Diastereoselective Preparation of Substituted δ-Valerolactones. Synthesis of (3R,4S)- and (3R,4R)-Simplactones
Antonio Osorio-Lozada; Horacio F. Olivo; Journal of Organic Chemistry 74 (2009) 1360–1363; doi:10.1021/jo8025548

data_4024316
_publ_section_title
;
Diastereoselective Preparation of Substituted \d-Valerolactones. Synthesis
of (3R,4S)- and (3R,4R)-Simplactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1360
_journal_page_last               1363
_journal_paper_doi               10.1021/jo8025548
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H17 N O2 S2'
_chemical_formula_sum            'C15 H17 N O2 S2'
_chemical_formula_weight         307.42
_chemical_name_systematic
; 
 ? 
;
_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                 100.596(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8141(6)
_cell_length_b                   26.756(3)
_cell_length_c                   11.7103(13)
_cell_measurement_reflns_used    4532
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.0
_cell_volume                     1482.6(3)
_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, 1997)'
_computing_publication_material  'SHELXTL v6.1 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL v6.1 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL v6.1 (Sheldrick, 1997)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0857
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15656
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5150
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0213P)^2^+0.5524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                3708
_reflns_number_total             5150
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8025548_si_003.cif
_cod_data_source_block           Oli08_3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4024316