Palladium-catalyzed decarboxylative α-allylation of thiazolidinones and azlactones with sulfonamido-substituted acyclic allylic carbonates.
Rao, Han-Wen; Zhao, Tian-Lan; Wang, Long; Deng, Hong-Dan; Zhang, Yan-Ping; You, Yong; Wang, Zhen-Hua; Zhao, Jian-Qiang; Yuan, Wei-Cheng; Organic & biomolecular chemistry 21 (2023) 8593–8602; doi:10.1039/d3ob01404e

data_7159588
_publ_section_title
;
 Palladium-catalyzed decarboxylative &#x3b1;-allylation of thiazolidinones
 and azlactones with sulfonamido-substituted acyclic allylic carbonates.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8593
_journal_page_last               8602
_journal_paper_doi               10.1039/d3ob01404e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C27 H25 Cl N2 O4 S'
_chemical_formula_sum            'C27 H25 Cl N2 O4 S'
_chemical_formula_weight         509.00
_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     dual
_audit_creation_date             2023-05-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-29 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                67.633(2)
_cell_angle_beta                 85.5240(10)
_cell_angle_gamma                70.287(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1642(2)
_cell_length_b                   11.1077(2)
_cell_length_c                   12.6071(2)
_cell_measurement_reflns_used    10345
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      71.2000
_cell_measurement_theta_min      4.5660
_cell_volume                     1237.05(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_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     12.00 132.00   0.50    0.50    --   42.10  57.00-180.00  240
  2  \w     -6.00  78.00   0.50    0.50    --   42.10 -82.00  30.00  168
  3  \w     27.00  86.00   0.50    0.50    --   42.10 -82.00-150.00  118
  4  \w     80.00 105.00   0.50    0.50    --   42.10  77.00 -90.00   50
  5  \w     11.00  87.00   0.50    0.50    --   42.10 -38.00 -30.00  152
  6  \w    106.00 132.00   0.50    0.50    --   42.10  77.00 -60.00   52
  7  \w    -46.00   2.00   0.50    0.50    --   42.10 -38.00 -30.00   96
  8  \w     83.00 130.00   0.50    0.50    --   42.10  77.00  60.00   94
  9  \w      2.00  67.00   0.50    0.50    --   42.10 -57.00-150.00  130
 10  \w     16.00 126.00   0.50    0.50    --  101.60 -82.00-180.00  220
 11  \w     71.00  97.00   0.50    0.50    --  101.60 -82.00 -90.00   52
 12  \w     47.00 145.00   0.50    0.50    --  101.60 -82.00-120.00  196
 13  \w     75.00 101.00   0.50    0.50    --  101.60 -82.00-150.00   52
 14  \w     73.00  99.00   0.50    0.50    --  101.60 -82.00 -30.00   52
 15  \w     12.00  65.00   0.50    0.50    --  101.60 -82.00 -90.00  106
 16  \w     63.00  89.00   0.50    0.50    --  101.60 -82.00 150.00   52
 17  \w     25.00 191.00   0.50    0.50    --  101.60  25.00   0.00  332
 18  \w     27.00 124.00   0.50    0.50    --  101.60 -82.00  30.00  194
 19  \w     84.00 148.00   0.50    0.50    --  101.60  64.00  90.00  128
 20  \w     46.00 132.00   0.50    0.50    --  101.60 -82.00 -60.00  172
 21  \w     15.00  51.00   0.50    0.50    --  101.60 -64.00 150.00   72
 22  \w     79.00 105.00   0.50    0.50    --  101.60 -64.00 150.00   52
 23  \w     13.00  87.00   0.50    0.50    --  101.60 -64.00  60.00  148
 24  \w    131.00 156.00   0.50    0.50    --  101.60  82.00   0.00   50
 25  \w     53.00  79.00   0.50    0.50    --  101.60 -50.00-120.00   52
 26  \w     96.00 132.00   0.50    0.50    --  101.60 -50.00-120.00   72
 27  \w     73.00 188.00   0.50    0.50    --  101.60  50.00-120.00  230
 28  \w     93.00 122.00   0.50    0.50    --  101.60  82.00   0.00   58
 29  \w     12.00  45.00   0.50    0.50    --  101.60 -82.00 150.00   66
 30  \w     73.00 106.00   0.50    0.50    --  101.60 -82.00  90.00   66
 31  \w    134.00 181.00   0.50    0.50    --  101.60  50.00-150.00   94
 32  \w    -23.00   4.00   0.50    0.50    --   42.10 -57.00-180.00   54
 33  \w    155.00 181.00   0.50    0.50    --  101.60  82.00 -30.00   52
 34  \w    166.00 191.00   0.50    0.50    --  101.60 -12.00 -60.00   50
 35  \w     61.00  87.00   0.50    0.50    --  101.60 -12.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0525949000
_diffrn_orient_matrix_UB_12      -0.1401463000
_diffrn_orient_matrix_UB_13      -0.0140050000
_diffrn_orient_matrix_UB_21      -0.0353096000
_diffrn_orient_matrix_UB_22      -0.0710469000
_diffrn_orient_matrix_UB_23      0.1244271000
_diffrn_orient_matrix_UB_31      -0.1483103000
_diffrn_orient_matrix_UB_32      0.0249370000
_diffrn_orient_matrix_UB_33      -0.0429086000
_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  0.0207
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12363
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.516
_diffrn_reflns_theta_min         3.798
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.5594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4510
_reflns_number_total             4679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01404e2.cif
_cod_data_source_block           0518zjq-1
_cod_depositor_comments          'Adding full bibliography for 7159588.cif.'
_cod_original_cell_volume        1237.06(4)
_cod_database_code               7159588
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S'
_olex2_refinement_description
;
1. 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
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              88670
_shelx_hkl_checksum              70883
_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 2.292
_oxdiff_exptl_absorpt_empirical_full_min 0.574