Nitrogen-centred helical acridiniums with a 6-7-6-6 fused ring skeleton.
Nakamura, Shuto; Kawaguchi, Soki; Nishimura, Yuta; Harimoto, Takashi; Hasegawa, Jun-Ya; Suzuki, Takanori; Ishigaki, Yusuke; Chemical communications (Cambridge, England) 62 (2026) 4268–4271; doi:10.1039/d5cc06029j

data_7135426
_publ_section_title
;
 Nitrogen-centred helical acridiniums with a 6-7-6-6 fused ring skeleton.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4268
_journal_page_last               4271
_journal_paper_doi               10.1039/d5cc06029j
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C34 H26 N O, B F4'
_chemical_formula_sum            'C34 H26 B F4 N O'
_chemical_formula_weight         551.37
_chemical_name_systematic        yi241204-nkmr4
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-10-17 deposited with the CCDC.	2026-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5153(3)
_cell_length_b                   13.2614(3)
_cell_length_c                   17.5945(4)
_cell_measurement_reflns_used    16631
_cell_measurement_temperature    200
_cell_measurement_theta_max      75.6770
_cell_measurement_theta_min      3.2860
_cell_volume                     2686.84(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (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      200
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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     57.00 116.00   0.50    0.53    --   42.91 150.00 134.00  118
  2  \w    -32.00  54.00   0.50    0.53    --   42.91 -48.00 120.00  172
  3  \w   -177.00 -83.00   0.50    2.33    -- -106.00 -48.00 120.00  188
  4  \w     39.00  93.00   0.50    2.33    --  112.36 -73.00 -38.00  108
  5  \w     39.00 110.00   0.50    2.33    --  112.36-123.00-108.00  142
  6  \w     85.00 178.00   0.50    2.33    --  112.36  73.00  90.00  186
  7  \w    -26.00  38.00   0.50    0.53    --  -42.91  19.00  30.00  128
  8  \w     73.00 118.00   0.50    0.53    --   42.91 125.00-150.00   90
  9  \w     73.00 118.00   0.50    0.53    --   42.91 125.00-180.00   90
 10  \w    -34.00  43.00   0.50    0.53    --   42.91 -38.00-150.00  154
 11  \w     73.00 118.00   0.50    0.53    --   42.91 125.00 -60.00   90
 12  \w    -71.00 -32.00   0.50    2.33    -- -106.00  61.00 120.00   78
 13  \w    -71.00 -32.00   0.50    2.33    -- -106.00  61.00  30.00   78
 14  \w   -105.00 -32.00   0.50    2.33    -- -106.00  77.00 -60.00  146
 15  \w    -71.00 -32.00   0.50    2.33    -- -106.00  61.00  60.00   78
 16  \w    -71.00 -32.00   0.50    2.33    -- -106.00  61.00 -60.00   78
 17  \w     39.00 105.00   0.50    2.33    --  112.36 -95.00  60.00  132
 18  \w     39.00  71.00   0.50    2.33    --  112.36 -61.00 150.00   64
 19  \w     90.00 178.00   0.50    2.33    --  112.36  45.00-180.00  176
 20  \w     39.00 105.00   0.50    2.33    --  112.36 -95.00 120.00  132
 21  \w     39.00 105.00   0.50    2.33    --  112.36 -95.00 150.00  132
 22  \w     14.00 117.00   0.50    0.53    --   42.91  77.00  30.00  206
 23  \w     21.00 117.00   0.50    0.53    --   42.91  57.00 150.00  192
 24  \w     14.00 117.00   0.50    0.53    --   42.91  77.00 -30.00  206
 25  \w     14.00 117.00   0.50    0.53    --   42.91  77.00-120.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0976457000
_diffrn_orient_matrix_UB_12      -0.0432509000
_diffrn_orient_matrix_UB_13      0.0502583000
_diffrn_orient_matrix_UB_21      0.0471249000
_diffrn_orient_matrix_UB_22      0.1072688000
_diffrn_orient_matrix_UB_23      0.0132141000
_diffrn_orient_matrix_UB_31      -0.0783854000
_diffrn_orient_matrix_UB_32      0.0107521000
_diffrn_orient_matrix_UB_33      0.0704757000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26167
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.455
_diffrn_reflns_theta_min         4.175
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_recrystallization_method
'obtained by recrystallization from CH3CN/Et2O'
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0664P)^2^+0.4834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                5287
_reflns_number_total             5541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06029j2.cif
_cod_data_source_block           yi241204-nkmr4_auto
_cod_original_cell_volume        2686.83(11)
_cod_database_code               7135426
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H26 N O B F4'
_chemical_oxdiff_usercomment     '200 K'
_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:
 C17(H17), C21(H21), C28(H28), C15(H15), C22(H22), C30(H30), C16(H16),
 C24(H24), C6(H6), C23(H23), C3(H3), C12(H12), C4(H4), C9(H9), C10(H10),
 C11(H11), C5(H5)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              2241
_shelx_hkl_checksum              68497
_olex2_submission_original_sample_id yi241204-nkmr4
_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 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.744