DTBP-mediated cross-dehydrogenative coupling of 3-aryl benzofuran-2(3H)-ones with toluenes/phenols for all-carbon quaternary centers
Tong, Zhou; Peng, Xinju; Tang, Zhi; Yang, Weijun; Deng, Wei; Yin, Shuang-Feng; Kambe, Nobuaki; Qiu, Renhua; RSC Advances 12 (2022) 35215–35220; doi:10.1039/D2RA06231C

data_7245993
_publ_section_title
;
 DTBP-mediated cross-dehydrogenative coupling of 3-aryl
 benzofuran-2(3H)-ones with toluenes/phenols for all-carbon quaternary
 centers
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              35215
_journal_page_last               35220
_journal_paper_doi               10.1039/D2RA06231C
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-27 deposited with the CCDC.	2022-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.571(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6597(9)
_cell_length_b                   9.1073(4)
_cell_length_c                   10.5974(6)
_cell_measurement_reflns_used    3745
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1210
_cell_measurement_theta_min      2.4330
_cell_volume                     1602.78(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.882
_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    -33.00  58.00   1.00    2.50    --  -11.43  57.00  30.00   91
  2  \w    -74.00  17.00   1.00    2.50    --  -11.43 -77.00 120.00   91
  3  \w    -81.00  17.00   1.00    2.50    --  -11.43 -57.00-120.00   98
;
_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      0.0322620000
_diffrn_orient_matrix_UB_12      -0.0435437000
_diffrn_orient_matrix_UB_13      -0.0189436000
_diffrn_orient_matrix_UB_21      0.0012552000
_diffrn_orient_matrix_UB_22      0.0429513000
_diffrn_orient_matrix_UB_23      -0.0555772000
_diffrn_orient_matrix_UB_31      0.0279459000
_diffrn_orient_matrix_UB_32      0.0483326000
_diffrn_orient_matrix_UB_33      0.0324650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5926
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.646
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.301
_diffrn_reflns_theta_min         2.453
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0376P)^2^+0.4721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.464
_reflns_Friedel_fraction_full    0.554
_reflns_Friedel_fraction_max     0.410
_reflns_number_gt                2758
_reflns_number_total             2822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra06231c2.cif
_cod_data_source_block           tz-1
_cod_database_code               7245993
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.94
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C19(H19), C17(H17), C4(H4), C2(H2), C3(H3), C5(H5),
 C12(H12), C13(H13), C20(H20), C14(H14), C11(H11)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.764