# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_2022_2b_autored
_database_code_depnum_ccdc_archive 'CCDC 2239586'
loop_
_audit_author_name
_audit_author_address
'Zhenghang Luo'
;Southwest University of Science and Technology 
China
;
_audit_update_record             
;
2023-12-02 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-12-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
4-amino-3,8-dinitro-pyrazolo[5,1-c][1,2,4]triazine
_chemical_formula_moiety         'C5 H3 N7 O4, H4 O2'
_chemical_formula_sum            'C5 H7 N7 O6'
_chemical_formula_weight         261.18
_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.2737(13)
_cell_length_b                   6.2094(8)
_cell_length_c                   9.4529(12)
_cell_angle_alpha                90
_cell_angle_beta                 114.864(16)
_cell_angle_gamma                90
_cell_volume                     493.88(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1710
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7260
_cell_measurement_theta_min      4.0690
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6317
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.146
_diffrn_reflns_theta_min         4.043
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '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                560
_reflns_number_total             1318
_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.

the exposure time is set as 150 s with a scan width of 1 degree
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0837
_refine_ls_restrained_S_all      0.947
_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)+(0.0841P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H6C(0.5) H6D(0.5)
2.a Riding coordinates:
 O5(H5A,H5B), O6(H6C,H6D)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.c X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.5348(6) 0.2500 0.0949(5) 0.0710(14) Uani 1 2 d S T P A 1
N6 N 0.8358(6) 0.2500 0.3145(5) 0.0436(12) Uani 1 2 d S T P A .
H6A H 0.9380 0.2500 0.3583 0.052 Uiso 1 2 calc RS T P . .
H6B H 0.7863 0.2500 0.2145 0.052 Uiso 1 2 calc RS T P . .
O5 O 0.1810(5) 0.2500 0.4241(5) 0.0688(14) Uani 1 2 d S T P . .
H5A H 0.2067 0.3528 0.4896 0.103 Uiso 0.5 1 d R . . . .
H5B H 0.2591 0.2193 0.4030 0.103 Uiso 0.5 1 d R . . . .
O6 O 0.3864(5) 0.2500 0.7490(5) 0.0645(13) Uani 1 2 d S T P . .
H6C H 0.4621 0.2882 0.7263 0.097 Uiso 0.5 1 d R . . . .
H6D H 0.4097 0.1312 0.7982 0.097 Uiso 0.5 1 d R . . . .
N4 N 0.8409(5) 0.2500 0.5593(5) 0.0346(11) Uani 1 2 d S T P A .
N2 N 0.5244(6) 0.2500 0.4557(6) 0.0558(15) Uani 1 2 d S T P . .
N5 N 1.0037(6) 0.2500 0.6336(6) 0.0512(13) Uani 1 2 d S T P A .
N3 N 0.6068(6) 0.2500 0.6072(6) 0.0485(13) Uani 1 2 d S T P A .
O4 O 1.0038(6) 0.2500 1.0688(5) 0.0726(14) Uani 1 2 d S T P B .
O3 O 0.7482(7) 0.2500 0.9559(5) 0.0856(17) Uani 1 2 d S T P B 2
O1 O 0.3412(6) 0.2500 0.1626(6) 0.0860(17) Uani 1 2 d S T P A .
N1 N 0.4798(6) 0.2500 0.1935(5) 0.0508(14) Uani 1 2 d S T P . .
C2 C 0.7579(7) 0.2500 0.3976(6) 0.0436(14) Uani 1 2 d S T P . .
N7 N 0.8764(8) 0.2500 0.9507(6) 0.0606(15) Uani 1 2 d S T P . .
C4 C 0.8875(8) 0.2500 0.8017(6) 0.0466(16) Uani 1 2 d S T P A .
C1 C 0.5944(7) 0.2500 0.3582(6) 0.0435(15) Uani 1 2 d S T P A .
C5 C 1.0342(8) 0.2500 0.7859(6) 0.0470(16) Uani 1 2 d S T P . .
H5 H 1.1349 0.2500 0.8680 0.056 Uiso 1 2 calc RS T P B .
C3 C 0.7628(8) 0.2500 0.6551(7) 0.0478(15) Uani 1 2 d S T P . .


_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
O2 N1 1.236(6) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C2 1.271(7) . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8495 . ?
O6 H6C 0.8498 . ?
O6 H6D 0.8499 . ?
N4 N5 1.371(6) . ?
N4 C2 1.393(7) . ?
N4 C3 1.377(7) . ?
N2 N3 1.309(7) . ?
N2 C1 1.332(7) . ?
N5 C5 1.346(7) . ?
N3 C3 1.321(7) . ?
O4 N7 1.238(6) . ?
O3 N7 1.210(6) . ?
O1 N1 1.192(6) . ?
N1 C1 1.470(7) . ?
C2 C1 1.401(8) . ?
N7 C4 1.454(7) . ?
C4 C5 1.430(8) . ?
C4 C3 1.382(8) . ?
C5 H5 0.9300 . ?

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
H6A N6 H6B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
H5A O5 H5B 109.5 . . ?
H6C O6 H6D 109.5 . . ?
N5 N4 C2 122.9(4) . . ?
N5 N4 C3 115.7(5) . . ?
C3 N4 C2 121.4(5) . . ?
N3 N2 C1 121.8(5) . . ?
C5 N5 N4 103.8(4) . . ?
N2 N3 C3 115.2(5) . . ?
O2 N1 C1 117.0(5) . . ?
O1 N1 O2 124.0(5) . . ?
O1 N1 C1 119.0(5) . . ?
N6 C2 N4 118.9(5) . . ?
N6 C2 C1 131.9(5) . . ?
N4 C2 C1 109.2(5) . . ?
O4 N7 C4 116.4(6) . . ?
O3 N7 O4 123.0(5) . . ?
O3 N7 C4 120.7(5) . . ?
C5 C4 N7 124.0(5) . . ?
C3 C4 N7 127.0(6) . . ?
C3 C4 C5 109.1(5) . . ?
N2 C1 N1 112.8(5) . . ?
N2 C1 C2 127.1(6) . . ?
C2 C1 N1 120.1(5) . . ?
N5 C5 C4 109.3(5) . . ?
N5 C5 H5 125.3 . . ?
C4 C5 H5 125.3 . . ?
N4 C3 C4 102.1(5) . . ?
N3 C3 N4 125.3(5) . . ?
N3 C3 C4 132.6(6) . . ?

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
O2 N1 C1 N2 180.000(1) . . . . ?
O2 N1 C1 C2 0.000(1) . . . . ?
N6 C2 C1 N2 180.000(2) . . . . ?
N6 C2 C1 N1 0.000(2) . . . . ?
N4 N5 C5 C4 0.000(2) . . . . ?
N4 C2 C1 N2 0.000(2) . . . . ?
N4 C2 C1 N1 180.000(1) . . . . ?
N2 N3 C3 N4 0.000(3) . . . . ?
N2 N3 C3 C4 180.000(2) . . . . ?
N5 N4 C2 N6 0.000(2) . . . . ?
N5 N4 C2 C1 180.000(1) . . . . ?
N5 N4 C3 N3 180.000(2) . . . . ?
N5 N4 C3 C4 0.000(2) . . . . ?
N3 N2 C1 N1 180.000(2) . . . . ?
N3 N2 C1 C2 0.000(2) . . . . ?
O4 N7 C4 C5 0.000(4) . . . . ?
O4 N7 C4 C3 180.000(3) . . . . ?
O3 N7 C4 C5 180.000(3) . . . . ?
O3 N7 C4 C3 0.000(4) . . . . ?
O1 N1 C1 N2 0.000(1) . . . . ?
O1 N1 C1 C2 180.000(1) . . . . ?
C2 N4 N5 C5 180.000(2) . . . . ?
C2 N4 C3 N3 0.000(3) . . . . ?
C2 N4 C3 C4 180.000(2) . . . . ?
N7 C4 C5 N5 180.000(3) . . . . ?
N7 C4 C3 N4 180.000(3) . . . . ?
N7 C4 C3 N3 0.000(4) . . . . ?
C1 N2 N3 C3 0.000(2) . . . . ?
C5 C4 C3 N4 0.000(2) . . . . ?
C5 C4 C3 N3 180.000(3) . . . . ?
C3 N4 N5 C5 0.000(2) . . . . ?
C3 N4 C2 N6 180.000(1) . . . . ?
C3 N4 C2 C1 0.000(2) . . . . ?
C3 C4 C5 N5 0.000(2) . . . . ?

_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_20221229_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2239587'
loop_
_audit_author_name
_audit_author_address
'Zhenghang Luo'
;Southwest University of Science and Technology 
China
;
_audit_update_record             
;
2023-12-02 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
4-amino-3,8-dinitro-pyrazolo[5,1-c][1,2,4]triazine
_chemical_formula_moiety         'C5 H3 N7 O4, C H4 O'
_chemical_formula_sum            'C6 H7 N7 O5'
_chemical_formula_weight         257.19
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.5784(8)
_cell_length_b                   26.550(2)
_cell_length_c                   4.5184(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1029.09(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      57.017
_cell_measurement_theta_min      6.248
_shelx_estimated_absorpt_T_max   0.867
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1792 before and 0.0511 after correction. The Ratio of minimum to maximum transmission is 0.7907. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8708
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.111
_diffrn_reflns_theta_min         5.341
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1593
_reflns_number_total             1830
_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.

the exposure time is set as 150 s with a scan width of 1 degree
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(6)
_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     165
_refine_ls_number_reflns         1830
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.110
_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)+(0.0456P)²+0.2127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0932
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.0(6)
 0.0(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 N4(H4A,H4B), O5(H5)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.0795(3) -0.19540(7) -0.6170(6) 0.0457(6) Uani 1 1 d . . . . .
O2 O -0.0716(2) -0.16705(7) -0.2675(6) 0.0462(6) Uani 1 1 d . . . . .
O4 O 0.2202(3) -0.44375(8) -0.8684(7) 0.0536(7) Uani 1 1 d . . . . .
O3 O 0.0847(3) -0.47518(8) -0.5083(6) 0.0545(7) Uani 1 1 d . . . . .
N3 N -0.0557(2) -0.33320(7) -0.2868(6) 0.0267(5) Uani 1 1 d . . . . .
N7 N 0.1263(2) -0.30466(8) -0.6528(6) 0.0316(6) Uani 1 1 d . . . . .
N2 N -0.1603(2) -0.31651(8) -0.0792(6) 0.0303(6) Uani 1 1 d . . . . .
N4 N -0.0987(3) -0.41655(8) -0.1737(6) 0.0350(6) Uani 1 1 d . . . . .
H4A H -0.1651 -0.4067 -0.0434 0.042 Uiso 1 1 d R . . . .
H4B H -0.0813 -0.4482 -0.1985 0.042 Uiso 1 1 d R . . . .
N1 N -0.0108(3) -0.20143(8) -0.4063(7) 0.0334(6) Uani 1 1 d . . . . .
N6 N 0.1570(2) -0.35226(9) -0.7069(6) 0.0345(6) Uani 1 1 d . . . . .
N5 N 0.1355(3) -0.43909(8) -0.6526(7) 0.0379(7) Uani 1 1 d . . . . .
C5 C -0.0247(3) -0.38346(9) -0.3328(7) 0.0285(7) Uani 1 1 d . . . . .
C3 C 0.0186(3) -0.29549(9) -0.4403(7) 0.0268(6) Uani 1 1 d . . . . .
C1 C -0.1526(3) -0.26648(10) -0.1044(7) 0.0300(6) Uani 1 1 d . . . . .
H1 H -0.2110 -0.2441 0.0088 0.036 Uiso 1 1 calc R . . . .
C4 C 0.0877(3) -0.38926(10) -0.5579(8) 0.0317(7) Uani 1 1 d . . . . .
C2 C -0.0461(3) -0.25184(9) -0.3214(7) 0.0268(6) Uani 1 1 d . . . . .
O5 O -0.8127(2) -0.09631(7) 1.2623(7) 0.0500(6) Uani 1 1 d . . . . .
H5 H -0.8600 -0.1231 1.2686 0.075 Uiso 1 1 d R . . . .
C6 C -0.9090(4) -0.05721(13) 1.3668(14) 0.0672(13) Uani 1 1 d . . . . .
H6A H -0.8472 -0.0276 1.4013 0.101 Uiso 1 1 calc GR . . . .
H6B H -0.9577 -0.0674 1.5484 0.101 Uiso 1 1 calc GR . . . .
H6C H -0.9877 -0.0499 1.2220 0.101 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.238(4) . ?
O2 N1 1.224(3) . ?
O4 N5 1.222(4) . ?
O3 N5 1.238(3) . ?
N3 N2 1.372(3) . ?
N3 C5 1.376(3) . ?
N3 C3 1.374(3) . ?
N7 N6 1.314(3) . ?
N7 C3 1.355(4) . ?
N2 C1 1.335(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8605 . ?
N4 C5 1.301(4) . ?
N1 C2 1.425(3) . ?
N6 C4 1.331(4) . ?
N5 C4 1.450(3) . ?
C5 C4 1.410(4) . ?
C3 C2 1.393(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.395(4) . ?
O5 H5 0.8196 . ?
O5 C6 1.408(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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 N3 C5 122.9(2) . . ?
N2 N3 C3 114.4(2) . . ?
C3 N3 C5 122.7(2) . . ?
N6 N7 C3 116.2(2) . . ?
C1 N2 N3 103.3(2) . . ?
H4A N4 H4B 120.1 . . ?
C5 N4 H4A 119.7 . . ?
C5 N4 H4B 120.2 . . ?
O1 N1 C2 117.5(2) . . ?
O2 N1 O1 124.3(2) . . ?
O2 N1 C2 118.2(3) . . ?
N7 N6 C4 121.8(2) . . ?
O4 N5 O3 123.4(2) . . ?
O4 N5 C4 119.7(3) . . ?
O3 N5 C4 116.8(3) . . ?
N3 C5 C4 110.3(2) . . ?
N4 C5 N3 118.5(3) . . ?
N4 C5 C4 131.2(2) . . ?
N3 C3 C2 103.1(2) . . ?
N7 C3 N3 122.9(2) . . ?
N7 C3 C2 134.0(2) . . ?
N2 C1 H1 124.1 . . ?
N2 C1 C2 111.7(2) . . ?
C2 C1 H1 124.1 . . ?
N6 C4 N5 113.5(3) . . ?
N6 C4 C5 126.1(2) . . ?
C5 C4 N5 120.4(3) . . ?
C3 C2 N1 126.4(3) . . ?
C3 C2 C1 107.5(2) . . ?
C1 C2 N1 126.2(2) . . ?
C6 O5 H5 109.8 . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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 N1 C2 C3 4.3(4) . . . . ?
O1 N1 C2 C1 -175.4(3) . . . . ?
O2 N1 C2 C3 -175.8(3) . . . . ?
O2 N1 C2 C1 4.4(4) . . . . ?
O4 N5 C4 N6 -6.4(4) . . . . ?
O4 N5 C4 C5 172.2(3) . . . . ?
O3 N5 C4 N6 174.6(3) . . . . ?
O3 N5 C4 C5 -6.8(4) . . . . ?
N3 N2 C1 C2 0.0(3) . . . . ?
N3 C5 C4 N6 0.5(4) . . . . ?
N3 C5 C4 N5 -177.9(2) . . . . ?
N3 C3 C2 N1 -179.1(2) . . . . ?
N3 C3 C2 C1 0.6(3) . . . . ?
N7 N6 C4 N5 179.2(2) . . . . ?
N7 N6 C4 C5 0.7(4) . . . . ?
N7 C3 C2 N1 0.4(5) . . . . ?
N7 C3 C2 C1 -179.8(3) . . . . ?
N2 N3 C5 N4 0.5(4) . . . . ?
N2 N3 C5 C4 -179.7(2) . . . . ?
N2 N3 C3 N7 179.7(2) . . . . ?
N2 N3 C3 C2 -0.7(3) . . . . ?
N2 C1 C2 N1 179.4(3) . . . . ?
N2 C1 C2 C3 -0.4(3) . . . . ?
N4 C5 C4 N6 -179.7(3) . . . . ?
N4 C5 C4 N5 1.9(5) . . . . ?
N6 N7 C3 N3 0.0(4) . . . . ?
N6 N7 C3 C2 -179.4(3) . . . . ?
C5 N3 N2 C1 179.0(2) . . . . ?
C5 N3 C3 N7 1.2(4) . . . . ?
C5 N3 C3 C2 -179.2(2) . . . . ?
C3 N3 N2 C1 0.5(3) . . . . ?
C3 N3 C5 N4 178.8(2) . . . . ?
C3 N3 C5 C4 -1.4(4) . . . . ?
C3 N7 N6 C4 -0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(6)
2 0.0(6)

