#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/47/2234760.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_2234760
loop_
_publ_author_name
'Karimian, Ramin'
'Hosseini-Monfared, Hassan'
'Bikas, Rahman'
'Arslan, N. Burcu'
'Kazak, Canan'
'Koroglu, Ahmet'
_publ_section_title
;
 (E,E)-N'-{4-[(2-Benzoylhydrazin-1-ylidene)methyl]benzylidene}benzohydrazide
;
_journal_coeditor_code           QM2059
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1433
_journal_paper_doi               10.1107/S1600536812014687
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C22 H18 N4 O2'
_chemical_formula_moiety         'C22 H18 N4 O2'
_chemical_formula_sum            'C22 H18 N4 O2'
_chemical_formula_weight         370.40
_chemical_name_systematic
;
(E,E)-N'-{4-[(2-Benzoylhydrazin-1-
ylidene)methyl]benzylidene}benzohydrazide
;
_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                90.00
_cell_angle_beta                 112.408(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.569(3)
_cell_length_b                   5.1845(3)
_cell_length_c                   12.5191(11)
_cell_measurement_reflns_used    8004
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      1.44
_cell_volume                     1834.3(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_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      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1045
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13265
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9760
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0510
_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)+(0.0207P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                965
_reflns_number_total             1905
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            qm2059.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234760
_cod_database_fobs_code          2234760
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
_atom_site_symmetry_multiplicity
C C1 0.84753(7) 0.1985(4) 0.32678(19) 0.0454(6) Uani d 1 1
C C2 0.84744(9) 0.3457(5) 0.4191(2) 0.0562(7) Uani d 1 1
C C3 0.81956(9) 0.2794(6) 0.4790(2) 0.0658(8) Uani d 1 1
C C4 0.79059(10) 0.0693(6) 0.4454(3) 0.0695(8) Uani d 1 1
C C5 0.78956(10) -0.0782(5) 0.3532(3) 0.0711(8) Uani d 1 1
C C6 0.81817(8) -0.0140(5) 0.2948(2) 0.0582(7) Uani d 1 1
C C7 0.87799(7) 0.2804(4) 0.26408(19) 0.0475(6) Uani d 1 1
C C8 0.94196(8) -0.0556(5) 0.1321(2) 0.0502(6) Uani d 1 1
C C10 0.96656(9) 0.1846(5) -0.0081(2) 0.0558(7) Uani d 1 1
C C11 1.00525(9) -0.2099(5) 0.0707(2) 0.0553(7) Uani d 1 1
C C12 0.97114(7) -0.0250(4) 0.06315(18) 0.0458(6) Uani d 1 1
N N1 0.89465(7) 0.0866(4) 0.21865(17) 0.0543(6) Uani d 1 1
N N2 0.92141(7) 0.1407(3) 0.15428(16) 0.0516(5) Uani d 1 1
O O1 0.88701(6) 0.5082(3) 0.25515(14) 0.0650(5) Uani d 1 1
H H1 0.8912(7) -0.074(4) 0.2351(18) 0.055(7) Uiso d 1 1
H H2 0.9404(6) -0.232(4) 0.1624(16) 0.052(6) Uiso d 1 1
H H3 0.8174(7) -0.118(4) 0.2312(19) 0.058(7) Uiso d 1 1
H H4 0.9424(8) 0.305(4) -0.0167(18) 0.065(7) Uiso d 1 1
H H5 1.0094(7) -0.343(4) 0.1209(18) 0.056(7) Uiso d 1 1
H H6 0.8219(8) 0.387(4) 0.546(2) 0.078(8) Uiso d 1 1
H H7 0.8670(7) 0.499(4) 0.4386(17) 0.068(7) Uiso d 1 1
H H8 0.7688(9) -0.228(5) 0.324(2) 0.101(10) Uiso d 1 1
H H9 0.7717(9) 0.017(5) 0.489(2) 0.096(9) 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_site_symmetry_1
_geom_angle
C6 C1 C2 . 118.3(2)
C6 C1 C7 . 122.8(2)
C2 C1 C7 . 118.9(2)
C3 C2 C1 . 121.0(3)
C3 C2 H7 . 121.3(13)
C1 C2 H7 . 117.7(13)
C4 C3 C2 . 119.6(3)
C4 C3 H6 . 122.6(14)
C2 C3 H6 . 117.8(14)
C3 C4 C5 . 120.5(3)
C3 C4 H9 . 120.0(15)
C5 C4 H9 . 119.4(15)
C4 C5 C6 . 119.7(3)
C4 C5 H8 . 124.0(17)
C6 C5 H8 . 116.3(17)
C5 C6 C1 . 120.8(3)
C5 C6 H3 . 119.3(13)
C1 C6 H3 . 119.9(13)
O1 C7 N1 . 123.0(2)
O1 C7 C1 . 121.95(19)
N1 C7 C1 . 115.0(2)
N2 C8 C12 . 120.0(2)
N2 C8 H2 . 123.2(11)
C12 C8 H2 . 116.7(11)
C11 C10 C12 5_755 120.8(2)
C11 C10 H4 5_755 120.5(13)
C12 C10 H4 . 118.5(13)
C10 C11 C12 5_755 120.8(2)
C10 C11 H5 5_755 120.9(13)
C12 C11 H5 . 118.2(13)
C10 C12 C11 . 118.4(2)
C10 C12 C8 . 122.1(2)
C11 C12 C8 . 119.5(2)
C7 N1 N2 . 120.0(2)
C7 N1 H1 . 120.9(14)
N2 N1 H1 . 118.9(14)
C8 N2 N1 . 114.51(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.381(3)
C1 C2 . 1.386(3)
C1 C7 . 1.490(3)
C2 C3 . 1.377(3)
C2 H7 . 0.97(2)
C3 C4 . 1.365(4)
C3 H6 . 0.99(2)
C4 C5 . 1.374(3)
C4 H9 . 0.98(3)
C5 C6 . 1.378(3)
C5 H8 . 0.98(3)
C6 H3 . 0.95(2)
C7 O1 . 1.228(2)
C7 N1 . 1.346(3)
C8 N2 . 1.281(3)
C8 C12 . 1.467(3)
C8 H2 . 1.00(2)
C10 C11 5_755 1.375(3)
C10 C12 . 1.379(3)
C10 H4 . 0.94(2)
C11 C10 5_755 1.375(3)
C11 C12 . 1.392(3)
C11 H5 . 0.91(2)
N1 N2 . 1.378(2)
N1 H1 . 0.87(2)
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 1_545 0.87(2) 2.19(2) 3.056(3) 171(2) 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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . 1.3(4)
C7 C1 C2 C3 . 179.4(2)
C1 C2 C3 C4 . -1.7(4)
C2 C3 C4 C5 . 0.9(4)
C3 C4 C5 C6 . 0.3(4)
C4 C5 C6 C1 . -0.7(4)
C2 C1 C6 C5 . -0.1(4)
C7 C1 C6 C5 . -178.1(2)
C6 C1 C7 O1 . 147.0(2)
C2 C1 C7 O1 . -30.9(3)
C6 C1 C7 N1 . -33.0(3)
C2 C1 C7 N1 . 149.0(2)
C11 C10 C12 C11 5_755 0.4(4)
C11 C10 C12 C8 5_755 179.2(2)
C10 C11 C12 C10 5_755 -0.4(4)
C10 C11 C12 C8 5_755 -179.3(2)
N2 C8 C12 C10 . -20.1(3)
N2 C8 C12 C11 . 158.7(2)
O1 C7 N1 N2 . -3.0(3)
C1 C7 N1 N2 . 177.04(19)
C12 C8 N2 N1 . 179.3(2)
C7 N1 N2 C8 . 168.7(2)
