The dithiolene ligand and tetrathiafulvalene precursor molecules 4,5-bis(bromomethyl)-1,3-dithiol-2-one and 4,5-bis[(dihydroxyphosphoryl)methyl]-1,3-dithiol-2-one
Arumugam, Kuppuswamy; Clark, Daniel Seth; Mague, Joel T.; Donahue, James P.; Acta Crystallographica Section C 67 (2011) o446–o449; doi:10.1107/S0108270111040431

data_2018285
_publ_section_title
;
 The dithiolene ligand and tetrathiafulvalene precursor molecules
 4,5-bis(bromomethyl)-1,3-dithiol-2-one and
 4,5-bis[(dihydroxyphosphoryl)methyl]-1,3-dithiol-2-one
;
_journal_coeditor_code           FN3090
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o446
_journal_page_last               o449
_journal_paper_doi               10.1107/S0108270111040431
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H4 Br2 O S2'
_chemical_formula_moiety         'C5 H4 Br2 O S2'
_chemical_formula_sum            'C5 H4 Br2 O S2'
_chemical_formula_weight         304.02
_chemical_name_systematic
;
4,5-bis(bromomethyl)-1,3-dithiol-2-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.8360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9026(15)
_cell_length_b                   7.8804(8)
_cell_length_c                   7.4012(7)
_cell_measurement_reflns_used    3880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      2.83
_cell_volume                     840.21(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008<i>a</i>)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008<i>a</i>)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008<i>a</i>)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008<i>a</i>)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7166
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    10.072
_exptl_absorpt_correction_T_max  0.4642
_exptl_absorpt_correction_T_min  0.3066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008<i>b</i>)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.403
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         1062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0164
_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/[\s^2^(Fo^2^)+(0.0223P)^2^+0.8485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0435
_reflns_number_gt                1005
_reflns_number_total             1062
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fn3090.cif
_cod_data_source_block           I
_cod_original_cell_volume        840.20(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018285
_cod_database_fobs_code          2018285