Controlling Axial Conformation in 2-Arylpyridines and 1-Arylisoquinolines: Application to the Asymmetric Synthesis of QUINAP by Dynamic Thermodynamic Resolution
Jonathan Clayden; Stephen P. Fletcher; Joseph J. W. McDouall; Stephen J. M. Rowbottom; Journal of the American Chemical Society 131 (2009) 5331–5343; doi:10.1021/ja900722q

data_4104177
_publ_section_title
;
 Controlling Axial Conformation in 2-Arylpyridines and
 1-Arylisoquinolines: Application to the Asymmetric Synthesis of QUINAP by
 Dynamic Thermodynamic Resolution
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5331
_journal_page_last               5343
_journal_paper_doi               10.1021/ja900722q
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C26 H19 N O S'
_chemical_formula_weight         393.48
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.159(3)
_cell_angle_beta                 95.365(2)
_cell_angle_gamma                106.548(2)
_cell_formula_units_Z            4
_cell_length_a                   10.5676(18)
_cell_length_b                   13.375(2)
_cell_length_c                   15.023(3)
_cell_measurement_reflns_used    951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.55
_cell_volume                     1953.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15602
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1049
_refine_ls_number_reflns         13884
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.4464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                13644
_reflns_number_total             13884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja900722q_si_001.cif
_cod_data_source_block           z:\s2797\work\s2797abs
_cod_original_sg_symbol_H-M      P1
_cod_database_code               4104177