Fungicide-inspired precursors of π-allylpalladium intermediates for palladium-catalyzed decarboxylative cycloadditions.
Li, Kuan; Zhen, Shuo; Wang, Wang; Du, Juan; Yu, Songcheng; Wu, Yongjun; Guo, Hongchao; Chemical science 14 (2023) 3024–3029; doi:10.1039/d3sc00112a

data_1568488
_publ_section_title
;
 Fungicide-inspired precursors of &#x3c0;-allylpalladium intermediates for
 palladium-catalyzed decarboxylative cycloadditions.
;
_journal_issue                   11
_journal_name_full               'Chemical science'
_journal_page_first              3024
_journal_page_last               3029
_journal_paper_doi               10.1039/d3sc00112a
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H21 N3 O2'
_chemical_formula_sum            'C27 H21 N3 O2'
_chemical_formula_weight         419.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-12 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.3873(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.30066(14)
_cell_length_b                   8.18447(13)
_cell_length_c                   16.4485(3)
_cell_measurement_reflns_used    14814
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3620
_cell_measurement_theta_min      2.7370
_cell_volume                     1082.41(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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     26.00 120.00   0.50    0.05    --   47.98  77.00 -30.00  188
  2  \w     26.00 120.00   0.50    0.05    --   47.98  77.00  30.00  188
  3  \w     34.00 120.00   0.50    0.05    --   47.98  57.00 120.00  172
  4  \w    -70.00  24.00   0.50    0.05    --  -47.98  78.00 -23.00  188
  5  \w    -69.00 -27.00   0.50    0.07    --  -99.00  61.00 -90.00   84
  6  \w    -69.00 -27.00   0.50    0.07    --  -99.00  61.00-180.00   84
  7  \w    -69.00 -27.00   0.50    0.07    --  -99.00  61.00 -60.00   84
  8  \w   -108.00 -27.00   0.50    0.07    --  -99.00  78.00 -23.00  162
  9  \w    -69.00 -27.00   0.50    0.07    --  -99.00  61.00  60.00   84
 10  \w     84.00 176.00   0.50    0.07    --  104.70  78.00 -23.00  184
 11  \w     94.00 176.00   0.50    0.07    --  104.70  45.00  30.00  164
 12  \w     94.00 176.00   0.50    0.07    --  104.70  45.00  60.00  164
 13  \w     94.00 176.00   0.50    0.07    --  104.70  45.00  90.00  164
 14  \w     90.00 176.00   0.50    0.07    --  104.70  61.00 150.00  172
 15  \w     94.00 178.00   0.50    0.07    --  104.70  15.00  90.00  168
 16  \w    -25.00  28.00   0.50    0.05    --   47.98 -19.00 -90.00  106
 17  \w    -23.00  70.00   0.50    0.05    --   47.98 -78.00-147.00  186
 18  \w     33.00  73.00   0.50    0.07    --  104.70 -61.00-180.00   80
 19  \w     33.00 112.00   0.50    0.07    --  104.70 -78.00-147.00  158
 20  \w     33.00  73.00   0.50    0.07    --  104.70 -61.00   0.00   80
 21  \w     33.00  73.00   0.50    0.07    --  104.70 -61.00  30.00   80
 22  \w     33.00  73.00   0.50    0.07    --  104.70 -61.00  60.00   80
 23  \w     33.00  73.00   0.50    0.07    --  104.70 -61.00  90.00   80
 24  \w     33.00 111.00   0.50    0.07    --  104.70-125.00  30.00  156
 25  \w     33.00 111.00   0.50    0.07    --  104.70-125.00   0.00  156
 26  \w     33.00 111.00   0.50    0.07    --  104.70-125.00 -60.00  156
 27  \w   -111.00 -27.00   0.50    0.07    --  -99.00 125.00-180.00  168
 28  \w   -119.00 -26.00   0.50    0.05    --  -47.98 -77.00-180.00  186
 29  \w   -119.00 -26.00   0.50    0.05    --  -47.98 -77.00 -60.00  186
 30  \w   -171.00 -80.00   0.50    0.07    --  -99.00 -78.00-147.00  182
 31  \w   -172.00 -88.00   0.50    0.07    --  -99.00 -30.00-120.00  168
 32  \w   -172.00 -88.00   0.50    0.07    --  -99.00 -30.00 -90.00  168
 33  \w   -171.00 -88.00   0.50    0.07    --  -99.00 -45.00 -60.00  166
 34  \w   -171.00 -84.00   0.50    0.07    --  -99.00 -61.00 150.00  174
 35  \w   -119.00 -74.00   0.50    0.05    --  -47.98-125.00 -60.00   90
 36  \w   -119.00 -74.00   0.50    0.05    --  -47.98-125.00   0.00   90
 37  \w   -119.00 -74.00   0.50    0.05    --  -47.98-125.00-180.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0449806000
_diffrn_orient_matrix_UB_12      -0.0125070000
_diffrn_orient_matrix_UB_13      0.0964918000
_diffrn_orient_matrix_UB_21      0.1021639000
_diffrn_orient_matrix_UB_22      0.1587126000
_diffrn_orient_matrix_UB_23      0.0061135000
_diffrn_orient_matrix_UB_31      -0.1556700000
_diffrn_orient_matrix_UB_32      0.1004357000
_diffrn_orient_matrix_UB_33      0.0023190000
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20288
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.666
_diffrn_reflns_theta_min         2.773
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1836 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4370
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0475P)^2^+0.1464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                4214
_reflns_number_total             4370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00112a2.cif
_cod_data_source_block           exp_2118_auto
_cod_depositor_comments
'Adding full bibliography for 1568487--1568489.cif.'
_cod_database_code               1568488
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_usercomment     2209175182
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.908
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C29(H29)
2.c X=CH2 refined with riding coordinates:
 C30(H30A,H30B)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_shelx_res_checksum              42597
_shelx_hkl_checksum              79690
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.797