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ISSN: 2056-9890

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

aDepartment of Chemical and Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China
*Correspondence e-mail: ayitwgx@yahoo.com.cn

(Received 22 October 2010; accepted 17 November 2010; online 24 November 2010)

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[Bujak, M. & Zaleski, J. (1999). Acta Cryst. C55, 1775-1778.]); Feng et al. (2007[Feng, W.-J., Wang, H.-B., Ma, X.-J., Li, H.-Y. & Jin, Z.-M. (2007). Acta Cryst. E63, m1786-m1787.]); Chen (2009[Chen, L.-Z. (2009). Acta Cryst. E65, m683.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • (C5H14N2)[SbCl4]Cl

  • Mr = 401.18

  • Orthorhombic, P 21 21 21

  • 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.8, Tmax = 0.9

  • 13665 measured reflections

  • 3086 independent reflections

  • 3003 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.019

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1299 Friedel pairs

  • Flack parameter: −0.037 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1E⋯Cl5i 0.90 2.29 3.190 (3) 179
N2—H2B⋯Cl5ii 0.90 2.27 3.150 (3) 166
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supporting information


Comment top

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) ° , φ = 97 (14)°. The crystal structure is stabilized by two intermolecular N—H···Cl hydrogen bonds, Table 1.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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) ° , φ = 97 (14)°. The crystal structure is stabilized by two intermolecular N—H···Cl hydrogen bonds, Table 1.

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

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of (I) with atom labels. Displacement ellipsoids were drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram.
(R)-2-Methylpiperazine-1,4-diium tetrachloridoantimonate(III) chloride top
Crystal data top
(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 top
Rigaku SCXmini
diffractometer
3086 independent reflections
Radiation source: fine-focus sealed tube3003 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.9°
ω scansh = 1010
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1314
Tmin = 0.8, Tmax = 0.9l = 2121
13665 measured reflections
Refinement top
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) = 0.042 w = 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 methodsAbsolute structure parameter: 0.037 (17)
Crystal data top
(C5H14N2)[SbCl4]ClV = 1361.6 (14) Å3
Mr = 401.18Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.745 (5) ŵ = 2.97 mm1
b = 10.773 (7) ÅT = 293 K
c = 16.318 (9) Å0.28 × 0.26 × 0.22 mm
Data collection top
Rigaku SCXmini
diffractometer
3086 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
3003 reflections with I > 2σ(I)
Tmin = 0.8, Tmax = 0.9Rint = 0.026
13665 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.042Δρmax = 0.90 e Å3
S = 1.08Δρmin = 0.33 e Å3
3086 reflectionsAbsolute structure: Flack (1983), 1283 Friedel pairs
119 parametersAbsolute structure parameter: 0.037 (17)
0 restraints
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
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) top
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, º) top
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, º) top
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) x1, y, z; (ii) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula(C5H14N2)[SbCl4]Cl
Mr401.18
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.745 (5), 10.773 (7), 16.318 (9)
V3)1361.6 (14)
Z4
Radiation typeMo Kα
µ (mm1)2.97
Crystal size (mm)0.28 × 0.26 × 0.22
Data collection
DiffractometerRigaku SCXmini
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.8, 0.9
No. of measured, independent and
observed [I > 2σ(I)] reflections
13665, 3086, 3003
Rint0.026
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.019, 0.042, 1.08
No. of reflections3086
No. of parameters119
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.90, 0.33
Absolute structureFlack (1983), 1283 Friedel pairs
Absolute structure parameter0.037 (17)

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1E···Cl5i0.902.293.190 (3)179.1
N2—H2B···Cl5ii0.902.273.150 (3)165.9
Symmetry codes: (i) x1, y, z; (ii) x+1, y1/2, z+3/2.
 

Acknowledgements

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

References

First citationBujak, M. & Zaleski, J. (1999). Acta Cryst. C55, 1775–1778.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationChen, L.-Z. (2009). Acta Cryst. E65, m683.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationFeng, W.-J., Wang, H.-B., Ma, X.-J., Li, H.-Y. & Jin, Z.-M. (2007). Acta Cryst. E63, m1786–m1787.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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