#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/03/2240361.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_2240361
loop_
_publ_author_name
'Giannetto, Antonino'
'Lanza, Santo'
'Bruno, Giuseppe'
'Nicoló, Francesco'
'Amiri Rudbari, Hadi'
_publ_section_title
;
 Crystal structure of N,N'-bis(4-methylphenyl)dithiooxamide
;
_journal_coeditor_code           HB7339
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o67
_journal_paper_doi               10.1107/S2056989014027911
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C32 H32 N4 S4'
_chemical_formula_sum            'C32 H32 N4 S4'
_chemical_formula_weight         600.85
_chemical_name_systematic
;
N,N'-Bis(4-methylphenyl)ethanedithioamide
;
_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
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.4390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.9423(7)
_cell_length_b                   11.3880(2)
_cell_length_c                   7.8049(2)
_cell_measurement_reflns_used    141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.0
_cell_measurement_theta_min      4.30
_cell_volume                     2976.02(11)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_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 0.971
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0656
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            45528
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.966
_diffrn_reflns_theta_min         1.216
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.032
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0780P)²+1.5950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1516
_reflns_number_gt                1626
_reflns_number_total             2621
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7339sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2240361
_cod_database_fobs_code          2240361
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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
S S1 0.99746(3) 0.81087(8) 0.00428(12) 0.0493(3) Uani d 1
N N1 0.94997(8) 0.9912(2) -0.1064(3) 0.0362(7) Uani d 1
H H1 0.9486 1.0665 -0.115 0.043 Uiso calc 1
C C1 0.98496(9) 0.9507(3) -0.0303(4) 0.0325(7) Uani d 1
C C2 0.91413(10) 0.9314(3) -0.1764(4) 0.0319(8) Uani d 1
C C3 0.91366(10) 0.8248(3) -0.2619(4) 0.0376(8) Uani d 1
H H3 0.9375 0.7876 -0.2728 0.045 Uiso calc 1
C C4 0.87745(10) 0.7739(3) -0.3311(4) 0.0341(8) Uani d 1
H H4 0.8773 0.7022 -0.3883 0.041 Uiso calc 1
C C5 0.84155(10) 0.8273(3) -0.3169(4) 0.0329(8) Uani d 1
C C6 0.84256(10) 0.9343(3) -0.2318(4) 0.0347(8) Uani d 1
H H6 0.8187 0.9716 -0.221 0.042 Uiso calc 1
C C7 0.87853(10) 0.9868(3) -0.1626(4) 0.0335(8) Uani d 1
H H7 0.8787 1.0591 -0.107 0.04 Uiso calc 1
C C8 0.80238(11) 0.7709(4) -0.3933(5) 0.0527(11) Uani d 1
H H8A 0.7807 0.8197 -0.371 0.079 Uiso calc 0.5
H H8B 0.8004 0.6952 -0.3411 0.079 Uiso calc 0.5
H H8C 0.8011 0.7618 -0.5164 0.079 Uiso calc 0.5
H H8D 0.8074 0.6981 -0.448 0.079 Uiso calc 0.5
H H8E 0.7878 0.8226 -0.4779 0.079 Uiso calc 0.5
H H8F 0.787 0.756 -0.3026 0.079 Uiso calc 0.5
S S2 0.74804(3) 0.06064(8) 0.49865(14) 0.0539(3) Uani d 1
C C9 0.73490(9) 0.2010(3) 0.4708(4) 0.0317(7) Uani d 1
C C10 0.66362(9) 0.1808(3) 0.3324(4) 0.0298(7) Uani d 1
C C11 0.62785(10) 0.2328(3) 0.3544(4) 0.0298(7) Uani d 1
H H11 0.628 0.3029 0.4157 0.036 Uiso calc 1
C C12 0.59213(10) 0.1807(3) 0.2856(4) 0.0350(8) Uani d 1
H H12 0.5683 0.2158 0.3016 0.042 Uiso calc 1
C C13 0.59114(10) 0.0767(3) 0.1928(4) 0.0349(8) Uani d 1
C C14 0.62709(11) 0.0269(3) 0.1714(4) 0.0383(9) Uani d 1
H H14 0.6269 -0.0427 0.1088 0.046 Uiso calc 1
C C15 0.66335(10) 0.0771(3) 0.2398(4) 0.0351(8) Uani d 1
H H15 0.6872 0.0417 0.2239 0.042 Uiso calc 1
C C16 0.55213(12) 0.0194(4) 0.1170(5) 0.0542(11) Uani d 1
H H16A 0.5304 0.0656 0.1446 0.081 Uiso calc 0.5
H H16B 0.551 -0.0579 0.1649 0.081 Uiso calc 0.5
H H16C 0.5502 0.014 -0.0069 0.081 Uiso calc 0.5
H H16D 0.5573 -0.0512 0.0572 0.081 Uiso calc 0.5
H H16E 0.5367 0.0724 0.0368 0.081 Uiso calc 0.5
H H16F 0.5375 0.0005 0.2086 0.081 Uiso calc 0.5
N N2 0.69939(8) 0.2412(2) 0.4032(3) 0.0345(7) Uani d 1
H H2 0.6974 0.3165 0.4014 0.041 Uiso calc 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 0 '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
C1 N1 C2 . . 130.9(3)
C1 N1 H1 . . 114.6
C2 N1 H1 . . 114.6
N1 C1 C1 . 5_775 112.7(3)
N1 C1 S1 . . 126.6(2)
C1 C1 S1 5_775 . 120.7(3)
C7 C2 C3 . . 119.8(3)
C7 C2 N1 . . 117.0(3)
C3 C2 N1 . . 123.1(3)
C2 C3 C4 . . 119.6(3)
C2 C3 H3 . . 120.2
C4 C3 H3 . . 120.2
C5 C4 C3 . . 121.4(3)
C5 C4 H4 . . 119.3
C3 C4 H4 . . 119.3
C4 C5 C6 . . 118.2(3)
C4 C5 C8 . . 120.8(3)
C6 C5 C8 . . 121.0(3)
C5 C6 C7 . . 121.1(3)
C5 C6 H6 . . 119.5
C7 C6 H6 . . 119.5
C2 C7 C6 . . 119.9(3)
C2 C7 H7 . . 120.1
C6 C7 H7 . . 120.1
C5 C8 H8A . . 109.5
C5 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C5 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C5 C8 H8D . . 109.5
H8A C8 H8D . . 141.1
H8B C8 H8D . . 56.3
H8C C8 H8D . . 56.3
C5 C8 H8E . . 109.5
H8A C8 H8E . . 56.3
H8B C8 H8E . . 141.1
H8C C8 H8E . . 56.3
H8D C8 H8E . . 109.5
C5 C8 H8F . . 109.5
H8A C8 H8F . . 56.3
H8B C8 H8F . . 56.3
H8C C8 H8F . . 141.1
H8D C8 H8F . . 109.5
H8E C8 H8F . . 109.5
N2 C9 C9 . 7_656 112.9(3)
N2 C9 S2 . . 126.5(2)
C9 C9 S2 7_656 . 120.6(3)
C15 C10 C11 . . 119.9(3)
C15 C10 N2 . . 123.1(3)
C11 C10 N2 . . 116.9(3)
C12 C11 C10 . . 120.0(3)
C12 C11 H11 . . 120
C10 C11 H11 . . 120
C11 C12 C13 . . 121.1(3)
C11 C12 H12 . . 119.4
C13 C12 H12 . . 119.4
C14 C13 C12 . . 117.9(3)
C14 C13 C16 . . 120.8(3)
C12 C13 C16 . . 121.3(3)
C13 C14 C15 . . 122.1(3)
C13 C14 H14 . . 118.9
C15 C14 H14 . . 118.9
C14 C15 C10 . . 119.0(3)
C14 C15 H15 . . 120.5
C10 C15 H15 . . 120.5
C13 C16 H16A . . 109.5
C13 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C13 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
C13 C16 H16D . . 109.5
H16A C16 H16D . . 141.1
H16B C16 H16D . . 56.3
H16C C16 H16D . . 56.3
C13 C16 H16E . . 109.5
H16A C16 H16E . . 56.3
H16B C16 H16E . . 141.1
H16C C16 H16E . . 56.3
H16D C16 H16E . . 109.5
C13 C16 H16F . . 109.5
H16A C16 H16F . . 56.3
H16B C16 H16F . . 56.3
H16C C16 H16F . . 141.1
H16D C16 H16F . . 109.5
H16E C16 H16F . . 109.5
C9 N2 C10 . . 130.8(3)
C9 N2 H2 . . 114.6
C10 N2 H2 . . 114.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C1 . 1.659(3)
N1 C1 . 1.321(4)
N1 C2 . 1.423(4)
N1 H1 . 0.86
C1 C1 5_775 1.538(6)
C2 C7 . 1.383(5)
C2 C3 . 1.384(5)
C3 C4 . 1.386(5)
C3 H3 . 0.93
C4 C5 . 1.383(5)
C4 H4 . 0.93
C5 C6 . 1.386(5)
C5 C8 . 1.508(5)
C6 C7 . 1.387(4)
C6 H6 . 0.93
C7 H7 . 0.93
C8 H8A . 0.96
C8 H8B . 0.96
C8 H8C . 0.96
C8 H8D . 0.96
C8 H8E . 0.96
C8 H8F . 0.96
S2 C9 . 1.664(3)
C9 N2 . 1.316(4)
C9 C9 7_656 1.534(6)
C10 C15 . 1.383(5)
C10 C11 . 1.387(4)
C10 N2 . 1.426(4)
C11 C12 . 1.378(4)
C11 H11 . 0.93
C12 C13 . 1.385(5)
C12 H12 . 0.93
C13 C14 . 1.381(5)
C13 C16 . 1.508(5)
C14 C15 . 1.383(5)
C14 H14 . 0.93
C15 H15 . 0.93
C16 H16A . 0.96
C16 H16B . 0.96
C16 H16C . 0.96
C16 H16D . 0.96
C16 H16E . 0.96
C16 H16F . 0.96
N2 H2 . 0.86
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
N1 H1 S1 5_775 0.86 2.35 2.904(3) 122
N2 H2 S2 7_656 0.86 2.35 2.901(3) 122
C7 H7 Cg1 6_576 0.93 2.90 3.587(3) 132
C11 H11 Cg1 4_645 0.93 2.77 3.524(3) 139
C14 H14 Cg2 6_555 0.93 2.88 3.654(3) 142
