#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:49:13 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/21/7242140.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_7242140
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 N6 O4'
_chemical_formula_weight         194.17
_chemical_name_systematic
'2,4,6-triamino-1,3,5-triazine-1,3-dioxide dihydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-11-25 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.091(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0471(9)
_cell_length_b                   11.869(3)
_cell_length_c                   16.879(4)
_cell_measurement_reflns_used    4213
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.080
_cell_measurement_theta_min      2.098
_cell_volume                     810.6(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4213
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.080
_diffrn_reflns_theta_min         2.098
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1581
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0341
_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)+(0.0483P)²+0.1293P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1331
_reflns_number_total             1581
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01427c2.cif
_cod_data_source_block           1_a_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7242134--7242143.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7242140
_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   0.926
_shelx_estimated_absorpt_t_max   0.959
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.3981(3) 0.69220(9) 0.69061(6) 0.0442(3) Uani 1 1 d . . . . .
N1 N 0.6739(3) 0.55672(10) 0.58556(7) 0.0378(3) Uani 1 1 d D . . . .
H10 H 0.777(4) 0.5139(13) 0.5515(9) 0.045 Uiso 1 1 d D U . . .
H1 H 0.557(4) 0.5288(14) 0.6244(9) 0.045 Uiso 1 1 d D U . . .
C1 C 0.7109(3) 0.66496(10) 0.57861(8) 0.0300(3) Uani 1 1 d . . . . .
N2 N 1.0957(4) 0.86036(11) 0.45285(8) 0.0449(3) Uani 1 1 d D . . . .
H3 H 1.120(4) 0.9347(12) 0.4472(11) 0.054 Uiso 1 1 d D U . . .
H2 H 1.174(4) 0.8132(14) 0.4190(10) 0.054 Uiso 1 1 d D U . . .
O2 O 1.0277(3) 0.64073(8) 0.46541(6) 0.0415(3) Uani 1 1 d . . . . .
C2 C 0.9263(3) 0.82294(11) 0.51352(8) 0.0314(3) Uani 1 1 d . . . . .
N3 N 0.5181(3) 0.91326(11) 0.68316(8) 0.0425(3) Uani 1 1 d D . . . .
H5 H 0.555(4) 0.9862(12) 0.6813(10) 0.051 Uiso 1 1 d D U . . .
H4 H 0.404(4) 0.8833(15) 0.7220(10) 0.051 Uiso 1 1 d D U . . .
O3 O 0.6697(3) 0.61564(9) 0.32869(7) 0.0480(3) Uani 1 1 d D . . . .
H9 H 0.546(4) 0.6697(14) 0.3243(11) 0.058 Uiso 1 1 d D U . . .
H8 H 0.788(4) 0.6270(15) 0.3731(10) 0.058 Uiso 1 1 d D U . . .
C3 C 0.6348(3) 0.84956(11) 0.62675(8) 0.0313(3) Uani 1 1 d . . . . .
O4 O 0.8902(3) 0.65881(10) 0.79585(7) 0.0489(3) Uani 1 1 d D . . . .
H7 H 0.714(4) 0.6654(16) 0.7636(10) 0.059 Uiso 1 1 d D U . . .
H6 H 1.050(4) 0.6686(16) 0.7637(10) 0.059 Uiso 1 1 d D U . . .
N4 N 0.5725(3) 0.73651(9) 0.63070(6) 0.0312(3) Uani 1 1 d . . . . .
N5 N 0.8874(3) 0.70914(9) 0.51897(6) 0.0311(3) Uani 1 1 d . . . . .
N6 N 0.8052(3) 0.89298(9) 0.56712(7) 0.0345(3) 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 120.97(12) . . ?
N1 C1 N4 120.85(12) . . ?
N5 C1 N4 118.18(11) . . ?
N2 C2 N6 121.42(12) . . ?
N2 C2 N5 116.62(12) . . ?
N6 C2 N5 121.96(12) . . ?
N3 C3 N6 121.58(13) . . ?
N3 C3 N4 117.46(12) . . ?
N6 C3 N4 120.95(12) . . ?
O1 N4 C1 118.12(11) . . ?
O1 N4 C3 121.21(10) . . ?
C1 N4 C3 120.38(11) . . ?
O2 N5 C1 120.07(11) . . ?
O2 N5 C2 120.05(11) . . ?
C1 N5 C2 119.88(11) . . ?
C2 N6 C3 118.32(12) . . ?
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 1.3506(14) . ?
N1 C1 1.2989(17) . ?
C1 N5 1.3514(17) . ?
C1 N4 1.3516(16) . ?
N2 C2 1.3200(18) . ?
O2 N5 1.3485(14) . ?
C2 N6 1.3291(17) . ?
C2 N5 1.3631(17) . ?
N3 C3 1.3108(17) . ?
C3 N6 1.3344(17) . ?
C3 N4 1.3672(17) . ?
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
N1 H10 O2 0.880(13) 2.019(14) 2.7803(16) 144.0(14) 3_766
N1 H1 O3 0.879(14) 2.107(15) 2.8791(17) 146.2(15) 3_666
N2 H3 N6 0.893(14) 2.083(14) 2.9750(18) 177.9(17) 3_776
N2 H2 O4 0.863(14) 2.296(17) 2.9352(18) 130.9(15) 4_675
N3 H5 O4 0.880(14) 2.095(14) 2.9584(18) 166.7(15) 2_656
N3 H4 O3 0.885(14) 2.050(15) 2.8763(17) 154.9(17) 4_576
O3 H9 O4 0.817(14) 2.181(15) 2.9545(17) 158.0(18) 4_575
O3 H8 O2 0.893(14) 1.826(14) 2.7179(17) 176.4(17) .
O3 H8 N5 0.893(14) 2.671(16) 3.4951(18) 153.9(15) .
O4 H7 O1 0.893(14) 1.787(15) 2.6728(18) 171.5(17) .
O4 H7 N4 0.893(14) 2.455(17) 3.1840(17) 139.2(14) .
O4 H6 O1 0.861(14) 1.910(15) 2.7708(15) 178.7(18) 1_655
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 O1 0.75(19) . . . . ?
N5 C1 N4 O1 -179.53(11) . . . . ?
N1 C1 N4 C3 174.68(13) . . . . ?
N5 C1 N4 C3 -5.61(19) . . . . ?
N3 C3 N4 O1 -0.19(19) . . . . ?
N6 C3 N4 O1 -179.52(12) . . . . ?
N3 C3 N4 C1 -173.92(12) . . . . ?
N6 C3 N4 C1 6.7(2) . . . . ?
N1 C1 N5 O2 0.16(19) . . . . ?
N4 C1 N5 O2 -179.56(11) . . . . ?
N1 C1 N5 C2 -179.17(13) . . . . ?
N4 C1 N5 C2 1.12(18) . . . . ?
N2 C2 N5 O2 2.07(19) . . . . ?
N6 C2 N5 O2 -176.80(12) . . . . ?
N2 C2 N5 C1 -178.61(13) . . . . ?
N6 C2 N5 C1 2.5(2) . . . . ?
N2 C2 N6 C3 179.65(13) . . . . ?
N5 C2 N6 C3 -1.5(2) . . . . ?
N3 C3 N6 C2 177.64(13) . . . . ?
N4 C3 N6 C2 -3.05(19) . . . . ?
