Enamides and Enesulfonamides as Nucleophiles: Formation of Complex Ring Systems through a Platinum(II)-Catalyzed Addition/Friedel-Crafts Pathway
Jennifer A. Kozak; Jennifer M. Dodd; Tyler J. Harrison; Katherine J. Jardine; Brian O. Patrick; Gregory R. Dake; Journal of Organic Chemistry 74 (2009) 6929–6935; doi:10.1021/jo901512m

data_4024868
_publ_section_title
;
Enamides and Enesulfonamides as Nucleophiles: Formation of Complex Ring
Systems through a Platinum(II)-Catalyzed Addition/Friedel-Crafts Pathway
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6929
_journal_page_last               6935
_journal_paper_doi               10.1021/jo901512m
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C25 H27 N O3'
_chemical_formula_weight         389.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 107.540(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6061(3)
_cell_length_b                   26.6832(9)
_cell_length_c                   8.2419(3)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.59
_cell_volume                     2014.36(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            27626
_diffrn_reflns_theta_full        28.15
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.7402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                4128
_reflns_number_total             4910
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901512m_si_004.cif
_cod_data_source_block           gd032
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024868