# 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 2018

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1836403'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
3-Nitro-4,4'-bipyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N5 O2'
_chemical_formula_sum            'C6 H5 N5 O2'
_chemical_formula_weight         179.15

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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   5.4831(2)
_cell_length_b                   5.4831(2)
_cell_length_c                   47.463(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1426.95(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6517
_cell_measurement_theta_min      3.741
_cell_measurement_theta_max      27.951

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS-2T'
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            6517
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_theta_min         3.741
_diffrn_reflns_theta_max         27.951
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1701
_reflns_number_gt                1589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.497
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       'IPDS Software (Stoe & Cie, 2000)'
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.2689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1701
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.103
_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
O1 O 0.3496(3) 0.1721(3) 0.03482(3) 0.0404(3) Uani 1 1 d . . . . .
O2 O 0.1047(3) 0.2056(3) 0.07039(3) 0.0395(3) Uani 1 1 d . . . . .
N1 N -0.5256(3) -0.0264(3) 0.11254(3) 0.0352(3) Uani 1 1 d . . . . .
N2 N -0.6414(3) -0.2344(3) 0.10531(3) 0.0363(4) Uani 1 1 d . . . . .
N3 N -0.0217(3) -0.4132(3) 0.01448(3) 0.0345(3) Uani 1 1 d . . . . .
N4 N 0.1331(3) -0.2275(3) 0.01753(3) 0.0323(3) Uani 1 1 d . . . . .
N5 N 0.1757(3) 0.0995(3) 0.04929(3) 0.0310(3) Uani 1 1 d . . . . .
C1 C -0.3316(3) 0.0143(4) 0.09588(4) 0.0337(4) Uani 1 1 d . . . . .
C2 C -0.3169(3) -0.1772(3) 0.07676(3) 0.0289(3) Uani 1 1 d . . . . .
C3 C -0.5151(3) -0.3270(3) 0.08395(4) 0.0337(4) Uani 1 1 d . . . . .
C4 C -0.1963(3) -0.4204(3) 0.03432(4) 0.0333(4) Uani 1 1 d . . . . .
C5 C -0.1588(3) -0.2269(3) 0.05262(3) 0.0284(3) Uani 1 1 d . . . . .
C6 C 0.0489(3) -0.1158(3) 0.04057(3) 0.0287(3) Uani 1 1 d . . . . .
H1N H -0.586(5) 0.059(5) 0.1265(5) 0.071(9) Uiso 1 1 d . . . . .
H2N H 0.007(5) -0.514(5) -0.0011(6) 0.047(6) Uiso 1 1 d . . . . .
H1 H -0.237(4) 0.157(5) 0.0982(4) 0.042(6) Uiso 1 1 d . . . . .
H3 H -0.567(5) -0.475(5) 0.0753(5) 0.051(6) Uiso 1 1 d . . . . .
H4 H -0.319(4) -0.543(4) 0.0344(4) 0.043(6) 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 N5 1.2407(19) . ?
O2 N5 1.2219(19) . ?
N1 C1 1.344(2) . ?
N1 N2 1.350(2) . ?
N1 H1N 0.88(3) . ?
N2 C3 1.329(2) . ?
N3 N4 1.333(2) . ?
N3 C4 1.343(2) . ?
N3 H2N 0.94(3) . ?
N4 C6 1.336(2) . ?
N5 C6 1.431(2) . ?
C1 C2 1.390(2) . ?
C1 H1 0.94(3) . ?
C2 C3 1.404(2) . ?
C2 C5 1.462(2) . ?
C3 H3 0.95(3) . ?
C4 C5 1.387(2) . ?
C4 H4 0.95(2) . ?
C5 C6 1.413(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 111.27(15) . . ?
C1 N1 H1N 131(2) . . ?
N2 N1 H1N 118(2) . . ?
C3 N2 N1 105.78(15) . . ?
N4 N3 C4 113.58(14) . . ?
N4 N3 H2N 115.6(15) . . ?
C4 N3 H2N 130.8(15) . . ?
N3 N4 C6 102.65(14) . . ?
O2 N5 O1 123.05(15) . . ?
O2 N5 C6 118.36(14) . . ?
O1 N5 C6 118.57(14) . . ?
N1 C1 C2 107.74(16) . . ?
N1 C1 H1 120.3(13) . . ?
C2 C1 H1 131.9(14) . . ?
C1 C2 C3 103.79(15) . . ?
C1 C2 C5 133.34(16) . . ?
C3 C2 C5 122.71(15) . . ?
N2 C3 C2 111.42(16) . . ?
N2 C3 H3 120.0(15) . . ?
C2 C3 H3 128.6(15) . . ?
N3 C4 C5 108.14(16) . . ?
N3 C4 H4 121.8(13) . . ?
C5 C4 H4 130.1(13) . . ?
C4 C5 C6 101.26(14) . . ?
C4 C5 C2 123.07(15) . . ?
C6 C5 C2 135.66(16) . . ?
N4 C6 C5 114.37(15) . . ?
N4 C6 N5 116.56(15) . . ?
C5 C6 N5 129.06(14) . . ?

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
C1 N1 N2 C3 0.8(2) . . . . ?
C4 N3 N4 C6 0.3(2) . . . . ?
N2 N1 C1 C2 -0.4(2) . . . . ?
N1 C1 C2 C3 -0.1(2) . . . . ?
N1 C1 C2 C5 175.16(18) . . . . ?
N1 N2 C3 C2 -0.9(2) . . . . ?
C1 C2 C3 N2 0.6(2) . . . . ?
C5 C2 C3 N2 -175.28(16) . . . . ?
N4 N3 C4 C5 -0.6(2) . . . . ?
N3 C4 C5 C6 0.6(2) . . . . ?
N3 C4 C5 C2 179.46(16) . . . . ?
C1 C2 C5 C4 -172.26(19) . . . . ?
C3 C2 C5 C4 2.3(3) . . . . ?
C1 C2 C5 C6 6.2(4) . . . . ?
C3 C2 C5 C6 -179.25(19) . . . . ?
N3 N4 C6 C5 0.1(2) . . . . ?
N3 N4 C6 N5 -178.67(14) . . . . ?
C4 C5 C6 N4 -0.4(2) . . . . ?
C2 C5 C6 N4 -179.12(18) . . . . ?
C4 C5 C6 N5 178.17(17) . . . . ?
C2 C5 C6 N5 -0.5(3) . . . . ?
O2 N5 C6 N4 -179.55(16) . . . . ?
O1 N5 C6 N4 1.7(2) . . . . ?
O2 N5 C6 C5 1.9(3) . . . . ?
O1 N5 C6 C5 -176.84(18) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.037


####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1836404'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
3,3'-Dinitro-4,4'-bipyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N6 O4'
_chemical_formula_sum            'C6 H4 N6 O4'
_chemical_formula_weight         224.15

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   15.9744(9)
_cell_length_b                   6.5428(8)
_cell_length_c                   8.9414(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.739(10)
_cell_angle_gamma                90
_cell_volume                     819.41(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    3236
_cell_measurement_theta_min      2.909
_cell_measurement_theta_max      28.031

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe Image Plate Diffraction System'
_diffrn_measurement_method       'φ oscillation scans'

_diffrn_reflns_number            3236
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.909
_diffrn_reflns_theta_max         28.031
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             986
_reflns_number_gt                829
_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       'IPDS Software (Stoe & Cie, 2000)'
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²+0.0723P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         986
_refine_ls_number_parameters     81
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.06740(6) 0.48068(16) 0.43536(13) 0.0395(3) Uani 1 1 d . . . . .
O2 O 0.18461(6) 0.56813(15) 0.39244(12) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.16833(6) 0.00680(17) 0.22016(13) 0.0272(3) Uani 1 1 d . . . . .
N2 N 0.19298(6) 0.19333(16) 0.28732(12) 0.0250(3) Uani 1 1 d . . . . .
N3 N 0.12394(6) 0.44694(16) 0.38240(12) 0.0242(3) Uani 1 1 d . . . . .
C1 C 0.08247(7) -0.05400(19) 0.19681(14) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.04609(7) 0.10353(17) 0.25163(13) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.11905(6) 0.25113(17) 0.30625(12) 0.0206(3) Uani 1 1 d . . . . .
H1N H 0.2117(11) -0.059(3) 0.207(2) 0.042(4) Uiso 1 1 d . . . . .
H1 H 0.0565(10) -0.184(2) 0.1502(19) 0.029(4) 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 N3 1.2248(12) . ?
O2 N3 1.2217(12) . ?
N1 N2 1.3334(15) . ?
N1 C1 1.3444(14) . ?
N1 H1N 0.869(18) . ?
N2 C3 1.3261(12) . ?
N3 C3 1.4352(15) . ?
C1 C2 1.3835(15) . ?
C1 H1 0.951(16) . ?
C2 C3 1.4078(14) . ?
C2 C2 1.4589(19) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 113.52(9) . . ?
N2 N1 H1N 115.5(11) . . ?
C1 N1 H1N 130.7(12) . . ?
C3 N2 N1 103.31(9) . . ?
O2 N3 O1 124.13(11) . . ?
O2 N3 C3 118.33(9) . . ?
O1 N3 C3 117.54(9) . . ?
N1 C1 C2 107.19(11) . . ?
N1 C1 H1 122.0(8) . . ?
C2 C1 H1 130.8(8) . . ?
C1 C2 C3 102.43(9) . . ?
C1 C2 C2 125.79(8) . 2 ?
C3 C2 C2 131.78(7) . 2 ?
N2 C3 C2 113.55(10) . . ?
N2 C3 N3 117.80(9) . . ?
C2 C3 N3 128.61(9) . . ?

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
C1 N1 N2 C3 -0.11(12) . . . . ?
N2 N1 C1 C2 0.26(13) . . . . ?
N1 C1 C2 C3 -0.27(12) . . . . ?
N1 C1 C2 C2 179.56(12) . . . 2 ?
N1 N2 C3 C2 -0.08(12) . . . . ?
N1 N2 C3 N3 178.00(9) . . . . ?
C1 C2 C3 N2 0.22(12) . . . . ?
C2 C2 C3 N2 -179.60(12) 2 . . . ?
C1 C2 C3 N3 -177.59(10) . . . . ?
C2 C2 C3 N3 2.6(2) 2 . . . ?
O2 N3 C3 N2 15.42(14) . . . . ?
O1 N3 C3 N2 -163.66(10) . . . . ?
O2 N3 C3 C2 -166.84(10) . . . . ?
O1 N3 C3 C2 14.08(16) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.056


####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1836406'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
3,5,3'-Trinitro-4,4'-bipyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H3 N7 O6'
_chemical_formula_sum            'C6 H3 N7 O6'
_chemical_formula_weight         269.15

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      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                   8.6064(8)
_cell_length_b                   11.9636(9)
_cell_length_c                   10.1200(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.148(10)
_cell_angle_gamma                90
_cell_volume                     950.81(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2.594
_cell_measurement_theta_max      28.009

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe Image Plate Diffraction System'
_diffrn_measurement_method       'φ oscillation scans'
_diffrn_reflns_number            8130
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.594
_diffrn_reflns_theta_max         28.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2294
_reflns_number_gt                1365
_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       'IPDS Software (Stoe & Cie, 2000)'
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2294
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_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
O1 O 0.01647(17) -0.07801(13) 0.21340(18) 0.0503(4) Uani 1 1 d . . . . .
O2 O 0.29130(16) -0.06404(12) 0.31299(15) 0.0434(4) Uani 1 1 d . . . . .
O3 O 0.08881(15) 0.40657(11) -0.03365(16) 0.0394(3) Uani 1 1 d . . . . .
O4 O 0.34954(15) 0.35051(12) 0.05652(17) 0.0424(4) Uani 1 1 d . . . . .
O5 O 0.59504(18) 0.12765(15) -0.07928(17) 0.0547(4) Uani 1 1 d . . . . .
O6 O 0.33470(16) 0.15007(14) -0.10764(16) 0.0483(4) Uani 1 1 d . . . . .
N1 N -0.01771(18) 0.12984(14) 0.11804(17) 0.0317(4) Uani 1 1 d . . . . .
N2 N -0.01070(16) 0.22826(14) 0.06117(16) 0.0304(4) Uani 1 1 d . . . . .
N3 N 0.7082(2) 0.11033(14) 0.33647(19) 0.0354(4) Uani 1 1 d . . . . .
N4 N 0.70137(17) 0.11789(13) 0.20220(18) 0.0337(4) Uani 1 1 d . . . . .
N5 N 0.14951(18) -0.02899(13) 0.23919(16) 0.0320(4) Uani 1 1 d . . . . .
N6 N 0.20012(17) 0.33797(13) 0.03135(16) 0.0289(3) Uani 1 1 d . . . . .
N7 N 0.48542(19) 0.13702(14) -0.03235(18) 0.0361(4) Uani 1 1 d . . . . .
C1 C 0.1352(2) 0.07971(15) 0.17561(18) 0.0260(4) Uani 1 1 d . . . . .
C2 C 0.25363(18) 0.14707(15) 0.15459(18) 0.0242(4) Uani 1 1 d . . . . .
C3 C 0.15095(19) 0.23727(15) 0.08198(18) 0.0248(4) Uani 1 1 d . . . . .
C4 C 0.5559(2) 0.11664(17) 0.3408(2) 0.0336(4) Uani 1 1 d . . . . .
C5 C 0.43758(19) 0.13053(15) 0.20140(19) 0.0261(4) Uani 1 1 d . . . . .
C6 C 0.5370(2) 0.13023(15) 0.1204(2) 0.0278(4) Uani 1 1 d . . . . .
H1N H -0.100(3) 0.1112(19) 0.126(2) 0.048(7) Uiso 1 1 d . . . . .
H2N H 0.797(3) 0.1046(17) 0.408(2) 0.036(6) Uiso 1 1 d . . . . .
H4 H 0.542(2) 0.1094(16) 0.427(2) 0.028(5) 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 N5 1.2159(19) . ?
O2 N5 1.2154(18) . ?
O3 N6 1.2282(19) . ?
O4 N6 1.2138(18) . ?
O5 N7 1.2226(19) . ?
O6 N7 1.216(2) . ?
N1 N2 1.323(2) . ?
N1 C1 1.343(2) . ?
N1 H1N 0.78(2) . ?
N2 C3 1.324(2) . ?
N3 C4 1.331(2) . ?
N3 N4 1.339(2) . ?
N3 H2N 0.81(2) . ?
N4 C6 1.323(2) . ?
N5 C1 1.434(2) . ?
N6 C3 1.439(2) . ?
N7 C6 1.425(2) . ?
C1 C2 1.382(2) . ?
C2 C3 1.398(2) . ?
C2 C5 1.468(2) . ?
C4 C5 1.371(3) . ?
C4 H4 0.93(2) . ?
C5 C6 1.407(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 112.04(14) . . ?
N2 N1 H1N 120.5(17) . . ?
C1 N1 H1N 126.7(17) . . ?
N1 N2 C3 103.61(14) . . ?
C4 N3 N4 113.25(16) . . ?
C4 N3 H2N 123.9(15) . . ?
N4 N3 H2N 122.8(15) . . ?
C6 N4 N3 103.55(14) . . ?
O2 N5 O1 125.88(16) . . ?
O2 N5 C1 117.97(14) . . ?
O1 N5 C1 116.16(15) . . ?
O4 N6 O3 123.85(16) . . ?
O4 N6 C3 118.00(14) . . ?
O3 N6 C3 118.15(13) . . ?
O6 N7 O5 124.28(17) . . ?
O6 N7 C6 117.78(15) . . ?
O5 N7 C6 117.93(15) . . ?
N1 C1 C2 109.04(16) . . ?
N1 C1 N5 119.25(15) . . ?
C2 C1 N5 131.66(15) . . ?
C1 C2 C3 100.58(13) . . ?
C1 C2 C5 129.59(16) . . ?
C3 C2 C5 129.78(15) . . ?
N2 C3 C2 114.71(15) . . ?
N2 C3 N6 117.04(15) . . ?
C2 C3 N6 128.23(14) . . ?
N3 C4 C5 107.42(17) . . ?
N3 C4 H4 122.2(11) . . ?
C5 C4 H4 130.3(11) . . ?
C4 C5 C6 103.10(14) . . ?
C4 C5 C2 126.66(15) . . ?
C6 C5 C2 130.18(16) . . ?
N4 C6 C5 112.66(17) . . ?
N4 C6 N7 117.66(15) . . ?
C5 C6 N7 129.63(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
C1 N1 N2 C3 1.4(2) . . . . ?
C4 N3 N4 C6 0.5(2) . . . . ?
N2 N1 C1 C2 -1.1(2) . . . . ?
N2 N1 C1 N5 -178.68(15) . . . . ?
O2 N5 C1 N1 -167.00(16) . . . . ?
O1 N5 C1 N1 13.1(2) . . . . ?
O2 N5 C1 C2 16.1(3) . . . . ?
O1 N5 C1 C2 -163.78(19) . . . . ?
N1 C1 C2 C3 0.36(19) . . . . ?
N5 C1 C2 C3 177.51(18) . . . . ?
N1 C1 C2 C5 177.95(17) . . . . ?
N5 C1 C2 C5 -4.9(3) . . . . ?
N1 N2 C3 C2 -1.1(2) . . . . ?
N1 N2 C3 N6 -179.70(15) . . . . ?
C1 C2 C3 N2 0.5(2) . . . . ?
C5 C2 C3 N2 -177.08(17) . . . . ?
C1 C2 C3 N6 178.86(17) . . . . ?
C5 C2 C3 N6 1.3(3) . . . . ?
O4 N6 C3 N2 176.02(16) . . . . ?
O3 N6 C3 N2 -3.4(2) . . . . ?
O4 N6 C3 C2 -2.3(3) . . . . ?
O3 N6 C3 C2 178.30(17) . . . . ?
N4 N3 C4 C5 -0.7(2) . . . . ?
N3 C4 C5 C6 0.5(2) . . . . ?
N3 C4 C5 C2 -176.74(18) . . . . ?
C1 C2 C5 C4 -58.2(3) . . . . ?
C3 C2 C5 C4 118.7(2) . . . . ?
C1 C2 C5 C6 125.2(2) . . . . ?
C3 C2 C5 C6 -57.8(3) . . . . ?
N3 N4 C6 C5 -0.1(2) . . . . ?
N3 N4 C6 N7 -177.89(16) . . . . ?
C4 C5 C6 N4 -0.3(2) . . . . ?
C2 C5 C6 N4 176.86(17) . . . . ?
C4 C5 C6 N7 177.19(19) . . . . ?
C2 C5 C6 N7 -5.7(3) . . . . ?
O6 N7 C6 N4 -178.91(17) . . . . ?
O5 N7 C6 N4 2.2(3) . . . . ?
O6 N7 C6 C5 3.7(3) . . . . ?
O5 N7 C6 C5 -175.19(19) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047


####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1836405'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
3,5-Dinitro-4,4'-bipyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N6 O4'
_chemical_formula_sum            'C6 H4 N6 O4'
_chemical_formula_weight         224.15

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   6.1653(7)
_cell_length_b                   15.7789(12)
_cell_length_c                   8.7387(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.434(10)
_cell_angle_gamma                90
_cell_volume                     811.06(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    3458
_cell_measurement_theta_min      3.555
_cell_measurement_theta_max      27.942

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe Image Plate Diffraction System'
_diffrn_measurement_method       'φ oscillation scans'
_diffrn_reflns_number            3458
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.555
_diffrn_reflns_theta_max         27.942
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             959
_reflns_number_gt                835
_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       'IPDS Software (Stoe & Cie, 2000)'
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0604P)²+0.1849P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         959
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
O1 O 0.54507(14) 0.21451(5) 0.42327(11) 0.0286(3) Uani 1 1 d . . . . .
O2 O 0.46179(16) 0.08296(6) 0.44194(14) 0.0398(3) Uani 1 1 d . . . . .
N1 N 0.08885(18) -0.10994(6) 0.22073(13) 0.0260(3) Uani 1 1 d . . . . .
N2 N 0.11129(15) 0.25476(5) 0.28851(11) 0.0188(3) Uani 1 1 d . . . . .
N3 N 0.40984(15) 0.15601(6) 0.39769(12) 0.0190(2) Uani 1 1 d . . . . .
C1 C 0.14665(18) -0.03036(7) 0.20282(14) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.0000 0.02324(9) 0.2500 0.0164(3) Uani 1 2 d S T P . .
C3 C 0.0000 0.11590(9) 0.2500 0.0148(3) Uani 1 2 d S T P . .
C4 C 0.17648(16) 0.17346(6) 0.31252(12) 0.0157(3) Uani 1 1 d . . . . .
H1N H 0.168(4) -0.1617(13) 0.210(3) 0.065(6) Uiso 1 1 d . . . . .
H1 H 0.272(3) -0.0187(9) 0.1638(19) 0.031(4) 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 N3 1.2187(12) . ?
O2 N3 1.2275(13) . ?
N1 C1 1.3272(15) . ?
N1 N1 1.341(2) 2 ?
N1 H1N 0.97(2) . ?
N2 N2 1.3352(17) 2 ?
N2 C4 1.3420(13) . ?
N3 C4 1.4346(13) . ?
C1 C2 1.3879(14) . ?
C1 H1 0.951(17) . ?
C2 C1 1.3879(14) 2 ?
C2 C3 1.4621(19) . ?
C3 C4 1.3968(13) 2 ?
C3 C4 1.3968(13) . ?

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
C1 N1 N1 108.90(7) . 2 ?
C1 N1 H1N 128.5(12) . . ?
N1 N1 H1N 122.1(12) 2 . ?
N2 N2 C4 107.05(6) 2 . ?
O1 N3 O2 123.63(10) . . ?
O1 N3 C4 118.33(9) . . ?
O2 N3 C4 118.04(9) . . ?
N1 C1 C2 108.64(10) . . ?
N1 C1 H1 120.1(9) . . ?
C2 C1 H1 131.3(9) . . ?
C1 C2 C1 104.91(13) . 2 ?
C1 C2 C3 127.55(7) . . ?
C1 C2 C3 127.55(7) 2 . ?
C4 C3 C4 98.89(12) 2 . ?
C4 C3 C2 130.56(6) 2 . ?
C4 C3 C2 130.56(6) . . ?
N2 C4 C3 113.50(9) . . ?
N2 C4 N3 118.12(9) . . ?
C3 C4 N3 128.38(9) . . ?

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 N1 C1 C2 -0.56(15) 2 . . . ?
N1 C1 C2 C1 0.22(6) . . . 2 ?
N1 C1 C2 C3 -179.79(6) . . . . ?
C1 C2 C3 C4 129.64(8) . . . 2 ?
C1 C2 C3 C4 -50.36(8) 2 . . 2 ?
C1 C2 C3 C4 -50.36(8) . . . . ?
C1 C2 C3 C4 129.64(8) 2 . . . ?
N2 N2 C4 C3 0.95(14) 2 . . . ?
N2 N2 C4 N3 -178.41(10) 2 . . . ?
C4 C3 C4 N2 -0.37(5) 2 . . . ?
C2 C3 C4 N2 179.63(5) . . . . ?
C4 C3 C4 N3 178.91(13) 2 . . . ?
C2 C3 C4 N3 -1.09(13) . . . . ?
O1 N3 C4 N2 -10.79(15) . . . . ?
O2 N3 C4 N2 168.62(11) . . . . ?
O1 N3 C4 C3 169.96(9) . . . . ?
O2 N3 C4 C3 -10.63(16) . . . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045


####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1836407'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
3,3',5,5'-Tetranitro-4,4'-bipyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N8 O8'
_chemical_formula_sum            'C6 H2 N8 O8'
_chemical_formula_weight         314.16

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      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'

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

_cell_length_a                   16.4281(13)
_cell_length_b                   16.4281(13)
_cell_length_c                   8.3705(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2259.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.480
_cell_measurement_theta_max      28.279

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.172
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS-2T'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            9974
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.480
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2783
_reflns_number_gt                2122
_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       'IPDS Software (Stoe & Cie, 2000)'
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2783
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
O1 O 0.13407(10) 0.21520(7) 0.13590(14) 0.0597(4) Uani 1 1 d . . . . .
O2 O 0.16418(7) 0.16763(6) -0.09971(12) 0.0414(3) Uani 1 1 d . . . . .
O3 O 0.18876(8) -0.16454(7) 0.31116(12) 0.0500(3) Uani 1 1 d . . . . .
O4 O 0.19492(7) -0.16750(6) 0.05114(11) 0.0408(3) Uani 1 1 d . . . . .
O5 O 0.06121(8) -0.13281(8) -0.35334(14) 0.0524(3) Uani 1 1 d . . . . .
O6 O 0.03844(6) -0.08035(7) -0.11807(12) 0.0423(3) Uani 1 1 d . . . . .
O7 O 0.40985(6) 0.03712(7) -0.19378(13) 0.0451(3) Uani 1 1 d . . . . .
O8 O 0.32808(6) 0.09471(6) -0.02345(11) 0.0343(2) Uani 1 1 d . . . . .
N1 N 0.13619(7) 0.06746(7) 0.26477(12) 0.0288(2) Uani 1 1 d . . . . .
N2 N 0.14532(7) -0.00984(7) 0.30683(12) 0.0292(2) Uani 1 1 d . . . . .
N3 N 0.20672(7) -0.06022(7) -0.37008(12) 0.0310(3) Uani 1 1 d . . . . .
N4 N 0.27786(7) -0.02260(8) -0.35046(12) 0.0325(3) Uani 1 1 d . . . . .
N5 N 0.15034(8) 0.16006(7) 0.04297(13) 0.0347(3) Uani 1 1 d . . . . .
N6 N 0.18546(7) -0.13217(7) 0.17850(12) 0.0319(3) Uani 1 1 d . . . . .
N7 N 0.08059(7) -0.09184(7) -0.23620(13) 0.0311(3) Uani 1 1 d . . . . .
N8 N 0.34277(7) 0.04902(7) -0.13670(12) 0.0280(2) Uani 1 1 d . . . . .
C1 C 0.15363(8) 0.07958(8) 0.10948(13) 0.0252(3) Uani 1 1 d . . . . .
C2 C 0.17487(7) 0.00618(7) 0.04081(12) 0.0215(2) Uani 1 1 d . . . . .
C3 C 0.16811(7) -0.04638(8) 0.17256(13) 0.0246(2) Uani 1 1 d . . . . .
C4 C 0.15964(8) -0.05506(7) -0.23966(13) 0.0241(2) Uani 1 1 d . . . . .
C5 C 0.20031(7) -0.01129(7) -0.12332(12) 0.0208(2) Uani 1 1 d . . . . .
C6 C 0.27336(8) 0.00638(8) -0.20255(13) 0.0240(2) Uani 1 1 d . . . . .
H1N H 0.1221(11) 0.1045(12) 0.340(2) 0.044(5) Uiso 1 1 d . . . . .
H2N H 0.1955(13) -0.0826(12) -0.462(2) 0.057(5) 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 N5 1.2236(15) . ?
O2 N5 1.2221(15) . ?
O3 N6 1.2324(14) . ?
O4 N6 1.2237(14) . ?
O5 N7 1.2312(15) . ?
O6 N7 1.2218(16) . ?
O7 N8 1.2170(15) . ?
O8 N8 1.2330(14) . ?
N1 N2 1.3263(16) . ?
N1 C1 1.3458(16) . ?
N1 H1N 0.904(18) . ?
N2 C3 1.3280(15) . ?
N3 N4 1.3321(16) . ?
N3 C4 1.3406(16) . ?
N3 H2N 0.87(2) . ?
N4 C6 1.3285(16) . ?
N5 C1 1.4355(17) . ?
N6 C3 1.4388(18) . ?
N7 C4 1.4325(17) . ?
N8 C6 1.4473(16) . ?
C1 C2 1.3807(16) . ?
C2 C3 1.4050(16) . ?
C2 C5 1.4644(15) . ?
C4 C5 1.3826(16) . ?
C5 C6 1.4015(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 111.96(11) . . ?
N2 N1 H1N 119.3(11) . . ?
C1 N1 H1N 128.7(11) . . ?
N1 N2 C3 103.89(10) . . ?
N4 N3 C4 112.12(10) . . ?
N4 N3 H2N 119.3(13) . . ?
C4 N3 H2N 128.5(14) . . ?
C6 N4 N3 103.43(10) . . ?
O2 N5 O1 125.91(13) . . ?
O2 N5 C1 117.76(11) . . ?
O1 N5 C1 116.33(11) . . ?
O4 N6 O3 125.08(12) . . ?
O4 N6 C3 117.36(10) . . ?
O3 N6 C3 117.55(11) . . ?
O6 N7 O5 125.61(12) . . ?
O6 N7 C4 117.71(11) . . ?
O5 N7 C4 116.68(11) . . ?
O7 N8 O8 125.23(12) . . ?
O7 N8 C6 119.09(11) . . ?
O8 N8 C6 115.68(10) . . ?
N1 C1 C2 109.07(11) . . ?
N1 C1 N5 120.18(11) . . ?
C2 C1 N5 130.72(11) . . ?
C1 C2 C3 100.95(10) . . ?
C1 C2 C5 129.34(11) . . ?
C3 C2 C5 129.68(11) . . ?
N2 C3 C2 114.13(11) . . ?
N2 C3 N6 117.99(10) . . ?
C2 C3 N6 127.84(10) . . ?
N3 C4 C5 109.12(11) . . ?
N3 C4 N7 120.85(10) . . ?
C5 C4 N7 130.03(11) . . ?
C4 C5 C6 100.85(10) . . ?
C4 C5 C2 128.66(11) . . ?
C6 C5 C2 130.37(11) . . ?
N4 C6 C5 114.48(11) . . ?
N4 C6 N8 118.98(11) . . ?
C5 C6 N8 126.49(10) . . ?

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
C1 N1 N2 C3 -0.76(14) . . . . ?
C4 N3 N4 C6 -0.05(15) . . . . ?
N2 N1 C1 C2 0.83(15) . . . . ?
N2 N1 C1 N5 -177.59(11) . . . . ?
O2 N5 C1 N1 -177.74(12) . . . . ?
O1 N5 C1 N1 2.54(19) . . . . ?
O2 N5 C1 C2 4.2(2) . . . . ?
O1 N5 C1 C2 -175.48(14) . . . . ?
N1 C1 C2 C3 -0.51(13) . . . . ?
N5 C1 C2 C3 177.69(13) . . . . ?
N1 C1 C2 C5 -178.56(12) . . . . ?
N5 C1 C2 C5 -0.4(2) . . . . ?
N1 N2 C3 C2 0.42(14) . . . . ?
N1 N2 C3 N6 178.34(11) . . . . ?
C1 C2 C3 N2 0.05(14) . . . . ?
C5 C2 C3 N2 178.09(11) . . . . ?
C1 C2 C3 N6 -177.63(12) . . . . ?
C5 C2 C3 N6 0.4(2) . . . . ?
O4 N6 C3 N2 169.76(12) . . . . ?
O3 N6 C3 N2 -9.47(18) . . . . ?
O4 N6 C3 C2 -12.6(2) . . . . ?
O3 N6 C3 C2 168.13(13) . . . . ?
N4 N3 C4 C5 0.13(15) . . . . ?
N4 N3 C4 N7 -179.82(11) . . . . ?
O6 N7 C4 N3 -175.15(12) . . . . ?
O5 N7 C4 N3 5.12(18) . . . . ?
O6 N7 C4 C5 4.9(2) . . . . ?
O5 N7 C4 C5 -174.82(13) . . . . ?
N3 C4 C5 C6 -0.14(13) . . . . ?
N7 C4 C5 C6 179.80(12) . . . . ?
N3 C4 C5 C2 -176.48(11) . . . . ?
N7 C4 C5 C2 3.5(2) . . . . ?
C1 C2 C5 C4 -112.30(16) . . . . ?
C3 C2 C5 C4 70.18(18) . . . . ?
C1 C2 C5 C6 72.41(19) . . . . ?
C3 C2 C5 C6 -105.11(17) . . . . ?
N3 N4 C6 C5 -0.04(15) . . . . ?
N3 N4 C6 N8 177.55(11) . . . . ?
C4 C5 C6 N4 0.11(14) . . . . ?
C2 C5 C6 N4 176.37(12) . . . . ?
C4 C5 C6 N8 -177.27(12) . . . . ?
C2 C5 C6 N8 -1.0(2) . . . . ?
O7 N8 C6 N4 -21.87(18) . . . . ?
O8 N8 C6 N4 158.91(12) . . . . ?
O7 N8 C6 C5 155.40(13) . . . . ?
O8 N8 C6 C5 -23.82(18) . . . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.039


####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1836408'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
3,3',5,5'-Tetranitro-4,4'-bipyrazole Hydrate
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N8 O8, H2 O'
_chemical_formula_sum            'C6 H4 N8 O9'
_chemical_formula_weight         332.17

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   11.1017(9)
_cell_length_b                   13.9227(10)
_cell_length_c                   8.2166(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.654(10)
_cell_angle_gamma                90
_cell_volume                     1188.38(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    5099
_cell_measurement_theta_min      2.446
_cell_measurement_theta_max      27.991

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe Image Plate Diffraction System'
_diffrn_measurement_method       'φ oscillation scans'
_diffrn_reflns_number            5099
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.446
_diffrn_reflns_theta_max         27.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_point_group_measured_fraction_full 0.831
_reflns_number_total             2319
_reflns_number_gt                2059
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_max     0.624
_reflns_Friedel_fraction_full    0.661

_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       'IPDS Software (Stoe & Cie, 2000)'
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2319
_refine_ls_number_parameters     224
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0501
_refine_ls_wR_factor_gt          0.0493
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_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
O1 O 0.06584(15) 0.09577(15) 0.2301(2) 0.0523(5) Uani 1 1 d . . . . .
O2 O -0.12595(13) 0.08090(14) 0.23632(18) 0.0434(4) Uani 1 1 d . . . . .
O3 O 0.34561(13) 0.19915(13) 0.91721(19) 0.0414(4) Uani 1 1 d . . . . .
O4 O 0.19935(15) 0.20127(13) 1.03580(19) 0.0398(4) Uani 1 1 d . . . . .
O5 O 0.33970(17) -0.01017(15) 0.7075(3) 0.0576(5) Uani 1 1 d . . . . .
O6 O 0.50830(14) -0.01601(13) 0.6343(2) 0.0446(4) Uani 1 1 d . . . . .
O7 O 0.11181(13) 0.33849(13) 0.4179(2) 0.0436(4) Uani 1 1 d . . . . .
O8 O 0.25709(14) 0.39449(12) 0.3236(2) 0.0383(4) Uani 1 1 d . . . . .
N1 N -0.04078(14) 0.11550(12) 0.5796(2) 0.0255(3) Uani 1 1 d . . . . .
N2 N 0.02187(13) 0.14019(13) 0.74313(19) 0.0259(3) Uani 1 1 d . . . . .
N3 N 0.40836(14) 0.24332(14) 0.44499(19) 0.0265(3) Uani 1 1 d . . . . .
N4 N 0.46532(13) 0.16142(13) 0.5091(2) 0.0277(3) Uani 1 1 d . . . . .
N5 N -0.01174(15) 0.09738(14) 0.3041(2) 0.0309(4) Uani 1 1 d . . . . .
N6 N 0.23536(15) 0.18867(13) 0.9135(2) 0.0281(3) Uani 1 1 d . . . . .
N7 N 0.21476(14) 0.33426(13) 0.39667(19) 0.0283(3) Uani 1 1 d . . . . .
N8 N 0.41269(15) 0.02404(14) 0.6422(2) 0.0334(4) Uani 1 1 d . . . . .
C1 C 0.03670(16) 0.11961(14) 0.4860(2) 0.0233(3) Uani 1 1 d . . . . .
C2 C 0.15741(16) 0.14853(14) 0.5900(2) 0.0231(4) Uani 1 1 d . . . . .
C3 C 0.14095(16) 0.15943(14) 0.7497(2) 0.0241(4) Uani 1 1 d . . . . .
C4 C 0.29282(17) 0.25102(15) 0.4611(2) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.26991(15) 0.17037(15) 0.5422(2) 0.0228(4) Uani 1 1 d . . . . .
C6 C 0.38237(17) 0.11724(14) 0.5670(2) 0.0254(4) Uani 1 1 d . . . . .
O1W O 0.70622(14) 0.09442(15) 0.4452(2) 0.0470(5) Uani 1 1 d . . . . .
H1N H -0.119(2) 0.1063(17) 0.539(3) 0.028(6) Uiso 1 1 d . . . . .
H2N H 0.437(2) 0.2881(19) 0.397(3) 0.033(6) Uiso 1 1 d . . . . .
H1W H 0.644(4) 0.108(3) 0.479(5) 0.078(11) Uiso 1 1 d . . . . .
H2W H 0.677(3) 0.056(3) 0.364(4) 0.063(9) 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 N5 1.217(2) . ?
O2 N5 1.213(2) . ?
O3 N6 1.222(2) . ?
O4 N6 1.218(2) . ?
O5 N8 1.216(2) . ?
O6 N8 1.221(2) . ?
O7 N7 1.2170(19) . ?
O8 N7 1.218(2) . ?
N1 N2 1.322(2) . ?
N1 C1 1.342(2) . ?
N1 H1N 0.83(2) . ?
N2 C3 1.331(2) . ?
N3 N4 1.320(2) . ?
N3 C4 1.340(2) . ?
N3 H2N 0.85(3) . ?
N4 C6 1.327(2) . ?
N5 C1 1.433(2) . ?
N6 C3 1.442(2) . ?
N7 C4 1.432(3) . ?
N8 C6 1.425(3) . ?
C1 C2 1.371(3) . ?
C2 C3 1.396(3) . ?
C2 C5 1.467(2) . ?
C4 C5 1.374(3) . ?
C5 C6 1.403(3) . ?
O1W H1W 0.85(4) . ?
O1W H2W 0.82(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 110.95(14) . . ?
N2 N1 H1N 123.5(15) . . ?
C1 N1 H1N 125.0(15) . . ?
N1 N2 C3 104.63(14) . . ?
N4 N3 C4 111.73(15) . . ?
N4 N3 H2N 127.8(16) . . ?
C4 N3 H2N 120.5(16) . . ?
N3 N4 C6 104.36(14) . . ?
O2 N5 O1 125.20(18) . . ?
O2 N5 C1 117.80(15) . . ?
O1 N5 C1 116.99(15) . . ?
O4 N6 O3 125.41(17) . . ?
O4 N6 C3 117.94(15) . . ?
O3 N6 C3 116.66(14) . . ?
O7 N7 O8 125.63(18) . . ?
O7 N7 C4 117.55(16) . . ?
O8 N7 C4 116.82(15) . . ?
O5 N8 O6 124.9(2) . . ?
O5 N8 C6 117.12(17) . . ?
O6 N8 C6 118.00(16) . . ?
N1 C1 C2 109.80(15) . . ?
N1 C1 N5 120.54(15) . . ?
C2 C1 N5 129.64(15) . . ?
C1 C2 C3 101.20(14) . . ?
C1 C2 C5 129.16(16) . . ?
C3 C2 C5 129.43(17) . . ?
N2 C3 C2 113.41(16) . . ?
N2 C3 N6 118.63(15) . . ?
C2 C3 N6 127.95(15) . . ?
N3 C4 C5 109.26(17) . . ?
N3 C4 N7 120.25(16) . . ?
C5 C4 N7 130.49(16) . . ?
C4 C5 C6 101.18(15) . . ?
C4 C5 C2 128.28(17) . . ?
C6 C5 C2 130.54(18) . . ?
N4 C6 C5 113.46(18) . . ?
N4 C6 N8 119.32(16) . . ?
C5 C6 N8 127.21(16) . . ?
H1W O1W H2W 106(3) . . ?

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
C1 N1 N2 C3 -0.3(2) . . . . ?
C4 N3 N4 C6 -0.1(2) . . . . ?
N2 N1 C1 C2 -0.1(2) . . . . ?
N2 N1 C1 N5 -178.88(17) . . . . ?
O2 N5 C1 N1 4.6(3) . . . . ?
O1 N5 C1 N1 -174.81(19) . . . . ?
O2 N5 C1 C2 -173.9(2) . . . . ?
O1 N5 C1 C2 6.7(3) . . . . ?
N1 C1 C2 C3 0.5(2) . . . . ?
N5 C1 C2 C3 179.07(19) . . . . ?
N1 C1 C2 C5 -174.69(18) . . . . ?
N5 C1 C2 C5 3.9(3) . . . . ?
N1 N2 C3 C2 0.6(2) . . . . ?
N1 N2 C3 N6 -179.73(16) . . . . ?
C1 C2 C3 N2 -0.7(2) . . . . ?
C5 C2 C3 N2 174.45(18) . . . . ?
C1 C2 C3 N6 179.72(18) . . . . ?
C5 C2 C3 N6 -5.1(3) . . . . ?
O4 N6 C3 N2 -5.3(3) . . . . ?
O3 N6 C3 N2 175.03(18) . . . . ?
O4 N6 C3 C2 174.3(2) . . . . ?
O3 N6 C3 C2 -5.4(3) . . . . ?
N4 N3 C4 C5 0.6(2) . . . . ?
N4 N3 C4 N7 -178.98(17) . . . . ?
O7 N7 C4 N3 -178.51(17) . . . . ?
O8 N7 C4 N3 2.1(3) . . . . ?
O7 N7 C4 C5 2.0(3) . . . . ?
O8 N7 C4 C5 -177.34(19) . . . . ?
N3 C4 C5 C6 -0.74(19) . . . . ?
N7 C4 C5 C6 178.76(19) . . . . ?
N3 C4 C5 C2 178.62(17) . . . . ?
N7 C4 C5 C2 -1.9(3) . . . . ?
C1 C2 C5 C4 76.1(3) . . . . ?
C3 C2 C5 C4 -97.7(3) . . . . ?
C1 C2 C5 C6 -104.7(3) . . . . ?
C3 C2 C5 C6 81.5(3) . . . . ?
N3 N4 C6 C5 -0.4(2) . . . . ?
N3 N4 C6 N8 178.56(16) . . . . ?
C4 C5 C6 N4 0.7(2) . . . . ?
C2 C5 C6 N4 -178.64(18) . . . . ?
C4 C5 C6 N8 -178.14(18) . . . . ?
C2 C5 C6 N8 2.5(3) . . . . ?
O5 N8 C6 N4 173.6(2) . . . . ?
O6 N8 C6 N4 -7.4(3) . . . . ?
O5 N8 C6 C5 -7.6(3) . . . . ?
O6 N8 C6 C5 171.34(19) . . . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.029




#   -------------  END of CIF  -----------------#

