Gold(I)-Catalyzed Enantioselective Ring Expansion of Allenylcyclopropanols
Florian Kleinbeck; F. Dean Toste; Journal of the American Chemical Society 131 (2009) 9178–9179; doi:10.1021/ja904055z

data_4104660
_publ_section_title
;
 Gold(I)-Catalyzed Enantioselective Ring Expansion of
 Allenylcyclopropanols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9178
_journal_page_last               9179
_journal_paper_doi               10.1021/ja904055z
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H19 Br N2 O2 S'
_chemical_formula_sum            'C19 H19 Br N2 O2 S'
_chemical_formula_weight         419.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.887(2)
_cell_angle_beta                 95.475(2)
_cell_angle_gamma                105.025(2)
_cell_formula_units_Z            20
_cell_length_a                   17.580(2)
_cell_length_b                   22.673(3)
_cell_length_c                   27.942(4)
_cell_measurement_reflns_used    8317
_cell_measurement_temperature    129(2)
_cell_measurement_theta_max      21.51
_cell_measurement_theta_min      2.63
_cell_volume                     9579(2)
_computing_cell_refinement       'Bruker APEX2 v 2009.3'
_computing_data_collection       'Bruker APEX2 v 2009.3'
_computing_data_reduction        'Bruker APEX2 v 2009.3'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      129(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0917
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            68460
_diffrn_reflns_theta_full        21.97
_diffrn_reflns_theta_max         21.97
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    2.269
_exptl_absorpt_correction_T_max  0.6024
_exptl_absorpt_correction_T_min  0.5301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             4280
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     4558
_refine_ls_number_reflns         44324
_refine_ls_number_restraints     3142
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1535
_reflns_number_gt                24694
_reflns_number_total             44324
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja904055z_si_002.cif
_cod_data_source_block           toste5bs
_cod_original_sg_symbol_H-M      'P 1 '
_cod_database_code               4104660