3-Chloro-2-methyl-anilinium dihydrogenphosphate.

The structure of the title compound, C(7)H(9)ClN(+)·H(2)PO(4) (-), contains inorganic layers built by (H(2)PO(4))(-) anions and which are parallel to the ab planes around z = . 3-Chloro-2-methyl-anilinium cations are anchored between the inorganic layers through N-H⋯O hydrogen bonds. Electrostatic and van der Waals inter-actions, as well as hydrogen bonds, maintain the structural cohesion.

Related literature

For related literature, see: Adams (1977 ▶); Blessing (1986 ▶); Chtioui & Jouini (2004 ▶); Desiraju (1989 ▶, 1995 ▶); Hebert (1978 ▶); Oueslati & Ben Nasr (2006 ▶).

Experimental

Crystal data

C7H9ClN+·H2PO4 −

M = 239.59

Monoclinic,

a = 16.942 (6) Å

b = 8.272 (2) Å

c = 7.979 (7) Å

β = 100.11 (5)°

V = 1100.8 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 292 K

0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: none

3304 measured reflections

1932 independent reflections

1736 reflections with I > 2σ(I)

R int = 0.027

2 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.08

1932 reflections

132 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.38 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 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001700/dn2313sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001700/dn2313Isup2.hkl

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

C7H9ClN+·H2PO4–	F000 = 496
Mr = 239.59	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.942 (6) Å	θ = 8–11º
b = 8.272 (2) Å	µ = 0.48 mm−1
c = 7.979 (7) Å	T = 292 K
β = 100.11 (5)º	Prism, colorless
V = 1100.8 (11) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Enraf–Nonius TurboCAD4 diffractometer	Rint = 0.027
Radiation source: fine-focus sealed tube	θmax = 25.0º
Monochromator: graphite	θmin = 2.4º
T = 292 K	h = −10→20
non–profiled ω scans	k = −9→0
Absorption correction: none	l = −9→9
3304 measured reflections	2 standard reflections
1932 independent reflections	every 120 min
1736 reflections with I > 2σ(I)	intensity decay: 1%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.6257P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122	(Δ/σ)max = 0.011
S = 1.08	Δρmax = 0.36 e Å−3
1932 reflections	Δρmin = −0.38 e Å−3
132 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)
Secondary atom site location: difference Fourier map

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
P1	0.43820 (3)	0.46630 (6)	0.23711 (6)	0.0298 (2)
O1	0.39492 (10)	0.5342 (2)	0.3800 (2)	0.0503 (5)
H1	0.4278	0.5477	0.4674	0.075*
O2	0.44438 (12)	0.60754 (19)	0.11002 (19)	0.0462 (5)
H2	0.4562	0.6914	0.1634	0.069*
O3	0.52069 (9)	0.40766 (18)	0.31601 (17)	0.0346 (4)
O4	0.38537 (10)	0.34256 (19)	0.13619 (18)	0.0408 (4)
Cl1	0.95781 (6)	0.6138 (3)	0.2672 (2)	0.1564 (8)
N1	0.65051 (11)	0.5738 (2)	0.1985 (2)	0.0342 (4)
H1A	0.6130	0.5026	0.2138	0.051*
H1B	0.6435	0.6023	0.0893	0.051*
H1C	0.6468	0.6609	0.2621	0.051*
C1	0.72967 (14)	0.5010 (3)	0.2480 (3)	0.0392 (5)
C2	0.79647 (15)	0.5918 (4)	0.2317 (3)	0.0524 (7)
C3	0.86992 (18)	0.5110 (6)	0.2839 (5)	0.0784 (10)
C4	0.8752 (2)	0.3579 (6)	0.3475 (6)	0.0954 (13)
H4	0.9252	0.3102	0.3805	0.114*
C5	0.8074 (2)	0.2742 (5)	0.3631 (6)	0.0875 (12)
H5	0.8110	0.1701	0.4078	0.105*
C6	0.73348 (18)	0.3460 (3)	0.3116 (4)	0.0617 (8)
H6	0.6867	0.2900	0.3199	0.074*
C7	0.7899 (2)	0.7623 (5)	0.1667 (5)	0.0807 (11)
H7A	0.7432	0.8123	0.1966	0.121*
H7B	0.7856	0.7619	0.0451	0.121*
H7C	0.8368	0.8219	0.2168	0.121*

	U11	U22	U33	U12	U13	U23
P1	0.0413 (4)	0.0243 (3)	0.0221 (3)	−0.0007 (2)	0.0007 (2)	−0.00082 (18)
O1	0.0444 (9)	0.0731 (13)	0.0312 (9)	0.0113 (9)	0.0005 (7)	−0.0125 (8)
O2	0.0800 (12)	0.0248 (8)	0.0297 (8)	−0.0045 (8)	−0.0020 (8)	0.0030 (6)
O3	0.0448 (9)	0.0301 (8)	0.0276 (7)	0.0037 (6)	0.0023 (6)	−0.0020 (6)
O4	0.0548 (9)	0.0355 (9)	0.0285 (7)	−0.0119 (7)	−0.0026 (7)	0.0004 (6)
Cl1	0.0485 (6)	0.2330 (19)	0.1867 (15)	−0.0312 (8)	0.0178 (7)	0.0464 (14)
N1	0.0391 (10)	0.0352 (9)	0.0272 (8)	−0.0005 (8)	0.0029 (7)	−0.0024 (7)
C1	0.0416 (12)	0.0449 (12)	0.0305 (11)	0.0019 (10)	0.0048 (9)	−0.0055 (9)
C2	0.0451 (14)	0.0698 (18)	0.0419 (13)	−0.0073 (13)	0.0061 (11)	−0.0006 (13)
C3	0.0414 (15)	0.118 (3)	0.075 (2)	−0.0034 (18)	0.0094 (15)	0.001 (2)
C4	0.060 (2)	0.113 (3)	0.109 (3)	0.035 (2)	0.005 (2)	0.011 (3)
C5	0.072 (2)	0.066 (2)	0.120 (3)	0.0236 (18)	0.005 (2)	0.017 (2)
C6	0.0540 (15)	0.0458 (15)	0.083 (2)	0.0069 (13)	0.0066 (14)	0.0043 (14)
C7	0.075 (2)	0.085 (2)	0.079 (2)	−0.0277 (19)	0.0063 (18)	0.0238 (19)

P1—O4	1.4980 (16)	C1—C2	1.383 (4)
P1—O3	1.5087 (17)	C2—C3	1.409 (4)
P1—O2	1.5626 (17)	C2—C7	1.500 (5)
P1—O1	1.5641 (19)	C3—C4	1.361 (6)
O1—H1	0.8200	C4—C5	1.365 (6)
O2—H2	0.8200	C4—H4	0.9300
Cl1—C3	1.740 (4)	C5—C6	1.382 (4)
N1—C1	1.460 (3)	C5—H5	0.9300
N1—H1A	0.8900	C6—H6	0.9300
N1—H1B	0.8900	C7—H7A	0.9600
N1—H1C	0.8900	C7—H7B	0.9600
C1—C6	1.377 (4)	C7—H7C	0.9600
O4—P1—O3	115.27 (9)	C3—C2—C7	123.8 (3)
O4—P1—O2	105.31 (10)	C4—C3—C2	123.3 (3)
O3—P1—O2	110.39 (10)	C4—C3—Cl1	118.8 (3)
O4—P1—O1	108.96 (11)	C2—C3—Cl1	117.9 (3)
O3—P1—O1	109.25 (10)	C3—C4—C5	120.3 (3)
O2—P1—O1	107.34 (11)	C3—C4—H4	119.9
P1—O1—H1	109.5	C5—C4—H4	119.9
P1—O2—H2	109.5	C4—C5—C6	119.2 (4)
C1—N1—H1A	109.5	C4—C5—H5	120.4
C1—N1—H1B	109.5	C6—C5—H5	120.4
H1A—N1—H1B	109.5	C1—C6—C5	119.4 (3)
C1—N1—H1C	109.5	C1—C6—H6	120.3
H1A—N1—H1C	109.5	C5—C6—H6	120.3
H1B—N1—H1C	109.5	C2—C7—H7A	109.5
C6—C1—C2	123.7 (3)	C2—C7—H7B	109.5
C6—C1—N1	117.7 (2)	H7A—C7—H7B	109.5
C2—C1—N1	118.6 (2)	C2—C7—H7C	109.5
C1—C2—C3	114.2 (3)	H7A—C7—H7C	109.5
C1—C2—C7	122.1 (3)	H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.82	1.83	2.634 (3)	166
O2—H2···O3ii	0.82	1.83	2.596 (2)	154
N1—H1A···O3	0.89	2.04	2.886 (3)	158
N1—H1B···O4iii	0.89	1.84	2.722 (3)	172
N1—H1C···O4ii	0.89	1.84	2.708 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82	1.83	2.634 (3)	166
O2—H2⋯O3ii	0.82	1.83	2.596 (2)	154
N1—H1A⋯O3	0.89	2.04	2.886 (3)	158
N1—H1B⋯O4iii	0.89	1.84	2.722 (3)	172
N1—H1C⋯O4ii	0.89	1.84	2.708 (3)	166

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