#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/64/7056416.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_7056416
loop_
_publ_author_name
'Liu, Tianlin'
'Qi, Xiujuan'
'Wang, Kangcai'
'Zhang, Jiaheng'
'Zhang, Wenquan'
'Zhang, Qinghua'
_publ_section_title
;
 Green primary energetic materials based on
 N-(3-nitro-1-(trinitromethyl)-1H-1,2,4-triazol-5-yl)nitramide
;
_journal_issue                   17
_journal_name_full               'New J. Chem.'
_journal_page_first              9070
_journal_page_last               9076
_journal_paper_doi               10.1039/C7NJ01917C
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C3 N9 O10, H2 O, H4 N'
_chemical_formula_sum            'C3 H6 N10 O11'
_chemical_formula_weight         358.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2017-07-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_audit_update_record
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.239(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5643(7)
_cell_length_b                   8.0022(7)
_cell_length_c                   10.6515(10)
_cell_measurement_reflns_used    1424
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.107
_cell_measurement_theta_min      3.184
_cell_volume                     644.60(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3901
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.693
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 856 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0372P)²+0.0561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                2298
_reflns_number_total             2752
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj01917c2.cif
_cod_data_source_block           a
_cod_database_code               7056416
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All N(H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N10-H10A = N10-H10B = N10-H10C = N10-H10D
 0.88 with sigma of 0.02
 O1W-H1WB = O1W-H1WA
 0.85 with sigma of 0.02
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
O1 O 0.2168(3) -0.5038(3) -0.1210(3) 0.0510(7) Uani 1 1 d . . .
O1W O -0.0253(3) -0.0963(4) -0.1818(3) 0.0561(7) Uani 1 1 d D . .
H1WA H 0.056(5) -0.147(6) -0.215(5) 0.084 Uiso 1 1 d DR . .
H1WB H -0.122(4) -0.114(7) -0.219(4) 0.084 Uiso 1 1 d DR . .
O2 O 0.2391(3) -0.3113(3) -0.2612(3) 0.0543(7) Uani 1 1 d . A 1
O3 O 0.3563(3) -1.0886(3) -0.0382(2) 0.0512(6) Uani 1 1 d . . .
O4 O 0.5889(3) -1.1902(3) -0.1271(3) 0.0502(6) Uani 1 1 d . . .
O5 O 0.8181(3) -0.5182(4) -0.1951(2) 0.0528(7) Uani 1 1 d . . .
O6 O 0.8008(3) -0.3722(3) -0.3658(3) 0.0553(7) Uani 1 1 d . . .
O7 O 0.7277(4) -0.5409(3) -0.5725(2) 0.0596(8) Uani 1 1 d . B 2
O8 O 0.4872(3) -0.6696(4) -0.5231(2) 0.0593(8) Uani 1 1 d . . .
O9 O 0.8506(3) -0.8844(3) -0.4695(3) 0.0556(7) Uani 1 1 d . . .
O10 O 1.0192(3) -0.7247(4) -0.3545(3) 0.0674(9) Uani 1 1 d . . .
N1 N 0.3860(3) -0.7977(3) -0.1664(2) 0.0303(6) Uani 1 1 d . . .
N2 N 0.6394(3) -0.9042(3) -0.2492(2) 0.0317(6) Uani 1 1 d . . .
N3 N 0.6049(3) -0.7458(3) -0.2941(3) 0.0323(6) Uani 1 1 d . . .
N4 N 0.4117(3) -0.5256(3) -0.2780(3) 0.0368(6) Uani 1 1 d . . .
N5 N 0.2840(3) -0.4482(3) -0.2168(3) 0.0359(6) Uani 1 1 d . . .
N6 N 0.4819(4) -1.0800(3) -0.1094(3) 0.0372(6) Uani 1 1 d . . .
N7 N 0.7856(3) -0.4976(4) -0.3063(3) 0.0367(6) Uani 1 1 d . . .
N8 N 0.6334(4) -0.6181(3) -0.5025(2) 0.0380(6) Uani 1 1 d . . .
N9 N 0.8814(3) -0.7672(4) -0.4019(3) 0.0392(7) Uani 1 1 d . . .
N10 N 0.0483(5) 0.1877(4) -0.0397(4) 0.0505(8) Uani 1 1 d D . .
H10A H 0.153(4) 0.227(6) -0.059(5) 0.076 Uiso 1 1 d DR . .
H10B H -0.001(6) 0.100(5) -0.073(4) 0.076 Uiso 1 1 d DR . .
H10C H -0.014(6) 0.263(5) -0.081(4) 0.076 Uiso 1 1 d DR . .
H10D H 0.071(6) 0.176(7) 0.037(3) 0.076 Uiso 1 1 d DR . .
C1 C 0.4525(4) -0.6816(4) -0.2407(3) 0.0295(6) Uani 1 1 d . . .
C2 C 0.5033(4) -0.9233(4) -0.1773(3) 0.0297(7) Uani 1 1 d . . .
C3 C 0.7183(4) -0.6594(4) -0.3726(3) 0.0312(7) 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
H1WA O1W H1WB 111(5)
C1 N1 C2 102.3(2)
C2 N2 N3 99.5(2)
N2 N3 C1 110.5(2)
N2 N3 C3 123.3(2)
C3 N3 C1 125.9(2)
N5 N4 C1 116.8(3)
O1 N5 O2 121.4(3)
O1 N5 N4 123.7(3)
O2 N5 N4 114.9(3)
O3 N6 C2 116.7(3)
O4 N6 O3 125.5(3)
O4 N6 C2 117.8(3)
O5 N7 C3 112.7(3)
O6 N7 O5 127.7(3)
O6 N7 C3 119.6(3)
O7 N8 C3 114.8(3)
O8 N8 O7 128.1(3)
O8 N8 C3 117.0(3)
O9 N9 C3 114.3(3)
O10 N9 O9 129.0(3)
O10 N9 C3 116.7(3)
H10A N10 H10B 125(5)
H10A N10 H10C 97(4)
H10A N10 H10D 96(4)
H10B N10 H10C 97(4)
H10B N10 H10D 113(5)
H10C N10 H10D 132(5)
N1 C1 N3 108.2(2)
N1 C1 N4 137.8(3)
N4 C1 N3 114.0(3)
N1 C2 N6 121.2(3)
N2 C2 N1 119.5(3)
N2 C2 N6 119.3(3)
N3 C3 N7 109.9(2)
N3 C3 N8 113.1(2)
N3 C3 N9 110.4(2)
N8 C3 N7 110.7(2)
N9 C3 N7 107.6(2)
N9 C3 N8 104.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.232(4)
O1W H1WA 0.83(3)
O1W H1WB 0.84(2)
O2 N5 1.238(4)
O3 N6 1.231(3)
O4 N6 1.214(3)
O5 N7 1.216(4)
O6 N7 1.194(4)
O7 N8 1.212(4)
O8 N8 1.196(4)
O9 N9 1.202(4)
O10 N9 1.198(4)
N1 C1 1.326(4)
N1 C2 1.347(4)
N2 N3 1.377(4)
N2 C2 1.305(4)
N3 C1 1.395(4)
N3 C3 1.395(4)
N4 N5 1.331(3)
N4 C1 1.344(4)
N6 C2 1.458(4)
N7 C3 1.555(4)
N8 C3 1.548(4)
N9 C3 1.543(4)
N10 H10A 0.88(2)
N10 H10B 0.87(3)
N10 H10C 0.88(2)
N10 H10D 0.84(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139177985
