Electrochemical and Chemical Oxidation of Dithia-, Diselena-, Ditellura-, Selenathia-, and Tellurathiamesocycles and Stability of the Oxidized Species
Dennis H. Evans; Nadine E. Gruhn; Jin Jin; Bo Li; Edward Lorance; Noriko Okumura; Norma A. Macías-Ruvalcaba; Uzma I. Zakai; Shao-Zhong Zhang; Eric Block; Richard S. Glass; Journal of Organic Chemistry 75 (2010) 1997–2009; doi:10.1021/jo9026484

data_4025308
_publ_section_title
;
 Electrochemical and Chemical Oxidation of Dithia-, Diselena-, Ditellura-,
 Selenathia-, and Tellurathiamesocycles and Stability of the Oxidized
 Species
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1997
_journal_page_last               2009
_journal_paper_doi               10.1021/jo9026484
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety
'[(Se (CH2)6 S)2 ((C6F5)3BOH)2]((C6F5)3BOH2)2'
_chemical_formula_sum            'C84 H30 B4 F60 O4 S2 Se2'
_chemical_formula_weight         2508.36
_chemical_melting_point          ?
_chemical_name_systematic
; 
 1,1'-Bis-5-thio-1-selenocanium Bis(B-hydroxy-tris[pentafluorophenyl)boron 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.8930(10)
_cell_angle_beta                 93.1830(10)
_cell_angle_gamma                93.9430(10)
_cell_formula_units_Z            1
_cell_length_a                   12.5471(7)
_cell_length_b                   12.9889(7)
_cell_length_c                   14.0208(7)
_cell_measurement_reflns_used    8938
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.20
_cell_volume                     2196.7(2)
_computing_cell_refinement       'SMART, SAINT'
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXP-93 (Sheldrick, 1993)'
_computing_publication_material  'SHELXCIF-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide \w exposures'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18751
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count na
_diffrn_standards_interval_time  na
_diffrn_standards_number         'none (area detector data)'
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_correction_T_min  0.7326
_exptl_absorpt_correction_type   'multi-scan (SADABS)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1226
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     712
_refine_ls_number_reflns         9378
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0697P)^2^+0.8289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                7294
_reflns_number_total             9378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9026484_si_002.cif
_cod_data_source_block           ([(1d)2]2+[HOB(C6F5)3-]2)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

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_database_code               4025308