Bis(4-amino-3,5-di­chloro­pyridinium) tetra­chloridomercurate(II)

Paul, A.C.; Crochet, A.; Stoeckli-Evans, H.; Kia, R.; Hemamalini, M.

doi:10.1107/S2414314625011204

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 12| December 2025| x251120

https://doi.org/10.1107/S2414314625011204

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Bis(4-amino-3,5-dichloropyridinium) tetrachloridomercurate(II)

Anaglit Catherine Paul,^a Aurélien Crochet,^b Helen Stoeckli-Evans,^c Reza Kia ^d and Madhukar Hemamalini ^a ^*

^aDepartment of Chemistry, Mother Teresa Women's University, Kodaikanal, Tamil Nadu, India, ^bChemistry Department, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland, ^cInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland, and ^dDepartment of Chemistry, Sharif University of Technology, Tehran, Iran
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 3 December 2025; accepted 11 December 2025; online 24 December 2025)

The asymmetric unit of the title compound, (C₅H₅Cl₂N₂)₂[HgCl₄], comprises two 4-amino-3,5-dichloropyridinium cations protonated at the pyridine N atoms and one tetrahedral tetrachloridomercurate(II) anion. The linking forces in the extended structure are predominantly N—H⋯Cl, bifurcated N—H⋯(Cl,Cl) and C—H⋯Cl hydrogen bonds, which connect the cations and anions into a three-dimensional network.

Keywords: crystal structure; hydrogen bonding; mercury.

CCDC reference: 2502353

Structure description

Following previous reports on the crystal structure of the parent 4-amino-3,5-dichloropyridine (Anantheeswary et al., 2024 ) and our recent work on 4-amino-3,5-dichloropyridinium 3-hydroxypicolinate monohydrate (Ashokan et al., 2023 ), we now describe the synthesis and structural characterization of the title salt, (C₅H₅Cl₂N₂)₂[HgCl₄].

The mercury(II) atom in the complex anion is coordinated by four chlorido ligands (Fig. 1) in a distorted tetrahedral shape (Table 1), which is typical behaviour for a d¹⁰ soft Lewis acid. The Hg—Cl bond lengths range from 2.485 (15) to 2.491 (14) Å, while Cl—Hg—Cl angles fall in the range 103.00 (5) to 121.6 (5)°. The 4-amino-3,5-dichloropyridinium cations are protonated at atoms N1 and N3 of the pyridine moiety. This protonation is evidenced by the increase in the internal angle C1—N1—C5 = 121.5 (5)° and C10—N3—C6 = 121.8 (5)° compared with the corresponding angle in neutral 4-amino-5,6-dichloro pyridine [116.4 (5)°] (Anantheeswary et al., 2024). Otherwise, the geometrical data for the title compound are in good agreement with literature data (Jellali et al., 2024 ). In the extended structure, the components are linked by numerous N—H⋯Cl, N—H⋯(Cl,Cl) and C—H⋯Cl (Table 2) hydrogen bonds as shown in Fig. 2, which generates a three-dimensional network. All the chlorido ions of the complex anion accept at least one hydrogen bond.

Table 1
Selected geometric parameters (Å, °)

Hg1—Cl7	2.4771 (15)	Hg1—Cl6	2.4854 (15)
Hg1—Cl8	2.4846 (15)	Hg1—Cl5	2.4908 (14)

Cl7—Hg1—Cl8	121.61 (5)	Cl7—Hg1—Cl5	105.31 (5)
Cl7—Hg1—Cl6	103.00 (5)	Cl8—Hg1—Cl5	103.92 (5)
Cl8—Hg1—Cl6	104.09 (5)	Cl6—Hg1—Cl5	120.16 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl8	0.87	2.53	3.202 (6)	134
N1—H1N⋯Cl8ⁱ	0.87	2.54	3.190 (6)	132
N2—H2NA⋯Cl7ⁱⁱ	0.87	2.60	3.439 (5)	162
N2—H2NB⋯Cl7ⁱⁱⁱ	0.87	2.51	3.338 (5)	159
N3—H3N⋯Cl5^iv	0.87	2.78	3.387 (5)	128
N3—H3N⋯Cl6^v	0.87	2.60	3.255 (6)	133
N4—H4NA⋯Cl5	0.87	2.47	3.229 (5)	146
N4—H4NB⋯Cl6^vi	0.87	2.46	3.265 (6)	154
C1—H1⋯Cl8	0.94	2.81	3.356 (6)	118
C5—H5⋯Cl8ⁱ	0.94	2.75	3.308 (6)	119
C10—H10⋯Cl5^iv	0.94	2.77	3.396 (6)	125
Symmetry codes: (i) ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) ; (v) $[-x+1, y+1, -z+{\script{1\over 2}}]$ ; (vi) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Figure 1
The asymmetric unit of the title compound with 50% probability displacement ellipsoids.

Figure 2
View of the crystal packing of the title compound along the b-axis direction with the complex anions shown in polyhedral representation.

A search of the Cambridge Structural Database (Version 5.43, update November 2022; Groom et al., 2016 ) for related structures revealed CSD refcodes BOLCUE: bis(3-amino-2-chloropyridinium)tetrakis(chlorido)mercurate(II) (Mrad et al., 2024 ); AGEWUF: 2-2′-bipyridinediium tetrabromidomercurate(II) (Ali et al., 2008 ); AJIKAG: bis(1,3-diethyl-1H-3,1-benzimidazole-3-ium)tetrabromidomercurate(II) (Li et al., 2009 ) and AQEDUX: bis(3-{[(pyridine-3-yl)methyl]amino}pyridine-1-ium) tetraiodidomercurate (Ye et al., 2016 ).

Synthesis and crystallization

4-Amino-3,5-dichloropyridine (45 mg) and mercury(II) chloride (67 mg) were used as starting materials. Each reagent was dissolved separately in methanol and water, respectively. The solutions were combined and stirred magnetically at room temperature, with the addition of 2 to 3 drops of dilute HCl to get a clear solution.. The resulting clear solution was left to stand for slow evaporation at room temperature. Colourless crystals suitable for X-ray diffraction were obtained after several days.

Refinement

Crystal data, data collection, and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	(C₅H₅Cl₂N₂)₂[HgCl₄]
M_r	670.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	250
a, b, c (Å)	18.0721 (6), 9.2125 (2), 23.7047 (8)
β (°)	101.652 (3)
V (Å³)	3865.2 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	9.07
Crystal size (mm)	0.76 × 0.54 × 0.34

Data collection
Diffractometer	STOE IPDS II
Absorption correction	Multi-scan (X-RED32; Stoe, 2023 )
T_min, T_max	0.035, 0.223
No. of measured, independent and observed [I > 2σ(I)] reflections	19023, 3877, 3645
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.621

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.13
No. of reflections	3877
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.34, −1.43
Computer programs: X-AREA WinXpose, Recipe, Integrate and LANA (Stoe, 2023), SHELXT2019/3 (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ), PLATON (Spek, 2020 ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2502353

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314625011204/hb4548sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625011204/hb4548Isup2.hkl

checkCIF report

Computing details top

Bis(4-amino-3,5-dichloropyridinium) tetrachloridomercurate(II) top

Crystal data top

(C₅H₅Cl₂N₂)₂[HgCl₄]	F(000) = 2512
M_r = 670.41	D_x = 2.304 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.0721 (6) Å	Cell parameters from 25660 reflections
b = 9.2125 (2) Å	θ = 1.8–26.8°
c = 23.7047 (8) Å	µ = 9.07 mm⁻¹
β = 101.652 (3)°	T = 250 K
V = 3865.2 (2) Å³	Block, colourless
Z = 8	0.76 × 0.54 × 0.34 mm

Data collection top

STOE IPDS II diffractometer	3877 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3645 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.041
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.2°, θ_min = 2.6°
rotation method, ω scans	h = −22→22
Absorption correction: multi-scan (X-RED32; Stoe, 2023)	k = −11→10
T_min = 0.035, T_max = 0.223	l = −29→29
19023 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0433P)² + 32.4079P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.001
3877 reflections	Δρ_max = 1.34 e Å⁻³
209 parameters	Δρ_min = −1.43 e Å⁻³
0 restraints	Extinction correction: (SHELXL-2019/3; Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.00160 (7)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were positioned geometrically [C—H = 0.94, N—H = 0.87 Å] and were refined using a riding model with U_iso(H) = 1.2 U_eq(carrier).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.77457 (8)	0.70283 (17)	0.41102 (6)	0.0390 (3)
Cl2	0.82254 (8)	0.30420 (17)	0.58344 (6)	0.0400 (3)
N1	0.6440 (3)	0.5048 (6)	0.4991 (2)	0.0369 (11)
H1N	0.596006	0.505840	0.499608	0.044*
N2	0.8697 (3)	0.5031 (6)	0.4970 (2)	0.0430 (12)
H2NA	0.900317	0.448533	0.521073	0.052*
H2NB	0.887166	0.557362	0.472618	0.052*
C1	0.6698 (3)	0.5874 (6)	0.4607 (3)	0.0349 (12)
H1	0.635829	0.644304	0.434454	0.042*
C2	0.7442 (3)	0.5896 (6)	0.4594 (2)	0.0319 (12)
C3	0.7973 (3)	0.5036 (6)	0.4975 (2)	0.0304 (11)
C4	0.7652 (3)	0.4178 (6)	0.5361 (2)	0.0312 (11)
C5	0.6903 (3)	0.4209 (7)	0.5366 (2)	0.0352 (12)
H5	0.670954	0.364034	0.563185	0.042*
Cl3	0.45226 (9)	0.82260 (17)	0.15818 (7)	0.0444 (4)
Cl4	0.29236 (11)	0.8407 (2)	0.32800 (7)	0.0536 (4)
N3	0.3817 (3)	1.1382 (6)	0.2446 (2)	0.0403 (11)
H3N	0.384547	1.232482	0.245097	0.048*
N4	0.3683 (3)	0.6958 (6)	0.2426 (2)	0.0453 (13)
H4NA	0.344345	0.651024	0.265793	0.054*
H4NB	0.389316	0.646303	0.218772	0.054*
C6	0.4142 (3)	1.0637 (6)	0.2073 (3)	0.0365 (12)
H6	0.439799	1.113270	0.182342	0.044*
C7	0.4101 (3)	0.9163 (6)	0.2059 (3)	0.0343 (12)
C8	0.3727 (3)	0.8380 (6)	0.2434 (2)	0.0326 (11)
C9	0.3399 (3)	0.9243 (6)	0.2810 (3)	0.0349 (12)
C10	0.3449 (4)	1.0711 (6)	0.2810 (3)	0.0397 (13)
H10	0.322599	1.125959	0.306576	0.048*
Hg1	0.46587 (2)	0.40614 (3)	0.37445 (2)	0.03929 (12)
Cl5	0.33340 (8)	0.42430 (15)	0.31931 (6)	0.0376 (3)
Cl6	0.57310 (10)	0.42101 (15)	0.32352 (8)	0.0447 (4)
Cl7	0.47767 (8)	0.15743 (18)	0.41499 (7)	0.0447 (4)
Cl8	0.48132 (7)	0.62415 (16)	0.43745 (6)	0.0352 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0401 (7)	0.0461 (8)	0.0348 (7)	−0.0001 (6)	0.0173 (6)	0.0071 (6)
Cl2	0.0328 (7)	0.0520 (8)	0.0353 (7)	0.0013 (6)	0.0067 (5)	0.0099 (6)
N1	0.023 (2)	0.052 (3)	0.038 (3)	0.000 (2)	0.0127 (19)	0.003 (2)
N2	0.026 (2)	0.062 (3)	0.042 (3)	0.002 (2)	0.011 (2)	0.015 (2)
C1	0.027 (3)	0.042 (3)	0.035 (3)	0.001 (2)	0.005 (2)	0.004 (2)
C2	0.033 (3)	0.039 (3)	0.026 (3)	−0.005 (2)	0.013 (2)	−0.001 (2)
C3	0.025 (2)	0.041 (3)	0.028 (2)	−0.002 (2)	0.011 (2)	−0.005 (2)
C4	0.029 (3)	0.039 (3)	0.026 (3)	0.001 (2)	0.007 (2)	0.002 (2)
C5	0.029 (3)	0.049 (3)	0.030 (3)	−0.003 (2)	0.013 (2)	0.006 (2)
Cl3	0.0522 (9)	0.0443 (8)	0.0431 (8)	−0.0036 (7)	0.0250 (7)	−0.0067 (6)
Cl4	0.0700 (11)	0.0523 (9)	0.0481 (9)	−0.0009 (8)	0.0345 (8)	0.0042 (7)
N3	0.048 (3)	0.028 (2)	0.045 (3)	0.003 (2)	0.010 (2)	−0.002 (2)
N4	0.060 (3)	0.036 (3)	0.048 (3)	0.001 (2)	0.029 (3)	−0.002 (2)
C6	0.037 (3)	0.035 (3)	0.037 (3)	−0.002 (2)	0.006 (2)	0.001 (2)
C7	0.038 (3)	0.034 (3)	0.032 (3)	−0.001 (2)	0.010 (2)	−0.001 (2)
C8	0.037 (3)	0.034 (3)	0.027 (3)	−0.002 (2)	0.007 (2)	0.000 (2)
C9	0.037 (3)	0.037 (3)	0.032 (3)	0.001 (2)	0.011 (2)	0.001 (2)
C10	0.048 (3)	0.034 (3)	0.039 (3)	0.005 (3)	0.012 (3)	−0.004 (2)
Hg1	0.03396 (16)	0.04079 (17)	0.04560 (17)	0.00137 (9)	0.01388 (10)	0.00097 (9)
Cl5	0.0353 (7)	0.0351 (7)	0.0416 (7)	−0.0016 (5)	0.0060 (6)	0.0068 (6)
Cl6	0.0570 (9)	0.0323 (7)	0.0555 (9)	0.0049 (6)	0.0370 (8)	0.0050 (6)
Cl7	0.0339 (7)	0.0474 (8)	0.0567 (9)	0.0056 (6)	0.0182 (6)	0.0199 (7)
Cl8	0.0288 (6)	0.0424 (7)	0.0378 (7)	−0.0016 (5)	0.0152 (5)	−0.0010 (6)

Geometric parameters (Å, º) top

Cl1—C2	1.719 (5)	N3—C10	1.342 (8)
Cl2—C4	1.720 (6)	N3—C6	1.344 (8)
N1—C5	1.337 (8)	N3—H3N	0.8700
N1—C1	1.340 (8)	N4—C8	1.312 (8)
N1—H1N	0.8700	N4—H4NA	0.8700
N2—C3	1.312 (7)	N4—H4NB	0.8700
N2—H2NA	0.8700	C6—C7	1.360 (8)
N2—H2NB	0.8700	C6—H6	0.9400
C1—C2	1.353 (8)	C7—C8	1.418 (8)
C1—H1	0.9400	C8—C9	1.411 (8)
C2—C3	1.418 (8)	C9—C10	1.355 (8)
C3—C4	1.418 (8)	C10—H10	0.9400
C4—C5	1.357 (8)	Hg1—Cl7	2.4771 (15)
C5—H5	0.9400	Hg1—Cl8	2.4846 (15)
Cl3—C7	1.719 (6)	Hg1—Cl6	2.4854 (15)
Cl4—C9	1.720 (6)	Hg1—Cl5	2.4908 (14)

C5—N1—C1	121.5 (5)	C8—N4—H4NA	120.0
C5—N1—H1N	119.2	C8—N4—H4NB	120.0
C1—N1—H1N	119.2	H4NA—N4—H4NB	120.0
C3—N2—H2NA	120.0	N3—C6—C7	119.8 (6)
C3—N2—H2NB	120.0	N3—C6—H6	120.1
H2NA—N2—H2NB	120.0	C7—C6—H6	120.1
N1—C1—C2	120.6 (5)	C6—C7—C8	121.6 (6)
N1—C1—H1	119.7	C6—C7—Cl3	119.2 (5)
C2—C1—H1	119.7	C8—C7—Cl3	119.2 (4)
C1—C2—C3	121.6 (5)	N4—C8—C9	122.7 (5)
C1—C2—Cl1	118.5 (5)	N4—C8—C7	122.2 (5)
C3—C2—Cl1	119.9 (4)	C9—C8—C7	115.0 (5)
N2—C3—C4	122.8 (5)	C10—C9—C8	121.8 (6)
N2—C3—C2	122.9 (5)	C10—C9—Cl4	119.2 (5)
C4—C3—C2	114.3 (5)	C8—C9—Cl4	119.0 (4)
C5—C4—C3	122.1 (5)	N3—C10—C9	120.1 (6)
C5—C4—Cl2	118.5 (4)	N3—C10—H10	120.0
C3—C4—Cl2	119.4 (4)	C9—C10—H10	120.0
N1—C5—C4	119.9 (5)	Cl7—Hg1—Cl8	121.61 (5)
N1—C5—H5	120.1	Cl7—Hg1—Cl6	103.00 (5)
C4—C5—H5	120.1	Cl8—Hg1—Cl6	104.09 (5)
C10—N3—C6	121.8 (5)	Cl7—Hg1—Cl5	105.31 (5)
C10—N3—H3N	119.1	Cl8—Hg1—Cl5	103.92 (5)
C6—N3—H3N	119.1	Cl6—Hg1—Cl5	120.16 (6)

C5—N1—C1—C2	−0.9 (9)	C10—N3—C6—C7	0.2 (9)
N1—C1—C2—C3	1.1 (9)	N3—C6—C7—C8	−0.8 (9)
N1—C1—C2—Cl1	−177.6 (5)	N3—C6—C7—Cl3	−179.8 (5)
C1—C2—C3—N2	179.7 (6)	C6—C7—C8—N4	−180.0 (6)
Cl1—C2—C3—N2	−1.6 (8)	Cl3—C7—C8—N4	−0.9 (8)
C1—C2—C3—C4	−0.1 (8)	C6—C7—C8—C9	1.0 (8)
Cl1—C2—C3—C4	178.5 (4)	Cl3—C7—C8—C9	180.0 (4)
N2—C3—C4—C5	179.2 (6)	N4—C8—C9—C10	−179.7 (6)
C2—C3—C4—C5	−1.0 (8)	C7—C8—C9—C10	−0.7 (9)
N2—C3—C4—Cl2	−1.7 (8)	N4—C8—C9—Cl4	0.4 (8)
C2—C3—C4—Cl2	178.2 (4)	C7—C8—C9—Cl4	179.4 (4)
C1—N1—C5—C4	−0.2 (9)	C6—N3—C10—C9	0.1 (10)
C3—C4—C5—N1	1.2 (9)	C8—C9—C10—N3	0.2 (10)
Cl2—C4—C5—N1	−178.0 (5)	Cl4—C9—C10—N3	−179.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl8	0.87	2.53	3.202 (6)	134
N1—H1N···Cl8ⁱ	0.87	2.54	3.190 (6)	132
N2—H2NA···Cl7ⁱⁱ	0.87	2.60	3.439 (5)	162
N2—H2NB···Cl7ⁱⁱⁱ	0.87	2.51	3.338 (5)	159
N3—H3N···Cl5^iv	0.87	2.78	3.387 (5)	128
N3—H3N···Cl6^v	0.87	2.60	3.255 (6)	133
N4—H4NA···Cl5	0.87	2.47	3.229 (5)	146
N4—H4NB···Cl6^vi	0.87	2.46	3.265 (6)	154
C1—H1···Cl8	0.94	2.81	3.356 (6)	118
C5—H5···Cl8ⁱ	0.94	2.75	3.308 (6)	119
C10—H10···Cl5^iv	0.94	2.77	3.396 (6)	125

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, −y+1/2, −z+1; (iii) x+1/2, y+1/2, z; (iv) x, y+1, z; (v) −x+1, y+1, −z+1/2; (vi) −x+1, y, −z+1/2.

Acknowledgements

HSE is grateful to the University of Neuchâtel for their support over the years.

References

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