##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2007-06-23
_journal_date_accepted     2007-06-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      8
_journal_page_first     o3351
_journal_page_last     o3352
_journal_paper_category     QO
_journal_coeditor_code     OM2142
_publ_contact_author_name     'Brito, Iván'
_publ_contact_author_address
;
Departamento de Química
Facultad de Ciencias Básicas
Universidad de Antofagasta
Casilla 170
Antofagasta, Chile
;
_publ_contact_author_email     ivanbritob@yahoo.com
_publ_contact_author_fax     '56(55)637814'
_publ_contact_author_phone     '56(55)637814'
_publ_section_title
;
5,5'-Dinitro-2,2'-dithiodipyridine
;
loop_
    _publ_author_name
    _publ_author_address
    'Brito, Iván'
;
Departamento de Química
Facultad de Ciencias Básicas
Universidad de Antofagasta
Casilla 170
Antofagasta
Chile
;
    'Mundaca, Aldo'
;
 Departamento de Química
 Facultad de Ciencias Básicas
 Universidad de Antofagasta
 Casilla 170
 Antofagasta
 Chile
;
    'Cárdenas, Alejandro'
;
 Departamento de Física
 Facultad de Ciencias Básicas
 Universidad de Antofagasta
 Casilla 170
 Antofagasta
 Chile
;
    'López-Rodríguez, Matías'
;
Instituto de Bio-Orgánica `Antonio González', Universidad de La Laguna,
Astrofísico Francisco Sánchez N°2, La Laguna, Tenerife, Spain
;
    'Vargas, Danitza'
;
 Departamento de Química
 Facultad de Ciencias Básicas
 Universidad de Antofagasta
 Casilla 170
 Antofagasta
 Chile
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
5,5'-Dinitro-2,2'-dithiodipyridine
;
_chemical_formula_moiety     'C10 H6 N4 O4 S2'
_chemical_formula_sum     'C10 H6 N4 O4 S2'
_chemical_formula_iupac     'C10 H6 N4 O4 S2'
_chemical_formula_weight     310.31
_chemical_melting_point        .428E-305
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     5.2610(15)
_cell_length_b     6.0440(13)
_cell_length_c     18.8070(19)
_cell_angle_alpha     90
_cell_angle_beta     92.839(12)
_cell_angle_gamma     90
_cell_volume     597.3(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2999
_cell_measurement_theta_min     3.5
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.725
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     316
_exptl_absorpt_coefficient_mu     0.466
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SORTAV; Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.842
_exptl_absorpt_correction_T_max     0.901
_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     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ scans, and ω scans with κ  offsets'
_diffrn_reflns_number     3529
_diffrn_reflns_av_R_equivalents     0.0671
_diffrn_reflns_theta_min     3.54
_diffrn_reflns_theta_max     27.52
_diffrn_reflns_theta_full     25.85
_diffrn_measured_fraction_theta_max     0.919
_diffrn_measured_fraction_theta_full     0.961
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     24
_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 > 2sigma(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     1267
_reflns_number_gt     1122
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0591
_refine_ls_wR_factor_ref     0.1394
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     1267
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'calc w=1/[σ²(Fo²)+1.3711P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.014
_refine_diff_density_max     0.481
_refine_diff_density_min     -0.31
_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'
    O O 0.0106 0.006 '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     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction     DENZO--SMN
_computing_structure_solution     'SIR97 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                  'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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_disorder_assembly
    _atom_site_disorder_group
    S S1 0.64977(15) 0.47850(13) 0.03722(4) 0.0348(3) Uani d . 1 . .
    O O1 0.4118(5) -0.4104(4) 0.22547(13) 0.0486(7) Uani d . 1 . .
    O O2 0.0696(5) -0.3958(5) 0.15797(16) 0.0615(9) Uani d . 1 . .
    N N1 0.2791(5) -0.3234(5) 0.17826(13) 0.0345(6) Uani d . 1 . .
    N N2 0.3161(5) 0.1460(4) 0.05263(13) 0.0314(6) Uani d . 1 . .
    C C1 0.5303(6) 0.2418(5) 0.07878(15) 0.0285(6) Uani d . 1 . .
    C C2 0.6740(6) 0.1634(5) 0.13849(16) 0.0328(7) Uani d . 1 . .
    H H2 0.8211 0.2363 0.155 0.039 Uiso calc R 1 . .
    C C3 0.5917(6) -0.0239(5) 0.17193(16) 0.0322(7) Uani d . 1 . .
    H H3 0.6816 -0.0821 0.2114 0.039 Uiso calc R 1 . .
    C C4 0.3700(6) -0.1227(5) 0.14469(15) 0.0281(6) Uani d . 1 . .
    C C5 0.2369(6) -0.0362(5) 0.08584(16) 0.0309(6) Uani d . 1 . .
    H H5 0.0886 -0.1061 0.0688 0.037 Uiso calc R 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 0.0363(5) 0.0301(4) 0.0372(4) -0.0081(3) -0.0048(3) 0.0063(3)
    O1 0.0510(15) 0.0434(15) 0.0504(14) -0.0051(12) -0.0078(11) 0.0192(11)
    O2 0.0546(17) 0.0570(18) 0.0706(18) -0.0317(15) -0.0185(13) 0.0224(15)
    N1 0.0384(15) 0.0303(14) 0.0346(13) -0.0055(11) 0.0002(11) 0.0023(11)
    N2 0.0293(13) 0.0298(14) 0.0347(13) -0.0020(11) -0.0022(10) 0.0018(10)
    C1 0.0319(15) 0.0249(14) 0.0289(14) -0.0001(12) 0.0037(11) -0.0011(11)
    C2 0.0306(15) 0.0326(17) 0.0347(15) -0.0058(13) -0.0029(12) -0.0004(12)
    C3 0.0338(16) 0.0321(16) 0.0300(14) 0.0016(13) -0.0042(11) 0.0025(12)
    C4 0.0298(15) 0.0236(14) 0.0311(14) 0.0000(12) 0.0026(11) -0.0002(11)
    C5 0.0299(15) 0.0299(16) 0.0327(15) -0.0043(12) -0.0006(11) -0.0007(12)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 . 1.761(3) no
    S1 S1 3_665 2.0719(15) no
    O1 N1 . 1.221(3) ?
    O2 N1 . 1.229(4) ?
    N1 C4 . 1.459(4) ?
    N2 C1 . 1.339(4) ?
    N2 C5 . 1.343(4) ?
    C1 C2 . 1.405(4) ?
    C2 C3 . 1.375(4) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.386(4) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.383(4) ?
    C5 H5 . 0.93 ?
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 S1 S1 . 3_665 97.22(11) yes
    O1 N1 O2 . . 123.0(3) ?
    O1 N1 C4 . . 119.0(3) ?
    O2 N1 C4 . . 118.0(3) ?
    C1 N2 C5 . . 117.3(3) ?
    N2 C1 C2 . . 123.9(3) yes
    N2 C1 S1 . . 120.0(2) yes
    C2 C1 S1 . . 116.0(2) yes
    C3 C2 C1 . . 118.3(3) yes
    C3 C2 H2 . . 120.9 ?
    C1 C2 H2 . . 120.9 ?
    C2 C3 C4 . . 117.7(3) ?
    C2 C3 H3 . . 121.2 ?
    C4 C3 H3 . . 121.2 ?
    C5 C4 C3 . . 121.1(3) ?
    C5 C4 N1 . . 119.8(3) yes
    C3 C4 N1 . . 119.1(3) ?
    N2 C5 C4 . . 121.7(3) ?
    N2 C5 H5 . . 119.1 ?
    C4 C5 H5 . . 119.1 ?
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
    C5 N2 C1 C2 . . . . -0.3(5) no
    C5 N2 C1 S1 . . . . 178.9(2) no
    S1 S1 C1 N2 3_665 . . . 5.2(3) no
    S1 S1 C1 C2 3_665 . . . -175.5(2) no
    N2 C1 C2 C3 . . . . 0.6(5) ?
    S1 C1 C2 C3 . . . . -178.6(2) ?
    C1 C2 C3 C4 . . . . -0.5(5) ?
    C2 C3 C4 C5 . . . . 0.2(5) ?
    C2 C3 C4 N1 . . . . 179.1(3) ?
    O1 N1 C4 C5 . . . . 172.6(3) ?
    O2 N1 C4 C5 . . . . -8.2(4) ?
    O1 N1 C4 C3 . . . . -6.4(4) ?
    O2 N1 C4 C3 . . . . 172.8(3) ?
    C1 N2 C5 C4 . . . . 0.0(4) ?
    C3 C4 C5 N2 . . . . 0.1(5) ?
    N1 C4 C5 N2 . . . . -178.9(3) ?
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
    C2 H2 O2 1_665 0.93 2.58 3.389(4) 146 yes
