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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/45/4504591.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_4504591
loop_
_publ_author_name
'Laus, G.'
'Kahlenberg, V.'
'Többens, D. M.'
'Jetti, R. K. R.'
'Griesser, U. J.'
'Schütz, J.'
'Kristeva, E.'
'Wurst, K.'
'Schottenberger, H.'
_publ_section_title
;
 Lattice Architecture and Hydrogen-Bonding Networks ofN-Aminoazolium
 andN,N‘-Diaminoazolium Chlorides
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              404
_journal_paper_doi               10.1021/cg0503595
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C2 H6 Cl N5'
_chemical_formula_weight         135.57
_chemical_name_common            '1,4-diamino-1,2,4-triazolium chloride'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6109(5)
_cell_length_b                   6.7780(9)
_cell_length_c                   16.3497(5)
_cell_measurement_reflns_used    8032
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      24.108
_cell_measurement_theta_min      0.998
_cell_volume                     621.79(10)
_computing_data_collection       KappaCCD
_computing_data_reduction
;
Denzo and Scalepark (Otwinowski&Minor, 1997)
;
_computing_molecular_graphics
;
BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME
;
_computing_publication_material
;
BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME
;
_computing_structure_refinement
;
BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME
;
_computing_structure_solution
;
BRUKER AXS SHELXTL Vers.6.12, DOS/WIN95/NT/2000/ME
;
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3390
_diffrn_reflns_theta_full        23.99
_diffrn_reflns_theta_max         23.99
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.516
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0299P)²+0.0818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0630
_reflns_number_gt                918
_reflns_number_total             972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0503595si20051106_031028.cif
_cod_data_source_block           CCDC277129
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4504591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl -0.09358(10) 1.33319(7) 0.10374(3) 0.0440(2) Uani 1 1 d .
N1 N -0.3265(3) 1.2075(2) 0.31856(10) 0.0354(4) Uani 1 1 d .
N2 N -0.5198(3) 1.3635(2) 0.40834(9) 0.0330(4) Uani 1 1 d .
N3 N -0.1953(3) 1.3731(3) 0.33426(11) 0.0476(5) Uani 1 1 d .
N4 N -0.2581(4) 1.0636(3) 0.26260(13) 0.0451(5) Uani 1 1 d .
H4A H -0.202(5) 1.124(3) 0.2217(16) 0.053(8) Uiso 1 1 d .
H4B H -0.148(5) 1.000(4) 0.2866(15) 0.058(9) Uiso 1 1 d .
N5 N -0.6972(4) 1.4076(3) 0.46711(13) 0.0443(5) Uani 1 1 d .
H5A H -0.777(5) 1.510(5) 0.4477(17) 0.069(9) Uiso 1 1 d .
H5B H -0.617(6) 1.445(4) 0.5077(16) 0.073(10) Uiso 1 1 d .
C1 C -0.5206(4) 1.2015(3) 0.36281(12) 0.0345(5) Uani 1 1 d .
H1 H -0.6375 1.1021 0.3624 0.041 Uiso 1 1 calc R
C2 C -0.3200(4) 1.4651(3) 0.38924(14) 0.0428(5) Uani 1 1 d .
H2 H -0.2771 1.5866 0.4127 0.051 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0525(4) 0.0357(3) 0.0438(3) 0.0030(2) 0.0064(3) 0.0115(2)
N1 0.0378(9) 0.0343(9) 0.0340(9) -0.0008(7) -0.0010(8) -0.0084(8)
N2 0.0341(9) 0.0336(9) 0.0313(8) 0.0034(7) -0.0028(7) -0.0045(7)
N3 0.0455(11) 0.0486(11) 0.0487(11) -0.0052(9) 0.0080(9) -0.0193(9)
N4 0.0510(13) 0.0443(12) 0.0398(11) -0.0049(9) 0.0043(10) -0.0025(10)
N5 0.0433(12) 0.0492(11) 0.0404(12) -0.0026(10) 0.0060(10) -0.0019(11)
C1 0.0343(11) 0.0335(11) 0.0357(10) 0.0033(9) -0.0014(9) -0.0068(9)
C2 0.0435(13) 0.0411(11) 0.0438(12) -0.0012(11) 0.0002(12) -0.0154(10)
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 N3 111.71(17)
C1 N1 N4 124.85(18)
N3 N1 N4 123.44(17)
C1 N2 C2 107.18(18)
C1 N2 N5 123.58(17)
C2 N2 N5 129.19(18)
C2 N3 N1 103.55(17)
H4A N4 H4B 110(3)
H4A N4 N1 106.5(16)
H4B N4 N1 104.6(18)
H4A N4 H4A 0(4)
H4B N4 H4A 110(3)
N1 N4 H4A 106.5(16)
H4A N4 H4B 110(3)
H4B N4 H4B 0(5)
N1 N4 H4B 104.6(18)
H4A N4 H4B 110(3)
H5B N5 H5A 108(3)
H5B N5 N2 103(2)
H5A N5 N2 106.2(18)
H5B N5 H5A 108(3)
H5A N5 H5A 0(5)
N2 N5 H5A 106.2(18)
H5B N5 H5B 0(2)
H5A N5 H5B 108(3)
N2 N5 H5B 103(2)
H5A N5 H5B 108(3)
N1 C1 N2 106.35(18)
N1 C1 H1 126.8
N2 C1 H1 126.8
N3 C2 N2 111.20(19)
N3 C2 H2 124.4
N2 C2 H2 124.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.308(3)
N1 N3 1.367(2)
N1 N4 1.391(3)
N2 C1 1.327(3)
N2 C2 1.352(3)
N2 N5 1.416(2)
N3 C2 1.299(3)
N4 H4A 0.84(3)
N4 H4B 0.85(3)
N4 H4A 0.84(3)
N4 H4B 0.85(3)
N5 H5B 0.84(3)
N5 H5A 0.88(3)
N5 H5A 0.88(3)
N5 H5B 0.84(3)
C1 H1 0.9400
C2 H2 0.9400
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
N4 H4A Cl1 0.84(3) 2.47(3) 3.307(2) 171(2) .
N4 H4B Cl1 0.85(3) 2.52(3) 3.333(3) 162(2) 3_545
N5 H5A Cl1 0.88(3) 2.46(3) 3.322(3) 166(2) 3_455
N5 H5B Cl1 0.84(3) 2.47(3) 3.277(2) 160(3) 2_485
C1 H1 Cl1 0.94 2.43 3.349(2) 165.7 3_445
C2 H2 Cl1 0.94 2.68 3.409(2) 134.8 3
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 14338429
