4-Methoxy-anilinium chloride.

The crystal structure of the title compound, C(7)H(10)NO(+)·Cl(-), was synthesized by the reaction of 4-methoxy-aniline and hydro-chloric acid. In the crystal structure, the ions are involved in inter-molecular N-H⋯Cl hydrogen bonds.

Related literature

For a similar organic acid-base product, see: Wu et al. (2006 ▶). This work is part of a systematic investigation of dielectric–ferroelectric materials, including organic ligands, metal–organic coordination compounds and organic–inorganic hybrid materials; see: Li et al. (2008 ▶); Hang et al. (2009 ▶).

Experimental

Crystal data

C7H10NO+·Cl−

M = 159.61

Orthorhombic,

a = 8.905 (2) Å

b = 8.489 (2) Å

c = 21.817 (4) Å

V = 1649.3 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.40 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 = 0.924, T max = 0.924

15436 measured reflections

1886 independent reflections

1452 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.165

S = 1.12

1886 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.54 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/S1600536809035429/im2133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035429/im2133Isup2.hkl

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

C7H10NO+·Cl−	F(000) = 672
Mr = 159.61	Dx = 1.286 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6458 reflections
a = 8.905 (2) Å	θ = 3.0–27.6°
b = 8.489 (2) Å	µ = 0.40 mm−1
c = 21.817 (4) Å	T = 298 K
V = 1649.3 (6) Å3	Prism, colourless
Z = 8	0.20 × 0.20 × 0.20 mm

Rigaku SCXmini diffractometer	1886 independent reflections
Radiation source: fine-focus sealed tube	1452 reflections with I > 2σ(I)
graphite	Rint = 0.058
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→11
Tmin = 0.924, Tmax = 0.924	l = −27→28
15436 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0824P)2 + 0.5018P] where P = (Fo2 + 2Fc2)/3
1886 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.53 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	0.75138 (6)	0.98509 (7)	0.52111 (3)	0.0470 (3)
O1	0.1534 (2)	0.1996 (2)	0.29469 (8)	0.0623 (6)
N1	0.0252 (3)	0.2494 (3)	0.04478 (10)	0.0617 (7)
H1D	−0.0468	0.3203	0.0383	0.093*
H1E	−0.0059	0.1553	0.0320	0.093*
H1F	0.1073	0.2770	0.0242	0.093*
C2	0.1175 (3)	0.2222 (3)	0.23454 (10)	0.0438 (6)
C5	0.0595 (3)	0.2423 (3)	0.11049 (11)	0.0441 (6)
C4	0.1677 (3)	0.1392 (3)	0.13138 (12)	0.0561 (7)
H4A	0.2203	0.0762	0.1039	0.067*
C6	−0.0179 (3)	0.3363 (3)	0.15081 (12)	0.0492 (6)
H6A	−0.0895	0.4069	0.1363	0.059*
C7	0.0108 (3)	0.3259 (3)	0.21326 (11)	0.0472 (6)
H7A	−0.0420	0.3890	0.2407	0.057*
C3	0.1970 (3)	0.1303 (4)	0.19295 (13)	0.0575 (7)
H3A	0.2710	0.0621	0.2071	0.069*
C1	0.0870 (4)	0.3025 (4)	0.33900 (13)	0.0761 (10)
H1A	0.1211	0.2740	0.3792	0.114*
H1B	−0.0203	0.2934	0.3371	0.114*
H1C	0.1157	0.4092	0.3304	0.114*

	U11	U22	U33	U12	U13	U23
Cl1	0.0461 (4)	0.0472 (4)	0.0478 (4)	−0.0017 (2)	0.0013 (3)	−0.0042 (2)
O1	0.0691 (13)	0.0735 (13)	0.0442 (10)	−0.0047 (11)	−0.0113 (9)	0.0042 (9)
N1	0.0690 (16)	0.0723 (16)	0.0439 (12)	−0.0200 (12)	−0.0091 (11)	0.0082 (11)
C2	0.0435 (14)	0.0466 (12)	0.0414 (13)	−0.0109 (11)	−0.0051 (10)	0.0065 (10)
C5	0.0440 (13)	0.0496 (13)	0.0388 (12)	−0.0143 (11)	−0.0040 (10)	0.0055 (10)
C4	0.0598 (16)	0.0597 (16)	0.0488 (15)	0.0083 (13)	0.0060 (12)	−0.0031 (12)
C6	0.0421 (13)	0.0499 (14)	0.0554 (14)	0.0024 (11)	−0.0056 (11)	0.0060 (12)
C7	0.0404 (13)	0.0526 (15)	0.0486 (13)	−0.0008 (11)	0.0000 (11)	−0.0056 (11)
C3	0.0570 (16)	0.0592 (16)	0.0564 (16)	0.0167 (14)	−0.0053 (13)	0.0062 (13)
C1	0.075 (2)	0.109 (3)	0.0448 (15)	−0.011 (2)	−0.0045 (14)	−0.0147 (16)

O1—C2	1.364 (3)	C4—C3	1.370 (4)
O1—C1	1.431 (4)	C4—H4A	0.9300
N1—C5	1.467 (3)	C6—C7	1.389 (4)
N1—H1D	0.8900	C6—H6A	0.9300
N1—H1E	0.8900	C7—H7A	0.9300
N1—H1F	0.8900	C3—H3A	0.9300
C2—C7	1.376 (4)	C1—H1A	0.9600
C2—C3	1.390 (4)	C1—H1B	0.9600
C5—C6	1.373 (4)	C1—H1C	0.9600
C5—C4	1.380 (4)
C2—O1—C1	117.9 (2)	C5—C6—C7	119.9 (2)
C5—N1—H1D	109.5	C5—C6—H6A	120.0
C5—N1—H1E	109.5	C7—C6—H6A	120.0
H1D—N1—H1E	109.5	C2—C7—C6	119.9 (2)
C5—N1—H1F	109.5	C2—C7—H7A	120.0
H1D—N1—H1F	109.5	C6—C7—H7A	120.0
H1E—N1—H1F	109.5	C4—C3—C2	120.8 (2)
O1—C2—C7	125.2 (2)	C4—C3—H3A	119.6
O1—C2—C3	115.4 (2)	C2—C3—H3A	119.6
C7—C2—C3	119.4 (2)	O1—C1—H1A	109.5
C6—C5—C4	120.5 (2)	O1—C1—H1B	109.5
C6—C5—N1	119.8 (2)	H1A—C1—H1B	109.5
C4—C5—N1	119.6 (2)	O1—C1—H1C	109.5
C3—C4—C5	119.5 (2)	H1A—C1—H1C	109.5
C3—C4—H4A	120.3	H1B—C1—H1C	109.5
C5—C4—H4A	120.3
C1—O1—C2—C7	−6.9 (4)	O1—C2—C7—C6	−178.8 (2)
C1—O1—C2—C3	173.4 (3)	C3—C2—C7—C6	0.9 (4)
C6—C5—C4—C3	0.4 (4)	C5—C6—C7—C2	0.4 (4)
N1—C5—C4—C3	−178.5 (2)	C5—C4—C3—C2	1.0 (4)
C4—C5—C6—C7	−1.1 (4)	O1—C2—C3—C4	178.1 (3)
N1—C5—C6—C7	177.8 (2)	C7—C2—C3—C4	−1.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1i	0.89	2.47	3.360 (3)	179
N1—H1E···Cl1ii	0.89	2.50	3.209 (2)	137
N1—H1F···Cl1iii	0.89	2.38	3.167 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯Cl1i	0.89	2.47	3.360 (3)	179
N1—H1E⋯Cl1ii	0.89	2.50	3.209 (2)	137
N1—H1F⋯Cl1iii	0.89	2.38	3.167 (2)	147

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