# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_cu_20230516_ys_nlg_a_28_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2323657'
loop_
_audit_author_name
_audit_author_address
'Frank '
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-01-05 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 N10 O2'
_chemical_formula_sum            'C6 H2 N10 O2'
_chemical_formula_weight         246.18
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.8098(2)
_cell_length_b                   6.1710(2)
_cell_length_c                   20.8098(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.748(2)
_cell_angle_gamma                90
_cell_volume                     874.09(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2224
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.510
_cell_measurement_theta_min      6.503
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    1.317
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1124 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.8521.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7841
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.044
_diffrn_reflns_theta_min         4.251
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1269
_reflns_number_total             1580
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1580
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.084
_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)+(0.0458P)²+0.1993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0945
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Restrained distances
 N11_$1-O2
 2.89 with sigma of 0.001
3.a X=CH2 refined with riding coordinates:
 N12(H12A,H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.6454(2) 1.3029(2) 0.43290(6) 0.0325(3) Uani 1 1 d . . . . .
O2 O 0.66720(17) 0.4271(2) 0.26746(6) 0.0324(3) Uani 1 1 d D . . . .
N3 N 0.6856(2) 1.1257(2) 0.39483(8) 0.0303(4) Uani 1 1 d . . . . .
N4 N 0.4613(2) 1.2863(2) 0.46085(8) 0.0306(4) Uani 1 1 d . . . . .
N5 N 0.2139(2) 1.0180(2) 0.45434(7) 0.0260(4) Uani 1 1 d . . . . .
N6 N 0.6120(2) 0.7068(2) 0.33039(7) 0.0248(3) Uani 1 1 d . . . . .
N7 N 0.5521(2) 0.5233(2) 0.30217(7) 0.0246(3) Uani 1 1 d . . . . .
N8 N 0.3744(2) 0.4300(2) 0.30809(7) 0.0249(3) Uani 1 1 d . . . . .
N9 N 0.0681(2) 0.4289(2) 0.35350(8) 0.0276(4) Uani 1 1 d . . . . .
N10 N 0.0428(2) 0.2597(2) 0.31904(8) 0.0292(4) Uani 1 1 d . . . . .
N11 N -0.0045(2) 0.1114(3) 0.29283(9) 0.0404(5) Uani 1 1 d . . . . .
N12 N 0.0010(2) 0.7371(2) 0.44489(8) 0.0305(4) Uani 1 1 d . . . . .
H12A H -0.073092 0.801653 0.473040 0.037 Uiso 1 1 calc R U . . .
H12B H -0.035299 0.611705 0.428260 0.037 Uiso 1 1 calc R U . . .
C1 C 0.3912(3) 1.1007(3) 0.43905(9) 0.0251(4) Uani 1 1 d . . . . .
C2 C 0.5301(3) 1.0031(3) 0.39843(8) 0.0237(4) Uani 1 1 d . . . . .
C3 C 0.4798(3) 0.7990(3) 0.36808(8) 0.0221(4) Uani 1 1 d . . . . .
C4 C 0.2942(3) 0.7184(3) 0.38134(8) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.1664(3) 0.8283(3) 0.42761(8) 0.0243(4) Uani 1 1 d . . . . .
C6 C 0.2492(2) 0.5261(3) 0.34701(8) 0.0227(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 1.3821(19) . ?
O1 N4 1.402(2) . ?
O2 N7 1.2341(18) . ?
N3 C2 1.305(2) . ?
N4 C1 1.316(2) . ?
N5 C1 1.357(2) . ?
N5 C5 1.332(2) . ?
N6 N7 1.334(2) . ?
N6 C3 1.339(2) . ?
N7 N8 1.350(2) . ?
N8 C6 1.333(2) . ?
N9 N10 1.275(2) . ?
N9 C6 1.382(2) . ?
N10 N11 1.108(2) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N12 C5 1.319(2) . ?
C1 C2 1.421(3) . ?
C2 C3 1.446(2) . ?
C3 C4 1.393(2) . ?
C4 C5 1.482(2) . ?
C4 C6 1.414(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 O1 N4 112.03(13) . . ?
C2 N3 O1 104.50(14) . . ?
C1 N4 O1 103.90(14) . . ?
C5 N5 C1 116.03(15) . . ?
N7 N6 C3 114.61(14) . . ?
O2 N7 N6 118.34(14) . . ?
O2 N7 N8 115.82(14) . . ?
N6 N7 N8 125.83(14) . . ?
C6 N8 N7 117.21(15) . . ?
N10 N9 C6 113.98(14) . . ?
N11 N10 N9 170.09(17) . . ?
H12A N12 H12B 120.0 . . ?
C5 N12 H12A 120.0 . . ?
C5 N12 H12B 120.0 . . ?
N4 C1 N5 124.21(17) . . ?
N4 C1 C2 109.41(16) . . ?
N5 C1 C2 126.37(16) . . ?
N3 C2 C1 110.15(16) . . ?
N3 C2 C3 131.43(17) . . ?
C1 C2 C3 118.40(16) . . ?
N6 C3 C2 118.14(15) . . ?
N6 C3 C4 126.47(16) . . ?
C4 C3 C2 115.40(15) . . ?
C3 C4 C5 121.27(15) . . ?
C3 C4 C6 112.55(15) . . ?
C6 C4 C5 126.17(16) . . ?
N5 C5 C4 122.28(16) . . ?
N12 C5 N5 117.37(16) . . ?
N12 C5 C4 120.33(16) . . ?
N8 C6 N9 117.07(15) . . ?
N8 C6 C4 123.24(16) . . ?
N9 C6 C4 119.69(15) . . ?

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 C2 C1 -0.40(19) . . . . ?
O1 N3 C2 C3 178.06(17) . . . . ?
O1 N4 C1 N5 179.64(16) . . . . ?
O1 N4 C1 C2 0.27(18) . . . . ?
O2 N7 N8 C6 177.77(14) . . . . ?
N3 O1 N4 C1 -0.54(18) . . . . ?
N3 C2 C3 N6 2.3(3) . . . . ?
N3 C2 C3 C4 -177.40(19) . . . . ?
N4 O1 N3 C2 0.59(18) . . . . ?
N4 C1 C2 N3 0.1(2) . . . . ?
N4 C1 C2 C3 -178.60(15) . . . . ?
N5 C1 C2 N3 -179.27(17) . . . . ?
N5 C1 C2 C3 2.0(3) . . . . ?
N6 N7 N8 C6 -2.0(2) . . . . ?
N6 C3 C4 C5 175.66(15) . . . . ?
N6 C3 C4 C6 -3.5(2) . . . . ?
N7 N6 C3 C2 -177.54(15) . . . . ?
N7 N6 C3 C4 2.1(2) . . . . ?
N7 N8 C6 N9 -179.32(14) . . . . ?
N7 N8 C6 C4 0.3(2) . . . . ?
N10 N9 C6 N8 -2.0(2) . . . . ?
N10 N9 C6 C4 178.38(16) . . . . ?
C1 N5 C5 N12 175.62(16) . . . . ?
C1 N5 C5 C4 -3.0(2) . . . . ?
C1 C2 C3 N6 -179.33(15) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C2 C3 C4 C5 -4.7(2) . . . . ?
C2 C3 C4 C6 176.15(14) . . . . ?
C3 N6 N7 O2 -178.91(15) . . . . ?
C3 N6 N7 N8 0.9(2) . . . . ?
C3 C4 C5 N5 6.1(3) . . . . ?
C3 C4 C5 N12 -172.49(16) . . . . ?
C3 C4 C6 N8 2.2(2) . . . . ?
C3 C4 C6 N9 -178.22(15) . . . . ?
C5 N5 C1 N4 179.77(17) . . . . ?
C5 N5 C1 C2 -1.0(3) . . . . ?
C5 C4 C6 N8 -176.97(16) . . . . ?
C5 C4 C6 N9 2.6(3) . . . . ?
C6 C4 C5 N5 -174.85(16) . . . . ?
C6 C4 C5 N12 6.6(3) . . . . ?

_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_cu_20230428_ys_nlg_1321_f_0m
_database_code_depnum_ccdc_archive 'CCDC 2357111'
loop_
_audit_author_name
_audit_author_address
'Frank '
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-05-22 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H N9 O3'
_chemical_formula_sum            'C6 H N9 O3'
_chemical_formula_weight         247.16
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   18.4623(6)
_cell_length_b                   9.1563(4)
_cell_length_c                   5.3802(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     909.50(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2818
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.560
_cell_measurement_theta_min      4.790
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1226 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.7462.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7335
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.198
_diffrn_reflns_theta_min         4.790
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                1384
_reflns_number_total             1559
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1559
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²+0.1747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1161
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 N9_$1-O1
 2.9 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.40867(19) 0.3194(3) 1.0284(7) 0.0593(10) Uani 1 1 d D . . . .
O2 O 0.23945(17) 0.5093(3) 0.1651(7) 0.0486(9) Uani 1 1 d . . . . .
O3 O 0.23859(17) 0.7041(3) -0.0642(6) 0.0447(8) Uani 1 1 d . . . . .
N1 N 0.25965(18) 0.6356(3) 0.1210(7) 0.0370(8) Uani 1 1 d . . . . .
N2 N 0.30739(16) 0.7093(3) 0.2688(7) 0.0330(7) Uani 1 1 d . . . . .
N3 N 0.32858(18) 0.4984(4) 0.5356(7) 0.0363(8) Uani 1 1 d . . . . .
H3 H 0.298547 0.440546 0.455388 0.044 Uiso 1 1 calc R U . . .
N4 N 0.3631(2) 0.3122(4) 0.8236(8) 0.0518(11) Uani 1 1 d . . . . .
N5 N 0.4394(2) 0.4536(4) 1.0666(9) 0.0499(10) Uani 1 1 d . . . . .
N6 N 0.46562(19) 0.7892(4) 0.9097(8) 0.0431(9) Uani 1 1 d . . . . .
N7 N 0.45855(17) 0.9066(4) 0.7625(8) 0.0419(8) Uani 1 1 d . . . . .
N8 N 0.39640(18) 0.9649(4) 0.3951(8) 0.0374(8) Uani 1 1 d . . . . .
N9 N 0.3817(2) 1.0344(3) 0.2420(9) 0.0526(11) Uani 1 1 d . . . . .
C1 C 0.4128(2) 0.8688(4) 0.5774(8) 0.0346(9) Uani 1 1 d . . . . .
C2 C 0.3876(2) 0.7256(4) 0.5991(8) 0.0325(8) Uani 1 1 d . . . . .
C3 C 0.3377(2) 0.6389(4) 0.4587(8) 0.0321(9) Uani 1 1 d . . . . .
C4 C 0.4243(2) 0.6820(4) 0.8112(8) 0.0346(9) Uani 1 1 d . . . . .
C5 C 0.4136(2) 0.5321(4) 0.8840(8) 0.0370(10) Uani 1 1 d . . . . .
C6 C 0.3661(2) 0.4465(4) 0.7382(9) 0.0379(9) 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 N4 1.388(5) . ?
O1 N5 1.368(5) . ?
O2 N1 1.238(4) . ?
O3 N1 1.240(5) . ?
N1 N2 1.366(5) . ?
N2 C3 1.331(5) . ?
N3 H3 0.8800 . ?
N3 C3 1.361(5) . ?
N3 C6 1.377(5) . ?
N4 C6 1.314(5) . ?
N5 C5 1.307(6) . ?
N6 N7 1.341(5) . ?
N6 C4 1.352(6) . ?
N7 C1 1.351(6) . ?
N8 N9 1.075(5) . ?
N8 C1 1.352(6) . ?
C1 C2 1.397(6) . ?
C2 C3 1.432(5) . ?
C2 C4 1.385(6) . ?
C4 C5 1.441(5) . ?
C5 C6 1.413(6) . ?

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
N5 O1 N4 114.4(3) . . ?
O2 N1 O3 122.2(4) . . ?
O2 N1 N2 123.0(4) . . ?
O3 N1 N2 114.9(3) . . ?
C3 N2 N1 118.6(3) . . ?
C3 N3 H3 119.8 . . ?
C3 N3 C6 120.3(3) . . ?
C6 N3 H3 119.8 . . ?
C6 N4 O1 102.0(3) . . ?
C5 N5 O1 103.3(4) . . ?
N7 N6 C4 107.2(4) . . ?
N6 N7 C1 106.9(3) . . ?
N9 N8 C1 175.6(4) . . ?
N7 C1 N8 120.6(4) . . ?
N7 C1 C2 112.7(4) . . ?
N8 C1 C2 126.7(4) . . ?
C1 C2 C3 133.7(4) . . ?
C4 C2 C1 100.2(4) . . ?
C4 C2 C3 126.1(4) . . ?
N2 C3 N3 129.7(4) . . ?
N2 C3 C2 114.0(3) . . ?
N3 C3 C2 116.3(3) . . ?
N6 C4 C2 112.9(4) . . ?
N6 C4 C5 131.5(4) . . ?
C2 C4 C5 115.6(4) . . ?
N5 C5 C4 132.7(4) . . ?
N5 C5 C6 109.8(4) . . ?
C6 C5 C4 117.5(4) . . ?
N3 C6 C5 124.1(3) . . ?
N4 C6 N3 125.4(4) . . ?
N4 C6 C5 110.6(4) . . ?

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 N4 C6 N3 -178.6(4) . . . . ?
O1 N4 C6 C5 1.2(5) . . . . ?
O1 N5 C5 C4 -179.1(4) . . . . ?
O1 N5 C5 C6 1.2(5) . . . . ?
O2 N1 N2 C3 5.0(5) . . . . ?
O3 N1 N2 C3 -174.0(3) . . . . ?
N1 N2 C3 N3 -0.2(6) . . . . ?
N1 N2 C3 C2 179.1(3) . . . . ?
N4 O1 N5 C5 -0.4(5) . . . . ?
N5 O1 N4 C6 -0.5(5) . . . . ?
N5 C5 C6 N3 178.2(4) . . . . ?
N5 C5 C6 N4 -1.6(5) . . . . ?
N6 N7 C1 N8 -178.4(3) . . . . ?
N6 N7 C1 C2 0.7(5) . . . . ?
N6 C4 C5 N5 0.7(8) . . . . ?
N6 C4 C5 C6 -179.6(4) . . . . ?
N7 N6 C4 C2 -1.1(5) . . . . ?
N7 N6 C4 C5 177.0(4) . . . . ?
N7 C1 C2 C3 177.5(4) . . . . ?
N7 C1 C2 C4 -1.3(4) . . . . ?
N8 C1 C2 C3 -3.4(7) . . . . ?
N8 C1 C2 C4 177.8(4) . . . . ?
C1 C2 C3 N2 -1.4(6) . . . . ?
C1 C2 C3 N3 178.0(4) . . . . ?
C1 C2 C4 N6 1.5(4) . . . . ?
C1 C2 C4 C5 -177.0(3) . . . . ?
C2 C4 C5 N5 178.9(5) . . . . ?
C2 C4 C5 C6 -1.5(5) . . . . ?
C3 N3 C6 N4 -177.9(4) . . . . ?
C3 N3 C6 C5 2.3(6) . . . . ?
C3 C2 C4 N6 -177.5(4) . . . . ?
C3 C2 C4 C5 4.1(6) . . . . ?
C4 N6 N7 C1 0.2(4) . . . . ?
C4 C2 C3 N2 177.1(3) . . . . ?
C4 C2 C3 N3 -3.4(6) . . . . ?
C4 C5 C6 N3 -1.6(6) . . . . ?
C4 C5 C6 N4 178.6(4) . . . . ?
C6 N3 C3 N2 179.4(4) . . . . ?
C6 N3 C3 C2 0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
