#------------------------------------------------------------------------------
#$Date: 2016-09-01 10:04:56 +0300 (Thu, 01 Sep 2016) $
#$Revision: 186120 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/64/7226438.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7226438
loop_
_publ_author_name
'Li, Yanan'
'Shu, Yuan-jie'
'Wang, Bozhou'
'Zhang, Shengyong'
'Zhai, Lian-jie'
_publ_section_title
;
 Synthesis, structure and properties of neutral energetic materials based
 on N-functionalization of 3,6-dinitropyrazolo[4,3-c]pyrazole
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA19556C
_journal_year                    2016
_chemical_formula_moiety         C6H4N8O10
_chemical_formula_sum            'C6 H4 N8 O10'
_chemical_formula_weight         348.17
_chemical_melting_point          ?
_chemical_name_systematic
; 
 1,4-dinitroxymethyl-3,6-dinitropyrazolo[4,3-c]pyrazole 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-06-27 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                85.500(11)
_cell_angle_beta                 78.807(10)
_cell_angle_gamma                71.153(9)
_cell_formula_units_Z            2
_cell_length_a                   7.743(4)
_cell_length_b                   8.302(5)
_cell_length_c                   10.605(6)
_cell_measurement_reflns_used    428
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.69
_cell_measurement_theta_min      3.18
_cell_volume                     632.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3141
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9386
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS(Sheldrick,1997)
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.006(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.0872
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1004P)²+1.1240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2173
_refine_ls_wR_factor_ref         0.2603
_reflns_number_gt                1182
_reflns_number_total             2222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra19556c2.cif
_cod_data_source_block           xb8321_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7226438
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
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_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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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_4
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
