3,4-Dimethyl-anilinium chloride monohydrate.

The crystal structure of the title compound, C(8)H(12)N(+)·Cl(-)·H(2)O, consists of hydro-phobic layers of dimethyl-anilinium cations parallel to the bc plane alternated by hydro-philic layers of chloride anions and water mol-ecules. The layers are linked by N-H⋯O and N-H⋯Cl hydrogen bonds involving the ammonium groups of the cations. The cohesion of the ionic structure is further stabilized by O-H⋯Cl hydrogen-bonding inter-actions.

Related literature

For crystal structures containing the dimethyl­anilinium cation, see: Bouacida (2008 ▶); Singh et al. (2002 ▶); Singh et al. (1995a ▶,b ▶); Linden et al. (1995 ▶); Fábry et al. (2001 ▶, 2002 ▶). For the crystal structures of related protonated amines, see: Bouacida et al. (2005a ▶,b ▶,c ▶, 2006 ▶, 2007 ▶); Benslimane et al. (2007 ▶); Rademeyer (2004a ▶,b ▶).

Experimental

Crystal data

C8H12N+·Cl−·H2O

M = 175.65

Orthorhombic,

a = 18.230 (18) Å

b = 6.7854 (14) Å

c = 7.916 (2) Å

V = 979.2 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 295 K

0.1 × 0.04 × 0.02 mm

Data collection

Enraf–Nonius KappaCCD diffractometer

Absorption correction: none

10115 measured reflections

2181 independent reflections

1403 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.109

S = 1.15

2181 reflections

109 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 976 Friedel pairs

Flack parameter: 0.01 (11)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶); and SCALEPACK program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg et al., 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006072/rz2296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006072/rz2296Isup2.hkl

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

C8H12N+·Cl−·H2O	F(000) = 376
Mr = 175.65	Dx = 1.191 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 9401 reflections
a = 18.230 (18) Å	θ = 3.7–27.5°
b = 6.7854 (14) Å	µ = 0.34 mm−1
c = 7.916 (2) Å	T = 295 K
V = 979.2 (10) Å3	Stalk, white
Z = 4	0.1 × 0.04 × 0.02 mm

Enraf–Nonius KappaCCD diffractometer	Rint = 0.078
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 3.7°
10115 measured reflections	h = −23→23
2181 independent reflections	k = −8→8
1403 reflections with I > 2σ(I)	l = −10→9

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0307P)2 + 0.3106P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.059	(Δ/σ)max < 0.001
wR(F2) = 0.109	Δρmax = 0.20 e Å−3
S = 1.15	Δρmin = −0.21 e Å−3
2181 reflections	Absolute structure: Flack (1983), 976 Friedel pairs
109 parameters	Flack parameter: 0.01 (11)
1 restraint

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

	x	y	z	Uiso*/Ueq
N1	0.06494 (14)	0.5513 (4)	0.2268 (4)	0.0433 (10)
C1	0.14146 (17)	0.4809 (5)	0.2159 (4)	0.0395 (11)
C2	0.1556 (2)	0.3036 (6)	0.1426 (5)	0.0447 (12)
C3	0.22856 (19)	0.2362 (5)	0.1269 (4)	0.0430 (13)
C4	0.28449 (18)	0.3555 (5)	0.1893 (5)	0.0444 (11)
C5	0.2677 (2)	0.5332 (6)	0.2641 (5)	0.0517 (14)
C6	0.1959 (2)	0.5966 (5)	0.2776 (5)	0.0467 (12)
C7	0.2432 (3)	0.0413 (6)	0.0454 (6)	0.0670 (19)
C8	0.3636 (2)	0.2894 (7)	0.1744 (7)	0.0693 (16)
O1W	0.0447 (3)	0.8297 (5)	0.4757 (4)	0.0818 (13)
Cl1	0.04002 (5)	0.77733 (12)	0.87943 (11)	0.0507 (3)
H1A	0.06154	0.64300	0.30678	0.0650*
H1B	0.03559	0.45076	0.25217	0.0650*
H1C	0.05158	0.60253	0.12795	0.0650*
H2	0.11712	0.22655	0.10264	0.0534*
H5	0.30525	0.61175	0.30623	0.0620*
H6	0.18505	0.71675	0.32834	0.0559*
H7A	0.27619	0.05896	−0.04794	0.1007*
H7B	0.19792	−0.01381	0.00532	0.1007*
H7C	0.26488	−0.04643	0.12637	0.1007*
H8A	0.39537	0.39319	0.21227	0.1038*
H8B	0.37436	0.25867	0.05870	0.1038*
H8C	0.37112	0.17444	0.24296	0.1038*
H1W	0.046 (3)	0.824 (9)	0.576 (7)	0.1038*
H2W	0.022 (3)	0.927 (8)	0.447 (7)	0.1038*

	U11	U22	U33	U12	U13	U23
N1	0.0455 (16)	0.0461 (17)	0.0383 (18)	0.0025 (13)	−0.0007 (14)	0.0048 (14)
C1	0.0384 (18)	0.044 (2)	0.0361 (19)	0.0062 (16)	0.0041 (17)	0.0089 (18)
C2	0.051 (2)	0.043 (2)	0.040 (2)	−0.0076 (17)	0.0008 (19)	0.0070 (18)
C3	0.060 (3)	0.039 (2)	0.0300 (17)	0.0022 (17)	0.004 (2)	0.0089 (17)
C4	0.047 (2)	0.051 (2)	0.0353 (19)	0.0013 (17)	0.0013 (19)	0.010 (2)
C5	0.052 (2)	0.051 (2)	0.052 (3)	−0.0056 (18)	−0.006 (2)	0.002 (2)
C6	0.049 (2)	0.045 (2)	0.046 (2)	0.0024 (18)	−0.0018 (19)	0.0034 (18)
C7	0.097 (4)	0.048 (3)	0.056 (3)	0.012 (2)	0.008 (3)	0.000 (2)
C8	0.052 (2)	0.082 (3)	0.074 (3)	0.009 (2)	0.007 (3)	0.011 (3)
O1W	0.127 (3)	0.066 (2)	0.0523 (18)	0.037 (2)	−0.004 (2)	−0.0054 (17)
Cl1	0.0555 (4)	0.0492 (5)	0.0475 (4)	0.0042 (4)	−0.0028 (6)	0.0044 (6)

O1W—H2W	0.81 (5)	C4—C5	1.378 (6)
O1W—H1W	0.80 (6)	C5—C6	1.382 (5)
N1—C1	1.477 (4)	C2—H2	0.9300
N1—H1A	0.8900	C5—H5	0.9300
N1—H1C	0.8900	C6—H6	0.9300
N1—H1B	0.8900	C7—H7B	0.9600
C1—C2	1.360 (5)	C7—H7C	0.9600
C1—C6	1.356 (5)	C7—H7A	0.9600
C2—C3	1.412 (5)	C8—H8C	0.9600
C3—C7	1.496 (6)	C8—H8A	0.9600
C3—C4	1.392 (5)	C8—H8B	0.9600
C4—C8	1.515 (5)
Cl1···O1W	3.217 (5)	C8···H7A	2.8400
Cl1···N1i	3.181 (4)	H1A···H2W	2.3400
Cl1···N1ii	3.177 (4)	H1A···O1W	1.8700
Cl1···O1Wiii	3.174 (5)	H1A···H6	2.3100
Cl1···H1W	2.43 (6)	H1A···H1W	2.4800
Cl1···H1Ci	2.3100	H1B···Cl1vi	2.3000
Cl1···H1Bii	2.3000	H1B···H2	2.4300
Cl1···H5iv	3.0900	H1C···Cl1vii	2.3100
Cl1···H2Wiii	2.36 (5)	H1W···H1A	2.4800
O1W···Cl1v	3.174 (5)	H1W···Cl1	2.43 (6)
O1W···N1	2.754 (5)	H2···H1B	2.4300
O1W···Cl1	3.217 (5)	H2···H7B	2.3300
O1W···H1A	1.8700	H2W···Cl1v	2.36 (5)
O1W···H6	2.9100	H2W···H1A	2.3400
N1···Cl1vi	3.177 (4)	H5···H8A	2.3300
N1···Cl1vii	3.181 (4)	H5···Cl1viii	3.0900
N1···O1W	2.754 (5)	H6···H1A	2.3100
C3···C5viii	3.509 (6)	H6···C7xi	3.0800
C3···C4viii	3.565 (6)	H6···O1W	2.9100
C4···C3iv	3.565 (6)	H7A···H8B	2.4000
C4···C7iv	3.570 (7)	H7A···C8	2.8400
C5···C3iv	3.509 (6)	H7A···C3viii	2.8400
C7···C4viii	3.570 (7)	H7A···C4viii	3.1000
C3···H7Aiv	2.8400	H7B···H2	2.3300
C4···H7Aiv	3.1000	H7C···C8	2.9300
C5···H7Cix	3.0500	H7C···C5xii	3.0500
C6···H7Cix	2.9800	H7C···C6xii	2.9800
C7···H8B	2.8100	H8A···H5	2.3300
C7···H8C	2.9500	H8B···C7	2.8100
C7···H6x	3.0800	H8B···H7A	2.4000
C8···H7C	2.9300	H8C···C7	2.9500
H1W—O1W—H2W	110 (6)	C3—C2—H2	120.00
H1A—N1—H1B	109.00	C1—C2—H2	120.00
H1A—N1—H1C	109.00	C4—C5—H5	120.00
C1—N1—H1B	109.00	C6—C5—H5	119.00
C1—N1—H1C	109.00	C5—C6—H6	121.00
H1B—N1—H1C	109.00	C1—C6—H6	120.00
C1—N1—H1A	109.00	C3—C7—H7A	109.00
N1—C1—C2	119.3 (3)	C3—C7—H7B	109.00
C2—C1—C6	121.8 (3)	H7A—C7—H7B	109.00
N1—C1—C6	118.9 (3)	H7A—C7—H7C	109.00
C1—C2—C3	120.2 (3)	C3—C7—H7C	110.00
C2—C3—C4	118.1 (3)	H7B—C7—H7C	109.00
C2—C3—C7	119.5 (4)	C4—C8—H8B	109.00
C4—C3—C7	122.4 (3)	C4—C8—H8C	109.00
C3—C4—C8	119.8 (3)	C4—C8—H8A	109.00
C5—C4—C8	120.3 (3)	H8A—C8—H8C	109.00
C3—C4—C5	119.9 (3)	H8B—C8—H8C	109.00
C4—C5—C6	121.1 (3)	H8A—C8—H8B	110.00
C1—C6—C5	119.0 (3)
N1—C1—C2—C3	178.3 (3)	C2—C3—C4—C8	−179.7 (4)
C6—C1—C2—C3	−0.9 (6)	C7—C3—C4—C5	−179.6 (4)
N1—C1—C6—C5	−178.5 (3)	C7—C3—C4—C8	0.5 (6)
C2—C1—C6—C5	0.6 (6)	C3—C4—C5—C6	−0.4 (6)
C1—C2—C3—C4	0.4 (5)	C8—C4—C5—C6	179.5 (4)
C1—C2—C3—C7	−179.8 (4)	C4—C5—C6—C1	0.0 (6)
C2—C3—C4—C5	0.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1W	0.8900	1.8700	2.754 (5)	174.00
N1—H1B···Cl1vi	0.8900	2.3000	3.177 (4)	167.00
N1—H1C···Cl1vii	0.8900	2.3100	3.181 (4)	167.00
O1W—H1W···Cl1	0.80 (6)	2.43 (6)	3.217 (5)	174 (7)
O1W—H2W···Cl1v	0.81 (5)	2.36 (5)	3.174 (5)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1W	0.89	1.87	2.754 (5)	174
N1—H1B⋯Cl1i	0.89	2.30	3.177 (4)	167
N1—H1C⋯Cl1ii	0.89	2.31	3.181 (4)	167
O1W—H1W⋯Cl1	0.80 (6)	2.43 (6)	3.217 (5)	174 (7)
O1W—H2W⋯Cl1iii	0.81 (5)	2.36 (5)	3.174 (5)	176 (2)

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