Iridium-Catalyzed [3 + 2] Annulation of 1,3-Dienes with ortho-Carbonylated Phenylboronic Acids. A Catalytic Process Involving Regioselective 1,2-Addition
Takahiro Nishimura; Yuichi Yasuhara; Tamio Hayashi; Journal of the American Chemical Society 129 (2007) 7506–7507; doi:10.1021/ja072369v

data_4109548
_publ_section_title
;
 Iridium-Catalyzed [3 + 2] Annulation of 1,3-Dienes with
 ortho-Carbonylated Phenylboronic Acids. A Catalytic Process Involving
 Regioselective 1,2-Addition
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7506
_journal_page_last               7507
_journal_paper_doi               10.1021/ja072369v
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 96.172(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.133(7)
_cell_length_b                   5.250(3)
_cell_length_c                   16.352(8)
_cell_measurement_reflns_used    8435
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1206.3(11)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11275
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0587P)^2^+0.5172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                2264
_reflns_number_total             2750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja072369vsi20070412_022128.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1206.3(12)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4109548