Vinyl benzotriazole to indole: an iodine-mediated denitrogenative transannulation approach for the synthesis of indoles.
Thakur, Deepika; Meena, Shivam A.; Sharma, Manvi; Nandy, Abhijit; Arora, Kirti; Banerjee, Shibdas; Verma, Akhilesh K.; Chemical communications (Cambridge, England)  (2025) –; doi:10.1039/d5cc05419b

data_7135178
_publ_section_title
;
 Vinyl benzotriazole to indole: an iodine-mediated denitrogenative
 transannulation approach for the synthesis of indoles.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d5cc05419b
_journal_year                    2025
_chemical_formula_moiety         'C18 H18 I N3 O2 S'
_chemical_formula_sum            'C18 H18 I N3 O2 S'
_chemical_formula_weight         467.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-10-16 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.755(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6989(2)
_cell_length_b                   13.6394(3)
_cell_length_c                   17.7709(6)
_cell_measurement_reflns_used    11064
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.8850
_cell_measurement_theta_min      1.9740
_cell_volume                     1844.35(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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      2.00  27.00   0.50    0.44    --    5.38  97.00-102.00   50
  2  \w    -49.00 -19.00   0.50    0.44    --    5.38 -19.00 -30.00   60
  3  \w    -21.00  26.00   0.50    0.44    --   -5.23 -99.00 -30.00   94
  4  \w    -23.00   2.00   0.50    0.44    --   -5.23 -99.00  90.00   50
  5  \w    -27.00  36.00   0.50    0.44    --    5.38 -97.00 149.00  126
  6  \w    -77.00  10.00   0.50    0.44    --   -5.23 -57.00  60.00  174
  7  \w    -35.00   8.00   0.50    0.44    --   -5.23  97.00-102.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0016148000
_diffrn_orient_matrix_UB_12      -0.0447635000
_diffrn_orient_matrix_UB_13      -0.0204160000
_diffrn_orient_matrix_UB_21      0.0653762000
_diffrn_orient_matrix_UB_22      -0.0193784000
_diffrn_orient_matrix_UB_23      0.0285709000
_diffrn_orient_matrix_UB_31      -0.0664166000
_diffrn_orient_matrix_UB_32      -0.0180144000
_diffrn_orient_matrix_UB_33      0.0199660000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18586
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.890
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_refine_diff_density_max         0.735
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0485P)^2^+3.1715P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3353
_reflns_number_total             3773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05419b2.cif
_cod_data_source_block           dt-223_auto
_cod_database_code               7135178
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O S I'
_chemical_oxdiff_usercomment     22-11-2024
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N12) = Uanis(N1) = Uanis(N2) = Uanis(C6) = Uanis(C11)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C7(H7), C18(H18), C15(H15), C17(H17), C8(H8), C9(H9),
 C10(H10)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              13962
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.633