An efficient and straightforward access to sulfur substituted [2.2]paracyclophanes: application to stereoselective sulfenate salt alkylation.
Lohier, Jean-François; Foucoin, Florian; Jaffrès, Paul-Alain; Garcia, José I; Sopková-de Oliveira Santos, Jana; Perrio, Stéphane; Metzner, Patrick; Organic letters 10 (2008) 1271–1274; doi:10.1021/ol800161m

data_1504594
_publ_section_title
;
 An efficient and straightforward access to sulfur substituted
 [2.2]paracyclophanes: application to stereoselective sulfenate salt
 alkylation.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1271
_journal_page_last               1274
_journal_paper_doi               10.1021/ol800161m
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 O S'
_chemical_formula_sum            'C17 H18 O S'
_chemical_formula_weight         270.37
_chemical_melting_point          426(2)
_chemical_name_systematic
;
 (Sp,Ss)*-4-methylsulfinyl-[2.2]-paracyclophane
;
_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                 93.048(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8811(9)
_cell_length_b                   9.2532(6)
_cell_length_c                   10.6560(7)
_cell_measurement_reflns_used    8425
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.47
_cell_measurement_theta_min      3.22
_cell_volume                     1366.77(15)
_computing_cell_refinement       'APEX2 software'
_computing_data_collection       'APEX2 software'
_computing_data_reduction        'APEX2 software'
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>, 2007)'
_computing_publication_material  'SHELXTL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Nonius ApexII KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            44550
_diffrn_reflns_theta_full        36.60
_diffrn_reflns_theta_max         36.60
_diffrn_reflns_theta_min         1.47
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.589
_exptl_crystal_size_mid          0.344
_exptl_crystal_size_min          0.231
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         6725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.2485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                5531
_reflns_number_total             6725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800161m-file002.cif
_cod_data_source_block           9b
_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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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               1504594