Au-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Isocyanoacetates with Maleimides
Silvia Padilla; Javier Adrio; Juan C. Carretero; Journal of Organic Chemistry 77 (2012) 4161–4166; doi:10.1021/jo3003425

data_4027158
_publ_section_title
;
 Au-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Isocyanoacetates
 with Maleimides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4161
_journal_page_last               4166
_journal_paper_doi               10.1021/jo3003425
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C22 H20 N2 O4 S'
_chemical_formula_weight         408.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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                 115.842(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9522(5)
_cell_length_b                   5.9178(2)
_cell_length_c                   14.1782(5)
_cell_measurement_temperature    100(2)
_cell_volume                     978.06(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10844
_diffrn_reflns_theta_full        27.32
_diffrn_reflns_theta_max         27.32
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4316
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0617P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                3665
_reflns_number_total             4316
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3003425_si_002.cif
_cod_data_source_block           datos_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4027158