Ketene Aminal Phosphates: Competent Substrates for Enantioselective Pd(0)-Catalyzed C–H Functionalizations
Grosheva, Daria; Cramer, Nicolai; ACS Catalysis 7 (2017) 7417–; doi:10.1021/acscatal.7b02783

data_4514217
_publ_section_title
;
 Ketene Aminal Phosphates: Competent Substrates for Enantioselective
 Pd(0)-Catalyzed C--H Functionalizations
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7417
_journal_paper_doi               10.1021/acscatal.7b02783
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H13 Cl2 N O'
_chemical_formula_sum            'C18 H13 Cl2 N O'
_chemical_formula_weight         330.19
_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_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.78730(10)
_cell_length_b                   12.3631(2)
_cell_length_c                   25.2600(4)
_cell_measurement_reflns_used    13191
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.1450
_cell_measurement_theta_min      3.4850
_cell_volume                     1495.04(5)
_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  'CIFTAB (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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    -30.00  67.00   1.00    1.03    --   40.91 -57.00 -90.00   97
  2  \w     30.00  89.00   1.00    1.03    --   40.91-125.00-180.00   59
  3  \w     65.00 144.00   1.00    6.06    --  111.85 -77.00-150.00   79
  4  \w     68.00  94.00   1.00    6.06    --   94.00  45.00-153.75   26
  5  \w     83.00 110.00   1.00    6.06    --  111.85  61.00-150.00   27
  6  \w    113.00 177.00   1.00    6.06    --  111.85  77.00-180.00   64
  7  \w    126.00 177.00   1.00    6.06    --  111.85  77.00 -90.00   51
  8  \w    118.00 175.00   1.00    6.06    --  111.85  77.00  30.00   57
  9  \w    135.00 162.00   1.00    6.06    --  111.85  77.00  90.00   27
 10  \w    126.00 174.00   1.00    6.06    --  111.85  77.00  60.00   48
 11  \w     94.00 121.00   1.00    1.03    --   62.00  77.00 -83.53   27
 12  \w     79.00 178.00   1.00    6.06    --  111.85  77.00 -30.00   99
 13  \w     88.00 116.00   1.00    1.03    --   54.00  73.00  29.69   28
 14  \w     89.00 115.00   1.00    1.03    --   58.00  76.00 108.14   26
 15  \w     79.00 111.00   1.00    6.06    --  111.85  77.00  60.00   32
 16  \w     85.00 113.00   1.00    6.06    --  111.85  61.00  60.00   28
 17  \w     79.00 104.00   1.00    6.06    --  111.85  77.00  30.00   25
 18  \w     79.00 174.00   1.00    6.06    --  111.85  77.00   0.00   95
 19  \w     84.00 123.00   1.00    6.06    --  111.85  61.00 -60.00   39
 20  \w     80.00 173.00   1.00    6.06    --  111.85  77.00-120.00   93
 21  \w     79.00 148.00   1.00    6.06    --  111.85  77.00-150.00   69
 22  \w     79.00 104.00   1.00    6.06    --  111.85  77.00 -90.00   25
 23  \w     79.00 143.00   1.00    6.06    --  111.85  77.00 -60.00   64
 24  \w     80.00 105.00   1.00    6.06    --  111.85  77.00-180.00   25
 25  \w     60.00 101.00   1.00    6.06    --   90.00  64.00 -91.95   41
 26  \w     41.00  84.00   1.00    1.03    --   74.00  77.00  47.88   43
 27  \w     41.00  67.00   1.00    1.03    --   74.00  77.00   5.74   26
 28  \w     29.00  65.00   1.00    1.03    --   62.00  77.00 -83.53   36
 29  \w     21.00  49.00   1.00    1.03    --   54.00  78.00-146.45   28
 30  \w     21.00  46.00   1.00    1.03    --   54.00  79.00-101.11   25
 31  \w      5.00  33.00   1.00    1.03    --   42.00  89.00 -47.52   28
 32  \w     20.00  46.00   1.00    1.03    --   54.00  81.00 -11.49   26
 33  \w     22.00  64.00   1.00    1.03    --   54.00  73.00  29.69   42
 34  \w     29.00  73.00   1.00    1.03    --   58.00  76.00 108.14   44
 35  \w     30.00 105.00   1.00    1.03    --   62.00  77.00 148.86   75
 36  \w     83.00 171.00   1.00    6.06    --  111.85  61.00 120.00   88
 37  \w     83.00 135.00   1.00    6.06    --  111.85  61.00  90.00   52
 38  \w     84.00 171.00   1.00    6.06    --  111.85  61.00 150.00   87
 39  \w     80.00 107.00   1.00    6.06    --  111.85  77.00  90.00   27
 40  \w     79.00 105.00   1.00    6.06    --  111.85  77.00 120.00   26
 41  \w     11.00  36.00   1.00    1.03    --   46.00  84.00  88.00   25
 42  \w     12.00  37.00   1.00    1.03    --   46.00  82.00 178.49   25
 43  \w    -64.00  31.00   1.00    1.03    --  -40.91  38.00  90.00   95
 44  \w    -44.00 -13.00   1.00    1.03    --  -40.91 -57.00-150.00   31
 45  \w    -30.00  73.00   1.00    1.03    --   40.91 -77.00-180.00  103
 46  \w     30.00 105.00   1.00    6.06    --  111.85 -94.00-180.00   75
 47  \w     59.00 101.00   1.00    6.06    --  111.85-125.00  60.00   42
 48  \w     30.00 105.00   1.00    6.06    --  111.85 -94.00  90.00   75
 49  \w   -112.00 -16.00   1.00    1.03    --  -40.91 -38.00 -60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_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  0.0553
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.978
_diffrn_reflns_theta_min         3.499
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.902
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.368
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.634
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.3502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0853
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3007
_reflns_number_total             3074
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b02783_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4514216--4514217.cif.'
_cod_database_code               4514217
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              71562
_shelx_hkl_checksum              93274