Ir(III)-Catalyzed C-H Functionalization of Triphenylphosphine Oxide Towards 3-Aryl Oxindoles.
Lou, Qin-Xin; Niu, Yuan; Qi, Zhi-Chao; Yang, Shang-Dong; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00999

data_4038843
_publ_section_title
;
 Ir(III)-Catalyzed C-H Functionalization of Triphenylphosphine Oxide
 Towards 3-Aryl Oxindoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00999
_journal_year                    2020
_chemical_formula_moiety         'C28 H22 N O3 P'
_chemical_formula_sum            'C28 H22 N O3 P'
_chemical_formula_weight         451.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-17 deposited with the CCDC.	2019-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                75.866(7)
_cell_angle_beta                 82.881(6)
_cell_angle_gamma                74.752(9)
_cell_formula_units_Z            2
_cell_length_a                   8.3188(8)
_cell_length_b                   9.3992(11)
_cell_length_c                   15.4909(9)
_cell_measurement_reflns_used    1791
_cell_measurement_temperature    291.63(10)
_cell_measurement_theta_max      69.7410
_cell_measurement_theta_min      9.8430
_cell_volume                     1130.91(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.63(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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      7.00  94.00   1.00    1.00    --   54.00 -99.00  30.00   87
  2  \w     51.00 135.00   1.00    1.00    --  108.00 -25.00  90.00   84
  3  \w     87.00 138.00   1.00    1.00    --  108.00  50.00 150.00   51
  4  \w     53.00 117.00   1.00    1.00    --  108.00 -63.00  30.00   64
  5  \w     91.00 116.00   1.00    1.00    --  108.00-111.00   0.00   25
  6  \w     58.00  84.00   1.00    1.00    --   54.00-125.00 -90.00   26
  7  \w     68.00 115.00   1.00    1.00    --  108.00-111.00-120.00   47
  8  \w     57.00  83.00   1.00    1.00    --  108.00-111.00   0.00   26
  9  \w     40.00 138.00   1.00    1.00    --  108.00 -77.00 -90.00   98
 10  \w     89.00 172.00   1.00    1.00    --  108.00  38.00 -90.00   83
 11  \w    104.00 129.00   1.00    1.00    --  108.00  94.00-151.00   25
 12  \w     76.00 115.00   1.00    1.00    --   54.00  57.00-180.00   39
 13  \w     38.00 124.00   1.00    1.00    --  108.00 -25.00 -30.00   86
 14  \w     41.00 124.00   1.00    1.00    --   54.00  38.00  90.00   83
 15  \w     34.00  95.00   1.00    1.00    --   54.00  38.00   0.00   61
 16  \w     35.00 127.00   1.00    1.00    --  108.00 -25.00-120.00   92
 17  \w     40.00 121.00   1.00    1.00    --  108.00 -63.00-180.00   81
 18  \w     41.00 145.00   1.00    1.00    --  108.00 -91.00  60.00  104
 19  \w     -6.00  28.00   1.00    1.00    --    0.00 -77.00  60.00   34
 20  \w    -13.00  60.00   1.00    1.00    --   54.00 -57.00 120.00   73
 21  \w    -68.00 -17.00   1.00    1.00    --    0.00 -77.00  60.00   51
 22  \w     -4.00  22.00   1.00    1.00    --   54.00 -57.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0774103000
_diffrn_orient_matrix_UB_12      0.1062432000
_diffrn_orient_matrix_UB_13      -0.0849436000
_diffrn_orient_matrix_UB_21      -0.0224516000
_diffrn_orient_matrix_UB_22      0.1368320000
_diffrn_orient_matrix_UB_23      0.0423055000
_diffrn_orient_matrix_UB_31      0.1746386000
_diffrn_orient_matrix_UB_32      0.0182778000
_diffrn_orient_matrix_UB_33      -0.0394360000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6616
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         5.001
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0752
_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^)+(0.1247P)^2^+0.1941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2115
_refine_ls_wR_factor_ref         0.2443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2686
_reflns_number_total             3867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00999_si_002.cif
_cod_data_source_block           louqx_0701
_cod_database_code               4038843
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 97.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C21(H21),
 C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31),
  C33(H33), C0AA(H0AA)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_shelx_res_checksum              19562
_shelx_hkl_checksum              49194
_olex2_date_sample_data_collection 2019-07-02
_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 2.707
_oxdiff_exptl_absorpt_empirical_full_min 0.588