Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)
Dautel, Olivier J.; Larsen, Jan; Fourmigué, Marc; Chemical Communications  (2000) 1117–; doi:10.1039/b001996h

data_7110922
_publ_section_title
;
 Electrophilic halogenation of thioethers: 5-chloro- and
 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an
 efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)
;
_journal_issue                   13
_journal_name_full               'Chemical Communications'
_journal_page_first              1117
_journal_paper_doi               10.1039/b001996h
_journal_year                    2000
_chemical_formula_sum            'C5 H2 Cl2 O S4'
_chemical_formula_weight         277.21
_chemical_melting_point          157
_chemical_name_common            dichloroethylendithiolone
_chemical_name_systematic
; 
5,6-Dichloro-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2one 
;
_space_group_IT_number           59
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2a'
_symmetry_space_group_name_H-M   'P m m n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.0595(21)
_cell_length_b                   7.4252(20)
_cell_length_c                   9.3827(22)
_cell_measurement_reflns_used    1365
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.75
_cell_volume                     491.8(2)
_computing_cell_refinement       'SELECT, CELL [STOE-IPDS]'
_computing_data_collection       'EXPOSE [STOE-IPDS]'
_computing_data_reduction        'INTEGRATE [STOE-IPDS]'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  STOE-IPDS
_diffrn_measurement_method       'Oscillation, Phi incr.= 2.5'
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2833
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    1.456
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_correction_T_min  0.7715
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'FACEIT, STOE-IPDS'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.875
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.0192
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.816
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     42
_refine_ls_number_reflns         558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.816
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                323
_reflns_number_total             558
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001996hsup1.cif
_cod_data_source_block           dop176me
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        491.8(4)
_cod_original_sg_symbol_H-M      Pmmn
_cod_database_code               7110922