Base-promoted [3+2] annulation of <i>N</i>-aminoisoquinolinium derivatives with cyclic iodonium ylide/2,2-difluorovinyl tosylate.
Liu, Xiang; Wu, Wen-Rong; Ma, Shaohong; Chen, Juan; Meng, Yuan-Jie; Yang, Zi-Feng; Zhang, Shang-Shi; Feng, Pengju; Chemical communications (Cambridge, England) 61 (2025) 17673–17676; doi:10.1039/d5cc05132k

data_7135091
_publ_section_title
;
 Base-promoted [3+2] annulation of <i>N</i>-aminoisoquinolinium
 derivatives with cyclic iodonium ylide/2,2-difluorovinyl tosylate.
;
_journal_issue                   90
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17673
_journal_page_last               17676
_journal_paper_doi               10.1039/d5cc05132k
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C17 H16 N2 O'
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-17
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-08-18 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.126(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8248(2)
_cell_length_b                   13.1914(3)
_cell_length_c                   11.6734(3)
_cell_measurement_reflns_used    3131
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.8270
_cell_measurement_theta_min      3.3380
_cell_volume                     1328.60(6)
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(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 0.972
_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    -51.00  32.00   1.00    1.00    --  -40.73  38.00 -60.00   83
  2  \w    -67.00  22.00   1.00    1.00    --  -40.73  77.00  30.00   89
  3  \w     40.00  90.00   1.00    1.00    --   40.73-125.00-120.00   50
  4  \w     25.00 108.00   1.00    1.00    --  107.58 -94.00-180.00   83
  5  \w     35.00 121.00   1.00    1.00    --  107.58 -30.00-180.00   86
  6  \w    143.00 177.00   1.00    1.00    --  107.58  45.00 -90.00   34
  7  \w    130.00 177.00   1.00    1.00    --  107.58 125.00 -90.00   47
  8  \w    103.00 129.00   1.00    1.00    --  107.58 125.00 -90.00   26
  9  \w     79.00 175.00   1.00    1.00    --  107.58  30.00   0.00   96
 10  \w     92.00 149.00   1.00    1.00    --  107.58  45.00  60.00   57
;
_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      0.1442802000
_diffrn_orient_matrix_UB_12      0.0355350000
_diffrn_orient_matrix_UB_13      0.0894304000
_diffrn_orient_matrix_UB_21      -0.0565659000
_diffrn_orient_matrix_UB_22      -0.0579914000
_diffrn_orient_matrix_UB_23      0.0976731000
_diffrn_orient_matrix_UB_31      0.0884951000
_diffrn_orient_matrix_UB_32      -0.0950211000
_diffrn_orient_matrix_UB_33      -0.0261302000
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.955
_diffrn_reflns_theta_min         5.124
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74037
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0750P)^2^+0.2773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2378
_reflns_number_total             2615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05132k2.cif
_cod_data_source_block           wnr
_cod_depositor_comments          'Adding full bibliography for 7135091.cif.'
_cod_database_code               7135091
_shelx_shelxl_version_number     2018/3
_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:
 C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              89954
_shelx_hkl_checksum              69417
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.505
_oxdiff_exptl_absorpt_empirical_full_min 0.593