Design of novel chiral N,N,O-tridentate phenanthroline ligands and their application to enantioselective addition of organozinc reagents to aldehydes
Yuki Naganawa; Tomoya Namba; Tomotaka Aoyama; Kentaro Shoji; Hisao Nishiyama; Chem.Commun. 50 (2014) 13224–; doi:10.1039/C4cc05020G

data_7115844
_publ_section_title
;
 Design of novel chiral N,N,O-tridentate phenanthroline ligands and their
 application to enantioselective addition of organozinc reagents to
 aldehydes
;
_journal_name_full               Chem.Commun.
_journal_page_first              13224
_journal_paper_doi               10.1039/C4cc05020G
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_sum            'C39 H26 N2 O'
_chemical_formula_weight         534.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
_cell_angle_beta                 97.144(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8103(7)
_cell_length_b                   17.0401(15)
_cell_length_c                   20.5041(16)
_cell_measurement_temperature    93.(2)
_cell_volume                     2707.7(4)
_computing_data_collection       'Bruker SMART APEXII'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'General Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      93.(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'bruker d8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17382
_diffrn_reflns_theta_full        25.12
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_min         2.33
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
;
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.198
_refine_ls_abs_structure_details
;
Flack x determined using 2690 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     761
_refine_ls_number_reflns         8726
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0409P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                7057
_reflns_number_total             8726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc05020g2.cif
_cod_data_source_block           I
_cod_database_code               7115844
_shelx_res_checksum              86691
_shelx_hkl_checksum              59331