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_4033451
_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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1653(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.48695(6)
_cell_length_b                   21.5010(3)
_cell_length_c                   13.58645(16)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      73.2430
_cell_measurement_theta_min      5.2330
_cell_volume                     1596.35(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_environment      N~2~
_diffrn_ambient_temperature      100.02(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 0.972
_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    -22.00  29.00   1.00    1.00    --  -41.49  57.00   0.00   51
  2  \w    -51.00 -25.00   1.00    1.00    --  -41.49  57.00   0.00   26
  3  \w   -117.00  -9.00   1.00    1.00    --  -41.49 -77.00-120.00  108
  4  \w     65.00  97.00   1.00    1.00    --   41.49-125.00-180.00   32
  5  \w     84.00 122.00   1.00    1.00    --  107.52 -61.00 -60.00   38
  6  \w    125.00 176.00   1.00    1.00    --  107.52  30.00 -60.00   51
  7  \w     98.00 142.00   1.00    1.00    --  107.52 125.00-180.00   44
  8  \w     84.00 178.00   1.00    1.00    --  107.52  45.00 -90.00   94
  9  \w     31.00 109.00   1.00    1.00    --  107.52 -94.00 -60.00   78
 10  \w     28.00  95.00   1.00    1.00    --  107.52 -94.00-180.00   67
 11  \w     34.00  96.00   1.00    1.00    --  107.52 -94.00 120.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1092460000
_diffrn_orient_matrix_UB_12      0.0660838000
_diffrn_orient_matrix_UB_13      0.0024334000
_diffrn_orient_matrix_UB_21      0.2085092000
_diffrn_orient_matrix_UB_22      -0.0216425000
_diffrn_orient_matrix_UB_23      0.0757382000
_diffrn_orient_matrix_UB_31      0.1550034000
_diffrn_orient_matrix_UB_32      -0.0173958000
_diffrn_orient_matrix_UB_33      -0.0849454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6212
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.450
_diffrn_reflns_theta_min         3.860
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85397
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0436P)^2^+0.6019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2915
_reflns_number_total             3122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02849_si_006.cif
_cod_data_source_block           20170329c
_cod_depositor_comments
'Adding full bibliography for 4033451--4033455.cif.'
_cod_database_code               4033451
_chemical_oxdiff_formula         c1h1o1
_reflns_odcompleteness_completeness 99.90
_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:
 C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c 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.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              42328
_shelx_hkl_checksum              2245
_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 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.668