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_7135427
_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         'C H2 Cl2, B F4, C32 H22 N O'
_chemical_formula_sum            'C33 H24 B Cl2 F4 N O'
_chemical_formula_weight         608.24
_chemical_name_systematic        yi240709-nkmr3
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-10
_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                 93.9884(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.5693(6)
_cell_length_b                   8.47276(18)
_cell_length_c                   26.6677(6)
_cell_measurement_reflns_used    8007
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.9070
_cell_measurement_theta_min      3.3050
_cell_volume                     5538.0(2)
_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 2018/2 (Sheldrick, 2018)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.948
_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   -122.00  26.00   0.50    0.50    --  -42.91  -8.00-117.00  296
  2  \w    -26.00  37.00   0.50    0.50    --  -42.91   8.00  57.00  126
  3  \w    -37.00  26.00   0.50    0.50    --   42.91  -8.00-117.00  126
  4  \w    -26.00 123.00   0.50    0.50    --   42.91   8.00  57.00  298
  5  \w   -177.00 -30.00   0.50    2.00    -- -106.00  -8.00-117.00  294
  6  \w     37.00 178.00   0.50    2.00    --  112.36   8.00  57.00  282
  7  \w    -96.00 -13.00   0.50    0.50    --  -42.91 125.00-120.00  166
  8  \w    -96.00 -13.00   0.50    0.50    --  -42.91 125.00 120.00  166
  9  \w   -112.00 -32.00   0.50    2.00    -- -106.00 125.00  90.00  160
 10  \w   -105.00 -32.00   0.50    2.00    -- -106.00  77.00 150.00  146
 11  \w   -112.00 -32.00   0.50    2.00    -- -106.00 125.00 150.00  160
 12  \w    -71.00 -32.00   0.50    2.00    -- -106.00  61.00 -60.00   78
 13  \w    -71.00 -32.00   0.50    2.00    -- -106.00  61.00 150.00   78
 14  \w    -71.00 -32.00   0.50    2.00    -- -106.00  61.00   0.00   78
 15  \w    -71.00 -32.00   0.50    2.00    -- -106.00  61.00-150.00   78
 16  \w    -71.00 -32.00   0.50    2.00    -- -106.00  61.00  90.00   78
 17  \w     39.00  71.00   0.50    2.00    --  112.36 -61.00   0.00   64
 18  \w     39.00  71.00   0.50    2.00    --  112.36 -61.00 -30.00   64
 19  \w     39.00 105.00   0.50    2.00    --  112.36 -95.00 -90.00  132
 20  \w     39.00 105.00   0.50    2.00    --  112.36 -95.00  60.00  132
 21  \w     14.00 117.00   0.50    0.50    --   42.91  77.00-150.00  206
 22  \w     14.00 117.00   0.50    0.50    --   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      0.0282929000
_diffrn_orient_matrix_UB_12      0.0159073000
_diffrn_orient_matrix_UB_13      -0.0495086000
_diffrn_orient_matrix_UB_21      0.0561029000
_diffrn_orient_matrix_UB_22      -0.0104414000
_diffrn_orient_matrix_UB_23      0.0294316000
_diffrn_orient_matrix_UB_31      -0.0006585000
_diffrn_orient_matrix_UB_32      -0.1808656000
_diffrn_orient_matrix_UB_33      -0.0060484000
_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  0.0574
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            25961
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.384
_diffrn_reflns_theta_min         3.323
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.596
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.459
_exptl_crystal_description       needle
_exptl_crystal_F_000             2496
_exptl_crystal_recrystallization_method
'obtained by recrystallization from CH2Cl2/Et2O'
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0508P)^2^+11.3196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4288
_reflns_number_total             5578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06029j2.cif
_cod_data_source_block           yi240709-nkmr3_autored
_cod_database_code               7135427
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C33 H24 B Cl2 F4 N O'
_chemical_oxdiff_usercomment     '150 K'
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.552
_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. Restrained distances
 Cl1A-C33A \\sim Cl1-C33
 with sigma of 0.02
 Cl2-C33 \\sim Cl2-C33A
 with sigma of 0.02
3. Others
 Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(C33)=Sof(H33A)=Sof(H33B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C33A(H33C,H33D)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C24(H24), C17(H17), C6(H6), C15(H15), C12(H12), C4(H4),
 C5(H5), C10(H10), C11(H11), C23(H23), C21(H21), C31(H31), C16(H16), C27(H27),
 C28(H28), C22(H22), C30(H30)
4.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_shelx_res_checksum              23102
_shelx_hkl_checksum              26480
_olex2_submission_original_sample_id SN014
_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 1.234
_oxdiff_exptl_absorpt_empirical_full_min 0.794