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_7135423
_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 H15 N O'
_chemical_formula_sum            'C25 H15 N O'
_chemical_formula_weight         345.38
_chemical_name_systematic        yi221201-nsmr
_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             2022-12-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2025-10-17 deposited with the CCDC.	2026-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.9520(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.95059(16)
_cell_length_b                   11.1282(2)
_cell_length_c                   17.1740(3)
_cell_measurement_reflns_used    11184
_cell_measurement_temperature    150
_cell_measurement_theta_max      77.0010
_cell_measurement_theta_min      3.9630
_cell_volume                     1673.52(5)
_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      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_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     66.00 106.00   0.50    0.33    --  112.39-115.00  53.00   80
  2  \w    117.00 143.00   0.50    0.33    --  112.39-172.00 -88.00   52
  3  \w     99.00 125.00   0.50    0.33    --  112.39  30.00  90.00   52
  4  \w     25.00  50.00   0.50    0.17    --   42.88-115.00  53.00   50
  5  \w    126.00 171.00   0.50    0.33    --  112.39  30.00  90.00   90
  6  \w     92.00 160.00   0.50    0.33    --  112.39  45.00 150.00  136
  7  \w     63.00 105.00   0.50    0.33    --  112.39 -95.00  90.00   84
  8  \w     39.00  82.00   0.50    0.33    --  112.39 -95.00  60.00   86
  9  \w     58.00  84.00   0.50    0.33    --  112.39 -77.00  60.00   52
 10  \w     39.00  67.00   0.50    0.33    --  112.39 -61.00  90.00   56
 11  \w     44.00  69.00   0.50    0.33    --  112.39 -61.00 -60.00   50
 12  \w     39.00  69.00   0.50    0.33    --  112.39 -61.00-180.00   60
 13  \w    -36.00  25.00   0.50    0.17    --   42.88 -19.00-120.00  122
 14  \w    -37.00  24.00   0.50    0.17    --   42.88 -19.00 120.00  122
 15  \w     85.00 111.00   0.50    0.17    --   42.88 125.00  30.00   52
 16  \w     82.00 110.00   0.50    0.17    --   42.88 125.00   0.00   56
 17  \w     45.00 118.00   0.50    0.17    --   42.88 172.00 -74.00  146
 18  \w     72.00  97.00   0.50    0.33    --  112.39 172.00 -74.00   50
 19  \w     75.00 106.00   0.50    0.17    --   42.88 125.00-180.00   62
 20  \w    -68.00 -33.00   0.50    0.33    -- -106.00  61.00 -30.00   70
 21  \w   -122.00 -36.00   0.50    0.17    --  -42.88 172.00 -74.00  172
 22  \w   -145.00 -53.00   0.50    0.33    -- -106.00 172.00 -74.00  184
 23  \w    -91.00  -6.00   0.50    0.17    --  -42.88 115.00 143.00  170
 24  \w   -109.00 -30.00   0.50    0.33    -- -106.00 115.00 143.00  158
 25  \w    -71.00 -32.00   0.50    0.33    -- -106.00  61.00 120.00   78
 26  \w   -177.00 -87.00   0.50    0.33    -- -106.00 -45.00 -30.00  180
 27  \w   -177.00 -80.00   0.50    0.33    -- -106.00-115.00  53.00  194
 28  \w   -118.00 -45.00   0.50    0.17    --  -42.88-172.00 -88.00  146
;
_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      0.1035860000
_diffrn_orient_matrix_UB_12      -0.0199809000
_diffrn_orient_matrix_UB_13      0.0825132000
_diffrn_orient_matrix_UB_21      -0.0089382000
_diffrn_orient_matrix_UB_22      0.1350106000
_diffrn_orient_matrix_UB_23      0.0183594000
_diffrn_orient_matrix_UB_31      -0.1419462000
_diffrn_orient_matrix_UB_32      -0.0231217000
_diffrn_orient_matrix_UB_33      0.0355185000
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13560
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.435
_diffrn_reflns_theta_min         4.766
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24625
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 'recrystallized from CH2Cl2/hexane'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0036(3)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0478P)^2^+0.5179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3225
_reflns_number_total             3397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06029j2.cif
_cod_data_source_block           yi221201-nsmr_auto
_cod_original_cell_volume        1673.51(6)
_cod_database_code               7135423
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H15 N O2'
_chemical_oxdiff_usercomment     '150 K'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C24(H24), C22(H22), C23(H23), C18(H18), C15(H15), C3(H3), C12(H12),
 C17(H17), C11(H11), C6(H6), C16(H16), C4(H4), C10(H10), C5(H5)
;
_shelx_res_checksum              92692
_shelx_hkl_checksum              20197
_olex2_submission_original_sample_id yi221201-nsmr
_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 3.322
_oxdiff_exptl_absorpt_empirical_full_min 0.700