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_4033454
_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 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2433(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.30129(8)
_cell_length_b                   22.3383(2)
_cell_length_c                   8.97393(10)
_cell_measurement_reflns_used    8919
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.1360
_cell_measurement_theta_min      5.0240
_cell_volume                     1654.23(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -54.00 -28.00   1.00    1.00    --  -41.49 -77.00  90.00   26
  2  \w    -70.00 -18.00   1.00    1.00    --  -41.49 -37.00  90.00   52
  3  \w   -103.00 -61.00   1.00    1.00    --  -41.49 -57.00  90.00   42
  4  \w   -116.00 -18.00   1.00    1.00    --  -41.49 -37.00  30.00   98
  5  \w    -94.00 -20.00   1.00    1.00    --  -41.49 -57.00 -60.00   74
  6  \w      8.00  64.00   1.00    1.00    --   41.49 -99.00-120.00   56
  7  \w     21.00  72.00   1.00    1.00    --   41.49 -99.00   0.00   51
  8  \w     36.00 120.00   1.00    1.00    --  107.19-125.00 -30.00   84
  9  \w     47.00 130.00   1.00    1.00    --  107.19 -30.00  90.00   83
 10  \w     81.00 108.00   1.00    1.00    --  107.19  45.00 150.00   27
 11  \w     82.00 110.00   1.00    1.00    --  107.19  45.00 120.00   28
 12  \w     82.00 135.00   1.00    1.00    --  107.19  45.00  90.00   53
 13  \w    150.00 177.00   1.00    1.00    --  107.19  61.00  90.00   27
 14  \w    128.00 177.00   1.00    1.00    --  107.19  61.00  30.00   49
 15  \w    112.00 178.00   1.00    1.00    --  107.19  77.00  90.00   66
 16  \w     96.00 127.00   1.00    1.00    --  107.19 125.00 -90.00   31
 17  \w    144.00 170.00   1.00    1.00    --  107.19 125.00-150.00   26
 18  \w    128.00 155.00   1.00    1.00    --  107.19  45.00-180.00   27
 19  \w     82.00 143.00   1.00    1.00    --  107.19  30.00-180.00   61
 20  \w     81.00 119.00   1.00    1.00    --  107.19  45.00-180.00   38
 21  \w     37.00  72.00   1.00    1.00    --  107.19 -45.00 -60.00   35
 22  \w     84.00 113.00   1.00    1.00    --  107.19  45.00  60.00   29
 23  \w     78.00 104.00   1.00    1.00    --  107.19  61.00  90.00   26
 24  \w     78.00 104.00   1.00    1.00    --  107.19  61.00  60.00   26
 25  \w     82.00 107.00   1.00    1.00    --  107.19  61.00  30.00   25
 26  \w     76.00 101.00   1.00    1.00    --  107.19  77.00  90.00   25
 27  \w     76.00 101.00   1.00    1.00    --  107.19  77.00 120.00   25
 28  \w     78.00 104.00   1.00    1.00    --  107.19  61.00 120.00   26
 29  \w     78.00 104.00   1.00    1.00    --  107.19  61.00 150.00   26
 30  \w     75.00 101.00   1.00    1.00    --  107.19  77.00 150.00   26
 31  \w     75.00 102.00   1.00    1.00    --  107.19  77.00  60.00   27
 32  \w     33.00 140.00   1.00    1.00    --  107.19 -77.00 120.00  107
 33  \w     10.00  57.00   1.00    1.00    --   41.49 -99.00-180.00   47
;
_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      0.1761119000
_diffrn_orient_matrix_UB_12      -0.0115503000
_diffrn_orient_matrix_UB_13      0.0667871000
_diffrn_orient_matrix_UB_21      0.0618299000
_diffrn_orient_matrix_UB_22      0.0321029000
_diffrn_orient_matrix_UB_23      -0.1346991000
_diffrn_orient_matrix_UB_31      0.0008521000
_diffrn_orient_matrix_UB_32      0.0599556000
_diffrn_orient_matrix_UB_33      0.0849422000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14226
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.280
_diffrn_reflns_theta_min         3.958
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88207
_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    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0408P)^2^+0.5673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3027
_reflns_number_total             3277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02849_si_002.cif
_cod_data_source_block           20160720b
_cod_depositor_comments
'Adding full bibliography for 4033451--4033455.cif.'
_cod_database_code               4033454
_chemical_oxdiff_formula         c1h1o1
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9A,H9B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              31143
_shelx_hkl_checksum              94724
_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 1.239
_oxdiff_exptl_absorpt_empirical_full_min 0.754