##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4.3
_journal_data_validation_number     ?
_journal_date_recd_electronic     2014-12-11
_journal_date_accepted     2014-12-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      2
_journal_page_first     o67
_journal_page_last     o67
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989014027911
_journal_coeditor_code     HB7339
_publ_contact_author_name     'Antonino Giannetto'
_publ_contact_author_address
;
Department of Chemical Sciences,
University of Messina,
Via F. Stagno d'Alcontres 31,
98166 Messina, Italy
;
_publ_contact_author_email     'giannetto@unime.it'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structure of N,N'-bis(4-methylphenyl)dithiooxamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Giannetto, Antonino' .
;
Department of Chemical Sciences,
University of Messina,
Via F. Stagno d'Alcontres 31,
98166 Messina, Italy
;
    'Lanza, Santo' .
;
Department of Chemical Sciences,
University of Messina,
Via F. Stagno d'Alcontres 31,
98166 Messina, Italy
;
    'Bruno, Giuseppe' .
;
Department of Chemical Sciences,
University of Messina,
Via F. Stagno d'Alcontres 31,
98166 Messina, Italy
;
    'Nicoló, Francesco' .
;
Department of Chemical Sciences,
University of Messina,
Via F. Stagno d'Alcontres 31,
98166 Messina, Italy
;
    'Amiri Rudbari, Hadi' .
;
Department of Chemistry,
University of Isfahan,
81746-73441 Isfahan, Iran
;
_publ_section_synopsis     .
data_I
_database_code_depnum_ccdc_archive 'CCDC 1040609'
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
N,N'-Bis(4-methylphenyl)ethanedithioamide
;
_chemical_name_common     ?
_chemical_formula_sum     'C16 H16 N2 S2'
_chemical_formula_iupac   'C16 H16 N2 S2'
_chemical_formula_weight     300.425 #600.85
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
_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.
;
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'
_cell_length_a     33.9423(7)
_cell_length_b     11.3880(2)
_cell_length_c     7.8049(2)
_cell_angle_alpha     90
_cell_angle_beta     99.4390(10)
_cell_angle_gamma     90
_cell_volume     2976.02(11)
_cell_formula_units_Z     8 #4
_cell_measurement_reflns_used     141
_cell_measurement_theta_min     4.30
_cell_measurement_theta_max     22.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prismatic
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.341
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1264
_exptl_absorpt_coefficient_mu     0.349
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_absorpt_correction_T_min     0.6571
_exptl_absorpt_correction_T_max     0.7449
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     45528
_diffrn_reflns_av_R_equivalents     0.0656
_diffrn_reflns_theta_min     1.216
_diffrn_reflns_theta_max     24.966
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.971
_diffrn_reflns_limit_h_min     -40
_diffrn_reflns_limit_h_max     40
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details     ?
_reflns_number_total     2621
_reflns_number_gt     1626
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0916
_refine_ls_R_factor_gt     0.0553
_refine_ls_wR_factor_ref     0.1516
_refine_ls_goodness_of_fit_ref     1.109
_refine_ls_restrained_S_all     1.109
_refine_ls_number_reflns     2621
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0780P)²+1.5950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0
_refine_diff_density_max     1.032
_refine_diff_density_min     -0.205
_refine_ls_extinction_method     none
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'
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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_disorder_assembly
    _atom_site_disorder_group
    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_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0357(5) 0.0427(6) 0.0649(6) -0.0054(4) -0.0051(4) 0.0079(4)
    N1 0.0268(17) 0.0327(16) 0.0462(16) -0.0045(13) -0.0025(13) 0.0003(12)
    C1 0.0267(16) 0.0429(18) 0.0283(15) -0.0072(15) 0.0052(12) 0.0001(14)
    C2 0.0230(17) 0.039(2) 0.0318(16) -0.0040(16) -0.0003(13) 0.0034(15)
    C3 0.0277(18) 0.045(2) 0.0396(18) 0.0023(17) 0.0048(14) -0.0032(16)
    C4 0.037(2) 0.0299(19) 0.0350(17) -0.0013(16) 0.0028(15) -0.0056(14)
    C5 0.0317(19) 0.035(2) 0.0302(16) -0.0052(17) 0.0000(14) 0.0018(15)
    C6 0.0272(18) 0.037(2) 0.0382(17) 0.0032(16) 0.0015(14) 0.0008(15)
    C7 0.0325(19) 0.0290(18) 0.0372(17) -0.0011(15) 0.0006(14) 0.0003(14)
    C8 0.034(2) 0.063(3) 0.059(2) -0.017(2) 0.0014(18) -0.013(2)
    S2 0.0350(5) 0.0349(5) 0.0861(7) -0.0018(4) -0.0067(5) 0.0092(5)
    C9 0.0255(16) 0.0361(17) 0.0341(16) -0.0004(14) 0.0063(13) 0.0050(13)
    C10 0.0256(17) 0.0305(19) 0.0322(15) -0.0034(15) 0.0011(13) 0.0031(14)
    C11 0.0300(18) 0.0228(17) 0.0361(16) 0.0048(14) 0.0041(14) -0.0014(13)
    C12 0.0229(17) 0.044(2) 0.0376(17) 0.0019(16) 0.0033(14) -0.0002(15)
    C13 0.0293(19) 0.040(2) 0.0335(17) -0.0041(17) 0.0001(14) 0.0033(16)
    C14 0.042(2) 0.035(2) 0.0369(17) -0.0029(17) 0.0026(16) -0.0066(15)
    C15 0.0305(18) 0.034(2) 0.0415(18) 0.0048(16) 0.0071(14) -0.0055(15)
    C16 0.039(2) 0.061(3) 0.060(2) -0.017(2) 0.0008(19) -0.015(2)
    N2 0.0249(16) 0.0296(16) 0.0475(16) -0.0021(12) 0.0017(13) -0.0009(12)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 . 1.659(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_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 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_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
