# 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 2023

####################################################################### 
# 
# 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. 
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data_kurz_socr_1_2
_database_code_depnum_ccdc_archive 'CCDC 2244540'
loop_
_audit_author_name
_audit_author_address
'Taisiya Sukhikh'
;NIIC SB RAS
Russia
;
_audit_update_record             
;
2023-02-25 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2023-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 N2 O3, C3 H5 N2'
_chemical_formula_sum            'C7 H8 N4 O3'
_chemical_formula_weight         196.17
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   21.3255(17)
_cell_length_b                   12.1156(10)
_cell_length_c                   14.6128(12)
_cell_angle_alpha                90
_cell_angle_beta                 119.235(3)
_cell_angle_gamma                90
_cell_volume                     3294.6(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2299
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0872 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.9242.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8779
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_min         1.597
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_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                2481
_reflns_number_total             3506
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.040
_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)+(0.0456P)²+2.2879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1195
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N11_2-H11_2 = N23_5-H23_5 = N11_1-H11_1 = N21_5-H21_5 = N21_6-H21_6 = N23_6-
 H23_6 = N11_3-H11_3 = N11_4-H11_4
 0.88 with sigma of 0.02
 C13_2-H13_2 = C13_1-H13_1 = C22_5-H22_5 = C25_5-H25_5 = C24_5-H24_5 = C25_6-
 H25_6 = C24_6-H24_6 = C13_3-H13_3 = C13_4-H13_5 = C22_6-H22_6
 0.95 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_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
O11_1 O 1.08334(11) 0.5000 0.63359(18) 0.0303(5) Uani 1 2 d S T P . .
O12_1 O 0.89317(8) 0.69599(12) 0.60306(12) 0.0264(4) Uani 1 1 d . . . . .
N11_1 N 0.98642(9) 0.59531(15) 0.61608(14) 0.0230(4) Uani 1 1 d D . . . .
H11_1 H 1.0098(11) 0.6581(15) 0.6220(17) 0.028 Uiso 1 1 d D U . . .
C11_1 C 1.02258(16) 0.5000 0.6221(2) 0.0224(7) Uani 1 2 d S T P . .
C12_1 C 0.91839(11) 0.59982(18) 0.60592(16) 0.0210(5) Uani 1 1 d . . . . .
C13_1 C 0.88433(16) 0.5000 0.6000(3) 0.0243(7) Uani 1 2 d DS T P . .
H13_1 H 0.8370(11) 0.5000 0.591(2) 0.029 Uiso 1 2 d DS U P . .
O11_2 O 0.99364(11) 0.5000 0.8731(2) 0.0343(6) Uani 1 2 d S T P . .
O12_2 O 0.81588(7) 0.69583(12) 0.88208(12) 0.0244(4) Uani 1 1 d . . . . .
N11_2 N 0.90189(9) 0.59514(15) 0.87292(15) 0.0238(4) Uani 1 1 d D . . . .
H11_2 H 0.9241(12) 0.6551(15) 0.8728(18) 0.029 Uiso 1 1 d D U . . .
C11_2 C 0.93605(16) 0.5000 0.8730(2) 0.0235(7) Uani 1 2 d S T P . .
C12_2 C 0.83877(10) 0.60045(18) 0.87803(16) 0.0211(5) Uani 1 1 d . . . . .
C13_2 C 0.80686(16) 0.5000 0.8787(3) 0.0235(7) Uani 1 2 d DS T P . .
H13_2 H 0.7642(12) 0.5000 0.885(2) 0.028 Uiso 1 2 d DS U P . .
O11_3 O 0.35869(10) 0.5000 0.56695(17) 0.0251(5) Uani 1 2 d S T P . .
O12_3 O 0.55835(7) 0.69552(12) 0.63447(12) 0.0240(4) Uani 1 1 d . . . . .
N11_3 N 0.46079(9) 0.59522(15) 0.60660(14) 0.0208(4) Uani 1 1 d D . . . .
H11_3 H 0.4398(11) 0.6582(15) 0.6040(17) 0.025 Uiso 1 1 d D U . . .
C11_3 C 0.42308(15) 0.5000 0.5925(2) 0.0197(6) Uani 1 2 d S T P . .
C12_3 C 0.53219(11) 0.60036(18) 0.62901(16) 0.0205(5) Uani 1 1 d . . . . .
C13_3 C 0.56777(15) 0.5000 0.6421(2) 0.0209(7) Uani 1 2 d DS T P . .
H13_3 H 0.6161(11) 0.5000 0.655(2) 0.025 Uiso 1 2 d DS U P . .
O11_4 O 0.30859(11) 0.5000 0.92914(18) 0.0269(5) Uani 1 2 d S T P . .
O12_4 O 0.46345(8) 0.69553(12) 0.86290(13) 0.0281(4) Uani 1 1 d . . . . .
N11_4 N 0.38717(9) 0.59502(15) 0.89576(14) 0.0212(4) Uani 1 1 d D . . . .
H11_4 H 0.3672(11) 0.6591(15) 0.8961(17) 0.025 Uiso 1 1 d D U . . .
C11_4 C 0.35812(15) 0.5000 0.9077(2) 0.0198(6) Uani 1 2 d S T P . .
C12_4 C 0.44260(10) 0.60022(18) 0.87103(16) 0.0208(5) Uani 1 1 d . . . . .
C13_4 C 0.46960(15) 0.5000 0.8587(2) 0.0218(7) Uani 1 2 d DS T P . .
N21_5 N 0.68305(10) 0.73985(16) 0.63686(15) 0.0254(4) Uani 1 1 d D . . . .
H21_5 H 0.6425(10) 0.7195(19) 0.6355(18) 0.030 Uiso 1 1 d D U . . .
N23_5 N 0.78044(10) 0.73784(15) 0.62701(15) 0.0254(4) Uani 1 1 d D . . . .
H23_5 H 0.8155(10) 0.7160(19) 0.6171(18) 0.030 Uiso 1 1 d D U . . .
C22_5 C 0.72763(12) 0.6767(2) 0.6218(2) 0.0308(6) Uani 1 1 d D . . . .
H13_5 H 0.5096(14) 0.5000 0.846(3) 0.037 Uiso 1 2 d DS U P . .
H22_5 H 0.7219(12) 0.6008(14) 0.6077(18) 0.037 Uiso 1 1 d D U . . .
C24_5 C 0.76925(13) 0.8436(2) 0.6454(2) 0.0313(6) Uani 1 1 d D . . . .
H24_5 H 0.8012(11) 0.8995(17) 0.6480(18) 0.038 Uiso 1 1 d D U . . .
C25_5 C 0.70809(13) 0.8454(2) 0.6514(2) 0.0329(6) Uani 1 1 d D . . . .
H25_5 H 0.6807(12) 0.9006(18) 0.6589(18) 0.039 Uiso 1 1 d D U . . .
N21_6 N 0.69207(9) 0.73723(15) 0.87789(14) 0.0238(4) Uani 1 1 d D . . . .
H21_6 H 0.7322(10) 0.7141(19) 0.8783(17) 0.029 Uiso 1 1 d D U . . .
N23_6 N 0.58897(10) 0.73822(16) 0.87093(15) 0.0244(4) Uani 1 1 d D . . . .
H23_6 H 0.5498(10) 0.7159(19) 0.8734(17) 0.029 Uiso 1 1 d D U . . .
C22_6 C 0.64247(12) 0.6746(2) 0.8810(2) 0.0289(5) Uani 1 1 d D . . . .
H22_6 H 0.6431(12) 0.5973(14) 0.8857(17) 0.035 Uiso 1 1 d D U . . .
C24_6 C 0.60518(13) 0.8442(2) 0.8618(2) 0.0302(5) Uani 1 1 d D . . . .
H24_6 H 0.5742(11) 0.9009(17) 0.8568(18) 0.036 Uiso 1 1 d D U . . .
C25_6 C 0.66970(13) 0.84377(19) 0.8659(2) 0.0308(6) Uani 1 1 d D . . . .
H25_6 H 0.7005(11) 0.8997(17) 0.8649(18) 0.037 Uiso 1 1 d D 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
O11_1 C11_1 1.223(3) . ?
O12_1 C12_1 1.275(2) . ?
N11_1 H11_1 0.891(16) . ?
N11_1 C11_1 1.367(2) . ?
N11_1 C12_1 1.385(3) . ?
C11_1 N11_1 1.367(2) 6_565 ?
C12_1 C13_1 1.391(3) . ?
C13_1 C12_1 1.391(3) 6_565 ?
C13_1 H13_1 0.951(18) . ?
O11_2 C11_2 1.228(3) . ?
O12_2 C12_2 1.267(2) . ?
N11_2 H11_2 0.867(16) . ?
N11_2 C11_2 1.363(2) . ?
N11_2 C12_2 1.386(3) . ?
C11_2 N11_2 1.363(2) 6_565 ?
C12_2 C13_2 1.397(3) . ?
C13_2 C12_2 1.397(3) 6_565 ?
C13_2 H13_2 0.958(17) . ?
O11_3 C11_3 1.235(3) . ?
O12_3 C12_3 1.266(2) . ?
N11_3 H11_3 0.877(16) . ?
N11_3 C11_3 1.363(2) . ?
N11_3 C12_3 1.394(2) . ?
C11_3 N11_3 1.363(2) 6_565 ?
C12_3 C13_3 1.396(2) . ?
C13_3 C12_3 1.396(2) 6_565 ?
C13_3 H13_3 0.955(17) . ?
O11_4 C11_4 1.240(3) . ?
O12_4 C12_4 1.264(3) . ?
N11_4 H11_4 0.886(16) . ?
N11_4 C11_4 1.358(2) . ?
N11_4 C12_4 1.396(3) . ?
C11_4 N11_4 1.358(2) 6_565 ?
C12_4 C13_4 1.393(2) . ?
C13_4 C12_4 1.393(3) 6_565 ?
C13_4 H13_5 0.962(18) . ?
N21_5 H21_5 0.890(16) . ?
N21_5 C22_5 1.320(3) . ?
N21_5 C25_5 1.362(3) . ?
N23_5 H23_5 0.870(16) . ?
N23_5 C22_5 1.319(3) . ?
N23_5 C24_5 1.354(3) . ?
C22_5 H22_5 0.937(16) . ?
C24_5 H24_5 0.947(16) . ?
C24_5 C25_5 1.349(3) . ?
C25_5 H25_5 0.930(16) . ?
N21_6 H21_6 0.897(16) . ?
N21_6 C22_6 1.320(3) . ?
N21_6 C25_6 1.357(3) . ?
N23_6 H23_6 0.894(16) . ?
N23_6 C22_6 1.324(3) . ?
N23_6 C24_6 1.354(3) . ?
C22_6 H22_6 0.939(16) . ?
C24_6 H24_6 0.931(16) . ?
C24_6 C25_6 1.348(3) . ?
C25_6 H25_6 0.949(16) . ?

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
C11_1 N11_1 H11_1 116.4(15) . . ?
C11_1 N11_1 C12_1 124.62(19) . . ?
C12_1 N11_1 H11_1 119.0(15) . . ?
O11_1 C11_1 N11_1 122.36(13) . . ?
O11_1 C11_1 N11_1 122.36(12) . 6_565 ?
N11_1 C11_1 N11_1 115.3(2) 6_565 . ?
O12_1 C12_1 N11_1 116.25(18) . . ?
O12_1 C12_1 C13_1 126.38(19) . . ?
N11_1 C12_1 C13_1 117.4(2) . . ?
C12_1 C13_1 C12_1 120.7(3) 6_565 . ?
C12_1 C13_1 H13_1 119.63(13) . . ?
C12_1 C13_1 H13_1 119.63(14) 6_565 . ?
C11_2 N11_2 H11_2 114.6(16) . . ?
C11_2 N11_2 C12_2 124.87(19) . . ?
C12_2 N11_2 H11_2 120.4(16) . . ?
O11_2 C11_2 N11_2 122.26(12) . 6_565 ?
O11_2 C11_2 N11_2 122.26(12) . . ?
N11_2 C11_2 N11_2 115.5(2) . 6_565 ?
O12_2 C12_2 N11_2 116.83(19) . . ?
O12_2 C12_2 C13_2 126.46(19) . . ?
N11_2 C12_2 C13_2 116.7(2) . . ?
C12_2 C13_2 C12_2 121.2(3) 6_565 . ?
C12_2 C13_2 H13_2 119.31(17) 6_565 . ?
C12_2 C13_2 H13_2 119.31(16) . . ?
C11_3 N11_3 H11_3 118.6(15) . . ?
C11_3 N11_3 C12_3 124.71(19) . . ?
C12_3 N11_3 H11_3 116.6(15) . . ?
O11_3 C11_3 N11_3 122.18(12) . . ?
O11_3 C11_3 N11_3 122.18(12) . 6_565 ?
N11_3 C11_3 N11_3 115.6(2) . 6_565 ?
O12_3 C12_3 N11_3 116.91(18) . . ?
O12_3 C12_3 C13_3 126.24(19) . . ?
N11_3 C12_3 C13_3 116.84(19) . . ?
C12_3 C13_3 C12_3 121.1(3) 6_565 . ?
C12_3 C13_3 H13_3 119.34(15) 6_565 . ?
C12_3 C13_3 H13_3 119.33(15) . . ?
C11_4 N11_4 H11_4 119.4(15) . . ?
C11_4 N11_4 C12_4 124.65(19) . . ?
C12_4 N11_4 H11_4 115.5(15) . . ?
O11_4 C11_4 N11_4 122.06(12) . 6_565 ?
O11_4 C11_4 N11_4 122.06(12) . . ?
N11_4 C11_4 N11_4 115.9(2) 6_565 . ?
O12_4 C12_4 N11_4 116.55(19) . . ?
O12_4 C12_4 C13_4 126.72(19) . . ?
C13_4 C12_4 N11_4 116.7(2) . . ?
C12_4 C13_4 C12_4 121.4(3) . 6_565 ?
C12_4 C13_4 H13_5 119.26(16) . . ?
C12_4 C13_4 H13_5 119.27(15) 6_565 . ?
C22_5 N21_5 H21_5 127.3(16) . . ?
C22_5 N21_5 C25_5 108.10(19) . . ?
C25_5 N21_5 H21_5 124.5(16) . . ?
C22_5 N23_5 H23_5 126.8(16) . . ?
C22_5 N23_5 C24_5 108.37(19) . . ?
C24_5 N23_5 H23_5 124.8(16) . . ?
N21_5 C22_5 H22_5 125.3(15) . . ?
N23_5 C22_5 N21_5 109.2(2) . . ?
N23_5 C22_5 H22_5 125.5(15) . . ?
N23_5 C24_5 H24_5 119.5(15) . . ?
C25_5 C24_5 N23_5 107.3(2) . . ?
C25_5 C24_5 H24_5 133.1(15) . . ?
N21_5 C25_5 H25_5 118.2(16) . . ?
C24_5 C25_5 N21_5 107.0(2) . . ?
C24_5 C25_5 H25_5 134.7(16) . . ?
C22_6 N21_6 H21_6 126.6(15) . . ?
C22_6 N21_6 C25_6 108.29(19) . . ?
C25_6 N21_6 H21_6 124.9(15) . . ?
C22_6 N23_6 H23_6 126.2(16) . . ?
C22_6 N23_6 C24_6 108.38(19) . . ?
C24_6 N23_6 H23_6 125.4(16) . . ?
N21_6 C22_6 N23_6 108.9(2) . . ?
N21_6 C22_6 H22_6 126.3(14) . . ?
N23_6 C22_6 H22_6 124.7(14) . . ?
N23_6 C24_6 H24_6 120.1(15) . . ?
C25_6 C24_6 N23_6 107.2(2) . . ?
C25_6 C24_6 H24_6 132.6(16) . . ?
N21_6 C25_6 H25_6 118.6(15) . . ?
C24_6 C25_6 N21_6 107.2(2) . . ?
C24_6 C25_6 H25_6 134.1(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11_1 H11_1 O12_3 0.891(16) 2.016(16) 2.906(2) 177(2) 8_565
N11_2 H11_2 O12_4 0.867(16) 2.030(16) 2.892(2) 173(2) 8_565
N11_3 H11_3 O12_1 0.877(16) 2.023(16) 2.900(2) 178(2) 8_465
N11_4 H11_4 O12_2 0.886(16) 2.028(16) 2.911(2) 175(2) 8_465
N21_5 H21_5 O12_3 0.890(16) 1.811(16) 2.697(2) 173(2) .
N23_5 H23_5 O12_1 0.870(16) 1.782(17) 2.642(2) 170(2) .
N21_6 H21_6 O12_2 0.897(16) 1.773(17) 2.659(2) 169(2) .
N23_6 H23_6 O12_4 0.894(16) 1.790(16) 2.672(2) 168(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
O12_1 C12_1 C13_1 C12_1 -178.83(17) . . . 6_565 ?
N11_1 C12_1 C13_1 C12_1 1.1(4) . . . 6_565 ?
C11_1 N11_1 C12_1 O12_1 178.9(2) . . . . ?
C11_1 N11_1 C12_1 C13_1 -1.0(4) . . . . ?
C12_1 N11_1 C11_1 O11_1 -178.2(3) . . . . ?
C12_1 N11_1 C11_1 N11_1 0.8(4) . . . 6_565 ?
O12_2 C12_2 C13_2 C12_2 -177.46(17) . . . 6_565 ?
N11_2 C12_2 C13_2 C12_2 2.2(4) . . . 6_565 ?
C11_2 N11_2 C12_2 O12_2 176.8(2) . . . . ?
C11_2 N11_2 C12_2 C13_2 -2.9(4) . . . . ?
C12_2 N11_2 C11_2 O11_2 -176.7(3) . . . . ?
C12_2 N11_2 C11_2 N11_2 3.5(4) . . . 6_565 ?
O12_3 C12_3 C13_3 C12_3 -176.71(16) . . . 6_565 ?
N11_3 C12_3 C13_3 C12_3 2.5(4) . . . 6_565 ?
C11_3 N11_3 C12_3 O12_3 176.4(2) . . . . ?
C11_3 N11_3 C12_3 C13_3 -2.9(3) . . . . ?
C12_3 N11_3 C11_3 O11_3 -175.8(2) . . . . ?
C12_3 N11_3 C11_3 N11_3 3.1(4) . . . 6_565 ?
O12_4 C12_4 C13_4 C12_4 179.16(17) . . . 6_565 ?
N11_4 C12_4 C13_4 C12_4 -0.3(4) . . . 6_565 ?
C11_4 N11_4 C12_4 O12_4 -179.9(2) . . . . ?
C11_4 N11_4 C12_4 C13_4 -0.4(3) . . . . ?
C12_4 N11_4 C11_4 O11_4 -179.6(2) . . . . ?
C12_4 N11_4 C11_4 N11_4 1.0(4) . . . 6_565 ?
N23_5 C24_5 C25_5 N21_5 0.3(3) . . . . ?
C22_5 N21_5 C25_5 C24_5 -0.5(3) . . . . ?
C22_5 N23_5 C24_5 C25_5 0.1(3) . . . . ?
C24_5 N23_5 C22_5 N21_5 -0.4(3) . . . . ?
C25_5 N21_5 C22_5 N23_5 0.5(3) . . . . ?
N23_6 C24_6 C25_6 N21_6 -0.2(3) . . . . ?
C22_6 N21_6 C25_6 C24_6 0.0(3) . . . . ?
C22_6 N23_6 C24_6 C25_6 0.4(3) . . . . ?
C24_6 N23_6 C22_6 N21_6 -0.4(3) . . . . ?
C25_6 N21_6 C22_6 N23_6 0.2(3) . . . . ?

_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_kurz_socr_2
_database_code_depnum_ccdc_archive 'CCDC 2244542'
loop_
_audit_author_name
_audit_author_address
'Taisiya Sukhikh'
;NIIC SB RAS
Russia
;
_audit_update_record             
;
2023-02-25 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2023-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C2 H1.5 N O S0.5), C3 H5 N2'
_chemical_formula_sum            'C7 H8 N4 O2 S'
_chemical_formula_weight         212.23
_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'
S S 0.1246 0.1234 '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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.5356(4)
_cell_length_b                   11.9051(6)
_cell_length_c                   10.5692(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.3500(10)
_cell_angle_gamma                90
_cell_volume                     993.33(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3442
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1229 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.8834.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8034
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_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                1775
_reflns_number_total             2121
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.050
_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)+(0.0394P)²+0.4305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0890
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N11(H11), C13(H13), N11(H11), C13(H13), N21(H21), N23(H23), C22(H22),
 C24(H24), C25(H25)
;
_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
S11_1 S 0.85159(8) 0.2500 0.57951(6) 0.02425(16) Uani 1 2 d S T P . .
O12_1 O 0.78839(15) 0.44938(9) 0.96369(11) 0.0255(3) Uani 1 1 d . . . . .
N11_1 N 0.80745(17) 0.34609(11) 0.79072(13) 0.0196(3) Uani 1 1 d . . . . .
H11_1 H 0.8095 0.4099 0.7494 0.024 Uiso 1 1 calc R U . . .
C12_1 C 0.8207(3) 0.2500 0.7270(2) 0.0192(5) Uani 1 2 d S T P . .
C13_1 C 0.7808(3) 0.2500 0.9784(2) 0.0215(5) Uani 1 2 d S T P . .
H13_1 H 0.7669 0.2500 1.0635 0.026 Uiso 1 2 calc R U P . .
C14_1 C 0.7909(2) 0.35176(13) 0.91669(16) 0.0200(3) Uani 1 1 d . . . . .
S11_2 S 0.76521(7) 0.7500 1.04991(5) 0.02136(16) Uani 1 2 d S T P . .
O12_2 O 0.83159(14) 0.55148(9) 0.66568(11) 0.0234(3) Uani 1 1 d . . . . .
N11_2 N 0.81026(16) 0.65350(11) 0.83928(12) 0.0176(3) Uani 1 1 d . . . . .
H11_2 H 0.8051 0.5895 0.8793 0.021 Uiso 1 1 calc R U . . .
C12_2 C 0.7986(3) 0.7500 0.9037(2) 0.0177(5) Uani 1 2 d S T P . .
C13_2 C 0.8418(3) 0.7500 0.6535(2) 0.0214(5) Uani 1 2 d S T P . .
H13_2 H 0.8585 0.7500 0.5696 0.026 Uiso 1 2 calc R U P . .
C14_2 C 0.82971(19) 0.64857(13) 0.71451(15) 0.0188(3) Uani 1 1 d . . . . .
N21_3 N 0.26876(17) 0.49002(12) 0.60593(13) 0.0238(3) Uani 1 1 d . . . . .
H21_3 H 0.2369 0.4646 0.5217 0.029 Uiso 1 1 calc R U . . .
N23_3 N 0.27592(18) 0.52168(12) 0.80788(13) 0.0247(3) Uani 1 1 d . . . . .
H23_3 H 0.2491 0.5210 0.8805 0.030 Uiso 1 1 calc R U . . .
C22_3 C 0.1915(2) 0.46982(15) 0.69076(16) 0.0248(4) Uani 1 1 d . . . . .
H22_3 H 0.0923 0.4256 0.6711 0.030 Uiso 1 1 calc R U . . .
C24_3 C 0.4114(2) 0.57631(16) 0.79770(17) 0.0307(4) Uani 1 1 d . . . . .
H24_3 H 0.4934 0.6197 0.8669 0.037 Uiso 1 1 calc R U . . .
C25_3 C 0.4060(2) 0.55675(18) 0.67048(18) 0.0344(4) Uani 1 1 d . . . . .
H25_3 H 0.4834 0.5843 0.6328 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11_1 C12_1 1.677(2) . ?
O12_1 C14_1 1.2671(19) . ?
N11_1 H11_1 0.8800 . ?
N11_1 C12_1 1.3540(17) . ?
N11_1 C14_1 1.393(2) . ?
C12_1 N11_1 1.3540(17) 4_565 ?
C13_1 H13_1 0.9500 . ?
C13_1 C14_1 1.3942(19) 4_565 ?
C13_1 C14_1 1.3942(19) . ?
S11_2 C12_2 1.674(2) . ?
O12_2 C14_2 1.2684(19) . ?
N11_2 H11_2 0.8800 . ?
N11_2 C12_2 1.3584(17) . ?
N11_2 C14_2 1.3916(19) . ?
C12_2 N11_2 1.3584(17) 4_575 ?
C13_2 H13_2 0.9500 . ?
C13_2 C14_2 1.3911(19) 4_575 ?
C13_2 C14_2 1.3911(19) . ?
N21_3 H21_3 0.8800 . ?
N21_3 C22_3 1.321(2) . ?
N21_3 C25_3 1.364(2) . ?
N23_3 H23_3 0.8800 . ?
N23_3 C22_3 1.325(2) . ?
N23_3 C24_3 1.366(2) . ?
C22_3 H22_3 0.9500 . ?
C24_3 H24_3 0.9500 . ?
C24_3 C25_3 1.348(2) . ?
C25_3 H25_3 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
C12_1 N11_1 H11_1 117.5 . . ?
C12_1 N11_1 C14_1 125.07(14) . . ?
C14_1 N11_1 H11_1 117.5 . . ?
N11_1 C12_1 S11_1 122.34(10) 4_565 . ?
N11_1 C12_1 S11_1 122.34(10) . . ?
N11_1 C12_1 N11_1 115.32(19) . 4_565 ?
C14_1 C13_1 H13_1 119.7 4_565 . ?
C14_1 C13_1 H13_1 119.7 . . ?
C14_1 C13_1 C14_1 120.7(2) . 4_565 ?
O12_1 C14_1 N11_1 116.23(14) . . ?
O12_1 C14_1 C13_1 126.89(15) . . ?
N11_1 C14_1 C13_1 116.87(15) . . ?
C12_2 N11_2 H11_2 117.7 . . ?
C12_2 N11_2 C14_2 124.66(14) . . ?
C14_2 N11_2 H11_2 117.7 . . ?
N11_2 C12_2 S11_2 122.23(9) . . ?
N11_2 C12_2 S11_2 122.23(9) 4_575 . ?
N11_2 C12_2 N11_2 115.51(19) 4_575 . ?
C14_2 C13_2 H13_2 119.8 4_575 . ?
C14_2 C13_2 H13_2 119.8 . . ?
C14_2 C13_2 C14_2 120.5(2) . 4_575 ?
O12_2 C14_2 N11_2 116.65(14) . . ?
O12_2 C14_2 C13_2 126.00(15) . . ?
C13_2 C14_2 N11_2 117.33(15) . . ?
C22_3 N21_3 H21_3 125.6 . . ?
C22_3 N21_3 C25_3 108.77(14) . . ?
C25_3 N21_3 H21_3 125.6 . . ?
C22_3 N23_3 H23_3 125.5 . . ?
C22_3 N23_3 C24_3 108.92(14) . . ?
C24_3 N23_3 H23_3 125.5 . . ?
N21_3 C22_3 N23_3 108.35(15) . . ?
N21_3 C22_3 H22_3 125.8 . . ?
N23_3 C22_3 H22_3 125.8 . . ?
N23_3 C24_3 H24_3 126.6 . . ?
C25_3 C24_3 N23_3 106.73(15) . . ?
C25_3 C24_3 H24_3 126.6 . . ?
N21_3 C25_3 H25_3 126.4 . . ?
C24_3 C25_3 N21_3 107.23(15) . . ?
C24_3 C25_3 H25_3 126.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11_1 H11_1 O12_2 0.88 1.95 2.8240(17) 175.9 .
N11_2 H11_2 O12_1 0.88 1.92 2.8028(17) 178.6 .
N21_3 H21_3 O12_2 0.88 1.85 2.7108(17) 165.8 3_666
N23_3 H23_3 O12_1 0.88 1.83 2.6939(17) 167.6 3_667

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
C12_1 N11_1 C14_1 O12_1 176.70(17) . . . . ?
C12_1 N11_1 C14_1 C13_1 -2.6(3) . . . . ?
C14_1 N11_1 C12_1 S11_1 -176.38(13) . . . . ?
C14_1 N11_1 C12_1 N11_1 3.5(3) . . . 4_565 ?
C14_1 C13_1 C14_1 O12_1 -177.80(12) 4_565 . . . ?
C14_1 C13_1 C14_1 N11_1 1.4(3) 4_565 . . . ?
C12_2 N11_2 C14_2 O12_2 -177.22(16) . . . . ?
C12_2 N11_2 C14_2 C13_2 1.5(3) . . . . ?
C14_2 N11_2 C12_2 S11_2 176.75(13) . . . . ?
C14_2 N11_2 C12_2 N11_2 -1.1(3) . . . 4_575 ?
C14_2 C13_2 C14_2 O12_2 176.78(12) 4_575 . . . ?
C14_2 C13_2 C14_2 N11_2 -1.8(3) 4_575 . . . ?
N23_3 C24_3 C25_3 N21_3 -0.5(2) . . . . ?
C22_3 N21_3 C25_3 C24_3 0.4(2) . . . . ?
C22_3 N23_3 C24_3 C25_3 0.4(2) . . . . ?
C24_3 N23_3 C22_3 N21_3 -0.2(2) . . . . ?
C25_3 N21_3 C22_3 N23_3 -0.1(2) . . . . ?

_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_kurz_socr_1_1
_database_code_depnum_ccdc_archive 'CCDC 2244541'
loop_
_audit_author_name
_audit_author_address
'Taisiya Sukhikh'
;NIIC SB RAS
Russia
;
_audit_update_record             
;
2023-02-25 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2023-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 N2 O3, C3 H5 N2'
_chemical_formula_sum            'C7 H8 N4 O3'
_chemical_formula_weight         196.17
_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      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                   12.0971(3)
_cell_length_b                   12.1081(3)
_cell_length_c                   13.3996(3)
_cell_angle_alpha                80.9330(10)
_cell_angle_beta                 73.8040(10)
_cell_angle_gamma                60.9000(10)
_cell_volume                     1646.31(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8961
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0826 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.9537.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20792
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.898
_diffrn_reflns_theta_min         1.583
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_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                6250
_reflns_number_total             7799
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         7799
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.044
_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)+(0.0480P)²+0.3590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1068
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N11_1-H11_1 = N13_1-H13_1 = N11_3-H11_3 = N13_3-H13_3 = N21_5-H21_5 = N23_5-
 H23_5 = N13_4-H13_4 = N11_4-H11_4 = N21_8-H21_8 = N23_8-H23_8 = N13_2-H13_2 =
 N11_2-H11_2 = N21_6-H21_6 = N23_6-H23_6 = N23_7-H23_7 = N21_7-H21_7
 0.88 with sigma of 0.02
 C24_6-H24_6 = C25_6-H25_6 = C15_2-H15_2 = C15_1-H15_1 = C15_3-H15_3 = C22_5-
 H22_5 = C24_5-H24_5 = C25_5-H25_5 = C22_6-H22_6 = C24_7-H24_7 = C25_7-H25_7 =
 C22_7-H22_7 = C15_4-H15_4 = C25_8-H25_8 = C24_8-H24_8 = C22_8-H22_8
 0.95 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_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
O11_1 O -0.04286(10) 1.03819(10) 0.87795(9) 0.0275(3) Uani 1 1 d . . . . .
O12_1 O 0.32189(10) 1.05283(10) 0.87924(9) 0.0264(2) Uani 1 1 d . . . . .
O13_1 O 0.31825(10) 0.66146(9) 0.88485(8) 0.0230(2) Uani 1 1 d . . . . .
N11_1 N 0.14076(11) 0.85068(11) 0.87972(10) 0.0200(3) Uani 1 1 d D . . . .
H11_1 H 0.0962(15) 0.8110(15) 0.8795(13) 0.024 Uiso 1 1 d D U . . .
N13_1 N 0.14322(12) 1.04023(11) 0.87788(10) 0.0205(3) Uani 1 1 d D . . . .
H13_1 H 0.1006(15) 1.1248(13) 0.8778(13) 0.025 Uiso 1 1 d D U . . .
C12_1 C 0.07305(14) 0.97981(13) 0.87829(11) 0.0204(3) Uani 1 1 d . . . . .
C14_1 C 0.27284(14) 0.98084(14) 0.87988(11) 0.0207(3) Uani 1 1 d . . . . .
C15_1 C 0.33646(14) 0.84896(14) 0.88269(12) 0.0232(3) Uani 1 1 d D . . . .
H15_1 H 0.4249(14) 0.8063(15) 0.8840(13) 0.028 Uiso 1 1 d D U . . .
C16_1 C 0.27060(13) 0.78141(13) 0.88286(11) 0.0189(3) Uani 1 1 d . . . . .
O11_2 O -0.19210(10) 1.33773(9) 0.55192(8) 0.0235(2) Uani 1 1 d . . . . .
O12_2 O -0.23985(9) 0.98244(9) 0.63000(8) 0.0217(2) Uani 1 1 d . . . . .
O13_2 O 0.14719(9) 0.98501(9) 0.64073(8) 0.0212(2) Uani 1 1 d . . . . .
N11_2 N -0.02502(11) 1.15949(11) 0.59922(9) 0.0179(2) Uani 1 1 d D . . . .
H11_2 H 0.0180(15) 1.2000(15) 0.5953(13) 0.021 Uiso 1 1 d D U . . .
N13_2 N -0.21447(11) 1.15885(11) 0.59654(9) 0.0185(3) Uani 1 1 d D . . . .
H13_2 H -0.2947(13) 1.2011(15) 0.5929(12) 0.022 Uiso 1 1 d D U . . .
C12_2 C -0.14659(13) 1.22547(13) 0.58044(11) 0.0179(3) Uani 1 1 d . . . . .
C14_2 C -0.16516(13) 1.03007(13) 0.62303(11) 0.0173(3) Uani 1 1 d . . . . .
C15_2 C -0.03948(13) 0.96773(13) 0.63863(11) 0.0184(3) Uani 1 1 d D . . . .
H15_2 H -0.0050(15) 0.8814(13) 0.6604(12) 0.022 Uiso 1 1 d D U . . .
C16_2 C 0.03321(13) 1.03120(13) 0.62787(10) 0.0171(3) Uani 1 1 d . . . . .
O11_3 O 0.35177(10) 0.33721(10) 0.93667(9) 0.0270(2) Uani 1 1 d . . . . .
O12_3 O 0.01044(10) 0.31083(10) 0.88521(9) 0.0262(2) Uani 1 1 d . . . . .
O13_3 O 0.02693(11) 0.69887(10) 0.83996(9) 0.0298(3) Uani 1 1 d . . . . .
N11_3 N 0.18762(12) 0.51594(12) 0.88719(10) 0.0210(3) Uani 1 1 d D . . . .
H11_3 H 0.2264(16) 0.5603(15) 0.8897(13) 0.025 Uiso 1 1 d D U . . .
N13_3 N 0.18189(11) 0.32623(11) 0.90485(10) 0.0198(3) Uani 1 1 d D . . . .
H13_3 H 0.2243(15) 0.2434(13) 0.9085(13) 0.024 Uiso 1 1 d D U . . .
C12_3 C 0.24682(13) 0.38975(13) 0.91089(11) 0.0194(3) Uani 1 1 d . . . . .
C14_3 C 0.05964(13) 0.38229(14) 0.88308(11) 0.0195(3) Uani 1 1 d . . . . .
C15_3 C 0.00332(14) 0.51245(14) 0.86110(11) 0.0208(3) Uani 1 1 d D . . . .
H15_3 H -0.0774(14) 0.5507(15) 0.8438(12) 0.025 Uiso 1 1 d D U . . .
C16_3 C 0.06675(14) 0.58199(14) 0.86157(11) 0.0220(3) Uani 1 1 d . . . . .
O11_4 O -0.51444(11) 0.92951(10) 0.62712(10) 0.0339(3) Uani 1 1 d . . . . .
O12_4 O -0.50697(10) 1.29319(9) 0.65154(9) 0.0257(2) Uani 1 1 d . . . . .
O13_4 O -0.88435(9) 1.29262(9) 0.61040(8) 0.0228(2) Uani 1 1 d . . . . .
N11_4 N -0.69967(11) 1.11383(11) 0.62193(10) 0.0208(3) Uani 1 1 d D . . . .
H11_4 H -0.7387(16) 1.0712(15) 0.6193(13) 0.025 Uiso 1 1 d D U . . .
N13_4 N -0.51508(12) 1.11483(11) 0.63774(10) 0.0205(3) Uani 1 1 d D . . . .
H13_4 H -0.4315(14) 1.0737(15) 0.6378(13) 0.025 Uiso 1 1 d D U . . .
C12_4 C -0.57287(14) 1.04533(13) 0.62880(12) 0.0215(3) Uani 1 1 d . . . . .
C14_4 C -0.57595(14) 1.24515(13) 0.64134(11) 0.0190(3) Uani 1 1 d . . . . .
C15_4 C -0.70425(14) 1.30967(13) 0.63172(12) 0.0215(3) Uani 1 1 d D . . . .
H15_4 H -0.7501(15) 1.4006(13) 0.6346(13) 0.026 Uiso 1 1 d D U . . .
C16_4 C -0.76834(13) 1.24441(13) 0.62116(11) 0.0188(3) Uani 1 1 d . . . . .
N21_5 N -0.23029(12) 0.87629(13) 0.86985(10) 0.0270(3) Uani 1 1 d D . . . .
H21_5 H -0.1449(14) 0.8123(15) 0.8645(13) 0.032 Uiso 1 1 d D U . . .
N23_5 N -0.43531(12) 0.97726(13) 0.87438(10) 0.0258(3) Uani 1 1 d D . . . .
H23_5 H -0.5163(14) 0.9914(17) 0.8765(13) 0.031 Uiso 1 1 d D U . . .
C22_5 C -0.33336(15) 0.86398(15) 0.86939(13) 0.0261(3) Uani 1 1 d D . . . .
H22_5 H -0.3363(17) 0.7878(14) 0.8678(14) 0.031 Uiso 1 1 d D U . . .
C24_5 C -0.39712(15) 1.06482(15) 0.87891(13) 0.0267(3) Uani 1 1 d D . . . .
H24_5 H -0.4583(16) 1.1523(13) 0.8847(13) 0.032 Uiso 1 1 d D U . . .
C25_5 C -0.26900(15) 1.00233(15) 0.87614(12) 0.0244(3) Uani 1 1 d D . . . .
H25_5 H -0.2097(15) 1.0276(16) 0.8792(13) 0.029 Uiso 1 1 d D U . . .
N21_6 N 0.16464(12) 1.26382(12) 0.36778(10) 0.0227(3) Uani 1 1 d D . . . .
H21_6 H 0.1837(16) 1.1821(13) 0.3690(13) 0.027 Uiso 1 1 d D U . . .
N23_6 N 0.05810(12) 1.46673(11) 0.37735(10) 0.0216(3) Uani 1 1 d D . . . .
H23_6 H -0.0057(15) 1.5468(14) 0.3814(13) 0.026 Uiso 1 1 d D U . . .
C22_6 C 0.04672(15) 1.36249(14) 0.38585(12) 0.0228(3) Uani 1 1 d D . . . .
H22_6 H -0.0327(14) 1.3577(16) 0.4044(13) 0.027 Uiso 1 1 d D U . . .
C24_6 C 0.18815(15) 1.43440(14) 0.35318(12) 0.0245(3) Uani 1 1 d D . . . .
H24_6 H 0.2143(16) 1.4978(15) 0.3493(13) 0.029 Uiso 1 1 d D U . . .
C25_6 C 0.25465(15) 1.30685(15) 0.34760(13) 0.0258(3) Uani 1 1 d D . . . .
H25_6 H 0.3449(14) 1.2472(15) 0.3346(13) 0.031 Uiso 1 1 d D U . . .
N21_7 N -0.23167(12) 1.38480(12) 0.87153(10) 0.0236(3) Uani 1 1 d D . . . .
H21_7 H -0.1525(14) 1.3661(16) 0.8800(13) 0.028 Uiso 1 1 d D U . . .
N23_7 N -0.43393(12) 1.48887(12) 0.86652(10) 0.0229(3) Uani 1 1 d D . . . .
H23_7 H -0.5149(14) 1.5515(15) 0.8750(13) 0.028 Uiso 1 1 d D U . . .
C22_7 C -0.34017(15) 1.49261(15) 0.89611(12) 0.0244(3) Uani 1 1 d D . . . .
H22_7 H -0.3477(16) 1.5603(14) 0.9318(13) 0.029 Uiso 1 1 d D U . . .
C24_7 C -0.38409(15) 1.37438(15) 0.82192(12) 0.0253(3) Uani 1 1 d D . . . .
H24_7 H -0.4365(16) 1.3520(16) 0.7973(13) 0.030 Uiso 1 1 d D U . . .
C25_7 C -0.25745(15) 1.30948(15) 0.82537(12) 0.0249(3) Uani 1 1 d D . . . .
H25_7 H -0.1903(15) 1.2245(14) 0.8058(13) 0.030 Uiso 1 1 d D U . . .
N21_8 N -0.31834(12) 1.25952(11) 0.36493(10) 0.0216(3) Uani 1 1 d D . . . .
H21_8 H -0.2551(15) 1.1782(13) 0.3588(13) 0.026 Uiso 1 1 d D U . . .
N23_8 N -0.41544(12) 1.46277(11) 0.36344(10) 0.0212(3) Uani 1 1 d D . . . .
H23_8 H -0.4319(16) 1.5438(13) 0.3581(13) 0.025 Uiso 1 1 d D U . . .
C22_8 C -0.30094(15) 1.36102(14) 0.34516(12) 0.0230(3) Uani 1 1 d D . . . .
H22_8 H -0.2197(14) 1.3618(16) 0.3243(13) 0.028 Uiso 1 1 d D U . . .
C24_8 C -0.51032(15) 1.42523(14) 0.39646(12) 0.0247(3) Uani 1 1 d D . . . .
H24_8 H -0.5991(14) 1.4862(15) 0.4147(13) 0.030 Uiso 1 1 d D U . . .
C25_8 C -0.44936(15) 1.29751(15) 0.39707(13) 0.0253(3) Uani 1 1 d D . . . .
H25_8 H -0.4792(16) 1.2371(15) 0.4161(13) 0.030 Uiso 1 1 d D 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
O11_1 C12_1 1.2265(17) . ?
O12_1 C14_1 1.2687(18) . ?
O13_1 C16_1 1.2745(17) . ?
N11_1 H11_1 0.879(13) . ?
N11_1 C12_1 1.3674(18) . ?
N11_1 C16_1 1.3844(18) . ?
N13_1 H13_1 0.895(13) . ?
N13_1 C12_1 1.3623(19) . ?
N13_1 C14_1 1.3774(18) . ?
C14_1 C15_1 1.395(2) . ?
C15_1 H15_1 0.939(14) . ?
C15_1 C16_1 1.391(2) . ?
O11_2 C12_2 1.2339(16) . ?
O12_2 C14_2 1.2651(17) . ?
O13_2 C16_2 1.2632(16) . ?
N11_2 H11_2 0.860(13) . ?
N11_2 C12_2 1.3655(17) . ?
N11_2 C16_2 1.3983(17) . ?
N13_2 H13_2 0.861(13) . ?
N13_2 C12_2 1.3646(18) . ?
N13_2 C14_2 1.3971(17) . ?
C14_2 C15_2 1.3915(19) . ?
C15_2 H15_2 0.948(13) . ?
C15_2 C16_2 1.391(2) . ?
O11_3 C12_3 1.2352(17) . ?
O12_3 C14_3 1.2600(17) . ?
O13_3 C16_3 1.2666(18) . ?
N11_3 H11_3 0.877(14) . ?
N11_3 C12_3 1.3630(18) . ?
N11_3 C16_3 1.3969(18) . ?
N13_3 H13_3 0.877(13) . ?
N13_3 C12_3 1.3630(19) . ?
N13_3 C14_3 1.3910(18) . ?
C14_3 C15_3 1.398(2) . ?
C15_3 H15_3 0.935(13) . ?
C15_3 C16_3 1.389(2) . ?
O11_4 C12_4 1.2262(17) . ?
O12_4 C14_4 1.2705(17) . ?
O13_4 C16_4 1.2731(16) . ?
N11_4 H11_4 0.862(14) . ?
N11_4 C12_4 1.3663(18) . ?
N11_4 C16_4 1.3828(18) . ?
N13_4 H13_4 0.883(14) . ?
N13_4 C12_4 1.3645(18) . ?
N13_4 C14_4 1.3814(17) . ?
C14_4 C15_4 1.392(2) . ?
C15_4 H15_4 0.964(13) . ?
C15_4 C16_4 1.392(2) . ?
N21_5 H21_5 0.933(14) . ?
N21_5 C22_5 1.328(2) . ?
N21_5 C25_5 1.371(2) . ?
N23_5 H23_5 0.902(14) . ?
N23_5 C22_5 1.321(2) . ?
N23_5 C24_5 1.361(2) . ?
C22_5 H22_5 0.944(14) . ?
C24_5 H24_5 0.952(14) . ?
C24_5 C25_5 1.346(2) . ?
C25_5 H25_5 0.918(14) . ?
N21_6 H21_6 0.898(13) . ?
N21_6 C22_6 1.3273(19) . ?
N21_6 C25_6 1.369(2) . ?
N23_6 H23_6 0.897(14) . ?
N23_6 C22_6 1.319(2) . ?
N23_6 C24_6 1.3748(19) . ?
C22_6 H22_6 0.951(13) . ?
C24_6 H24_6 0.953(14) . ?
C24_6 C25_6 1.354(2) . ?
C25_6 H25_6 0.954(14) . ?
N21_7 H21_7 0.907(14) . ?
N21_7 C22_7 1.328(2) . ?
N21_7 C25_7 1.369(2) . ?
N23_7 H23_7 0.889(14) . ?
N23_7 C22_7 1.324(2) . ?
N23_7 C24_7 1.375(2) . ?
C22_7 H22_7 0.967(14) . ?
C24_7 H24_7 0.947(14) . ?
C24_7 C25_7 1.350(2) . ?
C25_7 H25_7 0.970(14) . ?
N21_8 H21_8 0.905(14) . ?
N21_8 C22_8 1.3201(19) . ?
N21_8 C25_8 1.3717(19) . ?
N23_8 H23_8 0.896(14) . ?
N23_8 C22_8 1.3201(19) . ?
N23_8 C24_8 1.371(2) . ?
C22_8 H22_8 0.949(13) . ?
C24_8 H24_8 0.947(14) . ?
C24_8 C25_8 1.351(2) . ?
C25_8 H25_8 0.937(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12_1 N11_1 H11_1 115.8(11) . . ?
C12_1 N11_1 C16_1 124.61(12) . . ?
C16_1 N11_1 H11_1 119.6(11) . . ?
C12_1 N13_1 H13_1 116.9(11) . . ?
C12_1 N13_1 C14_1 124.89(12) . . ?
C14_1 N13_1 H13_1 118.2(11) . . ?
O11_1 C12_1 N11_1 122.91(13) . . ?
O11_1 C12_1 N13_1 121.79(13) . . ?
N13_1 C12_1 N11_1 115.30(12) . . ?
O12_1 C14_1 N13_1 115.99(13) . . ?
O12_1 C14_1 C15_1 126.73(13) . . ?
N13_1 C14_1 C15_1 117.27(13) . . ?
C14_1 C15_1 H15_1 118.8(11) . . ?
C16_1 C15_1 C14_1 120.75(13) . . ?
C16_1 C15_1 H15_1 120.4(11) . . ?
O13_1 C16_1 N11_1 116.43(13) . . ?
O13_1 C16_1 C15_1 126.41(13) . . ?
N11_1 C16_1 C15_1 117.15(13) . . ?
C12_2 N11_2 H11_2 118.0(11) . . ?
C12_2 N11_2 C16_2 124.66(12) . . ?
C16_2 N11_2 H11_2 117.3(11) . . ?
C12_2 N13_2 H13_2 116.6(11) . . ?
C12_2 N13_2 C14_2 124.85(12) . . ?
C14_2 N13_2 H13_2 118.5(11) . . ?
O11_2 C12_2 N11_2 122.25(13) . . ?
O11_2 C12_2 N13_2 122.49(12) . . ?
N13_2 C12_2 N11_2 115.26(12) . . ?
O12_2 C14_2 N13_2 116.26(12) . . ?
O12_2 C14_2 C15_2 126.89(13) . . ?
C15_2 C14_2 N13_2 116.85(12) . . ?
C14_2 C15_2 H15_2 118.8(10) . . ?
C14_2 C15_2 C16_2 121.26(12) . . ?
C16_2 C15_2 H15_2 119.8(10) . . ?
O13_2 C16_2 N11_2 116.15(12) . . ?
O13_2 C16_2 C15_2 126.86(12) . . ?
C15_2 C16_2 N11_2 116.99(12) . . ?
C12_3 N11_3 H11_3 118.4(11) . . ?
C12_3 N11_3 C16_3 124.86(13) . . ?
C16_3 N11_3 H11_3 116.7(11) . . ?
C12_3 N13_3 H13_3 116.8(11) . . ?
C12_3 N13_3 C14_3 124.76(12) . . ?
C14_3 N13_3 H13_3 118.1(11) . . ?
O11_3 C12_3 N11_3 122.01(13) . . ?
O11_3 C12_3 N13_3 122.55(13) . . ?
N13_3 C12_3 N11_3 115.44(12) . . ?
O12_3 C14_3 N13_3 116.79(13) . . ?
O12_3 C14_3 C15_3 126.39(13) . . ?
N13_3 C14_3 C15_3 116.83(13) . . ?
C14_3 C15_3 H15_3 117.6(10) . . ?
C16_3 C15_3 C14_3 121.30(13) . . ?
C16_3 C15_3 H15_3 121.0(10) . . ?
O13_3 C16_3 N11_3 116.62(13) . . ?
O13_3 C16_3 C15_3 126.68(13) . . ?
C15_3 C16_3 N11_3 116.69(13) . . ?
C12_4 N11_4 H11_4 116.4(11) . . ?
C12_4 N11_4 C16_4 124.62(12) . . ?
C16_4 N11_4 H11_4 118.9(11) . . ?
C12_4 N13_4 H13_4 117.5(11) . . ?
C12_4 N13_4 C14_4 124.77(12) . . ?
C14_4 N13_4 H13_4 117.7(11) . . ?
O11_4 C12_4 N11_4 122.70(13) . . ?
O11_4 C12_4 N13_4 122.00(13) . . ?
N13_4 C12_4 N11_4 115.31(12) . . ?
O12_4 C14_4 N13_4 115.79(12) . . ?
O12_4 C14_4 C15_4 127.02(13) . . ?
N13_4 C14_4 C15_4 117.18(13) . . ?
C14_4 C15_4 H15_4 119.5(10) . . ?
C14_4 C15_4 C16_4 120.87(13) . . ?
C16_4 C15_4 H15_4 119.6(10) . . ?
O13_4 C16_4 N11_4 116.15(12) . . ?
O13_4 C16_4 C15_4 126.66(13) . . ?
N11_4 C16_4 C15_4 117.20(12) . . ?
C22_5 N21_5 H21_5 127.4(11) . . ?
C22_5 N21_5 C25_5 108.18(13) . . ?
C25_5 N21_5 H21_5 124.4(11) . . ?
C22_5 N23_5 H23_5 124.1(12) . . ?
C22_5 N23_5 C24_5 108.58(13) . . ?
C24_5 N23_5 H23_5 127.3(12) . . ?
N21_5 C22_5 H22_5 126.9(11) . . ?
N23_5 C22_5 N21_5 108.85(14) . . ?
N23_5 C22_5 H22_5 124.2(11) . . ?
N23_5 C24_5 H24_5 120.7(11) . . ?
C25_5 C24_5 N23_5 107.42(14) . . ?
C25_5 C24_5 H24_5 131.8(11) . . ?
N21_5 C25_5 H25_5 119.6(11) . . ?
C24_5 C25_5 N21_5 106.97(14) . . ?
C24_5 C25_5 H25_5 133.4(11) . . ?
C22_6 N21_6 H21_6 126.7(11) . . ?
C22_6 N21_6 C25_6 108.45(13) . . ?
C25_6 N21_6 H21_6 124.9(11) . . ?
C22_6 N23_6 H23_6 127.7(11) . . ?
C22_6 N23_6 C24_6 108.62(12) . . ?
C24_6 N23_6 H23_6 123.5(11) . . ?
N21_6 C22_6 H22_6 125.0(11) . . ?
N23_6 C22_6 N21_6 108.99(13) . . ?
N23_6 C22_6 H22_6 126.0(11) . . ?
N23_6 C24_6 H24_6 120.0(10) . . ?
C25_6 C24_6 N23_6 106.79(14) . . ?
C25_6 C24_6 H24_6 133.0(11) . . ?
N21_6 C25_6 H25_6 119.1(11) . . ?
C24_6 C25_6 N21_6 107.15(14) . . ?
C24_6 C25_6 H25_6 133.8(11) . . ?
C22_7 N21_7 H21_7 125.8(11) . . ?
C22_7 N21_7 C25_7 108.52(13) . . ?
C25_7 N21_7 H21_7 125.6(11) . . ?
C22_7 N23_7 H23_7 124.0(11) . . ?
C22_7 N23_7 C24_7 108.60(13) . . ?
C24_7 N23_7 H23_7 127.4(11) . . ?
N21_7 C22_7 H22_7 124.3(10) . . ?
N23_7 C22_7 N21_7 108.75(14) . . ?
N23_7 C22_7 H22_7 127.0(10) . . ?
N23_7 C24_7 H24_7 121.8(11) . . ?
C25_7 C24_7 N23_7 106.86(14) . . ?
C25_7 C24_7 H24_7 131.3(11) . . ?
N21_7 C25_7 H25_7 120.0(10) . . ?
C24_7 C25_7 N21_7 107.26(14) . . ?
C24_7 C25_7 H25_7 132.7(10) . . ?
C22_8 N21_8 H21_8 126.3(11) . . ?
C22_8 N21_8 C25_8 108.55(12) . . ?
C25_8 N21_8 H21_8 125.1(11) . . ?
C22_8 N23_8 H23_8 127.8(11) . . ?
C22_8 N23_8 C24_8 108.54(13) . . ?
C24_8 N23_8 H23_8 123.6(11) . . ?
N21_8 C22_8 H22_8 126.1(11) . . ?
N23_8 C22_8 N21_8 109.04(13) . . ?
N23_8 C22_8 H22_8 124.8(11) . . ?
N23_8 C24_8 H24_8 120.2(11) . . ?
C25_8 C24_8 N23_8 106.96(13) . . ?
C25_8 C24_8 H24_8 132.8(11) . . ?
N21_8 C25_8 H25_8 120.0(11) . . ?
C24_8 C25_8 N21_8 106.91(14) . . ?
C24_8 C25_8 H25_8 133.1(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11_1 H11_1 O13_3 0.879(13) 2.100(14) 2.9561(17) 164.2(15) .
N13_1 H13_1 O12_3 0.895(13) 1.973(14) 2.8669(16) 176.5(16) 1_565
N11_2 H11_2 O13_4 0.860(13) 2.046(14) 2.8988(16) 171.2(15) 1_655
N13_2 H13_2 O12_4 0.861(13) 2.195(14) 3.0056(16) 156.6(15) .
N11_3 H11_3 O13_1 0.877(14) 1.999(14) 2.8751(16) 176.1(16) .
N13_3 H13_3 O12_1 0.877(13) 2.061(14) 2.9198(16) 165.9(15) 1_545
N11_4 H11_4 O13_2 0.862(14) 2.040(14) 2.8904(16) 168.8(16) 1_455
N13_4 H13_4 O12_2 0.883(14) 2.005(14) 2.8869(15) 177.0(16) .
N21_5 H21_5 O13_3 0.933(14) 1.816(14) 2.7444(17) 172.8(17) .
N23_5 H23_5 O12_1 0.902(14) 1.714(14) 2.6014(16) 167.2(17) 1_455
N21_6 H21_6 O12_2 0.898(13) 1.764(14) 2.6585(16) 173.4(16) 2_576
N23_6 H23_6 O13_4 0.897(14) 1.741(14) 2.6337(15) 173.3(16) 2_486
N21_7 H21_7 O12_3 0.907(14) 1.765(14) 2.6664(16) 171.8(17) 1_565
N23_7 H23_7 O13_1 0.889(14) 1.777(14) 2.6593(16) 171.6(17) 1_465
N21_8 H21_8 O13_2 0.905(14) 1.761(14) 2.6607(15) 172.4(16) 2_576
N23_8 H23_8 O12_4 0.896(14) 1.736(14) 2.6216(16) 169.3(16) 2_486

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
O12_1 C14_1 C15_1 C16_1 -179.86(15) . . . . ?
N13_1 C14_1 C15_1 C16_1 0.3(2) . . . . ?
C12_1 N11_1 C16_1 O13_1 179.33(13) . . . . ?
C12_1 N11_1 C16_1 C15_1 -1.2(2) . . . . ?
C12_1 N13_1 C14_1 O12_1 -179.92(13) . . . . ?
C12_1 N13_1 C14_1 C15_1 -0.1(2) . . . . ?
C14_1 N13_1 C12_1 O11_1 178.92(14) . . . . ?
C14_1 N13_1 C12_1 N11_1 -0.7(2) . . . . ?
C14_1 C15_1 C16_1 O13_1 179.69(14) . . . . ?
C14_1 C15_1 C16_1 N11_1 0.2(2) . . . . ?
C16_1 N11_1 C12_1 O11_1 -178.25(14) . . . . ?
C16_1 N11_1 C12_1 N13_1 1.4(2) . . . . ?
O12_2 C14_2 C15_2 C16_2 179.59(14) . . . . ?
N13_2 C14_2 C15_2 C16_2 -0.2(2) . . . . ?
C12_2 N11_2 C16_2 O13_2 179.03(13) . . . . ?
C12_2 N11_2 C16_2 C15_2 -0.6(2) . . . . ?
C12_2 N13_2 C14_2 O12_2 -176.67(13) . . . . ?
C12_2 N13_2 C14_2 C15_2 3.2(2) . . . . ?
C14_2 N13_2 C12_2 O11_2 176.17(13) . . . . ?
C14_2 N13_2 C12_2 N11_2 -4.5(2) . . . . ?
C14_2 C15_2 C16_2 O13_2 179.47(14) . . . . ?
C14_2 C15_2 C16_2 N11_2 -1.0(2) . . . . ?
C16_2 N11_2 C12_2 O11_2 -177.51(13) . . . . ?
C16_2 N11_2 C12_2 N13_2 3.2(2) . . . . ?
O12_3 C14_3 C15_3 C16_3 179.64(15) . . . . ?
N13_3 C14_3 C15_3 C16_3 -0.3(2) . . . . ?
C12_3 N11_3 C16_3 O13_3 -178.87(14) . . . . ?
C12_3 N11_3 C16_3 C15_3 0.3(2) . . . . ?
C12_3 N13_3 C14_3 O12_3 -176.73(13) . . . . ?
C12_3 N13_3 C14_3 C15_3 3.2(2) . . . . ?
C14_3 N13_3 C12_3 O11_3 175.46(13) . . . . ?
C14_3 N13_3 C12_3 N11_3 -4.1(2) . . . . ?
C14_3 C15_3 C16_3 O13_3 177.77(15) . . . . ?
C14_3 C15_3 C16_3 N11_3 -1.3(2) . . . . ?
C16_3 N11_3 C12_3 O11_3 -177.31(14) . . . . ?
C16_3 N11_3 C12_3 N13_3 2.2(2) . . . . ?
O12_4 C14_4 C15_4 C16_4 -179.90(14) . . . . ?
N13_4 C14_4 C15_4 C16_4 1.3(2) . . . . ?
C12_4 N11_4 C16_4 O13_4 177.48(13) . . . . ?
C12_4 N11_4 C16_4 C15_4 -2.3(2) . . . . ?
C12_4 N13_4 C14_4 O12_4 178.89(14) . . . . ?
C12_4 N13_4 C14_4 C15_4 -2.2(2) . . . . ?
C14_4 N13_4 C12_4 O11_4 -179.19(15) . . . . ?
C14_4 N13_4 C12_4 N11_4 0.8(2) . . . . ?
C14_4 C15_4 C16_4 O13_4 -178.98(14) . . . . ?
C14_4 C15_4 C16_4 N11_4 0.7(2) . . . . ?
C16_4 N11_4 C12_4 O11_4 -178.47(15) . . . . ?
C16_4 N11_4 C12_4 N13_4 1.5(2) . . . . ?
N23_5 C24_5 C25_5 N21_5 0.03(18) . . . . ?
C22_5 N21_5 C25_5 C24_5 -0.29(18) . . . . ?
C22_5 N23_5 C24_5 C25_5 0.24(18) . . . . ?
C24_5 N23_5 C22_5 N21_5 -0.43(18) . . . . ?
C25_5 N21_5 C22_5 N23_5 0.44(18) . . . . ?
N23_6 C24_6 C25_6 N21_6 0.33(18) . . . . ?
C22_6 N21_6 C25_6 C24_6 -0.44(18) . . . . ?
C22_6 N23_6 C24_6 C25_6 -0.10(18) . . . . ?
C24_6 N23_6 C22_6 N21_6 -0.18(17) . . . . ?
C25_6 N21_6 C22_6 N23_6 0.39(17) . . . . ?
N23_7 C24_7 C25_7 N21_7 -0.13(17) . . . . ?
C22_7 N21_7 C25_7 C24_7 0.35(17) . . . . ?
C22_7 N23_7 C24_7 C25_7 -0.13(17) . . . . ?
C24_7 N23_7 C22_7 N21_7 0.35(17) . . . . ?
C25_7 N21_7 C22_7 N23_7 -0.43(17) . . . . ?
N23_8 C24_8 C25_8 N21_8 0.32(18) . . . . ?
C22_8 N21_8 C25_8 C24_8 -0.26(18) . . . . ?
C22_8 N23_8 C24_8 C25_8 -0.27(18) . . . . ?
C24_8 N23_8 C22_8 N21_8 0.10(17) . . . . ?
C25_8 N21_8 C22_8 N23_8 0.10(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
