Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C–H Alkenylation/Directing Group Migration/Lactonization: A Combined Experimental and Computational Study
Zhao, Fei; Zhou, Zhi; Lu, Yangbin; Qiao, Jin; Zhang, Xiaoning; Gong, Xin; Liu, Siyu; Lin, Shuang; Wu, Xiaowei; Yi, Wei; ACS Catalysis 11 (2021) 13921–13934; doi:10.1021/acscatal.1c03846

data_4519172
_publ_section_title
;
 Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted
 Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C--H
 Alkenylation/Directing Group Migration/Lactonization: A Combined
 Experimental and Computational Study
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              13921
_journal_page_last               13934
_journal_paper_doi               10.1021/acscatal.1c03846
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H16 N2 O4'
_chemical_formula_sum            'C20 H16 N2 O4'
_chemical_formula_weight         348.35
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-17
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.065(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4452(14)
_cell_length_b                   8.0989(7)
_cell_length_c                   17.7051(15)
_cell_measurement_reflns_used    1845
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3940
_cell_measurement_theta_min      3.0330
_cell_volume                     1696.6(3)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -81.00  12.00   1.00    6.00    --  -11.59 -19.00 120.00   93
  2  \w    -86.00 -11.00   1.00    6.00    --  -11.59 -37.00  60.00   75
;
_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      -0.0152044000
_diffrn_orient_matrix_UB_12      0.0390746000
_diffrn_orient_matrix_UB_13      -0.0377057000
_diffrn_orient_matrix_UB_21      0.0578528000
_diffrn_orient_matrix_UB_22      0.0156163000
_diffrn_orient_matrix_UB_23      0.0049059000
_diffrn_orient_matrix_UB_31      0.0040572000
_diffrn_orient_matrix_UB_32      -0.0767709000
_diffrn_orient_matrix_UB_33      -0.0181925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6262
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.420
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79035
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0082(11)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0377P)^2^+0.5112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2186
_reflns_number_total             2988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03846_si_005.cif
_cod_data_source_block           zf-100
_cod_database_code               4519172
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.44
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              90968
_shelx_hkl_checksum              8977
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.774