Double aza[4,5]helicenes with a common naphthalene core: synthesis, crystal structure and optical properties.
Sokha, Samita J.; Marchenko, Sergey S.; Demidov, Oleg P.; Chernyshev, Anatoly V.; Metelitsa, Anatoly V.; Gulevskaya, Anna V.; Organic & biomolecular chemistry 23 (2025) 6162–6169; doi:10.1039/d5ob00739a

data_7160576
_publ_section_title
;
 Double aza[4,5]helicenes with a common naphthalene core: synthesis,
 crystal structure and optical properties.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6162
_journal_page_last               6169
_journal_paper_doi               10.1039/d5ob00739a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C35 H22 N2'
_chemical_formula_sum            'C35 H22 N2'
_chemical_formula_weight         470.54
_chemical_name_systematic
10-(p-Tolyl)naphtho[2,1-f]phenanthro[9,10-h]quinoxaline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2025-05-02 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.7960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3608(2)
_cell_length_b                   13.69670(10)
_cell_length_c                   11.10420(10)
_cell_measurement_reflns_used    11143
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4510
_cell_measurement_theta_min      4.3090
_cell_volume                     2331.11(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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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   -114.00 -15.00   1.00    2.29    --  -41.60 -47.00-148.00   99
  2  \w    -68.00  31.00   1.00    2.29    --  -41.60  47.00   0.00   99
  3  \w     15.00 114.00   1.00    2.29    --   41.60  47.00   0.00   99
  4  \w     39.00 138.00   1.00    9.17    --  112.00 -47.00-148.00   99
  5  \w     86.00 178.00   1.00    9.17    --  112.00  47.00   0.00   92
  6  \w     23.00  98.00   1.00    2.29    --   41.60-125.00-180.00   75
  7  \w      4.00  32.00   1.00    2.29    --   41.60  90.00-133.60   28
  8  \w     23.00  98.00   1.00    2.29    --   41.60-125.00  60.00   75
  9  \w     40.00 141.00   1.00    9.17    --  112.00 -61.00  90.00  101
 10  \w     86.00 178.00   1.00    9.17    --  112.00  45.00 -90.00   92
 11  \w     36.00 113.00   1.00    9.17    --  112.00-111.00  30.00   77
 12  \w     39.00 138.00   1.00    9.17    --  112.00 -46.00   0.01   99
 13  \w     36.00 140.00   1.00    9.17    --  112.00 -30.00  60.00  104
 14  \w     30.00 110.00   1.00    9.17    --  112.00 -95.00  90.00   80
 15  \w     89.00 137.00   1.00    9.17    --  112.00  30.00 -30.00   48
 16  \w     37.00  62.00   1.00    9.17    --  112.00-111.00-120.00   25
 17  \w     42.00  89.00   1.00    9.17    --  112.00 -30.00 -90.00   47
 18  \w    120.00 147.00   1.00    9.17    --  112.00  15.00 -60.00   27
 19  \w    108.00 176.00   1.00    9.17    --  112.00  16.00 -10.82   68
 20  \w     95.00 134.00   1.00    9.17    --  112.00 -30.00 -90.00   39
 21  \w     64.00  89.00   1.00    9.17    --  112.00  16.00 -10.82   25
 22  \w     65.00 103.00   1.00    9.17    --  112.00  15.00 -60.00   38
 23  \w     58.00  98.00   1.00    9.17    --  112.00 -95.00  30.00   40
 24  \w    100.00 150.00   1.00    9.17    --  112.00 111.00  30.00   50
 25  \w     95.00 144.00   1.00    9.17    --  112.00 -77.00-180.00   49
 26  \w     35.00  62.00   1.00    9.17    --  112.00 -15.00 -30.00   27
 27  \w     94.00 121.00   1.00    9.17    --  112.00 -15.00 -30.00   27
 28  \w     37.00 110.00   1.00    9.17    --  112.00-111.00-150.00   73
 29  \w     58.00  85.00   1.00    9.17    --  112.00-111.00 120.00   27
 30  \w     78.00 109.00   1.00    9.17    --  112.00 -95.00 -60.00   31
 31  \w     39.00  66.00   1.00    9.17    --  112.00-111.00-180.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0988909000
_diffrn_orient_matrix_UB_12      -0.0181856000
_diffrn_orient_matrix_UB_13      0.0000656000
_diffrn_orient_matrix_UB_21      -0.0036363000
_diffrn_orient_matrix_UB_22      0.0628042000
_diffrn_orient_matrix_UB_23      0.1147260000
_diffrn_orient_matrix_UB_31      -0.0171058000
_diffrn_orient_matrix_UB_32      0.0915640000
_diffrn_orient_matrix_UB_33      -0.0786846000
_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  0.0325
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.256
_diffrn_reflns_theta_min         4.329
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.526
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0651P)^2^+1.2521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4185
_reflns_number_total             4854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00739a2.cif
_cod_data_source_block           d_23_100_2_autored
_cod_depositor_comments
'Adding full bibliography for 7160574--7160577.cif.'
_cod_database_code               7160576
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C35 H22 N2'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.867
_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:
 C29(H29), C26(H26), C23(H23), C17(H17), C27(H27), C36(H36), C32(H32),
 C28(H28), C16(H16), C35(H35), C2(H2), C33(H33), C8(H8), C3(H3), C9(H9),
 C11(H11), C14(H14), C15(H15), C10(H10)
2.b Idealised Me refined as rotating group:
 C37(H37a,H37b,H37c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              41367
_shelx_fab_checksum              65434
_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 1.431
_oxdiff_exptl_absorpt_empirical_full_min 0.807