Palladium(II)-catalyzed Oxidative C(sp3)‒P Bond Formation via C(sp3)‒H Bond Activation
Chen, Lijin; Zhou, Zhenfei; Zhang, Saifei; Li, Xiaoqian; Ma, Xuebing; Dong, Jiaxing; Chemical Communications  (2019) –; doi:10.1039/C9CC07637A

data_7124349
_publ_section_title
;
 Palladium(II)-catalyzed Oxidative C(sp3)--P Bond Formation via C(sp3)--H
 Bond Activation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07637A
_journal_year                    2019
_chemical_formula_moiety         'C24 H22 N O3 P Pd'
_chemical_formula_sum            'C24 H22 N O3 P Pd'
_chemical_formula_weight         509.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2019-04-25 deposited with the CCDC.    2019-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                114.219(4)
_cell_angle_beta                 99.926(3)
_cell_angle_gamma                98.501(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8937(4)
_cell_length_b                   10.7491(4)
_cell_length_c                   12.9531(5)
_cell_measurement_reflns_used    22777
_cell_measurement_temperature    282(3)
_cell_measurement_theta_max      28.2120
_cell_measurement_theta_min      3.5810
_cell_volume                     1078.99(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      282(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.916
_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  10.00   1.00    2.11    --  -16.50 -77.00-150.00   94
  2  \w    -84.00   0.00   1.00    2.11    --  -16.50 -57.00  90.00   84
  3  \w    -51.00  33.00   1.00    2.11    --   16.50 -57.00-150.00   84
  4  \w    -10.00  84.00   1.00    2.11    --   16.50  77.00 150.00   94
  5  \w    -20.00  55.00   1.00    2.11    --   16.50 -99.00 -60.00   75
  6  \w    -20.00  55.00   1.00    2.11    --   16.50 -99.00  90.00   75
  7  \w    -20.00  55.00   1.00    2.11    --   16.50 -99.00   0.00   75
  8  \w     35.00  89.00   1.00    2.11    --   16.50 178.00-120.00   54
  9  \w     -2.00  80.00   1.00    2.11    --   16.50  38.00 -60.00   82
 10  \w      0.00  84.00   1.00    2.11    --   16.50  57.00   0.00   84
 11  \w    -76.00 -23.00   1.00    2.11    --  -16.50 -57.00  30.00   53
 12  \w    -67.00 -42.00   1.00    2.11    --  -16.50 119.00  53.58   25
 13  \w    -69.00 -44.00   1.00    2.11    --  -16.50 123.00 156.99   25
 14  \w     -9.00  63.00   1.00    2.11    --   16.35-112.00 -36.60   72
 15  \w     35.00  89.00   1.00    2.11    --   16.35 178.00 -90.00   54
 16  \w    -86.00  53.00   1.00    2.11    --  -16.50   0.00 150.00  139
 17  \w    -73.00 -27.00   1.00    2.11    --  -16.50 131.00 -19.63   46
 18  \w    -43.00  51.00   1.00    2.11    --  -16.50  77.00-150.00   94
 19  \w    -69.00 -22.00   1.00    2.11    --  -16.50 123.00  44.96   47
 20  \w    -69.00 -22.00   1.00    2.11    --  -16.50 123.00 156.99   47
 21  \w    -75.00 -29.00   1.00    2.11    --  -16.50 133.00 177.38   46
 22  \w    -75.00 -29.00   1.00    2.11    --  -16.50 133.00  85.44   46
 23  \w    -84.00   0.00   1.00    2.11    --  -16.50 -57.00   0.00   84
 24  \w    -53.00  86.00   1.00    2.11    --   16.35   0.00-150.00  139
 25  \w    -53.00  86.00   1.00    2.11    --   16.35   0.00-120.00  139
 26  \w    -53.00  86.00   1.00    2.11    --   16.35   0.00-180.00  139
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0135998000
_diffrn_orient_matrix_UB_12      -0.0679052000
_diffrn_orient_matrix_UB_13      -0.0471508000
_diffrn_orient_matrix_UB_21      -0.0738464000
_diffrn_orient_matrix_UB_22      0.0068583000
_diffrn_orient_matrix_UB_23      -0.0251426000
_diffrn_orient_matrix_UB_31      0.0364633000
_diffrn_orient_matrix_UB_32      0.0301065000
_diffrn_orient_matrix_UB_33      -0.0317457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            46678
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.464
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.569
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.346
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0610P)^2^+1.5590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4895
_reflns_number_total             5484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07637a2.cif
_cod_data_source_block           exp_1928
_cod_original_cell_volume        1078.99(8)
_cod_database_code               7124349
_chemical_oxdiff_formula         'C1 H1 O1 N1 P1 Pd1'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C16) = Uanis(C14) = Uanis(C17) = Uanis(C13) = Uanis(C12)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C13(H13), C14(H14), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
3.c Fitted hexagon refined as free rotating group:
 C15(C16,C17,C12,C13,C14)
;
_shelx_shelxl_version_number     2017/1
_olex2_date_sample_data_collection 2019-01-17
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.567