Facile synthesis of <i>N</i>-(α-furanyl) alkyl sulfoximines <i>via</i> gold catalyzed Michael addition/cyclization of enynones and sulfoximines.
Antony Haritha Mercy, A.; Padma Priya, V. R.; Hariprasad, R.; Gayathri, K.; Ravindra, S.; Chandra Nandi, Ganesh; Kataria, Ramesh; Organic & biomolecular chemistry 22 (2024) 945–949; doi:10.1039/d3ob01631e

data_7159763
_publ_section_title
;
 Facile synthesis of <i>N</i>-(&#x3b1;-furanyl) alkyl sulfoximines
 <i>via</i> gold catalyzed Michael addition/cyclization of enynones and
 sulfoximines.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              945
_journal_page_last               949
_journal_paper_doi               10.1039/d3ob01631e
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C24 H29 N O2 S'
_chemical_formula_sum            'C24 H29 N O2 S'
_chemical_formula_weight         395.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-26 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.364(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3206(4)
_cell_length_b                   9.0166(4)
_cell_length_c                   16.8696(8)
_cell_measurement_reflns_used    4849
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8080
_cell_measurement_theta_min      3.5840
_cell_volume                     1104.33(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -20.00   7.00   0.50   15.67    --   -9.32 108.00 -40.00   54
  2  \w     -2.00  24.00   0.50   15.67    --    9.60-108.00-137.00   52
  3  \w    -23.00  16.00   0.50   15.67    --   -9.32  38.00 120.00   78
  4  \w     26.00  52.00   0.50   15.67    --   -9.32  38.00 120.00   52
  5  \w    -17.00   9.00   0.50   15.67    --   -9.32 -77.00  60.00   52
  6  \w      8.00  56.00   0.50   15.67    --    9.60-125.00  90.00   96
  7  \w    -14.00  39.00   0.50   15.67    --    9.60 -99.00   0.00  106
  8  \w    -14.00  40.00   0.50   15.67    --    9.60 -99.00-120.00  108
  9  \w    -14.00  35.00   0.50   15.67    --    9.60 -99.00  90.00   98
 10  \w     13.00  54.00   0.50   15.67    --    9.60-125.00 -30.00   82
 11  \w    -52.00  23.00   0.50   15.67    --    9.60 -38.00 -90.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0377714000
_diffrn_orient_matrix_UB_12      0.0019848000
_diffrn_orient_matrix_UB_13      0.0366710000
_diffrn_orient_matrix_UB_21      -0.0237412000
_diffrn_orient_matrix_UB_22      -0.0760605000
_diffrn_orient_matrix_UB_23      -0.0045158000
_diffrn_orient_matrix_UB_31      0.0869042000
_diffrn_orient_matrix_UB_32      -0.0199077000
_diffrn_orient_matrix_UB_33      0.0208227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.872
_diffrn_reflns_Laue_measured_fraction_max 0.822
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8334
_diffrn_reflns_point_group_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.594
_diffrn_reflns_theta_min         3.199
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.31(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0447P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.889
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                2610
_reflns_number_total             3495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01631e2.cif
_cod_data_source_block           rk-112
_cod_depositor_comments          'Adding full bibliography for 7159763.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159763
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.69(10)
 0.31(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5), C15(H15), C12(H12)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C21(H21), C23(H23), C22(H22), C20(H20), C10(H10), C11(H11), C7(H7),
 C9(H9), C8(H8), C19(H19)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              15315
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.993
_oxdiff_exptl_absorpt_empirical_full_min 0.664