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_4026417
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H18 O S'
_chemical_formula_sum            'C20 H18 O S'
_chemical_formula_weight         306.40
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 115.0650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0201(5)
_cell_length_b                   9.6539(6)
_cell_length_c                   9.7094(6)
_cell_measurement_reflns_used    5539
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.32
_cell_volume                     765.86(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7907
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0501P)^2^+0.0782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                3636
_reflns_number_total             3713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200664m_si_002.cif
_cod_data_source_block           ijf0722m
_cod_database_code               4026417