Synthesis of Densely Substituted Sulfonylfurans and Dihydrofurans via Cascade Reactions of α-Functionalized Nitroalkenes with β-Ketosulfones.
Mane, Vaijinath; Sivanandan, Sudheesh T.; Santana, Rafael G.; Beatriz, Adilson; da Silva Júnior, Eufrânio N; Namboothiri, Irishi N. N.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00606

data_4038531
_publ_section_title
;
 Synthesis of Densely Substituted Sulfonylfurans and Dihydrofurans via
 Cascade Reactions of \a-Functionalized Nitroalkenes with \b-Ketosulfones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00606
_journal_year                    2020
_chemical_formula_moiety         'C27 H24 O6 S'
_chemical_formula_sum            'C27 H24 O6 S'
_chemical_formula_weight         476.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-08-20
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.941(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1028(3)
_cell_length_b                   10.8990(3)
_cell_length_c                   18.1775(5)
_cell_measurement_reflns_used    14296
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.8770
_cell_measurement_theta_min      2.3630
_cell_volume                     2345.88(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  2  \w    -68.50  13.50   0.50    8.00    --  -20.00 -72.00-108.00  164
  3  \w   -110.00  70.00   0.50    8.00    --  -20.00   0.00  36.00  360
  4  \w    -59.00  -1.50   0.50    8.00    --  -20.00  72.00 -36.00  115
  5  \w    -30.00   0.00   0.50    8.00    --  -20.00  72.00-108.00   60
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0505631000
_diffrn_orient_matrix_UB_12      -0.0092498000
_diffrn_orient_matrix_UB_13      0.0271358000
_diffrn_orient_matrix_UB_21      0.0234248000
_diffrn_orient_matrix_UB_22      0.0535220000
_diffrn_orient_matrix_UB_23      -0.0128501000
_diffrn_orient_matrix_UB_31      -0.0220051000
_diffrn_orient_matrix_UB_32      0.0358496000
_diffrn_orient_matrix_UB_33      0.0262391000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23094
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.54
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+1.1965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                3568
_reflns_number_total             4130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00606_si_004.cif
_cod_data_source_block           inn-sts-464_mo
_cod_database_code               4038531
_reflns_odcompleteness_completeness 91.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.08
_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:
 C2(H2A,H2B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.174
_oxdiff_exptl_absorpt_empirical_full_min 0.836