Regiochemistry in Cobalt-Mediated Intermolecular Pauson-Khand Reactions of Unsymmetrical Internal Heteroaromatic Alkynes with Norbornene
Benjamin E. Moulton; Adrian C. Whitwood; Anne K. Duhme-Klair; Jason M. Lynam; Ian J. S. Fairlamb; Journal of Organic Chemistry 76 (2011) 5320–5334; doi:10.1021/jo200664m

data_4026420
_publ_section_title
;
 Regiochemistry in Cobalt-Mediated Intermolecular Pauson-Khand Reactions
 of Unsymmetrical Internal Heteroaromatic Alkynes with Norbornene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5320
_journal_page_last               5334
_journal_paper_doi               10.1021/jo200664m
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C21 H19 N O'
_chemical_formula_sum            'C21 H19 N O'
_chemical_formula_weight         301.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.111(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2352(10)
_cell_length_b                   10.6341(13)
_cell_length_c                   17.786(2)
_cell_measurement_reflns_used    2179
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      24.79
_cell_measurement_theta_min      2.23
_cell_volume                     1553.6(3)
_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, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11921
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03;(Sheldrick)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0476P)^2^+0.4776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                1982
_reflns_number_total             2729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200664m_si_005.cif
_cod_data_source_block           ijf0730m
_cod_database_code               4026420