 -0.07099(18) 0.42835(15) 0.7881(3) 0.0532(6) Uani d . 1 . .
C C3 -0.1678(2) 0.45577(18) 0.8150(3) 0.0689(8) Uani d . 1 . .
H H3 -0.1900 0.5108 0.7906 0.083 Uiso calc R 1 . .
C C4 -0.2316(2) 0.4011(2) 0.8783(3) 0.0777(8) Uani d . 1 . .
H H4 -0.2970 0.4199 0.8958 0.093 Uiso calc R 1 . .
C C5 -0.2007(2) 0.3201(2) 0.9158(4) 0.0782(8) Uani d . 1 . .
H H5 -0.2440 0.2838 0.9593 0.094 Uiso calc R 1 . .
C C6 -0.10359(18) 0.29291(16) 0.8878(3) 0.0629(7) Uani d . 1 . .
H H6 -0.0821 0.2378 0.9130 0.075 Uiso calc R 1 . .
C C7 0.06430(17) 0.31710(14) 0.7935(3) 0.0477(6) Uani d . 1 . .
H H7 0.0918 0.3448 0.7103 0.057 Uiso calc R 1 . .
C C8 0.28308(17) 0.18075(13) 0.9401(3) 0.0456(5) Uani d . 1 . .
C C9 0.37276(17) 0.15184(13) 0.8685(3) 0.0467(6) Uani d . 1 . .
C C10 0.47380(19) 0.13301(16) 0.9881(3) 0.0693(7) Uani d . 1 . .
H H10 0.4844 0.1393 1.1119 0.083 Uiso calc R 1 . .
C C11 0.5597(2) 0.10505(18) 0.9289(4) 0.0772(8) Uani d . 1 . .
H H11 0.6276 0.0932 1.0121 0.093 Uiso calc R 1 . .
C C12 0.54480(19) 0.09484(15) 0.7470(3) 0.0598(7) Uani d . 1 . .
C C13 0.44375(19) 0.11214(15) 0.6249(3) 0.0620(7) Uani d . 1 . .
H H13 0.4330 0.1045 0.5014 0.074 Uiso calc R 1 . .
C C14 0.35890(17) 0.14068(13) 0.6849(3) 0.0527(6) Uani d . 1 . .
H H14 0.2912 0.1527 0.6013 0.063 Uiso calc R 1 . .
C C15 0.7272(2) 0.04266(18) 0.7970(4) 0.0888(9) Uani d . 1 . .
H H15A 0.7609 0.0897 0.8689 0.133 Uiso calc R 1 . .
H H15B 0.7745 0.0226 0.7295 0.133 Uiso calc R 1 . .
H H15C 0.7157 -0.0007 0.8750 0.133 Uiso calc R 1 . .
C C16 -0.0288(2) 0.56282(15) 0.6910(4) 0.0780(8) Uani d . 1 . .
H H16A -0.0998 0.5670 0.6022 0.117 Uiso calc R 1 . .
H H16B 0.0255 0.5890 0.6454 0.117 Uiso calc R 1 . .
H H16C -0.0309 0.5902 0.8006 0.117 Uiso calc R 1 . .
H H2 0.2197(19) 0.2603(13) 0.737(2) 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 . . 114.46(17) ?
C8 N2 N1 . . 118.77(17) ?
C8 N2 H2 . . 123.7(15) ?
N1 N2 H2 . . 115.9(15) ?
C2 O1 C16 . . 118.51(18) ?
C12 O3 C15 . . 117.7(2) ?
C6 C1 C2 . . 118.4(2) ?
C6 C1 C7 . . 121.9(2) ?
C2 C1 C7 . . 119.7(2) ?
O1 C2 C3 . . 124.4(2) ?
O1 C2 C1 . . 115.38(19) ?
C3 C2 C1 . . 120.2(2) ?
C4 C3 C2 . . 119.6(3) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C5 C4 C3 . . 121.3(2) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 118.7(3) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C1 C6 C5 . . 121.7(2) ?
C1 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
N1 C7 C1 . . 120.65(19) ?
N1 C7 H7 . . 119.7 ?
C1 C7 H7 . . 119.7 ?
O2 C8 N2 . . 122.35(19) ?
O2 C8 C9 . . 122.1(2) ?
N2 C8 C9 . . 115.56(19) ?
C10 C9 C14 . . 117.94(19) ?
C10 C9 C8 . . 119.13(19) ?
C14 C9 C8 . . 122.9(2) ?
C9 C10 C11 . . 121.5(2) ?
C9 C10 H10 . . 119.2 ?
C11 C10 H10 . . 119.2 ?
C12 C11 C10 . . 119.8(2) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
O3 C12 C11 . . 124.4(2) ?
O3 C12 C13 . . 115.9(2) ?
C11 C12 C13 . . 119.7(2) ?
C14 C13 C12 . . 120.2(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C9 . . 120.9(2) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 119.6 ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O1 C16 H16A . . 109.5 ?
O1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O1 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 C7 . 1.273(2) ?
N1 N2 . 1.383(2) ?
N2 C8 . 1.351(3) ?
N2 H2 . 0.898(9) ?
O1 C2 . 1.365(3) ?
O1 C16 . 1.424(3) ?
O2 C8 . 1.234(2) ?
O3 C12 . 1.364(2) ?
O3 C15 . 1.424(3) ?
C1 C6 . 1.377(3) ?
C1 C2 . 1.397(3) ?
C1 C7 . 1.460(3) ?
C2 C3 . 1.379(3) ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.366(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.481(3) ?
C9 C10 . 1.375(3) ?
C9 C14 . 1.387(3) ?
C10 C11 . 1.378(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.369(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.377(3) ?
C13 C14 . 1.372(3) ?
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
N2 H2 O2 4_565 0.898(9) 1.985(11) 2.859(2) 164(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7832862
