# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d_20_100_autored
_database_code_depnum_ccdc_archive 'CCDC 2448317'
loop_
_audit_author_name
_audit_author_address
'Oleg P. Demidov'
;North Caucasus Federal University
Russia
;
_audit_update_record             
;
2025-05-02 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_audit_creation_date             2022-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        6-Iodo-5-phenylphenanthro[9,10-f]quinoxaline
_chemical_formula_moiety         'C26 H15 I N2'
_chemical_formula_sum            'C26 H15 I N2'
_chemical_formula_weight         482.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H15 I N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.41874(11)
_cell_length_b                   7.27707(5)
_cell_length_c                   20.60254(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.5083(8)
_cell_angle_gamma                90
_cell_volume                     1947.67(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13683
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7950
_cell_measurement_theta_min      4.4120
_shelx_estimated_absorpt_T_max   0.519
_shelx_estimated_absorpt_T_min   0.083
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 1 -1 0.1046
8 0 -9 0.0422
1 0 12 0.0900
-1 0 -12 0.0936
-1 5 1 0.1830
4 0 10 0.0959
-4 0 -10 0.0987
0 -5 -2 0.1786
9 0 -5 0.0551
-8 1 9 0.0388
8 0 -9 0.0343
-6 0 12 0.0571
2 5 -1 0.1779
-1 0 13 0.0830
1 0 -13 0.0816
-8 0 9 0.0210

_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.058
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8.2162 1.2514 -0.5660 -0.5758 -0.7530 0.3185
7.6505 -0.3501 -9.0647 -0.0253 -0.9892 -0.1441
1.3795 -0.2683 12.2306 -0.9341 0.3301 0.1357
-1.3796 0.3874 -12.2078 0.9371 -0.3311 -0.1107
-0.5253 4.7114 0.6584 0.1751 -0.0023 0.9845
3.9420 -0.1539 10.0185 -0.9887 0.0253 0.1478
-3.9135 -0.1030 -10.0546 0.9792 -0.0251 -0.2014
-0.1063 -4.6354 -2.4278 -0.0039 -0.0086 -1.0000
8.5938 -0.0735 -5.4246 -0.3327 -0.9427 -0.0253
-7.5834 0.5513 9.1107 0.0244 0.9820 0.1872
7.7398 0.1065 -8.9180 -0.0251 -0.9986 -0.0464
-6.1321 -0.3008 11.5226 -0.2846 0.9569 0.0575
2.0450 4.5897 -1.1445 0.0839 -0.2892 0.9536
-1.2519 0.3894 13.2488 -0.7657 0.5856 0.2660
1.2867 -0.0728 -13.2983 0.7780 -0.5953 -0.2007
-7.7155 0.0568 8.9827 0.0250 0.9964 0.0815

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    1.00    --  -41.19 125.00 150.00   81
  2  ω   -115.00 -17.00   1.00    1.00    --  -41.19 -38.00-120.00   98
  3  ω   -115.00 -17.00   1.00    1.00    --  -41.19 -38.00 150.00   98
  4  ω      8.00  42.00   1.00    1.00    --   41.19  81.00 -29.19   34
  5  ω    -21.00  74.00   1.00    1.00    --   41.19 -77.00 120.00   95
  6  ω     30.00 165.00   1.00    1.00    --  112.00 -15.00  30.00  135
  7  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00 -90.00  101
  8  ω     39.00 138.00   1.00    1.00    --  112.00 -45.00  60.00   99
  9  ω     36.00 109.00   1.00    1.00    --  112.00-111.00 -60.00   73
 10  ω     83.00 178.00   1.00    1.00    --  112.00  61.00 -30.00   95
 11  ω     36.00 109.00   1.00    1.00    --  112.00-111.00   0.00   73
 12  ω     83.00 178.00   1.00    1.00    --  112.00  61.00 -90.00   95
 13  ω     36.00 109.00   1.00    1.00    --  112.00-111.00-180.00   73
 14  ω    103.00 178.00   1.00    1.00    --  112.00  77.00   0.00   75
 15  ω    103.00 178.00   1.00    1.00    --  112.00  77.00-180.00   75
 16  ω     36.00 109.00   1.00    1.00    --  112.00-111.00 -30.00   73
 17  ω    133.00 160.00   1.00    1.00    --  112.00  77.00 -60.00   27
 18  ω    103.00 172.00   1.00    1.00    --  112.00  77.00 150.00   69
 19  ω     38.00  84.00   1.00    1.00    --  112.00 -77.00 -90.00   46
 20  ω    118.00 145.00   1.00    1.00    --  112.00 -77.00 -90.00   27
 21  ω     33.00  62.00   1.00    1.00    --  112.00 -95.00  60.00   29
 22  ω     81.00 106.00   1.00    1.00    --  112.00 -95.00  60.00   25
 23  ω     62.00  87.00   1.00    1.00    --  112.00 178.00-150.00   25
 24  ω    114.00 157.00   1.00    1.00    --  112.00 111.00  60.00   43
 25  ω     30.00  61.00   1.00    1.00    --  112.00 -15.00 -90.00   31
 26  ω    114.00 165.00   1.00    1.00    --  112.00 -15.00 -90.00   51
 27  ω    115.00 147.00   1.00    1.00    --  112.00 111.00-180.00   32
 28  ω    150.00 177.00   1.00    1.00    --  112.00  77.00 120.00   27
 29  ω     81.00 106.00   1.00    1.00    --  112.00 -95.00  30.00   25
 30  ω     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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3866
_reflns_number_total             4060
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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+0.001xFc²λ³/sin(2θ)]^-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_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.062
_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/[σ²(Fo²)+(0.0440P)²+0.5997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0703
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.63328(2) 0.26169(2) 0.87959(2) 0.01615(8) Uani 1 1 d . . . . .
N2 N 0.43872(13) 0.3900(2) 0.92284(8) 0.0164(3) Uani 1 1 d . . . . .
N1 N 0.23493(13) 0.4533(2) 0.84973(8) 0.0152(3) Uani 1 1 d . . . . .
C3 C 0.41136(15) 0.3761(3) 0.85475(9) 0.0134(4) Uani 1 1 d . . . . .
C13 C 0.15514(15) 0.3902(3) 0.63329(9) 0.0130(4) Uani 1 1 d . . . . .
C4 C 0.48772(14) 0.3344(3) 0.81987(9) 0.0135(4) Uani 1 1 d . . . . .
C20 C 0.30801(14) 0.4032(3) 0.81740(9) 0.0123(4) Uani 1 1 d . . . . .
C11 C 0.21737(16) 0.5007(3) 0.53572(9) 0.0175(4) Uani 1 1 d . . . . .
H11 H 0.148667 0.495682 0.508814 0.021 Uiso 1 1 calc R U . . .
C19 C 0.28162(14) 0.3924(3) 0.74490(9) 0.0123(3) Uani 1 1 d . . . . .
C17 C 0.09330(15) 0.3267(3) 0.73209(9) 0.0144(4) Uani 1 1 d . . . . .
H17 H 0.105298 0.315508 0.779358 0.017 Uiso 1 1 calc R U . . .
C16 C -0.00379(17) 0.2932(3) 0.69224(11) 0.0169(4) Uani 1 1 d . . . . .
H16 H -0.058007 0.261793 0.712285 0.020 Uiso 1 1 calc R U . . .
C18 C 0.17559(14) 0.3773(3) 0.70430(9) 0.0127(4) Uani 1 1 d . . . . .
C10 C 0.29454(17) 0.5621(3) 0.50784(10) 0.0208(4) Uani 1 1 d . . . . .
H10 H 0.279506 0.594165 0.461704 0.025 Uiso 1 1 calc R U . . .
C21 C 0.54532(17) 0.2871(3) 0.71523(10) 0.0158(4) Uani 1 1 d . . . . .
C7 C 0.34073(15) 0.4471(3) 0.64282(9) 0.0135(4) Uani 1 1 d . . . . .
C15 C -0.02311(16) 0.3052(3) 0.62252(10) 0.0172(4) Uani 1 1 d . . . . .
H15 H -0.090097 0.281403 0.595098 0.021 Uiso 1 1 calc R U . . .
C5 C 0.46650(14) 0.3434(3) 0.75128(9) 0.0129(4) Uani 1 1 d . . . . .
C6 C 0.36327(14) 0.3923(3) 0.71358(9) 0.0125(4) Uani 1 1 d . . . . .
C12 C 0.23830(15) 0.4452(3) 0.60327(9) 0.0136(4) Uani 1 1 d . . . . .
C8 C 0.41771(15) 0.5217(3) 0.61408(10) 0.0168(4) Uani 1 1 d . . . . .
H8 H 0.486154 0.533680 0.640922 0.020 Uiso 1 1 calc R U . . .
C9 C 0.39495(16) 0.5770(3) 0.54783(10) 0.0188(4) Uani 1 1 d . . . . .
H9 H 0.447723 0.625280 0.529462 0.023 Uiso 1 1 calc R U . . .
C2 C 0.36589(16) 0.4374(3) 0.95206(9) 0.0182(4) Uani 1 1 d . . . . .
H2 H 0.382372 0.449056 0.999490 0.022 Uiso 1 1 calc R U . . .
C1 C 0.26432(16) 0.4715(3) 0.91509(10) 0.0180(4) Uani 1 1 d . . . . .
H1 H 0.215026 0.509107 0.938402 0.022 Uiso 1 1 calc R U . . .
C26 C 0.52554(16) 0.1341(3) 0.67322(10) 0.0188(4) Uani 1 1 d . . . . .
H26 H 0.462802 0.068346 0.667680 0.023 Uiso 1 1 calc R U . . .
C14 C 0.05591(15) 0.3518(3) 0.59382(10) 0.0164(4) Uani 1 1 d . . . . .
H14 H 0.042907 0.357919 0.546371 0.020 Uiso 1 1 calc R U . . .
C22 C 0.63722(16) 0.3836(3) 0.72232(10) 0.0205(4) Uani 1 1 d . . . . .
H22 H 0.651180 0.487179 0.751241 0.025 Uiso 1 1 calc R U . . .
C23 C 0.70825(17) 0.3298(4) 0.68764(12) 0.0269(5) Uani 1 1 d . . . . .
H23 H 0.769993 0.397851 0.692034 0.032 Uiso 1 1 calc R U . . .
C25 C 0.5985(2) 0.0777(3) 0.63924(11) 0.0275(5) Uani 1 1 d . . . . .
H25 H 0.585751 -0.027956 0.611304 0.033 Uiso 1 1 calc R U . . .
C24 C 0.6891(2) 0.1756(4) 0.64624(13) 0.0310(6) Uani 1 1 d . . . . .
H24 H 0.738258 0.137577 0.622839 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.0987(18) . ?
N2 C3 1.362(2) . ?
N2 C2 1.316(3) . ?
N1 C20 1.366(2) . ?
N1 C1 1.312(3) . ?
C3 C4 1.424(3) . ?
C3 C20 1.421(3) . ?
C13 C18 1.422(2) . ?
C13 C12 1.461(3) . ?
C13 C14 1.404(3) . ?
C4 C5 1.371(2) . ?
C20 C19 1.448(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.378(3) . ?
C11 C12 1.408(3) . ?
C19 C18 1.463(3) . ?
C19 C6 1.404(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.376(3) . ?
C17 C18 1.414(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.397(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.396(3) . ?
C21 C5 1.494(3) . ?
C21 C26 1.395(3) . ?
C21 C22 1.394(3) . ?
C7 C6 1.468(2) . ?
C7 C12 1.411(3) . ?
C7 C8 1.421(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.380(3) . ?
C5 C6 1.452(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.407(3) . ?
C1 H1 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.400(3) . ?
C14 H14 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.383(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.394(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.386(4) . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C3 116.82(17) . . ?
C1 N1 C20 117.36(18) . . ?
N2 C3 C4 119.55(17) . . ?
N2 C3 C20 121.48(17) . . ?
C20 C3 C4 118.97(16) . . ?
C18 C13 C12 118.87(17) . . ?
C14 C13 C18 119.56(17) . . ?
C14 C13 C12 121.58(17) . . ?
C3 C4 I1 116.08(13) . . ?
C5 C4 I1 122.59(14) . . ?
C5 C4 C3 121.33(17) . . ?
N1 C20 C3 119.70(16) . . ?
N1 C20 C19 119.84(17) . . ?
C3 C20 C19 120.28(17) . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.34(19) . . ?
C12 C11 H11 119.3 . . ?
C20 C19 C18 123.04(16) . . ?
C6 C19 C20 117.17(17) . . ?
C6 C19 C18 119.77(16) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.55(18) . . ?
C18 C17 H17 119.2 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.42(19) . . ?
C15 C16 H16 119.8 . . ?
C13 C18 C19 119.50(16) . . ?
C17 C18 C13 117.69(17) . . ?
C17 C18 C19 122.31(16) . . ?
C11 C10 H10 120.2 . . ?
C11 C10 C9 119.59(18) . . ?
C9 C10 H10 120.2 . . ?
C26 C21 C5 118.63(19) . . ?
C22 C21 C5 121.8(2) . . ?
C22 C21 C26 119.53(19) . . ?
C12 C7 C6 119.96(17) . . ?
C12 C7 C8 117.88(17) . . ?
C8 C7 C6 121.82(18) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.44(19) . . ?
C14 C15 H15 120.3 . . ?
C4 C5 C21 120.60(17) . . ?
C4 C5 C6 119.13(17) . . ?
C6 C5 C21 120.03(17) . . ?
C19 C6 C7 117.77(17) . . ?
C19 C6 C5 120.27(16) . . ?
C5 C6 C7 121.95(16) . . ?
C11 C12 C13 120.84(18) . . ?
C11 C12 C7 119.48(18) . . ?
C7 C12 C13 119.66(17) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.27(19) . . ?
C9 C8 H8 119.4 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.14(19) . . ?
C8 C9 H9 119.9 . . ?
N2 C2 H2 119.1 . . ?
N2 C2 C1 121.89(17) . . ?
C1 C2 H2 119.1 . . ?
N1 C1 C2 122.66(18) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C21 C26 H26 120.1 . . ?
C21 C26 C25 119.8(2) . . ?
C25 C26 H26 120.1 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.34(18) . . ?
C15 C14 H14 119.3 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 119.9(2) . . ?
C24 C23 H23 120.0 . . ?
C26 C25 H25 119.9 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C4 C5 C21 4.7(3) . . . . ?
I1 C4 C5 C6 179.11(14) . . . . ?
N2 C3 C4 I1 8.3(2) . . . . ?
N2 C3 C4 C5 -171.14(18) . . . . ?
N2 C3 C20 N1 3.3(3) . . . . ?
N2 C3 C20 C19 178.38(17) . . . . ?
N2 C2 C1 N1 2.0(3) . . . . ?
N1 C20 C19 C18 -19.2(3) . . . . ?
N1 C20 C19 C6 162.36(18) . . . . ?
C3 N2 C2 C1 0.3(3) . . . . ?
C3 C4 C5 C21 -175.89(18) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C3 C20 C19 C18 165.77(18) . . . . ?
C3 C20 C19 C6 -12.7(3) . . . . ?
C4 C3 C20 N1 -176.39(17) . . . . ?
C4 C3 C20 C19 -1.3(3) . . . . ?
C4 C5 C6 C19 -13.3(3) . . . . ?
C4 C5 C6 C7 165.22(18) . . . . ?
C20 N1 C1 C2 -1.5(3) . . . . ?
C20 C3 C4 I1 -171.98(14) . . . . ?
C20 C3 C4 C5 8.6(3) . . . . ?
C20 C19 C18 C13 172.23(17) . . . . ?
C20 C19 C18 C17 -16.1(3) . . . . ?
C20 C19 C6 C7 -158.61(17) . . . . ?
C20 C19 C6 C5 19.9(3) . . . . ?
C11 C10 C9 C8 3.3(3) . . . . ?
C17 C16 C15 C14 -0.3(3) . . . . ?
C16 C17 C18 C13 -0.8(3) . . . . ?
C16 C17 C18 C19 -172.67(19) . . . . ?
C16 C15 C14 C13 -1.0(3) . . . . ?
C18 C13 C12 C11 -165.31(18) . . . . ?
C18 C13 C12 C7 13.1(3) . . . . ?
C18 C13 C14 C15 1.4(3) . . . . ?
C18 C19 C6 C7 22.9(3) . . . . ?
C18 C19 C6 C5 -158.56(17) . . . . ?
C18 C17 C16 C15 1.2(3) . . . . ?
C10 C11 C12 C13 176.49(19) . . . . ?
C10 C11 C12 C7 -1.9(3) . . . . ?
C21 C5 C6 C19 161.15(19) . . . . ?
C21 C5 C6 C7 -20.4(3) . . . . ?
C21 C26 C25 C24 -1.3(3) . . . . ?
C21 C22 C23 C24 -1.4(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C5 C21 C26 C25 -179.54(19) . . . . ?
C5 C21 C22 C23 -179.15(19) . . . . ?
C6 C19 C18 C13 -9.4(3) . . . . ?
C6 C19 C18 C17 162.35(18) . . . . ?
C6 C7 C12 C13 0.6(3) . . . . ?
C6 C7 C12 C11 179.04(18) . . . . ?
C6 C7 C8 C9 -178.36(18) . . . . ?
C12 C13 C18 C19 -8.9(3) . . . . ?
C12 C13 C18 C17 179.01(17) . . . . ?
C12 C13 C14 C15 -178.08(19) . . . . ?
C12 C11 C10 C9 -2.6(3) . . . . ?
C12 C7 C6 C19 -18.6(3) . . . . ?
C12 C7 C6 C5 162.84(18) . . . . ?
C12 C7 C8 C9 -5.1(3) . . . . ?
C8 C7 C6 C19 154.45(19) . . . . ?
C8 C7 C6 C5 -24.1(3) . . . . ?
C8 C7 C12 C13 -172.75(18) . . . . ?
C8 C7 C12 C11 5.7(3) . . . . ?
C2 N2 C3 C4 176.84(18) . . . . ?
C2 N2 C3 C20 -2.9(3) . . . . ?
C1 N1 C20 C3 -1.0(3) . . . . ?
C1 N1 C20 C19 -176.09(17) . . . . ?
C26 C21 C5 C4 114.7(2) . . . . ?
C26 C21 C5 C6 -59.7(3) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
C26 C25 C24 C23 0.5(4) . . . . ?
C14 C13 C18 C19 171.61(18) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C14 C13 C12 C11 14.2(3) . . . . ?
C14 C13 C12 C7 -167.42(19) . . . . ?
C22 C21 C5 C4 -65.6(3) . . . . ?
C22 C21 C5 C6 120.1(2) . . . . ?
C22 C21 C26 C25 0.7(3) . . . . ?
C22 C23 C24 C25 0.8(4) . . . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d_32_bigpr_100_autored
_database_code_depnum_ccdc_archive 'CCDC 2448320'
loop_
_audit_author_name
_audit_author_address
'Oleg P. Demidov'
;North Caucasus Federal University
Russia
;
_audit_update_record             
;
2025-05-02 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_audit_creation_date             2024-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        
10-(p-Tolyl)naphtho[2,1-f]phenanthro[9,10-h]quinoline
_chemical_formula_moiety         'C36 H23 N'
_chemical_formula_sum            'C36 H23 N'
_chemical_formula_weight         469.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36 H23 N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2948(2)
_cell_length_b                   13.81900(10)
_cell_length_c                   11.13390(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.3860(10)
_cell_angle_gamma                90
_cell_volume                     2349.14(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18608
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1330
_cell_measurement_theta_min      4.2950
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.758
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 0 0 0.1304
10 -1 0 0.1452
1 -7 4 0.2026
-2 -7 4 0.1889
3 7 3 0.1710
-8 4 -3 0.2147
8 -3 3 0.2065
-1 -5 6 0.1443
1 6 -5 0.1834
0 -1 -1 0.2073

_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.285
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.8945 -0.0313 -0.0974 -0.4064 -0.8523 0.3292
9.8949 -0.5542 -0.1699 0.4157 0.8723 -0.2575
1.4248 -6.8742 4.4549 -0.6970 0.6593 0.2821
-1.7133 -6.9745 4.4342 -0.8303 0.3941 0.3940
2.9718 7.3822 3.3652 0.0085 0.0039 -1.0000
-7.6006 3.7116 -3.2224 0.1820 -0.9755 0.1237
7.6772 -3.3723 3.3493 -0.1810 0.9694 -0.1659
-1.0400 -5.4777 5.7079 -0.8931 0.4245 0.1490
1.2365 5.9356 -5.3868 0.8813 -0.4188 -0.2190
-0.0002 -1.0000 -1.0008 0.0779 0.0123 0.1593

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -16.00   1.00    1.00    --  -41.60 -46.00-130.00   98
  2  ω     16.00 114.00   1.00    1.00    --   41.60  46.00  19.00   98
  3  ω     39.00 138.00   1.00    1.41    --  112.00 -46.00-130.00   99
  4  ω     86.00 178.00   1.00    1.41    --  112.00  46.00  19.00   92
  5  ω    -68.00  31.00   1.00    1.00    --  -41.60  46.00  19.00   99
  6  ω     23.00  98.00   1.00    1.00    --   41.60-125.00  90.00   75
  7  ω     23.00  98.00   1.00    1.00    --   41.60-125.00-150.00   75
  8  ω      7.00  36.00   1.00    1.00    --   41.60  85.00 -99.63   29
  9  ω    100.00 178.00   1.00    1.41    --  112.00 111.00 -90.00   78
 10  ω     86.00 178.00   1.00    1.41    --  112.00  45.00  60.00   92
 11  ω     36.00 113.00   1.00    1.41    --  112.00-111.00 -90.00   77
 12  ω     86.00 178.00   1.00    1.41    --  112.00  45.00 -30.00   92
 13  ω    100.00 178.00   1.00    1.41    --  112.00 111.00-120.00   78
 14  ω     86.00 178.00   1.00    1.41    --  112.00  45.00  90.00   92
 15  ω     30.00 110.00   1.00    1.41    --  112.00 -95.00  30.00   80
 16  ω     83.00 178.00   1.00    1.41    --  112.00  61.00  30.00   95
 17  ω     86.00 178.00   1.00    1.41    --  112.00  45.00 150.00   92
 18  ω     33.00 146.00   1.00    1.41    --  112.00 -82.00 -30.99  113
 19  ω     59.00 178.00   1.00    1.41    --  112.00  15.00 120.00  119
 20  ω     36.00 113.00   1.00    1.41    --  112.00-111.00-120.00   77
 21  ω     79.00 178.00   1.00    1.41    --  112.00  77.00 -60.00   99
 22  ω     40.00 139.00   1.00    1.41    --  112.00 -51.00-155.15   99
 23  ω     33.00 146.00   1.00    1.41    --  112.00 -82.00  84.60  113
 24  ω     36.00 113.00   1.00    1.41    --  112.00-111.00  90.00   77
 25  ω     40.00 141.00   1.00    1.41    --  112.00 -61.00-120.00  101
 26  ω     36.00 113.00   1.00    1.41    --  112.00-111.00-150.00   77
 27  ω   -114.00 -13.00   1.00    1.00    --  -41.60 -57.00  90.00  101
 28  ω   -118.00 -27.00   1.00    1.00    --  -41.60 -77.00   0.00   91
 29  ω      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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4436
_reflns_number_total             4897
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.069
_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/[σ²(Fo²)+(0.0658P)²+2.6284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1511
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.23886(10) 0.54587(11) 0.76350(14) 0.0228(3) Uani 1 1 d . . . . .
C14 C 0.43672(11) 0.59105(12) 0.35747(15) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.36557(11) 0.61495(12) 0.67448(15) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.50082(11) 0.66863(12) 0.57749(15) 0.0179(3) Uani 1 1 d . . . . .
H7 H 0.523337 0.691586 0.653580 0.022 Uiso 1 1 calc R U . . .
C6 C 0.41576(11) 0.62679(12) 0.56889(15) 0.0171(3) Uani 1 1 d . . . . .
C15 C 0.37904(11) 0.59735(12) 0.45623(15) 0.0174(3) Uani 1 1 d . . . . .
C13 C 0.41434(11) 0.53773(12) 0.25106(15) 0.0188(3) Uani 1 1 d . . . . .
H13 H 0.360014 0.504285 0.244052 0.023 Uiso 1 1 calc R U . . .
C8 C 0.55154(11) 0.67726(12) 0.48125(15) 0.0173(3) Uani 1 1 d . . . . .
C22 C 0.14813(11) 0.53814(13) 0.32337(16) 0.0199(4) Uani 1 1 d . . . . .
C10 C 0.57727(11) 0.62705(12) 0.27166(16) 0.0189(3) Uani 1 1 d . . . . .
H10 H 0.633744 0.655830 0.278880 0.023 Uiso 1 1 calc R U . . .
C31 C 0.63723(11) 0.72859(12) 0.49600(15) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.52193(11) 0.63340(12) 0.36889(15) 0.0171(3) Uani 1 1 d . . . . .
C29 C 0.24829(11) 0.53299(12) 0.54765(15) 0.0185(3) Uani 1 1 d . . . . .
C30 C 0.28590(11) 0.56184(12) 0.66550(16) 0.0188(3) Uani 1 1 d . . . . .
C16 C 0.28730(11) 0.56809(12) 0.44616(15) 0.0183(3) Uani 1 1 d . . . . .
C23 C 0.12079(11) 0.47401(13) 0.41805(16) 0.0197(4) Uani 1 1 d . . . . .
C17 C 0.23116(11) 0.58288(12) 0.33638(16) 0.0193(4) Uani 1 1 d . . . . .
C28 C 0.16891(11) 0.47351(12) 0.53067(16) 0.0194(4) Uani 1 1 d . . . . .
C36 C 0.69685(11) 0.70542(12) 0.59116(15) 0.0188(4) Uani 1 1 d . . . . .
H36 H 0.683791 0.654351 0.644341 0.023 Uiso 1 1 calc R U . . .
C34 C 0.79673(11) 0.83082(13) 0.53299(16) 0.0201(4) Uani 1 1 d . . . . .
C12 C 0.46912(12) 0.53332(13) 0.15826(15) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.451767 0.498372 0.087337 0.024 Uiso 1 1 calc R U . . .
C18 C 0.25307(12) 0.65231(13) 0.25000(16) 0.0207(4) Uani 1 1 d . . . . .
H18 H 0.307330 0.685616 0.260290 0.025 Uiso 1 1 calc R U . . .
C4 C 0.39442(12) 0.65018(12) 0.78840(16) 0.0199(4) Uani 1 1 d . . . . .
H4 H 0.447528 0.685786 0.797534 0.024 Uiso 1 1 calc R U . . .
C19 C 0.19780(12) 0.67288(14) 0.15141(16) 0.0230(4) Uani 1 1 d . . . . .
H19 H 0.213937 0.719960 0.094603 0.028 Uiso 1 1 calc R U . . .
C11 C 0.55081(12) 0.58009(13) 0.16720(16) 0.0204(4) Uani 1 1 d . . . . .
H11 H 0.587513 0.579206 0.101280 0.025 Uiso 1 1 calc R U . . .
C32 C 0.65878(12) 0.80401(13) 0.41912(16) 0.0198(4) Uani 1 1 d . . . . .
H32 H 0.619235 0.821256 0.353611 0.024 Uiso 1 1 calc R U . . .
C33 C 0.73735(12) 0.85398(13) 0.43746(16) 0.0211(4) Uani 1 1 d . . . . .
H33 H 0.750798 0.904734 0.384029 0.025 Uiso 1 1 calc R U . . .
C3 C 0.34632(12) 0.63345(13) 0.88655(16) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.365158 0.657116 0.963902 0.026 Uiso 1 1 calc R U . . .
C26 C 0.07120(13) 0.34908(14) 0.59968(18) 0.0255(4) Uani 1 1 d . . . . .
H26 H 0.055474 0.305174 0.660417 0.031 Uiso 1 1 calc R U . . .
C27 C 0.14353(12) 0.40789(13) 0.61945(17) 0.0230(4) Uani 1 1 d . . . . .
H27 H 0.176838 0.404195 0.694080 0.028 Uiso 1 1 calc R U . . .
C35 C 0.77520(12) 0.75594(13) 0.60950(16) 0.0208(4) Uani 1 1 d . . . . .
H35 H 0.814641 0.739058 0.675277 0.025 Uiso 1 1 calc R U . . .
C2 C 0.26877(13) 0.58050(14) 0.86912(16) 0.0242(4) Uani 1 1 d . . . . .
H2 H 0.235493 0.568622 0.936991 0.029 Uiso 1 1 calc R U . . .
C24 C 0.04633(12) 0.41405(13) 0.40101(18) 0.0241(4) Uani 1 1 d . . . . .
H24 H 0.013118 0.415375 0.326184 0.029 Uiso 1 1 calc R U . . .
C37 C 0.88217(12) 0.88449(14) 0.55262(18) 0.0252(4) Uani 1 1 d . . . . .
H37A H 0.903832 0.902688 0.474663 0.038 Uiso 1 1 calc R U . . .
H37B H 0.925232 0.842746 0.595829 0.038 Uiso 1 1 calc R U . . .
H37C H 0.873012 0.942920 0.600147 0.038 Uiso 1 1 calc R U . . .
C21 C 0.09337(12) 0.55907(14) 0.22007(17) 0.0234(4) Uani 1 1 d . . . . .
H21 H 0.038376 0.527354 0.209044 0.028 Uiso 1 1 calc R U . . .
C25 C 0.02106(12) 0.35367(14) 0.49111(18) 0.0255(4) Uani 1 1 d . . . . .
H25 H -0.030291 0.315344 0.479320 0.031 Uiso 1 1 calc R U . . .
C20 C 0.11788(12) 0.62436(14) 0.13501(17) 0.0255(4) Uani 1 1 d . . . . .
H20 H 0.080553 0.636405 0.065371 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C30 1.360(2) . ?
N2 C2 1.326(2) . ?
C14 C15 1.452(2) . ?
C14 C13 1.420(2) . ?
C14 C9 1.427(2) . ?
C5 C6 1.451(2) . ?
C5 C30 1.421(2) . ?
C5 C4 1.405(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.422(2) . ?
C7 C8 1.365(2) . ?
C6 C15 1.404(2) . ?
C15 C16 1.458(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.369(2) . ?
C8 C31 1.491(2) . ?
C8 C9 1.439(2) . ?
C22 C23 1.457(3) . ?
C22 C17 1.412(2) . ?
C22 C21 1.412(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.416(2) . ?
C10 C11 1.372(2) . ?
C31 C36 1.394(2) . ?
C31 C32 1.400(2) . ?
C29 C30 1.457(2) . ?
C29 C16 1.396(2) . ?
C29 C28 1.469(2) . ?
C16 C17 1.466(2) . ?
C23 C28 1.416(2) . ?
C23 C24 1.412(2) . ?
C17 C18 1.413(3) . ?
C28 C27 1.413(3) . ?
C36 H36 0.9500 . ?
C36 C35 1.392(2) . ?
C34 C33 1.394(3) . ?
C34 C35 1.392(3) . ?
C34 C37 1.507(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.405(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.375(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.373(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(3) . ?
C11 H11 0.9500 . ?
C32 H32 0.9500 . ?
C32 C33 1.391(2) . ?
C33 H33 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.397(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.380(3) . ?
C26 C25 1.394(3) . ?
C27 H27 0.9500 . ?
C35 H35 0.9500 . ?
C2 H2 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.378(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C20 1.376(3) . ?
C25 H25 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C30 118.82(16) . . ?
C13 C14 C15 122.38(16) . . ?
C13 C14 C9 117.45(15) . . ?
C9 C14 C15 120.01(15) . . ?
C30 C5 C6 119.59(15) . . ?
C4 C5 C6 122.64(16) . . ?
C4 C5 C30 117.70(16) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C8 C7 C6 122.89(15) . . ?
C7 C6 C5 121.14(15) . . ?
C15 C6 C5 119.23(15) . . ?
C15 C6 C7 119.62(15) . . ?
C14 C15 C16 123.36(15) . . ?
C6 C15 C14 117.70(15) . . ?
C6 C15 C16 118.78(15) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 C14 121.64(16) . . ?
C12 C13 H13 119.2 . . ?
C7 C8 C31 119.47(15) . . ?
C7 C8 C9 118.79(16) . . ?
C9 C8 C31 121.71(15) . . ?
C17 C22 C23 119.13(16) . . ?
C21 C22 C23 122.14(16) . . ?
C21 C22 C17 118.70(17) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C11 C10 C9 121.19(16) . . ?
C36 C31 C8 120.39(15) . . ?
C36 C31 C32 117.94(16) . . ?
C32 C31 C8 121.60(15) . . ?
C14 C9 C8 119.27(15) . . ?
C10 C9 C14 119.37(15) . . ?
C10 C9 C8 121.28(16) . . ?
C30 C29 C28 123.25(15) . . ?
C16 C29 C30 117.99(15) . . ?
C16 C29 C28 118.68(15) . . ?
N2 C30 C5 121.29(16) . . ?
N2 C30 C29 118.61(16) . . ?
C5 C30 C29 119.74(15) . . ?
C15 C16 C17 122.62(15) . . ?
C29 C16 C15 119.31(15) . . ?
C29 C16 C17 117.79(16) . . ?
C28 C23 C22 119.16(16) . . ?
C24 C23 C22 121.55(16) . . ?
C24 C23 C28 119.27(17) . . ?
C22 C17 C16 120.22(16) . . ?
C22 C17 C18 118.40(16) . . ?
C18 C17 C16 120.76(16) . . ?
C23 C28 C29 119.57(16) . . ?
C27 C28 C29 121.89(16) . . ?
C27 C28 C23 118.23(16) . . ?
C31 C36 H36 119.5 . . ?
C35 C36 C31 121.03(16) . . ?
C35 C36 H36 119.5 . . ?
C33 C34 C37 121.18(16) . . ?
C35 C34 C33 118.07(16) . . ?
C35 C34 C37 120.75(16) . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.48(16) . . ?
C11 C12 H12 119.8 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.64(17) . . ?
C19 C18 H18 119.2 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.38(17) . . ?
C3 C4 H4 119.8 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.81(17) . . ?
C20 C19 H19 120.1 . . ?
C10 C11 C12 119.62(16) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C31 C32 H32 119.6 . . ?
C33 C32 C31 120.83(16) . . ?
C33 C32 H32 119.6 . . ?
C34 C33 H33 119.5 . . ?
C32 C33 C34 121.08(17) . . ?
C32 C33 H33 119.5 . . ?
C4 C3 H3 121.0 . . ?
C4 C3 C2 117.91(16) . . ?
C2 C3 H3 121.0 . . ?
C27 C26 H26 119.8 . . ?
C27 C26 C25 120.41(18) . . ?
C25 C26 H26 119.8 . . ?
C28 C27 H27 119.4 . . ?
C26 C27 C28 121.15(18) . . ?
C26 C27 H27 119.4 . . ?
C36 C35 C34 121.06(16) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
N2 C2 C3 123.90(17) . . ?
N2 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.09(18) . . ?
C25 C24 H24 119.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C22 C21 H21 119.3 . . ?
C20 C21 C22 121.49(17) . . ?
C20 C21 H21 119.3 . . ?
C26 C25 H25 120.2 . . ?
C24 C25 C26 119.69(17) . . ?
C24 C25 H25 120.2 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.78(17) . . ?
C21 C20 H20 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C15 C16 C29 150.01(16) . . . . ?
C14 C15 C16 C17 -36.3(2) . . . . ?
C14 C13 C12 C11 1.5(3) . . . . ?
C5 C6 C15 C14 -167.33(15) . . . . ?
C5 C6 C15 C16 8.3(2) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C7 C6 C15 C14 13.4(2) . . . . ?
C7 C6 C15 C16 -171.00(15) . . . . ?
C7 C8 C31 C36 49.4(2) . . . . ?
C7 C8 C31 C32 -127.61(18) . . . . ?
C7 C8 C9 C14 6.5(2) . . . . ?
C7 C8 C9 C10 -170.25(16) . . . . ?
C6 C5 C30 N2 177.32(15) . . . . ?
C6 C5 C30 C29 -9.7(2) . . . . ?
C6 C5 C4 C3 -177.16(16) . . . . ?
C6 C7 C8 C31 175.49(15) . . . . ?
C6 C7 C8 C9 -6.6(3) . . . . ?
C6 C15 C16 C29 -25.3(2) . . . . ?
C6 C15 C16 C17 148.39(16) . . . . ?
C15 C14 C13 C12 179.35(16) . . . . ?
C15 C14 C9 C8 3.5(2) . . . . ?
C15 C14 C9 C10 -179.72(15) . . . . ?
C15 C16 C17 C22 168.57(16) . . . . ?
C15 C16 C17 C18 -20.6(2) . . . . ?
C13 C14 C15 C6 161.96(16) . . . . ?
C13 C14 C15 C16 -13.4(3) . . . . ?
C13 C14 C9 C8 -172.05(15) . . . . ?
C13 C14 C9 C10 4.7(2) . . . . ?
C13 C12 C11 C10 2.7(3) . . . . ?
C8 C7 C6 C5 177.15(16) . . . . ?
C8 C7 C6 C15 -3.6(3) . . . . ?
C8 C31 C36 C35 -176.82(16) . . . . ?
C8 C31 C32 C33 177.09(16) . . . . ?
C22 C23 C28 C29 -3.7(2) . . . . ?
C22 C23 C28 C27 -177.38(16) . . . . ?
C22 C23 C24 C25 179.99(17) . . . . ?
C22 C17 C18 C19 -3.6(3) . . . . ?
C22 C21 C20 C19 -1.3(3) . . . . ?
C31 C8 C9 C14 -175.69(15) . . . . ?
C31 C8 C9 C10 7.6(2) . . . . ?
C31 C36 C35 C34 -0.4(3) . . . . ?
C31 C32 C33 C34 -0.3(3) . . . . ?
C9 C14 C15 C6 -13.4(2) . . . . ?
C9 C14 C15 C16 171.25(15) . . . . ?
C9 C14 C13 C12 -5.2(2) . . . . ?
C9 C8 C31 C36 -128.46(18) . . . . ?
C9 C8 C31 C32 54.6(2) . . . . ?
C9 C10 C11 C12 -3.1(3) . . . . ?
C29 C16 C17 C22 -17.6(2) . . . . ?
C29 C16 C17 C18 153.22(17) . . . . ?
C29 C28 C27 C26 -176.73(16) . . . . ?
C30 N2 C2 C3 0.3(3) . . . . ?
C30 C5 C6 C7 -171.95(15) . . . . ?
C30 C5 C6 C15 8.8(2) . . . . ?
C30 C5 C4 C3 -0.2(2) . . . . ?
C30 C29 C16 C15 24.3(2) . . . . ?
C30 C29 C16 C17 -149.73(15) . . . . ?
C30 C29 C28 C23 159.80(16) . . . . ?
C30 C29 C28 C27 -26.7(3) . . . . ?
C16 C29 C30 N2 166.24(16) . . . . ?
C16 C29 C30 C5 -7.0(2) . . . . ?
C16 C29 C28 C23 -16.7(2) . . . . ?
C16 C29 C28 C27 156.76(17) . . . . ?
C16 C17 C18 C19 -174.59(16) . . . . ?
C23 C22 C17 C16 -2.6(2) . . . . ?
C23 C22 C17 C18 -173.65(16) . . . . ?
C23 C22 C21 C20 175.93(17) . . . . ?
C23 C28 C27 C26 -3.2(3) . . . . ?
C23 C24 C25 C26 -2.1(3) . . . . ?
C17 C22 C23 C28 13.1(2) . . . . ?
C17 C22 C23 C24 -168.41(16) . . . . ?
C17 C22 C21 C20 -2.5(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C28 C29 C30 N2 -10.3(3) . . . . ?
C28 C29 C30 C5 176.52(15) . . . . ?
C28 C29 C16 C15 -159.01(15) . . . . ?
C28 C29 C16 C17 27.0(2) . . . . ?
C28 C23 C24 C25 -1.5(3) . . . . ?
C36 C31 C32 C33 0.1(3) . . . . ?
C18 C19 C20 C21 2.6(3) . . . . ?
C4 C5 C6 C7 5.0(3) . . . . ?
C4 C5 C6 C15 -174.31(16) . . . . ?
C4 C5 C30 N2 0.3(2) . . . . ?
C4 C5 C30 C29 173.27(15) . . . . ?
C4 C3 C2 N2 -0.2(3) . . . . ?
C11 C10 C9 C14 -0.7(2) . . . . ?
C11 C10 C9 C8 176.04(16) . . . . ?
C32 C31 C36 C35 0.3(2) . . . . ?
C33 C34 C35 C36 0.2(3) . . . . ?
C27 C26 C25 C24 3.1(3) . . . . ?
C35 C34 C33 C32 0.2(3) . . . . ?
C2 N2 C30 C5 -0.3(3) . . . . ?
C2 N2 C30 C29 -173.40(16) . . . . ?
C24 C23 C28 C29 177.76(15) . . . . ?
C24 C23 C28 C27 4.1(2) . . . . ?
C37 C34 C33 C32 179.64(16) . . . . ?
C37 C34 C35 C36 -179.33(16) . . . . ?
C21 C22 C23 C28 -165.31(17) . . . . ?
C21 C22 C23 C24 13.2(3) . . . . ?
C21 C22 C17 C16 175.82(16) . . . . ?
C21 C22 C17 C18 4.8(2) . . . . ?
C25 C26 C27 C28 -0.4(3) . . . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d_23_100_2_autored
_database_code_depnum_ccdc_archive 'CCDC 2448319'
loop_
_audit_author_name
_audit_author_address
'Oleg P. Demidov'
;North Caucasus Federal University
Russia
;
_audit_update_record             
;
2025-05-02 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_audit_creation_date             2022-06-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
10-(p-Tolyl)naphtho[2,1-f]phenanthro[9,10-h]quinoxaline
_chemical_formula_moiety         'C35 H22 N2'
_chemical_formula_sum            'C35 H22 N2'
_chemical_formula_weight         470.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C35 H22 N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3608(2)
_cell_length_b                   13.69670(10)
_cell_length_c                   11.10420(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.7960(10)
_cell_angle_gamma                90
_cell_volume                     2331.11(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11143
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4510
_cell_measurement_theta_min      4.3090
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.867
_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_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 3 -6 0.1207
1 -7 4 0.1121
2 5 6 0.1103
-2 -5 -6 0.1197
10 1 -1 0.0152
-5 6 -3 0.0985
-10 0 0 0.0116

_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.043
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.7329 3.4063 -5.8929 0.3068 -0.4486 0.8394
1.4246 -7.2288 3.9866 -0.0092 -0.0018 -1.0000
1.9899 4.8448 5.7585 -0.2845 0.9577 -0.0435
-1.9667 -4.9825 -5.6876 0.2847 -0.9583 0.0250
9.9009 0.9699 -0.9085 -0.9968 -0.0793 -0.0091
-4.5818 6.4732 -3.4395 0.3352 0.0286 0.9417
-9.9763 0.1028 0.3134 0.9847 0.0787 0.1554

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -15.00   1.00    2.29    --  -41.60 -47.00-148.00   99
  2  ω    -68.00  31.00   1.00    2.29    --  -41.60  47.00   0.00   99
  3  ω     15.00 114.00   1.00    2.29    --   41.60  47.00   0.00   99
  4  ω     39.00 138.00   1.00    9.17    --  112.00 -47.00-148.00   99
  5  ω     86.00 178.00   1.00    9.17    --  112.00  47.00   0.00   92
  6  ω     23.00  98.00   1.00    2.29    --   41.60-125.00-180.00   75
  7  ω      4.00  32.00   1.00    2.29    --   41.60  90.00-133.60   28
  8  ω     23.00  98.00   1.00    2.29    --   41.60-125.00  60.00   75
  9  ω     40.00 141.00   1.00    9.17    --  112.00 -61.00  90.00  101
 10  ω     86.00 178.00   1.00    9.17    --  112.00  45.00 -90.00   92
 11  ω     36.00 113.00   1.00    9.17    --  112.00-111.00  30.00   77
 12  ω     39.00 138.00   1.00    9.17    --  112.00 -46.00   0.01   99
 13  ω     36.00 140.00   1.00    9.17    --  112.00 -30.00  60.00  104
 14  ω     30.00 110.00   1.00    9.17    --  112.00 -95.00  90.00   80
 15  ω     89.00 137.00   1.00    9.17    --  112.00  30.00 -30.00   48
 16  ω     37.00  62.00   1.00    9.17    --  112.00-111.00-120.00   25
 17  ω     42.00  89.00   1.00    9.17    --  112.00 -30.00 -90.00   47
 18  ω    120.00 147.00   1.00    9.17    --  112.00  15.00 -60.00   27
 19  ω    108.00 176.00   1.00    9.17    --  112.00  16.00 -10.82   68
 20  ω     95.00 134.00   1.00    9.17    --  112.00 -30.00 -90.00   39
 21  ω     64.00  89.00   1.00    9.17    --  112.00  16.00 -10.82   25
 22  ω     65.00 103.00   1.00    9.17    --  112.00  15.00 -60.00   38
 23  ω     58.00  98.00   1.00    9.17    --  112.00 -95.00  30.00   40
 24  ω    100.00 150.00   1.00    9.17    --  112.00 111.00  30.00   50
 25  ω     95.00 144.00   1.00    9.17    --  112.00 -77.00-180.00   49
 26  ω     35.00  62.00   1.00    9.17    --  112.00 -15.00 -30.00   27
 27  ω     94.00 121.00   1.00    9.17    --  112.00 -15.00 -30.00   27
 28  ω     37.00 110.00   1.00    9.17    --  112.00-111.00-150.00   73
 29  ω     58.00  85.00   1.00    9.17    --  112.00-111.00 120.00   27
 30  ω     78.00 109.00   1.00    9.17    --  112.00 -95.00 -60.00   31
 31  ω     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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4185
_reflns_number_total             4854
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.037
_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/[σ²(Fo²)+(0.0651P)²+1.2521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40384(9) 0.34735(9) 0.78157(11) 0.0214(3) Uani 1 1 d . . . . .
N4 N 0.24558(9) 0.45085(10) 0.76801(12) 0.0238(3) Uani 1 1 d . . . . .
C21 C 0.41846(10) 0.37151(10) 0.56984(13) 0.0185(3) Uani 1 1 d . . . . .
C30 C 0.43797(10) 0.40743(10) 0.35866(13) 0.0181(3) Uani 1 1 d . . . . .
C22 C 0.36949(10) 0.38393(10) 0.67552(13) 0.0192(3) Uani 1 1 d . . . . .
C29 C 0.41514(10) 0.46155(10) 0.25199(13) 0.0197(3) Uani 1 1 d . . . . .
H29 H 0.360876 0.495014 0.244727 0.024 Uiso 1 1 calc R U . . .
C31 C 0.63781(10) 0.26881(10) 0.49726(13) 0.0193(3) Uani 1 1 d . . . . .
C26 C 0.57764(10) 0.37206(10) 0.27359(13) 0.0194(3) Uani 1 1 d . . . . .
H26 H 0.634094 0.343497 0.281169 0.023 Uiso 1 1 calc R U . . .
C25 C 0.52250(10) 0.36501(10) 0.37092(13) 0.0182(3) Uani 1 1 d . . . . .
C20 C 0.38089(10) 0.40129(10) 0.45749(13) 0.0184(3) Uani 1 1 d . . . . .
C6 C 0.25022(10) 0.46444(10) 0.54945(13) 0.0198(3) Uani 1 1 d . . . . .
C24 C 0.55271(10) 0.32082(10) 0.48353(13) 0.0187(3) Uani 1 1 d . . . . .
C13 C 0.15010(10) 0.45871(11) 0.32447(14) 0.0217(3) Uani 1 1 d . . . . .
C19 C 0.28922(10) 0.42959(10) 0.44745(13) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.28955(10) 0.43620(10) 0.66729(13) 0.0200(3) Uani 1 1 d . . . . .
C23 C 0.50293(10) 0.32954(10) 0.58035(13) 0.0194(3) Uani 1 1 d . . . . .
H23 H 0.525579 0.306829 0.656974 0.023 Uiso 1 1 calc R U . . .
C18 C 0.23302(10) 0.41432(11) 0.33728(13) 0.0203(3) Uani 1 1 d . . . . .
C34 C 0.79680(10) 0.16531(11) 0.53052(14) 0.0219(3) Uani 1 1 d . . . . .
C17 C 0.25537(10) 0.34460(11) 0.25050(14) 0.0218(3) Uani 1 1 d . . . . .
H17 H 0.309768 0.311619 0.260656 0.026 Uiso 1 1 calc R U . . .
C27 C 0.55079(10) 0.41939(11) 0.16889(13) 0.0217(3) Uani 1 1 d . . . . .
H27 H 0.587088 0.420230 0.102878 0.026 Uiso 1 1 calc R U . . .
C36 C 0.69876(10) 0.29205(11) 0.59157(13) 0.0207(3) Uani 1 1 d . . . . .
H36 H 0.686809 0.343582 0.645310 0.025 Uiso 1 1 calc R U . . .
C32 C 0.65770(10) 0.19251(11) 0.41944(13) 0.0213(3) Uani 1 1 d . . . . .
H32 H 0.617140 0.175106 0.354691 0.026 Uiso 1 1 calc R U . . .
C12 C 0.12301(10) 0.52339(11) 0.41959(14) 0.0220(3) Uani 1 1 d . . . . .
C28 C 0.46965(10) 0.46652(11) 0.15947(13) 0.0214(3) Uani 1 1 d . . . . .
H28 H 0.452361 0.502144 0.088466 0.026 Uiso 1 1 calc R U . . .
C16 C 0.19957(11) 0.32366(11) 0.15143(14) 0.0242(3) Uani 1 1 d . . . . .
H16 H 0.215697 0.276781 0.093910 0.029 Uiso 1 1 calc R U . . .
C35 C 0.77660(10) 0.24092(11) 0.60798(14) 0.0221(3) Uani 1 1 d . . . . .
H35 H 0.816918 0.257750 0.673246 0.026 Uiso 1 1 calc R U . . .
C2 C 0.35973(11) 0.36363(11) 0.87790(14) 0.0237(3) Uani 1 1 d . . . . .
H2 H 0.382018 0.339405 0.953971 0.028 Uiso 1 1 calc R U . . .
C7 C 0.17101(10) 0.52326(11) 0.53298(14) 0.0215(3) Uani 1 1 d . . . . .
C33 C 0.73594(10) 0.14218(11) 0.43599(14) 0.0223(3) Uani 1 1 d . . . . .
H33 H 0.748313 0.091014 0.381945 0.027 Uiso 1 1 calc R U . . .
C8 C 0.14514(10) 0.58847(11) 0.62285(15) 0.0247(3) Uani 1 1 d . . . . .
H8 H 0.177887 0.591315 0.698403 0.030 Uiso 1 1 calc R U . . .
C3 C 0.28123(11) 0.41549(12) 0.87081(14) 0.0259(3) Uani 1 1 d . . . . .
H3 H 0.252221 0.425810 0.942680 0.031 Uiso 1 1 calc R U . . .
C9 C 0.07313(11) 0.64800(12) 0.60256(16) 0.0277(3) Uani 1 1 d . . . . .
H9 H 0.056961 0.691440 0.663921 0.033 Uiso 1 1 calc R U . . .
C11 C 0.04915(10) 0.58419(12) 0.40185(15) 0.0260(3) Uani 1 1 d . . . . .
H11 H 0.016346 0.583339 0.326260 0.031 Uiso 1 1 calc R U . . .
C14 C 0.09492(10) 0.43727(12) 0.22120(15) 0.0253(3) Uani 1 1 d . . . . .
H14 H 0.039862 0.468777 0.210275 0.030 Uiso 1 1 calc R U . . .
C15 C 0.11948(11) 0.37138(12) 0.13583(15) 0.0270(3) Uani 1 1 d . . . . .
H15 H 0.081778 0.358527 0.066349 0.032 Uiso 1 1 calc R U . . .
C10 C 0.02378(11) 0.64465(12) 0.49188(17) 0.0285(4) Uani 1 1 d . . . . .
H10 H -0.026953 0.683956 0.479159 0.034 Uiso 1 1 calc R U . . .
C37 C 0.88195(11) 0.11072(12) 0.54771(16) 0.0276(3) Uani 1 1 d . . . . .
H37A H 0.923550 0.149228 0.598796 0.041 Uiso 1 1 calc R U . . .
H37B H 0.905592 0.099661 0.469018 0.041 Uiso 1 1 calc R U . . .
H37C H 0.872046 0.047777 0.586489 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C22 1.3541(19) . ?
N1 C2 1.323(2) . ?
N4 C5 1.3593(19) . ?
N4 C3 1.325(2) . ?
C21 C22 1.445(2) . ?
C21 C20 1.400(2) . ?
C21 C23 1.417(2) . ?
C30 C29 1.421(2) . ?
C30 C25 1.421(2) . ?
C30 C20 1.452(2) . ?
C22 C5 1.419(2) . ?
C29 H29 0.9500 . ?
C29 C28 1.369(2) . ?
C31 C24 1.488(2) . ?
C31 C36 1.395(2) . ?
C31 C32 1.403(2) . ?
C26 H26 0.9500 . ?
C26 C25 1.420(2) . ?
C26 C27 1.371(2) . ?
C25 C24 1.438(2) . ?
C20 C19 1.458(2) . ?
C6 C19 1.400(2) . ?
C6 C5 1.457(2) . ?
C6 C7 1.461(2) . ?
C24 C23 1.365(2) . ?
C13 C18 1.410(2) . ?
C13 C12 1.460(2) . ?
C13 C14 1.411(2) . ?
C19 C18 1.465(2) . ?
C23 H23 0.9500 . ?
C18 C17 1.415(2) . ?
C34 C35 1.394(2) . ?
C34 C33 1.395(2) . ?
C34 C37 1.508(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.379(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.401(2) . ?
C36 H36 0.9500 . ?
C36 C35 1.387(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.387(2) . ?
C12 C7 1.416(2) . ?
C12 C11 1.411(2) . ?
C28 H28 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.394(2) . ?
C35 H35 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.397(2) . ?
C7 C8 1.416(2) . ?
C33 H33 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.381(2) . ?
C3 H3 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.401(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.374(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(2) . ?
C15 H15 0.9500 . ?
C10 H10 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C22 116.74(14) . . ?
C3 N4 C5 117.10(14) . . ?
C20 C21 C22 118.89(13) . . ?
C20 C21 C23 120.85(13) . . ?
C23 C21 C22 120.26(13) . . ?
C29 C30 C20 122.15(13) . . ?
C25 C30 C29 117.81(13) . . ?
C25 C30 C20 119.85(13) . . ?
N1 C22 C21 117.95(13) . . ?
N1 C22 C5 121.90(13) . . ?
C5 C22 C21 120.11(13) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 C30 121.45(14) . . ?
C28 C29 H29 119.3 . . ?
C36 C31 C24 120.62(13) . . ?
C36 C31 C32 118.04(14) . . ?
C32 C31 C24 121.29(13) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C27 C26 C25 121.11(14) . . ?
C30 C25 C24 119.71(13) . . ?
C26 C25 C30 119.12(13) . . ?
C26 C25 C24 121.07(13) . . ?
C21 C20 C30 117.16(13) . . ?
C21 C20 C19 119.00(13) . . ?
C30 C20 C19 123.74(13) . . ?
C19 C6 C5 117.51(13) . . ?
C19 C6 C7 118.97(13) . . ?
C5 C6 C7 123.47(13) . . ?
C25 C24 C31 121.43(13) . . ?
C23 C24 C31 119.69(13) . . ?
C23 C24 C25 118.85(13) . . ?
C18 C13 C12 119.17(14) . . ?
C18 C13 C14 118.84(14) . . ?
C14 C13 C12 121.97(14) . . ?
C20 C19 C18 122.61(13) . . ?
C6 C19 C20 119.46(13) . . ?
C6 C19 C18 117.67(14) . . ?
N4 C5 C22 119.77(14) . . ?
N4 C5 C6 120.05(14) . . ?
C22 C5 C6 119.83(13) . . ?
C21 C23 H23 119.1 . . ?
C24 C23 C21 121.89(13) . . ?
C24 C23 H23 119.1 . . ?
C13 C18 C19 120.08(14) . . ?
C13 C18 C17 118.72(14) . . ?
C17 C18 C19 120.59(14) . . ?
C35 C34 C33 117.87(14) . . ?
C35 C34 C37 121.12(14) . . ?
C33 C34 C37 121.01(14) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.17(15) . . ?
C16 C17 H17 119.4 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.83(14) . . ?
C28 C27 H27 120.1 . . ?
C31 C36 H36 119.6 . . ?
C35 C36 C31 120.89(14) . . ?
C35 C36 H36 119.6 . . ?
C31 C32 H32 119.6 . . ?
C33 C32 C31 120.71(14) . . ?
C33 C32 H32 119.6 . . ?
C7 C12 C13 119.07(14) . . ?
C11 C12 C13 121.48(14) . . ?
C11 C12 C7 119.43(15) . . ?
C29 C28 C27 120.40(13) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.90(15) . . ?
C15 C16 H16 120.1 . . ?
C34 C35 H35 119.4 . . ?
C36 C35 C34 121.27(14) . . ?
C36 C35 H35 119.4 . . ?
N1 C2 H2 119.1 . . ?
N1 C2 C3 121.77(14) . . ?
C3 C2 H2 119.1 . . ?
C12 C7 C6 119.49(14) . . ?
C8 C7 C6 122.01(14) . . ?
C8 C7 C12 118.17(14) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 C34 121.23(14) . . ?
C32 C33 H33 119.4 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.11(15) . . ?
C9 C8 H8 119.4 . . ?
N4 C3 C2 122.71(14) . . ?
N4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.32(15) . . ?
C10 C9 H9 119.8 . . ?
C12 C11 H11 119.4 . . ?
C10 C11 C12 121.22(16) . . ?
C10 C11 H11 119.4 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.17(15) . . ?
C15 C14 H14 119.4 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.05(14) . . ?
C14 C15 H15 120.0 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.65(15) . . ?
C11 C10 H10 120.2 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C22 C5 N4 0.2(2) . . . . ?
N1 C22 C5 C6 -173.01(13) . . . . ?
N1 C2 C3 N4 0.6(2) . . . . ?
C21 C22 C5 N4 -177.44(13) . . . . ?
C21 C22 C5 C6 9.3(2) . . . . ?
C21 C20 C19 C6 25.6(2) . . . . ?
C21 C20 C19 C18 -148.27(14) . . . . ?
C30 C29 C28 C27 -1.2(2) . . . . ?
C30 C25 C24 C31 175.15(13) . . . . ?
C30 C25 C24 C23 -6.7(2) . . . . ?
C30 C20 C19 C6 -150.63(14) . . . . ?
C30 C20 C19 C18 35.5(2) . . . . ?
C22 N1 C2 C3 0.4(2) . . . . ?
C22 C21 C20 C30 167.09(12) . . . . ?
C22 C21 C20 C19 -9.4(2) . . . . ?
C22 C21 C23 C24 -176.91(13) . . . . ?
C29 C30 C25 C26 -4.62(19) . . . . ?
C29 C30 C25 C24 171.80(13) . . . . ?
C29 C30 C20 C21 -161.86(13) . . . . ?
C29 C30 C20 C19 14.4(2) . . . . ?
C31 C24 C23 C21 -174.93(13) . . . . ?
C31 C36 C35 C34 0.5(2) . . . . ?
C31 C32 C33 C34 0.4(2) . . . . ?
C26 C25 C24 C31 -8.5(2) . . . . ?
C26 C25 C24 C23 169.61(13) . . . . ?
C26 C27 C28 C29 -3.2(2) . . . . ?
C25 C30 C29 C28 5.1(2) . . . . ?
C25 C30 C20 C21 13.02(19) . . . . ?
C25 C30 C20 C19 -170.67(13) . . . . ?
C25 C26 C27 C28 3.6(2) . . . . ?
C25 C24 C23 C21 6.9(2) . . . . ?
C20 C21 C22 N1 174.62(12) . . . . ?
C20 C21 C22 C5 -7.6(2) . . . . ?
C20 C21 C23 C24 3.3(2) . . . . ?
C20 C30 C29 C28 -179.90(13) . . . . ?
C20 C30 C25 C26 -179.72(13) . . . . ?
C20 C30 C25 C24 -3.3(2) . . . . ?
C20 C19 C18 C13 -168.34(13) . . . . ?
C20 C19 C18 C17 20.7(2) . . . . ?
C6 C19 C18 C13 17.7(2) . . . . ?
C6 C19 C18 C17 -153.28(14) . . . . ?
C6 C7 C8 C9 175.80(14) . . . . ?
C24 C31 C36 C35 177.15(13) . . . . ?
C24 C31 C32 C33 -177.57(13) . . . . ?
C13 C18 C17 C16 3.4(2) . . . . ?
C13 C12 C7 C6 4.7(2) . . . . ?
C13 C12 C7 C8 178.26(13) . . . . ?
C13 C12 C11 C10 179.75(14) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C19 C6 C5 N4 -166.81(13) . . . . ?
C19 C6 C5 C22 6.4(2) . . . . ?
C19 C6 C7 C12 16.0(2) . . . . ?
C19 C6 C7 C8 -157.21(14) . . . . ?
C19 C18 C17 C16 174.51(14) . . . . ?
C5 N4 C3 C2 -1.1(2) . . . . ?
C5 C6 C19 C20 -23.6(2) . . . . ?
C5 C6 C19 C18 150.58(13) . . . . ?
C5 C6 C7 C12 -161.32(14) . . . . ?
C5 C6 C7 C8 25.4(2) . . . . ?
C23 C21 C22 N1 -5.2(2) . . . . ?
C23 C21 C22 C5 172.58(13) . . . . ?
C23 C21 C20 C30 -13.1(2) . . . . ?
C23 C21 C20 C19 170.39(13) . . . . ?
C18 C13 C12 C7 -14.0(2) . . . . ?
C18 C13 C12 C11 167.45(14) . . . . ?
C18 C13 C14 C15 2.4(2) . . . . ?
C18 C17 C16 C15 -0.2(2) . . . . ?
C17 C16 C15 C14 -2.0(2) . . . . ?
C27 C26 C25 C30 0.4(2) . . . . ?
C27 C26 C25 C24 -176.01(13) . . . . ?
C36 C31 C24 C25 128.11(15) . . . . ?
C36 C31 C24 C23 -50.0(2) . . . . ?
C36 C31 C32 C33 -0.2(2) . . . . ?
C32 C31 C24 C25 -54.6(2) . . . . ?
C32 C31 C24 C23 127.25(15) . . . . ?
C32 C31 C36 C35 -0.2(2) . . . . ?
C12 C13 C18 C19 2.9(2) . . . . ?
C12 C13 C18 C17 173.98(13) . . . . ?
C12 C13 C14 C15 -175.99(15) . . . . ?
C12 C7 C8 C9 2.5(2) . . . . ?
C12 C11 C10 C9 1.6(2) . . . . ?
C35 C34 C33 C32 -0.1(2) . . . . ?
C2 N1 C22 C21 176.96(13) . . . . ?
C2 N1 C22 C5 -0.8(2) . . . . ?
C7 C6 C19 C20 158.87(13) . . . . ?
C7 C6 C19 C18 -26.9(2) . . . . ?
C7 C6 C5 N4 10.6(2) . . . . ?
C7 C6 C5 C22 -176.20(13) . . . . ?
C7 C12 C11 C10 1.2(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C33 C34 C35 C36 -0.3(2) . . . . ?
C8 C9 C10 C11 -2.3(2) . . . . ?
C3 N4 C5 C22 0.7(2) . . . . ?
C3 N4 C5 C6 173.91(14) . . . . ?
C11 C12 C7 C6 -176.64(13) . . . . ?
C11 C12 C7 C8 -3.1(2) . . . . ?
C14 C13 C18 C19 -175.60(13) . . . . ?
C14 C13 C18 C17 -4.5(2) . . . . ?
C14 C13 C12 C7 164.45(14) . . . . ?
C14 C13 C12 C11 -14.1(2) . . . . ?
C37 C34 C35 C36 179.24(14) . . . . ?
C37 C34 C33 C32 -179.68(14) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.083 0.181 0.346 31.2 1.8 ?
2 0.083 0.319 0.846 31.2 1.8 ?
3 -0.083 0.681 0.154 31.2 1.8 ?
4 -0.083 0.819 0.654 31.2 1.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d_27_100_autored
_database_code_depnum_ccdc_archive 'CCDC 2448318'
loop_
_audit_author_name
_audit_author_address
'Oleg P. Demidov'
;North Caucasus Federal University
Russia
;
_audit_update_record             
;
2025-05-02 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_audit_creation_date             2022-06-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
9-(p-Tolyl)naphtho[2,1-a]phenanthro[9,10-c]phenazine
_chemical_formula_moiety         'C39 H24 N2, 0.5[C7H8]'
_chemical_formula_sum            'C39 H24 N2'
_chemical_formula_weight         520.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C39 H24 N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9067(3)
_cell_length_b                   11.7479(4)
_cell_length_c                   14.9100(5)
_cell_angle_alpha                94.611(3)
_cell_angle_beta                 100.588(3)
_cell_angle_gamma                107.817(3)
_cell_volume                     1444.35(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9091
_cell_measurement_temperature    100.01(15)
_cell_measurement_theta_max      75.7240
_cell_measurement_theta_min      4.5930
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.818
_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_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -4 -5 0.0590
-2 0 -8 0.0787
6 -3 -3 0.1748
-1 -7 0 0.0615
-1 -7 3 0.0656
0 6 4 0.0269
0 -6 -4 0.0306
0 -4 9 0.0611
-5 4 -3 0.1448
0 3 -9 0.0556
1 -2 -9 0.0295
1 -8 0 0.0253

_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.058
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.1586 -4.4514 -5.3627 0.4287 0.9005 0.0734
-1.5996 -0.2027 -8.3228 0.8701 0.4738 0.1358
5.7273 -2.5465 -2.9656 -0.0048 -0.0080 -1.0000
-1.1952 -6.5251 0.2017 -0.1814 0.9726 0.1454
-1.0577 -6.6285 3.0744 -0.4717 0.8662 0.1648
-0.2252 6.0108 4.3726 -0.2302 -0.9614 0.1504
0.1243 -5.9802 -4.3297 0.2308 0.9639 -0.1331
0.1190 -3.5214 8.8901 -0.9881 0.1290 0.0843
-4.9018 4.3471 -2.8791 0.6041 -0.0806 0.7928
0.1316 3.3915 -8.9814 0.9835 -0.1283 -0.1277
0.6119 -1.9074 -8.9784 0.7974 0.5497 -0.2489
0.9559 -7.5029 0.0527 -0.2786 0.9358 -0.2160

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -49.00   1.00    1.57    --  -41.85-160.00-174.00   70
  2  ω   -115.00 -21.00   1.00    1.57    --  -41.85 160.00-143.00   94
  3  ω    -88.00   4.00   1.00    1.57    --  -41.85 118.00  64.00   92
  4  ω     18.00  94.00   1.00    1.57    --   41.85-118.00 -22.00   76
  5  ω     42.00 120.00   1.00    1.57    --   41.85-160.00-174.00   78
  6  ω     42.00 141.00   1.00    6.30    --  112.00-160.00-174.00   99
  7  ω     37.00 114.00   1.00    6.30    --  112.00-118.00 -22.00   77
  8  ω     71.00 164.00   1.00    6.30    --  112.00 160.00-143.00   93
  9  ω     98.00 178.00   1.00    6.30    --  112.00 118.00  64.00   80
 10  ω   -114.00 -14.00   1.00    1.57    --  -41.85 -57.00  60.00  100
 11  ω   -116.00 -17.00   1.00    1.57    --  -41.85 -38.00 150.00   99
 12  ω      1.00  83.00   1.00    1.57    --   41.85 -99.00-120.00   82
 13  ω      1.00  83.00   1.00    1.57    --   41.85 -99.00   0.00   82
 14  ω    -32.00  66.00   1.00    1.57    --   41.85 -38.00-120.00   98
 15  ω    100.00 178.00   1.00    6.30    --  112.00 111.00  30.00   78
 16  ω     83.00 178.00   1.00    6.30    --  112.00  61.00  30.00   95
 17  ω     39.00 138.00   1.00    6.30    --  112.00 -45.00  90.00   99
 18  ω     86.00 178.00   1.00    6.30    --  112.00  45.00 -60.00   92
 19  ω     96.00 134.00   1.00    6.30    --  112.00 135.00 123.00   38
 20  ω     61.00  86.00   1.00    6.30    --  112.00  15.00-180.00   25
 21  ω    127.00 170.00   1.00    6.30    --  112.00  15.00-180.00   43
 22  ω     45.00 101.00   1.00    6.30    --  112.00-111.00-180.00   56
 23  ω     76.00 125.00   1.00    6.30    --  112.00-135.00 146.00   49
 24  ω     45.00  73.00   1.00    6.30    --  112.00-111.00 -90.00   28
 25  ω     75.00 101.00   1.00    6.30    --  112.00-111.00 -90.00   26
 26  ω     67.00 104.00   1.00    6.30    --  112.00 -61.00 -30.00   37
 27  ω     77.00 122.00   1.00    6.30    --  112.00 -30.00-120.00   45
 28  ω     89.00 125.00   1.00    6.30    --  112.00-135.00-123.00   36
 29  ω     41.00  66.00   1.00    6.30    --  112.00   0.00  -0.00   25
 30  ω    107.00 133.00   1.00    6.30    --  112.00   0.00  -0.00   26
 31  ω     87.00 113.00   1.00    6.30    --  112.00-111.00 -30.00   26
 32  ω     87.00 113.00   1.00    6.30    --  112.00  47.00 -81.47   26
 33  ω     37.00  69.00   1.00    6.30    --  112.00-111.00-120.00   32
 34  ω    153.00 178.00   1.00    6.30    --  112.00  95.00 164.00   25
 35  ω    153.00 178.00   1.00    6.30    --  112.00 111.00 120.00   25
 36  ω     64.00  90.00   1.00    6.30    --  112.00 178.00   0.00   26
 37  ω    106.00 132.00   1.00    6.30    --  112.00 111.00 120.00   26
 38  ω    -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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5012
_reflns_number_total             5821
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.053
_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/[σ²(Fo²)+(0.0574P)²+0.4060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1152
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.13197(12) 0.38721(9) 0.48414(7) 0.0222(2) Uani 1 1 d . . . . .
N2 N -0.00905(12) 0.46841(9) 0.32750(7) 0.0204(2) Uani 1 1 d . . . . .
C12 C 0.20277(14) 0.49457(10) 0.46120(8) 0.0196(2) Uani 1 1 d . . . . .
C24 C 0.50613(14) 0.76497(10) 0.34858(8) 0.0196(2) Uani 1 1 d . . . . .
C8 C 0.22775(14) 0.64622(10) 0.35098(8) 0.0201(2) Uani 1 1 d . . . . .
C7 C 0.13214(14) 0.53664(10) 0.38108(8) 0.0193(2) Uani 1 1 d . . . . .
C10 C 0.43569(14) 0.68082(10) 0.49393(8) 0.0196(2) Uani 1 1 d . . . . .
C5 C -0.08104(14) 0.35843(10) 0.34973(8) 0.0204(2) Uani 1 1 d . . . . .
C11 C 0.35128(14) 0.57364(10) 0.52167(8) 0.0202(2) Uani 1 1 d . . . . .
C19 C 0.45307(14) 0.79644(10) 0.26166(8) 0.0210(2) Uani 1 1 d . . . . .
C6 C -0.01004(14) 0.31693(11) 0.42842(8) 0.0216(2) Uani 1 1 d . . . . .
C31 C 0.54077(14) 0.61965(11) 0.67097(8) 0.0215(2) Uani 1 1 d . . . . .
C13 C 0.16862(14) 0.69189(10) 0.26802(8) 0.0207(2) Uani 1 1 d . . . . .
C32 C 0.40838(14) 0.54307(11) 0.60853(8) 0.0212(2) Uani 1 1 d . . . . .
H32 H 0.352985 0.466889 0.624001 0.025 Uiso 1 1 calc R U . . .
C33 C 0.59579(15) 0.57839(11) 0.75910(8) 0.0224(2) Uani 1 1 d . . . . .
C25 C 0.55876(14) 0.77075(11) 0.56316(8) 0.0208(2) Uani 1 1 d . . . . .
C23 C 0.67223(14) 0.78157(10) 0.37913(8) 0.0215(2) Uani 1 1 d . . . . .
H23 H 0.708538 0.756409 0.435727 0.026 Uiso 1 1 calc R U . . .
C30 C 0.61384(14) 0.73965(11) 0.65084(8) 0.0220(2) Uani 1 1 d . . . . .
C4 C -0.22913(15) 0.28185(11) 0.29232(9) 0.0238(3) Uani 1 1 d . . . . .
H4 H -0.277783 0.308667 0.239624 0.029 Uiso 1 1 calc R U . . .
C9 C 0.38769(14) 0.70041(10) 0.39859(8) 0.0193(2) Uani 1 1 d . . . . .
C18 C 0.28081(15) 0.76873(10) 0.22499(8) 0.0217(2) Uani 1 1 d . . . . .
C26 C 0.61312(15) 0.89413(11) 0.55014(9) 0.0235(3) Uani 1 1 d . . . . .
H26 H 0.572154 0.916596 0.493289 0.028 Uiso 1 1 calc R U . . .
C3 C -0.30159(15) 0.16963(11) 0.31288(9) 0.0249(3) Uani 1 1 d . . . . .
H3 H -0.400498 0.118675 0.274157 0.030 Uiso 1 1 calc R U . . .
C20 C 0.56928(16) 0.85133(11) 0.21168(9) 0.0250(3) Uani 1 1 d . . . . .
H20 H 0.534990 0.875086 0.154101 0.030 Uiso 1 1 calc R U . . .
C29 C 0.72966(15) 0.83239(12) 0.71833(9) 0.0259(3) Uani 1 1 d . . . . .
H29 H 0.770264 0.812669 0.776398 0.031 Uiso 1 1 calc R U . . .
C14 C 0.00224(15) 0.66908(11) 0.23262(9) 0.0260(3) Uani 1 1 d . . . . .
H14 H -0.074635 0.620957 0.262489 0.031 Uiso 1 1 calc R U . . .
C34 C 0.48233(15) 0.51225(11) 0.80524(9) 0.0242(3) Uani 1 1 d . . . . .
H34 H 0.370701 0.499332 0.782381 0.029 Uiso 1 1 calc R U . . .
C17 C 0.22291(16) 0.81422(11) 0.14602(9) 0.0265(3) Uani 1 1 d . . . . .
H17 H 0.297983 0.864905 0.116472 0.032 Uiso 1 1 calc R U . . .
C35 C 0.53047(16) 0.46512(12) 0.88409(9) 0.0270(3) Uani 1 1 d . . . . .
H35 H 0.450997 0.420565 0.914100 0.032 Uiso 1 1 calc R U . . .
C2 C -0.23079(16) 0.12840(11) 0.39135(9) 0.0271(3) Uani 1 1 d . . . . .
H2 H -0.282750 0.050120 0.404718 0.032 Uiso 1 1 calc R U . . .
C21 C 0.73063(16) 0.87099(12) 0.24469(9) 0.0278(3) Uani 1 1 d . . . . .
H21 H 0.807280 0.909961 0.210868 0.033 Uiso 1 1 calc R U . . .
C22 C 0.78225(15) 0.83365(11) 0.32814(9) 0.0252(3) Uani 1 1 d . . . . .
H22 H 0.893540 0.844246 0.349723 0.030 Uiso 1 1 calc R U . . .
C38 C 0.75827(16) 0.59635(12) 0.79565(9) 0.0276(3) Uani 1 1 d . . . . .
H38 H 0.838175 0.641813 0.766315 0.033 Uiso 1 1 calc R U . . .
C16 C 0.06049(17) 0.78690(12) 0.11090(9) 0.0293(3) Uani 1 1 d . . . . .
H16 H 0.023810 0.816474 0.056508 0.035 Uiso 1 1 calc R U . . .
C27 C 0.72297(16) 0.98135(11) 0.61745(10) 0.0278(3) Uani 1 1 d . . . . .
H27 H 0.757533 1.063128 0.607027 0.033 Uiso 1 1 calc R U . . .
C1 C -0.08882(16) 0.19996(11) 0.44789(9) 0.0270(3) Uani 1 1 d . . . . .
H1 H -0.042589 0.171452 0.500393 0.032 Uiso 1 1 calc R U . . .
C37 C 0.80536(16) 0.54887(13) 0.87429(10) 0.0300(3) Uani 1 1 d . . . . .
H37 H 0.917004 0.562323 0.897587 0.036 Uiso 1 1 calc R U . . .
C28 C 0.78444(16) 0.94960(12) 0.70194(10) 0.0289(3) Uani 1 1 d . . . . .
H28 H 0.864010 1.009364 0.747766 0.035 Uiso 1 1 calc R U . . .
C36 C 0.69246(17) 0.48195(12) 0.91976(9) 0.0277(3) Uani 1 1 d . . . . .
C15 C -0.05063(16) 0.71548(12) 0.15538(10) 0.0287(3) Uani 1 1 d . . . . .
H15 H -0.163134 0.698722 0.132407 0.034 Uiso 1 1 calc R U . . .
C39 C 0.74312(19) 0.42659(13) 1.00306(10) 0.0360(3) Uani 1 1 d . . . . .
H39A H 0.647651 0.384834 1.026067 0.054 Uiso 1 1 calc R U . . .
H39B H 0.818898 0.490319 1.051371 0.054 Uiso 1 1 calc R U . . .
H39C H 0.795749 0.368628 0.985877 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.3293(15) . ?
N1 C6 1.3551(16) . ?
N2 C7 1.3316(15) . ?
N2 C5 1.3529(15) . ?
C12 C7 1.4409(16) . ?
C12 C11 1.4494(16) . ?
C24 C19 1.4137(16) . ?
C24 C23 1.4126(16) . ?
C24 C9 1.4610(16) . ?
C8 C7 1.4651(16) . ?
C8 C13 1.4613(16) . ?
C8 C9 1.3925(17) . ?
C10 C11 1.3929(16) . ?
C10 C25 1.4433(17) . ?
C10 C9 1.4650(16) . ?
C5 C6 1.4219(17) . ?
C5 C4 1.4203(17) . ?
C11 C32 1.4174(16) . ?
C19 C18 1.4548(17) . ?
C19 C20 1.4123(17) . ?
C6 C1 1.4192(17) . ?
C31 C32 1.3708(17) . ?
C31 C33 1.4877(17) . ?
C31 C30 1.4420(17) . ?
C13 C18 1.4149(17) . ?
C13 C14 1.4118(17) . ?
C32 H32 0.9500 . ?
C33 C34 1.3997(18) . ?
C33 C38 1.3931(17) . ?
C25 C30 1.4262(17) . ?
C25 C26 1.4225(16) . ?
C23 H23 0.9500 . ?
C23 C22 1.3763(17) . ?
C30 C29 1.4206(17) . ?
C4 H4 0.9500 . ?
C4 C3 1.3658(17) . ?
C18 C17 1.4087(17) . ?
C26 H26 0.9500 . ?
C26 C27 1.3691(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.4171(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3710(19) . ?
C29 H29 0.9500 . ?
C29 C28 1.3714(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3798(19) . ?
C34 H34 0.9500 . ?
C34 C35 1.3919(18) . ?
C17 H17 0.9500 . ?
C17 C16 1.3713(19) . ?
C35 H35 0.9500 . ?
C35 C36 1.3893(18) . ?
C2 H2 0.9500 . ?
C2 C1 1.3638(18) . ?
C21 H21 0.9500 . ?
C21 C22 1.3973(18) . ?
C22 H22 0.9500 . ?
C38 H38 0.9500 . ?
C38 C37 1.3890(19) . ?
C16 H16 0.9500 . ?
C16 C15 1.395(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.405(2) . ?
C1 H1 0.9500 . ?
C37 H37 0.9500 . ?
C37 C36 1.393(2) . ?
C28 H28 0.9500 . ?
C36 C39 1.5074(18) . ?
C15 H15 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C6 117.40(11) . . ?
C7 N2 C5 117.92(10) . . ?
N1 C12 C7 122.04(11) . . ?
N1 C12 C11 118.54(11) . . ?
C7 C12 C11 119.34(10) . . ?
C19 C24 C9 119.79(11) . . ?
C23 C24 C19 118.66(11) . . ?
C23 C24 C9 120.94(11) . . ?
C13 C8 C7 122.89(11) . . ?
C9 C8 C7 117.53(11) . . ?
C9 C8 C13 119.20(11) . . ?
N2 C7 C12 120.42(10) . . ?
N2 C7 C8 119.65(11) . . ?
C12 C7 C8 119.27(10) . . ?
C11 C10 C25 117.67(11) . . ?
C11 C10 C9 118.82(11) . . ?
C25 C10 C9 123.36(11) . . ?
N2 C5 C6 121.40(11) . . ?
N2 C5 C4 119.32(11) . . ?
C4 C5 C6 119.27(11) . . ?
C10 C11 C12 119.16(11) . . ?
C10 C11 C32 120.50(11) . . ?
C32 C11 C12 120.34(11) . . ?
C24 C19 C18 119.39(11) . . ?
C20 C19 C24 118.81(11) . . ?
C20 C19 C18 121.77(11) . . ?
N1 C6 C5 120.80(11) . . ?
N1 C6 C1 119.93(11) . . ?
C1 C6 C5 119.27(11) . . ?
C32 C31 C33 118.65(11) . . ?
C32 C31 C30 118.34(11) . . ?
C30 C31 C33 122.87(11) . . ?
C18 C13 C8 119.42(11) . . ?
C14 C13 C8 122.16(11) . . ?
C14 C13 C18 118.27(11) . . ?
C11 C32 H32 118.9 . . ?
C31 C32 C11 122.27(11) . . ?
C31 C32 H32 118.9 . . ?
C34 C33 C31 120.06(11) . . ?
C38 C33 C31 122.27(11) . . ?
C38 C33 C34 117.54(12) . . ?
C30 C25 C10 119.96(11) . . ?
C26 C25 C10 121.17(11) . . ?
C26 C25 C30 118.44(11) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 C24 121.01(11) . . ?
C22 C23 H23 119.5 . . ?
C25 C30 C31 119.52(11) . . ?
C29 C30 C31 122.22(11) . . ?
C29 C30 C25 118.02(11) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.98(12) . . ?
C3 C4 H4 120.0 . . ?
C24 C9 C10 121.74(10) . . ?
C8 C9 C24 118.56(11) . . ?
C8 C9 C10 119.39(10) . . ?
C13 C18 C19 119.40(11) . . ?
C17 C18 C19 121.46(11) . . ?
C17 C18 C13 119.12(11) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.69(12) . . ?
C27 C26 H26 119.2 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.70(12) . . ?
C2 C3 H3 119.7 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.24(12) . . ?
C21 C20 H20 119.4 . . ?
C30 C29 H29 119.1 . . ?
C28 C29 C30 121.79(12) . . ?
C28 C29 H29 119.1 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.14(12) . . ?
C15 C14 H14 119.4 . . ?
C33 C34 H34 119.5 . . ?
C35 C34 C33 121.04(12) . . ?
C35 C34 H34 119.5 . . ?
C18 C17 H17 119.3 . . ?
C16 C17 C18 121.40(12) . . ?
C16 C17 H17 119.3 . . ?
C34 C35 H35 119.4 . . ?
C36 C35 C34 121.29(13) . . ?
C36 C35 H35 119.4 . . ?
C3 C2 H2 119.7 . . ?
C1 C2 C3 120.67(12) . . ?
C1 C2 H2 119.7 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.95(11) . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.15(12) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C33 C38 H38 119.5 . . ?
C37 C38 C33 121.08(13) . . ?
C37 C38 H38 119.5 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.71(12) . . ?
C15 C16 H16 120.1 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.83(12) . . ?
C28 C27 H27 120.1 . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.10(12) . . ?
C2 C1 H1 119.9 . . ?
C38 C37 H37 119.3 . . ?
C38 C37 C36 121.45(12) . . ?
C36 C37 H37 119.3 . . ?
C29 C28 C27 120.05(12) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C35 C36 C37 117.58(12) . . ?
C35 C36 C39 120.97(13) . . ?
C37 C36 C39 121.43(13) . . ?
C14 C15 C16 120.25(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C12 C7 N2 0.66(17) . . . . ?
N1 C12 C7 C8 -170.02(10) . . . . ?
N1 C12 C11 C10 173.39(10) . . . . ?
N1 C12 C11 C32 -7.59(16) . . . . ?
N1 C6 C1 C2 -179.22(11) . . . . ?
N2 C5 C6 N1 0.54(17) . . . . ?
N2 C5 C6 C1 -178.87(11) . . . . ?
N2 C5 C4 C3 178.72(11) . . . . ?
C12 N1 C6 C5 -1.27(16) . . . . ?
C12 N1 C6 C1 178.14(11) . . . . ?
C12 C11 C32 C31 -174.57(11) . . . . ?
C24 C19 C18 C13 -11.49(16) . . . . ?
C24 C19 C18 C17 170.17(11) . . . . ?
C24 C19 C20 C21 1.96(18) . . . . ?
C24 C23 C22 C21 -0.08(18) . . . . ?
C8 C13 C18 C19 2.77(16) . . . . ?
C8 C13 C18 C17 -178.84(10) . . . . ?
C8 C13 C14 C15 178.49(11) . . . . ?
C7 N2 C5 C6 0.82(16) . . . . ?
C7 N2 C5 C4 -177.98(10) . . . . ?
C7 C12 C11 C10 -9.77(16) . . . . ?
C7 C12 C11 C32 169.25(10) . . . . ?
C7 C8 C13 C18 -157.53(11) . . . . ?
C7 C8 C13 C14 27.11(17) . . . . ?
C7 C8 C9 C24 149.16(10) . . . . ?
C7 C8 C9 C10 -24.56(15) . . . . ?
C10 C11 C32 C31 4.45(17) . . . . ?
C10 C25 C30 C31 -2.70(16) . . . . ?
C10 C25 C30 C29 -177.15(11) . . . . ?
C10 C25 C26 C27 176.20(11) . . . . ?
C5 N2 C7 C12 -1.38(16) . . . . ?
C5 N2 C7 C8 169.26(10) . . . . ?
C5 C6 C1 C2 0.19(18) . . . . ?
C5 C4 C3 C2 0.16(18) . . . . ?
C11 C12 C7 N2 -176.07(10) . . . . ?
C11 C12 C7 C8 13.26(16) . . . . ?
C11 C10 C25 C30 13.02(16) . . . . ?
C11 C10 C25 C26 -159.30(11) . . . . ?
C11 C10 C9 C24 -145.08(11) . . . . ?
C11 C10 C9 C8 28.44(16) . . . . ?
C19 C24 C23 C22 3.66(17) . . . . ?
C19 C24 C9 C8 15.15(16) . . . . ?
C19 C24 C9 C10 -171.28(10) . . . . ?
C19 C18 C17 C16 179.24(12) . . . . ?
C19 C20 C21 C22 1.66(19) . . . . ?
C6 N1 C12 C7 0.70(16) . . . . ?
C6 N1 C12 C11 177.45(10) . . . . ?
C6 C5 C4 C3 -0.11(17) . . . . ?
C31 C33 C34 C35 175.22(11) . . . . ?
C31 C33 C38 C37 -175.03(11) . . . . ?
C31 C30 C29 C28 -172.25(12) . . . . ?
C13 C8 C7 N2 6.16(17) . . . . ?
C13 C8 C7 C12 176.91(10) . . . . ?
C13 C8 C9 C24 -23.96(16) . . . . ?
C13 C8 C9 C10 162.31(10) . . . . ?
C13 C18 C17 C16 0.88(18) . . . . ?
C13 C14 C15 C16 -0.36(19) . . . . ?
C32 C31 C33 C34 -39.76(16) . . . . ?
C32 C31 C33 C38 136.01(12) . . . . ?
C32 C31 C30 C25 -6.92(16) . . . . ?
C32 C31 C30 C29 167.29(11) . . . . ?
C33 C31 C32 C11 -177.83(10) . . . . ?
C33 C31 C30 C25 177.34(10) . . . . ?
C33 C31 C30 C29 -8.45(18) . . . . ?
C33 C34 C35 C36 -0.01(19) . . . . ?
C33 C38 C37 C36 -0.2(2) . . . . ?
C25 C10 C11 C12 165.08(10) . . . . ?
C25 C10 C11 C32 -13.94(16) . . . . ?
C25 C10 C9 C24 39.67(16) . . . . ?
C25 C10 C9 C8 -146.81(11) . . . . ?
C25 C30 C29 C28 2.04(18) . . . . ?
C25 C26 C27 C28 -0.12(19) . . . . ?
C23 C24 C19 C18 173.84(10) . . . . ?
C23 C24 C19 C20 -4.53(16) . . . . ?
C23 C24 C9 C8 -155.78(11) . . . . ?
C23 C24 C9 C10 17.79(16) . . . . ?
C30 C31 C32 C11 6.25(17) . . . . ?
C30 C31 C33 C34 135.97(12) . . . . ?
C30 C31 C33 C38 -48.26(17) . . . . ?
C30 C25 C26 C27 3.77(17) . . . . ?
C30 C29 C28 C27 1.62(19) . . . . ?
C4 C5 C6 N1 179.35(11) . . . . ?
C4 C5 C6 C1 -0.06(17) . . . . ?
C4 C3 C2 C1 -0.03(19) . . . . ?
C9 C24 C19 C18 2.70(16) . . . . ?
C9 C24 C19 C20 -175.67(10) . . . . ?
C9 C24 C23 C22 174.69(11) . . . . ?
C9 C8 C7 N2 -166.70(11) . . . . ?
C9 C8 C7 C12 4.05(16) . . . . ?
C9 C8 C13 C18 15.21(16) . . . . ?
C9 C8 C13 C14 -160.15(11) . . . . ?
C9 C10 C11 C12 -10.44(16) . . . . ?
C9 C10 C11 C32 170.54(10) . . . . ?
C9 C10 C25 C30 -171.68(10) . . . . ?
C9 C10 C25 C26 16.00(17) . . . . ?
C18 C19 C20 C21 -176.38(12) . . . . ?
C18 C13 C14 C15 3.09(18) . . . . ?
C18 C17 C16 C15 1.9(2) . . . . ?
C26 C25 C30 C31 169.83(11) . . . . ?
C26 C25 C30 C29 -4.62(16) . . . . ?
C26 C27 C28 C29 -2.62(19) . . . . ?
C3 C2 C1 C6 -0.15(19) . . . . ?
C20 C19 C18 C13 166.84(11) . . . . ?
C20 C19 C18 C17 -11.51(18) . . . . ?
C20 C21 C22 C23 -2.62(19) . . . . ?
C14 C13 C18 C19 178.30(10) . . . . ?
C14 C13 C18 C17 -3.31(17) . . . . ?
C34 C33 C38 C37 0.84(18) . . . . ?
C34 C35 C36 C37 0.66(19) . . . . ?
C34 C35 C36 C39 -177.64(12) . . . . ?
C17 C16 C15 C14 -2.2(2) . . . . ?
C38 C33 C34 C35 -0.74(18) . . . . ?
C38 C37 C36 C35 -0.56(19) . . . . ?
C38 C37 C36 C39 177.73(12) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.779 0.000 0.000 258.1 53.1 '1 toluene'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
