# 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_20240110_NLG_TMJ_110_0m
_database_code_depnum_ccdc_archive 'CCDC 2336156'
loop_
_audit_author_name
_audit_author_address
A
;Nanjing university of science and technology
China
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V118 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C4 H4 N8 O2'
_chemical_formula_moiety         ?
_chemical_formula_weight         196.15
_chemical_melting_point          ?
_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                   3.5520(3)
_cell_length_b                   12.0748(9)
_cell_length_c                   16.4467(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.551(5)
_cell_angle_gamma                90
_cell_volume                     705.36(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5322
_cell_measurement_theta_min      4.543
_cell_measurement_theta_max      66.6615
_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            9392
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_theta_min         2.687
_diffrn_reflns_theta_max         66.540
_diffrn_reflns_theta_full        66.540
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1240
_reflns_number_gt                1052
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       
'Bruker BIS 8.5.0.27 Release/2023-03-20 && ToolAlignment 2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1693P)²+1.7984P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1240
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0924
_refine_ls_wR_factor_ref         0.2814
_refine_ls_wR_factor_gt          0.2405
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

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'

_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_
_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
C1 C 0.872(2) 0.2072(5) -0.0030(4) 0.0303(16) Uani 1 1 d . . . . .
H1 H 0.766436 0.135772 -0.011224 0.036 Uiso 1 1 calc R U . . .
C2 C 0.891(2) 0.2136(5) 0.1492(4) 0.0263(16) Uani 1 1 d . . . . .
C3 C 0.860(2) 0.1105(5) 0.2615(4) 0.0288(15) Uani 1 1 d . . . . .
C4 C 0.974(2) 0.1062(5) 0.1799(4) 0.0273(15) Uani 1 1 d . . . . .
N1 N 0.9460(17) 0.2548(4) 0.0696(3) 0.0276(14) Uani 1 1 d . . . . .
N2 N 0.971(2) 0.2766(5) -0.0605(3) 0.0325(14) Uani 1 1 d . . . . .
N3 N 1.105(2) 0.3686(5) -0.0215(3) 0.0348(16) Uani 1 1 d . . . . .
N4 N 1.0911(19) 0.3572(4) 0.0564(3) 0.0328(15) Uani 1 1 d . . . . .
N5 N 0.740(2) 0.2781(4) 0.2038(3) 0.0288(14) Uani 1 1 d . . . . .
N6 N 0.731(2) 0.2135(4) 0.2727(3) 0.0287(14) Uani 1 1 d . . . . .
H6 H 0.648582 0.237687 0.319788 0.034 Uiso 1 1 calc R U . . .
N7 N 0.875(2) 0.0322(4) 0.3195(3) 0.0362(16) Uani 1 1 d . . . . .
H7A H 0.796483 0.047093 0.368930 0.043 Uiso 1 1 calc R U . . .
H7B H 0.962922 -0.034097 0.308090 0.043 Uiso 1 1 calc R U . . .
N8 N 1.1537(18) 0.0178(4) 0.1425(3) 0.0271(14) Uani 1 1 d . . . . .
O1 O 1.1833(18) -0.0703(4) 0.1802(3) 0.0380(14) Uani 1 1 d . . . . .
O2 O 1.2785(17) 0.0310(4) 0.0731(3) 0.0326(13) Uani 1 1 d . . . . .


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
C1 N2 1.313(8) . ?
C1 N1 1.349(8) . ?
C1 H1 0.9500 . ?
C2 N5 1.307(8) . ?
C2 N1 1.416(8) . ?
C2 C4 1.422(8) . ?
C3 N6 1.338(8) . ?
C3 N7 1.344(8) . ?
C3 C4 1.407(8) . ?
C4 N8 1.390(8) . ?
N1 N4 1.358(8) . ?
N2 N3 1.366(8) . ?
N3 N4 1.290(8) . ?
N5 N6 1.377(7) . ?
N6 H6 0.8800 . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N8 O1 1.235(7) . ?
N8 O2 1.238(7) . ?

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 C1 N1 108.3(6) . . ?
N2 C1 H1 125.9 . . ?
N1 C1 H1 125.9 . . ?
N5 C2 N1 119.1(5) . . ?
N5 C2 C4 112.6(5) . . ?
N1 C2 C4 128.3(6) . . ?
N6 C3 N7 124.6(6) . . ?
N6 C3 C4 105.6(5) . . ?
N7 C3 C4 129.9(6) . . ?
N8 C4 C3 126.0(5) . . ?
N8 C4 C2 129.6(6) . . ?
C3 C4 C2 104.1(5) . . ?
C1 N1 N4 108.6(5) . . ?
C1 N1 C2 129.9(5) . . ?
N4 N1 C2 121.5(5) . . ?
C1 N2 N3 106.0(5) . . ?
N4 N3 N2 111.3(5) . . ?
N3 N4 N1 105.9(5) . . ?
C2 N5 N6 104.0(5) . . ?
C3 N6 N5 113.7(5) . . ?
C3 N6 H6 123.1 . . ?
N5 N6 H6 123.1 . . ?
C3 N7 H7A 120.0 . . ?
C3 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
O1 N8 O2 123.0(5) . . ?
O1 N8 C4 118.4(5) . . ?
O2 N8 C4 118.6(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
N6 C3 C4 N8 174.7(7) . . . . ?
N7 C3 C4 N8 -4.3(13) . . . . ?
N6 C3 C4 C2 -0.7(8) . . . . ?
N7 C3 C4 C2 -179.6(8) . . . . ?
N5 C2 C4 N8 -175.8(7) . . . . ?
N1 C2 C4 N8 5.5(13) . . . . ?
N5 C2 C4 C3 -0.6(9) . . . . ?
N1 C2 C4 C3 -179.3(7) . . . . ?
N2 C1 N1 N4 0.7(8) . . . . ?
N2 C1 N1 C2 -179.7(7) . . . . ?
N5 C2 N1 C1 -134.7(8) . . . . ?
C4 C2 N1 C1 43.9(12) . . . . ?
N5 C2 N1 N4 44.8(10) . . . . ?
C4 C2 N1 N4 -136.6(7) . . . . ?
N1 C1 N2 N3 -0.5(8) . . . . ?
C1 N2 N3 N4 0.1(8) . . . . ?
N2 N3 N4 N1 0.4(8) . . . . ?
C1 N1 N4 N3 -0.7(8) . . . . ?
C2 N1 N4 N3 179.7(6) . . . . ?
N1 C2 N5 N6 -179.5(6) . . . . ?
C4 C2 N5 N6 1.6(9) . . . . ?
N7 C3 N6 N5 -179.2(7) . . . . ?
C4 C3 N6 N5 1.8(9) . . . . ?
C2 N5 N6 C3 -2.2(9) . . . . ?
C3 C4 N8 O1 8.5(11) . . . . ?
C2 C4 N8 O1 -177.4(7) . . . . ?
C3 C4 N8 O2 -171.2(7) . . . . ?
C2 C4 N8 O2 3.0(11) . . . . ?

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2336158'
loop_
_audit_author_name
_audit_author_address
B
;Nanjing university of science and technology
China
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_audit_creation_date             2023-04-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 N8 O2, H2 N'
_chemical_formula_sum            'C4 H6 N9 O2'
_chemical_formula_weight         212.18
_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 0.0033 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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   6.7678(18)
_cell_length_b                   9.599(3)
_cell_length_c                   25.029(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.879(8)
_cell_angle_gamma                90
_cell_volume                     1617.4(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3033
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.90
_cell_measurement_theta_min      3.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1036
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17583
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.131
_diffrn_reflns_theta_max         25.131
_diffrn_reflns_theta_min         2.274
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                933
_reflns_number_total             1430
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0734
_refine_ls_restrained_S_all      1.076
_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)+(0.0204P)²+10.9281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1630
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.700(8)
 0.300(8)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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 0.0235(6) 0.5685(4) 0.25474(14) 0.0441(11) Uani 1 1 d . . . . .
O2 O 0.0447(7) 0.7868(4) 0.27791(15) 0.0504(12) Uani 1 1 d . . . . .
N1 N 0.1645(8) 0.3642(5) 0.3306(2) 0.0364(12) Uani 1 1 d . . . . .
H1A H 0.124(8) 0.365(5) 0.299(2) 0.032(17) Uiso 1 1 d . . . . .
H1B H 0.205(8) 0.289(6) 0.347(2) 0.036(16) Uiso 1 1 d . . . . .
N2 N 0.0750(6) 0.6602(4) 0.28801(16) 0.0330(11) Uani 1 1 d . . . . .
N3 N 0.2843(7) 0.4935(4) 0.40660(16) 0.0330(11) Uani 1 1 d . . . . .
H3 H 0.309(13) 0.419(9) 0.436(3) 0.13(3) Uiso 1 1 d . . . . .
N4 N 0.3043(7) 0.6318(4) 0.42349(16) 0.0359(12) Uani 1 1 d . . . . .
N5 N 0.2228(6) 0.8525(4) 0.38845(16) 0.0311(11) Uani 1 1 d . . . . .
N6 N 0.1732(7) 0.9071(5) 0.43519(18) 0.0437(13) Uani 1 1 d . . . . .
N7 N 0.1819(8) 1.0416(5) 0.4299(2) 0.0484(13) Uani 1 1 d . . . . .
N8 N 0.2361(7) 1.0762(4) 0.38031(19) 0.0435(13) Uani 1 1 d . . . . .
C1 C 0.2012(8) 0.4848(5) 0.3561(2) 0.0304(12) Uani 1 1 d . . . . .
C2 C 0.1625(8) 0.6229(5) 0.33809(19) 0.0292(12) Uani 1 1 d . . . . .
C3 C 0.2303(8) 0.7055(5) 0.3825(2) 0.0302(12) Uani 1 1 d . . . . .
C4 C 0.2597(9) 0.9577(6) 0.3557(2) 0.0391(14) Uani 1 1 d . . . . .
H4 H 0.300(10) 0.945(7) 0.319(3) 0.09(2) Uiso 1 1 d . . . . .
N9 N 0.3415(8) 0.3020(5) 0.4872(2) 0.0444(13) Uani 1 1 d . . . . .
H9A H 0.435(7) 0.317(5) 0.512(2) 0.025(14) Uiso 1 1 d . . . . .
H9B H 0.352(10) 0.207(7) 0.475(2) 0.07(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 N2 1.237(5) . ?
O2 N2 1.254(5) . ?
N1 H1A 0.82(5) . ?
N1 H1B 0.87(6) . ?
N1 C1 1.333(6) . ?
N2 C2 1.378(6) . ?
N3 H3 1.03(8) . ?
N3 N4 1.396(6) . ?
N3 C1 1.332(6) . ?
N4 C3 1.304(6) . ?
N5 N6 1.355(6) . ?
N5 C3 1.420(6) . ?
N5 C4 1.340(7) . ?
N6 N7 1.299(6) . ?
N7 N8 1.372(6) . ?
N8 C4 1.311(7) . ?
C1 C2 1.416(7) . ?
C2 C3 1.403(7) . ?
C4 H4 0.99(7) . ?
N9 N9 1.451(10) 2_556 ?
N9 H9A 0.85(5) . ?
N9 H9B 0.97(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
H1A N1 H1B 122(5) . . ?
C1 N1 H1A 119(4) . . ?
C1 N1 H1B 118(3) . . ?
O1 N2 O2 121.7(4) . . ?
O1 N2 C2 119.5(4) . . ?
O2 N2 C2 118.8(4) . . ?
N4 N3 H3 116(4) . . ?
C1 N3 H3 131(5) . . ?
C1 N3 N4 111.4(4) . . ?
C3 N4 N3 105.1(4) . . ?
N6 N5 C3 119.3(4) . . ?
C4 N5 N6 108.3(4) . . ?
C4 N5 C3 132.4(5) . . ?
N7 N6 N5 106.2(4) . . ?
N6 N7 N8 110.6(4) . . ?
C4 N8 N7 105.7(4) . . ?
N1 C1 C2 129.9(5) . . ?
N3 C1 N1 123.3(5) . . ?
N3 C1 C2 106.8(4) . . ?
N2 C2 C1 125.5(4) . . ?
N2 C2 C3 130.5(4) . . ?
C3 C2 C1 104.0(4) . . ?
N4 C3 N5 118.1(4) . . ?
N4 C3 C2 112.6(4) . . ?
C2 C3 N5 129.2(4) . . ?
N5 C4 H4 124(4) . . ?
N8 C4 N5 109.2(5) . . ?
N8 C4 H4 127(4) . . ?
N9 N9 H9A 107(3) 2_556 . ?
N9 N9 H9B 103(4) 2_556 . ?
H9A N9 H9B 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
O1 N2 C2 C1 0.0(8) . . . . ?
O1 N2 C2 C3 -178.9(5) . . . . ?
O2 N2 C2 C1 178.1(5) . . . . ?
O2 N2 C2 C3 -0.9(9) . . . . ?
N1 C1 C2 N2 -0.1(9) . . . . ?
N1 C1 C2 C3 179.1(6) . . . . ?
N2 C2 C3 N4 179.6(5) . . . . ?
N2 C2 C3 N5 1.7(10) . . . . ?
N3 N4 C3 N5 177.5(4) . . . . ?
N3 N4 C3 C2 -0.7(6) . . . . ?
N3 C1 C2 N2 -179.3(5) . . . . ?
N3 C1 C2 C3 -0.1(6) . . . . ?
N4 N3 C1 N1 -179.6(5) . . . . ?
N4 N3 C1 C2 -0.3(6) . . . . ?
N5 N6 N7 N8 0.1(6) . . . . ?
N6 N5 C3 N4 -39.7(7) . . . . ?
N6 N5 C3 C2 138.1(6) . . . . ?
N6 N5 C4 N8 0.3(6) . . . . ?
N6 N7 N8 C4 0.0(6) . . . . ?
N7 N8 C4 N5 -0.2(6) . . . . ?
C1 N3 N4 C3 0.6(6) . . . . ?
C1 C2 C3 N4 0.5(6) . . . . ?
C1 C2 C3 N5 -177.4(5) . . . . ?
C3 N5 N6 N7 178.7(5) . . . . ?
C3 N5 C4 N8 -178.5(5) . . . . ?
C4 N5 N6 N7 -0.3(6) . . . . ?
C4 N5 C3 N4 139.0(6) . . . . ?
C4 N5 C3 C2 -43.1(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.700(8)
2 0.300(8)

