# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_gul015
_database_code_depnum_ccdc_archive 'CCDC 2067439'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-03-02 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H N9 O6'
_chemical_formula_sum            'C4 H N9 O6'
_chemical_formula_weight         271.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   6.2831(10)
_cell_length_b                   6.0046(10)
_cell_length_c                   13.003(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.560(3)
_cell_angle_gamma                90
_cell_volume                     490.38(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1798
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      26.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8776
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         29.990
_diffrn_reflns_theta_full        29.990
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2859
_reflns_number_gt                2016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2859
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.986
_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
O1 O -0.0340(4) 0.6030(5) 0.8818(2) 0.0332(7) Uani 1 1 d . . . . .
O2 O 0.5789(4) 0.8340(4) 0.8093(2) 0.0287(6) Uani 1 1 d . . . . .
O3 O 0.5970(4) 0.3098(5) 0.8583(2) 0.0337(7) Uani 1 1 d . . . . .
O4 O 0.3980(5) 0.1355(5) 0.9673(2) 0.0372(7) Uani 1 1 d . . . . .
N2 N 0.0781(5) 0.4254(6) 0.9223(3) 0.0300(8) Uani 1 1 d . . . . .
N3 N 0.4339(5) 0.2810(6) 0.9042(2) 0.0266(7) Uani 1 1 d . . . . .
N5 N 0.0875(5) 0.7286(6) 0.8169(3) 0.0292(8) Uani 1 1 d . . . . .
N7 N 0.4456(5) 0.7178(5) 0.7599(2) 0.0223(7) Uani 1 1 d . . . . .
N8 N 0.4384(5) 0.6643(5) 0.6648(2) 0.0230(6) Uani 1 1 d . . . . .
C3 C 0.2643(6) 0.4416(6) 0.8819(3) 0.0233(8) Uani 1 1 d . . . . .
C4 C 0.2694(6) 0.6284(7) 0.8171(3) 0.0239(8) Uani 1 1 d . . . . .
O1' O 0.7280(4) 0.6483(5) 0.3146(2) 0.0294(6) Uani 1 1 d . . . . .
O2' O 0.9965(4) 0.8685(4) 0.3471(2) 0.0294(6) Uani 1 1 d . . . . .
N1' N 0.6047(4) 0.7480(5) 0.6099(2) 0.0217(6) Uani 1 1 d . . . . .
N2' N 0.6092(5) 0.6758(5) 0.5110(2) 0.0224(7) Uani 1 1 d . . . . .
N3' N 0.8381(5) 0.7644(5) 0.3723(2) 0.0238(7) Uani 1 1 d . . . . .
N4' N 0.8755(5) 0.9241(5) 0.5454(2) 0.0238(7) Uani 1 1 d . . . . .
C3' C 0.7738(5) 0.7865(6) 0.4782(3) 0.0209(7) Uani 1 1 d . . . . .
C5' C 0.7668(6) 0.9009(6) 0.6287(3) 0.0247(8) Uani 1 1 d . . . . .
H5' H 0.794029 0.976361 0.691909 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.375(4) . ?
O1 N5 1.378(4) . ?
O2 N7 1.254(4) . ?
O3 N3 1.212(4) . ?
O4 N3 1.223(4) . ?
N2 C3 1.299(5) . ?
N3 C3 1.461(5) . ?
N5 C4 1.292(5) . ?
N7 N8 1.277(4) . ?
N7 C4 1.452(5) . ?
N8 N1' 1.376(4) . ?
C3 C4 1.404(6) . ?
O1' N3' 1.225(4) . ?
O2' N3' 1.227(4) . ?
N1' N2' 1.358(4) . ?
N1' C5' 1.388(4) . ?
N2' C3' 1.311(5) . ?
N3' C3' 1.451(5) . ?
N4' C5' 1.303(5) . ?
N4' C3' 1.351(5) . ?
C5' H5' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 N5 111.9(3) . . ?
C3 N2 O1 104.2(3) . . ?
O3 N3 O4 127.3(3) . . ?
O3 N3 C3 115.4(3) . . ?
O4 N3 C3 117.2(3) . . ?
C4 N5 O1 104.4(3) . . ?
O2 N7 N8 129.9(3) . . ?
O2 N7 C4 116.8(3) . . ?
N8 N7 C4 113.3(3) . . ?
N7 N8 N1' 113.8(3) . . ?
N2 C3 C4 109.8(3) . . ?
N2 C3 N3 122.1(3) . . ?
C4 C3 N3 128.2(3) . . ?
N5 C4 C3 109.8(3) . . ?
N5 C4 N7 120.9(3) . . ?
C3 C4 N7 129.2(3) . . ?
N2' N1' N8 114.2(3) . . ?
N2' N1' C5' 110.1(3) . . ?
N8 N1' C5' 135.6(3) . . ?
C3' N2' N1' 100.6(3) . . ?
O1' N3' O2' 125.1(3) . . ?
O1' N3' C3' 117.8(3) . . ?
O2' N3' C3' 117.1(3) . . ?
C5' N4' C3' 102.9(3) . . ?
N2' C3' N4' 117.6(3) . . ?
N2' C3' N3' 120.4(3) . . ?
N4' C3' N3' 122.1(3) . . ?
N4' C5' N1' 108.9(3) . . ?
N4' C5' H5' 125.6 . . ?
N1' C5' H5' 125.6 . . ?

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
N5 O1 N2 C3 -0.5(4) . . . . ?
N2 O1 N5 C4 0.6(4) . . . . ?
O2 N7 N8 N1' 0.4(5) . . . . ?
C4 N7 N8 N1' -180.0(3) . . . . ?
O1 N2 C3 C4 0.2(4) . . . . ?
O1 N2 C3 N3 -179.3(3) . . . . ?
O3 N3 C3 N2 177.0(3) . . . . ?
O4 N3 C3 N2 -3.8(5) . . . . ?
O3 N3 C3 C4 -2.4(6) . . . . ?
O4 N3 C3 C4 176.7(4) . . . . ?
O1 N5 C4 C3 -0.4(4) . . . . ?
O1 N5 C4 N7 -177.4(3) . . . . ?
N2 C3 C4 N5 0.1(5) . . . . ?
N3 C3 C4 N5 179.6(4) . . . . ?
N2 C3 C4 N7 176.8(4) . . . . ?
N3 C3 C4 N7 -3.7(7) . . . . ?
O2 N7 C4 N5 96.6(4) . . . . ?
N8 N7 C4 N5 -83.1(4) . . . . ?
O2 N7 C4 C3 -79.8(5) . . . . ?
N8 N7 C4 C3 100.5(4) . . . . ?
N7 N8 N1' N2' 174.4(3) . . . . ?
N7 N8 N1' C5' -10.1(5) . . . . ?
N8 N1' N2' C3' 177.6(3) . . . . ?
C5' N1' N2' C3' 0.9(4) . . . . ?
N1' N2' C3' N4' -0.4(4) . . . . ?
N1' N2' C3' N3' -178.7(3) . . . . ?
C5' N4' C3' N2' -0.2(4) . . . . ?
C5' N4' C3' N3' 178.0(3) . . . . ?
O1' N3' C3' N2' 3.4(5) . . . . ?
O2' N3' C3' N2' -178.3(3) . . . . ?
O1' N3' C3' N4' -174.9(3) . . . . ?
O2' N3' C3' N4' 3.5(5) . . . . ?
C3' N4' C5' N1' 0.8(4) . . . . ?
N2' N1' C5' N4' -1.2(4) . . . . ?
N8 N1' C5' N4' -176.9(4) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.072


####################################################################### 
# 
# 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_gul053
_database_code_depnum_ccdc_archive 'CCDC 2067440'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-03-02 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 N9 O4'
_chemical_formula_sum            'C4 H3 N9 O4'
_chemical_formula_weight         241.15

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.8786(8)
_cell_length_b                   7.9416(13)
_cell_length_c                   22.587(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     875.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1491
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      22.45

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11090
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.803
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        29.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2555
_reflns_number_gt                1987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2555
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O1 O 0.5881(4) 0.0391(2) 0.73012(8) 0.0258(4) Uani 1 1 d . . . . .
O2 O 0.9451(4) 0.4770(2) 0.69248(8) 0.0290(5) Uani 1 1 d . . . . .
N2 N 0.3963(4) 0.0247(3) 0.68353(9) 0.0223(5) Uani 1 1 d . . . . .
N5 N 0.7245(5) 0.1891(3) 0.72830(10) 0.0237(5) Uani 1 1 d . . . . .
N6 N 0.2712(6) 0.2020(3) 0.60514(11) 0.0311(6) Uani 1 1 d . . . . .
H6B H 0.141(7) 0.130(4) 0.5930(14) 0.039(9) Uiso 1 1 d . . . . .
H6A H 0.283(6) 0.296(4) 0.5856(13) 0.031(8) Uiso 1 1 d . . . . .
N7 N 0.7295(4) 0.4301(3) 0.66818(9) 0.0183(5) Uani 1 1 d . . . . .
N8 N 0.5790(4) 0.5102(3) 0.63086(9) 0.0170(4) Uani 1 1 d . . . . .
C3 C 0.4171(5) 0.1672(3) 0.65377(11) 0.0179(5) Uani 1 1 d . . . . .
C4 C 0.6225(5) 0.2658(3) 0.68248(11) 0.0166(5) Uani 1 1 d . . . . .
O1' O 0.4824(4) 0.9646(2) 0.47899(8) 0.0300(5) Uani 1 1 d . . . . .
O2' O 0.8256(4) 1.1103(2) 0.51151(9) 0.0303(5) Uani 1 1 d . . . . .
N1' N 0.6821(4) 0.6674(3) 0.61642(8) 0.0160(4) Uani 1 1 d . . . . .
N2' N 0.5599(4) 0.7370(2) 0.56803(9) 0.0170(4) Uani 1 1 d . . . . .
N3' N 0.6668(4) 0.9913(3) 0.51413(9) 0.0207(5) Uani 1 1 d . . . . .
N4' N 0.9088(4) 0.9011(3) 0.60211(9) 0.0193(5) Uani 1 1 d . . . . .
C3' C 0.7073(5) 0.8735(3) 0.56264(11) 0.0167(5) Uani 1 1 d . . . . .
C5' C 0.8913(5) 0.7682(3) 0.63658(11) 0.0191(5) Uani 1 1 d . . . . .
H5' H 1.004346 0.745583 0.669888 0.023 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N5 1.365(3) . ?
O1 N2 1.412(3) . ?
O2 N7 1.244(3) . ?
N2 C3 1.320(3) . ?
N5 C4 1.300(3) . ?
N6 C3 1.338(3) . ?
N6 H6B 0.90(3) . ?
N6 H6A 0.87(3) . ?
N7 N8 1.287(3) . ?
N7 C4 1.441(3) . ?
N8 N1' 1.384(3) . ?
C3 C4 1.428(3) . ?
O1' N3' 1.218(3) . ?
O2' N3' 1.223(3) . ?
N1' N2' 1.362(3) . ?
N1' C5' 1.375(3) . ?
N2' C3' 1.306(3) . ?
N3' C3' 1.455(3) . ?
N4' C5' 1.314(3) . ?
N4' C3' 1.345(3) . ?
C5' H5' 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
N5 O1 N2 111.76(17) . . ?
C3 N2 O1 105.0(2) . . ?
C4 N5 O1 104.3(2) . . ?
C3 N6 H6B 120(2) . . ?
C3 N6 H6A 124(2) . . ?
H6B N6 H6A 116(3) . . ?
O2 N7 N8 128.6(2) . . ?
O2 N7 C4 118.6(2) . . ?
N8 N7 C4 112.8(2) . . ?
N7 N8 N1' 113.14(19) . . ?
N2 C3 N6 123.7(2) . . ?
N2 C3 C4 107.0(2) . . ?
N6 C3 C4 129.3(2) . . ?
N5 C4 C3 111.9(2) . . ?
N5 C4 N7 117.6(2) . . ?
C3 C4 N7 130.5(2) . . ?
N2' N1' C5' 110.74(19) . . ?
N2' N1' N8 113.31(18) . . ?
C5' N1' N8 135.8(2) . . ?
C3' N2' N1' 99.83(19) . . ?
O1' N3' O2' 124.8(2) . . ?
O1' N3' C3' 118.6(2) . . ?
O2' N3' C3' 116.6(2) . . ?
C5' N4' C3' 102.4(2) . . ?
N2' C3' N4' 118.4(2) . . ?
N2' C3' N3' 122.0(2) . . ?
N4' C3' N3' 119.6(2) . . ?
N4' C5' N1' 108.7(2) . . ?
N4' C5' H5' 125.7 . . ?
N1' C5' H5' 125.7 . . ?

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
N5 O1 N2 C3 -0.2(3) . . . . ?
N2 O1 N5 C4 0.0(3) . . . . ?
O2 N7 N8 N1' 1.4(3) . . . . ?
C4 N7 N8 N1' -179.33(19) . . . . ?
O1 N2 C3 N6 178.7(3) . . . . ?
O1 N2 C3 C4 0.4(3) . . . . ?
O1 N5 C4 C3 0.2(3) . . . . ?
O1 N5 C4 N7 -179.3(2) . . . . ?
N2 C3 C4 N5 -0.4(3) . . . . ?
N6 C3 C4 N5 -178.6(3) . . . . ?
N2 C3 C4 N7 179.0(2) . . . . ?
N6 C3 C4 N7 0.8(5) . . . . ?
O2 N7 C4 N5 13.4(3) . . . . ?
N8 N7 C4 N5 -165.9(2) . . . . ?
O2 N7 C4 C3 -165.9(2) . . . . ?
N8 N7 C4 C3 14.7(4) . . . . ?
N7 N8 N1' N2' 166.4(2) . . . . ?
N7 N8 N1' C5' -8.5(4) . . . . ?
C5' N1' N2' C3' 0.6(2) . . . . ?
N8 N1' N2' C3' -175.7(2) . . . . ?
N1' N2' C3' N4' -0.5(3) . . . . ?
N1' N2' C3' N3' 176.8(2) . . . . ?
C5' N4' C3' N2' 0.3(3) . . . . ?
C5' N4' C3' N3' -177.1(2) . . . . ?
O1' N3' C3' N2' 3.0(4) . . . . ?
O2' N3' C3' N2' -176.2(2) . . . . ?
O1' N3' C3' N4' -179.7(2) . . . . ?
O2' N3' C3' N4' 1.2(3) . . . . ?
C3' N4' C5' N1' 0.1(3) . . . . ?
N2' N1' C5' N4' -0.4(3) . . . . ?
N8 N1' C5' N4' 174.6(2) . . . . ?

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
_geom_hbond_publ_flag
N6 H6B O2' 0.90(3) 2.40(3) 3.119(3) 137(3) 1_445 yes
N6 H6B N4' 0.90(3) 2.15(4) 2.973(3) 152(3) 1_445 yes
N6 H6A N8 0.87(3) 2.46(3) 2.930(3) 115(2) . yes
N6 H6A O2' 0.87(3) 2.33(3) 3.039(3) 140(2) 4_466 yes

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.245
_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_gul034
_database_code_depnum_ccdc_archive 'CCDC 2067441'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-03-02 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H2 N18 O8'
_chemical_formula_sum            'C8 H2 N18 O8'
_chemical_formula_weight         478.28

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.283(8)
_cell_length_b                   7.552(2)
_cell_length_c                   13.411(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1750.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      17.69

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19761
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         30.035
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2574
_reflns_number_gt                1843
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0330P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2574
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O1 O 0.52772(6) 0.93066(15) 0.15073(8) 0.0315(3) Uani 1 1 d . . . . .
O2 O 0.66671(6) 0.47230(16) 0.10293(7) 0.0297(3) Uani 1 1 d . . . . .
N2 N 0.57844(7) 0.81321(18) 0.19622(9) 0.0286(3) Uani 1 1 d . . . . .
N3 N 0.48807(7) 0.57756(18) -0.00675(10) 0.0264(3) Uani 1 1 d . . . . .
N5 N 0.48982(8) 0.85383(18) 0.07234(10) 0.0301(3) Uani 1 1 d . . . . .
N7 N 0.61759(7) 0.51554(17) 0.16667(9) 0.0229(3) Uani 1 1 d . . . . .
N8 N 0.60002(7) 0.44294(16) 0.24999(9) 0.0232(3) Uani 1 1 d . . . . .
C3 C 0.57091(8) 0.6693(2) 0.14539(10) 0.0236(3) Uani 1 1 d . . . . .
C4 C 0.51625(8) 0.6923(2) 0.06734(11) 0.0251(3) Uani 1 1 d . . . . .
O1' O 0.66172(6) 0.04487(16) 0.53150(8) 0.0345(3) Uani 1 1 d . . . . .
O2' O 0.71101(8) -0.16305(18) 0.44087(10) 0.0456(3) Uani 1 1 d . . . . .
N1' N 0.64293(7) 0.29496(16) 0.27137(8) 0.0211(3) Uani 1 1 d . . . . .
N2' N 0.62847(7) 0.22762(17) 0.36363(9) 0.0235(3) Uani 1 1 d . . . . .
N3' N 0.68387(7) -0.01675(18) 0.45249(10) 0.0277(3) Uani 1 1 d . . . . .
N4' N 0.72148(7) 0.06836(17) 0.28312(9) 0.0255(3) Uani 1 1 d . . . . .
C3' C 0.67707(8) 0.0953(2) 0.36456(10) 0.0226(3) Uani 1 1 d . . . . .
C5' C 0.69950(8) 0.1978(2) 0.22431(11) 0.0247(3) Uani 1 1 d . . . . .
H5' H 0.719452 0.220724 0.159580 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N5 1.3679(18) . ?
O1 N2 1.3882(17) . ?
O2 N7 1.2482(15) . ?
N2 C3 1.289(2) . ?
N3 N3 1.255(3) 5_665 ?
N3 C4 1.405(2) . ?
N5 C4 1.304(2) . ?
N7 N8 1.2812(17) . ?
N7 C3 1.4424(19) . ?
N8 N1' 1.3716(17) . ?
C3 C4 1.421(2) . ?
O1' N3' 1.2190(17) . ?
O2' N3' 1.2103(18) . ?
N1' N2' 1.3608(17) . ?
N1' C5' 1.3757(18) . ?
N2' C3' 1.3056(19) . ?
N3' C3' 1.456(2) . ?
N4' C5' 1.312(2) . ?
N4' C3' 1.3503(19) . ?
C5' H5' 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
N5 O1 N2 111.66(12) . . ?
C3 N2 O1 104.03(12) . . ?
N3 N3 C4 111.08(15) 5_665 . ?
C4 N5 O1 105.57(12) . . ?
O2 N7 N8 130.28(13) . . ?
O2 N7 C3 117.10(12) . . ?
N8 N7 C3 112.61(11) . . ?
N7 N8 N1' 113.76(11) . . ?
N2 C3 C4 110.72(14) . . ?
N2 C3 N7 121.16(13) . . ?
C4 C3 N7 128.03(14) . . ?
N5 C4 N3 119.44(13) . . ?
N5 C4 C3 108.02(14) . . ?
N3 C4 C3 132.53(14) . . ?
N2' N1' N8 113.28(11) . . ?
N2' N1' C5' 110.39(12) . . ?
N8 N1' C5' 136.30(12) . . ?
C3' N2' N1' 100.16(11) . . ?
O2' N3' O1' 125.60(14) . . ?
O2' N3' C3' 117.22(13) . . ?
O1' N3' C3' 117.19(13) . . ?
C5' N4' C3' 102.09(12) . . ?
N2' C3' N4' 118.25(13) . . ?
N2' C3' N3' 120.29(13) . . ?
N4' C3' N3' 121.45(13) . . ?
N4' C5' N1' 109.11(13) . . ?
N4' C5' H5' 125.4 . . ?
N1' C5' H5' 125.4 . . ?

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
N5 O1 N2 C3 0.21(15) . . . . ?
N2 O1 N5 C4 -0.62(15) . . . . ?
O2 N7 N8 N1' 0.4(2) . . . . ?
C3 N7 N8 N1' 179.20(11) . . . . ?
O1 N2 C3 C4 0.26(15) . . . . ?
O1 N2 C3 N7 176.89(11) . . . . ?
O2 N7 C3 N2 -111.41(16) . . . . ?
N8 N7 C3 N2 69.59(17) . . . . ?
O2 N7 C3 C4 64.58(19) . . . . ?
N8 N7 C3 C4 -114.41(16) . . . . ?
O1 N5 C4 N3 179.93(12) . . . . ?
O1 N5 C4 C3 0.74(15) . . . . ?
N3 N3 C4 N5 -171.59(16) 5_665 . . . ?
N3 N3 C4 C3 7.4(3) 5_665 . . . ?
N2 C3 C4 N5 -0.67(17) . . . . ?
N7 C3 C4 N5 -177.01(13) . . . . ?
N2 C3 C4 N3 -179.71(14) . . . . ?
N7 C3 C4 N3 4.0(3) . . . . ?
N7 N8 N1' N2' 174.74(12) . . . . ?
N7 N8 N1' C5' -2.8(2) . . . . ?
N8 N1' N2' C3' -178.48(11) . . . . ?
C5' N1' N2' C3' -0.26(15) . . . . ?
N1' N2' C3' N4' -0.19(17) . . . . ?
N1' N2' C3' N3' 178.41(13) . . . . ?
C5' N4' C3' N2' 0.58(18) . . . . ?
C5' N4' C3' N3' -178.01(13) . . . . ?
O2' N3' C3' N2' 158.85(15) . . . . ?
O1' N3' C3' N2' -21.1(2) . . . . ?
O2' N3' C3' N4' -22.6(2) . . . . ?
O1' N3' C3' N4' 157.43(14) . . . . ?
C3' N4' C5' N1' -0.68(16) . . . . ?
N2' N1' C5' N4' 0.64(16) . . . . ?
N8 N1' C5' N4' 178.27(14) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.050


