# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_dc1
_database_code_depnum_ccdc_archive 'CCDC 2301657'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2023-12-27 downloaded from the CCDC.
;
_audit_creation_date             2023-12-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C16 H10 N8), 0.5(C4 H6 N2)'
_chemical_formula_sum            'C50 H33 N25'
_chemical_formula_weight         984.01
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   21.273(4)
_cell_length_b                   7.2489(12)
_cell_length_c                   15.064(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2322.9(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1117
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.1873
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6837
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_min         2.704
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                1720
_reflns_number_total             4592
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.146
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.717
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4592
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1546
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      0.745
_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)+(0.0133P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0456
_refine_ls_wR_factor_ref         0.0579
_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. Uiso/Uaniso restraints and constraints
Uanis(C2S) \\sim Ueq, Uanis(C1S) \\sim Ueq, Uanis(N1S) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H2SA(0.5) H2SB(0.5) H2SC(0.5)
4.a Riding coordinates:
 C2S(H2SA,H2SB,H2SC)
4.b Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C12(H12), C8(H8), C4A(H4A), C16(H16), C15(H15), C13(H13), C14(H14),
 C4(H4), C7A(H7A), C7(H7), C5A(H5A), C6A(H6A), C6(H6), C5(H5)
;
_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
N3A N 0.52802(16) 0.9538(4) 0.3433(2) 0.0366(10) Uani 1 1 d . . . . .
N7 N 0.34233(19) 0.5485(5) 0.3921(2) 0.0365(10) Uani 1 1 d . . . . .
N3 N 0.29397(19) 0.4575(5) 0.4332(2) 0.0369(10) Uani 1 1 d . . . . .
N6 N 0.4130(2) 0.6769(5) 0.3100(2) 0.0511(12) Uani 1 1 d . . . . .
N5 N 0.43866(19) 0.6541(5) 0.3925(2) 0.0548(11) Uani 1 1 d . . . . .
N2 N 0.20988(19) 0.3365(5) 0.4884(2) 0.0518(12) Uani 1 1 d . . . . .
N8 N 0.4016(2) 0.5337(5) 0.5304(2) 0.0556(13) Uani 1 1 d . . . . .
N1A N 0.6097(2) 0.8477(5) 0.4144(3) 0.0573(12) Uani 1 1 d . . . . .
N4 N 0.3551(2) 0.4615(5) 0.5709(2) 0.0586(12) Uani 1 1 d . . . . .
N4A N 0.52713(17) 0.9631(5) 0.50554(19) 0.0581(13) Uani 1 1 d . . . . .
N2A N 0.6180(2) 0.8256(5) 0.3254(3) 0.0551(12) Uani 1 1 d . . . . .
C10 C 0.3548(3) 0.6148(6) 0.3091(3) 0.0410(13) Uani 1 1 d . . . . .
N1 N 0.2512(2) 0.3547(5) 0.5569(2) 0.0572(13) Uani 1 1 d . . . . .
C2 C 0.2352(2) 0.3983(6) 0.4128(3) 0.0435(13) Uani 1 1 d . . . . .
C1A C 0.5547(3) 0.9253(6) 0.4251(3) 0.0469(13) Uani 1 1 d . . . . .
C3A C 0.5645(2) 0.8738(6) 0.1882(3) 0.0414(13) Uani 1 1 d . . . . .
C11 C 0.3169(2) 0.6303(6) 0.2298(3) 0.0368(12) Uani 1 1 d . . . . .
C2A C 0.5693(2) 0.8881(6) 0.2822(3) 0.0408(13) Uani 1 1 d . . . . .
C3 C 0.2032(2) 0.3825(6) 0.3282(3) 0.0405(13) Uani 1 1 d . . . . .
C8A C 0.5171(2) 0.7776(5) 0.1494(3) 0.0481(13) Uani 1 1 d . . . . .
H8A H 0.484725 0.729932 0.183990 0.058 Uiso 1 1 calc R U . . .
C1 C 0.3017(3) 0.4266(6) 0.5237(3) 0.0438(13) Uani 1 1 d . . . . .
C9 C 0.3953(3) 0.5767(6) 0.4404(3) 0.0458(13) Uani 1 1 d . . . . .
C12 C 0.2615(2) 0.7269(6) 0.2295(3) 0.0463(13) Uani 1 1 d . . . . .
H12 H 0.244499 0.770977 0.282278 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2292(2) 0.2872(6) 0.2600(3) 0.0475(14) Uani 1 1 d . . . . .
H8 H 0.269603 0.239182 0.264602 0.057 Uiso 1 1 calc R U . . .
C4A C 0.6131(2) 0.9428(6) 0.1389(3) 0.0538(14) Uani 1 1 d . . . . .
H4A H 0.645908 1.005260 0.166447 0.065 Uiso 1 1 calc R U . . .
C16 C 0.3429(2) 0.5659(6) 0.1529(3) 0.0514(14) Uani 1 1 d . . . . .
H16 H 0.380735 0.501496 0.154142 0.062 Uiso 1 1 calc R U . . .
C15 C 0.3126(3) 0.5976(7) 0.0737(3) 0.0614(16) Uani 1 1 d . . . . .
H15 H 0.329562 0.553324 0.020963 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2314(2) 0.7578(6) 0.1508(3) 0.0608(15) Uani 1 1 d . . . . .
H13 H 0.193501 0.821476 0.149830 0.073 Uiso 1 1 calc R U . . .
C14 C 0.2574(3) 0.6947(6) 0.0728(3) 0.0663(17) Uani 1 1 d . . . . .
H14 H 0.237257 0.718006 0.019173 0.080 Uiso 1 1 calc R U . . .
C4 C 0.1439(3) 0.4522(7) 0.3212(3) 0.0671(16) Uani 1 1 d . . . . .
H4 H 0.126628 0.517055 0.368499 0.081 Uiso 1 1 calc R U . . .
C7A C 0.5170(3) 0.7503(6) 0.0586(3) 0.0645(16) Uani 1 1 d . . . . .
H7A H 0.484806 0.683603 0.031838 0.077 Uiso 1 1 calc R U . . .
C7 C 0.1948(3) 0.2632(7) 0.1845(3) 0.0720(18) Uani 1 1 d . . . . .
H7 H 0.212144 0.198406 0.137192 0.086 Uiso 1 1 calc R U . . .
C5A C 0.6130(3) 0.9189(7) 0.0480(3) 0.0699(18) Uani 1 1 d . . . . .
H5A H 0.645357 0.967538 0.013789 0.084 Uiso 1 1 calc R U . . .
C6A C 0.5649(3) 0.8230(7) 0.0083(3) 0.0702(18) Uani 1 1 d . . . . .
H6A H 0.564750 0.807187 -0.052916 0.084 Uiso 1 1 calc R U . . .
C6 C 0.1364(4) 0.3318(9) 0.1774(4) 0.093(2) Uani 1 1 d . . . . .
H6 H 0.113824 0.313520 0.125273 0.112 Uiso 1 1 calc R U . . .
C5 C 0.1096(3) 0.4280(9) 0.2457(4) 0.097(2) Uani 1 1 d . . . . .
H5 H 0.069097 0.475561 0.240814 0.116 Uiso 1 1 calc R U . . .
C2S C 0.500000 0.500000 0.6956(4) 0.215(6) Uani 1 2 d S TU P . .
H2SA H 0.504450 0.624170 0.674397 0.323 Uiso 0.5 1 d R U P A -1
H2SB H 0.461130 0.449230 0.674397 0.323 Uiso 0.5 1 d R U P A -1
H2SC H 0.534420 0.426600 0.674397 0.323 Uiso 0.5 1 d R U P A -1
N1S N 0.500000 0.500000 0.8544(5) 0.230(6) Uani 1 2 d S TU P . .
C1S C 0.500000 0.500000 0.7843(6) 0.150(5) Uani 1 2 d S TU P . .


_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
N3A N3A 1.368(6) 2_675 ?
N3A C1A 1.372(5) . ?
N3A C2A 1.359(5) . ?
N7 N3 1.370(4) . ?
N7 C10 1.365(4) . ?
N7 C9 1.357(5) . ?
N3 C2 1.357(5) . ?
N3 C1 1.392(4) . ?
N6 N5 1.367(4) . ?
N6 C10 1.319(6) . ?
N5 C9 1.298(5) . ?
N2 N1 1.361(5) . ?
N2 C2 1.338(5) . ?
N8 N4 1.274(5) . ?
N8 C9 1.397(4) . ?
N1A N2A 1.362(4) . ?
N1A C1A 1.308(5) . ?
N4 C1 1.365(5) . ?
N4A N4A 1.272(7) 2_675 ?
N4A C1A 1.373(5) . ?
N2A C2A 1.306(5) . ?
C10 C11 1.446(5) . ?
N1 C1 1.295(5) . ?
C2 C3 1.449(6) . ?
C3A C2A 1.423(5) . ?
C3A C8A 1.358(5) . ?
C3A C4A 1.367(6) . ?
C11 C12 1.371(5) . ?
C11 C16 1.366(5) . ?
C3 C8 1.357(5) . ?
C3 C4 1.363(6) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.382(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.362(6) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.380(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.376(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.370(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.362(6) . ?
C7A H7A 0.9300 . ?
C7A C6A 1.375(6) . ?
C7 H7 0.9300 . ?
C7 C6 1.343(7) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.374(6) . ?
C6A H6A 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.368(7) . ?
C5 H5 0.9300 . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 0.9601 . ?
C2S C1S 1.335(8) . ?
N1S C1S 1.056(9) . ?

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
N3A N3A C1A 115.7(3) 2_675 . ?
C2A N3A N3A 137.3(2) . 2_675 ?
C2A N3A C1A 106.8(4) . . ?
C10 N7 N3 136.7(4) . . ?
C9 N7 N3 117.0(4) . . ?
C9 N7 C10 106.1(4) . . ?
N7 N3 C1 115.6(4) . . ?
C2 N3 N7 137.9(4) . . ?
C2 N3 C1 106.2(4) . . ?
C10 N6 N5 110.0(4) . . ?
C9 N5 N6 105.9(4) . . ?
C2 N2 N1 110.7(4) . . ?
N4 N8 C9 118.9(4) . . ?
C1A N1A N2A 106.8(4) . . ?
N8 N4 C1 118.2(4) . . ?
N4A N4A C1A 118.1(3) 2_675 . ?
C2A N2A N1A 110.2(4) . . ?
N7 C10 C11 132.6(5) . . ?
N6 C10 N7 107.0(4) . . ?
N6 C10 C11 120.4(4) . . ?
C1 N1 N2 106.4(4) . . ?
N3 C2 C3 131.1(4) . . ?
N2 C2 N3 106.5(4) . . ?
N2 C2 C3 122.2(4) . . ?
N3A C1A N4A 125.9(5) . . ?
N1A C1A N3A 108.9(4) . . ?
N1A C1A N4A 125.2(4) . . ?
C8A C3A C2A 121.2(4) . . ?
C8A C3A C4A 121.0(4) . . ?
C4A C3A C2A 117.3(5) . . ?
C12 C11 C10 121.5(4) . . ?
C16 C11 C10 116.6(4) . . ?
C16 C11 C12 121.3(4) . . ?
N3A C2A C3A 130.8(5) . . ?
N2A C2A N3A 107.3(3) . . ?
N2A C2A C3A 121.8(5) . . ?
C8 C3 C2 121.0(5) . . ?
C8 C3 C4 120.4(4) . . ?
C4 C3 C2 118.4(4) . . ?
C3A C8A H8A 120.0 . . ?
C3A C8A C7A 120.1(5) . . ?
C7A C8A H8A 120.0 . . ?
N4 C1 N3 125.4(5) . . ?
N1 C1 N3 110.2(5) . . ?
N1 C1 N4 124.4(4) . . ?
N7 C9 N8 124.4(5) . . ?
N5 C9 N7 110.9(4) . . ?
N5 C9 N8 124.6(5) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.3(4) . . ?
C13 C12 H12 120.4 . . ?
C3 C8 H8 120.7 . . ?
C3 C8 C7 118.6(5) . . ?
C7 C8 H8 120.7 . . ?
C3A C4A H4A 120.3 . . ?
C3A C4A C5A 119.4(5) . . ?
C5A C4A H4A 120.3 . . ?
C11 C16 H16 120.4 . . ?
C11 C16 C15 119.2(4) . . ?
C15 C16 H16 120.4 . . ?
C16 C15 H15 120.1 . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.5 . . ?
C8A C7A H7A 120.4 . . ?
C6A C7A C8A 119.3(5) . . ?
C6A C7A H7A 120.4 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.1(6) . . ?
C6 C7 H7 119.5 . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A C4A 119.8(5) . . ?
C6A C5A H5A 120.1 . . ?
C7A C6A H6A 119.8 . . ?
C5A C6A C7A 120.4(5) . . ?
C5A C6A H6A 119.8 . . ?
C7 C6 H6 119.5 . . ?
C7 C6 C5 121.0(6) . . ?
C5 C6 H6 119.5 . . ?
C4 C5 C6 118.0(6) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
N1S C1S C2S 180.0 . . ?

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
N3A N3A C1A N1A -175.6(5) 2_675 . . . ?
N3A N3A C1A N4A 7.4(7) 2_675 . . . ?
N3A N3A C2A N2A 174.3(6) 2_675 . . . ?
N3A N3A C2A C3A -8.7(10) 2_675 . . . ?
N7 N3 C2 N2 -172.8(4) . . . . ?
N7 N3 C2 C3 12.4(9) . . . . ?
N7 N3 C1 N4 -7.3(7) . . . . ?
N7 N3 C1 N1 174.4(4) . . . . ?
N7 C10 C11 C12 57.6(8) . . . . ?
N7 C10 C11 C16 -131.0(5) . . . . ?
N3 N7 C10 N6 -174.9(4) . . . . ?
N3 N7 C10 C11 7.1(9) . . . . ?
N3 N7 C9 N5 176.2(4) . . . . ?
N3 N7 C9 N8 -5.8(6) . . . . ?
N3 C2 C3 C8 53.9(7) . . . . ?
N3 C2 C3 C4 -131.7(5) . . . . ?
N6 N5 C9 N7 -0.1(5) . . . . ?
N6 N5 C9 N8 -178.1(4) . . . . ?
N6 C10 C11 C12 -120.1(5) . . . . ?
N6 C10 C11 C16 51.3(6) . . . . ?
N5 N6 C10 N7 -0.6(5) . . . . ?
N5 N6 C10 C11 177.7(4) . . . . ?
N2 N1 C1 N3 0.4(6) . . . . ?
N2 N1 C1 N4 -177.9(4) . . . . ?
N2 C2 C3 C8 -120.2(5) . . . . ?
N2 C2 C3 C4 54.2(6) . . . . ?
N8 N4 C1 N3 2.3(7) . . . . ?
N8 N4 C1 N1 -179.7(5) . . . . ?
N1A N2A C2A N3A 0.4(5) . . . . ?
N1A N2A C2A C3A -176.9(4) . . . . ?
N4 N8 C9 N7 0.7(7) . . . . ?
N4 N8 C9 N5 178.4(5) . . . . ?
N4A N4A C1A N3A -2.5(8) 2_675 . . . ?
N4A N4A C1A N1A -179.0(5) 2_675 . . . ?
N2A N1A C1A N3A -0.3(5) . . . . ?
N2A N1A C1A N4A 176.7(4) . . . . ?
C10 N7 N3 C2 -3.9(9) . . . . ?
C10 N7 N3 C1 -176.5(5) . . . . ?
C10 N7 C9 N5 -0.3(5) . . . . ?
C10 N7 C9 N8 177.7(4) . . . . ?
C10 N6 N5 C9 0.4(5) . . . . ?
C10 C11 C12 C13 171.6(4) . . . . ?
C10 C11 C16 C15 -171.9(4) . . . . ?
N1 N2 C2 N3 -0.1(5) . . . . ?
N1 N2 C2 C3 175.3(4) . . . . ?
C2 N3 C1 N4 177.8(5) . . . . ?
C2 N3 C1 N1 -0.4(5) . . . . ?
C2 N2 N1 C1 -0.2(5) . . . . ?
C2 C3 C8 C7 174.5(4) . . . . ?
C2 C3 C4 C5 -174.6(5) . . . . ?
C1A N3A C2A N2A -0.6(5) . . . . ?
C1A N3A C2A C3A 176.4(5) . . . . ?
C1A N1A N2A C2A -0.1(6) . . . . ?
C3A C8A C7A C6A -0.6(8) . . . . ?
C3A C4A C5A C6A -1.4(8) . . . . ?
C11 C12 C13 C14 -1.0(7) . . . . ?
C11 C16 C15 C14 0.8(7) . . . . ?
C2A N3A C1A N1A 0.5(5) . . . . ?
C2A N3A C1A N4A -176.5(5) . . . . ?
C2A C3A C8A C7A -173.6(4) . . . . ?
C2A C3A C4A C5A 174.8(4) . . . . ?
C3 C8 C7 C6 -0.2(9) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C8A C3A C2A N3A -57.6(7) . . . . ?
C8A C3A C2A N2A 119.0(6) . . . . ?
C8A C3A C4A C5A 1.9(8) . . . . ?
C8A C7A C6A C5A 1.1(9) . . . . ?
C1 N3 C2 N2 0.3(5) . . . . ?
C1 N3 C2 C3 -174.5(4) . . . . ?
C9 N7 N3 C2 -178.9(5) . . . . ?
C9 N7 N3 C1 8.4(6) . . . . ?
C9 N7 C10 N6 0.5(5) . . . . ?
C9 N7 C10 C11 -177.4(5) . . . . ?
C9 N8 N4 C1 1.2(6) . . . . ?
C12 C11 C16 C15 -0.6(7) . . . . ?
C12 C13 C14 C15 1.3(8) . . . . ?
C8 C3 C4 C5 -0.1(8) . . . . ?
C8 C7 C6 C5 0.1(10) . . . . ?
C4A C3A C2A N3A 129.6(6) . . . . ?
C4A C3A C2A N2A -53.9(6) . . . . ?
C4A C3A C8A C7A -1.0(8) . . . . ?
C4A C5A C6A C7A -0.2(9) . . . . ?
C16 C11 C12 C13 0.7(7) . . . . ?
C16 C15 C14 C13 -1.2(8) . . . . ?
C4 C3 C8 C7 0.2(7) . . . . ?
C7 C6 C5 C4 0.0(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 2301658'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-10-17 deposited with the CCDC.	2023-12-27 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_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         'C20 H18 N8 O4, C6 H6 O2, 1(C3 H3)'
_chemical_formula_sum            'C29 H27 N8 O6'
_chemical_formula_weight         583.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   14.290(3)
_cell_length_b                   7.870(3)
_cell_length_c                   25.420(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.45(2)
_cell_angle_gamma                90
_cell_volume                     2811.2(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1913
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.19410
_exptl_absorpt_correction_T_min  0.86097
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.1484
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17062
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         2.713
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1913
_reflns_number_total             5705
_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       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5705
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.1729
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      0.889
_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)+(0.0050P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0453
_refine_ls_wR_factor_ref         0.0505
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-C24
 1.43 with sigma of 0.02
 C7S-C7S_$1
 1.43 with sigma of 0.02
 C8S-C8S_$1
 1.43 with sigma of 0.02
 C22-C21
 1.43 with sigma of 0.02
 C9S-C7S
 1.43 with sigma of 0.02
 C9S-C8S
 1.43 with sigma of 0.02
 C22-C23
 1.43 with sigma of 0.02
 C7S-C9S
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C21) \\sim Ueq, Uanis(C7S) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C9S)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C8S) \\sim Ueq, Uanis(C24) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C7S(0.6) H7S(0.6) C8S(0.6) H8S(0.6) C9S(0.6) H9S(0.6) C21(0.2)
 H21(0.2) C22(0.4) H22(0.4) C24(0.2) H24(0.2) C23(0.4) H23(0.4)
5.a Riding coordinates:
 O4(H5), O5(H6)
5.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
5.c Aromatic/amide H refined with riding coordinates:
 C2S(H2S), C4S(H4S), C5S(H5S), C6S(H6S), C8(H8), C9(H9), C10(H10), C14(H14),
 C15(H15), C16(H16), C7S(H7S), C8S(H8S), C9S(H9S), C21(H21), C22(H22), C24(H24),
  C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.62361(11) 0.6660(2) 0.07638(6) 0.0642(5) Uani 1 1 d . . . . .
N1 N 0.9199(2) 0.0819(3) -0.07001(10) 0.0795(8) Uani 1 1 d . . . . .
C1 C 0.8317(2) 0.0925(3) -0.05506(12) 0.0611(8) Uani 1 1 d . . . . .
O2 O 0.74337(10) 0.51196(18) 0.01892(6) 0.0548(4) Uani 1 1 d . . . . .
C2S C 0.7590(2) 0.6244(4) -0.15057(9) 0.0651(8) Uani 1 1 d . . . . .
H2S H 0.803217 0.703951 -0.134468 0.078 Uiso 1 1 calc R U . . .
N2 N 0.98867(19) 0.1658(3) -0.04265(12) 0.0860(8) Uani 1 1 d . . . . .
C2 C 0.9755(2) 0.2502(4) 0.00219(14) 0.0665(9) Uani 1 1 d . . . . .
O3 O 0.79716(11) 0.05379(19) 0.09228(6) 0.0568(5) Uani 1 1 d . . . . .
N3 N 1.04206(17) 0.3236(3) 0.03574(12) 0.0828(8) Uani 1 1 d . . . . .
C3 C 0.9123(2) 0.3184(3) 0.07157(12) 0.0537(7) Uani 1 1 d . . . . .
C3S C 0.7861(2) 0.4610(4) -0.15907(11) 0.0744(9) Uani 1 1 d . . . . .
O4 O 0.69702(12) 0.0671(2) 0.17293(7) 0.0748(5) Uani 1 1 d . . . . .
H5 H 0.674507 0.891529 -0.144173 0.090 Uiso 1 1 d R U . . .
N4 N 1.00195(17) 0.3670(3) 0.07855(9) 0.0707(7) Uani 1 1 d . . . . .
C4 C 0.71738(19) 0.1749(3) -0.01359(10) 0.0472(6) Uani 1 1 d . . . . .
C4S C 0.7224(3) 0.3431(3) -0.18348(12) 0.0896(10) Uani 1 1 d . . . . .
H4S H 0.741546 0.232895 -0.189432 0.108 Uiso 1 1 calc R U . . .
O5 O 0.63308(12) 0.8266(2) -0.15855(6) 0.0935(6) Uani 1 1 d . . . . .
H6 H 0.915627 0.492483 -0.123444 0.112 Uiso 1 1 d R U . . .
N5 N 0.7519(2) 0.0312(2) -0.08141(9) 0.0687(7) Uani 1 1 d . . . . .
C5 C 0.85481(17) 0.3316(3) 0.11254(10) 0.0515(7) Uani 1 1 d . . . . .
C5S C 0.6296(3) 0.3918(5) -0.19889(11) 0.0948(11) Uani 1 1 d . . . . .
H5S H 0.585494 0.312638 -0.215302 0.114 Uiso 1 1 calc R U . . .
N6 N 0.68110(15) 0.0828(2) -0.05556(9) 0.0631(6) Uani 1 1 d . . . . .
C6 C 0.80040(18) 0.1935(3) 0.12397(10) 0.0514(7) Uani 1 1 d . . . . .
O6 O 0.87756(15) 0.4093(2) -0.14350(8) 0.1218(8) Uani 1 1 d . . . . .
C6S C 0.5997(2) 0.5531(5) -0.19095(11) 0.0815(9) Uani 1 1 d . . . . .
H6S H 0.536363 0.583996 -0.202009 0.098 Uiso 1 1 calc R U . . .
N7 N 0.81385(17) 0.1824(2) -0.01175(8) 0.0490(5) Uani 1 1 d . . . . .
C1S C 0.6650(3) 0.6679(4) -0.16638(10) 0.0656(8) Uani 1 1 d . . . . .
C7 C 0.74875(18) 0.2063(4) 0.16546(10) 0.0587(7) Uani 1 1 d . . . . .
N8 N 0.89221(16) 0.2483(2) 0.02212(9) 0.0516(6) Uani 1 1 d . . . . .
C8 C 0.75474(19) 0.3546(4) 0.19531(10) 0.0737(8) Uani 1 1 d . . . . .
H8 H 0.720856 0.364161 0.223140 0.088 Uiso 1 1 calc R U . . .
C9 C 0.8105(2) 0.4881(3) 0.18408(11) 0.0721(9) Uani 1 1 d . . . . .
H9 H 0.813776 0.587295 0.204192 0.086 Uiso 1 1 calc R U . . .
C10 C 0.86096(18) 0.4749(3) 0.14358(11) 0.0619(8) Uani 1 1 d . . . . .
H10 H 0.899906 0.564104 0.136959 0.074 Uiso 1 1 calc R U . . .
C11 C 0.65859(17) 0.2553(3) 0.02011(9) 0.0484(7) Uani 1 1 d . . . . .
C12 C 0.66908(17) 0.4256(3) 0.03329(9) 0.0476(7) Uani 1 1 d . . . . .
C13 C 0.60778(18) 0.5010(3) 0.06358(10) 0.0546(7) Uani 1 1 d . . . . .
C14 C 0.53753(17) 0.4027(4) 0.07902(9) 0.0628(8) Uani 1 1 d . . . . .
H14 H 0.496005 0.451783 0.098873 0.075 Uiso 1 1 calc R U . . .
C15 C 0.52761(17) 0.2324(3) 0.06555(10) 0.0621(8) Uani 1 1 d . . . . .
H15 H 0.480565 0.167276 0.076755 0.075 Uiso 1 1 calc R U . . .
C16 C 0.58733(18) 0.1612(3) 0.03577(9) 0.0582(7) Uani 1 1 d . . . . .
H16 H 0.579893 0.047511 0.025877 0.070 Uiso 1 1 calc R U . . .
C17 C 0.56618(18) 0.7423(3) 0.10960(9) 0.0898(9) Uani 1 1 d . . . . .
H17A H 0.584385 0.859043 0.115707 0.135 Uiso 1 1 calc R U . . .
H17B H 0.500606 0.736351 0.092479 0.135 Uiso 1 1 calc R U . . .
H17C H 0.574542 0.683207 0.143171 0.135 Uiso 1 1 calc R U . . .
C18 C 0.72248(15) 0.6543(3) -0.01506(9) 0.0748(8) Uani 1 1 d . . . . .
H18A H 0.780681 0.702883 -0.021964 0.112 Uiso 1 1 calc R U . . .
H18B H 0.683815 0.619374 -0.048197 0.112 Uiso 1 1 calc R U . . .
H18C H 0.688734 0.737437 0.001903 0.112 Uiso 1 1 calc R U . . .
C19 C 0.83274(16) -0.1007(3) 0.11773(9) 0.0754(8) Uani 1 1 d . . . . .
H19A H 0.826945 -0.190205 0.091680 0.113 Uiso 1 1 calc R U . . .
H19B H 0.898473 -0.086451 0.133731 0.113 Uiso 1 1 calc R U . . .
H19C H 0.796750 -0.129396 0.144905 0.113 Uiso 1 1 calc R U . . .
C20 C 0.6456(2) 0.0721(3) 0.21526(11) 0.1236(12) Uani 1 1 d . . . . .
H20A H 0.612054 -0.033080 0.216469 0.185 Uiso 1 1 calc R U . . .
H20B H 0.688880 0.088487 0.248453 0.185 Uiso 1 1 calc R U . . .
H20C H 0.600917 0.164289 0.209682 0.185 Uiso 1 1 calc R U . . .
C7S C 0.9706(7) 0.1489(11) -0.2313(4) 0.098(4) Uani 0.6 1 d D U P A 1
H7S H 0.950254 0.250737 -0.218587 0.118 Uiso 0.6 1 calc R U P A 1
C8S C 0.9706(6) -0.1642(12) -0.2308(3) 0.089(3) Uani 0.6 1 d D U P A 1
H8S H 0.951201 -0.266410 -0.217901 0.107 Uiso 0.6 1 calc R U P A 1
C9S C 0.9411(8) -0.0112(9) -0.2121(5) 0.092(3) Uani 0.6 1 d D U P A 1
H9S H 0.901611 -0.011980 -0.186761 0.110 Uiso 0.6 1 calc R U P A 1
C21 C 1.000000 0.173(3) -0.250000 0.084(8) Uani 0.4 2 d DS TU P B 2
H21 H 1.000001 0.290877 -0.249999 0.101 Uiso 0.4 2 calc R U P B 2
C22 C 0.9512(10) 0.0818(13) -0.2189(6) 0.068(4) Uani 0.4 1 d D U P B 2
H22 H 0.915483 0.141450 -0.197825 0.082 Uiso 0.4 1 calc R U P B 2
C24 C 1.000000 -0.180(3) -0.250000 0.091(9) Uani 0.4 2 d DS TU P B 2
H24 H 0.999998 -0.297685 -0.250001 0.109 Uiso 0.4 2 calc R U P B 2
C23 C 0.9505(14) -0.0928(16) -0.2161(8) 0.096(6) Uani 0.4 1 d D U P B 2
H23 H 0.918579 -0.149928 -0.192618 0.116 Uiso 0.4 1 calc R U P B 2


_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 C13 1.348(2) . ?
O1 C17 1.414(2) . ?
N1 C1 1.383(3) . ?
N1 N2 1.280(3) . ?
C1 N5 1.306(3) . ?
C1 N7 1.371(3) . ?
O2 C12 1.365(2) . ?
O2 C18 1.413(2) . ?
C2S H2S 0.9300 . ?
C2S C3S 1.372(3) . ?
C2S C1S 1.373(3) . ?
N2 C2 1.361(3) . ?
C2 N3 1.293(3) . ?
C2 N8 1.376(3) . ?
O3 C6 1.359(2) . ?
O3 C19 1.427(2) . ?
N3 N4 1.362(3) . ?
C3 N4 1.317(3) . ?
C3 C5 1.443(3) . ?
C3 N8 1.355(3) . ?
C3S C4S 1.368(3) . ?
C3S O6 1.357(3) . ?
O4 C7 1.354(3) . ?
O4 C20 1.409(2) . ?
C4 N6 1.316(2) . ?
C4 N7 1.372(3) . ?
C4 C11 1.450(3) . ?
C4S H4S 0.9300 . ?
C4S C5S 1.367(3) . ?
O5 H5 0.8165 . ?
O5 C1S 1.357(3) . ?
N5 N6 1.364(3) . ?
C5 C6 1.397(3) . ?
C5 C10 1.370(3) . ?
C5S H5S 0.9300 . ?
C5S C6S 1.366(3) . ?
C6 C7 1.396(3) . ?
O6 H6 0.9399 . ?
C6S H6S 0.9300 . ?
C6S C1S 1.366(3) . ?
N7 N8 1.384(2) . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 C16 1.375(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.360(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C7S C7S 1.380(13) 2_754 ?
C7S H7S 0.9300 . ?
C7S C9S 1.441(10) . ?
C8S C8S 1.399(14) 2_754 ?
C8S H8S 0.9300 . ?
C8S C9S 1.388(11) . ?
C9S H9S 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.351(14) 2_754 ?
C21 C22 1.351(14) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(15) . ?
C24 H24 0.9300 . ?
C24 C23 1.390(16) . ?
C24 C23 1.390(16) 2_754 ?
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
C13 O1 C17 117.59(19) . . ?
N2 N1 C1 117.9(3) . . ?
N5 C1 N1 126.3(3) . . ?
N5 C1 N7 109.2(3) . . ?
N7 C1 N1 124.3(3) . . ?
C12 O2 C18 118.03(18) . . ?
C3S C2S H2S 120.8 . . ?
C3S C2S C1S 118.5(3) . . ?
C1S C2S H2S 120.8 . . ?
N1 N2 C2 119.8(3) . . ?
N2 C2 N8 124.3(3) . . ?
N3 C2 N2 125.0(3) . . ?
N3 C2 N8 110.1(3) . . ?
C6 O3 C19 116.72(18) . . ?
C2 N3 N4 105.9(3) . . ?
N4 C3 C5 123.3(3) . . ?
N4 C3 N8 106.3(2) . . ?
N8 C3 C5 130.2(3) . . ?
C4S C3S C2S 121.6(3) . . ?
O6 C3S C2S 121.3(3) . . ?
O6 C3S C4S 117.1(3) . . ?
C7 O4 C20 117.3(2) . . ?
C3 N4 N3 111.0(2) . . ?
N6 C4 N7 107.3(2) . . ?
N6 C4 C11 122.3(3) . . ?
N7 C4 C11 130.3(3) . . ?
C3S C4S H4S 121.0 . . ?
C5S C4S C3S 118.1(3) . . ?
C5S C4S H4S 121.0 . . ?
C1S O5 H5 113.9 . . ?
C1 N5 N6 107.4(2) . . ?
C6 C5 C3 120.4(3) . . ?
C10 C5 C3 119.3(3) . . ?
C10 C5 C6 120.0(2) . . ?
C4S C5S H5S 118.9 . . ?
C6S C5S C4S 122.1(3) . . ?
C6S C5S H5S 118.9 . . ?
C4 N6 N5 109.7(2) . . ?
O3 C6 C5 117.8(2) . . ?
O3 C6 C7 122.7(2) . . ?
C7 C6 C5 119.4(2) . . ?
C3S O6 H6 112.4 . . ?
C5S C6S H6S 120.8 . . ?
C5S C6S C1S 118.4(3) . . ?
C1S C6S H6S 120.8 . . ?
C1 N7 C4 106.4(2) . . ?
C1 N7 N8 116.5(2) . . ?
C4 N7 N8 137.0(2) . . ?
O5 C1S C2S 121.6(3) . . ?
O5 C1S C6S 117.1(3) . . ?
C6S C1S C2S 121.3(3) . . ?
O4 C7 C6 115.1(2) . . ?
O4 C7 C8 125.8(3) . . ?
C8 C7 C6 119.1(3) . . ?
C2 N8 N7 115.5(3) . . ?
C3 N8 C2 106.6(2) . . ?
C3 N8 N7 137.9(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C4 121.2(2) . . ?
C16 C11 C4 118.3(2) . . ?
C16 C11 C12 120.4(2) . . ?
O2 C12 C11 118.2(2) . . ?
O2 C12 C13 122.1(2) . . ?
C11 C12 C13 119.5(2) . . ?
O1 C13 C12 116.5(2) . . ?
O1 C13 C14 124.8(2) . . ?
C14 C13 C12 118.7(2) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.3(2) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.3 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7S C7S H7S 120.5 2_754 . ?
C7S C7S C9S 119.1(6) 2_754 . ?
C9S C7S H7S 120.5 . . ?
C8S C8S H8S 120.1 2_754 . ?
C9S C8S C8S 119.8(6) . 2_754 ?
C9S C8S H8S 120.1 . . ?
C7S C9S H9S 119.4 . . ?
C8S C9S C7S 121.1(11) . . ?
C8S C9S H9S 119.4 . . ?
C22 C21 H21 122.0 . . ?
C22 C21 H21 122.0 2_754 . ?
C22 C21 C22 116(2) 2_754 . ?
C21 C22 H22 117.7 . . ?
C21 C22 C23 124.6(16) . . ?
C23 C22 H22 117.7 . . ?
C23 C24 H24 119.4 2_754 . ?
C23 C24 H24 119.4 . . ?
C23 C24 C23 121(3) 2_754 . ?
C22 C23 C24 116.7(19) . . ?
C22 C23 H23 121.6 . . ?
C24 C23 H23 121.6 . . ?

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
O1 C13 C14 C15 -178.1(2) . . . . ?
N1 C1 N5 N6 -174.5(2) . . . . ?
N1 C1 N7 C4 174.3(2) . . . . ?
N1 C1 N7 N8 -8.1(3) . . . . ?
N1 N2 C2 N3 172.4(3) . . . . ?
N1 N2 C2 N8 2.1(4) . . . . ?
C1 N1 N2 C2 5.4(4) . . . . ?
C1 N5 N6 C4 -0.1(3) . . . . ?
C1 N7 N8 C2 14.5(3) . . . . ?
C1 N7 N8 C3 -167.1(3) . . . . ?
O2 C12 C13 O1 2.3(4) . . . . ?
O2 C12 C13 C14 -176.5(2) . . . . ?
C2S C3S C4S C5S -0.7(5) . . . . ?
N2 N1 C1 N5 172.1(3) . . . . ?
N2 N1 C1 N7 -2.3(4) . . . . ?
N2 C2 N3 N4 -170.2(2) . . . . ?
N2 C2 N8 C3 168.7(2) . . . . ?
N2 C2 N8 N7 -12.5(4) . . . . ?
C2 N3 N4 C3 0.9(3) . . . . ?
O3 C6 C7 O4 1.8(4) . . . . ?
O3 C6 C7 C8 -178.9(2) . . . . ?
N3 C2 N8 C3 -2.8(3) . . . . ?
N3 C2 N8 N7 176.0(2) . . . . ?
C3 C5 C6 O3 -5.7(3) . . . . ?
C3 C5 C6 C7 177.0(2) . . . . ?
C3 C5 C10 C9 -177.2(3) . . . . ?
C3S C2S C1S O5 179.1(2) . . . . ?
C3S C2S C1S C6S -1.2(4) . . . . ?
C3S C4S C5S C6S 0.4(5) . . . . ?
O4 C7 C8 C9 179.6(3) . . . . ?
N4 C3 C5 C6 -132.2(3) . . . . ?
N4 C3 C5 C10 41.6(4) . . . . ?
N4 C3 N8 C2 3.3(3) . . . . ?
N4 C3 N8 N7 -175.2(2) . . . . ?
C4 N7 N8 C2 -168.9(2) . . . . ?
C4 N7 N8 C3 9.5(4) . . . . ?
C4 C11 C12 O2 -7.4(3) . . . . ?
C4 C11 C12 C13 176.7(2) . . . . ?
C4 C11 C16 C15 -177.3(2) . . . . ?
C4S C5S C6S C1S -0.6(5) . . . . ?
N5 C1 N7 C4 -1.0(3) . . . . ?
N5 C1 N7 N8 176.63(19) . . . . ?
C5 C3 N4 N3 173.4(2) . . . . ?
C5 C3 N8 C2 -172.4(3) . . . . ?
C5 C3 N8 N7 9.1(5) . . . . ?
C5 C6 C7 O4 179.0(2) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C5S C6S C1S C2S 0.9(4) . . . . ?
C5S C6S C1S O5 -179.4(2) . . . . ?
N6 C4 N7 C1 0.9(2) . . . . ?
N6 C4 N7 N8 -176.0(2) . . . . ?
N6 C4 C11 C12 -129.8(2) . . . . ?
N6 C4 C11 C16 45.8(3) . . . . ?
C6 C5 C10 C9 -3.3(4) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
O6 C3S C4S C5S 179.2(3) . . . . ?
N7 C1 N5 N6 0.7(3) . . . . ?
N7 C4 N6 N5 -0.5(3) . . . . ?
N7 C4 C11 C12 46.5(4) . . . . ?
N7 C4 C11 C16 -138.0(3) . . . . ?
C1S C2S C3S C4S 1.1(4) . . . . ?
C1S C2S C3S O6 -178.8(3) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
N8 C2 N3 N4 1.2(3) . . . . ?
N8 C3 N4 N3 -2.7(3) . . . . ?
N8 C3 C5 C6 42.8(4) . . . . ?
N8 C3 C5 C10 -143.3(3) . . . . ?
C8 C9 C10 C5 1.9(4) . . . . ?
C10 C5 C6 O3 -179.5(2) . . . . ?
C10 C5 C6 C7 3.2(4) . . . . ?
C11 C4 N6 N5 176.5(2) . . . . ?
C11 C4 N7 C1 -175.8(2) . . . . ?
C11 C4 N7 N8 7.3(4) . . . . ?
C11 C12 C13 O1 178.10(19) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C11 C16 C15 -1.7(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C11 1.6(4) . . . . ?
C16 C11 C12 O2 177.2(2) . . . . ?
C16 C11 C12 C13 1.2(3) . . . . ?
C17 O1 C13 C12 -176.4(2) . . . . ?
C17 O1 C13 C14 2.3(3) . . . . ?
C18 O2 C12 C11 120.6(2) . . . . ?
C18 O2 C12 C13 -63.5(3) . . . . ?
C19 O3 C6 C5 118.9(2) . . . . ?
C19 O3 C6 C7 -63.9(3) . . . . ?
C20 O4 C7 C6 178.4(2) . . . . ?
C20 O4 C7 C8 -0.9(4) . . . . ?
C7S C7S C9S C8S 0(2) 2_754 . . . ?
C8S C8S C9S C7S -0.4(19) 2_754 . . . ?
C21 C22 C23 C24 -3(3) . . . . ?
C22 C21 C22 C23 1.8(14) 2_754 . . . ?
C23 C24 C23 C22 1.6(13) 2_754 . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
