Direct Synthesis of Pentasubstituted Pyrroles and Hexasubstituted Pyrrolines from Propargyl Sulfonylamides and Allenamides
Ye, Changqing; Jiao, Yihang; Chiou, Mong-Feng; Li, Yajun; Bao, Hongli; Chemical Science  (2021) –; doi:10.1039/D1SC02090K

data_1563269
_publ_section_title
;
 Direct Synthesis of Pentasubstituted Pyrroles and Hexasubstituted
 Pyrrolines from Propargyl Sulfonylamides and Allenamides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02090K
_journal_year                    2021
_chemical_formula_moiety         'C26 H21 N3 O'
_chemical_formula_sum            'C26 H21 N3 O'
_chemical_formula_weight         391.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-24 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.819(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.8324(4)
_cell_length_b                   9.05410(10)
_cell_length_c                   21.9042(4)
_cell_measurement_reflns_used    23659
_cell_measurement_temperature    110.43(10)
_cell_measurement_theta_max      60.4580
_cell_measurement_theta_min      3.2310
_cell_volume                     4633.13(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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      110.43(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.977
_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     -1.00  24.00   0.50    0.05    --   72.03 -77.00  30.00   50
  2  \w     38.00  73.00   0.50    0.05    --   72.03 -77.00  30.00   70
  3  \w     14.00  65.00   0.50    0.05    --   72.03 -57.00 -30.00  102
  4  \w      7.00  96.00   0.50    0.05    --   72.03 -77.00-180.00  178
  5  \w      2.00  51.00   0.50    0.05    --   72.03 -57.00-180.00   98
  6  \w     -2.00  43.00   0.50    0.05    --   72.03 -38.00 -30.00   90
  7  \w      5.00  41.00   0.50    0.05    --   72.03 -38.00  90.00   72
  8  \w      5.00  32.00   0.50    0.05    --   72.03 -38.00-120.00   54
  9  \w     -1.00  26.00   0.50    0.05    --   72.03 -19.00-120.00   54
 10  \w      0.00  25.00   0.50    0.05    --   72.03 -19.00   0.00   50
 11  \w     -3.00  22.00   0.50    0.05    --   72.03 -19.00 -90.00   50
 12  \w      1.00  34.00   0.50    0.05    --   72.03 -38.00-150.00   66
 13  \w     -3.00  26.00   0.50    0.05    --   72.03 -19.00-150.00   58
 14  \w     56.00 145.00   0.50    0.05    --   72.03  57.00 -60.00  178
 15  \w    104.00 144.00   0.50    0.05    --   72.03 125.00-180.00   80
 16  \w     21.00  56.00   0.50    0.05    --   72.03-125.00 120.00   70
 17  \w     64.00 112.00   0.50    0.05    --   72.03-125.00 120.00   96
 18  \w     68.00 106.00   0.50    0.05    --   72.03 -99.00-180.00   76
 19  \w     75.00 106.00   0.50    0.05    --   72.03-125.00-180.00   62
 20  \w     20.00  62.00   0.50    0.05    --   72.03-125.00-180.00   84
 21  \w      9.00  34.00   0.50    0.05    --   72.03 -99.00-180.00   50
 22  \w    -63.00  -3.00   0.50    0.05    --   -1.72 -77.00 -30.00  120
 23  \w    -49.00  15.00   0.50    0.05    --   -1.72 -57.00   0.00  128
 24  \w    -66.00 -19.00   0.50    0.05    --  -75.46  57.00 120.00   94
 25  \w    -13.00  27.00   0.50    0.05    --   -1.72  57.00 120.00   80
 26  \w     32.00  65.00   0.50    0.05    --   -1.72  57.00 120.00   66
 27  \w    -66.00 -40.00   0.50    0.05    --  -75.46  57.00-180.00   52
 28  \w    -66.00 -25.00   0.50    0.05    --  -75.46 125.00 -90.00   82
 29  \w    -96.00 -62.00   0.50    0.05    --  -75.46 125.00 -60.00   68
 30  \w    -98.00 -69.00   0.50    0.05    --  -75.46 125.00 -90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0554461000
_diffrn_orient_matrix_UB_12      -0.0341557000
_diffrn_orient_matrix_UB_13      0.0282278000
_diffrn_orient_matrix_UB_21      0.0127673000
_diffrn_orient_matrix_UB_22      0.0776798000
_diffrn_orient_matrix_UB_23      -0.0453365000
_diffrn_orient_matrix_UB_31      0.0074779000
_diffrn_orient_matrix_UB_32      0.1209575000
_diffrn_orient_matrix_UB_33      0.0370097000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28636
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.460
_diffrn_reflns_theta_min         4.554
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       plank
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0440P)^2^+3.2990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4918
_reflns_number_total             5187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02090k2.cif
_cod_data_source_block           ycq-13-140
_cod_original_cell_volume        4633.12(14)
_cod_database_code               1563269
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHON
_diffrn_oxdiff_digest_frames
;
015863926324b7eeccc7910dded7fea6980243698bd
;
_diffrn_oxdiff_digest_hkl
;
01ede481a03cc6105f1b8385daa5cabcb1bb23
;
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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.a Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00C(H00C), C00E(H00E), C00G(H00G), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC)
;
_shelx_res_checksum              61987
_shelx_hkl_checksum              13021
_shelx_fab_checksum              479
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.598