Synthesis of Sulfonylated Lactones via Ag-Catalyzed Cascade Sulfonylation/Cyclization of 1,6-Enynes with Sodium Sulfinates.
Wu, Wanqing; Yi, Songjian; Yu, Yue; Huang, Wei; Jiang, Huanfeng; The Journal of organic chemistry 82 (2017) 1224–1230; doi:10.1021/acs.joc.6b02416

data_4032131
_publ_section_title
;
 Synthesis of Sulfonylated Lactones via Ag-Catalyzed Cascade
 Sulfonylation/Cyclization of 1,6-Enynes with Sodium Sulfinates.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1224
_journal_page_last               1230
_journal_paper_doi               10.1021/acs.joc.6b02416
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H18 O4 S'
_chemical_formula_sum            'C19 H18 O4 S'
_chemical_formula_weight         342.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                96.267(6)
_cell_angle_beta                 111.946(5)
_cell_angle_gamma                99.630(5)
_cell_formula_units_Z            2
_cell_length_a                   8.9705(4)
_cell_length_b                   9.4409(7)
_cell_length_c                   10.5838(7)
_cell_measurement_temperature    293(2)
_cell_volume                     805.10(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5395
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.489
_diffrn_reflns_theta_min         5.550
_exptl_absorpt_coefficient_mu    1.964
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             360
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0049(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.5407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2447
_reflns_number_total             2798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02416_si_002.cif
_cod_data_source_block           0705-2
_cod_depositor_comments          'Adding full bibliography for 4032131.cif.'
_cod_original_cell_volume        805.10(9)
_cod_database_code               4032131
_shelxl_version_number           2014-1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C14(H14A,H14B)
2.b Me refined with riding coordinates:
 C13(H13A,H13B,H13C)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C3(H3), C6(H6), C5(H5), C17(H17), C12(H12), C11(H11), C8(H8),
 C7(H7), C10(H10)
2.d Fitted hexagon refined as free rotating group:
 C2(C1,C3,C6,C5,C4), C12(C11,C8,C7,C9,C10)
;
_shelx_res_checksum              34791
_shelx_hkl_checksum              50077
_olex2_submission_special_instructions 'No special instructions were received'