Palladium-catalysed fragmentary esterification-induced allylic alkylation of allyl carbonates and cyclic vinylogous anhydrides.
Wu, Shu-Yi; Li, Yang; Shen, Peng; Yang, Xin-Han; Ran, Guang-Yao; Chemical communications (Cambridge, England) 60 (2024) 1416–1419; doi:10.1039/d3cc05758e

data_7132581
_publ_section_title
;
 Palladium-catalysed fragmentary esterification-induced allylic alkylation
 of allyl carbonates and cyclic vinylogous anhydrides.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1416
_journal_page_last               1419
_journal_paper_doi               10.1039/d3cc05758e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C25 H26 O5'
_chemical_formula_sum            'C25 H26 O5'
_chemical_formula_weight         406.46
_chemical_name_systematic        1
_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     iterative
_audit_creation_date             2023-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-26 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                64.873(2)
_cell_angle_beta                 69.562(2)
_cell_angle_gamma                83.168(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1019(2)
_cell_length_b                   10.7180(3)
_cell_length_c                   11.1905(2)
_cell_measurement_reflns_used    4840
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.1260
_cell_measurement_theta_min      4.5460
_cell_volume                     1027.30(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.959
_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     89.00 132.00   0.50    0.50    --   42.30  65.00 150.00   86
  2  \w     33.00  63.00   0.50    0.50    --   42.30 -65.00 -90.00   60
  3  \w    -47.00  28.00   0.50    0.50    --   42.30 -43.00 -60.00  150
  4  \w     20.00  61.00   0.50    0.50    --   42.30 -82.00  30.00   82
  5  \w    -41.00   3.00   0.50    0.50    --   42.30 -77.00-120.00   88
  6  \w     31.00  63.00   0.50    0.50    --   42.30 -77.00 120.00   64
  7  \w    -39.00  13.00   0.50    0.50    --   42.30 -82.00  60.00  104
  8  \w    -38.00 -12.00   0.50    0.50    --   42.30 -65.00 -90.00   52
  9  \w    -39.00  22.00   0.50    0.50    --   42.30 -77.00 120.00  122
 10  \w     23.00  70.00   0.50    0.50    --   42.30 -82.00  60.00   94
 11  \w     54.00  79.00   0.50    0.50    --   42.30  65.00 150.00   50
 12  \w     11.00  66.00   0.50    0.50    --   42.30 -77.00-120.00  110
 13  \w    -36.00  25.00   0.50    0.50    --   42.30 -65.00-180.00  122
 14  \w     39.00  65.00   0.50    0.50    --   42.30 -43.00 -60.00   52
 15  \w     53.00 120.00   0.50    0.50    --   42.30  77.00-120.00  134
 16  \w     17.00  46.00   0.50    0.50    --   42.30  77.00-120.00   58
 17  \w     36.00  61.00   0.50    0.50    --   42.30 -65.00-180.00   50
 18  \w     45.00  90.00   0.50    0.50    --   93.70 -82.00 120.00   90
 19  \w    141.00 167.00   0.50    0.50    --   93.70  33.00 -60.00   52
 20  \w     60.00  88.00   0.50    0.50    --   93.70  33.00 -60.00   56
 21  \w     63.00  89.00   0.50    0.50    --   93.70  42.00   0.00   52
 22  \w      6.00 104.00   0.50    0.50    --   93.70  25.00  90.00  196
 23  \w     77.00 103.00   0.50    0.50    --   93.70 -82.00-120.00   52
 24  \w     32.00  86.00   0.50    0.50    --   93.70 -82.00  60.00  108
 25  \w      7.00 167.00   0.50    0.50    --   93.70  17.00-120.00  320
 26  \w      7.00 111.00   0.50    0.50    --   93.70 -82.00  90.00  208
 27  \w    126.00 152.00   0.50    0.50    --   93.70  68.00-180.00   52
 28  \w     94.00 119.00   0.50    0.50    --   93.70 -82.00 -60.00   50
 29  \w     15.00 110.00   0.50    0.50    --   93.70 -59.00 -60.00  190
 30  \w    142.00 167.00   0.50    0.50    --   93.70  82.00 150.00   50
 31  \w     60.00  99.00   0.50    0.50    --   93.70 -82.00   0.00   78
 32  \w    110.00 137.00   0.50    0.50    --   93.70  82.00 150.00   54
 33  \w     33.00  99.00   0.50    0.50    --   93.70 -82.00-150.00  132
 34  \w      9.00  62.00   0.50    0.50    --   93.70 -82.00 -60.00  106
 35  \w      5.00  42.00   0.50    0.50    --   93.70 -82.00   0.00   74
 36  \w     65.00 102.00   0.50    0.50    --   93.70 -82.00 150.00   74
 37  \w    124.00 181.00   0.50    0.50    --   93.70  25.00  90.00  114
 38  \w     11.00  69.00   0.50    0.50    --   93.70 -82.00-120.00  116
 39  \w      4.00 113.00   0.50    0.50    --   93.70 -50.00  90.00  218
 40  \w     70.00  95.00   0.50    0.50    --   93.70 -82.00  30.00   50
 41  \w      4.00 104.00   0.50    0.50    --   93.70 -82.00 -81.28  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II 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      -0.1480556000
_diffrn_orient_matrix_UB_12      -0.0506786000
_diffrn_orient_matrix_UB_13      0.1087106000
_diffrn_orient_matrix_UB_21      0.0448028000
_diffrn_orient_matrix_UB_22      -0.1505302000
_diffrn_orient_matrix_UB_23      0.0354492000
_diffrn_orient_matrix_UB_31      0.0508969000
_diffrn_orient_matrix_UB_32      0.0026464000
_diffrn_orient_matrix_UB_33      0.1136469000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8925
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.271
_diffrn_reflns_theta_min         4.559
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0574
_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^)+(0.1001P)^2^+0.1005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1698
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             3616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05758e2.cif
_cod_data_source_block           122_auto
_cod_depositor_comments          'Adding full bibliography for 7132581.cif.'
_cod_original_cell_volume        1027.30(4)
_cod_database_code               7132581
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.957
_diffrn_oxdiff_digest_frames
;
01400a72c4b50f1dd41177f7ea0a92e6c400029b88b
;
_diffrn_oxdiff_digest_hkl
;
010c1f1d239835292370000d27ab75cae3ef30
;
_reflns_odcompleteness_completeness 97.19
_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:
 C1(H1), C4(H4), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B), C17(H17A,H17B),
 C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C11(H11), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_shelx_res_checksum              7160
_shelx_hkl_checksum              23996
_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 17.942
_oxdiff_exptl_absorpt_empirical_full_min 0.404