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_7135424
_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         'C25 H16 N, B F4'
_chemical_formula_sum            'C25 H16 B F4 N'
_chemical_formula_weight         417.20
_chemical_name_systematic        yi250626-nkmr1
_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             2025-06-27
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-10-17 deposited with the CCDC.	2026-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.4206(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.75691(12)
_cell_length_b                   7.33195(9)
_cell_length_c                   26.2699(3)
_cell_measurement_reflns_used    9313
_cell_measurement_temperature    150
_cell_measurement_theta_max      77.0630
_cell_measurement_theta_min      3.3680
_cell_volume                     1867.49(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.950
_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    -55.00  32.00   0.50    2.53    --  -43.16  49.00 111.00  174
  2  \w   -118.00 -21.00   0.50    2.53    --  -43.16 -49.00 -35.00  194
  3  \w   -177.00 -83.00   0.50    6.79    -- -106.00 -49.00 -35.00  188
  4  \w     90.00 178.00   0.50    6.79    --  112.36  49.00 111.00  176
  5  \w     73.00 118.00   0.50    2.53    --   43.16 125.00   0.00   90
  6  \w     73.00 118.00   0.50    2.53    --   43.16 125.00 -30.00   90
  7  \w    -36.00  26.00   0.50    2.53    --   43.16 -19.00-180.00  124
  8  \w    -71.00 -32.00   0.50    6.79    -- -106.00  61.00 -60.00   78
  9  \w   -177.00 -82.00   0.50    6.79    -- -106.00 -61.00  60.00  190
 10  \w    -71.00 -32.00   0.50    6.79    -- -106.00  61.00-150.00   78
 11  \w   -112.00 -32.00   0.50    6.79    -- -106.00 125.00 120.00  160
 12  \w    -71.00 -32.00   0.50    6.79    -- -106.00  61.00  30.00   78
 13  \w     39.00  71.00   0.50    6.79    --  112.36 -61.00 -60.00   64
 14  \w     39.00  71.00   0.50    6.79    --  112.36 -61.00 120.00   64
 15  \w     39.00  71.00   0.50    6.79    --  112.36 -61.00  90.00   64
 16  \w     39.00  71.00   0.50    6.79    --  112.36 -61.00   0.00   64
 17  \w     39.00 105.00   0.50    6.79    --  112.36 -77.00  60.00  132
 18  \w     39.00  71.00   0.50    6.79    --  112.36 -61.00-180.00   64
 19  \w     89.00 178.00   0.50    6.79    --  112.36  30.00-150.00  178
 20  \w     39.00  71.00   0.50    6.79    --  112.36 -61.00 -30.00   64
 21  \w     39.00  71.00   0.50    6.79    --  112.36 -61.00 -90.00   64
 22  \w     39.00 105.00   0.50    6.79    --  112.36 -95.00   0.00  132
 23  \w     21.00 118.00   0.50    2.53    --   43.16  49.00 111.00  194
 24  \w     14.00 116.00   0.50    2.53    --   43.16  77.00-120.00  204
 25  \w     13.00  97.00   0.50    2.53    --   43.16-125.00   0.00  168
 26  \w     14.00 116.00   0.50    2.53    --   43.16  77.00 -30.00  204
 27  \w     14.00 116.00   0.50    2.53    --   43.16  77.00 150.00  204
;
_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      -0.1107191000
_diffrn_orient_matrix_UB_12      0.0998175000
_diffrn_orient_matrix_UB_13      -0.0361037000
_diffrn_orient_matrix_UB_21      0.1132042000
_diffrn_orient_matrix_UB_22      0.0780761000
_diffrn_orient_matrix_UB_23      -0.0302080000
_diffrn_orient_matrix_UB_31      -0.0132137000
_diffrn_orient_matrix_UB_32      -0.1675762000
_diffrn_orient_matrix_UB_33      -0.0355933000
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17546
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.335
_diffrn_reflns_theta_min         4.684
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.484
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method
'obtained by recrystallization from MeCN/Et2O'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0545P)^2^+1.5423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3334
_reflns_number_total             3780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06029j2.cif
_cod_data_source_block           yi250626-nkmr1_autored
_cod_original_cell_volume        1867.48(4)
_cod_database_code               7135424
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H16 N B F4'
_chemical_oxdiff_usercomment     '150 K'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.762
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
B1A \\sim F4A \\sim F1A \\sim F2A \\sim F3A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
F4 \\sim B1 \\sim F1 \\sim F2 \\sim F3: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 B1A, F4A, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4, B1, F1, F2, F3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(B1A)=Sof(F4A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(B1)=Sof(F4)=Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Free rotating group:
 B1(F4,F1,F2,F3), B1A(F4A,F1A,F2A,F3A)
5.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C3(H3), C9(H9), C4(H4), C15(H15), C12(H12), C6(H6), C5(H5),
 C10(H10), C19(H19), C11(H11), C23(H23), C17(H17), C21(H21), C16(H16), C22(H22)
;
_shelx_res_checksum              60336
_shelx_hkl_checksum              6713
_olex2_submission_original_sample_id yi250626-nkmr1
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.532