Silver or copper-catalyzed ring opening [3+2] annulation of 2-polyfluoroalkyl chromones/6-polyfluoroalkyl pyran-4H-ones with methylene isocyanides: regioselective synthesis of 3-polyfluoroalkyl pyrroles
Kochnev, Ivan A.; Barkov, Alexey Yu.; New Journal of Chemistry 49 (2025) 20254–20263; doi:10.1039/D5NJ03333K

data_7064108
_publ_section_title
;
 Silver or copper-catalyzed ring opening [3+2] annulation of
 2-polyfluoroalkyl chromones/6-polyfluoroalkyl pyran-4H-ones with
 methylene isocyanides: regioselective synthesis of 3-polyfluoroalkyl
 pyrroles
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20254
_journal_page_last               20263
_journal_paper_doi               10.1039/D5NJ03333K
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C17 H13 F3 N2 O3'
_chemical_formula_sum            'C17 H13 F3 N2 O3'
_chemical_formula_weight         350.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-18
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-09-26 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0298(7)
_cell_length_b                   7.5259(7)
_cell_length_c                   31.6005(19)
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.7080
_cell_measurement_theta_min      3.0080
_cell_volume                     3098.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_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      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.844
_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    -39.00  -6.00   1.00   60.00    --  -19.06 -77.00-180.00   33
  2  \w    -32.00   0.00   1.00   60.00    --  -19.06 -77.00  60.00   32
  3  \w    -14.00  46.00   1.00   60.00    --   21.56 -19.00  60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8639
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.176
_diffrn_reflns_theta_min         3.015
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
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    1.502
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1781
_refine_ls_R_factor_gt           0.0631
_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^)+(0.0387P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1361
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1771
_reflns_number_total             4226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03333k2.cif
_cod_data_source_block           exp_1812
_cod_depositor_comments
'Adding full bibliography for 7064105--7064108.cif.'
_cod_database_code               7064108
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.941
_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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C10(H10), C9(H9), C8(H8)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
;