Synthesis of 2-alkenylfurans via a Ag(i)-catalyzed tandem cyclization/cross-coupling reaction of enynones with iodonium ylides.
Peng, Haiyun; Wan, Yinbo; Zhang, Yu; Deng, Guisheng; Chemical communications (Cambridge, England) 56 (2020) 1417–1420; doi:10.1039/c9cc08561k

data_7125678
_publ_section_title
;
 Synthesis of 2-alkenylfurans via a Ag(i)-catalyzed tandem
 cyclization/cross-coupling reaction of enynones with iodonium ylides.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1417
_journal_page_last               1420
_journal_paper_doi               10.1039/c9cc08561k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C21 H20 O7'
_chemical_formula_sum            'C21 H20 O7'
_chemical_formula_weight         384.37
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-12 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   12.1107(2)
_cell_length_b                   12.1107(2)
_cell_length_c                   52.4973(14)
_cell_measurement_reflns_used    27012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2550
_cell_measurement_theta_min      3.9090
_cell_volume                     7699.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -30.00  54.00   1.00    1.00    --   34.86 -38.00   0.00   84
  2  \w      1.00  72.00   1.00    1.00    --   34.86 -99.00 -60.00   71
  3  \w     13.00  73.00   1.00    1.00    --   34.86 -99.00-180.00   60
  4  \w     36.00 106.00   1.00   10.00    --  105.25 -94.00-150.00   70
  5  \w     43.00 129.00   1.00   10.00    --  105.25 -77.00 -90.00   86
  6  \w     88.00 116.00   1.00   10.00    --  105.25-111.00   0.00   28
  7  \w     81.00 107.00   1.00   10.00    --  105.25 -94.00 120.00   26
  8  \w     43.00  68.00   1.00   10.00    --  105.25-111.00   0.00   25
  9  \w     36.00 106.00   1.00   10.00    --  105.25 -94.00  60.00   70
 10  \w     39.00 123.00   1.00   10.00    --  105.25 -61.00  60.00   84
 11  \w     84.00 175.00   1.00   10.00    --  105.25  30.00 -30.00   91
 12  \w    147.00 172.00   1.00   10.00    --  105.25  61.00 -30.00   25
 13  \w    125.00 173.00   1.00   10.00    --  105.25  77.00  30.00   48
 14  \w    129.00 173.00   1.00   10.00    --  105.25  77.00  60.00   44
 15  \w    114.00 173.00   1.00   10.00    --  105.25  77.00   0.00   59
 16  \w    121.00 168.00   1.00   10.00    --  105.25  61.00 -60.00   47
 17  \w    148.00 173.00   1.00   10.00    --  105.25  77.00-150.00   25
 18  \w    124.00 166.00   1.00   10.00    --  105.25  61.00-180.00   42
 19  \w    125.00 161.00   1.00   10.00    --  105.25  77.00 -90.00   36
 20  \w     87.00 113.00   1.00   10.00    --  105.25  61.00 -30.00   26
 21  \w     87.00 112.00   1.00   10.00    --  105.25  61.00   0.00   25
 22  \w     87.00 112.00   1.00   10.00    --  105.25  61.00  30.00   25
 23  \w     87.00 112.00   1.00   10.00    --  105.25  61.00  60.00   25
 24  \w     87.00 172.00   1.00   10.00    --  105.25  61.00  90.00   85
 25  \w    112.00 173.00   1.00   10.00    --  105.25  77.00 120.00   61
 26  \w    116.00 167.00   1.00   10.00    --  105.25  77.00 150.00   51
 27  \w     87.00 113.00   1.00   10.00    --  105.25  61.00 150.00   26
 28  \w     87.00 112.00   1.00   10.00    --  105.25  61.00 120.00   25
 29  \w     84.00 129.00   1.00   10.00    --  105.25  30.00  90.00   45
 30  \w     84.00 109.00   1.00   10.00    --  105.25  30.00  60.00   25
 31  \w     84.00 115.00   1.00   10.00    --  105.25  30.00  30.00   31
 32  \w     79.00 104.00   1.00   10.00    --  105.25  77.00 120.00   25
 33  \w     79.00 104.00   1.00   10.00    --  105.25  77.00  90.00   25
 34  \w     79.00 104.00   1.00   10.00    --  105.25  77.00  60.00   25
 35  \w     79.00 104.00   1.00   10.00    --  105.25  77.00  30.00   25
 36  \w     79.00 104.00   1.00   10.00    --  105.25  77.00   0.00   25
 37  \w     79.00 104.00   1.00   10.00    --  105.25  77.00 -30.00   25
 38  \w     87.00 115.00   1.00   10.00    --  105.25  61.00 -60.00   28
 39  \w     87.00 113.00   1.00   10.00    --  105.25  61.00 -90.00   26
 40  \w     87.00 172.00   1.00   10.00    --  105.25  61.00-120.00   85
 41  \w     87.00 160.00   1.00   10.00    --  105.25  61.00-150.00   73
 42  \w     84.00 119.00   1.00   10.00    --  105.25  30.00-180.00   35
 43  \w     87.00 121.00   1.00   10.00    --  105.25  61.00-180.00   34
 44  \w     79.00 104.00   1.00   10.00    --  105.25  77.00 -90.00   25
 45  \w     79.00 104.00   1.00   10.00    --  105.25  77.00 -60.00   25
 46  \w     79.00 104.00   1.00   10.00    --  105.25  77.00-120.00   25
 47  \w     79.00 104.00   1.00   10.00    --  105.25  77.00-150.00   25
 48  \w     79.00 104.00   1.00   10.00    --  105.25  77.00-180.00   25
 49  \w     85.00 112.00   1.00   10.00    --  105.25  30.00 -60.00   27
 50  \w     51.00  89.00   1.00    1.00    --   34.86  57.00-180.00   38
 51  \w     56.00 100.00   1.00    1.00    --   34.86  77.00 -90.00   44
 52  \w     51.00  77.00   1.00    1.00    --   34.86  77.00 -60.00   26
 53  \w     18.00  45.00   1.00    1.00    --   34.86  57.00-180.00   27
 54  \w      8.00 101.00   1.00    1.00    --   34.86  77.00-150.00   93
 55  \w     10.00 100.00   1.00    1.00    --   34.86  77.00   0.00   90
 56  \w     68.00  99.00   1.00    1.00    --   34.86  77.00  60.00   31
 57  \w     79.00 104.00   1.00   10.00    --  105.25  77.00 150.00   25
 58  \w     84.00 115.00   1.00   10.00    --  105.25  30.00 150.00   31
 59  \w     20.00 102.00   1.00    1.00    --   34.86  57.00 120.00   82
 60  \w     10.00  56.00   1.00    1.00    --   34.86  77.00  60.00   46
 61  \w      8.00  44.00   1.00    1.00    --   34.86  77.00 -60.00   36
 62  \w      8.00  45.00   1.00    1.00    --   34.86  77.00 -90.00   37
 63  \w    -32.00  36.00   1.00    1.00    --   34.86 -57.00-150.00   68
 64  \w    -22.00  24.00   1.00    1.00    --   34.86 -77.00   0.00   46
 65  \w     30.00  83.00   1.00    1.00    --   34.86-125.00  90.00   53
 66  \w    -51.00  25.00   1.00    1.00    --  -34.86  57.00 150.00   76
 67  \w     -2.00  24.00   1.00    1.00    --   34.86  95.00 114.47   26
 68  \w    -61.00 -10.00   1.00    1.00    --  -34.86 -19.00  60.00   51
 69  \w    -63.00 -16.00   1.00    1.00    --  -34.86 -38.00 -30.00   47
 70  \w   -100.00 -74.00   1.00    1.00    --  -34.86 -19.00  60.00   26
 71  \w   -103.00 -78.00   1.00    1.00    --  -34.86 -38.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0371298000
_diffrn_orient_matrix_UB_12      0.1031432000
_diffrn_orient_matrix_UB_13      -0.0149239000
_diffrn_orient_matrix_UB_21      0.1170089000
_diffrn_orient_matrix_UB_22      0.0118156000
_diffrn_orient_matrix_UB_23      -0.0111670000
_diffrn_orient_matrix_UB_31      -0.0331497000
_diffrn_orient_matrix_UB_32      -0.0735220000
_diffrn_orient_matrix_UB_33      -0.0226780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            52528
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.580
_diffrn_reflns_theta_max         66.580
_diffrn_reflns_theta_min         3.367
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+2.3392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3204
_reflns_number_total             3419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08561k2.cif
_cod_data_source_block           exp_788
_cod_depositor_comments          'Adding full bibliography for 7125678.cif.'
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7125678
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H100 O7'
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.787
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_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 5.326
_oxdiff_exptl_absorpt_empirical_full_min 0.577