# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2080045'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-04-26 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N7'
_chemical_formula_sum            'C13 H9 N7'
_chemical_formula_weight         263.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0047 0.0021 '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 0.0086 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   4.3400(9)
_cell_length_b                   25.450(5)
_cell_length_c                   11.540(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.909(12)
_cell_angle_gamma                90
_cell_volume                     1255.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      24.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   'Scala (Evans, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.79313
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15588
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.786
_diffrn_reflns_theta_max         30.939
_diffrn_reflns_theta_full        28.417
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2846
_reflns_number_gt                1355
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0937P)²+0.007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2846
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1853
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.7322(5) 0.35249(8) 0.39000(18) 0.0783(6) Uani 1 1 d . . . . .
N2 N 0.9320(5) 0.39212(8) 0.41988(18) 0.0781(6) Uani 1 1 d . . . . .
N3 N 1.0114(6) 0.40077(8) 0.53575(18) 0.0864(6) Uani 1 1 d . . . . .
N4 N 0.8651(7) 0.35861(11) 0.7032(2) 0.1061(8) Uani 1 1 d . . . . .
N5 N 1.0671(7) 0.38384(11) 0.7659(2) 0.1013(8) Uani 1 1 d . . . . .
N6 N 1.2371(8) 0.40396(13) 0.8370(3) 0.1300(11) Uani 1 1 d . . . . .
N7 N 0.4353(5) 0.27357(9) 0.60566(18) 0.0871(6) Uani 1 1 d . . . . .
C1 C 0.8512(7) 0.36418(10) 0.5819(2) 0.0817(7) Uani 1 1 d . . . . .
C2 C 0.6774(6) 0.33393(10) 0.4931(2) 0.0757(7) Uani 1 1 d . . . . .
C3 C 1.0534(6) 0.42301(10) 0.3355(2) 0.0808(7) Uani 1 1 d . . . . .
C4 C 0.9987(8) 0.40872(13) 0.2206(3) 0.1038(9) Uani 1 1 d . . . . .
H4 H 0.8796 0.3781 0.1962 0.125 Uiso 1 1 calc R U . . .
C5 C 1.1181(9) 0.43916(15) 0.1394(3) 0.1177(11) Uani 1 1 d . . . . .
H5 H 1.0820 0.4293 0.0588 0.141 Uiso 1 1 calc R U . . .
C6 C 1.2881(8) 0.48344(15) 0.1746(3) 0.1120(10) Uani 1 1 d . . . . .
H6 H 1.3681 0.5044 0.1184 0.134 Uiso 1 1 calc R U . . .
C7 C 1.3427(8) 0.49758(12) 0.2909(3) 0.1041(9) Uani 1 1 d . . . . .
H7 H 1.4610 0.5282 0.3155 0.125 Uiso 1 1 calc R U . . .
C8 C 1.2255(7) 0.46719(11) 0.3720(3) 0.0910(8) Uani 1 1 d . . . . .
H8 H 1.2633 0.4767 0.4528 0.109 Uiso 1 1 calc R U . . .
C9 C 0.4702(6) 0.28898(10) 0.4979(2) 0.0747(6) Uani 1 1 d . . . . .
C10 C 0.3254(6) 0.26319(11) 0.3974(2) 0.0843(7) Uani 1 1 d . . . . .
H10 H 0.3524 0.2752 0.3219 0.101 Uiso 1 1 calc R U . . .
C11 C 0.1439(7) 0.22039(11) 0.4080(3) 0.0907(8) Uani 1 1 d . . . . .
H11 H 0.0441 0.2022 0.3399 0.109 Uiso 1 1 calc R U . . .
C12 C 0.1066(7) 0.20388(12) 0.5171(3) 0.0919(8) Uani 1 1 d . . . . .
H12 H -0.0179 0.1740 0.5270 0.110 Uiso 1 1 calc R U . . .
C13 C 0.2544(7) 0.23172(12) 0.6119(3) 0.0947(8) Uani 1 1 d . . . . .
H13 H 0.2260 0.2204 0.6878 0.114 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.336(3) . ?
N1 C2 1.339(3) . ?
N2 N3 1.340(3) . ?
N2 C3 1.422(3) . ?
N3 C1 1.328(3) . ?
N4 N5 1.219(4) . ?
N4 C1 1.397(3) . ?
N5 N6 1.127(4) . ?
N7 C13 1.332(3) . ?
N7 C9 1.337(3) . ?
C1 C2 1.395(4) . ?
C2 C9 1.462(4) . ?
C3 C4 1.355(4) . ?
C3 C8 1.375(4) . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.370(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.386(4) . ?
C10 C11 1.362(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.363(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9500 . ?
C13 H13 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 N1 C2 104.1(2) . . ?
N1 N2 N3 115.2(2) . . ?
N1 N2 C3 122.8(2) . . ?
N3 N2 C3 122.0(2) . . ?
C1 N3 N2 102.9(2) . . ?
N5 N4 C1 116.3(3) . . ?
N6 N5 N4 170.0(3) . . ?
C13 N7 C9 116.5(2) . . ?
N3 C1 C2 110.3(2) . . ?
N3 C1 N4 122.5(3) . . ?
C2 C1 N4 127.2(3) . . ?
N1 C2 C1 107.6(2) . . ?
N1 C2 C9 121.0(2) . . ?
C1 C2 C9 131.4(2) . . ?
C4 C3 C8 120.9(3) . . ?
C4 C3 N2 119.9(3) . . ?
C8 C3 N2 119.2(2) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 119.7(3) . . ?
C3 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
N7 C9 C10 122.2(3) . . ?
N7 C9 C2 115.7(2) . . ?
C10 C9 C2 122.1(2) . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 117.7(3) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
N7 C13 C12 124.8(3) . . ?
N7 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?

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
C2 N1 N2 N3 -0.1(3) . . . . ?
C2 N1 N2 C3 179.8(2) . . . . ?
N1 N2 N3 C1 0.0(3) . . . . ?
C3 N2 N3 C1 -179.8(2) . . . . ?
N2 N3 C1 C2 0.0(3) . . . . ?
N2 N3 C1 N4 179.9(2) . . . . ?
N5 N4 C1 N3 -10.6(4) . . . . ?
N5 N4 C1 C2 169.2(3) . . . . ?
N2 N1 C2 C1 0.1(2) . . . . ?
N2 N1 C2 C9 -179.0(2) . . . . ?
N3 C1 C2 N1 -0.1(3) . . . . ?
N4 C1 C2 N1 -179.9(3) . . . . ?
N3 C1 C2 C9 178.9(2) . . . . ?
N4 C1 C2 C9 -0.9(5) . . . . ?
N1 N2 C3 C4 -8.3(4) . . . . ?
N3 N2 C3 C4 171.5(2) . . . . ?
N1 N2 C3 C8 171.7(2) . . . . ?
N3 N2 C3 C8 -8.4(4) . . . . ?
C8 C3 C4 C5 0.0(5) . . . . ?
N2 C3 C4 C5 180.0(3) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C4 C3 C8 C7 0.4(4) . . . . ?
N2 C3 C8 C7 -179.6(2) . . . . ?
C6 C7 C8 C3 -0.3(4) . . . . ?
C13 N7 C9 C10 0.3(4) . . . . ?
C13 N7 C9 C2 -178.1(2) . . . . ?
N1 C2 C9 N7 179.4(2) . . . . ?
C1 C2 C9 N7 0.5(4) . . . . ?
N1 C2 C9 C10 0.9(4) . . . . ?
C1 C2 C9 C10 -177.9(2) . . . . ?
N7 C9 C10 C11 -0.7(4) . . . . ?
C2 C9 C10 C11 177.7(2) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C9 N7 C13 C12 0.4(4) . . . . ?
C11 C12 C13 N7 -0.7(5) . . . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2080046'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-04-26 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N5'
_chemical_formula_sum            'C13 H9 N5'
_chemical_formula_weight         235.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   7.2746(10)
_cell_length_b                   13.4066(18)
_cell_length_c                   10.9808(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.693(3)
_cell_angle_gamma                90
_cell_volume                     1065.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3955
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.43

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14255
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.405
_diffrn_reflns_theta_max         30.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3234
_reflns_number_gt                2390
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+0.2588P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3234
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.29743(15) 0.58294(8) 0.57107(9) 0.0208(2) Uani 1 1 d . . . . .
N2 N 0.37544(15) 0.50305(8) 0.62917(10) 0.0207(2) Uani 1 1 d . . . . .
N3 N 0.50835(15) 0.51966(9) 0.72336(10) 0.0233(3) Uani 1 1 d . . . . .
C3A C 0.51431(18) 0.61970(10) 0.72450(11) 0.0215(3) Uani 1 1 d . . . . .
N4 N 0.61366(16) 0.69045(9) 0.79056(10) 0.0237(2) Uani 1 1 d . . . . .
N5 N 0.54131(15) 0.77582(8) 0.73598(10) 0.0210(2) Uani 1 1 d . . . . .
C6 C 0.60125(19) 0.86879(10) 0.77144(12) 0.0236(3) Uani 1 1 d . . . . .
H6 H 0.693571 0.876949 0.838183 0.028 Uiso 1 1 calc R U . . .
C7 C 0.52692(19) 0.94973(10) 0.70983(12) 0.0254(3) Uani 1 1 d . . . . .
H7 H 0.570205 1.014552 0.732865 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3870(2) 0.93893(10) 0.61259(12) 0.0254(3) Uani 1 1 d . . . . .
H8 H 0.335055 0.996316 0.571724 0.030 Uiso 1 1 calc R U . . .
C9 C 0.32567(18) 0.84584(10) 0.57675(12) 0.0223(3) Uani 1 1 d . . . . .
H9 H 0.231832 0.838043 0.510857 0.027 Uiso 1 1 calc R U . . .
C9A C 0.40340(17) 0.76250(10) 0.63873(11) 0.0199(3) Uani 1 1 d . . . . .
C9B C 0.38585(17) 0.65820(10) 0.63226(11) 0.0201(3) Uani 1 1 d . . . . .
C10 C 0.32130(18) 0.40497(9) 0.59295(11) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.40562(19) 0.32366(10) 0.65336(12) 0.0237(3) Uani 1 1 d . . . . .
H11 H 0.498842 0.333128 0.719271 0.028 Uiso 1 1 calc R U . . .
C12 C 0.3517(2) 0.22836(10) 0.61605(13) 0.0263(3) Uani 1 1 d . . . . .
H12 H 0.409037 0.172110 0.656431 0.032 Uiso 1 1 calc R U . . .
C13 C 0.2145(2) 0.21438(10) 0.51997(13) 0.0263(3) Uani 1 1 d . . . . .
H13 H 0.178375 0.148876 0.494706 0.032 Uiso 1 1 calc R U . . .
C14 C 0.13056(19) 0.29660(10) 0.46126(12) 0.0249(3) Uani 1 1 d . . . . .
H14 H 0.036336 0.287194 0.395954 0.030 Uiso 1 1 calc R U . . .
C15 C 0.18314(19) 0.39217(10) 0.49715(12) 0.0234(3) Uani 1 1 d . . . . .
H15 H 0.125619 0.448402 0.456861 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9B 1.3407(16) . ?
N1 N2 1.3433(14) . ?
N2 N3 1.3622(15) . ?
N2 C10 1.4182(16) . ?
N3 C3A 1.3420(18) . ?
C3A N4 1.3580(17) . ?
C3A C9B 1.4063(17) . ?
N4 N5 1.3723(15) . ?
N5 C6 1.3644(17) . ?
N5 C9A 1.4022(16) . ?
C6 C7 1.3621(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.4075(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3700(18) . ?
C8 H8 0.9500 . ?
C9 C9A 1.3982(17) . ?
C9 H9 0.9500 . ?
C9A C9B 1.4053(18) . ?
C10 C11 1.3870(18) . ?
C10 C15 1.3916(18) . ?
C11 C12 1.3863(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3875(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3832(18) . ?
C14 H14 0.9500 . ?
C15 H15 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
C9B N1 N2 101.71(10) . . ?
N1 N2 N3 117.70(10) . . ?
N1 N2 C10 120.90(10) . . ?
N3 N2 C10 121.40(10) . . ?
C3A N3 N2 100.97(10) . . ?
N3 C3A N4 135.89(12) . . ?
N3 C3A C9B 109.97(11) . . ?
N4 C3A C9B 114.13(12) . . ?
C3A N4 N5 100.86(10) . . ?
C6 N5 N4 122.64(11) . . ?
C6 N5 C9A 121.19(11) . . ?
N4 N5 C9A 116.16(11) . . ?
C7 C6 N5 119.09(12) . . ?
C7 C6 H6 120.5 . . ?
N5 C6 H6 120.5 . . ?
C6 C7 C8 121.09(13) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 120.14(13) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C9A 118.93(12) . . ?
C8 C9 H9 120.5 . . ?
C9A C9 H9 120.5 . . ?
C9 C9A N5 119.55(12) . . ?
C9 C9A C9B 137.75(12) . . ?
N5 C9A C9B 102.69(11) . . ?
N1 C9B C3A 109.65(11) . . ?
N1 C9B C9A 144.17(12) . . ?
C3A C9B C9A 106.16(11) . . ?
C11 C10 C15 121.10(12) . . ?
C11 C10 N2 119.82(12) . . ?
C15 C10 N2 119.08(11) . . ?
C12 C11 C10 118.97(12) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 120.59(12) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.65(13) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.47(13) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 119.22(12) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?

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
C9B N1 N2 N3 -0.19(14) . . . . ?
C9B N1 N2 C10 -179.92(11) . . . . ?
N1 N2 N3 C3A 0.02(14) . . . . ?
C10 N2 N3 C3A 179.75(11) . . . . ?
N2 N3 C3A N4 -178.80(15) . . . . ?
N2 N3 C3A C9B 0.17(14) . . . . ?
N3 C3A N4 N5 179.17(15) . . . . ?
C9B C3A N4 N5 0.24(14) . . . . ?
C3A N4 N5 C6 -179.20(11) . . . . ?
C3A N4 N5 C9A -0.55(14) . . . . ?
N4 N5 C6 C7 177.71(12) . . . . ?
C9A N5 C6 C7 -0.87(19) . . . . ?
N5 C6 C7 C8 1.5(2) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C7 C8 C9 C9A 0.4(2) . . . . ?
C8 C9 C9A N5 0.21(19) . . . . ?
C8 C9 C9A C9B -178.75(15) . . . . ?
C6 N5 C9A C9 0.02(19) . . . . ?
N4 N5 C9A C9 -178.64(11) . . . . ?
C6 N5 C9A C9B 179.31(11) . . . . ?
N4 N5 C9A C9B 0.64(14) . . . . ?
N2 N1 C9B C3A 0.28(13) . . . . ?
N2 N1 C9B C9A 178.27(18) . . . . ?
N3 C3A C9B N1 -0.30(15) . . . . ?
N4 C3A C9B N1 178.91(11) . . . . ?
N3 C3A C9B C9A -179.08(11) . . . . ?
N4 C3A C9B C9A 0.13(15) . . . . ?
C9 C9A C9B N1 0.6(3) . . . . ?
N5 C9A C9B N1 -178.46(17) . . . . ?
C9 C9A C9B C3A 178.65(15) . . . . ?
N5 C9A C9B C3A -0.43(13) . . . . ?
N1 N2 C10 C11 179.16(11) . . . . ?
N3 N2 C10 C11 -0.56(18) . . . . ?
N1 N2 C10 C15 -1.09(18) . . . . ?
N3 N2 C10 C15 179.19(11) . . . . ?
C15 C10 C11 C12 0.71(19) . . . . ?
N2 C10 C11 C12 -179.54(12) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C10 0.0(2) . . . . ?
C11 C10 C15 C14 -0.5(2) . . . . ?
N2 C10 C15 C14 179.73(11) . . . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2080047'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-04-26 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 N5'
_chemical_formula_sum            'C17 H11 N5'
_chemical_formula_weight         285.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   6.09350(10)
_cell_length_b                   9.7182(2)
_cell_length_c                   22.0737(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.3540(10)
_cell_angle_gamma                90
_cell_volume                     1307.13(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7496
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      32.52

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31021
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         32.609
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4776
_reflns_number_gt                3551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4776
_refine_ls_number_parameters     277
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.6909(4) 0.4957(2) 0.59579(14) 0.0233(3) Uani 0.7 1 d . . P A 1
N2 N 0.5323(7) 0.4805(3) 0.63838(13) 0.0228(3) Uani 0.7 1 d . . P A 1
N3 N 0.3489(7) 0.5596(3) 0.63289(13) 0.0249(4) Uani 0.7 1 d . . P A 1
N4 N 0.3001(5) 0.7325(3) 0.54605(11) 0.0291(4) Uani 0.7 1 d . . P A 1
N5 N 0.4581(4) 0.75182(19) 0.50395(10) 0.0276(3) Uani 0.7 1 d . . P A 1
C1 C 0.3924(3) 0.6335(2) 0.58186(12) 0.0204(4) Uani 0.7 1 d . . P A 1
C2 C 0.6012(4) 0.5949(2) 0.56003(10) 0.0205(4) Uani 0.7 1 d . . P A 1
C3 C 0.6465(4) 0.6726(2) 0.50808(12) 0.0255(3) Uani 0.7 1 d D . P A 1
C4 C 0.8055(2) 0.69123(16) 0.46436(6) 0.0299(3) Uani 0.7 1 d D . P A 1
H4A H 0.935402 0.637182 0.465485 0.036 Uiso 0.7 1 calc R U P A 1
C5 C 0.7770(3) 0.78698(16) 0.41949(7) 0.0327(3) Uani 0.7 1 d D . P A 1
H5A H 0.887240 0.796657 0.389537 0.039 Uiso 0.7 1 calc R U P A 1
C6 C 0.5926(4) 0.8702(3) 0.41632(10) 0.0284(5) Uani 0.7 1 d D . P A 1
C7 C 0.5635(7) 0.9716(4) 0.37139(13) 0.0396(7) Uani 0.7 1 d D . P A 1
H7A H 0.673615 0.985608 0.341730 0.047 Uiso 0.7 1 calc R U P A 1
C8 C 0.3751(7) 1.0508(4) 0.37040(14) 0.0425(8) Uani 0.7 1 d D . P A 1
H8A H 0.356565 1.118710 0.339854 0.051 Uiso 0.7 1 calc R U P A 1
C9 C 0.2124(6) 1.0323(4) 0.41345(17) 0.0407(7) Uani 0.7 1 d D . P A 1
H9A H 0.084306 1.087963 0.412433 0.049 Uiso 0.7 1 calc R U P A 1
C10 C 0.2373(4) 0.9322(3) 0.45807(13) 0.0319(5) Uani 0.7 1 d D . P A 1
H10A H 0.126396 0.918653 0.487544 0.038 Uiso 0.7 1 calc R U P A 1
C11 C 0.4269(3) 0.85227(17) 0.45892(7) 0.0242(4) Uani 0.7 1 d D . P A 1
C12 C 0.5495(7) 0.3868(3) 0.68633(12) 0.0254(3) Uani 0.7 1 d D . P A 1
C13 C 0.3755(6) 0.3710(4) 0.72628(19) 0.0351(4) Uani 0.7 1 d D . P A 1
H13A H 0.247889 0.426613 0.722441 0.042 Uiso 0.7 1 calc R U P A 1
C14 C 0.3911(6) 0.2728(5) 0.77191(18) 0.0428(5) Uani 0.7 1 d D . P A 1
H14A H 0.272728 0.260376 0.799186 0.051 Uiso 0.7 1 calc R U P A 1
C15 C 0.5791(7) 0.1925(4) 0.77782(16) 0.0414(5) Uani 0.7 1 d D . P A 1
H15A H 0.587550 0.124266 0.808585 0.050 Uiso 0.7 1 calc R U P A 1
C16 C 0.7541(5) 0.2119(4) 0.73885(18) 0.0400(5) Uani 0.7 1 d D . P A 1
H16A H 0.883516 0.158332 0.743622 0.048 Uiso 0.7 1 calc R U P A 1
C17 C 0.7412(5) 0.3097(4) 0.69263(13) 0.0307(4) Uani 0.7 1 d D . P A 1
H17A H 0.860900 0.323558 0.665951 0.037 Uiso 0.7 1 calc R U P A 1
N1A N 0.6435(7) 0.6758(4) 0.5072(2) 0.0232(4) Uani 0.3 1 d D . P B 2
N2A N 0.4558(8) 0.7519(3) 0.50416(17) 0.0232(4) Uani 0.3 1 d D . P B 2
N3A N 0.3037(10) 0.7249(5) 0.5493(2) 0.0232(4) Uani 0.3 1 d D . P B 2
N4A N 0.3483(16) 0.5636(8) 0.6271(3) 0.0232(4) Uani 0.3 1 d D . P B 2
N5A N 0.5241(16) 0.4812(7) 0.6359(3) 0.0232(4) Uani 0.3 1 d D . P B 2
C1A C 0.4209(10) 0.6278(6) 0.5779(3) 0.0232(4) Uani 0.3 1 d D . P B 2
C2A C 0.6247(11) 0.5924(5) 0.5559(2) 0.0232(4) Uani 0.3 1 d D . P B 2
C3A C 0.6931(9) 0.4920(5) 0.5961(4) 0.0232(4) Uani 0.3 1 d D . P B 2
C4A C 0.8813(5) 0.4115(3) 0.60124(12) 0.0232(4) Uani 0.3 1 d D . P B 2
H4AA H 0.996964 0.420262 0.572824 0.028 Uiso 0.3 1 calc R U P B 2
C5A C 0.8968(5) 0.3187(3) 0.64840(11) 0.0232(4) Uani 0.3 1 d D . P B 2
H5AA H 1.025296 0.263970 0.652313 0.028 Uiso 0.3 1 calc R U P B 2
C6A C 0.7292(10) 0.3031(8) 0.6904(3) 0.0232(4) Uani 0.3 1 d D . P B 2
C7A C 0.7447(8) 0.2089(7) 0.7379(3) 0.0232(4) Uani 0.3 1 d D . P B 2
H7AA H 0.872224 0.153306 0.742024 0.028 Uiso 0.3 1 calc R U P B 2
C8A C 0.5743(10) 0.1958(7) 0.7792(3) 0.0232(4) Uani 0.3 1 d D . P B 2
H8AA H 0.585383 0.131479 0.811490 0.028 Uiso 0.3 1 calc R U P B 2
C9A C 0.3872(9) 0.2775(8) 0.7730(3) 0.0232(4) Uani 0.3 1 d D . P B 2
H9AA H 0.270855 0.268737 0.801152 0.028 Uiso 0.3 1 calc R U P B 2
C10A C 0.3702(10) 0.3717(7) 0.7257(3) 0.0232(4) Uani 0.3 1 d D . P B 2
H10B H 0.242602 0.427196 0.721617 0.028 Uiso 0.3 1 calc R U P B 2
C11A C 0.5415(14) 0.3844(7) 0.6844(2) 0.0232(4) Uani 0.3 1 d D . P B 2
C12A C 0.4361(9) 0.8488(4) 0.45847(19) 0.0529(18) Uani 0.3 1 d D . P B 2
C13A C 0.2490(11) 0.9312(7) 0.4547(4) 0.0529(18) Uani 0.3 1 d D . P B 2
H13B H 0.134989 0.920808 0.483540 0.063 Uiso 0.3 1 calc R U P B 2
C14A C 0.2297(16) 1.0286(9) 0.4087(5) 0.0529(18) Uani 0.3 1 d D . P B 2
H14B H 0.102354 1.084803 0.406140 0.063 Uiso 0.3 1 calc R U P B 2
C15A C 0.3970(18) 1.0437(9) 0.3665(4) 0.0529(18) Uani 0.3 1 d D . P B 2
H15B H 0.383579 1.110253 0.335135 0.063 Uiso 0.3 1 calc R U P B 2
C16A C 0.5836(17) 0.9616(10) 0.3701(3) 0.0529(18) Uani 0.3 1 d D . P B 2
H16B H 0.697383 0.972086 0.341258 0.063 Uiso 0.3 1 calc R U P B 2
C17A C 0.6041(12) 0.8638(8) 0.4162(3) 0.0529(18) Uani 0.3 1 d D . P B 2
H17B H 0.731550 0.807735 0.418778 0.063 Uiso 0.3 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
N1 C2 1.359(2) . ?
N1 N2 1.361(2) . ?
N2 N3 1.361(2) . ?
N2 C12 1.399(2) . ?
N3 C1 1.363(2) . ?
N4 N5 1.355(2) . ?
N4 C1 1.364(2) . ?
N5 C3 1.385(2) . ?
N5 C11 1.4052(19) . ?
C1 C2 1.4139(19) . ?
C2 C3 1.402(2) . ?
C3 C4 1.383(3) . ?
C4 C5 1.3694(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5A 0.9500 . ?
C6 C11 1.3951(17) . ?
C6 C7 1.4082(17) . ?
C7 C8 1.3822(19) . ?
C7 H7A 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3919(17) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3922(17) . ?
C10 H10A 0.9500 . ?
C12 C13 1.3916(18) . ?
C12 C17 1.3937(18) . ?
C13 C14 1.3909(19) . ?
C13 H13A 0.9500 . ?
C14 C15 1.391(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.388(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.3966(18) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
N1A C2A 1.351(3) . ?
N1A N2A 1.363(3) . ?
N2A C12A 1.385(2) . ?
N2A N3A 1.390(3) . ?
N3A C1A 1.339(3) . ?
N4A C1A 1.329(3) . ?
N4A N5A 1.350(3) . ?
N5A C3A 1.362(3) . ?
N5A C11A 1.430(3) . ?
C1A C2A 1.380(3) . ?
C2A C3A 1.382(3) . ?
C3A C4A 1.392(3) . ?
C4A C5A 1.380(3) . ?
C4A H4AA 0.9500 . ?
C5A C6A 1.391(3) . ?
C5A H5AA 0.9500 . ?
C6A C7A 1.395(2) . ?
C6A C11A 1.396(2) . ?
C7A C8A 1.392(2) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.396(2) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.391(2) . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.396(2) . ?
C10A H10B 0.9500 . ?
C12A C13A 1.395(2) . ?
C12A C17A 1.397(2) . ?
C13A C14A 1.393(2) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.394(3) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.391(3) . ?
C15A H15B 0.9500 . ?
C16A C17A 1.397(2) . ?
C16A H16B 0.9500 . ?
C17A H17B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N2 101.2(2) . . ?
N1 N2 N3 117.6(3) . . ?
N1 N2 C12 122.9(4) . . ?
N3 N2 C12 119.5(4) . . ?
N2 N3 C1 102.0(3) . . ?
N5 N4 C1 101.7(3) . . ?
N4 N5 C3 118.0(2) . . ?
N4 N5 C11 119.2(2) . . ?
C3 N5 C11 122.8(2) . . ?
N3 C1 N4 140.2(3) . . ?
N3 C1 C2 108.8(3) . . ?
N4 C1 C2 111.0(3) . . ?
N1 C2 C3 141.0(3) . . ?
N1 C2 C1 110.5(2) . . ?
C3 C2 C1 108.5(2) . . ?
C4 C3 N5 117.7(2) . . ?
C4 C3 C2 141.5(2) . . ?
N5 C3 C2 100.7(2) . . ?
C5 C4 C3 120.46(18) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 122.16(15) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C5 C6 C11 118.88(14) . . ?
C5 C6 C7 122.83(17) . . ?
C11 C6 C7 118.28(13) . . ?
C8 C7 C6 120.08(14) . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C7 C8 C9 120.90(13) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C8 C9 C10 119.97(13) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C11 119.08(14) . . ?
C9 C10 H10A 120.5 . . ?
C11 C10 H10A 120.5 . . ?
C10 C11 C6 121.68(12) . . ?
C10 C11 N5 120.40(14) . . ?
C6 C11 N5 117.91(14) . . ?
C13 C12 C17 121.27(14) . . ?
C13 C12 N2 119.8(4) . . ?
C17 C12 N2 118.9(4) . . ?
C14 C13 C12 119.04(15) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
C13 C14 C15 120.37(15) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C16 C15 C14 120.07(14) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C17 120.35(15) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C12 C17 C16 118.84(14) . . ?
C12 C17 H17A 120.6 . . ?
C16 C17 H17A 120.6 . . ?
C2A N1A N2A 106.8(5) . . ?
N1A N2A C12A 118.3(4) . . ?
N1A N2A N3A 115.1(4) . . ?
C12A N2A N3A 126.6(4) . . ?
C1A N3A N2A 96.6(6) . . ?
C1A N4A N5A 97.3(7) . . ?
N4A N5A C3A 117.7(7) . . ?
N4A N5A C11A 123.6(9) . . ?
C3A N5A C11A 118.8(9) . . ?
N4A C1A N3A 122.4(7) . . ?
N4A C1A C2A 118.4(7) . . ?
N3A C1A C2A 119.2(7) . . ?
N1A C2A C1A 102.2(6) . . ?
N1A C2A C3A 155.2(7) . . ?
C1A C2A C3A 102.6(5) . . ?
N5A C3A C2A 104.0(5) . . ?
N5A C3A C4A 122.0(8) . . ?
C2A C3A C4A 134.0(8) . . ?
C5A C4A C3A 118.8(5) . . ?
C5A C4A H4AA 120.6 . . ?
C3A C4A H4AA 120.6 . . ?
C4A C5A C6A 121.8(5) . . ?
C4A C5A H5AA 119.1 . . ?
C6A C5A H5AA 119.1 . . ?
C5A C6A C7A 121.7(6) . . ?
C5A C6A C11A 118.7(6) . . ?
C7A C6A C11A 119.6(2) . . ?
C8A C7A C6A 120.4(2) . . ?
C8A C7A H7AA 119.8 . . ?
C6A C7A H7AA 119.8 . . ?
C7A C8A C9A 119.7(2) . . ?
C7A C8A H8AA 120.1 . . ?
C9A C8A H8AA 120.1 . . ?
C10A C9A C8A 120.4(2) . . ?
C10A C9A H9AA 119.8 . . ?
C8A C9A H9AA 119.8 . . ?
C9A C10A C11A 119.7(2) . . ?
C9A C10A H10B 120.2 . . ?
C11A C10A H10B 120.2 . . ?
C10A C11A C6A 120.3(2) . . ?
C10A C11A N5A 119.7(7) . . ?
C6A C11A N5A 120.0(7) . . ?
N2A C12A C13A 120.0(2) . . ?
N2A C12A C17A 119.8(2) . . ?
C13A C12A C17A 120.19(19) . . ?
C14A C13A C12A 119.9(2) . . ?
C14A C13A H13B 120.0 . . ?
C12A C13A H13B 120.0 . . ?
C13A C14A C15A 120.0(2) . . ?
C13A C14A H14B 120.0 . . ?
C15A C14A H14B 120.0 . . ?
C16A C15A C14A 120.1(2) . . ?
C16A C15A H15B 119.9 . . ?
C14A C15A H15B 119.9 . . ?
C15A C16A C17A 120.1(2) . . ?
C15A C16A H16B 119.9 . . ?
C17A C16A H16B 119.9 . . ?
C12A C17A C16A 119.6(2) . . ?
C12A C17A H17B 120.2 . . ?
C16A C17A H17B 120.2 . . ?

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
C2 N1 N2 N3 0.63(17) . . . . ?
C2 N1 N2 C12 179.80(14) . . . . ?
N1 N2 N3 C1 -0.07(18) . . . . ?
C12 N2 N3 C1 -179.27(13) . . . . ?
C1 N4 N5 C3 0.98(16) . . . . ?
C1 N4 N5 C11 -177.79(15) . . . . ?
N2 N3 C1 N4 -179.72(19) . . . . ?
N2 N3 C1 C2 -0.52(16) . . . . ?
N5 N4 C1 N3 178.46(19) . . . . ?
N5 N4 C1 C2 -0.73(16) . . . . ?
N2 N1 C2 C3 179.23(19) . . . . ?
N2 N1 C2 C1 -0.92(15) . . . . ?
N3 C1 C2 N1 0.96(17) . . . . ?
N4 C1 C2 N1 -179.59(13) . . . . ?
N3 C1 C2 C3 -179.13(13) . . . . ?
N4 C1 C2 C3 0.32(17) . . . . ?
N4 N5 C3 C4 178.91(17) . . . . ?
C11 N5 C3 C4 -2.4(2) . . . . ?
N4 N5 C3 C2 -0.79(16) . . . . ?
C11 N5 C3 C2 177.93(15) . . . . ?
N1 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 -179.3(2) . . . . ?
N1 C2 C3 N5 -179.90(19) . . . . ?
C1 C2 C3 N5 0.24(15) . . . . ?
N5 C3 C4 C5 1.2(2) . . . . ?
C2 C3 C4 C5 -179.2(2) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C5 C6 C11 -2.5(3) . . . . ?
C4 C5 C6 C7 178.29(17) . . . . ?
C5 C6 C7 C8 179.5(3) . . . . ?
C11 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C6 0.2(2) . . . . ?
C9 C10 C11 N5 179.04(14) . . . . ?
C5 C6 C11 C10 -179.8(3) . . . . ?
C7 C6 C11 C10 -0.5(2) . . . . ?
C5 C6 C11 N5 1.3(3) . . . . ?
C7 C6 C11 N5 -179.39(14) . . . . ?
N4 N5 C11 C10 0.9(2) . . . . ?
C3 N5 C11 C10 -177.83(19) . . . . ?
N4 N5 C11 C6 179.77(17) . . . . ?
C3 N5 C11 C6 1.1(2) . . . . ?
N1 N2 C12 C13 -176.31(16) . . . . ?
N3 N2 C12 C13 2.8(2) . . . . ?
N1 N2 C12 C17 3.0(2) . . . . ?
N3 N2 C12 C17 -177.85(14) . . . . ?
C17 C12 C13 C14 -2.4(3) . . . . ?
N2 C12 C13 C14 176.91(17) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C14 C15 C16 C17 -1.5(3) . . . . ?
C13 C12 C17 C16 2.2(3) . . . . ?
N2 C12 C17 C16 -177.13(16) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C2A N1A N2A C12A 178.5(2) . . . . ?
C2A N1A N2A N3A 0.00(8) . . . . ?
N1A N2A N3A C1A 0.01(8) . . . . ?
C12A N2A N3A C1A -178.4(2) . . . . ?
C1A N4A N5A C3A 0.0(2) . . . . ?
C1A N4A N5A C11A 179.98(18) . . . . ?
N5A N4A C1A N3A 179.98(16) . . . . ?
N5A N4A C1A C2A 0.0(2) . . . . ?
N2A N3A C1A N4A -179.99(16) . . . . ?
N2A N3A C1A C2A -0.02(16) . . . . ?
N2A N1A C2A C1A -0.01(14) . . . . ?
N2A N1A C2A C3A 180.0(4) . . . . ?
N4A C1A C2A N1A 179.99(15) . . . . ?
N3A C1A C2A N1A 0.0(2) . . . . ?
N4A C1A C2A C3A 0.0(2) . . . . ?
N3A C1A C2A C3A -179.98(15) . . . . ?
N4A N5A C3A C2A 0.0(2) . . . . ?
C11A N5A C3A C2A -179.99(16) . . . . ?
N4A N5A C3A C4A -179.88(17) . . . . ?
C11A N5A C3A C4A 0.1(3) . . . . ?
N1A C2A C3A N5A 180.0(3) . . . . ?
C1A C2A C3A N5A 0.01(19) . . . . ?
N1A C2A C3A C4A -0.1(5) . . . . ?
C1A C2A C3A C4A 179.9(2) . . . . ?
N5A C3A C4A C5A -0.3(3) . . . . ?
C2A C3A C4A C5A 179.81(19) . . . . ?
C3A C4A C5A C6A 0.5(2) . . . . ?
C4A C5A C6A C7A 179.74(17) . . . . ?
C4A C5A C6A C11A -0.3(3) . . . . ?
C5A C6A C7A C8A 179.91(17) . . . . ?
C11A C6A C7A C8A 0.0(3) . . . . ?
C6A C7A C8A C9A 0.0(3) . . . . ?
C7A C8A C9A C10A 0.0(3) . . . . ?
C8A C9A C10A C11A 0.0(3) . . . . ?
C9A C10A C11A C6A 0.0(3) . . . . ?
C9A C10A C11A N5A 179.99(17) . . . . ?
C5A C6A C11A C10A -179.91(17) . . . . ?
C7A C6A C11A C10A 0.0(3) . . . . ?
C5A C6A C11A N5A 0.1(3) . . . . ?
C7A C6A C11A N5A -179.97(17) . . . . ?
N4A N5A C11A C10A 0.0(3) . . . . ?
C3A N5A C11A C10A -179.98(17) . . . . ?
N4A N5A C11A C6A -179.99(18) . . . . ?
C3A N5A C11A C6A 0.0(3) . . . . ?
N1A N2A C12A C13A -178.3(4) . . . . ?
N3A N2A C12A C13A 0.0(4) . . . . ?
N1A N2A C12A C17A 1.7(4) . . . . ?
N3A N2A C12A C17A 180.0(4) . . . . ?
N2A C12A C13A C14A 179.99(9) . . . . ?
C17A C12A C13A C14A 0.01(12) . . . . ?
C12A C13A C14A C15A 0.0(2) . . . . ?
C13A C14A C15A C16A 0.0(3) . . . . ?
C14A C15A C16A C17A -0.1(3) . . . . ?
N2A C12A C17A C16A 179.96(12) . . . . ?
C13A C12A C17A C16A -0.06(19) . . . . ?
C15A C16A C17A C12A 0.1(3) . . . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045

