#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227366.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227366
loop_
_publ_author_name
'Kong, Lingqian'
'Qiao, Yan'
'Gao, Zhiqing'
'Ju, Xiuping'
_publ_section_title
;
 1,5-Bis(1-phenylethylidene)carbonohydrazide
;
_journal_coeditor_code           CV2776
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2901
_journal_paper_doi               10.1107/S1600536810042121
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H18 N4 O'
_chemical_formula_moiety         'C17 H18 N4 O'
_chemical_formula_sum            'C17 H18 N4 O'
_chemical_formula_weight         294.35
_chemical_name_systematic
;
1,5-Bis(1-phenylethylidene)carbonohydrazide
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 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                 104.6810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9393(12)
_cell_length_b                   5.4858(5)
_cell_length_c                   22.703(2)
_cell_measurement_reflns_used    1233
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.150
_cell_measurement_theta_min      2.845
_cell_volume                     1558.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7406
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0490
_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)+(0.0747P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1481
_reflns_number_gt                1389
_reflns_number_total             2757
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv2776.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               2227366
_cod_database_fobs_code          2227366
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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_disorder_assembly
_atom_site_disorder_group
O O5 0.86754(12) 0.0739(3) 0.46156(9) 0.0764(6) Uani d . 1 . .
N N1 0.96224(16) 0.4666(4) 0.58368(10) 0.0631(6) Uani d . 1 . .
N N2 0.96359(15) 0.2825(4) 0.54321(10) 0.0679(6) Uani d . 1 . .
H H2 1.0196 0.1938 0.5466 0.082 Uiso calc RD 1 . .
N N3 0.79610(14) 0.4095(4) 0.49611(9) 0.0668(6) Uani d . 1 . .
H H3 0.8087 0.5299 0.5212 0.080 Uiso calc R 1 . .
N N4 0.69764(15) 0.3902(4) 0.45574(9) 0.0596(6) Uani d . 1 . .
C C1 0.87369(18) 0.2428(5) 0.49730(13) 0.0614(7) Uani d . 1 . .
C C2 0.63193(18) 0.5649(4) 0.45685(10) 0.0542(6) Uani d . 1 . .
C C3 0.65842(18) 0.7846(5) 0.49701(13) 0.0795(8) Uani d . 1 . .
H H3A 0.6503 0.7461 0.5368 0.119 Uiso calc R 1 . .
H H3B 0.6111 0.9157 0.4800 0.119 Uiso calc R 1 . .
H H3C 0.7309 0.8329 0.5000 0.119 Uiso calc R 1 . .
C C4 0.52443(18) 0.5423(5) 0.41536(11) 0.0551(6) Uani d . 1 . .
C C5 0.4445(2) 0.7041(6) 0.41690(14) 0.0928(10) Uani d . 1 . .
H H5 0.4592 0.8337 0.4442 0.111 Uiso calc R 1 . .
C C6 0.3434(2) 0.6811(7) 0.37943(17) 0.1109(12) Uani d . 1 . .
H H6 0.2909 0.7936 0.3818 0.133 Uiso calc R 1 . .
C C7 0.3200(2) 0.4948(7) 0.33899(14) 0.0934(10) Uani d . 1 . .
H H7 0.2518 0.4792 0.3133 0.112 Uiso calc R 1 . .
C C8 0.3977(2) 0.3314(6) 0.33648(14) 0.1002(11) Uani d . 1 . .
H H8 0.3828 0.2028 0.3089 0.120 Uiso calc R 1 . .
C C9 0.4984(2) 0.3561(6) 0.37467(13) 0.0836(9) Uani d . 1 . .
H H9 0.5503 0.2416 0.3726 0.100 Uiso calc R 1 . .
C C10 1.04459(19) 0.5073(5) 0.62766(12) 0.0618(7) Uani d . 1 . .
C C11 1.14821(18) 0.3686(5) 0.63824(12) 0.0783(8) Uani d . 1 . .
H H11A 1.1447 0.2260 0.6622 0.117 Uiso calc R 1 . .
H H11B 1.2060 0.4706 0.6595 0.117 Uiso calc R 1 . .
H H11C 1.1600 0.3207 0.5998 0.117 Uiso calc RD 1 . .
C C12 1.03396(18) 0.7066(5) 0.66970(11) 0.0613(7) Uani d . 1 . .
C C13 0.9504(2) 0.8704(6) 0.65627(13) 0.0774(8) Uani d . 1 . .
H H13 0.8986 0.8551 0.6197 0.093 Uiso calc R 1 . .
C C14 0.9416(2) 1.0546(6) 0.69527(16) 0.0880(9) Uani d . 1 . .
H H14 0.8835 1.1601 0.6853 0.106 Uiso calc R 1 . .
C C15 1.0179(3) 1.0851(6) 0.74911(15) 0.0845(9) Uani d . 1 . .
H H15 1.0131 1.2126 0.7753 0.101 Uiso calc R 1 . .
C C16 1.1002(2) 0.9256(7) 0.76324(14) 0.0906(10) Uani d . 1 . .
H H16 1.1521 0.9426 0.7998 0.109 Uiso calc R 1 . .
C C17 1.1083(2) 0.7385(6) 0.72431(14) 0.0815(9) Uani d . 1 . .
H H17 1.1655 0.6309 0.7352 0.098 Uiso calc R 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 N1 N2 . . 120.1(2) ?
C1 N2 N1 . . 118.4(2) ?
C1 N2 H2 . . 120.8 ?
N1 N2 H2 . . 120.8 ?
C1 N3 N4 . . 121.3(2) ?
C1 N3 H3 . . 119.3 ?
N4 N3 H3 . . 119.3 ?
C2 N4 N3 . . 115.9(2) ?
O5 C1 N3 . . 125.2(2) ?
O5 C1 N2 . . 121.8(2) ?
N3 C1 N2 . . 113.0(3) ?
N4 C2 C4 . . 116.5(2) ?
N4 C2 C3 . . 124.2(2) ?
C4 C2 C3 . . 119.3(2) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C9 C4 C5 . . 116.4(2) ?
C9 C4 C2 . . 121.9(2) ?
C5 C4 C2 . . 121.7(2) ?
C4 C5 C6 . . 122.1(3) ?
C4 C5 H5 . . 119.0 ?
C6 C5 H5 . . 119.0 ?
C7 C6 C5 . . 120.2(3) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C8 . . 119.0(3) ?
C6 C7 H7 . . 120.5 ?
C8 C7 H7 . . 120.5 ?
C7 C8 C9 . . 120.1(3) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C4 C9 C8 . . 122.2(3) ?
C4 C9 H9 . . 118.9 ?
C8 C9 H9 . . 118.9 ?
N1 C10 C12 . . 115.9(2) ?
N1 C10 C11 . . 124.5(3) ?
C12 C10 C11 . . 119.6(2) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C17 C12 C13 . . 116.5(3) ?
C17 C12 C10 . . 121.2(2) ?
C13 C12 C10 . . 122.3(2) ?
C14 C13 C12 . . 121.8(3) ?
C14 C13 H13 . . 119.1 ?
C12 C13 H13 . . 119.1 ?
C13 C14 C15 . . 120.5(3) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C16 C15 C14 . . 118.5(3) ?
C16 C15 H15 . . 120.7 ?
C14 C15 H15 . . 120.7 ?
C15 C16 C17 . . 120.9(3) ?
C15 C16 H16 . . 119.5 ?
C17 C16 H16 . . 119.5 ?
C12 C17 C16 . . 121.7(3) ?
C12 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
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
O5 C1 . 1.221(3) ?
N1 C10 . 1.282(3) ?
N1 N2 . 1.368(3) ?
N2 C1 . 1.368(3) ?
N2 H2 . 0.8600 ?
N3 C1 . 1.353(3) ?
N3 N4 . 1.372(2) ?
N3 H3 . 0.8600 ?
N4 C2 . 1.286(3) ?
C2 C4 . 1.474(3) ?
C2 C3 . 1.498(3) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C9 . 1.361(3) ?
C4 C5 . 1.370(3) ?
C5 C6 . 1.374(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.356(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.358(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.377(3) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C12 . 1.480(4) ?
C10 C11 . 1.507(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C17 . 1.374(3) ?
C12 C13 . 1.379(3) ?
C13 C14 . 1.367(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.373(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.353(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.376(4) ?
C16 H16 . 0.9300 ?
C17 H17 . 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
C3 H3C O5 1_565 0.96 2.53 3.405(3) 151.0
N2 H2 O5 3_756 0.86 2.11 2.955(3) 166.3
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656209
