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_7160577
_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         'C39 H24 N2, 0.5[C7H8]'
_chemical_formula_sum            'C39 H24 N2'
_chemical_formula_weight         520.60
_chemical_name_systematic
9-(p-Tolyl)naphtho[2,1-a]phenanthro[9,10-c]phenazine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-28
_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                94.611(3)
_cell_angle_beta                 100.588(3)
_cell_angle_gamma                107.817(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9067(3)
_cell_length_b                   11.7479(4)
_cell_length_c                   14.9100(5)
_cell_measurement_reflns_used    9091
_cell_measurement_temperature    100.01(15)
_cell_measurement_theta_max      75.7240
_cell_measurement_theta_min      4.5930
_cell_volume                     1444.35(9)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.961
_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   -119.00 -49.00   1.00    1.57    --  -41.85-160.00-174.00   70
  2  \w   -115.00 -21.00   1.00    1.57    --  -41.85 160.00-143.00   94
  3  \w    -88.00   4.00   1.00    1.57    --  -41.85 118.00  64.00   92
  4  \w     18.00  94.00   1.00    1.57    --   41.85-118.00 -22.00   76
  5  \w     42.00 120.00   1.00    1.57    --   41.85-160.00-174.00   78
  6  \w     42.00 141.00   1.00    6.30    --  112.00-160.00-174.00   99
  7  \w     37.00 114.00   1.00    6.30    --  112.00-118.00 -22.00   77
  8  \w     71.00 164.00   1.00    6.30    --  112.00 160.00-143.00   93
  9  \w     98.00 178.00   1.00    6.30    --  112.00 118.00  64.00   80
 10  \w   -114.00 -14.00   1.00    1.57    --  -41.85 -57.00  60.00  100
 11  \w   -116.00 -17.00   1.00    1.57    --  -41.85 -38.00 150.00   99
 12  \w      1.00  83.00   1.00    1.57    --   41.85 -99.00-120.00   82
 13  \w      1.00  83.00   1.00    1.57    --   41.85 -99.00   0.00   82
 14  \w    -32.00  66.00   1.00    1.57    --   41.85 -38.00-120.00   98
 15  \w    100.00 178.00   1.00    6.30    --  112.00 111.00  30.00   78
 16  \w     83.00 178.00   1.00    6.30    --  112.00  61.00  30.00   95
 17  \w     39.00 138.00   1.00    6.30    --  112.00 -45.00  90.00   99
 18  \w     86.00 178.00   1.00    6.30    --  112.00  45.00 -60.00   92
 19  \w     96.00 134.00   1.00    6.30    --  112.00 135.00 123.00   38
 20  \w     61.00  86.00   1.00    6.30    --  112.00  15.00-180.00   25
 21  \w    127.00 170.00   1.00    6.30    --  112.00  15.00-180.00   43
 22  \w     45.00 101.00   1.00    6.30    --  112.00-111.00-180.00   56
 23  \w     76.00 125.00   1.00    6.30    --  112.00-135.00 146.00   49
 24  \w     45.00  73.00   1.00    6.30    --  112.00-111.00 -90.00   28
 25  \w     75.00 101.00   1.00    6.30    --  112.00-111.00 -90.00   26
 26  \w     67.00 104.00   1.00    6.30    --  112.00 -61.00 -30.00   37
 27  \w     77.00 122.00   1.00    6.30    --  112.00 -30.00-120.00   45
 28  \w     89.00 125.00   1.00    6.30    --  112.00-135.00-123.00   36
 29  \w     41.00  66.00   1.00    6.30    --  112.00   0.00  -0.00   25
 30  \w    107.00 133.00   1.00    6.30    --  112.00   0.00  -0.00   26
 31  \w     87.00 113.00   1.00    6.30    --  112.00-111.00 -30.00   26
 32  \w     87.00 113.00   1.00    6.30    --  112.00  47.00 -81.47   26
 33  \w     37.00  69.00   1.00    6.30    --  112.00-111.00-120.00   32
 34  \w    153.00 178.00   1.00    6.30    --  112.00  95.00 164.00   25
 35  \w    153.00 178.00   1.00    6.30    --  112.00 111.00 120.00   25
 36  \w     64.00  90.00   1.00    6.30    --  112.00 178.00   0.00   26
 37  \w    106.00 132.00   1.00    6.30    --  112.00 111.00 120.00   26
 38  \w    -91.00 -66.00   1.00    1.57    --  -41.60 -38.00 167.00   25
;
_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      -0.0375586000
_diffrn_orient_matrix_UB_12      0.0316541000
_diffrn_orient_matrix_UB_13      -0.0980997000
_diffrn_orient_matrix_UB_21      -0.0812559000
_diffrn_orient_matrix_UB_22      -0.1353452000
_diffrn_orient_matrix_UB_23      -0.0380102000
_diffrn_orient_matrix_UB_31      -0.1632984000
_diffrn_orient_matrix_UB_32      0.0080875000
_diffrn_orient_matrix_UB_33      0.0148733000
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18700
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.306
_diffrn_reflns_theta_min         3.995
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.588
_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    1.197
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0574P)^2^+0.4060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5012
_reflns_number_total             5821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00739a2.cif
_cod_data_source_block           d_27_100_autored
_cod_depositor_comments
'Adding full bibliography for 7160574--7160577.cif.'
_cod_database_code               7160577
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C39 H24 N2'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.818
_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:
 C32(H32), C23(H23), C4(H4), C26(H26), C3(H3), C20(H20), C29(H29), C14(H14),
 C34(H34), C17(H17), C35(H35), C2(H2), C21(H21), C22(H22), C38(H38), C16(H16),
 C27(H27), C1(H1), C37(H37), C28(H28), C15(H15)
2.b Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              56545
_shelx_fab_checksum              1231
_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 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.773