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_4519173
_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         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-02-26
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_cell_angle_alpha                92.576(8)
_cell_angle_beta                 90.425(7)
_cell_angle_gamma                90.701(8)
_cell_formula_units_Z            4
_cell_length_a                   5.2145(4)
_cell_length_b                   15.0019(17)
_cell_length_c                   21.3360(12)
_cell_measurement_reflns_used    2042
_cell_measurement_temperature    179(40)
_cell_measurement_theta_max      72.5360
_cell_measurement_theta_min      2.9060
_cell_volume                     1667.2(2)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179(40)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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     59.00  95.00   0.75    9.10    --   40.98  19.00  90.00   48
  2  \w     32.00  83.00   0.75   15.00    --  108.20 -30.00  90.00   68
  3  \w    131.00 177.50   0.75   15.00    --  108.20  30.00  90.00   62
  4  \w     45.00 117.00   0.75   15.00    --  108.20-125.00   0.00   96
  5  \w     35.00 139.25   0.75   15.00    --  108.20 -15.00 120.00  139
  6  \w     28.00  82.00   0.75    9.10    --   40.98 -99.00 120.00   72
  7  \w     33.00 127.50   0.75   15.00    --  108.20 -77.00   0.00  126
  8  \w     53.00  81.50   0.75   15.00    --  108.20 -94.00-180.00   38
  9  \w   -111.00 -18.75   0.75    9.10    --  -40.98 -57.00-180.00  123
 10  \w   -115.00 -49.75   0.75    9.10    --  -40.98 -38.00 -90.00   87
 11  \w    -35.00  -2.00   0.75    5.00    --  -41.11 125.00 -60.00   44
 12  \w    -68.00 -41.00   0.75    5.00    --  -41.11 125.00 -60.00   36
 13  \w     12.75  66.00   0.75    5.00    --   41.11 -38.00  30.00   71
 14  \w     23.00  66.50   0.75    5.00    --   41.11-125.00 -30.00   58
 15  \w    -28.00  -1.00   0.75    5.00    --   41.11 -38.00  30.00   36
 16  \w     60.00  86.25   0.75   10.00    --  108.20 -94.00 120.00   35
 17  \w    125.50 178.00   0.75   10.00    --  108.20  61.00 120.00   70
 18  \w     37.00 112.00   0.75   10.00    --  108.20 -30.00 -30.00  100
 19  \w     95.00 120.50   0.75   10.00    --  108.20-125.00 150.00   34
 20  \w     56.00 129.50   0.75   10.00    --  108.20 -45.00-180.00   98
 21  \w     79.00  97.75   0.75   10.00    --  108.20  61.00 120.00   25
;
_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      -0.0088067000
_diffrn_orient_matrix_UB_12      0.0627401000
_diffrn_orient_matrix_UB_13      0.0591047000
_diffrn_orient_matrix_UB_21      0.0459148000
_diffrn_orient_matrix_UB_22      0.0808875000
_diffrn_orient_matrix_UB_23      -0.0406718000
_diffrn_orient_matrix_UB_31      -0.2917453000
_diffrn_orient_matrix_UB_32      0.0095616000
_diffrn_orient_matrix_UB_33      -0.0087674000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_av_unetI/netI     0.1362
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5747
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         2.073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61477
_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    1.272
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         5747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.1135
_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^)+(0.1914P)^2^+0.9327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3191
_refine_ls_wR_factor_ref         0.3639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3476
_reflns_number_total             5747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03846_si_004.cif
_cod_data_source_block           88-2
_cod_database_code               4519173
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 97.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.627(8)
 0.373(8)
2. 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
3.a Ternary CH refined with riding coordinates:
 C16(H16), C37(H37)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C38(H38A,
 H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C14(H14),
 C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C35(H35)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              57188
_shelx_hkl_checksum              54147
_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 3.236
_oxdiff_exptl_absorpt_empirical_full_min 0.379