#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:49:13 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/21/7242142.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_7242142
loop_
_publ_author_name
'Feng, Zhicun'
'Zhang, Yu'
'Li, Yanan'
'Xu, Kangzhen'
_publ_section_title
;
 Adjacent N→ O and C--NH2 groups --- a highly efficient
 amphoteric structure for energetic materials resulting from
 tautomerization proved by crystal engineering
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1544
_journal_page_last               1549
_journal_paper_doi               10.1039/D0CE01427C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C3 H10 N8 O9'
_chemical_formula_weight         302.19
_chemical_name_systematic
'2,4,6-triamino-1,3-dihydroxy-1,3,5-triazine-1,3-diium dinitrate monohydrate'
_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   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-02-08 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                114.164(6)
_cell_angle_beta                 94.456(6)
_cell_angle_gamma                107.497(7)
_cell_formula_units_Z            2
_cell_length_a                   7.448(3)
_cell_length_b                   8.709(4)
_cell_length_c                   10.072(4)
_cell_measurement_reflns_used    2,968
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.088
_cell_measurement_theta_min      2.278
_cell_volume                     553.2(4)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker Smart Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2968
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.088
_diffrn_reflns_theta_min         2.278
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0591
_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)+(0.0838P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1275
_reflns_number_total             2131
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01427c2.cif
_cod_data_source_block           1_a_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7242134--7242143.cif.'
_cod_original_cell_volume        553.1(4)
_cod_database_code               7242142
_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_min   0.912
_shelx_estimated_absorpt_t_max   0.964
_shelxl_version_number           2013-2
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
O1 O 0.0946(4) 0.3651(4) 0.7747(3) 0.0414(8) Uani 1 1 d D . . . .
H6 H 0.147(6) 0.296(5) 0.794(5) 0.050 Uiso 1 1 d D U . . .
N1 N 0.1658(5) 0.4091(4) 0.5355(3) 0.0320(8) Uani 1 1 d D . . . .
H7 H 0.175(5) 0.426(5) 0.456(3) 0.038 Uiso 1 1 d D U . . .
H1 H 0.079(5) 0.313(4) 0.532(4) 0.038 Uiso 1 1 d D U . . .
C1 C 0.2801(5) 0.5235(5) 0.6647(4) 0.0255(8) Uani 1 1 d . . . . .
O2 O 0.4697(4) 0.6880(4) 0.5608(3) 0.0351(7) Uani 1 1 d D . . . .
H5 H 0.401(5) 0.741(5) 0.546(5) 0.042 Uiso 1 1 d D U . . .
N2 N 0.6870(5) 0.9318(5) 0.8320(4) 0.0405(9) Uani 1 1 d D . . . .
H8 H 0.704(6) 0.945(6) 0.751(3) 0.049 Uiso 1 1 d D U . . .
H2 H 0.772(5) 1.011(5) 0.916(3) 0.049 Uiso 1 1 d D U . . .
C2 C 0.5452(5) 0.7945(5) 0.8232(4) 0.0314(9) Uani 1 1 d . . . . .
N3 N 0.3253(5) 0.6014(5) 1.0404(4) 0.0389(9) Uani 1 1 d D . . . .
H4 H 0.391(5) 0.686(4) 1.127(3) 0.047 Uiso 1 1 d D U . . .
H3 H 0.227(4) 0.509(4) 1.031(5) 0.047 Uiso 1 1 d D U . . .
O3 O -0.0888(4) 0.2066(5) 0.1948(4) 0.0592(10) Uani 1 1 d . . . . .
C3 C 0.3669(5) 0.6294(5) 0.9273(4) 0.0307(9) Uani 1 1 d . . . . .
O4 O 0.0355(5) 0.2668(5) 0.0290(3) 0.0578(9) Uani 1 1 d . . . . .
N4 N 0.2568(4) 0.5018(4) 0.7878(3) 0.0284(8) Uani 1 1 d . . . . .
O5 O 0.1951(4) 0.4141(4) 0.2576(3) 0.0449(8) Uani 1 1 d . . . . .
N5 N 0.4278(4) 0.6704(4) 0.6852(3) 0.0278(7) Uani 1 1 d . . . . .
N6 N 0.5123(4) 0.7736(4) 0.9439(3) 0.0336(8) Uani 1 1 d . . . . .
O6 O 0.1864(4) 0.9883(4) 0.4072(4) 0.0500(9) Uani 1 1 d . . . . .
N8 N 0.2662(5) 0.8917(5) 0.4247(4) 0.0342(8) Uani 1 1 d . . . . .
O8 O 0.2238(4) 0.8358(4) 0.5227(3) 0.0351(7) Uani 1 1 d . . . . .
O9 O 0.2457(5) 0.1453(4) 0.7734(3) 0.0463(8) Uani 1 1 d D . . . .
H11 H 0.254(6) 0.123(6) 0.846(3) 0.056 Uiso 1 1 d D U . . .
H10 H 0.219(7) 0.052(4) 0.692(3) 0.056 Uiso 1 1 d D U . . .
N7 N 0.0475(5) 0.2953(5) 0.1608(4) 0.0348(8) Uani 1 1 d . . . . .
O7 O 0.3854(4) 0.8481(4) 0.3553(3) 0.0449(8) Uani 1 1 d . . . . .
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
N1 C1 N5 122.6(3) . . ?
N1 C1 N4 121.6(3) . . ?
N5 C1 N4 115.8(3) . . ?
N2 C2 N6 121.7(4) . . ?
N2 C2 N5 118.2(3) . . ?
N6 C2 N5 120.2(3) . . ?
N3 C3 N6 122.0(3) . . ?
N3 C3 N4 117.5(3) . . ?
N6 C3 N4 120.4(3) . . ?
C1 N4 C3 122.1(3) . . ?
C1 N4 O1 117.4(3) . . ?
C3 N4 O1 119.3(3) . . ?
C1 N5 C2 122.5(3) . . ?
C1 N5 O2 117.8(3) . . ?
C2 N5 O2 119.6(3) . . ?
C3 N6 C2 118.8(3) . . ?
O6 N8 O7 123.2(3) . . ?
O6 N8 O8 117.9(3) . . ?
O7 N8 O8 118.9(3) . . ?
O4 N7 O3 119.5(4) . . ?
O4 N7 O5 119.5(3) . . ?
O3 N7 O5 121.0(3) . . ?
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 N4 1.370(4) . ?
N1 C1 1.292(5) . ?
C1 N5 1.339(4) . ?
C1 N4 1.344(4) . ?
O2 N5 1.371(4) . ?
N2 C2 1.301(5) . ?
C2 N6 1.331(5) . ?
C2 N5 1.370(5) . ?
N3 C3 1.300(5) . ?
O3 N7 1.243(4) . ?
C3 N6 1.327(5) . ?
C3 N4 1.369(5) . ?
O4 N7 1.237(4) . ?
O5 N7 1.247(4) . ?
O6 N8 1.224(4) . ?
N8 O7 1.226(4) . ?
N8 O8 1.288(4) . ?
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
O1 H6 O9 0.881(19) 1.64(2) 2.492(4) 162(4) .
N1 H7 O5 0.872(19) 1.98(2) 2.840(4) 169(4) .
N1 H7 N7 0.872(19) 2.68(3) 3.449(5) 148(3) .
N1 H1 O8 0.875(19) 2.13(3) 2.882(4) 144(3) 2_566
O2 H5 N8 0.822(19) 2.48(2) 3.256(5) 157(4) .
O2 H5 O8 0.822(19) 1.81(2) 2.621(4) 172(4) .
O2 H5 O7 0.822(19) 2.47(3) 3.051(4) 129(3) .
N2 H8 O6 0.879(19) 2.06(2) 2.916(5) 166(4) 2_676
N2 H8 N8 0.879(19) 2.68(3) 3.499(5) 156(4) 2_676
N2 H8 O7 0.879(19) 2.65(3) 3.309(5) 132(3) 2_676
N2 H2 O3 0.87(2) 2.54(2) 3.371(5) 159(4) 1_666
N2 H2 O4 0.87(2) 2.25(3) 3.016(5) 146(4) 1_666
N3 H4 O9 0.86(2) 2.54(3) 3.167(5) 130(3) 2_667
N3 H4 O7 0.86(2) 2.16(3) 2.915(5) 147(4) 1_556
N3 H3 O4 0.874(19) 2.15(2) 3.011(5) 167(4) 1_556
O9 H11 O3 0.836(18) 2.60(4) 3.093(4) 119(3) 2_556
O9 H11 N6 0.836(18) 2.29(3) 2.941(4) 135(4) 2_667
O9 H10 N8 0.840(19) 2.59(2) 3.342(5) 150(4) 1_545
O9 H10 O8 0.840(19) 1.97(2) 2.787(4) 165(5) 1_545
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
N1 C1 N4 C3 -174.6(4) . . . . ?
N5 C1 N4 C3 5.2(5) . . . . ?
N1 C1 N4 O1 -7.1(5) . . . . ?
N5 C1 N4 O1 172.6(3) . . . . ?
N3 C3 N4 C1 175.8(4) . . . . ?
N6 C3 N4 C1 -5.4(6) . . . . ?
N3 C3 N4 O1 8.6(5) . . . . ?
N6 C3 N4 O1 -172.7(3) . . . . ?
N1 C1 N5 C2 177.9(4) . . . . ?
N4 C1 N5 C2 -1.8(5) . . . . ?
N1 C1 N5 O2 -7.0(5) . . . . ?
N4 C1 N5 O2 173.2(3) . . . . ?
N2 C2 N5 C1 179.0(4) . . . . ?
N6 C2 N5 C1 -1.4(6) . . . . ?
N2 C2 N5 O2 4.0(5) . . . . ?
N6 C2 N5 O2 -176.4(3) . . . . ?
N3 C3 N6 C2 -179.3(4) . . . . ?
N4 C3 N6 C2 1.9(6) . . . . ?
N2 C2 N6 C3 -179.1(4) . . . . ?
N5 C2 N6 C3 1.3(6) . . . . ?
