Dearomative oxyphosphorylation of indoles enables facile access to 2,2-disubstituted indolin-3-ones.
Xiong, Ting; Zhou, Xingcui; Jiang, Jun; Organic & biomolecular chemistry 20 (2022) 5721–5725; doi:10.1039/d2ob01063a

data_7158773
_publ_section_title
;
 Dearomative oxyphosphorylation of indoles enables facile access to
 2,2-disubstituted indolin-3-ones.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5721
_journal_page_last               5725
_journal_paper_doi               10.1039/d2ob01063a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C18 H20 N O4 P'
_chemical_formula_sum            'C18 H20 N O4 P'
_chemical_formula_weight         345.32
_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     iterative
_audit_creation_date             2021-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-17 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                73.336(2)
_cell_angle_beta                 75.766(2)
_cell_angle_gamma                60.403(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8688(7)
_cell_length_b                   9.9088(7)
_cell_length_c                   10.7278(8)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.516
_cell_measurement_theta_min      3.304
_cell_volume                     866.99(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18052
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_min         3.655
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.9242.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3970
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+0.4677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1673
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3309
_reflns_number_total             3970
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01063a2.cif
_cod_data_source_block           111
_cod_depositor_comments          'Adding full bibliography for 7158773.cif.'
_cod_database_code               7158773
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.938
_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. Uiso/Uaniso restraints and constraints
Uanis(C17B) \\sim Ueq, Uanis(C18A) \\sim Ueq, Uanis(C18B) \\sim Ueq,
Uanis(C17A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C17B) = Uanis(C18B) = Uanis(C18A) = Uanis(C17A)
3. Others
 Sof(C17B)=Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C17A)=Sof(H17A)=Sof(H17B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17A(H17A,H17B), C17B(H17C,H17D)
4.b Aromatic/amide H refined with riding coordinates:
 N10(H10), C1(H1), C14(H14), C10(H10A), C4(H4), C3(H3), C2(H2), C11(H11),
 C13(H13), C12(H12)
4.c Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C16(H16A,H16B,H16C), C18B(H18D,H18E,H18F)
;
_shelx_res_checksum              43944
_olex2_submission_special_instructions 'No special instructions were received'