#------------------------------------------------------------------------------
#$Date: 2026-03-05 13:35:00 +0100 (Thu 05 de Mar de 2026) $
#$Revision: 304891 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/12/7251237.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_7251237
loop_
_publ_author_name
'Jiang, Xiu'e'
'Xu, Zeyu'
'Fan, Mingren'
'Wang, Ruihui'
'Wang, Yi'
'Zhang, Qinghua'
_publ_section_title
;
 Synthesis of energetic materials derived from hydroxynitropyrazine
;
_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
;
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 λ/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/[σ²(Fo²)+(0.0546P)²+0.4546P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.997
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.9364(3) 0.3853(2) 0.59858(8) 0.0254(4) Uani 1 1 d . . . . .
O002 O 0.4968(3) 0.2893(2) 0.81436(8) 0.0266(4) Uani 1 1 d . . . . .
O003 O 1.4236(4) 0.1730(2) 0.58484(9) 0.0334(4) Uani 1 1 d . . . . .
O004 O 1.1526(4) -0.1444(2) 0.87742(9) 0.0309(4) Uani 1 1 d . . . . .
O005 O 0.7478(4) 0.0030(2) 0.90584(9) 0.0321(4) Uani 1 1 d . . . . .
N006 N -0.0022(4) 0.4646(2) 0.86249(10) 0.0194(4) Uani 1 1 d . . . . .
H006 H 0.126958 0.454699 0.828502 0.023 Uiso 1 1 calc R U . . .
O007 O 0.1718(4) 0.6188(3) 0.70978(10) 0.0401(5) Uani 1 1 d G . . . .
H00I H 0.165571 0.677256 0.666135 0.060 Uiso 1 1 d G U . . .
H00J H 0.326031 0.538070 0.711064 0.060 Uiso 1 1 d G U . . .
N008 N 0.9447(4) -0.0239(2) 0.86325(10) 0.0225(4) Uani 1 1 d . . . . .
N009 N 0.7143(4) 0.3360(2) 0.70678(10) 0.0219(4) Uani 1 1 d . . . . .
N00A N 1.1417(4) 0.0470(2) 0.75091(10) 0.0211(4) Uani 1 1 d . . . . .
N00B N -0.3799(4) 0.5603(2) 0.92095(10) 0.0237(4) Uani 1 1 d . . . . .
H00D H -0.542428 0.623911 0.932496 0.028 Uiso 1 1 calc R U . . .
N00C N 1.3911(4) 0.0848(3) 0.64322(10) 0.0263(5) Uani 1 1 d . . . . .
N00D N -0.2238(4) 0.4116(3) 0.96475(10) 0.0243(5) Uani 1 1 d . . . . .
O00E O 1.5599(5) -0.0494(3) 0.66757(11) 0.0629(7) Uani 1 1 d . . . . .
N00F N -0.3197(4) 0.7168(3) 0.80327(11) 0.0285(5) Uani 1 1 d . . . . .
H00E H -0.478965 0.794827 0.804190 0.034 Uiso 1 1 calc R U . . .
H00F H -0.209927 0.722532 0.765040 0.034 Uiso 1 1 calc R U . . .
N00G N 0.2086(4) 0.2165(3) 0.94772(11) 0.0276(5) Uani 1 1 d . . . . .
H00G H 0.200294 0.148674 0.989695 0.033 Uiso 1 1 calc R U . . .
H00H H 0.352813 0.191408 0.918766 0.033 Uiso 1 1 calc R U . . .
C00H C 0.0032(5) 0.3569(3) 0.92804(12) 0.0219(5) Uani 1 1 d . . . . .
C00I C 0.9299(5) 0.0915(3) 0.79397(12) 0.0200(5) Uani 1 1 d . . . . .
C00J C 0.6979(5) 0.2411(3) 0.77506(12) 0.0201(5) Uani 1 1 d . . . . .
C00K C 0.9265(5) 0.2924(3) 0.66398(12) 0.0206(5) Uani 1 1 d . . . . .
C00L C -0.2445(5) 0.5894(3) 0.85994(12) 0.0214(5) Uani 1 1 d . . . . .
C00M C 1.1484(4) 0.1431(3) 0.68694(11) 0.0197(5) Uani 1 1 d . . . . .
C00N C 0.7051(5) 0.5342(3) 0.57832(13) 0.0298(6) Uani 1 1 d . . . . .
H00A H 0.731274 0.589108 0.528515 0.045 Uiso 1 1 calc R U . . .
H00B H 0.700569 0.620260 0.609918 0.045 Uiso 1 1 calc R U . . .
H00C H 0.526857 0.494072 0.582801 0.045 Uiso 1 1 calc R U . . .
N2 N 1.1330(11) -0.1692(7) 0.5723(3) 0.0450(13) Uani 0.5 1 d D U P A -1
C3 C 1.052(5) -0.0532(19) 0.5276(10) 0.031(3) Uani 0.5 1 d D U P A -1
C4 C 0.941(6) 0.0967(19) 0.4716(10) 0.034(3) Uani 0.5 1 d D U P A -1
H4A H 1.056978 0.089224 0.428191 0.050 Uiso 0.5 1 calc R U P A -1
H4B H 0.944528 0.206552 0.488358 0.050 Uiso 0.5 1 calc R U P A -1
H4C H 0.746128 0.094781 0.460915 0.050 Uiso 0.5 1 calc R U P A -1
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
C00K O001 C00N 116.90(17) . . ?
C00H N006 H006 126.5 . . ?
C00L N006 H006 126.5 . . ?
C00L N006 C00H 107.07(19) . . ?
H00I O007 H00J 104.5 . . ?
O004 N008 C00I 119.17(18) . . ?
O005 N008 O004 122.31(19) . . ?
O005 N008 C00I 118.52(18) . . ?
C00K N009 C00J 121.41(19) . . ?
C00I N00A C00M 118.83(19) . . ?
N00D N00B H00D 125.5 . . ?
C00L N00B H00D 125.5 . . ?
C00L N00B N00D 108.95(18) . . ?
O003 N00C O00E 122.5(2) . . ?
O003 N00C C00M 119.36(19) . . ?
O00E N00C C00M 118.07(19) . . ?
C00H N00D N00B 106.26(18) . . ?
H00E N00F H00F 120.0 . . ?
C00L N00F H00E 120.0 . . ?
C00L N00F H00F 120.0 . . ?
H00G N00G H00H 120.0 . . ?
C00H N00G H00G 120.0 . . ?
C00H N00G H00H 120.0 . . ?
N00D C00H N006 109.6(2) . . ?
N00D C00H N00G 127.4(2) . . ?
N00G C00H N006 123.1(2) . . ?
N00A C00I N008 114.05(19) . . ?
N00A C00I C00J 123.9(2) . . ?
C00J C00I N008 122.09(19) . . ?
O002 C00J N009 119.3(2) . . ?
O002 C00J C00I 125.9(2) . . ?
N009 C00J C00I 114.77(19) . . ?
O001 C00K C00M 119.46(19) . . ?
N009 C00K O001 120.2(2) . . ?
N009 C00K C00M 120.4(2) . . ?
N00B C00L N006 108.2(2) . . ?
N00B C00L N00F 128.5(2) . . ?
N00F C00L N006 123.4(2) . . ?
N00A C00M N00C 115.04(19) . . ?
N00A C00M C00K 120.8(2) . . ?
C00K C00M N00C 124.19(19) . . ?
O001 C00N H00A 109.5 . . ?
O001 C00N H00B 109.5 . . ?
O001 C00N H00C 109.5 . . ?
H00A C00N H00B 109.5 . . ?
H00A C00N H00C 109.5 . . ?
H00B C00N H00C 109.5 . . ?
N2 C3 C4 178.2(15) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
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
O001 C00K 1.326(3) . ?
O001 C00N 1.448(3) . ?
O002 C00J 1.236(3) . ?
O003 N00C 1.220(2) . ?
O004 N008 1.230(2) . ?
O005 N008 1.230(2) . ?
N006 H006 0.8800 . ?
N006 C00H 1.371(3) . ?
N006 C00L 1.358(3) . ?
O007 H00I 0.8700 . ?
O007 H00J 0.8700 . ?
N008 C00I 1.452(3) . ?
N009 C00J 1.382(3) . ?
N009 C00K 1.307(3) . ?
N00A C00I 1.310(3) . ?
N00A C00M 1.312(3) . ?
N00B H00D 0.8800 . ?
N00B N00D 1.402(3) . ?
N00B C00L 1.312(3) . ?
N00C O00E 1.221(3) . ?
N00C C00M 1.449(3) . ?
N00D C00H 1.310(3) . ?
N00F H00E 0.8800 . ?
N00F H00F 0.8800 . ?
N00F C00L 1.336(3) . ?
N00G H00G 0.8800 . ?
N00G H00H 0.8800 . ?
N00G C00H 1.330(3) . ?
C00I C00J 1.449(3) . ?
C00K C00M 1.431(3) . ?
C00N H00A 0.9800 . ?
C00N H00B 0.9800 . ?
C00N H00C 0.9800 . ?
N2 C3 1.143(8) . ?
C3 C4 1.464(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
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
O001 C00K C00M N00A -178.8(2) . . . . ?
O001 C00K C00M N00C 0.6(3) . . . . ?
O003 N00C C00M N00A -175.2(2) . . . . ?
O003 N00C C00M C00K 5.3(3) . . . . ?
O004 N008 C00I N00A 3.5(3) . . . . ?
O004 N008 C00I C00J -177.0(2) . . . . ?
O005 N008 C00I N00A -176.6(2) . . . . ?
O005 N008 C00I C00J 2.9(3) . . . . ?
N008 C00I C00J O002 1.8(4) . . . . ?
N008 C00I C00J N009 -179.24(19) . . . . ?
N009 C00K C00M N00A 0.5(3) . . . . ?
N009 C00K C00M N00C 179.9(2) . . . . ?
N00A C00I C00J O002 -178.7(2) . . . . ?
N00A C00I C00J N009 0.2(3) . . . . ?
N00B N00D C00H N006 -0.1(3) . . . . ?
N00B N00D C00H N00G -178.1(2) . . . . ?
N00D N00B C00L N006 -0.4(2) . . . . ?
N00D N00B C00L N00F 179.6(2) . . . . ?
O00E N00C C00M N00A 2.8(3) . . . . ?
O00E N00C C00M C00K -176.7(2) . . . . ?
C00H N006 C00L N00B 0.3(2) . . . . ?
C00H N006 C00L N00F -179.7(2) . . . . ?
C00I N00A C00M N00C 179.6(2) . . . . ?
C00I N00A C00M C00K -0.9(3) . . . . ?
C00J N009 C00K O001 179.68(19) . . . . ?
C00J N009 C00K C00M 0.4(3) . . . . ?
C00K N009 C00J O002 178.3(2) . . . . ?
C00K N009 C00J C00I -0.7(3) . . . . ?
C00L N006 C00H N00D -0.1(3) . . . . ?
C00L N006 C00H N00G 177.9(2) . . . . ?
C00L N00B N00D C00H 0.4(3) . . . . ?
C00M N00A C00I N008 -179.92(19) . . . . ?
C00M N00A C00I C00J 0.6(3) . . . . ?
C00N O001 C00K N009 0.3(3) . . . . ?
C00N O001 C00K C00M 179.6(2) . . . . ?
