Regio- and Stereocontrol in the Michael-Initiated Ring-Closure Reactions of γ,δ-Epoxy-α,β-unsaturated Esters, Ketones, Sulfones, and Amides
Ramesh C. Dhakal; R. Karl Dieter; Journal of Organic Chemistry 78 (2013) 12426–12439; doi:10.1021/jo402075d

data_4028853
_publ_section_title
;
 Regio- and Stereocontrol in the Michael-Initiated Ring-Closure Reactions
 of \g,\d-Epoxy-\a,\b-unsaturated Esters, Ketones, Sulfones, and Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12426
_journal_page_last               12439
_journal_paper_doi               10.1021/jo402075d
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C15 H22 O3 S'
_chemical_formula_weight         282.39
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6271(16)
_cell_length_b                   13.257(4)
_cell_length_c                   20.571(7)
_cell_measurement_reflns_used    4443
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      26.3910
_cell_measurement_theta_min      3.7541
_cell_volume                     1534.6(8)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC,2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC,2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC,2006)'
_computing_molecular_graphics    'SHELXTL 6.10 (Sheldrick,2008)'
_computing_publication_material  'SHELXTL 6.10 (Sheldrick,2008)'
_computing_structure_refinement  'SHELXTL 6.10 (Sheldrick,2008)'
_computing_structure_solution    'SHELXTL 6.10 (Sheldrick,2008)'
_diffrn_ambient_temperature      178(2)
_diffrn_detector_area_resol_mean 14.9365
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
    Number of images: 260
               Slice: -40.0000 - 90.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 27.0801
              2theta: -0.0260
scan:
    Number of images: 220
               Slice: -30.0000 - 80.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 27.0801
              2theta: -0.0260

;
_diffrn_measurement_device
;
Mercury 1K CCD
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3 circle
;
_diffrn_measurement_method       omega
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12308
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.8654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R., (1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.44(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0582
_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^)+(0.0872P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                2424
_reflns_number_total             3128
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402075d_si_002.cif
_cod_data_source_block           ramesh1
_cod_original_cell_volume        1534.6(9)
_cod_database_code               4028853