Novel preparation of non-racemic 1-[??-(1-azacycloalkyl)benzyl]-2-naphthols from Betti base and their application as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes
Lu, Jun; Xu, Xuenong; Wang, Shaozhong; Wang, Cunde; Hu, Yuefei; Hu, Hongwen; Journal of the Chemical Society, Perkin Transactions 1  (2002) 2900–; doi:10.1039/b204534f

data_7204450
_publ_section_title
;
 Novel preparation of non-racemic
 1-[??-(1-azacycloalkyl)benzyl]-2-naphthols from Betti base and their
 application as chiral ligands in the asymmetric addition of
 diethylzinc to aryl aldehydes
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2900
_journal_paper_doi               10.1039/b204534f
_journal_year                    2002
_chemical_formula_sum            'C22 H20 N O'
_chemical_formula_weight         314.39
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.813(4)
_cell_length_b                   10.354(3)
_cell_length_c                   16.491(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14.60
_cell_measurement_theta_min      11.12
_cell_volume                     1675.5(9)
_computing_cell_refinement       'CAD4, Enraf-Nonius'
_computing_data_collection       'CAD4, Enraf-Nonius'
_computing_molecular_graphics    'ORTEP-3 for Windows V1.05(Farrugia, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       'omega/2-theta 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2135
_diffrn_reflns_theta_full        27.17
_diffrn_reflns_theta_max         27.17
_diffrn_reflns_theta_min         2.32
_diffrn_standards_interval_time  3600
_diffrn_standards_number         100
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_type   'North, Phillips & Mathews, 1968'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(3)
_refine_ls_extinction_coef       0.0143(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.2770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                1384
_reflns_number_total             2135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b204534f.txt
_cod_data_source_block           lu0112
_cod_database_code               7204450