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_4519174
_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         'C19 H22 N2 O5'
_chemical_formula_sum            'C19 H22 N2 O5'
_chemical_formula_weight         358.38
_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             2020-08-17
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                88.373(7)
_cell_angle_beta                 77.566(7)
_cell_angle_gamma                71.735(8)
_cell_formula_units_Z            2
_cell_length_a                   9.1689(8)
_cell_length_b                   9.1690(8)
_cell_length_c                   11.0996(9)
_cell_measurement_reflns_used    2955
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8930
_cell_measurement_theta_min      4.0540
_cell_volume                     864.57(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 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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.950
_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    -57.00 -11.00   1.00    1.49    --  -41.11 125.00-180.00   46
  2  \w   -116.00 -38.00   1.00    1.49    --  -41.11 -37.00  30.00   78
  3  \w   -120.00  -9.00   1.00    1.49    --  -41.11 -19.00  90.00  111
  4  \w     24.00  97.00   1.00    1.49    --   41.11-125.00   0.00   73
  5  \w     36.00  63.00   1.00    2.00    --  108.20-125.00 -30.00   27
  6  \w     85.00 113.00   1.00    2.00    --  108.20-125.00 -30.00   28
  7  \w     70.00 112.00   1.00    2.00    --  108.20 -45.00 -30.00   42
  8  \w     56.00  84.00   1.00    2.00    --  108.20 -45.00  90.00   28
  9  \w     32.00 129.00   1.00    2.00    --  108.20 -30.00 120.00   97
 10  \w     83.00 171.00   1.00    2.00    --  108.20  45.00 120.00   88
 11  \w     43.00 121.00   1.00    2.00    --  108.20-125.00 120.00   78
 12  \w     38.00  95.00   1.00    2.00    --  108.20-125.00  60.00   57
 13  \w     26.00  76.00   1.00    2.00    --  108.20 -94.00 150.00   50
 14  \w     27.00 159.00   1.00    2.00    --  108.20 -15.00 -60.00  132
 15  \w     54.00 101.00   1.00    2.00    --  108.20 -94.00-180.00   47
 16  \w     35.00  73.00   1.00    1.49    --   41.11-125.00-180.00   38
 17  \w     40.00 137.00   1.00    2.00    --  108.20 -61.00-150.00   97
;
_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      0.0467771000
_diffrn_orient_matrix_UB_12      -0.1103269000
_diffrn_orient_matrix_UB_13      -0.1139235000
_diffrn_orient_matrix_UB_21      0.0977839000
_diffrn_orient_matrix_UB_22      0.0967444000
_diffrn_orient_matrix_UB_23      -0.0715541000
_diffrn_orient_matrix_UB_31      0.1452937000
_diffrn_orient_matrix_UB_32      -0.0991444000
_diffrn_orient_matrix_UB_33      0.0462380000
_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  0.0434
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5816
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.226
_diffrn_reflns_theta_min         4.082
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55745
_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    1.377
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0912P)^2^+0.3574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2803
_reflns_number_total             3353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03846_si_003.cif
_cod_data_source_block           scr-1
_cod_database_code               4519174
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5A), C7(H7)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              63220
_shelx_hkl_checksum              19399
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.454