(R)-2-Methyl-piperazine-1,4-diium tetra-chloridoanti-monate(III) chloride.

In the complex anion of the title compound, (C(5)H(14)N(2))[SbCl(4)]Cl, the Sb atom is tetra-coordinate within a saw-horse configuration. The cation adopts a chair conformation. The crystal structure is stabilized by inter-molecular N-H⋯Cl hydrogen bonds.

Related literature

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

Experimental

Crystal data

(C5H14N2)[SbCl4]Cl

M = 401.18

Orthorhombic,

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 ▶) 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 ▶), 1299 Friedel pairs

Flack parameter: −0.037 (17)

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

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

(C5H14N2)[SbCl4]Cl	F(000) = 776
Mr = 401.18	Dx = 1.957 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3003 reflections
a = 7.745 (5) Å	θ = 2.9–27.5°
b = 10.773 (7) Å	µ = 2.97 mm−1
c = 16.318 (9) Å	T = 293 K
V = 1361.6 (14) Å3	Block, colorless
Z = 4	0.28 × 0.26 × 0.22 mm

Rigaku SCXmini diffractometer	3086 independent reflections
Radiation source: fine-focus sealed tube	3003 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.9°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→14
Tmin = 0.8, Tmax = 0.9	l = −21→21
13665 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019	H-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 reflections	Δρmax = 0.90 e Å−3
119 parameters	Δρmin = −0.33 e Å−3
0 restraints	Absolute structure: Flack (1983), 1283 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.037 (17)

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.

	x	y	z	Uiso*/Ueq
Sb1	0.83387 (2)	0.572289 (14)	0.552350 (9)	0.02499 (5)
C1	0.3416 (5)	0.7218 (3)	0.70580 (19)	0.0533 (8)
H1A	0.2382	0.7109	0.6742	0.080*
H1B	0.4391	0.6931	0.6748	0.080*
H1C	0.3562	0.8082	0.7185	0.080*
C2	0.3278 (4)	0.6485 (2)	0.78422 (15)	0.0306 (5)
H2	0.4326	0.6617	0.8167	0.037*
C3	0.3079 (4)	0.5122 (3)	0.76750 (17)	0.0380 (7)
H3A	0.2117	0.4997	0.7304	0.046*
H3B	0.4114	0.4817	0.7407	0.046*
C4	0.1252 (4)	0.4866 (3)	0.8900 (2)	0.0479 (8)
H4A	0.1130	0.4402	0.9406	0.058*
H4B	0.0214	0.4743	0.8577	0.058*
C5	0.1455 (5)	0.6213 (3)	0.90911 (17)	0.0428 (7)
H5A	0.2425	0.6329	0.9459	0.051*
H5B	0.0424	0.6515	0.9363	0.051*
Cl1	0.59794 (9)	0.41872 (8)	0.59619 (5)	0.03962 (16)
Cl2	1.05446 (8)	0.42321 (8)	0.59260 (5)	0.03824 (16)
Cl3	0.82868 (11)	0.47961 (7)	0.41391 (4)	0.04005 (15)
Cl4	1.08779 (11)	0.72263 (7)	0.49885 (5)	0.04645 (19)
Cl5	0.84080 (12)	0.67609 (6)	0.71841 (4)	0.04331 (16)
N1	0.1748 (3)	0.69351 (19)	0.83223 (13)	0.0326 (5)
H1D	0.1906	0.7739	0.8451	0.039*
H1E	0.0799	0.6883	0.8006	0.039*
N2	0.2777 (3)	0.4395 (2)	0.84360 (15)	0.0375 (5)
H2A	0.3721	0.4439	0.8757	0.045*
H2B	0.2606	0.3593	0.8305	0.045*

	U11	U22	U33	U12	U13	U23
Sb1	0.02595 (8)	0.02336 (8)	0.02566 (7)	0.00076 (7)	0.00008 (7)	0.00201 (6)
C1	0.0526 (18)	0.063 (2)	0.0443 (16)	−0.003 (2)	0.0064 (18)	0.0194 (15)
C2	0.0271 (12)	0.0357 (14)	0.0289 (12)	−0.0029 (13)	−0.0017 (13)	0.0037 (10)
C3	0.0417 (18)	0.0405 (16)	0.0317 (14)	0.0067 (14)	0.0011 (14)	−0.0054 (11)
C4	0.046 (2)	0.0357 (17)	0.062 (2)	0.0015 (13)	0.0161 (16)	0.0157 (14)
C5	0.054 (2)	0.0423 (16)	0.0323 (14)	0.0061 (15)	0.0106 (15)	0.0039 (12)
Cl1	0.0315 (3)	0.0423 (4)	0.0450 (4)	−0.0033 (3)	0.0028 (3)	0.0054 (3)
Cl2	0.0314 (3)	0.0346 (4)	0.0488 (4)	0.0052 (3)	−0.0072 (3)	0.0052 (4)
Cl3	0.0360 (3)	0.0527 (4)	0.0314 (3)	−0.0035 (4)	0.0012 (4)	−0.0102 (3)
Cl4	0.0452 (4)	0.0438 (5)	0.0504 (4)	−0.0103 (4)	0.0059 (3)	−0.0038 (4)
Cl5	0.0481 (4)	0.0430 (4)	0.0389 (3)	0.0054 (4)	−0.0081 (4)	−0.0019 (3)
N1	0.0381 (12)	0.0246 (11)	0.0350 (11)	0.0031 (11)	−0.0027 (12)	0.0009 (8)
N2	0.0374 (12)	0.0264 (12)	0.0486 (13)	0.0024 (10)	−0.0033 (11)	−0.0007 (11)

Sb1—Cl2	2.4351 (12)	C3—H3B	0.9700
Sb1—Cl3	2.4702 (14)	C4—N2	1.492 (4)
Sb1—Cl1	2.5667 (13)	C4—C5	1.493 (4)
Sb1—Cl4	2.6932 (13)	C4—H4A	0.9700
C1—C2	1.507 (4)	C4—H4B	0.9700
C1—H1A	0.9600	C5—N1	1.493 (3)
C1—H1B	0.9600	C5—H5A	0.9700
C1—H1C	0.9600	C5—H5B	0.9700
C2—N1	1.501 (4)	N1—H1D	0.9000
C2—C3	1.502 (4)	N1—H1E	0.9000
C2—H2	0.9800	N2—H2A	0.9000
C3—N2	1.486 (4)	N2—H2B	0.9000
C3—H3A	0.9700
Cl2—Sb1—Cl3	89.51 (4)	N2—C4—C5	110.7 (3)
Cl2—Sb1—Cl1	89.95 (5)	N2—C4—H4A	109.5
Cl3—Sb1—Cl1	89.02 (4)	C5—C4—H4A	109.5
Cl2—Sb1—Cl4	88.38 (5)	N2—C4—H4B	109.5
Cl3—Sb1—Cl4	87.62 (4)	C5—C4—H4B	109.5
Cl1—Sb1—Cl4	176.26 (3)	H4A—C4—H4B	108.1
C2—C1—H1A	109.5	C4—C5—N1	110.3 (2)
C2—C1—H1B	109.5	C4—C5—H5A	109.6
H1A—C1—H1B	109.5	N1—C5—H5A	109.6
C2—C1—H1C	109.5	C4—C5—H5B	109.6
H1A—C1—H1C	109.5	N1—C5—H5B	109.6
H1B—C1—H1C	109.5	H5A—C5—H5B	108.1
N1—C2—C3	109.2 (3)	C5—N1—C2	113.0 (2)
N1—C2—C1	109.3 (3)	C5—N1—H1D	109.0
C3—C2—C1	111.4 (2)	C2—N1—H1D	109.0
N1—C2—H2	109.0	C5—N1—H1E	109.0
C3—C2—H2	109.0	C2—N1—H1E	109.0
C1—C2—H2	109.0	H1D—N1—H1E	107.8
N2—C3—C2	112.3 (2)	C3—N2—C4	111.7 (2)
N2—C3—H3A	109.1	C3—N2—H2A	109.3
C2—C3—H3A	109.1	C4—N2—H2A	109.3
N2—C3—H3B	109.1	C3—N2—H2B	109.3
C2—C3—H3B	109.1	C4—N2—H2B	109.3
H3A—C3—H3B	107.9	H2A—N2—H2B	107.9

D—H···A	D—H	H···A	D···A	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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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) ; (ii) .