Metal-free C-H sulfonamidation of pyrroles by visible light photoredox catalysis.
Meyer, Andreas Uwe; Berger, Anna Lucia; König, Burkhard; Chemical communications (Cambridge, England) 52 (2016) 10918–10921; doi:10.1039/c6cc06111g

data_7125020
_publ_section_title
;
 Metal-free C-H sulfonamidation of pyrroles by visible light photoredox
 catalysis.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10918
_journal_page_last               10921
_journal_paper_doi               10.1039/c6cc06111g
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         '2(C15 H20 N2 O2 S)'
_chemical_formula_sum            'C30 H40 N4 O4 S2'
_chemical_formula_weight         584.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-07-21
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_audit_update_record
;
2016-07-21 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.174(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0343(3)
_cell_length_b                   7.58100(10)
_cell_length_c                   23.5816(3)
_cell_measurement_reflns_used    23477
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.4040
_cell_measurement_theta_min      3.6700
_cell_volume                     3045.18(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (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      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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   -117.00 -14.00   1.00    3.50    --  -40.71 -37.00-120.00  103
  2  \w    -98.00  -2.00   1.00    3.50    --  -40.71 125.00-150.00   96
  3  \w   -115.00 -11.00   1.00    3.50    --  -40.71 -57.00-180.00  104
  4  \w    -34.00  68.00   1.00    3.50    --   40.71 -46.00  40.00  102
  5  \w     32.00  77.00   1.00   14.00    --  106.98 -45.00-180.00   45
  6  \w     73.00 158.00   1.00   14.00    --  106.98 125.00  30.00   85
  7  \w     46.00 158.00   1.00   14.00    --  106.98  15.00-120.00  112
  8  \w     32.00  77.00   1.00   14.00    --  106.98 -45.00   0.00   45
  9  \w     77.00 158.00   1.00   14.00    --  106.98  61.00  90.00   81
 10  \w     73.00 158.00   1.00   14.00    --  106.98  77.00-120.00   85
 11  \w     32.00  77.00   1.00   14.00    --  106.98 -45.00 -90.00   45
 12  \w     77.00 158.00   1.00   14.00    --  106.98  61.00 120.00   81
 13  \w     29.00  69.00   1.00   14.00    --  106.98 -30.00 -60.00   40
 14  \w     29.00  69.00   1.00   14.00    --  106.98 -30.00 -30.00   40
 15  \w     77.00 158.00   1.00   14.00    --  106.98  61.00 -30.00   81
 16  \w     73.00 158.00   1.00   14.00    --  106.98  77.00 -90.00   85
 17  \w     77.00 158.00   1.00   14.00    --  106.98  61.00-120.00   81
 18  \w     75.00 158.00   1.00   14.00    --  106.98  68.00 -59.96   83
 19  \w    -98.00  -2.00   1.00    3.50    --  -40.71 125.00 120.00   96
 20  \w   -119.00  -7.00   1.00    3.50    --  -40.71 -77.00  60.00  112
 21  \w   -119.00  -7.00   1.00    3.50    --  -40.71 -77.00 150.00  112
 22  \w      2.00  98.00   1.00    3.50    --   40.71-125.00  30.00   96
 23  \w      7.00 119.00   1.00    3.50    --   40.71  77.00  60.00  112
 24  \w      7.00 119.00   1.00    3.50    --   40.71  77.00 -30.00  112
 25  \w     32.00 121.00   1.00   14.00    --  106.98-125.00-120.00   89
 26  \w     73.00 158.00   1.00   14.00    --  106.98  77.00-180.00   85
 27  \w     32.00  77.00   1.00   14.00    --  106.98 -45.00  90.00   45
 28  \w     23.00 109.00   1.00   14.00    --  106.98 -94.00 -60.00   86
 29  \w     77.00 158.00   1.00   14.00    --  106.98  61.00  60.00   81
 30  \w     28.00 141.00   1.00   14.00    --  106.98 -77.00   0.00  113
 31  \w     23.00 109.00   1.00   14.00    --  106.98 -94.00  90.00   86
 32  \w     77.00 102.00   1.00   14.00    --  106.98  61.00 150.00   25
 33  \w     79.00 158.00   1.00   14.00    --  106.98  45.00  30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0522636000
_diffrn_orient_matrix_UB_12      0.0489643000
_diffrn_orient_matrix_UB_13      0.0640734000
_diffrn_orient_matrix_UB_21      0.0684020000
_diffrn_orient_matrix_UB_22      -0.1050398000
_diffrn_orient_matrix_UB_23      -0.0090197000
_diffrn_orient_matrix_UB_31      0.0277355000
_diffrn_orient_matrix_UB_32      0.1668986000
_diffrn_orient_matrix_UB_33      -0.0244476000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            45303
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.550
_diffrn_reflns_theta_min         3.749
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.914
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0547P)^2^+1.6355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5586
_reflns_number_total             6102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06111g2.cif
_cod_data_source_block           p089
_cod_database_code               7125020
_chemical_oxdiff_formula         'C15 H20 N2 O2 S'
_chemical_oxdiff_usercomment     'Meyer_Koenig_AM-1273 (AM-III-025)'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C2(H2), C6(H6), C3(H3), C26(H26), C23(H23), C38(H38), C16(H16),
 C25(H25), C5(H5), C17(H17), C18(H18), C37(H37), C36(H36)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C30(H30A,H30B,H30C), C20(H20A,H20B,H20C), C34(H34A,H34B,
 H34C), C14(H14A,H14B,H14C), C40(H40A,H40B,H40C), C31(H31A,H31B,H31C), C11(H11A,
 H11B,H11C)
;
_shelx_res_checksum              27767
_shelx_hkl_checksum              45098
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-19
_olex2_date_sample_submission    2016-06-15
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a Lindemann tube with inert oil'
_olex2_submission_original_sample_id AM-1273(AM-III-025)
_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.701