Asymmetric Induction during Yang Cyclization of α-Oxoamides: The Power of a Covalently Linked Chiral Auxiliary Is Enhanced in the Crystalline State
Arunkumar Natarajan; Joel T. Mague; V. Ramamurthy; Journal of the American Chemical Society 127 (2005) 3568–3576; doi:10.1021/ja043999p

data_4111527
_publ_section_title
;
 Asymmetric Induction during Yang Cyclization of \a-Oxoamides: The Power
 of a Covalently Linked Chiral Auxiliary Is Enhanced in the Crystalline
 State
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3568
_journal_page_last               3576
_journal_paper_doi               10.1021/ja043999p
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C23 H28 N2 O3'
_chemical_formula_weight         380.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 98.2230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4713(5)
_cell_length_b                   14.9511(12)
_cell_length_c                   10.7063(9)
_cell_measurement_reflns_used    6596
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.261
_cell_measurement_theta_min      2.356
_cell_volume                     1025.22(14)
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9040
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.8254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      0
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.7788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                4471
_reflns_number_total             4736
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja043999psi20041001_024101.cif
_cod_data_source_block           1c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constrained' was replaced with
the value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               4111527