A modular approach to highly functionalized 3-sulfonylfurans via conjugate addition of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates and sequential 5-endo-trig iodocyclization
Miao, Maozhong; Xu, Huaping; Luo, Yi; Jin, Mengchao; Chen, Zhengkai; Xu, Jianfeng; Ren, Hongjun; Organic Chemistry Frontiers 4 (2017) 1824–; doi:10.1039/C7QO00362E

data_1553804
_publ_section_title
;
 A modular approach to highly functionalized 3-sulfonylfurans via
 conjugate addition of 3-cyclopropylideneprop-2-en-1-ones with sodium
 sulfinates and sequential 5-endo-trig iodocyclization
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1824
_journal_paper_doi               10.1039/C7QO00362E
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C28 H29 I O4 S'
_chemical_formula_sum            'C28 H29 I O4 S'
_chemical_formula_weight         588.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2017-04-10 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.892(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0087(6)
_cell_length_b                   17.7464(7)
_cell_length_c                   12.6045(7)
_cell_measurement_reflns_used    4288
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3983
_cell_measurement_theta_min      2.9163
_cell_volume                     2607.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0394115000
_diffrn_orient_matrix_UB_12      -0.0021916000
_diffrn_orient_matrix_UB_13      -0.0517719000
_diffrn_orient_matrix_UB_21      0.0293678000
_diffrn_orient_matrix_UB_22      -0.0320251000
_diffrn_orient_matrix_UB_23      -0.0131674000
_diffrn_orient_matrix_UB_31      -0.0358744000
_diffrn_orient_matrix_UB_32      -0.0238048000
_diffrn_orient_matrix_UB_33      0.0225099000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18518
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4753
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0665
_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^)+(0.0738P)^2^+6.9313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1759
_refine_ls_wR_factor_ref         0.1906
_reflns_number_gt                3471
_reflns_number_total             4753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00362e2.cif
_cod_data_source_block           160530_yq5_c2k
_cod_database_code               1553804
_chemical_oxdiff_formula         c28h29i1s1o4
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19-C18
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C18 \\sim C24 \\sim O4 \\sim C19 \\sim C20 \\sim C21 \\sim C23 \\sim C22 \\sim
C25 \\sim C26: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
4. Others
 Sof(H27C)=Sof(H27D)=Sof(I1A)=Sof(C28A)=Sof(H28C)=Sof(H28D)=1-FVAR(1)
 Sof(H27A)=Sof(H27B)=Sof(I1)=Sof(C28)=Sof(H28A)=Sof(H28B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C21(H21)
5.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C27(H27C,H27D), C17(H17A,H17B), C20(H20A,H20B), C22(H22A,
 H22B), C23(H23A,H23B), C28(H28A,H28B), C28A(H28C,H28D)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C8(H8)
5.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;