#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/04/2210498.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_2210498
loop_
_publ_author_name
'Wang, Jing'
'Wang, Wei'
'Chi, Hai-Jun'
'Yang, Qing-Shan '
_publ_section_title
;
 trans-2,2'-[(2-Butene-1,4-diyl)dithio]bis(4,5-dihydro-1,3-thiazine)
;
_journal_coeditor_code           BH2046
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4621
_journal_page_last               o4622
_journal_paper_doi               10.1107/S1600536806038190
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H18 N2 S4'
_chemical_formula_moiety         'C12 H18 N2 S4'
_chemical_formula_sum            'C12 H18 N2 S4'
_chemical_formula_weight         318.52
_chemical_melting_point          357
_chemical_name_systematic
;
trans-2,2'-[(2-Butene-1,4-diyl)dithio]bis(4,5-dihydro-1,3-thiazine)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 114.100(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.282(5)
_cell_length_b                   10.578(6)
_cell_length_c                   9.625(6)
_cell_measurement_reflns_used    1520
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      3.01
_cell_volume                     769.7(8)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4202
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.965
_refine_diff_density_min         -0.481
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0586P)²+0.568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1440
_reflns_number_gt                1102
_reflns_number_total             1567
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2046.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210498
_cod_database_fobs_code          2210498
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'
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 0.69683(13) 0.41117(10) 0.41364(13) 0.0713(4) Uani d . 1
S S2 0.38467(11) 0.36247(8) 0.14298(11) 0.0526(3) Uani d . 1
N N1 0.4859(4) 0.5980(3) 0.2323(3) 0.0493(7) Uani d . 1
C C1 0.7903(5) 0.5460(4) 0.5323(4) 0.0609(10) Uani d . 1
H H1A 0.7285 0.5601 0.5975 0.073 Uiso calc R 1
H H1B 0.9135 0.5293 0.5969 0.073 Uiso calc R 1
C C2 0.7778(7) 0.6600(5) 0.4415(5) 0.0859(15) Uani d . 1
H H2A 0.8506 0.6476 0.3852 0.103 Uiso calc R 1
H H2B 0.8280 0.7301 0.5108 0.103 Uiso calc R 1
C C3 0.5978(5) 0.6964(4) 0.3323(5) 0.0668(11) Uani d . 1
H H3A 0.5358 0.7314 0.3900 0.080 Uiso calc R 1
H H3B 0.6096 0.7637 0.2686 0.080 Uiso calc R 1
C C4 0.5198(4) 0.4831(3) 0.2605(3) 0.0392(7) Uani d . 1
C C5 0.2224(4) 0.4546(3) -0.0102(4) 0.0482(8) Uani d . 1
H H5A 0.2834 0.5204 -0.0401 0.058 Uiso calc R 1
H H5B 0.1645 0.3999 -0.0975 0.058 Uiso calc R 1
C C6 0.0848(4) 0.5143(3) 0.0315(3) 0.0423(7) Uani d . 1
H H6 0.1214 0.5757 0.1072 0.051 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 0.0539(6) 0.0510(6) 0.0752(7) 0.0060(5) -0.0080(5) 0.0096(5)
S2 0.0453(5) 0.0386(5) 0.0609(6) 0.0024(4) 0.0084(4) -0.0093(4)
N1 0.0444(15) 0.0390(15) 0.0498(16) 0.0011(12) 0.0043(13) 0.0010(12)
C1 0.047(2) 0.079(3) 0.0443(19) 0.0019(19) 0.0060(16) -0.0029(19)
C2 0.084(3) 0.065(3) 0.074(3) -0.021(2) -0.003(2) -0.008(2)
C3 0.069(2) 0.041(2) 0.066(2) -0.0096(18) 0.0021(19) -0.0044(18)
C4 0.0328(15) 0.0423(17) 0.0396(16) 0.0024(13) 0.0119(13) -0.0014(13)
C5 0.0443(18) 0.053(2) 0.0400(17) -0.0015(15) 0.0094(14) -0.0040(15)
C6 0.0420(15) 0.0389(17) 0.0377(16) -0.0004(14) 0.0078(13) -0.0013(13)
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
_geom_angle_publ_flag
C4 S1 C1 . 100.59(17) ?
C4 S2 C5 . 101.36(16) ?
C4 N1 C3 . 121.5(3) ?
C2 C1 S1 . 111.5(3) ?
C2 C1 H1A . 109.3 ?
S1 C1 H1A . 109.3 ?
C2 C1 H1B . 109.3 ?
S1 C1 H1B . 109.3 ?
H1A C1 H1B . 108.0 ?
C1 C2 C3 . 116.2(4) ?
C1 C2 H2A . 108.2 ?
C3 C2 H2A . 108.2 ?
C1 C2 H2B . 108.2 ?
C3 C2 H2B . 108.2 ?
H2A C2 H2B . 107.4 ?
N1 C3 C2 . 117.7(3) ?
N1 C3 H3A . 107.9 ?
C2 C3 H3A . 107.9 ?
N1 C3 H3B . 107.9 ?
C2 C3 H3B . 107.9 ?
H3A C3 H3B . 107.2 ?
N1 C4 S2 . 122.3(2) ?
N1 C4 S1 . 129.3(3) yes
S1 C4 S2 . 108.36(18) yes
C6 C5 S2 . 113.6(2) ?
C6 C5 H5A . 108.8 ?
S2 C5 H5A . 108.8 ?
C6 C5 H5B . 108.8 ?
S2 C5 H5B . 108.8 ?
H5A C5 H5B . 107.7 ?
C6 C6 C5 3_565 124.5(4) ?
C6 C6 H6 3_565 117.8 ?
C5 C6 H6 . 117.8 ?
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 C4 . 1.771(3) yes
S1 C1 . 1.793(4) yes
S2 C4 . 1.768(3) yes
S2 C5 . 1.819(3) yes
N1 C4 . 1.252(4) yes
N1 C3 . 1.463(4) yes
C1 C2 . 1.468(6) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.482(6) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C5 C6 . 1.494(5) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C6 3_565 1.318(6) yes
C6 H6 . 0.9300 ?
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
C4 S1 C1 C2 . -35.0(4)
S1 C1 C2 C3 . 57.0(5)
C4 N1 C3 C2 . 17.3(6)
C1 C2 C3 N1 . -48.5(6)
C3 N1 C4 S2 . 179.0(3)
C3 N1 C4 S1 . -0.6(5)
C5 S2 C4 N1 . 3.7(3)
C5 S2 C4 S1 . -176.68(17)
C1 S1 C4 N1 . 9.4(4)
C1 S1 C4 S2 . -170.19(18)
C4 S2 C5 C6 . -77.0(3)
S2 C5 C6 C6 3_565 -115.0(4)
