##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-1-[2-(Methylsulfanyl)phenyl]-2-({(E)-2-[2-
(methylsulfanyl)phenyl]hydrazinylidene}(nitro)methyl)diazene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H15 N5 O2 S2'
_chemical_formula_sum     'C15 H15 N5 O2 S2'
_chemical_formula_iupac     'C15 H15 N5 O2 S2'
_chemical_formula_weight     361.44
_chemical_melting_point     417
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     4.7283(2)
_cell_length_b     17.9791(10)
_cell_length_c     19.3865(8)
_cell_angle_alpha     90.00
_cell_angle_beta     103.646(2)
_cell_angle_gamma     90.00
_cell_volume     1601.54(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8473
_cell_measurement_theta_min     2.27
_cell_measurement_theta_max     28.34
_cell_measurement_temperature     200(2)
_exptl_crystal_description     platelet
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.79
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.499
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     752
_exptl_absorpt_coefficient_mu     0.352
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.87040
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details     ?
_diffrn_ambient_temperature     200(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     '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     14965
_diffrn_reflns_av_R_equivalents     0.0194
_diffrn_reflns_av_sigmaI/netI     0.0183
_diffrn_reflns_theta_min     2.16
_diffrn_reflns_theta_max     28.34
_diffrn_reflns_theta_full     28.34
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3960
_reflns_number_gt     3301
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0409
_refine_ls_R_factor_gt     0.0306
_refine_ls_wR_factor_gt     0.0784
_refine_ls_wR_factor_ref     0.0860
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     3960
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0396P)²+0.7279P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.310
_refine_diff_density_min     -0.248
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    '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, 2010)'
_computing_cell_refinement     'SAINT (Bruker, 2010)'
_computing_data_reduction     'SAINT (Bruker, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
             'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
   'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
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 -0.33810(7) -0.05295(2) 0.125542(19) 0.02859(10) Uani d . 1 1 . .
    S S2 0.10204(8) 0.22354(2) 0.39420(2) 0.03395(11) Uani d . 1 1 . .
    O O1 0.2660(3) -0.13599(7) 0.23524(7) 0.0451(3) Uani d . 1 1 . .
    O O2 0.6661(3) -0.11093(7) 0.31138(6) 0.0419(3) Uani d . 1 1 . .
    N N1 -0.0436(2) 0.06137(7) 0.24775(6) 0.0261(2) Uani d . 1 1 . .
    N N2 0.0632(2) -0.00197(7) 0.23768(6) 0.0254(2) Uani d . 1 1 . .
    N N3 0.4414(3) 0.00974(7) 0.34898(6) 0.0262(2) Uani d . 1 1 . .
    N N4 0.3493(3) 0.07389(7) 0.36783(6) 0.0275(3) Uani d . 1 1 . .
    H H4 0.2011 0.0966 0.3397 0.033 Uiso calc R 1 1 . .
    N N5 0.4207(3) -0.09471(7) 0.27813(6) 0.0288(3) Uani d . 1 1 . .
    C C1 -0.6361(3) -0.08689(10) 0.05684(8) 0.0368(3) Uani d . 1 1 . .
    H H1A -0.8170 -0.0839 0.0731 0.055 Uiso calc R 1 1 . .
    H H1B -0.5993 -0.1387 0.0460 0.055 Uiso calc R 1 1 . .
    H H1C -0.6541 -0.0565 0.0141 0.055 Uiso calc R 1 1 . .
    C C2 0.2794(4) 0.25326(9) 0.32603(9) 0.0364(3) Uani d . 1 1 . .
    H H2A 0.4660 0.2766 0.3481 0.055 Uiso calc R 1 1 . .
    H H2B 0.1553 0.2892 0.2948 0.055 Uiso calc R 1 1 . .
    H H2C 0.3132 0.2101 0.2982 0.055 Uiso calc R 1 1 . .
    C C3 0.3021(3) -0.02142(8) 0.29019(7) 0.0244(3) Uani d . 1 1 . .
    C C11 -0.2889(3) 0.08284(8) 0.19544(7) 0.0242(3) Uani d . 1 1 . .
    C C12 -0.4468(3) 0.03812(8) 0.13894(7) 0.0241(3) Uani d . 1 1 . .
    C C13 -0.6941(3) 0.07045(9) 0.09478(8) 0.0292(3) Uani d . 1 1 . .
    H H13 -0.8071 0.0420 0.0569 0.035 Uiso calc R 1 1 . .
    C C14 -0.7781(3) 0.14243(9) 0.10470(8) 0.0326(3) Uani d . 1 1 . .
    H H14 -0.9475 0.1623 0.0737 0.039 Uiso calc R 1 1 . .
    C C15 -0.6196(3) 0.18619(9) 0.15909(8) 0.0321(3) Uani d . 1 1 . .
    H H15 -0.6756 0.2361 0.1650 0.039 Uiso calc R 1 1 . .
    C C16 -0.3795(3) 0.15564(8) 0.20428(8) 0.0292(3) Uani d . 1 1 . .
    H H16 -0.2721 0.1847 0.2425 0.035 Uiso calc R 1 1 . .
    C C21 0.4883(3) 0.10600(8) 0.43295(7) 0.0259(3) Uani d . 1 1 . .
    C C22 0.3908(3) 0.17503(8) 0.45127(7) 0.0264(3) Uani d . 1 1 . .
    C C23 0.5239(3) 0.20576(9) 0.51675(8) 0.0328(3) Uani d . 1 1 . .
    H H23 0.4580 0.2523 0.5301 0.039 Uiso calc R 1 1 . .
    C C24 0.7501(4) 0.16978(10) 0.56265(8) 0.0364(3) Uani d . 1 1 . .
    H H24 0.8379 0.1913 0.6073 0.044 Uiso calc R 1 1 . .
    C C25 0.8481(4) 0.10248(10) 0.54336(9) 0.0400(4) Uani d . 1 1 . .
    H H25 1.0057 0.0780 0.5746 0.048 Uiso calc R 1 1 . .
    C C26 0.7182(4) 0.07032(9) 0.47872(8) 0.0371(4) Uani d . 1 1 . .
    H H26 0.7863 0.0239 0.4657 0.045 Uiso calc R 1 1 . .
_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 C12 . 1.7538(15) ?
    S1 C1 . 1.8018(15) ?
    S2 C22 . 1.7710(14) ?
    S2 C2 . 1.8050(17) ?
    O1 N5 . 1.2208(16) ?
    O2 N5 . 1.2226(16) ?
    N1 N2 . 1.2793(17) ?
    N1 C11 . 1.4028(17) ?
    N2 C3 . 1.3754(17) ?
    N3 C3 . 1.3009(17) ?
    N3 N4 . 1.3148(17) ?
    N4 C21 . 1.4029(17) ?
    N4 H4 . 0.8800 ?
    N5 C3 . 1.4720(18) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 H2A . 0.9800 ?
    C2 H2B . 0.9800 ?
    C2 H2C . 0.9800 ?
    C11 C16 . 1.400(2) ?
    C11 C12 . 1.4205(18) ?
    C12 C13 . 1.4018(19) ?
    C13 C14 . 1.381(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.385(2) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.374(2) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C21 C26 . 1.387(2) ?
    C21 C22 . 1.399(2) ?
    C22 C23 . 1.391(2) ?
    C23 C24 . 1.380(2) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.379(2) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.385(2) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
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
    C12 S1 C1 . . 102.72(7) ?
    C22 S2 C2 . . 100.39(7) ?
    N2 N1 C11 . . 115.05(11) ?
    N1 N2 C3 . . 113.46(11) ?
    C3 N3 N4 . . 119.26(12) ?
    N3 N4 C21 . . 119.70(11) ?
    N3 N4 H4 . . 120.1 ?
    C21 N4 H4 . . 120.1 ?
    O1 N5 O2 . . 123.76(13) ?
    O1 N5 C3 . . 117.59(12) ?
    O2 N5 C3 . . 118.65(11) ?
    S1 C1 H1A . . 109.5 ?
    S1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    S1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    S2 C2 H2A . . 109.5 ?
    S2 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 109.5 ?
    S2 C2 H2C . . 109.5 ?
    H2A C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    N3 C3 N2 . . 134.15(13) ?
    N3 C3 N5 . . 113.05(11) ?
    N2 C3 N5 . . 112.77(11) ?
    C16 C11 N1 . . 113.16(12) ?
    C16 C11 C12 . . 120.20(12) ?
    N1 C11 C12 . . 126.61(13) ?
    C13 C12 C11 . . 116.57(13) ?
    C13 C12 S1 . . 121.87(11) ?
    C11 C12 S1 . . 121.56(10) ?
    C14 C13 C12 . . 121.98(13) ?
    C14 C13 H13 . . 119.0 ?
    C12 C13 H13 . . 119.0 ?
    C13 C14 C15 . . 121.09(14) ?
    C13 C14 H14 . . 119.5 ?
    C15 C14 H14 . . 119.5 ?
    C16 C15 C14 . . 118.39(14) ?
    C16 C15 H15 . . 120.8 ?
    C14 C15 H15 . . 120.8 ?
    C15 C16 C11 . . 121.74(13) ?
    C15 C16 H16 . . 119.1 ?
    C11 C16 H16 . . 119.1 ?
    C26 C21 C22 . . 120.22(13) ?
    C26 C21 N4 . . 121.02(13) ?
    C22 C21 N4 . . 118.76(12) ?
    C23 C22 C21 . . 118.61(13) ?
    C23 C22 S2 . . 119.38(12) ?
    C21 C22 S2 . . 122.01(10) ?
    C24 C23 C22 . . 121.13(14) ?
    C24 C23 H23 . . 119.4 ?
    C22 C23 H23 . . 119.4 ?
    C25 C24 C23 . . 119.69(14) ?
    C25 C24 H24 . . 120.2 ?
    C23 C24 H24 . . 120.2 ?
    C24 C25 C26 . . 120.40(15) ?
    C24 C25 H25 . . 119.8 ?
    C26 C25 H25 . . 119.8 ?
    C25 C26 C21 . . 119.93(15) ?
    C25 C26 H26 . . 120.0 ?
    C21 C26 H26 . . 120.0 ?
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
    C11 N1 N2 C3 . . . . -179.60(11) ?
    C3 N3 N4 C21 . . . . 176.56(13) ?
    N4 N3 C3 N2 . . . . 1.0(2) ?
    N4 N3 C3 N5 . . . . -176.84(12) ?
    N1 N2 C3 N3 . . . . 1.7(2) ?
    N1 N2 C3 N5 . . . . 179.48(11) ?
    O1 N5 C3 N3 . . . . 161.94(13) ?
    O2 N5 C3 N3 . . . . -17.90(19) ?
    O1 N5 C3 N2 . . . . -16.36(18) ?
    O2 N5 C3 N2 . . . . 163.80(13) ?
    N2 N1 C11 C16 . . . . -173.42(12) ?
    N2 N1 C11 C12 . . . . 8.4(2) ?
    C16 C11 C12 C13 . . . . -0.93(19) ?
    N1 C11 C12 C13 . . . . 177.12(13) ?
    C16 C11 C12 S1 . . . . 179.31(11) ?
    N1 C11 C12 S1 . . . . -2.65(19) ?
    C1 S1 C12 C13 . . . . -7.47(13) ?
    C1 S1 C12 C11 . . . . 172.28(12) ?
    C11 C12 C13 C14 . . . . 1.0(2) ?
    S1 C12 C13 C14 . . . . -179.22(11) ?
    C12 C13 C14 C15 . . . . 0.2(2) ?
    C13 C14 C15 C16 . . . . -1.6(2) ?
    C14 C15 C16 C11 . . . . 1.6(2) ?
    N1 C11 C16 C15 . . . . -178.69(13) ?
    C12 C11 C16 C15 . . . . -0.4(2) ?
    N3 N4 C21 C26 . . . . -1.4(2) ?
    N3 N4 C21 C22 . . . . 178.64(13) ?
    C26 C21 C22 C23 . . . . -1.7(2) ?
    N4 C21 C22 C23 . . . . 178.25(13) ?
    C26 C21 C22 S2 . . . . 179.03(12) ?
    N4 C21 C22 S2 . . . . -1.06(19) ?
    C2 S2 C22 C23 . . . . 108.63(13) ?
    C2 S2 C22 C21 . . . . -72.07(13) ?
    C21 C22 C23 C24 . . . . 0.8(2) ?
    S2 C22 C23 C24 . . . . -179.83(12) ?
    C22 C23 C24 C25 . . . . 0.5(2) ?
    C23 C24 C25 C26 . . . . -0.9(3) ?
    C24 C25 C26 C21 . . . . 0.1(3) ?
    C22 C21 C26 C25 . . . . 1.2(2) ?
    N4 C21 C26 C25 . . . . -178.72(15) ?
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
    N4 H4 S2 . 0.88 2.60 3.0248(13) 110.4
    N4 H4 N1 . 0.88 1.99 2.6229(16) 128.2
    C2 H2B O1 2 0.98 2.36 3.253(2) 151.1
    C25 H25 O2 3_756 0.95 2.45 3.1901(19) 134.1
data_global
_journal_date_recd_electronic     2011-12-09
_journal_date_accepted     2011-12-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      1
_journal_page_first     o199
_journal_page_last     o200
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536811054080
_journal_coeditor_code     ZQ2147
_publ_contact_author_name     'Karel G. von Eschwege'
_publ_contact_author_address
;
Department of Chemistry, University of the Free State, PO Box 339,
Bloemfontein 9300, South Africa
;
_publ_contact_author_email     'veschwkg@ufs.ac.za'
_publ_contact_author_fax     '+27 (0)86 695 3248'
_publ_contact_author_phone     '+27 (0)51 401 2923'
_publ_section_title
;\
(E)-1-[2-(Methylsulfanyl)phenyl]-2-({(E)-2-[2-(methylsulfanyl)\
phenyl]hydrazinylidene}(nitro)methyl)diazene
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Eschwege, Karel G. von' .
;
Department of Chemistry
University of the Free State
PO Box 339
Bloemfontein 9300
South Africa
;
    'Muller, Fabian' .
;
Department of Chemistry
University of the Free State
PO Box 339
Bloemfontein 9300
South Africa
;
    'Hosten, Eric C.' .
;
Department of Chemistry
Nelson Mandela Metropolitan University
PO Box 77000
Port Elizabeth 6031
South Africa
;
