2,5-Dimethyl-anilinium chloride monohydrate.

In the title compound, C(8)H(12)N(+)·Cl(-)·H(2)O, the crystal packing is influenced by O-H⋯Cl, N-H⋯Cl and N-H⋯O hydrogen bonds, resulting in a two-dimensional network propagating parallel to (001).

Related literature

For related literature, see: Aloui et al. (2006 ▶); Masse et al. (1993 ▶); Blessing (1986 ▶).

Experimental

Crystal data

C8H12N+·Cl−·H2O

M = 175.65

Monoclinic,

a = 7.515 (4) Å

b = 7.441 (3) Å

c = 9.019 (2) Å

β = 102.87 (3)°

V = 491.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 293 (2) K

0.50 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: none

2058 measured reflections

1260 independent reflections

1166 reflections with I > 2σ(I)

R int = 0.025

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

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.081

S = 1.10

1260 reflections

111 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), unique data only

Flack parameter: 0.17 (9)

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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041287/hb2876sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041287/hb2876Isup2.hkl

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

C8H12N+·Cl−·H2O	F(000) = 188
Mr = 175.65	Dx = 1.187 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 7.515 (4) Å	θ = 9.0–10.8°
b = 7.441 (3) Å	µ = 0.34 mm−1
c = 9.019 (2) Å	T = 293 K
β = 102.87 (3)°	Plate, colourless
V = 491.7 (4) Å3	0.50 × 0.30 × 0.20 mm
Z = 2

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.025
Radiation source: Enraf Nonius FR590	θmax = 28.0°, θmin = 2.3°
graphite	h = −9→9
non–profiled ω scans	k = 0→9
2058 measured reflections	l = −5→11
1260 independent reflections	2 standard reflections every 120 min
1166 reflections with I > 2σ(I)	intensity decay: 5%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.0061P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1260 reflections	Δρmax = 0.20 e Å−3
111 parameters	Δρmin = −0.13 e Å−3
1 restraint	Absolute structure: Flack (1983), unique data only
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.17 (9)

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
H30	0.343 (5)	0.410 (6)	0.541 (3)	0.068 (9)*
H31	0.467 (5)	0.287 (7)	0.548 (4)	0.101 (13)*
Cl1	0.77059 (6)	0.20498 (11)	0.51544 (5)	0.05039 (16)
C1	0.7901 (2)	0.5395 (3)	1.1684 (2)	0.0384 (4)
N1	0.8345 (2)	0.5589 (3)	1.33479 (17)	0.0417 (4)
H1A	0.7624	0.6418	1.3617	0.062*
H1B	0.9505	0.5923	1.3660	0.062*
H1C	0.8174	0.4543	1.3774	0.062*
C6	0.9259 (3)	0.5724 (3)	1.0904 (2)	0.0431 (4)
H6	1.0405	0.6101	1.1431	0.052*
C2	0.6147 (2)	0.4859 (3)	1.0962 (2)	0.0427 (4)
C5	0.8914 (3)	0.5491 (3)	0.9335 (3)	0.0487 (5)
C3	0.5844 (3)	0.4628 (4)	0.9399 (2)	0.0541 (5)
H3	0.4698	0.4248	0.8873	0.065*
C7	0.4674 (3)	0.4531 (4)	1.1817 (3)	0.0560 (6)
H7A	0.5086	0.3654	1.2599	0.084*
H7B	0.3597	0.4097	1.1128	0.084*
H7C	0.4399	0.5634	1.2271	0.084*
C4	0.7171 (3)	0.4937 (4)	0.8597 (3)	0.0551 (6)
H4	0.6902	0.4773	0.7548	0.066*
O1	0.3659 (3)	0.3043 (4)	0.5526 (3)	0.0783 (6)
C8	1.0363 (4)	0.5817 (4)	0.8458 (3)	0.0682 (7)
H8A	1.1339	0.6502	0.9071	0.102*
H8B	0.9850	0.6472	0.7546	0.102*
H8C	1.0828	0.4687	0.8197	0.102*

	U11	U22	U33	U12	U13	U23
Cl1	0.0441 (2)	0.0462 (2)	0.0622 (3)	0.0054 (3)	0.01468 (18)	0.0086 (3)
C1	0.0394 (9)	0.0301 (8)	0.0461 (9)	−0.0005 (7)	0.0105 (7)	−0.0040 (7)
N1	0.0388 (7)	0.0414 (8)	0.0458 (8)	−0.0036 (7)	0.0115 (6)	−0.0009 (7)
C6	0.0421 (9)	0.0341 (9)	0.0555 (11)	−0.0039 (8)	0.0157 (8)	−0.0023 (9)
C2	0.0378 (8)	0.0371 (9)	0.0541 (11)	−0.0006 (8)	0.0120 (8)	−0.0042 (9)
C5	0.0574 (11)	0.0372 (9)	0.0567 (11)	−0.0024 (9)	0.0237 (9)	−0.0033 (10)
C3	0.0486 (11)	0.0568 (14)	0.0545 (12)	−0.0063 (11)	0.0064 (9)	−0.0123 (11)
C7	0.0400 (10)	0.0655 (16)	0.0649 (14)	−0.0104 (11)	0.0169 (9)	−0.0068 (12)
C4	0.0658 (13)	0.0554 (13)	0.0450 (11)	−0.0011 (12)	0.0143 (9)	−0.0082 (10)
O1	0.0586 (11)	0.0618 (13)	0.1229 (18)	0.0097 (10)	0.0381 (11)	0.0362 (12)
C8	0.0852 (18)	0.0626 (17)	0.0694 (15)	−0.0123 (15)	0.0439 (14)	−0.0039 (14)

C1—C6	1.383 (3)	C3—C4	1.376 (3)
C1—C2	1.393 (3)	C3—H3	0.9300
C1—N1	1.470 (2)	C7—H7A	0.9600
N1—H1A	0.8900	C7—H7B	0.9600
N1—H1B	0.8900	C7—H7C	0.9600
N1—H1C	0.8900	C4—H4	0.9300
C6—C5	1.391 (3)	O1—H30	0.80 (4)
C6—H6	0.9300	O1—H31	0.78 (4)
C2—C3	1.388 (3)	C8—H8A	0.9600
C2—C7	1.503 (3)	C8—H8B	0.9600
C5—C4	1.393 (3)	C8—H8C	0.9600
C5—C8	1.501 (3)
C6—C1—C2	122.80 (19)	C4—C3—H3	118.7
C6—C1—N1	118.46 (17)	C2—C3—H3	118.7
C2—C1—N1	118.73 (18)	C2—C7—H7A	109.5
C1—N1—H1A	109.5	C2—C7—H7B	109.5
C1—N1—H1B	109.5	H7A—C7—H7B	109.5
H1A—N1—H1B	109.5	C2—C7—H7C	109.5
C1—N1—H1C	109.5	H7A—C7—H7C	109.5
H1A—N1—H1C	109.5	H7B—C7—H7C	109.5
H1B—N1—H1C	109.5	C3—C4—C5	120.8 (2)
C1—C6—C5	120.3 (2)	C3—C4—H4	119.6
C1—C6—H6	119.9	C5—C4—H4	119.6
C5—C6—H6	119.9	H30—O1—H31	110 (4)
C3—C2—C1	115.72 (19)	C5—C8—H8A	109.5
C3—C2—C7	121.90 (19)	C5—C8—H8B	109.5
C1—C2—C7	122.38 (19)	H8A—C8—H8B	109.5
C6—C5—C4	117.7 (2)	C5—C8—H8C	109.5
C6—C5—C8	121.6 (2)	H8A—C8—H8C	109.5
C4—C5—C8	120.7 (2)	H8B—C8—H8C	109.5
C4—C3—C2	122.7 (2)
C2—C1—C6—C5	−1.2 (3)	C1—C6—C5—C8	−179.4 (2)
N1—C1—C6—C5	177.61 (19)	C1—C2—C3—C4	−1.2 (4)
C6—C1—C2—C3	1.5 (3)	C7—C2—C3—C4	179.4 (3)
N1—C1—C2—C3	−177.3 (2)	C2—C3—C4—C5	0.6 (4)
C6—C1—C2—C7	−179.1 (2)	C6—C5—C4—C3	−0.2 (4)
N1—C1—C2—C7	2.1 (3)	C8—C5—C4—C3	179.7 (3)
C1—C6—C5—C4	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H30···Cl1i	0.81 (4)	2.37 (4)	3.168 (3)	171 (4)
O1—H31···Cl1	0.78 (4)	2.44 (4)	3.219 (3)	174 (5)
N1—H1A···O1ii	0.89	1.82	2.705 (4)	171
N1—H1B···Cl1iii	0.89	2.29	3.167 (2)	169
N1—H1C···Cl1iv	0.89	2.30	3.189 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H30⋯Cl1i	0.81 (4)	2.37 (4)	3.168 (3)	171 (4)
O1—H31⋯Cl1	0.78 (4)	2.44 (4)	3.219 (3)	174 (5)
N1—H1A⋯O1ii	0.89	1.82	2.705 (4)	171
N1—H1B⋯Cl1iii	0.89	2.29	3.167 (2)	169
N1—H1C⋯Cl1iv	0.89	2.30	3.189 (3)	173

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