# Supplementary Information (SI) for Dalton Transactions.
# 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_dk_kp_tzno_0666_0m
_database_code_depnum_ccdc_archive 'CCDC 2381172'
loop_
_audit_author_name
_audit_author_address
'Priyanka Das'
;IIT Roorkee
India
;
_audit_update_record             
;
2024-09-01 deposited with the CCDC.	2024-10-04 downloaded from the CCDC.
;
_audit_creation_date             2024-02-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N8 O6'
_chemical_formula_sum            'C6 H6 N8 O6'
_chemical_formula_weight         286.19
_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                   8.4322(6)
_cell_length_b                   6.1733(4)
_cell_length_c                   10.2585(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.420(2)
_cell_angle_gamma                90
_cell_volume                     519.42(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8012
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1369 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.9019.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.144
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13652
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.815
_diffrn_reflns_theta_min         2.041
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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         0.825
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2173
_reflns_number_total             2208
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.069
_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)+(0.0388P)²+0.0750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0642
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
1.b Aromatic/amide H refined with riding coordinates:
 N6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.16929(18) -0.0106(3) 0.46230(14) 0.0230(3) Uani 1 1 d . . . . .
O2 O 0.03653(19) -0.0502(3) 0.61890(15) 0.0248(4) Uani 1 1 d . . . . .
O3 O 0.11081(19) 0.2483(3) 0.84687(15) 0.0207(3) Uani 1 1 d . . . . .
H3 H 0.072(4) 0.122(6) 0.831(3) 0.038(9) Uiso 1 1 d . . . . .
O4 O 0.2928(2) 0.5917(3) 0.98798(15) 0.0272(4) Uani 1 1 d . . . . .
O5 O 0.3779(2) 0.8294(3) 0.86289(17) 0.0285(4) Uani 1 1 d . . . . .
O6 O 0.99327(17) 0.8834(2) 0.89022(13) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.35353(19) 0.5178(3) 0.66292(15) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.3075(2) 0.3544(3) 0.57909(16) 0.0168(4) Uani 1 1 d . . . . .
N3 N 0.13435(19) 0.0462(3) 0.56678(16) 0.0166(4) Uani 1 1 d . . . . .
N4 N 0.3230(2) 0.6510(3) 0.88285(18) 0.0204(4) Uani 1 1 d . . . . .
N5 N 0.6869(2) 0.4987(3) 0.79705(16) 0.0172(3) Uani 1 1 d . . . . .
N6 N 0.8392(2) 0.5653(3) 0.86785(17) 0.0175(4) Uani 1 1 d . . . . .
H6 H 0.908364 0.480949 0.922558 0.021 Uiso 1 1 calc R U . . .
N7 N 0.7309(2) 0.8397(3) 0.75310(16) 0.0148(3) Uani 1 1 d . . . . .
N8 N 0.6936(2) 1.0481(3) 0.70186(17) 0.0179(4) Uani 1 1 d . . . . .
H8A H 0.765(3) 1.087(4) 0.658(2) 0.014(6) Uiso 1 1 d . . . . .
H8B H 0.693(3) 1.142(5) 0.771(3) 0.025(7) Uiso 1 1 d . . . . .
C1 C 0.2105(2) 0.2338(3) 0.6359(2) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.1945(2) 0.3142(4) 0.7609(2) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.2901(2) 0.4993(3) 0.77423(19) 0.0172(4) Uani 1 1 d . . . . .
C4 C 0.4662(2) 0.6774(3) 0.6302(2) 0.0174(4) Uani 1 1 d . . . . .
H4A H 0.419564 0.824399 0.631248 0.021 Uiso 1 1 calc R U . . .
H4B H 0.481483 0.649379 0.538841 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6273(2) 0.6669(3) 0.72845(18) 0.0152(4) Uani 1 1 d . . . . .
C6 C 0.8697(2) 0.7737(3) 0.84367(19) 0.0160(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.227(2) . ?
O2 N3 1.235(2) . ?
O3 H3 0.85(4) . ?
O3 C2 1.316(3) . ?
O4 N4 1.220(3) . ?
O5 N4 1.230(3) . ?
O6 C6 1.242(3) . ?
N1 N2 1.324(2) . ?
N1 C3 1.373(2) . ?
N1 C4 1.461(3) . ?
N2 C1 1.335(3) . ?
N3 C1 1.430(3) . ?
N4 C3 1.433(3) . ?
N5 N6 1.383(2) . ?
N5 C5 1.290(3) . ?
N6 H6 0.8800 . ?
N6 C6 1.346(3) . ?
N7 N8 1.398(2) . ?
N7 C5 1.365(3) . ?
N7 C6 1.376(3) . ?
N8 H8A 0.87(3) . ?
N8 H8B 0.92(3) . ?
C1 C2 1.410(3) . ?
C2 C3 1.387(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.493(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
C2 O3 H3 113(2) . . ?
N2 N1 C3 111.37(16) . . ?
N2 N1 C4 118.21(16) . . ?
C3 N1 C4 130.31(17) . . ?
N1 N2 C1 104.98(16) . . ?
O1 N3 O2 124.07(17) . . ?
O1 N3 C1 119.56(16) . . ?
O2 N3 C1 116.37(16) . . ?
O4 N4 O5 125.41(19) . . ?
O4 N4 C3 116.67(18) . . ?
O5 N4 C3 117.91(18) . . ?
C5 N5 N6 104.12(17) . . ?
N5 N6 H6 123.8 . . ?
C6 N6 N5 112.41(17) . . ?
C6 N6 H6 123.8 . . ?
C5 N7 N8 124.81(16) . . ?
C5 N7 C6 107.54(16) . . ?
C6 N7 N8 127.47(17) . . ?
N7 N8 H8A 109.4(17) . . ?
N7 N8 H8B 109.3(18) . . ?
H8A N8 H8B 111(2) . . ?
N2 C1 N3 119.04(17) . . ?
N2 C1 C2 113.45(18) . . ?
C2 C1 N3 127.50(18) . . ?
O3 C2 C1 132.9(2) . . ?
O3 C2 C3 125.34(19) . . ?
C3 C2 C1 101.74(18) . . ?
N1 C3 N4 123.36(18) . . ?
N1 C3 C2 108.43(18) . . ?
C2 C3 N4 128.21(19) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 C5 110.71(16) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
N5 C5 N7 112.12(17) . . ?
N5 C5 C4 125.58(19) . . ?
N7 C5 C4 122.29(18) . . ?
O6 C6 N6 129.0(2) . . ?
O6 C6 N7 127.19(19) . . ?
N6 C6 N7 103.80(17) . . ?

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 N3 C1 N2 5.9(3) . . . . ?
O1 N3 C1 C2 -175.21(19) . . . . ?
O2 N3 C1 N2 -174.76(18) . . . . ?
O2 N3 C1 C2 4.2(3) . . . . ?
O3 C2 C3 N1 -177.98(18) . . . . ?
O3 C2 C3 N4 2.4(3) . . . . ?
O4 N4 C3 N1 -163.11(18) . . . . ?
O4 N4 C3 C2 16.5(3) . . . . ?
O5 N4 C3 N1 17.3(3) . . . . ?
O5 N4 C3 C2 -163.1(2) . . . . ?
N1 N2 C1 N3 177.57(16) . . . . ?
N1 N2 C1 C2 -1.5(2) . . . . ?
N1 C4 C5 N5 26.2(3) . . . . ?
N1 C4 C5 N7 -155.25(18) . . . . ?
N2 N1 C3 N4 178.56(18) . . . . ?
N2 N1 C3 C2 -1.1(2) . . . . ?
N2 N1 C4 C5 -112.98(19) . . . . ?
N2 C1 C2 O3 178.8(2) . . . . ?
N2 C1 C2 C3 0.8(2) . . . . ?
N3 C1 C2 O3 -0.2(4) . . . . ?
N3 C1 C2 C3 -178.14(19) . . . . ?
N5 N6 C6 O6 -179.99(19) . . . . ?
N5 N6 C6 N7 -0.4(2) . . . . ?
N6 N5 C5 N7 -1.3(2) . . . . ?
N6 N5 C5 C4 177.33(18) . . . . ?
N8 N7 C5 N5 -174.41(17) . . . . ?
N8 N7 C5 C4 6.9(3) . . . . ?
N8 N7 C6 O6 -5.4(3) . . . . ?
N8 N7 C6 N6 175.00(18) . . . . ?
C1 C2 C3 N1 0.2(2) . . . . ?
C1 C2 C3 N4 -179.5(2) . . . . ?
C3 N1 N2 C1 1.6(2) . . . . ?
C3 N1 C4 C5 62.9(3) . . . . ?
C4 N1 N2 C1 178.18(17) . . . . ?
C4 N1 C3 N4 2.5(3) . . . . ?
C4 N1 C3 C2 -177.19(19) . . . . ?
C5 N5 N6 C6 1.1(2) . . . . ?
C5 N7 C6 O6 179.2(2) . . . . ?
C5 N7 C6 N6 -0.4(2) . . . . ?
C6 N7 C5 N5 1.1(2) . . . . ?
C6 N7 C5 C4 -177.59(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cdnphy_0464_0m
_database_code_depnum_ccdc_archive 'CCDC 2381173'
loop_
_audit_author_name
_audit_author_address
'Priyanka Das'
;IIT Roorkee
India
;
_audit_update_record             
;
2024-09-01 deposited with the CCDC.	2024-10-04 downloaded from the CCDC.
;
_audit_creation_date             2024-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H7 N9 O5'
_chemical_formula_sum            'C6 H7 N9 O5'
_chemical_formula_weight         285.21
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.2377(4)
_cell_length_b                   7.5343(4)
_cell_length_c                   38.309(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2089.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6314
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.8998.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            29940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.110
_diffrn_reflns_theta_min         2.126
_diffrn_ambient_temperature      108.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1912
_reflns_number_total             2311
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.8158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N9(H9A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4C,H4D)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
;
_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 0.84364(14) 0.61800(15) 0.46637(3) 0.0215(3) Uani 1 1 d . . . . .
O2 O 0.57465(15) 0.69999(15) 0.48605(3) 0.0230(3) Uani 1 1 d . . . . .
O3 O 0.07570(14) 0.36563(15) 0.40022(3) 0.0203(3) Uani 1 1 d . . . . .
O4 O 0.24639(15) 0.22080(15) 0.36279(3) 0.0212(3) Uani 1 1 d . . . . .
O5 O 0.40868(15) 0.29738(14) 0.24868(3) 0.0199(3) Uani 1 1 d . . . . .
N1 N 0.56355(15) 0.34846(16) 0.39513(3) 0.0121(3) Uani 1 1 d . . . . .
N2 N 0.68378(16) 0.42904(17) 0.41571(3) 0.0131(3) Uani 1 1 d . . . . .
N3 N 0.67409(17) 0.61697(17) 0.46532(3) 0.0160(3) Uani 1 1 d . . . . .
N4 N 0.24905(17) 0.56150(18) 0.45330(3) 0.0182(3) Uani 1 1 d . . . . .
H4A H 0.134409 0.537611 0.447263 0.022 Uiso 1 1 calc R U . . .
H4B H 0.271328 0.629627 0.471478 0.022 Uiso 1 1 calc R U . . .
N5 N 0.22797(17) 0.31984(18) 0.38823(3) 0.0157(3) Uani 1 1 d . . . . .
N6 N 0.61337(17) 0.47983(17) 0.32287(3) 0.0159(3) Uani 1 1 d . . . . .
N7 N 0.54361(18) 0.48996(18) 0.28924(3) 0.0169(3) Uani 1 1 d . . . . .
H7 H 0.561(3) 0.590(3) 0.2772(5) 0.029(5) Uiso 1 1 d . . . . .
N8 N 0.50838(17) 0.21977(17) 0.30512(3) 0.0148(3) Uani 1 1 d . . . . .
N9 N 0.45178(19) 0.04199(18) 0.30773(4) 0.0189(3) Uani 1 1 d . . . . .
H9A H 0.331592 0.035396 0.304472 0.023 Uiso 1 1 d R U . . .
H9B H 0.507(3) -0.023(3) 0.2897(5) 0.028(5) Uiso 1 1 d . . . . .
C1 C 0.5825(2) 0.5160(2) 0.43925(4) 0.0132(3) Uani 1 1 d . . . . .
C2 C 0.3897(2) 0.4941(2) 0.43481(4) 0.0136(3) Uani 1 1 d . . . . .
C3 C 0.38500(19) 0.3845(2) 0.40548(4) 0.0134(3) Uani 1 1 d . . . . .
C4 C 0.6347(2) 0.2383(2) 0.36653(3) 0.0137(3) Uani 1 1 d . . . . .
H4C H 0.581748 0.117532 0.368352 0.016 Uiso 1 1 calc R U . . .
H4D H 0.770607 0.228349 0.368611 0.016 Uiso 1 1 calc R U . . .
C5 C 0.58690(19) 0.3156(2) 0.33179(4) 0.0135(3) Uani 1 1 d . . . . .
C6 C 0.4804(2) 0.3328(2) 0.27743(4) 0.0154(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2278(16) . ?
O2 N3 1.2409(16) . ?
O3 N5 1.2428(16) . ?
O4 N5 1.2346(16) . ?
O5 C6 1.2465(18) . ?
N1 N2 1.3219(16) . ?
N1 C3 1.3789(18) . ?
N1 C4 1.4675(18) . ?
N2 C1 1.3340(18) . ?
N3 C1 1.4198(19) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C2 1.3403(19) . ?
N5 C3 1.4022(19) . ?
N6 N7 1.3857(17) . ?
N6 C5 1.2982(19) . ?
N7 H7 0.89(2) . ?
N7 C6 1.348(2) . ?
N8 N9 1.4043(18) . ?
N8 C5 1.3740(18) . ?
N8 C6 1.3754(19) . ?
N9 H9A 0.8802 . ?
N9 H9B 0.935(19) . ?
C1 C2 1.415(2) . ?
C2 C3 1.395(2) . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C4 C5 1.4930(19) . ?

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 C3 110.78(12) . . ?
N2 N1 C4 118.29(11) . . ?
C3 N1 C4 130.92(12) . . ?
N1 N2 C1 105.49(12) . . ?
O1 N3 O2 123.76(13) . . ?
O1 N3 C1 119.52(12) . . ?
O2 N3 C1 116.72(12) . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
O3 N5 C3 116.62(12) . . ?
O4 N5 O3 123.72(13) . . ?
O4 N5 C3 119.65(12) . . ?
C5 N6 N7 104.09(12) . . ?
N6 N7 H7 118.4(12) . . ?
C6 N7 N6 112.80(13) . . ?
C6 N7 H7 128.1(12) . . ?
C5 N8 N9 124.66(12) . . ?
C5 N8 C6 108.01(12) . . ?
C6 N8 N9 127.06(12) . . ?
N8 N9 H9A 109.4 . . ?
N8 N9 H9B 108.6(12) . . ?
H9A N9 H9B 106.8 . . ?
N2 C1 N3 118.84(13) . . ?
N2 C1 C2 113.78(13) . . ?
C2 C1 N3 127.38(13) . . ?
N4 C2 C1 129.89(14) . . ?
N4 C2 C3 129.14(14) . . ?
C3 C2 C1 100.96(12) . . ?
N1 C3 N5 123.74(13) . . ?
N1 C3 C2 108.99(13) . . ?
C2 C3 N5 127.27(13) . . ?
N1 C4 H4C 109.4 . . ?
N1 C4 H4D 109.4 . . ?
N1 C4 C5 111.34(12) . . ?
H4C C4 H4D 108.0 . . ?
C5 C4 H4C 109.4 . . ?
C5 C4 H4D 109.4 . . ?
N6 C5 N8 111.48(12) . . ?
N6 C5 C4 124.89(13) . . ?
N8 C5 C4 123.64(13) . . ?
O5 C6 N7 128.78(14) . . ?
O5 C6 N8 127.60(14) . . ?
N7 C6 N8 103.59(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
O1 N3 C1 N2 -2.2(2) . . . . ?
O1 N3 C1 C2 177.61(15) . . . . ?
O2 N3 C1 N2 177.90(13) . . . . ?
O2 N3 C1 C2 -2.3(2) . . . . ?
O3 N5 C3 N1 -178.91(13) . . . . ?
O3 N5 C3 C2 0.4(2) . . . . ?
O4 N5 C3 N1 2.0(2) . . . . ?
O4 N5 C3 C2 -178.69(14) . . . . ?
N1 N2 C1 N3 -179.93(12) . . . . ?
N1 N2 C1 C2 0.21(17) . . . . ?
N1 C4 C5 N6 49.2(2) . . . . ?
N1 C4 C5 N8 -130.68(14) . . . . ?
N2 N1 C3 N5 178.84(13) . . . . ?
N2 N1 C3 C2 -0.57(17) . . . . ?
N2 N1 C4 C5 -113.92(14) . . . . ?
N2 C1 C2 N4 -179.76(15) . . . . ?
N2 C1 C2 C3 -0.53(17) . . . . ?
N3 C1 C2 N4 0.4(3) . . . . ?
N3 C1 C2 C3 179.63(14) . . . . ?
N4 C2 C3 N1 179.87(15) . . . . ?
N4 C2 C3 N5 0.5(3) . . . . ?
N6 N7 C6 O5 179.47(15) . . . . ?
N6 N7 C6 N8 1.17(16) . . . . ?
N7 N6 C5 N8 1.66(16) . . . . ?
N7 N6 C5 C4 -178.26(13) . . . . ?
N9 N8 C5 N6 -175.41(13) . . . . ?
N9 N8 C5 C4 4.5(2) . . . . ?
N9 N8 C6 O5 -4.2(3) . . . . ?
N9 N8 C6 N7 174.09(13) . . . . ?
C1 C2 C3 N1 0.63(16) . . . . ?
C1 C2 C3 N5 -178.76(15) . . . . ?
C3 N1 N2 C1 0.22(16) . . . . ?
C3 N1 C4 C5 66.9(2) . . . . ?
C4 N1 N2 C1 -179.09(12) . . . . ?
C4 N1 C3 N5 -2.0(2) . . . . ?
C4 N1 C3 C2 178.63(14) . . . . ?
C5 N6 N7 C6 -1.79(17) . . . . ?
C5 N8 C6 O5 -178.44(15) . . . . ?
C5 N8 C6 N7 -0.11(15) . . . . ?
C6 N8 C5 N6 -1.04(17) . . . . ?
C6 N8 C5 C4 178.88(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
