#------------------------------------------------------------------------------
#$Date: 2022-11-23 03:23:10 +0100 (Wed 23 de Nov de 2022) $
#$Revision: 279486 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/58/7245894.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_7245894
loop_
_publ_author_name
'Ding, Lujia'
'Ge, Ruirong'
'Wang, Pengcheng'
'Li, Dongxue'
'Lin, Qiuhan'
'Lu, Ming'
'Xu, Yuangang'
_publ_section_title
;
 A series of N-trinitromethyl-substituted polynitro-pyrazoles:
 high-energy-density materials with positive oxygen balances
;
_journal_issue                   51
_journal_name_full               'RSC Advances'
_journal_page_first              33304
_journal_page_last               33312
_journal_paper_doi               10.1039/D2RA06149J
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C4 N6 O9, 2(H2 O)'
_chemical_formula_sum            'C4 H4 N6 O11'
_chemical_formula_weight         312.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-09-03 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                78.002(3)
_cell_angle_beta                 80.654(3)
_cell_angle_gamma                62.508(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6403(9)
_cell_length_b                   7.7898(8)
_cell_length_c                   11.2231(11)
_cell_measurement_reflns_used    4206
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.98
_cell_volume                     577.88(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8706
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.982
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0537
_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)+(0.0713P)²+0.5042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1465
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1961
_reflns_number_total             2639
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra06149j2.cif
_cod_data_source_block           DLJ_012_a
_cod_database_code               7245894
_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.
;
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_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_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
C1 C 0.9612(3) 0.7240(3) 0.0761(2) 0.0240(5) Uani 1 1 d . . . . .
C2 C 0.7715(3) 0.7555(3) 0.0558(2) 0.0259(5) Uani 1 1 d . . . . .
C3 C 0.6757(3) 0.7354(3) 0.1737(2) 0.0266(5) Uani 1 1 d . . . . .
C4 C 0.7948(4) 0.6591(3) 0.3764(2) 0.0299(5) Uani 1 1 d . . . . .
N1 N 0.8187(3) 0.6963(3) 0.25047(17) 0.0293(4) Uani 1 1 d . . . . .
N2 N 0.9955(3) 0.6881(3) 0.19044(17) 0.0288(4) Uani 1 1 d . . . . .
N3 N 1.1174(3) 0.7343(3) -0.01405(17) 0.0295(4) Uani 1 1 d . . . . .
N4 N 0.6931(3) 0.7819(3) -0.05420(18) 0.0301(5) Uani 1 1 d . . . . .
N6 N 0.7630(3) 0.8027(3) 0.44295(19) 0.0331(5) Uani 1 1 d . . . . .
N7 N 0.7956(3) 0.4813(3) 0.42937(18) 0.0331(5) Uani 1 1 d . . . . .
O1 O 1.2850(3) 0.6064(3) 0.00065(19) 0.0489(5) Uani 1 1 d . . . . .
O2 O 1.0725(3) 0.8684(3) -0.09956(16) 0.0443(5) Uani 1 1 d . . . . .
O3 O 0.8060(3) 0.7482(3) -0.14808(16) 0.0424(5) Uani 1 1 d . . . . .
O4 O 0.5146(3) 0.8306(3) -0.05326(18) 0.0412(5) Uani 1 1 d . . . . .
O5 O 0.8278(3) 0.3628(3) 0.35990(18) 0.0458(5) Uani 1 1 d . . . . .
O6 O 0.7649(4) 0.4420(3) 0.54070(17) 0.0588(6) Uani 1 1 d . . . . .
O7 O 0.7391(4) 0.7795(3) 0.55571(17) 0.0539(6) Uani 1 1 d . . . . .
O8 O 0.7664(3) 0.9568(3) 0.38450(19) 0.0490(5) Uani 1 1 d . . . . .
O9 O 0.5131(3) 0.7385(3) 0.21142(16) 0.0371(4) Uani 1 1 d . . . . .
O10 O 0.4755(4) 0.3746(4) 0.2479(2) 0.0585(6) Uani 1 1 d D . . . .
H10A H 0.501(6) 0.474(5) 0.238(4) 0.088 Uiso 1 1 d D U . . .
H10B H 0.384(5) 0.384(6) 0.306(3) 0.088 Uiso 1 1 d D U . . .
O11 O 0.1637(4) 0.9556(3) 0.3381(2) 0.0620(6) Uani 1 1 d D . . . .
H11A H 0.278(4) 0.902(6) 0.294(3) 0.093 Uiso 1 1 d D U . . .
H11B H 0.158(6) 0.862(5) 0.394(3) 0.093 Uiso 1 1 d D U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
_geom_angle_publ_flag
N2 C1 C2 114.5(2) . . ?
N2 C1 N3 117.3(2) . . ?
C2 C1 N3 128.1(2) . . ?
N4 C2 C1 129.1(2) . . ?
N4 C2 C3 125.1(2) . . ?
C1 C2 C3 105.53(19) . . ?
O9 C3 N1 123.1(2) . . ?
O9 C3 C2 134.1(2) . . ?
N1 C3 C2 102.69(19) . . ?
N6 C4 N1 118.8(2) . . ?
N6 C4 N7 123.2(2) . . ?
N1 C4 N7 117.9(2) . . ?
C4 N1 C3 123.9(2) . . ?
C4 N1 N2 121.59(19) . . ?
C3 N1 N2 114.40(18) . . ?
C1 N2 N1 102.84(18) . . ?
O1 N3 O2 124.3(2) . . ?
O1 N3 C1 117.34(18) . . ?
O2 N3 C1 118.34(19) . . ?
O4 N4 O3 122.4(2) . . ?
O4 N4 C2 118.5(2) . . ?
O3 N4 C2 119.0(2) . . ?
O7 N6 O8 120.7(2) . . ?
O7 N6 C4 122.1(2) . . ?
O8 N6 C4 117.1(2) . . ?
O6 N7 O5 121.2(2) . . ?
O6 N7 C4 121.6(2) . . ?
O5 N7 C4 117.3(2) . . ?
H10A O10 H10B 110(3) . . ?
H11A O11 H11B 106(3) . . ?
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
C1 N2 1.299(3) . ?
C1 C2 1.403(3) . ?
C1 N3 1.455(3) . ?
C2 N4 1.395(3) . ?
C2 C3 1.421(3) . ?
C3 O9 1.236(3) . ?
C3 N1 1.385(3) . ?
C4 N6 1.380(3) . ?
C4 N1 1.382(3) . ?
C4 N7 1.386(3) . ?
N1 N2 1.388(3) . ?
N3 O1 1.217(3) . ?
N3 O2 1.220(3) . ?
N4 O4 1.235(3) . ?
N4 O3 1.238(3) . ?
N6 O7 1.236(3) . ?
N6 O8 1.252(3) . ?
N7 O6 1.234(3) . ?
N7 O5 1.244(3) . ?
O10 H10A 0.863(18) . ?
O10 H10B 0.863(18) . ?
O11 H11A 0.887(19) . ?
O11 H11B 0.869(18) . ?
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
N2 C1 C2 N4 -174.4(2) . . . . ?
N3 C1 C2 N4 8.2(4) . . . . ?
N2 C1 C2 C3 -0.4(3) . . . . ?
N3 C1 C2 C3 -177.7(2) . . . . ?
N4 C2 C3 O9 -1.6(4) . . . . ?
C1 C2 C3 O9 -176.0(2) . . . . ?
N4 C2 C3 N1 175.0(2) . . . . ?
C1 C2 C3 N1 0.6(2) . . . . ?
N6 C4 N1 C3 -105.6(3) . . . . ?
N7 C4 N1 C3 71.8(3) . . . . ?
N6 C4 N1 N2 77.5(3) . . . . ?
N7 C4 N1 N2 -105.2(3) . . . . ?
O9 C3 N1 C4 -0.8(3) . . . . ?
C2 C3 N1 C4 -177.9(2) . . . . ?
O9 C3 N1 N2 176.4(2) . . . . ?
C2 C3 N1 N2 -0.7(2) . . . . ?
C2 C1 N2 N1 -0.1(2) . . . . ?
N3 C1 N2 N1 177.58(17) . . . . ?
C4 N1 N2 C1 177.7(2) . . . . ?
C3 N1 N2 C1 0.5(2) . . . . ?
N2 C1 N3 O1 45.7(3) . . . . ?
C2 C1 N3 O1 -137.0(2) . . . . ?
N2 C1 N3 O2 -135.0(2) . . . . ?
C2 C1 N3 O2 42.3(3) . . . . ?
C1 C2 N4 O4 -171.6(2) . . . . ?
C3 C2 N4 O4 15.4(3) . . . . ?
C1 C2 N4 O3 11.2(3) . . . . ?
C3 C2 N4 O3 -161.8(2) . . . . ?
N1 C4 N6 O7 179.5(2) . . . . ?
N7 C4 N6 O7 2.4(4) . . . . ?
N1 C4 N6 O8 -3.0(3) . . . . ?
N7 C4 N6 O8 179.8(2) . . . . ?
N6 C4 N7 O6 1.0(4) . . . . ?
N1 C4 N7 O6 -176.2(2) . . . . ?
N6 C4 N7 O5 -179.3(2) . . . . ?
N1 C4 N7 O5 3.5(3) . . . . ?
