Rongalite induced metal-free C(sp<sup>2</sup>)-H functionalization of indoles: direct access to 3-(sulfonylmethyl) indoles.
Thunga, Sanjeeva; Singh, Neetika; Inapanuri, Madhu; Kokatla, Hari Prasad; Organic & biomolecular chemistry 22 (2024) 8787–8792; doi:10.1039/d4ob01356e

data_7160172
_publ_section_title
;
 Rongalite induced metal-free C(sp<sup>2</sup>)-H functionalization of
 indoles: direct access to 3-(sulfonylmethyl) indoles.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8787
_journal_page_last               8792
_journal_paper_doi               10.1039/d4ob01356e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C17 H17 N O3 S'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.40
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-02 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.219(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6272(2)
_cell_length_b                   16.6924(2)
_cell_length_c                   9.08710(10)
_cell_measurement_reflns_used    7031
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.1830
_cell_measurement_theta_min      5.8170
_cell_volume                     1522.15(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9711
_diffrn_measured_fraction_theta_max 0.9711
_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     54.00  82.00   0.50    5.00    --    0.00  37.00 -90.00   56
  2  \w    -23.00  71.00   0.50    5.00    --    0.00  57.00 150.00  188
  3  \w    -19.00  56.00   0.50    5.00    --    0.00  37.00  30.00  150
  4  \w     47.00 121.00   0.50    8.20    --  107.20 -45.00 -30.00  148
  5  \w     81.00 196.00   0.50    8.20    --  107.20  82.00  90.00  230
  6  \w    106.00 133.00   0.50    8.20    --  107.20  15.00-120.00   54
  7  \w     18.00  63.00   0.50    8.20    --  107.20 -30.00 -60.00   90
  8  \w    146.00 171.00   0.50    8.20    --  107.20  15.00-120.00   50
  9  \w     24.00 126.00   0.50    8.20    --  107.20 -45.00 120.00  204
 10  \w     70.00 119.00   0.50    8.20    --  107.20 -30.00 -60.00   98
 11  \w     72.00 127.00   0.50    8.20    --  107.20 -77.00 -60.00  110
 12  \w     50.00 123.00   0.50    8.20    --  107.20 -15.00-120.00  146
 13  \w     20.00  45.00   0.50    8.20    --  107.20 -15.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0264572000
_diffrn_orient_matrix_UB_12      0.0786724000
_diffrn_orient_matrix_UB_13      0.0734068000
_diffrn_orient_matrix_UB_21      -0.1001917000
_diffrn_orient_matrix_UB_22      0.0254616000
_diffrn_orient_matrix_UB_23      -0.1581133000
_diffrn_orient_matrix_UB_31      -0.1133028000
_diffrn_orient_matrix_UB_32      -0.0409942000
_diffrn_orient_matrix_UB_33      0.0427094000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8378
_diffrn_reflns_theta_full        79.6459
_diffrn_reflns_theta_max         79.65
_diffrn_reflns_theta_min         4.41
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.3762
_exptl_crystal_description       block
_exptl_crystal_F_000             667.3275
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3256
_refine_diff_density_min         -0.4873
_refine_diff_density_rms         0.0585
_refine_ls_d_res_high            0.7837
_refine_ls_d_res_low             10.0349
_refine_ls_goodness_of_fit_ref   1.0312
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0312
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.9170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                3123
_reflns_number_total             3221
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob01356e2.cif
_cod_data_source_block           exp_522_001
_cod_depositor_comments
'Adding full bibliography for 7160172--7160173.cif.'
_cod_database_code               7160172
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C00C(H00a,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I),
 C00K(H00K)
2.c Idealised Me refined as rotating group:
 C00L(H00f,H00g,H00j), C00M(H00l,H00m,H00n)
;
_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 1.600
_oxdiff_exptl_absorpt_empirical_full_min 0.781