Asymmetric Copper(I)-Catalyzed Azide-Alkyne Cycloaddition to Quaternary Oxindoles
Feng Zhou; Chen Tan; Jing Tang; Yan-Yan Zhang; Wei-Ming Gao; Hai-Hong Wu; Yi-Hua Yu; Jian Zhou; Journal of the American Chemical Society 135 (2013) 10994–10997; doi:10.1021/ja4066656

data_4120233
_publ_section_title
;
 Asymmetric Copper(I)-Catalyzed Azide-Alkyne Cycloaddition to Quaternary
 Oxindoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10994
_journal_page_last               10997
_journal_paper_doi               10.1021/ja4066656
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H23 Cl N4 O2'
_chemical_formula_weight         482.95
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.846(12)
_cell_length_b                   13.173(6)
_cell_length_c                   7.666(4)
_cell_measurement_temperature    296(2)
_cell_volume                     2509(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1434
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28782
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.9605
_exptl_absorpt_correction_T_min  0.9166
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0890P)^2^+1.2403P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                3374
_reflns_number_total             4406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4066656_si_004.cif
_cod_data_source_block           z
_cod_database_code               4120233