Oxazinanones as chiral auxiliaries: synthesis and evaluation in enolate alkylations and aldol reactions.
Davies, Stephen G.; Garner, A. Christopher; Roberts, Paul M.; Smith, Andrew D.; Sweet, Miles J.; Thomson, James E.; Organic & biomolecular chemistry 4 (2006) 2753–2768; doi:10.1039/b604073j

data_7151234
_publ_section_title
;
 Oxazinanones as chiral auxiliaries: synthesis and evaluation in
 enolate alkylations and aldol reactions.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2753
_journal_page_last               2768
_journal_paper_doi               10.1039/b604073j
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H29 N1 O4'
_chemical_formula_sum            'C16 H29 N O4'
_chemical_formula_weight         299.41
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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
_audit_creation_date             04-18-08
_audit_creation_method           CRYSTALS_ver_12-03-99
_cell_angle_alpha                89.749(2)
_cell_angle_beta                 79.982(2)
_cell_angle_gamma                64.9723(11)
_cell_formula_units_Z            2
_cell_length_a                   8.8735(2)
_cell_length_b                   9.7635(3)
_cell_length_c                   11.2480(3)
_cell_measurement_reflns_used    3610
_cell_measurement_temperature    190
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     866.90(4)
_computing_cell_refinement
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
COLLECT (Nonius BV, 1997)
;
_computing_data_reduction
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_molecular_graphics
;
CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al 2001)
;
_computing_structure_solution
;
USER DEFINED STRUCTURE SOLUTION
;
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
;
Enraf Nonius Kappa CCD
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.01
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7230
_diffrn_reflns_theta_full        24.873
_diffrn_reflns_theta_max         27.408
_diffrn_reflns_theta_min         5.109
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       ' plate '
_exptl_crystal_F_000             328.000
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1334
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         3145
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000145
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method = Prince modified Chebychev polynomial, (Watkin, 1994)
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

0.647 0.842E-01 0.320
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0482
_refine_ls_wR_factor_gt          0.0380
_refine_ls_wR_factor_ref         0.0380
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3145
_reflns_number_total             3878
_reflns_threshold_expression     I>2.00u(I)
_cod_data_source_file            b604073j.txt
_cod_data_source_block           compound_3
_cod_original_formula_sum        'C16 H29 N1 O4'
_cod_database_code               7151234