4-Butyl­anilinium perchlorate

Abstract

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,

• a = 4.8825 (10) Å

• b = 7.9565 (16) Å

• c = 15.452 (3) Å

• β = 97.35 (3)°

• V = 595.4 (2) ų

• 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[F ² > 2σ(F ²)] = 0.084

• wR(F ²) = 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

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.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811022860/xu5241Isup3.cml

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

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) ; (ii) ; (iii) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All H atoms attached to C atoms were fixed geometrically and treated as riding with C–H = 0.93 Å (aromatic), C–H = 0.96 Å (methyl) and C–H = 0.97 Å (methylene), with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for the others. All NH₃⁺ hydrogen atoms were calculated geometrically and were refined using a riding model with N—H = 0.86 Å and U_iso(H) = 1.5U_eq(N).

Figures

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.

Crystal data

C10H16N+·ClO4−	F(000) = 264
Mr = 249.69	Dx = 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

Rigaku Mercury2 diffractometer	1466 independent reflections
Radiation source: fine-focus sealed tube	1102 reflections with I > 2σ(I)
graphite	Rint = 0.064
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.7°
CCD profile fitting scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.910, Tmax = 1.000	l = −19→20
6108 measured reflections

Refinement

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(Fo2) + (0.1129P)2 + 1.2735P] where P = (Fo2 + 2Fc2)/3
1466 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 0.80 e Å−3
2 restraints	Δρmin = −0.39 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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 codes: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, °)

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