# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_xb8321_0m
_database_code_depnum_ccdc_archive 'CCDC 1410323'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,4-dinitroxymethyl-3,6-dinitropyrazolo[4,3-c]pyrazole 
;
_chemical_name_common            ?
_chemical_melting_point          none
_chemical_formula_moiety         C6H4N8O10
_chemical_formula_sum            'C6 H4 N8 O10'
_chemical_formula_weight         348.17

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.743(4)
_cell_length_b                   8.302(5)
_cell_length_c                   10.605(6)
_cell_angle_alpha                85.500(11)
_cell_angle_beta                 78.807(10)
_cell_angle_gamma                71.153(9)
_cell_volume                     632.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    428
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      20.69

_exptl_crystal_description       block
_exptl_crystal_colour            yellowish
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9386
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_process_details   SADABS(Sheldrick,1997)

_exptl_special_details           
; 
 Sheldrick, G. M. (1997). SADABS. University of G?ttingen,
Germany. 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3141
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0971
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2222
_reflns_number_gt                1182
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1004P)²+1.1240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.006(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2222
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.0872
_refine_ls_wR_factor_ref         0.2603
_refine_ls_wR_factor_gt          0.2173
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2108(8) 0.7077(8) 0.7135(6) 0.0720(19) Uani 1 1 d . . .
N2 N 0.2149(7) 0.5207(7) 0.5533(5) 0.0488(14) Uani 1 1 d . . .
N3 N 0.3369(6) 0.4274(6) 0.4569(5) 0.0421(12) Uani 1 1 d . . .
N4 N 0.2782(12) 0.0661(10) 0.4507(8) 0.083(2) Uani 1 1 d . . .
N5 N 0.2718(9) 0.3881(9) -0.0138(7) 0.0690(18) Uani 1 1 d . . .
N6 N 0.1915(6) 0.0633(6) -0.0470(5) 0.0406(12) Uani 1 1 d . . .
N7 N 0.2691(6) -0.0429(6) 0.0427(5) 0.0446(13) Uani 1 1 d . . .
N8 N 0.1903(9) -0.2418(7) 0.2003(6) 0.0624(16) Uani 1 1 d . . .
O1 O 0.0434(7) 0.7416(8) 0.7467(6) 0.100(2) Uani 1 1 d . . .
O2 O 0.3083(7) 0.7656(8) 0.7636(5) 0.090(2) Uani 1 1 d . . .
O3 O 0.3641(8) 0.1649(8) 0.3612(6) 0.0914(18) Uani 1 1 d . . .
O4 O 0.3373(15) -0.0723(10) 0.4496(11) 0.181(5) Uani 1 1 d . . .
O5 O 0.1532(14) 0.1568(14) 0.5175(10) 0.188(5) Uani 1 1 d . . .
O6 O 0.3468(8) 0.2893(8) 0.0594(5) 0.0795(17) Uani 1 1 d . . .
O7 O 0.2175(11) 0.5405(9) -0.0133(9) 0.140(3) Uani 1 1 d . . .
O8 O 0.2302(6) 0.3292(6) -0.1213(5) 0.0591(13) Uani 1 1 d . . .
O9 O 0.3469(7) -0.2947(7) 0.2226(6) 0.0854(18) Uani 1 1 d . . .
O10 O 0.0615(7) -0.2907(7) 0.2555(5) 0.0819(17) Uani 1 1 d . . .
C1 C 0.3066(8) 0.5941(8) 0.6093(6) 0.0459(15) Uani 1 1 d . . .
C2 C 0.5078(7) 0.4473(7) 0.4509(5) 0.0385(14) Uani 1 1 d . . .
C3 C 0.2729(9) 0.3451(7) 0.3697(7) 0.0502(16) Uani 1 1 d . . .
H3A H 0.2916 0.3962 0.2849 0.060 Uiso 1 1 calc R . .
H3B H 0.1407 0.3656 0.3972 0.060 Uiso 1 1 calc R . .
C4 C 0.3018(8) 0.1482(8) -0.1329(6) 0.0463(16) Uani 1 1 d . . .
H4A H 0.3071 0.1185 -0.2205 0.056 Uiso 1 1 calc R . .
H4B H 0.4273 0.1089 -0.1153 0.056 Uiso 1 1 calc R . .
C5 C 0.0175(7) 0.0560(7) -0.0475(5) 0.0383(14) Uani 1 1 d . . .
C6 C 0.1439(8) -0.1156(7) 0.1005(6) 0.0431(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.048(4) 0.100(5) 0.070(4) -0.045(4) 0.003(3) -0.022(3)
N2 0.043(3) 0.056(3) 0.048(3) -0.013(3) -0.005(2) -0.014(2)
N3 0.036(3) 0.045(3) 0.048(3) -0.010(2) -0.012(2) -0.012(2)
N4 0.106(6) 0.057(5) 0.089(5) 0.021(4) -0.030(5) -0.030(4)
N5 0.072(4) 0.059(5) 0.083(5) -0.019(4) -0.009(4) -0.030(3)
N6 0.033(3) 0.042(3) 0.049(3) -0.005(2) -0.008(2) -0.014(2)
N7 0.035(3) 0.043(3) 0.057(3) -0.002(3) -0.011(2) -0.012(2)
N8 0.063(4) 0.059(4) 0.075(4) 0.004(3) -0.032(3) -0.022(3)
O1 0.037(3) 0.154(6) 0.107(4) -0.081(4) 0.006(3) -0.019(3)
O2 0.066(3) 0.117(5) 0.091(4) -0.065(4) 0.002(3) -0.028(3)
O3 0.086(4) 0.097(5) 0.098(4) -0.018(4) -0.016(3) -0.033(3)
O4 0.253(11) 0.054(5) 0.266(12) 0.027(6) -0.135(10) -0.045(6)
O5 0.161(9) 0.172(9) 0.190(10) -0.068(8) 0.011(7) -0.004(7)
O6 0.088(4) 0.085(4) 0.069(4) -0.024(3) -0.018(3) -0.024(3)
O7 0.182(8) 0.057(4) 0.191(8) -0.033(5) -0.045(6) -0.038(4)
O8 0.056(3) 0.050(3) 0.077(3) 0.004(2) -0.018(2) -0.023(2)
O9 0.071(4) 0.090(4) 0.111(4) 0.035(3) -0.055(3) -0.032(3)
O10 0.068(3) 0.102(4) 0.088(4) 0.034(3) -0.030(3) -0.043(3)
C1 0.040(3) 0.052(4) 0.044(3) -0.016(3) -0.008(3) -0.009(3)
C2 0.041(3) 0.035(3) 0.039(3) -0.003(2) -0.010(3) -0.010(3)
C3 0.053(4) 0.038(4) 0.067(4) -0.005(3) -0.023(3) -0.015(3)
C4 0.038(3) 0.054(4) 0.052(4) -0.011(3) -0.002(3) -0.023(3)
C5 0.030(3) 0.032(3) 0.051(3) -0.009(2) -0.004(3) -0.006(2)
C6 0.041(3) 0.041(3) 0.048(3) -0.003(3) -0.017(3) -0.008(3)

_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
N1 O1 1.219(7) . ?
N1 O2 1.230(7) . ?
N1 C1 1.434(8) . ?
N2 C1 1.315(7) . ?
N2 N3 1.346(6) . ?
N3 C2 1.375(7) . ?
N3 C3 1.436(7) . ?
N4 O4 1.091(9) . ?
N4 O5 1.163(10) . ?
N4 O3 1.414(9) . ?
N5 O6 1.175(8) . ?
N5 O7 1.198(8) . ?
N5 O8 1.405(8) . ?
N6 N7 1.338(7) . ?
N6 C5 1.369(7) . ?
N6 C4 1.430(7) . ?
N7 C6 1.331(7) . ?
N8 O9 1.212(7) . ?
N8 O10 1.225(7) . ?
N8 C6 1.441(8) . ?
O3 C3 1.435(8) . ?
O8 C4 1.430(7) . ?
C1 C2 1.397(8) 2_666 ?
C2 C2 1.375(11) 2_666 ?
C2 C1 1.397(8) 2_666 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C5 1.365(11) 2 ?
C5 C6 1.398(8) 2 ?
C6 C5 1.398(8) 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
O1 N1 O2 124.3(5) . . ?
O1 N1 C1 120.0(6) . . ?
O2 N1 C1 115.6(5) . . ?
C1 N2 N3 107.0(5) . . ?
N2 N3 C2 109.7(4) . . ?
N2 N3 C3 119.8(5) . . ?
C2 N3 C3 130.0(5) . . ?
O4 N4 O5 131.8(12) . . ?
O4 N4 O3 119.2(10) . . ?
O5 N4 O3 109.0(9) . . ?
O6 N5 O7 130.6(8) . . ?
O6 N5 O8 119.4(6) . . ?
O7 N5 O8 110.0(7) . . ?
N7 N6 C5 110.6(5) . . ?
N7 N6 C4 118.5(4) . . ?
C5 N6 C4 130.5(5) . . ?
C6 N7 N6 106.2(4) . . ?
O9 N8 O10 124.7(6) . . ?
O9 N8 C6 120.8(6) . . ?
O10 N8 C6 114.5(6) . . ?
N4 O3 C3 114.5(6) . . ?
N5 O8 C4 113.1(5) . . ?
N2 C1 C2 111.3(5) . 2_666 ?
N2 C1 N1 119.9(5) . . ?
C2 C1 N1 128.7(6) 2_666 . ?
C2 C2 N3 107.4(6) 2_666 . ?
C2 C2 C1 104.7(6) 2_666 2_666 ?
N3 C2 C1 148.0(5) . 2_666 ?
N3 C3 O3 113.9(5) . . ?
N3 C3 H3A 108.8 . . ?
O3 C3 H3A 108.8 . . ?
N3 C3 H3B 108.8 . . ?
O3 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N6 C4 O8 112.4(4) . . ?
N6 C4 H4A 109.1 . . ?
O8 C4 H4A 109.1 . . ?
N6 C4 H4B 109.1 . . ?
O8 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C5 C5 N6 107.4(6) 2 . ?
C5 C5 C6 104.9(6) 2 2 ?
N6 C5 C6 147.7(6) . 2 ?
N7 C6 C5 110.9(5) . 2 ?
N7 C6 N8 119.2(5) . . ?
C5 C6 N8 129.9(6) 2 . ?

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 N2 N3 C2 -1.7(7) . . . . ?
C1 N2 N3 C3 -173.9(5) . . . . ?
C5 N6 N7 C6 -0.9(6) . . . . ?
C4 N6 N7 C6 -174.3(5) . . . . ?
O4 N4 O3 C3 178.9(8) . . . . ?
O5 N4 O3 C3 -3.4(10) . . . . ?
O6 N5 O8 C4 -5.0(8) . . . . ?
O7 N5 O8 C4 176.1(6) . . . . ?
N3 N2 C1 C2 1.0(7) . . . 2_666 ?
N3 N2 C1 N1 177.7(6) . . . . ?
O1 N1 C1 N2 -2.9(11) . . . . ?
O2 N1 C1 N2 177.3(7) . . . . ?
O1 N1 C1 C2 173.1(7) . . . 2_666 ?
O2 N1 C1 C2 -6.7(11) . . . 2_666 ?
N2 N3 C2 C2 1.7(8) . . . 2_666 ?
C3 N3 C2 C2 172.9(6) . . . 2_666 ?
N2 N3 C2 C1 179.8(9) . . . 2_666 ?
C3 N3 C2 C1 -9.0(14) . . . 2_666 ?
N2 N3 C3 O3 -124.3(6) . . . . ?
C2 N3 C3 O3 65.2(9) . . . . ?
N4 O3 C3 N3 89.6(7) . . . . ?
N7 N6 C4 O8 -117.9(6) . . . . ?
C5 N6 C4 O8 70.2(7) . . . . ?
N5 O8 C4 N6 78.1(6) . . . . ?
N7 N6 C5 C5 1.4(7) . . . 2 ?
C4 N6 C5 C5 173.8(6) . . . 2 ?
N7 N6 C5 C6 179.1(8) . . . 2 ?
C4 N6 C5 C6 -8.5(13) . . . 2 ?
N6 N7 C6 C5 0.1(6) . . . 2 ?
N6 N7 C6 N8 178.1(5) . . . . ?
O9 N8 C6 N7 -7.7(9) . . . . ?
O10 N8 C6 N7 174.0(6) . . . . ?
O9 N8 C6 C5 169.9(6) . . . 2 ?
O10 N8 C6 C5 -8.4(10) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_xb8881
_database_code_depnum_ccdc_archive 'CCDC 1434787'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,4-diamino-3,6-dinitropyrazolo[4,3-c]pyrazole 
;
_chemical_name_common            ?
_chemical_melting_point          none
_chemical_formula_moiety         C4H4N8O4
_chemical_formula_sum            'C4 H4 N8 O4'
_chemical_formula_weight         228.15

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.082(2)
_cell_length_b                   5.4849(13)
_cell_length_c                   16.575(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     825.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2044
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9515
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3659
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         25.09
_reflns_number_total             736
_reflns_number_gt                690
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.1878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         736
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.91365(13) 0.3274(2) 0.36017(7) 0.0362(3) Uani 1 1 d . . .
N2 N 0.86091(12) 0.31381(19) 0.50191(6) 0.0323(3) Uani 1 1 d . . .
N3 N 0.89811(12) 0.17243(19) 0.56434(6) 0.0305(3) Uani 1 1 d . . .
N4 N 0.83558(16) 0.2219(2) 0.63958(7) 0.0381(3) Uani 1 1 d . . .
O1 O 0.84216(13) 0.5134(2) 0.35175(7) 0.0548(4) Uani 1 1 d . . .
O2 O 0.97739(14) 0.2221(2) 0.30522(6) 0.0537(4) Uani 1 1 d . . .
C1 C 0.92890(14) 0.2206(2) 0.43810(7) 0.0300(3) Uani 1 1 d . . .
C2 C 0.98851(13) -0.0134(2) 0.54078(8) 0.0288(3) Uani 1 1 d . . .
H4A H 0.779(2) 0.093(4) 0.6510(11) 0.052(5) Uiso 1 1 d . . .
H4B H 0.904(2) 0.221(3) 0.6739(12) 0.053(5) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0363(6) 0.0379(7) 0.0344(6) 0.0056(5) -0.0013(5) 0.0018(5)
N2 0.0347(6) 0.0288(6) 0.0333(7) 0.0009(4) -0.0015(4) 0.0012(4)
N3 0.0338(6) 0.0300(6) 0.0277(6) -0.0023(4) 0.0002(4) 0.0024(5)
N4 0.0457(7) 0.0396(7) 0.0288(7) -0.0039(5) 0.0044(5) 0.0032(6)
O1 0.0603(7) 0.0501(7) 0.0541(7) 0.0202(5) 0.0060(5) 0.0214(5)
O2 0.0687(8) 0.0619(8) 0.0306(6) 0.0048(5) 0.0042(5) 0.0194(6)
C1 0.0321(7) 0.0285(7) 0.0294(7) 0.0003(5) -0.0022(5) -0.0008(5)
C2 0.0300(6) 0.0291(7) 0.0273(6) -0.0022(5) -0.0021(4) -0.0009(5)

_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
N1 O1 1.2172(16) . ?
N1 O2 1.2240(15) . ?
N1 C1 1.4250(17) . ?
N2 C1 1.3274(16) . ?
N2 N3 1.3364(15) . ?
N3 C2 1.3659(16) . ?
N3 N4 1.3969(16) . ?
N4 H4A 0.89(2) . ?
N4 H4B 0.84(2) . ?
C1 C2 1.4057(17) 5_756 ?
C2 C2 1.376(3) 5_756 ?
C2 C1 1.4057(17) 5_756 ?

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
O1 N1 O2 124.21(11) . . ?
O1 N1 C1 120.02(12) . . ?
O2 N1 C1 115.76(11) . . ?
C1 N2 N3 106.01(10) . . ?
N2 N3 C2 111.32(10) . . ?
N2 N3 N4 118.41(10) . . ?
C2 N3 N4 130.13(11) . . ?
N3 N4 H4A 105.7(11) . . ?
N3 N4 H4B 107.4(13) . . ?
H4A N4 H4B 106.2(17) . . ?
N2 C1 C2 111.17(11) . 5_756 ?
N2 C1 N1 121.24(12) . . ?
C2 C1 N1 127.59(12) 5_756 . ?
N3 C2 C2 107.00(13) . 5_756 ?
N3 C2 C1 148.50(12) . 5_756 ?
C2 C2 C1 104.50(13) 5_756 5_756 ?

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 N2 N3 C2 -0.72(14) . . . . ?
C1 N2 N3 N4 -176.87(12) . . . . ?
N3 N2 C1 C2 0.32(14) . . . 5_756 ?
N3 N2 C1 N1 -179.96(11) . . . . ?
O1 N1 C1 N2 3.1(2) . . . . ?
O2 N1 C1 N2 -177.78(12) . . . . ?
O1 N1 C1 C2 -177.27(13) . . . 5_756 ?
O2 N1 C1 C2 1.9(2) . . . 5_756 ?
N2 N3 C2 C2 0.84(17) . . . 5_756 ?
N4 N3 C2 C2 176.41(14) . . . 5_756 ?
N2 N3 C2 C1 179.75(19) . . . 5_756 ?
N4 N3 C2 C1 -4.7(3) . . . 5_756 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.151
_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_xb7189_0m
_database_code_depnum_ccdc_archive 'CCDC 1487948'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 3,6-dinitropyrazolo[4,3-c]-pyrazole 
;
_chemical_name_common            ?
_chemical_melting_point          none
_chemical_formula_moiety         C4H6N6O6
_chemical_formula_sum            'C4 H6 N6 O6'
_chemical_formula_weight         234.15

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0574(14)
_cell_length_b                   9.395(3)
_cell_length_c                   9.872(3)
_cell_angle_alpha                100.110(4)
_cell_angle_beta                 97.281(4)
_cell_angle_gamma                100.102(4)
_cell_volume                     448.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1752
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.02

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9429
_exptl_absorpt_correction_T_max  0.9603
_exptl_absorpt_process_details   SADABS(Sheldrick,1997)

_exptl_special_details           
; 
 Sheldrick, G. M. (1997). SADABS. University of G?ttingen,
Germany. 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2225
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.09
_reflns_number_total             1579
_reflns_number_gt                1445
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.3601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.105(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1579
_refine_ls_number_parameters     162
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.3566(4) 0.13907(19) 0.8617(2) 0.0639(5) Uani 1 1 d D . .
N5 N 0.2729(4) 0.52399(19) 0.85306(19) 0.0449(5) Uani 1 1 d . . .
O3 O 0.0894(4) 0.63616(17) 0.45435(19) 0.0611(5) Uani 1 1 d . . .
O1 O 0.0633(4) 0.85727(18) 0.9378(2) 0.0633(5) Uani 1 1 d . . .
O4 O 0.3764(4) 0.69475(18) 0.3192(2) 0.0633(5) Uani 1 1 d . . .
N4 N 0.2777(4) 0.97173(19) 0.35581(19) 0.0443(5) Uani 1 1 d . . .
O5 O 0.3246(5) 0.3675(2) 0.3444(2) 0.0688(6) Uani 1 1 d D . .
N2 N 0.2130(4) 0.72430(19) 0.39503(19) 0.0448(5) Uani 1 1 d . . .
N6 N 0.1935(4) 0.40338(18) 0.90548(19) 0.0435(5) Uani 1 1 d . . .
H6 H 0.2465 0.3214 0.8842 0.052 Uiso 1 1 calc R . .
N1 N 0.1847(4) 0.7691(2) 0.8781(2) 0.0493(5) Uani 1 1 d . . .
O2 O 0.3314(4) 0.79712(19) 0.7933(2) 0.0689(6) Uani 1 1 d . . .
N3 N 0.1869(4) 1.09570(18) 0.40087(19) 0.0429(5) Uani 1 1 d . . .
H3 H 0.2329 1.1781 0.3751 0.052 Uiso 1 1 calc R . .
C13 C 0.1581(4) 0.8707(2) 0.4195(2) 0.0403(5) Uani 1 1 d . . .
C14 C 0.0181(4) 0.4284(2) 0.9965(2) 0.0398(5) Uani 1 1 d . . .
C15 C 0.1468(4) 0.6260(2) 0.9115(2) 0.0420(5) Uani 1 1 d . . .
C16 C 0.0125(4) 1.0724(2) 0.4927(2) 0.0389(5) Uani 1 1 d . . .
H5A H 0.276(6) 0.440(3) 0.386(3) 0.081(10) Uiso 1 1 d D . .
H6A H 0.265(6) 0.069(3) 0.882(3) 0.083(11) Uiso 1 1 d D . .
H5B H 0.452(5) 0.405(3) 0.309(3) 0.079(10) Uiso 1 1 d D . .
H6B H 0.452(5) 0.109(3) 0.807(3) 0.067(9) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O6 0.0809(13) 0.0373(9) 0.0893(14) 0.0197(9) 0.0485(11) 0.0223(9)
N5 0.0541(11) 0.0345(9) 0.0522(11) 0.0128(8) 0.0173(9) 0.0152(8)
O3 0.0817(13) 0.0368(9) 0.0793(12) 0.0236(8) 0.0403(10) 0.0195(8)
O1 0.0854(13) 0.0388(9) 0.0843(13) 0.0219(8) 0.0451(10) 0.0298(9)
O4 0.0816(13) 0.0438(9) 0.0805(12) 0.0182(8) 0.0450(10) 0.0267(9)
N4 0.0533(11) 0.0339(9) 0.0513(11) 0.0126(8) 0.0154(9) 0.0146(8)
O5 0.0895(15) 0.0380(9) 0.1000(15) 0.0271(10) 0.0587(12) 0.0252(9)
N2 0.0550(11) 0.0332(9) 0.0509(11) 0.0107(8) 0.0165(9) 0.0140(8)
N6 0.0534(11) 0.0301(9) 0.0533(11) 0.0108(8) 0.0158(9) 0.0176(8)
N1 0.0624(12) 0.0354(10) 0.0590(12) 0.0158(9) 0.0241(10) 0.0175(9)
O2 0.0946(14) 0.0481(10) 0.0861(13) 0.0307(9) 0.0555(12) 0.0273(9)
N3 0.0537(11) 0.0297(9) 0.0518(11) 0.0157(8) 0.0166(9) 0.0123(8)
C13 0.0480(12) 0.0310(10) 0.0453(12) 0.0105(9) 0.0099(9) 0.0124(9)
C14 0.0462(12) 0.0307(10) 0.0446(11) 0.0080(8) 0.0078(9) 0.0125(8)
C15 0.0502(13) 0.0317(10) 0.0486(12) 0.0117(9) 0.0131(10) 0.0134(9)
C16 0.0448(12) 0.0316(10) 0.0434(11) 0.0114(8) 0.0093(9) 0.0105(8)

_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
O6 H6A 0.807(18) . ?
O6 H6B 0.811(18) . ?
N5 C15 1.331(3) . ?
N5 N6 1.346(2) . ?
O3 N2 1.225(2) . ?
O1 N1 1.229(2) . ?
O4 N2 1.219(2) . ?
N4 C13 1.329(3) . ?
N4 N3 1.350(2) . ?
O5 H5A 0.821(18) . ?
O5 H5B 0.825(18) . ?
N2 C13 1.436(3) . ?
N6 C14 1.361(3) . ?
N6 H6 0.8600 . ?
N1 O2 1.219(2) . ?
N1 C15 1.426(3) . ?
N3 C16 1.361(3) . ?
N3 H3 0.8600 . ?
C13 C16 1.404(3) 2_576 ?
C14 C14 1.380(4) 2_567 ?
C14 C15 1.409(3) 2_567 ?
C15 C14 1.409(3) 2_567 ?
C16 C16 1.379(4) 2_576 ?
C16 C13 1.404(3) 2_576 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H6A O6 H6B 109(3) . . ?
C15 N5 N6 105.91(17) . . ?
C13 N4 N3 105.67(17) . . ?
H5A O5 H5B 103(3) . . ?
O4 N2 O3 124.09(18) . . ?
O4 N2 C13 119.59(18) . . ?
O3 N2 C13 116.32(18) . . ?
N5 N6 C14 111.01(16) . . ?
N5 N6 H6 124.5 . . ?
C14 N6 H6 124.5 . . ?
O2 N1 O1 123.94(19) . . ?
O2 N1 C15 119.38(18) . . ?
O1 N1 C15 116.68(18) . . ?
N4 N3 C16 110.73(16) . . ?
N4 N3 H3 124.6 . . ?
C16 N3 H3 124.6 . . ?
N4 C13 C16 111.81(18) . 2_576 ?
N4 C13 N2 120.11(18) . . ?
C16 C13 N2 128.08(19) 2_576 . ?
N6 C14 C14 107.7(2) . 2_567 ?
N6 C14 C15 148.24(19) . 2_567 ?
C14 C14 C15 104.1(2) 2_567 2_567 ?
N5 C15 C14 111.31(18) . 2_567 ?
N5 C15 N1 120.81(19) . . ?
C14 C15 N1 127.88(19) 2_567 . ?
N3 C16 C16 107.9(2) . 2_576 ?
N3 C16 C13 148.21(19) . 2_576 ?
C16 C16 C13 103.9(2) 2_576 2_576 ?

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
C15 N5 N6 C14 0.0(2) . . . . ?
C13 N4 N3 C16 0.3(2) . . . . ?
N3 N4 C13 C16 -0.1(2) . . . 2_576 ?
N3 N4 C13 N2 -179.53(18) . . . . ?
O4 N2 C13 N4 2.4(3) . . . . ?
O3 N2 C13 N4 -178.0(2) . . . . ?
O4 N2 C13 C16 -177.0(2) . . . 2_576 ?
O3 N2 C13 C16 2.7(3) . . . 2_576 ?
N5 N6 C14 C14 0.0(3) . . . 2_567 ?
N5 N6 C14 C15 179.9(3) . . . 2_567 ?
N6 N5 C15 C14 -0.1(3) . . . 2_567 ?
N6 N5 C15 N1 -179.7(2) . . . . ?
O2 N1 C15 N5 1.1(3) . . . . ?
O1 N1 C15 N5 -179.2(2) . . . . ?
O2 N1 C15 C14 -178.4(2) . . . 2_567 ?
O1 N1 C15 C14 1.3(4) . . . 2_567 ?
N4 N3 C16 C16 -0.4(3) . . . 2_576 ?
N4 N3 C16 C13 -179.8(3) . . . 2_576 ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.053
