4-Eth-oxy-anilinium chloride.

The title compound, C(8)H(12)NO(+)·Cl(-), consists of an almost planar protonated 4-eth-oxy-anilinium cation with the N atom showing the biggest deviation from the plane formed by all non-H atoms of the cation [0.066 (1) Å]. In the crystal, N-H⋯Cl hydrogen bonds link cations and anions into chains along the a axis. Additional C-H⋯π and π-π inter-actions [centroid-centroid distance = 4.873 (2) Å] stabilize the crystal structure.

Related literature

For background to phase-transition materials, see: Li et al. (2008 ▶); Ye et al. (2009 ▶); Zhang et al. (2009 ▶). For similar structures, see: Fu (2009 ▶); Jiang et al. (1996 ▶); Zhao (2009 ▶).

Experimental

Crystal data

C8H12NO+·Cl−

M = 173.64

Orthorhombic,

a = 11.422 (2) Å

b = 7.0890 (14) Å

c = 22.887 (5) Å

V = 1853.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.36 mm−1

T = 298 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.879, T max = 0.931

17046 measured reflections

2116 independent reflections

1655 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.106

S = 1.08

2116 reflections

112 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.23 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025973/im2216sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025973/im2216Isup2.hkl

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

C8H12NO+·Cl−	F(000) = 736
Mr = 173.64	Dx = 1.245 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7266 reflections
a = 11.422 (2) Å	θ = 3.0–27.7°
b = 7.0890 (14) Å	µ = 0.36 mm−1
c = 22.887 (5) Å	T = 298 K
V = 1853.2 (6) Å3	Prism, colourless
Z = 8	0.40 × 0.30 × 0.20 mm

Rigaku SCXmini diffractometer	2116 independent reflections
Radiation source: fine-focus sealed tube	1655 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.5°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.879, Tmax = 0.931	l = −29→29
17046 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.7382P] where P = (Fo2 + 2Fc2)/3
2116 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.23 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	0.36897 (4)	0.14153 (8)	0.73645 (2)	0.0565 (2)
C3	0.39597 (14)	0.6120 (3)	0.64180 (8)	0.0382 (4)
O1	0.39659 (12)	0.76724 (19)	0.46863 (5)	0.0495 (4)
C6	0.39549 (15)	0.7056 (3)	0.52510 (8)	0.0384 (4)
N1	0.39087 (15)	0.5668 (3)	0.70418 (7)	0.0456 (4)
H1D	0.323 (2)	0.619 (3)	0.7215 (10)	0.072 (7)*
H1C	0.451 (2)	0.614 (4)	0.7224 (11)	0.081 (8)*
H1B	0.387 (2)	0.442 (5)	0.7096 (12)	0.084 (9)*
C7	0.34271 (19)	0.6523 (3)	0.42485 (8)	0.0509 (5)
H7A	0.2601	0.6365	0.4333	0.061*
H7B	0.3791	0.5287	0.4240	0.061*
C5	0.34210 (18)	0.5419 (3)	0.54364 (9)	0.0511 (5)
H5A	0.3060	0.4626	0.5168	0.061*
C4	0.34242 (17)	0.4958 (3)	0.60251 (9)	0.0507 (5)
H4A	0.3061	0.3858	0.6152	0.061*
C1	0.45119 (17)	0.8200 (3)	0.56533 (8)	0.0468 (5)
H1A	0.4890	0.9289	0.5528	0.056*
C8	0.3583 (2)	0.7490 (4)	0.36708 (9)	0.0651 (6)
H8A	0.3226	0.6748	0.3369	0.098*
H8B	0.4403	0.7631	0.3590	0.098*
H8C	0.3220	0.8711	0.3684	0.098*
C2	0.45113 (17)	0.7739 (3)	0.62369 (8)	0.0456 (5)
H2A	0.4882	0.8517	0.6507	0.055*

	U11	U22	U33	U12	U13	U23
Cl1	0.0385 (3)	0.0715 (4)	0.0596 (3)	−0.0036 (2)	−0.0107 (2)	0.0117 (3)
C3	0.0278 (8)	0.0501 (11)	0.0366 (9)	0.0017 (7)	−0.0005 (7)	0.0041 (8)
O1	0.0676 (9)	0.0474 (8)	0.0334 (7)	−0.0125 (7)	−0.0020 (6)	0.0020 (6)
C6	0.0387 (9)	0.0406 (10)	0.0359 (9)	−0.0017 (8)	0.0015 (7)	0.0015 (8)
N1	0.0329 (9)	0.0653 (13)	0.0387 (9)	0.0010 (8)	−0.0008 (7)	0.0082 (9)
C7	0.0576 (12)	0.0565 (12)	0.0387 (10)	−0.0041 (10)	−0.0017 (8)	−0.0069 (9)
C5	0.0571 (12)	0.0524 (12)	0.0438 (11)	−0.0209 (10)	−0.0067 (9)	0.0004 (9)
C4	0.0510 (11)	0.0532 (12)	0.0477 (11)	−0.0204 (9)	−0.0022 (8)	0.0079 (10)
C1	0.0583 (12)	0.0393 (10)	0.0428 (10)	−0.0122 (9)	0.0003 (9)	0.0029 (8)
C8	0.0884 (17)	0.0686 (15)	0.0382 (11)	0.0068 (13)	−0.0028 (10)	−0.0032 (11)
C2	0.0511 (11)	0.0438 (11)	0.0418 (10)	−0.0087 (9)	−0.0053 (8)	−0.0045 (8)

C3—C4	1.364 (3)	C7—H7A	0.9700
C3—C2	1.373 (3)	C7—H7B	0.9700
C3—N1	1.464 (2)	C5—C4	1.386 (3)
O1—C6	1.364 (2)	C5—H5A	0.9300
O1—C7	1.431 (2)	C4—H4A	0.9300
C6—C5	1.378 (3)	C1—C2	1.375 (3)
C6—C1	1.382 (3)	C1—H1A	0.9300
N1—H1D	0.94 (2)	C8—H8A	0.9600
N1—H1C	0.87 (3)	C8—H8B	0.9600
N1—H1B	0.90 (3)	C8—H8C	0.9600
C7—C8	1.500 (3)	C2—H2A	0.9300
C4—C3—C2	120.75 (17)	C6—C5—C4	119.76 (18)
C4—C3—N1	119.51 (18)	C6—C5—H5A	120.1
C2—C3—N1	119.70 (17)	C4—C5—H5A	120.1
C6—O1—C7	118.49 (15)	C3—C4—C5	119.98 (18)
O1—C6—C5	124.45 (17)	C3—C4—H4A	120.0
O1—C6—C1	116.03 (16)	C5—C4—H4A	120.0
C5—C6—C1	119.51 (17)	C2—C1—C6	120.50 (17)
C3—N1—H1D	110.9 (14)	C2—C1—H1A	119.7
C3—N1—H1C	110.6 (17)	C6—C1—H1A	119.7
H1D—N1—H1C	107 (2)	C7—C8—H8A	109.5
C3—N1—H1B	110.7 (18)	C7—C8—H8B	109.5
H1D—N1—H1B	107 (2)	H8A—C8—H8B	109.5
H1C—N1—H1B	111 (2)	C7—C8—H8C	109.5
O1—C7—C8	107.79 (18)	H8A—C8—H8C	109.5
O1—C7—H7A	110.1	H8B—C8—H8C	109.5
C8—C7—H7A	110.1	C3—C2—C1	119.47 (17)
O1—C7—H7B	110.1	C3—C2—H2A	120.3
C8—C7—H7B	110.1	C1—C2—H2A	120.3
H7A—C7—H7B	108.5
C7—O1—C6—C5	−2.4 (3)	C6—C5—C4—C3	−0.3 (3)
C7—O1—C6—C1	178.51 (17)	O1—C6—C1—C2	177.53 (18)
C6—O1—C7—C8	−178.74 (17)	C5—C6—C1—C2	−1.6 (3)
O1—C6—C5—C4	−177.57 (19)	C4—C3—C2—C1	0.7 (3)
C1—C6—C5—C4	1.5 (3)	N1—C3—C2—C1	−177.14 (18)
C2—C3—C4—C5	−0.8 (3)	C6—C1—C2—C3	0.5 (3)
N1—C3—C4—C5	177.04 (18)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1i	0.94 (2)	2.23 (3)	3.104 (2)	154 (2)
N1—H1C···Cl1ii	0.87 (3)	2.27 (3)	3.107 (2)	161 (2)
N1—H1B···Cl1	0.90 (3)	2.23 (3)	3.114 (2)	172 (2)
C4—H4A···Cg1iii	0.93	2.91	3.654 (2)	138
C7—H7B···Cg1iv	0.97	2.89	3.710 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯Cl1i	0.94 (2)	2.23 (3)	3.104 (2)	154 (2)
N1—H1C⋯Cl1ii	0.87 (3)	2.27 (3)	3.107 (2)	161 (2)
N1—H1B⋯Cl1	0.90 (3)	2.23 (3)	3.114 (2)	172 (2)
C4—H4A⋯Cg1iii	0.93	2.91	3.654 (2)	138
C7—H7B⋯Cg1iv	0.97	2.89	3.710 (2)	143

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