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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401390X/wk6018sup1.cif
Contains datablocks I, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680401390X/wk6018Isup2.hkl
Contains datablock I

CCDC reference: 245139

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 top

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 top
Crystal data top
[Zn(C5H14N2)Cl2]F(000) = 976
Mr = 238.45Dx = 1.555 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ac2abCell parameters from 16870 reflections
a = 12.921 (2) Åθ = 2.8–29.0°
b = 11.882 (2) ŵ = 2.88 mm1
c = 13.264 (2) ÅT = 293 K
V = 2036.5 (6) Å3Block, colourless
Z = 80.4 × 0.2 × 0.2 mm
Data collection top
Rigaku R-axis IIC image plate system
diffractometer
2646 independent reflections
Radiation source: Rotating anode, Rigaku RU2002322 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 105 pixels mm-1θmax = 29.0°, θmin = 2.8°
ψ scansh = 1717
Absorption correction: multi-scan
CrystalClear (Rigaku, 2000)
k = 1616
Tmin = 0.400, Tmax = 0.561l = 1718
16870 measured reflections
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.5567P]
where P = (Fo2 + 2Fc2)/3
2646 reflections(Δ/σ)max = 0.001
95 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.45 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Zn10.05202 (2)0.80679 (2)0.81725 (2)0.04269 (11)
Cl10.10676 (5)0.64073 (5)0.76398 (6)0.05975 (18)
Cl20.09926 (6)0.80692 (7)0.89456 (7)0.0699 (2)
N10.06246 (17)0.93083 (19)0.70873 (18)0.0499 (5)
N20.16574 (16)0.89478 (16)0.89549 (15)0.0461 (4)
C10.0715 (3)0.8971 (3)0.6024 (2)0.0763 (9)
H1A0.01370.85050.58450.114*
H1B0.13460.85570.59290.114*
H1C0.07220.96290.56050.114*
C20.1496 (2)1.0039 (2)0.7393 (2)0.0581 (6)
H2A0.13961.07900.71230.070*
H2B0.21390.97420.71250.070*
C30.1554 (2)1.0090 (2)0.8517 (2)0.0567 (6)
H3A0.21431.05440.87160.068*
H3B0.09341.04450.87790.068*
C40.2698 (2)0.8506 (3)0.8774 (3)0.0688 (7)
H4A0.27520.77630.90540.103*
H4B0.31990.89890.90870.103*
H4C0.28250.84740.80610.103*
C50.1476 (3)0.9019 (3)1.0053 (2)0.0766 (9)
H5A0.07920.93011.01760.115*
H5B0.19750.95181.03500.115*
H5C0.15450.82841.03470.115*
H60.012 (3)0.970 (3)0.715 (2)0.067 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04233 (17)0.03522 (16)0.05051 (18)0.00460 (9)0.00257 (10)0.00111 (10)
Cl10.0576 (3)0.0386 (3)0.0830 (5)0.0003 (2)0.0026 (3)0.0088 (3)
Cl20.0535 (4)0.0724 (5)0.0839 (5)0.0100 (3)0.0223 (3)0.0069 (4)
N10.0460 (10)0.0459 (11)0.0579 (11)0.0084 (9)0.0016 (9)0.0100 (9)
N20.0476 (10)0.0426 (10)0.0479 (10)0.0060 (8)0.0004 (8)0.0003 (8)
C10.084 (2)0.088 (2)0.0563 (16)0.0081 (18)0.0010 (15)0.0094 (15)
C20.0573 (14)0.0473 (13)0.0696 (16)0.0069 (11)0.0043 (12)0.0177 (12)
C30.0593 (14)0.0359 (11)0.0749 (17)0.0084 (10)0.0075 (13)0.0024 (11)
C40.0507 (14)0.0695 (18)0.086 (2)0.0057 (13)0.0107 (14)0.0035 (16)
C50.102 (3)0.079 (2)0.0487 (15)0.0141 (19)0.0010 (15)0.0067 (14)
Geometric parameters (Å, º) top
Zn1—N12.065 (2)C1—H1C0.9600
Zn1—N22.081 (2)C2—C31.494 (4)
Zn1—Cl22.2074 (8)C2—H2A0.9700
Zn1—Cl12.2120 (7)C2—H2B0.9700
N1—C11.470 (4)C3—H3A0.9700
N1—C21.479 (4)C3—H3B0.9700
N1—H60.80 (3)C4—H4A0.9600
N2—C41.463 (3)C4—H4B0.9600
N2—C51.478 (3)C4—H4C0.9600
N2—C31.482 (3)C5—H5A0.9600
C1—H1A0.9600C5—H5B0.9600
C1—H1B0.9600C5—H5C0.9600
N1—Zn1—N286.73 (9)N1—C2—C3109.6 (2)
N1—Zn1—Cl2112.41 (6)N1—C2—H2A109.7
N2—Zn1—Cl2113.17 (6)C3—C2—H2A109.7
N1—Zn1—Cl1113.15 (7)N1—C2—H2B109.7
N2—Zn1—Cl1112.44 (6)C3—C2—H2B109.7
Cl2—Zn1—Cl1115.61 (3)H2A—C2—H2B108.2
C1—N1—C2111.3 (2)N2—C3—C2111.0 (2)
C1—N1—Zn1118.6 (2)N2—C3—H3A109.4
C2—N1—Zn1106.12 (15)C2—C3—H3A109.4
C1—N1—H6108 (2)N2—C3—H3B109.4
C2—N1—H6104 (3)C2—C3—H3B109.4
Zn1—N1—H6107 (2)H3A—C3—H3B108.0
C4—N2—C5109.1 (2)N2—C4—H4A109.5
C4—N2—C3110.3 (2)N2—C4—H4B109.5
C5—N2—C3108.6 (2)H4A—C4—H4B109.5
C4—N2—Zn1112.74 (17)N2—C4—H4C109.5
C5—N2—Zn1114.12 (18)H4A—C4—H4C109.5
C3—N2—Zn1101.60 (15)H4B—C4—H4C109.5
N1—C1—H1A109.5N2—C5—H5A109.5
N1—C1—H1B109.5N2—C5—H5B109.5
H1A—C1—H1B109.5H5A—C5—H5B109.5
N1—C1—H1C109.5N2—C5—H5C109.5
H1A—C1—H1C109.5H5A—C5—H5C109.5
H1B—C1—H1C109.5H5B—C5—H5C109.5
 

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