Synthesis of energetic materials derived from hydroxynitropyrazine
Jiang, Xiu'e; Xu, Zeyu; Fan, Mingren; Wang, Ruihui; Wang, Yi; Zhang, Qinghua; CrystEngComm 28 (2026) 163–168; doi:10.1039/D5CE01009H

data_7251237
_publ_section_title
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 Synthesis of energetic materials derived from hydroxynitropyrazine
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_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              163
_journal_page_last               168
_journal_paper_doi               10.1039/D5CE01009H
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         '2(C5 H3 N4 O6), 2(C2 H6 N5), 2(H2 O), C2 H3 N'
_chemical_formula_sum            'C16 H25 N19 O14'
_chemical_formula_weight         707.55
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-31
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
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2025-04-21 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                79.632(2)
_cell_angle_beta                 87.383(2)
_cell_angle_gamma                77.4320(10)
_cell_formula_units_Z            1
_cell_length_a                   4.8568(2)
_cell_length_b                   7.9049(3)
_cell_length_c                   18.9454(9)
_cell_measurement_reflns_used    2941
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.68
_cell_volume                     698.33(5)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0595
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8029
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_min         2.186
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5439
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1288 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.7297.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       needle
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0517
_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/[\s^2^(Fo^2^)+(0.0546P)^2^+0.4546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2087
_reflns_number_total             2836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01009h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7251237--7251239.cif.'
_cod_database_code               7251237
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.997
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N2-C3
 1.14 with sigma of 0.02
 C3-N2
 1.137 with sigma of 0.01
 C3-C4
 1.456 with sigma of 0.01
 C4-N2
 2.593 with sigma of 0.02
 N2-C4
 2.59 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N2 \\sim C3 \\sim C4: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
4. Rigid body (RIGU) restrains
 N2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: N2(0.5) C3(0.5) C4(0.5) H4A(0.5) H4B(0.5) H4C(0.5)
6.a Free rotating group:
 O007(H00I,H00J)
6.b Aromatic/amide H refined with riding coordinates:
 N006(H006), N00B(H00D)
6.c X=CH2 refined with riding coordinates:
 N00F(H00E,H00F), N00G(H00G,H00H)
6.d Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              73524
_olex2_submission_special_instructions 'No special instructions were received'