4-Butyl­anilinium perchlorate

Cai, X.-W.; Lu, H.-F.

doi:10.1107/S1600536811022860

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1690

doi:10.1107/S1600536811022860

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4-Butylanilinium perchlorate

Xing-Wei Cai ^a ^* and Hong-Fei Lu ^a

^aSchool of Biological and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, People's Republic of China
^*Correspondence e-mail: cxwchem@yahoo.com.cn

(Received 9 June 2011; accepted 13 June 2011; online 18 June 2011)

In the crystal structure of the title salt, C₁₀H₁₆N⁺·ClO₄⁻, the 4-butylanilinium cation is mirror symmetric, the butyl C atoms and anilinium N atom and 1,4-position C atoms of the benzene ring being located on the mirror plane; the perchlorate anion is also mirror symmetric, with two O atoms and one Cl atom lying on the mirror plane. Trifurcated N—H⋯O hydrogen bonding is observed between the cation and anion in the crystal structure.

Related literature

For related amine derivatives and their applications, see: Fender et al. (2002 ); Kryatova et al. (2004 ); Fu et al. (2010 ); Aminabhavi et al. (1986 ).

Experimental

Crystal data

C₁₀H₁₆N⁺·ClO₄⁻
M_r = 249.69
Monoclinic, P 2₁ /m
a = 4.8825 (10) Å
b = 7.9565 (16) Å
c = 15.452 (3) Å
β = 97.35 (3)°
V = 595.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 298 K
0.10 × 0.03 × 0.03 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.910, T_max = 1.000
6108 measured reflections
1466 independent reflections
1102 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.255
S = 1.15
1466 reflections
97 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.39 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	2.21	2.873 (8)	134
N1—H1A⋯O2	0.86	2.33	2.951 (7)	129
N1—H1A⋯O2ⁱⁱ	0.86	2.33	2.951 (7)	129
N1—H1B⋯O2ⁱⁱⁱ	0.86	2.17	2.960 (4)	153
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z]$ ; (iii) -x+2, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811022860/xu5241sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022860/xu5241Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022860/xu5241Isup3.cml

checkCIF report

Comment top

The amino derivatives have found wide range of applications in material science, such as molecular recognition, fluorescence and dielectric behavior (Fender et al., 2002; Kryatova et al., 2004). And there has been an increased interest in the preparation of salts of amide (Aminabhavi et al., 1986; Fu et al. 2010). We report here the crystal structure of the title compound, 4-butylanilinium monoperchlorate.

In the title compound (Fig. 1), the asymmetric unit is composed of half ClO₄^- anion and half C₁₀H₁₆N⁺ organic cation. The N atom of the amine group is protonated. The butyl group is approximately perpendicular to the benzene plane, the torsion angle C3–C4–C5–C6 = 88.5 (6)°.

In the crystal structure, the trifurcated N—H···O hydrogen bonding is observed between the cation and anion (Table 1).

Related literature top

For related amine derivatives and their applications, see: Fender et al. (2002); Kryatova et al. (2004); Fu et al. (2010); Aminabhavi et al. (1986).

Experimental top

4-Butylanilinium perchlorate was obtained commercially from Alfa Aesar. Colourless block-shaped crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol/water (2:1 v/v) solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the asymmetric unit with the atomic numbering scheme. The displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. Part of the crystal packing of the title compound along the a axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

4-Butylanilinium perchlorate top

Crystal data top

C₁₀H₁₆N⁺·ClO₄⁻	F(000) = 264
M_r = 249.69	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1466 reflections
a = 4.8825 (10) Å	θ = 3.7–27.5°
b = 7.9565 (16) Å	µ = 0.32 mm⁻¹
c = 15.452 (3) Å	T = 298 K
β = 97.35 (3)°	Block, colorless
V = 595.4 (2) Å³	0.10 × 0.03 × 0.03 mm
Z = 2

Data collection top

Rigaku Mercury2 diffractometer	1466 independent reflections
Radiation source: fine-focus sealed tube	1102 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.7°
CCD profile fitting scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.910, T_max = 1.000	l = −19→20
6108 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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.255	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.1129P)² + 1.2735P] where P = (F_o² + 2F_c²)/3
1466 reflections	(Δ/σ)_max < 0.001
97 parameters	Δρ_max = 0.80 e Å⁻³
2 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₀H₁₆N⁺·ClO₄⁻	V = 595.4 (2) Å³
M_r = 249.69	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 4.8825 (10) Å	µ = 0.32 mm⁻¹
b = 7.9565 (16) Å	T = 298 K
c = 15.452 (3) Å	0.10 × 0.03 × 0.03 mm
β = 97.35 (3)°

Data collection top

Rigaku Mercury2 diffractometer	1466 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1102 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.064
6108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	2 restraints
wR(F²) = 0.255	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.80 e Å⁻³
1466 reflections	Δρ_min = −0.39 e Å⁻³
97 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6840 (3)	0.2500	0.58920 (10)	0.0330 (5)
O3	0.7917 (12)	0.2500	0.6775 (3)	0.0577 (14)
O2	0.7792 (8)	0.1039 (4)	0.5470 (2)	0.0512 (10)
O1	0.3918 (11)	0.2500	0.5797 (4)	0.0584 (15)
C1	0.8370 (13)	0.2500	0.3416 (4)	0.0338 (13)
N1	1.0745 (12)	0.2500	0.4098 (4)	0.0408 (13)
H1A	1.0715	0.2500	0.4653	0.061*
H1B	1.1566	0.1543	0.4106	0.061*
C4	0.3891 (14)	0.2500	0.2140 (4)	0.0397 (15)
C5	0.1577 (18)	0.2500	0.1403 (5)	0.055 (2)
H5	0.053 (13)	0.348 (8)	0.144 (4)	0.066*
C2	0.7268 (10)	0.0998 (6)	0.3113 (3)	0.0429 (11)
H2	0.8012	−0.0013	0.3336	0.052*
C6	0.2653 (17)	0.2500	0.0523 (5)	0.0499 (18)
H6	0.349 (12)	0.155 (7)	0.048 (4)	0.060*
C7	0.043 (2)	0.2500	−0.0246 (6)	0.067 (3)
H7	−0.091 (14)	0.344 (8)	−0.021 (4)	0.081*
C3	0.5053 (11)	0.1013 (6)	0.2476 (3)	0.0461 (12)
H3	0.4305	−0.0003	0.2263	0.055*
C8	0.151 (3)	0.2500	−0.1102 (6)	0.091 (3)
H8A	−0.0007	0.2500	−0.1562	0.136*
H8B	0.2620	0.3485	−0.1149	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0304 (8)	0.0272 (7)	0.0404 (8)	0.000	0.0010 (5)	0.000
O3	0.071 (4)	0.054 (3)	0.045 (3)	0.000	−0.002 (2)	0.000
O2	0.057 (2)	0.0303 (18)	0.068 (2)	0.0049 (15)	0.0126 (17)	−0.0083 (16)
O1	0.035 (3)	0.049 (3)	0.090 (4)	0.000	0.006 (3)	0.000
C1	0.034 (3)	0.035 (3)	0.033 (3)	0.000	0.008 (2)	0.000
N1	0.044 (3)	0.036 (3)	0.042 (3)	0.000	0.002 (2)	0.000
C4	0.036 (3)	0.051 (4)	0.032 (3)	0.000	0.006 (3)	0.000
C5	0.048 (5)	0.069 (5)	0.046 (4)	0.000	−0.001 (3)	0.000
C2	0.048 (3)	0.031 (2)	0.049 (3)	−0.0007 (19)	0.003 (2)	0.0057 (19)
C6	0.050 (5)	0.053 (5)	0.046 (4)	0.000	0.004 (3)	0.000
C7	0.089 (7)	0.060 (5)	0.047 (5)	0.000	−0.014 (4)	0.000
C3	0.055 (3)	0.036 (3)	0.047 (3)	−0.009 (2)	0.004 (2)	−0.004 (2)
C8	0.099 (9)	0.120 (10)	0.050 (5)	0.000	−0.003 (5)	0.000

Geometric parameters (Å, º) top

Cl1—O3	1.398 (5)	C5—C6	1.520 (11)
Cl1—O1	1.415 (5)	C5—H5	0.94 (6)
Cl1—O2	1.439 (3)	C2—C3	1.366 (7)
Cl1—O2ⁱ	1.439 (3)	C2—H2	0.9300
C1—C2	1.369 (5)	C6—C7	1.503 (12)
C1—C2ⁱ	1.369 (5)	C6—H6	0.86 (6)
C1—N1	1.464 (8)	C7—C8	1.486 (15)
N1—H1A	0.8600	C7—H7	1.00 (7)
N1—H1B	0.8601	C3—H3	0.9300
C4—C3ⁱ	1.384 (6)	C8—H8A	0.9601
C4—C3	1.384 (6)	C8—H8B	0.9600
C4—C5	1.498 (10)

O3—Cl1—O1	110.5 (4)	C6—C5—H5	108 (4)
O3—Cl1—O2	109.8 (2)	C3—C2—C1	118.6 (4)
O1—Cl1—O2	109.4 (2)	C3—C2—H2	120.7
O3—Cl1—O2ⁱ	109.8 (2)	C1—C2—H2	120.7
O1—Cl1—O2ⁱ	109.4 (2)	C7—C6—C5	114.2 (8)
O2—Cl1—O2ⁱ	107.8 (3)	C7—C6—H6	104 (4)
C2—C1—C2ⁱ	121.7 (6)	C5—C6—H6	107 (4)
C2—C1—N1	119.2 (3)	C8—C7—C6	113.6 (10)
C2ⁱ—C1—N1	119.2 (3)	C8—C7—H7	111 (4)
C1—N1—H1A	127.2	C6—C7—H7	112 (4)
C1—N1—H1B	109.6	C2—C3—C4	121.8 (5)
H1A—N1—H1B	93.1	C2—C3—H3	119.1
C3ⁱ—C4—C3	117.4 (6)	C4—C3—H3	119.1
C3ⁱ—C4—C5	121.2 (3)	C7—C8—H8A	109.3
C3—C4—C5	121.2 (3)	C7—C8—H8B	109.6
C4—C5—C6	111.5 (7)	H8A—C8—H8B	109.5
C4—C5—H5	108 (4)

C3ⁱ—C4—C5—C6	88.1 (6)	C5—C6—C7—C8	180.0
C3—C4—C5—C6	−88.1 (6)	C1—C2—C3—C4	−0.6 (9)
C2ⁱ—C1—C2—C3	1.6 (10)	C3ⁱ—C4—C3—C2	−0.3 (10)
N1—C1—C2—C3	−180.0 (5)	C5—C4—C3—C2	176.1 (6)
C4—C5—C6—C7	180.0

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱⁱ	0.86	2.21	2.873 (8)	134
N1—H1A···O2	0.86	2.33	2.951 (7)	129
N1—H1A···O2ⁱ	0.86	2.33	2.951 (7)	129
N1—H1B···O2ⁱⁱⁱ	0.86	2.17	2.960 (4)	153

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₆N⁺·ClO₄⁻
M_r	249.69
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	298
a, b, c (Å)	4.8825 (10), 7.9565 (16), 15.452 (3)
β (°)	97.35 (3)
V (Å³)	595.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.10 × 0.03 × 0.03

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.910, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6108, 1466, 1102
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.255, 1.15
No. of reflections	1466
No. of parameters	97
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.39

Computer programs: CrystalClear (Rigaku, 2005), 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	2.21	2.873 (8)	134
N1—H1A···O2	0.86	2.33	2.951 (7)	129
N1—H1A···O2ⁱⁱ	0.86	2.33	2.951 (7)	129
N1—H1B···O2ⁱⁱⁱ	0.86	2.17	2.960 (4)	153

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

Acknowledgements

This work was supported by a start-up grant from Jiangsu University of Science and Technology, China.

References

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