#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/62/2016214.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_2016214
loop_
_publ_author_name
'Brito, Iván'
'Mundaca, Aldo'
'Cárdenas, Alejandro'
'López-Rodríguez, Matías'
_publ_section_title
;
 5-(5-Nitropyridin-2-yldithio)-1-phenyl-1H-tetrazole
;
_journal_coeditor_code           SF3052
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o606
_journal_page_last               o608
_journal_paper_doi               10.1107/S010827010704142X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H8 N6 O2 S2'
_chemical_formula_moiety         'C12 H8 N6 O2 S2'
_chemical_formula_sum            'C12 H8 N6 O2 S2'
_chemical_formula_weight         332.36
_chemical_melting_point          .393E-305
_chemical_name_systematic
;
5-(5-Nitropyridin-2-yldithio)-1-phenyl-1H-tetrazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.233(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4161(2)
_cell_length_b                   21.6740(6)
_cell_length_c                   9.0312(3)
_cell_measurement_reflns_used    9419
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.37
_cell_volume                     1378.76(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ scans, and ω scans with κ  offsets'
_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  0.0544
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9028
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.16
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.16
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.056P)²+0.8023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1387
_reflns_number_gt                2656
_reflns_number_total             3104
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3052.cif
_cod_data_source_block           I
_cod_original_cell_volume        1378.76(7)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2016214
_cod_database_fobs_code          2016214
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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 0.41164(9) 0.66766(3) 0.27264(8) 0.0411(2) Uani d 1
S S2 0.42461(9) 0.57611(3) 0.22318(7) 0.0410(2) Uani d 1
O O1 -0.2424(4) 0.54863(15) -0.4551(3) 0.0801(8) Uani d 1
O O2 -0.1135(4) 0.45827(12) -0.4252(3) 0.0643(7) Uani d 1
N N1 0.1820(3) 0.67965(9) 0.4621(2) 0.0279(4) Uani d 1
N N2 -0.0045(3) 0.68553(11) 0.4463(2) 0.0370(5) Uani d 1
N N3 -0.0952(3) 0.68203(12) 0.2983(3) 0.0432(6) Uani d 1
N N4 0.0271(3) 0.67471(11) 0.2149(2) 0.0403(5) Uani d 1
N N5 0.2520(3) 0.50604(10) -0.0048(3) 0.0417(5) Uani d 1
N N6 -0.1230(4) 0.51153(13) -0.3850(3) 0.0492(6) Uani d 1
C C1 0.3200(3) 0.67998(11) 0.6153(2) 0.0265(5) Uani d 1
C C2 0.4414(4) 0.63069(13) 0.6632(3) 0.0358(6) Uani d 1
C C3 0.5655(4) 0.63095(15) 0.8136(3) 0.0444(7) Uani d 1
C C4 0.5656(4) 0.67993(16) 0.9122(3) 0.0453(7) Uani d 1
C C5 0.4430(4) 0.72875(14) 0.8630(3) 0.0400(6) Uani d 1
C C6 0.3182(3) 0.72941(13) 0.7115(3) 0.0328(5) Uani d 1
C C7 0.1981(3) 0.67277(11) 0.3181(3) 0.0310(5) Uani d 1
C C8 0.2624(3) 0.56573(12) 0.0327(3) 0.0309(5) Uani d 1
C C9 0.1584(4) 0.61202(12) -0.0628(3) 0.0331(5) Uani d 1
C C10 0.0317(4) 0.59435(13) -0.2035(3) 0.0349(6) Uani d 1
C C11 0.0185(3) 0.53267(13) -0.2408(3) 0.0356(6) Uani d 1
C C12 0.1311(4) 0.49009(14) -0.1427(4) 0.0443(7) Uani d 1
H H2 0.442(4) 0.5990(14) 0.606(3) 0.033(7) Uiso d 1
H H3 0.647(5) 0.5982(17) 0.857(4) 0.058(9) Uiso d 1
H H4 0.644(4) 0.6795(14) 1.007(4) 0.046(8) Uiso d 1
H H5 0.445(4) 0.7619(15) 0.938(4) 0.048(8) Uiso d 1
H H6 0.237(4) 0.7605(13) 0.679(3) 0.032(7) Uiso d 1
H H9 0.168(4) 0.6540(14) -0.033(3) 0.042(8) Uiso d 1
H H10 -0.046(5) 0.6227(16) -0.267(4) 0.052(9) Uiso d 1
H H12 0.126(5) 0.4497(19) -0.156(4) 0.067(11) Uiso d 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C7 S1 S2 102.68(9) y
C8 S2 S1 105.70(9) y
C7 N1 N2 107.75(18) ?
C7 N1 C1 132.4(2) ?
N2 N1 C1 119.77(18) ?
N3 N2 N1 106.6(2) ?
N2 N3 N4 111.0(2) ?
C7 N4 N3 105.9(2) ?
C12 N5 C8 117.2(2) ?
O1 N6 O2 124.8(3) y
O1 N6 C11 117.2(3) ?
O2 N6 C11 117.9(3) ?
C2 C1 C6 122.5(2) ?
C2 C1 N1 119.7(2) ?
C6 C1 N1 117.6(2) ?
C1 C2 C3 118.4(3) ?
C1 C2 H2 123.7(18) ?
C3 C2 H2 118.0(18) ?
C2 C3 C4 120.1(3) ?
C2 C3 H3 124(2) ?
C4 C3 H3 116(2) ?
C5 C4 C3 121.0(2) ?
C5 C4 H4 120(2) ?
C3 C4 H4 119(2) ?
C4 C5 C6 119.6(3) ?
C4 C5 H5 118.2(17) ?
C6 C5 H5 122.2(18) ?
C1 C6 C5 118.4(2) ?
C1 C6 H6 121.4(17) ?
C5 C6 H6 120.1(17) ?
N4 C7 N1 108.8(2) ?
N4 C7 S1 125.03(19) y
N1 C7 S1 126.05(18) y
N5 C8 C9 124.5(2) ?
N5 C8 S2 109.64(18) y
C9 C8 S2 125.8(2) y
C10 C9 C8 117.2(2) ?
C10 C9 H9 119.9(18) ?
C8 C9 H9 122.9(18) ?
C11 C10 C9 118.2(2) ?
C11 C10 H10 121(2) ?
C9 C10 H10 121(2) ?
C12 C11 C10 121.0(2) ?
C12 C11 N6 119.1(3) ?
C10 C11 N6 119.8(2) ?
N5 C12 C11 121.8(3) ?
N5 C12 H12 112(2) ?
C11 C12 H12 126(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 1.760(2) y
S1 S2 2.0427(10) y
S2 C8 1.779(2) y
O1 N6 1.217(4) ?
O2 N6 1.219(3) ?
N1 C7 1.351(3) ?
N1 N2 1.351(3) ?
N1 C1 1.441(3) y
N2 N3 1.297(3) ?
N3 N4 1.357(3) ?
N4 C7 1.318(3) ?
N5 C12 1.332(4) ?
N5 C8 1.334(3) ?
N6 C11 1.467(3) ?
C1 C2 1.377(3) ?
C1 C6 1.382(3) ?
C2 C3 1.382(4) ?
C2 H2 0.86(3) ?
C3 C4 1.386(5) ?
C3 H3 0.94(4) ?
C4 C5 1.375(4) ?
C4 H4 0.87(3) ?
C5 C6 1.391(3) ?
C5 H5 0.99(3) ?
C6 H6 0.89(3) ?
C8 C9 1.389(3) ?
C9 C10 1.378(4) ?
C9 H9 0.94(3) ?
C10 C11 1.375(4) ?
C10 H10 0.91(3) ?
C11 C12 1.368(4) ?
C12 H12 0.88(4) ?
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
C3 H3 N5 3_666 0.94(4) 2.61(4) 3.488(4) 156(3) yes
C9 H9 S1 . 0.95(3) 2.80(3) 3.256(3) 110.5(19) yes
C6 H6 Cg1 4_565 0.89(3) 2.84(3) 3.558(3) 139(2) yes
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
_geom_torsion_publ_flag
C7 S1 S2 C8 76.98(12) y
C7 N1 N2 N3 0.2(3) ?
C1 N1 N2 N3 -178.3(2) ?
N1 N2 N3 N4 -0.8(3) ?
N2 N3 N4 C7 1.0(3) ?
C7 N1 C1 C2 -55.4(4) ?
N2 N1 C1 C2 122.7(3) ?
C7 N1 C1 C6 127.6(3) ?
N2 N1 C1 C6 -54.3(3) ?
C6 C1 C2 C3 0.1(4) ?
N1 C1 C2 C3 -176.7(2) ?
C1 C2 C3 C4 0.1(4) ?
C2 C3 C4 C5 0.2(4) ?
C3 C4 C5 C6 -0.7(4) ?
C2 C1 C6 C5 -0.6(4) ?
N1 C1 C6 C5 176.3(2) ?
C4 C5 C6 C1 0.9(4) ?
N3 N4 C7 N1 -0.9(3) ?
N3 N4 C7 S1 -176.67(19) ?
N2 N1 C7 N4 0.5(3) ?
C1 N1 C7 N4 178.7(2) ?
N2 N1 C7 S1 176.19(19) ?
C1 N1 C7 S1 -5.6(4) ?
S2 S1 C7 N4 -79.3(2) y
S2 S1 C7 N1 105.7(2) ?
C12 N5 C8 C9 -1.1(4) ?
C12 N5 C8 S2 177.8(2) ?
S1 S2 C8 N5 -175.69(16) y
S1 S2 C8 C9 3.1(2) ?
N5 C8 C9 C10 2.2(4) ?
S2 C8 C9 C10 -176.44(18) ?
C8 C9 C10 C11 -0.8(4) ?
C9 C10 C11 C12 -1.5(4) ?
C9 C10 C11 N6 176.2(2) ?
O1 N6 C11 C12 167.2(3) ?
O2 N6 C11 C12 -12.3(4) ?
O1 N6 C11 C10 -10.5(4) ?
O2 N6 C11 C10 170.0(2) ?
C8 N5 C12 C11 -1.4(4) ?
C10 C11 C12 N5 2.7(4) ?
N6 C11 C12 N5 -174.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133070
