3,3'-Diphosphoryl-1,1'-bi-2-naphthol-Zn(II) Complexes as Conjugate Acid-Base Catalysts for Enantioselective Dialkylzinc Addition to Aldehydes
Manabu Hatano; Takashi Miyamoto; Kazuaki Ishihara; Journal of Organic Chemistry 71 (2006) 6474–6484; doi:10.1021/jo060908t

data_4021897
_publ_section_title
;
 3,3'-Diphosphoryl-1,1'-bi-2-naphthol-Zn(II) Complexes as Conjugate
 Acid-Base Catalysts for Enantioselective Dialkylzinc Addition to Aldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6474
_journal_page_last               6484
_journal_paper_doi               10.1021/jo060908t
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C44 H32 O4 P2'
_chemical_formula_weight         686.64
_chemical_name_common            (R)-3,3'-bis(diphenylphosphinoyl)-BINOL
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.282(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            12
_cell_length_a                   10.709(5)
_cell_length_b                   18.515(5)
_cell_length_c                   53.426(5)
_cell_measurement_temperature    173(2)
_cell_volume                     10593(6)
_computing_cell_refinement       'Bruker SMART APEX'
_computing_data_collection       'Bruker SMART APEX'
_computing_data_reduction        'Bruker SMART APEX'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  'ORTEP 3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'omega mode '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       73
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            40115
_diffrn_reflns_theta_full        29.31
_diffrn_reflns_theta_max         29.31
_diffrn_reflns_theta_min         0.76
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SMART APEX'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4296
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1375
_refine_ls_number_reflns         25528
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.061
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+6.5856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                21519
_reflns_number_total             25528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060908tsi20060503_011655.cif
_cod_depositor_comments
;

2020-12-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C264 H192 O24 P12'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     4119.82
_cod_database_code               4021897