Bis(2-ethyl-1H-imidazol-3-ium) tetra­chloridomercurate(II)

Zhu, R.-Q.

doi:10.1107/S1600536811055371

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m148

doi:10.1107/S1600536811055371

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Bis(2-ethyl-1H-imidazol-3-ium) tetrachloridomercurate(II)

Run-Qiang Zhu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: zhurunqiang@163.com

(Received 13 December 2011; accepted 23 December 2011; online 14 January 2012)

The crystal structure of the title compound, (C₅H₉N₂)₂[HgCl₄], consists of discrete tetrachloridomercurate dications and discrete 2-methylimidazolium cations. In the complex anion, the mercury cations are coordinated by four chloride anions with distances between 2.4568 (14) and 2.4936 (15) Å in a tetrahedral geometry. In the crystal, the cations and anions are connected by intermolecular N—H⋯Cl interactions. One C atom of the cations is disordered and was refined using a split model (occupancy ratio 0.75:0.25).

Related literature

For a related structure and background to this study, see: Zhu (2011 ).

Experimental

Crystal data

(C₅H₉N₂)₂[HgCl₄]
M_r = 536.67
Triclinic, $[P \overline 1]$
a = 7.5784 (15) Å
b = 8.0972 (16) Å
c = 14.661 (3) Å
α = 92.42 (3)°
β = 97.88 (3)°
γ = 98.17 (3)°
V = 880.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 9.34 mm⁻¹
T = 293 K
0.33 × 0.28 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.216, T_max = 0.459
9149 measured reflections
4032 independent reflections
3437 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.064
S = 1.05
4032 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl3ⁱ	0.86	2.42	3.227 (4)	157
N2—H2N⋯Cl4ⁱⁱ	0.86	2.37	3.188 (4)	158
N3—H3N⋯Cl2	0.86	2.37	3.220 (4)	171
N4—H4N⋯Cl2ⁱⁱⁱ	0.86	2.47	3.285 (4)	159
Symmetry codes: (i) x, y+1, z+1; (ii) -x+2, -y+1, -z+1; (iii) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055371/nc2260sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055371/nc2260Isup2.hkl

checkCIF report

Related literature top

For a related structure and background to this study, see: Zhu (2011).

Experimental top

A mixture of HgCl₂ (4.26 g, 25 mmol), hydrochloric acid (50 mmol, 36%, 8 ml), and 2 - ethyl imidazole (4.8 g, 50 mmol) in 30 ml water was stirred for 10 minutes at room temperature. On slow evaporation of solvent colourless crystals of the title compound grew within two weeks.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with labeling and displacement ellipsoids drawn at the 30% probability level. Intermolecular hydrogen bonding is shown as dashed lines and disordering as full and open bonds..
	Fig. 2. Crystal structure of the title compound with intermolecular hydrogen bonding shown as dashed lines. A-atoms not involved in hydrogen bonding are omitted for clarity.

Bis(2-ethyl-1H-imidazol-3-ium) tetrachloridomercurate(II) top

Crystal data top

(C₅H₉N₂)₂[HgCl₄]	Z = 2
M_r = 536.67	F(000) = 508
Triclinic, P1	D_x = 2.025 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5784 (15) Å	Cell parameters from 4032 reflections
b = 8.0972 (16) Å	θ = 2.3–27.5°
c = 14.661 (3) Å	µ = 9.34 mm⁻¹
α = 92.42 (3)°	T = 293 K
β = 97.88 (3)°	Block, colourless
γ = 98.17 (3)°	0.33 × 0.28 × 0.20 mm
V = 880.4 (3) Å³

Data collection top

Rigaku SCXmini diffractometer	3437 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.216, T_max = 0.459	l = −19→19
9149 measured reflections	2 standard reflections every 150 reflections
4032 independent reflections	intensity decay: none

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0134P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4032 reflections	Δρ_max = 0.80 e Å⁻³
178 parameters	Δρ_min = −0.72 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0113 (4)

Crystal data top

(C₅H₉N₂)₂[HgCl₄]	γ = 98.17 (3)°
M_r = 536.67	V = 880.4 (3) Å³
Triclinic, P1	Z = 2
a = 7.5784 (15) Å	Mo Kα radiation
b = 8.0972 (16) Å	µ = 9.34 mm⁻¹
c = 14.661 (3) Å	T = 293 K
α = 92.42 (3)°	0.33 × 0.28 × 0.20 mm
β = 97.88 (3)°

Data collection top

Rigaku SCXmini diffractometer	3437 reflections with I > 2σ(I)
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	R_int = 0.044
T_min = 0.216, T_max = 0.459	2 standard reflections every 150 reflections
9149 measured reflections	intensity decay: none
4032 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.05	Δρ_max = 0.80 e Å⁻³
4032 reflections	Δρ_min = −0.72 e Å⁻³
178 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Hg1	0.79183 (2)	0.20862 (2)	0.266500 (12)	0.05040 (10)
C1	0.8846 (6)	0.7508 (6)	1.0072 (3)	0.0491 (11)
C2	1.1813 (6)	0.8008 (6)	1.0293 (3)	0.0573 (13)
H2	1.3004	0.8002	1.0206	0.069*
C3	1.1239 (7)	0.8776 (7)	1.0993 (3)	0.0585 (13)
H3	1.1950	0.9403	1.1492	0.070*
C4	0.6932 (6)	0.6871 (7)	0.9695 (4)	0.0713 (16)
H4A	0.6255	0.7802	0.9668	0.086*
H4B	0.6434	0.6101	1.0116	0.086*
C5	0.6688 (8)	0.6002 (8)	0.8757 (4)	0.0884 (19)
H5A	0.7108	0.6775	0.8327	0.133*
H5B	0.5434	0.5589	0.8567	0.133*
H5C	0.7365	0.5085	0.8775	0.133*
C6	0.5651 (7)	0.7388 (7)	0.3880 (4)	0.0593 (13)
C7	0.2790 (7)	0.7388 (7)	0.3359 (3)	0.0616 (14)
H7	0.1715	0.7778	0.3157	0.074*
C8	0.3024 (7)	0.5809 (7)	0.3409 (3)	0.0594 (13)
H8	0.2153	0.4872	0.3255	0.071*
C9	0.7550 (11)	0.8057 (10)	0.4345 (7)	0.079 (3)	0.75
H9A	0.8126	0.8820	0.3945	0.095*	0.75
H9B	0.7478	0.8690	0.4912	0.095*	0.75
C9'	0.771 (4)	0.770 (4)	0.3870 (18)	0.066 (8)*	0.25
H9C	0.7969	0.7341	0.3268	0.080*	0.25
H9D	0.8152	0.8883	0.3977	0.080*	0.25
C10	0.8631 (8)	0.6817 (9)	0.4553 (5)	0.099 (2)
H10A	0.9809	0.7330	0.4838	0.149*	0.75
H10B	0.8729	0.6193	0.3995	0.149*	0.75
H10C	0.8097	0.6078	0.4968	0.149*	0.75
H10D	0.9795	0.7445	0.4775	0.149*	0.25
H10E	0.8776	0.5746	0.4291	0.149*	0.25
H10F	0.7946	0.6664	0.5055	0.149*	0.25
N1	0.9390 (5)	0.8458 (5)	1.0834 (3)	0.0551 (10)
H1N	0.8690	0.8828	1.1183	0.066*
N2	1.0314 (5)	0.7232 (5)	0.9728 (3)	0.0530 (10)
H2N	1.0323	0.6648	0.9225	0.064*
N3	0.4807 (6)	0.5828 (5)	0.3731 (3)	0.0577 (11)
H3N	0.5303	0.4948	0.3828	0.069*
N4	0.4401 (6)	0.8336 (5)	0.3658 (3)	0.0570 (11)
H4N	0.4583	0.9411	0.3696	0.068*
Cl1	1.08854 (17)	0.11817 (17)	0.30103 (10)	0.0661 (4)
Cl2	0.62204 (16)	0.22853 (13)	0.39872 (8)	0.0516 (3)
Cl3	0.60382 (15)	−0.01229 (18)	0.15686 (8)	0.0652 (4)
Cl4	0.84770 (16)	0.47931 (15)	0.19336 (8)	0.0567 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.05255 (14)	0.04618 (14)	0.05352 (14)	0.00583 (9)	0.01238 (9)	0.00504 (9)
C1	0.048 (3)	0.043 (3)	0.060 (3)	0.010 (2)	0.014 (2)	0.014 (2)
C2	0.048 (3)	0.058 (3)	0.066 (3)	0.006 (2)	0.010 (3)	0.007 (3)
C3	0.065 (3)	0.051 (3)	0.055 (3)	0.002 (3)	−0.002 (3)	0.009 (3)
C4	0.053 (3)	0.076 (4)	0.083 (4)	0.001 (3)	0.012 (3)	0.011 (3)
C5	0.068 (4)	0.101 (5)	0.088 (4)	0.004 (4)	−0.006 (3)	−0.003 (4)
C6	0.052 (3)	0.051 (3)	0.076 (4)	0.004 (3)	0.016 (3)	0.012 (3)
C7	0.058 (3)	0.065 (4)	0.064 (3)	0.012 (3)	0.011 (3)	0.016 (3)
C8	0.061 (3)	0.055 (3)	0.058 (3)	0.001 (3)	0.001 (3)	0.002 (3)
C9	0.075 (6)	0.044 (5)	0.118 (8)	0.006 (4)	0.013 (6)	0.011 (5)
C10	0.077 (4)	0.105 (6)	0.108 (5)	0.011 (4)	−0.007 (4)	0.002 (4)
N1	0.063 (3)	0.052 (3)	0.057 (3)	0.013 (2)	0.027 (2)	0.010 (2)
N2	0.063 (2)	0.050 (2)	0.048 (2)	0.009 (2)	0.015 (2)	0.0008 (19)
N3	0.074 (3)	0.037 (2)	0.068 (3)	0.019 (2)	0.017 (2)	0.008 (2)
N4	0.071 (3)	0.036 (2)	0.067 (3)	0.007 (2)	0.020 (2)	0.010 (2)
Cl1	0.0564 (7)	0.0618 (8)	0.0825 (9)	0.0211 (6)	0.0061 (7)	0.0030 (7)
Cl2	0.0655 (7)	0.0368 (6)	0.0575 (7)	0.0104 (5)	0.0234 (6)	0.0046 (5)
Cl3	0.0490 (6)	0.0764 (9)	0.0646 (8)	−0.0031 (6)	0.0088 (6)	−0.0196 (7)
Cl4	0.0670 (7)	0.0450 (7)	0.0610 (7)	0.0097 (6)	0.0157 (6)	0.0124 (6)

Geometric parameters (Å, º) top

Hg1—Cl1	2.4568 (14)	C7—C8	1.320 (7)
Hg1—Cl2	2.4811 (13)	C7—N4	1.353 (6)
Hg1—Cl4	2.4885 (14)	C7—H7	0.9300
Hg1—Cl3	2.4936 (15)	C8—N3	1.366 (6)
C1—N1	1.312 (6)	C8—H8	0.9300
C1—N2	1.325 (5)	C9—C10	1.402 (10)
C1—C4	1.490 (6)	C9—H9A	0.9700
C2—C3	1.332 (6)	C9—H9B	0.9700
C2—N2	1.366 (6)	C9'—C10	1.41 (3)
C2—H2	0.9300	C9'—H9C	0.9700
C3—N1	1.373 (6)	C9'—H9D	0.9700
C3—H3	0.9300	C10—H10A	0.9600
C4—C5	1.494 (7)	C10—H10B	0.9600
C4—H4A	0.9700	C10—H10C	0.9600
C4—H4B	0.9700	C10—H10D	0.9600
C5—H5A	0.9600	C10—H10E	0.9601
C5—H5B	0.9600	C10—H10F	0.9600
C5—H5C	0.9600	N1—H1N	0.8602
C6—N4	1.317 (6)	N2—H2N	0.8606
C6—N3	1.327 (6)	N3—H3N	0.8598
C6—C9	1.519 (10)	N4—H4N	0.8599
C6—C9'	1.55 (3)

Cl1—Hg1—Cl2	115.95 (5)	C10—C9'—H9C	109.3
Cl1—Hg1—Cl4	105.47 (5)	C6—C9'—H9C	109.3
Cl2—Hg1—Cl4	112.40 (4)	C10—C9'—H9D	109.3
Cl1—Hg1—Cl3	106.12 (5)	C6—C9'—H9D	109.3
Cl2—Hg1—Cl3	105.11 (4)	H9C—C9'—H9D	108.0
Cl4—Hg1—Cl3	111.73 (5)	C9—C10—C9'	32.0 (9)
N1—C1—N2	106.7 (4)	C9—C10—H10A	109.5
N1—C1—C4	125.2 (4)	C9'—C10—H10A	117.4
N2—C1—C4	128.1 (5)	C9—C10—H10B	109.5
C3—C2—N2	106.8 (4)	C9'—C10—H10B	77.9
C3—C2—H2	126.6	H10A—C10—H10B	109.5
N2—C2—H2	126.6	C9—C10—H10C	109.5
C2—C3—N1	106.4 (4)	C9'—C10—H10C	126.8
C2—C3—H3	126.8	H10A—C10—H10C	109.5
N1—C3—H3	126.8	H10B—C10—H10C	109.5
C1—C4—C5	113.8 (5)	C9—C10—H10D	103.4
C1—C4—H4A	108.8	C9'—C10—H10D	109.5
C5—C4—H4A	108.8	H10A—C10—H10D	8.0
C1—C4—H4B	108.8	H10B—C10—H10D	107.7
C5—C4—H4B	108.8	H10C—C10—H10D	117.0
H4A—C4—H4B	107.7	C9—C10—H10E	137.6
C4—C5—H5A	109.5	C9'—C10—H10E	109.5
C4—C5—H5B	109.5	H10A—C10—H10E	106.2
H5A—C5—H5B	109.5	H10B—C10—H10E	35.0
C4—C5—H5C	109.5	H10C—C10—H10E	78.5
H5A—C5—H5C	109.5	H10D—C10—H10E	109.5
H5B—C5—H5C	109.5	C9—C10—H10F	83.0
N4—C6—N3	105.3 (4)	C9'—C10—H10F	109.5
N4—C6—C9	123.8 (5)	H10A—C10—H10F	104.5
N3—C6—C9	130.2 (6)	H10B—C10—H10F	136.5
N4—C6—C9'	131.4 (12)	H10C—C10—H10F	31.4
N3—C6—C9'	117.9 (11)	H10D—C10—H10F	109.5
C9—C6—C9'	29.3 (9)	H10E—C10—H10F	109.5
C8—C7—N4	107.3 (5)	C1—N1—C3	110.2 (4)
C8—C7—H7	126.3	C1—N1—H1N	124.9
N4—C7—H7	126.3	C3—N1—H1N	124.9
C7—C8—N3	106.1 (5)	C1—N2—C2	109.9 (4)
C7—C8—H8	126.9	C1—N2—H2N	125.1
N3—C8—H8	126.9	C2—N2—H2N	125.0
C10—C9—C6	114.1 (6)	C6—N3—C8	110.5 (4)
C10—C9—H9A	108.7	C6—N3—H3N	125.1
C6—C9—H9A	108.7	C8—N3—H3N	124.4
C10—C9—H9B	108.7	C6—N4—C7	110.8 (4)
C6—C9—H9B	108.7	C6—N4—H4N	124.7
H9A—C9—H9B	107.6	C7—N4—H4N	124.5
C10—C9'—C6	111.5 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl3ⁱ	0.86	2.42	3.227 (4)	157
N2—H2N···Cl4ⁱⁱ	0.86	2.37	3.188 (4)	158
N3—H3N···Cl2	0.86	2.37	3.220 (4)	171
N4—H4N···Cl2ⁱⁱⁱ	0.86	2.47	3.285 (4)	159

Symmetry codes: (i) x, y+1, z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	(C₅H₉N₂)₂[HgCl₄]
M_r	536.67
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5784 (15), 8.0972 (16), 14.661 (3)
α, β, γ (°)	92.42 (3), 97.88 (3), 98.17 (3)
V (Å³)	880.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	9.34
Crystal size (mm)	0.33 × 0.28 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.216, 0.459
No. of measured, independent and observed [I > 2σ(I)] reflections	9149, 4032, 3437
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.064, 1.05
No. of reflections	4032
No. of parameters	178
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.72

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl3ⁱ	0.86	2.42	3.227 (4)	157.2
N2—H2N···Cl4ⁱⁱ	0.86	2.37	3.188 (4)	158.2
N3—H3N···Cl2	0.86	2.37	3.220 (4)	170.9
N4—H4N···Cl2ⁱⁱⁱ	0.86	2.47	3.285 (4)	159.1

Symmetry codes: (i) x, y+1, z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y+1, z.

Acknowledgements

This work was supported by Southeast University.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, R.-Q. (2011). Acta Cryst. E67, m112. Web of Science CrossRef IUCr Journals Google Scholar