#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203265.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_2203265
loop_
_publ_author_name
'Brewer, A. David'
'Ferguson, George'
'Lough, Alan J.'
'Strunk, Richard J.'
_publ_section_title
;
 2,3-Dihydro-5,6-dimethyl-1,4-dithiine 1,1,4-trioxide
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o392
_journal_page_last               o394
_journal_paper_doi               10.1107/S1600536804003356
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C6 H10 O3 S2'
_chemical_formula_moiety         'C6 H10 O3 S2'
_chemical_formula_sum            'C6 H10 O3 S2'
_chemical_formula_weight         194.28
_chemical_name_systematic        ?
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.5919(5)
_cell_length_b                   9.2507(10)
_cell_length_c                   7.9146(9)
_cell_measurement_reflns_used    761
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      2.57
_cell_volume                     409.41(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLATON (Spek, 2002)'
_computing_publication_material
'SHELXL97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3121
_diffrn_reflns_theta_full        25.45
_diffrn_reflns_theta_max         25.45
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.288
_refine_ls_abs_structure_details 'Flack (1983), 287 Friedel pairs'
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.09(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0563P)²+0.467P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                672
_reflns_number_total             761
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6407.cif
_cod_data_source_block           I
_cod_database_code               2203265
_cod_database_fobs_code          2203265
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
loop_
_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_type_symbol
S1 0.7090(2) 0.36431(15) 0.80083(19) 0.0466(5) Uani d . 1 S
O1 0.9651(13) 0.3655(11) 0.7621(11) 0.073(3) Uani d P 0.50 O
O2 0.5815(9) 0.2289(4) 0.8227(6) 0.0657(14) Uani d . 1 O
C1 0.5848(9) 0.4496(5) 0.6167(7) 0.0388(13) Uani d . 1 C
C2 0.6317(10) 0.4823(6) 0.9686(7) 0.0470(14) Uani d . 1 C
C3 0.6853(14) 0.3898(7) 0.4581(8) 0.0669(18) Uani d . 1 C
H2A 0.6747 0.4365 1.0775 0.056 Uiso calc R 1 H
H2B 0.7249 0.5729 0.9581 0.056 Uiso calc R 1 H
H3A 0.5545 0.3604 0.3832 0.100 Uiso calc R 1 H
H3B 0.7852 0.3057 0.4843 0.100 Uiso calc R 1 H
H3C 0.7826 0.4637 0.4020 0.100 Uiso calc R 1 H
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 0.0502(8) 0.0419(8) 0.0476(8) 0.0083(6) -0.0123(6) -0.0111(6)
O1 0.030(3) 0.103(7) 0.085(6) 0.023(4) -0.020(4) -0.053(6)
O2 0.096(4) 0.037(2) 0.064(3) 0.0007(19) -0.029(3) 0.005(2)
C1 0.044(3) 0.038(3) 0.035(3) 0.001(2) 0.000(2) -0.010(2)
C2 0.069(4) 0.043(3) 0.029(2) 0.007(3) -0.014(2) -0.007(2)
C3 0.089(5) 0.065(4) 0.047(3) -0.001(4) 0.014(3) -0.020(3)
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'
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'
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
O1 S1 O2 . 120.8(5) yes
O1 S1 C1 . 101.8(4) yes
O1 S1 C2 . 113.0(4) yes
O2 S1 C1 . 106.6(3) yes
O2 S1 C2 . 108.8(3) yes
C1 S1 C2 . 104.1(2) yes
C1 C1 S1 2_665 125.70(16) yes
C1 C1 C3 2_665 122.2(4) yes
C3 C1 S1 . 112.1(4) yes
C2 C2 S1 2_665 111.8(4) yes
C2 C2 H2A 2_665 109.3 no
S1 C2 H2A . 109.3 no
C2 C2 H2B 2_665 109.3 no
S1 C2 H2B . 109.3 no
H2A C2 H2B . 107.9 no
C1 C3 H3A . 109.5 no
C1 C3 H3B . 109.5 no
H3A C3 H3B . 109.5 no
C1 C3 H3C . 109.5 no
H3A C3 H3C . 109.5 no
H3B C3 H3C . 109.5 no
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 O1 . 1.464(8) yes
S1 O2 . 1.451(5) yes
S1 C1 . 1.797(5) yes
S1 C2 . 1.772(5) yes
C1 C1 2_665 1.330(10) yes
C1 C3 . 1.482(7) yes
C2 C2 2_665 1.509(11) yes
C2 H2A . 0.99 no
C2 H2B . 0.99 no
C3 H3A . 0.98 no
C3 H3B . 0.98 no
C3 H3C . 0.98 no
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 H2B O1 2_765 0.99 2.40 3.120(10) 130 yes
C2 H2B O2 4_657 0.99 2.50 3.241(7) 131 yes
C3 H3A O1 3_456 0.98 2.44 3.183(11) 133 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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 C1 C1 2_665 96.5(7) no
O1 S1 C1 C1 2_665 -136.1(7) no
C2 S1 C1 C1 2_665 -18.5(8) no
O2 S1 C1 C3 . -80.8(5) no
O1 S1 C1 C3 . 46.7(6) no
C2 S1 C1 C3 . 164.3(4) no
O2 S1 C2 C2 2_665 -62.0(5) no
O1 S1 C2 C2 2_665 160.9(6) no
C1 S1 C2 C2 2_665 51.3(6) no
