Cis and trans selective 1,4-addition of a lithium dithioester enolate to 4-O-TBS-2-cyclohexenone.
Spivey, Alan C.; Martin, Laetitia J.; Grainger, Damian M.; Ortner, Jörg; White, Andrew J. P.; Organic letters 8 (2006) 3891–3894; doi:10.1021/ol0611090

data_1506083
_publ_section_title
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 Cis and trans selective 1,4-addition of a lithium dithioester enolate to
 4-O-TBS-2-cyclohexenone.
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_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              3891
_journal_page_last               3894
_journal_paper_doi               10.1021/ol0611090
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C8 H10 O3'
_chemical_formula_weight         154.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.59(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.921(3)
_cell_length_b                   6.2036(17)
_cell_length_c                   11.144(3)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.8409
_cell_measurement_theta_min      3.9898
_cell_volume                     750.0(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_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      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54248
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6957
_diffrn_reflns_theta_full        71.02
_diffrn_reflns_theta_max         71.02
_diffrn_reflns_theta_min         8.19
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.97662
_exptl_absorpt_correction_T_min  0.87326
_exptl_absorpt_correction_type   'numeric analytical'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shards
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0014(16)
_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_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1425
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0896P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                813
_reflns_number_total             1425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0611090si20060804_022632.cif
_cod_data_source_block           Compound_7t
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1506083