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#$Date: 2022-08-05 00:54:42 +0300 (Fri, 05 Aug 2022) $
#$Revision: 277070 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/04/7130477.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_7130477
loop_
_publ_author_name
'Bellas, Michael K.'
'Matzger, Adam J.'
_publ_section_title
;
 Peroxosolvate discovery method leads to first cocrystal with three
 energetic components.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8806
_journal_page_last               8809
_journal_paper_doi               10.1039/d2cc02024f
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C3 H2 N4 O4, C2 H4 N4 O, H2 O1'
_chemical_formula_sum            'C5 H8 N8 O6'
_chemical_formula_weight         276.19
_chemical_name_common            DDH
_chemical_name_systematic
3,4-diaminofurazan-3,4-dinitro-1H-pyrazole-hydrate
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-09 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.36177(4)
_cell_length_b                   8.07141(5)
_cell_length_c                   25.18846(16)
_cell_measurement_reflns_used    19647
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0440
_cell_measurement_theta_min      3.5030
_cell_volume                     1090.082(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            26839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.310
_diffrn_reflns_theta_min         3.509
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       blade
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_coef       0.0023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0564P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2208
_reflns_number_total             2275
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02024f2.cif
_cod_data_source_block           DDH
_cod_original_cell_volume        1090.081(13)
_cod_database_code               7130477
_shelx_shelxl_version_number     2018/3
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_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
O4 O -0.0083(4) 0.0723(2) 0.28964(6) 0.0497(5) Uani 1 1 d . . . . .
O18 O 1.3900(3) 0.6017(3) 0.45046(7) 0.0507(5) Uani 1 1 d . . . . .
O17 O 1.4331(4) 0.7576(2) 0.38142(8) 0.0538(5) Uani 1 1 d . . . . .
O15 O 0.9293(4) 0.5350(2) 0.49345(6) 0.0522(5) Uani 1 1 d . . . . .
O19 O 0.5462(4) 0.3441(3) 0.24781(7) 0.0532(5) Uani 1 1 d D . . . .
H19A H 0.453(7) 0.372(5) 0.2209(12) 0.080 Uiso 1 1 d D U . . .
H19B H 0.439(7) 0.285(4) 0.2661(14) 0.080 Uiso 1 1 d D U . . .
O14 O 0.7726(4) 0.3012(3) 0.46817(7) 0.0576(6) Uani 1 1 d . . . . .
N9 N 0.7695(4) 0.4205(2) 0.36827(7) 0.0337(4) Uani 1 1 d . . . . .
N10 N 0.8564(3) 0.4861(2) 0.32278(6) 0.0347(4) Uani 1 1 d . . . . .
H10 H 0.787892 0.469160 0.292391 0.042 Uiso 1 1 calc R U . . .
N13 N 0.8737(4) 0.4340(2) 0.45943(7) 0.0361(4) Uani 1 1 d . . . . .
N16 N 1.3242(4) 0.6509(2) 0.40689(7) 0.0355(4) Uani 1 1 d . . . . .
N3 N 0.1941(4) 0.1522(3) 0.31341(7) 0.0399(4) Uani 1 1 d . . . . .
N6 N -0.0920(4) -0.0655(3) 0.41926(7) 0.0415(5) Uani 1 1 d . . . . .
H6A H -0.081431 0.005482 0.444776 0.050 Uiso 1 1 d R U . . .
H6B H -0.243331 -0.101258 0.417336 0.050 Uiso 1 1 d R U . . .
N7 N 0.3380(4) 0.1727(3) 0.40118(8) 0.0429(5) Uani 1 1 d . . . . .
H7A H 0.469065 0.215960 0.386582 0.052 Uiso 1 1 d R U . . .
H7B H 0.262365 0.248316 0.419533 0.052 Uiso 1 1 d R U . . .
N5 N -0.1437(4) -0.0171(3) 0.32735(7) 0.0438(5) Uani 1 1 d . . . . .
C12 C 1.1105(4) 0.5769(2) 0.38285(8) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.1823(4) 0.1139(2) 0.36345(8) 0.0301(4) Uani 1 1 d . . . . .
C8 C 0.9252(4) 0.4754(2) 0.40470(7) 0.0293(4) Uani 1 1 d . . . . .
C1 C -0.0293(4) 0.0071(3) 0.37226(8) 0.0318(4) Uani 1 1 d . . . . .
C11 C 1.0582(4) 0.5796(3) 0.32924(8) 0.0338(4) Uani 1 1 d . . . . .
H11 H 1.146259 0.635550 0.302959 0.041 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
N5 O4 N3 110.52(14) . . ?
H19A O19 H19B 100(3) . . ?
C8 N9 N10 103.95(17) . . ?
C11 N10 N9 113.66(17) . . ?
C11 N10 H10 123.2 . . ?
N9 N10 H10 123.2 . . ?
O15 N13 O14 124.64(19) . . ?
O15 N13 C8 117.97(18) . . ?
O14 N13 C8 117.37(18) . . ?
O18 N16 O17 124.3(2) . . ?
O18 N16 C12 118.58(19) . . ?
O17 N16 C12 117.11(19) . . ?
C2 N3 O4 105.57(18) . . ?
C1 N6 H6A 110.2 . . ?
C1 N6 H6B 109.1 . . ?
H6A N6 H6B 109.0 . . ?
C2 N7 H7A 110.1 . . ?
C2 N7 H7B 109.5 . . ?
H7A N7 H7B 108.8 . . ?
C1 N5 O4 105.59(18) . . ?
C11 C12 C8 104.47(17) . . ?
C11 C12 N16 124.90(19) . . ?
C8 C12 N16 130.36(18) . . ?
N3 C2 N7 124.7(2) . . ?
N3 C2 C1 109.24(18) . . ?
N7 C2 C1 126.01(18) . . ?
N9 C8 C12 111.88(17) . . ?
N9 C8 N13 117.75(18) . . ?
C12 C8 N13 130.22(18) . . ?
N5 C1 N6 125.0(2) . . ?
N5 C1 C2 109.07(19) . . ?
N6 C1 C2 125.78(19) . . ?
N10 C11 C12 106.04(18) . . ?
N10 C11 H11 127.0 . . ?
C12 C11 H11 127.0 . . ?
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
O4 N5 1.397(3) . ?
O4 N3 1.397(3) . ?
O18 N16 1.219(3) . ?
O17 N16 1.223(3) . ?
O15 N13 1.220(3) . ?
O19 H19A 0.87(2) . ?
O19 H19B 0.88(2) . ?
O14 N13 1.221(3) . ?
N9 C8 1.318(3) . ?
N9 N10 1.346(2) . ?
N10 C11 1.329(3) . ?
N10 H10 0.8600 . ?
N13 C8 1.445(3) . ?
N16 C12 1.427(3) . ?
N3 C2 1.299(3) . ?
N6 C1 1.363(3) . ?
N6 H6A 0.8629 . ?
N6 H6B 0.8625 . ?
N7 C2 1.351(3) . ?
N7 H7A 0.8665 . ?
N7 H7B 0.8666 . ?
N5 C1 1.301(3) . ?
C12 C11 1.379(3) . ?
C12 C8 1.401(3) . ?
C2 C1 1.442(3) . ?
C11 H11 0.9300 . ?
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
C8 N9 N10 C11 -0.2(2) . . . . ?
N5 O4 N3 C2 -0.3(2) . . . . ?
N3 O4 N5 C1 0.1(3) . . . . ?
O18 N16 C12 C11 -158.8(2) . . . . ?
O17 N16 C12 C11 19.4(3) . . . . ?
O18 N16 C12 C8 14.2(3) . . . . ?
O17 N16 C12 C8 -167.5(2) . . . . ?
O4 N3 C2 N7 -176.6(2) . . . . ?
O4 N3 C2 C1 0.3(2) . . . . ?
N10 N9 C8 C12 0.4(2) . . . . ?
N10 N9 C8 N13 176.42(18) . . . . ?
C11 C12 C8 N9 -0.5(2) . . . . ?
N16 C12 C8 N9 -174.6(2) . . . . ?
C11 C12 C8 N13 -175.8(2) . . . . ?
N16 C12 C8 N13 10.0(4) . . . . ?
O15 N13 C8 N9 -146.4(2) . . . . ?
O14 N13 C8 N9 32.2(3) . . . . ?
O15 N13 C8 C12 28.8(3) . . . . ?
O14 N13 C8 C12 -152.6(2) . . . . ?
O4 N5 C1 N6 -176.2(2) . . . . ?
O4 N5 C1 C2 0.1(3) . . . . ?
N3 C2 C1 N5 -0.3(3) . . . . ?
N7 C2 C1 N5 176.6(2) . . . . ?
N3 C2 C1 N6 176.0(2) . . . . ?
N7 C2 C1 N6 -7.1(3) . . . . ?
N9 N10 C11 C12 -0.1(2) . . . . ?
C8 C12 C11 N10 0.3(2) . . . . ?
N16 C12 C11 N10 174.88(19) . . . . ?
