Lewis Acid/Brønsted Base-Assisted Palladium Catalysis: Stereoselective Construction of Skeletally Diverse Spiro-Ketolactams from Vinylethylene Carbonates
Huang, Qian-Wei; Qi, Ting; Liu, Yue; Zhang, Xiang; Li, Qing-Zhu; Gou, Chuan; Tao, Ying-Mao; Leng, Hai-Jun; Li, Jun-Long; ACS Catalysis  (2021) 10148–10158; doi:10.1021/acscatal.1c01724

data_4518925
_publ_section_title
;
 Lewis Acid/Br\/onsted Base-Assisted Palladium Catalysis: Stereoselective
 Construction of Skeletally Diverse Spiro-Ketolactams from Vinylethylene
 Carbonates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10148
_journal_page_last               10158
_journal_paper_doi               10.1021/acscatal.1c01724
_journal_year                    2021
_chemical_formula_moiety         'C28 H24 Cl N O3, C H Cl3'
_chemical_formula_sum            'C29 H25 Cl4 N O3'
_chemical_formula_weight         577.30
_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     direct
_audit_creation_date             2019-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                82.201(4)
_cell_angle_beta                 85.137(5)
_cell_angle_gamma                66.119(6)
_cell_formula_units_Z            2
_cell_length_a                   10.2188(7)
_cell_length_b                   10.9667(6)
_cell_length_c                   13.7130(7)
_cell_measurement_reflns_used    5009
_cell_measurement_temperature    294.0(3)
_cell_measurement_theta_max      71.3760
_cell_measurement_theta_min      4.4540
_cell_volume                     1391.45(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      294.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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    -53.00  31.00   1.00    4.69    --  -36.54  57.00 150.00   84
  2  \w    -90.00  -2.00   1.00    4.69    --  -36.54 125.00 150.00   88
  3  \w   -104.00 -10.00   1.00    4.69    --  -36.54 -77.00  30.00   94
  4  \w   -104.00 -10.00   1.00    4.69    --  -36.54 -77.00-150.00   94
  5  \w   -104.00 -20.00   1.00    4.69    --  -36.54 -57.00 -90.00   84
  6  \w     23.00  90.00   1.00    4.69    --   36.54-125.00  60.00   67
  7  \w     20.00 104.00   1.00    4.69    --   36.54  57.00  60.00   84
  8  \w     20.00 104.00   1.00    4.69    --   36.54  57.00 -30.00   84
  9  \w     39.00 124.00   1.00   18.78    --  106.21 -61.00  30.00   85
 10  \w     37.00 109.00   1.00   18.78    --  106.21 -94.00   0.00   72
 11  \w     57.00 150.00   1.00   18.78    --  106.21 178.00 -30.00   93
 12  \w     36.00 113.00   1.00   18.78    --  106.21-111.00 120.00   77
 13  \w     36.00 113.00   1.00   18.78    --  106.21-113.00 -51.00   77
 14  \w     38.00 124.00   1.00   18.78    --  106.21 -45.00-180.00   86
 15  \w     88.00 173.00   1.00   18.78    --  106.21  61.00 150.00   85
 16  \w     36.00 128.00   1.00   18.78    --  106.21 -30.00 120.00   92
 17  \w    100.00 176.00   1.00   18.78    --  106.21 111.00  90.00   76
 18  \w     38.00 124.00   1.00   18.78    --  106.21 -45.00 -60.00   86
 19  \w     79.00 174.00   1.00   18.78    --  106.21  77.00  90.00   95
 20  \w     39.00 133.00   1.00   18.78    --  106.21 -77.00 150.00   94
 21  \w     37.00 175.00   1.00   18.78    --  106.21   0.00 -60.00  138
 22  \w    -53.00  31.00   1.00    4.69    --  -36.54  57.00  60.00   84
 23  \w   -106.00 -18.00   1.00    4.69    --  -36.54 -38.00  90.00   88
 24  \w    -63.00  31.00   1.00    4.69    --  -36.54  77.00 -60.00   94
 25  \w     10.00 100.00   1.00    4.69    --   36.54  77.00-180.00   90
 26  \w     10.00 104.00   1.00    4.69    --   36.54  77.00   0.00   94
 27  \w     10.00 104.00   1.00    4.69    --   36.54  77.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0336004000
_diffrn_orient_matrix_UB_12      -0.0274006000
_diffrn_orient_matrix_UB_13      0.1104313000
_diffrn_orient_matrix_UB_21      -0.1563566000
_diffrn_orient_matrix_UB_22      0.1004388000
_diffrn_orient_matrix_UB_23      -0.0141407000
_diffrn_orient_matrix_UB_31      -0.0404525000
_diffrn_orient_matrix_UB_32      -0.1142753000
_diffrn_orient_matrix_UB_33      -0.0218312000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.574
_diffrn_reflns_theta_min         4.437
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       needle
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0753
_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^)+(0.1459P)^2^+0.5880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.2379
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4290
_reflns_number_total             5331
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01724_si_003.cif
_cod_data_source_block           ljl-hqw-1216
_cod_original_cell_volume        1391.45(15)
_cod_database_code               4518925
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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
2.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00G(H00G), C00V(H00V)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00K(H00D,H00F), C00L(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011)
;
_shelx_res_checksum              74823
_shelx_hkl_checksum              98880
_olex2_date_sample_data_collection 2019-12-16
_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 3.155
_oxdiff_exptl_absorpt_empirical_full_min 0.566