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_4519175
_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 O4'
_chemical_formula_sum            'C19 H22 N2 O4'
_chemical_formula_weight         342.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.872(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4740(3)
_cell_length_b                   30.8299(18)
_cell_length_c                   10.1841(6)
_cell_measurement_reflns_used    2056
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      72.2750
_cell_measurement_theta_min      2.8490
_cell_volume                     1668.57(17)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_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      1.00  46.00   1.00    2.00    --   40.73  19.00-150.00   45
  2  \w     57.00 129.00   1.00    3.00    --  107.58 -30.00-180.00   72
  3  \w     81.00 177.00   1.00    3.00    --  107.58  30.00-180.00   96
  4  \w    105.00 131.00   1.00    3.00    --  107.58 -45.00   0.00   26
  5  \w     48.00 108.00   1.00    3.00    --  107.58 -94.00 -60.00   60
  6  \w     26.00  87.00   1.00    2.00    --   40.73-125.00  30.00   61
  7  \w     25.00 104.00   1.00    3.00    --  107.58 -94.00  90.00   79
  8  \w     95.00 145.00   1.00    3.00    --  107.58 125.00   0.00   50
  9  \w    148.00 176.00   1.00    3.00    --  107.58 125.00   0.00   28
 10  \w   -114.00 -17.00   1.00    2.00    --  -40.73 -38.00  60.00   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      0.0294649000
_diffrn_orient_matrix_UB_12      -0.0349654000
_diffrn_orient_matrix_UB_13      0.1107784000
_diffrn_orient_matrix_UB_21      -0.0458376000
_diffrn_orient_matrix_UB_22      -0.0356558000
_diffrn_orient_matrix_UB_23      -0.1090942000
_diffrn_orient_matrix_UB_31      0.2847408000
_diffrn_orient_matrix_UB_32      -0.0021400000
_diffrn_orient_matrix_UB_33      0.0088795000
_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  0.0448
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6063
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.063
_diffrn_reflns_theta_min         2.867
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50020
_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    1.363
_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         0.456
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0754
_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^)+(0.1150P)^2^+0.7501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1950
_refine_ls_wR_factor_ref         0.2075
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2716
_reflns_number_total             3281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03846_si_002.cif
_cod_data_source_block           scr-6-0927
_cod_original_cell_volume        1668.56(18)
_cod_database_code               4519175
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.80
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C8(H8)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              18174
_shelx_hkl_checksum              65415
_olex2_date_sample_data_collection 2020-09-26
_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 1.464
_oxdiff_exptl_absorpt_empirical_full_min 0.589