Ligand-Controlled Regiodivergent π-Allyl Palladium Catalysis Enables a Switch between [3+2] and [3+3] Cycloadditions
Xia, Yu; Bao, Qiao-Fei; Li, Yuke; Wang, Lijing; Zhang, Bo-Sheng; Liu, Hong-Chao; Liang, Yong-Min; Chemical Communications  (2019) –; doi:10.1039/C9CC00611G

data_7123189
_publ_section_title
;
 Ligand-Controlled Regiodivergent \p-Allyl Palladium Catalysis Enables a
 Switch between [3+2] and [3+3] Cycloadditions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00611G
_journal_year                    2019
_chemical_formula_moiety         'C24 H24 O'
_chemical_formula_sum            'C24 H24 O'
_chemical_formula_weight         328.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-01-14 deposited with the CCDC.    2019-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                102.076(15)
_cell_angle_beta                 98.045(16)
_cell_angle_gamma                106.355(16)
_cell_formula_units_Z            2
_cell_length_a                   7.4217(15)
_cell_length_b                   11.0439(17)
_cell_length_c                   12.509(2)
_cell_measurement_reflns_used    674
_cell_measurement_temperature    295.08(10)
_cell_measurement_theta_max      21.6390
_cell_measurement_theta_min      3.9020
_cell_volume                     940.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.08(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega    5.00   51.50   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273   57.0000   30.0000 31

  2 omega  -10.00   95.00   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  120.0000 70

  3 omega   18.00   93.00   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -90.0000 50

  4 omega   11.00   72.50   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -180.0000 41

  5 omega  -20.00   61.00   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000    0.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0939297000
_diffrn_orient_matrix_UB_12      -0.0028502000
_diffrn_orient_matrix_UB_13      -0.0015061000
_diffrn_orient_matrix_UB_21      0.0387228000
_diffrn_orient_matrix_UB_22      0.0681364000
_diffrn_orient_matrix_UB_23      0.0256347000
_diffrn_orient_matrix_UB_31      0.0080474000
_diffrn_orient_matrix_UB_32      -0.0126032000
_diffrn_orient_matrix_UB_33      0.0534902000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5869
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1686
_refine_ls_R_factor_gt           0.0736
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1909
_reflns_number_gt                1577
_reflns_number_total             3699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc00611g2.cif
_cod_data_source_block           xiay_0504
_cod_database_code               7123189
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_olex2_date_sample_data_collection 2018-05-04
_olex2_submission_special_instructions 'No special instructions were received'