#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/64/7056413.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_7056413
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, H5 N2'
_chemical_formula_sum            'C3 H7 N11 O11'
_chemical_formula_weight         373.20
_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                 94.923(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2280(4)
_cell_length_b                   7.3357(3)
_cell_length_c                   11.3167(5)
_cell_measurement_reflns_used    2730
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.48
_cell_volume                     680.54(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6258
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         1.806
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0505 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 957 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0369
_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)+(0.0419P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2575
_reflns_number_total             3060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj01917c2.cif
_cod_data_source_block           mo_2016281_0m
_cod_database_code               7056413
#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) groups, All N(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
;
_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 0.1718(3) 0.2560(4) 0.5112(2) 0.0719(7) Uani 1 1 d . . .
O1W O 1.0390(2) 1.0594(3) 0.80338(18) 0.0515(5) Uani 1 1 d . . .
H1WA H 1.1049 1.0637 0.7496 0.077 Uiso 1 1 d G . .
H1WB H 0.9484 1.0155 0.7747 0.077 Uiso 1 1 d G . .
O2 O 0.0222(3) 0.4166(4) 0.6211(3) 0.0796(8) Uani 1 1 d . . .
O3 O 0.5008(3) 0.4988(4) 0.48172(19) 0.0636(7) Uani 1 1 d . . .
O4 O 0.2750(4) 0.6410(3) 0.43071(18) 0.0704(8) Uani 1 1 d . A 2
O5 O 0.3992(3) -0.0574(3) 0.8812(2) 0.0574(6) Uani 1 1 d . . .
O6 O 0.6186(3) 0.0526(3) 0.97226(18) 0.0505(5) Uani 1 1 d . . .
O7 O 0.2106(3) 0.8058(3) 0.62512(19) 0.0600(6) Uani 1 1 d . . .
O8 O 0.2161(3) 0.6385(3) 0.78236(17) 0.0549(6) Uani 1 1 d . . .
O9 O 0.7382(3) 0.8795(3) 0.7478(2) 0.0581(6) Uani 1 1 d . B 1
O10 O 0.7972(3) 0.6439(3) 0.8548(2) 0.0790(9) Uani 1 1 d . . .
N1 N 0.1472(3) 0.3783(3) 0.5780(2) 0.0466(6) Uani 1 1 d . . .
N2 N 0.3671(3) 0.5518(3) 0.49702(18) 0.0429(6) Uani 1 1 d . . .
N3 N 0.2341(3) 0.6674(3) 0.67893(19) 0.0375(5) Uani 1 1 d . . .
N4 N 0.4080(3) 0.3992(3) 0.69161(18) 0.0336(5) Uani 1 1 d . . .
N5 N 0.3686(3) 0.2356(3) 0.74094(18) 0.0327(5) Uani 1 1 d . . .
N6 N 0.5043(3) 0.0578(3) 0.89601(19) 0.0367(5) Uani 1 1 d . . .
N7 N 0.6088(3) 0.3485(3) 0.82933(17) 0.0307(5) Uani 1 1 d . . .
N8 N 0.5876(3) 0.6386(3) 0.71557(19) 0.0387(5) Uani 1 1 d . . .
N9 N 0.7132(3) 0.7194(3) 0.7753(2) 0.0412(6) Uani 1 1 d . . .
C1 C 0.2967(3) 0.4968(4) 0.6146(2) 0.0321(6) Uani 1 1 d . . .
C2 C 0.5502(3) 0.4698(4) 0.7493(2) 0.0305(5) Uani 1 1 d . . .
C3 C 0.4932(3) 0.2169(3) 0.8189(2) 0.0298(5) Uani 1 1 d . . .
N10 N 1.0918(3) 0.8173(3) 1.0019(2) 0.0360(5) Uani 1 1 d . . .
H10A H 1.082(4) 0.694(5) 0.991(3) 0.054 Uiso 1 1 d R . .
H10B H 1.108(4) 0.870(5) 0.929(3) 0.054 Uiso 1 1 d R . .
H10C H 1.182(4) 0.848(4) 1.056(3) 0.054 Uiso 1 1 d R . .
N11 N 0.9495(3) 0.9038(4) 1.0425(2) 0.0424(6) Uani 1 1 d . . .
H11A H 0.953(5) 0.871(5) 1.116(4) 0.064 Uiso 1 1 d R . .
H11B H 0.868(5) 0.855(5) 1.003(3) 0.064 Uiso 1 1 d R . .
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
O1 N1 O2 128.5(3)
O1 N1 C1 114.7(3)
O2 N1 C1 116.7(3)
O3 N2 O4 128.4(3)
O3 N2 C1 117.2(2)
O4 N2 C1 114.4(2)
O7 N3 O8 128.0(3)
O7 N3 C1 119.5(2)
O8 N3 C1 112.6(2)
N5 N4 C1 122.2(2)
N5 N4 C2 110.69(19)
C2 N4 C1 125.4(2)
C3 N5 N4 99.7(2)
O5 N6 O6 125.0(2)
O5 N6 C3 118.0(2)
O6 N6 C3 116.9(2)
C2 N7 C3 101.96(19)
N9 N8 C2 117.2(2)
O9 N9 N8 115.8(2)
O10 N9 O9 121.4(2)
O10 N9 N8 122.7(2)
N1 C1 N2 105.4(2)
N1 C1 N3 107.0(2)
N2 C1 N3 110.8(2)
N4 C1 N1 110.1(2)
N4 C1 N2 113.2(2)
N4 C1 N3 110.12(18)
N7 C2 N4 108.1(2)
N7 C2 N8 137.2(2)
N8 C2 N4 114.6(2)
N5 C3 N6 119.8(2)
N5 C3 N7 119.4(2)
N7 C3 N6 120.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.201(4)
O2 N1 1.208(4)
O3 N2 1.194(4)
O4 N2 1.211(3)
O5 N6 1.210(3)
O6 N6 1.221(3)
O7 N3 1.191(3)
O8 N3 1.211(3)
O9 N9 1.237(3)
O10 N9 1.220(3)
N1 C1 1.535(3)
N2 C1 1.550(3)
N3 C1 1.558(3)
N4 N5 1.374(3)
N4 C1 1.405(3)
N4 C2 1.390(3)
N5 C3 1.302(3)
N6 C3 1.455(3)
N7 C2 1.331(3)
N7 C3 1.353(3)
N8 N9 1.326(3)
N8 C2 1.339(3)
N10 N11 1.441(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168349251
