Tertiary Aromatic Amide for Memory of Chirality: Access to Enantioenriched α-Substituted Valine
Mathieu Branca; Didier Gori; Régis Guillot; Valérie Alezra; Cyrille Kouklovsky; Journal of the American Chemical Society 130 (2008) 5864–5865; doi:10.1021/ja801165z

data_4107750
_publ_contact_author_address
;Laboratoire de Chimie des Proc\'ed\'es et Substances Naturelles, 
Institut de Chimie Mol\'eculaire et des Mat\'eriaux d?Orsay CNRS, UMR 8182
B\^at 410, Univ. Paris-Sud 
F-91405 Orsay, 
France
;
_publ_contact_author_email       valezra@icmo.u-psud.fr
_publ_contact_author_fax         '(+33) 1-6915-4679'
_publ_contact_author_name        'Val\'erie Alezra'
_publ_section_title
;
 Tertiary Aromatic Amide for Memory of Chirality: Access to
 Enantioenriched \a-Substituted Valine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5864
_journal_page_last               5865
_journal_paper_doi               10.1021/ja801165z
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 N O3'
_chemical_formula_sum            'C19 H21 N O3'
_chemical_formula_weight         311.37
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.7576(7)
_cell_length_b                   12.0196(7)
_cell_length_c                   24.3109(16)
_cell_measurement_reflns_used    8230
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      34.60
_cell_measurement_theta_min      2.41
_cell_volume                     3435.7(4)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            45680
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         34.80
_diffrn_reflns_theta_min         2.38
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         11308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.3790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                9574
_reflns_number_total             11308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja801165z-file001.cif
_cod_data_source_block           452GuillotICMMO
_cod_database_code               4107750