Di­chloro(N,N,N′-tri­methyl­ethyl­enedi­amine)zinc(II)

The title compound, [ZnCl₂(CH₃NHCH₂CH₂NHCH₃)], crystallizes as tetrahedral monomers. The complex is chiral but forms racemic crystals. Molecules which have the (R)-configuration at nitro­gen have a δ-conformation of the five-membered chelate ring, and those with (S)-configuration have λ-conformation. Intermolecular N—H...Cl hydrogen bonds [H...Cl = 2.56 (4) Å] form infinite chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.098
• Data-to-parameter ratio = 27.9

checkCIF/PLATON results

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Computing details

Data collection: CrystalClear (Rigaku 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997), PLUTON (Spek, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

dichloro-N,N,N'-rimethylethylenediaminozinc

Crystal data

[Zn(C5H14N2)Cl2]	F(000) = 976
Mr = 238.45	Dx = 1.555 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ac2ab	Cell parameters from 16870 reflections
a = 12.921 (2) Å	θ = 2.8–29.0°
b = 11.882 (2) Å	µ = 2.88 mm^−1
c = 13.264 (2) Å	T = 293 K
V = 2036.5 (6) Å^3	Block, colourless
Z = 8	0.4 × 0.2 × 0.2 mm

Data collection

Rigaku R-axis IIC image plate system diffractometer	2646 independent reflections
Radiation source: Rotating anode, Rigaku RU200	2322 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 105 pixels mm^-1	θmax = 29.0°, θmin = 2.8°
ψ scans	h = −17→17
Absorption correction: multi-scan CrystalClear (Rigaku, 2000)	k = −16→16
Tmin = 0.400, Tmax = 0.561	l = −17→18
16870 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.5567P] where P = (Fo^2 + 2Fc^2)/3
2646 reflections	(Δ/σ)max = 0.001
95 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.05202 (2)	0.80679 (2)	0.81725 (2)	0.04269 (11)
Cl1	0.10676 (5)	0.64073 (5)	0.76398 (6)	0.05975 (18)
Cl2	−0.09926 (6)	0.80692 (7)	0.89456 (7)	0.0699 (2)
N1	0.06246 (17)	0.93083 (19)	0.70873 (18)	0.0499 (5)
N2	0.16574 (16)	0.89478 (16)	0.89549 (15)	0.0461 (4)
C1	0.0715 (3)	0.8971 (3)	0.6024 (2)	0.0763 (9)
H1A	0.0137	0.8505	0.5845	0.114*
H1B	0.1346	0.8557	0.5929	0.114*
H1C	0.0722	0.9629	0.5605	0.114*
C2	0.1496 (2)	1.0039 (2)	0.7393 (2)	0.0581 (6)
H2A	0.1396	1.0790	0.7123	0.070*
H2B	0.2139	0.9742	0.7125	0.070*
C3	0.1554 (2)	1.0090 (2)	0.8517 (2)	0.0567 (6)
H3A	0.2143	1.0544	0.8716	0.068*
H3B	0.0934	1.0445	0.8779	0.068*
C4	0.2698 (2)	0.8506 (3)	0.8774 (3)	0.0688 (7)
H4A	0.2752	0.7763	0.9054	0.103*
H4B	0.3199	0.8989	0.9087	0.103*
H4C	0.2825	0.8474	0.8061	0.103*
C5	0.1476 (3)	0.9019 (3)	1.0053 (2)	0.0766 (9)
H5A	0.0792	0.9301	1.0176	0.115*
H5B	0.1975	0.9518	1.0350	0.115*
H5C	0.1545	0.8284	1.0347	0.115*
H6	0.012 (3)	0.970 (3)	0.715 (2)	0.067 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.04233 (17)	0.03522 (16)	0.05051 (18)	−0.00460 (9)	0.00257 (10)	0.00111 (10)
Cl1	0.0576 (3)	0.0386 (3)	0.0830 (5)	0.0003 (2)	0.0026 (3)	−0.0088 (3)
Cl2	0.0535 (4)	0.0724 (5)	0.0839 (5)	−0.0100 (3)	0.0223 (3)	−0.0069 (4)
N1	0.0460 (10)	0.0459 (11)	0.0579 (11)	0.0084 (9)	0.0016 (9)	0.0100 (9)
N2	0.0476 (10)	0.0426 (10)	0.0479 (10)	−0.0060 (8)	−0.0004 (8)	−0.0003 (8)
C1	0.084 (2)	0.088 (2)	0.0563 (16)	0.0081 (18)	−0.0010 (15)	0.0094 (15)
C2	0.0573 (14)	0.0473 (13)	0.0696 (16)	−0.0069 (11)	0.0043 (12)	0.0177 (12)
C3	0.0593 (14)	0.0359 (11)	0.0749 (17)	−0.0084 (10)	0.0075 (13)	−0.0024 (11)
C4	0.0507 (14)	0.0695 (18)	0.086 (2)	0.0057 (13)	−0.0107 (14)	−0.0035 (16)
C5	0.102 (3)	0.079 (2)	0.0487 (15)	−0.0141 (19)	0.0010 (15)	−0.0067 (14)

Geometric parameters (Å, º)

Zn1—N1	2.065 (2)	C1—H1C	0.9600
Zn1—N2	2.081 (2)	C2—C3	1.494 (4)
Zn1—Cl2	2.2074 (8)	C2—H2A	0.9700
Zn1—Cl1	2.2120 (7)	C2—H2B	0.9700
N1—C1	1.470 (4)	C3—H3A	0.9700
N1—C2	1.479 (4)	C3—H3B	0.9700
N1—H6	0.80 (3)	C4—H4A	0.9600
N2—C4	1.463 (3)	C4—H4B	0.9600
N2—C5	1.478 (3)	C4—H4C	0.9600
N2—C3	1.482 (3)	C5—H5A	0.9600
C1—H1A	0.9600	C5—H5B	0.9600
C1—H1B	0.9600	C5—H5C	0.9600
N1—Zn1—N2	86.73 (9)	N1—C2—C3	109.6 (2)
N1—Zn1—Cl2	112.41 (6)	N1—C2—H2A	109.7
N2—Zn1—Cl2	113.17 (6)	C3—C2—H2A	109.7
N1—Zn1—Cl1	113.15 (7)	N1—C2—H2B	109.7
N2—Zn1—Cl1	112.44 (6)	C3—C2—H2B	109.7
Cl2—Zn1—Cl1	115.61 (3)	H2A—C2—H2B	108.2
C1—N1—C2	111.3 (2)	N2—C3—C2	111.0 (2)
C1—N1—Zn1	118.6 (2)	N2—C3—H3A	109.4
C2—N1—Zn1	106.12 (15)	C2—C3—H3A	109.4
C1—N1—H6	108 (2)	N2—C3—H3B	109.4
C2—N1—H6	104 (3)	C2—C3—H3B	109.4
Zn1—N1—H6	107 (2)	H3A—C3—H3B	108.0
C4—N2—C5	109.1 (2)	N2—C4—H4A	109.5
C4—N2—C3	110.3 (2)	N2—C4—H4B	109.5
C5—N2—C3	108.6 (2)	H4A—C4—H4B	109.5
C4—N2—Zn1	112.74 (17)	N2—C4—H4C	109.5
C5—N2—Zn1	114.12 (18)	H4A—C4—H4C	109.5
C3—N2—Zn1	101.60 (15)	H4B—C4—H4C	109.5
N1—C1—H1A	109.5	N2—C5—H5A	109.5
N1—C1—H1B	109.5	N2—C5—H5B	109.5
H1A—C1—H1B	109.5	H5A—C5—H5B	109.5
N1—C1—H1C	109.5	N2—C5—H5C	109.5
H1A—C1—H1C	109.5	H5A—C5—H5C	109.5
H1B—C1—H1C	109.5	H5B—C5—H5C	109.5