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_7123191
_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 H18 O'
_chemical_formula_sum            'C24 H18 O'
_chemical_formula_weight         322.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-16
_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                90.00
_cell_angle_beta                 98.487(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.5655(10)
_cell_length_b                   6.0870(3)
_cell_length_c                   27.2088(14)
_cell_measurement_reflns_used    1549
_cell_measurement_temperature    293.36(10)
_cell_measurement_theta_max      24.1290
_cell_measurement_theta_min      3.5950
_cell_volume                     3368.8(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      293.36(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  -16.00   18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1983  -99.0000   90.0000 34

  2 omega   51.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   57.0000  -30.0000 45

  3 omega  -19.00   78.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108  -99.0000  -60.0000 97

  4 omega   57.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108 -178.0000   30.0000 26

  5 omega  -21.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   38.0000  120.0000 88
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0067288000
_diffrn_orient_matrix_UB_12      0.1142905000
_diffrn_orient_matrix_UB_13      0.0000258000
_diffrn_orient_matrix_UB_21      0.0097512000
_diffrn_orient_matrix_UB_22      -0.0096227000
_diffrn_orient_matrix_UB_23      -0.0238476000
_diffrn_orient_matrix_UB_31      -0.0327923000
_diffrn_orient_matrix_UB_32      0.0206007000
_diffrn_orient_matrix_UB_33      -0.0112378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6751
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98068
_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    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0459P)^2^+0.1636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                2083
_reflns_number_total             3323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc00611g2.cif
_cod_data_source_block           xiay_0514
_cod_original_cell_volume        3368.7(3)
_cod_database_code               7123191
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C24(H24)
;
_olex2_date_sample_data_collection 2018-05-14
_olex2_submission_special_instructions 'No special instructions were received'