Chirality Sensing of Amines, Diamines, Amino Acids, Amino Alcohols, and α-Hydroxy Acids with a Single Probe
Keith W. Bentley; Yea G. Nam; Jaslynn M. Murphy; Christian Wolf; Journal of the American Chemical Society 135 (2013) 18052–18055; doi:10.1021/ja410428b

data_4121255
_publ_contact_author             'Christian Wolf'
_publ_contact_author_email       cw27@georgetown.edu
_publ_section_title
;
 Chirality Sensing of Amines, Diamines, Amino Acids, Amino Alcohols, and
 \a-Hydroxy Acids with a Single Probe
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18052
_journal_page_last               18055
_journal_paper_doi               10.1021/ja410428b
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C70 H61 N4 O4.5 Zn2'
_chemical_formula_sum            'C70 H61 N4 O4.5 Zn2'
_chemical_formula_weight         1160.96
_chemical_name_common            '[2,2-binaphthol]'
_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                85.326(2)
_cell_angle_beta                 78.118(2)
_cell_angle_gamma                78.408(2)
_cell_formula_units_Z            2
_cell_length_a                   12.5034(16)
_cell_length_b                   14.2812(18)
_cell_length_c                   16.244(2)
_cell_measurement_reflns_used    5782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.268
_cell_measurement_theta_min      2.316
_cell_volume                     2778.1(6)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker APEXII'
_computing_molecular_graphics
'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565'
_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 0.952
_diffrn_measured_fraction_theta_max 0.952
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32793
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.9136
_exptl_absorpt_correction_T_min  0.7154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS based on Blessing's method; Blessing, Act Cryst. (1995) A51 33-38'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             1210
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.985
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.963(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1452
_refine_ls_number_reflns         24379
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0862P)^2^+0.7497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1760
_reflns_number_gt                17475
_reflns_number_total             24379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja410428b_si_003.cif
_cod_data_source_block           Katie_ligand
_cod_original_formula_sum        'C35 H30.50 N2 O2.25 Zn'
_cod_database_code               4121255