# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_777a
_database_code_depnum_ccdc_archive 'CCDC 2278515'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N4 O4'
_chemical_formula_weight         224.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.0461(7)
_cell_length_b                   7.5519(6)
_cell_length_c                   9.8725(9)
_cell_angle_alpha                96.563(6)
_cell_angle_beta                 102.071(6)
_cell_angle_gamma                108.791(5)
_cell_volume                     476.88(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3105
_cell_measurement_theta_min      4.67
_cell_measurement_theta_max      67.64

_exptl_crystal_description       block
_exptl_crystal_colour            yellow_lemon
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    1.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5681
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.671
_diffrn_reflns_theta_max         67.751
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1696
_reflns_number_gt                1520
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.1164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0051(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1696
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 1.0429(2) 0.56110(18) 0.85622(14) 0.0629(4) Uani 1 1 d . . . . .
N2 N 0.9061(2) 0.3820(2) 0.78355(17) 0.0560(4) Uani 1 1 d . . . . .
C3 C 0.8232(2) 0.4064(2) 0.66013(17) 0.0395(4) Uani 1 1 d . . . . .
N4 N 0.6782(2) 0.25454(18) 0.56133(15) 0.0441(3) Uani 1 1 d . . . . .
H4A H 0.647(4) 0.144(4) 0.589(3) 0.077(7) Uiso 1 1 d . . . . .
C5 C 0.5767(2) 0.2522(2) 0.42682(17) 0.0400(4) Uani 1 1 d . . . . .
O6 O 0.4487(2) 0.10166(16) 0.35502(13) 0.0545(3) Uani 1 1 d . . . . .
C7 C 0.6106(2) 0.4236(2) 0.36428(18) 0.0407(4) Uani 1 1 d . . . . .
H7A H 0.527(3) 0.392(3) 0.268(2) 0.049(5) Uiso 1 1 d . . . . .
C8 C 0.7326(2) 0.6071(2) 0.41390(16) 0.0374(3) Uani 1 1 d . . . . .
C9 C 0.7292(2) 0.7521(2) 0.31992(17) 0.0424(4) Uani 1 1 d . . . . .
O10 O 0.8387(2) 0.91549(16) 0.36072(14) 0.0642(4) Uani 1 1 d . . . . .
O11 O 0.59427(19) 0.67951(16) 0.19626(13) 0.0541(3) Uani 1 1 d . . . . .
C12 C 0.5840(3) 0.8093(3) 0.0960(2) 0.0594(5) Uani 1 1 d . . . . .
H12A H 0.443(4) 0.752(3) 0.037(3) 0.073(6) Uiso 1 1 d . . . . .
H12B H 0.605(3) 0.940(4) 0.154(3) 0.072(6) Uiso 1 1 d . . . . .
C13 C 0.7420(4) 0.8206(4) 0.0168(3) 0.0744(6) Uani 1 1 d . . . . .
H13A H 0.719(4) 0.889(4) -0.058(3) 0.079(7) Uiso 1 1 d . . . . .
H13B H 0.885(4) 0.879(4) 0.088(3) 0.088(8) Uiso 1 1 d . . . . .
H13C H 0.744(5) 0.704(5) -0.028(3) 0.106(10) Uiso 1 1 d . . . . .
N14 N 0.8686(2) 0.69169(19) 0.54269(15) 0.0446(4) Uani 1 1 d . . . . .
H14A H 0.933(3) 0.810(3) 0.554(2) 0.060(6) Uiso 1 1 d . . . . .
C15 C 0.9076(2) 0.6027(2) 0.65354(16) 0.0378(3) Uani 1 1 d . . . . .
N16 N 1.0407(2) 0.6959(2) 0.77268(15) 0.0516(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N16 1.3832(18) . ?
O1 N2 1.3862(19) . ?
N2 C3 1.297(2) . ?
C3 N4 1.372(2) . ?
C3 C15 1.423(2) . ?
N4 C5 1.366(2) . ?
C5 O6 1.223(2) . ?
C5 C7 1.469(2) . ?
C7 C8 1.342(2) . ?
C8 N14 1.361(2) . ?
C8 C9 1.517(2) . ?
C9 O10 1.193(2) . ?
C9 O11 1.312(2) . ?
O11 C12 1.478(2) . ?
C12 C13 1.476(3) . ?
N14 C15 1.373(2) . ?
C15 N16 1.297(2) . ?

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
N16 O1 N2 110.54(12) . . ?
C3 N2 O1 105.64(13) . . ?
N2 C3 N4 120.38(14) . . ?
N2 C3 C15 108.95(15) . . ?
N4 C3 C15 130.67(14) . . ?
C5 N4 C3 128.65(13) . . ?
O6 C5 N4 118.96(14) . . ?
O6 C5 C7 117.95(15) . . ?
N4 C5 C7 123.08(14) . . ?
C8 C7 C5 132.96(16) . . ?
C7 C8 N14 129.54(14) . . ?
C7 C8 C9 119.58(14) . . ?
N14 C8 C9 110.88(13) . . ?
O10 C9 O11 125.70(15) . . ?
O10 C9 C8 120.87(15) . . ?
O11 C9 C8 113.41(13) . . ?
C9 O11 C12 117.23(13) . . ?
C13 C12 O11 109.94(17) . . ?
C8 N14 C15 126.11(14) . . ?
N16 C15 N14 121.57(14) . . ?
N16 C15 C3 109.44(14) . . ?
N14 C15 C3 128.97(15) . . ?
C15 N16 O1 105.43(13) . . ?

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
N4 H4A O6 0.88(3) 1.94(3) 2.8257(17) 175(2) 2_656 yes
N14 H14A O10 0.84(2) 2.12(2) 2.9246(19) 160(2) 2_776 yes

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_1443cs
_database_code_depnum_ccdc_archive 'CCDC 2278516'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N4 O4'
_chemical_formula_weight         224.18

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   23.936(2)
_cell_length_b                   5.1742(5)
_cell_length_c                   7.7436(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     959.03(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1203
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      24.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2251
_exptl_absorpt_correction_T_max  0.2732
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6293
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.702
_diffrn_reflns_theta_max         28.237
_diffrn_reflns_theta_full        25.242
_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 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.854
_reflns_number_total             1977
_reflns_number_gt                1023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.560
_reflns_Friedel_fraction_max     0.647
_reflns_Friedel_fraction_full    0.681

_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 
; 
 Flack x determined using 295 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -1.9(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1977
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_restrained_S_all      0.826
_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 0.08903(9) 0.3920(5) 0.6136(3) 0.0581(7) Uani 1 1 d . . . . .
N2 N 0.09789(11) 0.6125(5) 0.5115(4) 0.0560(9) Uani 1 1 d . . . . .
C3 C 0.15190(13) 0.6241(6) 0.4984(4) 0.0380(8) Uani 1 1 d . . . . .
N4 N 0.18276(10) 0.8005(5) 0.4066(3) 0.0376(7) Uani 1 1 d . . . . .
H4 H 0.166058 0.922946 0.352132 0.045 Uiso 1 1 calc R U . . .
C5 C 0.23953(12) 0.7838(6) 0.4008(4) 0.0337(7) Uani 1 1 d . . . . .
O6 O 0.26708(8) 0.9348(4) 0.3145(3) 0.0444(6) Uani 1 1 d . . . . .
C7 C 0.26751(12) 0.5726(5) 0.5029(4) 0.0303(7) Uani 1 1 d . . . . .
C8 C 0.32341(11) 0.5727(6) 0.5033(4) 0.0356(8) Uani 1 1 d . . . . .
H8 H 0.341596 0.700801 0.440630 0.043 Uiso 1 1 calc R U . . .
C9 C 0.35762(13) 0.3855(7) 0.5954(4) 0.0393(9) Uani 1 1 d . . . . .
O10 O 0.33874(9) 0.2120(4) 0.6831(3) 0.0498(7) Uani 1 1 d . . . . .
O11 O 0.41148(9) 0.4298(4) 0.5712(3) 0.0574(8) Uani 1 1 d . . . . .
C12 C 0.45179(13) 0.2516(8) 0.6468(5) 0.0731(12) Uani 1 1 d . . . . .
H12A H 0.435458 0.167527 0.746705 0.088 Uiso 1 1 calc R U . . .
H12B H 0.484575 0.346266 0.684501 0.088 Uiso 1 1 calc R U . . .
C13 C 0.46807(15) 0.0552(8) 0.5177(7) 0.0974(16) Uani 1 1 d . . . . .
H13A H 0.496302 -0.055261 0.565644 0.146 Uiso 1 1 calc R U . . .
H13B H 0.482481 0.139626 0.416639 0.146 Uiso 1 1 calc R U . . .
H13C H 0.436005 -0.046204 0.486842 0.146 Uiso 1 1 calc R U . . .
N14 N 0.23420(9) 0.3956(4) 0.5895(3) 0.0350(7) Uani 1 1 d . . . . .
H14 H 0.249380 0.270243 0.645384 0.042 Uiso 1 1 calc R U . . .
C15 C 0.17722(13) 0.4197(6) 0.5864(4) 0.0334(8) Uani 1 1 d . . . . .
N16 N 0.13990(10) 0.2733(5) 0.6574(4) 0.0467(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.404(3) . ?
O1 N16 1.405(3) . ?
N2 C3 1.298(3) . ?
C3 N4 1.372(4) . ?
C3 C15 1.397(4) . ?
N4 C5 1.362(3) . ?
C5 O6 1.221(3) . ?
C5 C7 1.506(4) . ?
C7 C8 1.338(3) . ?
C7 N14 1.387(3) . ?
C8 C9 1.455(4) . ?
C9 O10 1.213(3) . ?
C9 O11 1.323(3) . ?
O11 C12 1.457(4) . ?
C12 C13 1.478(5) . ?
N14 C15 1.370(3) . ?
C15 N16 1.293(3) . ?

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 N16 111.1(2) . . ?
C3 N2 O1 103.4(3) . . ?
N2 C3 N4 127.4(3) . . ?
N2 C3 C15 111.0(3) . . ?
N4 C3 C15 121.5(3) . . ?
C5 N4 C3 120.8(3) . . ?
O6 C5 N4 121.1(3) . . ?
O6 C5 C7 120.8(3) . . ?
N4 C5 C7 118.2(3) . . ?
C8 C7 N14 125.0(3) . . ?
C8 C7 C5 116.5(3) . . ?
N14 C7 C5 118.5(2) . . ?
C7 C8 C9 124.3(3) . . ?
O10 C9 O11 124.8(3) . . ?
O10 C9 C8 123.9(3) . . ?
O11 C9 C8 111.3(3) . . ?
C9 O11 C12 118.6(3) . . ?
O11 C12 C13 109.7(3) . . ?
C15 N14 C7 120.2(3) . . ?
N16 C15 N14 128.8(3) . . ?
N16 C15 C3 110.5(3) . . ?
N14 C15 C3 120.6(3) . . ?
C15 N16 O1 103.9(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
N4 H4 O10 0.86 1.99 2.792(3) 154.6 4_564 yes
N14 H14 O6 0.86 2.21 2.953(3) 144.6 4_545 yes
N14 H14 O10 0.86 2.18 2.773(3) 125.9 . yes

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_zz511
_database_code_depnum_ccdc_archive 'CCDC 2278517'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N4 O4'
_chemical_formula_weight         224.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.9852(3)
_cell_length_b                   9.8017(6)
_cell_length_c                   10.6338(7)
_cell_angle_alpha                67.729(4)
_cell_angle_beta                 86.664(4)
_cell_angle_gamma                83.011(4)
_cell_volume                     477.23(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3175
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      67.09

_exptl_crystal_description       block
_exptl_crystal_colour            pale_yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6151
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.493
_diffrn_reflns_theta_max         67.475
_diffrn_reflns_theta_full        67.475
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1688
_reflns_number_gt                1523
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²+0.1686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_number_reflns         1688
_refine_ls_number_parameters     247
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1578
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.107
_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 0.8684(4) 0.3116(2) 0.30694(18) 0.0752(6) Uani 1 1 d . . . . .
N2 N 0.6449(5) 0.3999(3) 0.3293(3) 0.0784(7) Uani 1 1 d . . . . .
C3 C 0.5331(5) 0.3180(3) 0.4401(3) 0.0619(6) Uani 1 1 d D . . . .
N4 N 0.3040(5) 0.3666(3) 0.4950(3) 0.0688(6) Uani 1 1 d . . . . .
H4 H 0.236(6) 0.446(4) 0.444(3) 0.067(8) Uiso 1 1 d . . . . .
C5 C 0.1723(6) 0.2894(3) 0.6117(3) 0.0670(7) Uani 1 1 d . . . . .
O6 O -0.0394(4) 0.3427(2) 0.64310(19) 0.0740(6) Uani 1 1 d . . . . .
C7 C 0.2532(11) 0.1376(7) 0.7160(6) 0.0495(13) Uani 0.599(11) 1 d . . P A 1
H7A H 0.163(15) 0.104(11) 0.790(11) 0.07(3) Uiso 0.599(11) 1 d . . P A 1
C8 C 0.4598(7) 0.0384(4) 0.7117(3) 0.0402(14) Uani 0.599(11) 1 d D . P A 1
C9 C 0.5114(17) -0.1123(10) 0.8262(9) 0.053(2) Uani 0.599(11) 1 d D . P A 1
O10 O 0.6600(13) -0.2078(7) 0.8138(7) 0.0760(15) Uani 0.599(11) 1 d D . P A 1
O11 O 0.3495(14) -0.1204(7) 0.9303(7) 0.0667(16) Uani 0.599(11) 1 d D . P A 1
N14 N 0.6536(15) 0.0471(8) 0.6101(7) 0.0464(17) Uani 0.599(11) 1 d D . P A 1
H14 H 0.770(15) -0.024(9) 0.632(8) 0.08(3) Uiso 0.599(11) 1 d . . P A 1
C12 C 0.360(3) -0.2607(14) 1.0493(16) 0.069(3) Uani 0.599(11) 1 d D . P A 1
H12A H 0.545517 -0.306839 1.062733 0.082 Uiso 0.599(11) 1 calc R U P A 1
H12B H 0.301977 -0.240407 1.129635 0.082 Uiso 0.599(11) 1 calc R U P A 1
C13 C 0.188(4) -0.363(2) 1.0320(19) 0.114(6) Uani 0.599(11) 1 d D . P A 1
H13A H 0.199489 -0.453525 1.111090 0.171 Uiso 0.599(11) 1 calc R U P A 1
H13B H 0.004163 -0.318606 1.020281 0.171 Uiso 0.599(11) 1 calc R U P A 1
H13C H 0.247467 -0.384974 0.953444 0.171 Uiso 0.599(11) 1 calc R U P A 1
C15 C 0.6829(17) 0.1719(11) 0.4950(11) 0.043(3) Uani 0.599(11) 1 d D . P A 1
C7A C 0.3657(18) 0.1428(8) 0.6605(9) 0.054(2) Uani 0.401(11) 1 d D . P A 2
C8A C 0.2720(18) 0.0584(12) 0.7790(13) 0.065(3) Uani 0.401(11) 1 d D . P A 2
H8A H 0.094(16) 0.096(8) 0.827(8) 0.04(2) Uiso 0.401(11) 1 d . . P A 2
N14A N 0.591(3) 0.0930(17) 0.6012(16) 0.056(3) Uani 0.401(11) 1 d D . P A 2
H14A H 0.70(3) 0.000(14) 0.614(13) 0.04(4) Uiso 0.401(11) 1 d . . P A 2
C9A C 0.406(3) -0.0961(13) 0.8584(13) 0.061(3) Uani 0.401(11) 1 d D . P A 2
O10A O 0.600(3) -0.1505(16) 0.8158(13) 0.101(6) Uani 0.401(11) 1 d D . P A 2
O11A O 0.286(2) -0.1468(13) 0.9787(12) 0.071(2) Uani 0.401(11) 1 d D . P A 2
C12A C 0.398(5) -0.296(2) 1.065(3) 0.065(4) Uani 0.401(11) 1 d D . P A 2
H12C H 0.418470 -0.302223 1.157334 0.079 Uiso 0.401(11) 1 calc R U P A 2
H12D H 0.573055 -0.321823 1.030482 0.079 Uiso 0.401(11) 1 calc R U P A 2
C13A C 0.201(4) -0.393(2) 1.060(2) 0.073(4) Uani 0.401(11) 1 d D . P A 2
H13T H 0.262573 -0.494263 1.115177 0.109 Uiso 0.401(11) 1 calc R U P A 2
H13F H 0.029280 -0.365306 1.093905 0.109 Uiso 0.401(11) 1 calc R U P A 2
H13G H 0.182862 -0.384779 0.967875 0.109 Uiso 0.401(11) 1 calc R U P A 2
C15A C 0.686(4) 0.186(2) 0.4841(18) 0.062(7) Uani 0.401(11) 1 d D . P A 2
N16 N 0.8890(5) 0.1722(2) 0.4102(2) 0.0598(5) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N16 1.388(3) . ?
O1 N2 1.391(3) . ?
N2 C3 1.288(4) . ?
C3 C15A 1.345(15) . ?
C3 N4 1.368(4) . ?
C3 C15 1.452(8) . ?
N4 C5 1.363(4) . ?
N4 H4 0.81(3) . ?
C5 O6 1.206(4) . ?
C5 C7 1.503(7) . ?
C5 C7A 1.555(8) . ?
C7 C8 1.339(8) . ?
C7 H7A 0.86(10) . ?
C8 N14 1.392(8) . ?
C8 C9 1.520(9) . ?
C9 O10 1.164(10) . ?
C9 O11 1.315(8) . ?
O11 C12 1.471(12) . ?
N14 C15 1.380(11) . ?
N14 H14 0.82(8) . ?
C12 C13 1.467(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 N16 1.326(7) . ?
C7A C8A 1.313(15) . ?
C7A N14A 1.384(14) . ?
C8A C9A 1.518(17) . ?
C8A H8A 1.09(9) . ?
N14A C15A 1.335(16) . ?
N14A H14A 0.96(14) . ?
C9A O10A 1.195(13) . ?
C9A O11A 1.321(10) . ?
O11A C12A 1.460(16) . ?
C12A C13A 1.470(17) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C13A H13T 0.9600 . ?
C13A H13F 0.9600 . ?
C13A H13G 0.9600 . ?
C15A N16 1.273(15) . ?

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
N16 O1 N2 110.39(19) . . ?
C3 N2 O1 105.8(2) . . ?
N2 C3 C15A 106.6(7) . . ?
N2 C3 N4 123.0(2) . . ?
C15A C3 N4 130.4(7) . . ?
N2 C3 C15 110.7(4) . . ?
N4 C3 C15 126.3(4) . . ?
C5 N4 C3 127.4(2) . . ?
C5 N4 H4 120(2) . . ?
C3 N4 H4 112(2) . . ?
O6 C5 N4 120.2(2) . . ?
O6 C5 C7 110.8(3) . . ?
N4 C5 C7 128.9(3) . . ?
O6 C5 C7A 140.2(5) . . ?
N4 C5 C7A 99.5(4) . . ?
C8 C7 C5 128.8(5) . . ?
C8 C7 H7A 111(7) . . ?
C5 C7 H7A 121(6) . . ?
C7 C8 N14 129.6(5) . . ?
C7 C8 C9 122.0(5) . . ?
N14 C8 C9 108.4(5) . . ?
O10 C9 O11 126.9(9) . . ?
O10 C9 C8 122.2(8) . . ?
O11 C9 C8 110.6(7) . . ?
C9 O11 C12 118.7(9) . . ?
C15 N14 C8 124.8(6) . . ?
C15 N14 H14 122(5) . . ?
C8 N14 H14 113(5) . . ?
C13 C12 O11 111.5(13) . . ?
C13 C12 H12A 109.3 . . ?
O11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
O11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N16 C15 N14 119.8(6) . . ?
N16 C15 C3 106.4(6) . . ?
N14 C15 C3 133.8(6) . . ?
C8A C7A N14A 121.0(9) . . ?
C8A C7A C5 106.6(8) . . ?
N14A C7A C5 132.3(9) . . ?
C7A C8A C9A 122.1(10) . . ?
C7A C8A H8A 122(4) . . ?
C9A C8A H8A 116(4) . . ?
C15A N14A C7A 118.4(12) . . ?
C15A N14A H14A 104(8) . . ?
C7A N14A H14A 137(8) . . ?
O10A C9A O11A 129.3(15) . . ?
O10A C9A C8A 122.3(14) . . ?
O11A C9A C8A 108.3(14) . . ?
C9A O11A C12A 113.4(18) . . ?
O11A C12A C13A 104.9(18) . . ?
O11A C12A H12C 110.8 . . ?
C13A C12A H12C 110.8 . . ?
O11A C12A H12D 110.8 . . ?
C13A C12A H12D 110.8 . . ?
H12C C12A H12D 108.8 . . ?
C12A C13A H13T 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13T C13A H13F 109.5 . . ?
C12A C13A H13G 109.5 . . ?
H13T C13A H13G 109.5 . . ?
H13F C13A H13G 109.5 . . ?
N16 C15A N14A 131.8(13) . . ?
N16 C15A C3 116.4(13) . . ?
N14A C15A C3 111.8(12) . . ?
C15A N16 O1 100.8(8) . . ?
C15 N16 O1 106.8(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
_geom_hbond_publ_flag
N4 H4 O6 0.81(3) 2.07(4) 2.856(3) 166(3) 2_566 yes
N14^a H14^a O10^a 0.82(8) 2.18(8) 2.612(9) 113(6) . yes
N14^a H14^a N16 0.82(8) 2.24(8) 2.994(7) 154(7) 2_756 yes
N14A^b H14A^b O10A^b 0.96(14) 2.16(12) 2.60(2) 106(9) . yes

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046

