Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.
Denmark, Scott E.; Jaunet, Alex; The Journal of organic chemistry 79 (2014) 140–171; doi:10.1021/jo4023765

data_4029087
_publ_contact_author
; 
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Catalytic, enantioselective, intramolecular carbosulfenylation of
 olefins. Preparative and stereochemical aspects.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              140
_journal_page_last               171
_journal_paper_doi               10.1021/jo4023765
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 O4 S'
_chemical_formula_sum            'C24 H22 O4 S'
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_chemical_name_systematic
; 
? 
;
_space_group_IT_number           4
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_atom_sites_solution_hydrogens   geom
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_audit_creation_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.598(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7172(12)
_cell_length_b                   10.941(2)
_cell_length_c                   15.717(3)
_cell_measurement_reflns_used    3320
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      22.81
_cell_measurement_theta_min      2.27
_cell_volume                     982.1(3)
_computing_cell_refinement       'SAINT V7.68A (Bruker, 2005)'
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_computing_data_reduction
; 
SAINT V7.68A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens Platform/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
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_exptl_crystal_colour            colourless
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_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
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; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (0 -1 -2) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
Flack (1983),  1900 Friedels 
Hooft,R.; Straver, L.; Spek, A. (2008) 
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0427P)^2^+0.0034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                3571
_reflns_number_total             4038
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4023765_si_003.cif
_cod_data_source_block           bm53uas
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        982.1(4)
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               4029087
_refine_ls_abs_structure_hooft   0.07(4)