2,6-Dimethyl-anilinium chloride monohydrate.

In the title hydrated mol-ecular salt, C(8)H(12)N(+)·Cl(-)·H(2)O, the component species inter-act by way of N-H⋯O, N-H⋯Cl and O-H⋯Cl hydrogen bonds, resulting in a three-dimensional network.

Related literature

For related structures, see: Abid et al. (2007 ▶); Mrad et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H12N+·Cl−·H2O

M = 175.65

Monoclinic,

a = 8.676 (3) Å

b = 14.144 (3) Å

c = 7.913 (6) Å

β = 101.88 (5)°

V = 950.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 (2) K

0.20 × 0.13 × 0.10 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: none

3722 measured reflections

2244 independent reflections

1827 reflections with I > 2σ(I)

R int = 0.033

2 standard reflections frequency: 120 min intensity decay: 5%

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.04

2244 reflections

156 parameters

H-atom parameters not refined

Δρmax = 0.17 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039159/hb2860sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039159/hb2860Isup2.hkl

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

C8H12N+·Cl–·H2O	F000 = 376
Mr = 175.65	Dx = 1.228 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.676 (3) Å	θ = 9.2–10.8º
b = 14.144 (3) Å	µ = 0.35 mm−1
c = 7.913 (6) Å	T = 293 (2) K
β = 101.88 (5)º	Block, colourless
V = 950.2 (8) Å3	0.20 × 0.13 × 0.10 mm
Z = 4

Enraf–Nonius TurboCAD-4 diffractometer	θmax = 28.0º
Monochromator: graphite	θmin = 2.8º
T = 293 K	h = −5→11
Non–profiled ω scans	k = −18→0
Absorption correction: none	l = −10→10
3722 measured reflections	2 standard reflections
2244 independent reflections	every 120 min
1827 reflections with I > 2σ(I)	intensity decay: 5%
Rint = 0.033

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters not refined
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0408P)2 + 0.1063P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2244 reflections	Δρmax = 0.17 e Å−3
156 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
H8	0.3326 (19)	0.0879 (11)	0.050 (2)	0.048 (4)*
H7	0.3721 (19)	0.1013 (11)	0.233 (2)	0.045 (4)*
H5	−0.159 (2)	0.2065 (13)	0.033 (2)	0.058 (4)*
H6	0.3494 (19)	0.0085 (13)	0.161 (2)	0.053 (4)*
H3	−0.121 (2)	−0.0291 (12)	0.318 (2)	0.055 (4)*
H13	0.171 (2)	0.2037 (14)	−0.109 (2)	0.066 (5)*
H11	0.265 (2)	−0.0493 (14)	0.427 (3)	0.070 (6)*
H17	0.056 (2)	0.2698 (15)	−0.066 (2)	0.073 (5)*
H2	0.488 (3)	0.2297 (19)	0.405 (3)	0.083 (7)*
H4	−0.278 (2)	0.0943 (13)	0.191 (2)	0.067 (5)*
H1	0.472 (3)	0.1562 (17)	0.518 (3)	0.090 (7)*
H10	0.215 (2)	−0.1099 (13)	0.268 (2)	0.062 (5)*
H9	0.124 (2)	−0.1045 (14)	0.406 (3)	0.071 (6)*
H12	0.215 (3)	0.2560 (15)	0.065 (3)	0.087 (7)*
N1	0.31170 (12)	0.06739 (8)	0.14878 (14)	0.0353 (2)
C7	0.1308 (2)	0.22609 (11)	−0.0155 (2)	0.0510 (3)
C8	0.1800 (2)	−0.07172 (12)	0.3454 (2)	0.0512 (3)
C1	0.14475 (13)	0.07516 (8)	0.15925 (14)	0.0322 (2)
C6	0.05793 (14)	0.15126 (9)	0.07822 (14)	0.0359 (3)
C5	−0.09996 (16)	0.15637 (10)	0.08975 (17)	0.0435 (3)
C2	0.08245 (14)	0.00745 (9)	0.25368 (15)	0.0367 (3)
C3	−0.07586 (16)	0.01607 (10)	0.26089 (17)	0.0445 (3)
C4	−0.16594 (15)	0.08936 (11)	0.18003 (18)	0.0466 (3)
O1	0.48995 (14)	0.16863 (9)	0.41224 (15)	0.0580 (3)
Cl1	0.45854 (4)	0.11499 (2)	0.81025 (4)	0.04716 (12)

	U11	U22	U33	U12	U13	U23
N1	0.0319 (5)	0.0398 (5)	0.0364 (5)	0.0052 (4)	0.0125 (4)	0.0025 (4)
C7	0.0553 (9)	0.0467 (7)	0.0546 (8)	0.0130 (7)	0.0200 (7)	0.0119 (6)
C8	0.0580 (9)	0.0523 (8)	0.0493 (8)	0.0100 (7)	0.0253 (7)	0.0123 (7)
C1	0.0282 (5)	0.0398 (6)	0.0296 (5)	0.0024 (4)	0.0083 (4)	−0.0058 (4)
C6	0.0370 (6)	0.0389 (6)	0.0318 (5)	0.0050 (5)	0.0074 (4)	−0.0049 (4)
C5	0.0356 (6)	0.0504 (7)	0.0428 (6)	0.0102 (6)	0.0039 (5)	−0.0091 (6)
C2	0.0378 (6)	0.0416 (6)	0.0328 (5)	0.0007 (5)	0.0121 (4)	−0.0047 (5)
C3	0.0402 (7)	0.0524 (8)	0.0452 (6)	−0.0068 (6)	0.0186 (5)	−0.0077 (6)
C4	0.0298 (6)	0.0602 (8)	0.0508 (7)	−0.0003 (5)	0.0107 (5)	−0.0145 (6)
O1	0.0654 (7)	0.0543 (7)	0.0509 (6)	0.0072 (5)	0.0039 (5)	−0.0041 (5)
Cl1	0.04621 (19)	0.04719 (19)	0.0534 (2)	0.01013 (14)	0.02267 (14)	0.00643 (13)

N1—C1	1.4718 (16)	C1—C2	1.3907 (17)
N1—H8	0.883 (18)	C1—C6	1.3921 (17)
N1—H7	0.896 (17)	C6—C5	1.3934 (18)
N1—H6	0.893 (18)	C5—C4	1.380 (2)
C7—C6	1.504 (2)	C5—H5	0.935 (18)
C7—H13	0.93 (2)	C2—C3	1.3917 (18)
C7—H17	0.92 (2)	C3—C4	1.374 (2)
C7—H12	0.96 (2)	C3—H3	0.918 (18)
C8—C2	1.498 (2)	C4—H4	1.00 (2)
C8—H11	0.93 (2)	O1—H2	0.87 (3)
C8—H10	0.92 (2)	O1—H1	0.90 (3)
C8—H9	0.88 (2)
C1—N1—H8	114.1 (10)	C2—C1—N1	118.34 (11)
C1—N1—H7	110.5 (10)	C6—C1—N1	118.50 (11)
H8—N1—H7	106.5 (15)	C1—C6—C5	117.13 (12)
C1—N1—H6	114.0 (11)	C1—C6—C7	121.91 (11)
H8—N1—H6	105.3 (15)	C5—C6—C7	120.95 (12)
H7—N1—H6	105.9 (14)	C4—C5—C6	121.09 (13)
C6—C7—H13	114.5 (12)	C4—C5—H5	121.5 (11)
C6—C7—H17	110.9 (13)	C6—C5—H5	117.4 (11)
H13—C7—H17	103.3 (16)	C1—C2—C3	117.24 (12)
C6—C7—H12	108.9 (13)	C1—C2—C8	122.14 (12)
H13—C7—H12	108.2 (18)	C3—C2—C8	120.62 (12)
H17—C7—H12	111.0 (18)	C4—C3—C2	121.22 (13)
C2—C8—H11	111.7 (12)	C4—C3—H3	119.6 (11)
C2—C8—H10	110.5 (11)	C2—C3—H3	119.2 (11)
H11—C8—H10	109.9 (17)	C3—C4—C5	120.15 (12)
C2—C8—H9	109.7 (13)	C3—C4—H4	118.9 (11)
H11—C8—H9	104.3 (18)	C5—C4—H4	120.9 (11)
H10—C8—H9	110.5 (17)	H2—O1—H1	105 (2)
C2—C1—C6	123.14 (11)
C2—C1—C6—C5	−2.12 (17)	N1—C1—C2—C3	−179.68 (10)
N1—C1—C6—C5	179.69 (10)	C6—C1—C2—C8	−177.60 (12)
C2—C1—C6—C7	176.85 (12)	N1—C1—C2—C8	0.60 (18)
N1—C1—C6—C7	−1.34 (17)	C1—C2—C3—C4	−0.96 (18)
C1—C6—C5—C4	0.94 (17)	C8—C2—C3—C4	178.78 (14)
C7—C6—C5—C4	−178.04 (13)	C2—C3—C4—C5	−0.1 (2)
C6—C1—C2—C3	2.13 (17)	C6—C5—C4—C3	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1	0.90 (2)	2.41 (2)	3.305 (3)	173 (2)
O1—H2···Cl1i	0.87 (3)	2.32 (3)	3.163 (3)	165 (2)
N1—H6···Cl1ii	0.893 (18)	2.392 (18)	3.235 (3)	157.5 (15)
N1—H7···O1	0.896 (16)	1.835 (16)	2.731 (3)	177.3 (17)
N1—H8···Cl1iii	0.883 (16)	2.414 (16)	3.265 (3)	162.8 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1	0.90 (2)	2.41 (2)	3.305 (3)	173 (2)
O1—H2⋯Cl1i	0.87 (3)	2.32 (3)	3.163 (3)	165 (2)
N1—H6⋯Cl1ii	0.893 (18)	2.392 (18)	3.235 (3)	157.5 (15)
N1—H7⋯O1	0.896 (16)	1.835 (16)	2.731 (3)	177.3 (17)
N1—H8⋯Cl1iii	0.883 (16)	2.414 (16)	3.265 (3)	162.8 (15)

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