Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles
Zhang, Yu-Zhen; Mo, Zu-Yu; Wang, Heng-Shan; Wen, Xiao-An; Tang, Hai-Tao; Pan, Ying-Ming; Green Chemistry 21 (2019) 3807–; doi:10.1039/C9GC01201J

data_7232950
_publ_section_title
;
 Electrochemically enabled chemoselective sulfonylation and hydrazination
 of indoles
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              3807
_journal_paper_doi               10.1039/C9GC01201J
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C22 H21 N3 O4 S2'
_chemical_formula_sum            'C22 H21 N3 O4 S2'
_chemical_formula_weight         455.54
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-17 deposited with the CCDC.    2019-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                77.758(6)
_cell_angle_beta                 85.300(6)
_cell_angle_gamma                72.021(7)
_cell_formula_units_Z            4
_cell_length_a                   12.0153(10)
_cell_length_b                   12.5845(10)
_cell_length_c                   15.2028(9)
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    293.75(10)
_cell_measurement_theta_max      73.9390
_cell_measurement_theta_min      2.9500
_cell_volume                     2136.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.962
_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    -57.00  33.00   1.00    1.00    --  -39.92  57.00-150.00   90
  2  \w    -95.00  -2.00   1.00    1.00    --  -39.92 125.00-120.00   93
  3  \w     47.00  96.00   1.00    1.00    --   39.92-125.00  60.00   49
  4  \w     38.00 124.00   1.00    1.00    --  108.83 -61.00   0.00   86
  5  \w     75.00 102.00   1.00    1.00    --  108.83 -94.00 -30.00   27
  6  \w     69.00  99.00   1.00    1.00    --  108.83 -94.00   0.00   30
  7  \w     54.00 121.00   1.00    1.00    --  108.83-125.00 -60.00   67
  8  \w     42.00 135.00   1.00    1.00    --  108.83 -61.00-120.00   93
  9  \w     81.00 149.00   1.00    1.00    --  108.83  30.00 -30.00   68
 10  \w    139.00 166.00   1.00    1.00    --  108.83  45.00 -90.00   27
 11  \w     83.00 125.00   1.00    1.00    --  108.83  45.00 -90.00   42
 12  \w     33.00 137.00   1.00    1.00    --  108.83 -30.00  90.00  104
 13  \w     78.00 117.00   1.00    1.00    --  108.83-125.00 150.00   39
 14  \w     33.00 138.00   1.00    1.00    --  108.83 -77.00 120.00  105
 15  \w     27.00 158.00   1.00    1.00    --  108.83 -15.00 -60.00  131
 16  \w   -113.00 -23.00   1.00    1.00    --  -39.92 -37.00 -30.00   90
 17  \w   -114.00 -16.00   1.00    1.00    --  -39.92 -37.00  60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1331287000
_diffrn_orient_matrix_UB_12      -0.0289695000
_diffrn_orient_matrix_UB_13      0.0103647000
_diffrn_orient_matrix_UB_21      0.0048380000
_diffrn_orient_matrix_UB_22      -0.1213031000
_diffrn_orient_matrix_UB_23      0.0501096000
_diffrn_orient_matrix_UB_31      0.0207329000
_diffrn_orient_matrix_UB_32      -0.0409807000
_diffrn_orient_matrix_UB_33      -0.0902053000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14728
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.597
_diffrn_reflns_theta_min         2.975
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         8394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0740
_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^)+(0.0598P)^2^+46.8060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7050
_reflns_number_total             8394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc01201j2.cif
_cod_data_source_block           181225
_cod_depositor_comments          'Adding full bibliography for 7232950.cif.'
_cod_database_code               7232950
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.821
_shelx_estimated_absorpt_t_min   0.749
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 N3B(H3B), N1(H1), N1B(H1B), N2B(H2B), N2(H2), C13B(H13B), C3(H3A), C19B(H19B),
  C2(H2A), C5(H5), C15B(H15B), C21(H21), C21B(H21B), C11(H11), C14(H14),
 C17B(H17B), C12B(H12B), C10(H10), C14B(H14B), C19(H19), C18B(H18B), C17(H17),
 C12(H12), C4(H4), C2B(H2BA), C18(H18), C6B(H6B), C4B(H4B), C5B(H5B)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15C,H15D), C22B(H22A,H22B,H22C), C22(H22D,H22E,H22F), C7B(H7BA,H7BB,
 H7BC)
;
_olex2_date_sample_data_collection 2019-01-25
_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 1.504
_oxdiff_exptl_absorpt_empirical_full_min 0.488