Stereoselective Rhodium-Catalyzed [3 + 2 + 1] Carbocyclization of Alkenylidenecyclopropanes with Carbon Monoxide: Theoretical Evidence for a Trimethylenemethane Metallacycle Intermediate
Shivnath Mazumder; Deju Shang; Daniela E. Negru; Mu-Hyun Baik; P. Andrew Evans; Journal of the American Chemical Society 134 (2012) 20569–20572; doi:10.1021/ja305467x

data_4119032
_publ_section_title
;
 Stereoselective Rhodium-Catalyzed [3 + 2 + 1] Carbocyclization of
 Alkenylidenecyclopropanes with Carbon Monoxide: Theoretical Evidence for
 a Trimethylenemethane Metallacycle Intermediate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20569
_journal_page_last               20572
_journal_paper_doi               10.1021/ja305467x
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C16 H19 N O3 S'
_chemical_formula_weight         305.38
_chemical_name_common            DJS01
_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                 92.492(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2766(12)
_cell_length_b                   7.5631(11)
_cell_length_c                   23.141(3)
_cell_measurement_reflns_used    3460
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1447.2(4)
_computing_cell_refinement       'SAINT v6.45a (Bruker, 2005)'
_computing_data_collection       'SMART v.5.632 (Bruker, 2005)'
_computing_data_reduction        'SAINT v6.45a (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX detector'
_diffrn_measurement_method       '\w scans with a narrow frame width'
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8135
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008-1 (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0530P)^2^+0.4646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                2608
_reflns_number_total             3060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305467x_si_001.cif
_cod_data_source_block           djs01
_cod_database_code               4119032