Palladium-catalyzed decarboxylation of vinyloxazolidine-2,4-diones used in the divergent reaction with 2-alkynylphenols and 2-alkynylanilines.
Yang, Zhong-Lie; Wang, Zhen-Hua; Zhang, Yan-Ping; You, Yong; Zhao, Jian-Qiang; Zhou, Ming-Qiang; Yuan, Wei-Cheng; Organic & biomolecular chemistry 23 (2025) 3942–3950; doi:10.1039/d5ob00051c

data_7160427
_publ_section_title
;
 Palladium-catalyzed decarboxylation of vinyloxazolidine-2,4-diones used
 in the divergent reaction with 2-alkynylphenols and 2-alkynylanilines.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3942
_journal_page_last               3950
_journal_paper_doi               10.1039/d5ob00051c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C32 H27 N O3'
_chemical_formula_sum            'C32 H27 N O3'
_chemical_formula_weight         473.54
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-14
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-12-16 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.4772(4)
_cell_length_b                   32.4772(4)
_cell_length_c                   5.00380(10)
_cell_measurement_reflns_used    7692
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      73.2940
_cell_measurement_theta_min      2.7090
_cell_volume                     5277.85(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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(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 0.973
_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   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00  90.00   99
  2  \w     16.00 115.00   1.00    1.00    --   40.73  38.00  30.00   99
  3  \w     32.00  96.00   1.00    1.00    --   40.73-139.00  37.00   64
  4  \w    115.00 160.00   1.00    3.72    --  106.95  61.00 -30.00   45
  5  \w     82.00 107.00   1.00    3.72    --  106.95  45.00   0.00   25
  6  \w     35.00 126.00   1.00    3.72    --  106.95 -45.00 120.00   91
  7  \w     94.00 168.00   1.00    3.72    --  106.95 125.00  30.00   74
  8  \w    102.00 156.00   1.00    3.72    --  106.95 125.00  60.00   54
  9  \w     79.00 104.00   1.00    3.72    --  106.95  61.00 -30.00   25
 10  \w     83.00 156.00   1.00    3.72    --  106.95  30.00  30.00   73
;
_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      0.0345973000
_diffrn_orient_matrix_UB_12      0.0180132000
_diffrn_orient_matrix_UB_13      0.1752671000
_diffrn_orient_matrix_UB_21      -0.0133044000
_diffrn_orient_matrix_UB_22      0.0438637000
_diffrn_orient_matrix_UB_23      -0.0792472000
_diffrn_orient_matrix_UB_31      -0.0296028000
_diffrn_orient_matrix_UB_32      0.0013446000
_diffrn_orient_matrix_UB_33      0.2403976000
_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  0.0181
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            9975
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.416
_diffrn_reflns_theta_min         2.721
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64051
_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            'light colourless'
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0465P)^2^+1.0227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.580
_reflns_Friedel_fraction_full    0.789
_reflns_Friedel_fraction_max     0.720
_reflns_number_gt                4438
_reflns_number_total             4583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00051c2.cif
_cod_data_source_block           yx-1
_cod_depositor_comments
'Adding full bibliography for 7160426--7160427.cif.'
_cod_original_cell_volume        5277.85(17)
_cod_database_code               7160427
_shelx_shelxl_version_number     2017/1
_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:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27),
  C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              99937
_shelx_fab_checksum              8385
_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 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.659