Electrochemical reaction of indole-tethered alkynes enabling stereoselective synthesis of iodovinyl spiroindolenine-cyclopentanes
He, Jingrui; Zhou, Xinrui; Mei, Haibo; Makarem, Ata; Javahershenas, Ramin; Soloshonok, Vadim A.; Han, Jianlin; Chemical Communications 61 (2025) 7454–7457; doi:10.1039/D5CC01342A

data_7134413
_publ_section_title
;
 Electrochemical reaction of indole-tethered alkynes enabling
 stereoselective synthesis of iodovinyl spiroindolenine-cyclopentanes
;
_journal_issue                   41
_journal_name_full               'Chemical Communications'
_journal_page_first              7454
_journal_page_last               7457
_journal_paper_doi               10.1039/D5CC01342A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C26 H26 I N O4'
_chemical_formula_sum            'C26 H26 I N O4'
_chemical_formula_weight         543.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-07-02
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-02-21 deposited with the CCDC.	2025-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9209(3)
_cell_length_b                   13.7113(2)
_cell_length_c                   22.3081(3)
_cell_measurement_reflns_used    12546
_cell_measurement_temperature    293.00(13)
_cell_measurement_theta_max      73.2370
_cell_measurement_theta_min      2.7740
_cell_volume                     4869.77(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_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     81.00 106.00   0.50    0.60    --   99.00-102.00-111.00   50
  2  \w     57.00 101.00   0.50    0.60    --   99.00-125.00 -60.00   88
  3  \w    -70.00 -33.00   0.50    0.60    --  -99.00  61.00-180.00   74
  4  \w    -70.00 -33.00   0.50    0.60    --  -99.00  61.00-150.00   74
  5  \w    -64.00 -30.00   0.50    0.60    --  -99.00  61.00 -90.00   68
  6  \w    -21.00  28.00   0.50    0.17    --  -45.87  19.00 -90.00   98
  7  \w    -20.00  18.00   0.50    0.17    --  -45.87  19.00   0.00   76
  8  \w   -105.00 -32.00   0.50    0.60    --  -99.00 102.00  -8.00  146
  9  \w    -89.00 -35.00   0.50    0.17    --  -45.87 120.00-109.00  108
 10  \w     35.00  70.00   0.50    0.60    --   99.00 -61.00 -60.00   70
 11  \w     27.00  52.00   0.50    0.60    --   99.00 -45.00 -30.00   50
 12  \w     28.00  53.00   0.50    0.60    --   99.00 -45.00  60.00   50
 13  \w     90.00 174.00   0.50    0.60    --   99.00  24.00 178.00  168
 14  \w    -17.00  29.00   0.50    0.17    --   45.87 -19.00  90.00   92
 15  \w   -165.00 -80.00   0.50    0.60    --  -99.00-120.00 165.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0859095000
_diffrn_orient_matrix_UB_12      -0.0516533000
_diffrn_orient_matrix_UB_13      -0.0020025000
_diffrn_orient_matrix_UB_21      -0.0430367000
_diffrn_orient_matrix_UB_22      0.0942224000
_diffrn_orient_matrix_UB_23      0.0217287000
_diffrn_orient_matrix_UB_31      -0.0115640000
_diffrn_orient_matrix_UB_32      0.0328753000
_diffrn_orient_matrix_UB_33      -0.0655005000
_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  0.0478
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21453
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.314
_diffrn_reflns_theta_min         3.963
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+11.5117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4083
_reflns_number_total             4768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01342a2.cif
_cod_data_source_block           hjr-3
_cod_depositor_comments          'Adding full bibliography for 7134413.cif.'
_cod_database_code               7134413
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N I'
_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.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C21(H21A,H21B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C19(H19)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              15651
_shelx_hkl_checksum              33591
_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 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.673