Bis(2-trifluoro-methyl-1H-benzimidazol-3-ium) tetra-chloridomercurate dihydrate.

In the title compound, (C(8)H(6)F(3)N(2))(2)[HgCl(4)]·2H(2)O, the Hg(II) cation is coordinated by four Cl(-) anions in a distorted tetra-hedral geometry. In the crystal, the 2-trifluoro-methyl-1H-benzimidazolium cations link to the [HgCl(4)](2-) complex anions and lattice water mol-ecules via N-H⋯Cl and N-H⋯O hydrogen bonds, and the lattice water mol-ecules further link to the Hg complex anion and the organic cations via O-H⋯Cl and O-H⋯F hydrogen bonding. One of the trifluoro-methyl 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 = 752.72

Triclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.119

S = 1.08

5564 reflections

326 parameters

9 restraints

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −1.28 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018855/xu5519sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C8H6F3N2)2[HgCl4]·2H2O	Z = 2
Mr = 752.72	F(000) = 716
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0373P)2 + 1.355P] where P = (Fo2 + 2Fc2)/3
5564 reflections	(Δ/σ)max = 0.022
326 parameters	Δρmax = 0.57 e Å−3
9 restraints	Δρmin = −1.28 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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···Cl2iv	0.85	2.55	3.279 (6)	144
O2—H2B···F5v	0.85	2.41	3.224 (13)	160
O2—H2D···Cl3vi	0.85	2.50	3.339 (10)	172

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⋯Cl2iv	0.85	2.55	3.279 (6)	144
O2—H2B⋯F5v	0.85	2.41	3.224 (13)	160
O2—H2D⋯Cl3vi	0.85	2.50	3.339 (10)	172

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .