Mercury(II)-Mediated Cleavage of Cyclopropylcarbinols by an Intramolecular Sulfinyl Group as a Stereo- and Regioselective Route to Stereotriads and Stereotetrads
Sadagopan Raghavan; Vaddela Sudheer Babu; B. Sridhar; Journal of Organic Chemistry 76 (2011) 557–565; doi:10.1021/jo1019909

data_4025985
_publ_section_title
;
 Mercury(II)-Mediated Cleavage of Cyclopropylcarbinols by an
 Intramolecular Sulfinyl Group as a Stereo- and Regioselective Route to
 Stereotriads and Stereotetrads
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              557
_journal_page_last               565
_journal_paper_doi               10.1021/jo1019909
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H26 O3 S'
_chemical_formula_sum            'C20 H26 O3 S'
_chemical_formula_weight         346.47
_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_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                 98.465(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2606(6)
_cell_length_b                   6.0075(3)
_cell_length_c                   32.5420(18)
_cell_measurement_reflns_used    4592
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.94
_cell_measurement_theta_min      2.53
_cell_volume                     1984.05(19)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            19320
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6995
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0822P)^2^+0.1523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                5738
_reflns_number_total             6995
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo1019909_si_001.cif
_cod_data_source_block           ag28m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025985