The tert-Butylsulfinyl Group as a Highly Efficient Chiral Auxiliary in Asymmetric Pauson-Khand Reactions
Javier Adrio; Juan C. Carretero; Journal of the American Chemical Society 121 (1999) 7411–7412; doi:10.1021/ja990546p

data_4116489
_publ_section_title
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 The tert-Butylsulfinyl Group as a Highly Efficient Chiral Auxiliary in
 Asymmetric Pauson-Khand Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7411
_journal_page_last               7412
_journal_paper_doi               10.1021/ja990546p
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C12 H18 O2 S'
_chemical_formula_weight         226.32
_chemical_name_systematic
;
 (4R,5S,S(S))-4-(tert-butylsulfinyl)bicyclo(3.3.0)oct-1-en-3-one
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.526(3)
_cell_length_b                   10.774(3)
_cell_length_c                   10.818(5)
_cell_measurement_temperature    296(2)
_cell_volume                     1226.8(7)
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  XL
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1342
_diffrn_reflns_theta_max         57.02
_diffrn_reflns_theta_min         5.80
_exptl_absorpt_coefficient_mu    2.174
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       'Transparent blocks'
_exptl_crystal_F_000             488
_exptl_crystal_size_max          O.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0179(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   0.586
_refine_ls_goodness_of_fit_obs   0.582
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.586
_refine_ls_restrained_S_obs      0.582
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_obs          0.0353
_refine_ls_shift/esd_max         0.092
_refine_ls_shift/esd_mean        0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1354P)^2^+1.1054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1055
_refine_ls_wR_factor_obs         0.1026
_reflns_number_observed          1159
_reflns_number_total             1207
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja990546p.cif
_cod_data_source_block           jcjav
_cod_depositor_comments
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The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1354P)^2^+1.1054P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1354P)^2^+1.1054P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1227.00(7)
_cod_database_code               4116489