Diastereoselective conjugate addition of organocuprates to chiral N-enoyl oxazolidinethiones.
Sabala, Rocío; Hernández-García, Luis; Ortiz, Aurelio; Romero, Moisés; Olivo, Horacio F.; Organic letters 12 (2010) 4268–4270; doi:10.1021/ol101687e

data_1503184
_publ_section_title
;
 Diastereoselective conjugate addition of organocuprates to chiral N-enoyl
 oxazolidinethiones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4268
_journal_page_last               4270
_journal_paper_doi               10.1021/ol101687e
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H21 N O2 S'
_chemical_formula_sum            'C21 H21 N O2 S'
_chemical_formula_weight         351.45
_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                   4.5421(9)
_cell_length_b                   10.033(2)
_cell_length_c                   37.818(8)
_cell_measurement_reflns_used    3107
_cell_measurement_temperature    155(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.0
_cell_volume                     1723.4(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor,1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor,1997)'
_computing_molecular_graphics    'SHELXTL v6.1 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL v6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL v6.1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      155(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD 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  0.0682
_diffrn_reflns_av_sigmaI/netI    0.1072
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            10583
_diffrn_reflns_theta_full        24.25
_diffrn_reflns_theta_max         24.25
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor,1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.2936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                1620
_reflns_number_total             2693
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101687e_si_004.cif
_cod_data_source_block           oli94
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1723.3(6)
_cod_database_code               1503184