Synthesis of Programmable Tetra-ortho-Substituted Biaryl Compounds Using Diels-Alder Cycloadditions/Cycloreversions of Disubstituted Alkynyl Stannanes
Johanna R. Perkins; Rich G. Carter; Journal of the American Chemical Society 130 (2008) 3290–3291; doi:10.1021/ja7113486

data_4107569
_publ_section_title
;
 Synthesis of Programmable Tetra-ortho-Substituted Biaryl Compounds Using
 Diels-Alder Cycloadditions/Cycloreversions of Disubstituted Alkynyl
 Stannanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3290
_journal_page_last               3291
_journal_paper_doi               10.1021/ja7113486
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C26 H20 Cl N O4'
_chemical_formula_weight         445.88
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.9150(10)
_cell_angle_beta                 97.1090(10)
_cell_angle_gamma                101.6470(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0105(7)
_cell_length_b                   10.8432(9)
_cell_length_c                   13.9873(12)
_cell_measurement_reflns_used    4517
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.65
_cell_volume                     1101.94(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  '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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12443
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.9368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4764
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0494P)^2^+0.6492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                4056
_reflns_number_total             4764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7113486-file005.cif
_cod_data_source_block           rc24
_cod_database_code               4107569