Adducts of Thianthrene- and Phenoxathiin Cation Radical Salts with Symmetrical Alkynes. Structure and Formation of Cumulenes on Alumina Leading to α-Diketones, α-Hydroxyalkynes, and α-Acetamidoalkynes
Shine, Henry J.; Rangappa, Paramashivappa; Marx, John N.; Shelly, Dennis C.; Ould-Ely, Teyeb; Whitmire, Kenton H.; The Journal of Organic Chemistry 70 (2005) 3877–3883; doi:10.1021/jo050198b

data_4028892
_publ_section_title
;
 Adducts of Thianthrene- and Phenoxathiin Cation Radical Salts with
 Symmetrical Alkynes. Structure and Formation of Cumulenes on Alumina
 Leading to \a-Diketones, \a-Hydroxyalkynes, and \a-Acetamidoalkynes
;
_journal_issue                   10
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              3877
_journal_page_last               3883
_journal_paper_doi               10.1021/jo050198b
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C36 H36 B2 F8 N2 S4'
_chemical_formula_weight         798.53
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.531(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6373(16)
_cell_length_b                   18.901(3)
_cell_length_c                   11.2859(18)
_cell_measurement_reflns_used    1855
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.535
_cell_measurement_theta_min      4.312
_cell_volume                     1937.5(5)
_computing_cell_refinement       'SHELXTL 6.10, (Bruker AXS, 2001)'
_computing_data_collection       'SHELXTL 6.10, (Bruker AXS, 2001)'
_computing_data_reduction        'SHELXTL 6.10, (Bruker AXS, 2001)'
_computing_molecular_graphics    'SHELXTL 6.10, (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL 6.10, (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker AXS'
_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  0.1125
_diffrn_reflns_av_sigmaI/netI    0.1089
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9947
_diffrn_reflns_theta_full        24.78
_diffrn_reflns_theta_max         24.78
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.756835
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.0878
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2134
_refine_ls_wR_factor_ref         0.2444
_reflns_number_gt                1762
_reflns_number_total             3304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo050198bsup1.cif
_cod_data_source_block           "'4,5-bis_5-thianthreniumyl-4-octene_2BF4'"
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1937.5(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4028892