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_7160173
_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         '0.5(C25 H25 N O2 S)'
_chemical_formula_sum            'C12.5 H12.5 N0.5 O S0.5'
_chemical_formula_weight         201.77
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-24
_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                96.935(2)
_cell_angle_beta                 104.121(2)
_cell_angle_gamma                102.127(2)
_cell_formula_units_Z            4
_cell_length_a                   8.4532(2)
_cell_length_b                   10.3709(2)
_cell_length_c                   12.4478(3)
_cell_measurement_reflns_used    7200
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.1210
_cell_measurement_theta_min      5.5970
_cell_volume                     1017.51(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 0.9650
_diffrn_measured_fraction_theta_max 0.9650
_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    -73.00 -48.00   0.50    1.00    --    0.00 -19.00-150.00   50
  2  \w     27.00  68.00   0.50    1.00    --    0.00  37.00-180.00   82
  3  \w    -35.00  21.00   0.50    1.00    --    0.00 -19.00-150.00  112
  4  \w    -75.00  17.00   0.50    1.00    --    0.00 -37.00 150.00  184
  5  \w    -11.00  88.00   0.50    1.00    --    0.00  37.00 120.00  198
  6  \w     44.00  94.00   0.50    3.08    --  107.20 -30.00 -90.00  100
  7  \w     81.00 195.00   0.50    3.08    --  107.20  15.00  30.00  228
  8  \w     46.00  77.00   0.50    3.08    --  107.20 -45.00 150.00   62
  9  \w     28.00 140.00   0.50    3.08    --  107.20 -82.00 120.00  224
 10  \w     38.00 135.00   0.50    3.08    --  107.20 -15.00 -30.00  194
 11  \w    102.00 186.00   0.50    3.08    --  107.20  15.00 -60.00  168
 12  \w     39.00 140.00   0.50    3.08    --  107.20 -82.00 -90.00  202
 13  \w     92.00 196.00   0.50    3.08    --  107.20  30.00 -30.00  208
 14  \w     48.00  82.00   0.50    3.08    --  107.20 -61.00  30.00   68
 15  \w     46.00 100.00   0.50    3.08    --  107.20 -82.00 -60.00  108
 16  \w     81.00 117.00   0.50    3.08    --  107.20 -45.00 150.00   72
 17  \w     39.00 127.00   0.50    3.08    --  107.20 -61.00 120.00  176
 18  \w     92.00 136.00   0.50    3.08    --  107.20 -82.00   0.00   88
 19  \w     89.00 114.00   0.50    3.08    --  107.20 -82.00-180.00   50
 20  \w     43.00 110.00   0.50    3.08    --  107.20 -82.00  30.00  134
 21  \w     46.00  71.00   0.50    3.08    --  107.20 -82.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0195809000
_diffrn_orient_matrix_UB_12      0.0035947000
_diffrn_orient_matrix_UB_13      0.1200925000
_diffrn_orient_matrix_UB_21      0.1702189000
_diffrn_orient_matrix_UB_22      0.1048807000
_diffrn_orient_matrix_UB_23      0.0468220000
_diffrn_orient_matrix_UB_31      -0.0910414000
_diffrn_orient_matrix_UB_32      0.1133908000
_diffrn_orient_matrix_UB_33      -0.0150395000
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10533
_diffrn_reflns_theta_full        79.7486
_diffrn_reflns_theta_max         79.75
_diffrn_reflns_theta_min         3.72
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69174
_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            colourless
_exptl_crystal_density_diffrn    1.3171
_exptl_crystal_description       block
_exptl_crystal_F_000             429.8533
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3287
_refine_diff_density_min         -0.4861
_refine_diff_density_rms         0.0542
_refine_ls_d_res_high            0.7834
_refine_ls_d_res_low             11.8714
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0231
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0512P)^2^+0.6500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3973
_reflns_number_total             4274
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob01356e2.cif
_cod_data_source_block           exp_538_23
_cod_depositor_comments
'Adding full bibliography for 7160172--7160173.cif.'
_cod_database_code               7160173
_reflns_odcompleteness_completeness 99.53
_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:
 C00M(H00a,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00F(H00F), C00L(H00L), C00P(H00q), C00R(H00s), C00J(H00J),
 C00E(H00E), C00Q(H00r), C00G(H00G), C00H(H00H), C00B(H00B)
2.c Idealised Me refined as rotating group:
 C00N(H00d,H00i,H00m), C00O(H00n,H00o,H00p), C00S(H00t,H00u,H00v), C00T(H00w,
 H00x,H00y)
;
_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 1.799
_oxdiff_exptl_absorpt_empirical_full_min 0.699