#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235030.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_2235030
loop_
_publ_author_name
'Abdel-Aziz, Hatem A.'
'Quah, Ching Kheng'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Phenyl-N'-(2-phenylacetyl)acetohydrazide
;
_journal_coeditor_code           HB6773
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1680
_journal_paper_doi               10.1107/S1600536812019861
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H16 N2 O2'
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_name_systematic
;
2-Phenyl-N'-(2-phenylacetyl)acetohydrazide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.271(2)
_cell_angle_beta                 92.613(2)
_cell_angle_gamma                90.830(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4531(6)
_cell_length_b                   7.9283(9)
_cell_length_c                   15.1758(17)
_cell_measurement_reflns_used    3410
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      4.04
_cell_volume                     653.50(13)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII DUO CCD'
_diffrn_measurement_method       'φ and 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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12991
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0709P)²+0.1901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1340
_reflns_number_gt                2428
_reflns_number_total             3458
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6773.cif
_cod_data_source_block           I
_cod_database_code               2235030
_cod_database_fobs_code          2235030
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.40065(18) 0.64320(12) 0.06665(6) 0.0165(2) Uani d 1 1
O O2 1.08994(18) 0.85895(12) -0.07188(6) 0.0166(2) Uani d 1 1
N N1 0.7067(2) 0.81353(14) 0.02864(7) 0.0131(2) Uani d 1 1
N N2 0.7869(2) 0.68791(14) -0.03185(7) 0.0136(2) Uani d 1 1
C C1 0.2796(3) 0.94134(17) 0.29275(9) 0.0154(3) Uani d 1 1
C C2 0.3026(3) 0.90738(18) 0.38118(9) 0.0185(3) Uani d 1 1
C C3 0.4978(3) 0.81340(18) 0.41175(9) 0.0184(3) Uani d 1 1
C C4 0.6710(3) 0.75379(18) 0.35344(9) 0.0180(3) Uani d 1 1
C C5 0.6502(2) 0.78955(17) 0.26515(9) 0.0153(3) Uani d 1 1
C C6 0.4540(2) 0.88282(16) 0.23362(8) 0.0127(3) Uani d 1 1
C C7 0.4336(3) 0.92581(17) 0.13786(8) 0.0129(3) Uani d 1 1
C C8 0.5093(2) 0.78171(16) 0.07486(8) 0.0120(3) Uani d 1 1
C C9 0.9839(2) 0.71983(16) -0.07846(8) 0.0120(3) Uani d 1 1
C C10 1.0630(3) 0.57244(17) -0.13972(8) 0.0137(3) Uani d 1 1
C C11 1.0445(2) 0.61346(16) -0.23584(8) 0.0127(3) Uani d 1 1
C C12 1.2278(3) 0.70965(18) -0.27062(9) 0.0162(3) Uani d 1 1
C C13 1.2100(3) 0.74792(18) -0.35846(9) 0.0186(3) Uani d 1 1
C C14 1.0109(3) 0.68811(19) -0.41296(9) 0.0200(3) Uani d 1 1
C C15 0.8286(3) 0.59203(19) -0.37894(9) 0.0196(3) Uani d 1 1
C C16 0.8446(3) 0.55437(17) -0.29055(9) 0.0161(3) Uani d 1 1
H H1N1 0.787(3) 0.915(2) 0.0321(11) 0.023(5) Uiso d 1 1
H H1N2 0.705(3) 0.593(2) -0.0350(11) 0.017(4) Uiso d 1 1
H H1A 0.148(3) 1.007(2) 0.2720(11) 0.022(4) Uiso d 1 1
H H2A 0.175(3) 0.951(2) 0.4219(10) 0.017(4) Uiso d 1 1
H H3A 0.519(4) 0.786(2) 0.4710(13) 0.031(5) Uiso d 1 1
H H4A 0.809(3) 0.686(2) 0.3727(11) 0.021(4) Uiso d 1 1
H H5A 0.775(3) 0.747(2) 0.2245(11) 0.018(4) Uiso d 1 1
H H7A 0.529(3) 1.028(2) 0.1304(10) 0.018(4) Uiso d 1 1
H H7B 0.259(4) 0.953(2) 0.1223(12) 0.027(5) Uiso d 1 1
H H10A 0.967(3) 0.471(2) -0.1318(10) 0.016(4) Uiso d 1 1
H H10B 1.240(3) 0.554(2) -0.1200(11) 0.021(4) Uiso d 1 1
H H12A 1.373(3) 0.757(2) -0.2322(11) 0.022(4) Uiso d 1 1
H H13A 1.339(3) 0.814(2) -0.3815(12) 0.029(5) Uiso d 1 1
H H14A 1.002(3) 0.713(2) -0.4733(12) 0.028(5) Uiso d 1 1
H H16A 0.720(3) 0.489(2) -0.2662(12) 0.029(5) Uiso d 1 1
H H15A 0.692(3) 0.549(2) -0.4190(11) 0.017(4) Uiso d 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
C8 N1 N2 118.83(11)
C8 N1 H1N1 123.8(11)
N2 N1 H1N1 117.2(11)
C9 N2 N1 118.90(11)
C9 N2 H1N2 125.2(11)
N1 N2 H1N2 115.9(11)
C2 C1 C6 120.35(13)
C2 C1 H1A 120.4(10)
C6 C1 H1A 119.2(10)
C1 C2 C3 120.42(13)
C1 C2 H2A 118.5(9)
C3 C2 H2A 121.0(9)
C4 C3 C2 119.67(13)
C4 C3 H3A 117.1(12)
C2 C3 H3A 123.2(12)
C3 C4 C5 120.00(13)
C3 C4 H4A 121.6(10)
C5 C4 H4A 118.4(10)
C4 C5 C6 120.81(12)
C4 C5 H5A 119.2(9)
C6 C5 H5A 120.0(9)
C5 C6 C1 118.74(12)
C5 C6 C7 121.05(11)
C1 C6 C7 120.17(12)
C8 C7 C6 112.43(11)
C8 C7 H7A 111.1(10)
C6 C7 H7A 110.0(9)
C8 C7 H7B 108.1(11)
C6 C7 H7B 108.9(10)
H7A C7 H7B 105.9(14)
O1 C8 N1 121.88(12)
O1 C8 C7 122.94(12)
N1 C8 C7 115.18(11)
O2 C9 N2 122.08(12)
O2 C9 C10 123.08(12)
N2 C9 C10 114.84(11)
C11 C10 C9 111.62(11)
C11 C10 H10A 110.1(9)
C9 C10 H10A 111.1(10)
C11 C10 H10B 110.7(10)
C9 C10 H10B 104.3(10)
H10A C10 H10B 108.8(14)
C16 C11 C12 119.24(12)
C16 C11 C10 120.29(12)
C12 C11 C10 120.47(12)
C13 C12 C11 120.42(14)
C13 C12 H12A 118.5(10)
C11 C12 H12A 121.0(10)
C12 C13 C14 120.18(13)
C12 C13 H13A 119.3(11)
C14 C13 H13A 120.5(11)
C15 C14 C13 119.70(13)
C15 C14 H14A 120.6(12)
C13 C14 H14A 119.7(12)
C14 C15 C16 120.35(14)
C14 C15 H15A 118.1(10)
C16 C15 H15A 121.5(10)
C11 C16 C15 120.10(13)
C11 C16 H16A 118.7(11)
C15 C16 H16A 121.2(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.2355(16)
O2 C9 1.2332(16)
N1 C8 1.3426(16)
N1 N2 1.3922(14)
N1 H1N1 0.908(19)
N2 C9 1.3443(16)
N2 H1N2 0.869(18)
C1 C2 1.3888(19)
C1 C6 1.3977(18)
C1 H1A 0.950(18)
C2 C3 1.390(2)
C2 H2A 1.000(16)
C3 C4 1.388(2)
C3 H3A 0.942(19)
C4 C5 1.3899(19)
C4 H4A 0.977(17)
C5 C6 1.3960(18)
C5 H5A 0.986(17)
C6 C7 1.5167(18)
C7 C8 1.5089(18)
C7 H7A 0.975(18)
C7 H7B 1.002(19)
C9 C10 1.5183(18)
C10 C11 1.5172(18)
C10 H10A 0.972(17)
C10 H10B 1.013(18)
C11 C16 1.3934(19)
C11 C12 1.3951(18)
C12 C13 1.3884(19)
C12 H12A 1.009(18)
C13 C14 1.390(2)
C13 H13A 0.963(19)
C14 C15 1.385(2)
C14 H14A 0.949(18)
C15 C16 1.3948(19)
C15 H15A 0.980(17)
C16 H16A 0.954(19)
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 H1N2 O1 2_665 0.867(16) 1.970(16) 2.8076(15) 162.4(16) yes
C10 H10A O1 2_665 0.971(16) 2.465(16) 3.3103(18) 145.3(13) yes
N1 H1N1 O2 2_775 0.907(16) 1.948(16) 2.8283(15) 163.2(15) yes
C7 H7A O2 2_775 0.973(16) 2.479(16) 3.3209(18) 144.8(13) yes
C7 H7B O2 2_675 1.00(2) 2.56(2) 3.4929(19) 155.2(13) 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
C8 N1 N2 C9 179.72(11)
C6 C1 C2 C3 -0.6(2)
C1 C2 C3 C4 0.2(2)
C2 C3 C4 C5 0.6(2)
C3 C4 C5 C6 -1.1(2)
C4 C5 C6 C1 0.6(2)
C4 C5 C6 C7 178.53(13)
C2 C1 C6 C5 0.2(2)
C2 C1 C6 C7 -177.69(13)
C5 C6 C7 C8 39.28(18)
C1 C6 C7 C8 -142.87(13)
N2 N1 C8 O1 1.69(19)
N2 N1 C8 C7 -179.17(11)
C6 C7 C8 O1 62.54(17)
C6 C7 C8 N1 -116.59(13)
N1 N2 C9 O2 -2.93(19)
N1 N2 C9 C10 177.53(11)
O2 C9 C10 C11 -61.91(17)
N2 C9 C10 C11 117.63(13)
C9 C10 C11 C16 -100.39(15)
C9 C10 C11 C12 80.05(15)
C16 C11 C12 C13 0.8(2)
C10 C11 C12 C13 -179.64(12)
C11 C12 C13 C14 -1.1(2)
C12 C13 C14 C15 0.9(2)
C13 C14 C15 C16 -0.3(2)
C12 C11 C16 C15 -0.3(2)
C10 C11 C16 C15 -179.84(12)
C14 C15 C16 C11 0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 208354
2 PubChem 238532
