4-Ethoxy-anilinium perchlorate.

In the title compound, C(8)H(12)NO(+)·ClO(4) (-), there are strong hydrogen bonds between the ammonium groups and the perchlorate O atoms.

Related literature

This study is a part of systematic investigation of dielectric–ferroelectric materials, including organic ligands (Li et al., 2008 ▶), metal-organic coordination compounds (Hang et al., 2009 ▶) and organic–inorganic hybrids.

Experimental

Crystal data

C8H12NO+·ClO4 −

M = 237.64

Monoclinic,

a = 5.0663 (10) Å

b = 22.601 (5) Å

c = 9.2091 (18) Å

β = 91.49 (3)°

V = 1054.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.36 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 = 0.928, T max = 0.93

9440 measured reflections

2415 independent reflections

1795 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.138

S = 1.04

2415 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.47 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/S1600536809035041/jh2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035041/jh2099Isup2.hkl

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

C8H12NO+·ClO4−	F(000) = 496
Mr = 237.64	Dx = 1.497 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4042 reflections
a = 5.0663 (10) Å	θ = 3.5–27.6°
b = 22.601 (5) Å	µ = 0.36 mm−1
c = 9.2091 (18) Å	T = 298 K
β = 91.49 (3)°	Prism, colourless
V = 1054.1 (4) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2415 independent reflections
Radiation source: fine-focus sealed tube	1795 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.5°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −29→29
Tmin = 0.928, Tmax = 0.93	l = −11→10
9440 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0663P)2 + 0.3412P] where P = (Fo2 + 2Fc2)/3
2415 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	−0.00925 (11)	0.32367 (2)	0.57673 (6)	0.0340 (2)
N1	0.4143 (4)	0.28041 (9)	0.2574 (2)	0.0385 (5)
H1A	0.5458	0.2568	0.2319	0.058*
H1B	0.2657	0.2595	0.2616	0.058*
H1F	0.4517	0.2961	0.3441	0.058*
O5	0.2716 (4)	0.31960 (9)	0.5619 (2)	0.0524 (5)
C7	0.5402 (5)	0.33118 (11)	0.0325 (3)	0.0407 (6)
H7A	0.6706	0.3028	0.0205	0.049*
O1	0.2682 (4)	0.46533 (8)	−0.1381 (2)	0.0491 (5)
C6	0.3806 (5)	0.32820 (10)	0.1488 (3)	0.0343 (5)
C3	0.3145 (5)	0.41839 (11)	−0.0489 (3)	0.0379 (6)
O4	−0.0842 (4)	0.28604 (9)	0.6953 (2)	0.0508 (5)
C8	0.5097 (5)	0.37615 (11)	−0.0678 (3)	0.0412 (6)
H8A	0.6187	0.3782	−0.1473	0.049*
O3	−0.1320 (4)	0.30237 (11)	0.4463 (2)	0.0690 (7)
C4	0.1528 (5)	0.41445 (12)	0.0693 (3)	0.0481 (7)
H4B	0.0210	0.4425	0.0814	0.058*
C5	0.1838 (5)	0.36977 (13)	0.1689 (3)	0.0477 (7)
H5B	0.0749	0.3674	0.2485	0.057*
C2	0.4325 (7)	0.47354 (13)	−0.2604 (3)	0.0537 (8)
H2A	0.4204	0.4397	−0.3249	0.064*
H2B	0.6153	0.4786	−0.2289	0.064*
O2	−0.0857 (5)	0.38241 (9)	0.6044 (3)	0.0738 (7)
C1	0.3323 (8)	0.52830 (15)	−0.3361 (4)	0.0750 (11)
H1C	0.4367	0.5360	−0.4196	0.112*
H1D	0.3447	0.5613	−0.2707	0.112*
H1E	0.1513	0.5226	−0.3664	0.112*

	U11	U22	U33	U12	U13	U23
Cl1	0.0336 (4)	0.0366 (3)	0.0317 (4)	−0.0012 (2)	0.0009 (2)	0.0012 (2)
N1	0.0387 (13)	0.0395 (12)	0.0367 (12)	−0.0015 (9)	−0.0069 (9)	0.0010 (9)
O5	0.0312 (11)	0.0653 (13)	0.0610 (14)	−0.0010 (8)	0.0053 (9)	0.0067 (10)
C7	0.0417 (15)	0.0362 (14)	0.0441 (15)	0.0104 (11)	0.0001 (12)	−0.0050 (11)
O1	0.0579 (13)	0.0459 (11)	0.0442 (12)	0.0144 (9)	0.0143 (9)	0.0122 (8)
C6	0.0343 (14)	0.0338 (12)	0.0344 (14)	−0.0023 (10)	−0.0052 (10)	0.0007 (10)
C3	0.0384 (15)	0.0376 (13)	0.0379 (15)	0.0027 (10)	0.0016 (11)	0.0014 (10)
O4	0.0505 (13)	0.0586 (12)	0.0437 (11)	−0.0009 (9)	0.0078 (9)	0.0163 (9)
C8	0.0474 (17)	0.0410 (14)	0.0357 (15)	0.0051 (11)	0.0103 (12)	−0.0004 (11)
O3	0.0636 (16)	0.1054 (19)	0.0375 (12)	−0.0328 (13)	−0.0096 (10)	−0.0041 (11)
C4	0.0420 (17)	0.0505 (16)	0.0523 (18)	0.0139 (12)	0.0129 (13)	0.0090 (13)
C5	0.0413 (17)	0.0547 (17)	0.0477 (17)	0.0079 (12)	0.0135 (13)	0.0097 (13)
C2	0.074 (2)	0.0434 (16)	0.0442 (17)	0.0078 (13)	0.0200 (15)	0.0042 (12)
O2	0.0894 (18)	0.0380 (12)	0.0948 (18)	0.0172 (11)	0.0180 (14)	0.0021 (11)
C1	0.113 (3)	0.059 (2)	0.055 (2)	0.0190 (19)	0.026 (2)	0.0138 (16)

Cl1—O2	1.408 (2)	C6—C5	1.386 (4)
Cl1—O3	1.422 (2)	C3—C4	1.382 (4)
Cl1—O5	1.4358 (19)	C3—C8	1.389 (3)
Cl1—O4	1.4426 (19)	C8—H8A	0.9300
N1—C6	1.479 (3)	C4—C5	1.371 (4)
N1—H1A	0.8900	C4—H4B	0.9300
N1—H1B	0.8900	C5—H5B	0.9300
N1—H1F	0.8900	C2—C1	1.502 (4)
C7—C6	1.361 (4)	C2—H2A	0.9700
C7—C8	1.379 (4)	C2—H2B	0.9700
C7—H7A	0.9300	C1—H1C	0.9600
O1—C3	1.358 (3)	C1—H1D	0.9600
O1—C2	1.430 (3)	C1—H1E	0.9600
O2—Cl1—O3	110.83 (16)	C7—C8—C3	119.4 (2)
O2—Cl1—O5	110.84 (14)	C7—C8—H8A	120.3
O3—Cl1—O5	108.09 (13)	C3—C8—H8A	120.3
O2—Cl1—O4	109.88 (14)	C5—C4—C3	121.0 (2)
O3—Cl1—O4	108.77 (13)	C5—C4—H4B	119.5
O5—Cl1—O4	108.36 (12)	C3—C4—H4B	119.5
C6—N1—H1A	109.5	C4—C5—C6	118.7 (3)
C6—N1—H1B	109.5	C4—C5—H5B	120.7
H1A—N1—H1B	109.5	C6—C5—H5B	120.7
C6—N1—H1F	109.5	O1—C2—C1	106.0 (2)
H1A—N1—H1F	109.5	O1—C2—H2A	110.5
H1B—N1—H1F	109.5	C1—C2—H2A	110.5
C6—C7—C8	120.3 (2)	O1—C2—H2B	110.5
C6—C7—H7A	119.8	C1—C2—H2B	110.5
C8—C7—H7A	119.8	H2A—C2—H2B	108.7
C3—O1—C2	118.9 (2)	C2—C1—H1C	109.5
C7—C6—C5	121.1 (2)	C2—C1—H1D	109.5
C7—C6—N1	120.5 (2)	H1C—C1—H1D	109.5
C5—C6—N1	118.4 (2)	C2—C1—H1E	109.5
O1—C3—C4	115.5 (2)	H1C—C1—H1E	109.5
O1—C3—C8	125.0 (2)	H1D—C1—H1E	109.5
C4—C3—C8	119.5 (2)
C8—C7—C6—C5	0.4 (4)	O1—C3—C4—C5	−178.6 (2)
C8—C7—C6—N1	−179.4 (2)	C8—C3—C4—C5	0.6 (4)
C2—O1—C3—C4	178.1 (3)	C3—C4—C5—C6	−0.2 (4)
C2—O1—C3—C8	−1.1 (4)	C7—C6—C5—C4	−0.3 (4)
C6—C7—C8—C3	0.0 (4)	N1—C6—C5—C4	179.5 (2)
O1—C3—C8—C7	178.6 (2)	C3—O1—C2—C1	179.9 (3)
C4—C3—C8—C7	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.89	2.14	3.019 (3)	167
N1—H1B···O4ii	0.89	2.13	2.981 (3)	161
N1—H1B···Cl1ii	0.89	2.87	3.567 (2)	136
N1—H1F···O3iii	0.89	2.29	2.889 (3)	124
N1—H1F···O5	0.89	2.29	3.046 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.89	2.14	3.019 (3)	167
N1—H1B⋯O4ii	0.89	2.13	2.981 (3)	161
N1—H1B⋯Cl1ii	0.89	2.87	3.567 (2)	136
N1—H1F⋯O3iii	0.89	2.29	2.889 (3)	124
N1—H1F⋯O5	0.89	2.29	3.046 (3)	143

Symmetry codes: (i) ; (ii) ; (iii) .