Enantioselective Cyclopropenation of Alkynes with Acceptor/Acceptor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis
Xin Cui; Xue Xu; Hongjian Lu; Shifa Zhu; Lukasz Wojtas; X. Peter Zhang; Journal of the American Chemical Society 133 (2011) 3304–3307; doi:10.1021/ja111334j

data_4105759
_publ_section_title
;
 Enantioselective Cyclopropenation of Alkynes with
 Acceptor/Acceptor-Substituted Diazo Reagents via Co(II)-Based
 Metalloradical Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3304
_journal_page_last               3307
_journal_paper_doi               10.1021/ja111334j
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H14 Br N O2'
_chemical_formula_sum            'C15 H14 Br N O2'
_chemical_formula_weight         320.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        '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                   5.7660(1)
_cell_length_b                   13.9219(2)
_cell_length_c                   18.1101(2)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.85
_cell_measurement_theta_min      4.005
_cell_volume                     1453.76(4)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_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 0.998
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18467
_diffrn_reflns_theta_full        67.40
_diffrn_reflns_theta_max         67.40
_diffrn_reflns_theta_min         4.00
_exptl_absorpt_coefficient_mu    3.835
_exptl_absorpt_correction_T_max  0.5970
_exptl_absorpt_correction_T_min  0.3092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1063 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.022(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0208
_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^)+(0.0250P)^2^+0.4794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0525
_reflns_number_gt                2578
_reflns_number_total             2596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja111334j_si_003.cif
_cod_data_source_block           3df
_cod_database_code               4105759