Catalytic Kinetic Resolution of Cyclic Secondary Amines
Michael Binanzer; Sheng-Ying Hsieh; Jeffrey W. Bode; Journal of the American Chemical Society 133 (2011) 19698–19701; doi:10.1021/ja209472h

data_4107205
_publ_contact_author_email       schweizer@org.chem.ethz.ch
_publ_contact_author_name        'B. Schweizer'
_publ_section_title
;
 Catalytic Kinetic Resolution of Cyclic Secondary Amines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19698
_journal_page_last               19701
_journal_paper_doi               10.1021/ja209472h
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C11 H11 N O3'
_chemical_formula_sum            'C11 H11 N O3'
_chemical_formula_weight         205.22
_chemical_name_systematic
; 
 (4aR,9aS)-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one 
;
_chemical_temperature_decomposition 483
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6161(4)
_cell_length_b                   10.4035(8)
_cell_length_c                   19.2977(13)
_cell_measurement_reflns_used    370
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      53.03
_cell_measurement_theta_min      4.58
_cell_volume                     926.74(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Platon, Ortep'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement
'OLEX2 (Dolomanov, 2009), SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2652
_diffrn_reflns_theta_full        59.99
_diffrn_reflns_theta_max         59.99
_diffrn_reflns_theta_min         4.58
_exptl_absorpt_coefficient_mu    0.899
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.794
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         1334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.794
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                1001
_reflns_number_total             1334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja209472h_si_002.cif
_cod_data_source_block           cu_jb180511_0m
_cod_database_code               4107205