#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/12/2211287.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_2211287
loop_
_publ_author_name
'Li-Rong Wen'
'Jian-Xia Zhou'
'En-Tao Sun'
_publ_section_title
;
 3,3'-(Butane-1,4-diyldithio)bis(5-phenyl-1,2,4-triazine)
;
_journal_coeditor_code           BI2083
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5399
_journal_page_last               o5400
_journal_paper_doi               10.1107/S1600536806045338
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H20 N6 S2'
_chemical_formula_moiety         'C22 H20 N6 S2'
_chemical_formula_sum            'C22 H20 N6 S2'
_chemical_formula_weight         432.56
_chemical_name_systematic
;
3,3'-(Butane-1,4-diyldithio)bis(5-phenyl-1,2,4-triazine)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 113.553(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.323(5)
_cell_length_b                   11.434(6)
_cell_length_c                   9.562(5)
_cell_measurement_reflns_used    1562
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.79
_cell_volume                     1034.6(9)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5764
_diffrn_reflns_theta_full        26.62
_diffrn_reflns_theta_max         26.62
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.2027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                1434
_reflns_number_total             2153
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2083.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211287
_cod_database_fobs_code          2211287
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'
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
S S1 0.62874(7) 0.43165(5) 0.23737(7) 0.0500(2) Uani d . 1
N N1 0.73106(17) 0.46983(15) 0.03468(18) 0.0366(4) Uani d . 1
N N2 0.6841(2) 0.64002(16) 0.1511(2) 0.0492(5) Uani d . 1
N N3 0.7200(2) 0.70811(16) 0.0582(2) 0.0562(6) Uani d . 1
C C1 0.8206(2) 0.36087(19) -0.1727(2) 0.0428(6) Uani d . 1
H H1 0.7803 0.3158 -0.1196 0.051 Uiso calc R 1
C C2 0.8724(2) 0.3071(2) -0.2679(3) 0.0507(6) Uani d . 1
H H2 0.8670 0.2262 -0.2793 0.061 Uiso calc R 1
C C3 0.9325(2) 0.3731(2) -0.3466(2) 0.0490(6) Uani d . 1
H H3 0.9678 0.3370 -0.4113 0.059 Uiso calc R 1
C C4 0.9403(2) 0.4913(2) -0.3298(3) 0.0518(6) Uani d . 1
H H4 0.9815 0.5355 -0.3827 0.062 Uiso calc R 1
C C5 0.8878(2) 0.5465(2) -0.2350(2) 0.0456(6) Uani d . 1
H H5 0.8928 0.6274 -0.2251 0.055 Uiso calc R 1
C C6 0.8273(2) 0.48061(18) -0.1543(2) 0.0330(5) Uani d . 1
C C7 0.7710(2) 0.53748(18) -0.0521(2) 0.0351(5) Uani d . 1
C C8 0.7585(3) 0.65854(19) -0.0425(3) 0.0496(6) Uani d . 1
H H8 0.7784 0.7059 -0.1105 0.059 Uiso calc R 1
C C9 0.6857(2) 0.52553(19) 0.1300(2) 0.0372(5) Uani d . 1
C C10 0.5766(2) 0.5314(2) 0.3512(2) 0.0431(6) Uani d . 1
H H10A 0.6566 0.5788 0.4142 0.052 Uiso calc R 1
H H10B 0.5027 0.5831 0.2857 0.052 Uiso calc R 1
C C11 0.5232(2) 0.46043(19) 0.4507(2) 0.0420(5) Uani d . 1
H H11A 0.5976 0.4088 0.5154 0.050 Uiso calc R 1
H H11B 0.4442 0.4125 0.3869 0.050 Uiso calc R 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 0.0000 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'
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
C9 S1 C10 . . 102.64(11)
C7 N1 C9 . . 115.60(18)
C9 N2 N3 . . 116.69(17)
C8 N3 N2 . . 118.81(19)
C2 C1 C6 . . 121.10(19)
C2 C1 H1 . . 119.5
C6 C1 H1 . . 119.5
C1 C2 C3 . . 119.8(2)
C1 C2 H2 . . 120.1
C3 C2 H2 . . 120.1
C4 C3 C2 . . 119.9(2)
C4 C3 H3 . . 120.0
C2 C3 H3 . . 120.0
C3 C4 C5 . . 120.8(2)
C3 C4 H4 . . 119.6
C5 C4 H4 . . 119.6
C4 C5 C6 . . 119.9(2)
C4 C5 H5 . . 120.1
C6 C5 H5 . . 120.1
C1 C6 C5 . . 118.52(18)
C1 C6 C7 . . 120.64(17)
C5 C6 C7 . . 120.84(19)
N1 C7 C8 . . 118.75(18)
N1 C7 C6 . . 117.73(18)
C8 C7 C6 . . 123.52(18)
N3 C8 C7 . . 122.7(2)
N3 C8 H8 . . 118.6
C7 C8 H8 . . 118.6
N2 C9 N1 . . 126.99(19)
N2 C9 S1 . . 119.41(15)
N1 C9 S1 . . 113.58(16)
C11 C10 S1 . . 108.19(16)
C11 C10 H10A . . 110.1
S1 C10 H10A . . 110.1
C11 C10 H10B . . 110.1
S1 C10 H10B . . 110.1
H10A C10 H10B . . 108.4
C10 C11 C11 . 3_666 110.9(2)
C10 C11 H11A . . 109.5
C11 C11 H11A 3_666 . 109.5
C10 C11 H11B . . 109.5
C11 C11 H11B 3_666 . 109.5
H11A C11 H11B . . 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C9 . 1.742(2)
S1 C10 . 1.802(2)
N1 C7 . 1.315(2)
N1 C9 . 1.340(2)
N2 C9 . 1.326(3)
N2 N3 . 1.340(2)
N3 C8 . 1.308(3)
C1 C2 . 1.373(3)
C1 C6 . 1.379(3)
C1 H1 . 0.930
C2 C3 . 1.376(3)
C2 H2 . 0.930
C3 C4 . 1.359(4)
C3 H3 . 0.930
C4 C5 . 1.380(3)
C4 H4 . 0.930
C5 C6 . 1.392(3)
C5 H5 . 0.930
C6 C7 . 1.473(3)
C7 C8 . 1.397(3)
C8 H8 . 0.930
C10 C11 . 1.512(3)
C10 H10A . 0.970
C10 H10B . 0.970
C11 C11 3_666 1.516(4)
C11 H11A . 0.970
C11 H11B . 0.970
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_4
_geom_torsion
C9 N2 N3 C8 . -2.3(3)
C6 C1 C2 C3 . 0.1(4)
C1 C2 C3 C4 . 0.0(4)
C2 C3 C4 C5 . -0.4(4)
C3 C4 C5 C6 . 0.6(4)
C2 C1 C6 C5 . 0.1(3)
C2 C1 C6 C7 . 179.8(2)
C4 C5 C6 C1 . -0.5(3)
C4 C5 C6 C7 . 179.8(2)
C9 N1 C7 C8 . -2.2(3)
C9 N1 C7 C6 . 177.52(17)
C1 C6 C7 N1 . 8.4(3)
C5 C6 C7 N1 . -171.90(19)
C1 C6 C7 C8 . -171.8(2)
C5 C6 C7 C8 . 7.8(3)
N2 N3 C8 C7 . -3.4(4)
N1 C7 C8 N3 . 5.9(4)
C6 C7 C8 N3 . -173.8(2)
N3 N2 C9 N1 . 6.3(3)
N3 N2 C9 S1 . -175.63(16)
C7 N1 C9 N2 . -3.9(3)
C7 N1 C9 S1 . 177.98(15)
C10 S1 C9 N2 . 1.5(2)
C10 S1 C9 N1 . 179.81(16)
C9 S1 C10 C11 . 179.65(16)
S1 C10 C11 C11 3_666 -179.7(2)
