Facile Assembly of Chiral Tetrahydrothiopyrans Containing Four Consecutive Stereocenters via an Organocatalytic Enantioselective Michael-Michael Cascade.
Wang, Shengzheng; Zhang, Yongqiang; Dong, Guoqiang; Wu, Shanchao; Fang, Kun; Li, Zhengang; Miao, Zhenyuan; Yao, Jianzhong; Li, Hao; Li, Jian; Zhang, Wannian; Wang, Wei; Sheng, Chunquan; Organic letters 16 (2014) 692–695; doi:10.1021/ol4033557

data_1513464
_publ_section_title
;
 Facile Assembly of Chiral Tetrahydrothiopyrans Containing Four
 Consecutive Stereocenters via an Organocatalytic Enantioselective
 Michael-Michael Cascade.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              692
_journal_page_last               695
_journal_paper_doi               10.1021/ol4033557
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C27 H23 Br O3 S'
_chemical_formula_weight         507.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.404(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.361(5)
_cell_length_b                   5.4611(8)
_cell_length_c                   13.461(2)
_cell_measurement_temperature    296(2)
_cell_volume                     2304.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8177
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.009
_diffrn_reflns_theta_min         1.299
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 1650 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.012(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4473
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0376P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                4105
_reflns_number_total             4473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol4033557_si_002.cif
_cod_data_source_block           3b
_cod_original_cell_volume        2304.8(6)
_cod_database_code               1513464
_shelx_estimated_absorpt_t_min   0.764
_shelx_estimated_absorpt_t_max   0.863
_shelxl_version_number           2013-2
_shelx_res_checksum              61702
_shelx_hkl_checksum              4423