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_7160574
_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         'C26 H15 I N2'
_chemical_formula_sum            'C26 H15 I N2'
_chemical_formula_weight         482.30
_chemical_name_systematic        6-Iodo-5-phenylphenanthro[9,10-f]quinoxaline
_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             2022-03-21
_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                 104.5083(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.41874(11)
_cell_length_b                   7.27707(5)
_cell_length_c                   20.60254(15)
_cell_measurement_reflns_used    13683
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7950
_cell_measurement_theta_min      4.4120
_cell_volume                     1947.67(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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      100.00(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 0.997
_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    -87.00  -6.00   1.00    1.00    --  -41.19 125.00 150.00   81
  2  \w   -115.00 -17.00   1.00    1.00    --  -41.19 -38.00-120.00   98
  3  \w   -115.00 -17.00   1.00    1.00    --  -41.19 -38.00 150.00   98
  4  \w      8.00  42.00   1.00    1.00    --   41.19  81.00 -29.19   34
  5  \w    -21.00  74.00   1.00    1.00    --   41.19 -77.00 120.00   95
  6  \w     30.00 165.00   1.00    1.00    --  112.00 -15.00  30.00  135
  7  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00 -90.00  101
  8  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00  60.00   99
  9  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 -60.00   73
 10  \w     83.00 178.00   1.00    1.00    --  112.00  61.00 -30.00   95
 11  \w     36.00 109.00   1.00    1.00    --  112.00-111.00   0.00   73
 12  \w     83.00 178.00   1.00    1.00    --  112.00  61.00 -90.00   95
 13  \w     36.00 109.00   1.00    1.00    --  112.00-111.00-180.00   73
 14  \w    103.00 178.00   1.00    1.00    --  112.00  77.00   0.00   75
 15  \w    103.00 178.00   1.00    1.00    --  112.00  77.00-180.00   75
 16  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 -30.00   73
 17  \w    133.00 160.00   1.00    1.00    --  112.00  77.00 -60.00   27
 18  \w    103.00 172.00   1.00    1.00    --  112.00  77.00 150.00   69
 19  \w     38.00  84.00   1.00    1.00    --  112.00 -77.00 -90.00   46
 20  \w    118.00 145.00   1.00    1.00    --  112.00 -77.00 -90.00   27
 21  \w     33.00  62.00   1.00    1.00    --  112.00 -95.00  60.00   29
 22  \w     81.00 106.00   1.00    1.00    --  112.00 -95.00  60.00   25
 23  \w     62.00  87.00   1.00    1.00    --  112.00 178.00-150.00   25
 24  \w    114.00 157.00   1.00    1.00    --  112.00 111.00  60.00   43
 25  \w     30.00  61.00   1.00    1.00    --  112.00 -15.00 -90.00   31
 26  \w    114.00 165.00   1.00    1.00    --  112.00 -15.00 -90.00   51
 27  \w    115.00 147.00   1.00    1.00    --  112.00 111.00-180.00   32
 28  \w    150.00 177.00   1.00    1.00    --  112.00  77.00 120.00   27
 29  \w     81.00 106.00   1.00    1.00    --  112.00 -95.00  30.00   25
 30  \w     32.00  58.00   1.00    1.00    --  112.00 -95.00  30.00   26
;
_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      -0.0803686000
_diffrn_orient_matrix_UB_12      0.0375050000
_diffrn_orient_matrix_UB_13      -0.0664887000
_diffrn_orient_matrix_UB_21      -0.0868162000
_diffrn_orient_matrix_UB_22      -0.0152510000
_diffrn_orient_matrix_UB_23      0.0364482000
_diffrn_orient_matrix_UB_31      0.0081338000
_diffrn_orient_matrix_UB_32      0.2078152000
_diffrn_orient_matrix_UB_33      0.0147400000
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21006
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.114
_diffrn_reflns_theta_min         3.565
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.019
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.645
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.00137(8)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+0.5997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3866
_reflns_number_total             4060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00739a2.cif
_cod_data_source_block           d_20_100_autored
_cod_depositor_comments
'Adding full bibliography for 7160574--7160577.cif.'
_cod_database_code               7160574
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H15 I N2'
_shelx_estimated_absorpt_t_max   0.519
_shelx_estimated_absorpt_t_min   0.083
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C17(H17), C16(H16), C10(H10), C15(H15), C8(H8), C9(H9), C2(H2),
 C1(H1), C26(H26), C14(H14), C22(H22), C23(H23), C25(H25), C24(H24)
;
_shelx_res_checksum              64041
_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 48.860
_oxdiff_exptl_absorpt_empirical_full_min 0.555