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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Page m344
doi:10.1107/S1600536813014323

Tetra­ethyl­ammonium tri­chlorido(N,N′-di­methyl­formamide-κO)zinc

Guo-Ping Chao,a Hua-Tian Shi,b Qun Chena and Qian-Feng Zhangb,a*

aDepartment of Applied Chemistry, School of Petrochemical Engineering, Changzhou University, Jiangsu 213164, People's Republic of China, and bInstitute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma'anshan, Anhui 243002, People's Republic of China
*Correspondence e-mail: zhangqf@ahut.edu.cn

(Received 8 May 2013; accepted 23 May 2013; online 31 May 2013)

The title complex salt, (C8H20N)[ZnCl3(C3H7NO)], contains one [Et4N]+ cation (Et is ethyl) and one [ZnCl3(DMF)]− anion (DMF is di­methyl­formamide). In the anion, the zinc atom is tetra­hedrally coordinated by a DMF ligand via the O atom and by three terminal Cl atoms. The average Zn—Cl bond length and Cl—Zn—Cl angle are 2.243 (11) Å and 114 (3)°, respectively.

Related literature

For background to zinc complexes: see: Folting et al. (1984[Folting, K., Huffman, J. C., Bansemer, R. L. & Caulton, K. G. (1984). Inorg. Chem. 23, 3289-3292.]); Gavens et al. (1982[Gavens, P. D., Bottrill, N., Kelland, J. W. & McMeeking, J. (1982). In Comprehensive Organometallic Chemistry, edited by G. Wilkinson, F. G. A. Stone & E. W. Abel. Oxford: Pergamon Press.]); For related structures, see: Bottomley et al. (1989[Bottomley, F., Ferris, E. C. & White, P. S. (1989). Acta Cryst. C45, 816-817.]); Hsu et al. (2008[Hsu, C.-Y., Yeh, C.-W., Wu, C.-P., Lin, C.-H. & Chen, J.-D. (2008). Acta Cryst. E64, m1412.]); Price et al. (1998[Price, C., Rees, N. H., Elsegood, M. R. J., Clegg, W. & Houlton, A. (1998). J. Chem. Soc. Dalton Trans. pp. 2001-2006.]); Shevchenko et al. (2008[Shevchenko, D. V., Kokozay, V. N., Krasovska, M. V. & Shishkin, O. V. (2008). Inorg. Chem. Commun. 11, 1209-1211.]); For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • (C8H20N)[ZnCl3(C3H7NO)]

  • Mr = 375.07

  • Monoclinic, P 21 /c

  • a = 12.3250 (18) Å

  • b = 8.8409 (13) Å

  • c = 16.721 (2) Å

  • β = 98.558 (2)°

  • V = 1801.7 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.80 mm−1

  • T = 296 K

  • 0.29 × 0.20 × 0.16 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.]) Tmin = 0.623, Tmax = 0.762

  • 10673 measured reflections

  • 4047 independent reflections

  • 3310 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.078

  • S = 1.04

  • 4047 reflections

  • 169 parameters

  • H-atom parameters constrained

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813014323/ds2232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813014323/ds2232Isup2.hkl

checkCIF report


Comment top

Inclusion of electropositive metal ions such as A13+, Mg2+, and Zn2+ in recipes for Ziegler-Natta olefin polymerization catalysts can substantially alter catalyst performance (Gavens et al., 1982). For example, the reactivity of ZnC12 toward early-transition-metal halides may yield a series of new materials for the function of co-catalysts (Folting et al., 1984). Actually, the direct reaction of ZnCl2 with other transition metal compounds has obvious limitation due to its solubility, it is necessary to develop new organometallic reagent of zinc metal. The reaction of anhydrous ZnCl2 with equal equivalent of [Et4N]Cl in DMF yielded soluble [Et4N][ZnCl3(DMF)] which was structurally characterized in this paper.

The title compound crystallizes in the monoclinic crystal system, containing two independent ions: [Et4N]+ cation and [ZnCl3(DMF)]- anion. The molecular structure of the title compound is depicted in Fig. 1. In [ZnCl3(DMF)]- anion, the zinc atom adopts a distorted tetrahedral geometry with a {three chloride and one oxygen} donor set involving the carbonyl oxygen O(1) of the N,N'-dimethylformide. Bond lengths to the metal atom are Zn(1)—Cl(1) 2.2397 (6), Zn(1)—Cl(2) 2.2332 (6), Zn(1)—Cl(3) 2.2552 (6) [av. Zn(1)—Cl = 2.2427 (6) Å] and Zn(1)—O(1) 2.0482 (14) Å, which agree well with those in [ZnCl3(LH)] (L = 1-(2-hydroxyethyl)-(2-aminoethyl-N2)-5-methylisocytosine) (Price et al., 1998) and [Co(L1)Cl2][ZnCl3(DMF)] (L1 = 4,6,6-trimethyl-1,9-diamino-3,7-diazanon-3-ene) (Shevchenko et al., 2008). The tetrahedral coordination geometry around the zinc atom is considerably distorted, which is indicated by the Cl—Zn—Cl and O—Zn—Cl angles being in the ranges 104.46 (2)—116.71 (2) and 101.98 (5)—104.46 (5)°, respectively. The Zn—O bond length in the title compound (2.0482 (14) Å) is compared with those in (C13H28N2)2[Zn2(C8H4O4)Cl6].4H2O (1.956 (3) Å) (Hsu et al., 2008), [ZnCl(C4H8O)(µ-Cl)]n (1.981 (3) Å) (Bottomley et al., 1989), and [Co(L1)Cl2][ZnCl3(DMF)] (L1 = 4,6,6-trimethyl-1,9-diamino-3,7-diazanon-3-ene) (2.01 (1) Å) (Shevchenko et al., 2008). The [Et4N]+ cation in the title compound has its expected structure as well as normal distances and angles, which will not be discussed further (Allen et al., 1987).

Related literature top

For background to zinc complexes: see: Folting et al. (1984); Gavens et al. (1982); For related structures, see: Bottomley et al. (1989); Hsu et al. (2008); Price et al. (1998); Shevchenko et al. (2008); For a description of the Cambridge Structural Database, see: Allen (2002). For standard bond lengths, see: Allen et al., (1987).

Experimental top

Equal equivalent of anhydrous ZnCl2 and [Et4N]Cl was mixed in DMF, the mixture was stirred for 2 h at room temperature, and then Et2O was added slowly to clearly colourless solution and the precipitate that formed was filtered off with suction, washed with Et2O three times and dried in vacuo, yielding a white solid in ca. 94 %. Colourless crystals were obtained by slow diffusion of Et2O into a DMF solution of the white powder over several days. Anal. Calcd. for C11H27N2OCl3Zn: C, 35.22; H, 7.26; N, 7.47%. Found: C, 35.15; H, 7.22; N, 7.43%.

Refinement top

The structure was solved by direct methods and refined by full-matrix least-squares procedure based on F2. All C Hydrogen atoms were placed in geometrically idealized positions and refined isotropically with a riding model for both C-sp2 [C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C)] and C-sp3 [C—H = 0.96—0.97 Å and with Uiso(H) = 1.5Ueq(C)].

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound in a unit cell.
Tetraethylammonium trichlorido(N,N'-dimethylformamide-κO)zinc top
Crystal data top
(C8H20N)[ZnCl3(C3H7NO)]F(000) = 784
Mr = 375.07Dx = 1.383 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4191 reflections
a = 12.3250 (18) Åθ = 2.5–27.1°
b = 8.8409 (13) ŵ = 1.80 mm−1
c = 16.721 (2) ÅT = 296 K
β = 98.558 (2)°Block, colourless
V = 1801.7 (5) Å30.29 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		4047 independent reflections
Radiation source: fine-focus sealed tube3310 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
phi and ω scansθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		h = −15→15
Tmin = 0.623, Tmax = 0.762k = −6→11
10673 measured reflectionsl = −21→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0411P)2 + 0.2235P]
where P = (Fo2 + 2Fc2)/3
4047 reflections(Δ/σ)max = 0.001
169 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.53 e Å−3
Crystal data top
(C8H20N)[ZnCl3(C3H7NO)]V = 1801.7 (5) Å3
Mr = 375.07Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.3250 (18) ŵ = 1.80 mm−1
b = 8.8409 (13) ÅT = 296 K
c = 16.721 (2) Å0.29 × 0.20 × 0.16 mm
β = 98.558 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		4047 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		3310 reflections with I > 2σ(I)
Tmin = 0.623, Tmax = 0.762Rint = 0.024
10673 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.078H-atom parameters constrained
S = 1.04Δρmax = 0.46 e Å−3
4047 reflectionsΔρmin = −0.53 e Å−3
169 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
xyzUiso*/Ueq
Zn10.768184 (17)0.26604 (3)0.138235 (13)0.04102 (9)
Cl10.86974 (6)0.22428 (7)0.03995 (4)0.06676 (17)
Cl20.66678 (4)0.47639 (6)0.12929 (3)0.05385 (14)
Cl30.68562 (4)0.05121 (6)0.17003 (3)0.05772 (15)
O10.88052 (12)0.30791 (17)0.23893 (8)0.0539 (4)
N10.99317 (13)0.22084 (17)0.34825 (9)0.0408 (3)
N20.67697 (12)0.71220 (18)0.39112 (9)0.0373 (3)
C10.91867 (15)0.2034 (2)0.28445 (11)0.0426 (4)
H10.89240.10620.27230.051*
C21.03514 (19)0.0923 (3)0.39750 (14)0.0609 (6)
H2A0.99980.00160.37550.091*
H2B1.02050.10650.45180.091*
H2C1.11290.08400.39780.091*
C31.03536 (19)0.3696 (3)0.37379 (14)0.0603 (6)
H3A0.99780.44530.33890.091*
H3B1.11250.37380.37080.091*
H3C1.02360.38790.42840.091*
C40.61949 (17)0.5862 (2)0.33990 (13)0.0513 (5)
H4A0.54180.59120.34360.062*
H4B0.62770.60480.28390.062*
C50.6591 (2)0.4277 (3)0.36167 (19)0.0823 (8)
H5A0.73450.41820.35400.123*
H5B0.61530.35630.32760.123*
H5C0.65270.40770.41720.123*
C60.79920 (17)0.7070 (3)0.38967 (14)0.0565 (5)
H6A0.82760.61290.41430.068*
H6B0.83330.78910.42280.068*
C70.8331 (2)0.7187 (3)0.30666 (16)0.0644 (6)
H7A0.80580.63270.27480.097*
H7B0.91170.72130.31180.097*
H7C0.80340.80960.28070.097*
C80.62689 (19)0.8583 (2)0.35567 (13)0.0553 (5)
H8A0.63730.86350.29940.066*
H8B0.54850.85510.35700.066*
C90.6723 (3)1.0009 (3)0.39742 (17)0.0973 (11)
H9A0.65891.00010.45250.146*
H9B0.63701.08720.37000.146*
H9C0.74981.00620.39630.146*
C100.66162 (17)0.6958 (3)0.47938 (11)0.0500 (5)
H10A0.68990.59790.49860.060*
H10B0.70570.77230.51060.060*
C110.54520 (19)0.7095 (3)0.49624 (13)0.0574 (6)
H11A0.51740.80830.48070.086*
H11B0.54360.69460.55290.086*
H11C0.50040.63430.46580.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03799 (13)0.04580 (15)0.03841 (13)−0.00102 (9)0.00288 (9)0.00403 (9)
Cl10.0766 (4)0.0652 (4)0.0659 (4)0.0039 (3)0.0349 (3)−0.0006 (3)
Cl20.0537 (3)0.0524 (3)0.0547 (3)0.0098 (2)0.0054 (2)0.0019 (2)
Cl30.0477 (3)0.0563 (3)0.0674 (3)−0.0095 (2)0.0027 (2)0.0181 (3)
O10.0539 (8)0.0539 (9)0.0486 (8)−0.0036 (7)−0.0099 (6)0.0072 (7)
N10.0372 (8)0.0447 (9)0.0398 (8)0.0018 (7)0.0037 (6)0.0020 (7)
N20.0352 (8)0.0417 (8)0.0350 (7)−0.0015 (6)0.0050 (6)0.0012 (6)
C10.0365 (10)0.0467 (11)0.0443 (10)−0.0015 (8)0.0047 (8)−0.0015 (8)
C20.0649 (14)0.0563 (13)0.0574 (13)0.0154 (11)−0.0050 (10)0.0062 (11)
C30.0624 (13)0.0561 (13)0.0572 (13)−0.0133 (11)−0.0087 (10)0.0020 (10)
C40.0497 (11)0.0536 (12)0.0513 (11)−0.0106 (10)0.0103 (9)−0.0124 (10)
C50.105 (2)0.0462 (14)0.103 (2)−0.0076 (14)0.0391 (17)−0.0047 (14)
C60.0352 (10)0.0756 (15)0.0582 (13)−0.0051 (10)0.0055 (9)−0.0006 (11)
C70.0483 (13)0.0777 (17)0.0728 (16)−0.0048 (11)0.0274 (11)−0.0004 (12)
C80.0700 (14)0.0486 (12)0.0504 (11)0.0135 (11)0.0190 (10)0.0112 (10)
C90.170 (3)0.0429 (14)0.089 (2)−0.0056 (17)0.055 (2)−0.0052 (13)
C100.0515 (12)0.0628 (13)0.0356 (10)−0.0011 (10)0.0056 (8)0.0050 (9)
C110.0590 (13)0.0689 (15)0.0474 (12)−0.0043 (11)0.0184 (10)0.0022 (10)
Geometric parameters (Å, º) top
Zn1—O12.0482 (14)C5—H5A0.9600
Zn1—Cl22.2332 (6)C5—H5B0.9600
Zn1—Cl12.2397 (6)C5—H5C0.9600
Zn1—Cl32.2552 (6)C6—C71.512 (3)
O1—C11.244 (2)C6—H6A0.9700
N1—C11.309 (2)C6—H6B0.9700
N1—C21.452 (3)C7—H7A0.9600
N1—C31.455 (3)C7—H7B0.9600
N2—C61.511 (2)C7—H7C0.9600
N2—C81.514 (2)C8—C91.508 (3)
N2—C41.515 (2)C8—H8A0.9700
N2—C101.523 (2)C8—H8B0.9700
C1—H10.9300C9—H9A0.9600
C2—H2A0.9600C9—H9B0.9600
C2—H2B0.9600C9—H9C0.9600
C2—H2C0.9600C10—C111.508 (3)
C3—H3A0.9600C10—H10A0.9700
C3—H3B0.9600C10—H10B0.9700
C3—H3C0.9600C11—H11A0.9600
C4—C51.511 (3)C11—H11B0.9600
C4—H4A0.9700C11—H11C0.9600
C4—H4B0.9700
O1—Zn1—Cl2101.98 (5)C4—C5—H5C109.5
O1—Zn1—Cl1104.46 (5)H5A—C5—H5C109.5
Cl2—Zn1—Cl1117.16 (2)H5B—C5—H5C109.5
O1—Zn1—Cl3103.41 (4)N2—C6—C7115.17 (19)
Cl2—Zn1—Cl3116.71 (2)N2—C6—H6A108.5
Cl1—Zn1—Cl3110.80 (2)C7—C6—H6A108.5
C1—O1—Zn1121.10 (14)N2—C6—H6B108.5
C1—N1—C2121.17 (17)C7—C6—H6B108.5
C1—N1—C3121.48 (17)H6A—C6—H6B107.5
C2—N1—C3117.33 (17)C6—C7—H7A109.5
C6—N2—C8111.66 (15)C6—C7—H7B109.5
C6—N2—C4110.61 (15)H7A—C7—H7B109.5
C8—N2—C4106.07 (16)C6—C7—H7C109.5
C6—N2—C10106.30 (14)H7A—C7—H7C109.5
C8—N2—C10111.01 (15)H7B—C7—H7C109.5
C4—N2—C10111.27 (15)C9—C8—N2115.5 (2)
O1—C1—N1124.53 (19)C9—C8—H8A108.4
O1—C1—H1117.7N2—C8—H8A108.4
N1—C1—H1117.7C9—C8—H8B108.4
N1—C2—H2A109.5N2—C8—H8B108.4
N1—C2—H2B109.5H8A—C8—H8B107.5
H2A—C2—H2B109.5C8—C9—H9A109.5
N1—C2—H2C109.5C8—C9—H9B109.5
H2A—C2—H2C109.5H9A—C9—H9B109.5
H2B—C2—H2C109.5C8—C9—H9C109.5
N1—C3—H3A109.5H9A—C9—H9C109.5
N1—C3—H3B109.5H9B—C9—H9C109.5
H3A—C3—H3B109.5C11—C10—N2115.63 (17)
N1—C3—H3C109.5C11—C10—H10A108.4
H3A—C3—H3C109.5N2—C10—H10A108.4
H3B—C3—H3C109.5C11—C10—H10B108.4
C5—C4—N2116.02 (19)N2—C10—H10B108.4
C5—C4—H4A108.3H10A—C10—H10B107.4
N2—C4—H4A108.3C10—C11—H11A109.5
C5—C4—H4B108.3C10—C11—H11B109.5
N2—C4—H4B108.3H11A—C11—H11B109.5
H4A—C4—H4B107.4C10—C11—H11C109.5
C4—C5—H5A109.5H11A—C11—H11C109.5
C4—C5—H5B109.5H11B—C11—H11C109.5
H5A—C5—H5B109.5

Experimental details

Crystal data
Chemical formula(C8H20N)[ZnCl3(C3H7NO)]
Mr375.07
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)12.3250 (18), 8.8409 (13), 16.721 (2)
β (°) 98.558 (2)
V (Å3)1801.7 (5)
Z4
Radiation typeMo Kα
µ (mm−1)1.80
Crystal size (mm)0.29 × 0.20 × 0.16
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.623, 0.762
No. of measured, independent and
observed [I > 2σ(I)] reflections		10673, 4047, 3310
Rint0.024
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.078, 1.04
No. of reflections4047
No. of parameters169
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.46, −0.53

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This project was supported by the Natural Science Foundation of China (90922008).

References

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ISSN: 2056-9890
Volume 69| Part 6| June 2013| Page m344
doi:10.1107/S1600536813014323
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