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_7125021
_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         'C12 H16 N2 O2 S2'
_chemical_formula_sum            'C12 H16 N2 O2 S2'
_chemical_formula_weight         284.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-29
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-21 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.435(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6626(5)
_cell_length_b                   5.39440(16)
_cell_length_c                   18.2386(6)
_cell_measurement_reflns_used    6561
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.1540
_cell_measurement_theta_min      4.9490
_cell_volume                     1323.60(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 0.991
_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    -70.00  33.00   1.00    2.00    --  -40.71  57.00  30.00  103
  2  \w     14.00 117.00   1.00    2.00    --   40.71  37.00   0.00  103
  3  \w     14.00 117.00   1.00    2.00    --   40.71  37.00  90.00  103
  4  \w      2.00  98.00   1.00    2.00    --   40.71-125.00 -90.00   96
  5  \w     23.00 109.00   1.00    8.00    --  106.98 -94.00  30.00   86
  6  \w     77.00 158.00   1.00    8.00    --  106.98  61.00 -90.00   81
  7  \w     79.00 158.00   1.00    8.00    --  106.98  50.00 -45.00   79
  8  \w     29.00  69.00   1.00    8.00    --  106.98 -30.00  90.00   40
  9  \w     23.00 109.00   1.00    8.00    --  106.98 -94.00-150.00   86
 10  \w     73.00 158.00   1.00    8.00    --  106.98  77.00  30.00   85
 11  \w     77.00 158.00   1.00    8.00    --  106.98  61.00   0.00   81
 12  \w     73.00 158.00   1.00    8.00    --  106.98  77.00  60.00   85
 13  \w     23.00 109.00   1.00    8.00    --  106.98 -94.00-120.00   86
 14  \w     77.00 158.00   1.00    8.00    --  106.98  61.00  30.00   81
 15  \w     77.00 158.00   1.00    8.00    --  106.98  61.00  90.00   81
 16  \w     32.00 121.00   1.00    8.00    --  106.98-125.00-150.00   89
 17  \w     29.00  69.00   1.00    8.00    --  106.98 -30.00  30.00   40
 18  \w    -67.00  35.00   1.00    2.00    --  -40.71  37.00 150.00  102
 19  \w     11.00 115.00   1.00    2.00    --   40.71  57.00 150.00  104
 20  \w      7.00  71.00   1.00    2.00    --   40.71  77.00  30.00   64
 21  \w     11.00 115.00   1.00    2.00    --   40.71  57.00-120.00  104
;
_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      0.0311192000
_diffrn_orient_matrix_UB_12      0.0851407000
_diffrn_orient_matrix_UB_13      0.0872451000
_diffrn_orient_matrix_UB_21      0.0852498000
_diffrn_orient_matrix_UB_22      0.1537439000
_diffrn_orient_matrix_UB_23      -0.0061805000
_diffrn_orient_matrix_UB_31      -0.0699919000
_diffrn_orient_matrix_UB_32      0.2248545000
_diffrn_orient_matrix_UB_33      -0.0287328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12291
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.425
_diffrn_reflns_theta_min         4.992
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
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    1.427
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0438P)^2^+0.6307P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2442
_reflns_number_total             2655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06111g2.cif
_cod_data_source_block           mp_nc
_cod_database_code               7125021
_chemical_oxdiff_formula         'C12 H16 N2 O2 S2'
_chemical_oxdiff_usercomment     'Meyer_Koenig_AM-1269 (AM-III-021),F.3-5'
_reflns_odcompleteness_completeness 99.92
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C10
 1.374 with sigma of 0.001
 C9-C10A
 1.374 with sigma of 0.001
 C9-S2 \\sim S2-C12
 with sigma of 0.001
 C9-S2A \\sim S2A-C12A
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C12 \\sim C11A \\sim C12A \\sim C11 \\sim C10 \\sim C10A: within 1.7A with
sigma of 0.005 and sigma for terminal atoms of 0.005
S2A \\sim S2: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.005
4. Others
 Sof(S2A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(S2)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C12A(H12A),
 C11A(H11A), C10A(H10A)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              55157
_shelx_hkl_checksum              79618
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-21
_olex2_date_sample_submission    2016-06-15
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with inert oil'
_olex2_submission_original_sample_id AM-1269(AM-III-021),F.3-5
_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 2.056
_oxdiff_exptl_absorpt_empirical_full_min 0.641