Novel mono substituted pyridoimidazoisoquinoliniums via a silver-catalyzed intramolecular cyclization and their applications in cellular imaging
Kawakubo, Masato; Inoh, Yoshikazu; Murata, Yuki; Matsumura, Mio; Furuno, Tadahide; Yasuike, Shuji; RSC Advances 14 (2024) 9758–9762; doi:10.1039/D4RA01210K

data_7248339
_publ_section_title
;
 Novel mono substituted pyridoimidazoisoquinoliniums via a
 silver-catalyzed intramolecular cyclization and their applications in
 cellular imaging
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              9758
_journal_page_last               9762
_journal_paper_doi               10.1039/D4RA01210K
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C23 H17 F3 N2 O3 S'
_chemical_formula_sum            'C23 H17 F3 N2 O3 S'
_chemical_formula_weight         458.44
_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             2021-05-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-01-11 deposited with the CCDC.	2024-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                81.216(2)
_cell_angle_beta                 83.633(2)
_cell_angle_gamma                76.137(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5716(2)
_cell_length_b                   10.5701(3)
_cell_length_c                   13.3435(4)
_cell_measurement_reflns_used    6767
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.2020
_cell_measurement_theta_min      3.3370
_cell_volume                     1021.57(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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     21.00  47.00   0.50    0.20    --   40.40  50.00   0.00   52
  2  \w     81.00 106.00   0.50    0.20    --   40.40  50.00   0.00   50
  3  \w     78.00 104.00   0.50    0.20    --   40.40  63.00  90.00   52
  4  \w     63.00  90.00   0.50    0.20    --   40.40 138.00 120.00   54
  5  \w     74.00 162.00   0.50    0.20    --   96.04  59.00 120.00  176
  6  \w    102.00 165.00   0.50    0.20    --   96.04  77.00  30.00  126
  7  \w    101.00 163.00   0.50    0.20    --   96.04  59.00  90.00  124
  8  \w     96.00 121.00   0.50    0.20    --   96.04  85.00 142.00   50
  9  \w     70.00 165.00   0.50    0.20    --   96.04  77.00  60.00  190
 10  \w     85.00 153.00   0.50    0.20    --   96.04  33.00-120.00  136
 11  \w     71.00 163.00   0.50    0.20    --   96.04  77.00-180.00  184
 12  \w     61.00  87.00   0.50    0.20    --   40.40 138.00-180.00   52
 13  \w     -3.00  22.00   0.50    0.20    --  -40.71  37.00 -60.00   50
 14  \w     -1.00  24.00   0.50    0.20    --  -40.71  37.00 -90.00   50
 15  \w    -12.00  28.00   0.50    0.20    --  -40.71  77.00 -60.00   80
 16  \w    -30.00  26.00   0.50    0.20    --  -40.71  25.00-120.00  112
 17  \w    -38.00  -9.00   0.50    0.20    --  -40.71  37.00 -60.00   58
 18  \w    -38.00 -12.00   0.50    0.20    --  -40.71  37.00 -90.00   52
 19  \w    -67.00 -23.00   0.50    0.20    --  -40.71  77.00 -60.00   88
 20  \w    -57.00 -31.00   0.50    0.20    --  -96.35  50.00-120.00   52
 21  \w    -55.00 -30.00   0.50    0.20    --  -96.35  50.00 -90.00   50
 22  \w    -69.00 -31.00   0.50    0.20    --  -96.35  59.00 -90.00   76
 23  \w    -82.00 -31.00   0.50    0.20    --  -96.35  68.00 -90.00  102
 24  \w    -83.00 -30.00   0.50    0.20    --  -96.35  77.00 -60.00  106
 25  \w   -107.00 -29.00   0.50    0.20    --  -96.35  96.00 -60.00  156
 26  \w   -104.00 -79.00   0.50    0.20    --  -96.35  77.00 -90.00   50
 27  \w   -113.00 -30.00   0.50    0.20    --  -96.35 117.00 -60.00  166
 28  \w    -22.00  29.00   0.50    0.20    --  -40.71  25.00 120.00  102
 29  \w     -7.00  25.00   0.50    0.20    --  -40.71  85.00 142.00   64
 30  \w     26.00  69.00   0.50    0.20    --   40.40  63.00  90.00   86
 31  \w      3.00  31.00   0.50    0.20    --   40.40 -25.00  60.00   56
 32  \w     10.00  69.00   0.50    0.20    --   40.40 -85.00  23.00  118
 33  \w     34.00  79.00   0.50    0.20    --   40.40-138.00  30.00   90
 34  \w     44.00  70.00   0.50    0.20    --   40.40-138.00 -90.00   52
 35  \w     52.00  77.00   0.50    0.20    --   96.04 -85.00  23.00   50
 36  \w     37.00  68.00   0.50    0.20    --   96.04 -59.00  60.00   62
 37  \w     39.00  69.00   0.50    0.20    --   96.04 -59.00  30.00   60
 38  \w      8.00  33.00   0.50    0.20    --   40.40 -37.00 -30.00   50
 39  \w    -29.00  -4.00   0.50    0.20    --   40.40 -85.00  23.00   50
 40  \w    -21.00  13.00   0.50    0.20    --   40.40 -37.00 120.00   68
 41  \w    -28.00  -3.00   0.50    0.20    --   40.40 -25.00  60.00   50
 42  \w    -61.00 -17.00   0.50    0.20    --  -40.71  85.00 142.00   88
 43  \w    -87.00 -61.00   0.50    0.20    --  -96.35 117.00 150.00   52
 44  \w   -113.00 -88.00   0.50    0.20    --  -96.35 117.00 150.00   50
 45  \w   -121.00 -69.00   0.50    0.20    --  -96.35  85.00 142.00  104
 46  \w   -119.00 -29.00   0.50    0.20    --  -96.35 144.00  90.00  180
 47  \w   -123.00 -33.00   0.50    0.20    --  -96.35 144.00 -60.00  180
 48  \w   -137.00-111.00   0.50    0.20    --  -96.35 -33.00-120.00   52
 49  \w   -163.00 -98.00   0.50    0.20    --  -96.35-117.00   0.00  130
 50  \w   -130.00-104.00   0.50    0.20    --  -96.35 -85.00  23.00   52
 51  \w   -118.00 -73.00   0.50    0.20    --  -96.35 -68.00  30.00   90
 52  \w   -156.00-130.00   0.50    0.20    --  -96.35 -68.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1811036000
_diffrn_orient_matrix_UB_12      0.1024382000
_diffrn_orient_matrix_UB_13      0.0124669000
_diffrn_orient_matrix_UB_21      0.0523861000
_diffrn_orient_matrix_UB_22      0.0226422000
_diffrn_orient_matrix_UB_23      0.1030757000
_diffrn_orient_matrix_UB_31      0.0929612000
_diffrn_orient_matrix_UB_32      0.1091860000
_diffrn_orient_matrix_UB_33      -0.0543158000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8540
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.332
_diffrn_reflns_theta_min         3.362
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
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    1.490
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0549P)^2^+0.3700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3503
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra01210k2.cif
_cod_data_source_block           20210528mat2
_cod_database_code               7248339
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H17 F3 N2 O3 S1'
_chemical_oxdiff_usercomment     MKA21-15
_shelx_estimated_absorpt_t_max   0.766
_shelx_estimated_absorpt_t_min   0.579
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C12(H12), C21(H21), C20(H20), C9(H9), C6(H6), C2(H2),
 C18(H18), C10(H10), C3(H3), C11(H11), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c)
;
_shelx_res_checksum              20909
_shelx_hkl_checksum              39453
_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 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.746