#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/51/2225197.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_2225197
loop_
_publ_author_name
'Wang, Ping'
'Li, Cong'
'Su, Yong-Qing'
_publ_section_title
;
 N'-(2-Methoxybenzylidene)nicotinohydrazide
;
_journal_coeditor_code           CI5028
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o542
_journal_paper_doi               10.1107/S1600536810003831
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H13 N3 O2'
_chemical_formula_moiety         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27
_chemical_name_systematic
;
N'-(2-Methoxybenzylidene)nicotinohydrazide
;
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3264(13)
_cell_length_b                   9.3264(13)
_cell_length_c                   15.594(3)
_cell_measurement_reflns_used    2214
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.5
_cell_volume                     1356.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6623
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1519
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.001
_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+0.084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                1313
_reflns_number_total             1519
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5028.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 'Tetragonal' changed to 'tetragonal'
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_database_code               2225197
_cod_database_fobs_code          2225197
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
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 0.54565(17) 0.50653(18) 0.21981(11) 0.0443(4) Uani d . 1 . .
N N2 0.41517(19) 0.53627(19) 0.18161(11) 0.0457(4) Uani d D 1 . .
N N3 0.0801(2) 0.6980(3) 0.03464(14) 0.0763(7) Uani d . 1 . .
O O1 0.84079(19) 0.3686(2) 0.05708(12) 0.0681(5) Uani d . 1 . .
O O2 0.33671(17) 0.66164(18) 0.29682(10) 0.0586(4) Uani d . 1 . .
C C1 0.7782(2) 0.4068(2) 0.20059(15) 0.0454(5) Uani d . 1 . .
C C2 0.8837(2) 0.3667(2) 0.14119(15) 0.0508(5) Uani d . 1 . .
C C3 1.0208(3) 0.3312(3) 0.1677(2) 0.0635(7) Uani d . 1 . .
H H3 1.0901 0.3046 0.1279 0.076 Uiso calc R 1 . .
C C4 1.0535(3) 0.3360(3) 0.2543(2) 0.0662(7) Uani d . 1 . .
H H4 1.1455 0.3123 0.2724 0.079 Uiso calc R 1 . .
C C5 0.9519(3) 0.3753(3) 0.31421(19) 0.0621(6) Uani d . 1 . .
H H5 0.9751 0.3784 0.3722 0.075 Uiso calc R 1 . .
C C6 0.8156(3) 0.4098(2) 0.28694(15) 0.0516(5) Uani d . 1 . .
H H6 0.7469 0.4358 0.3273 0.062 Uiso calc R 1 . .
C C7 0.6357(2) 0.4433(2) 0.17089(15) 0.0466(5) Uani d . 1 . .
H H7 0.6091 0.4202 0.1151 0.056 Uiso calc R 1 . .
C C8 0.3205(2) 0.6206(2) 0.22245(13) 0.0420(5) Uani d . 1 . .
C C9 0.1932(2) 0.6646(2) 0.17108(14) 0.0428(5) Uani d . 1 . .
C C10 0.0723(3) 0.7159(3) 0.21159(16) 0.0623(7) Uani d . 1 . .
H H10 0.0690 0.7228 0.2710 0.075 Uiso calc R 1 . .
C C11 -0.0433(3) 0.7567(4) 0.1626(2) 0.0797(9) Uani d . 1 . .
H H11 -0.1265 0.7907 0.1884 0.096 Uiso calc R 1 . .
C C12 -0.0339(3) 0.7463(4) 0.07564(19) 0.0779(9) Uani d . 1 . .
H H12 -0.1125 0.7749 0.0432 0.093 Uiso calc R 1 . .
C C13 0.1914(3) 0.6590(3) 0.08281(14) 0.0571(6) Uani d . 1 . .
H H13 0.2732 0.6259 0.0550 0.069 Uiso calc R 1 . .
C C14 0.9423(4) 0.3294(4) -0.0070(2) 0.0921(11) Uani d . 1 . .
H H14A 1.0234 0.3926 -0.0041 0.138 Uiso calc R 1 . .
H H14B 0.8987 0.3366 -0.0626 0.138 Uiso calc R 1 . .
H H14C 0.9734 0.2325 0.0026 0.138 Uiso calc R 1 . .
H H2 0.394(3) 0.496(3) 0.1309(11) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 . . 114.42(17) ?
C8 N2 N1 . . 119.46(17) ?
C8 N2 H2 . . 120.9(19) ?
N1 N2 H2 . . 119.6(19) ?
C12 N3 C13 . . 116.6(2) ?
C2 O1 C14 . . 118.3(2) ?
C6 C1 C2 . . 118.0(2) ?
C6 C1 C7 . . 122.3(2) ?
C2 C1 C7 . . 119.7(2) ?
O1 C2 C3 . . 123.9(2) ?
O1 C2 C1 . . 115.1(2) ?
C3 C2 C1 . . 121.0(2) ?
C4 C3 C2 . . 119.1(2) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C5 C4 C3 . . 121.1(2) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C6 C5 C4 . . 119.1(3) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C1 . . 121.7(2) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
N1 C7 C1 . . 121.4(2) ?
N1 C7 H7 . . 119.3 ?
C1 C7 H7 . . 119.3 ?
O2 C8 N2 . . 123.23(19) ?
O2 C8 C9 . . 121.28(18) ?
N2 C8 C9 . . 115.49(17) ?
C13 C9 C10 . . 117.4(2) ?
C13 C9 C8 . . 122.5(2) ?
C10 C9 C8 . . 120.1(2) ?
C11 C10 C9 . . 118.9(2) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C12 C11 C10 . . 118.8(3) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
N3 C12 C11 . . 124.0(3) ?
N3 C12 H12 . . 118.0 ?
C11 C12 H12 . . 118.0 ?
N3 C13 C9 . . 124.3(2) ?
N3 C13 H13 . . 117.9 ?
C9 C13 H13 . . 117.9 ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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 . 1.279(3) ?
N1 N2 . 1.383(2) ?
N2 C8 . 1.343(3) ?
N2 H2 . 0.897(10) ?
N3 C12 . 1.320(4) ?
N3 C13 . 1.332(3) ?
O1 C2 . 1.371(3) ?
O1 C14 . 1.424(3) ?
O2 C8 . 1.231(2) ?
C1 C6 . 1.391(3) ?
C1 C2 . 1.402(3) ?
C1 C7 . 1.448(3) ?
C2 C3 . 1.385(3) ?
C3 C4 . 1.385(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.380(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.379(3) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 H7 . 0.93 ?
C8 C9 . 1.489(3) ?
C9 C13 . 1.378(3) ?
C9 C10 . 1.378(3) ?
C10 C11 . 1.375(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.362(4) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
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 3_654 0.900(10) 2.05(2) 2.897(2) 157(3)
C4 H4 O1 4_665 0.93 2.58 3.469(3) 160
C11 H11 N3 4_465 0.93 2.53 3.429(4) 164
C13 H13 N1 3_654 0.93 2.56 3.487(3) 176
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5271129
2 PubChem 6880286
