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_4033453
_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 H17 Br O4'
_chemical_formula_sum            'C20 H17 Br O4'
_chemical_formula_weight         401.24
_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             2016-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                103.393(2)
_cell_angle_beta                 104.933(2)
_cell_angle_gamma                101.202(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2565(2)
_cell_length_b                   8.9113(2)
_cell_length_c                   12.9798(3)
_cell_measurement_reflns_used    5867
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.2010
_cell_measurement_theta_min      5.2890
_cell_volume                     864.27(4)
_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      100.01(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 0.991
_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      3.00  75.00   1.00    1.00    --   41.49 -99.00 120.00   72
  2  \w      2.00  43.00   1.00    1.00    --   41.49 -99.00  30.00   41
  3  \w     47.00  97.00   1.00    1.00    --   41.49-125.00 -30.00   50
  4  \w     58.00  84.00   1.00    1.00    --  112.00 -77.00  30.00   26
  5  \w     96.00 144.00   1.00    1.00    --  112.00 -77.00  30.00   48
  6  \w     90.00 116.00   1.00    1.00    --  112.00-111.00 150.00   26
  7  \w     75.00 133.00   1.00    1.00    --  112.00 -30.00 120.00   58
  8  \w     85.00 152.00   1.00    1.00    --  112.00  30.00 120.00   67
  9  \w    102.00 178.00   1.00    1.00    --  112.00  45.00 150.00   76
 10  \w    116.00 172.00   1.00    1.00    --  112.00 111.00  90.00   56
 11  \w    132.00 178.00   1.00    1.00    --  112.00 111.00   0.00   46
 12  \w    117.00 144.00   1.00    1.00    --  112.00 178.00  30.00   27
 13  \w     81.00 110.00   1.00    1.00    --  112.00 178.00  30.00   29
 14  \w     68.00 137.00   1.00    1.00    --  112.00 178.00   0.00   69
 15  \w     58.00 149.00   1.00    1.00    --  112.00 178.00 -60.00   91
 16  \w    114.00 165.00   1.00    1.00    --  112.00 111.00-150.00   51
 17  \w    132.00 177.00   1.00    1.00    --  112.00  30.00-150.00   45
 18  \w     98.00 124.00   1.00    1.00    --  112.00  30.00-150.00   26
 19  \w     97.00 136.00   1.00    1.00    --  112.00 -45.00 -90.00   39
 20  \w     84.00 113.00   1.00    1.00    --  112.00-111.00 -30.00   29
 21  \w     74.00 113.00   1.00    1.00    --  112.00-111.00-120.00   39
 22  \w     36.00  69.00   1.00    1.00    --  112.00-111.00-150.00   33
 23  \w     30.00 102.00   1.00    1.00    --  112.00 -94.00   0.00   72
 24  \w     42.00 110.00   1.00    1.00    --  112.00-111.00  90.00   68
 25  \w     40.00  65.00   1.00    1.00    --  112.00-111.00 150.00   25
 26  \w    -46.00  -2.00   1.00    1.00    --  -41.49 125.00 -30.00   44
 27  \w   -116.00 -22.00   1.00    1.00    --  -41.49 -37.00 150.00   94
 28  \w   -116.00 -17.00   1.00    1.00    --  -41.49 -37.00-120.00   99
;
_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      0.0276091000
_diffrn_orient_matrix_UB_12      0.1795258000
_diffrn_orient_matrix_UB_13      0.0102195000
_diffrn_orient_matrix_UB_21      0.0660579000
_diffrn_orient_matrix_UB_22      -0.0241393000
_diffrn_orient_matrix_UB_23      -0.1017542000
_diffrn_orient_matrix_UB_31      -0.1873546000
_diffrn_orient_matrix_UB_32      -0.0354417000
_diffrn_orient_matrix_UB_33      -0.0780563000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7447
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.411
_diffrn_reflns_theta_min         3.691
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80431
_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            yellowish
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.4423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             3561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02849_si_003.cif
_cod_data_source_block           20161226a
_cod_depositor_comments
'Adding full bibliography for 4033451--4033455.cif.'
_cod_database_code               4033453
_chemical_oxdiff_formula         c1h1Br1O1
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              6593
_shelx_hkl_checksum              900
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-26
_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 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.745