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_7133198
_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, 0.6(C H2 Cl2)'
_chemical_formula_sum            'C29.6 H25.2 Cl1.2 N O3 P'
_chemical_formula_weight         516.42
_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                91.104(5)
_cell_angle_beta                 99.247(6)
_cell_angle_gamma                107.898(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9338(7)
_cell_length_b                   11.4115(6)
_cell_length_c                   13.4261(9)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.5820
_cell_measurement_theta_min      6.6860
_cell_volume                     1425.68(17)
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9759
_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    -19.00  12.00   1.00    1.00    --    0.00 104.00 -64.00   31
  2  \w     11.00  82.00   1.00    2.00    --   54.00-104.00-165.00   71
  3  \w     70.00  96.00   1.00    2.00    --  108.00-104.00-165.00   26
  4  \w    104.00 169.00   1.00    2.00    --  108.00 104.00 -64.00   65
  5  \w    -21.00   7.00   1.00    1.00    --    0.00 -77.00 150.00   28
  6  \w    -16.00  24.00   1.00    1.00    --    0.00 -77.00  90.00   40
  7  \w     -4.00  21.00   1.00    1.00    --    0.00 -77.00-180.00   25
  8  \w    -13.00  40.00   1.00    1.00    --    0.00  77.00  60.00   53
  9  \w     89.00 115.00   1.00    2.00    --   54.00  57.00-120.00   26
 10  \w    -16.00  57.00   1.00    2.00    --   54.00 -77.00-120.00   73
 11  \w     19.00  74.00   1.00    2.00    --   54.00 -57.00  90.00   55
 12  \w    -19.00  98.00   1.00    2.00    --   54.00 -19.00 -90.00  117
 13  \w     42.00 122.00   1.00    2.00    --   54.00  57.00  90.00   80
 14  \w     38.00 103.00   1.00    2.00    --   54.00-125.00  60.00   65
 15  \w     33.00  64.00   1.00    2.00    --   54.00-125.00   0.00   31
 16  \w     87.00 174.00   1.00    2.00    --  108.00  50.00 -90.00   87
 17  \w     36.00 109.00   1.00    2.00    --  108.00-111.00 150.00   73
 18  \w    105.00 177.00   1.00    2.00    --  108.00 111.00   0.00   72
 19  \w    107.00 134.00   1.00    2.00    --  108.00  77.00 -90.00   27
 20  \w    120.00 146.00   1.00    2.00    --  108.00 111.00 -30.00   26
 21  \w     54.00 125.00   1.00    2.00    --  108.00 -50.00 -30.00   71
 22  \w    108.00 174.00   1.00    2.00    --  108.00  77.00 -30.00   66
 23  \w    110.00 137.00   1.00    2.00    --  108.00 178.00-180.00   27
 24  \w     67.00  93.00   1.00    2.00    --  108.00 178.00-180.00   26
 25  \w     71.00 105.00   1.00    2.00    --  108.00-111.00 -60.00   34
 26  \w     77.00 123.00   1.00    2.00    --  108.00 -50.00-120.00   46
 27  \w     81.00 106.00   1.00    2.00    --  108.00-111.00 -30.00   25
 28  \w    150.00 175.00   1.00    2.00    --  108.00 111.00 -30.00   25
 29  \w     49.00 107.00   1.00    2.00    --  108.00 -91.00   0.00   58
 30  \w     44.00  69.00   1.00    2.00    --  108.00 -50.00-120.00   25
 31  \w     37.00  71.00   1.00    2.00    --  108.00-111.00 -30.00   34
 32  \w    124.00 163.00   1.00    2.00    --  108.00  50.00 120.00   39
 33  \w     36.00  62.00   1.00    2.00    --  108.00 -91.00 150.00   26
 34  \w     70.00  96.00   1.00    2.00    --  108.00 -50.00-180.00   26
 35  \w     75.00 151.00   1.00    2.00    --  108.00  25.00  60.00   76
;
_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      0.1593984000
_diffrn_orient_matrix_UB_12      0.0288603000
_diffrn_orient_matrix_UB_13      0.0478988000
_diffrn_orient_matrix_UB_21      -0.0325846000
_diffrn_orient_matrix_UB_22      0.0389986000
_diffrn_orient_matrix_UB_23      0.1016718000
_diffrn_orient_matrix_UB_31      -0.0304903000
_diffrn_orient_matrix_UB_32      -0.1337174000
_diffrn_orient_matrix_UB_33      0.0309258000
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10015
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         4.75
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92222
_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            yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.090
_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     350
_refine_ls_number_reflns         5070
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1196P)^2^+1.4681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2079
_reflns_number_gt                4118
_reflns_number_total             5070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4cc01984a2.cif
_cod_data_source_block           exp_1357
_cod_depositor_comments
'Adding full bibliography for 7133196--7133198.cif.'
_cod_original_cell_volume        1425.67(16)
_cod_original_formula_sum        'C29.60 H25.20 Cl1.20 N O3 P'
_cod_database_code               7133198
_diffrn_oxdiff_digest_frames
;
0192709b5a6f92c48f1d603c06eaebf1070002832b7
;
_diffrn_oxdiff_digest_hkl
;
01743002a3073f09793c1e19647de681d02887
;
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1'-C30' = Cl2'-C30'
 1.7 with sigma of 0.01
 Cl1-C30 = Cl2-C30
 1.7 with sigma of 0.01
 Cl1'-Cl2' \\sim Cl1-Cl2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C30') = Uanis(C30)
Uanis(Cl2') = Uanis(Cl1')
4. Others
 Fixed Sof: C30(0.5) H30A(0.5) H30B(0.5) Cl2(0.5) Cl1(0.5) Cl1'(0.1) Cl2'(0.1)
 C30'(0.1) H30C(0.1) H30D(0.1)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C30'(H30C,H30D)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H22), C10(H10), C9(H9), C18(H18), C24(H24), C20(H20), C19(H19),
 C12(H12), C21(H21), C16(H16), C2(H2), C5(H5), C15(H15), C25(H25), C13(H13),
 C28(H28), C26(H26), C3(H3), C4(H4), C27(H27)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.849