4-Acetyl­pyridinium perchlorate

Fu, X.

doi:10.1107/S1600536809024805

organic compounds

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Volume 65| Part 8| August 2009| Page o1804

doi:10.1107/S1600536809024805

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4-Acetylpyridinium perchlorate

Xue-qun Fu ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fuxuequn222@163.com

(Received 27 June 2009; accepted 27 June 2009; online 8 July 2009)

In the crystal of the title molecular salt, C₇H₈NO⁺·ClO₄⁻, the ions are linked by N—H⋯O hydrogen bonds, resulting in chains propagating in [010]. The packing is reinforced by C—H⋯O interactions.

Related literature

For the synthesis, see: Piner (1934 ).

Experimental

Crystal data

C₇H₈NO⁺·ClO₄⁻
M_r = 221.59
Monoclinic, P 2₁ /c
a = 5.4657 (11) Å
b = 12.621 (3) Å
c = 13.490 (3) Å
β = 97.88 (3)°
V = 921.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.41 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 = 0.921, T_max = 0.921
9446 measured reflections
2108 independent reflections
1619 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.167
S = 1.06
2108 reflections
127 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.90 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.14	2.896 (5)	146
C1—H1B⋯O5ⁱⁱ	0.93	2.49	2.963 (5)	112
C2—H2A⋯O3ⁱⁱⁱ	0.93	2.59	3.435 (6)	151
C5—H5A⋯O4ⁱ	0.93	2.46	3.332 (6)	156
C7—H7B⋯O3ⁱⁱⁱ	0.96	2.58	3.488 (6)	158
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024805/hb5018sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024805/hb5018Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound contains a 4-Acetylpyridinium cation and a perchlorate anion (Fig 1). The bond length of O5—C6 and C6—C7 are 1.202 (5)Å and 1.492 (6)Å respectively, and the average bond length of Cl—O is 1.428 (3) Å. The N—H···O and C—H···O hydrogen bonding (Table 1) (N1—H···O1 2.896 (5) Å, C1—H···O5 2.963 (5) Å) make great contribution to the stability of the crystal structure and link the molecules to chains along the b axis (Fig 2).

Related literature top

For the synthesis, see: Piner (1934).

Experimental top

4-Acetylpyridine was obtained according to the method described by Piner (1934) and colourless prisms of (I) were recrystallised from ethanol.

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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (all H atoms have been omitted for clarity).
	Fig. 2. A view of the packing of (I) showing chains along the b axis. Dashed lines indicate hydrogen bonds.

4-Acetylpyridinium perchlorate top

Crystal data top

C₇H₈NO⁺·ClO₄⁻	F(000) = 456
M_r = 221.59	D_x = 1.597 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4087 reflections
a = 5.4657 (11) Å	θ = 3.1–27.6°
b = 12.621 (3) Å	µ = 0.41 mm⁻¹
c = 13.490 (3) Å	T = 298 K
β = 97.88 (3)°	Prism, colourless
V = 921.8 (4) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	2108 independent reflections
Radiation source: fine-focus sealed tube	1619 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
T_min = 0.921, T_max = 0.921	l = −17→17
9446 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0688P)² + 0.9865P] where P = (F_o² + 2F_c²)/3
2108 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.65 e Å⁻³
7 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

C₇H₈NO⁺·ClO₄⁻	V = 921.8 (4) Å³
M_r = 221.59	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.4657 (11) Å	µ = 0.41 mm⁻¹
b = 12.621 (3) Å	T = 298 K
c = 13.490 (3) Å	0.20 × 0.20 × 0.20 mm
β = 97.88 (3)°

Data collection top

Rigaku SCXmini diffractometer	2108 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1619 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.921	R_int = 0.049
9446 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	7 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.06	Δρ_max = 0.65 e Å⁻³
2108 reflections	Δρ_min = −0.90 e Å⁻³
127 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
Cl1	0.13491 (18)	0.20125 (8)	0.11005 (7)	0.0477 (3)
O5	0.3901 (6)	0.6009 (3)	0.1267 (2)	0.0640 (9)
C2	0.7259 (7)	0.3883 (3)	0.2591 (3)	0.0472 (9)
H2A	0.8394	0.3735	0.2155	0.057*
C6	0.5616 (7)	0.5419 (3)	0.1489 (3)	0.0442 (9)
C3	0.5618 (7)	0.4719 (3)	0.2396 (3)	0.0395 (8)
C4	0.3922 (7)	0.4908 (4)	0.3048 (3)	0.0495 (10)
H4A	0.2785	0.5457	0.2926	0.059*
C7	0.7761 (9)	0.5359 (4)	0.0917 (3)	0.0584 (11)
H7A	0.7509	0.5840	0.0361	0.088*
H7B	0.7913	0.4650	0.0676	0.088*
H7C	0.9244	0.5550	0.1347	0.088*
O4	0.0611 (7)	0.0968 (3)	0.0755 (3)	0.0790 (11)
O3	−0.0390 (8)	0.2749 (3)	0.0608 (3)	0.0814 (11)
O2	0.1393 (7)	0.2069 (3)	0.2155 (2)	0.0809 (12)
C5	0.3935 (8)	0.4281 (4)	0.3873 (3)	0.0589 (12)
H5A	0.2811	0.4403	0.4320	0.071*
N1	0.5561 (8)	0.3493 (3)	0.4037 (3)	0.0607 (10)
H1A	0.5546	0.3108	0.4562	0.073*
O1	0.3763 (6)	0.2204 (3)	0.0851 (2)	0.0645 (6)
C1	0.7196 (9)	0.3275 (4)	0.3430 (3)	0.0575 (11)
H1B	0.8296	0.2716	0.3571	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0506 (6)	0.0518 (6)	0.0440 (5)	0.0087 (4)	0.0186 (4)	0.0039 (4)
O5	0.065 (2)	0.064 (2)	0.062 (2)	0.0170 (16)	0.0035 (15)	0.0069 (15)
C2	0.051 (2)	0.043 (2)	0.050 (2)	0.0003 (17)	0.0159 (18)	−0.0036 (17)
C6	0.049 (2)	0.042 (2)	0.041 (2)	−0.0013 (17)	0.0036 (17)	−0.0046 (16)
C3	0.0386 (18)	0.0403 (19)	0.0396 (18)	−0.0047 (15)	0.0058 (15)	−0.0044 (15)
C4	0.042 (2)	0.056 (2)	0.052 (2)	0.0015 (18)	0.0117 (17)	−0.0060 (19)
C7	0.066 (3)	0.067 (3)	0.045 (2)	−0.002 (2)	0.017 (2)	0.009 (2)
O4	0.085 (3)	0.060 (2)	0.097 (3)	−0.0072 (19)	0.032 (2)	−0.0063 (19)
O3	0.100 (3)	0.079 (2)	0.065 (2)	0.037 (2)	0.009 (2)	0.0155 (18)
O2	0.094 (3)	0.109 (3)	0.0421 (18)	0.030 (2)	0.0173 (17)	0.0069 (17)
C5	0.054 (3)	0.075 (3)	0.051 (2)	−0.014 (2)	0.020 (2)	−0.006 (2)
N1	0.073 (3)	0.058 (2)	0.052 (2)	−0.016 (2)	0.0125 (19)	0.0106 (18)
O1	0.0571 (11)	0.0787 (12)	0.0614 (11)	0.0010 (10)	0.0210 (10)	−0.0032 (10)
C1	0.067 (3)	0.046 (2)	0.060 (3)	0.000 (2)	0.011 (2)	0.007 (2)

Geometric parameters (Å, º) top

Cl1—O2	1.421 (3)	C4—C5	1.365 (6)
Cl1—O1	1.427 (3)	C4—H4A	0.9300
Cl1—O3	1.427 (3)	C7—H7A	0.9600
Cl1—O4	1.437 (4)	C7—H7B	0.9600
O5—C6	1.202 (5)	C7—H7C	0.9600
C2—C1	1.372 (6)	C5—N1	1.332 (6)
C2—C3	1.386 (5)	C5—H5A	0.9300
C2—H2A	0.9300	N1—C1	1.321 (6)
C6—C7	1.492 (6)	N1—H1A	0.8600
C6—C3	1.509 (5)	C1—H1B	0.9300
C3—C4	1.384 (5)

O2—Cl1—O1	109.8 (2)	C3—C4—H4A	120.4
O2—Cl1—O3	110.7 (2)	C6—C7—H7A	109.5
O1—Cl1—O3	111.0 (2)	C6—C7—H7B	109.5
O2—Cl1—O4	109.6 (2)	H7A—C7—H7B	109.5
O1—Cl1—O4	107.8 (2)	C6—C7—H7C	109.5
O3—Cl1—O4	107.9 (2)	H7A—C7—H7C	109.5
C1—C2—C3	119.5 (4)	H7B—C7—H7C	109.5
C1—C2—H2A	120.2	N1—C5—C4	119.8 (4)
C3—C2—H2A	120.2	N1—C5—H5A	120.1
O5—C6—C7	123.0 (4)	C4—C5—H5A	120.1
O5—C6—C3	118.6 (4)	C1—N1—C5	123.1 (4)
C7—C6—C3	118.4 (3)	C1—N1—H1A	118.5
C4—C3—C2	118.9 (4)	C5—N1—H1A	118.5
C4—C3—C6	119.2 (3)	N1—C1—C2	119.4 (4)
C2—C3—C6	121.9 (3)	N1—C1—H1B	120.3
C5—C4—C3	119.3 (4)	C2—C1—H1B	120.3
C5—C4—H4A	120.4

C1—C2—C3—C4	−1.1 (6)	C2—C3—C4—C5	1.1 (6)
C1—C2—C3—C6	179.5 (4)	C6—C3—C4—C5	−179.4 (4)
O5—C6—C3—C4	−12.0 (5)	C3—C4—C5—N1	−0.4 (6)
C7—C6—C3—C4	167.1 (4)	C4—C5—N1—C1	−0.3 (7)
O5—C6—C3—C2	167.4 (4)	C5—N1—C1—C2	0.3 (7)
C7—C6—C3—C2	−13.4 (5)	C3—C2—C1—N1	0.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.14	2.896 (5)	146
C1—H1B···O5ⁱⁱ	0.93	2.49	2.963 (5)	112
C2—H2A···O3ⁱⁱⁱ	0.93	2.59	3.435 (6)	151
C5—H5A···O4ⁱ	0.93	2.46	3.332 (6)	156
C7—H7B···O3ⁱⁱⁱ	0.96	2.58	3.488 (6)	158

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

Experimental details

Crystal data
Chemical formula	C₇H₈NO⁺·ClO₄⁻
M_r	221.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	5.4657 (11), 12.621 (3), 13.490 (3)
β (°)	97.88 (3)
V (Å³)	921.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.921, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	9446, 2108, 1619
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.167, 1.06
No. of reflections	2108
No. of parameters	127
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.90

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.14	2.896 (5)	146
C1—H1B···O5ⁱⁱ	0.93	2.49	2.963 (5)	112
C2—H2A···O3ⁱⁱⁱ	0.93	2.59	3.435 (6)	151
C5—H5A···O4ⁱ	0.93	2.46	3.332 (6)	156
C7—H7B···O3ⁱⁱⁱ	0.96	2.58	3.488 (6)	158

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

Acknowledgements

The author thanks the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Piner, R. (1934). Ber. Dtsch Chem. Ges. B34, 4250–4251. Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar