Intramolecular Methylation of an Allyl Sulfone via Lithium Alkoxyaluminate; Application to the Enantioselective Synthesis of the CD Ring of Vitamin D(3).
Sikervar, Vikas; Fuchs, Philip L.; Organic letters 14 (2012) 2922–2924; doi:10.1021/ol301144a

data_1507747
_publ_section_title
;
 Intramolecular Methylation of an Allyl Sulfone via Lithium
 Alkoxyaluminate; Application to the Enantioselective Synthesis of the CD
 Ring of Vitamin D(3).
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2922
_journal_page_last               2924
_journal_paper_doi               10.1021/ol301144a
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H32 O4 S1 Si1'
_chemical_formula_sum            'C21 H32 O4 S Si'
_chemical_formula_weight         408.64
_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_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                90.00
_cell_angle_beta                 100.3508(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.53160(10)
_cell_length_b                   31.8491(6)
_cell_length_c                   9.4105(2)
_cell_measurement_reflns_used    17184
_cell_measurement_temperature    150.00(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     2220.61(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 2003)
;
_computing_publication_material  'SHELX97(Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution
;
 Direct methods (SIR2004, Burla et al., 2005)
;
_diffrn_ambient_temperature      150.00(2)
_diffrn_measured_fraction_theta_full 0.9860
_diffrn_measured_fraction_theta_max 0.9860
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17184
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         0.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.9565
_exptl_absorpt_correction_T_min  0.8360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.43
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.12(6)
_refine_ls_extinction_coef       0.38E-01
_refine_ls_extinction_method     'SHELXL97 (Sheldrick 2008)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         9573
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.073
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.124
_refine_ls_wR_factor_ref         0.134
_reflns_Friedel_coverage         0.9431
_reflns_number_gt                7446
_reflns_number_total             9573
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            ol301144a_si_003.cif
_cod_data_source_block           CDSF
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
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 

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        2220.60(7)
_cod_original_formula_sum        'C21 H32 O4 S1 Si1'
_cod_database_code               1507747