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_7135425
_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         'B F4, C34 H26 N'
_chemical_formula_sum            'C34 H26 B F4 N'
_chemical_formula_weight         535.37
_chemical_name_systematic        yi240209-nsmr
_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             2024-02-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_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                   11.24384(10)
_cell_length_b                   13.79725(13)
_cell_length_c                   17.01571(15)
_cell_measurement_reflns_used    14426
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.6930
_cell_measurement_theta_min      4.1010
_cell_volume                     2639.72(4)
_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 0.979
_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   -120.00 -20.00   0.50    1.27    --  -42.91 -38.00  45.00  200
  2  \w   -113.00 -32.00   0.50    6.34    -- -106.00 128.00-104.00  162
  3  \w     81.00 178.00   0.50    6.34    --  112.36  83.00  10.00  194
  4  \w     90.00 178.00   0.50    6.34    --  112.36  38.00-159.00  176
  5  \w     39.00 114.00   0.50    6.34    --  112.36-128.00-178.00  150
  6  \w    -26.00  38.00   0.50    1.27    --  -42.91  19.00   0.00  128
  7  \w    -34.00  43.00   0.50    1.27    --   42.91 -38.00-120.00  154
  8  \w     73.00 118.00   0.50    1.27    --   42.91 125.00  30.00   90
  9  \w   -105.00 -32.00   0.50    6.34    -- -106.00  77.00-150.00  146
 10  \w     39.00  71.00   0.50    6.34    --  112.36 -61.00-120.00   64
 11  \w     39.00  71.00   0.50    6.34    --  112.36 -61.00 120.00   64
 12  \w     39.00  71.00   0.50    6.34    --  112.36 -61.00  90.00   64
 13  \w     39.00  71.00   0.50    6.34    --  112.36 -61.00 -90.00   64
 14  \w     39.00 105.00   0.50    6.34    --  112.36 -95.00-150.00  132
 15  \w     39.00  69.00   0.50    6.34    --  112.36 -61.00  30.00   60
 16  \w   -154.00-129.00   0.50   10.28    -- -106.00 -38.00  45.00   50
 17  \w     77.00 103.00   0.50    3.70    --   43.16 125.00  60.00   52
 18  \w     73.00  98.00   0.50    3.70    --   43.16 125.00-180.00   50
 19  \w    -95.00 -47.00   0.50   10.28    -- -106.00  77.00 -90.00   96
 20  \w     76.00 101.00   0.50   10.28    --  112.36-125.00  90.00   50
 21  \w     46.00  73.00   0.50   10.28    --  112.36-125.00  90.00   54
 22  \w    124.00 150.00   0.50   10.28    --  112.36  61.00 -60.00   52
 23  \w     39.00  64.00   0.50   10.28    --  112.36 -61.00  60.00   50
 24  \w    110.00 135.00   0.50   10.28    --  112.36  38.00-159.00   50
 25  \w     39.00  64.00   0.50   10.28    --  112.36 -61.00 -60.00   50
 26  \w   -106.00 -22.00   0.50    3.70    --  -43.16 142.00  66.00  168
 27  \w   -116.00 -20.00   0.50    3.70    --  -43.16 -57.00 -60.00  192
 28  \w   -116.00 -14.00   0.50    3.70    --  -43.16 -77.00  30.00  204
 29  \w   -116.00 -14.00   0.50    3.70    --  -43.16 -77.00-150.00  204
 30  \w     14.00 116.00   0.50    3.70    --   43.16  77.00 150.00  204
 31  \w     62.00  87.00   0.50   10.28    --  112.36  15.00 150.00   50
 32  \w    110.00 135.00   0.50   10.28    --  112.36  38.00-159.00   50
;
_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      0.0361373000
_diffrn_orient_matrix_UB_12      0.0629056000
_diffrn_orient_matrix_UB_13      0.0708754000
_diffrn_orient_matrix_UB_21      -0.0573226000
_diffrn_orient_matrix_UB_22      -0.0742390000
_diffrn_orient_matrix_UB_23      0.0560784000
_diffrn_orient_matrix_UB_31      0.1190823000
_diffrn_orient_matrix_UB_32      -0.0547561000
_diffrn_orient_matrix_UB_33      0.0054321000
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26421
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.602
_diffrn_reflns_theta_min         4.125
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39207
_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    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'obtained by recrystallization from THF/hexane'
_exptl_crystal_size_max          0.114
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5436
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0483P)^2^+0.4552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                5127
_reflns_number_total             5436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06029j2.cif
_cod_data_source_block           yi240209-nsmr_auto
_cod_database_code               7135425
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H26 B F4 N'
_chemical_oxdiff_usercomment     '150 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. Restrained distances
 F1-B1 \\sim F3-B1 \\sim F2-B1 \\sim F4-B1 \\sim F4A-B1 \\sim F3A-B1 \\sim
F2A-B1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F4 \\sim F2 \\sim F3: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
F4A \\sim F2A \\sim F3A: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 F4, F2, F3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4A, F2A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: F3(0.5) F2(0.5) F4(0.5) F4A(0.5) F3A(0.5) F2A(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C3(H3), C15(H15), C28(H28), C24(H24), C22(H22), C21(H21),
 C30(H30), C12(H12), C23(H23), C9(H9), C6(H6), C10(H10), C5(H5), C11(H11),
 C4(H4)
6.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              62922
_shelx_hkl_checksum              32070
_olex2_submission_original_sample_id yi240209-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 2.049
_oxdiff_exptl_absorpt_empirical_full_min 0.728