#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/49/2234973.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_2234973
loop_
_publ_author_name
'Kesternich, Víctor'
'Gahona, Paulo'
'Pérez-Fehrmann, Marcia'
'Brito, Iván'
'López-Rodríguez, Matías'
_publ_section_title
;
 2-Amino-N'-phenylbenzohydrazide
;
_journal_coeditor_code           DS2196
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1847
_journal_paper_doi               10.1107/S1600536812022362
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H13 N3 O'
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_chemical_name_systematic
;
2-Amino-N'-phenylbenzohydrazide
;
_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                 94.08(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1190(12)
_cell_length_b                   19.921(4)
_cell_length_c                   9.6490(19)
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      3.9
_cell_volume                     1173.2(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_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  0.0920
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17096
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.58
_diffrn_reflns_theta_min         3.92
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.494
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0683
_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)+(0.0568P)²+0.7268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1627
_reflns_number_gt                2330
_reflns_number_total             2923
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2196.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234973
_cod_database_fobs_code          2234973
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_symmetry_multiplicity
O O1 0.6118(2) 0.71063(8) 0.36635(13) 0.0430(4) Uani d . 1 1
N N1 0.5506(3) 0.73222(8) 0.58950(15) 0.0377(4) Uani d . 1 1
H H1 0.5943 0.7527 0.6648 0.045 Uiso calc R 1 1
N N2 0.3725(3) 0.68841(9) 0.59083(17) 0.0407(4) Uani d . 1 1
H H2 0.2401 0.7021 0.5736 0.049 Uiso calc R 1 1
N N3 1.0637(3) 0.73656(12) 0.3383(2) 0.0499(5) Uani d . 1 1
H H3A 0.956(5) 0.7108(13) 0.312(3) 0.059(8) Uiso d . 1 1
H H3B 1.161(5) 0.7445(14) 0.273(3) 0.073(8) Uiso d . 1 1
C C1 0.6555(3) 0.74322(9) 0.47424(17) 0.0313(4) Uani d . 1 1
C C2 0.8220(3) 0.79772(9) 0.48509(17) 0.0323(4) Uani d . 1 1
C C3 0.7862(3) 0.85526(10) 0.5633(2) 0.0421(5) Uani d . 1 1
H H3 0.6585 0.8587 0.6095 0.051 Uiso calc R 1 1
C C4 0.9359(4) 0.90690(12) 0.5732(3) 0.0560(6) Uani d . 1 1
H H4 0.9095 0.9450 0.6253 0.067 Uiso calc R 1 1
C C5 1.1263(4) 0.90142(13) 0.5046(3) 0.0575(6) Uani d . 1 1
H H5 1.2291 0.9359 0.5115 0.069 Uiso calc R 1 1
C C6 1.1644(3) 0.84588(12) 0.4269(2) 0.0483(5) Uani d . 1 1
H H6 1.2936 0.8431 0.3820 0.058 Uiso calc R 1 1
C C7 1.0137(3) 0.79316(10) 0.41334(18) 0.0364(4) Uani d . 1 1
C C8 0.4207(3) 0.62058(11) 0.62176(19) 0.0387(4) Uani d . 1 1
C C9 0.6191(4) 0.59962(12) 0.6849(2) 0.0484(5) Uani d . 1 1
H H9 0.7320 0.6304 0.7030 0.058 Uiso calc R 1 1
C C10 0.6494(5) 0.53310(14) 0.7208(3) 0.0668(7) Uani d . 1 1
H H10 0.7826 0.5195 0.7642 0.080 Uiso calc R 1 1
C C11 0.4861(6) 0.48666(14) 0.6935(3) 0.0756(9) Uani d . 1 1
H H11 0.5089 0.4417 0.7165 0.091 Uiso calc R 1 1
C C12 0.2896(6) 0.50745(15) 0.6322(3) 0.0744(9) Uani d . 1 1
H H12 0.1780 0.4763 0.6141 0.089 Uiso calc R 1 1
C C13 0.2535(4) 0.57384(14) 0.5967(2) 0.0574(6) Uani d . 1 1
H H13 0.1181 0.5873 0.5562 0.069 Uiso calc R 1 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
C1 N1 N2 121.98(15)
C1 N1 H1 119.0
N2 N1 H1 119.0
N1 N2 C8 116.67(15)
N1 N2 H2 121.7
C8 N2 H2 121.7
C7 N3 H3A 116.4(18)
C7 N3 H3B 113.5(18)
H3A N3 H3B 115(3)
O1 C1 N1 121.54(17)
O1 C1 C2 123.18(16)
N1 C1 C2 115.26(15)
C3 C2 C7 119.10(18)
C3 C2 C1 120.27(16)
C7 C2 C1 120.60(17)
C4 C3 C2 121.46(19)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C5 119.1(2)
C3 C4 H4 120.5
C5 C4 H4 120.5
C6 C5 C4 120.6(2)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 121.5(2)
C5 C6 H6 119.2
C7 C6 H6 119.2
N3 C7 C6 119.45(18)
N3 C7 C2 122.17(19)
C6 C7 C2 118.23(18)
C9 C8 C13 119.1(2)
C9 C8 N2 123.09(18)
C13 C8 N2 117.7(2)
C10 C9 C8 119.9(2)
C10 C9 H9 120.0
C8 C9 H9 120.0
C11 C10 C9 121.1(3)
C11 C10 H10 119.5
C9 C10 H10 119.5
C12 C11 C10 119.0(3)
C12 C11 H11 120.5
C10 C11 H11 120.5
C11 C12 C13 121.2(3)
C11 C12 H12 119.4
C13 C12 H12 119.4
C12 C13 C8 119.7(3)
C12 C13 H13 120.2
C8 C13 H13 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.240(2)
N1 C1 1.341(2)
N1 N2 1.397(2)
N1 H1 0.8600
N2 C8 1.411(3)
N2 H2 0.8600
N3 C7 1.386(3)
N3 H3A 0.86(3)
N3 H3B 0.91(3)
C1 C2 1.487(3)
C2 C3 1.398(3)
C2 C7 1.407(2)
C3 C4 1.376(3)
C3 H3 0.9300
C4 C5 1.385(4)
C4 H4 0.9300
C5 C6 1.366(4)
C5 H5 0.9300
C6 C7 1.397(3)
C6 H6 0.9300
C8 C9 1.384(3)
C8 C13 1.392(3)
C9 C10 1.379(4)
C9 H9 0.9300
C10 C11 1.374(4)
C10 H10 0.9300
C11 C12 1.366(5)
C11 H11 0.9300
C12 C13 1.380(4)
C12 H12 0.9300
C13 H13 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
_geom_hbond_publ_flag
N1 H1 O1 4_576 0.86 2.07 2.903(2) 162 y
N3 H3A O1 . 0.86(3) 2.21(3) 2.845(2) 131(2) y
N2 H2 N3 1_455 0.86 2.54 3.126(3) 126 y
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
C1 N1 N2 C8 89.2(2)
N2 N1 C1 O1 -6.4(3)
N2 N1 C1 C2 172.28(16)
O1 C1 C2 C3 142.55(19)
N1 C1 C2 C3 -36.1(2)
O1 C1 C2 C7 -35.3(3)
N1 C1 C2 C7 146.01(17)
C7 C2 C3 C4 -1.0(3)
C1 C2 C3 C4 -178.95(19)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C6 0.7(4)
C4 C5 C6 C7 0.3(4)
C5 C6 C7 N3 -177.3(2)
C5 C6 C7 C2 -1.6(3)
C3 C2 C7 N3 177.46(18)
C1 C2 C7 N3 -4.6(3)
C3 C2 C7 C6 1.9(3)
C1 C2 C7 C6 179.85(16)
N1 N2 C8 C9 17.7(3)
N1 N2 C8 C13 -167.37(17)
C13 C8 C9 C10 0.6(3)
N2 C8 C9 C10 175.5(2)
C8 C9 C10 C11 0.8(4)
C9 C10 C11 C12 -1.3(4)
C10 C11 C12 C13 0.4(4)
C11 C12 C13 C8 0.9(4)
C9 C8 C13 C12 -1.4(3)
N2 C8 C13 C12 -176.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10581058
