2,4-Dimethyl-anilinium perchlorate.

The crystal packing of the title compound, C(8)H(12)N(+)·ClO(4) (-), is stabilized by N-H⋯O hydrogen bonds, the protonated amine group acting as a hydrogen-bond donor with the perchlorate O atoms as acceptors. These connect neighbouring cations and anions, forming a two-dimensional network. Variable-temperature dielectric constant measurements on the salt indicated that no distinct phase transition occurred within the measured temperature range of 80-293 K.

Related literature

For the synthesis and characterization of 2,4-dimethyl­anilinium phosphate, see: Fábry et al. (2001 ▶). For the structure of 2,4,6-trimethyl­anilinium iodide, see: Lemmerer & Billing (2007 ▶).

Experimental

Crystal data

C8H12N+·ClO4 −

M = 221.64

Monoclinic,

a = 9.3299 (19) Å

b = 7.1947 (14) Å

c = 15.176 (3) Å

β = 97.43 (3)°

V = 1010.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 293 K

0.45 × 0.30 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.884, T max = 0.950

9986 measured reflections

2318 independent reflections

1970 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.09

2318 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.38 e Å−3

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: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017253/sj2798sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017253/sj2798Isup2.hkl

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

C8H12N+·ClO4−	F(000) = 464
Mr = 221.64	Dx = 1.457 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1970 reflections
a = 9.3299 (19) Å	θ = 3.1–27.5°
b = 7.1947 (14) Å	µ = 0.37 mm−1
c = 15.176 (3) Å	T = 293 K
β = 97.43 (3)°	Prism, colorless
V = 1010.2 (3) Å3	0.45 × 0.30 × 0.15 mm
Z = 4

Rigaku SCXmini diffractometer	2318 independent reflections
Radiation source: fine-focus sealed tube	1970 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.884, Tmax = 0.950	l = −19→19
9986 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.4369P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2318 reflections	Δρmax = 0.22 e Å−3
130 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (1)

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 > 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.

	x	y	z	Uiso*/Ueq
Cl1	0.44022 (5)	0.20914 (6)	0.11652 (3)	0.03993 (17)
N1	0.37293 (19)	0.7004 (2)	0.12219 (13)	0.0489 (5)
H1A	0.4247	0.6911	0.1755	0.073*
H1B	0.3888	0.8107	0.0986	0.073*
H1C	0.3987	0.6108	0.0870	0.073*
C5	0.1146 (2)	0.7244 (3)	0.05939 (13)	0.0400 (4)
O2	0.47637 (18)	0.3056 (2)	0.19934 (10)	0.0576 (4)
C6	−0.0291 (2)	0.7058 (3)	0.07285 (14)	0.0453 (5)
H6	−0.1004	0.7328	0.0259	0.054*
O3	0.4530 (2)	0.3369 (2)	0.04594 (11)	0.0687 (5)
C1	0.2174 (2)	0.6817 (2)	0.13112 (13)	0.0374 (4)
C3	0.0362 (2)	0.6056 (3)	0.22160 (14)	0.0508 (5)
H3	0.0108	0.5647	0.2756	0.061*
C2	0.1796 (2)	0.6221 (3)	0.21116 (14)	0.0489 (5)
H2	0.2508	0.5931	0.2579	0.059*
O1	0.5376 (2)	0.0565 (2)	0.11199 (14)	0.0717 (5)
C4	−0.0713 (2)	0.6491 (3)	0.15282 (14)	0.0447 (5)
O4	0.29667 (19)	0.1392 (3)	0.11030 (13)	0.0764 (6)
C8	0.1543 (3)	0.7883 (4)	−0.02867 (16)	0.0648 (7)
H8A	0.0687	0.7957	−0.0711	0.097*
H8B	0.2206	0.7014	−0.0493	0.097*
H8C	0.1989	0.9086	−0.0219	0.097*
C7	−0.2294 (3)	0.6367 (5)	0.1648 (2)	0.0716 (8)
H7A	−0.2563	0.7443	0.1962	0.107*
H7B	−0.2455	0.5269	0.1981	0.107*
H7C	−0.2869	0.6309	0.1076	0.107*

	U11	U22	U33	U12	U13	U23
Cl1	0.0472 (3)	0.0343 (3)	0.0378 (3)	−0.00671 (19)	0.00362 (19)	0.00247 (18)
N1	0.0431 (10)	0.0372 (9)	0.0668 (12)	−0.0048 (7)	0.0083 (8)	−0.0034 (8)
C5	0.0499 (11)	0.0324 (9)	0.0376 (10)	−0.0001 (8)	0.0056 (8)	−0.0034 (8)
O2	0.0645 (10)	0.0629 (11)	0.0441 (9)	−0.0085 (8)	0.0022 (7)	−0.0104 (7)
C6	0.0447 (11)	0.0460 (11)	0.0425 (11)	0.0061 (9)	−0.0051 (8)	−0.0041 (9)
O3	0.1083 (15)	0.0501 (9)	0.0500 (9)	−0.0033 (10)	0.0185 (9)	0.0161 (8)
C1	0.0360 (9)	0.0281 (9)	0.0475 (11)	−0.0009 (7)	0.0035 (8)	−0.0033 (8)
C3	0.0580 (13)	0.0563 (14)	0.0386 (10)	−0.0109 (11)	0.0086 (9)	0.0008 (10)
C2	0.0499 (12)	0.0486 (12)	0.0449 (11)	−0.0038 (10)	−0.0067 (9)	0.0094 (10)
O1	0.0846 (13)	0.0446 (9)	0.0855 (13)	0.0141 (9)	0.0097 (10)	−0.0015 (9)
C4	0.0407 (10)	0.0450 (11)	0.0490 (11)	−0.0020 (9)	0.0087 (8)	−0.0127 (10)
O4	0.0571 (11)	0.0905 (14)	0.0783 (12)	−0.0318 (10)	−0.0041 (9)	−0.0005 (11)
C8	0.0829 (18)	0.0708 (17)	0.0423 (12)	−0.0117 (14)	0.0141 (11)	0.0031 (12)
C7	0.0469 (13)	0.090 (2)	0.0805 (18)	−0.0010 (14)	0.0197 (12)	−0.0212 (16)

Cl1—O4	1.4225 (17)	C1—C2	1.377 (3)
Cl1—O3	1.4281 (16)	C3—C2	1.373 (3)
Cl1—O1	1.4326 (18)	C3—C4	1.386 (3)
Cl1—O2	1.4372 (16)	C3—H3	0.9300
N1—C1	1.481 (2)	C2—H2	0.9300
N1—H1A	0.8900	C4—C7	1.512 (3)
N1—H1B	0.8900	C8—H8A	0.9600
N1—H1C	0.8900	C8—H8B	0.9600
C5—C6	1.388 (3)	C8—H8C	0.9600
C5—C1	1.389 (3)	C7—H7A	0.9600
C5—C8	1.504 (3)	C7—H7B	0.9600
C6—C4	1.385 (3)	C7—H7C	0.9600
C6—H6	0.9300
O4—Cl1—O3	110.33 (13)	C2—C3—C4	121.0 (2)
O4—Cl1—O1	108.85 (13)	C2—C3—H3	119.5
O3—Cl1—O1	110.01 (12)	C4—C3—H3	119.5
O4—Cl1—O2	109.96 (11)	C3—C2—C1	119.57 (19)
O3—Cl1—O2	108.19 (11)	C3—C2—H2	120.2
O1—Cl1—O2	109.48 (11)	C1—C2—H2	120.2
C1—N1—H1A	109.5	C6—C4—C3	117.8 (2)
C1—N1—H1B	109.5	C6—C4—C7	121.0 (2)
H1A—N1—H1B	109.5	C3—C4—C7	121.2 (2)
C1—N1—H1C	109.5	C5—C8—H8A	109.5
H1A—N1—H1C	109.5	C5—C8—H8B	109.5
H1B—N1—H1C	109.5	H8A—C8—H8B	109.5
C6—C5—C1	116.46 (18)	C5—C8—H8C	109.5
C6—C5—C8	120.9 (2)	H8A—C8—H8C	109.5
C1—C5—C8	122.6 (2)	H8B—C8—H8C	109.5
C4—C6—C5	123.14 (19)	C4—C7—H7A	109.5
C4—C6—H6	118.4	C4—C7—H7B	109.5
C5—C6—H6	118.4	H7A—C7—H7B	109.5
C2—C1—C5	122.05 (19)	C4—C7—H7C	109.5
C2—C1—N1	118.36 (18)	H7A—C7—H7C	109.5
C5—C1—N1	119.58 (18)	H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1i	0.89	2.24	3.002 (3)	143
N1—H1B···O4i	0.89	2.53	3.236 (3)	137
N1—H1A···O2ii	0.89	2.16	2.983 (3)	153
N1—H1C···O3	0.89	2.15	2.994 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.89	2.24	3.002 (3)	143
N1—H1B⋯O4i	0.89	2.53	3.236 (3)	137
N1—H1A⋯O2ii	0.89	2.16	2.983 (3)	153
N1—H1C⋯O3	0.89	2.15	2.994 (3)	159

Symmetry codes: (i) ; (ii) .