Evidence for Effective p(Z)-π(Ar) Conjugations (Z = S, Se, and Te, as Well as Z = O) in 9-(Arylchalcogenyl)triptycenes: Experimental and Theoretical Investigations
Satoko Hayashi; Takashi Nakamoto; Mao Minoura; Waro Nakanishi; Journal of Organic Chemistry 74 (2009) 4763–4771; doi:10.1021/jo900488r

data_4024624
_publ_section_title
;
Evidence for Effective p(Z)-\p(Ar) Conjugations (Z = S, Se, and Te, as
Well as Z = O) in 9-(Arylchalcogenyl)triptycenes: Experimental and
Theoretical Investigations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4763
_journal_page_last               4771
_journal_paper_doi               10.1021/jo900488r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C26 H17 N O2 S'
_chemical_formula_weight         407.47
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   8.0498(4)
_cell_length_b                   14.0184(7)
_cell_length_c                   34.4239(17)
_cell_measurement_reflns_used    5421
_cell_measurement_temperature    233
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.46
_cell_volume                     3884.6(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233
_diffrn_detector_area_resol_mean 8.333
_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       'phi and omega 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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0101
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            40776
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9628
_exptl_absorpt_correction_T_min  0.9276
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0674P)^2^+2.9785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                4117
_reflns_number_total             4450
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900488r_si_005.cif
_cod_data_source_block           2j
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4024624