# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a1
_database_code_depnum_ccdc_archive 'CCDC 2279089'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2023-07-04 deposited with the CCDC.	2024-10-01 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         'C6 H6 N4 O4, H2 O2'
_chemical_formula_sum            'C6 H8 N4 O6'
_chemical_formula_weight         232.16

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3836(3)
_cell_length_b                   8.3568(3)
_cell_length_c                   15.1792(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.580(1)
_cell_angle_gamma                90
_cell_volume                     926.12(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6448
_cell_measurement_theta_min      2.714
_cell_measurement_theta_max      30.529

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.8937
_exptl_transmission_factor_max   0.9281
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12635
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.714
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_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             2228
_reflns_number_gt                1987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0383P)²+0.3966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0037(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2228
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0768
_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 0.70820(12) 0.20900(11) 0.62786(6) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.53004(11) 0.13041(11) 0.60598(6) 0.0209(2) Uani 1 1 d . . . . .
H1 H 0.747(2) 0.201(2) 0.5781(13) 0.037(5) Uiso 1 1 d . . . . .
H2 H 0.556(2) 0.034(2) 0.6276(11) 0.031(4) Uiso 1 1 d . . . . .
O3 O 0.56307(12) 0.83625(10) 0.67347(5) 0.0203(2) Uani 1 1 d . . . . .
O4 O 0.81027(11) 0.30917(9) 0.43597(5) 0.01407(18) Uani 1 1 d . . . . .
O5 O 0.80393(12) 0.00958(10) 0.47353(5) 0.0198(2) Uani 1 1 d . . . . .
O6 O 0.91583(12) -0.05856(10) 0.35345(6) 0.0213(2) Uani 1 1 d . . . . .
N1 N 0.63447(14) 0.57187(12) 0.68546(7) 0.0170(2) Uani 1 1 d . . . . .
H11 H 0.675(2) 0.487(2) 0.6621(11) 0.028(4) Uiso 1 1 d . . . . .
H12 H 0.626(2) 0.577(2) 0.7410(12) 0.029(4) Uiso 1 1 d . . . . .
N2 N 0.65065(14) 0.71049(12) 0.55524(6) 0.0160(2) Uani 1 1 d . . . . .
H21 H 0.626(2) 0.794(2) 0.5261(11) 0.027(4) Uiso 1 1 d . . . . .
N3 N 0.71400(13) 0.57604(11) 0.51965(6) 0.0141(2) Uani 1 1 d . . . . .
N4 N 0.86373(13) 0.04207(12) 0.40348(6) 0.0157(2) Uani 1 1 d . . . . .
C1 C 0.61340(15) 0.70993(14) 0.64113(7) 0.0146(2) Uani 1 1 d . . . . .
C2 C 0.76173(15) 0.59318(14) 0.44194(7) 0.0149(2) Uani 1 1 d . . . . .
C3 C 0.82424(15) 0.45612(14) 0.39766(7) 0.0141(2) Uani 1 1 d . . . . .
C4 C 0.89460(16) 0.44181(15) 0.31952(7) 0.0163(2) Uani 1 1 d . . . . .
C5 C 0.92530(15) 0.27677(14) 0.30720(7) 0.0161(2) Uani 1 1 d . . . . .
C6 C 0.87206(15) 0.20457(14) 0.37929(7) 0.0148(2) Uani 1 1 d . . . . .
H3 H 0.757(2) 0.6934(18) 0.4109(10) 0.020(4) Uiso 1 1 d . . . . .
H4 H 0.919(2) 0.528(2) 0.2842(10) 0.026(4) Uiso 1 1 d . . . . .
H5 H 0.971(2) 0.2266(19) 0.2594(11) 0.024(4) Uiso 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 O2 1.4634(12) . ?
O1 H1 0.849(19) . ?
O2 H2 0.881(19) . ?
O3 C1 1.2441(14) . ?
O4 C6 1.3526(13) . ?
O4 C3 1.3693(13) . ?
O5 N4 1.2407(12) . ?
O6 N4 1.2326(13) . ?
N1 C1 1.3330(15) . ?
N1 H11 0.863(18) . ?
N1 H12 0.856(17) . ?
N2 N3 1.3596(13) . ?
N2 C1 1.3720(14) . ?
N2 H21 0.833(17) . ?
N3 C2 1.2884(14) . ?
N4 C6 1.4104(15) . ?
C2 C3 1.4385(16) . ?
C2 H3 0.960(15) . ?
C3 C4 1.3693(15) . ?
C4 C5 1.4146(17) . ?
C4 H4 0.929(16) . ?
C5 C6 1.3581(16) . ?
C5 H5 0.945(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
O2 O1 H1 99.8(12) . . ?
O1 O2 H2 100.7(11) . . ?
C6 O4 C3 104.81(8) . . ?
C1 N1 H11 121.6(11) . . ?
C1 N1 H12 115.8(11) . . ?
H11 N1 H12 121.6(16) . . ?
N3 N2 C1 120.29(10) . . ?
N3 N2 H21 123.0(11) . . ?
C1 N2 H21 116.6(11) . . ?
C2 N3 N2 115.42(10) . . ?
O6 N4 O5 124.22(10) . . ?
O6 N4 C6 117.83(9) . . ?
O5 N4 C6 117.95(9) . . ?
O3 C1 N1 123.67(10) . . ?
O3 C1 N2 119.08(10) . . ?
N1 C1 N2 117.24(10) . . ?
N3 C2 C3 119.33(10) . . ?
N3 C2 H3 123.5(9) . . ?
C3 C2 H3 117.2(9) . . ?
O4 C3 C4 110.60(10) . . ?
O4 C3 C2 117.77(9) . . ?
C4 C3 C2 131.60(11) . . ?
C3 C4 C5 106.78(10) . . ?
C3 C4 H4 124.3(10) . . ?
C5 C4 H4 128.9(10) . . ?
C6 C5 C4 104.79(10) . . ?
C6 C5 H5 127.1(10) . . ?
C4 C5 H5 128.1(10) . . ?
O4 C6 C5 113.02(10) . . ?
O4 C6 N4 115.13(9) . . ?
C5 C6 N4 131.81(11) . . ?

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
C1 N2 N3 C2 -173.46(10) . . . . ?
N3 N2 C1 O3 176.94(10) . . . . ?
N3 N2 C1 N1 -2.81(16) . . . . ?
N2 N3 C2 C3 -177.78(10) . . . . ?
C6 O4 C3 C4 -0.50(12) . . . . ?
C6 O4 C3 C2 177.94(10) . . . . ?
N3 C2 C3 O4 7.37(16) . . . . ?
N3 C2 C3 C4 -174.58(12) . . . . ?
O4 C3 C4 C5 0.56(13) . . . . ?
C2 C3 C4 C5 -177.59(12) . . . . ?
C3 C4 C5 C6 -0.38(13) . . . . ?
C3 O4 C6 C5 0.25(12) . . . . ?
C3 O4 C6 N4 -177.59(9) . . . . ?
C4 C5 C6 O4 0.08(13) . . . . ?
C4 C5 C6 N4 177.46(12) . . . . ?
O6 N4 C6 O4 178.95(9) . . . . ?
O5 N4 C6 O4 -0.81(15) . . . . ?
O6 N4 C6 C5 1.62(18) . . . . ?
O5 N4 C6 C5 -178.15(12) . . . . ?
H1 O1 O2 H2 98.3(17) . . . . ?

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
O1 H1 O4 0.849(19) 2.449(19) 3.2261(12) 152.5(16) . yes
O1 H1 O5 0.849(19) 2.334(19) 3.0429(13) 141.3(16) . yes
O2 H2 O3 0.881(19) 1.791(19) 2.6603(13) 168.8(16) 1_545 yes
N1 H11 O1 0.863(18) 2.404(18) 3.2246(14) 159.1(15) . yes
N1 H12 O6 0.856(17) 2.477(17) 3.2171(13) 145.2(14) 4_566 yes
N2 H21 O5 0.833(17) 2.433(17) 3.0798(13) 135.1(14) 1_565 yes

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.047


####################################################################### 
# 
# 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_a2
_database_code_depnum_ccdc_archive 'CCDC 2279090'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2023-07-04 deposited with the CCDC.	2024-10-01 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         'C6 H6 N4 O4, 1.5(H2 O2)'
_chemical_formula_sum            'C6 H9 N4 O7'
_chemical_formula_weight         249.17

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   12.6420(4)
_cell_length_b                   8.4671(3)
_cell_length_c                   18.6298(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.447(1)
_cell_angle_gamma                90
_cell_volume                     1954.49(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7267
_cell_measurement_theta_min      2.914
_cell_measurement_theta_max      30.518

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   0.8903
_exptl_transmission_factor_max   0.9281
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15596
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.231
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_full        25.242
_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             2855
_reflns_number_gt                2473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0405P)²+1.4921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2855
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59926(6) 0.58029(10) 0.21347(4) 0.01740(17) Uani 1 1 d . . . . .
O2 O 0.64191(6) 0.45897(9) 0.17041(4) 0.01631(16) Uani 1 1 d . . . . .
H1 H 0.6529(14) 0.648(2) 0.2201(9) 0.030(4) Uiso 1 1 d . . . . .
H2 H 0.6742(14) 0.398(2) 0.2080(10) 0.034(4) Uiso 1 1 d . . . . .
O7 O 0.53713(7) 0.43546(10) 0.49574(5) 0.02236(19) Uani 1 1 d . . . . .
H7 H 0.5128(15) 0.366(2) 0.5198(10) 0.040(5) Uiso 1 1 d . . . . .
N1 N 0.59717(7) 0.35843(11) 0.34506(5) 0.01551(18) Uani 1 1 d . . . . .
H11 H 0.5701(13) 0.3567(18) 0.3827(8) 0.023(4) Uiso 1 1 d . . . . .
H12 H 0.5791(13) 0.4336(19) 0.3126(9) 0.024(4) Uiso 1 1 d . . . . .
N2 N 0.71507(7) 0.15640(10) 0.39158(5) 0.01299(17) Uani 1 1 d . . . . .
H21 H 0.7635(13) 0.0874(18) 0.3838(8) 0.024(4) Uiso 1 1 d . . . . .
N3 N 0.66404(7) 0.14332(10) 0.44900(4) 0.01202(17) Uani 1 1 d . . . . .
N4 N 0.43688(7) 0.17373(10) 0.63476(5) 0.01310(17) Uani 1 1 d . . . . .
O3 O 0.72295(6) 0.26721(9) 0.28299(4) 0.01509(16) Uani 1 1 d . . . . .
O4 O 0.56100(6) 0.12208(8) 0.56032(4) 0.01203(15) Uani 1 1 d . . . . .
O5 O 0.40162(6) 0.27951(9) 0.59031(4) 0.01828(17) Uani 1 1 d . . . . .
O6 O 0.39825(6) 0.13965(10) 0.68828(4) 0.01904(17) Uani 1 1 d . . . . .
C1 C 0.67812(8) 0.26396(12) 0.33724(5) 0.01233(19) Uani 1 1 d . . . . .
C2 C 0.69860(8) 0.03666(12) 0.49711(5) 0.01239(19) Uani 1 1 d . . . . .
C3 C 0.64482(8) 0.02015(12) 0.55809(5) 0.01187(18) Uani 1 1 d . . . . .
C4 C 0.66036(8) -0.07865(12) 0.61756(6) 0.01396(19) Uani 1 1 d . . . . .
C5 C 0.58243(8) -0.03670(12) 0.65958(6) 0.01408(19) Uani 1 1 d . . . . .
C6 C 0.52621(8) 0.08424(12) 0.62229(5) 0.01214(19) Uani 1 1 d . . . . .
H3 H 0.7586(12) -0.0318(17) 0.4958(8) 0.016(3) Uiso 1 1 d . . . . .
H4 H 0.7152(12) -0.1553(17) 0.6273(8) 0.018(3) Uiso 1 1 d . . . . .
H5 H 0.5709(12) -0.0808(18) 0.7043(8) 0.023(4) Uiso 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 O2 1.4701(10) . ?
O1 H1 0.876(18) . ?
O2 H2 0.899(18) . ?
O7 O7 1.4697(15) 5_666 ?
O7 H7 0.837(19) . ?
N1 C1 1.3295(13) . ?
N1 H11 0.839(16) . ?
N1 H12 0.876(16) . ?
N2 N3 1.3589(11) . ?
N2 C1 1.3730(13) . ?
N2 H21 0.879(16) . ?
N3 C2 1.2862(13) . ?
N4 O6 1.2284(11) . ?
N4 O5 1.2409(11) . ?
N4 C6 1.4169(13) . ?
O3 C1 1.2531(12) . ?
O4 C6 1.3530(12) . ?
O4 C3 1.3738(12) . ?
C2 C3 1.4419(13) . ?
C2 H3 0.959(14) . ?
C3 C4 1.3710(14) . ?
C4 C5 1.4197(14) . ?
C4 H4 0.941(15) . ?
C5 C6 1.3566(14) . ?
C5 H5 0.950(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
O2 O1 H1 100.1(11) . . ?
O1 O2 H2 97.8(11) . . ?
O7 O7 H7 99.0(13) 5_666 . ?
C1 N1 H11 122.1(10) . . ?
C1 N1 H12 117.5(10) . . ?
H11 N1 H12 119.7(15) . . ?
N3 N2 C1 119.30(8) . . ?
N3 N2 H21 122.1(10) . . ?
C1 N2 H21 117.7(10) . . ?
C2 N3 N2 117.20(9) . . ?
O6 N4 O5 124.27(9) . . ?
O6 N4 C6 117.75(9) . . ?
O5 N4 C6 117.97(8) . . ?
C6 O4 C3 105.10(8) . . ?
O3 C1 N1 123.80(9) . . ?
O3 C1 N2 117.84(9) . . ?
N1 C1 N2 118.35(9) . . ?
N3 C2 C3 117.97(9) . . ?
N3 C2 H3 124.6(8) . . ?
C3 C2 H3 117.4(8) . . ?
C4 C3 O4 110.27(8) . . ?
C4 C3 C2 132.97(9) . . ?
O4 C3 C2 116.76(8) . . ?
C3 C4 C5 106.81(9) . . ?
C3 C4 H4 124.0(9) . . ?
C5 C4 H4 129.2(9) . . ?
C6 C5 C4 104.89(9) . . ?
C6 C5 H5 126.2(9) . . ?
C4 C5 H5 129.0(9) . . ?
O4 C6 C5 112.93(9) . . ?
O4 C6 N4 114.70(8) . . ?
C5 C6 N4 132.33(9) . . ?

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
C1 N2 N3 C2 177.23(9) . . . . ?
N3 N2 C1 O3 -176.08(9) . . . . ?
N3 N2 C1 N1 3.93(14) . . . . ?
N2 N3 C2 C3 -179.47(8) . . . . ?
C6 O4 C3 C4 0.32(11) . . . . ?
C6 O4 C3 C2 -179.08(8) . . . . ?
N3 C2 C3 C4 180.00(11) . . . . ?
N3 C2 C3 O4 -0.78(14) . . . . ?
O4 C3 C4 C5 -0.11(12) . . . . ?
C2 C3 C4 C5 179.15(10) . . . . ?
C3 C4 C5 C6 -0.14(11) . . . . ?
C3 O4 C6 C5 -0.42(11) . . . . ?
C3 O4 C6 N4 -178.54(8) . . . . ?
C4 C5 C6 O4 0.36(12) . . . . ?
C4 C5 C6 N4 178.04(10) . . . . ?
O6 N4 C6 O4 176.52(8) . . . . ?
O5 N4 C6 O4 -2.28(13) . . . . ?
O6 N4 C6 C5 -1.13(16) . . . . ?
O5 N4 C6 C5 -179.93(11) . . . . ?
H1 O1 O2 H2 91.3(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
_geom_hbond_publ_flag
O1 H1 O3 0.876(18) 1.878(18) 2.7390(11) 167.1(16) 4_655 yes
O2 H2 O3 0.899(18) 1.794(18) 2.6893(11) 173.2(17) . yes
O7 H7 O5 0.837(19) 2.23(2) 2.9968(12) 152.8(17) . yes
O7 H7 O4 0.837(19) 2.238(19) 2.9043(11) 136.6(17) . yes
N1 H11 O7 0.839(16) 2.324(16) 3.1188(13) 158.1(14) . yes
N1 H12 O1 0.876(16) 2.282(16) 3.0927(13) 153.9(14) . yes
N2 H21 O2 0.879(16) 2.028(16) 2.8681(11) 159.7(14) 4_645 yes

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048


####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 2279091'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2023-07-04 deposited with the CCDC.	2024-10-01 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         '2(C6 H6 N4 O4), 7(H2 O2)'
_chemical_formula_sum            'C12 H26 N8 O22'
_chemical_formula_weight         634.41

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      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                   8.8432(3)
_cell_length_b                   12.7456(5)
_cell_length_c                   13.2427(5)
_cell_angle_alpha                105.6813(13)
_cell_angle_beta                 108.5010(13)
_cell_angle_gamma                103.7032(14)
_cell_volume                     1274.85(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7300
_cell_measurement_theta_min      2.576
_cell_measurement_theta_max      30.531

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   0.8807
_exptl_transmission_factor_max   0.9281
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19704
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.774
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6764
_reflns_number_gt                5311
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0463P)²+0.6905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6764
_refine_ls_number_parameters     495
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.028
_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 0.42064(15) 0.32771(10) 0.06934(10) 0.0233(3) Uani 1 1 d . . . . .
H1 H 0.466(3) 0.3556(19) 0.144(2) 0.036(6) Uiso 1 1 d . . . . .
O2 O 0.44310(16) 0.21504(10) 0.04677(10) 0.0231(2) Uani 1 1 d . . . . .
H2A H 0.518(5) 0.218(4) 0.012(4) 0.031(11) Uiso 0.5 1 d . . P A 3
H2B H 0.329(6) 0.175(4) 0.008(4) 0.039(12) Uiso 0.5 1 d . . P B 4
O3 O -0.05707(18) 0.85683(11) 0.05985(10) 0.0324(3) Uani 1 1 d . . . . .
H3 H -0.030(3) 0.8772(19) 0.135(2) 0.038(6) Uiso 1 1 d . . . . .
O4 O -0.05824(16) 0.73866(10) 0.03521(10) 0.0219(2) Uani 1 1 d . . . . .
H4 H -0.165(3) 0.707(2) 0.000(2) 0.054(8) Uiso 1 1 d . . . . .
O5 O 0.26483(16) 0.51730(11) 0.09283(11) 0.0294(3) Uani 1 1 d . . . . .
H5 H 0.298(3) 0.5350(19) 0.173(2) 0.043(6) Uiso 1 1 d . . . . .
O6 O 0.15126(17) 0.58343(11) 0.08006(10) 0.0274(3) Uani 1 1 d . . . . .
H6B H 0.201322 0.640973 0.067373 0.041 Uiso 0.5 1 d R U P C 4
H6A H 0.047(9) 0.523(7) 0.045(5) 0.10(3) Uiso 0.5 1 d . . P D -3
O7 O 0.82172(19) 0.26570(12) 0.07475(11) 0.0385(4) Uani 1 1 d D . . . .
H7 H 0.905(2) 0.2563(15) 0.059(2) 0.058 Uiso 1 1 d D U . . .
O8 O 0.68776(15) 0.23116(10) -0.03916(10) 0.0219(2) Uani 1 1 d D . . . .
H8B H 0.598(3) 0.224(4) -0.026(3) 0.029(11) Uiso 0.5 1 d D . P E 4
H8A H 0.716(6) 0.291(2) -0.055(4) 0.043(13) Uiso 0.5 1 d D . P F 3
O9 O 0.66166(16) 0.04032(12) 0.13691(11) 0.0304(3) Uani 1 1 d D . . . .
H9 H 0.729(2) 0.047(2) 0.2048(11) 0.046 Uiso 1 1 d D U . . .
O10 O 0.78275(17) 0.03452(11) 0.08443(11) 0.0282(3) Uani 1 1 d D . . . .
H10 H 0.802(3) 0.1023(11) 0.0817(19) 0.042 Uiso 1 1 d D U . . .
O11 O 0.98595(15) 0.18237(9) 0.38840(10) 0.0198(2) Uani 1 1 d . . . . .
H11 H 1.028(3) 0.2003(18) 0.4607(19) 0.034(6) Uiso 1 1 d . . . . .
O12 O 0.88378(14) 0.06036(9) 0.35284(10) 0.0188(2) Uani 1 1 d . . . . .
H12 H 0.956(3) 0.029(2) 0.341(2) 0.045(7) Uiso 1 1 d . . . . .
O21A O 0.46378(17) 0.67581(10) 0.37016(10) 0.0200(3) Uani 0.927(2) 1 d D . P G
1
O22A O 0.37470(15) 0.55018(10) 0.32674(10) 0.0182(3) Uani 0.927(2) 1 d D . P G
1
O21B O 0.392(2) 0.6408(13) 0.3796(13) 0.0200(3) Uani 0.073(2) 1 d D . P G 2
O22B O 0.4841(18) 0.5994(13) 0.3131(13) 0.0182(3) Uani 0.073(2) 1 d D . P G 2
H21 H 0.489(2) 0.6890(18) 0.4453(15) 0.042(6) Uiso 1 1 d D . . . .
H22 H 0.470(2) 0.532(2) 0.331(2) 0.058(8) Uiso 1 1 d D . . . .
O13 O 0.56265(13) 0.41316(9) 0.30087(8) 0.0155(2) Uani 1 1 d . . . . .
O14 O 1.11657(12) 0.32424(8) 0.64673(8) 0.0126(2) Uani 1 1 d . . . . .
O15 O 1.21296(14) 0.15106(9) 0.58942(9) 0.0185(2) Uani 1 1 d . . . . .
O16 O 1.38827(15) 0.19453(10) 0.76598(9) 0.0228(2) Uani 1 1 d . . . . .
N11 N 0.71713(18) 0.29323(11) 0.30071(12) 0.0161(3) Uani 1 1 d . . . . .
H16 H 0.789(3) 0.2721(17) 0.3371(17) 0.022(5) Uiso 1 1 d . . . . .
H17 H 0.667(3) 0.2598(17) 0.2339(18) 0.022(5) Uiso 1 1 d . . . . .
N12 N 0.75621(16) 0.43128(11) 0.46952(10) 0.0146(2) Uani 1 1 d . . . . .
H18 H 0.733(2) 0.4873(18) 0.5044(17) 0.026(5) Uiso 1 1 d . . . . .
N13 N 0.87964(15) 0.39600(10) 0.52718(10) 0.0137(2) Uani 1 1 d . . . . .
N14 N 1.28307(16) 0.21299(10) 0.69331(10) 0.0147(2) Uani 1 1 d . . . . .
C11 C 0.67426(17) 0.37879(12) 0.35304(12) 0.0127(3) Uani 1 1 d . . . . .
C12 C 0.95855(18) 0.45377(12) 0.63601(12) 0.0137(3) Uani 1 1 d . . . . .
C13 C 1.08774(18) 0.41997(12) 0.70291(12) 0.0129(3) Uani 1 1 d . . . . .
C14 C 1.18975(19) 0.46449(13) 0.81777(12) 0.0152(3) Uani 1 1 d . . . . .
C15 C 1.28822(19) 0.39283(13) 0.83594(12) 0.0159(3) Uani 1 1 d . . . . .
C16 C 1.23781(18) 0.31099(12) 0.73039(12) 0.0135(3) Uani 1 1 d . . . . .
H13 H 0.935(2) 0.5175(16) 0.6763(15) 0.017(4) Uiso 1 1 d . . . . .
H14 H 1.191(2) 0.5302(16) 0.8732(16) 0.020(5) Uiso 1 1 d . . . . .
H15 H 1.372(2) 0.3995(15) 0.9058(15) 0.017(4) Uiso 1 1 d . . . . .
O23 O 0.04186(13) 0.91668(9) 0.28854(9) 0.0155(2) Uani 1 1 d . . . . .
O24 O 0.59689(12) 0.81922(8) 0.62772(8) 0.0122(2) Uani 1 1 d . . . . .
O25 O 0.68962(14) 0.64285(9) 0.57189(9) 0.0180(2) Uani 1 1 d . . . . .
O26 O 0.86726(14) 0.68978(10) 0.74890(9) 0.0217(2) Uani 1 1 d . . . . .
N21 N 0.18869(17) 0.79245(11) 0.28206(11) 0.0158(3) Uani 1 1 d . . . . .
H26 H 0.258(2) 0.7673(16) 0.3180(15) 0.016(4) Uiso 1 1 d . . . . .
H27 H 0.132(2) 0.7592(17) 0.2143(17) 0.021(5) Uiso 1 1 d . . . . .
N22 N 0.24121(16) 0.93252(11) 0.45359(10) 0.0142(2) Uani 1 1 d . . . . .
H28 H 0.218(2) 0.9847(17) 0.4895(16) 0.025(5) Uiso 1 1 d . . . . .
N23 N 0.36065(15) 0.89306(10) 0.50872(10) 0.0131(2) Uani 1 1 d . . . . .
N24 N 0.76151(15) 0.70705(10) 0.67560(10) 0.0145(2) Uani 1 1 d . . . . .
C21 C 0.15237(18) 0.88003(12) 0.33792(12) 0.0129(3) Uani 1 1 d . . . . .
C22 C 0.44381(18) 0.95159(12) 0.61730(12) 0.0130(3) Uani 1 1 d . . . . .
C23 C 0.56959(18) 0.91573(12) 0.68382(12) 0.0122(3) Uani 1 1 d . . . . .
C24 C 0.67136(18) 0.96010(12) 0.79876(12) 0.0141(3) Uani 1 1 d . . . . .
C25 C 0.76838(18) 0.88768(12) 0.81722(12) 0.0146(3) Uani 1 1 d . . . . .
C26 C 0.71717(18) 0.80547(12) 0.71167(12) 0.0127(3) Uani 1 1 d . . . . .
H23 H 0.424(2) 1.0160(16) 0.6566(15) 0.017(4) Uiso 1 1 d . . . . .
H24 H 0.673(2) 1.0269(15) 0.8538(15) 0.016(4) Uiso 1 1 d . . . . .
H25 H 0.851(2) 0.8928(15) 0.8876(15) 0.015(4) Uiso 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 O2 1.4602(16) . ?
O1 H1 0.87(2) . ?
O2 H2A 0.92(4) . ?
O2 H2B 0.91(5) . ?
O3 O4 1.4491(16) . ?
O3 H3 0.89(2) . ?
O4 H4 0.84(3) . ?
O5 O6 1.4553(16) . ?
O5 H5 0.95(2) . ?
O6 H6B 0.8498 . ?
O6 H6A 0.92(7) . ?
O7 O8 1.4603(16) . ?
O7 H7 0.847(10) . ?
O8 H8B 0.853(10) . ?
O8 H8A 0.853(10) . ?
O9 O10 1.4551(17) . ?
O9 H9 0.877(10) . ?
O10 H10 0.853(9) . ?
O11 O12 1.4578(15) . ?
O11 H11 0.85(2) . ?
O12 H12 0.86(2) . ?
O21A O22A 1.4602(16) . ?
O21A H21 0.906(16) . ?
O22A H22 0.914(16) . ?
O21B O22B 1.46(2) . ?
O21B H21 0.926(16) . ?
O22B H22 0.933(16) . ?
O13 C11 1.2566(17) . ?
O14 C16 1.3559(16) . ?
O14 C13 1.3727(16) . ?
O15 N14 1.2410(16) . ?
O16 N14 1.2266(16) . ?
N11 C11 1.3294(18) . ?
N11 H16 0.82(2) . ?
N11 H17 0.79(2) . ?
N12 C11 1.3621(18) . ?
N12 N13 1.3659(16) . ?
N12 H18 0.85(2) . ?
N13 C12 1.2849(18) . ?
N14 C16 1.4112(18) . ?
C12 C13 1.4397(19) . ?
C12 H13 0.950(18) . ?
C13 C14 1.367(2) . ?
C14 C15 1.419(2) . ?
C14 H14 0.947(18) . ?
C15 C16 1.3552(19) . ?
C15 H15 0.952(18) . ?
O23 C21 1.2556(17) . ?
O24 C26 1.3570(16) . ?
O24 C23 1.3726(16) . ?
O25 N24 1.2457(15) . ?
O26 N24 1.2256(15) . ?
N21 C21 1.3307(18) . ?
N21 H26 0.833(19) . ?
N21 H27 0.80(2) . ?
N22 C21 1.3581(18) . ?
N22 N23 1.3647(16) . ?
N22 H28 0.82(2) . ?
N23 C22 1.2861(18) . ?
N24 C26 1.4084(18) . ?
C22 C23 1.4349(19) . ?
C22 H23 0.934(18) . ?
C23 C24 1.3677(19) . ?
C24 C25 1.418(2) . ?
C24 H24 0.952(18) . ?
C25 C26 1.3558(19) . ?
C25 H25 0.957(18) . ?

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
O2 O1 H1 99.8(14) . . ?
O1 O2 H2A 106(3) . . ?
O1 O2 H2B 93(3) . . ?
O4 O3 H3 97.9(14) . . ?
O3 O4 H4 94.7(17) . . ?
O6 O5 H5 97.0(13) . . ?
O5 O6 H6B 105.5 . . ?
O5 O6 H6A 100(5) . . ?
O8 O7 H7 102.4(18) . . ?
O7 O8 H8B 103(3) . . ?
O7 O8 H8A 102(3) . . ?
O10 O9 H9 96.5(15) . . ?
O9 O10 H10 96.4(15) . . ?
O12 O11 H11 99.1(14) . . ?
O11 O12 H12 99.1(16) . . ?
O22A O21A H21 96.7(13) . . ?
O21A O22A H22 94.2(14) . . ?
O22B O21B H21 95.1(18) . . ?
O21B O22B H22 91.3(17) . . ?
C16 O14 C13 104.63(11) . . ?
C11 N11 H16 121.2(13) . . ?
C11 N11 H17 118.9(14) . . ?
H16 N11 H17 119.8(19) . . ?
C11 N12 N13 119.34(12) . . ?
C11 N12 H18 119.3(13) . . ?
N13 N12 H18 121.2(13) . . ?
C12 N13 N12 116.02(12) . . ?
O16 N14 O15 124.51(12) . . ?
O16 N14 C16 117.81(12) . . ?
O15 N14 C16 117.68(12) . . ?
O13 C11 N11 123.54(13) . . ?
O13 C11 N12 118.72(13) . . ?
N11 C11 N12 117.74(13) . . ?
N13 C12 C13 119.17(13) . . ?
N13 C12 H13 123.8(11) . . ?
C13 C12 H13 117.0(11) . . ?
C14 C13 O14 110.65(12) . . ?
C14 C13 C12 131.66(13) . . ?
O14 C13 C12 117.67(12) . . ?
C13 C14 C15 106.80(13) . . ?
C13 C14 H14 125.3(11) . . ?
C15 C14 H14 127.9(11) . . ?
C16 C15 C14 104.77(13) . . ?
C16 C15 H15 126.4(11) . . ?
C14 C15 H15 128.8(11) . . ?
C15 C16 O14 113.15(12) . . ?
C15 C16 N14 131.83(13) . . ?
O14 C16 N14 114.95(12) . . ?
C26 O24 C23 104.50(10) . . ?
C21 N21 H26 120.5(12) . . ?
C21 N21 H27 117.7(14) . . ?
H26 N21 H27 121.2(18) . . ?
C21 N22 N23 119.71(12) . . ?
C21 N22 H28 119.2(14) . . ?
N23 N22 H28 121.0(14) . . ?
C22 N23 N22 115.23(12) . . ?
O26 N24 O25 124.43(12) . . ?
O26 N24 C26 117.57(12) . . ?
O25 N24 C26 118.00(11) . . ?
O23 C21 N21 123.08(13) . . ?
O23 C21 N22 118.98(13) . . ?
N21 C21 N22 117.93(13) . . ?
N23 C22 C23 119.68(13) . . ?
N23 C22 H23 123.0(11) . . ?
C23 C22 H23 117.3(11) . . ?
C24 C23 O24 110.72(12) . . ?
C24 C23 C22 131.35(13) . . ?
O24 C23 C22 117.93(12) . . ?
C23 C24 C25 106.85(12) . . ?
C23 C24 H24 124.8(10) . . ?
C25 C24 H24 128.3(11) . . ?
C26 C25 C24 104.67(13) . . ?
C26 C25 H25 126.3(10) . . ?
C24 C25 H25 129.0(10) . . ?
C25 C26 O24 113.26(12) . . ?
C25 C26 N24 131.42(13) . . ?
O24 C26 N24 115.25(12) . . ?

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
C11 N12 N13 C12 176.06(13) . . . . ?
N13 N12 C11 O13 -179.01(12) . . . . ?
N13 N12 C11 N11 1.1(2) . . . . ?
N12 N13 C12 C13 178.62(12) . . . . ?
C16 O14 C13 C14 0.46(15) . . . . ?
C16 O14 C13 C12 -177.83(12) . . . . ?
N13 C12 C13 C14 -179.86(15) . . . . ?
N13 C12 C13 O14 -2.0(2) . . . . ?
O14 C13 C14 C15 -0.38(17) . . . . ?
C12 C13 C14 C15 177.60(15) . . . . ?
C13 C14 C15 C16 0.14(17) . . . . ?
C14 C15 C16 O14 0.15(17) . . . . ?
C14 C15 C16 N14 -176.77(15) . . . . ?
C13 O14 C16 C15 -0.37(16) . . . . ?
C13 O14 C16 N14 177.10(12) . . . . ?
O16 N14 C16 C15 -0.8(2) . . . . ?
O15 N14 C16 C15 178.79(16) . . . . ?
O16 N14 C16 O14 -177.73(12) . . . . ?
O15 N14 C16 O14 1.91(19) . . . . ?
C21 N22 N23 C22 176.85(13) . . . . ?
N23 N22 C21 O23 179.39(12) . . . . ?
N23 N22 C21 N21 -1.4(2) . . . . ?
N22 N23 C22 C23 178.55(12) . . . . ?
C26 O24 C23 C24 0.42(15) . . . . ?
C26 O24 C23 C22 -178.57(12) . . . . ?
N23 C22 C23 C24 -178.40(15) . . . . ?
N23 C22 C23 O24 0.3(2) . . . . ?
O24 C23 C24 C25 -0.30(17) . . . . ?
C22 C23 C24 C25 178.51(15) . . . . ?
C23 C24 C25 C26 0.05(17) . . . . ?
C24 C25 C26 O24 0.22(17) . . . . ?
C24 C25 C26 N24 -176.76(15) . . . . ?
C23 O24 C26 C25 -0.39(16) . . . . ?
C23 O24 C26 N24 177.10(12) . . . . ?
O26 N24 C26 C25 -1.7(2) . . . . ?
O25 N24 C26 C25 177.59(15) . . . . ?
O26 N24 C26 O24 -178.60(12) . . . . ?
O25 N24 C26 O24 0.66(19) . . . . ?
H1 O1 O2 H2A -114(3) . . . . ?
H1 O1 O2 H2B 120(3) . . . . ?
H3 O3 O4 H4 108(2) . . . . ?
H5 O5 O6 H6A -105(5) . . . . ?
H5 O5 O6 H6B 110.0 . . . . ?
H7 O7 O8 H8A -78(3) . . . . ?
H7 O7 O8 H8B 167(3) . . . . ?
H9 O9 O10 H10 -108(2) . . . . ?
H11 O11 O12 H12 -94(2) . . . . ?
H21 O21A O22A H22 -92(2) . . . . ?
H21 O21B O22B H22 97(3) . . . . ?

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
O1 H1 O13 0.87(2) 1.82(2) 2.6958(15) 180(2) . yes
O2 H2A^c O8 0.92(4) 1.82(4) 2.7379(17) 173(4) . yes
O2 H2B^d O3 0.91(5) 2.17(5) 3.0409(19) 159(4) 2_565 yes
O3 H3 O23 0.89(2) 1.81(2) 2.6967(16) 175(2) . yes
O4 H4 O1 0.84(3) 2.03(3) 2.8582(17) 166(2) 2_565 yes
O5 H5 O22A^a 0.95(2) 1.87(2) 2.8125(17) 171(2) . yes
O6 H6A^c O6 0.92(7) 1.86(6) 2.728(3) 155(7) 2_565 yes
O6 H6B^d O8 0.85 1.89 2.7371(19) 179.9 2_665 yes
O7 H7 O4 0.847(10) 2.121(13) 2.906(2) 154(2) 2_665 yes
O8 H8B^d O2 0.853(10) 1.910(16) 2.7379(17) 163(4) . yes
O8 H8A^c O6 0.853(10) 1.916(18) 2.7371(19) 161(4) 2_665 yes
O9 H9 O12 0.877(10) 1.935(10) 2.8112(17) 178(2) . yes
O10 H10 O7 0.853(9) 2.078(10) 2.9272(19) 173(2) . yes
O11 H11 O14 0.85(2) 2.29(2) 3.0766(15) 153.2(19) . yes
O11 H11 O15 0.85(2) 2.30(2) 2.9728(16) 136.7(18) . yes
O12 H12 O23 0.86(2) 1.85(2) 2.6755(15) 160(2) 1_645 yes
O21A^a H21 O24 0.906(16) 2.262(18) 3.0696(15) 148.3(17) . yes
O21A^a H21 O25 0.906(16) 2.33(2) 2.9866(16) 129.0(17) . yes
O21B^b H21 O24 0.926(16) 2.262(18) 3.079(14) 147(2) . yes
O21B^b H21 O25 0.926(16) 2.33(2) 3.014(15) 130(2) . yes
O22A^a H22 O13 0.914(16) 1.90(2) 2.7098(15) 146.7(18) . yes
O22B^b H22 O13 0.933(16) 1.90(2) 2.605(15) 130.7(17) . yes
N11 H16 O11 0.82(2) 2.33(2) 3.1181(18) 163.5(18) . yes
N11 H17 O2 0.79(2) 2.45(2) 3.1696(19) 153.7(18) . yes
N12 H18 O25 0.85(2) 2.12(2) 2.9562(16) 169.2(19) . yes
C12 H13 O26 0.950(18) 2.441(18) 3.3795(18) 169.7(15) . yes
N21 H26 O21A^a 0.833(19) 2.408(19) 3.2155(18) 163.6(16) . yes
N21 H26 O21B^b 0.833(19) 2.38(2) 3.188(16) 162.8(17) . yes
N21 H27 O4 0.80(2) 2.34(2) 3.0779(18) 154.3(18) . yes
N22 H28 O15 0.82(2) 2.19(2) 2.9938(16) 166.4(19) 1_465 yes
C22 H23 O16 0.934(18) 2.494(18) 3.4270(18) 176.8(15) 1_465 yes

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.055





