Oxidative [3+2] annulation of activated pyridines for the synthesis of indolizinyl sulfonyl fluorides: a class of important pharmacophores.
Zhang, Sen; Fayad, Eman; Katouah, Hanadi A.; Huang, Yi-Yong; Qin, Hua-Li; Chemical communications (Cambridge, England) 61 (2025) 10586–10589; doi:10.1039/d5cc02186c

data_7134729
_publ_section_title
;
 Oxidative [3+2] annulation of activated pyridines for the synthesis of
 indolizinyl sulfonyl fluorides: a class of important pharmacophores.
;
_journal_issue                   57
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10586
_journal_page_last               10589
_journal_paper_doi               10.1039/d5cc02186c
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C17 H14 F N O4 S'
_chemical_formula_sum            'C17 H14 F N O4 S'
_chemical_formula_weight         347.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-11 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                89.993(2)
_cell_angle_beta                 77.842(2)
_cell_angle_gamma                70.533(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4933(3)
_cell_length_b                   9.7205(2)
_cell_length_c                   9.7983(2)
_cell_measurement_reflns_used    5282
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6350
_cell_measurement_theta_min      4.6360
_cell_volume                     830.96(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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    -60.00 -21.00   0.50    0.06    --  -39.95  84.00-108.00   78
  2  \w     26.00  76.00   0.50    0.06    --   39.95 -84.00 131.00  100
  3  \w     -4.00  22.00   0.50    0.06    --   39.95 -84.00 131.00   52
  4  \w   -171.00 -79.00   0.50    0.25    --  -94.50 -84.00 131.00  184
  5  \w     93.00 119.00   0.50    0.25    --  108.87 -84.00 131.00   52
  6  \w     53.00  79.00   0.50    0.25    --  108.87 -84.00 131.00   52
  7  \w    -65.00 -15.00   0.50    0.06    --  -39.95 -57.00-180.00  100
  8  \w      4.00  38.00   0.50    0.06    --  -39.95  84.00-108.00   68
  9  \w    -27.00  26.00   0.50    0.06    --  -39.95  19.00-120.00  106
 10  \w    -26.00  42.00   0.50    0.06    --  -39.95  19.00 -60.00  136
 11  \w   -113.00 -76.00   0.50    0.06    --  -39.95 -57.00-180.00   74
 12  \w    -14.00  41.00   0.50    0.06    --  -39.95  37.00 -30.00  110
 13  \w     63.00 125.00   0.50    0.06    --   39.95 178.00-180.00  124
 14  \w    -51.00 -15.00   0.50    0.25    --  -94.50  45.00  30.00   72
 15  \w   -131.00 -95.00   0.50    0.25    --  -94.50  84.00-108.00   72
 16  \w   -149.00 -73.00   0.50    0.25    --  -94.50-125.00 -60.00  152
 17  \w   -105.00 -72.00   0.50    0.25    --  -94.50  77.00 -30.00   66
 18  \w    -51.00 -26.00   0.50    0.25    --  -94.50  45.00-150.00   50
 19  \w   -113.00 -72.00   0.50    0.25    --  -94.50 -45.00-180.00   82
 20  \w   -174.00-121.00   0.50    0.25    --  -94.50 -45.00-180.00  106
 21  \w   -175.00 -92.00   0.50    0.25    --  -94.50 -94.00 -90.00  166
 22  \w    -67.00 -41.00   0.50    0.25    --  -94.50  84.00-108.00   52
 23  \w    -58.00 -32.00   0.50    0.25    --  -94.50  77.00 -30.00   52
 24  \w     96.00 139.00   0.50    0.25    --  108.87 125.00-150.00   86
 25  \w     68.00 108.00   0.50    0.25    --  108.87-125.00 120.00   80
 26  \w     35.00  65.00   0.50    0.25    --  108.87-125.00  90.00   60
 27  \w     63.00 104.00   0.50    0.25    --  108.87 -77.00 -90.00   82
 28  \w     36.00 111.00   0.50    0.25    --  108.87-125.00 -90.00  150
 29  \w     80.00 172.00   0.50    0.25    --  108.87  61.00 -60.00  184
 30  \w     35.00 111.00   0.50    0.25    --  108.87-125.00-180.00  152
 31  \w     44.00  70.00   0.50    0.25    --  108.87 -61.00 150.00   52
 32  \w     76.00 106.00   0.50    0.25    --  108.87-125.00  90.00   60
 33  \w     40.00  71.00   0.50    0.25    --  108.87 -61.00  60.00   62
 34  \w     37.00 111.00   0.50    0.25    --  108.87-125.00 -30.00  148
 35  \w    102.00 144.00   0.50    0.25    --  108.87 125.00 -30.00   84
 36  \w     99.00 158.00   0.50    0.25    --  108.87 125.00 120.00  118
 37  \w    117.00 158.00   0.50    0.25    --  108.87  45.00   0.00   82
 38  \w     70.00 104.00   0.50    0.25    --  108.87 -94.00 -30.00   68
 39  \w    105.00 159.00   0.50    0.25    --  108.87  84.00-108.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0745058000
_diffrn_orient_matrix_UB_12      -0.0552174000
_diffrn_orient_matrix_UB_13      0.1339714000
_diffrn_orient_matrix_UB_21      0.1537445000
_diffrn_orient_matrix_UB_22      -0.0487437000
_diffrn_orient_matrix_UB_23      0.0459551000
_diffrn_orient_matrix_UB_31      -0.0446288000
_diffrn_orient_matrix_UB_32      0.1516418000
_diffrn_orient_matrix_UB_33      0.0771871000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7922
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         4.630
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.491
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1010P)^2^+0.1396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2575
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02186c2.cif
_cod_data_source_block           so2f
_cod_depositor_comments          'Adding full bibliography for 7134729.cif.'
_cod_database_code               7134729
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S F'
_shelx_estimated_absorpt_t_max   0.823
_shelx_estimated_absorpt_t_min   0.794
_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. Restrained distances
 S1-F1 \\sim S1-F1A
 with sigma of 0.02
 S1-O3 \\sim S1-O3A
 with sigma of 0.02
 S1-O4 \\sim S1-O4A
 with sigma of 0.02
3. Rigid bond restraints
 S1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
4. Uiso/Uaniso restraints and constraints
Uanis(S1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F1A) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(O4A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(F1A)=Sof(O3A)=Sof(O4A)=1-FVAR(1)
 Sof(F1)=Sof(O3)=Sof(O4)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
6.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              56739
_shelx_hkl_checksum              24531
_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 1.837
_oxdiff_exptl_absorpt_empirical_full_min 0.604