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_7133196
_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         'C28 H22 N O2 P'
_chemical_formula_sum            'C28 H22 N O2 P'
_chemical_formula_weight         435.44
_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             2023-05-11
_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                83.016(4)
_cell_angle_beta                 81.790(4)
_cell_angle_gamma                62.191(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2305(5)
_cell_length_b                   9.3886(6)
_cell_length_c                   15.0613(6)
_cell_measurement_reflns_used    3534
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5310
_cell_measurement_theta_min      7.5320
_cell_volume                     1140.40(12)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9812
_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    -16.00  25.00   1.00    1.00    --    0.00  37.00-126.00   41
  2  \w     45.00  72.00   1.00    1.00    --    0.00  37.00-126.00   27
  3  \w     34.00  62.00   1.00    1.00    --   54.00  37.00-126.00   28
  4  \w    -17.00  36.00   1.00    1.00    --   54.00 -37.00  77.00   53
  5  \w     74.00 101.00   1.00    1.00    --  108.00 -37.00  77.00   27
  6  \w     94.00 157.00   1.00    1.00    --  108.00  37.00-126.00   63
  7  \w     -2.00  24.00   1.00    1.00    --    0.00 -77.00  30.00   26
  8  \w    -63.00 -12.00   1.00    1.00    --    0.00 -37.00  77.00   51
  9  \w     51.00 126.00   1.00    1.00    --   54.00  37.00 -30.00   75
 10  \w     24.00  94.00   1.00    1.00    --   54.00 -99.00 150.00   70
 11  \w    -15.00  67.00   1.00    1.00    --   54.00 -57.00   0.00   82
 12  \w      7.00  96.00   1.00    1.00    --   54.00 -99.00 -60.00   89
 13  \w     66.00  93.00   1.00    1.00    --   54.00  37.00-126.00   27
 14  \w     42.00 123.00   1.00    1.00    --   54.00  57.00-120.00   81
 15  \w     92.00 178.00   1.00    1.00    --  108.00  37.00 120.00   86
 16  \w     86.00 177.00   1.00    1.00    --  108.00  50.00-180.00   91
 17  \w     41.00 104.00   1.00    1.00    --  108.00 -50.00-120.00   63
 18  \w     39.00 130.00   1.00    1.00    --  108.00 -50.00 150.00   91
 19  \w     77.00 108.00   1.00    1.00    --  108.00-111.00 -30.00   31
 20  \w    106.00 173.00   1.00    1.00    --  108.00 111.00  60.00   67
 21  \w     68.00 108.00   1.00    1.00    --  108.00-111.00 -90.00   40
 22  \w     46.00  98.00   1.00    1.00    --  108.00 -91.00-180.00   52
 23  \w     65.00 123.00   1.00    1.00    --  108.00 178.00  90.00   58
 24  \w     54.00 105.00   1.00    1.00    --  108.00 -91.00 120.00   51
 25  \w    106.00 131.00   1.00    1.00    --  108.00 111.00-150.00   25
 26  \w     85.00 136.00   1.00    1.00    --  108.00 178.00 120.00   51
 27  \w     38.00 125.00   1.00    1.00    --  108.00 -50.00  30.00   87
 28  \w    108.00 133.00   1.00    1.00    --  108.00 111.00  90.00   25
 29  \w     37.00 108.00   1.00    1.00    --  108.00-111.00  90.00   71
;
_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      -0.1735867000
_diffrn_orient_matrix_UB_12      0.1047092000
_diffrn_orient_matrix_UB_13      0.0448840000
_diffrn_orient_matrix_UB_21      -0.0555832000
_diffrn_orient_matrix_UB_22      -0.1232342000
_diffrn_orient_matrix_UB_23      -0.0198689000
_diffrn_orient_matrix_UB_31      0.0522309000
_diffrn_orient_matrix_UB_32      -0.0916593000
_diffrn_orient_matrix_UB_33      0.0911765000
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8124
_diffrn_reflns_theta_full        70.36
_diffrn_reflns_theta_max         70.37
_diffrn_reflns_theta_min         5.34
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74486
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0422P)^2^+0.4617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                3657
_reflns_number_total             4282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4cc01984a2.cif
_cod_data_source_block           exp_1456
_cod_depositor_comments
'Adding full bibliography for 7133196--7133198.cif.'
_cod_original_cell_volume        1140.40(11)
_cod_database_code               7133196
_chemical_oxdiff_formula         'C1 H1 N1 O1 P1'
_diffrn_oxdiff_digest_frames
;
01f538f1cf4301f6abced5ab71a4b30885000287d63
;
_diffrn_oxdiff_digest_hkl
;
01cbd2d2be71365a031520a96439f9446fc356
;
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27), N1(H1A)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.627