One-Point Binding Ligands for Asymmetric Gold Catalysis: Phosphoramidites with a TADDOL-Related but Acyclic Backbone
Henrik Teller; Matthieu Corbet; Luca Mantilli; Gopinadhanpillai Gopakumar; Richard Goddard; Walter Thiel; Alois Fürstner; Journal of the American Chemical Society 134 (2012) 15331–15342; doi:10.1021/ja303641p

data_4118616
_publ_section_title
;
 One-Point Binding Ligands for Asymmetric Gold Catalysis: Phosphoramidites
 with a TADDOL-Related but Acyclic Backbone
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15331
_journal_page_last               15342
_journal_paper_doi               10.1021/ja303641p
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        pentane/dichloromethane/acetonitrile
_chemical_formula_moiety         '4(C21 H21 N3 O7), C H2 Cl2, C2 H3 N'
_chemical_formula_sum            'C87 H89 Cl2 N13 O28'
_chemical_formula_weight         1835.61
_chemical_name_systematic
;
(3,5-dinitro)-(3-(2,2-dimethylvinyl)-4,6-dimethoxy-2,3-dihydroindolyl)methanone
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                COB-CB-069-01
_audit_creation_date             2012-04-13
_cell_angle_alpha                90.00
_cell_angle_beta                 122.791(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            1
_cell_length_a                   24.4670(11)
_cell_length_b                   7.0733(3)
_cell_length_c                   15.2093(7)
_cell_measurement_reflns_used    9084
_cell_measurement_temperature    100
_cell_measurement_theta_max      65.8578
_cell_measurement_theta_min      3.4568
_cell_volume                     2212.73(18)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30030
_diffrn_reflns_theta_full        66.47
_diffrn_reflns_theta_max         66.47
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7127
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1175P)^2^+2.8766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1712
_reflns_number_gt                3234
_reflns_number_total             3332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303641p_si_008.cif
_cod_data_source_block           7290
_cod_original_cell_volume        2212.73(17)
_cod_original_sg_symbol_Hall     'c 2y'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4118616