4-Bromo-2,6-dimethyl-anilinium bromide monohydrate.

In the title compound, C(8)H(11)BrN(+)·Br(-)·H(2)O, a network of N-H⋯O, N-H⋯Br and O-H⋯Br hydrogen bonds helps to consolidate the crystal packing.

Related literature

For related literature, see: Hirao & Fukuhara (1998 ▶); MacDiamid et al. (1998 ▶); Wakayama (1998 ▶); Wang et al. (2002 ▶).

Experimental

Crystal data

C8H11BrN+·Br−·H2O

M = 298.99

Monoclinic,

a = 7.1630 (14) Å

b = 18.649 (4) Å

c = 8.4770 (17) Å

β = 109.98 (3)°

V = 1064.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 7.58 mm−1

T = 293 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.152, T max = 0.221

2077 measured reflections

2077 independent reflections

1346 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.096

S = 0.97

2077 reflections

120 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.52 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064896/lw2046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064896/lw2046Isup2.hkl

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

C8H11BrN+·Br–·H2O	F000 = 584
Mr = 298.99	Dx = 1.866 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.1630 (14) Å	θ = 9–13º
b = 18.649 (4) Å	µ = 7.58 mm−1
c = 8.4770 (17) Å	T = 293 (2) K
β = 109.98 (3)º	Block, colorless
V = 1064.2 (4) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0000
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 2.2º
T = 293(2) K	h = −8→8
ω/2θ scans	k = 0→22
Absorption correction: ψ scan(North et al., 1968)	l = 0→10
Tmin = 0.152, Tmax = 0.221	3 standard reflections
2077 measured reflections	every 200 reflections
2077 independent reflections	intensity decay: none
1346 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0437P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2077 reflections	Δρmax = 0.42 e Å−3
120 parameters	Δρmin = −0.52 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.93285 (11)	0.38204 (3)	0.77315 (8)	0.0490 (2)
Br2	0.47862 (10)	0.69675 (3)	0.95867 (8)	0.0407 (2)
C1	0.7335 (8)	0.5937 (3)	0.4804 (7)	0.0276 (13)
C2	0.6858 (8)	0.5297 (3)	0.3931 (7)	0.0310 (13)
C3	0.7483 (8)	0.4664 (3)	0.4828 (7)	0.0346 (14)
H3	0.7195	0.4224	0.4282	0.041*
C4	0.8528 (9)	0.4691 (3)	0.6521 (7)	0.0368 (15)
C5	0.9007 (8)	0.5334 (3)	0.7373 (7)	0.0330 (14)
H5	0.9728	0.5338	0.8517	0.040*
C6	0.8412 (8)	0.5966 (3)	0.6519 (6)	0.0298 (13)
C7	0.5756 (9)	0.5250 (3)	0.2060 (6)	0.0410 (16)
H7A	0.4469	0.5466	0.1799	0.062*
H7B	0.5605	0.4755	0.1723	0.062*
H7C	0.6494	0.5497	0.1472	0.062*
C8	0.8945 (9)	0.6665 (3)	0.7470 (7)	0.0420 (16)
H8A	0.7752	0.6910	0.7436	0.063*
H8B	0.9682	0.6960	0.6964	0.063*
H8C	0.9739	0.6569	0.8616	0.063*
N1	0.6621 (7)	0.6625 (2)	0.3935 (5)	0.0336 (12)
H1A	0.6039	0.6545	0.2841	0.050*
H1B	0.7645	0.6921	0.4099	0.050*
H1C	0.5749	0.6822	0.4343	0.050*
O1	0.4192 (8)	0.7175 (3)	0.5552 (6)	0.0494 (12)
H1	0.442 (3)	0.710 (4)	0.657 (3)	0.05 (2)*
H2	0.306 (3)	0.736 (4)	0.518 (3)	0.09 (3)*

	U11	U22	U33	U12	U13	U23
Br1	0.0650 (5)	0.0365 (4)	0.0427 (4)	0.0084 (4)	0.0147 (3)	0.0129 (3)
Br2	0.0445 (4)	0.0422 (4)	0.0337 (3)	0.0045 (3)	0.0113 (3)	0.0053 (3)
C1	0.030 (3)	0.028 (3)	0.027 (3)	−0.001 (2)	0.012 (3)	0.000 (2)
C2	0.035 (3)	0.033 (3)	0.027 (3)	−0.001 (3)	0.014 (3)	−0.006 (3)
C3	0.040 (4)	0.027 (3)	0.034 (3)	−0.005 (3)	0.011 (3)	−0.005 (3)
C4	0.038 (4)	0.039 (4)	0.033 (3)	−0.001 (3)	0.011 (3)	0.010 (3)
C5	0.037 (4)	0.034 (3)	0.024 (3)	0.002 (3)	0.006 (3)	0.002 (3)
C6	0.031 (3)	0.034 (3)	0.023 (3)	−0.001 (3)	0.008 (3)	−0.006 (2)
C7	0.054 (4)	0.038 (4)	0.025 (3)	−0.006 (3)	0.006 (3)	−0.009 (3)
C8	0.045 (4)	0.048 (4)	0.027 (3)	0.003 (3)	0.003 (3)	−0.004 (3)
N1	0.037 (3)	0.032 (3)	0.033 (3)	0.002 (2)	0.012 (2)	0.000 (2)
O1	0.052 (3)	0.069 (4)	0.026 (3)	0.019 (3)	0.012 (2)	0.005 (2)

Br1—C4	1.901 (6)	C7—H7A	0.9600
C1—C2	1.384 (7)	C7—H7B	0.9600
C1—C6	1.395 (7)	C7—H7C	0.9600
C1—N1	1.481 (6)	C8—H8A	0.9600
C2—C3	1.393 (7)	C8—H8B	0.9600
C2—C7	1.513 (7)	C8—H8C	0.9600
C3—C4	1.374 (7)	N1—H1A	0.8900
C3—H3	0.9300	N1—H1B	0.8900
C4—C5	1.381 (8)	N1—H1C	0.8900
C5—C6	1.373 (7)	O1—H1	0.84 (2)
C5—H5	0.9300	O1—H2	0.84 (2)
C6—C8	1.511 (7)
C2—C1—C6	122.6 (5)	C2—C7—H7B	109.5
C2—C1—N1	120.0 (5)	H7A—C7—H7B	109.5
C6—C1—N1	117.3 (5)	C2—C7—H7C	109.5
C1—C2—C3	117.6 (5)	H7A—C7—H7C	109.5
C1—C2—C7	123.8 (5)	H7B—C7—H7C	109.5
C3—C2—C7	118.5 (5)	C6—C8—H8A	109.5
C4—C3—C2	119.9 (5)	C6—C8—H8B	109.5
C4—C3—H3	120.1	H8A—C8—H8B	109.5
C2—C3—H3	120.1	C6—C8—H8C	109.5
C3—C4—C5	121.8 (5)	H8A—C8—H8C	109.5
C3—C4—Br1	119.3 (5)	H8B—C8—H8C	109.5
C5—C4—Br1	118.9 (4)	C1—N1—H1A	109.5
C6—C5—C4	119.5 (5)	C1—N1—H1B	109.5
C6—C5—H5	120.2	H1A—N1—H1B	109.5
C4—C5—H5	120.2	C1—N1—H1C	109.5
C5—C6—C1	118.5 (5)	H1A—N1—H1C	109.5
C5—C6—C8	118.9 (5)	H1B—N1—H1C	109.5
C1—C6—C8	122.6 (5)	H1—O1—H2	106 (3)
C2—C7—H7A	109.5
C6—C1—C2—C3	0.4 (8)	C3—C4—C5—C6	0.7 (9)
N1—C1—C2—C3	−176.9 (5)	Br1—C4—C5—C6	−179.0 (4)
C6—C1—C2—C7	−177.7 (5)	C4—C5—C6—C1	0.0 (8)
N1—C1—C2—C7	5.0 (8)	C4—C5—C6—C8	179.9 (5)
C1—C2—C3—C4	0.2 (9)	C2—C1—C6—C5	−0.6 (8)
C7—C2—C3—C4	178.5 (5)	N1—C1—C6—C5	176.8 (5)
C2—C3—C4—C5	−0.8 (9)	C2—C1—C6—C8	179.5 (6)
C2—C3—C4—Br1	178.9 (4)	N1—C1—C6—C8	−3.1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2···Br2i	0.84 (2)	2.56 (3)	3.380 (5)	169 (3)
O1—H1···Br2	0.84 (2)	2.50 (2)	3.322 (5)	174 (3)
N1—H1C···O1	0.89	1.87	2.754 (6)	170
N1—H1B···Br2ii	0.89	2.53	3.388 (5)	163
N1—H1A···Br2iii	0.89	2.71	3.523 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H2⋯Br2i	0.84 (2)	2.56 (3)	3.380 (5)	169 (3)
O1—H1⋯Br2	0.84 (2)	2.50 (2)	3.322 (5)	174 (3)
N1—H1C⋯O1	0.89	1.87	2.754 (6)	170
N1—H1B⋯Br2ii	0.89	2.53	3.388 (5)	163
N1—H1A⋯Br2iii	0.89	2.71	3.523 (4)	153

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