4-Eth-oxy-anilinium bromide.

The title compound, C(8)H(12)NO(+)·Br(-), is built up from roughly planar (r.m.s. deviation for the non-H atoms = 0.062 Å) protonated 4-eth-oxy-anilimium cations and Br(-) anions. In the crystal, the cations and anions are linked by N-H⋯Br and N-H⋯(Br,Br) hydrogen bonds, generating (100) sheets. Very weak C-H⋯π inter-actions may also help to stabilize the crystal structure.

Related literature

For a related structure containing the same cation, see: Fu (2009 ▶).

Experimental

Crystal data

C8H12NO+·Br−

M = 218.09

Monoclinic,

a = 11.842 (2) Å

b = 6.5263 (13) Å

c = 12.488 (3) Å

β = 96.44 (3)°

V = 959.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.23 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 = 0.237, T max = 0.429

9286 measured reflections

2200 independent reflections

1579 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.173

S = 1.11

2200 reflections

100 parameters

H-atom parameters constrained

Δρmax = 1.55 e Å−3

Δρmin = −0.42 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048713/hb5753sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048713/hb5753Isup2.hkl

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

C8H12NO+·Br−	F(000) = 440
Mr = 218.09	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3858 reflections
a = 11.842 (2) Å	θ = 3.1–27.7°
b = 6.5263 (13) Å	µ = 4.23 mm−1
c = 12.488 (3) Å	T = 298 K
β = 96.44 (3)°	Prism, colourless
V = 959.0 (3) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2200 independent reflections
Radiation source: fine-focus sealed tube	1579 reflections with I > 2σ(I)
graphite	Rint = 0.073
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.3°
ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −8→8
Tmin = 0.237, Tmax = 0.429	l = −16→16
9286 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0748P)2 + 1.0824P] where P = (Fo2 + 2Fc2)/3
2200 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 1.55 e Å−3
0 restraints	Δρmin = −0.42 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
Br1	0.01352 (5)	0.76484 (8)	0.12594 (4)	0.0493 (3)
O1	0.5504 (4)	0.2634 (6)	0.0985 (5)	0.0665 (14)
N1	0.0856 (4)	0.2654 (7)	0.1354 (4)	0.0514 (12)
H1B	0.0671	0.3613	0.1810	0.077*
H1C	0.0632	0.1434	0.1568	0.077*
H1D	0.0516	0.2921	0.0697	0.077*
C6	0.4385 (6)	0.2722 (9)	0.1145 (6)	0.0575 (16)
C4	0.2549 (5)	0.1252 (9)	0.0666 (5)	0.0551 (15)
H4A	0.2087	0.0301	0.0274	0.066*
C3	0.2087 (5)	0.2643 (7)	0.1331 (5)	0.0458 (13)
C5	0.3688 (5)	0.1288 (10)	0.0589 (5)	0.0608 (17)
H5A	0.4001	0.0332	0.0156	0.073*
C1	0.3918 (6)	0.4084 (9)	0.1824 (6)	0.0640 (18)
H1A	0.4380	0.5023	0.2225	0.077*
C8	0.7385 (6)	0.3844 (11)	0.1062 (6)	0.073 (2)
H8A	0.7906	0.4880	0.1355	0.109*
H8B	0.7315	0.3907	0.0289	0.109*
H8C	0.7665	0.2519	0.1296	0.109*
C2	0.2756 (6)	0.4042 (10)	0.1902 (5)	0.0630 (17)
H2A	0.2438	0.4972	0.2346	0.076*
C7	0.6253 (6)	0.4193 (11)	0.1441 (6)	0.075 (2)
H7A	0.6314	0.4131	0.2221	0.089*
H7B	0.5965	0.5534	0.1213	0.089*

	U11	U22	U33	U12	U13	U23
Br1	0.0600 (4)	0.0431 (4)	0.0460 (4)	−0.0070 (3)	0.0119 (3)	−0.0002 (2)
O1	0.046 (2)	0.064 (3)	0.090 (4)	−0.0075 (19)	0.010 (2)	−0.017 (2)
N1	0.043 (3)	0.061 (3)	0.050 (3)	−0.007 (2)	0.009 (2)	0.000 (2)
C6	0.050 (4)	0.056 (4)	0.068 (4)	−0.004 (3)	0.012 (3)	−0.002 (3)
C4	0.045 (3)	0.055 (3)	0.067 (4)	−0.011 (3)	0.016 (3)	−0.019 (3)
C3	0.045 (3)	0.044 (3)	0.049 (3)	0.002 (2)	0.010 (2)	−0.002 (2)
C5	0.048 (4)	0.059 (4)	0.077 (5)	−0.007 (3)	0.016 (3)	−0.025 (3)
C1	0.052 (4)	0.064 (4)	0.077 (5)	−0.010 (3)	0.009 (3)	−0.027 (3)
C8	0.053 (4)	0.083 (5)	0.082 (5)	−0.014 (4)	0.006 (4)	0.013 (4)
C2	0.061 (4)	0.061 (4)	0.068 (4)	0.002 (3)	0.011 (3)	−0.021 (3)
C7	0.060 (5)	0.074 (5)	0.088 (6)	−0.021 (4)	−0.001 (4)	0.002 (4)

O1—C6	1.363 (9)	C3—C2	1.358 (8)
O1—C7	1.426 (7)	C5—H5A	0.9300
N1—C3	1.461 (8)	C1—C2	1.390 (9)
N1—H1B	0.8900	C1—H1A	0.9300
N1—H1C	0.8900	C8—C7	1.489 (9)
N1—H1D	0.8900	C8—H8A	0.9600
C6—C5	1.382 (9)	C8—H8B	0.9600
C6—C1	1.385 (9)	C8—H8C	0.9600
C4—C5	1.362 (8)	C2—H2A	0.9300
C4—C3	1.384 (7)	C7—H7A	0.9700
C4—H4A	0.9300	C7—H7B	0.9700
C6—O1—C7	118.9 (5)	C6—C1—C2	119.8 (6)
C3—N1—H1B	109.5	C6—C1—H1A	120.1
C3—N1—H1C	109.5	C2—C1—H1A	120.1
H1B—N1—H1C	109.5	C7—C8—H8A	109.5
C3—N1—H1D	109.5	C7—C8—H8B	109.5
H1B—N1—H1D	109.5	H8A—C8—H8B	109.5
H1C—N1—H1D	109.5	C7—C8—H8C	109.5
O1—C6—C5	115.7 (6)	H8A—C8—H8C	109.5
O1—C6—C1	125.3 (6)	H8B—C8—H8C	109.5
C5—C6—C1	119.0 (6)	C3—C2—C1	120.0 (6)
C5—C4—C3	119.5 (5)	C3—C2—H2A	120.0
C5—C4—H4A	120.3	C1—C2—H2A	120.0
C3—C4—H4A	120.3	O1—C7—C8	107.8 (6)
C2—C3—C4	120.6 (6)	O1—C7—H7A	110.1
C2—C3—N1	120.8 (5)	C8—C7—H7A	110.1
C4—C3—N1	118.5 (5)	O1—C7—H7B	110.1
C4—C5—C6	121.1 (6)	C8—C7—H7B	110.1
C4—C5—H5A	119.5	H7A—C7—H7B	108.5
C6—C5—H5A	119.5
C7—O1—C6—C5	173.5 (6)	O1—C6—C1—C2	178.9 (7)
C7—O1—C6—C1	−7.8 (10)	C5—C6—C1—C2	−2.6 (11)
C5—C4—C3—C2	0.3 (10)	C4—C3—C2—C1	−0.1 (10)
C5—C4—C3—N1	176.6 (6)	N1—C3—C2—C1	−176.3 (6)
C3—C4—C5—C6	−1.6 (10)	C6—C1—C2—C3	1.3 (11)
O1—C6—C5—C4	−178.6 (6)	C6—O1—C7—C8	−174.7 (6)
C1—C6—C5—C4	2.7 (11)

Cg1 is the centroid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Br1	0.89	2.78	3.368 (4)	125
N1—H1B···Br1i	0.89	2.76	3.324 (5)	122
N1—H1C···Br1ii	0.89	2.56	3.375 (4)	153
N1—H1D···Br1iii	0.89	2.51	3.348 (5)	158
C7—H7A···Cg1iv	0.97	3.01	3.674 (8)	127
C8—H8B···Cg1v	0.96	2.96	3.677 (8)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Br1	0.89	2.78	3.368 (4)	125
N1—H1B⋯Br1i	0.89	2.76	3.324 (5)	122
N1—H1C⋯Br1ii	0.89	2.56	3.375 (4)	153
N1—H1D⋯Br1iii	0.89	2.51	3.348 (5)	158
C7—H7A⋯Cg1iv	0.97	3.01	3.674 (8)	127
C8—H8B⋯Cg1v	0.96	2.96	3.677 (8)	132

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