Palladium/Xu-Phos-Catalyzed Asymmetric Carboamination towards Isoxazolidines and Pyrrolidines
Wang, Yuzhuo; Wang, Lei; Chen, Mingjie; Tu, Youshao; Liu, Yu; Zhang, Junliang; Chemical Science  (2021) –; doi:10.1039/D1SC01337H

data_1562386
_publ_section_title
;
 Palladium/Xu-Phos-Catalyzed Asymmetric Carboamination towards
 Isoxazolidines and Pyrrolidines
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01337H
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H20 Cl N O3'
_chemical_formula_sum            'C15 H20 Cl N O3'
_chemical_formula_weight         297.783
_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'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-03
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-01-03 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5536(1)
_cell_length_b                   10.5647(1)
_cell_length_c                   15.0670(1)
_cell_measurement_reflns_used    27717
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.1260
_cell_measurement_theta_min      4.6510
_cell_volume                     1520.73(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9944
_diffrn_measured_fraction_theta_max 0.9944
_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     35.00  76.00   1.00    1.00    --    0.00  38.00 -90.00   41
  2  \w     60.00  85.00   1.00    1.00    --    0.00  19.00 120.00   25
  3  \w     53.00  84.00   1.00    1.00    --    0.00  77.00-180.00   31
  4  \w    -16.00  20.00   1.00    1.00    --    0.00 -57.00 -90.00   36
  5  \w      8.00  66.00   1.00    1.00    --    0.00  82.00  30.00   58
  6  \w     52.00  78.00   1.00    1.00    --    0.00  38.00   0.00   26
  7  \w    -18.00  49.00   1.00    1.00    --    0.00  38.00   0.00   67
  8  \w    -30.00  -3.00   1.00    1.00    --    0.00  82.00  30.00   27
  9  \w    -84.00 -41.00   1.00    1.00    --    0.00 -57.00 -90.00   43
 10  \w     -9.00  25.00   1.00    1.00    --    0.00  38.00 -90.00   34
 11  \w    -22.00  46.00   1.00    1.00    --    0.00  19.00 120.00   68
 12  \w     29.00  81.00   1.00    1.00    --    0.00  38.00 150.00   52
 13  \w    -29.00   8.00   1.00    1.00    --    0.00  77.00-180.00   37
 14  \w    -19.00  21.00   1.00    1.00    --    0.00  38.00 150.00   40
 15  \w     65.00  90.00   1.00    1.00    --   95.80  82.00 150.00   25
 16  \w     26.00 128.00   1.00    1.00    --   95.80 -82.00-150.00  102
 17  \w     73.00 115.00   1.00    1.00    --   95.80  55.00 135.18   42
 18  \w     81.00 127.00   1.00    1.00    --   95.80 -82.00  60.00   46
 19  \w     64.00 110.00   1.00    1.00    --   95.80 -61.00-150.00   46
 20  \w     69.00  95.00   1.00    1.00    --   95.80  66.00   6.49   26
 21  \w     72.00 121.00   1.00    1.00    --   95.80  59.00   7.14   49
 22  \w     63.00  94.00   1.00    1.00    --   95.80  82.00-180.00   31
 23  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 24  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 25  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 26  \w     75.00 168.00   1.00    1.00    --   95.80  45.00-120.00   93
 27  \w     72.00 185.00   1.00    1.00    --   95.80  61.00 -90.00  113
 28  \w     67.00  93.00   1.00    1.00    --   95.80  82.00-120.00   26
 29  \w     65.00  93.00   1.00    1.00    --   95.80  77.00 120.00   28
 30  \w      6.00 117.00   1.00    1.00    --   95.80 -61.00   0.00  111
 31  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-120.00   26
 32  \w     66.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   25
 33  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 34  \w    126.00 170.00   1.00    1.00    --   95.80  82.00 -60.00   44
 35  \w    143.00 182.00   1.00    1.00    --   95.80  59.00-102.36   39
 36  \w    143.00 169.00   1.00    1.00    --   95.80  74.00  84.62   26
 37  \w     72.00 114.00   1.00    1.00    --   95.80  61.00 -60.00   42
 38  \w     75.00 173.00   1.00    1.00    --   95.80  45.00   0.00   98
 39  \w     71.00 184.00   1.00    1.00    --   95.80  61.00  90.00  113
 40  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 41  \w      8.00  34.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 42  \w     41.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00   87
 43  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -60.00   26
 44  \w     75.00 185.00   1.00    1.00    --   95.80  45.00-150.00  110
 45  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 46  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 47  \w      8.00 127.00   1.00    1.00    --   95.80 -82.00   0.00  119
 48  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 49  \w     63.00  99.00   1.00    1.00    --   95.80  82.00 120.00   36
 50  \w     75.00 133.00   1.00    1.00    --   95.80  45.00  90.00   58
 51  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 52  \w     77.00 103.00   1.00    1.00    --   95.80  45.00-180.00   26
 53  \w     72.00  98.00   1.00    1.00    --   95.80  59.00-102.36   26
 54  \w     75.00 154.00   1.00    1.00    --   95.80  45.00  60.00   79
 55  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 56  \w     65.00  91.00   1.00    1.00    --   95.80  82.00   0.00   26
 57  \w    110.00 184.00   1.00    1.00    --   95.80  82.00   0.00   74
 58  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 59  \w     38.00 109.00   1.00    1.00    --   95.80 -82.00 150.00   71
 60  \w     76.00 160.00   1.00    1.00    --   95.80  30.00-180.00   84
 61  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 62  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 63  \w    120.00 145.00   1.00    1.00    --   95.80  55.00 135.18   25
 64  \w     66.00  91.00   1.00    1.00    --   95.80  74.00  84.62   25
 65  \w    119.00 185.00   1.00    1.00    --   95.80  43.00 -21.36   66
 66  \w     75.00 111.00   1.00    1.00    --   95.80  43.00 -21.36   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0239517000
_diffrn_orient_matrix_UB_12      0.1388604000
_diffrn_orient_matrix_UB_13      0.0271592000
_diffrn_orient_matrix_UB_21      0.0343540000
_diffrn_orient_matrix_UB_22      -0.0427710000
_diffrn_orient_matrix_UB_23      0.0952586000
_diffrn_orient_matrix_UB_31      0.1558136000
_diffrn_orient_matrix_UB_32      -0.0119397000
_diffrn_orient_matrix_UB_33      -0.0252178000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.9944
_diffrn_reflns_Laue_measured_fraction_max 0.9944
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36528
_diffrn_reflns_point_group_measured_fraction_full 0.9949
_diffrn_reflns_point_group_measured_fraction_max 0.9926
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         5.11
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.285
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             635.363
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.1329
_refine_diff_density_min         -0.2676
_refine_diff_density_rms         0.0342
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.017(9)
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             8.6501
_refine_ls_goodness_of_fit_ref   1.0359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0359
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.0054
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.3555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0587
_reflns_Friedel_coverage         0.990
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                3063
_reflns_number_total             3079
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1sc01337h2.cif
_cod_data_source_block           exp_1472
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1562386
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C7(H7a,H7b), C10(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C1(H1)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c)
;
_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 2.440
_oxdiff_exptl_absorpt_empirical_full_min 0.667