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#$Date: 2025-08-22 00:13:44 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301852 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060603.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_7060603
loop_
_publ_author_name
'Chen, Xiang'
'Guo, Zhaoqi'
'Zhang, Cong'
'Zhang, Jianguo'
'Ma, Haixia'
_publ_section_title
;
 Boosting intermolecular interactions of fused cyclic explosives: the way
 to thermostable and insensitive energetic materials with high density
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9358
_journal_page_last               9367
_journal_paper_doi               10.1039/D1NJ00924A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C3 H N6 O, H4 N, H2 O'
_chemical_formula_sum            'C3 H7 N7 O2'
_chemical_formula_weight         173.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-31 deposited with the CCDC.	2021-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.823(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0295(11)
_cell_length_b                   12.201(3)
_cell_length_c                   14.678(4)
_cell_measurement_reflns_used    2879
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      34.83
_cell_measurement_theta_min      3.62
_cell_volume                     721.3(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4877
_diffrn_reflns_point_group_measured_fraction_full 0.757
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.850
_diffrn_reflns_theta_min         3.617
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.3881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1687 before and 0.0935 after correction. The Ratio of minimum to maximum transmission is 0.5196. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2185
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0622
_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)+(0.0719P)²+0.3526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1592
_reflns_Friedel_coverage         0.402
_reflns_Friedel_fraction_full    0.531
_reflns_Friedel_fraction_max     0.397
_reflns_number_gt                1984
_reflns_number_total             2185
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00924a2.cif
_cod_data_source_block           b
_cod_depositor_comments
'Adding full bibliography for 7060601--7060604.cif.'
_cod_original_cell_volume        721.2(3)
_cod_database_code               7060603
_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_max   0.980
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O2-H2A = O2-H2B
 0.85 with sigma of 0.02
 H2A-H2B
 1.34 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
O1 O 0.4727(6) 0.23788(18) 0.41106(16) 0.0318(5) Uani 1 1 d . . . . .
N6 N 1.2768(6) 0.38558(17) 0.70227(18) 0.0240(4) Uani 1 1 d . . . . .
N7 N 0.7060(6) 0.53450(18) 0.35930(17) 0.0224(4) Uani 1 1 d . . . . .
H7A H 0.835(11) 0.487(4) 0.341(3) 0.034 Uiso 1 1 d R . . . .
H7B H 0.612(12) 0.516(4) 0.408(3) 0.034 Uiso 1 1 d R . . . .
H7C H 0.571(12) 0.554(3) 0.313(3) 0.034 Uiso 1 1 d R . . . .
H7D H 0.814(11) 0.592(4) 0.372(3) 0.034 Uiso 1 1 d R . . . .
N2 N 0.9513(5) 0.34643(16) 0.58516(14) 0.0157(4) Uani 1 1 d . . . . .
N1 N 0.7320(5) 0.35087(16) 0.51215(15) 0.0181(4) Uani 1 1 d . . . . .
N3 N 0.8203(6) 0.15146(17) 0.51215(17) 0.0237(5) Uani 1 1 d . . . . .
N5 N 1.2928(5) 0.27500(19) 0.68917(16) 0.0234(4) Uani 1 1 d . . . . .
N4 N 1.0253(6) 0.15361(17) 0.58024(17) 0.0230(5) Uani 1 1 d . . . . .
C3 C 1.0712(6) 0.42763(18) 0.63875(18) 0.0209(4) Uani 1 1 d . . . . .
H3 H 1.018682 0.501515 0.632387 0.025 Uiso 1 1 calc R . . . .
C2 C 1.0922(6) 0.25343(18) 0.61838(17) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.6708(6) 0.2517(2) 0.47720(18) 0.0195(4) Uani 1 1 d . . . . .
O2 O 0.6494(6) 0.11927(13) 0.79810(18) 0.0289(4) Uani 1 1 d D . . . .
H2A H 0.765(12) 0.153(3) 0.836(3) 0.043 Uiso 1 1 d DR . . . .
H2B H 0.541(12) 0.158(3) 0.762(3) 0.043 Uiso 1 1 d DR . . . .
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
C3 N6 N5 108.3(2) . . ?
H7A N7 H7B 112(5) . . ?
H7A N7 H7C 109(4) . . ?
H7A N7 H7D 109(4) . . ?
H7B N7 H7C 116(4) . . ?
H7B N7 H7D 106(4) . . ?
H7C N7 H7D 104(4) . . ?
C3 N2 N1 129.78(19) . . ?
C3 N2 C2 105.55(19) . . ?
C2 N2 N1 124.67(19) . . ?
C1 N1 N2 111.84(19) . . ?
N4 N3 C1 120.7(2) . . ?
C2 N5 N6 106.1(2) . . ?
N3 N4 C2 117.0(2) . . ?
N6 C3 N2 109.3(2) . . ?
N6 C3 H3 125.4 . . ?
N2 C3 H3 125.4 . . ?
N2 C2 N4 121.7(2) . . ?
N5 C2 N2 110.8(2) . . ?
N5 C2 N4 127.5(2) . . ?
O1 C1 N1 121.8(2) . . ?
O1 C1 N3 114.2(2) . . ?
N1 C1 N3 124.0(2) . . ?
H2A O2 H2B 115(4) . . ?
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
O1 C1 1.248(3) . ?
N6 N5 1.365(3) . ?
N6 C3 1.330(3) . ?
N7 H7A 0.83(5) . ?
N7 H7B 0.85(5) . ?
N7 H7C 0.89(5) . ?
N7 H7D 0.85(4) . ?
N2 N1 1.368(3) . ?
N2 C3 1.345(3) . ?
N2 C2 1.353(3) . ?
N1 C1 1.334(3) . ?
N3 N4 1.276(3) . ?
N3 C1 1.450(3) . ?
N5 C2 1.323(3) . ?
N4 C2 1.364(3) . ?
C3 H3 0.9300 . ?
O2 H2A 0.82(2) . ?
O2 H2B 0.83(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
_geom_hbond_publ_flag
N7 H7A O2 0.83(5) 1.93(5) 2.761(3) 178(5) 4_554 yes
N7 H7B N1 0.85(5) 2.57(4) 3.170(3) 129(4) . yes
N7 H7B N3 0.85(5) 2.57(5) 3.116(4) 124(4) 3_455 yes
N7 H7C N6 0.89(5) 2.11(5) 3.000(3) 175(4) 2_464 yes
N7 H7D O1 0.85(4) 1.97(4) 2.800(3) 168(5) 3 yes
O2 H2A O1 0.82(2) 1.91(2) 2.710(3) 166(5) 4 yes
O2 H2B N5 0.83(2) 2.02(2) 2.843(3) 170(5) 1_455 yes
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
N6 N5 C2 N2 0.6(3) . . . . ?
N6 N5 C2 N4 -179.5(3) . . . . ?
N2 N1 C1 O1 178.8(3) . . . . ?
N2 N1 C1 N3 -0.3(4) . . . . ?
N1 N2 C3 N6 179.5(2) . . . . ?
N1 N2 C2 N5 -180.0(2) . . . . ?
N1 N2 C2 N4 0.2(4) . . . . ?
N3 N4 C2 N2 -0.7(4) . . . . ?
N3 N4 C2 N5 179.5(3) . . . . ?
N5 N6 C3 N2 0.5(3) . . . . ?
N4 N3 C1 O1 -179.4(3) . . . . ?
N4 N3 C1 N1 -0.2(4) . . . . ?
C3 N6 N5 C2 -0.7(3) . . . . ?
C3 N2 N1 C1 -179.2(3) . . . . ?
C3 N2 C2 N5 -0.3(3) . . . . ?
C3 N2 C2 N4 179.8(3) . . . . ?
C2 N2 N1 C1 0.3(3) . . . . ?
C2 N2 C3 N6 -0.1(3) . . . . ?
C1 N3 N4 C2 0.7(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350227
