Enantioselective carbenoid insertion into phenolic O-H bonds with a chiral copper(I) imidazoindolephosphine complex.
Osako, Takao; Panichakul, Duanghathai; Uozumi, Yasuhiro; Organic letters 14 (2012) 194–197; doi:10.1021/ol202977j

data_1503511
_publ_section_title
;
 Enantioselective carbenoid insertion into phenolic O-H bonds with a
 chiral copper(I) imidazoindolephosphine complex.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              194
_journal_page_last               197
_journal_paper_doi               10.1021/ol202977j
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C64 H80 Cl2 Cu2 N4 O3 P2'
_chemical_formula_sum            'C64 H80 Cl2 Cu2 N4 O3 P2'
_chemical_formula_weight         1213.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.158(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   15.131(8)
_cell_length_b                   11.066(5)
_cell_length_c                   19.286(9)
_cell_measurement_reflns_used    10528
_cell_measurement_temperature    153
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.13
_cell_volume                     3168(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      153
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23442
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1276.00
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_platon_squeeze_details
;
;
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.487
_refine_ls_extinction_coef       267(169)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     775
_refine_ls_number_reflns         7232
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0114Fo^2^ + 1.0000\s(Fo^2^)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                7105
_reflns_number_total             7265
_reflns_threshold_expression     F>2.0\s(F)
_cod_data_source_file            ol202977j_si_003.cif
_cod_data_source_block           '_chiral2'
_cod_database_code               1503511