Mono- and Dicarbonyl-Bridged Tricyclic Heterocyclic Acceptors: Synthesis and Electronic Properties
Yulia A. Getmanenko; Chad Risko; Paul Tongwa; Eung-Gun Kim; Hong Li; Bhupinder Sandhu; Tatiana Timofeeva; Jean-Luc Brédas; Seth R. Marder; Journal of Organic Chemistry 76 (2011) 2660–2671; doi:10.1021/jo102502u

data_4026197
_publ_section_title
;
 Mono- and Dicarbonyl-Bridged Tricyclic Heterocyclic Acceptors: Synthesis
 and Electronic Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2660
_journal_page_last               2671
_journal_paper_doi               10.1021/jo102502u
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C25 H42 N2 O S2 Si2'
_chemical_formula_sum            'C25 H42 N2 O S2 Si2'
_chemical_formula_weight         506.91
_chemical_name_common
;
  2,6-Bis(triisopropylsilyl)-cyclopenta[2,1-b;3,4-b']dithiazole-4-one
;
_chemical_name_systematic
;
  2,6-Bis(triisopropylsilyl)-cyclopenta[2,1-b;3,4-b']dithiazole-4-one
;
_space_group_IT_number           114
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_atom_sites_solution_hydrogens   mixed
_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            4
_cell_length_a                   14.4658(19)
_cell_length_b                   14.4658(19)
_cell_length_c                   13.4820(18)
_cell_measurement_reflns_used    3685
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.82
_cell_volume                     2821.2(6)
_computing_cell_refinement       'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0781
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32630
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.9713
_exptl_absorpt_correction_T_min  0.9171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.36(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0587P)^2^+1.2890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                2527
_reflns_number_total             2771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102502u_si_002.cif
_cod_data_source_block           str1
_cod_database_code               4026197