Reagent-Directed Allylic Quadraselection. Chemoselective Anti- and Syn-Lawton SN2' Methylation of Seven-Membered Epoxyvinylsulfones
Wan Pyo Hong; Ahmad El-Awa; Philip L. Fuchs; Journal of the American Chemical Society 131 (2009) 9150–9151; doi:10.1021/ja9017557

data_4104644
_publ_contact_author_address
;    Department of Chemistry
     Purdue University
     560 Oval Dr.
     W. Lafayette
     IN 47907-2084
     USA
;
_publ_contact_author_email       pfuchs@purdue.edu
_publ_contact_author_name        'Philip L. Fuchs'
_publ_contact_author_phone       1(765)4945242
_publ_section_title
;
 Reagent-Directed Allylic Quadraselection. Chemoselective Anti- and
 Syn-Lawton SN2' Methylation of Seven-Membered Epoxyvinylsulfones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9150
_journal_page_last               9151
_journal_paper_doi               10.1021/ja9017557
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H48 O4 S1 Si2'
_chemical_formula_sum            'C27 H48 O4 S Si2'
_chemical_formula_weight         524.92
_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)'
_audit_creation_date             4-09-08
_audit_creation_method           'SHELXL and local programs'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.4158(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0832(3)
_cell_length_b                   12.9599(2)
_cell_length_c                   20.2495(6)
_cell_measurement_reflns_used    23580
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     3156.86(13)
_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, 1997)
;
_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
_diffrn_measured_fraction_theta_full 0.9893
_diffrn_measured_fraction_theta_max 0.9893
_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  0.066
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23580
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9756
_exptl_absorpt_correction_T_min  0.8639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         13028
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.088
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0199P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.078
_refine_ls_wR_factor_ref         0.089
_reflns_Friedel_coverage         0.8531
_reflns_number_gt                8716
_reflns_number_total             13028
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            ja9017557_si_003.cif
_cod_data_source_block           136287
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
according to the built-in table from CIF Core 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 '_exptl_absorpt__process_details' was replaced with
'_exptl_absorpt_process_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_formula_sum        'C27 H48 O4 S1 Si2'
_cod_database_code               4104644