N-Heterocyclic Carbene/Palladium Cascade Catalysis: Construction of 2,2-Disubstitiuted Benzofuranones from the Reaction of 3-(2-Formylphenoxy)propenoates with Allylic Esters.
Liu, Yu-Jie; Ding, Ya-Li; Niu, Shuang-Shuo; Ma, Jin-Tao; Cheng, Ying; The Journal of organic chemistry 83 (2018) 1913–1923; doi:10.1021/acs.joc.7b02849

data_4033452
_publ_section_title
;
 N-Heterocyclic Carbene/Palladium Cascade Catalysis: Construction of
 2,2-Disubstitiuted Benzofuranones from the Reaction of
 3-(2-Formylphenoxy)propenoates with Allylic Esters.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1913
_journal_page_last               1923
_journal_paper_doi               10.1021/acs.joc.7b02849
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H18 O5'
_chemical_formula_sum            'C20 H18 O5'
_chemical_formula_weight         338.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.817(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3733(4)
_cell_length_b                   8.5291(3)
_cell_length_c                   15.5173(6)
_cell_measurement_reflns_used    3501
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.9680
_cell_measurement_theta_min      5.8290
_cell_volume                     1725.84(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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     21.00  74.00   1.00    1.00    --   41.49 -99.00   0.00   53
  2  \w     42.00 131.00   1.00    1.00    --  107.52 -61.00   0.00   89
  3  \w    100.00 129.00   1.00    1.00    --  107.52 -30.00 -90.00   29
  4  \w     88.00 115.00   1.00    1.00    --  107.52  45.00 -90.00   27
  5  \w    148.00 175.00   1.00    1.00    --  107.52  45.00 -90.00   27
  6  \w     94.00 176.00   1.00    1.00    --  107.52 125.00   0.00   82
  7  \w     79.00 175.00   1.00    1.00    --  107.52  61.00 150.00   96
  8  \w     83.00 122.00   1.00    1.00    --  107.52-125.00  30.00   39
  9  \w     36.00 114.00   1.00    1.00    --  107.52-125.00 -30.00   78
 10  \w     15.00  70.00   1.00    1.00    --   41.49 -99.00-180.00   55
 11  \w   -117.00  -3.00   1.00    1.00    --  -41.49   0.00 -60.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0373360000
_diffrn_orient_matrix_UB_12      -0.1270256000
_diffrn_orient_matrix_UB_13      -0.0562339000
_diffrn_orient_matrix_UB_21      0.0371525000
_diffrn_orient_matrix_UB_22      0.1287010000
_diffrn_orient_matrix_UB_23      -0.0551590000
_diffrn_orient_matrix_UB_31      0.1055080000
_diffrn_orient_matrix_UB_32      -0.0007149000
_diffrn_orient_matrix_UB_33      0.0646410000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6719
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.482
_diffrn_reflns_theta_min         3.954
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
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    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0687P)^2^+0.4798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2972
_reflns_number_total             3386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02849_si_004.cif
_cod_data_source_block           20170223d
_cod_depositor_comments
'Adding full bibliography for 4033451--4033455.cif.'
_cod_original_cell_volume        1725.83(11)
_cod_database_code               4033452
_chemical_oxdiff_formula         c1h1o1i1
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 Ternary CH refined with riding coordinates:
 C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              88290
_shelx_hkl_checksum              10953
_shelx_shelxl_version_number     2014/7
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.757