Formal [4 + 1] annulation of fluorinated sulfonium salt with cyclic unsaturated imines to access CF<sub>3</sub>-substituted pyrroles.
Chen, Tao; Wang, Aoning; Zhang, Linxue; Wei, Chenlong; Huang, Juhui; Liu, Xiang; Fu, Zhenqian; Organic & biomolecular chemistry 19 (2021) 3128–3133; doi:10.1039/d1ob00218j

data_7157971
_publ_section_title
;
 Formal [4 + 1] annulation of fluorinated sulfonium salt with cyclic
 unsaturated imines to access CF<sub>3</sub>-substituted pyrroles.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3128
_journal_page_last               3133
_journal_paper_doi               10.1039/d1ob00218j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C26 H21 Cl F3 N O2 S'
_chemical_formula_sum            'C26 H21 Cl F3 N O2 S'
_chemical_formula_weight         503.95
_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     dual
_audit_creation_date             2019-11-15
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.31 svn.r3677 for OlexSys, GUI svn.r5972)
;
_audit_update_record
;
2020-04-20 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.239(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7555(2)
_cell_length_b                   19.8449(4)
_cell_length_c                   15.1282(3)
_cell_measurement_reflns_used    8753
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4730
_cell_measurement_theta_min      2.8900
_cell_volume                     2275.42(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_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    -65.00 -33.00   1.00    1.00    --  -40.98  38.00-120.00   32
  2  \w    -94.00 -17.00   1.00    1.00    --  -40.98 125.00-180.00   77
  3  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00  60.00   99
  4  \w     44.00  96.00   1.00    1.00    --   40.98-125.00  30.00   52
  5  \w     31.00 140.00   1.00    1.00    --  106.95 -77.00 -90.00  109
  6  \w    107.00 133.00   1.00    1.00    --  106.95 -30.00 -90.00   26
  7  \w     74.00 149.00   1.00    1.00    --  106.95  77.00  60.00   75
  8  \w    114.00 160.00   1.00    1.00    --  106.95  94.00  16.00   46
  9  \w     94.00 175.00   1.00    1.00    --  106.95 125.00 -60.00   81
 10  \w     81.00 131.00   1.00    1.00    --  106.95  77.00 120.00   50
 11  \w     38.00  90.00   1.00    1.00    --  106.95 -30.00 -90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0202981000
_diffrn_orient_matrix_UB_12      -0.0555835000
_diffrn_orient_matrix_UB_13      -0.0725868000
_diffrn_orient_matrix_UB_21      -0.0701444000
_diffrn_orient_matrix_UB_22      0.0457571000
_diffrn_orient_matrix_UB_23      -0.0583382000
_diffrn_orient_matrix_UB_31      0.0706562000
_diffrn_orient_matrix_UB_32      0.0292065000
_diffrn_orient_matrix_UB_33      -0.0467019000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9280
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.606
_diffrn_reflns_theta_min         3.728
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0529P)^2^+0.8391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4124
_reflns_number_total             4479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00218j2.cif
_cod_data_source_block           ct3r-3
_cod_depositor_comments          'Adding full bibliography for 7157971.cif.'
_cod_database_code               7157971
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C21(H21), C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              14320
_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 1.817
_oxdiff_exptl_absorpt_empirical_full_min 0.776