2,3-Dimethyl-anilinium chloride monohydrate.

The crystal structure of the title salt, C(8)H(12)N(+)·Cl(-)·H(2)O, consists of discrete organic cations, chloride anions and water mol-ecules which are connected by N-H⋯Cl, N-H⋯O and O-H⋯Cl hydrogen bonds. These inter-actions lead to the formation of layers lying parallel to the ab plane.

Related literature

For related structures, see: Dai & Chen (2010 ▶); Abid et al. (2007 ▶). For hydrogen bonds, see: Steiner (2002 ▶); Jayaraman et al. (2002 ▶).

Experimental

Crystal data

C8H12N+·Cl−·H2O

M = 175.65

Orthorhombic,

a = 7.4910 (15) Å

b = 7.5031 (15) Å

c = 17.430 (4) Å

V = 979.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 298 K

0.45 × 0.4 × 0.2 mm

Data collection

Stoe IPDS 2T diffractometer

4645 measured reflections

2616 independent reflections

2095 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.03

2616 reflections

122 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), with 1088 Friedel pairs

Flack parameter: 0.13 (9)

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811043765/bt5667sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043765/bt5667Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043765/bt5667Isup3.cml

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

C8H12N+·Cl−·H2O	F(000) = 376.0
Mr = 175.65	Dx = 1.191 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2616 reflections
a = 7.4910 (15) Å	θ = 2.3–29.2°
b = 7.5031 (15) Å	µ = 0.34 mm−1
c = 17.430 (4) Å	T = 298 K
V = 979.7 (4) Å3	Block, colourless
Z = 4	0.45 × 0.4 × 0.2 mm

Stoe IPDS 2T diffractometer	2095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 29.2°, θmin = 2.3°
Detector resolution: 0.15 pixels mm-1	h = −10→8
rotation method scans	k = −10→8
4645 measured reflections	l = −23→20
2616 independent reflections

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.048P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2616 reflections	Δρmax = 0.20 e Å−3
122 parameters	Δρmin = −0.16 e Å−3
2 restraints	Absolute structure: Flack (1983), with 1088 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.13 (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
O1	0.3476 (2)	0.2420 (2)	0.73382 (12)	0.0800 (5)
Cl1	0.76090 (5)	0.33674 (6)	0.75167 (3)	0.06069 (15)
N1	0.1163 (2)	0.4774 (2)	0.67017 (9)	0.0491 (3)
C2	0.2579 (2)	0.5132 (2)	0.54351 (9)	0.0463 (3)
C1	0.1057 (2)	0.4777 (2)	0.58624 (11)	0.0446 (4)
C6	−0.0577 (3)	0.4395 (3)	0.55285 (12)	0.0621 (5)
H6	−0.1572	0.4147	0.5829	0.075*
C3	0.2418 (3)	0.5139 (2)	0.46329 (11)	0.0571 (4)
C7	0.4338 (3)	0.5486 (4)	0.58231 (14)	0.0649 (5)
H7A	0.4885	0.4375	0.5962	0.097*
H7B	0.4144	0.6187	0.6276	0.097*
H7C	0.5109	0.6123	0.5479	0.097*
C5	−0.0691 (3)	0.4392 (4)	0.47360 (14)	0.0780 (7)
H5	−0.1771	0.4134	0.4497	0.094*
C8	0.4007 (4)	0.5513 (4)	0.41222 (15)	0.0825 (8)
H8A	0.3627	0.5547	0.3596	0.124*
H8B	0.4880	0.4588	0.4187	0.124*
H8C	0.4522	0.6640	0.4259	0.124*
C4	0.0778 (4)	0.4766 (3)	0.43060 (13)	0.0709 (6)
H4	0.0676	0.4771	0.3774	0.085*
H1C	0.021 (3)	0.451 (3)	0.6876 (13)	0.060 (6)*
H1A	0.147 (3)	0.591 (3)	0.6905 (11)	0.052 (5)*
H1B	0.198 (3)	0.400 (4)	0.6859 (13)	0.079 (8)*
H1W	0.331 (4)	0.134 (2)	0.7337 (15)	0.088 (9)*
H2W	0.456 (3)	0.257 (6)	0.7323 (19)	0.131 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0518 (8)	0.0643 (9)	0.1239 (15)	0.0014 (7)	−0.0103 (9)	0.0200 (10)
Cl1	0.0443 (2)	0.0566 (2)	0.0812 (3)	−0.00063 (17)	0.0040 (3)	0.0132 (2)
N1	0.0374 (7)	0.0507 (8)	0.0594 (9)	−0.0041 (6)	0.0022 (6)	−0.0012 (7)
C2	0.0419 (8)	0.0394 (7)	0.0576 (9)	−0.0017 (8)	−0.0004 (8)	0.0003 (6)
C1	0.0398 (7)	0.0380 (8)	0.0561 (9)	−0.0005 (7)	−0.0032 (7)	−0.0018 (7)
C6	0.0409 (8)	0.0708 (12)	0.0747 (12)	−0.0062 (8)	−0.0069 (8)	−0.0036 (10)
C3	0.0653 (11)	0.0487 (9)	0.0572 (10)	−0.0009 (11)	−0.0005 (10)	−0.0004 (7)
C7	0.0406 (9)	0.0825 (14)	0.0716 (12)	−0.0129 (9)	0.0035 (9)	−0.0003 (11)
C5	0.0602 (12)	0.0918 (17)	0.0822 (15)	−0.0073 (12)	−0.0260 (11)	−0.0093 (13)
C8	0.0918 (18)	0.0905 (18)	0.0652 (13)	−0.0146 (15)	0.0186 (13)	0.0035 (14)
C4	0.0820 (15)	0.0731 (14)	0.0576 (12)	−0.0029 (12)	−0.0156 (10)	−0.0011 (10)

O1—H1W	0.820 (17)	C3—C4	1.383 (3)
O1—H2W	0.820 (18)	C3—C8	1.512 (3)
N1—C1	1.465 (2)	C7—H7A	0.9600
N1—H1C	0.80 (2)	C7—H7B	0.9600
N1—H1A	0.95 (2)	C7—H7C	0.9600
N1—H1B	0.89 (3)	C5—C4	1.361 (3)
C2—C1	1.388 (2)	C5—H5	0.9300
C2—C3	1.404 (2)	C8—H8A	0.9600
C2—C7	1.505 (3)	C8—H8B	0.9600
C1—C6	1.385 (2)	C8—H8C	0.9600
C6—C5	1.384 (3)	C4—H4	0.9300
C6—H6	0.9300
H1W—O1—H2W	107 (4)	C2—C7—H7A	109.5
C1—N1—H1C	109.4 (16)	C2—C7—H7B	109.5
C1—N1—H1A	112.5 (11)	H7A—C7—H7B	109.5
H1C—N1—H1A	107 (2)	C2—C7—H7C	109.5
C1—N1—H1B	110.2 (15)	H7A—C7—H7C	109.5
H1C—N1—H1B	110 (2)	H7B—C7—H7C	109.5
H1A—N1—H1B	108 (2)	C4—C5—C6	120.0 (2)
C1—C2—C3	117.70 (16)	C4—C5—H5	120.0
C1—C2—C7	120.81 (15)	C6—C5—H5	120.0
C3—C2—C7	121.49 (16)	C3—C8—H8A	109.5
C6—C1—C2	122.69 (18)	C3—C8—H8B	109.5
C6—C1—N1	117.83 (17)	H8A—C8—H8B	109.5
C2—C1—N1	119.47 (15)	C3—C8—H8C	109.5
C5—C6—C1	118.3 (2)	H8A—C8—H8C	109.5
C5—C6—H6	120.8	H8B—C8—H8C	109.5
C1—C6—H6	120.8	C5—C4—C3	122.2 (2)
C4—C3—C2	119.08 (19)	C5—C4—H4	118.9
C4—C3—C8	119.6 (2)	C3—C4—H4	118.9
C2—C3—C8	121.29 (19)
C3—C2—C1—C6	1.5 (3)	C7—C2—C3—C4	178.6 (2)
C7—C2—C1—C6	−178.15 (18)	C1—C2—C3—C8	−180.0 (2)
C3—C2—C1—N1	−179.41 (16)	C7—C2—C3—C8	−0.3 (3)
C7—C2—C1—N1	0.9 (3)	C1—C6—C5—C4	−0.3 (4)
C2—C1—C6—C5	−0.8 (3)	C6—C5—C4—C3	0.7 (4)
N1—C1—C6—C5	−179.9 (2)	C2—C3—C4—C5	0.0 (4)
C1—C2—C3—C4	−1.1 (3)	C8—C3—C4—C5	178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.95 (2)	2.21 (2)	3.1581 (17)	172.6 (17)
N1—H1B···O1	0.89 (3)	1.83 (3)	2.711 (2)	170 (2)
N1—H1C···Cl1ii	0.80 (2)	2.41 (2)	3.1964 (17)	171 (2)
O1—H1W···Cl1iii	0.82 (2)	2.35 (2)	3.1578 (19)	169 (3)
O1—H2W···Cl1	0.82 (2)	2.39 (2)	3.1920 (18)	168 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.95 (2)	2.21 (2)	3.1581 (17)	172.6 (17)
N1—H1B⋯O1	0.89 (3)	1.83 (3)	2.711 (2)	170 (2)
N1—H1C⋯Cl1ii	0.80 (2)	2.41 (2)	3.1964 (17)	171 (2)
O1—H1W⋯Cl1iii	0.82 (2)	2.35 (2)	3.1578 (19)	169 (3)
O1—H2W⋯Cl1	0.82 (2)	2.39 (2)	3.1920 (18)	168 (4)

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