Pd-catalyzed decarboxylative 1,4-addition reactions of benzofuran-based azadienes with allyl phenyl carbonates.
Cai, Lu-Yu; Song, Xiu-Qing; Wang, Kuo; Zhang, Yue; Zhao, Hong-Wu; Organic & biomolecular chemistry 21 (2023) 6556–6564; doi:10.1039/d3ob00968h

data_7159490
_publ_section_title
;
 Pd-catalyzed decarboxylative 1,4-addition reactions of benzofuran-based
 azadienes with allyl phenyl carbonates.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6556
_journal_page_last               6564
_journal_paper_doi               10.1039/d3ob00968h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C31 H27 N O4 S'
_chemical_formula_sum            'C31 H27 N O4 S'
_chemical_formula_weight         509.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-29 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                83.169(5)
_cell_angle_beta                 72.223(6)
_cell_angle_gamma                71.119(6)
_cell_formula_units_Z            2
_cell_length_a                   10.3471(7)
_cell_length_b                   11.5677(8)
_cell_length_c                   12.0428(7)
_cell_measurement_reflns_used    8010
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.3140
_cell_measurement_theta_min      1.8000
_cell_volume                     1298.42(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.898
_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   -115.00  65.00   1.00    4.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    4.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    4.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0160919000
_diffrn_orient_matrix_UB_12      0.0187321000
_diffrn_orient_matrix_UB_13      -0.0537710000
_diffrn_orient_matrix_UB_21      0.0444524000
_diffrn_orient_matrix_UB_22      0.0381746000
_diffrn_orient_matrix_UB_23      -0.0120226000
_diffrn_orient_matrix_UB_31      0.0589441000
_diffrn_orient_matrix_UB_32      -0.0489230000
_diffrn_orient_matrix_UB_33      -0.0281368000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19778
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.884
_diffrn_reflns_theta_min         1.776
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         8711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0761
_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^)+(0.0873P)^2^+0.6661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.2166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5093
_reflns_number_total             8711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00968h2.cif
_cod_data_source_block           r20211201b
_cod_depositor_comments          'Adding full bibliography for 7159490.cif.'
_cod_database_code               7159490
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C26(H26), C27(H27), C30(H30)
2.d X=CH2 refined with riding coordinates:
 C31(H31A,H31B)
2.e Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              8358
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.723