#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230504.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_2230504
loop_
_publ_author_name
'Feng, Lei'
'Ji, Haiwei'
'Wang, Renliang'
'Ge, Haiyan'
'Li, Li'
_publ_section_title
;
 1,5-Bis(1-phenylethylidene)thiocarbonohydrazide
;
_journal_coeditor_code           VM2088
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1514
_journal_paper_doi               10.1107/S1600536811018320
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H18 N4 S'
_chemical_formula_moiety         'C17 H18 N4 S'
_chemical_formula_sum            'C17 H18 N4 S'
_chemical_formula_weight         310.41
_chemical_name_systematic
;
1,5-Bis(1-phenylethylidene)thiocarbonohydrazide
;
_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                76.62(3)
_cell_angle_beta                 76.39(3)
_cell_angle_gamma                82.35(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5947(15)
_cell_length_b                   8.8202(18)
_cell_length_c                   13.084(3)
_cell_measurement_reflns_used    1351
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.126
_cell_measurement_theta_min      2.593
_cell_volume                     825.8(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4272
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.191
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2876
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0468
_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)+(0.0718P)²+0.2086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                2033
_reflns_number_total             2876
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2088.cif
_cod_data_source_block           I
_cod_database_code               2230504
_cod_database_fobs_code          2230504
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.91194(11) 0.69768(7) -0.10817(5) 0.0688(3) Uani d . 1 1 . .
N N1 0.7946(3) 0.9200(2) 0.00704(14) 0.0560(6) Uani d . 1 1 . .
H H1 0.7779 0.9500 0.0669 0.067 Uiso calc RD 1 1 . .
N N2 0.7386(3) 1.0205(2) -0.07909(14) 0.0521(5) Uani d . 1 1 . .
N N3 0.9241(3) 0.6971(2) 0.09311(14) 0.0566(6) Uani d . 1 1 . .
H H3 0.9787 0.6046 0.0982 0.068 Uiso calc R 1 1 . .
N N4 0.8830(3) 0.7712(2) 0.17832(15) 0.0520(5) Uani d . 1 1 . .
C C1 0.8745(3) 0.7765(3) -0.00005(18) 0.0524(6) Uani d . 1 1 . .
C C2 0.6582(3) 1.1530(3) -0.06107(18) 0.0498(6) Uani d . 1 1 . .
C C3 0.6205(4) 1.2028(3) 0.0448(2) 0.0677(8) Uani d . 1 1 . .
H H3A 0.6098 1.1120 0.1022 0.102 Uiso calc RD 1 1 . .
H H3B 0.5091 1.2689 0.0525 0.102 Uiso calc R 1 1 . .
H H3C 0.7185 1.2592 0.0474 0.102 Uiso calc R 1 1 . .
C C4 0.6017(3) 1.2612(2) -0.15566(18) 0.0514(6) Uani d . 1 1 . .
C C5 0.6339(4) 1.2169(3) -0.25393(19) 0.0617(7) Uani d . 1 1 . .
H H5 0.6893 1.1180 -0.2604 0.074 Uiso calc R 1 1 . .
C C6 0.5846(4) 1.3179(3) -0.3422(2) 0.0701(8) Uani d . 1 1 . .
H H6 0.6078 1.2867 -0.4076 0.084 Uiso calc R 1 1 . .
C C7 0.5015(4) 1.4645(3) -0.3343(2) 0.0704(8) Uani d . 1 1 . .
H H7 0.4694 1.5324 -0.3942 0.085 Uiso calc R 1 1 . .
C C8 0.4666(4) 1.5095(3) -0.2381(2) 0.0748(8) Uani d . 1 1 . .
H H8 0.4092 1.6080 -0.2321 0.090 Uiso calc R 1 1 . .
C C9 0.5164(4) 1.4089(3) -0.1491(2) 0.0661(8) Uani d . 1 1 . .
H H9 0.4921 1.4411 -0.0839 0.079 Uiso calc R 1 1 . .
C C10 0.9131(3) 0.6990(3) 0.27089(18) 0.0516(6) Uani d . 1 1 . .
C C11 0.9913(4) 0.5327(3) 0.2956(2) 0.0708(8) Uani d . 1 1 . .
H H11A 0.9160 0.4657 0.2797 0.106 Uiso calc R 1 1 . .
H H11B 0.9961 0.5032 0.3703 0.106 Uiso calc R 1 1 . .
H H11C 1.1118 0.5228 0.2525 0.106 Uiso calc R 1 1 . .
C C12 0.8641(3) 0.7926(3) 0.35463(18) 0.0528(6) Uani d . 1 1 . .
C C13 0.8581(5) 0.9550(3) 0.3268(2) 0.0790(9) Uani d . 1 1 . .
H H13 0.8894 1.0049 0.2550 0.095 Uiso calc R 1 1 . .
C C14 0.8063(7) 1.0415(4) 0.4049(3) 0.1186(16) Uani d . 1 1 . .
H H14 0.8012 1.1501 0.3855 0.142 Uiso calc R 1 1 . .
C C15 0.7621(7) 0.9703(4) 0.5109(3) 0.1202(16) Uani d . 1 1 . .
H H15 0.7270 1.0304 0.5631 0.144 Uiso calc R 1 1 . .
C C16 0.7691(5) 0.8118(4) 0.5402(2) 0.0960(12) Uani d . 1 1 . .
H H16 0.7384 0.7633 0.6124 0.115 Uiso calc R 1 1 . .
C C17 0.8217(4) 0.7239(3) 0.4628(2) 0.0696(8) Uani d . 1 1 . .
H H17 0.8291 0.6154 0.4834 0.084 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'
S S 0.1246 0.1234 '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
C1 N1 N2 . . 121.73(18) ?
C1 N1 H1 . . 119.1 ?
N2 N1 H1 . . 119.1 ?
C2 N2 N1 . . 115.81(18) ?
C1 N3 N4 . . 117.21(18) ?
C1 N3 H3 . . 121.4 ?
N4 N3 H3 . . 121.4 ?
C10 N4 N3 . . 120.56(19) ?
N1 C1 N3 . . 112.62(19) ?
N1 C1 S1 . . 125.52(17) ?
N3 C1 S1 . . 121.86(17) ?
N2 C2 C4 . . 114.99(19) ?
N2 C2 C3 . . 125.2(2) ?
C4 C2 C3 . . 119.78(19) ?
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 ?
C5 C4 C9 . . 117.8(2) ?
C5 C4 C2 . . 120.7(2) ?
C9 C4 C2 . . 121.6(2) ?
C6 C5 C4 . . 120.8(2) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C7 C6 C5 . . 120.6(2) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C8 C7 C6 . . 119.5(2) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C9 . . 120.2(2) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C8 C9 C4 . . 121.1(2) ?
C8 C9 H9 . . 119.5 ?
C4 C9 H9 . . 119.5 ?
N4 C10 C12 . . 114.8(2) ?
N4 C10 C11 . . 124.5(2) ?
C12 C10 C11 . . 120.7(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 . . 117.6(2) ?
C17 C12 C10 . . 121.9(2) ?
C13 C12 C10 . . 120.5(2) ?
C14 C13 C12 . . 120.2(3) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C14 C13 . . 120.7(3) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C16 C15 C14 . . 120.2(3) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 119.6(3) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C16 C17 C12 . . 121.6(3) ?
C16 C17 H17 . . 119.2 ?
C12 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
S1 C1 . 1.667(2) ?
N1 C1 . 1.343(3) ?
N1 N2 . 1.378(2) ?
N1 H1 . 0.8600 ?
N2 C2 . 1.290(3) ?
N3 C1 . 1.367(3) ?
N3 N4 . 1.374(3) ?
N3 H3 . 0.8600 ?
N4 C10 . 1.288(3) ?
C2 C4 . 1.490(3) ?
C2 C3 . 1.502(3) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.387(3) ?
C4 C9 . 1.388(3) ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.376(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.363(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.388(3) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C12 . 1.471(3) ?
C10 C11 . 1.499(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C17 . 1.383(3) ?
C12 C13 . 1.392(3) ?
C13 C14 . 1.368(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.366(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.358(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.370(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
N3 H3 S1 2_765 0.86 2.67 3.515(2) 169
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C2 . . . . 177.7(2) ?
C1 N3 N4 C10 . . . . 174.7(2) ?
N2 N1 C1 N3 . . . . 178.3(2) ?
N2 N1 C1 S1 . . . . -1.9(4) ?
N4 N3 C1 N1 . . . . 1.4(3) ?
N4 N3 C1 S1 . . . . -178.43(18) ?
N1 N2 C2 C4 . . . . 179.0(2) ?
N1 N2 C2 C3 . . . . -0.8(4) ?
N2 C2 C4 C5 . . . . 0.8(4) ?
C3 C2 C4 C5 . . . . -179.5(2) ?
N2 C2 C4 C9 . . . . -178.9(3) ?
C3 C2 C4 C9 . . . . 0.8(4) ?
C9 C4 C5 C6 . . . . 0.9(4) ?
C2 C4 C5 C6 . . . . -178.8(3) ?
C4 C5 C6 C7 . . . . -0.4(5) ?
C5 C6 C7 C8 . . . . -0.5(5) ?
C6 C7 C8 C9 . . . . 0.7(5) ?
C7 C8 C9 C4 . . . . -0.2(5) ?
C5 C4 C9 C8 . . . . -0.6(4) ?
C2 C4 C9 C8 . . . . 179.1(3) ?
N3 N4 C10 C12 . . . . 179.5(2) ?
N3 N4 C10 C11 . . . . -0.6(4) ?
N4 C10 C12 C17 . . . . 155.1(3) ?
C11 C10 C12 C17 . . . . -24.8(4) ?
N4 C10 C12 C13 . . . . -24.6(4) ?
C11 C10 C12 C13 . . . . 155.6(3) ?
C17 C12 C13 C14 . . . . -1.9(5) ?
C10 C12 C13 C14 . . . . 177.7(3) ?
C12 C13 C14 C15 . . . . 0.8(6) ?
C13 C14 C15 C16 . . . . 0.0(7) ?
C14 C15 C16 C17 . . . . 0.3(7) ?
C15 C16 C17 C12 . . . . -1.5(6) ?
C13 C12 C17 C16 . . . . 2.3(5) ?
C10 C12 C17 C16 . . . . -177.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5427550
