Bis(2-trifluoro­methyl-1H-benzimidazol-3-ium) tetra­chloridomercurate dihydrate

Liu, M.-L.

doi:10.1107/S1600536812018855

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m716

doi:10.1107/S1600536812018855

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Bis(2-trifluoromethyl-1H-benzimidazol-3-ium) tetrachloridomercurate dihydrate

Ming-Liang Liu ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: jgsdxlml@163.com

(Received 20 April 2012; accepted 26 April 2012; online 2 May 2012)

In the title compound, (C₈H₆F₃N₂)₂[HgCl₄]·2H₂O, the Hg^II cation is coordinated by four Cl⁻ anions in a distorted tetrahedral geometry. In the crystal, the 2-trifluoromethyl-1H-benzimidazolium cations link to the [HgCl₄]²⁻ complex anions and lattice water molecules via N—H⋯Cl and N—H⋯O hydrogen bonds, and the lattice water molecules further link to the Hg complex anion and the organic cations via O—H⋯Cl and O—H⋯F hydrogen bonding. One of the trifluoromethyl groups is disordered over two orientations in a 0.59 (4):0.41 (4) ratio.

Related literature

For background to ferroelectric complexes, see: Fu et al. (2011 ); Ye et al. (2009 ). Zhang et al. (2009 , 2010 , 2012 ). For related structures, see: Liu (2011a ,b , 2012a ,b ,c ).

Experimental

Crystal data

(C₈H₆F₃N₂)₂[HgCl₄]·2H₂O
M_r = 752.72
Triclinic, $[P \overline 1]$
a = 9.2485 (18) Å
b = 10.029 (2) Å
c = 14.754 (3) Å
α = 79.40 (3)°
β = 75.79 (3)°
γ = 67.74 (3)°
V = 1221.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 6.81 mm⁻¹
T = 293 K
0.36 × 0.32 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.095, T_max = 0.152
12786 measured reflections
5564 independent reflections
4040 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.119
S = 1.08
5564 reflections
326 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −1.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl2ⁱ	0.86	2.23	3.081 (6)	170
N2—H2A⋯O1ⁱⁱ	0.86	1.80	2.656 (8)	174
N3—H3A⋯O2	0.86	1.76	2.608 (9)	166
N4—H4A⋯Cl1	0.86	2.21	3.069 (6)	175
O1—H1C⋯F3ⁱⁱⁱ	0.85	2.25	2.994 (18)	146
O1—H1B⋯Cl2^iv	0.85	2.55	3.279 (6)	144
O2—H2B⋯F5^v	0.85	2.41	3.224 (13)	160
O2—H2D⋯Cl3^vi	0.85	2.50	3.339 (10)	172
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) x, y-1, z; (iv) x, y-1, z+1; (v) -x+1, -y, -z+1; (vi) -x, -y+1, -z+1.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812018855/xu5519sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018855/xu5519Isup2.hkl

checkCIF report

Comment top

Recently much attention has been devoted to simple molecular-ionic compounds containing inorganic and organic ions due to the tunability of their special structural features and their potential ferroelectrics property. Ferroelectric materials that exhibit reversible electric polarization in response to an external electric field have found many applications such as nonvolatile memory storage, electronics and optics. The freezing of a certain functional group at low temperature forces significant orientational motions of the guest molecules and thus induces the formation of the ferroelectric phase. (Fu et al, 2011; Ye et al. 2009; Zhang et al. 2009; Zhang et al. 2012; Zhang et al. 2010). In our laboratory, the title compound has been synthesized to investigate to its potentialferroelectric properties. However, it was found that the dielectric constant of the compound as a function of temperature indicates that the permittivity is basically temperature-independent (ε = C/(T–T₀)), suggesting that this compound is not ferroelectric or there may be no distinct phase transition occurring within the measured temperature (below the melting point).

The title compound,(C₈H₆F₃N₂)₂⁺.HgCl₄^2-.2H₂O, has an asymmetric unit that consists of two 2-trifluoromethyl-1H-benzimidazol cations, one tetrachloridomercuriate anion and two water molecules (Fig 1). The atoms of the benzimidazole ring are nearly coplanar and the triflouromethyl group lies out of this plane. The mercury cation is coordinated by six Cl^- anions in distorted tetrahedral geometry.the average Hg—Cl bond distances range from 2.364 (2) Å to 2.564 (2) Å, the Cl—Hg—Cl angles range from 102.24 (8)°to 120.36 (9)°. In the crystal structure, the 2-trifluoromethyl-1H-benzimidazolecations are linked to adjacent tetrachloridomercuriate anions and watermolecules by N—H···O, N—H···Cl and O—H···Cl hydrogen bonds to form one dimensional chains parallel to ac plane (Fig 2). One of the trifluoromethyl is disordered.

Related literature top

For background to ferroelectric complexes, see: Fu et al. (2011); Ye et al. (2009). Zhang et al. (2009, 2010, 2012). For related structures, see: Liu (2011a,b, 2012a,b,c).

Experimental top

0.144 g (1 mmol) of 2-trifluoromethyl-1H-benzimidazol was firstly dissolved in 30 ml of ethanol which was added hydrochloric acid, to which 0.271 g (1 mmol) of mercuric chloride was added to give a solution at the ambient temperature. Single crystals suitable for X-ray structure analysis were obtained by the slow evaporation of the above solution after 5 days in air.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the title compound with view along the b axis. For the sake of clarity only the major component of the disordered trifluoromethyl group is shown.

Bis(2-trifluoromethyl-1H-benzimidazol-3-ium) tetrachloridomercurate dihydrate top

Crystal data top

(C₈H₆F₃N₂)₂[HgCl₄]·2H₂O	Z = 2
M_r = 752.72	F(000) = 716
Triclinic, P1	D_x = 2.047 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2485 (18) Å	Cell parameters from 4366 reflections
b = 10.029 (2) Å	θ = 3.0–26.0°
c = 14.754 (3) Å	µ = 6.81 mm⁻¹
α = 79.40 (3)°	T = 293 K
β = 75.79 (3)°	Block, colourless
γ = 67.74 (3)°	0.36 × 0.32 × 0.28 mm
V = 1221.4 (4) Å³

Data collection top

Rigaku SCXmini diffractometer	5564 independent reflections
Radiation source: fine-focus sealed tube	4040 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
CCD_Profile_fitting scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −12→12
T_min = 0.095, T_max = 0.152	k = −13→12
12786 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0373P)² + 1.355P] where P = (F_o² + 2F_c²)/3
5564 reflections	(Δ/σ)_max = 0.022
326 parameters	Δρ_max = 0.57 e Å⁻³
9 restraints	Δρ_min = −1.28 e Å⁻³

Crystal data top

(C₈H₆F₃N₂)₂[HgCl₄]·2H₂O	γ = 67.74 (3)°
M_r = 752.72	V = 1221.4 (4) Å³
Triclinic, P1	Z = 2
a = 9.2485 (18) Å	Mo Kα radiation
b = 10.029 (2) Å	µ = 6.81 mm⁻¹
c = 14.754 (3) Å	T = 293 K
α = 79.40 (3)°	0.36 × 0.32 × 0.28 mm
β = 75.79 (3)°

Data collection top

Rigaku SCXmini diffractometer	5564 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	4040 reflections with I > 2σ(I)
T_min = 0.095, T_max = 0.152	R_int = 0.061
12786 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	9 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	Δρ_max = 0.57 e Å⁻³
5564 reflections	Δρ_min = −1.28 e Å⁻³
326 parameters

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. 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 > 2sigma(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)
F1	0.7017 (13)	0.721 (2)	0.7840 (6)	0.093 (6)	0.59 (4)
F2	0.499 (3)	0.677 (2)	0.8538 (16)	0.123 (10)	0.59 (4)
F3	0.535 (3)	0.8571 (9)	0.8821 (10)	0.112 (9)	0.59 (4)
F1'	0.656 (4)	0.652 (3)	0.7911 (14)	0.137 (16)	0.41 (4)
F3'	0.639 (4)	0.841 (2)	0.843 (3)	0.16 (2)	0.41 (4)
F2'	0.4537 (9)	0.751 (3)	0.8841 (12)	0.102 (11)	0.41 (4)
N1	0.7197 (6)	0.4910 (6)	0.9609 (4)	0.0463 (14)
H1A	0.6964	0.4371	0.9319	0.056*
N2	0.7409 (6)	0.6807 (6)	0.9988 (4)	0.0446 (13)
H2A	0.7328	0.7692	0.9978	0.053*
C1	0.6080 (8)	0.7210 (7)	0.8664 (5)	0.064 (2)
C2	0.6894 (8)	0.6313 (8)	0.9408 (5)	0.0446 (16)
C3	0.7956 (7)	0.4460 (7)	1.0370 (5)	0.0392 (15)
C4	0.8554 (9)	0.3110 (8)	1.0833 (5)	0.0522 (18)
H4	0.8479	0.2294	1.0662	0.063*
C5	0.9278 (9)	0.3035 (8)	1.1571 (5)	0.0532 (18)
H5	0.9701	0.2150	1.1913	0.064*
C6	0.9371 (8)	0.4285 (9)	1.1801 (5)	0.0535 (18)
H6	0.9860	0.4200	1.2300	0.064*
C7	0.8793 (8)	0.5611 (8)	1.1340 (5)	0.0456 (16)
H7	0.8871	0.6425	1.1511	0.055*
C8	0.8083 (7)	0.5692 (7)	1.0604 (5)	0.0376 (14)
F4	0.2353 (11)	0.1121 (7)	0.5538 (6)	0.146 (3)
F5	0.3648 (10)	0.1573 (10)	0.4248 (7)	0.167 (4)
F6	0.1251 (8)	0.2625 (7)	0.4538 (6)	0.124 (2)
N3	0.3498 (7)	0.3080 (7)	0.5958 (4)	0.0579 (16)
H3A	0.3878	0.2271	0.6286	0.070*
N4	0.2323 (7)	0.4628 (7)	0.4921 (4)	0.0526 (15)
H4A	0.1822	0.4993	0.4462	0.063*
C9	0.2500 (13)	0.2136 (11)	0.4902 (7)	0.076 (3)
C10	0.2768 (8)	0.3277 (8)	0.5263 (5)	0.0503 (17)
C11	0.3561 (8)	0.4384 (9)	0.6076 (5)	0.0516 (18)
C12	0.4205 (10)	0.4786 (14)	0.6680 (6)	0.079 (3)
H12	0.4753	0.4119	0.7117	0.095*
C13	0.3997 (13)	0.6218 (17)	0.6601 (8)	0.097 (4)
H13	0.4396	0.6534	0.7008	0.116*
C14	0.3236 (14)	0.7196 (14)	0.5960 (9)	0.098 (4)
H14	0.3153	0.8155	0.5935	0.117*
C15	0.2581 (11)	0.6842 (10)	0.5344 (7)	0.072 (2)
H15	0.2037	0.7525	0.4912	0.086*
C16	0.2792 (9)	0.5380 (9)	0.5415 (5)	0.0524 (18)
Hg2	0.11556 (4)	0.82505 (3)	0.24321 (2)	0.05631 (13)
Cl1	0.0685 (3)	0.6016 (2)	0.32320 (13)	0.0606 (5)
Cl2	0.3673 (3)	0.7252 (2)	0.11954 (14)	0.0653 (5)
Cl3	−0.1015 (4)	0.9354 (3)	0.1548 (2)	0.1100 (11)
Cl4	0.1746 (4)	0.9720 (3)	0.32658 (19)	0.1004 (9)
O1	0.2620 (9)	0.0518 (6)	1.0084 (5)	0.099 (2)
H1C	0.3067	0.0060	0.9601	0.148*
H1B	0.2751	−0.0072	1.0576	0.148*
O2	0.4458 (11)	0.0872 (10)	0.7187 (7)	0.166 (4)
H2B	0.5002	0.0086	0.6939	0.249*
H2D	0.3630	0.0783	0.7558	0.249*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.066 (7)	0.132 (15)	0.054 (7)	−0.020 (8)	−0.006 (5)	0.016 (7)
F2	0.085 (14)	0.187 (19)	0.124 (17)	−0.076 (13)	−0.071 (14)	0.047 (14)
F3	0.130 (16)	0.066 (9)	0.099 (9)	0.029 (8)	−0.054 (10)	0.000 (7)
F1'	0.11 (3)	0.20 (3)	0.055 (12)	0.015 (19)	−0.030 (13)	−0.034 (13)
F3'	0.15 (3)	0.16 (3)	0.21 (4)	−0.10 (2)	−0.13 (3)	0.13 (3)
F2'	0.041 (8)	0.17 (3)	0.056 (9)	−0.001 (11)	−0.007 (7)	0.001 (12)
N1	0.040 (3)	0.054 (4)	0.053 (3)	−0.023 (3)	−0.011 (3)	−0.007 (3)
N2	0.037 (3)	0.032 (3)	0.061 (4)	−0.011 (2)	−0.009 (3)	0.001 (3)
C1	0.060 (6)	0.069 (6)	0.057 (5)	−0.020 (5)	−0.013 (4)	0.007 (5)
C2	0.031 (4)	0.050 (4)	0.050 (4)	−0.016 (3)	−0.002 (3)	−0.002 (3)
C3	0.031 (3)	0.037 (4)	0.047 (4)	−0.011 (3)	−0.001 (3)	−0.009 (3)
C4	0.046 (4)	0.048 (4)	0.067 (5)	−0.024 (4)	−0.005 (4)	−0.007 (4)
C5	0.053 (5)	0.047 (4)	0.054 (4)	−0.017 (4)	−0.008 (4)	0.004 (4)
C6	0.037 (4)	0.069 (5)	0.054 (4)	−0.022 (4)	−0.002 (3)	−0.005 (4)
C7	0.039 (4)	0.051 (4)	0.050 (4)	−0.019 (3)	−0.002 (3)	−0.016 (3)
C8	0.028 (3)	0.039 (3)	0.045 (4)	−0.014 (3)	0.002 (3)	−0.006 (3)
F4	0.238 (10)	0.076 (4)	0.153 (6)	−0.092 (5)	−0.050 (6)	0.011 (4)
F5	0.130 (6)	0.189 (8)	0.213 (9)	−0.090 (6)	0.056 (6)	−0.144 (7)
F6	0.119 (5)	0.108 (5)	0.188 (7)	−0.048 (4)	−0.078 (5)	−0.035 (5)
N3	0.041 (4)	0.063 (4)	0.059 (4)	−0.012 (3)	−0.014 (3)	0.013 (3)
N4	0.057 (4)	0.065 (4)	0.044 (3)	−0.031 (3)	−0.017 (3)	0.005 (3)
C9	0.078 (7)	0.074 (6)	0.085 (7)	−0.035 (5)	−0.005 (6)	−0.022 (6)
C10	0.037 (4)	0.054 (4)	0.055 (4)	−0.014 (3)	−0.010 (3)	0.003 (4)
C11	0.038 (4)	0.080 (5)	0.040 (4)	−0.027 (4)	−0.006 (3)	0.002 (4)
C12	0.047 (5)	0.137 (10)	0.056 (5)	−0.038 (6)	0.000 (4)	−0.015 (6)
C13	0.080 (8)	0.163 (13)	0.074 (7)	−0.069 (8)	0.011 (6)	−0.055 (8)
C14	0.100 (9)	0.119 (9)	0.101 (8)	−0.078 (8)	0.019 (7)	−0.040 (8)
C15	0.065 (6)	0.079 (6)	0.075 (6)	−0.037 (5)	−0.003 (5)	−0.008 (5)
C16	0.044 (4)	0.067 (5)	0.054 (4)	−0.032 (4)	−0.004 (4)	−0.007 (4)
Hg2	0.0667 (2)	0.0587 (2)	0.05325 (19)	−0.03158 (16)	−0.01580 (15)	−0.00235 (14)
Cl1	0.0810 (14)	0.0633 (12)	0.0535 (11)	−0.0420 (11)	−0.0290 (10)	0.0135 (9)
Cl2	0.0645 (13)	0.0756 (13)	0.0635 (12)	−0.0374 (11)	0.0002 (10)	−0.0144 (11)
Cl3	0.133 (3)	0.0746 (16)	0.155 (3)	−0.0507 (17)	−0.103 (2)	0.0420 (17)
Cl4	0.158 (3)	0.0916 (18)	0.0906 (17)	−0.0746 (19)	−0.0426 (18)	−0.0120 (15)
O1	0.142 (7)	0.050 (3)	0.112 (5)	−0.033 (4)	−0.048 (5)	0.006 (4)
O2	0.122 (7)	0.135 (7)	0.152 (8)	0.018 (6)	−0.038 (6)	0.076 (7)

Geometric parameters (Å, º) top

F1—C1	1.308 (2)	N3—C10	1.308 (9)
F2—C1	1.309 (2)	N3—C11	1.375 (10)
F3—C1	1.309 (2)	N3—H3A	0.8599
F1'—C1	1.309 (2)	N4—C10	1.300 (9)
F3'—C1	1.309 (2)	N4—C16	1.376 (9)
F2'—C1	1.309 (2)	N4—H4A	0.8601
N1—C2	1.317 (9)	C9—C10	1.469 (11)
N1—C3	1.386 (8)	C11—C16	1.377 (10)
N1—H1A	0.8600	C11—C12	1.374 (12)
N2—C2	1.318 (8)	C12—C13	1.361 (15)
N2—C8	1.357 (8)	C12—H12	0.9300
N2—H2A	0.8600	C13—C14	1.347 (16)
C1—C2	1.453 (10)	C13—H13	0.9300
C3—C4	1.371 (9)	C14—C15	1.368 (14)
C3—C8	1.395 (8)	C14—H14	0.9300
C4—C5	1.390 (10)	C15—C16	1.391 (11)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.395 (10)	Hg2—Cl4	2.364 (2)
C5—H5	0.9300	Hg2—Cl3	2.455 (3)
C6—C7	1.350 (10)	Hg2—Cl1	2.4734 (19)
C6—H6	0.9300	Hg2—Cl2	2.564 (2)
C7—C8	1.377 (9)	O1—H1C	0.8500
C7—H7	0.9300	O1—H1B	0.8500
F4—C9	1.274 (11)	O2—H2B	0.8500
F5—C9	1.274 (11)	O2—H2D	0.8500
F6—C9	1.281 (11)

C2—N1—C3	107.7 (6)	N2—C8—C3	106.5 (6)
C2—N1—H1A	126.1	C7—C8—C3	120.8 (6)
C3—N1—H1A	126.2	C10—N3—C11	108.6 (6)
C2—N2—C8	108.9 (6)	C10—N3—H3A	125.8
C2—N2—H2A	125.6	C11—N3—H3A	125.7
C8—N2—H2A	125.5	C10—N4—C16	108.4 (6)
F1—C1—F2'	127.4 (10)	C10—N4—H4A	125.9
F1—C1—F3'	68.6 (15)	C16—N4—H4A	125.7
F2'—C1—F3'	109.5 (15)	F4—C9—F5	107.8 (10)
F1—C1—F3	106.1 (10)	F4—C9—F6	107.4 (9)
F2'—C1—F3	70.4 (12)	F5—C9—F6	105.6 (10)
F1—C1—F2	104.5 (11)	F4—C9—C10	112.6 (9)
F3'—C1—F2	135.0 (11)	F5—C9—C10	110.9 (8)
F3—C1—F2	105.9 (12)	F6—C9—C10	112.3 (8)
F2'—C1—F1'	103.1 (16)	N4—C10—N3	110.6 (7)
F3'—C1—F1'	107.4 (18)	N4—C10—C9	124.1 (8)
F3—C1—F1'	134.0 (13)	N3—C10—C9	125.2 (8)
F2—C1—F1'	68.8 (14)	N3—C11—C16	105.9 (6)
F1—C1—C2	113.7 (8)	N3—C11—C12	132.9 (9)
F2'—C1—C2	115.1 (9)	C16—C11—C12	121.2 (9)
F3'—C1—C2	111.0 (9)	C13—C12—C11	116.1 (10)
F3—C1—C2	113.6 (7)	C13—C12—H12	121.9
F2—C1—C2	112.1 (7)	C11—C12—H12	121.9
F1'—C1—C2	110.1 (9)	C14—C13—C12	122.8 (10)
N1—C2—N2	110.7 (6)	C14—C13—H13	118.6
N1—C2—C1	125.2 (6)	C12—C13—H13	118.6
N2—C2—C1	124.1 (6)	C13—C14—C15	123.0 (11)
C4—C3—N1	130.9 (6)	C13—C14—H14	118.5
C4—C3—C8	122.9 (6)	C15—C14—H14	118.5
N1—C3—C8	106.2 (6)	C14—C15—C16	114.7 (10)
C3—C4—C5	116.0 (6)	C14—C15—H15	122.6
C3—C4—H4	122.0	C16—C15—H15	122.6
C5—C4—H4	122.0	C11—C16—N4	106.5 (7)
C4—C5—C6	120.1 (7)	C11—C16—C15	122.1 (8)
C4—C5—H5	119.9	N4—C16—C15	131.4 (8)
C6—C5—H5	119.9	Cl4—Hg2—Cl3	119.35 (10)
C7—C6—C5	123.8 (7)	Cl4—Hg2—Cl1	120.36 (8)
C7—C6—H6	118.1	Cl3—Hg2—Cl1	102.26 (8)
C5—C6—H6	118.1	Cl4—Hg2—Cl2	105.49 (10)
C6—C7—C8	116.4 (6)	Cl3—Hg2—Cl2	105.13 (11)
C6—C7—H7	121.8	Cl1—Hg2—Cl2	102.10 (8)
C8—C7—H7	121.8	H1C—O1—H1B	109.5
N2—C8—C7	132.7 (6)	H2B—O2—H2D	109.5

C3—N1—C2—N2	0.2 (8)	N1—C3—C8—N2	0.0 (7)
C3—N1—C2—C1	−178.8 (6)	C4—C3—C8—C7	−1.7 (10)
C8—N2—C2—N1	−0.2 (8)	N1—C3—C8—C7	−179.9 (6)
C8—N2—C2—C1	178.9 (6)	C16—N4—C10—N3	0.3 (8)
F1—C1—C2—N1	−84.6 (15)	C16—N4—C10—C9	−178.9 (8)
F2'—C1—C2—N1	75.3 (19)	C11—N3—C10—N4	−0.9 (9)
F3'—C1—C2—N1	−160 (2)	C11—N3—C10—C9	178.3 (8)
F3—C1—C2—N1	153.8 (14)	F4—C9—C10—N4	−150.4 (9)
F2—C1—C2—N1	33.7 (19)	F5—C9—C10—N4	88.8 (12)
F1'—C1—C2—N1	−41 (3)	F6—C9—C10—N4	−29.0 (13)
F1—C1—C2—N2	96.5 (14)	F4—C9—C10—N3	30.4 (13)
F2'—C1—C2—N2	−103.6 (17)	F5—C9—C10—N3	−90.4 (12)
F3'—C1—C2—N2	22 (2)	F6—C9—C10—N3	151.8 (9)
F3—C1—C2—N2	−25.1 (14)	C10—N3—C11—C16	1.1 (8)
F2—C1—C2—N2	−145.2 (16)	C10—N3—C11—C12	−178.6 (8)
F1'—C1—C2—N2	140 (2)	N3—C11—C12—C13	−178.5 (8)
C2—N1—C3—C4	−178.1 (7)	C16—C11—C12—C13	1.8 (12)
C2—N1—C3—C8	−0.1 (7)	C11—C12—C13—C14	−1.4 (15)
N1—C3—C4—C5	178.9 (7)	C12—C13—C14—C15	1.3 (17)
C8—C3—C4—C5	1.3 (10)	C13—C14—C15—C16	−1.4 (15)
C3—C4—C5—C6	−0.3 (10)	N3—C11—C16—N4	−0.9 (8)
C4—C5—C6—C7	−0.2 (11)	C12—C11—C16—N4	178.8 (7)
C5—C6—C7—C8	−0.2 (10)	N3—C11—C16—C15	178.1 (7)
C2—N2—C8—C7	180.0 (7)	C12—C11—C16—C15	−2.2 (12)
C2—N2—C8—C3	0.1 (7)	C10—N4—C16—C11	0.4 (8)
C6—C7—C8—N2	−178.8 (7)	C10—N4—C16—C15	−178.5 (8)
C6—C7—C8—C3	1.1 (9)	C14—C15—C16—C11	1.9 (12)
C4—C3—C8—N2	178.2 (6)	C14—C15—C16—N4	−179.5 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2ⁱ	0.86	2.23	3.081 (6)	170
N2—H2A···O1ⁱⁱ	0.86	1.80	2.656 (8)	174
N3—H3A···O2	0.86	1.76	2.608 (9)	166
N4—H4A···Cl1	0.86	2.21	3.069 (6)	175
O1—H1C···F3ⁱⁱⁱ	0.85	2.25	2.994 (18)	146
O1—H1B···Cl2^iv	0.85	2.55	3.279 (6)	144
O2—H2B···F5^v	0.85	2.41	3.224 (13)	160
O2—H2D···Cl3^vi	0.85	2.50	3.339 (10)	172

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

Experimental details

Crystal data
Chemical formula	(C₈H₆F₃N₂)₂[HgCl₄]·2H₂O
M_r	752.72
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.2485 (18), 10.029 (2), 14.754 (3)
α, β, γ (°)	79.40 (3), 75.79 (3), 67.74 (3)
V (Å³)	1221.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.81
Crystal size (mm)	0.36 × 0.32 × 0.28

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.095, 0.152
No. of measured, independent and observed [I > 2σ(I)] reflections	12786, 5564, 4040
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.119, 1.08
No. of reflections	5564
No. of parameters	326
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −1.28

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2ⁱ	0.86	2.23	3.081 (6)	170.2
N2—H2A···O1ⁱⁱ	0.86	1.80	2.656 (8)	174.0
N3—H3A···O2	0.86	1.76	2.608 (9)	166.1
N4—H4A···Cl1	0.86	2.21	3.069 (6)	175.2
O1—H1C···F3ⁱⁱⁱ	0.85	2.25	2.994 (18)	145.9
O1—H1B···Cl2^iv	0.85	2.55	3.279 (6)	144.3
O2—H2B···F5^v	0.85	2.41	3.224 (13)	159.9
O2—H2D···Cl3^vi	0.85	2.50	3.339 (10)	171.8

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

Acknowledgements

The author thanks an anonymous advisor from the Ordered Matter Science Research Centre, Southeast University, for great help in the revision of this paper.

References

Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G. & Huang, S.-P. (2011). J. Am. Chem. Soc. 133, 12780–12786. Web of Science CSD CrossRef CAS PubMed Google Scholar
Liu, M.-L. (2011a). Acta Cryst. E67, o2821. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, M.-L. (2011b). Acta Cryst. E67, o3473. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, M.-L. (2012a). Acta Cryst. E68, o342. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, M.-L. (2012b). Acta Cryst. E68, o1012. CSD CrossRef IUCr Journals Google Scholar
Liu, M.-L. (2012c). Acta Cryst. E68, o1076. CSD CrossRef IUCr Journals 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
Ye, H.-Y., Fu, D.-W., Zhang, Y., Zhang, W., Xiong, R.-G. & Huang, S.-P. (2009). J. Am. Chem. Soc. 131, 42–43. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhang, W., Chen, L.-Z., Xiong, R.-G., Nakamura, T. & Huang, S.-P. (2009). J. Am. Chem. Soc. 131, 12544–12545. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhang, W. & Xiong, R.-G. (2012). Chem. Rev. 112, 1163–1195. Web of Science CrossRef CAS PubMed Google Scholar
Zhang, W., Ye, H.-Y., Cai, H.-L., Ge, J.-Z., Xiong, R.-G. & Huang, S.-P. (2010). J. Am. Chem. Soc. 132, 7300–7302. Web of Science CSD CrossRef CAS PubMed Google Scholar

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Volume 68| Part 6| June 2012| Page m716

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(2-tri­fluoro­methyl-1H-benzimidazol-3-ium) tetra­chloridomercurate dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(2-trifluoromethyl-1H-benzimidazol-3-ium) tetrachloridomercurate dihydrate