#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/85/2218576.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_2218576
loop_
_publ_author_name
'Shan, Shang'
'Tian, Yu-Liang'
'Wang, Shan-Heng'
'Wang, Wen-Long'
'Xu, Ying-Li'
_publ_section_title
;
 Benzyl 3-[(E)-benzylidene]dithiocarbazate
;
_journal_coeditor_code           XU2422
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1014
_journal_paper_doi               10.1107/S1600536808012944
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H14 N2 S2'
_chemical_formula_moiety         'C15 H14 N2 S2'
_chemical_formula_sum            'C15 H14 N2 S2'
_chemical_formula_weight         286.40
_chemical_name_systematic
;
Benzyl 3-[(E)-benzylidene]dithiocarbazate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/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                 97.652(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0053(18)
_cell_length_b                   23.075(8)
_cell_length_c                   12.646(5)
_cell_measurement_reflns_used    6568
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.9
_cell_volume                     1447.6(9)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15395
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.77
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0321
_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)+(0.0424P)²+0.226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                2115
_reflns_number_total             2653
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2422.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218576
_cod_database_fobs_code          2218576
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
S S1 -0.16273(11) 0.58470(2) 0.94815(4) 0.06114(17) Uani d . 1
S S2 0.02011(10) 0.602875(18) 0.73176(4) 0.05159(15) Uani d . 1
N N1 0.3232(3) 0.50304(6) 0.78197(11) 0.0493(4) Uani d . 1
N N2 0.1740(3) 0.51871(6) 0.86146(11) 0.0516(4) Uani d . 1
H H2N 0.1829 0.4979 0.9183 0.062 Uiso calc R 1
C C1 0.6444(3) 0.43585(7) 0.72802(14) 0.0486(4) Uani d . 1
C C2 0.6602(4) 0.46157(8) 0.62992(16) 0.0599(5) Uani d . 1
H H2 0.5621 0.4951 0.6109 0.072 Uiso calc R 1
C C3 0.8199(5) 0.43796(10) 0.56054(17) 0.0721(6) Uani d . 1
H H3 0.8285 0.4554 0.4948 0.087 Uiso calc R 1
C C4 0.9663(4) 0.38875(10) 0.5882(2) 0.0764(6) Uani d . 1
H H4 1.0736 0.3728 0.5411 0.092 Uiso calc R 1
C C5 0.9551(4) 0.36326(10) 0.68450(19) 0.0766(6) Uani d . 1
H H5 1.0555 0.3300 0.7029 0.092 Uiso calc R 1
C C6 0.7955(4) 0.38637(8) 0.75514(17) 0.0632(5) Uani d . 1
H H6 0.7894 0.3687 0.8209 0.076 Uiso calc R 1
C C7 0.4749(4) 0.45888(7) 0.80289(15) 0.0529(4) Uani d . 1
H H7 0.4769 0.4407 0.8687 0.064 Uiso calc R 1
C C8 0.0160(3) 0.56550(7) 0.85190(13) 0.0458(4) Uani d . 1
C C9 -0.2180(4) 0.66100(7) 0.74434(14) 0.0531(4) Uani d . 1
H H9A -0.3989 0.6455 0.7419 0.064 Uiso calc R 1
H H9B -0.1716 0.6810 0.8117 0.064 Uiso calc R 1
C C10 -0.2041(4) 0.70207(7) 0.65275(14) 0.0494(4) Uani d . 1
C C11 -0.3930(4) 0.69963(9) 0.56287(17) 0.0667(5) Uani d . 1
H H11 -0.5313 0.6725 0.5594 0.080 Uiso calc R 1
C C12 -0.3804(5) 0.73660(11) 0.47831(19) 0.0829(7) Uani d . 1
H H12 -0.5085 0.7340 0.4181 0.099 Uiso calc R 1
C C13 -0.1794(5) 0.77726(10) 0.4826(2) 0.0791(7) Uani d . 1
H H13 -0.1727 0.8028 0.4261 0.095 Uiso calc R 1
C C14 0.0112(5) 0.77991(9) 0.5708(2) 0.0763(6) Uani d . 1
H H14 0.1498 0.8069 0.5738 0.092 Uiso calc R 1
C C15 -0.0015(4) 0.74263(8) 0.65529(17) 0.0646(5) Uani d . 1
H H15 0.1288 0.7449 0.7149 0.077 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'
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
C8 S2 C9 101.79(8)
C7 N1 N2 115.03(14)
C8 N2 N1 121.23(14)
C8 N2 H2N 119.4
N1 N2 H2N 119.4
C2 C1 C6 118.64(17)
C2 C1 C7 122.28(16)
C6 C1 C7 119.08(17)
C3 C2 C1 120.55(19)
C3 C2 H2 119.7
C1 C2 H2 119.7
C4 C3 C2 120.1(2)
C4 C3 H3 120.0
C2 C3 H3 120.0
C5 C4 C3 120.2(2)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.5(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 120.0(2)
C5 C6 H6 120.0
C1 C6 H6 120.0
N1 C7 C1 122.63(16)
N1 C7 H7 118.7
C1 C7 H7 118.7
N2 C8 S1 121.27(13)
N2 C8 S2 113.71(12)
S1 C8 S2 125.02(10)
C10 C9 S2 107.43(11)
C10 C9 H9A 110.2
S2 C9 H9A 110.2
C10 C9 H9B 110.2
S2 C9 H9B 110.2
H9A C9 H9B 108.5
C15 C10 C11 117.96(18)
C15 C10 C9 121.28(17)
C11 C10 C9 120.75(17)
C12 C11 C10 121.2(2)
C12 C11 H11 119.4
C10 C11 H11 119.4
C13 C12 C11 120.2(2)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 119.4(2)
C14 C13 H13 120.3
C12 C13 H13 120.3
C13 C14 C15 120.3(2)
C13 C14 H14 119.9
C15 C14 H14 119.9
C10 C15 C14 121.0(2)
C10 C15 H15 119.5
C14 C15 H15 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.6636(17) y
S2 C8 1.7495(17) y
S2 C9 1.8153(18) y
N1 C7 1.277(2) y
N1 N2 1.3777(19) y
N2 C8 1.334(2) y
N2 H2N 0.8600 ?
C1 C2 1.387(3) ?
C1 C6 1.387(3) ?
C1 C7 1.454(2) ?
C2 C3 1.375(3) ?
C2 H2 0.9300 ?
C3 C4 1.372(3) ?
C3 H3 0.9300 ?
C4 C5 1.360(3) ?
C4 H4 0.9300 ?
C5 C6 1.382(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C9 C10 1.505(2) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C15 1.377(3) ?
C10 C11 1.379(3) ?
C11 C12 1.376(3) ?
C11 H11 0.9300 ?
C12 C13 1.371(3) ?
C12 H12 0.9300 ?
C13 C14 1.370(3) ?
C13 H13 0.9300 ?
C14 C15 1.380(3) ?
C14 H14 0.9300 ?
C15 H15 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
N2 H2N S1 3_567 0.86 2.56 3.396(2) 165 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740022
