# 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_anna_zam277_2_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2470464'
loop_
_audit_author_name
_audit_author_address
'Nicolai Aksenov'
;North Caucasus Federal University
Russia
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_audit_creation_date             2025-07-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N3 O2'
_chemical_formula_sum            'C26 H21 N3 O2'
_chemical_formula_weight         407.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C26H21N3O2
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'
O O 0.0492 0.0322 '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                   10.0806(3)
_cell_length_b                   13.6026(5)
_cell_length_c                   16.0009(6)
_cell_angle_alpha                68.051(4)
_cell_angle_beta                 80.115(3)
_cell_angle_gamma                89.958(3)
_cell_volume                     2000.00(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12001
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7520
_cell_measurement_theta_min      5.4890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856.000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -3 -10 0.1207
5 6 4 0.1205
-4 -5 2 0.1501
3 8 3 0.1361
-2 -8 -7 0.1421
-1 -4 -10 0.1267
-5 -2 -8 0.1118
6 2 3 0.1263
6 4 0 0.1295
-6 -2 -3 0.1304
1 -4 6 0.1533
-7 -1 -1 0.1318
5 -5 0 0.1228
-5 5 0 0.1110
5 -6 -3 0.1275
-3 7 2 0.1368
-5 5 3 0.1250
-4 5 6 0.1283
4 -6 -6 0.1334
0 2 10 0.1045
2 9 5 0.1588
1 -1 -9 0.0878

_exptl_crystal_preparation       'Prepared by cycloaddition reaction'
_exptl_crystal_recrystallization_method 
'Crystallized by slow evaporation of saturated solution in EtOAc.'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
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
-2.7584 -2.5055 -10.0068 0.5635 -0.8178 0.1169
5.0050 5.6925 3.9273 -0.3432 0.5016 0.7941
-3.8385 -4.8524 2.4588 -0.0010 -0.0093 -1.0000
3.1849 7.6850 3.4996 0.0132 0.5937 0.8046
-2.0005 -7.9729 -6.9139 -0.0210 -0.8733 -0.4868
-0.8233 -3.7657 -10.3598 0.2766 -0.9321 0.2337
-4.9307 -1.6103 -8.0306 0.7838 -0.5998 -0.1610
6.3186 2.2988 2.8382 -0.6733 0.2361 0.7007
5.5210 3.8243 0.1732 -0.3683 0.1279 0.9209
-6.3409 -2.1607 -3.0340 0.6934 -0.2432 -0.6783
1.0378 -4.3493 6.4714 -0.6834 0.2429 -0.6885
-6.5036 -0.5044 -1.0939 0.7413 -0.0172 -0.6710
5.4493 -4.7909 0.3872 -0.9503 -0.2828 0.1303
-5.3865 4.8967 -0.4389 0.9526 0.2834 -0.1108
4.7904 -5.8334 -2.8126 -0.8114 -0.5593 0.1700
-3.4615 7.4793 1.9237 0.8110 0.5581 0.1756
-5.1055 5.1351 3.0336 0.7903 0.5450 -0.2801
-4.3796 4.5290 5.8838 0.5474 0.7133 -0.4376
3.6872 -6.2983 -5.7039 -0.5968 -0.7786 0.1941
-0.2102 2.2420 10.0805 -0.2517 0.8501 -0.4625
1.5007 8.5378 5.2295 0.1864 0.7850 0.5907
1.0735 -0.8508 -9.3765 0.2189 -0.7414 0.6344

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9943
_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         76.413
_diffrn_reflns_theta_min         3.030
_diffrn_ambient_temperature      293(2)
_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 0.5684
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  33.00   1.00    1.02    --  -40.44  71.00-174.00  105
  2  ω   -114.00  -9.00   1.00    1.02    --  -40.44 -71.00  54.00  105
  3  ω      9.00 114.00   1.00    1.02    --   40.44  71.00-174.00  105
  4  ω    -33.00  72.00   1.00    1.02    --   40.44 -71.00  54.00  105
  5  ω     81.00 178.00   1.00    4.08    --  112.00  71.00-174.00   97
  6  ω     38.00 143.00   1.00    4.08    --  112.00 -71.00  54.00  105
  7  ω   -120.00   1.00   1.00    1.02    --  -40.44 -19.00 -90.00  121
  8  ω      6.00  80.00   1.00    1.02    --   40.44 -99.00-120.00   74
  9  ω     16.00 115.00   1.00    1.02    --   40.44  38.00 -30.00   99
 10  ω      5.00  31.00   1.00    1.02    --   40.44  86.00  39.44   26
 11  ω      7.00  42.00   1.00    1.02    --   40.44  79.00 -13.67   35
 12  ω     39.00 109.00   1.00    4.08    --  112.00-111.00-180.00   70
 13  ω    103.00 178.00   1.00    4.08    --  112.00  77.00 150.00   75
 14  ω     39.00 109.00   1.00    4.08    --  112.00-111.00 -30.00   70
 15  ω     30.00 106.00   1.00    4.08    --  112.00 -95.00  60.00   76
 16  ω     39.00 109.00   1.00    4.08    --  112.00-111.00 150.00   70
 17  ω     86.00 178.00   1.00    4.08    --  112.00  45.00 -90.00   92
 18  ω     39.00 138.00   1.00    4.08    --  112.00 -45.00-180.00   99
 19  ω     39.00 138.00   1.00    4.08    --  112.00 -45.00-180.00   99
 20  ω     61.00 146.00   1.00    4.08    --  112.00 178.00  30.00   85
 21  ω    104.00 178.00   1.00    4.08    --  112.00 111.00 150.00   74
 22  ω     34.00 146.00   1.00    4.08    --  112.00 -81.00 143.83  112
 23  ω     61.00 146.00   1.00    4.08    --  112.00 178.00 -60.00   85
 24  ω    103.00 178.00   1.00    4.08    --  112.00  77.00 120.00   75
 25  ω     39.00 109.00   1.00    4.08    --  112.00-111.00   0.00   70
 26  ω    103.00 178.00   1.00    4.08    --  112.00  77.00   0.00   75
 27  ω     86.00 178.00   1.00    4.08    --  112.00  45.00 -60.00   92
 28  ω     39.00 109.00   1.00    4.08    --  112.00-111.00 120.00   70
 29  ω    102.00 129.00   1.00    4.08    --  112.00 -45.00 120.00   27
 30  ω     40.00  65.00   1.00    4.08    --  112.00 -95.00  30.00   25
 31  ω     70.00 105.00   1.00    4.08    --  112.00 -95.00  30.00   35
 32  ω     77.00 112.00   1.00    4.08    --  112.00 -45.00  30.00   35
 33  ω     41.00 123.00   1.00    4.08    --  112.00 -61.00-180.00   82
 34  ω     62.00  95.00   1.00    4.08    --  112.00 178.00  30.00   33
 35  ω    105.00 166.00   1.00    4.08    --  112.00 111.00-150.00   61
 36  ω    125.00 174.00   1.00    4.08    --  112.00  45.00-150.00   49
 37  ω    102.00 138.00   1.00    4.08    --  112.00 -45.00 -30.00   36
 38  ω     80.00 109.00   1.00    4.08    --  112.00-111.00-120.00   29
 39  ω    107.00 137.00   1.00    4.08    --  112.00 -45.00-150.00   30
 40  ω    105.00 142.00   1.00    4.08    --  112.00 111.00  60.00   37
 41  ω     49.00  76.00   1.00    4.08    --  112.00 -45.00 -30.00   27
 42  ω     41.00  81.00   1.00    4.08    --  112.00 -61.00 -90.00   40
 43  ω    104.00 160.00   1.00    4.08    --  112.00  77.00-150.00   56
 44  ω     33.00  60.00   1.00    4.08    --  112.00 -15.00  60.00   27
 45  ω    116.00 162.00   1.00    4.08    --  112.00 -15.00  60.00   46
 46  ω     77.00 106.00   1.00    4.08    --  112.00-111.00-150.00   29
 47  ω     81.00 108.00   1.00    4.08    --  112.00-111.00 -90.00   27
 48  ω     55.00 109.00   1.00    4.08    --  112.00-111.00  90.00   54
 49  ω    108.00 135.00   1.00    4.08    --  112.00  77.00-120.00   27
 50  ω     41.00  68.00   1.00    4.08    --  112.00 -95.00 120.00   27
 51  ω     87.00 177.00   1.00    4.08    --  112.00  45.00 150.00   90
 52  ω     83.00 158.00   1.00    4.08    --  112.00  61.00-180.00   75
 53  ω     39.00 109.00   1.00    4.08    --  112.00-111.00  30.00   70
 54  ω    110.00 137.00   1.00    4.08    --  112.00 -77.00 -60.00   27
 55  ω     97.00 124.00   1.00    4.08    --  112.00 -81.00-125.61   27
 56  ω    102.00 129.00   1.00    4.08    --  112.00 -82.00 176.56   27
 57  ω    131.00 167.00   1.00    4.08    --  112.00 111.00  90.00   36
;
_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      -0.1120907000
_diffrn_orient_matrix_UB_12      0.0674392000
_diffrn_orient_matrix_UB_13      -0.0423017000
_diffrn_orient_matrix_UB_21      -0.0134840000
_diffrn_orient_matrix_UB_22      0.0495916000
_diffrn_orient_matrix_UB_23      0.0730229000
_diffrn_orient_matrix_UB_31      0.1069335000
_diffrn_orient_matrix_UB_32      0.0893002000
_diffrn_orient_matrix_UB_33      -0.0635163000
_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                7540
_reflns_number_total             9943
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.90 64-bit (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         9943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      0.939
_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)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1163
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5540(11)
 0.4460(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C16(H16), C42(H42)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C17(H17A,H17B), C45(H45A,H45B), C18(H18A,H18B), C44(H44A,
 H44B), C43(H43A,H43B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C47(H47), C14(H14), C5(H5), C21(H21), C11(H11), C51(H51),
 C4(H4), C48(H48), C13(H13), C37(H37), C3(H3A), C41(H41), C49(H49), C38(H38),
 C12(H12), C39(H39), C29(H29), C24(H24), C31(H31), C50(H50), C30(H30), C32(H32),
  C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.20767(17) 0.43780(12) 0.39711(9) 0.0391(3) Uani 1 1 d . . . . .
O4 O 0.65108(17) 0.06320(12) 0.60500(9) 0.0414(3) Uani 1 1 d . . . . .
O1 O -0.1389(2) 0.42249(14) 0.41845(11) 0.0528(4) Uani 1 1 d . . . . .
N1 N 0.01913(16) 0.40945(12) 0.23816(10) 0.0295(3) Uani 1 1 d . . . . .
O3 O 0.3150(2) 0.08069(13) 0.58852(11) 0.0530(4) Uani 1 1 d . . . . .
N2 N -0.10797(18) 0.55735(13) 0.22222(10) 0.0334(3) Uani 1 1 d . . . . .
N6 N 0.3735(2) -0.07888(16) 0.58022(12) 0.0421(4) Uani 1 1 d . . . . .
N4 N 0.38146(17) 0.07737(13) 0.77447(11) 0.0335(3) Uani 1 1 d . . . . .
N3 N -0.0816(2) 0.58680(17) 0.41614(12) 0.0436(4) Uani 1 1 d . . . . .
N5 N 0.24429(19) -0.06619(14) 0.78151(11) 0.0364(3) Uani 1 1 d . . . . .
C1 C 0.0313(2) 0.30543(14) 0.29670(12) 0.0324(4) Uani 1 1 d . . . . .
C6 C 0.1202(2) 0.29977(16) 0.35627(12) 0.0347(4) Uani 1 1 d . . . . .
C7 C 0.15215(19) 0.40783(15) 0.34806(11) 0.0302(3) Uani 1 1 d . . . . .
C46 C 0.5608(2) -0.05013(14) 0.81373(12) 0.0313(4) Uani 1 1 d . . . . .
C36 C 0.4161(2) -0.17425(17) 0.63746(13) 0.0383(4) Uani 1 1 d . . . . .
C15 C -0.00807(19) 0.56015(14) 0.27883(11) 0.0296(3) Uani 1 1 d . . . . .
C8 C 0.09917(18) 0.48175(13) 0.26218(10) 0.0263(3) Uani 1 1 d . . . . .
C20 C 0.0380(2) 0.66982(15) 0.27016(12) 0.0333(4) Uani 1 1 d . . . . .
C9 C 0.22346(18) 0.53410(14) 0.18812(11) 0.0279(3) Uani 1 1 d . . . . .
C40 C 0.4175(2) -0.17135(15) 0.72357(12) 0.0348(4) Uani 1 1 d . . . . .
C10 C 0.2422(2) 0.52057(17) 0.10474(12) 0.0359(4) Uani 1 1 d . . . . .
H10 H 0.178128 0.479896 0.093860 0.043 Uiso 1 1 calc R U . . .
C2 C -0.0341(2) 0.21314(17) 0.29996(16) 0.0431(5) Uani 1 1 d . . . . .
H2 H -0.098172 0.216087 0.263746 0.052 Uiso 1 1 calc R U . . .
C28 C 0.5406(2) 0.19418(16) 0.65559(13) 0.0363(4) Uani 1 1 d . . . . .
C16 C -0.1142(2) 0.44951(16) 0.22199(13) 0.0351(4) Uani 1 1 d . . . . .
H16 H -0.186045 0.404490 0.270941 0.042 Uiso 1 1 calc R U . . .
C35 C 0.3501(2) -0.00885(16) 0.62180(12) 0.0365(4) Uani 1 1 d . . . . .
C47 C 0.5294(2) -0.05529(16) 0.90345(13) 0.0382(4) Uani 1 1 d . . . . .
H47 H 0.454618 -0.022500 0.920883 0.046 Uiso 1 1 calc R U . . .
C14 C 0.3225(2) 0.59319(16) 0.20411(13) 0.0348(4) Uani 1 1 d . . . . .
H14 H 0.312909 0.601554 0.259882 0.042 Uiso 1 1 calc R U . . .
C26 C 0.4742(2) 0.00873(14) 0.74330(11) 0.0298(3) Uani 1 1 d . . . . .
C27 C 0.5703(2) 0.08826(15) 0.65828(12) 0.0333(4) Uani 1 1 d . . . . .
C52 C -0.0852(2) 0.51145(16) 0.37994(12) 0.0362(4) Uani 1 1 d . . . . .
C34 C 0.3742(2) -0.06476(14) 0.72240(11) 0.0308(4) Uani 1 1 d . . . . .
C25 C -0.0082(2) 0.68018(18) 0.35369(14) 0.0403(4) Uani 1 1 d . . . . .
C5 C 0.1548(2) 0.20269(17) 0.41495(14) 0.0433(5) Uani 1 1 d . . . . .
H5 H 0.216019 0.199484 0.453096 0.052 Uiso 1 1 calc R U . . .
C21 C 0.1127(2) 0.75464(16) 0.19882(14) 0.0414(4) Uani 1 1 d . . . . .
H21 H 0.143585 0.749969 0.142307 0.050 Uiso 1 1 calc R U . . .
C19 C -0.0844(3) 0.63262(17) 0.12582(14) 0.0412(5) Uani 1 1 d . . . . .
H19A H 0.010126 0.639720 0.097652 0.049 Uiso 1 1 calc R U . . .
H19B H -0.114270 0.702098 0.120724 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3551(2) 0.5670(2) 0.03809(14) 0.0458(5) Uani 1 1 d . . . . .
H11 H 0.366538 0.557385 -0.017196 0.055 Uiso 1 1 calc R U . . .
C51 C 0.6731(2) -0.10001(17) 0.78979(14) 0.0393(4) Uani 1 1 d . . . . .
H51 H 0.695391 -0.098327 0.730387 0.047 Uiso 1 1 calc R U . . .
C33 C 0.4218(2) 0.18362(16) 0.71856(14) 0.0364(4) Uani 1 1 d . . . . .
C4 C 0.0956(3) 0.11107(18) 0.41498(18) 0.0512(6) Uani 1 1 d . . . . .
H4 H 0.119238 0.045108 0.452143 0.061 Uiso 1 1 calc R U . . .
C48 C 0.6085(3) -0.10897(18) 0.96753(15) 0.0476(5) Uani 1 1 d . . . . .
H48 H 0.585565 -0.112729 1.027526 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4357(2) 0.63960(18) 0.13629(15) 0.0429(5) Uani 1 1 d . . . . .
H13 H 0.501422 0.678922 0.147131 0.052 Uiso 1 1 calc R U . . .
C37 C 0.4538(3) -0.2613(2) 0.61657(17) 0.0518(6) Uani 1 1 d . . . . .
H37 H 0.452580 -0.261671 0.558710 0.062 Uiso 1 1 calc R U . . .
C17 C -0.1442(3) 0.46254(19) 0.12759(16) 0.0478(5) Uani 1 1 d . . . . .
H17A H -0.067737 0.444705 0.091296 0.057 Uiso 1 1 calc R U . . .
H17B H -0.222774 0.417451 0.133940 0.057 Uiso 1 1 calc R U . . .
C3 C 0.0006(3) 0.11688(17) 0.35960(18) 0.0514(6) Uani 1 1 d . . . . .
H3A H -0.040820 0.054202 0.362748 0.062 Uiso 1 1 calc R U . . .
C41 C 0.4570(3) -0.25866(16) 0.79045(14) 0.0417(4) Uani 1 1 d . . . . .
H41 H 0.457836 -0.258537 0.848432 0.050 Uiso 1 1 calc R U . . .
C49 C 0.7206(3) -0.15651(19) 0.94220(16) 0.0494(5) Uani 1 1 d . . . . .
H49 H 0.774540 -0.191154 0.984604 0.059 Uiso 1 1 calc R U . . .
C38 C 0.4937(3) -0.3482(2) 0.68450(19) 0.0539(6) Uani 1 1 d . . . . .
H38 H 0.519419 -0.407751 0.672086 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4512(2) 0.6279(2) 0.05335(14) 0.0482(5) Uani 1 1 d . . . . .
H12 H 0.525909 0.660635 0.007866 0.058 Uiso 1 1 calc R U . . .
C39 C 0.4956(3) -0.34718(18) 0.77019(18) 0.0501(5) Uani 1 1 d . . . . .
H39 H 0.522816 -0.405917 0.814875 0.060 Uiso 1 1 calc R U . . .
C29 C 0.6020(3) 0.29365(17) 0.59688(15) 0.0460(5) Uani 1 1 d . . . . .
H29 H 0.682839 0.300004 0.556601 0.055 Uiso 1 1 calc R U . . .
C45 C 0.2151(3) -0.14834(19) 0.87512(14) 0.0457(5) Uani 1 1 d . . . . .
H45A H 0.294260 -0.159784 0.903680 0.055 Uiso 1 1 calc R U . . .
H45B H 0.180907 -0.215194 0.875566 0.055 Uiso 1 1 calc R U . . .
C42 C 0.2383(2) 0.03860(17) 0.78859(14) 0.0387(4) Uani 1 1 d . . . . .
H42 H 0.193492 0.087125 0.741079 0.046 Uiso 1 1 calc R U . . .
C24 C 0.0202(3) 0.7716(2) 0.3680(2) 0.0591(7) Uani 1 1 d . . . . .
H24 H -0.010817 0.776886 0.424239 0.071 Uiso 1 1 calc R U . . .
C31 C 0.4160(3) 0.37140(19) 0.6604(2) 0.0571(6) Uani 1 1 d . . . . .
H31 H 0.373342 0.432059 0.660376 0.069 Uiso 1 1 calc R U . . .
C50 C 0.7523(3) -0.1524(2) 0.85396(17) 0.0494(5) Uani 1 1 d . . . . .
H50 H 0.827579 -0.185005 0.836920 0.059 Uiso 1 1 calc R U . . .
C30 C 0.5382(3) 0.38286(18) 0.6007(2) 0.0550(6) Uani 1 1 d . . . . .
H30 H 0.577215 0.450369 0.563255 0.066 Uiso 1 1 calc R U . . .
C18 C -0.1703(3) 0.5796(2) 0.08341(17) 0.0535(6) Uani 1 1 d . . . . .
H18A H -0.142181 0.606046 0.017315 0.064 Uiso 1 1 calc R U . . .
H18B H -0.265031 0.590969 0.098057 0.064 Uiso 1 1 calc R U . . .
C44 C 0.1070(3) -0.0973(3) 0.9215(2) 0.0647(7) Uani 1 1 d . . . . .
H44A H 0.019976 -0.105960 0.906132 0.078 Uiso 1 1 calc R U . . .
H44B H 0.099181 -0.128322 0.987652 0.078 Uiso 1 1 calc R U . . .
C32 C 0.3558(3) 0.27302(18) 0.71990(18) 0.0483(5) Uani 1 1 d . . . . .
H32 H 0.274219 0.266898 0.759346 0.058 Uiso 1 1 calc R U . . .
C43 C 0.1557(3) 0.0180(2) 0.88437(17) 0.0531(6) Uani 1 1 d . . . . .
H43A H 0.211409 0.031820 0.923078 0.064 Uiso 1 1 calc R U . . .
H43B H 0.080127 0.062778 0.880357 0.064 Uiso 1 1 calc R U . . .
C22 C 0.1408(3) 0.84681(18) 0.21286(19) 0.0540(6) Uani 1 1 d . . . . .
H22 H 0.190653 0.904022 0.165235 0.065 Uiso 1 1 calc R U . . .
C23 C 0.0956(3) 0.8545(2) 0.2965(2) 0.0616(7) Uani 1 1 d . . . . .
H23 H 0.116440 0.916466 0.304762 0.074 Uiso 1 1 calc R U . . .
H6 H 0.369(3) -0.063(2) 0.523(2) 0.053(8) Uiso 1 1 d . . . . .
H3 H -0.127(4) 0.579(3) 0.473(2) 0.075(11) Uiso 1 1 d . . . . .


_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
O2 C7 1.219(2) . ?
O4 C27 1.218(3) . ?
O1 C52 1.211(3) . ?
N1 C1 1.394(2) . ?
N1 C8 1.468(2) . ?
N1 C16 1.477(3) . ?
O3 C35 1.213(3) . ?
N2 C15 1.475(2) . ?
N2 C16 1.470(3) . ?
N2 C19 1.476(2) . ?
N6 C36 1.397(3) . ?
N6 C35 1.351(3) . ?
N6 H6 0.86(3) . ?
N4 C26 1.477(2) . ?
N4 C33 1.401(3) . ?
N4 C42 1.487(3) . ?
N3 C52 1.356(3) . ?
N3 C25 1.399(3) . ?
N3 H3 0.92(4) . ?
N5 C34 1.474(3) . ?
N5 C45 1.475(3) . ?
N5 C42 1.472(3) . ?
C1 C6 1.399(3) . ?
C1 C2 1.398(3) . ?
C6 C7 1.457(3) . ?
C6 C5 1.390(3) . ?
C7 C8 1.550(2) . ?
C46 C47 1.391(3) . ?
C46 C26 1.528(2) . ?
C46 C51 1.390(3) . ?
C36 C40 1.395(3) . ?
C36 C37 1.382(3) . ?
C15 C8 1.578(2) . ?
C15 C20 1.511(3) . ?
C15 C52 1.558(2) . ?
C8 C9 1.530(2) . ?
C20 C25 1.396(3) . ?
C20 C21 1.387(3) . ?
C9 C10 1.395(2) . ?
C9 C14 1.397(3) . ?
C40 C34 1.508(3) . ?
C40 C41 1.382(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C28 C27 1.458(3) . ?
C28 C33 1.396(3) . ?
C28 C29 1.396(3) . ?
C16 H16 0.9800 . ?
C16 C17 1.537(3) . ?
C35 C34 1.565(2) . ?
C47 H47 0.9300 . ?
C47 C48 1.393(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.393(3) . ?
C26 C27 1.552(3) . ?
C26 C34 1.579(3) . ?
C25 C24 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.391(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.516(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C51 H51 0.9300 . ?
C51 C50 1.391(3) . ?
C33 C32 1.391(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.396(4) . ?
C48 H48 0.9300 . ?
C48 C49 1.378(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.378(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.389(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.526(3) . ?
C3 H3A 0.9300 . ?
C41 H41 0.9300 . ?
C41 C39 1.398(3) . ?
C49 H49 0.9300 . ?
C49 C50 1.373(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.380(4) . ?
C12 H12 0.9300 . ?
C39 H39 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.389(4) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C45 C44 1.526(4) . ?
C42 H42 0.9800 . ?
C42 C43 1.537(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.377(4) . ?
C31 H31 0.9300 . ?
C31 C30 1.393(5) . ?
C31 C32 1.384(4) . ?
C50 H50 0.9300 . ?
C30 H30 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44 C43 1.503(4) . ?
C32 H32 0.9300 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C22 H22 0.9300 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9300 . ?

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
C1 N1 C8 108.66(14) . . ?
C1 N1 C16 121.31(16) . . ?
C8 N1 C16 111.36(15) . . ?
C15 N2 C19 118.05(17) . . ?
C16 N2 C15 106.92(15) . . ?
C16 N2 C19 107.45(15) . . ?
C36 N6 H6 125(2) . . ?
C35 N6 C36 112.16(16) . . ?
C35 N6 H6 123(2) . . ?
C26 N4 C42 111.06(15) . . ?
C33 N4 C26 108.54(15) . . ?
C33 N4 C42 119.21(17) . . ?
C52 N3 C25 111.99(16) . . ?
C52 N3 H3 124(2) . . ?
C25 N3 H3 124(2) . . ?
C34 N5 C45 118.39(18) . . ?
C42 N5 C34 106.73(16) . . ?
C42 N5 C45 108.15(16) . . ?
N1 C1 C6 112.42(17) . . ?
N1 C1 C2 127.02(19) . . ?
C2 C1 C6 120.56(19) . . ?
C1 C6 C7 107.45(17) . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 C7 130.9(2) . . ?
O2 C7 C6 129.06(17) . . ?
O2 C7 C8 125.06(17) . . ?
C6 C7 C8 105.88(15) . . ?
C47 C46 C26 120.93(18) . . ?
C51 C46 C47 118.23(18) . . ?
C51 C46 C26 120.84(16) . . ?
C40 C36 N6 109.97(18) . . ?
C37 C36 N6 127.8(2) . . ?
C37 C36 C40 122.2(2) . . ?
N2 C15 C8 104.00(14) . . ?
N2 C15 C20 115.25(15) . . ?
N2 C15 C52 105.50(15) . . ?
C20 C15 C8 119.99(16) . . ?
C20 C15 C52 102.03(15) . . ?
C52 C15 C8 109.19(14) . . ?
N1 C8 C7 104.14(14) . . ?
N1 C8 C15 102.35(14) . . ?
N1 C8 C9 112.02(13) . . ?
C7 C8 C15 115.82(13) . . ?
C9 C8 C7 106.60(14) . . ?
C9 C8 C15 115.38(14) . . ?
C25 C20 C15 108.33(17) . . ?
C21 C20 C15 132.84(17) . . ?
C21 C20 C25 118.83(19) . . ?
C10 C9 C8 120.63(16) . . ?
C10 C9 C14 118.82(17) . . ?
C14 C9 C8 120.51(15) . . ?
C36 C40 C34 108.53(17) . . ?
C41 C40 C36 118.97(19) . . ?
C41 C40 C34 132.49(18) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.67(19) . . ?
C11 C10 H10 119.7 . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 H2 121.4 . . ?
C33 C28 C27 107.42(18) . . ?
C29 C28 C27 130.5(2) . . ?
C29 C28 C33 121.7(2) . . ?
N1 C16 H16 110.5 . . ?
N1 C16 C17 114.19(17) . . ?
N2 C16 N1 105.16(15) . . ?
N2 C16 H16 110.5 . . ?
N2 C16 C17 105.65(16) . . ?
C17 C16 H16 110.5 . . ?
O3 C35 N6 126.89(18) . . ?
O3 C35 C34 125.61(19) . . ?
N6 C35 C34 107.50(17) . . ?
C46 C47 H47 119.6 . . ?
C46 C47 C48 120.8(2) . . ?
C48 C47 H47 119.6 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.84(18) . . ?
C13 C14 H14 120.1 . . ?
N4 C26 C46 112.46(14) . . ?
N4 C26 C27 103.79(14) . . ?
N4 C26 C34 102.24(15) . . ?
C46 C26 C27 107.33(15) . . ?
C46 C26 C34 115.05(15) . . ?
C27 C26 C34 115.41(14) . . ?
O4 C27 C28 128.81(18) . . ?
O4 C27 C26 124.72(17) . . ?
C28 C27 C26 106.44(16) . . ?
O1 C52 N3 126.63(18) . . ?
O1 C52 C15 125.79(19) . . ?
N3 C52 C15 107.57(17) . . ?
N5 C34 C40 115.87(16) . . ?
N5 C34 C35 105.48(16) . . ?
N5 C34 C26 104.55(14) . . ?
C40 C34 C35 101.78(15) . . ?
C40 C34 C26 118.92(16) . . ?
C35 C34 C26 109.43(15) . . ?
C20 C25 N3 110.05(18) . . ?
C24 C25 N3 127.8(2) . . ?
C24 C25 C20 122.1(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 C6 118.1(2) . . ?
C4 C5 H5 120.9 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.2(2) . . ?
C22 C21 H21 120.4 . . ?
N2 C19 H19A 111.4 . . ?
N2 C19 H19B 111.4 . . ?
N2 C19 C18 101.87(19) . . ?
H19A C19 H19B 109.3 . . ?
C18 C19 H19A 111.4 . . ?
C18 C19 H19B 111.4 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.26(19) . . ?
C12 C11 H11 119.9 . . ?
C46 C51 H51 119.7 . . ?
C46 C51 C50 120.5(2) . . ?
C50 C51 H51 119.7 . . ?
C28 C33 N4 112.57(18) . . ?
C32 C33 N4 127.1(2) . . ?
C32 C33 C28 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C47 C48 H48 119.9 . . ?
C49 C48 C47 120.1(2) . . ?
C49 C48 H48 119.9 . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.6 . . ?
C36 C37 H37 121.0 . . ?
C36 C37 C38 118.1(2) . . ?
C38 C37 H37 121.0 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C18 C17 C16 104.53(18) . . ?
C18 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C2 C3 C4 122.2(2) . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
C40 C41 H41 120.3 . . ?
C40 C41 C39 119.4(2) . . ?
C39 C41 H41 120.3 . . ?
C48 C49 H49 120.2 . . ?
C50 C49 C48 119.6(2) . . ?
C50 C49 H49 120.2 . . ?
C37 C38 H38 119.6 . . ?
C39 C38 C37 120.7(2) . . ?
C39 C38 H38 119.6 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C41 C39 H39 119.7 . . ?
C38 C39 C41 120.6(2) . . ?
C38 C39 H39 119.7 . . ?
C28 C29 H29 121.1 . . ?
C30 C29 C28 117.7(2) . . ?
C30 C29 H29 121.1 . . ?
N5 C45 H45A 111.6 . . ?
N5 C45 H45B 111.6 . . ?
N5 C45 C44 100.7(2) . . ?
H45A C45 H45B 109.4 . . ?
C44 C45 H45A 111.6 . . ?
C44 C45 H45B 111.6 . . ?
N4 C42 H42 110.4 . . ?
N4 C42 C43 114.81(18) . . ?
N5 C42 N4 105.19(16) . . ?
N5 C42 H42 110.4 . . ?
N5 C42 C43 105.29(18) . . ?
C43 C42 H42 110.4 . . ?
C25 C24 H24 120.9 . . ?
C23 C24 C25 118.1(2) . . ?
C23 C24 H24 120.9 . . ?
C30 C31 H31 118.8 . . ?
C32 C31 H31 118.8 . . ?
C32 C31 C30 122.4(2) . . ?
C51 C50 H50 119.7 . . ?
C49 C50 C51 120.7(2) . . ?
C49 C50 H50 119.7 . . ?
C29 C30 C31 120.1(2) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C19 C18 C17 102.97(18) . . ?
C19 C18 H18A 111.2 . . ?
C19 C18 H18B 111.2 . . ?
C17 C18 H18A 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
C45 C44 H44A 110.9 . . ?
C45 C44 H44B 110.9 . . ?
H44A C44 H44B 108.9 . . ?
C43 C44 C45 104.3(2) . . ?
C43 C44 H44A 110.9 . . ?
C43 C44 H44B 110.9 . . ?
C33 C32 H32 121.2 . . ?
C31 C32 C33 117.6(3) . . ?
C31 C32 H32 121.2 . . ?
C42 C43 H43A 110.8 . . ?
C42 C43 H43B 110.8 . . ?
C44 C43 C42 104.7(2) . . ?
C44 C43 H43A 110.8 . . ?
C44 C43 H43B 110.8 . . ?
H43A C43 H43B 108.9 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.9(2) . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.9(2) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?

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
O2 C7 C8 N1 -169.39(18) . . . . ?
O2 C7 C8 C15 -57.9(2) . . . . ?
O2 C7 C8 C9 72.0(2) . . . . ?
N1 C1 C6 C7 10.2(2) . . . . ?
N1 C1 C6 C5 -174.67(18) . . . . ?
N1 C1 C2 C3 175.5(2) . . . . ?
N1 C8 C9 C10 7.1(2) . . . . ?
N1 C8 C9 C14 -170.60(17) . . . . ?
N1 C16 C17 C18 -121.8(2) . . . . ?
O3 C35 C34 N5 59.6(3) . . . . ?
O3 C35 C34 C40 -179.0(2) . . . . ?
O3 C35 C34 C26 -52.4(3) . . . . ?
N2 C15 C8 N1 -26.22(16) . . . . ?
N2 C15 C8 C7 -138.80(15) . . . . ?
N2 C15 C8 C9 95.69(17) . . . . ?
N2 C15 C20 C25 113.19(19) . . . . ?
N2 C15 C20 C21 -67.0(3) . . . . ?
N2 C15 C52 O1 60.3(3) . . . . ?
N2 C15 C52 N3 -119.39(18) . . . . ?
N2 C16 C17 C18 -6.7(3) . . . . ?
N2 C19 C18 C17 -41.2(2) . . . . ?
N6 C36 C40 C34 -0.9(2) . . . . ?
N6 C36 C40 C41 -180.0(2) . . . . ?
N6 C36 C37 C38 179.6(2) . . . . ?
N6 C35 C34 N5 -119.58(19) . . . . ?
N6 C35 C34 C40 1.8(2) . . . . ?
N6 C35 C34 C26 128.45(18) . . . . ?
N4 C26 C27 O4 -169.89(19) . . . . ?
N4 C26 C27 C28 8.61(19) . . . . ?
N4 C26 C34 N5 -25.67(17) . . . . ?
N4 C26 C34 C40 -156.84(15) . . . . ?
N4 C26 C34 C35 86.91(17) . . . . ?
N4 C33 C32 C31 177.9(2) . . . . ?
N4 C42 C43 C44 -121.2(2) . . . . ?
N3 C25 C24 C23 179.5(3) . . . . ?
N5 C45 C44 C43 -40.4(3) . . . . ?
N5 C42 C43 C44 -6.0(3) . . . . ?
C1 N1 C8 C7 -4.29(19) . . . . ?
C1 N1 C8 C15 -125.29(15) . . . . ?
C1 N1 C8 C9 110.53(16) . . . . ?
C1 N1 C16 N2 138.45(16) . . . . ?
C1 N1 C16 C17 -106.2(2) . . . . ?
C1 C6 C7 O2 167.2(2) . . . . ?
C1 C6 C7 C8 -12.3(2) . . . . ?
C1 C6 C5 C4 -1.9(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C6 C1 C2 C3 -4.5(3) . . . . ?
C6 C7 C8 N1 10.06(18) . . . . ?
C6 C7 C8 C15 121.59(17) . . . . ?
C6 C7 C8 C9 -108.53(16) . . . . ?
C6 C5 C4 C3 -2.1(4) . . . . ?
C7 C6 C5 C4 172.0(2) . . . . ?
C7 C8 C9 C10 120.45(18) . . . . ?
C7 C8 C9 C14 -57.3(2) . . . . ?
C46 C47 C48 C49 1.0(4) . . . . ?
C46 C26 C27 O4 70.9(2) . . . . ?
C46 C26 C27 C28 -110.65(17) . . . . ?
C46 C26 C34 N5 96.54(18) . . . . ?
C46 C26 C34 C40 -34.6(2) . . . . ?
C46 C26 C34 C35 -150.88(16) . . . . ?
C46 C51 C50 C49 0.5(4) . . . . ?
C36 N6 C35 O3 178.4(2) . . . . ?
C36 N6 C35 C34 -2.5(3) . . . . ?
C36 C40 C34 N5 113.34(19) . . . . ?
C36 C40 C34 C35 -0.5(2) . . . . ?
C36 C40 C34 C26 -120.73(19) . . . . ?
C36 C40 C41 C39 0.5(3) . . . . ?
C36 C37 C38 C39 -0.1(4) . . . . ?
C15 N2 C16 N1 -26.21(18) . . . . ?
C15 N2 C16 C17 -147.33(17) . . . . ?
C15 N2 C19 C18 159.12(18) . . . . ?
C15 C8 C9 C10 -109.4(2) . . . . ?
C15 C8 C9 C14 72.8(2) . . . . ?
C15 C20 C25 N3 -0.5(3) . . . . ?
C15 C20 C25 C24 178.7(2) . . . . ?
C15 C20 C21 C22 -179.0(2) . . . . ?
C8 N1 C1 C6 -3.4(2) . . . . ?
C8 N1 C1 C2 176.57(19) . . . . ?
C8 N1 C16 N2 8.67(19) . . . . ?
C8 N1 C16 C17 124.02(17) . . . . ?
C8 C15 C20 C25 -121.29(18) . . . . ?
C8 C15 C20 C21 58.5(3) . . . . ?
C8 C15 C52 O1 -50.9(3) . . . . ?
C8 C15 C52 N3 129.37(18) . . . . ?
C8 C9 C10 C11 -179.40(19) . . . . ?
C8 C9 C14 C13 179.44(19) . . . . ?
C20 C15 C8 N1 -156.88(15) . . . . ?
C20 C15 C8 C7 90.55(19) . . . . ?
C20 C15 C8 C9 -35.0(2) . . . . ?
C20 C15 C52 O1 -178.9(2) . . . . ?
C20 C15 C52 N3 1.4(2) . . . . ?
C20 C25 C24 C23 0.5(4) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C14 C13 C12 0.0(4) . . . . ?
C40 C36 C37 C38 0.2(4) . . . . ?
C40 C41 C39 C38 -0.4(4) . . . . ?
C10 C9 C14 C13 1.7(3) . . . . ?
C10 C11 C12 C13 1.7(4) . . . . ?
C2 C1 C6 C7 -169.82(18) . . . . ?
C2 C1 C6 C5 5.3(3) . . . . ?
C28 C33 C32 C31 -3.3(3) . . . . ?
C28 C29 C30 C31 -1.1(4) . . . . ?
C16 N1 C1 C6 -134.38(18) . . . . ?
C16 N1 C1 C2 45.6(3) . . . . ?
C16 N1 C8 C7 131.85(15) . . . . ?
C16 N1 C8 C15 10.85(17) . . . . ?
C16 N1 C8 C9 -113.33(16) . . . . ?
C16 N2 C15 C8 32.79(17) . . . . ?
C16 N2 C15 C20 166.20(15) . . . . ?
C16 N2 C15 C52 -82.09(18) . . . . ?
C16 N2 C19 C18 38.2(2) . . . . ?
C16 C17 C18 C19 29.5(3) . . . . ?
C35 N6 C36 C40 2.2(3) . . . . ?
C35 N6 C36 C37 -177.3(2) . . . . ?
C47 C46 C26 N4 14.0(2) . . . . ?
C47 C46 C26 C27 127.52(18) . . . . ?
C47 C46 C26 C34 -102.5(2) . . . . ?
C47 C46 C51 C50 -0.8(3) . . . . ?
C47 C48 C49 C50 -1.3(4) . . . . ?
C14 C9 C10 C11 -1.6(3) . . . . ?
C14 C13 C12 C11 -1.7(4) . . . . ?
C26 N4 C33 C28 -4.4(2) . . . . ?
C26 N4 C33 C32 174.5(2) . . . . ?
C26 N4 C42 N5 9.8(2) . . . . ?
C26 N4 C42 C43 125.08(19) . . . . ?
C26 C46 C47 C48 -179.98(19) . . . . ?
C26 C46 C51 C50 179.3(2) . . . . ?
C27 C28 C33 N4 10.1(2) . . . . ?
C27 C28 C33 C32 -168.87(19) . . . . ?
C27 C28 C29 C30 169.5(2) . . . . ?
C27 C26 C34 N5 -137.58(16) . . . . ?
C27 C26 C34 C40 91.25(19) . . . . ?
C27 C26 C34 C35 -25.0(2) . . . . ?
C52 N3 C25 C20 1.5(3) . . . . ?
C52 N3 C25 C24 -177.6(3) . . . . ?
C52 C15 C8 N1 86.01(16) . . . . ?
C52 C15 C8 C7 -26.6(2) . . . . ?
C52 C15 C8 C9 -152.08(15) . . . . ?
C52 C15 C20 C25 -0.6(2) . . . . ?
C52 C15 C20 C21 179.3(2) . . . . ?
C34 N5 C45 C44 158.9(2) . . . . ?
C34 N5 C42 N4 -26.86(19) . . . . ?
C34 N5 C42 C43 -148.53(17) . . . . ?
C34 C40 C41 C39 -178.3(2) . . . . ?
C34 C26 C27 O4 -58.9(3) . . . . ?
C34 C26 C27 C28 119.61(17) . . . . ?
C25 N3 C52 O1 178.5(2) . . . . ?
C25 N3 C52 C15 -1.8(3) . . . . ?
C25 C20 C21 C22 0.8(3) . . . . ?
C25 C24 C23 C22 0.5(5) . . . . ?
C5 C6 C7 O2 -7.3(4) . . . . ?
C5 C6 C7 C8 173.2(2) . . . . ?
C5 C4 C3 C2 2.8(4) . . . . ?
C21 C20 C25 N3 179.7(2) . . . . ?
C21 C20 C25 C24 -1.2(4) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
C19 N2 C15 C8 -88.36(19) . . . . ?
C19 N2 C15 C20 45.0(2) . . . . ?
C19 N2 C15 C52 156.76(17) . . . . ?
C19 N2 C16 N1 101.44(18) . . . . ?
C19 N2 C16 C17 -19.7(2) . . . . ?
C51 C46 C47 C48 0.0(3) . . . . ?
C51 C46 C26 N4 -166.04(18) . . . . ?
C51 C46 C26 C27 -52.5(2) . . . . ?
C51 C46 C26 C34 77.4(2) . . . . ?
C33 N4 C26 C46 112.84(17) . . . . ?
C33 N4 C26 C27 -2.84(19) . . . . ?
C33 N4 C26 C34 -123.20(15) . . . . ?
C33 N4 C42 N5 137.10(17) . . . . ?
C33 N4 C42 C43 -107.6(2) . . . . ?
C33 C28 C27 O4 167.1(2) . . . . ?
C33 C28 C27 C26 -11.3(2) . . . . ?
C33 C28 C29 C30 -2.3(3) . . . . ?
C48 C49 C50 C51 0.6(4) . . . . ?
C37 C36 C40 C34 178.6(2) . . . . ?
C37 C36 C40 C41 -0.5(4) . . . . ?
C37 C38 C39 C41 0.2(4) . . . . ?
C41 C40 C34 N5 -67.8(3) . . . . ?
C41 C40 C34 C35 178.4(2) . . . . ?
C41 C40 C34 C26 58.2(3) . . . . ?
C29 C28 C27 O4 -5.6(4) . . . . ?
C29 C28 C27 C26 176.0(2) . . . . ?
C29 C28 C33 N4 -176.45(19) . . . . ?
C29 C28 C33 C32 4.6(3) . . . . ?
C45 N5 C34 C40 43.7(2) . . . . ?
C45 N5 C34 C35 155.41(17) . . . . ?
C45 N5 C34 C26 -89.2(2) . . . . ?
C45 N5 C42 N4 101.52(19) . . . . ?
C45 N5 C42 C43 -20.2(2) . . . . ?
C45 C44 C43 C42 28.8(3) . . . . ?
C42 N4 C26 C46 -114.27(17) . . . . ?
C42 N4 C26 C27 130.06(16) . . . . ?
C42 N4 C26 C34 9.70(18) . . . . ?
C42 N4 C33 C28 -132.80(19) . . . . ?
C42 N4 C33 C32 46.1(3) . . . . ?
C42 N5 C34 C40 165.85(16) . . . . ?
C42 N5 C34 C35 -82.45(18) . . . . ?
C42 N5 C34 C26 32.93(18) . . . . ?
C42 N5 C45 C44 37.5(2) . . . . ?
C30 C31 C32 C33 0.0(4) . . . . ?
C32 C31 C30 C29 2.3(4) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted on the glass stick by acrylic glue.'
_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 1.763
_oxdiff_exptl_absorpt_empirical_full_min 0.647
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5540(11) 13060 29062 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4460(11) 0 29062 nmt 1.0006 0.0005 -0.0037 -0.0014 -1.0004 0.0009 0.5359
-0.0009 -1.0002

_twin_special_details            
;
Component 2 rotated by -179.9503° 
around [0.97 -0.00 0.26] (reciprocal) or [1.00 0.00 -0.00] (direct)
;
####################################################################### 
# 
# 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_anna_ark1118_1
_database_code_depnum_ccdc_archive 'CCDC 2470466'
loop_
_audit_author_name
_audit_author_address
'Nicolai Aksenov'
;North Caucasus Federal University
Russia
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_audit_creation_date             2025-07-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 N3 O'
_chemical_formula_sum            'C28 H21 N3 O'
_chemical_formula_weight         415.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
O O 0.0492 0.0322 '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                   10.16710(10)
_cell_length_b                   15.24880(10)
_cell_length_c                   14.09840(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.2150(10)
_cell_angle_gamma                90
_cell_volume                     2168.45(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8170
_cell_measurement_theta_min      4.2550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 2 6 0.0637
-4 -2 -6 0.0759
-6 1 4 0.1305
-1 9 2 0.1463
0 10 2 0.1447
6 5 -2 0.0903
-1 -10 -1 0.1220
0 0 9 0.0775
-4 -1 -6 0.0675
-1 -10 -1 0.1172
1 7 -7 0.1020
-6 1 -1 0.1223
-1 -7 7 0.1327
5 0 6 0.0639

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Crystallized by slow evaporation of saturated solution in EtOAc.'
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.135
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
3.9480 2.0442 6.3430 0.2080 0.8657 -0.4554
-4.3826 -2.1696 -5.7276 -0.1978 -0.8225 0.5332
-6.2670 1.4050 3.6295 -0.3187 0.1925 0.9281
-1.1256 9.4681 2.3415 -0.8531 0.5217 -0.0090
0.3926 9.7175 1.5704 -0.8268 0.5062 -0.2451
5.8007 4.5091 -2.2943 -0.2068 0.1289 -0.9699
-0.8896 -9.6792 -1.2959 0.8079 -0.4948 0.3201
0.0732 -0.3400 9.0608 0.3263 0.9228 0.2050
-4.4866 -1.3284 -5.7654 -0.2817 -0.8016 0.5274
-0.6406 -9.7080 -1.4231 0.8186 -0.4998 0.2830
0.9234 6.6936 -6.7262 -0.7887 -0.4303 -0.4390
-6.3893 1.4905 -0.7039 -0.4718 -0.2547 0.8441
-0.5876 -6.7233 6.7151 0.8075 0.4404 0.3924
4.6572 -0.4446 5.6091 0.4486 0.7314 -0.5136

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35509
_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         75.999
_diffrn_reflns_theta_min         4.289
_diffrn_ambient_temperature      293(2)
_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    -83.00   8.00   1.00    5.00    --  -41.19 108.00-151.00   91
  2  ω     13.00  85.00   1.00    5.00    --   41.19-108.00 111.00   72
  3  ω    104.00 178.00   1.00   20.00    --  112.00 108.00-151.00   74
  4  ω     37.00 108.00   1.00   20.00    --  112.00-108.00 111.00   71
  5  ω   -115.00 -17.00   1.00    5.00    --  -41.19 -38.00  30.00   98
  6  ω     13.00 113.00   1.00    5.00    --   41.19  57.00  30.00  100
  7  ω      7.00  33.00   1.00    5.00    --   41.19  84.00  -1.43   26
  8  ω      7.00  34.00   1.00    5.00    --   41.19  83.00 -17.11   27
  9  ω     61.00 146.00   1.00   20.00    --  112.00 178.00-120.00   85
 10  ω     36.00 140.00   1.00   20.00    --  112.00 -30.00 -90.00  104
 11  ω    103.00 178.00   1.00   20.00    --  112.00  77.00   0.00   75
 12  ω     40.00 141.00   1.00   20.00    --  112.00 -61.00 120.00  101
 13  ω     30.00 106.00   1.00   20.00    --  112.00 -95.00 150.00   76
 14  ω     40.00 141.00   1.00   20.00    --  112.00 -61.00 120.00  101
 15  ω     39.00 109.00   1.00   20.00    --  112.00-111.00 -60.00   70
 16  ω     39.00 109.00   1.00   20.00    --  112.00-111.00 150.00   70
 17  ω     39.00 138.00   1.00   20.00    --  112.00 -45.00 -90.00   99
 18  ω     84.00 178.00   1.00   20.00    --  112.00  30.00  30.00   94
 19  ω     36.00 145.00   1.00   20.00    --  112.00 -77.00-180.00  109
 20  ω     61.00 146.00   1.00   20.00    --  112.00 178.00  90.00   85
 21  ω     61.00 146.00   1.00   20.00    --  112.00 178.00  90.00   85
 22  ω     30.00 106.00   1.00   20.00    --  112.00 -95.00 120.00   76
 23  ω     30.00 106.00   1.00   20.00    --  112.00 -95.00 120.00   76
 24  ω     84.00 178.00   1.00   20.00    --  112.00  30.00  90.00   94
 25  ω     39.00 109.00   1.00   20.00    --  112.00-111.00 -90.00   70
 26  ω     30.00 106.00   1.00   20.00    --  112.00 -95.00-150.00   76
 27  ω    103.00 178.00   1.00   20.00    --  112.00  77.00   0.00   75
 28  ω     40.00 103.00   1.00   20.00    --  112.00 -61.00-120.00   63
 29  ω     39.00 109.00   1.00   20.00    --  112.00-111.00 120.00   70
 30  ω    104.00 178.00   1.00   20.00    --  112.00 111.00 -60.00   74
 31  ω     86.00 178.00   1.00   20.00    --  112.00  45.00 120.00   92
 32  ω     26.00 178.00   1.00   20.00    --  112.00  -4.00  83.55  152
 33  ω     40.00 103.00   1.00   20.00    --  112.00 -61.00-120.00   63
;
_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      0.0487851000
_diffrn_orient_matrix_UB_12      -0.0922540000
_diffrn_orient_matrix_UB_13      0.0321533000
_diffrn_orient_matrix_UB_21      0.0364627000
_diffrn_orient_matrix_UB_22      0.0340044000
_diffrn_orient_matrix_UB_23      0.1028242000
_diffrn_orient_matrix_UB_31      -0.1400604000
_diffrn_orient_matrix_UB_32      -0.0232658000
_diffrn_orient_matrix_UB_33      0.0228854000
_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                4214
_reflns_number_total             4510
_reflns_odcompleteness_completeness 98.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.86
_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 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.90 64-bit (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0038(3)
_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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.039
_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)+(0.0595P)²+0.3604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1140
_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:
 C20(H20), C15(H15), C10(H10), C16(H16), C19(H19), C24(H24), C28(H28),
 C11(H11), C12(H12), C14(H14), C26(H26), C2(H2), C27(H27), C25(H25), C13(H13),
 C5(H5), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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 0.12467(9) 0.45122(6) 0.29626(7) 0.0443(2) Uani 1 1 d . . . . .
N2 N 0.31561(9) 0.42061(6) 0.23522(7) 0.0448(2) Uani 1 1 d . . . . .
N3 N 0.23614(9) 0.47090(6) 0.16811(7) 0.0436(2) Uani 1 1 d . . . . .
O1 O 0.39038(10) 0.35868(8) 0.45339(7) 0.0706(3) Uani 1 1 d . . . . .
C21 C 0.43119(10) 0.38352(7) 0.20788(8) 0.0406(2) Uani 1 1 d . . . . .
C22 C 0.12949(10) 0.48897(7) 0.20404(8) 0.0423(2) Uani 1 1 d . . . . .
C20 C 0.48217(11) 0.41459(7) 0.12691(8) 0.0460(3) Uani 1 1 d . . . . .
H20 H 0.437448 0.458205 0.089654 0.055 Uiso 1 1 calc R U . . .
C23 C 0.02002(11) 0.54042(7) 0.15493(8) 0.0451(3) Uani 1 1 d . . . . .
C9 C 0.18204(10) 0.29464(7) 0.28867(8) 0.0429(2) Uani 1 1 d . . . . .
C8 C 0.23557(10) 0.38683(7) 0.30740(8) 0.0427(2) Uani 1 1 d . . . . .
C15 C 0.49929(12) 0.31739(8) 0.26146(9) 0.0524(3) Uani 1 1 d . . . . .
H15 H 0.466615 0.295374 0.315400 0.063 Uiso 1 1 calc R U . . .
C7 C 0.30378(12) 0.40356(9) 0.41153(9) 0.0520(3) Uani 1 1 d . . . . .
C1 C 0.14047(12) 0.50893(8) 0.37631(9) 0.0505(3) Uani 1 1 d . . . . .
C10 C 0.18014(12) 0.25499(8) 0.20029(9) 0.0517(3) Uani 1 1 d . . . . .
H10 H 0.220283 0.282682 0.152650 0.062 Uiso 1 1 calc R U . . .
C17 C 0.66916(12) 0.31524(9) 0.15504(9) 0.0545(3) Uani 1 1 d . . . . .
C6 C 0.24027(13) 0.48129(9) 0.44560(9) 0.0570(3) Uani 1 1 d . . . . .
C16 C 0.61578(12) 0.28446(9) 0.23431(10) 0.0557(3) Uani 1 1 d . . . . .
H16 H 0.659813 0.240003 0.270656 0.067 Uiso 1 1 calc R U . . .
C19 C 0.59920(12) 0.38059(9) 0.10197(9) 0.0536(3) Uani 1 1 d . . . . .
H19 H 0.632044 0.402230 0.047925 0.064 Uiso 1 1 calc R U . . .
C24 C 0.04451(13) 0.60362(9) 0.08878(10) 0.0568(3) Uani 1 1 d . . . . .
H24 H 0.130901 0.614172 0.076591 0.068 Uiso 1 1 calc R U . . .
C28 C -0.10924(12) 0.52576(8) 0.17316(11) 0.0587(3) Uani 1 1 d . . . . .
H28 H -0.126736 0.484259 0.218270 0.070 Uiso 1 1 calc R U . . .
C11 C 0.11902(13) 0.17435(9) 0.18191(11) 0.0612(3) Uani 1 1 d . . . . .
H11 H 0.118024 0.148465 0.122096 0.073 Uiso 1 1 calc R U . . .
C12 C 0.06002(14) 0.13274(9) 0.25185(12) 0.0652(4) Uani 1 1 d . . . . .
H12 H 0.018810 0.078767 0.239482 0.078 Uiso 1 1 calc R U . . .
C14 C 0.12307(14) 0.25141(9) 0.35892(10) 0.0587(3) Uani 1 1 d . . . . .
H14 H 0.124458 0.276533 0.419147 0.070 Uiso 1 1 calc R U . . .
C26 C -0.18697(14) 0.63544(10) 0.05759(11) 0.0658(4) Uani 1 1 d . . . . .
H26 H -0.256525 0.666759 0.024315 0.079 Uiso 1 1 calc R U . . .
C2 C 0.06808(15) 0.58476(9) 0.38913(12) 0.0652(4) Uani 1 1 d . . . . .
H2 H 0.001328 0.604075 0.342663 0.078 Uiso 1 1 calc R U . . .
C27 C -0.21220(13) 0.57340(10) 0.12369(13) 0.0677(4) Uani 1 1 d . . . . .
H27 H -0.298934 0.563262 0.135351 0.081 Uiso 1 1 calc R U . . .
C25 C -0.05923(15) 0.65110(11) 0.04077(11) 0.0671(4) Uani 1 1 d . . . . .
H25 H -0.042153 0.693848 -0.003119 0.081 Uiso 1 1 calc R U . . .
C13 C 0.06205(16) 0.17088(11) 0.33974(12) 0.0709(4) Uani 1 1 d . . . . .
H13 H 0.022161 0.142582 0.387114 0.085 Uiso 1 1 calc R U . . .
C5 C 0.26988(19) 0.52720(13) 0.53122(12) 0.0805(5) Uani 1 1 d . . . . .
H5 H 0.336453 0.508130 0.577960 0.097 Uiso 1 1 calc R U . . .
C18 C 0.7994(2) 0.28107(18) 0.12923(16) 0.0866(6) Uani 1 1 d . . . . .
C3 C 0.0998(2) 0.62994(13) 0.47387(14) 0.0865(5) Uani 1 1 d . . . . .
H3 H 0.053884 0.681190 0.483756 0.104 Uiso 1 1 calc R U . . .
C4 C 0.1974(2) 0.60181(14) 0.54450(14) 0.0954(6) Uani 1 1 d . . . . .
H4 H 0.214299 0.633285 0.601230 0.114 Uiso 1 1 calc R U . . .
H18A H 0.792(3) 0.218(2) 0.130(2) 0.154(12) Uiso 1 1 d . . . . .
H18B H 0.873(4) 0.300(2) 0.171(3) 0.179(13) Uiso 1 1 d . . . . .
H18C H 0.811(3) 0.287(2) 0.064(3) 0.169(12) Uiso 1 1 d . . . . .


_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 1.4284(14) . ?
N1 C8 1.4885(13) . ?
N1 C1 1.4243(15) . ?
N2 N3 1.3943(12) . ?
N2 C21 1.4011(13) . ?
N2 C8 1.4735(13) . ?
N3 C22 1.2831(14) . ?
O1 C7 1.2089(16) . ?
C21 C20 1.3946(15) . ?
C21 C15 1.3912(16) . ?
C22 C23 1.4628(15) . ?
C20 H20 0.9300 . ?
C20 C19 1.3832(16) . ?
C23 C24 1.3853(18) . ?
C23 C28 1.3886(16) . ?
C9 C8 1.5185(15) . ?
C9 C10 1.3829(17) . ?
C9 C14 1.3871(16) . ?
C8 C7 1.5638(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3840(17) . ?
C7 C6 1.4596(19) . ?
C1 C6 1.383(2) . ?
C1 C2 1.3944(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.3873(19) . ?
C17 C16 1.3843(19) . ?
C17 C19 1.3875(19) . ?
C17 C18 1.5093(18) . ?
C6 C5 1.395(2) . ?
C16 H16 0.9300 . ?
C19 H19 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.3840(18) . ?
C28 H28 0.9300 . ?
C28 C27 1.3880(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.387(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.375(2) . ?
C26 C25 1.370(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C27 H27 0.9300 . ?
C25 H25 0.9300 . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.381(3) . ?
C18 H18A 0.96(3) . ?
C18 H18B 0.94(4) . ?
C18 H18C 0.94(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9300 . ?

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
C22 N1 C8 104.47(8) . . ?
C1 N1 C22 117.31(9) . . ?
C1 N1 C8 108.39(9) . . ?
N3 N2 C21 118.03(9) . . ?
N3 N2 C8 109.74(8) . . ?
C21 N2 C8 127.15(9) . . ?
C22 N3 N2 107.26(9) . . ?
C20 C21 N2 119.92(9) . . ?
C15 C21 N2 121.37(10) . . ?
C15 C21 C20 118.68(10) . . ?
N1 C22 C23 122.41(9) . . ?
N3 C22 N1 113.58(9) . . ?
N3 C22 C23 123.98(10) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.05(11) . . ?
C19 C20 H20 120.0 . . ?
C24 C23 C22 120.09(10) . . ?
C24 C23 C28 119.40(11) . . ?
C28 C23 C22 120.51(11) . . ?
C10 C9 C8 121.71(10) . . ?
C10 C9 C14 118.50(11) . . ?
C14 C9 C8 119.56(11) . . ?
N1 C8 C9 110.00(8) . . ?
N1 C8 C7 103.42(9) . . ?
N2 C8 N1 99.98(8) . . ?
N2 C8 C9 114.86(9) . . ?
N2 C8 C7 111.91(9) . . ?
C9 C8 C7 114.92(9) . . ?
C21 C15 H15 120.1 . . ?
C16 C15 C21 119.85(11) . . ?
C16 C15 H15 120.1 . . ?
O1 C7 C8 125.16(12) . . ?
O1 C7 C6 128.62(12) . . ?
C6 C7 C8 106.21(10) . . ?
C6 C1 N1 111.78(11) . . ?
C6 C1 C2 120.90(13) . . ?
C2 C1 N1 127.32(13) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.74(12) . . ?
C11 C10 H10 119.6 . . ?
C16 C17 C19 116.90(11) . . ?
C16 C17 C18 121.49(14) . . ?
C19 C17 C18 121.59(14) . . ?
C1 C6 C7 109.31(11) . . ?
C1 C6 C5 121.17(14) . . ?
C5 C6 C7 129.49(14) . . ?
C15 C16 C17 122.42(11) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C20 C19 C17 122.09(11) . . ?
C20 C19 H19 119.0 . . ?
C17 C19 H19 119.0 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.19(12) . . ?
C25 C24 H24 119.9 . . ?
C23 C28 H28 120.2 . . ?
C27 C28 C23 119.63(13) . . ?
C27 C28 H28 120.2 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.10(13) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.76(13) . . ?
C13 C12 H12 120.1 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.29(13) . . ?
C13 C14 H14 119.9 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 119.93(13) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.10(16) . . ?
C3 C2 H2 121.4 . . ?
C28 C27 H27 119.7 . . ?
C26 C27 C28 120.51(13) . . ?
C26 C27 H27 119.7 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.32(14) . . ?
C26 C25 H25 119.8 . . ?
C12 C13 C14 120.60(13) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C6 C5 H5 121.0 . . ?
C4 C5 C6 118.03(17) . . ?
C4 C5 H5 121.0 . . ?
C17 C18 H18A 105.6(18) . . ?
C17 C18 H18B 113(2) . . ?
C17 C18 H18C 115(2) . . ?
H18A C18 H18B 111(3) . . ?
H18A C18 H18C 97(3) . . ?
H18B C18 H18C 114(3) . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.46(17) . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 120.31(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?

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 C23 C24 153.57(11) . . . . ?
N1 C22 C23 C28 -27.22(16) . . . . ?
N1 C8 C7 O1 171.70(12) . . . . ?
N1 C8 C7 C6 -7.39(11) . . . . ?
N1 C1 C6 C7 3.44(14) . . . . ?
N1 C1 C6 C5 -178.29(13) . . . . ?
N1 C1 C2 C3 179.02(13) . . . . ?
N2 N3 C22 N1 -1.68(12) . . . . ?
N2 N3 C22 C23 -179.50(10) . . . . ?
N2 C21 C20 C19 177.34(11) . . . . ?
N2 C21 C15 C16 -177.65(11) . . . . ?
N2 C8 C7 O1 -81.56(15) . . . . ?
N2 C8 C7 C6 99.35(11) . . . . ?
N3 N2 C21 C20 16.53(15) . . . . ?
N3 N2 C21 C15 -165.29(11) . . . . ?
N3 N2 C8 N1 -21.97(11) . . . . ?
N3 N2 C8 C9 95.69(10) . . . . ?
N3 N2 C8 C7 -130.93(10) . . . . ?
N3 C22 C23 C24 -28.80(17) . . . . ?
N3 C22 C23 C28 150.41(12) . . . . ?
O1 C7 C6 C1 -176.31(13) . . . . ?
O1 C7 C6 C5 5.6(2) . . . . ?
C21 N2 N3 C22 172.35(10) . . . . ?
C21 N2 C8 N1 -175.90(10) . . . . ?
C21 N2 C8 C9 -58.23(15) . . . . ?
C21 N2 C8 C7 75.15(14) . . . . ?
C21 C20 C19 C17 0.28(19) . . . . ?
C21 C15 C16 C17 0.4(2) . . . . ?
C22 N1 C8 N2 19.69(10) . . . . ?
C22 N1 C8 C9 -101.53(10) . . . . ?
C22 N1 C8 C7 135.25(9) . . . . ?
C22 N1 C1 C6 -126.40(11) . . . . ?
C22 N1 C1 C2 53.99(16) . . . . ?
C22 C23 C24 C25 178.65(12) . . . . ?
C22 C23 C28 C27 -178.03(12) . . . . ?
C20 C21 C15 C16 0.55(18) . . . . ?
C23 C24 C25 C26 -0.6(2) . . . . ?
C23 C28 C27 C26 -0.6(2) . . . . ?
C9 C8 C7 O1 51.79(16) . . . . ?
C9 C8 C7 C6 -127.30(10) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C9 C14 C13 C12 0.5(2) . . . . ?
C8 N1 C22 N3 -12.47(12) . . . . ?
C8 N1 C22 C23 165.38(10) . . . . ?
C8 N1 C1 C6 -8.49(13) . . . . ?
C8 N1 C1 C2 171.89(12) . . . . ?
C8 N2 N3 C22 15.73(12) . . . . ?
C8 N2 C21 C20 168.58(11) . . . . ?
C8 N2 C21 C15 -13.24(18) . . . . ?
C8 C9 C10 C11 -173.58(11) . . . . ?
C8 C9 C14 C13 173.61(12) . . . . ?
C8 C7 C6 C1 2.73(13) . . . . ?
C8 C7 C6 C5 -175.35(14) . . . . ?
C15 C21 C20 C19 -0.89(18) . . . . ?
C7 C6 C5 C4 177.23(16) . . . . ?
C1 N1 C22 N3 107.52(11) . . . . ?
C1 N1 C22 C23 -74.62(13) . . . . ?
C1 N1 C8 N2 -106.12(10) . . . . ?
C1 N1 C8 C9 132.66(9) . . . . ?
C1 N1 C8 C7 9.44(11) . . . . ?
C1 C6 C5 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C10 C9 C8 N1 96.38(12) . . . . ?
C10 C9 C8 N2 -15.45(15) . . . . ?
C10 C9 C8 C7 -147.42(11) . . . . ?
C10 C9 C14 C13 -0.98(19) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C16 C17 C19 C20 0.6(2) . . . . ?
C19 C17 C16 C15 -1.0(2) . . . . ?
C24 C23 C28 C27 1.2(2) . . . . ?
C28 C23 C24 C25 -0.6(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C14 C9 C8 N1 -78.03(13) . . . . ?
C14 C9 C8 N2 170.14(10) . . . . ?
C14 C9 C8 C7 38.17(15) . . . . ?
C14 C9 C10 C11 0.88(18) . . . . ?
C2 C1 C6 C7 -176.92(11) . . . . ?
C2 C1 C6 C5 1.4(2) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C27 C26 C25 C24 1.2(2) . . . . ?
C25 C26 C27 C28 -0.5(2) . . . . ?
C18 C17 C16 C15 177.31(17) . . . . ?
C18 C17 C19 C20 -177.66(16) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted on the glass stick by acrylic glue.'
_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 1.504
_oxdiff_exptl_absorpt_empirical_full_min 0.782
####################################################################### 
# 
# 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_anna_ark1114_1
_database_code_depnum_ccdc_archive 'CCDC 2470465'
loop_
_audit_author_name
_audit_author_address
'Nicolai Aksenov'
;North Caucasus Federal University
Russia
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_audit_creation_date             2025-07-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N2 O2'
_chemical_formula_sum            'C21 H14 N2 O2'
_chemical_formula_weight         326.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
O O 0.0492 0.0322 '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                   11.1565(2)
_cell_length_b                   9.31590(10)
_cell_length_c                   15.0212(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.6470(10)
_cell_angle_gamma                90
_cell_volume                     1553.62(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15889
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6000
_cell_measurement_theta_min      3.9190
_shelx_estimated_absorpt_T_max   0.821
_shelx_estimated_absorpt_T_min   0.738
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 -5 0.1505
3 4 -6 0.1674
-3 3 8 0.2067
2 -2 -9 0.2319
7 -2 1 0.1412
1 1 9 0.1836
-3 2 9 0.1919
-7 2 -1 0.1365
-7 1 -2 0.1375
6 -2 -4 0.1513
-3 0 -8 0.2430
4 -5 -4 0.1748
2 -5 5 0.1395
6 3 -5 0.1565
4 5 2 0.1720
-3 -5 -4 0.1709
-6 -2 6 0.1562
7 -1 -3 0.1387
-7 0 0 0.1083
-1 5 -5 0.1172

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
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
1.3389 -4.9854 -5.3784 -0.1409 -0.5819 0.8009
2.6417 4.1692 -6.4160 0.2058 0.8652 0.4572
-2.6260 2.5822 8.3933 0.0278 0.1069 -0.9939
2.0015 -1.8287 -9.1224 0.1208 -0.0180 0.9925
6.8746 -1.6751 0.5276 -0.9369 0.1217 0.3278
1.4058 0.9725 9.2045 -0.5775 0.0773 -0.8127
-2.8496 1.9860 8.7161 0.0092 0.0010 -1.0000
-6.8271 1.5801 -1.1014 0.9549 -0.1242 -0.2697
-6.7147 1.4335 -1.9175 0.9746 -0.1269 -0.1846
6.1618 -2.2173 -4.4789 -0.6296 0.0805 0.7727
-3.0576 -0.4299 -8.3622 0.7615 -0.1009 0.6402
3.8011 -4.7783 -3.5900 -0.5159 -0.4437 0.7328
2.2421 -4.6337 5.1587 -0.7547 -0.6454 -0.1179
5.7535 2.5129 -5.0561 -0.3182 0.7694 0.5539
4.1264 4.6845 2.1099 -0.3702 0.8896 -0.2674
-3.1523 -4.7312 -3.9055 0.3396 -0.8147 0.4700
-5.6320 -1.9333 5.9974 0.2855 -0.6914 -0.6636
7.0288 -0.6008 -3.0655 -0.7243 0.3461 0.5964
-7.1868 -0.1440 -0.2064 0.8687 -0.4140 -0.2720
-0.8550 5.0871 -4.9983 0.6020 0.7866 0.1369

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.935
_diffrn_reflns_theta_min         3.982
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  15.00   1.00    1.00    --  -41.19  99.00 124.00   96
  2  ω      6.00  81.00   1.00    1.00    --   41.19 -99.00  18.00   75
  3  ω    104.00 178.00   1.00    1.00    --  112.00  99.00 124.00   74
  4  ω     32.00 107.00   1.00    1.00    --  112.00 -99.00  18.00   75
  5  ω   -115.00 -17.00   1.00    1.00    --  -41.19 -38.00-180.00   98
  6  ω      7.00  33.00   1.00    1.00    --   41.19  84.00-110.63   26
  7  ω     17.00 115.00   1.00    1.00    --   41.19  38.00  60.00   98
  8  ω     17.00 115.00   1.00    1.00    --   41.19  38.00  60.00   98
  9  ω     39.00 109.00   1.00    1.00    --  112.00-111.00 120.00   70
 10  ω    103.00 178.00   1.00    1.00    --  112.00  77.00  90.00   75
 11  ω     61.00 146.00   1.00    1.00    --  112.00 178.00 -90.00   85
 12  ω     39.00 138.00   1.00    1.00    --  112.00 -45.00 120.00   99
 13  ω     36.00 145.00   1.00    1.00    --  112.00 -77.00  30.00  109
 14  ω     36.00 145.00   1.00    1.00    --  112.00 -77.00  30.00  109
 15  ω     39.00 138.00   1.00    1.00    --  112.00 -45.00   0.00   99
 16  ω     39.00 109.00   1.00    1.00    --  112.00-111.00 -60.00   70
 17  ω     84.00 178.00   1.00    1.00    --  112.00  30.00 120.00   94
 18  ω     84.00 178.00   1.00    1.00    --  112.00  30.00 120.00   94
 19  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00-150.00  101
 20  ω     30.00 106.00   1.00    1.00    --  112.00 -95.00  30.00   76
 21  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00-150.00  101
 22  ω     39.00 138.00   1.00    1.00    --  112.00 -45.00 120.00   99
 23  ω    103.00 178.00   1.00    1.00    --  112.00  77.00-180.00   75
 24  ω     59.00 178.00   1.00    1.00    --  112.00  15.00   0.00  119
 25  ω     59.00 178.00   1.00    1.00    --  112.00  15.00   0.00  119
 26  ω     39.00  89.00   1.00    1.00    --  112.00 -45.00   0.00   50
 27  ω     66.00 100.00   1.00    1.00    --  112.00 178.00 -90.00   34
 28  ω    139.00 177.00   1.00    1.00    --  112.00  30.00  90.00   38
 29  ω     44.00  90.00   1.00    1.00    --  112.00 -45.00  60.00   46
 30  ω     48.00  73.00   1.00    1.00    --  112.00-111.00 -30.00   25
 31  ω     73.00  98.00   1.00    1.00    --  112.00-111.00   0.00   25
 32  ω     68.00  94.00   1.00    1.00    --  112.00 -50.00-123.82   26
 33  ω    114.00 140.00   1.00    1.00    --  112.00 111.00   0.00   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      -0.1204404000
_diffrn_orient_matrix_UB_12      0.0493976000
_diffrn_orient_matrix_UB_13      -0.0495706000
_diffrn_orient_matrix_UB_21      0.0550829000
_diffrn_orient_matrix_UB_22      0.1484644000
_diffrn_orient_matrix_UB_23      -0.0157019000
_diffrn_orient_matrix_UB_31      0.0414676000
_diffrn_orient_matrix_UB_32      -0.0535344000
_diffrn_orient_matrix_UB_33      -0.0889696000
_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                3121
_reflns_number_total             3234
_reflns_odcompleteness_completeness 98.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.86
_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 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.90 64-bit (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0022(3)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.056
_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)+(0.0400P)²+0.6790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0858
_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:
 C5(H5), C11(H11), C8(H8), C6(H6), C15(H15), C21(H21), C17(H17), C14(H14),
 C12(H12), C7(H7), C13(H13), C20(H20), C19(H19), C18(H18)
;
_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
O1 O 0.17766(7) 0.50885(8) 0.22706(5) 0.01924(18) Uani 1 1 d . . . . .
O2 O 0.12600(7) 0.21936(9) 0.14457(5) 0.02267(19) Uani 1 1 d . . . . .
N1 N 0.26538(8) 0.37534(9) 0.34609(6) 0.01478(19) Uani 1 1 d . . . . .
N2 N 0.16831(8) 0.58544(10) 0.30877(6) 0.0180(2) Uani 1 1 d . . . . .
C10 C 0.22020(9) 0.55217(11) 0.46700(7) 0.0162(2) Uani 1 1 d . . . . .
C9 C 0.21358(9) 0.24339(11) 0.37483(7) 0.0146(2) Uani 1 1 d . . . . .
C1 C 0.21494(9) 0.50582(11) 0.37292(7) 0.0156(2) Uani 1 1 d . . . . .
C16 C 0.36160(9) 0.38031(11) 0.20195(6) 0.0156(2) Uani 1 1 d . . . . .
C3 C 0.16778(9) 0.24561(12) 0.22017(7) 0.0163(2) Uani 1 1 d . . . . .
C5 C 0.10253(9) 0.03413(12) 0.31555(7) 0.0179(2) Uani 1 1 d . . . . .
H5 H 0.065331 -0.018683 0.266237 0.021 Uiso 1 1 calc R U . . .
C11 C 0.12222(10) 0.62432(11) 0.49715(7) 0.0181(2) Uani 1 1 d . . . . .
H11 H 0.050847 0.638634 0.458200 0.022 Uiso 1 1 calc R U . . .
C8 C 0.21550(9) 0.19267(12) 0.46174(7) 0.0173(2) Uani 1 1 d . . . . .
H8 H 0.253813 0.244862 0.510903 0.021 Uiso 1 1 calc R U . . .
C4 C 0.15808(9) 0.16532(12) 0.30284(7) 0.0156(2) Uani 1 1 d . . . . .
C22 C 0.24581(9) 0.38007(11) 0.24695(7) 0.0154(2) Uani 1 1 d . . . . .
C6 C 0.10303(10) -0.01721(12) 0.40204(7) 0.0195(2) Uani 1 1 d . . . . .
H6 H 0.065433 -0.106241 0.412662 0.023 Uiso 1 1 calc R U . . .
C15 C 0.32447(10) 0.52970(12) 0.52462(7) 0.0201(2) Uani 1 1 d . . . . .
H15 H 0.390556 0.479054 0.504410 0.024 Uiso 1 1 calc R U . . .
C21 C 0.39777(10) 0.49892(12) 0.15562(7) 0.0204(2) Uani 1 1 d . . . . .
H21 H 0.350002 0.583528 0.151759 0.024 Uiso 1 1 calc R U . . .
C17 C 0.43171(10) 0.25657(13) 0.20669(8) 0.0219(2) Uani 1 1 d . . . . .
H17 H 0.407220 0.175237 0.238480 0.026 Uiso 1 1 calc R U . . .
C14 C 0.33122(11) 0.58181(13) 0.61181(8) 0.0226(2) Uani 1 1 d . . . . .
H14 H 0.402445 0.567819 0.650978 0.027 Uiso 1 1 calc R U . . .
C12 C 0.12982(10) 0.67507(12) 0.58449(8) 0.0217(2) Uani 1 1 d . . . . .
H12 H 0.063387 0.724298 0.605260 0.026 Uiso 1 1 calc R U . . .
C7 C 0.15868(10) 0.06154(12) 0.47387(7) 0.0191(2) Uani 1 1 d . . . . .
H7 H 0.157795 0.024661 0.532763 0.023 Uiso 1 1 calc R U . . .
C13 C 0.23399(11) 0.65421(12) 0.64161(7) 0.0221(2) Uani 1 1 d . . . . .
H13 H 0.238730 0.689552 0.701175 0.027 Uiso 1 1 calc R U . . .
C20 C 0.50462(11) 0.49338(14) 0.11474(8) 0.0254(3) Uani 1 1 d . . . . .
H20 H 0.529947 0.575001 0.083623 0.030 Uiso 1 1 calc R U . . .
C19 C 0.57404(10) 0.37010(15) 0.11908(8) 0.0269(3) Uani 1 1 d . . . . .
H19 H 0.646410 0.366684 0.090690 0.032 Uiso 1 1 calc R U . . .
C18 C 0.53732(11) 0.25159(15) 0.16511(8) 0.0272(3) Uani 1 1 d . . . . .
H18 H 0.584636 0.166629 0.168206 0.033 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
O1 N2 1.4323(11) . ?
O1 C22 1.4358(12) . ?
O2 C3 1.2094(13) . ?
N1 C9 1.4424(13) . ?
N1 C1 1.4146(13) . ?
N1 C22 1.4845(12) . ?
N2 C1 1.2848(14) . ?
C10 C1 1.4733(14) . ?
C10 C11 1.3961(15) . ?
C10 C15 1.3957(15) . ?
C9 C8 1.3865(14) . ?
C9 C4 1.3964(14) . ?
C16 C22 1.5158(14) . ?
C16 C21 1.3869(15) . ?
C16 C17 1.3909(15) . ?
C3 C4 1.4629(14) . ?
C3 C22 1.5556(14) . ?
C5 H5 0.9500 . ?
C5 C4 1.3918(15) . ?
C5 C6 1.3840(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3893(15) . ?
C8 H8 0.9500 . ?
C8 C7 1.3965(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3985(16) . ?
C15 H15 0.9500 . ?
C15 C14 1.3918(15) . ?
C21 H21 0.9500 . ?
C21 C20 1.3946(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3876(16) . ?
C14 H14 0.9500 . ?
C14 C13 1.3884(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3885(17) . ?
C7 H7 0.9500 . ?
C13 H13 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.3832(18) . ?
C19 H19 0.9500 . ?
C19 C18 1.3858(18) . ?
C18 H18 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
N2 O1 C22 108.65(7) . . ?
C9 N1 C22 107.57(8) . . ?
C1 N1 C9 117.70(8) . . ?
C1 N1 C22 103.70(8) . . ?
C1 N2 O1 107.27(8) . . ?
C11 C10 C1 119.58(9) . . ?
C15 C10 C1 120.19(9) . . ?
C15 C10 C11 120.16(10) . . ?
C8 C9 N1 127.06(9) . . ?
C8 C9 C4 121.08(10) . . ?
C4 C9 N1 111.86(9) . . ?
N1 C1 C10 123.07(9) . . ?
N2 C1 N1 115.18(9) . . ?
N2 C1 C10 121.68(10) . . ?
C21 C16 C22 121.85(10) . . ?
C21 C16 C17 119.74(10) . . ?
C17 C16 C22 118.40(9) . . ?
O2 C3 C4 129.79(10) . . ?
O2 C3 C22 124.05(9) . . ?
C4 C3 C22 106.17(8) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C6 C5 C4 118.13(10) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.55(10) . . ?
C12 C11 H11 120.2 . . ?
C9 C8 H8 121.4 . . ?
C9 C8 C7 117.12(10) . . ?
C7 C8 H8 121.4 . . ?
C9 C4 C3 109.08(9) . . ?
C5 C4 C9 121.37(9) . . ?
C5 C4 C3 129.53(10) . . ?
O1 C22 N1 104.84(8) . . ?
O1 C22 C16 111.29(8) . . ?
O1 C22 C3 110.34(8) . . ?
N1 C22 C16 113.56(8) . . ?
N1 C22 C3 105.00(8) . . ?
C16 C22 C3 111.45(8) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.23(10) . . ?
C7 C6 H6 119.9 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.73(10) . . ?
C14 C15 H15 120.1 . . ?
C16 C21 H21 120.2 . . ?
C16 C21 C20 119.67(11) . . ?
C20 C21 H21 120.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.18(11) . . ?
C18 C17 H17 119.9 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.07(10) . . ?
C13 C14 H14 120.0 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.36(10) . . ?
C13 C12 H12 119.8 . . ?
C8 C7 C6 122.07(10) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C14 C13 C12 120.12(10) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.59(11) . . ?
C19 C20 H20 119.7 . . ?
C20 C19 H19 120.2 . . ?
C20 C19 C18 119.56(10) . . ?
C18 C19 H19 120.2 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.25(11) . . ?
C19 C18 H18 119.9 . . ?

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
O1 N2 C1 N1 3.02(12) . . . . ?
O1 N2 C1 C10 -179.94(8) . . . . ?
O2 C3 C4 C9 -175.39(11) . . . . ?
O2 C3 C4 C5 3.19(19) . . . . ?
O2 C3 C22 O1 61.70(13) . . . . ?
O2 C3 C22 N1 174.17(10) . . . . ?
O2 C3 C22 C16 -62.47(13) . . . . ?
N1 C9 C8 C7 179.72(9) . . . . ?
N1 C9 C4 C3 -1.46(12) . . . . ?
N1 C9 C4 C5 179.82(9) . . . . ?
N2 O1 C22 N1 6.05(10) . . . . ?
N2 O1 C22 C16 -117.12(8) . . . . ?
N2 O1 C22 C3 118.62(8) . . . . ?
C10 C11 C12 C13 -0.05(16) . . . . ?
C10 C15 C14 C13 0.82(17) . . . . ?
C9 N1 C1 N2 -117.83(10) . . . . ?
C9 N1 C1 C10 65.17(13) . . . . ?
C9 N1 C22 O1 121.21(8) . . . . ?
C9 N1 C22 C16 -117.10(9) . . . . ?
C9 N1 C22 C3 4.89(10) . . . . ?
C9 C8 C7 C6 0.69(16) . . . . ?
C1 N1 C9 C8 -66.15(13) . . . . ?
C1 N1 C9 C4 114.18(10) . . . . ?
C1 N1 C22 O1 -4.17(10) . . . . ?
C1 N1 C22 C16 117.51(9) . . . . ?
C1 N1 C22 C3 -120.49(8) . . . . ?
C1 C10 C11 C12 -176.41(10) . . . . ?
C1 C10 C15 C14 176.01(10) . . . . ?
C16 C21 C20 C19 0.78(17) . . . . ?
C16 C17 C18 C19 0.40(18) . . . . ?
C5 C6 C7 C8 -0.23(16) . . . . ?
C11 C10 C1 N1 -143.10(10) . . . . ?
C11 C10 C1 N2 40.09(15) . . . . ?
C11 C10 C15 C14 -1.16(16) . . . . ?
C11 C12 C13 C14 -0.28(17) . . . . ?
C8 C9 C4 C3 178.84(9) . . . . ?
C8 C9 C4 C5 0.12(15) . . . . ?
C4 C9 C8 C7 -0.63(15) . . . . ?
C4 C3 C22 O1 -118.17(9) . . . . ?
C4 C3 C22 N1 -5.70(10) . . . . ?
C4 C3 C22 C16 117.66(9) . . . . ?
C4 C5 C6 C7 -0.30(15) . . . . ?
C22 O1 N2 C1 -5.74(11) . . . . ?
C22 N1 C9 C8 177.31(10) . . . . ?
C22 N1 C9 C4 -2.36(11) . . . . ?
C22 N1 C1 N2 0.78(11) . . . . ?
C22 N1 C1 C10 -176.22(9) . . . . ?
C22 C16 C21 C20 -179.47(10) . . . . ?
C22 C16 C17 C18 178.92(10) . . . . ?
C22 C3 C4 C9 4.47(11) . . . . ?
C22 C3 C4 C5 -176.95(10) . . . . ?
C6 C5 C4 C9 0.35(15) . . . . ?
C6 C5 C4 C3 -178.08(10) . . . . ?
C15 C10 C1 N1 39.71(15) . . . . ?
C15 C10 C1 N2 -137.10(11) . . . . ?
C15 C10 C11 C12 0.77(16) . . . . ?
C15 C14 C13 C12 -0.11(17) . . . . ?
C21 C16 C22 O1 5.77(13) . . . . ?
C21 C16 C22 N1 -112.25(11) . . . . ?
C21 C16 C22 C3 129.41(10) . . . . ?
C21 C16 C17 C18 -0.13(17) . . . . ?
C21 C20 C19 C18 -0.50(18) . . . . ?
C17 C16 C22 O1 -173.25(9) . . . . ?
C17 C16 C22 N1 68.73(12) . . . . ?
C17 C16 C22 C3 -49.62(12) . . . . ?
C17 C16 C21 C20 -0.46(16) . . . . ?
C20 C19 C18 C17 -0.09(18) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted on the glass stick by acrylic glue.'
_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.810
