4-(2-Methyl-piperidin-1-ylcarbon-yl)pyridinium hexachloridoantimonate(V).

In the hexa-chlorido-animonate anion of the title compound, (C(12)H(17)N(2)O)[SbCl(6)], the Sb(5+)ion is in a slightly distorted octa-hedral coordination. In the 4-(2-methyl-piperidine-1-carbon-yl) pyridinium cation, the dihedral angle between the mean planes of the pyridine and piperzine rings is 66.3 (3)°. The mean plane of the carbonyl group is twisted by 80.5 (7)° and 42.7 (4)° relative to the mean planes of the pyridine and piperzine rings, respectively. The methyl group is in an R configuration relative to the piperidine ring which is in a slightly distorted chair conformation. The crystal packing is stabilized by N-H⋯O hydrogen bonds between cations, which form infinite zigzag chains parallel to [010].

Related literature

For the use of halogenidoanti­monate salts in the study of phase transitions in dielectric–ferroelectric materials, see: Jakubas et al. (2005 ▶); Bednarska-Bolek et al. (2000 ▶). For related structures, see: Chen (2009 ▶); Clemente & Marzotto (2003 ▶); Kulicka et al. (2006 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

(C12H17N2O)[SbCl6]

M = 539.73

Monoclinic,

a = 8.1067 (16) Å

b = 12.700 (3) Å

c = 19.677 (4) Å

β = 99.06 (3)°

V = 2000.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.18 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.638, T max = 0.646

17300 measured reflections

3918 independent reflections

2731 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.178

S = 1.06

3918 reflections

199 parameters

8 restraints

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.82 e Å−3

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: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809036587/jj2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036587/jj2004Isup2.hkl

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

(C12H17N2O)[SbCl6]	F(000) = 1056
Mr = 539.73	Dx = 1.792 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7472 reflections
a = 8.1067 (16) Å	θ = 3.0–27.7°
b = 12.700 (3) Å	µ = 2.18 mm−1
c = 19.677 (4) Å	T = 298 K
β = 99.06 (3)°	Prism, colourless
V = 2000.6 (7) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	3918 independent reflections
Radiation source: fine-focus sealed tube	2731 reflections with I > 2σ(I)
graphite	Rint = 0.065
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.638, Tmax = 0.646	l = −24→24
17300 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0594P)2 + 10.7201P] where P = (Fo2 + 2Fc2)/3
3918 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 1.08 e Å−3
8 restraints	Δρmin = −0.82 e Å−3

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
C1	0.5950 (13)	0.2859 (8)	0.2451 (5)	0.092 (3)
H1A	0.5293	0.2434	0.2685	0.110*
C2	0.6745 (15)	0.3710 (9)	0.2774 (6)	0.107 (4)
H2A	0.6625	0.3868	0.3226	0.129*
C3	0.7859 (12)	0.4104 (8)	0.1821 (6)	0.089 (3)
H3A	0.8534	0.4541	0.1604	0.107*
C4	0.7082 (13)	0.3263 (7)	0.1474 (5)	0.076 (3)
H4A	0.7221	0.3128	0.1022	0.091*
C5	0.6107 (9)	0.2626 (6)	0.1797 (4)	0.0474 (18)
C6	0.5366 (10)	0.1615 (6)	0.1476 (4)	0.055 (2)
C7	0.2968 (10)	0.2610 (6)	0.0863 (6)	0.067 (3)
H7A	0.3572	0.3219	0.1069	0.080*
H7B	0.2776	0.2704	0.0368	0.080*
C8	0.1374 (15)	0.2526 (9)	0.1110 (6)	0.094 (3)
H8A	0.0691	0.3133	0.0955	0.113*
H8B	0.1566	0.2531	0.1610	0.113*
C9	0.0415 (15)	0.1501 (9)	0.0851 (7)	0.102 (4)
H9A	−0.0581	0.1434	0.1064	0.123*
H9B	0.0074	0.1538	0.0356	0.123*
C10	0.1563 (13)	0.0526 (8)	0.1035 (5)	0.084 (3)
H10A	0.1810	0.0446	0.1530	0.100*
H10B	0.0998	−0.0105	0.0843	0.100*
C11	0.3164 (11)	0.0675 (7)	0.0745 (5)	0.068 (3)
H11A	0.3906	0.0087	0.0906	0.081*
C12	0.2905 (13)	0.0667 (7)	−0.0031 (5)	0.079 (3)
H12A	0.3957	0.0775	−0.0187	0.119*
H12B	0.2148	0.1221	−0.0204	0.119*
H12C	0.2446	0.0001	−0.0196	0.119*
Cl1	0.3262 (6)	0.7906 (3)	0.19673 (17)	0.1303 (14)
Cl2	0.3231 (4)	0.7842 (2)	0.03045 (15)	0.0970 (9)
Cl3	0.0105 (4)	0.6753 (4)	0.0955 (2)	0.1479 (18)
Cl4	0.2771 (8)	0.5277 (3)	0.19805 (19)	0.192 (3)
Cl5	0.5929 (5)	0.6406 (5)	0.1308 (3)	0.199 (3)
Cl6	0.2773 (6)	0.5279 (2)	0.02829 (18)	0.1324 (15)
N1	0.7664 (10)	0.4296 (6)	0.2450 (5)	0.075 (2)
H1B	0.8162	0.4831	0.2658	0.091*
N2	0.3972 (9)	0.1656 (5)	0.1039 (4)	0.0623 (19)
O1	0.6169 (8)	0.0811 (5)	0.1647 (4)	0.082 (2)
Sb1	0.30206 (7)	0.65548 (4)	0.11435 (3)	0.0571 (2)

	U11	U22	U33	U12	U13	U23
C1	0.122 (9)	0.096 (8)	0.059 (6)	−0.040 (7)	0.024 (6)	−0.011 (6)
C2	0.165 (13)	0.102 (9)	0.048 (6)	−0.028 (9)	−0.004 (7)	−0.014 (6)
C3	0.089 (8)	0.075 (7)	0.110 (9)	−0.023 (6)	0.036 (7)	−0.017 (6)
C4	0.105 (8)	0.055 (6)	0.074 (6)	−0.022 (5)	0.035 (6)	−0.021 (5)
C5	0.047 (4)	0.050 (4)	0.040 (4)	−0.001 (3)	−0.008 (3)	0.004 (3)
C6	0.056 (5)	0.044 (4)	0.059 (5)	0.005 (4)	−0.010 (4)	0.005 (4)
C7	0.048 (5)	0.036 (4)	0.110 (7)	0.007 (4)	−0.008 (5)	0.001 (4)
C8	0.095 (9)	0.093 (8)	0.091 (8)	0.013 (7)	0.003 (6)	−0.014 (6)
C9	0.083 (8)	0.107 (10)	0.121 (10)	0.009 (7)	0.030 (7)	0.004 (8)
C10	0.094 (8)	0.078 (7)	0.076 (7)	−0.011 (6)	0.003 (6)	−0.005 (5)
C11	0.068 (6)	0.046 (5)	0.080 (6)	−0.011 (4)	−0.015 (5)	−0.006 (4)
C12	0.082 (7)	0.059 (6)	0.093 (8)	−0.001 (5)	0.004 (6)	−0.015 (5)
Cl1	0.184 (4)	0.121 (3)	0.083 (2)	−0.041 (3)	0.011 (2)	−0.042 (2)
Cl2	0.147 (3)	0.0595 (15)	0.0860 (19)	−0.0035 (16)	0.0231 (18)	0.0139 (13)
Cl3	0.0633 (18)	0.239 (5)	0.145 (3)	−0.026 (2)	0.0295 (19)	−0.056 (3)
Cl4	0.368 (8)	0.126 (3)	0.080 (2)	−0.056 (4)	0.026 (3)	0.043 (2)
Cl5	0.076 (2)	0.262 (6)	0.243 (6)	0.065 (3)	−0.019 (3)	0.038 (5)
Cl6	0.251 (5)	0.0584 (17)	0.102 (2)	−0.001 (2)	0.069 (3)	−0.0125 (16)
N1	0.069 (5)	0.056 (5)	0.091 (6)	−0.011 (4)	−0.020 (5)	−0.017 (4)
N2	0.056 (4)	0.035 (3)	0.087 (5)	0.000 (3)	−0.018 (4)	−0.002 (3)
O1	0.086 (5)	0.050 (4)	0.095 (5)	0.009 (3)	−0.032 (4)	0.012 (3)
Sb1	0.0608 (4)	0.0543 (4)	0.0552 (4)	−0.0006 (3)	0.0061 (2)	0.0038 (3)

C1—C5	1.347 (12)	C9—C10	1.557 (15)
C1—C2	1.364 (15)	C9—H9A	0.9700
C1—H1A	0.9300	C9—H9B	0.9700
C2—N1	1.291 (15)	C10—C11	1.509 (14)
C2—H2A	0.9300	C10—H10A	0.9700
C3—N1	1.295 (13)	C10—H10B	0.9700
C3—C4	1.367 (13)	C11—N2	1.481 (10)
C3—H3A	0.9300	C11—C12	1.508 (13)
C4—C5	1.355 (11)	C11—H11A	0.9800
C4—H4A	0.9300	C12—H12A	0.9600
C5—C6	1.514 (10)	C12—H12B	0.9600
C6—O1	1.229 (9)	C12—H12C	0.9600
C6—N2	1.309 (10)	Cl1—Sb1	2.347 (3)
C7—C8	1.455 (14)	Cl2—Sb1	2.348 (3)
C7—N2	1.470 (9)	Cl3—Sb1	2.348 (3)
C7—H7A	0.9700	Cl4—Sb1	2.343 (3)
C7—H7B	0.9700	Cl5—Sb1	2.336 (4)
C8—C9	1.560 (15)	Cl6—Sb1	2.330 (3)
C8—H8A	0.9700	N1—H1B	0.8600
C8—H8B	0.9700
C5—C1—C2	120.7 (10)	C9—C10—H10A	109.8
C5—C1—H1A	119.6	C11—C10—H10B	109.8
C2—C1—H1A	119.6	C9—C10—H10B	109.8
N1—C2—C1	119.6 (10)	H10A—C10—H10B	108.3
N1—C2—H2A	120.2	N2—C11—C12	112.6 (8)
C1—C2—H2A	120.2	N2—C11—C10	108.1 (8)
N1—C3—C4	120.6 (10)	C12—C11—C10	113.0 (8)
N1—C3—H3A	119.7	N2—C11—H11A	107.6
C4—C3—H3A	119.7	C12—C11—H11A	107.6
C5—C4—C3	119.3 (9)	C10—C11—H11A	107.6
C5—C4—H4A	120.4	C11—C12—H12A	109.5
C3—C4—H4A	120.4	C11—C12—H12B	109.5
C1—C5—C4	117.8 (8)	H12A—C12—H12B	109.5
C1—C5—C6	119.6 (8)	C11—C12—H12C	109.5
C4—C5—C6	122.2 (7)	H12A—C12—H12C	109.5
O1—C6—N2	125.3 (7)	H12B—C12—H12C	109.5
O1—C6—C5	115.6 (7)	C2—N1—C3	122.1 (9)
N2—C6—C5	119.0 (6)	C2—N1—H1B	119.0
C8—C7—N2	110.4 (8)	C3—N1—H1B	119.0
C8—C7—H7A	109.6	C6—N2—C7	125.2 (7)
N2—C7—H7A	109.6	C6—N2—C11	120.4 (6)
C8—C7—H7B	109.6	C7—N2—C11	114.0 (6)
N2—C7—H7B	109.6	Cl6—Sb1—Cl5	90.8 (2)
H7A—C7—H7B	108.1	Cl6—Sb1—Cl4	91.26 (14)
C7—C8—C9	112.0 (9)	Cl5—Sb1—Cl4	92.5 (2)
C7—C8—H8A	109.2	Cl6—Sb1—Cl1	177.11 (13)
C9—C8—H8A	109.2	Cl5—Sb1—Cl1	89.5 (2)
C7—C8—H8B	109.2	Cl4—Sb1—Cl1	91.60 (16)
C9—C8—H8B	109.2	Cl6—Sb1—Cl3	89.46 (16)
H8A—C8—H8B	107.9	Cl5—Sb1—Cl3	178.1 (2)
C10—C9—C8	109.8 (10)	Cl4—Sb1—Cl3	89.4 (2)
C10—C9—H9A	109.7	Cl1—Sb1—Cl3	90.17 (15)
C8—C9—H9A	109.7	Cl6—Sb1—Cl2	88.89 (11)
C10—C9—H9B	109.7	Cl5—Sb1—Cl2	88.32 (18)
C8—C9—H9B	109.7	Cl4—Sb1—Cl2	179.19 (19)
H9A—C9—H9B	108.2	Cl1—Sb1—Cl2	88.24 (13)
C11—C10—C9	109.3 (9)	Cl3—Sb1—Cl2	89.84 (16)
C11—C10—H10A	109.8
C5—C1—C2—N1	−0.4 (11)	C9—C10—C11—C12	−66.8 (11)
N1—C3—C4—C5	−0.3 (14)	C1—C2—N1—C3	0.1 (13)
C2—C1—C5—C4	0.3 (13)	C4—C3—N1—C2	0.2 (15)
C2—C1—C5—C6	173.5 (7)	O1—C6—N2—C7	176.7 (9)
C3—C4—C5—C1	0.1 (14)	C5—C6—N2—C7	−4.7 (14)
C3—C4—C5—C6	−173.0 (8)	O1—C6—N2—C11	4.7 (15)
C1—C5—C6—O1	−77.7 (11)	C5—C6—N2—C11	−176.7 (8)
C4—C5—C6—O1	95.2 (11)	C8—C7—N2—C6	−112.8 (10)
C1—C5—C6—N2	103.5 (10)	C8—C7—N2—C11	59.6 (11)
C4—C5—C6—N2	−83.6 (12)	C12—C11—N2—C6	−123.4 (10)
N2—C7—C8—C9	−53.9 (12)	C10—C11—N2—C6	111.1 (10)
C7—C8—C9—C10	53.4 (13)	C12—C11—N2—C7	63.8 (11)
C8—C9—C10—C11	−55.2 (12)	C10—C11—N2—C7	−61.8 (11)
C9—C10—C11—N2	58.5 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1i	0.86	1.87	2.689 (9)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.86	1.87	2.689 (9)	159

Symmetry code: (i) .