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_7135179
_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         'C22 H19 N O3 S'
_chemical_formula_sum            'C22 H19 N O3 S'
_chemical_formula_weight         377.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-12-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-05-22 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1706(8)
_cell_length_b                   11.7513(8)
_cell_length_c                   21.1278(12)
_cell_measurement_reflns_used    7041
_cell_measurement_temperature    295.0(2)
_cell_measurement_theta_max      29.4850
_cell_measurement_theta_min      1.9560
_cell_volume                     3766.5(4)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -33.00   0.00   0.50    6.00    --   -5.54  98.00 163.00   66
  2  \w     -9.00  24.00   0.50    6.00    --   -5.54 -98.00  56.00   66
  3  \w    -78.00 -12.00   0.50    6.00    --   -5.54 -57.00 -30.00  132
  4  \w    -21.00  24.00   0.50    6.00    --   -5.54 -99.00-120.00   90
;
_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      0.0095895000
_diffrn_orient_matrix_UB_12      -0.0431474000
_diffrn_orient_matrix_UB_13      0.0117694000
_diffrn_orient_matrix_UB_21      0.0241196000
_diffrn_orient_matrix_UB_22      -0.0123744000
_diffrn_orient_matrix_UB_23      -0.0294644000
_diffrn_orient_matrix_UB_31      0.0545097000
_diffrn_orient_matrix_UB_32      0.0130281000
_diffrn_orient_matrix_UB_33      0.0109728000
_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  0.0617
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20539
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         1.928
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78988
_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    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1756 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_coef       0.0011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         7412
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0508P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                4876
_reflns_number_total             7412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05419b2.cif
_cod_data_source_block           dt-153_auto
_cod_database_code               7135179
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     04-12-2024
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C00D(H00D), C00K(H00K), C00M(H00M), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C013(H013), C014(H014), C015(H015),
 C016(H016), C017(H017), C018(H018), C01A(H01A), C01B(H01J), C01D(H01E),
 C01E(H01K), C01F(H01F)
2.b Idealised Me refined as rotating group:
 C01C(H01B,H01C,H01D), C01G(H01G,H01H,H01I), C01H(H01L,H01M,H01N), C01I(H01O,
 H01P,H01Q)
;
_shelx_res_checksum              91636
_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 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.740