# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_compd6
_database_code_depnum_ccdc_archive 'CCDC 2178043'
loop_
_audit_author_name
_audit_author_address
'Dheeraj Kumar'
;IIT Roorkee
India
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2023-07-20 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         'C10 H5 N7 O10'
_chemical_formula_sum            'C10 H5 N7 O10'
_chemical_formula_weight         383.21

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                   6.911(2)
_cell_length_b                   20.066(7)
_cell_length_c                   11.124(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.903(15)
_cell_angle_gamma                90
_cell_volume                     1476.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    8317
_cell_measurement_theta_min      0.965
_cell_measurement_theta_max      0.972

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   0.965
_exptl_transmission_factor_max   0.972
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(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            47494
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.030
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3669
_reflns_number_gt                2778
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.1000P)²+0.5101P] 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_number_reflns         3658
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_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
N1 N 0.3339(2) 0.54324(7) 0.24352(13) 0.0365(3) Uani 1 1 d . . . . .
N2 N 0.5124(2) 0.53592(7) 0.32926(14) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.8192(2) 0.54051(8) 0.53716(17) 0.0623(4) Uani 1 1 d . . . . .
O1 O 0.6709(2) 0.61554(10) 0.61694(16) 0.0656(5) Uani 1 1 d . . . . .
O10 O 0.0460(3) 0.83579(8) 0.41270(17) 0.0700(5) Uani 1 1 d . . . . .
N3 N 0.6758(2) 0.57711(8) 0.53382(16) 0.0416(4) Uani 1 1 d . . . . .
N7 N 0.0412(3) 0.81686(8) 0.51613(17) 0.0463(4) Uani 1 1 d . . . . .
O5 O 0.1689(3) 0.55924(9) 0.80851(16) 0.0715(5) Uani 1 1 d . . . . .
O9 O -0.0140(3) 0.85088(8) 0.58981(18) 0.0695(5) Uani 1 1 d . . . . .
N5 N 0.1146(3) 0.61653(9) 0.79481(15) 0.0475(4) Uani 1 1 d . . . . .
O6 O 0.0380(3) 0.64565(10) 0.86453(17) 0.0775(6) Uani 1 1 d . . . . .
N6 N -0.0050(3) 0.75624(9) 0.74602(17) 0.0527(4) Uani 1 1 d . . . . .
O7 O 0.1111(3) 0.78174(10) 0.83765(16) 0.0740(5) Uani 1 1 d . . . . .
O8 O -0.1885(3) 0.75859(10) 0.71659(19) 0.0764(6) Uani 1 1 d . . . . .
N4 N 0.0128(3) 0.60202(10) 0.21278(17) 0.0547(5) Uani 1 1 d . . . . .
C4 C 0.5004(2) 0.57327(8) 0.42534(16) 0.0332(3) Uani 1 1 d . . . . .
C5 C 0.2401(2) 0.64625(8) 0.49518(15) 0.0322(3) Uani 1 1 d . . . . .
C3 C 0.3146(2) 0.60555(8) 0.40653(15) 0.0330(3) Uani 1 1 d . . . . .
C6 C 0.2196(3) 0.61639(8) 0.60346(15) 0.0343(3) Uani 1 1 d . . . . .
H6 H 0.258387 0.572256 0.621402 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1833(3) 0.71213(9) 0.46968(16) 0.0357(4) Uani 1 1 d . . . . .
H10 H 0.197694 0.732490 0.397660 0.043 Uiso 1 1 calc R U . . .
O3 O -0.0515(3) 0.58238(13) 0.10769(18) 0.0917(7) Uani 1 1 d . . . . .
C8 C 0.0830(3) 0.71890(9) 0.66031(16) 0.0369(4) Uani 1 1 d . . . . .
C2 C 0.2138(3) 0.58462(9) 0.28692(16) 0.0368(4) Uani 1 1 d . . . . .
C9 C 0.1052(3) 0.74763(8) 0.55162(16) 0.0359(4) Uani 1 1 d . . . . .
C7 C 0.1412(3) 0.65248(9) 0.68465(15) 0.0359(4) Uani 1 1 d . . . . .
C1 C 0.2955(4) 0.50524(10) 0.12565(19) 0.0526(5) Uani 1 1 d . . . . .
H1A H 0.413063 0.479426 0.126961 0.079 Uiso 1 1 calc R U . . .
H1B H 0.266074 0.535524 0.055850 0.079 Uiso 1 1 calc R U . . .
H1C H 0.182427 0.476009 0.117309 0.079 Uiso 1 1 calc R U . . .
O4 O -0.0840(4) 0.63596(19) 0.2624(3) 0.1603(17) 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
N1 N2 1.330(2) . ?
N1 C2 1.358(2) . ?
N1 C1 1.473(2) . ?
N2 C4 1.327(2) . ?
O2 N3 1.225(2) . ?
O1 N3 1.212(2) . ?
O10 N7 1.221(2) . ?
N3 C4 1.443(2) . ?
N7 O9 1.210(2) . ?
N7 C9 1.476(2) . ?
O5 N5 1.205(3) . ?
N5 O6 1.209(2) . ?
N5 C7 1.479(2) . ?
N6 O7 1.212(2) . ?
N6 O8 1.215(3) . ?
N6 C8 1.476(2) . ?
N4 O3 1.190(3) . ?
N4 O4 1.196(3) . ?
N4 C2 1.437(2) . ?
C4 C3 1.399(2) . ?
C5 C10 1.385(2) . ?
C5 C6 1.389(2) . ?
C5 C3 1.483(2) . ?
C3 C2 1.376(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C10 C9 1.384(2) . ?
C10 H10 0.9300 . ?
C8 C9 1.387(3) . ?
C8 C7 1.396(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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 N1 C2 110.36(14) . . ?
N2 N1 C1 118.08(15) . . ?
C2 N1 C1 131.49(17) . . ?
C4 N2 N1 104.66(14) . . ?
O1 N3 O2 124.08(17) . . ?
O1 N3 C4 117.95(16) . . ?
O2 N3 C4 117.96(16) . . ?
O9 N7 O10 124.25(18) . . ?
O9 N7 C9 118.58(17) . . ?
O10 N7 C9 117.17(16) . . ?
O5 N5 O6 123.95(18) . . ?
O5 N5 C7 117.43(16) . . ?
O6 N5 C7 118.62(18) . . ?
O7 N6 O8 126.44(19) . . ?
O7 N6 C8 117.46(18) . . ?
O8 N6 C8 116.09(18) . . ?
O3 N4 O4 122.8(2) . . ?
O3 N4 C2 120.39(19) . . ?
O4 N4 C2 116.78(18) . . ?
N2 C4 C3 114.24(15) . . ?
N2 C4 N3 118.01(15) . . ?
C3 C4 N3 127.74(15) . . ?
C10 C5 C6 119.69(15) . . ?
C10 C5 C3 121.47(14) . . ?
C6 C5 C3 118.79(15) . . ?
C2 C3 C4 100.83(14) . . ?
C2 C3 C5 129.42(15) . . ?
C4 C3 C5 129.55(15) . . ?
C7 C6 C5 119.85(16) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C9 C10 C5 119.87(15) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
C9 C8 C7 117.87(15) . . ?
C9 C8 N6 121.50(17) . . ?
C7 C8 N6 120.60(16) . . ?
N1 C2 C3 109.90(15) . . ?
N1 C2 N4 122.22(16) . . ?
C3 C2 N4 127.88(16) . . ?
C10 C9 C8 121.52(16) . . ?
C10 C9 N7 116.87(16) . . ?
C8 C9 N7 121.59(15) . . ?
C6 C7 C8 121.20(15) . . ?
C6 C7 N5 116.86(16) . . ?
C8 C7 N5 121.89(15) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_kp_hncptot_0016_0ma
_database_code_depnum_ccdc_archive 'CCDC 2270163'
loop_
_audit_author_name
_audit_author_address
'Dheeraj Kumar'
;IIT Roorkee
India
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2023-06-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H4 N7 O11, 2(H2 O), C3 H7 N8'
_chemical_formula_sum            'C13 H15 N15 O13'
_chemical_formula_weight         589.40
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2504(7)
_cell_length_b                   22.4474(12)
_cell_length_c                   7.5543(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.1480(10)
_cell_angle_gamma                90
_cell_volume                     2234.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9808
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.925
_cell_measurement_theta_min      2.384
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7438
_exptl_absorpt_correction_T_min  0.7251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1262 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.9749.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   block
_exptl_crystal_colour            'Clear Light Yellow'
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            154320
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.258
_diffrn_reflns_theta_min         1.792
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST Photon III C7'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4218
_reflns_number_total             5004
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+2.3042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O13(H13C,H13D), O12(H12A)
2.b Rotating group:
 N15(H15A,H15B), N13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N8(H8), C9(H9)
2.d X=CH2 refined with riding coordinates:
 N14(H14A,H14B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O001 O 0.17167(9) 0.53024(6) 0.61476(17) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.56297(11) 0.53167(7) 0.62235(19) 0.0299(3) Uani 1 1 d . . . . .
O13 O 0.08378(12) 0.28250(7) 0.7590(2) 0.0343(4) Uani 1 1 d G . . . .
H13C H 0.074198 0.309911 0.677509 0.051 Uiso 1 1 d G U . . .
H13D H 0.111637 0.253191 0.706639 0.051 Uiso 1 1 d G U . . .
O9 O 0.24530(12) 0.44885(7) 1.10138(19) 0.0337(4) Uani 1 1 d . . . . .
O10 O 0.51859(12) 0.57955(7) 1.21184(19) 0.0346(4) Uani 1 1 d . . . . .
O8 O 0.16654(12) 0.43742(7) 0.8405(2) 0.0379(4) Uani 1 1 d . . . . .
O4 O 0.68881(11) 0.57239(8) 0.5038(2) 0.0362(4) Uani 1 1 d . . . . .
O6 O 0.29318(14) 0.58347(7) 0.35503(19) 0.0370(4) Uani 1 1 d . . . . .
O1 O 0.35130(12) 0.72144(7) 0.8481(2) 0.0359(4) Uani 1 1 d . . . . .
O11 O 0.58432(11) 0.62526(8) 1.0007(2) 0.0369(4) Uani 1 1 d . . . . .
N10 N -0.00464(11) 0.41843(7) 0.2203(2) 0.0187(3) Uani 1 1 d . . . . .
N8 N 0.08248(12) 0.42907(7) 0.4698(2) 0.0225(3) Uani 1 1 d . . . . .
H8 H 0.124662 0.444173 0.556074 0.027 Uiso 1 1 calc R U . . .
N11 N -0.06929(12) 0.41747(7) 0.0610(2) 0.0210(3) Uani 1 1 d . . . . .
N6 N 0.22817(12) 0.46401(7) 0.9446(2) 0.0225(3) Uani 1 1 d . . . . .
N12 N -0.08203(12) 0.33408(7) 0.2261(2) 0.0227(3) Uani 1 1 d . . . . .
N5 N 0.29170(11) 0.61235(7) 0.4899(2) 0.0202(3) Uani 1 1 d . . . . .
O12 O 0.15920(15) 0.31961(8) 1.1011(2) 0.0417(4) Uani 1 1 d G . . . .
H12A H 0.135171 0.312955 0.991202 0.062 Uiso 1 1 d G U . . .
N9 N 0.03902(12) 0.37232(7) 0.4788(2) 0.0232(3) Uani 1 1 d . . . . .
O5 O 0.25835(14) 0.66310(7) 0.4921(2) 0.0410(4) Uani 1 1 d . . . . .
N7 N 0.51695(12) 0.59524(7) 1.0561(2) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.41478(14) 0.79922(7) 0.7306(2) 0.0425(4) Uani 1 1 d . . . . .
N14 N 0.07679(13) 0.51305(7) 0.2764(2) 0.0258(4) Uani 1 1 d . . . . .
H14A H 0.115118 0.535098 0.352899 0.031 Uiso 1 1 calc R U . . .
H14B H 0.053680 0.527727 0.171800 0.031 Uiso 1 1 calc R U . . .
N4 N 0.60873(12) 0.57456(8) 0.5708(2) 0.0250(4) Uani 1 1 d . . . . .
N15 N -0.18249(13) 0.34064(8) -0.0499(2) 0.0276(4) Uani 1 1 d . . . . .
H15A H -0.225617 0.319336 0.004466 0.033 Uiso 1 1 d R U . . .
H15B H -0.215428 0.369077 -0.112103 0.033 Uiso 1 1 d R U . . .
N3 N 0.40966(13) 0.74550(8) 0.7559(2) 0.0273(4) Uani 1 1 d . . . . .
N1 N 0.60476(12) 0.68426(8) 0.5437(2) 0.0270(4) Uani 1 1 d . . . . .
N13 N -0.11623(13) 0.27704(7) 0.2610(3) 0.0299(4) Uani 1 1 d . . . . .
H13A H -0.063847 0.252835 0.277070 0.036 Uiso 1 1 d R U . . .
H13B H -0.147689 0.277815 0.357836 0.036 Uiso 1 1 d R U . . .
N2 N 0.55210(13) 0.73081(8) 0.5925(2) 0.0290(4) Uani 1 1 d . . . . .
C11 C 0.05405(13) 0.45812(8) 0.3182(2) 0.0197(4) Uani 1 1 d . . . . .
C7 C 0.25257(13) 0.54022(8) 0.7118(2) 0.0177(4) Uani 1 1 d . . . . .
C12 C -0.01329(13) 0.36961(8) 0.3227(2) 0.0201(4) Uani 1 1 d . . . . .
C8 C 0.28480(13) 0.51343(8) 0.8810(2) 0.0192(4) Uani 1 1 d . . . . .
C13 C -0.11375(14) 0.36523(8) 0.0716(2) 0.0211(4) Uani 1 1 d . . . . .
C10 C 0.43063(13) 0.57681(8) 0.9329(2) 0.0192(4) Uani 1 1 d . . . . .
C3 C 0.48121(13) 0.64457(8) 0.6836(2) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.41200(13) 0.60222(8) 0.7612(2) 0.0185(4) Uani 1 1 d . . . . .
C6 C 0.32405(13) 0.58419(8) 0.6626(2) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.56432(14) 0.63207(9) 0.5949(2) 0.0219(4) Uani 1 1 d . . . . .
C9 C 0.36814(13) 0.53351(8) 0.9909(2) 0.0196(4) Uani 1 1 d . . . . .
H9 H 0.382366 0.517336 1.107127 0.024 Uiso 1 1 calc R U . . .
C4 C 0.47908(14) 0.70674(9) 0.6768(3) 0.0233(4) Uani 1 1 d . . . . .
C1 C 0.69085(17) 0.69541(12) 0.4404(3) 0.0394(5) Uani 1 1 d . . . . .
H1A H 0.678404 0.675806 0.324155 0.059 Uiso 1 1 calc R U . . .
H1B H 0.753119 0.679459 0.504871 0.059 Uiso 1 1 calc R U . . .
H1C H 0.698375 0.738392 0.423193 0.059 Uiso 1 1 calc R U . . .
H12B H 0.184(3) 0.3543(17) 1.112(5) 0.078(12) 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
O001 C7 1.252(2) . ?
O3 N4 1.224(2) . ?
O13 H13C 0.8698 . ?
O13 H13D 0.8699 . ?
O9 N6 1.230(2) . ?
O10 N7 1.226(2) . ?
O8 N6 1.226(2) . ?
O4 N4 1.225(2) . ?
O6 N5 1.209(2) . ?
O1 N3 1.220(2) . ?
O11 N7 1.227(2) . ?
N10 N11 1.401(2) . ?
N10 C11 1.350(2) . ?
N10 C12 1.354(2) . ?
N8 H8 0.8800 . ?
N8 N9 1.403(2) . ?
N8 C11 1.336(2) . ?
N11 C13 1.319(2) . ?
N6 C8 1.450(2) . ?
N12 N13 1.393(2) . ?
N12 C12 1.362(2) . ?
N12 C13 1.387(2) . ?
N5 O5 1.223(2) . ?
N5 C6 1.472(2) . ?
O12 H12A 0.8698 . ?
O12 H12B 0.85(4) . ?
N9 C12 1.303(2) . ?
N7 C10 1.455(2) . ?
O2 N3 1.224(2) . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
N14 C11 1.316(2) . ?
N4 C2 1.438(3) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8802 . ?
N15 C13 1.341(2) . ?
N3 C4 1.442(3) . ?
N1 N2 1.330(2) . ?
N1 C2 1.362(2) . ?
N1 C1 1.471(3) . ?
N13 H13A 0.8796 . ?
N13 H13B 0.8803 . ?
N2 C4 1.329(3) . ?
C7 C8 1.436(2) . ?
C7 C6 1.444(2) . ?
C8 C9 1.384(2) . ?
C10 C5 1.414(2) . ?
C10 C9 1.378(3) . ?
C3 C5 1.484(3) . ?
C3 C2 1.378(3) . ?
C3 C4 1.397(3) . ?
C5 C6 1.375(2) . ?
C9 H9 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
H13C O13 H13D 104.5 . . ?
C11 N10 N11 138.10(16) . . ?
C11 N10 C12 107.48(15) . . ?
C12 N10 N11 113.40(15) . . ?
N9 N8 H8 123.0 . . ?
C11 N8 H8 123.0 . . ?
C11 N8 N9 113.92(15) . . ?
C13 N11 N10 101.42(14) . . ?
O9 N6 C8 118.83(15) . . ?
O8 N6 O9 121.62(16) . . ?
O8 N6 C8 119.52(15) . . ?
C12 N12 N13 130.49(16) . . ?
C12 N12 C13 106.30(15) . . ?
C13 N12 N13 123.18(15) . . ?
O6 N5 O5 123.31(16) . . ?
O6 N5 C6 119.15(16) . . ?
O5 N5 C6 117.37(15) . . ?
H12A O12 H12B 110.7 . . ?
C12 N9 N8 100.35(15) . . ?
O10 N7 O11 123.09(16) . . ?
O10 N7 C10 117.63(16) . . ?
O11 N7 C10 119.28(16) . . ?
H14A N14 H14B 120.0 . . ?
C11 N14 H14A 120.0 . . ?
C11 N14 H14B 120.0 . . ?
O3 N4 O4 125.55(18) . . ?
O3 N4 C2 116.25(16) . . ?
O4 N4 C2 118.19(17) . . ?
H15A N15 H15B 109.5 . . ?
C13 N15 H15A 109.4 . . ?
C13 N15 H15B 109.2 . . ?
O1 N3 O2 125.06(18) . . ?
O1 N3 C4 116.16(17) . . ?
O2 N3 C4 118.75(18) . . ?
N2 N1 C2 111.30(16) . . ?
N2 N1 C1 118.23(18) . . ?
C2 N1 C1 130.40(19) . . ?
N12 N13 H13A 109.0 . . ?
N12 N13 H13B 109.4 . . ?
H13A N13 H13B 109.5 . . ?
C4 N2 N1 104.12(16) . . ?
N8 C11 N10 103.90(16) . . ?
N14 C11 N10 128.32(17) . . ?
N14 C11 N8 127.77(17) . . ?
O001 C7 C8 126.92(16) . . ?
O001 C7 C6 121.04(16) . . ?
C8 C7 C6 112.00(15) . . ?
N10 C12 N12 105.10(15) . . ?
N9 C12 N10 114.20(16) . . ?
N9 C12 N12 140.55(18) . . ?
C7 C8 N6 120.02(15) . . ?
C9 C8 N6 117.28(16) . . ?
C9 C8 C7 122.68(17) . . ?
N11 C13 N12 113.72(16) . . ?
N11 C13 N15 126.87(17) . . ?
N15 C13 N12 119.41(17) . . ?
C5 C10 N7 121.32(16) . . ?
C9 C10 N7 117.08(16) . . ?
C9 C10 C5 121.60(16) . . ?
C2 C3 C5 128.42(17) . . ?
C2 C3 C4 101.51(17) . . ?
C4 C3 C5 130.06(17) . . ?
C10 C5 C3 124.47(15) . . ?
C6 C5 C10 115.65(16) . . ?
C6 C5 C3 119.87(16) . . ?
C7 C6 N5 112.64(14) . . ?
C5 C6 N5 120.23(16) . . ?
C5 C6 C7 127.08(16) . . ?
N1 C2 N4 123.89(17) . . ?
N1 C2 C3 108.80(17) . . ?
C3 C2 N4 127.12(17) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.45(17) . . ?
C10 C9 H9 119.8 . . ?
N2 C4 N3 118.89(18) . . ?
N2 C4 C3 114.27(18) . . ?
C3 C4 N3 126.79(18) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
O001 C7 C8 N6 8.6(3) . . . . ?
O001 C7 C8 C9 -170.14(18) . . . . ?
O001 C7 C6 N5 -1.8(2) . . . . ?
O001 C7 C6 C5 175.56(18) . . . . ?
O3 N4 C2 N1 -179.41(17) . . . . ?
O3 N4 C2 C3 6.3(3) . . . . ?
O9 N6 C8 C7 -166.90(17) . . . . ?
O9 N6 C8 C9 11.9(3) . . . . ?
O10 N7 C10 C5 167.28(17) . . . . ?
O10 N7 C10 C9 -12.8(2) . . . . ?
O8 N6 C8 C7 15.0(3) . . . . ?
O8 N6 C8 C9 -166.19(18) . . . . ?
O4 N4 C2 N1 1.6(3) . . . . ?
O4 N4 C2 C3 -172.67(18) . . . . ?
O6 N5 C6 C7 -70.7(2) . . . . ?
O6 N5 C6 C5 111.7(2) . . . . ?
O1 N3 C4 N2 -172.24(18) . . . . ?
O1 N3 C4 C3 5.2(3) . . . . ?
O11 N7 C10 C5 -12.9(3) . . . . ?
O11 N7 C10 C9 166.96(18) . . . . ?
N10 N11 C13 N12 0.5(2) . . . . ?
N10 N11 C13 N15 -178.46(19) . . . . ?
N8 N9 C12 N10 0.8(2) . . . . ?
N8 N9 C12 N12 -173.6(2) . . . . ?
N11 N10 C11 N8 170.93(19) . . . . ?
N11 N10 C11 N14 -8.0(4) . . . . ?
N11 N10 C12 N12 2.6(2) . . . . ?
N11 N10 C12 N9 -173.73(16) . . . . ?
N6 C8 C9 C10 174.37(16) . . . . ?
N9 N8 C11 N10 -3.6(2) . . . . ?
N9 N8 C11 N14 175.26(18) . . . . ?
O5 N5 C6 C7 104.75(19) . . . . ?
O5 N5 C6 C5 -72.8(2) . . . . ?
N7 C10 C5 C3 6.1(3) . . . . ?
N7 C10 C5 C6 -175.44(16) . . . . ?
N7 C10 C9 C8 -179.65(16) . . . . ?
O2 N3 C4 N2 6.0(3) . . . . ?
O2 N3 C4 C3 -176.58(19) . . . . ?
N1 N2 C4 N3 177.07(16) . . . . ?
N1 N2 C4 C3 -0.7(2) . . . . ?
N13 N12 C12 N10 176.12(18) . . . . ?
N13 N12 C12 N9 -9.1(4) . . . . ?
N13 N12 C13 N11 -177.37(17) . . . . ?
N13 N12 C13 N15 1.7(3) . . . . ?
N2 N1 C2 N4 -175.83(17) . . . . ?
N2 N1 C2 C3 -0.6(2) . . . . ?
C11 N10 N11 C13 -168.5(2) . . . . ?
C11 N10 C12 N12 173.25(15) . . . . ?
C11 N10 C12 N9 -3.1(2) . . . . ?
C11 N8 N9 C12 1.8(2) . . . . ?
C7 C8 C9 C10 -6.8(3) . . . . ?
C12 N10 N11 C13 -1.97(19) . . . . ?
C12 N10 C11 N8 3.88(19) . . . . ?
C12 N10 C11 N14 -175.02(19) . . . . ?
C12 N12 C13 N11 1.0(2) . . . . ?
C12 N12 C13 N15 -179.92(17) . . . . ?
C8 C7 C6 N5 -179.61(15) . . . . ?
C8 C7 C6 C5 -2.2(3) . . . . ?
C13 N12 C12 N10 -2.1(2) . . . . ?
C13 N12 C12 N9 172.7(2) . . . . ?
C10 C5 C6 N5 173.63(16) . . . . ?
C10 C5 C6 C7 -3.6(3) . . . . ?
C3 C5 C6 N5 -7.8(3) . . . . ?
C3 C5 C6 C7 174.98(17) . . . . ?
C5 C10 C9 C8 0.2(3) . . . . ?
C5 C3 C2 N4 -6.0(3) . . . . ?
C5 C3 C2 N1 178.94(17) . . . . ?
C5 C3 C4 N3 4.0(3) . . . . ?
C5 C3 C4 N2 -178.41(17) . . . . ?
C6 C7 C8 N6 -173.76(16) . . . . ?
C6 C7 C8 C9 7.5(2) . . . . ?
C2 N1 N2 C4 0.8(2) . . . . ?
C2 C3 C5 C10 84.9(3) . . . . ?
C2 C3 C5 C6 -93.5(2) . . . . ?
C2 C3 C4 N3 -177.22(18) . . . . ?
C2 C3 C4 N2 0.3(2) . . . . ?
C9 C10 C5 C3 -173.80(17) . . . . ?
C9 C10 C5 C6 4.7(3) . . . . ?
C4 C3 C5 C10 -96.7(2) . . . . ?
C4 C3 C5 C6 84.9(3) . . . . ?
C4 C3 C2 N4 175.18(17) . . . . ?
C4 C3 C2 N1 0.2(2) . . . . ?
C1 N1 N2 C4 178.07(18) . . . . ?
C1 N1 C2 N4 7.3(3) . . . . ?
C1 N1 C2 C3 -177.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile water'
