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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1629.
Published online 2010 November 24. doi:  10.1107/S1600536810047689
PMCID: PMC3011473

(R)-2-Methyl­piperazine-1,4-diium tetra­chloridoanti­monate(III) chloride

Abstract

In the complex anion of the title compound, (C5H14N2)[SbCl4]Cl, the Sb atom is tetra­coordinate within a saw-horse configuration. The cation adopts a chair conformation. The crystal structure is stabilized by inter­molecular N—H(...)Cl hydrogen bonds.

Related literature

For related structures, see: Bujak & Zaleski (1999 [triangle]); Feng et al. (2007 [triangle]); Chen (2009 [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]).

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Object name is e-66-m1629-scheme1.jpg

Experimental

Crystal data

  • (C5H14N2)[SbCl4]Cl
  • M r = 401.18
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1629-efi1.jpg
  • a = 7.745 (5) Å
  • b = 10.773 (7) Å
  • c = 16.318 (9) Å
  • V = 1361.6 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.97 mm−1
  • T = 293 K
  • 0.28 × 0.26 × 0.22 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.8, T max = 0.9
  • 13665 measured reflections
  • 3086 independent reflections
  • 3003 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.019
  • wR(F 2) = 0.042
  • S = 1.08
  • 3086 reflections
  • 119 parameters
  • H-atom parameters constrained
  • Δρmax = 0.90 e Å−3
  • Δρmin = −0.33 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1299 Friedel pairs
  • Flack parameter: −0.037 (17)

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047689/bx2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047689/bx2322Isup2.hkl

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

Acknowledgments

This work was supported by a start-up grant from Anyang Institute of Technology.

supplementary crystallographic information

Comment

Rencently, the crystal structure of some halogenoantimonate salts has been reported (Feng et al., 2007; Bujak & Zaleski, 1999; Chen, 2009).The construction of new members of this family is important in the development of modern coordination chemistry. We report here the crystal structure of the title compound. In the complex anion of the title compound, C5H14N2. SbCl4.Cl, the Sb atom is tetracoordinate and has a saw-horse geometry.The cation complex adopt chair conformation with Cremer & Pople (1975) puckering parameters: QT = 0.556 (3) Å,

θ = 1.8 (3) ° , [var phi] = 97 (14)°. The crystal structure is stabilized by two intermolecular N—H···Cl hydrogen bonds, Table 1.

Experimental

A mixture of (R)-2-Methylpiperazine (2 mmol, 0.2 g), SbCl3(2 mmol, 0.46 g) and 10% aqueous HCl (20 ml) were mixed and dissolved in 10 ml water by heating to 353 K (0.5 h) forming a clear solution. The reaction mixture was cooled slowly to room temperature, crystals of the title compound were formed after 13 days.

Refinement

All H atoms were placed in calculated positions, with C—H = 0.93–0.98Å and N—H = 0.90 Å, and re?ned using a riding model, with Uiso(H)=1.2Ueq(C,N) or 1.5 Ueq(C) for methyl H atoms.

Figures

Fig. 1.
A view of (I) with atom labels. Displacement ellipsoids were drawn at the 30% probability level.
Fig. 2.
Packing diagram.

Crystal data

(C5H14N2)[SbCl4]ClF(000) = 776
Mr = 401.18Dx = 1.957 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3003 reflections
a = 7.745 (5) Åθ = 2.9–27.5°
b = 10.773 (7) ŵ = 2.97 mm1
c = 16.318 (9) ÅT = 293 K
V = 1361.6 (14) Å3Block, colorless
Z = 40.28 × 0.26 × 0.22 mm

Data collection

Rigaku SCXmini diffractometer3086 independent reflections
Radiation source: fine-focus sealed tube3003 reflections with I > 2σ(I)
graphiteRint = 0.026
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.9°
ω scansh = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −13→14
Tmin = 0.8, Tmax = 0.9l = −21→21
13665 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.042w = 1/[σ2(Fo2) + (0.0207P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
3086 reflectionsΔρmax = 0.90 e Å3
119 parametersΔρmin = −0.33 e Å3
0 restraintsAbsolute structure: Flack (1983), 1283 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.037 (17)

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 (Å2)

xyzUiso*/Ueq
Sb10.83387 (2)0.572289 (14)0.552350 (9)0.02499 (5)
C10.3416 (5)0.7218 (3)0.70580 (19)0.0533 (8)
H1A0.23820.71090.67420.080*
H1B0.43910.69310.67480.080*
H1C0.35620.80820.71850.080*
C20.3278 (4)0.6485 (2)0.78422 (15)0.0306 (5)
H20.43260.66170.81670.037*
C30.3079 (4)0.5122 (3)0.76750 (17)0.0380 (7)
H3A0.21170.49970.73040.046*
H3B0.41140.48170.74070.046*
C40.1252 (4)0.4866 (3)0.8900 (2)0.0479 (8)
H4A0.11300.44020.94060.058*
H4B0.02140.47430.85770.058*
C50.1455 (5)0.6213 (3)0.90911 (17)0.0428 (7)
H5A0.24250.63290.94590.051*
H5B0.04240.65150.93630.051*
Cl10.59794 (9)0.41872 (8)0.59619 (5)0.03962 (16)
Cl21.05446 (8)0.42321 (8)0.59260 (5)0.03824 (16)
Cl30.82868 (11)0.47961 (7)0.41391 (4)0.04005 (15)
Cl41.08779 (11)0.72263 (7)0.49885 (5)0.04645 (19)
Cl50.84080 (12)0.67609 (6)0.71841 (4)0.04331 (16)
N10.1748 (3)0.69351 (19)0.83223 (13)0.0326 (5)
H1D0.19060.77390.84510.039*
H1E0.07990.68830.80060.039*
N20.2777 (3)0.4395 (2)0.84360 (15)0.0375 (5)
H2A0.37210.44390.87570.045*
H2B0.26060.35930.83050.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb10.02595 (8)0.02336 (8)0.02566 (7)0.00076 (7)0.00008 (7)0.00201 (6)
C10.0526 (18)0.063 (2)0.0443 (16)−0.003 (2)0.0064 (18)0.0194 (15)
C20.0271 (12)0.0357 (14)0.0289 (12)−0.0029 (13)−0.0017 (13)0.0037 (10)
C30.0417 (18)0.0405 (16)0.0317 (14)0.0067 (14)0.0011 (14)−0.0054 (11)
C40.046 (2)0.0357 (17)0.062 (2)0.0015 (13)0.0161 (16)0.0157 (14)
C50.054 (2)0.0423 (16)0.0323 (14)0.0061 (15)0.0106 (15)0.0039 (12)
Cl10.0315 (3)0.0423 (4)0.0450 (4)−0.0033 (3)0.0028 (3)0.0054 (3)
Cl20.0314 (3)0.0346 (4)0.0488 (4)0.0052 (3)−0.0072 (3)0.0052 (4)
Cl30.0360 (3)0.0527 (4)0.0314 (3)−0.0035 (4)0.0012 (4)−0.0102 (3)
Cl40.0452 (4)0.0438 (5)0.0504 (4)−0.0103 (4)0.0059 (3)−0.0038 (4)
Cl50.0481 (4)0.0430 (4)0.0389 (3)0.0054 (4)−0.0081 (4)−0.0019 (3)
N10.0381 (12)0.0246 (11)0.0350 (11)0.0031 (11)−0.0027 (12)0.0009 (8)
N20.0374 (12)0.0264 (12)0.0486 (13)0.0024 (10)−0.0033 (11)−0.0007 (11)

Geometric parameters (Å, °)

Sb1—Cl22.4351 (12)C3—H3B0.9700
Sb1—Cl32.4702 (14)C4—N21.492 (4)
Sb1—Cl12.5667 (13)C4—C51.493 (4)
Sb1—Cl42.6932 (13)C4—H4A0.9700
C1—C21.507 (4)C4—H4B0.9700
C1—H1A0.9600C5—N11.493 (3)
C1—H1B0.9600C5—H5A0.9700
C1—H1C0.9600C5—H5B0.9700
C2—N11.501 (4)N1—H1D0.9000
C2—C31.502 (4)N1—H1E0.9000
C2—H20.9800N2—H2A0.9000
C3—N21.486 (4)N2—H2B0.9000
C3—H3A0.9700
Cl2—Sb1—Cl389.51 (4)N2—C4—C5110.7 (3)
Cl2—Sb1—Cl189.95 (5)N2—C4—H4A109.5
Cl3—Sb1—Cl189.02 (4)C5—C4—H4A109.5
Cl2—Sb1—Cl488.38 (5)N2—C4—H4B109.5
Cl3—Sb1—Cl487.62 (4)C5—C4—H4B109.5
Cl1—Sb1—Cl4176.26 (3)H4A—C4—H4B108.1
C2—C1—H1A109.5C4—C5—N1110.3 (2)
C2—C1—H1B109.5C4—C5—H5A109.6
H1A—C1—H1B109.5N1—C5—H5A109.6
C2—C1—H1C109.5C4—C5—H5B109.6
H1A—C1—H1C109.5N1—C5—H5B109.6
H1B—C1—H1C109.5H5A—C5—H5B108.1
N1—C2—C3109.2 (3)C5—N1—C2113.0 (2)
N1—C2—C1109.3 (3)C5—N1—H1D109.0
C3—C2—C1111.4 (2)C2—N1—H1D109.0
N1—C2—H2109.0C5—N1—H1E109.0
C3—C2—H2109.0C2—N1—H1E109.0
C1—C2—H2109.0H1D—N1—H1E107.8
N2—C3—C2112.3 (2)C3—N2—C4111.7 (2)
N2—C3—H3A109.1C3—N2—H2A109.3
C2—C3—H3A109.1C4—N2—H2A109.3
N2—C3—H3B109.1C3—N2—H2B109.3
C2—C3—H3B109.1C4—N2—H2B109.3
H3A—C3—H3B107.9H2A—N2—H2B107.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1E···Cl5i0.902.293.190 (3)179
N2—H2B···Cl5ii0.902.273.150 (3)166

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2322).

References

  • Bujak, M. & Zaleski, J. (1999). Acta Cryst. C55, 1775–1778.
  • Chen, L.-Z. (2009). Acta Cryst. E65, m683. [PMC free article] [PubMed]
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Feng, W.-J., Wang, H.-B., Ma, X.-J., Li, H.-Y. & Jin, Z.-M. (2007). Acta Cryst. E63, m1786–m1787.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography