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_4033455
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                81.578(5)
_cell_angle_beta                 89.377(5)
_cell_angle_gamma                88.703(6)
_cell_formula_units_Z            4
_cell_length_a                   8.6301(6)
_cell_length_b                   8.6645(7)
_cell_length_c                   22.6154(12)
_cell_measurement_reflns_used    5474
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.0500
_cell_measurement_theta_min      5.0990
_cell_volume                     1672.4(2)
_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 0.965
_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      1.00  47.00   1.00    1.00    --   41.49 -99.00   0.00   46
  2  \w     10.00  37.00   1.00    1.00    --   41.49 -99.00  30.00   27
  3  \w      2.00  80.00   1.00    1.00    --   41.49 -99.00  90.00   78
  4  \w     28.00 107.00   1.00    2.00    --  107.52 -94.00   0.00   79
  5  \w     35.00 121.00   1.00    2.00    --  107.52-125.00-120.00   86
  6  \w     33.00 140.00   1.00    2.00    --  107.52 -77.00  30.00  107
  7  \w     82.00 175.00   1.00    2.00    --  107.52  45.00-150.00   93
  8  \w    112.00 176.00   1.00    2.00    --  107.52 125.00   0.00   64
  9  \w     95.00 134.00   1.00    2.00    --  107.52 125.00  30.00   39
 10  \w     83.00 158.00   1.00    2.00    --  107.52  61.00 120.00   75
 11  \w     85.00 167.00   1.00    2.00    --  107.52  77.00 150.00   82
 12  \w     78.00 178.00   1.00    2.00    --  107.52  61.00  90.00  100
 13  \w     35.00  94.00   1.00    2.00    --  107.52 -94.00 -60.00   59
 14  \w    -32.00  -2.00   1.00    1.00    --  -41.49 125.00-150.00   30
 15  \w   -112.00 -17.00   1.00    1.00    --  -41.49 -37.00-150.00   95
 16  \w    -81.00 -54.00   1.00    1.00    --  -41.49 125.00-150.00   27
 17  \w   -113.00 -21.00   1.00    1.00    --  -41.49 -37.00 120.00   92
;
_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      -0.1727106000
_diffrn_orient_matrix_UB_12      -0.0110891000
_diffrn_orient_matrix_UB_13      -0.0150228000
_diffrn_orient_matrix_UB_21      0.0183918000
_diffrn_orient_matrix_UB_22      -0.1786677000
_diffrn_orient_matrix_UB_23      0.0048389000
_diffrn_orient_matrix_UB_31      -0.0414354000
_diffrn_orient_matrix_UB_32      -0.0166023000
_diffrn_orient_matrix_UB_33      0.0670316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11887
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.858
_diffrn_reflns_theta_min         3.952
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96715
_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    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0484P)^2^+0.4742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5625
_reflns_number_total             6544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02849_si_005.cif
_cod_data_source_block           20170223e
_cod_depositor_comments
'Adding full bibliography for 4033451--4033455.cif.'
_cod_original_cell_volume        1672.37(19)
_cod_database_code               4033455
_chemical_oxdiff_formula         c1h1o1I1
_reflns_odcompleteness_completeness 99.93
_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), C33(H33), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C29(H29A,H29B), C32(H32A,H32B)
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), C22(H22), C23(H23), C24(H24), C25(H25), C36(H36), C37(H37), C38(H38),
  C39(H39), C40(H40)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              85383
_shelx_hkl_checksum              51077
_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 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.898