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_7125018
_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         'C18 H24 N2 O2 S'
_chemical_formula_sum            'C18 H24 N2 O2 S'
_chemical_formula_weight         332.45
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-27
_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                 96.5156(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.79743(16)
_cell_length_b                   13.38129(20)
_cell_length_c                   11.85342(17)
_cell_measurement_reflns_used    8875
_cell_measurement_temperature    123.02(10)
_cell_measurement_theta_max      76.2670
_cell_measurement_theta_min      4.9590
_cell_volume                     1701.56(4)
_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      123.02(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 0.997
_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    1.50    --  -40.71 -37.00 -60.00  103
  2  \w     14.00 117.00   1.00    1.50    --   40.71  37.00 -90.00  103
  3  \w    -33.00  70.00   1.00    1.50    --   40.71 -57.00 120.00  103
  4  \w     35.00  69.00   1.00    3.00    --  113.00 -30.00-150.00   34
  5  \w     35.00  69.00   1.00    3.00    --  113.00 -30.00-180.00   34
  6  \w     85.00 158.00   1.00    3.00    --  113.00  45.00 150.00   73
  7  \w     35.00  69.00   1.00    3.00    --  113.00 -30.00 -90.00   34
  8  \w     24.00 158.00   1.00    3.00    --  113.00   0.00 150.00  134
  9  \w     35.00  69.00   1.00    3.00    --  113.00 -30.00 -60.00   34
 10  \w     83.00 158.00   1.00    3.00    --  113.00  61.00 120.00   75
 11  \w     38.00  77.00   1.00    3.00    --  113.00 -45.00  90.00   39
 12  \w     34.00 147.00   1.00    3.00    --  113.00 -77.00 -30.00  113
 13  \w     83.00 158.00   1.00    3.00    --  113.00  61.00  30.00   75
 14  \w     38.00  77.00   1.00    3.00    --  113.00 -45.00 -60.00   39
 15  \w     39.00 143.00   1.00    3.00    --  113.00 -61.00  90.00  104
 16  \w     52.00 158.00   1.00    3.00    --  113.00  15.00  90.00  106
 17  \w     35.00  69.00   1.00    3.00    --  113.00 -30.00-120.00   34
 18  \w     35.00 150.00   1.00    3.00    --  113.00 178.00 -90.00  115
 19  \w     61.00 147.00   1.00    3.00    --  113.00 -77.00 105.85   86
;
_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      -0.1115857000
_diffrn_orient_matrix_UB_12      0.0721514000
_diffrn_orient_matrix_UB_13      -0.0053634000
_diffrn_orient_matrix_UB_21      -0.0341743000
_diffrn_orient_matrix_UB_22      -0.0417634000
_diffrn_orient_matrix_UB_23      0.1135576000
_diffrn_orient_matrix_UB_31      0.0836258000
_diffrn_orient_matrix_UB_32      0.0794569000
_diffrn_orient_matrix_UB_33      0.0646841000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13860
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         76.495
_diffrn_reflns_theta_min         5.003
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.954
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.6855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3333
_reflns_number_total             3557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06111g2.cif
_cod_data_source_block           p094
_cod_database_code               7125018
_chemical_oxdiff_formula         'C18 H24 N2 O2 S'
_chemical_oxdiff_usercomment     Meyer_Koenig_AM-1274(AM-III-026)
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C18(H18A,H18B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C9(H9), C7(H7), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              71191
_shelx_hkl_checksum              7278
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-27
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with inert oil'
_olex2_submission_original_sample_id AM-1274(AM-III-026)
_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 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.696