Gold-catalyzed redox cycloisomerization/nucleophilic addition/reduction: direct access to 2-phosphoryl indolin-3-ones.
Zhou, Xingcui; Xiong, Ting; Jiang, Jun; Chemical communications (Cambridge, England) 58 (2022) 8568–8571; doi:10.1039/d2cc02774g

data_7130432
_publ_section_title
;
 Gold-catalyzed redox cycloisomerization/nucleophilic addition/reduction:
 direct access to 2-phosphoryl indolin-3-ones.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8568
_journal_page_last               8571
_journal_paper_doi               10.1039/d2cc02774g
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C18 H20 N O4 P'
_chemical_formula_sum            'C18 H20 N O4 P'
_chemical_formula_weight         345.32
_chemical_name_systematic
'diethyl (S)-(3-oxo-2-phenylindolin-2-yl)phosphonate'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2022-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                76.027(6)
_cell_angle_beta                 74.128(7)
_cell_angle_gamma                60.531(8)
_cell_formula_units_Z            2
_cell_length_a                   9.8117(8)
_cell_length_b                   9.8216(7)
_cell_length_c                   10.5478(8)
_cell_measurement_reflns_used    3149
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.7470
_cell_measurement_theta_min      2.4140
_cell_volume                     844.24(13)
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -58.00  34.00   1.00    1.00    --   12.05 -57.00  90.00   92
  2  \w    -12.00  79.00   1.00    1.00    --   12.05  77.00   0.00   91
  3  \w    -15.00  80.00   1.00    1.00    --   12.05  57.00-120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0158277000
_diffrn_orient_matrix_UB_12      0.0761196000
_diffrn_orient_matrix_UB_13      0.0088107000
_diffrn_orient_matrix_UB_21      -0.0703294000
_diffrn_orient_matrix_UB_22      0.0337117000
_diffrn_orient_matrix_UB_23      -0.0268845000
_diffrn_orient_matrix_UB_31      -0.0440119000
_diffrn_orient_matrix_UB_32      -0.0080089000
_diffrn_orient_matrix_UB_33      0.0645619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5418
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.401
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78409
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0566P)^2^+0.5010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2565
_reflns_number_total             2975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02774g2.cif
_cod_data_source_block           exp_3804
_cod_database_code               7130432
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.973
_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, All C(H,H,H,H,H,H) groups
2. Others
 Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15B(H15C,H15D), C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
3.c Idealised Me refined as rotating group:
 C16(H16D,H16E,H16F), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              64973
_shelx_hkl_checksum              43849
_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.649