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_4135554
_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_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.95290(10)
_cell_length_b                   11.39470(10)
_cell_length_c                   15.93630(10)
_cell_measurement_reflns_used    7874
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      79.0670
_cell_measurement_theta_min      4.7880
_cell_volume                     1262.57(2)
_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      294.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.969
_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    -84.00  94.00   0.50    0.50    --    5.00   5.00 159.00  356
  2  \w   -139.00  40.00   0.50    0.50    --  -49.60  -5.00 -19.00  358
  3  \w   -199.00 -53.00   0.50    2.00    -- -110.00  -5.00 -19.00  292
  4  \w    -14.00  40.00   0.50    0.50    --  -49.60  57.00-120.00  108
  5  \w    -78.00  32.00   0.50    0.50    --  -49.60  57.00-150.00  220
  6  \w   -140.00 -97.00   0.50    2.00    -- -110.00 -38.00 -90.00   86
  7  \w   -142.00 -93.00   0.50    2.00    -- -110.00  72.00 -30.00   98
  8  \w   -198.00 -82.00   0.50    2.00    -- -110.00 -57.00 -60.00  232
  9  \w   -142.00 -21.00   0.50    2.00    -- -110.00  72.00 -60.00  242
 10  \w   -102.00 -21.00   0.50    2.00    -- -110.00  72.00   0.00  162
 11  \w   -197.00-150.00   0.50    2.00    -- -110.00 -38.00 -90.00   94
 12  \w   -152.00-126.00   0.50    2.00    -- -110.00 -57.00  30.00   52
 13  \w   -110.00 -85.00   0.50    2.00    -- -110.00   5.00 159.00   50
;
_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      0.0053539000
_diffrn_orient_matrix_UB_12      -0.1109717000
_diffrn_orient_matrix_UB_13      -0.0552099000
_diffrn_orient_matrix_UB_21      0.0127397000
_diffrn_orient_matrix_UB_22      -0.0769514000
_diffrn_orient_matrix_UB_23      0.0792849000
_diffrn_orient_matrix_UB_31      -0.2211046000
_diffrn_orient_matrix_UB_32      -0.0070595000
_diffrn_orient_matrix_UB_33      0.0032247000
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9167
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.308
_diffrn_reflns_theta_min         4.771
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56248
_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    1.290
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_coef       0.031(3)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0852P)^2^+0.1301P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                2547
_reflns_number_total             2593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11504_si_003.cif
_cod_data_source_block           p200615a
_cod_database_code               4135554
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H15NO3
_reflns_odcompleteness_completeness 98.17
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.c X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              91602
_shelx_hkl_checksum              13499
_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 2.246
_oxdiff_exptl_absorpt_empirical_full_min 0.497