Palladium-catalyzed enantioselective rearrangement of dienyl cyclopropanes.
Xu, Qi; Lu, Chuan-Jun; Guo, Chang-Qiu; Feng, Jia; Liu, Ren-Rong; Chemical science 14 (2023) 3346–3351; doi:10.1039/d2sc06548g

data_1568556
_publ_section_title
;
 Palladium-catalyzed enantioselective rearrangement of dienyl
 cyclopropanes.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3346
_journal_page_last               3351
_journal_paper_doi               10.1039/d2sc06548g
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 O4'
_chemical_formula_sum            'C20 H24 O4'
_chemical_formula_weight         328.39
_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             2022-04-30
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-04 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4788(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.73185(8)
_cell_length_b                   5.91229(7)
_cell_length_c                   19.8978(2)
_cell_measurement_reflns_used    6131
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.2770
_cell_measurement_theta_min      4.4520
_cell_volume                     908.736(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_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     98.00 132.00   0.50    0.50    --   42.30  77.00-180.00   68
  2  \w     80.00 105.00   0.50    0.50    --   42.30  77.00 150.00   50
  3  \w      0.00  79.00   0.50    0.50    --   42.30 -82.00 -90.00  158
  4  \w     89.00 115.00   0.50    0.50    --   42.30  77.00-150.00   52
  5  \w     82.00 124.00   0.50    0.50    --   42.30  77.00  30.00   84
  6  \w     93.00 131.00   0.50    0.50    --   42.30  77.00 -30.00   76
  7  \w     79.00 123.00   0.50    0.50    --  101.60  77.00  30.00   88
  8  \w     12.00 109.00   0.50    0.50    --  101.60 -38.00 -90.00  194
  9  \w     48.00  88.00   0.50    0.50    --  101.60 -50.00 120.00   80
 10  \w     93.00 154.00   0.50    0.50    --  101.60  50.00  90.00  122
 11  \w    113.00 152.00   0.50    0.50    --  101.60  82.00 -60.00   78
 12  \w     12.00 114.00   0.50    0.50    --  101.60 -38.00 120.00  204
 13  \w     91.00 127.00   0.50    0.50    --  101.60 -50.00 120.00   72
 14  \w     12.00  38.00   0.50    0.50    --  101.60 -50.00 120.00   52
 15  \w     89.00 148.00   0.50    0.50    --  101.60  25.00  30.00  118
 16  \w     81.00 122.00   0.50    0.50    --   42.30  77.00   0.00   82
 17  \w     88.00 131.00   0.50    0.50    --   42.30  77.00  60.00   86
 18  \w    -33.00  -1.00   0.50    0.50    --   42.30 -57.00 -30.00   64
 19  \w     24.00  84.00   0.50    0.50    --   42.30  57.00-180.00  120
 20  \w      5.00  59.00   0.50    0.50    --   42.30 -57.00 -30.00  108
 21  \w     89.00 124.00   0.50    0.50    --   42.30  57.00-180.00   70
 22  \w     87.00 115.00   0.50    0.50    --  101.60  50.00 120.00   56
 23  \w    113.00 190.00   0.50    0.50    --  101.60  38.00-180.00  154
 24  \w     50.00 107.00   0.50    0.50    --  101.60 -82.00 -90.00  114
 25  \w     13.00  47.00   0.50    0.50    --  101.60 -82.00 -90.00   68
 26  \w     96.00 127.00   0.50    0.50    --  101.60 -63.00 -90.00   62
 27  \w    140.00 182.00   0.50    0.50    --  101.60  50.00 120.00   84
 28  \w    106.00 151.00   0.50    0.50    --  101.60  38.00-150.00   90
 29  \w     30.00  56.00   0.50    1.00    --  101.60  25.00  90.00   52
 30  \w     65.00 102.00   0.50    1.00    --  101.60  38.00-150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB 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      -0.0685935000
_diffrn_orient_matrix_UB_12      0.1824130000
_diffrn_orient_matrix_UB_13      0.0472438000
_diffrn_orient_matrix_UB_21      -0.1814002000
_diffrn_orient_matrix_UB_22      -0.0220427000
_diffrn_orient_matrix_UB_23      -0.0345135000
_diffrn_orient_matrix_UB_31      -0.0461773000
_diffrn_orient_matrix_UB_32      -0.1848292000
_diffrn_orient_matrix_UB_33      0.0508436000
_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  0.0114
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6616
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.469
_diffrn_reflns_theta_min         4.448
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1293 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(6)
_refine_ls_extinction_coef       0.0266(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0352P)^2^+0.1510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0682
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                3218
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06548g2.cif
_cod_data_source_block           1-67-1
_cod_depositor_comments          'Adding full bibliography for 1568556.cif.'
_cod_original_cell_volume        908.734(17)
_cod_database_code               1568556
_shelx_shelxl_version_number     2017/1
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              47668
_shelx_hkl_checksum              64214
_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.533