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_1563268
_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         'C24 H17 F2 N3 O2 S'
_chemical_formula_sum            'C24 H17 F2 N3 O2 S'
_chemical_formula_weight         449.46
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-18
_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                 94.11(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.864(4)
_cell_length_b                   9.0235(19)
_cell_length_c                   17.39(2)
_cell_measurement_reflns_used    1353
_cell_measurement_temperature    292.90(11)
_cell_measurement_theta_max      64.6360
_cell_measurement_theta_min      3.9600
_cell_volume                     4361(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      292.90(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2083
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.973
_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    -33.00  72.00   1.00    1.00    --    0.00  77.00  90.00  105
  2  \w    -33.00  72.00   1.00    1.00    --    0.00  77.00  90.00  105
  3  \w     26.00 120.00   1.00    1.00    --   49.59  57.00 -30.00   94
  4  \w     26.00 120.00   1.00    1.00    --   49.59  57.00-150.00   94
  5  \w     27.00 112.00   1.00    1.00    --   49.59-130.00 -75.00   85
  6  \w    -24.00  81.00   1.00    1.00    --   49.59 -38.00  60.00  105
  7  \w    100.00 173.00   1.00    1.00    --   99.19 111.00 -30.00   73
  8  \w    100.00 173.00   1.00    1.00    --   99.19 111.00 -90.00   73
  9  \w     81.00 169.00   1.00    1.00    --   99.19  50.00-150.00   88
 10  \w     88.00 145.00   1.00    1.00    --   99.19 178.00 120.00   57
 11  \w     65.00 109.00   1.00    1.00    --   99.19-111.00 120.00   44
 12  \w     55.00 166.00   1.00    1.00    --   99.19  25.00 -30.00  111
 13  \w    112.00 165.00   1.00    1.00    --   99.19 130.00  -2.00   53
 14  \w     28.00 123.00   1.00    1.00    --   99.19 -50.00-120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0444645000
_diffrn_orient_matrix_UB_12      -0.0071399000
_diffrn_orient_matrix_UB_13      -0.0607817000
_diffrn_orient_matrix_UB_21      0.0324317000
_diffrn_orient_matrix_UB_22      0.0011225000
_diffrn_orient_matrix_UB_23      -0.0664649000
_diffrn_orient_matrix_UB_31      0.0029619000
_diffrn_orient_matrix_UB_32      -0.1696887000
_diffrn_orient_matrix_UB_33      0.0022437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8983
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        65.440
_diffrn_reflns_theta_max         65.440
_diffrn_reflns_theta_min         5.099
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0617P)^2^+1.3026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3035
_reflns_number_total             3649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02090k2.cif
_cod_data_source_block           jyy
_cod_original_cell_volume        4362(6)
_cod_database_code               1563268
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W)
;
_shelx_res_checksum              70443
_shelx_hkl_checksum              47265
_olex2_date_sample_data_collection 2019-02-16
_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 1.608
_oxdiff_exptl_absorpt_empirical_full_min 0.748