1,1'-(Butane-1,4-di-yl)diimidazole-3,3'-diium tetra-chloridozincate(II) dihydrate.

In the title compound, (C(10)H(16)N(4))[ZnCl(4)]·2H(2)O, the cation lies abouton a center of inversion and the anion about a twofold rotation axis. The Zn(II) atom is four-coordinate in a tetra-hedral environment. The cations, anions and water mol-ecules are linked by N-H⋯O, N-H⋯Cl and O-H⋯Cl hydrogen bonds into a two-dimensional network.

Related literature

For background and the synthesis of 1,1′-(1,4-butanedi­yl)diimidazole, see: Ma et al. (2003 ▶)

Experimental

Crystal data

(C10H16N4)[ZnCl4]·2H2O

M = 435.47

Monoclinic,

a = 7.4010 (15) Å

b = 10.927 (2) Å

c = 11.058 (2) Å

β = 95.23 (3)°

V = 890.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.99 mm−1

T = 291 (2) K

0.18 × 0.17 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.713, T max = 0.751

8575 measured reflections

2042 independent reflections

1760 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.081

S = 1.07

2042 reflections

101 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.37 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800874X/ng2438sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800874X/ng2438Isup2.hkl

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

(C10H16N4)[ZnCl4]·2H2O	F000 = 444
Mr = 435.47	Dx = 1.624 Mg m−3
Monoclinic, P2/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 6883 reflections
a = 7.4010 (15) Å	θ = 3.2–27.5º
b = 10.927 (2) Å	µ = 1.99 mm−1
c = 11.058 (2) Å	T = 291 (2) K
β = 95.23 (3)º	Block, colorless
V = 890.6 (3) Å3	0.18 × 0.17 × 0.15 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	2042 independent reflections
Radiation source: fine-focus sealed tube	1760 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
T = 291(2) K	θmax = 27.5º
ω scans	θmin = 3.2º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.713, Tmax = 0.751	k = −14→14
8575 measured reflections	l = −14→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0301P)2 + 0.5173P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.47 e Å−3
2042 reflections	Δρmin = −0.37 e Å−3
101 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (3)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
Zn1	0.7500	0.75494 (3)	0.2500	0.03710 (15)
C1	0.4713 (3)	0.1878 (2)	0.2017 (2)	0.0405 (5)
H1	0.4499	0.1104	0.1684	0.049*
C2	0.4320 (4)	0.2946 (2)	0.1464 (2)	0.0469 (6)
H2	0.3790	0.3056	0.0676	0.056*
C3	0.5555 (4)	0.3335 (2)	0.3300 (2)	0.0448 (6)
H4	0.6019	0.3752	0.3993	0.054*
C4	0.6136 (3)	0.1221 (2)	0.4085 (2)	0.0450 (6)
H5	0.6771	0.1641	0.4770	0.054*
H6	0.6995	0.0680	0.3742	0.054*
C5	0.4626 (3)	0.0464 (2)	0.4529 (2)	0.0376 (5)
H7	0.3985	0.0040	0.3849	0.045*
H8	0.3770	0.0997	0.4885	0.045*
Cl2	0.87983 (10)	0.63431 (6)	0.11389 (5)	0.0543 (2)
Cl3	0.96871 (9)	0.86758 (5)	0.35304 (6)	0.0529 (2)
H3	0.475 (4)	0.461 (3)	0.216 (3)	0.066 (9)*
N1	0.5489 (2)	0.21294 (16)	0.31649 (16)	0.0347 (4)
N2	0.4846 (3)	0.3841 (2)	0.2278 (2)	0.0499 (5)
O1	0.3280 (3)	0.6019 (2)	0.1132 (2)	0.0775 (7)
H9	0.2192	0.6042	0.1319	0.116*
H10	0.3814	0.6708	0.1191	0.116*

	U11	U22	U33	U12	U13	U23
Zn1	0.0465 (2)	0.0277 (2)	0.0365 (2)	0.000	0.00102 (15)	0.000
C1	0.0413 (12)	0.0380 (12)	0.0412 (12)	0.0001 (10)	−0.0009 (10)	−0.0065 (10)
C2	0.0495 (14)	0.0545 (14)	0.0359 (12)	0.0036 (12)	0.0001 (10)	0.0056 (11)
C3	0.0631 (16)	0.0326 (11)	0.0393 (12)	−0.0061 (10)	0.0085 (11)	−0.0020 (10)
C4	0.0403 (13)	0.0434 (13)	0.0499 (13)	−0.0007 (10)	−0.0029 (10)	0.0146 (11)
C5	0.0362 (11)	0.0354 (11)	0.0408 (12)	0.0017 (9)	0.0019 (9)	0.0055 (10)
Cl2	0.0739 (5)	0.0480 (4)	0.0405 (3)	0.0215 (3)	0.0029 (3)	−0.0024 (3)
Cl3	0.0563 (4)	0.0355 (3)	0.0639 (4)	−0.0094 (3)	−0.0101 (3)	0.0011 (3)
N1	0.0374 (10)	0.0297 (8)	0.0371 (9)	−0.0009 (7)	0.0030 (8)	0.0036 (7)
N2	0.0659 (15)	0.0330 (10)	0.0522 (12)	0.0040 (10)	0.0135 (10)	0.0086 (9)
O1	0.0740 (15)	0.0611 (13)	0.0940 (17)	−0.0160 (11)	−0.0113 (12)	0.0114 (12)

Zn1—Cl3	2.2577 (8)	C3—H4	0.9300
Zn1—Cl3i	2.2577 (8)	C4—N1	1.470 (3)
Zn1—Cl2	2.2782 (8)	C4—C5	1.508 (3)
Zn1—Cl2i	2.2782 (7)	C4—H5	0.9700
C1—C2	1.337 (3)	C4—H6	0.9700
C1—N1	1.372 (3)	C5—C5ii	1.521 (4)
C1—H1	0.9300	C5—H7	0.9700
C2—N2	1.362 (3)	C5—H8	0.9700
C2—H2	0.9300	N2—H3	0.85 (3)
C3—N2	1.322 (3)	O1—H9	0.8500
C3—N1	1.326 (3)	O1—H10	0.8501
Cl3—Zn1—Cl3i	113.93 (4)	C5—C4—H5	109.0
Cl3—Zn1—Cl2	108.83 (3)	N1—C4—H6	109.0
Cl3i—Zn1—Cl2	107.95 (3)	C5—C4—H6	109.0
Cl3—Zn1—Cl2i	107.95 (3)	H5—C4—H6	107.8
Cl3i—Zn1—Cl2i	108.83 (3)	C4—C5—C5ii	110.7 (2)
Cl2—Zn1—Cl2i	109.29 (4)	C4—C5—H7	109.5
C2—C1—N1	107.7 (2)	C5ii—C5—H7	109.5
C2—C1—H1	126.2	C4—C5—H8	109.5
N1—C1—H1	126.2	C5ii—C5—H8	109.5
C1—C2—N2	106.7 (2)	H7—C5—H8	108.1
C1—C2—H2	126.7	C3—N1—C1	108.14 (19)
N2—C2—H2	126.7	C3—N1—C4	125.9 (2)
N2—C3—N1	108.1 (2)	C1—N1—C4	125.95 (19)
N2—C3—H4	125.9	C3—N2—C2	109.4 (2)
N1—C3—H4	125.9	C3—N2—H3	125 (2)
N1—C4—C5	113.02 (19)	C2—N2—H3	126 (2)
N1—C4—H5	109.0	H9—O1—H10	113.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10···Cl3i	0.85	2.43	3.275 (2)	177
O1—H9···Cl2iii	0.85	2.52	3.337 (3)	161
N2—H3···Cl2i	0.85 (3)	2.82 (3)	3.350 (2)	122 (3)
N2—H3···O1	0.85 (3)	2.15 (3)	2.890 (3)	145 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H10⋯Cl3i	0.85	2.43	3.275 (2)	177
O1—H9⋯Cl2ii	0.85	2.52	3.337 (3)	161
N2—H3⋯Cl2i	0.85 (3)	2.82 (3)	3.350 (2)	122 (3)
N2—H3⋯O1	0.85 (3)	2.15 (3)	2.890 (3)	145 (3)

Symmetry codes: (i) ; (ii) .