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_7160575
_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         'C36 H23 N'
_chemical_formula_sum            'C36 H23 N'
_chemical_formula_weight         469.55
_chemical_name_systematic
10-(p-Tolyl)naphtho[2,1-f]phenanthro[9,10-h]quinoline
_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             2024-03-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-02 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.3860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2948(2)
_cell_length_b                   13.81900(10)
_cell_length_c                   11.13390(10)
_cell_measurement_reflns_used    18608
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1330
_cell_measurement_theta_min      4.2950
_cell_volume                     2349.14(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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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 -16.00   1.00    1.00    --  -41.60 -46.00-130.00   98
  2  \w     16.00 114.00   1.00    1.00    --   41.60  46.00  19.00   98
  3  \w     39.00 138.00   1.00    1.41    --  112.00 -46.00-130.00   99
  4  \w     86.00 178.00   1.00    1.41    --  112.00  46.00  19.00   92
  5  \w    -68.00  31.00   1.00    1.00    --  -41.60  46.00  19.00   99
  6  \w     23.00  98.00   1.00    1.00    --   41.60-125.00  90.00   75
  7  \w     23.00  98.00   1.00    1.00    --   41.60-125.00-150.00   75
  8  \w      7.00  36.00   1.00    1.00    --   41.60  85.00 -99.63   29
  9  \w    100.00 178.00   1.00    1.41    --  112.00 111.00 -90.00   78
 10  \w     86.00 178.00   1.00    1.41    --  112.00  45.00  60.00   92
 11  \w     36.00 113.00   1.00    1.41    --  112.00-111.00 -90.00   77
 12  \w     86.00 178.00   1.00    1.41    --  112.00  45.00 -30.00   92
 13  \w    100.00 178.00   1.00    1.41    --  112.00 111.00-120.00   78
 14  \w     86.00 178.00   1.00    1.41    --  112.00  45.00  90.00   92
 15  \w     30.00 110.00   1.00    1.41    --  112.00 -95.00  30.00   80
 16  \w     83.00 178.00   1.00    1.41    --  112.00  61.00  30.00   95
 17  \w     86.00 178.00   1.00    1.41    --  112.00  45.00 150.00   92
 18  \w     33.00 146.00   1.00    1.41    --  112.00 -82.00 -30.99  113
 19  \w     59.00 178.00   1.00    1.41    --  112.00  15.00 120.00  119
 20  \w     36.00 113.00   1.00    1.41    --  112.00-111.00-120.00   77
 21  \w     79.00 178.00   1.00    1.41    --  112.00  77.00 -60.00   99
 22  \w     40.00 139.00   1.00    1.41    --  112.00 -51.00-155.15   99
 23  \w     33.00 146.00   1.00    1.41    --  112.00 -82.00  84.60  113
 24  \w     36.00 113.00   1.00    1.41    --  112.00-111.00  90.00   77
 25  \w     40.00 141.00   1.00    1.41    --  112.00 -61.00-120.00  101
 26  \w     36.00 113.00   1.00    1.41    --  112.00-111.00-150.00   77
 27  \w   -114.00 -13.00   1.00    1.00    --  -41.60 -57.00  90.00  101
 28  \w   -118.00 -27.00   1.00    1.00    --  -41.60 -77.00   0.00   91
 29  \w      4.00  32.00   1.00    1.00    --   41.60  90.00 124.74   28
;
_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      0.0420809000
_diffrn_orient_matrix_UB_12      0.0362050000
_diffrn_orient_matrix_UB_13      -0.1140496000
_diffrn_orient_matrix_UB_21      0.0859158000
_diffrn_orient_matrix_UB_22      -0.0522406000
_diffrn_orient_matrix_UB_23      0.0398968000
_diffrn_orient_matrix_UB_31      -0.0323124000
_diffrn_orient_matrix_UB_32      -0.0915926000
_diffrn_orient_matrix_UB_33      -0.0676839000
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33115
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.512
_diffrn_reflns_theta_min         4.315
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.342
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.285
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0658P)^2^+2.6284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1511
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4436
_reflns_number_total             4897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00739a2.cif
_cod_data_source_block           d_32_bigpr_100_autored
_cod_depositor_comments
'Adding full bibliography for 7160574--7160577.cif.'
_cod_database_code               7160575
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C36 H23 N'
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.758
_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:
 C7(H7), C13(H13), C10(H10), C36(H36), C12(H12), C18(H18), C4(H4), C19(H19),
 C11(H11), C32(H32), C33(H33), C3(H3), C26(H26), C27(H27), C35(H35), C2(H2),
 C24(H24), C21(H21), C25(H25), C20(H20)
2.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_shelx_res_checksum              77517
_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 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.816