#------------------------------------------------------------------------------
#$Date: 2025-11-29 23:08:40 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303935 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/07/7160786.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_7160786
loop_
_publ_author_name
'Sun, Huanyu'
'Zeng, Zhiwei'
'Chen, Chunhui'
'Mai, Xiancheng'
'Wang, Jia'
'Huang, Wei'
'Tang, Yongxing'
'Liu, Yuji'
_publ_section_title
;
 Design, synthesis and characterization of a carbonyl-containing
 high-density pyrazolotriazine-based energetic compound.
;
_journal_issue                   42
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9652
_journal_page_last               9657
_journal_paper_doi               10.1039/d5ob01264c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '2(C6 H11 N9), 2(Cl), H2 O'
_chemical_formula_sum            'C12 H24 Cl2 N18 O'
_chemical_formula_weight         507.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2nrmgj
_audit_creation_date             2025-06-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-06-19 deposited with the CCDC.	2025-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.1790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7890(2)
_cell_length_b                   10.83470(10)
_cell_length_c                   15.9281(2)
_cell_measurement_reflns_used    5669
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      5.06
_cell_volume                     2553.97(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8528
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.177
_diffrn_reflns_theta_min         5.059
_exptl_absorpt_coefficient_mu    2.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         1.002
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0711
_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)+(0.1225P)²+4.7989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2130
_refine_ls_wR_factor_ref         0.2141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2304
_reflns_number_total             2434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01264c2.cif
_cod_data_source_block           1_a_sq
_cod_depositor_comments
'Adding full bibliography for 7160786--7160787.cif.'
_cod_original_cell_volume        2553.97(5)
_cod_database_code               7160786
_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.
;
_shelx_estimated_absorpt_t_max   0.815
_shelx_estimated_absorpt_t_min   0.741
_olex2_refinement_description
;
1. Others
 Fixed Sof: O1(0.5) H1D(0.5) H1E(0.5)
2.a Riding coordinates:
 N9(H9A,H9B), O1(H1D,H1E)
2.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B), N8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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'
'-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
C2 C 0.47420(17) 0.6229(2) 0.62825(19) 0.0288(6) Uani 1 1 d . . . . .
C5 C 0.61808(17) 0.3895(2) 0.61606(18) 0.0272(6) Uani 1 1 d . . . . .
C3 C 0.48946(16) 0.4980(2) 0.62174(18) 0.0276(5) Uani 1 1 d . . . . .
C1 C 0.55019(16) 0.6854(2) 0.63153(18) 0.0274(5) Uani 1 1 d . . . . .
C6 C 0.62918(17) 0.1770(2) 0.62064(19) 0.0301(6) Uani 1 1 d . . . . .
C4 C 0.39754(18) 0.6796(3) 0.6255(2) 0.0346(6) Uani 1 1 d . . . . .
Cl1 Cl 0.75587(5) 0.88345(6) 0.63731(6) 0.0435(3) Uani 1 1 d . . . . .
N1 N 0.56119(16) 0.8116(2) 0.63452(18) 0.0346(5) Uani 1 1 d . . . . .
H1A H 0.6185 0.8293 0.6511 0.052 Uiso 1 1 calc R U . . .
H1B H 0.5469 0.8436 0.6771 0.052 Uiso 1 1 calc R U . . .
H1C H 0.5253 0.8433 0.5773 0.052 Uiso 1 1 calc R U . . .
N3 N 0.60856(15) 0.60948(19) 0.62632(17) 0.0288(5) Uani 1 1 d . . . . .
N4 N 0.57042(13) 0.4925(2) 0.61925(15) 0.0273(5) Uani 1 1 d . . . . .
N5 N 0.43967(17) 0.4004(2) 0.6169(2) 0.0431(7) Uani 1 1 d . . . . .
H5A H 0.4574 0.3276 0.6119 0.052 Uiso 1 1 calc R U . . .
H5B H 0.3897 0.4100 0.6189 0.052 Uiso 1 1 calc R U . . .
N6 N 0.69467(15) 0.4135(2) 0.61418(18) 0.0339(5) Uani 1 1 d . . . . .
H6A H 0.7263 0.3540 0.6096 0.041 Uiso 1 1 calc R U . . .
H6B H 0.7127 0.4885 0.6175 0.041 Uiso 1 1 calc R U . . .
N7 N 0.58136(15) 0.2821(2) 0.61171(18) 0.0339(5) Uani 1 1 d . . . . .
N8 N 0.70337(16) 0.1530(2) 0.70029(19) 0.0396(6) Uani 1 1 d . . . . .
H8A H 0.7310 0.0840 0.7069 0.048 Uiso 1 1 calc R U . . .
H8B H 0.7242 0.2064 0.7456 0.048 Uiso 1 1 calc R U . . .
N9 N 0.59602(19) 0.0976(2) 0.5506(2) 0.0448(7) Uani 1 1 d . . . . .
H9A H 0.5560 0.0496 0.5566 0.054 Uiso 1 1 d R U . . .
H9B H 0.6406 0.0514 0.5523 0.054 Uiso 1 1 d R U . . .
N2 N 0.3368(2) 0.7316(3) 0.6228(2) 0.0551(8) Uani 1 1 d . . . . .
O1 O 0.8069(5) 0.6123(4) 0.5885(4) 0.0571(15) Uani 0.5 1 d . . P . .
H1D H 0.8021 0.6630 0.6267 0.086 Uiso 0.5 1 d R U P . .
H1E H 0.7783 0.6463 0.5342 0.086 Uiso 0.5 1 d R U P . .
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'
Cl Cl 0.3639 0.7018 '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
C3 C2 C1 105.8(2) . . ?
C3 C2 C4 128.4(3) . . ?
C4 C2 C1 125.7(2) . . ?
N6 C5 N4 115.2(2) . . ?
N7 C5 N4 117.0(2) . . ?
N7 C5 N6 127.8(2) . . ?
N4 C3 C2 105.2(2) . . ?
N5 C3 C2 130.3(2) . . ?
N5 C3 N4 124.5(2) . . ?
N1 C1 C2 125.3(2) . . ?
N3 C1 C2 112.5(2) . . ?
N3 C1 N1 122.2(2) . . ?
N8 C6 N7 120.5(3) . . ?
N9 C6 N7 118.0(2) . . ?
N9 C6 N8 121.3(3) . . ?
N2 C4 C2 176.5(3) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N3 N4 104.2(2) . . ?
C5 N4 N3 118.7(2) . . ?
C3 N4 C5 128.9(2) . . ?
C3 N4 N3 112.2(2) . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C5 N6 H6A 120.0 . . ?
C5 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C5 N7 C6 120.0(2) . . ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C6 N9 H9A 109.4 . . ?
C6 N9 H9B 109.3 . . ?
H9A N9 H9B 109.5 . . ?
H1D O1 H1E 104.5 . . ?
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
C2 C3 1.390(4) . ?
C2 C1 1.424(4) . ?
C2 C4 1.408(3) . ?
C5 N4 1.388(3) . ?
C5 N6 1.326(3) . ?
C5 N7 1.303(3) . ?
C3 N4 1.380(3) . ?
C3 N5 1.327(4) . ?
C1 N1 1.377(4) . ?
C1 N3 1.312(3) . ?
C6 N7 1.362(3) . ?
C6 N8 1.318(4) . ?
C6 N9 1.306(4) . ?
C4 N2 1.148(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N3 N4 1.400(3) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 H9A 0.8899 . ?
N9 H9B 0.8901 . ?
O1 H1D 0.8501 . ?
O1 H1E 0.8501 . ?
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
C2 C3 N4 C5 177.7(2) . . . . ?
C2 C3 N4 N3 1.5(3) . . . . ?
C2 C1 N3 N4 0.1(3) . . . . ?
C3 C2 C1 N1 177.4(3) . . . . ?
C3 C2 C1 N3 0.8(3) . . . . ?
C1 C2 C3 N4 -1.3(3) . . . . ?
C1 C2 C3 N5 179.8(3) . . . . ?
C1 N3 N4 C5 -177.6(2) . . . . ?
C1 N3 N4 C3 -1.0(3) . . . . ?
C4 C2 C3 N4 174.5(3) . . . . ?
C4 C2 C3 N5 -4.4(5) . . . . ?
C4 C2 C1 N1 1.5(4) . . . . ?
C4 C2 C1 N3 -175.1(3) . . . . ?
N1 C1 N3 N4 -176.7(2) . . . . ?
N4 C5 N7 C6 -171.6(2) . . . . ?
N5 C3 N4 C5 -3.3(5) . . . . ?
N5 C3 N4 N3 -179.5(3) . . . . ?
N6 C5 N4 C3 180.0(3) . . . . ?
N6 C5 N4 N3 -4.0(3) . . . . ?
N6 C5 N7 C6 11.2(4) . . . . ?
N7 C5 N4 C3 2.4(4) . . . . ?
N7 C5 N4 N3 178.5(2) . . . . ?
N8 C6 N7 C5 63.0(4) . . . . ?
N9 C6 N7 C5 -121.4(3) . . . . ?
