A cascade reaction of indolyl-migratory isocyanide insertion, scaffold rearrangement and redox-neutral event with isocyanide as a C<sub>(sp<sup>3</sup>)</sub>H-N synthon efficiently constructs indolylisoindolinones.
Sisodiya, Shailendra; Acharya, Ayan; Nagpure, Mithilesh; Roy, Nibedita; Giri, Santosh K.; Yadav, Hare Ram; R Choudhury, Angshuman; Guchhait, Sankar K.; Chemical communications (Cambridge, England)  (2022) –; doi:10.1039/d2cc04273h

data_7130809
_publ_section_title
;
 A cascade reaction of indolyl-migratory isocyanide insertion, scaffold
 rearrangement and redox-neutral event with isocyanide as a
 C<sub>(sp<sup>3</sup>)</sub>H-N synthon efficiently constructs
 indolylisoindolinones.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc04273h
_journal_year                    2022
_chemical_formula_moiety         'C20 H20 N2 O'
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_weight         304.38
_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
_audit_creation_date             2022-07-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-25 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                91.596(14)
_cell_angle_beta                 106.105(17)
_cell_angle_gamma                99.60(2)
_cell_formula_units_Z            4
_cell_length_a                   10.581(6)
_cell_length_b                   11.314(5)
_cell_length_c                   14.595(9)
_cell_measurement_reflns_used    1348
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      2.2
_cell_volume                     1650.1(16)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_unetI/netI     0.1204
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15149
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         1.457
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         7521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.2459
_refine_ls_R_factor_gt           0.1109
_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^)+(0.1653P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2658
_refine_ls_wR_factor_ref         0.3776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2678
_reflns_number_total             7521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04273h2.cif
_cod_data_source_block           sss226_rt
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1650.0(16)
_cod_database_code               7130809
_shelx_shelxl_version_number     2014/7
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C5(H5), C23(H23), C10(H10), C26(H26), C30(H30),
 C21(H21), C1(H1A), C33(H33), C24(H24), C25(H25), C32(H32), C13(H13), C31(H31),
 C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C37(H37A,H37B,
 H37C), C38(H38A,H38B,H38C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              21406
_shelx_hkl_checksum              75444
_olex2_submission_special_instructions 'No special instructions were received'