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_7123190
_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         'C20 H16 O'
_chemical_formula_sum            'C20 H15 O'
_chemical_formula_weight         271.32
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-01-14 deposited with the CCDC.    2019-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                63.150(10)
_cell_angle_beta                 73.885(7)
_cell_angle_gamma                82.681(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7455(6)
_cell_length_b                   9.5862(9)
_cell_length_c                   9.8123(10)
_cell_measurement_reflns_used    2599
_cell_measurement_temperature    120.00(14)
_cell_measurement_theta_max      73.8140
_cell_measurement_theta_min      5.1690
_cell_volume                     705.10(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_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    -66.00  29.00   1.00    1.00    --  -41.14  38.00  30.00   95
  2  \w    -73.00  27.00   1.00    1.00    --  -41.14  77.00 120.00  100
  3  \w    100.00 130.00   1.00    1.00    --   41.14 178.00   0.00   30
  4  \w     90.00 126.00   1.00    1.00    --  107.98  61.00-150.00   36
  5  \w    135.00 170.00   1.00    1.00    --  107.98  61.00-150.00   35
  6  \w    112.00 174.00   1.00    1.00    --  107.98  61.00 -30.00   62
  7  \w     65.00 178.00   1.00    1.00    --  107.98  15.00 -60.00  113
  8  \w     74.00 119.00   1.00    1.00    --  107.98-125.00-180.00   45
  9  \w     41.00  67.00   1.00    1.00    --  107.98-125.00-180.00   26
 10  \w     43.00 134.00   1.00    1.00    --  107.98 -45.00 -90.00   91
 11  \w     66.00 113.00   1.00    1.00    --  107.98 -45.00   0.00   47
 12  \w     59.00 105.00   1.00    1.00    --  107.98 -95.00  30.00   46
 13  \w     34.00 137.00   1.00    1.00    --  107.98 -77.00 150.00  103
 14  \w     29.00 105.00   1.00    1.00    --  107.98 -98.00 -48.00   76
 15  \w   -108.00 -20.00   1.00    1.00    --  -41.14 -38.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0080249000
_diffrn_orient_matrix_UB_12      -0.1697558000
_diffrn_orient_matrix_UB_13      0.0208233000
_diffrn_orient_matrix_UB_21      -0.1821625000
_diffrn_orient_matrix_UB_22      -0.0132825000
_diffrn_orient_matrix_UB_23      0.0642812000
_diffrn_orient_matrix_UB_31      -0.0193281000
_diffrn_orient_matrix_UB_32      0.0587527000
_diffrn_orient_matrix_UB_33      -0.1686472000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4288
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.008
_diffrn_reflns_theta_min         5.172
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0515
_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^)+(0.1010P)^2^+0.1290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2456
_reflns_number_total             2743
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00611g2.cif
_cod_data_source_block           exp_2320
_cod_original_cell_volume        705.10(12)
_cod_database_code               7123190
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H004 of C004, H003 of C003, H00E of C00E, H00F of C00F,
  H00G of C00G, H00H of C00H, H00I of C00I, H00J of C00J, H007 of C007, H008 of
  C008, H00B of C00B, H00C of C00C
 At 1.5 times of:
  H00K of C00L
2.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C003(H003), C004(H004), C007(H007), C008(H008), C00B(H00B), C00C(H00C),
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
2.d Idealised tetrahedral OH refined as rotating group:
 C00L(H00K)
;
_shelx_shelxl_version_number     2014/7
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.860
_oxdiff_exptl_absorpt_empirical_full_min 0.391