Benzyl-triethyl-ammonium aqua-trichlorido-zincate.

In the crystal structure of the title mol-ecular salt, (C(13)H(22)N)[ZnCl(3)(H(2)O)], the distorted tetrahedral anions are linked by O-H⋯Cl hydrogen bonds, generating [100] chains. Weak cation-to-anion C-H⋯Cl inter-actions generate a three-dimensional network.

Related literature

For background literature concerning mol­ecular salts, see: Tan et al. (2010 ▶); Jin et al. (2011 ▶).

Experimental

Crystal data

(C13H22N)[ZnCl3(H2O)]

M = 382.05

Orthorhombic,

a = 8.3236 (17) Å

b = 13.484 (3) Å

c = 15.808 (3) Å

V = 1774.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.83 mm−1

T = 291 K

0.28 × 0.24 × 0.22 mm

Data collection

Rigaku Mercury2 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.629, T max = 0.689

18427 measured reflections

4054 independent reflections

3522 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.077

S = 1.09

4054 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 1735 Friedel pairs

Flack parameter: 0.022 (13)

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048823/hb6492sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048823/hb6492Isup2.hkl

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

(C13H22N)[ZnCl3(H2O)]	F(000) = 792
Mr = 382.05	Dx = 1.430 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	θ = 3.0–27.5°
a = 8.3236 (17) Å	µ = 1.83 mm−1
b = 13.484 (3) Å	T = 291 K
c = 15.808 (3) Å	Block, colorless
V = 1774.2 (6) Å3	0.28 × 0.24 × 0.22 mm
Z = 4

Rigaku Mercury2 CCD diffractometer	4054 independent reflections
Radiation source: fine-focus sealed tube	3522 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
Tmin = 0.629, Tmax = 0.689	l = −20→20
18427 measured reflections

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) = 0.077	w = 1/[σ2(Fo2) + (0.0349P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
4054 reflections	Δρmax = 0.27 e Å−3
177 parameters	Δρmin = −0.37 e Å−3
0 restraints	Absolute structure: Flack (1983), 1735 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.022 (13)

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
C1	1.0907 (4)	0.6986 (3)	0.6677 (2)	0.0704 (9)
H1A	1.1371	0.6335	0.6665	0.106*
H1B	1.1646	0.7440	0.6937	0.106*
H1C	1.0684	0.7200	0.6110	0.106*
C2	0.9359 (4)	0.6962 (2)	0.71813 (18)	0.0526 (7)
H2A	0.9607	0.6758	0.7755	0.063*
H2B	0.8929	0.7630	0.7208	0.063*
C3	0.9403 (5)	0.4758 (2)	0.7474 (2)	0.0691 (10)
H3A	1.0262	0.5159	0.7691	0.104*
H3B	0.9807	0.4112	0.7333	0.104*
H3C	0.8578	0.4696	0.7896	0.104*
C4	0.8714 (3)	0.52380 (19)	0.66941 (17)	0.0485 (7)
H4A	0.7847	0.4827	0.6482	0.058*
H4B	0.9541	0.5262	0.6262	0.058*
C5	0.5348 (4)	0.5569 (2)	0.7260 (2)	0.0631 (8)
H5A	0.5022	0.5662	0.6683	0.095*
H5B	0.4453	0.5694	0.7628	0.095*
H5C	0.5714	0.4900	0.7338	0.095*
C6	0.6706 (3)	0.6286 (2)	0.74693 (16)	0.0482 (6)
H6A	0.6267	0.6951	0.7503	0.058*
H6B	0.7131	0.6119	0.8023	0.058*
C7	0.7509 (3)	0.66402 (18)	0.59743 (15)	0.0425 (6)
H7A	0.8416	0.6621	0.5589	0.051*
H7B	0.6717	0.6173	0.5765	0.051*
C8	0.6785 (3)	0.76674 (19)	0.59399 (15)	0.0412 (6)
C9	0.7711 (4)	0.8488 (2)	0.57179 (18)	0.0594 (8)
H9	0.8812	0.8415	0.5639	0.071*
C10	0.7015 (5)	0.9410 (2)	0.5613 (2)	0.0720 (10)
H10	0.7649	0.9950	0.5462	0.086*
C11	0.5380 (5)	0.9536 (2)	0.57303 (18)	0.0646 (9)
H11	0.4911	1.0156	0.5657	0.078*
C12	0.4475 (4)	0.8747 (2)	0.59527 (18)	0.0566 (8)
H12	0.3378	0.8831	0.6040	0.068*
C13	0.5148 (4)	0.7814 (2)	0.60535 (16)	0.0481 (6)
H13	0.4496	0.7281	0.6199	0.058*
Cl1	0.82104 (9)	0.72961 (7)	0.14959 (5)	0.0678 (2)
Cl2	1.23689 (9)	0.63181 (6)	0.11597 (5)	0.0603 (2)
Cl3	0.89340 (10)	0.55114 (6)	−0.02493 (5)	0.0620 (2)
N1	0.8077 (2)	0.62856 (15)	0.68371 (12)	0.0372 (5)
O1	1.0364 (2)	0.78841 (15)	−0.01861 (15)	0.0646 (6)
H1D	0.9476	0.8264	−0.0434	0.136 (18)*
H1E	1.1189	0.7929	−0.0579	0.120 (16)*
Zn1	1.00040 (4)	0.66907 (2)	0.056683 (18)	0.04478 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0440 (17)	0.089 (2)	0.078 (2)	−0.0088 (17)	−0.0040 (16)	−0.007 (2)
C2	0.0519 (16)	0.0584 (17)	0.0473 (15)	−0.0004 (14)	−0.0111 (13)	−0.0131 (14)
C3	0.083 (2)	0.061 (2)	0.0629 (19)	0.0251 (17)	0.0060 (17)	0.0056 (16)
C4	0.0562 (18)	0.0413 (15)	0.0479 (15)	0.0091 (13)	0.0042 (13)	−0.0071 (12)
C5	0.055 (2)	0.0617 (17)	0.0730 (19)	−0.0036 (15)	0.0157 (15)	0.0108 (16)
C6	0.0527 (16)	0.0529 (15)	0.0389 (14)	0.0097 (14)	0.0095 (12)	0.0028 (12)
C7	0.0488 (14)	0.0457 (13)	0.0331 (12)	−0.0015 (13)	−0.0011 (11)	−0.0044 (11)
C8	0.0447 (14)	0.0463 (14)	0.0326 (12)	−0.0064 (12)	−0.0026 (11)	0.0016 (11)
C9	0.0538 (18)	0.0612 (18)	0.0630 (19)	−0.0098 (15)	0.0029 (15)	0.0122 (15)
C10	0.082 (3)	0.0537 (18)	0.080 (2)	−0.0145 (18)	−0.002 (2)	0.0219 (18)
C11	0.091 (3)	0.0474 (16)	0.0556 (17)	0.0096 (17)	−0.0104 (17)	0.0049 (14)
C12	0.0546 (18)	0.0683 (19)	0.0469 (16)	0.0142 (15)	−0.0009 (13)	0.0061 (15)
C13	0.0450 (16)	0.0538 (15)	0.0456 (14)	−0.0046 (15)	−0.0037 (14)	0.0050 (11)
Cl1	0.0499 (4)	0.0890 (6)	0.0646 (5)	−0.0015 (4)	0.0090 (4)	−0.0227 (4)
Cl2	0.0412 (4)	0.0740 (5)	0.0658 (5)	−0.0034 (4)	−0.0119 (3)	0.0041 (4)
Cl3	0.0608 (5)	0.0689 (5)	0.0565 (4)	−0.0192 (4)	−0.0050 (4)	−0.0113 (4)
N1	0.0378 (11)	0.0402 (10)	0.0337 (10)	0.0039 (10)	0.0030 (9)	−0.0056 (9)
O1	0.0423 (12)	0.0623 (12)	0.0893 (15)	−0.0024 (10)	0.0078 (11)	0.0192 (12)
Zn1	0.03494 (16)	0.05128 (17)	0.04811 (17)	−0.00472 (16)	−0.00111 (15)	−0.00287 (12)

C1—C2	1.515 (4)	C7—C8	1.511 (4)
C1—H1A	0.9600	C7—N1	1.521 (3)
C1—H1B	0.9600	C7—H7A	0.9700
C1—H1C	0.9600	C7—H7B	0.9700
C2—N1	1.506 (3)	C8—C13	1.389 (4)
C2—H2A	0.9700	C8—C9	1.394 (4)
C2—H2B	0.9700	C9—C10	1.382 (4)
C3—C4	1.506 (4)	C9—H9	0.9300
C3—H3A	0.9600	C10—C11	1.384 (5)
C3—H3B	0.9600	C10—H10	0.9300
C3—H3C	0.9600	C11—C12	1.350 (5)
C4—N1	1.526 (3)	C11—H11	0.9300
C4—H4A	0.9700	C12—C13	1.386 (4)
C4—H4B	0.9700	C12—H12	0.9300
C5—C6	1.523 (4)	C13—H13	0.9300
C5—H5A	0.9600	Cl1—Zn1	2.2478 (8)
C5—H5B	0.9600	Cl2—Zn1	2.2373 (9)
C5—H5C	0.9600	Cl3—Zn1	2.2330 (8)
C6—N1	1.517 (3)	O1—Zn1	2.024 (2)
C6—H6A	0.9700	O1—H1D	0.9808
C6—H6B	0.9700	O1—H1E	0.9280
C2—C1—H1A	109.5	N1—C7—H7A	108.2
C2—C1—H1B	109.5	C8—C7—H7B	108.2
H1A—C1—H1B	109.5	N1—C7—H7B	108.2
C2—C1—H1C	109.5	H7A—C7—H7B	107.3
H1A—C1—H1C	109.5	C13—C8—C9	117.5 (3)
H1B—C1—H1C	109.5	C13—C8—C7	121.1 (2)
N1—C2—C1	115.2 (2)	C9—C8—C7	121.1 (2)
N1—C2—H2A	108.5	C10—C9—C8	120.9 (3)
C1—C2—H2A	108.5	C10—C9—H9	119.6
N1—C2—H2B	108.5	C8—C9—H9	119.6
C1—C2—H2B	108.5	C9—C10—C11	120.4 (3)
H2A—C2—H2B	107.5	C9—C10—H10	119.8
C4—C3—H3A	109.5	C11—C10—H10	119.8
C4—C3—H3B	109.5	C12—C11—C10	119.2 (3)
H3A—C3—H3B	109.5	C12—C11—H11	120.4
C4—C3—H3C	109.5	C10—C11—H11	120.4
H3A—C3—H3C	109.5	C11—C12—C13	121.3 (3)
H3B—C3—H3C	109.5	C11—C12—H12	119.4
C3—C4—N1	114.1 (2)	C13—C12—H12	119.4
C3—C4—H4A	108.7	C12—C13—C8	120.7 (3)
N1—C4—H4A	108.7	C12—C13—H13	119.6
C3—C4—H4B	108.7	C8—C13—H13	119.6
N1—C4—H4B	108.7	C2—N1—C6	107.17 (19)
H4A—C4—H4B	107.6	C2—N1—C7	110.7 (2)
C6—C5—H5A	109.5	C6—N1—C7	110.93 (19)
C6—C5—H5B	109.5	C2—N1—C4	111.6 (2)
H5A—C5—H5B	109.5	C6—N1—C4	111.1 (2)
C6—C5—H5C	109.5	C7—N1—C4	105.44 (18)
H5A—C5—H5C	109.5	Zn1—O1—H1D	122.6
H5B—C5—H5C	109.5	Zn1—O1—H1E	123.8
N1—C6—C5	114.5 (2)	H1D—O1—H1E	104.8
N1—C6—H6A	108.6	O1—Zn1—Cl3	106.59 (7)
C5—C6—H6A	108.6	O1—Zn1—Cl2	107.13 (6)
N1—C6—H6B	108.6	Cl3—Zn1—Cl2	115.66 (4)
C5—C6—H6B	108.6	O1—Zn1—Cl1	101.18 (7)
H6A—C6—H6B	107.6	Cl3—Zn1—Cl1	111.79 (3)
C8—C7—N1	116.38 (19)	Cl2—Zn1—Cl1	113.09 (3)
C8—C7—H7A	108.2
N1—C7—C8—C13	−90.3 (3)	C1—C2—N1—C7	−64.5 (3)
N1—C7—C8—C9	95.6 (3)	C1—C2—N1—C4	52.7 (3)
C13—C8—C9—C10	−0.3 (4)	C5—C6—N1—C2	−175.1 (2)
C7—C8—C9—C10	174.1 (3)	C5—C6—N1—C7	63.9 (3)
C8—C9—C10—C11	0.3 (5)	C5—C6—N1—C4	−53.0 (3)
C9—C10—C11—C12	0.3 (5)	C8—C7—N1—C2	−60.2 (3)
C10—C11—C12—C13	−0.9 (5)	C8—C7—N1—C6	58.7 (3)
C11—C12—C13—C8	0.9 (4)	C8—C7—N1—C4	179.0 (2)
C9—C8—C13—C12	−0.3 (4)	C3—C4—N1—C2	57.5 (3)
C7—C8—C13—C12	−174.7 (2)	C3—C4—N1—C6	−62.0 (3)
C1—C2—N1—C6	174.4 (2)	C3—C4—N1—C7	177.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Cl2i	0.98	2.17	3.121 (2)	163
O1—H1E···Cl1ii	0.93	2.24	3.155 (2)	168
C1—H1B···Cl1iii	0.96	2.82	3.599 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯Cl2i	0.98	2.17	3.121 (2)	163
O1—H1E⋯Cl1ii	0.93	2.24	3.155 (2)	168
C1—H1B⋯Cl1iii	0.96	2.82	3.599 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) .