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ISSN: 2056-9890

4-Acetyl­pyridinium perchlorate

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[Piner, R. (1934). Ber. Dtsch Chem. Ges. B34, 4250-4251.]).

[Scheme 1]

Experimental

Crystal data
  • C7H8NO+·ClO4

  • Mr = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.921, Tmax = 0.921

  • 9446 measured reflections

  • 2108 independent reflections

  • 1619 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.90 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[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: SHELXTL.

Supporting information


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.

Refinement top

The positional parameters of all the H atoms were calculated geometrically and refined as riding with Uiso(H) = 1.2Ueq(carrier).

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
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (all H atoms have been omitted for clarity).
[Figure 2] 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+·ClO4F(000) = 456
Mr = 221.59Dx = 1.597 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4087 reflections
a = 5.4657 (11) Åθ = 3.1–27.6°
b = 12.621 (3) ŵ = 0.41 mm1
c = 13.490 (3) ÅT = 298 K
β = 97.88 (3)°Prism, colourless
V = 921.8 (4) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku SCXmini
diffractometer
2108 independent reflections
Radiation source: fine-focus sealed tube1619 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 77
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1616
Tmin = 0.921, Tmax = 0.921l = 1717
9446 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0688P)2 + 0.9865P]
where P = (Fo2 + 2Fc2)/3
2108 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.65 e Å3
7 restraintsΔρmin = 0.90 e Å3
Crystal data top
C7H8NO+·ClO4V = 921.8 (4) Å3
Mr = 221.59Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.4657 (11) ŵ = 0.41 mm1
b = 12.621 (3) ÅT = 298 K
c = 13.490 (3) Å0.20 × 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)
Tmin = 0.921, Tmax = 0.921Rint = 0.049
9446 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0627 restraints
wR(F2) = 0.167H-atom parameters constrained
S = 1.06Δρmax = 0.65 e Å3
2108 reflectionsΔρmin = 0.90 e Å3
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
xyzUiso*/Ueq
Cl10.13491 (18)0.20125 (8)0.11005 (7)0.0477 (3)
O50.3901 (6)0.6009 (3)0.1267 (2)0.0640 (9)
C20.7259 (7)0.3883 (3)0.2591 (3)0.0472 (9)
H2A0.83940.37350.21550.057*
C60.5616 (7)0.5419 (3)0.1489 (3)0.0442 (9)
C30.5618 (7)0.4719 (3)0.2396 (3)0.0395 (8)
C40.3922 (7)0.4908 (4)0.3048 (3)0.0495 (10)
H4A0.27850.54570.29260.059*
C70.7761 (9)0.5359 (4)0.0917 (3)0.0584 (11)
H7A0.75090.58400.03610.088*
H7B0.79130.46500.06760.088*
H7C0.92440.55500.13470.088*
O40.0611 (7)0.0968 (3)0.0755 (3)0.0790 (11)
O30.0390 (8)0.2749 (3)0.0608 (3)0.0814 (11)
O20.1393 (7)0.2069 (3)0.2155 (2)0.0809 (12)
C50.3935 (8)0.4281 (4)0.3873 (3)0.0589 (12)
H5A0.28110.44030.43200.071*
N10.5561 (8)0.3493 (3)0.4037 (3)0.0607 (10)
H1A0.55460.31080.45620.073*
O10.3763 (6)0.2204 (3)0.0851 (2)0.0645 (6)
C10.7196 (9)0.3275 (4)0.3430 (3)0.0575 (11)
H1B0.82960.27160.35710.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0506 (6)0.0518 (6)0.0440 (5)0.0087 (4)0.0186 (4)0.0039 (4)
O50.065 (2)0.064 (2)0.062 (2)0.0170 (16)0.0035 (15)0.0069 (15)
C20.051 (2)0.043 (2)0.050 (2)0.0003 (17)0.0159 (18)0.0036 (17)
C60.049 (2)0.042 (2)0.041 (2)0.0013 (17)0.0036 (17)0.0046 (16)
C30.0386 (18)0.0403 (19)0.0396 (18)0.0047 (15)0.0058 (15)0.0044 (15)
C40.042 (2)0.056 (2)0.052 (2)0.0015 (18)0.0117 (17)0.0060 (19)
C70.066 (3)0.067 (3)0.045 (2)0.002 (2)0.017 (2)0.009 (2)
O40.085 (3)0.060 (2)0.097 (3)0.0072 (19)0.032 (2)0.0063 (19)
O30.100 (3)0.079 (2)0.065 (2)0.037 (2)0.009 (2)0.0155 (18)
O20.094 (3)0.109 (3)0.0421 (18)0.030 (2)0.0173 (17)0.0069 (17)
C50.054 (3)0.075 (3)0.051 (2)0.014 (2)0.020 (2)0.006 (2)
N10.073 (3)0.058 (2)0.052 (2)0.016 (2)0.0125 (19)0.0106 (18)
O10.0571 (11)0.0787 (12)0.0614 (11)0.0010 (10)0.0210 (10)0.0032 (10)
C10.067 (3)0.046 (2)0.060 (3)0.000 (2)0.011 (2)0.007 (2)
Geometric parameters (Å, º) top
Cl1—O21.421 (3)C4—C51.365 (6)
Cl1—O11.427 (3)C4—H4A0.9300
Cl1—O31.427 (3)C7—H7A0.9600
Cl1—O41.437 (4)C7—H7B0.9600
O5—C61.202 (5)C7—H7C0.9600
C2—C11.372 (6)C5—N11.332 (6)
C2—C31.386 (5)C5—H5A0.9300
C2—H2A0.9300N1—C11.321 (6)
C6—C71.492 (6)N1—H1A0.8600
C6—C31.509 (5)C1—H1B0.9300
C3—C41.384 (5)
O2—Cl1—O1109.8 (2)C3—C4—H4A120.4
O2—Cl1—O3110.7 (2)C6—C7—H7A109.5
O1—Cl1—O3111.0 (2)C6—C7—H7B109.5
O2—Cl1—O4109.6 (2)H7A—C7—H7B109.5
O1—Cl1—O4107.8 (2)C6—C7—H7C109.5
O3—Cl1—O4107.9 (2)H7A—C7—H7C109.5
C1—C2—C3119.5 (4)H7B—C7—H7C109.5
C1—C2—H2A120.2N1—C5—C4119.8 (4)
C3—C2—H2A120.2N1—C5—H5A120.1
O5—C6—C7123.0 (4)C4—C5—H5A120.1
O5—C6—C3118.6 (4)C1—N1—C5123.1 (4)
C7—C6—C3118.4 (3)C1—N1—H1A118.5
C4—C3—C2118.9 (4)C5—N1—H1A118.5
C4—C3—C6119.2 (3)N1—C1—C2119.4 (4)
C2—C3—C6121.9 (3)N1—C1—H1B120.3
C5—C4—C3119.3 (4)C2—C1—H1B120.3
C5—C4—H4A120.4
C1—C2—C3—C41.1 (6)C2—C3—C4—C51.1 (6)
C1—C2—C3—C6179.5 (4)C6—C3—C4—C5179.4 (4)
O5—C6—C3—C412.0 (5)C3—C4—C5—N10.4 (6)
C7—C6—C3—C4167.1 (4)C4—C5—N1—C10.3 (7)
O5—C6—C3—C2167.4 (4)C5—N1—C1—C20.3 (7)
C7—C6—C3—C213.4 (5)C3—C2—C1—N10.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.142.896 (5)146
C1—H1B···O5ii0.932.492.963 (5)112
C2—H2A···O3iii0.932.593.435 (6)151
C5—H5A···O4i0.932.463.332 (6)156
C7—H7B···O3iii0.962.583.488 (6)158
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC7H8NO+·ClO4
Mr221.59
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)5.4657 (11), 12.621 (3), 13.490 (3)
β (°) 97.88 (3)
V3)921.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.921, 0.921
No. of measured, independent and
observed [I > 2σ(I)] reflections
9446, 2108, 1619
Rint0.049
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.167, 1.06
No. of reflections2108
No. of parameters127
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.142.896 (5)146
C1—H1B···O5ii0.932.492.963 (5)112
C2—H2A···O3iii0.932.593.435 (6)151
C5—H5A···O4i0.932.463.332 (6)156
C7—H7B···O3iii0.962.583.488 (6)158
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, 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

First citationPiner, R. (1934). Ber. Dtsch Chem. Ges. B34, 4250–4251.  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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ISSN: 2056-9890
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