Highly Stereoselective Olefin Cyclopropanation of Diazooxindoles Catalyzed by a C2-Symmetric Spiroketal Bisphosphine/Au(I) Complex
Zhong-Yan Cao; Xiaoming Wang; Chen Tan; Xiao-Li Zhao; Jian Zhou; Kuiling Ding; Journal of the American Chemical Society 135 (2013) 8197–8200; doi:10.1021/ja4040895

data_4119873
_publ_section_title
;
 Highly Stereoselective Olefin Cyclopropanation of Diazooxindoles
 Catalyzed by a C2-Symmetric Spiroketal Bisphosphine/Au(I) Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8197
_journal_page_last               8200
_journal_paper_doi               10.1021/ja4040895
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H16 Br N O3 S'
_chemical_formula_weight         466.34
_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                 97.115(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4359(13)
_cell_length_b                   7.5627(11)
_cell_length_c                   27.646(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1957.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22087
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    2.232
_exptl_absorpt_correction_T_max  0.8416
_exptl_absorpt_correction_T_min  0.3957
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.605
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6705
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0965
_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^)+(0.1247P)^2^+10.8283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2647
_refine_ls_wR_factor_ref         0.2746
_reflns_number_gt                5486
_reflns_number_total             6705
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4040895_si_005.cif
_cod_data_source_block           z
_cod_database_code               4119873