#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:01:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180284 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/70/7117022.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_7117022
loop_
_publ_author_name
'Jiaheng Zhang'
'Damon A. Parrish'
'Jean'ne M. Shreeve'
_publ_section_title
;
 Curious cases of 3,6-dinitropyrazolo[4,3-c]pyrazole-based energetic
 cocrystals with high nitrogen content: an alternative to salt formation
;
_journal_name_full               Chem.Commun.
_journal_page_first              7337
_journal_paper_doi               10.1039/C5cc01745A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         '2(C2 H4 N4), C4 H2 N6 O4'
_chemical_formula_sum            'C8 H10 N14 O4'
_chemical_formula_weight         366.30
_chemical_name_systematic
; 
 4H-1,2,4-triazol-4-amine 3,6-dinitro-1,4-dihydropyrazolo[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_date             2013-08-01
_audit_creation_method
'from SHELXTL CIF, local template and enCIFer'
_audit_update_record
;
2015-02-10 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                82.822(5)
_cell_angle_beta                 77.868(3)
_cell_angle_gamma                71.330(3)
_cell_formula_units_Z            1
_cell_length_a                   5.4207(13)
_cell_length_b                   6.797(2)
_cell_length_c                   10.530(3)
_cell_measurement_temperature    150(2)
_cell_volume                     358.65(17)
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '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  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3234
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0375P)²+0.1667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                1298
_reflns_number_total             1460
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c5cc01745a2.cif
_cod_data_source_block           shrv248
_cod_original_cell_volume        358.62(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117022
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1687(2) 0.03072(18) 0.34633(11) 0.0171(3) Uani 1 1 d . . .
H1 H 1.1642 0.0923 0.2678 0.021 Uiso 1 1 calc R . .
N2 N 1.3844(2) -0.10702(18) 0.38459(11) 0.0183(3) Uani 1 1 d . . .
C3 C 1.3091(3) -0.1632(2) 0.50895(13) 0.0169(3) Uani 1 1 d . . .
C4 C 1.0412(3) -0.0611(2) 0.55366(12) 0.0160(3) Uani 1 1 d . . .
N5 N 1.4931(2) -0.30783(18) 0.58092(11) 0.0195(3) Uani 1 1 d . . .
O6 O 1.7217(2) -0.38708(17) 0.52592(11) 0.0268(3) Uani 1 1 d . . .
O7 O 1.4066(2) -0.34327(18) 0.69641(10) 0.0285(3) Uani 1 1 d . . .
N8 N 0.4222(2) 0.24647(19) 1.03269(11) 0.0197(3) Uani 1 1 d . . .
N9 N 0.1900(2) 0.20955(18) 1.10045(11) 0.0189(3) Uani 1 1 d . . .
C10 C 0.0323(3) 0.2337(2) 1.01721(13) 0.0174(3) Uani 1 1 d . . .
H10 H -0.1394 0.2171 1.0379 0.021 Uiso 1 1 calc R . .
N11 N 0.1507(2) 0.28571(18) 0.89786(11) 0.0165(3) Uani 1 1 d . . .
C12 C 0.3915(3) 0.2927(2) 0.91202(13) 0.0183(3) Uani 1 1 d . . .
H12 H 0.5192 0.3265 0.8436 0.022 Uiso 1 1 calc R . .
N13 N 0.0353(3) 0.3225(2) 0.78502(12) 0.0221(3) Uani 1 1 d . . .
H13A H 0.165(4) 0.274(3) 0.7183(18) 0.027 Uiso 1 1 d . . .
H13B H -0.020(3) 0.459(3) 0.7697(17) 0.027 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 0.0156(5) 0.0200(6) 0.0140(5) 0.0016(4) -0.0024(4) -0.0043(5)
N2 0.0164(6) 0.0201(6) 0.0175(6) -0.0007(4) -0.0027(4) -0.0047(5)
C3 0.0149(6) 0.0181(7) 0.0171(6) -0.0010(5) -0.0026(5) -0.0047(5)
C4 0.0163(6) 0.0174(6) 0.0147(6) -0.0009(5) -0.0023(5) -0.0061(5)
N5 0.0182(6) 0.0192(6) 0.0209(6) -0.0003(5) -0.0044(5) -0.0051(5)
O6 0.0154(5) 0.0288(6) 0.0309(6) -0.0033(4) -0.0031(4) 0.0004(4)
O7 0.0280(6) 0.0333(6) 0.0194(5) 0.0068(4) -0.0047(4) -0.0056(5)
N8 0.0151(6) 0.0246(6) 0.0190(6) 0.0010(5) -0.0016(5) -0.0072(5)
N9 0.0143(6) 0.0221(6) 0.0181(6) 0.0006(5) -0.0004(4) -0.0048(5)
C10 0.0142(6) 0.0172(7) 0.0190(7) -0.0004(5) -0.0012(5) -0.0039(5)
N11 0.0155(6) 0.0185(6) 0.0152(5) -0.0004(4) -0.0031(4) -0.0045(5)
C12 0.0148(6) 0.0213(7) 0.0185(7) -0.0002(5) -0.0007(5) -0.0067(5)
N13 0.0223(6) 0.0292(7) 0.0155(6) -0.0002(5) -0.0059(5) -0.0075(5)
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
N2 N1 C4 110.22(11) . 2_756
N2 N1 H1 124.9 . .
C4 N1 H1 124.9 2_756 .
C3 N2 N1 106.26(11) . .
N2 C3 C4 111.43(12) . .
N2 C3 N5 120.96(12) . .
C4 C3 N5 127.59(12) . .
N1 C4 C4 108.36(15) 2_756 2_756
N1 C4 C3 147.91(13) 2_756 .
C4 C4 C3 103.73(14) 2_756 .
O6 N5 O7 124.67(12) . .
O6 N5 C3 119.38(12) . .
O7 N5 C3 115.95(11) . .
C12 N8 N9 106.36(11) . .
C10 N9 N8 107.82(11) . .
N9 C10 N11 109.59(12) . .
N9 C10 H10 125.2 . .
N11 C10 H10 125.2 . .
C10 N11 C12 105.82(11) . .
C10 N11 N13 124.31(11) . .
C12 N11 N13 129.87(11) . .
N8 C12 N11 110.41(12) . .
N8 C12 H12 124.8 . .
N11 C12 H12 124.8 . .
N11 N13 H13A 107.5(11) . .
N11 N13 H13B 106.5(11) . .
H13A N13 H13B 106.1(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 N2 1.3448(16) .
N1 C4 1.3588(17) 2_756
N1 H1 0.8800 .
N2 C3 1.3332(18) .
C3 C4 1.4005(18) .
C3 N5 1.4280(18) .
C4 N1 1.3588(17) 2_756
C4 C4 1.381(3) 2_756
N5 O6 1.2290(16) .
N5 O7 1.2312(16) .
N8 C12 1.3025(18) .
N8 N9 1.3915(16) .
N9 C10 1.3096(18) .
C10 N11 1.3458(18) .
C10 H10 0.9500 .
N11 C12 1.3608(17) .
N11 N13 1.4156(16) .
C12 H12 0.9500 .
N13 H13A 0.893(18) .
N13 H13B 0.88(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N9 0.88 1.84 2.7150(18) 174.4 1_654
N13 H13A N2 0.893(18) 2.419(19) 3.2517(18) 155.2(15) 2_756
N13 H13B N9 0.88(2) 2.591(19) 3.303(2) 138.5(14) 2_567
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
C4 N1 N2 C3 0.09(14) 2_756 . . .
N1 N2 C3 C4 -0.22(15) . . . .
N1 N2 C3 N5 -179.23(11) . . . .
N2 C3 C4 N1 179.9(2) . . . 2_756
N5 C3 C4 N1 -1.2(3) . . . 2_756
N2 C3 C4 C4 0.26(18) . . . 2_756
N5 C3 C4 C4 179.19(14) . . . 2_756
N2 C3 N5 O6 -2.62(19) . . . .
C4 C3 N5 O6 178.54(13) . . . .
N2 C3 N5 O7 177.23(12) . . . .
C4 C3 N5 O7 -1.6(2) . . . .
C12 N8 N9 C10 0.50(15) . . . .
N8 N9 C10 N11 -0.25(15) . . . .
N9 C10 N11 C12 -0.08(15) . . . .
N9 C10 N11 N13 179.73(12) . . . .
N9 N8 C12 N11 -0.56(15) . . . .
C10 N11 C12 N8 0.41(15) . . . .
N13 N11 C12 N8 -179.39(13) . . . .
