#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235038.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_2235038
loop_
_publ_author_name
'Tahir, M. Nawaz'
'Umar, M. Naveed'
'Ali, Akbar'
'Shad, Hazoor Ahmad'
_publ_section_title
;
 2-[(E)-3,4-Dimethoxybenzylidene]hydrazinecarboxamide
;
_journal_coeditor_code           HB6783
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1724
_journal_paper_doi               10.1107/S1600536812020739
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H13 N3 O3'
_chemical_formula_moiety         'C10 H13 N3 O3'
_chemical_formula_sum            'C10 H13 N3 O3'
_chemical_formula_weight         223.23
_chemical_name_systematic
;
2-[(E)-3,4-Dimethoxybenzylidene]hydrazinecarboxamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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
_cell_angle_beta                 126.2340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.2300(7)
_cell_length_b                   7.6367(3)
_cell_length_c                   15.6482(6)
_cell_measurement_reflns_used    1389
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.27
_cell_volume                     2142.76(14)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7933
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.203
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0429
_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)+(0.0592P)²+0.0283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                1389
_reflns_number_total             2115
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6783.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235038
_cod_database_fobs_code          2235038
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
O O1 0.30582(7) -0.13305(19) 0.72476(10) 0.0464(5) Uani 1.000 -16
O O2 0.34785(7) 0.03543(19) 0.62646(10) 0.0454(5) Uani 1.000 -16
O O3 -0.01303(7) 0.24827(17) -0.02345(10) 0.0447(5) Uani 1.000 -16
N N1 0.10093(8) 0.0967(2) 0.23838(12) 0.0404(5) Uani 1.000 -16
N N2 0.04892(8) 0.0982(2) 0.12929(12) 0.0421(5) Uani 1.000 -16
N N3 0.06302(9) 0.3952(2) 0.13090(13) 0.0445(6) Uani 1.000 -16
C C1 0.15297(10) -0.0591(2) 0.40077(15) 0.0347(6) Uani 1.000 -16
C C2 0.22548(10) 0.0085(2) 0.45703(15) 0.0356(6) Uani 1.000 -16
C C3 0.27503(10) -0.0179(2) 0.56479(14) 0.0331(6) Uani 1.000 -16
C C4 0.25221(10) -0.1097(2) 0.61917(15) 0.0345(6) Uani 1.000 -16
C C5 0.18023(10) -0.1725(3) 0.56366(15) 0.0394(7) Uani 1.000 -16
C C6 0.13153(10) -0.1495(3) 0.45538(15) 0.0397(7) Uani 1.000 -16
C C7 0.28984(13) -0.2490(3) 0.78007(16) 0.0527(8) Uani 1.000 -16
C C8 0.37782(11) 0.1099(3) 0.57544(17) 0.0490(8) Uani 1.000 -16
C C9 0.10014(10) -0.0369(3) 0.28603(15) 0.0400(7) Uani 1.000 -16
C C10 0.03155(9) 0.2502(3) 0.07501(15) 0.0347(6) Uani 1.000 -16
H H2 0.24028 0.07157 0.42152 0.0427 Uiso 1.000 -16
H H2A 0.02764 0.00235 0.09601 0.0505 Uiso 1.000 -16
H H3A 0.05296 0.49443 0.09922 0.0534 Uiso 1.000 -16
H H3B 0.09351 0.38993 0.19885 0.0534 Uiso 1.000 -16
H H5 0.16442 -0.23070 0.59936 0.0473 Uiso 1.000 -16
H H6 0.08359 -0.19543 0.41857 0.0476 Uiso 1.000 -16
H H7A 0.24962 -0.20238 0.77979 0.0791 Uiso 1.000 -16
H H7B 0.33332 -0.26156 0.85185 0.0791 Uiso 1.000 -16
H H7C 0.27580 -0.36131 0.74591 0.0791 Uiso 1.000 -16
H H8A 0.35195 0.21675 0.54077 0.0735 Uiso 1.000 -16
H H8B 0.37181 0.02896 0.52397 0.0735 Uiso 1.000 -16
H H8C 0.42987 0.13423 0.62723 0.0735 Uiso 1.000 -16
H H9 0.06472 -0.12360 0.24658 0.0479 Uiso 1.000 -16
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
_geom_angle_publ_flag
C4 O1 C7 117.75(18) no
C3 O2 C8 118.26(15) no
N2 N1 C9 116.05(17) no
N1 N2 C10 120.10(15) no
N1 N2 H2A 120.00 no
C10 N2 H2A 120.00 no
C10 N3 H3A 120.00 no
C10 N3 H3B 120.00 no
H3A N3 H3B 120.00 no
C2 C1 C6 118.95(18) no
C2 C1 C9 121.3(2) no
C6 C1 C9 119.7(2) no
C1 C2 C3 120.4(2) no
C2 C3 C4 119.9(2) no
O2 C3 C4 114.88(16) no
O2 C3 C2 125.2(2) no
O1 C4 C5 125.2(2) no
O1 C4 C3 115.4(2) no
C3 C4 C5 119.39(18) no
C4 C5 C6 120.3(2) no
C1 C6 C5 121.0(2) no
N1 C9 C1 122.29(19) no
O3 C10 N3 123.4(2) no
N2 C10 N3 117.33(17) no
O3 C10 N2 119.32(19) no
C1 C2 H2 120.00 no
C3 C2 H2 120.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
C1 C6 H6 120.00 no
C5 C6 H6 120.00 no
O1 C7 H7A 109.00 no
O1 C7 H7B 109.00 no
O1 C7 H7C 109.00 no
H7A C7 H7B 109.00 no
H7A C7 H7C 109.00 no
H7B C7 H7C 109.00 no
O2 C8 H8A 109.00 no
O2 C8 H8B 109.00 no
O2 C8 H8C 109.00 no
H8A C8 H8B 109.00 no
H8A C8 H8C 109.00 no
H8B C8 H8C 109.00 no
N1 C9 H9 119.00 no
C1 C9 H9 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 1.362(2) no
O1 C7 1.422(3) no
O2 C3 1.368(3) no
O2 C8 1.426(3) no
O3 C10 1.245(2) no
N1 N2 1.385(2) no
N1 C9 1.270(3) no
N2 C10 1.353(3) no
N3 C10 1.326(3) no
N2 H2A 0.8600 no
N3 H3A 0.8600 no
N3 H3B 0.8600 no
C1 C9 1.463(3) no
C1 C2 1.401(3) no
C1 C6 1.384(3) no
C2 C3 1.379(3) no
C3 C4 1.408(3) no
C4 C5 1.379(3) no
C5 C6 1.380(3) no
C2 H2 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C7 H7A 0.9600 no
C7 H7B 0.9600 no
C7 H7C 0.9600 no
C8 H8A 0.9600 no
C8 H8B 0.9600 no
C8 H8C 0.9600 no
C9 H9 0.9300 no
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
_geom_hbond_publ_flag
N2 H2A O3 3_555 0.86 2.15 2.970(2) 159 yes
N3 H3A O3 3_565 0.86 2.19 3.044(2) 170 yes
N3 H3B N1 . 0.86 2.30 2.657(2) 105 yes
N3 H3B O1 7_556 0.86 2.59 3.019(2) 112 yes
N3 H3B O2 7_556 0.86 2.30 3.119(2) 160 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C7 O1 C4 C3 -169.75(18) no
C7 O1 C4 C5 8.3(3) no
C8 O2 C3 C2 -6.2(3) no
C8 O2 C3 C4 172.38(17) no
C9 N1 N2 C10 162.2(2) no
N2 N1 C9 C1 178.4(2) no
N1 N2 C10 O3 177.1(2) no
N1 N2 C10 N3 -3.6(3) no
C6 C1 C2 C3 1.3(3) no
C9 C1 C2 C3 -178.29(19) no
C2 C1 C6 C5 0.4(3) no
C9 C1 C6 C5 180.0(2) no
C2 C1 C9 N1 -31.7(3) no
C6 C1 C9 N1 148.8(2) no
C1 C2 C3 O2 176.97(18) no
C1 C2 C3 C4 -1.5(3) no
O2 C3 C4 O1 -0.4(2) no
O2 C3 C4 C5 -178.58(18) no
C2 C3 C4 O1 178.23(17) no
C2 C3 C4 C5 0.1(3) no
O1 C4 C5 C6 -176.4(2) no
C3 C4 C5 C6 1.6(3) no
C4 C5 C6 C1 -1.9(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5286827
2 PubChem 6907483
