# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_dhhfhdhh_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2293510'
loop_
_audit_author_name
_audit_author_address
'Priyanka Das'
;IIT Roorkee
India
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 N8 O10, H2 O'
_chemical_formula_sum            'C7 H6 N8 O11'
_chemical_formula_weight         378.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9010(6)
_cell_length_b                   7.1701(4)
_cell_length_c                   10.0087(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.195(2)
_cell_angle_gamma                90
_cell_volume                     671.03(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    305(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             384.0
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.095
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20668
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.503
_diffrn_reflns_theta_min         2.155
_diffrn_ambient_temperature      305(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2642
_reflns_number_total             2788
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.794
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      0.794
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          ?
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1277(2) -0.1409(3) 0.5434(3) 0.0535(5) Uani 1 1 d . . . . .
O2 O -0.0124(3) -0.0221(4) 0.3499(3) 0.0659(7) Uani 1 1 d . . . . .
O3 O 0.0571(2) 0.3390(3) 0.27154(19) 0.0471(5) Uani 1 1 d . . . . .
H6 H 0.059641 0.447442 0.246434 0.071 Uiso 1 1 calc R U . . .
O4 O 0.2224(3) 0.6735(3) 0.3275(2) 0.0512(5) Uani 1 1 d . . . . .
O5 O 0.4169(2) 0.6759(3) 0.5099(2) 0.0530(5) Uani 1 1 d . . . . .
O6 O 0.1020(3) 0.5281(4) 0.9745(3) 0.0563(6) Uani 1 1 d . . . . .
O7 O 0.1597(3) 0.8126(3) 1.0301(2) 0.0497(5) Uani 1 1 d . . . . .
O8 O 0.36389(19) 0.9900(3) 0.9215(2) 0.0386(4) Uani 1 1 d . . . . .
H3 H 0.282194 1.028718 0.905830 0.058 Uiso 1 1 calc R U . . .
O9 O 0.5796(2) 0.9722(3) 0.7924(3) 0.0576(6) Uani 1 1 d . . . . .
O10 O 0.6610(2) 0.6948(4) 0.7805(3) 0.0534(6) Uani 1 1 d . . . . .
N1 N 0.0913(2) -0.0151(4) 0.4571(2) 0.0412(5) Uani 1 1 d . . . . .
N2 N 0.3043(3) 0.6034(3) 0.4362(2) 0.0381(5) Uani 1 1 d . . . . .
N3 N 0.2807(2) 0.1701(3) 0.6036(2) 0.0334(4) Uani 1 1 d . . . . .
N4 N 0.3380(2) 0.3366(3) 0.59934(19) 0.0309(4) Uani 1 1 d . . . . .
N5 N 0.4099(2) 0.5418(3) 0.8000(2) 0.0298(4) Uani 1 1 d . . . . .
N6 N 0.3038(2) 0.5030(3) 0.8498(2) 0.0324(4) Uani 1 1 d . . . . .
N7 N 0.1707(2) 0.6673(3) 0.9731(2) 0.0360(5) Uani 1 1 d . . . . .
N8 N 0.5702(2) 0.8021(4) 0.7939(2) 0.0366(5) Uani 1 1 d . . . . .
C1 C 0.1738(3) 0.1548(4) 0.4833(2) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.1557(3) 0.3135(4) 0.3966(2) 0.0349(5) Uani 1 1 d . . . . .
C3 C 0.2651(2) 0.4283(4) 0.4757(2) 0.0332(5) Uani 1 1 d . . . . .
C4 C 0.4559(2) 0.3933(4) 0.7238(2) 0.0333(5) Uani 1 1 d . . . . .
H4 H 0.534791 0.437494 0.695107 0.040 Uiso 1 1 calc R U . . .
H5 H 0.488951 0.286942 0.785832 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2754(2) 0.6629(4) 0.9007(2) 0.0302(5) Uani 1 1 d . . . . .
C6 C 0.3596(2) 0.8132(4) 0.8833(2) 0.0294(5) Uani 1 1 d . . . . .
C7 C 0.4471(2) 0.7258(3) 0.8191(2) 0.0295(5) Uani 1 1 d . . . . .
O11 O 0.1078(3) 0.1436(3) 0.8682(3) 0.0554(6) Uani 1 1 d . . . . .
H7 H 0.099(6) 0.263(9) 0.850(6) 0.095(17) Uiso 1 1 d . . . . .
H8 H 0.071(7) 0.163(12) 0.928(6) 0.11(2) 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 N1 1.219(3) . ?
O3 C2 1.322(3) . ?
O4 N2 1.230(3) . ?
O5 N2 1.231(3) . ?
O7 N7 1.210(3) . ?
O8 C6 1.321(3) . ?
O9 N8 1.224(4) . ?
O10 N8 1.224(3) . ?
N1 O2 1.218(3) . ?
N1 C1 1.442(4) . ?
N2 C3 1.408(3) . ?
N3 C1 1.321(3) . ?
N4 N3 1.328(3) . ?
N4 C3 1.378(3) . ?
N4 C4 1.457(3) . ?
N5 C4 1.467(3) . ?
N5 C7 1.366(3) . ?
N6 N5 1.332(3) . ?
N6 C5 1.322(4) . ?
N7 O6 1.211(3) . ?
N7 C5 1.446(3) . ?
N8 C7 1.431(3) . ?
C2 C1 1.406(4) . ?
C3 C2 1.384(4) . ?
C5 C6 1.408(4) . ?
C7 C6 1.387(4) . ?

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
O1 N1 O2 124.2(3) . . ?
O1 N1 C1 118.6(2) . . ?
O2 N1 C1 117.2(3) . . ?
O4 N2 O5 124.1(2) . . ?
O4 N2 C3 116.7(2) . . ?
O5 N2 C3 119.1(2) . . ?
C1 N3 N4 105.5(2) . . ?
N3 N4 C3 110.78(19) . . ?
N3 N4 C4 116.98(19) . . ?
C3 N4 C4 132.1(2) . . ?
N6 N5 C4 117.5(2) . . ?
N6 N5 C7 111.1(2) . . ?
C7 N5 C4 131.1(2) . . ?
C5 N6 N5 104.9(2) . . ?
O6 N7 C5 119.0(2) . . ?
O7 N7 O6 124.5(2) . . ?
O7 N7 C5 116.5(2) . . ?
O9 N8 O10 124.3(2) . . ?
O9 N8 C7 117.1(2) . . ?
O10 N8 C7 118.5(2) . . ?
N3 C1 N1 118.2(2) . . ?
N3 C1 C2 113.4(2) . . ?
C2 C1 N1 128.4(2) . . ?
O3 C2 C1 126.9(3) . . ?
O3 C2 C3 130.9(3) . . ?
C3 C2 C1 102.2(2) . . ?
N4 C3 N2 124.5(2) . . ?
N4 C3 C2 108.1(2) . . ?
C2 C3 N2 127.3(2) . . ?
N4 C4 N5 110.42(18) . . ?
N6 C5 N7 119.4(2) . . ?
N6 C5 C6 114.0(2) . . ?
C6 C5 N7 126.6(2) . . ?
O8 C6 C5 131.5(2) . . ?
O8 C6 C7 127.0(2) . . ?
C7 C6 C5 101.4(2) . . ?
N5 C7 N8 123.4(2) . . ?
N5 C7 C6 108.6(2) . . ?
C6 C7 N8 127.4(2) . . ?

####################################################################### 
# 
# 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_DK_PB_PSTOT_0249
_database_code_depnum_ccdc_archive 'CCDC 2293511'
loop_
_audit_author_name
_audit_author_address
'Priyanka Das'
;IIT Roorkee
India
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_audit_creation_date             2023-08-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C7 H2 N8 O10, 2(C2 H7 N6)'
_chemical_formula_sum            'C11 H16 N20 O10'
_chemical_formula_weight         588.379
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   32.034(3)
_cell_length_b                   5.3339(5)
_cell_length_c                   29.714(3)
_cell_angle_alpha                90
_cell_angle_beta                 121.034(3)
_cell_angle_gamma                90
_cell_volume                     4350.3(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6858
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      24.4746
_cell_measurement_theta_min      2.5442
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7170
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2418.274
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.163
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9968
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            45335
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9968
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         1.48
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_device_type  'Bruker D8 QUEST Photon III C7'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              33
_reflns_limit_h_min              -39
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              36
_reflns_limit_l_min              0
_reflns_number_gt                3382
_reflns_number_total             4306
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5234
_refine_diff_density_min         -0.4047
_refine_diff_density_rms         0.0771
_refine_ls_d_res_high            0.8083
_refine_ls_d_res_low             13.7243
_refine_ls_goodness_of_fit_ref   1.0708
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.0702
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+5.8154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1082
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H) groups, H16 of N16, All N(H,H) groups
 At 1.2 times of:
  H11 of N11
2. Restrained distances
 N19-H19a
 0.89 with sigma of 0.02
 N19-H19b
 0.89 with sigma of 0.02
 H19a-H19b
 1.5 with sigma of 0.04
 C10-H19a = C10-H19b
 2 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 N11(H11)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.55938(5) 0.9080(3) 0.75135(6) 0.0263(4) Uani 1.000000 .
O2 O 0.55281(6) 0.6837(3) 0.80884(6) 0.0315(4) Uani 1.000000 .
O3 O 0.61549(5) 0.2600(3) 0.85218(5) 0.0230(3) Uani 1.000000 .
O4 O 0.68951(6) -0.0745(3) 0.86012(6) 0.0290(4) Uani 1.000000 .
O5 O 0.72743(7) 0.0489(4) 0.82104(9) 0.0620(7) Uani 1.000000 .
O6 O 0.71336(6) 1.1115(3) 0.65552(7) 0.0410(5) Uani 1.000000 .
O7 O 0.65454(6) 1.0492(3) 0.57557(6) 0.0336(4) Uani 1.000000 .
O8 O 0.58969(5) 0.6397(3) 0.55627(5) 0.0235(3) Uani 1.000000 .
O9 O 0.55674(5) 0.2179(3) 0.58958(6) 0.0270(4) Uani 1.000000 .
O10 O 0.59727(5) 0.1356(3) 0.67396(6) 0.0280(4) Uani 1.000000 .
N1 N 0.57048(6) 0.7258(3) 0.78079(7) 0.0228(4) Uani 1.000000 .
N2 N 0.69395(7) 0.0672(4) 0.82950(7) 0.0284(5) Uani 1.000000 .
N3 N 0.62518(6) 0.5899(3) 0.75407(7) 0.0214(4) Uani 1.000000 .
N4 N 0.65807(6) 0.4116(3) 0.76772(7) 0.0212(4) Uani 1.000000 .
N5 N 0.66184(6) 0.5188(3) 0.69152(7) 0.0201(4) Uani 1.000000 .
N6 N 0.68529(6) 0.7173(3) 0.68844(7) 0.0217(4) Uani 1.000000 .
N7 N 0.67752(6) 0.9929(4) 0.62238(7) 0.0253(4) Uani 1.000000 .
N8 N 0.59070(6) 0.2601(3) 0.63526(7) 0.0214(4) Uani 1.000000 .
C1 C 0.60570(7) 0.5533(4) 0.78412(8) 0.0187(4) Uani 1.000000 .
C2 C 0.62527(7) 0.3420(4) 0.81885(8) 0.0189(4) Uani 1.000000 .
C3 C 0.65972(7) 0.2578(4) 0.80582(8) 0.0201(5) Uani 1.000000 .
C4 C 0.68512(8) 0.3811(5) 0.74019(9) 0.0236(5) Uani 1.000000 .
H4a H 0.6848(9) 0.204(5) 0.7321(10) 0.0353(7) Uiso 1.000000 R
H4b H 0.7165(9) 0.461(5) 0.7616(10) 0.0353(7) Uiso 1.000000 R
C5 C 0.66093(7) 0.7833(4) 0.63818(8) 0.0204(5) Uani 1.000000 .
C6 C 0.61943(7) 0.6270(4) 0.60465(8) 0.0195(4) Uani 1.000000 .
C7 C 0.62230(7) 0.4548(4) 0.64272(8) 0.0198(4) Uani 1.000000 .
N9 N 0.68844(6) -0.2529(3) 1.00627(6) 0.0187(4) Uani 1.000000 .
N10 N 0.70520(6) 0.0766(3) 0.97310(7) 0.0226(4) Uani 1.000000 .
N11 N 0.66219(6) -0.0414(3) 0.93570(7) 0.0223(4) Uani 1.000000 .
H11 H 0.64386(6) 0.0104(3) 0.90306(7) 0.0267(5) Uiso 1.000000 R
N12 N 0.69185(7) -0.4482(4) 1.03927(8) 0.0239(4) Uani 1.000000 .
H12a H 0.6896(9) -0.387(5) 1.0653(10) 0.0359(6) Uiso 1.000000 R
H12b H 0.7177(10) -0.534(5) 1.0478(10) 0.0359(6) Uiso 1.000000 R
N13 N 0.75872(7) -0.0055(4) 1.06391(7) 0.0241(4) Uani 1.000000 .
H13a H 0.7791(9) 0.090(5) 1.0639(10) 0.0362(6) Uiso 1.000000 R
H13b H 0.7692(9) -0.128(5) 1.0875(10) 0.0362(6) Uiso 1.000000 R
N14 N 0.61475(7) -0.3913(4) 0.93091(8) 0.0245(4) Uani 1.000000 .
H14a H 0.6111(9) -0.507(5) 0.9476(10) 0.0368(6) Uiso 1.000000 R
H14b H 0.6012(9) -0.403(5) 0.8975(11) 0.0368(6) Uiso 1.000000 R
C8 C 0.65237(7) -0.2384(4) 0.95495(8) 0.0193(4) Uani 1.000000 .
C9 C 0.71977(7) -0.0541(4) 1.01562(8) 0.0192(4) Uani 1.000000 .
N15 N 0.51145(6) 1.1266(3) 0.39868(6) 0.0186(4) Uani 1.000000 .
N16 N 0.56337(6) 0.9706(4) 0.47327(7) 0.0232(4) Uani 1.000000 .
H16 H 0.5786(9) 0.920(5) 0.5065(10) 0.0349(6) Uiso 1.000000 R
N17 N 0.56429(6) 0.8176(4) 0.43574(7) 0.0247(4) Uani 1.000000 .
N18 N 0.47589(7) 1.2916(4) 0.36258(7) 0.0222(4) Uani 1.000000 .
H18a H 0.4512(9) 1.200(5) 0.3411(10) 0.0334(6) Uiso 1.000000 R
H18b H 0.4876(9) 1.389(5) 0.3459(10) 0.0334(6) Uiso 1.000000 R
N19 N 0.51992(7) 0.8275(4) 0.34256(7) 0.0237(4) Uani 1.000000 D
H19a H 0.5001(8) 0.929(4) 0.3152(7) 0.0355(6) Uiso 1.000000 DR
H19b H 0.5436(7) 0.763(4) 0.3390(9) 0.0355(6) Uiso 1.000000 DR
N20 N 0.52001(7) 1.3336(4) 0.47324(8) 0.0258(4) Uani 1.000000 .
H20a H 0.5427(10) 1.384(5) 0.5050(11) 0.0388(7) Uiso 1.000000 R
H20b H 0.4988(10) 1.435(5) 0.4513(11) 0.0388(7) Uiso 1.000000 R
C10 C 0.53260(7) 0.9182(4) 0.39096(8) 0.0201(5) Uani 1.000000 D
C11 C 0.53145(7) 1.1541(4) 0.45113(8) 0.0200(5) Uani 1.000000 .


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 N1 1.231(2) . ?
O2 N1 1.246(2) . ?
O3 C2 1.261(2) . ?
O4 N2 1.246(2) . ?
O5 N2 1.225(2) . ?
O6 N7 1.234(2) . ?
O7 N7 1.229(2) . ?
O8 C6 1.251(2) . ?
O9 N8 1.247(2) . ?
O10 N8 1.248(2) . ?
N1 C1 1.419(3) . ?
N2 C3 1.391(3) . ?
N3 N4 1.319(2) . ?
N3 C1 1.341(3) . ?
N4 C3 1.377(3) . ?
N4 C4 1.475(3) . ?
N5 N6 1.328(2) . ?
N5 C4 1.441(3) . ?
N5 C7 1.389(3) . ?
N6 C5 1.327(3) . ?
N7 C5 1.418(3) . ?
N8 C7 1.386(3) . ?
C1 C2 1.436(3) . ?
C2 C3 1.418(3) . ?
C4 H4a 0.97(3) . ?
C4 H4b 0.97(3) . ?
C5 C6 1.445(3) . ?
C6 C7 1.423(3) . ?
N9 N12 1.396(2) . ?
N9 C8 1.360(3) . ?
N9 C9 1.386(3) . ?
N10 N11 1.397(2) . ?
N10 C9 1.301(3) . ?
N11 H11 0.8800 . ?
N11 C8 1.310(3) . ?
N12 H12a 0.88(3) . ?
N12 H12b 0.86(3) . ?
N13 H13a 0.83(3) . ?
N13 H13b 0.89(3) . ?
N13 C9 1.355(3) . ?
N14 H14a 0.84(3) . ?
N14 H14b 0.86(3) . ?
N14 C8 1.319(3) . ?
N15 N18 1.401(2) . ?
N15 C10 1.381(3) . ?
N15 C11 1.353(3) . ?
N16 H16 0.89(3) . ?
N16 N17 1.394(3) . ?
N16 C11 1.320(3) . ?
N17 C10 1.303(3) . ?
N18 H18a 0.87(3) . ?
N18 H18b 0.92(3) . ?
N19 H19a 0.908(15) . ?
N19 H19b 0.886(15) . ?
N19 C10 1.366(3) . ?
N20 H20a 0.88(3) . ?
N20 H20b 0.85(3) . ?
N20 C11 1.316(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
O2 N1 O1 123.61(18) . . ?
C1 N1 O1 119.28(17) . . ?
C1 N1 O2 117.11(17) . . ?
O5 N2 O4 122.88(19) . . ?
C3 N2 O4 117.11(18) . . ?
C3 N2 O5 119.97(19) . . ?
C1 N3 N4 105.24(16) . . ?
C3 N4 N3 111.61(17) . . ?
C4 N4 N3 120.90(17) . . ?
C4 N4 C3 127.29(18) . . ?
C4 N5 N6 117.20(17) . . ?
C7 N5 N6 111.59(17) . . ?
C7 N5 C4 130.09(19) . . ?
C5 N6 N5 105.27(16) . . ?
O7 N7 O6 123.08(19) . . ?
C5 N7 O6 119.57(18) . . ?
C5 N7 O7 117.33(17) . . ?
O10 N8 O9 123.05(17) . . ?
C7 N8 O9 117.69(17) . . ?
C7 N8 O10 119.26(17) . . ?
N3 C1 N1 119.04(18) . . ?
C2 C1 N1 126.57(18) . . ?
C2 C1 N3 114.33(18) . . ?
C1 C2 O3 130.05(19) . . ?
C3 C2 O3 130.41(19) . . ?
C3 C2 C1 99.52(17) . . ?
N4 C3 N2 122.49(18) . . ?
C2 C3 N2 127.95(19) . . ?
C2 C3 N4 109.31(18) . . ?
N5 C4 N4 110.63(17) . . ?
H4a C4 N4 107.9(15) . . ?
H4a C4 N5 108.3(15) . . ?
H4b C4 N4 107.2(14) . . ?
H4b C4 N5 105.2(15) . . ?
H4b C4 H4a 118(2) . . ?
N7 C5 N6 118.57(18) . . ?
C6 C5 N6 114.90(18) . . ?
C6 C5 N7 126.52(18) . . ?
C5 C6 O8 130.20(19) . . ?
C7 C6 O8 130.32(19) . . ?
C7 C6 C5 99.48(17) . . ?
N8 C7 N5 123.29(18) . . ?
C6 C7 N5 108.76(18) . . ?
C6 C7 N8 127.88(18) . . ?
C8 N9 N12 122.91(17) . . ?
C9 N9 N12 130.08(17) . . ?
C9 N9 C8 106.88(17) . . ?
C9 N10 N11 104.13(17) . . ?
H11 N11 N10 124.01(10) . . ?
C8 N11 N10 111.99(17) . . ?
C8 N11 H11 124.01(11) . . ?
H12a N12 N9 109.1(18) . . ?
H12b N12 N9 108.5(17) . . ?
H12b N12 H12a 116(2) . . ?
H13b N13 H13a 119(2) . . ?
C9 N13 H13a 114.3(18) . . ?
C9 N13 H13b 117.4(17) . . ?
H14b N14 H14a 119(3) . . ?
C8 N14 H14a 120.2(18) . . ?
C8 N14 H14b 116.6(18) . . ?
N11 C8 N9 106.18(17) . . ?
N14 C8 N9 125.7(2) . . ?
N14 C8 N11 128.1(2) . . ?
N10 C9 N9 110.80(18) . . ?
N13 C9 N9 122.33(19) . . ?
N13 C9 N10 126.8(2) . . ?
C10 N15 N18 130.78(17) . . ?
C11 N15 N18 121.93(17) . . ?
C11 N15 C10 107.29(17) . . ?
N17 N16 H16 119.0(17) . . ?
C11 N16 H16 128.3(17) . . ?
C11 N16 N17 111.45(17) . . ?
C10 N17 N16 104.44(17) . . ?
H18a N18 N15 106.4(17) . . ?
H18b N18 N15 111.7(15) . . ?
H18b N18 H18a 113(2) . . ?
H19b N19 H19a 112(2) . . ?
C10 N19 H19a 115.1(15) . . ?
C10 N19 H19b 117.0(15) . . ?
H20b N20 H20a 121(3) . . ?
C11 N20 H20a 117.7(17) . . ?
C11 N20 H20b 113.4(18) . . ?
N17 C10 N15 110.65(18) . . ?
N19 C10 N15 123.71(19) . . ?
N19 C10 N17 125.6(2) . . ?
N16 C11 N15 106.17(18) . . ?
N20 C11 N15 124.45(19) . . ?
N20 C11 N16 129.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 N3 -1.6(2) . . . . ?
O1 N1 C1 C2 175.39(17) . . . . ?
O2 N1 C1 N3 179.13(18) . . . . ?
O2 N1 C1 C2 -3.9(2) . . . . ?
O3 C2 C1 N1 1.7(3) . . . . ?
O3 C2 C1 N3 178.9(2) . . . . ?
O3 C2 C3 N2 -4.1(3) . . . . ?
O3 C2 C3 N4 -178.4(2) . . . . ?
O4 N2 C3 N4 -173.89(18) . . . . ?
O4 N2 C3 C2 12.5(2) . . . . ?
O5 N2 C3 N4 8.2(3) . . . . ?
O5 N2 C3 C2 -165.4(2) . . . . ?
O6 N7 C5 N6 -1.4(2) . . . . ?
O6 N7 C5 C6 179.19(19) . . . . ?
O7 N7 C5 N6 179.49(19) . . . . ?
O7 N7 C5 C6 0.1(2) . . . . ?
O8 C6 C5 N6 -179.8(2) . . . . ?
O8 C6 C5 N7 -0.4(3) . . . . ?
O8 C6 C7 N5 -179.8(2) . . . . ?
O8 C6 C7 N8 -2.8(3) . . . . ?
O9 N8 C7 N5 -179.22(17) . . . . ?
O9 N8 C7 C6 4.1(2) . . . . ?
O10 N8 C7 N5 0.7(2) . . . . ?
O10 N8 C7 C6 -175.90(18) . . . . ?
N1 C1 N3 N4 176.51(19) . . . . ?
N1 C1 C2 C3 -176.6(2) . . . . ?
N2 C3 N4 N3 -175.1(2) . . . . ?
N2 C3 N4 C4 10.2(3) . . . . ?
N2 C3 C2 C1 174.2(2) . . . . ?
N3 N4 C3 C2 -0.43(18) . . . . ?
N3 N4 C4 N5 -15.1(2) . . . . ?
N3 C1 C2 C3 0.58(19) . . . . ?
N4 C3 C2 C1 -0.08(18) . . . . ?
N4 C4 N5 N6 111.43(18) . . . . ?
N4 C4 N5 C7 -81.9(2) . . . . ?
N5 N6 C5 N7 -179.99(15) . . . . ?
N5 N6 C5 C6 -0.52(18) . . . . ?
N5 C7 C6 C5 0.17(17) . . . . ?
N6 C5 C6 C7 0.21(19) . . . . ?
N7 C5 C6 C7 179.6(2) . . . . ?
N8 C7 C6 C5 177.2(2) . . . . ?
N9 C8 N11 N10 1.17(18) . . . . ?
N9 C9 N10 N11 1.45(18) . . . . ?
N10 N11 C8 N14 179.41(17) . . . . ?
N15 C10 N17 N16 -0.54(18) . . . . ?
N15 C11 N16 N17 -0.93(19) . . . . ?
N16 N17 C10 N19 -177.95(15) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
N19 H19a 1 0.8900 0.0200 -0.0181
N19 H19b 1 0.8900 0.0200 0.0041
H19a H19b 1 1.5000 0.0400 0.0154
C10 H19a 1 2.0000 0.0400 0.0656
C10 H19b 1 2.0000 0.0400 0.0640

