Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides.
Gillbard, Simone M.; Chung, Chieh-Hsu; Karad, Somnath Narayan; Panchal, Heena; Lewis, William; Lam, Hon Wai; Chemical communications (Cambridge, England) 54 (2018) 11769–11772; doi:10.1039/c8cc06649c

data_7122367
_publ_section_title
;
 Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative
 cyclizations of N-tosyl alkynamides.
;
_journal_issue                   83
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11769
_journal_page_last               11772
_journal_paper_doi               10.1039/c8cc06649c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C31 H27 N O2 S'
_chemical_formula_sum            'C31 H27 N O2 S'
_chemical_formula_weight         477.59
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-08-08 deposited with the CCDC.
2018-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.932(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8229(3)
_cell_length_b                   24.8007(12)
_cell_length_c                   15.1265(7)
_cell_measurement_reflns_used    5654
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3500
_cell_measurement_theta_min      3.6030
_cell_volume                     2513.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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   -112.00  -7.00   1.00   15.00    --  -38.50 -77.00  90.00  105
  2  \w    -94.00  -2.00   1.00   15.00    --  -38.50 125.00-150.00   92
  3  \w     21.00 116.00   1.00   15.00    --   43.38  38.00 -90.00   95
  4  \w     31.00  91.00   1.00   60.00    --  106.13 -30.00-150.00   60
  5  \w     35.00  98.00   1.00   60.00    --  106.13 -45.00 120.00   63
  6  \w     31.00  91.00   1.00   60.00    --  106.13 -30.00 -90.00   60
  7  \w     43.00  98.00   1.00   60.00    --  106.13 -45.00 -30.00   55
  8  \w    144.00 173.00   1.00   60.00    --  106.13 125.00 -60.00   29
  9  \w     94.00 120.00   1.00   60.00    --  106.13 125.00 -60.00   26
 10  \w     36.00 107.00   1.00   60.00    --  106.13 -95.00  90.00   71
 11  \w     35.00  98.00   1.00   60.00    --  106.13 -45.00  60.00   63
 12  \w     75.00 102.00   1.00   60.00    --  106.13-109.00  75.00   27
 13  \w     82.00 177.00   1.00   60.00    --  106.13  45.00-150.00   95
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1474584000
_diffrn_orient_matrix_UB_12      -0.0334988000
_diffrn_orient_matrix_UB_13      -0.0681783000
_diffrn_orient_matrix_UB_21      -0.0529501000
_diffrn_orient_matrix_UB_22      0.0506628000
_diffrn_orient_matrix_UB_23      -0.0587899000
_diffrn_orient_matrix_UB_31      0.1681151000
_diffrn_orient_matrix_UB_32      -0.0134151000
_diffrn_orient_matrix_UB_33      -0.0514061000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12859
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.519
_diffrn_reflns_theta_min         3.469
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.362
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.262
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0642P)^2^+1.3018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4294
_reflns_number_total             5011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06649c2.cif
_cod_data_source_block           snkhlc
_cod_depositor_comments          'Adding full bibliography for 7122367.cif.'
_cod_database_code               7122367
_nottingham_internal_coll_name   SNKHLC
_nottingham_internal_coll_number 17496
_nottingham_internal_coll_client SNK/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '15.00, 60.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   07/02/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_process_date 13/02/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 13/2/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 13/2/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 13/2/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 13/2/2018
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C31 H27 N O2 S'
_chemical_oxdiff_usercomment
'SNKHLC #17496 SN-1257 IN FOMBLIN FILM ON A MICROMOUNT FOR SNK/HWL'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C19(H19), C21(H21),
 C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              17936
_olex2_date_sample_data_collection 2018-02-07
_olex2_date_sample_submission    2018-02-06
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_original_sample_id CHC-01-36
_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 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.665