Silver-catalyzed P-centered anion nucleophilic addition to isocyanide: access to 2-phosphinoyl indoles/indol-3-ols.
Liu, Yong; Jia, Mengying; Wang, Guodong; Yang, Wenhui; Xu, Xianxiu; Chemical communications (Cambridge, England) 60 (2024) 7196–7199; doi:10.1039/d4cc01984a

data_7133197
_publ_section_title
;
 Silver-catalyzed P-centered anion nucleophilic addition to isocyanide:
 access to 2-phosphinoyl indoles/indol-3-ols.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7196
_journal_page_last               7199
_journal_paper_doi               10.1039/d4cc01984a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C29 H24 N O3 P'
_chemical_formula_sum            'C29 H24 N O3 P'
_chemical_formula_weight         465.46
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2024-02-23 deposited with the CCDC.	2024-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.272(7)
_cell_angle_beta                 112.661(8)
_cell_angle_gamma                92.657(7)
_cell_formula_units_Z            2
_cell_length_a                   10.1021(9)
_cell_length_b                   10.6285(9)
_cell_length_c                   12.0861(10)
_cell_measurement_reflns_used    1957
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.1010
_cell_measurement_theta_min      7.9600
_cell_volume                     1187.71(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9783
_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   2.00   1.00    1.00    --    0.00 -39.00 -74.00   60
  2  \w     -9.00  28.00   1.00    1.00    --    0.00  39.00  79.00   37
  3  \w     51.00 125.00   1.00    1.50    --   54.00  39.00  79.00   74
  4  \w    -17.00  79.00   1.00    1.50    --   54.00 -39.00 -74.00   96
  5  \w     83.00 166.00   1.00    1.50    --  108.00  39.00  79.00   83
  6  \w     40.00 101.00   1.00    1.50    --  108.00 -39.00 -74.00   61
  7  \w     31.00  66.00   1.00    1.00    --    0.00  39.00  79.00   35
  8  \w    -21.00   4.00   1.00    1.00    --    0.00 -77.00-120.00   25
  9  \w    -18.00  78.00   1.00    1.50    --   54.00 -37.00 150.00   96
 10  \w     70.00 123.00   1.00    1.50    --   54.00  57.00  90.00   53
 11  \w     -9.00  55.00   1.00    1.50    --   54.00 -77.00 150.00   64
 12  \w     27.00  83.00   1.00    1.50    --   54.00-125.00 -60.00   56
 13  \w     35.00  60.00   1.00    1.50    --   54.00-125.00 -30.00   25
 14  \w     39.00  96.00   1.00    1.50    --   54.00 -99.00  30.00   57
 15  \w     88.00 168.00   1.00    1.50    --  108.00  63.00 -60.00   80
 16  \w     49.00  83.00   1.00    1.50    --  108.00 -50.00  60.00   34
 17  \w    105.00 170.00   1.00    1.50    --  108.00  77.00   0.00   65
 18  \w     49.00  99.00   1.00    1.50    --  108.00 -91.00-150.00   50
 19  \w    103.00 172.00   1.00    1.50    --  108.00  77.00 -30.00   69
 20  \w     37.00  62.00   1.00    1.50    --  108.00-111.00 120.00   25
 21  \w    138.00 176.00   1.00    1.50    --  108.00  37.00 -90.00   38
 22  \w    152.00 178.00   1.00    1.50    --  108.00 111.00-180.00   26
 23  \w     83.00 120.00   1.00    1.50    --  108.00  37.00 -90.00   37
 24  \w    105.00 131.00   1.00    1.50    --  108.00 111.00-180.00   26
 25  \w     56.00 106.00   1.00    1.50    --  108.00 -91.00 -30.00   50
 26  \w     57.00 128.00   1.00    1.50    --  108.00 -63.00-150.00   71
 27  \w     37.00  63.00   1.00    1.50    --  108.00-111.00 -60.00   26
 28  \w     81.00 109.00   1.00    1.50    --  108.00-111.00 -60.00   28
 29  \w     70.00 108.00   1.00    1.50    --  108.00-111.00 120.00   38
 30  \w    105.00 130.00   1.00    1.50    --  108.00 -50.00  60.00   25
 31  \w     54.00 106.00   1.00    1.50    --  108.00 -63.00   0.00   52
 32  \w     37.00 104.00   1.00    1.50    --  108.00-111.00-180.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0239771000
_diffrn_orient_matrix_UB_12      -0.1207272000
_diffrn_orient_matrix_UB_13      -0.0682240000
_diffrn_orient_matrix_UB_21      0.1367977000
_diffrn_orient_matrix_UB_22      0.0678771000
_diffrn_orient_matrix_UB_23      -0.0023975000
_diffrn_orient_matrix_UB_31      0.0907722000
_diffrn_orient_matrix_UB_32      -0.0466360000
_diffrn_orient_matrix_UB_33      0.1212181000
_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  0.0488
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8165
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         3.99
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.278
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                3124
_reflns_number_total             4223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4cc01984a2.cif
_cod_data_source_block           exp_1356
_cod_depositor_comments
'Adding full bibliography for 7133196--7133198.cif.'
_cod_original_cell_volume        1187.71(17)
_cod_database_code               7133197
_diffrn_oxdiff_digest_frames
;
0141000713c520ebb116300df224a15888000289569
;
_diffrn_oxdiff_digest_hkl
;
01e96b152c7cb191b4f1287f7f0a8eedf81b83
;
_reflns_odcompleteness_completeness 99.88
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24),
  C25(H25), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.513
_oxdiff_exptl_absorpt_empirical_full_min 0.654