# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_ZTW240417_1_a
_database_code_depnum_ccdc_archive 'CCDC 2379757'
loop_
_audit_author_name
_audit_author_address
'TongWei Zhang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2024-08-26 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
3-((3,4-dinitro-1H-pyrazol-1-yl)methyl)-1,2,4-oxadiazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N6 O5'
_chemical_formula_sum            'C6 H4 N6 O5'
_chemical_formula_weight         240.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.229(5)
_cell_length_b                   5.3345(15)
_cell_length_c                   23.556(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1913.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3940
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            13949
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.675
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             4058
_reflns_number_gt                2382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_max     0.849
_reflns_Friedel_fraction_full    0.901

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+0.8799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 796 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4058
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1572
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5107(6) 0.4460(15) 0.7590(3) 0.055(2) Uani 1 1 d . . . . .
H1 H 0.519818 0.601518 0.775884 0.066 Uiso 1 1 calc R U . . .
C2 C 0.5057(4) 0.1612(13) 0.7018(3) 0.0400(17) Uani 1 1 d . . . . .
C3 C 0.5114(4) 0.0198(12) 0.6476(3) 0.0397(17) Uani 1 1 d . . . . .
H3A H 0.505311 -0.157908 0.655361 0.048 Uiso 1 1 calc R U . . .
H3B H 0.463193 0.069486 0.623110 0.048 Uiso 1 1 calc R U . . .
C4 C 0.6111(5) 0.2381(12) 0.5801(3) 0.0374(19) Uani 1 1 d . . . . .
H4 H 0.572136 0.359908 0.567317 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6966(5) 0.2061(13) 0.5629(3) 0.0369(18) Uani 1 1 d . . . . .
C6 C 0.7264(4) 0.0033(12) 0.5948(3) 0.0349(15) Uani 1 1 d . . . . .
C7 C 0.2522(7) 0.5190(18) 0.2402(4) 0.072(3) Uani 1 1 d . . . . .
H7 H 0.255217 0.359193 0.224530 0.087 Uiso 1 1 calc R U . . .
C8 C 0.2511(5) 0.8223(16) 0.2968(3) 0.0412(17) Uani 1 1 d . . . . .
C9 C 0.2546(4) 0.9645(13) 0.3508(3) 0.0447(17) Uani 1 1 d . . . . .
H9A H 0.245359 1.141235 0.343220 0.054 Uiso 1 1 calc R U . . .
H9B H 0.208052 0.907535 0.375803 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3594(5) 0.7591(10) 0.4197(3) 0.0321(17) Uani 1 1 d . . . . .
H10 H 0.322624 0.636990 0.434771 0.039 Uiso 1 1 calc R U . . .
C11 C 0.4695(4) 1.0087(12) 0.4004(2) 0.0327(15) Uani 1 1 d . . . . .
C12 C 0.4441(4) 0.8050(13) 0.4338(2) 0.0333(16) Uani 1 1 d . . . . .
N1 N 0.4807(6) 0.0596(13) 0.7484(3) 0.073(2) Uani 1 1 d . . . . .
N2 N 0.5278(5) 0.4090(13) 0.7073(3) 0.0622(19) Uani 1 1 d . . . . .
N3 N 0.6652(4) -0.0824(9) 0.62974(19) 0.0374(14) Uani 1 1 d . . . . .
N4 N 0.5948(3) 0.0642(10) 0.61805(18) 0.0324(13) Uani 1 1 d . . . . .
N5 N 0.8137(4) -0.1062(14) 0.6000(3) 0.0509(16) Uani 1 1 d . . . . .
N6 N 0.7376(5) 0.3293(14) 0.5164(3) 0.0536(17) Uani 1 1 d . . . . .
N7 N 0.2282(6) 0.9261(13) 0.2504(3) 0.067(2) Uani 1 1 d . . . . .
N8 N 0.2677(5) 0.5689(14) 0.2932(3) 0.062(2) Uani 1 1 d . . . . .
N9 N 0.3395(3) 0.9296(10) 0.3786(2) 0.0316(12) Uani 1 1 d . . . . .
N10 N 0.4068(3) 1.0854(10) 0.3668(2) 0.0365(13) Uani 1 1 d . . . . .
N11 N 0.4871(4) 0.6802(14) 0.4803(2) 0.0441(15) Uani 1 1 d . . . . .
N12 N 0.5545(4) 1.1199(14) 0.3945(3) 0.0508(16) Uani 1 1 d . . . . .
O1 O 0.4801(5) 0.2598(10) 0.7875(2) 0.079(2) Uani 1 1 d . . . . .
O2 O 0.8190(4) -0.3230(13) 0.6133(4) 0.098(2) Uani 1 1 d . . . . .
O3 O 0.8748(4) 0.0384(12) 0.5944(3) 0.0840(19) Uani 1 1 d . . . . .
O4 O 0.7996(5) 0.2340(11) 0.4934(2) 0.081(2) Uani 1 1 d . . . . .
O5 O 0.7060(4) 0.5295(12) 0.5011(3) 0.092(2) Uani 1 1 d . . . . .
O6 O 0.2315(5) 0.7256(11) 0.2107(2) 0.075(2) Uani 1 1 d . . . . .
O7 O 0.4813(4) 0.4590(10) 0.4841(2) 0.0663(16) Uani 1 1 d . . . . .
O8 O 0.5265(5) 0.8092(13) 0.5140(3) 0.085(2) Uani 1 1 d . . . . .
O9 O 0.6160(3) 1.0067(13) 0.4169(3) 0.0834(19) Uani 1 1 d . . . . .
O10 O 0.5621(4) 1.3188(14) 0.3707(3) 0.085(2) 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
C1 N2 1.262(9) . ?
C1 O1 1.285(9) . ?
C1 H1 0.9300 . ?
C2 N1 1.282(9) . ?
C2 N2 1.371(10) . ?
C2 C3 1.485(9) . ?
C3 N4 1.469(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N4 1.312(7) . ?
C4 C5 1.374(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(9) . ?
C5 N6 1.422(9) . ?
C6 N3 1.326(8) . ?
C6 N5 1.457(9) . ?
C7 N8 1.299(11) . ?
C7 O6 1.341(10) . ?
C7 H7 0.9300 . ?
C8 N7 1.275(9) . ?
C8 N8 1.378(10) . ?
C8 C9 1.482(11) . ?
C9 N9 1.462(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.355(9) . ?
C10 N9 1.361(7) . ?
C10 H10 0.9300 . ?
C11 N10 1.304(7) . ?
C11 C12 1.397(9) . ?
C11 N12 1.431(9) . ?
C12 N11 1.438(8) . ?
N1 O1 1.410(9) . ?
N3 N4 1.354(7) . ?
N5 O2 1.201(8) . ?
N5 O3 1.215(8) . ?
N6 O4 1.201(8) . ?
N6 O5 1.225(8) . ?
N7 O6 1.422(9) . ?
N9 N10 1.349(7) . ?
N11 O7 1.187(8) . ?
N11 O8 1.210(8) . ?
N12 O10 1.205(9) . ?
N12 O9 1.233(8) . ?

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 O1 117.2(7) . . ?
N2 C1 H1 121.4 . . ?
O1 C1 H1 121.4 . . ?
N1 C2 N2 113.6(6) . . ?
N1 C2 C3 122.6(7) . . ?
N2 C2 C3 123.8(6) . . ?
N4 C3 C2 112.1(5) . . ?
N4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
N4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N4 C4 C5 107.0(6) . . ?
N4 C4 H4 126.5 . . ?
C5 C4 H4 126.5 . . ?
C4 C5 C6 104.3(6) . . ?
C4 C5 N6 125.9(6) . . ?
C6 C5 N6 129.1(7) . . ?
N3 C6 C5 111.9(6) . . ?
N3 C6 N5 116.9(6) . . ?
C5 C6 N5 130.9(6) . . ?
N8 C7 O6 111.9(8) . . ?
N8 C7 H7 124.0 . . ?
O6 C7 H7 124.0 . . ?
N7 C8 N8 115.0(7) . . ?
N7 C8 C9 121.6(7) . . ?
N8 C8 C9 123.3(6) . . ?
N9 C9 C8 110.6(5) . . ?
N9 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N9 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C12 C10 N9 105.4(6) . . ?
C12 C10 H10 127.3 . . ?
N9 C10 H10 127.3 . . ?
N10 C11 C12 112.6(5) . . ?
N10 C11 N12 118.2(6) . . ?
C12 C11 N12 128.8(6) . . ?
C10 C12 C11 105.3(5) . . ?
C10 C12 N11 122.5(6) . . ?
C11 C12 N11 131.6(6) . . ?
C2 N1 O1 103.9(6) . . ?
C1 N2 C2 101.0(6) . . ?
C6 N3 N4 103.4(5) . . ?
C4 N4 N3 113.4(6) . . ?
C4 N4 C3 126.9(6) . . ?
N3 N4 C3 119.7(5) . . ?
O2 N5 O3 126.1(7) . . ?
O2 N5 C6 118.0(7) . . ?
O3 N5 C6 115.7(7) . . ?
O4 N6 O5 123.1(6) . . ?
O4 N6 C5 119.8(7) . . ?
O5 N6 C5 117.1(6) . . ?
C8 N7 O6 103.2(6) . . ?
C7 N8 C8 103.1(7) . . ?
N10 N9 C10 112.9(5) . . ?
N10 N9 C9 120.1(5) . . ?
C10 N9 C9 126.9(6) . . ?
C11 N10 N9 103.7(5) . . ?
O7 N11 O8 123.5(7) . . ?
O7 N11 C12 119.0(6) . . ?
O8 N11 C12 117.5(7) . . ?
O10 N12 O9 123.9(7) . . ?
O10 N12 C11 119.7(6) . . ?
O9 N12 C11 116.3(7) . . ?
C1 O1 N1 104.1(6) . . ?
C7 O6 N7 106.6(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
N1 C2 C3 N4 -132.6(8) . . . . ?
N2 C2 C3 N4 46.2(9) . . . . ?
N4 C4 C5 C6 -0.7(7) . . . . ?
N4 C4 C5 N6 170.1(7) . . . . ?
C4 C5 C6 N3 -0.9(7) . . . . ?
N6 C5 C6 N3 -171.3(7) . . . . ?
C4 C5 C6 N5 -173.3(7) . . . . ?
N6 C5 C6 N5 16.2(12) . . . . ?
N7 C8 C9 N9 -128.6(8) . . . . ?
N8 C8 C9 N9 54.7(9) . . . . ?
N9 C10 C12 C11 1.3(6) . . . . ?
N9 C10 C12 N11 173.4(5) . . . . ?
N10 C11 C12 C10 -0.9(7) . . . . ?
N12 C11 C12 C10 -173.7(6) . . . . ?
N10 C11 C12 N11 -172.0(6) . . . . ?
N12 C11 C12 N11 15.2(11) . . . . ?
N2 C2 N1 O1 4.3(9) . . . . ?
C3 C2 N1 O1 -176.8(7) . . . . ?
O1 C1 N2 C2 -0.6(11) . . . . ?
N1 C2 N2 C1 -2.5(10) . . . . ?
C3 C2 N2 C1 178.5(7) . . . . ?
C5 C6 N3 N4 2.0(6) . . . . ?
N5 C6 N3 N4 175.6(5) . . . . ?
C5 C4 N4 N3 2.1(7) . . . . ?
C5 C4 N4 C3 -178.5(6) . . . . ?
C6 N3 N4 C4 -2.6(6) . . . . ?
C6 N3 N4 C3 178.0(5) . . . . ?
C2 C3 N4 C4 -90.9(7) . . . . ?
C2 C3 N4 N3 88.4(7) . . . . ?
N3 C6 N5 O2 33.3(10) . . . . ?
C5 C6 N5 O2 -154.6(8) . . . . ?
N3 C6 N5 O3 -141.5(7) . . . . ?
C5 C6 N5 O3 30.7(11) . . . . ?
C4 C5 N6 O4 -155.4(8) . . . . ?
C6 C5 N6 O4 13.2(12) . . . . ?
C4 C5 N6 O5 23.5(11) . . . . ?
C6 C5 N6 O5 -167.9(7) . . . . ?
N8 C8 N7 O6 -1.5(9) . . . . ?
C9 C8 N7 O6 -178.5(6) . . . . ?
O6 C7 N8 C8 3.0(11) . . . . ?
N7 C8 N8 C7 -0.8(10) . . . . ?
C9 C8 N8 C7 176.1(8) . . . . ?
C12 C10 N9 N10 -1.4(7) . . . . ?
C12 C10 N9 C9 -177.4(6) . . . . ?
C8 C9 N9 N10 89.3(7) . . . . ?
C8 C9 N9 C10 -94.9(7) . . . . ?
C12 C11 N10 N9 0.1(6) . . . . ?
N12 C11 N10 N9 173.8(5) . . . . ?
C10 N9 N10 C11 0.8(6) . . . . ?
C9 N9 N10 C11 177.2(5) . . . . ?
C10 C12 N11 O7 48.2(9) . . . . ?
C11 C12 N11 O7 -142.0(7) . . . . ?
C10 C12 N11 O8 -130.8(7) . . . . ?
C11 C12 N11 O8 39.0(10) . . . . ?
N10 C11 N12 O10 19.2(10) . . . . ?
C12 C11 N12 O10 -168.3(8) . . . . ?
N10 C11 N12 O9 -163.9(7) . . . . ?
C12 C11 N12 O9 8.6(10) . . . . ?
N2 C1 O1 N1 3.1(11) . . . . ?
C2 N1 O1 C1 -4.3(9) . . . . ?
N8 C7 O6 N7 -3.9(11) . . . . ?
C8 N7 O6 C7 3.1(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 O4 0.93 2.44 3.282(8) 150.7 4_455 yes
C9 H9A N8 0.97 2.59 3.504(10) 157.1 1_565 yes
C7 H7 N7 0.93 2.42 3.193(12) 140.0 1_545 yes
C4 H4 O7 0.93 2.46 3.226(9) 140.2 . yes
C3 H3B O3 0.97 2.58 3.384(9) 140.6 4_455 yes
C3 H3B O2 0.97 2.57 3.215(9) 124.0 4_445 yes
C3 H3A N2 0.97 2.64 3.558(10) 158.7 1_545 yes
C1 H1 O10 0.93 2.59 3.119(10) 116.2 2_675 yes
C1 H1 N1 0.93 2.60 3.314(11) 134.3 1_565 yes

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_ZTW240425_1_a
_database_code_depnum_ccdc_archive 'CCDC 2379758'
loop_
_audit_author_name
_audit_author_address
'TongWei Zhang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2024-08-26 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
5-((3,4-dinitro-1H-pyrazol-1-yl)methyl)-2-methyl-2H-tetrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N8 O4'
_chemical_formula_sum            'C6 H6 N8 O4'
_chemical_formula_weight         254.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   6.7014(3)
_cell_length_b                   7.4750(4)
_cell_length_c                   11.2966(5)
_cell_angle_alpha                97.876(2)
_cell_angle_beta                 104.754(2)
_cell_angle_gamma                107.211(2)
_cell_volume                     508.71(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4292
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      27.39

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            7846
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2314
_reflns_number_gt                1844
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.1143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2314
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8188(2) 0.78596(19) 0.80655(13) 0.0308(3) Uani 1 1 d . . . . .
C2 C 0.9733(2) 0.69795(19) 0.84623(12) 0.0293(3) Uani 1 1 d . . . . .
C3 C 0.8500(2) 0.51089(19) 0.83678(13) 0.0303(3) Uani 1 1 d . . . . .
H3 H 0.902091 0.412592 0.855823 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4450(2) 0.3336(2) 0.78125(15) 0.0375(4) Uani 1 1 d . . . . .
H4A H 0.387849 0.358023 0.850187 0.045 Uiso 1 1 calc R U . . .
H4B H 0.486076 0.220142 0.786010 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2704(2) 0.29628(19) 0.66006(14) 0.0330(3) Uani 1 1 d . . . . .
C6 C -0.2480(3) 0.2522(3) 0.47474(19) 0.0553(5) Uani 1 1 d . . . . .
H6A H -0.346389 0.144107 0.492247 0.083 Uiso 1 1 calc R U . . .
H6B H -0.279555 0.236703 0.385393 0.083 Uiso 1 1 calc R U . . .
H6C H -0.266901 0.368249 0.509701 0.083 Uiso 1 1 calc R U . . .
N1 N 0.64013(19) 0.49830(16) 0.79474(11) 0.0315(3) Uani 1 1 d . . . . .
N2 N 0.6158(2) 0.66616(17) 0.77593(12) 0.0346(3) Uani 1 1 d . . . . .
N3 N 0.8486(2) 0.98616(17) 0.80610(12) 0.0381(3) Uani 1 1 d . . . . .
N4 N 1.2091(2) 0.77110(18) 0.88380(12) 0.0380(3) Uani 1 1 d . . . . .
N5 N 0.2840(2) 0.2314(2) 0.54720(14) 0.0505(4) Uani 1 1 d . . . . .
N6 N 0.0953(2) 0.2109(2) 0.46502(13) 0.0525(4) Uani 1 1 d . . . . .
N7 N -0.0222(2) 0.26351(19) 0.53064(12) 0.0388(3) Uani 1 1 d . . . . .
N8 N 0.0800(2) 0.31881(18) 0.65308(12) 0.0380(3) Uani 1 1 d . . . . .
O1 O 0.7085(2) 1.02109(17) 0.73041(13) 0.0557(4) Uani 1 1 d . . . . .
O2 O 1.0114(2) 1.10714(16) 0.88477(11) 0.0574(4) Uani 1 1 d . . . . .
O3 O 1.2998(2) 0.91111(18) 0.84860(13) 0.0586(4) Uani 1 1 d . . . . .
O4 O 1.30485(19) 0.68365(19) 0.94738(12) 0.0551(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
C1 N2 1.3143(19) . ?
C1 C2 1.3974(19) . ?
C1 N3 1.4509(17) . ?
C2 C3 1.3710(19) . ?
C2 N4 1.4351(18) . ?
C3 N1 1.3347(18) . ?
C3 H3 0.9300 . ?
C4 N1 1.4640(18) . ?
C4 C5 1.486(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N8 1.3203(18) . ?
C5 N5 1.336(2) . ?
C6 N7 1.455(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N1 N2 1.3501(15) . ?
N3 O1 1.2158(17) . ?
N3 O2 1.2247(17) . ?
N4 O3 1.2181(17) . ?
N4 O4 1.2237(17) . ?
N5 N6 1.317(2) . ?
N6 N7 1.3132(19) . ?
N7 N8 1.3215(18) . ?

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 C2 112.23(12) . . ?
N2 C1 N3 117.09(12) . . ?
C2 C1 N3 130.38(13) . . ?
C3 C2 C1 104.60(12) . . ?
C3 C2 N4 124.22(13) . . ?
C1 C2 N4 131.12(13) . . ?
N1 C3 C2 106.14(12) . . ?
N1 C3 H3 126.9 . . ?
C2 C3 H3 126.9 . . ?
N1 C4 C5 111.85(12) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N8 C5 N5 112.44(13) . . ?
N8 C5 C4 122.95(14) . . ?
N5 C5 C4 124.57(13) . . ?
N7 C6 H6A 109.5 . . ?
N7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 N1 N2 113.31(11) . . ?
C3 N1 C4 127.28(11) . . ?
N2 N1 C4 119.05(11) . . ?
C1 N2 N1 103.71(11) . . ?
O1 N3 O2 125.13(13) . . ?
O1 N3 C1 117.91(13) . . ?
O2 N3 C1 116.93(13) . . ?
O3 N4 O4 124.56(14) . . ?
O3 N4 C2 118.72(13) . . ?
O4 N4 C2 116.70(13) . . ?
N6 N5 C5 106.10(13) . . ?
N7 N6 N5 106.02(13) . . ?
N6 N7 N8 113.67(12) . . ?
N6 N7 C6 123.24(14) . . ?
N8 N7 C6 123.01(14) . . ?
C5 N8 N7 101.76(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
N2 C1 C2 C3 0.62(16) . . . . ?
N3 C1 C2 C3 173.96(14) . . . . ?
N2 C1 C2 N4 177.68(14) . . . . ?
N3 C1 C2 N4 -9.0(3) . . . . ?
C1 C2 C3 N1 -0.22(15) . . . . ?
N4 C2 C3 N1 -177.54(13) . . . . ?
N1 C4 C5 N8 -113.36(15) . . . . ?
N1 C4 C5 N5 68.75(19) . . . . ?
C2 C3 N1 N2 -0.22(16) . . . . ?
C2 C3 N1 C4 -173.22(13) . . . . ?
C5 C4 N1 C3 -136.28(15) . . . . ?
C5 C4 N1 N2 51.09(18) . . . . ?
C2 C1 N2 N1 -0.74(16) . . . . ?
N3 C1 N2 N1 -175.04(12) . . . . ?
C3 N1 N2 C1 0.59(16) . . . . ?
C4 N1 N2 C1 174.22(12) . . . . ?
N2 C1 N3 O1 -32.10(19) . . . . ?
C2 C1 N3 O1 154.82(15) . . . . ?
N2 C1 N3 O2 146.11(14) . . . . ?
C2 C1 N3 O2 -27.0(2) . . . . ?
C3 C2 N4 O3 154.45(15) . . . . ?
C1 C2 N4 O3 -22.1(2) . . . . ?
C3 C2 N4 O4 -23.9(2) . . . . ?
C1 C2 N4 O4 159.58(15) . . . . ?
N8 C5 N5 N6 -0.28(19) . . . . ?
C4 C5 N5 N6 177.81(14) . . . . ?
C5 N5 N6 N7 0.07(19) . . . . ?
N5 N6 N7 N8 0.16(19) . . . . ?
N5 N6 N7 C6 -176.67(15) . . . . ?
N5 C5 N8 N7 0.35(17) . . . . ?
C4 C5 N8 N7 -177.77(13) . . . . ?
N6 N7 N8 C5 -0.31(17) . . . . ?
C6 N7 N8 C5 176.52(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O2 0.93 2.63 3.5573(18) 173.0 1_545 yes
C4 H4B O1 0.97 2.52 3.390(2) 148.9 1_545 yes
C4 H4B O3 0.97 2.57 3.2735(19) 129.9 1_445 yes

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_ZTW240410_1_a
_database_code_depnum_ccdc_archive 'CCDC 2379760'
loop_
_audit_author_name
_audit_author_address
'TongWei Zhang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2024-08-26 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
3-((3,4-dinitro-1H-pyrazol-1-yl)methyl)-5-(trifluoromethyl)-1,2,4-oxadiazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 F3 N6 O5'
_chemical_formula_sum            'C7 H3 F3 N6 O5'
_chemical_formula_weight         308.15

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8436(5)
_cell_length_b                   8.0309(5)
_cell_length_c                   15.9838(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.681(2)
_cell_angle_gamma                90
_cell_volume                     1129.63(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4903
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            11013
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2584
_reflns_number_gt                1810
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²+0.4965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2584
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7126(2) 0.4618(3) 0.54945(13) 0.0370(5) Uani 1 1 d . . . . .
C2 C 0.7311(2) 0.3468(3) 0.48629(13) 0.0353(5) Uani 1 1 d . . . . .
C3 C 0.7014(2) 0.1952(3) 0.52051(13) 0.0346(5) Uani 1 1 d . . . . .
H3 H 0.703039 0.091682 0.494491 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6340(2) 0.1085(3) 0.66364(13) 0.0371(5) Uani 1 1 d . . . . .
H4A H 0.706155 0.121452 0.712988 0.045 Uiso 1 1 calc R U . . .
H4B H 0.642752 -0.004129 0.642796 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4765(2) 0.1363(2) 0.68720(13) 0.0339(5) Uani 1 1 d . . . . .
C6 C 0.2433(2) 0.1352(3) 0.68182(14) 0.0382(5) Uani 1 1 d . . . . .
C7 C 0.0747(3) 0.1175(3) 0.66210(18) 0.0551(7) Uani 1 1 d . . . . .
F1 F 0.0063(2) 0.2602(3) 0.66501(19) 0.1090(9) Uani 1 1 d . . . . .
F2 F 0.04044(18) 0.0547(3) 0.58727(12) 0.0867(6) Uani 1 1 d . . . . .
F3 F 0.0182(2) 0.0163(3) 0.71524(14) 0.1109(9) Uani 1 1 d . . . . .
N1 N 0.66967(18) 0.2268(2) 0.59910(11) 0.0333(4) Uani 1 1 d . . . . .
N2 N 0.6763(2) 0.3911(2) 0.61883(11) 0.0398(5) Uani 1 1 d . . . . .
N3 N 0.34801(19) 0.0905(2) 0.63684(11) 0.0381(5) Uani 1 1 d . . . . .
N4 N 0.4517(2) 0.2058(3) 0.75736(12) 0.0459(5) Uani 1 1 d . . . . .
N5 N 0.7368(2) 0.6412(2) 0.54874(13) 0.0485(5) Uani 1 1 d . . . . .
N6 N 0.7583(2) 0.3807(2) 0.40143(12) 0.0453(5) Uani 1 1 d . . . . .
O1 O 0.29190(18) 0.2047(2) 0.75490(10) 0.0462(4) Uani 1 1 d . . . . .
O2 O 0.6288(2) 0.7304(2) 0.55233(13) 0.0677(6) Uani 1 1 d . . . . .
O3 O 0.8644(3) 0.6883(3) 0.5453(2) 0.1059(10) Uani 1 1 d . . . . .
O4 O 0.7409(3) 0.5229(2) 0.37705(12) 0.0822(7) Uani 1 1 d . . . . .
O5 O 0.7928(2) 0.2665(2) 0.35754(11) 0.0602(5) 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
C1 N2 1.314(3) . ?
C1 C2 1.390(3) . ?
C1 N5 1.457(3) . ?
C2 C3 1.371(3) . ?
C2 N6 1.427(3) . ?
C3 N1 1.338(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.460(3) . ?
C4 C5 1.495(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N4 1.291(3) . ?
C5 N3 1.376(3) . ?
C6 N3 1.278(3) . ?
C6 O1 1.327(3) . ?
C6 C7 1.500(3) . ?
C7 F1 1.299(3) . ?
C7 F2 1.306(3) . ?
C7 F3 1.310(3) . ?
N1 N2 1.356(2) . ?
N4 O1 1.410(2) . ?
N5 O3 1.196(3) . ?
N5 O2 1.200(3) . ?
N6 O5 1.212(3) . ?
N6 O4 1.212(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
N2 C1 C2 112.43(18) . . ?
N2 C1 N5 118.85(19) . . ?
C2 C1 N5 128.6(2) . . ?
C3 C2 C1 105.06(18) . . ?
C3 C2 N6 127.26(19) . . ?
C1 C2 N6 127.35(19) . . ?
N1 C3 C2 105.77(18) . . ?
N1 C3 H3 127.1 . . ?
C2 C3 H3 127.1 . . ?
N1 C4 C5 110.68(17) . . ?
N1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N4 C5 N3 115.02(18) . . ?
N4 C5 C4 121.70(19) . . ?
N3 C5 C4 123.28(19) . . ?
N3 C6 O1 115.06(19) . . ?
N3 C6 C7 128.0(2) . . ?
O1 C6 C7 117.0(2) . . ?
F1 C7 F2 107.9(3) . . ?
F1 C7 F3 108.4(2) . . ?
F2 C7 F3 106.6(2) . . ?
F1 C7 C6 111.5(2) . . ?
F2 C7 C6 111.4(2) . . ?
F3 C7 C6 110.9(2) . . ?
C3 N1 N2 113.26(17) . . ?
C3 N1 C4 128.30(17) . . ?
N2 N1 C4 118.43(17) . . ?
C1 N2 N1 103.47(17) . . ?
C6 N3 C5 101.43(18) . . ?
C5 N4 O1 103.21(17) . . ?
O3 N5 O2 124.9(2) . . ?
O3 N5 C1 116.9(2) . . ?
O2 N5 C1 118.1(2) . . ?
O5 N6 O4 124.0(2) . . ?
O5 N6 C2 118.81(19) . . ?
O4 N6 C2 117.2(2) . . ?
C6 O1 N4 105.28(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
N2 C1 C2 C3 0.8(2) . . . . ?
N5 C1 C2 C3 176.9(2) . . . . ?
N2 C1 C2 N6 174.6(2) . . . . ?
N5 C1 C2 N6 -9.3(4) . . . . ?
C1 C2 C3 N1 -0.5(2) . . . . ?
N6 C2 C3 N1 -174.3(2) . . . . ?
N1 C4 C5 N4 -105.6(2) . . . . ?
N1 C4 C5 N3 74.5(2) . . . . ?
N3 C6 C7 F1 -123.8(3) . . . . ?
O1 C6 C7 F1 56.5(3) . . . . ?
N3 C6 C7 F2 -3.2(4) . . . . ?
O1 C6 C7 F2 177.1(2) . . . . ?
N3 C6 C7 F3 115.3(3) . . . . ?
O1 C6 C7 F3 -64.3(3) . . . . ?
C2 C3 N1 N2 0.1(2) . . . . ?
C2 C3 N1 C4 -178.26(18) . . . . ?
C5 C4 N1 C3 -117.0(2) . . . . ?
C5 C4 N1 N2 64.7(2) . . . . ?
C2 C1 N2 N1 -0.7(2) . . . . ?
N5 C1 N2 N1 -177.25(18) . . . . ?
C3 N1 N2 C1 0.4(2) . . . . ?
C4 N1 N2 C1 178.92(17) . . . . ?
O1 C6 N3 C5 0.3(2) . . . . ?
C7 C6 N3 C5 -179.4(2) . . . . ?
N4 C5 N3 C6 -0.8(2) . . . . ?
C4 C5 N3 C6 179.13(19) . . . . ?
N3 C5 N4 O1 1.0(2) . . . . ?
C4 C5 N4 O1 -178.97(17) . . . . ?
N2 C1 N5 O3 110.1(3) . . . . ?
C2 C1 N5 O3 -65.8(4) . . . . ?
N2 C1 N5 O2 -69.4(3) . . . . ?
C2 C1 N5 O2 114.7(3) . . . . ?
C3 C2 N6 O5 -17.8(3) . . . . ?
C1 C2 N6 O5 169.8(2) . . . . ?
C3 C2 N6 O4 160.1(2) . . . . ?
C1 C2 N6 O4 -12.3(4) . . . . ?
N3 C6 O1 N4 0.3(2) . . . . ?
C7 C6 O1 N4 179.98(18) . . . . ?
C5 N4 O1 C6 -0.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4B O2 0.97 2.57 3.517(3) 164.8 1_545 yes
C4 H4A O5 0.97 2.53 3.424(3) 153.8 4_566 yes
C3 H3 N3 0.93 2.56 3.400(3) 150.2 3_656 yes

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.083



