Tris(2-amino­pyridinium) hexa­chlorido­indate(III)

Jin, X.-D.; Sun, L.-C.; Wang, H.-B.; Ge, C.-H.

doi:10.1107/S1600536811043285

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1602

doi:10.1107/S1600536811043285

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Tris(2-aminopyridinium) hexachloridoindate(III)

Xu-Dong Jin,^a ^* Li-Cai Sun,^a Hai-Bo Wang ^a and Chun-Hua Ge ^a

^aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
^*Correspondence e-mail: jinxudong@yahoo.com

(Received 16 September 2011; accepted 19 October 2011; online 29 October 2011)

The Schiff base (E)-4-chloro-2-[(pyridin-2-ylimino)methyl]phenol was reacted with InCl₃·4H₂O, generating the title molecular salt, (C₅H₇N₂)₃[InCl₆]. The octahedral hexachloridoindate(III) anion is located on an inversion centre, and one half of the anion and two crystallographically independent cations form the asymmetric unit. One of the cations is located on a twofold rotation axis and its intra-ring C and N atoms simulate this symmetry by exchanging their positions in statistical disorder. In the crystal, weak N—H⋯Cl hydrogen bonds and two types of π–π interactions with centroid–centroid separations of 4.047 (3) and 4.202 (3) Å are observed.

Related literature

For the synthesis of 2-aminopyridine and salicylaldehyde Schiff bases, see: Burlova et al.(2008 ).

Experimental

Crystal data

(C₅H₇N₂)₃[InCl₆]
M_r = 612.90
Monoclinic, C 2/c
a = 18.6491 (17) Å
b = 16.2454 (14) Å
c = 8.4004 (5) Å
β = 112.214 (1)°
V = 2356.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.70 mm⁻¹
T = 298 K
0.46 × 0.43 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.509, T_max = 0.925
5734 measured reflections
2053 independent reflections
1672 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.08
2053 reflections
130 parameters
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Selected bond lengths (Å)

In1—Cl1	2.5121 (11)
In1—Cl2	2.5406 (11)
In1—Cl3	2.5120 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl2ⁱ	0.86	2.43	3.242	158
N2—H2A⋯Cl2ⁱ	0.86	2.58	3.354	150
N2—H2B⋯Cl1ⁱⁱ	0.86	2.75	3.558	157
N2—H2B⋯Cl3ⁱⁱ	0.86	2.82	3.359	122
N3—H3a⋯Cl3ⁱⁱⁱ	0.86	2.70	3.549	169
N3—H3a⋯Cl2ⁱⁱⁱ	0.86	2.91	3.337	112
N4—H4A⋯Cl1	0.86	2.56	3.358	154
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043285/kp2354sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043285/kp2354Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811043285/kp2354Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811043285/kp2354Isup4.mol

Supporting information file. DOI: 10.1107/S1600536811043285/kp2354Isup5.mol

checkCIF report

Comment top

Instead of an expected formation of a Schiff base indium complex, the reaction of the Schiff base with InCl₃.4H₂O in anhydrous alcohol leads to the title compound (Fig. 1). It could be reasonably explained that the Schiff base molecule decomposed in presence of water when a reactant InCl₃.4H₂O in alcohol was heated at 333 K.

A single-crystal analysis reveals that the asymmetric unit of the complex comprises a half of a hexachloro-indium anion and two 2-amino pyridinium cations. The indium (III) ion is located at the inversion centre (the special position 1/4, 1/4, 1/2 in the space group C2/c) surrounded by six Cl atoms in the octahedral coordination (Table 1, Fig. 2). The three crystallographically independent In—Cl bond lengths [2.5120 (12), 2.5121 (11) and 2.5406 (11) Å] (Table 1, Fig. 2) characterise the coordination. One of pyridinium cations involves the two C atoms (C6 and C9) located at the twofold axis whereas the atoms C8, C7 and N3 are in general position (Fig. 2). However, C7 and N3 (pp = 1/2) are in statistical disorder to simulate the twofold symmetry. The N1—C5 cation is in general position. The pyridinium cations (one in general position and one in a special position - totally three cations per structural unit) balance the charge of InCl₆^3-. An interplanar angle between two pyridine rings of N1/C1–C5 and N3/C6–C9 is 67.37°. A pair of weak π–π stacking interactions are found between the almost parallel pyridine rings, N1/C1–C5 and its symmetry related moiety (symmetry code: -x + 1, y, -z + 3/2) with the centroid separation of 4.047 (3) Å, perpendicular distance of 3.647 (2) Å and an angle of 9°. In addition, another pair of π–π stacking interactions (with amino groups in staggered arrangement in stacked rings) is observed in the crystal packing between the antiparallel aromatic rings, N3/C6–C9 and its symmetry related ring (symmetry code: -x + 1, -y + 1, -z + 1), with the interplanar spacing of 3.847 (3) Å, slippage of 1.690 Å and the centroid separation of 4.202 (3) Å. In the crystal packing, looking down the c axis, a cavity can be seen (Fig. 3).

Related literature top

For the synthesis of 2-aminopyridine and salicylaldehyde Schiff bases, see: Burlova et al.(2008).

Experimental top

In this work, the Schiff base was prepared according to the similar method (Burlova et al., 2008). A mixture of 5-chlorosalicylaldehyde (0.470 g, 3.0 mmol) and 2-aminopyridine (0.285 g, 3.0 mmol) in 12 ml anhydrous alcohol was stirred at 333 K for 2 h, a yellow Schiff base precipitate was filtered and dried. Then a solution of Schiff base (0.235 g, 1.0 mmol) in 10 ml anhydrous alcohol was added to another solution of InCl₃.4H₂O (0.293 g, 1.0 mmol) in 3 ml of anhydrous alcohol. The mixture was stirred at 333 K for ca 2.5 h, concentrated and left to stand at room temperature. Yellow single crystals suitable for X-ray analysis were obtained by slow solvent evaporation in 10 d.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

	Fig. 1. The chemical reaction scheme.
	Fig. 2. ORTEP drawing of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are drawn as small spheres of arbitrary radii. The atoms C7/N3 are statistically disordered exchanging location (50:50) to simulate the twofold rotation symmetry.
	Fig. 3. A view of a packing section of the title compound, stacking along the c axis. Dashed lines indicate intramolecular hydrogen bonds.

Tris(2-aminopyridinium) hexachloridoindate(III) top

Crystal data top

(C₅H₇N₂)₃[InCl₆]	F(000) = 1216
M_r = 612.90	D_x = 1.728 Mg m⁻³
Monoclinic, C2/c	Melting point: 465.0 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 18.6491 (17) Å	Cell parameters from 3465 reflections
b = 16.2454 (14) Å	θ = 2.5–28.3°
c = 8.4004 (5) Å	µ = 1.70 mm⁻¹
β = 112.214 (1)°	T = 298 K
V = 2356.1 (3) Å³	Plate, yellow
Z = 4	0.46 × 0.43 × 0.05 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2053 independent reflections
Radiation source: fine-focus sealed tube	1672 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→14
T_min = 0.509, T_max = 0.925	k = −19→19
5734 measured reflections	l = −9→9

Refinement top

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0466P)² + 6.8482P] where P = (F_o² + 2F_c²)/3
2053 reflections	(Δ/σ)_max = 0.001
130 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

(C₅H₇N₂)₃[InCl₆]	V = 2356.1 (3) Å³
M_r = 612.90	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.6491 (17) Å	µ = 1.70 mm⁻¹
b = 16.2454 (14) Å	T = 298 K
c = 8.4004 (5) Å	0.46 × 0.43 × 0.05 mm
β = 112.214 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2053 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1672 reflections with I > 2σ(I)
T_min = 0.509, T_max = 0.925	R_int = 0.030
5734 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.08	Δρ_max = 0.96 e Å⁻³
2053 reflections	Δρ_min = −0.79 e Å⁻³
130 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
In1	0.2500	0.2500	0.5000	0.03637 (17)
Cl1	0.37640 (6)	0.17532 (7)	0.57322 (15)	0.0487 (3)
Cl2	0.19049 (7)	0.15088 (7)	0.25064 (15)	0.0490 (3)
Cl3	0.20941 (7)	0.15470 (7)	0.68614 (16)	0.0529 (3)
N1	0.3380 (2)	0.8489 (2)	0.6354 (5)	0.0473 (9)
H1	0.3042	0.8353	0.6775	0.057*
N2	0.3012 (3)	0.9833 (3)	0.6428 (7)	0.0728 (14)
H2A	0.2669	0.9670	0.6813	0.087*
H2B	0.3061	1.0349	0.6263	0.087*
N3	0.4384 (3)	0.4542 (3)	0.6425 (7)	0.0632 (13)	0.50
H3	0.3987	0.4285	0.5728	0.076*	0.50
N4	0.5000	0.3304 (4)	0.7500	0.083 (2)
H4A	0.4605	0.3039	0.6810	0.099*
C1	0.3466 (3)	0.9288 (3)	0.6088 (6)	0.0471 (11)
C2	0.4025 (3)	0.9494 (3)	0.5426 (7)	0.0593 (13)
H2	0.4109	1.0042	0.5228	0.071*
C3	0.4442 (3)	0.8897 (4)	0.5076 (7)	0.0645 (15)
H3A	0.4812	0.9037	0.4630	0.077*
C4	0.4331 (3)	0.8075 (4)	0.5366 (7)	0.0653 (15)
H4	0.4623	0.7665	0.5126	0.078*
C5	0.3792 (3)	0.7888 (3)	0.6000 (7)	0.0581 (13)
H5	0.3702	0.7341	0.6195	0.070*
C6	0.5000	0.4118 (4)	0.7500	0.0477 (16)
C7	0.4384 (3)	0.4542 (3)	0.6425 (7)	0.0632 (13)	0.50
H7	0.3954	0.4264	0.5671	0.076*	0.50
C8	0.4397 (5)	0.5396 (5)	0.6454 (11)	0.103 (3)
H8	0.3972	0.5688	0.5719	0.123*
C9	0.5000	0.5795 (7)	0.7500	0.117 (4)
H9	0.5000	0.6368	0.7500	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
In1	0.0320 (3)	0.0386 (3)	0.0448 (3)	0.00200 (17)	0.02156 (19)	−0.00423 (18)
Cl1	0.0379 (6)	0.0538 (7)	0.0584 (7)	0.0112 (5)	0.0227 (5)	−0.0016 (5)
Cl2	0.0460 (6)	0.0546 (7)	0.0533 (7)	−0.0071 (5)	0.0265 (5)	−0.0144 (5)
Cl3	0.0598 (7)	0.0535 (7)	0.0597 (7)	0.0051 (6)	0.0388 (6)	0.0072 (5)
N1	0.055 (2)	0.049 (2)	0.052 (2)	0.0054 (19)	0.0357 (19)	0.0002 (18)
N2	0.076 (3)	0.047 (2)	0.108 (4)	−0.001 (2)	0.050 (3)	0.006 (3)
N3	0.039 (3)	0.075 (3)	0.069 (3)	−0.005 (2)	0.013 (2)	0.004 (3)
N4	0.054 (4)	0.045 (4)	0.156 (8)	0.000	0.047 (4)	0.000
C1	0.051 (3)	0.046 (3)	0.047 (3)	0.004 (2)	0.021 (2)	0.004 (2)
C2	0.060 (3)	0.056 (3)	0.068 (3)	0.017 (3)	0.031 (3)	0.000 (3)
C3	0.061 (3)	0.079 (4)	0.070 (4)	0.013 (3)	0.043 (3)	0.000 (3)
C4	0.068 (4)	0.068 (4)	0.076 (4)	−0.004 (3)	0.046 (3)	0.009 (3)
C5	0.074 (4)	0.047 (3)	0.069 (3)	−0.003 (3)	0.044 (3)	0.000 (3)
C6	0.043 (4)	0.044 (4)	0.065 (4)	0.000	0.030 (3)	0.000
C7	0.039 (3)	0.075 (3)	0.069 (3)	−0.005 (2)	0.013 (2)	0.004 (3)
C8	0.086 (5)	0.086 (5)	0.120 (6)	0.033 (4)	0.020 (5)	0.042 (5)
C9	0.122 (11)	0.065 (6)	0.155 (12)	0.000	0.043 (9)	0.000

Geometric parameters (Å, º) top

In1—Cl1ⁱ	2.5121 (11)	N4—H4A	0.8600
In1—Cl1	2.5121 (11)	C1—C2	1.395 (7)
In1—Cl2ⁱ	2.5406 (11)	C2—C3	1.344 (7)
In1—Cl2	2.5406 (11)	C2—H2	0.9300
In1—Cl3ⁱ	2.5120 (12)	C3—C4	1.386 (8)
In1—Cl3	2.5120 (12)	C3—H3A	0.9300
N1—C1	1.336 (6)	C4—C5	1.339 (7)
N1—C5	1.344 (6)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N2—C1	1.330 (6)	C6—C7ⁱⁱ	1.351 (6)
N2—H2A	0.8600	C6—N3ⁱⁱ	1.351 (6)
N2—H2B	0.8600	C8—C9	1.307 (10)
N3—C6	1.351 (6)	C8—H8	0.9300
N3—C8	1.387 (9)	C9—C8ⁱⁱ	1.307 (10)
N3—H3	0.8600	C9—H9	0.9300
N4—C6	1.322 (9)

Cl3ⁱ—In1—Cl3	180.00 (4)	N2—C1—C2	123.9 (5)
Cl3ⁱ—In1—Cl1ⁱ	91.47 (4)	N1—C1—C2	117.1 (5)
Cl3—In1—Cl1ⁱ	88.53 (4)	C3—C2—C1	119.6 (5)
Cl3ⁱ—In1—Cl1	88.53 (4)	C3—C2—H2	120.2
Cl3—In1—Cl1	91.47 (4)	C1—C2—H2	120.2
Cl1ⁱ—In1—Cl1	180.0	C2—C3—C4	121.3 (5)
Cl3ⁱ—In1—Cl2ⁱ	88.97 (4)	C2—C3—H3A	119.3
Cl3—In1—Cl2ⁱ	91.03 (4)	C4—C3—H3A	119.3
Cl1ⁱ—In1—Cl2ⁱ	88.44 (4)	C5—C4—C3	118.3 (6)
Cl1—In1—Cl2ⁱ	91.56 (4)	C5—C4—H4	120.9
Cl3ⁱ—In1—Cl2	91.03 (4)	C3—C4—H4	120.9
Cl3—In1—Cl2	88.97 (4)	C4—C5—N1	120.1 (5)
Cl1ⁱ—In1—Cl2	91.56 (4)	C4—C5—H5	120.0
Cl1—In1—Cl2	88.44 (4)	N1—C5—H5	120.0
Cl2ⁱ—In1—Cl2	180.00 (4)	N4—C6—C7ⁱⁱ	120.7 (3)
C1—N1—C5	123.6 (4)	N4—C6—N3ⁱⁱ	120.7 (3)
C1—N1—H1	118.2	C7ⁱⁱ—C6—N3ⁱⁱ	0.0 (7)
C5—N1—H1	118.2	N4—C6—N3	120.7 (3)
C1—N2—H2A	120.0	C7ⁱⁱ—C6—N3	118.7 (6)
C1—N2—H2B	120.0	N3ⁱⁱ—C6—N3	118.7 (6)
H2A—N2—H2B	120.0	C9—C8—N3	120.9 (7)
C6—N3—C8	119.6 (5)	C9—C8—H8	119.6
C6—N3—H3	120.2	N3—C8—H8	119.6
C8—N3—H3	120.2	C8—C9—C8ⁱⁱ	120.5 (11)
C6—N4—H4A	120.0	C8—C9—H9	119.8
N2—C1—N1	118.9 (5)	C8ⁱⁱ—C9—H9	119.8

C5—N1—C1—N2	177.8 (5)	C1—N1—C5—C4	1.0 (8)
C5—N1—C1—C2	−0.9 (7)	C8—N3—C6—N4	179.8 (5)
N2—C1—C2—C3	−178.1 (5)	C8—N3—C6—C7ⁱⁱ	−0.2 (5)
N1—C1—C2—C3	0.5 (8)	C8—N3—C6—N3ⁱⁱ	−0.2 (5)
C1—C2—C3—C4	−0.3 (9)	C6—N3—C8—C9	0.4 (11)
C2—C3—C4—C5	0.3 (9)	N3—C8—C9—C8ⁱⁱ	−0.2 (5)
C3—C4—C5—N1	−0.6 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱⁱⁱ	0.86	2.43	3.242	158
N2—H2A···Cl2ⁱⁱⁱ	0.86	2.58	3.354	150
N2—H2B···Cl1^iv	0.86	2.75	3.558	157
N2—H2B···Cl3^iv	0.86	2.82	3.359	122
N3—H3a···Cl3ⁱ	0.86	2.70	3.549	169
N3—H3a···Cl2ⁱ	0.86	2.91	3.337	112
N4—H4A···Cl1	0.86	2.56	3.358	154

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

Experimental details

Crystal data
Chemical formula	(C₅H₇N₂)₃[InCl₆]
M_r	612.90
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	18.6491 (17), 16.2454 (14), 8.4004 (5)
β (°)	112.214 (1)
V (Å³)	2356.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.70
Crystal size (mm)	0.46 × 0.43 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.509, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	5734, 2053, 1672
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.100, 1.08
No. of reflections	2053
No. of parameters	130
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.79

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Selected bond lengths (Å) top

In1—Cl1	2.5121 (11)	In1—Cl3	2.5120 (12)
In1—Cl2	2.5406 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱ	0.860	2.431	3.242	157.62
N2—H2A···Cl2ⁱ	0.860	2.582	3.354	149.92
N2—H2B···Cl1ⁱⁱ	0.860	2.750	3.558	157.00
N2—H2B···Cl3ⁱⁱ	0.860	2.824	3.359	121.95
N3—H3a···Cl3ⁱⁱⁱ	0.860	2.702	3.549	168.53
N3—H3a···Cl2ⁱⁱⁱ	0.860	2.914	3.337	112.30
N4—H4A···Cl1	0.860	2.564	3.358	154.02

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

Acknowledgements

This work was financially supported by the Foundation of Liaoning Educational Committee (grant No. 2008T065), the Science and Technology Foundation of Liaoning Province (grant No. 20071027) and the Scientific Research Foundation for Returned Overseas Chinese Scholars (grant No. 2005546).

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