Enantioselective Inverse Electron Demand (3 + 2) Cycloaddition of Palladium-Oxyallyl Enabled by a Hydrogen-Bond-Donating Ligand.
Zheng, Yin; Qin, Tianzhu; Zi, Weiwei; Journal of the American Chemical Society 143 (2021) 1038–1045; doi:10.1021/jacs.0c11504

data_4135556
_publ_section_title
;
 Enantioselective Inverse Electron Demand (3 + 2) Cycloaddition of
 Palladium-Oxyallyl Enabled by a Hydrogen-Bond-Donating Ligand.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1038
_journal_page_last               1045
_journal_paper_doi               10.1021/jacs.0c11504
_journal_volume                  143
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H16 F N O3'
_chemical_formula_sum            'C19 H16 F N O3'
_chemical_formula_weight         325.33
_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             2019-12-11
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5935)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.9668(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.38073(7)
_cell_length_b                   6.43018(5)
_cell_length_c                   12.80016(10)
_cell_measurement_reflns_used    8437
_cell_measurement_temperature    291.15
_cell_measurement_theta_max      78.7040
_cell_measurement_theta_min      3.6000
_cell_volume                     821.448(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      291.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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   -140.00 -17.00   0.50    0.50    --  -50.10 -72.00  90.00  246
  2  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00 -90.00  238
  3  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00  90.00  238
  4  \w   -143.00 -21.00   0.50    2.00    -- -110.00  72.00-120.00  244
  5  \w   -143.00 -21.00   0.50    2.00    -- -110.00  72.00  60.00  244
  6  \w   -141.00 -21.00   0.50    2.00    -- -110.00  38.00 -90.00  240
  7  \w   -143.00 -21.00   0.50    2.00    -- -110.00  72.00-150.00  244
  8  \w   -199.00 -81.00   0.50    2.00    -- -110.00 -57.00 -90.00  236
  9  \w   -199.00 -81.00   0.50    2.00    -- -110.00 -57.00 120.00  236
 10  \w   -141.00 -21.00   0.50    2.00    -- -110.00  38.00 -60.00  240
 11  \w   -199.00 -79.00   0.50    2.00    -- -110.00 -38.00   0.00  240
 12  \w    -26.00  94.00   0.50    0.50    --    5.00  38.00-150.00  240
 13  \w    -24.00  94.00   0.50    0.50    --    5.00  57.00   0.00  236
 14  \w   -140.00 -17.00   0.50    0.50    --  -50.10 -72.00 -30.00  246
 15  \w   -199.00-155.00   0.50    2.00    -- -110.00 -19.00  90.00   88
 16  \w   -199.00 -59.00   0.50    2.00    -- -110.00 -19.00 -90.00  280
 17  \w   -199.00 -79.00   0.50    2.00    -- -110.00 -38.00-180.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0251564000
_diffrn_orient_matrix_UB_12      0.2173443000
_diffrn_orient_matrix_UB_13      -0.0410888000
_diffrn_orient_matrix_UB_21      -0.1504318000
_diffrn_orient_matrix_UB_22      0.0208656000
_diffrn_orient_matrix_UB_23      -0.0583413000
_diffrn_orient_matrix_UB_31      -0.0235374000
_diffrn_orient_matrix_UB_32      0.0987617000
_diffrn_orient_matrix_UB_33      0.1028681000
_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  0.0206
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10938
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.211
_diffrn_reflns_theta_min         3.592
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1323 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_coef       0.0044(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3331
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0562P)^2^+0.0958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                3241
_reflns_number_total             3331
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11504_si_002.cif
_cod_data_source_block           p20191211b
_cod_database_code               4135556
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H16NO3F
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
;
_shelx_res_checksum              29688
_shelx_hkl_checksum              11739
_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 14.521
_oxdiff_exptl_absorpt_empirical_full_min 0.682