4-Methyl-anilinium nitrate.

The asymmetric unit of the title compound, C(7)H(10)N(+)·NO(3) (-), consists of a 4-methyl-anilinium cation protonated at the amino group and a nitrate anion. In the crystal, anions and cations are linked through N-H⋯O and N-H⋯(O,O) hydrogen bonds, buiding a corrugated layer structure parallel to (001).

Related literature

For related structures, see: Benali-Cherif, Kateb et al. (2007 ▶); Benali-Cherif, Allouche et al. (2007 ▶); Benali-Cherif, Boussekine et al. (2007 ▶); Asath Bahadur et al. (2007 ▶). For the bio­logical effects of toluidine exposure in man, see: Kennedy et al. (1984 ▶).

Experimental

Crystal data

C7H10N+·NO3 −

M = 170.17

Monoclinic,

a = 5.6725 (9) Å

b = 8.5507 (8) Å

c = 17.621 (2) Å

β = 98.771 (2)°

V = 844.69 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.2 × 0.15 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

24550 measured reflections

2791 independent reflections

1228 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.125

S = 0.91

2791 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.19 e Å−3

Data collection: KappaCCD (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Pearce et al., 2000 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041488/dn2484sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041488/dn2484Isup2.hkl

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

C7H10N+·NO3−	F(000) = 360
Mr = 170.17	Dx = 1.338 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 24550 reflections
a = 5.6725 (9) Å	θ = 2.7–31.5°
b = 8.5507 (8) Å	µ = 0.11 mm−1
c = 17.621 (2) Å	T = 100 K
β = 98.771 (2)°	Prism, brown
V = 844.69 (18) Å3	0.2 × 0.15 × 0.1 mm
Z = 4

Nonius KappaCCD diffractometer	1228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
graphite	θmax = 31.5°, θmin = 2.7°
ω–θ scans	h = −8→5
24550 measured reflections	k = −12→12
2791 independent reflections	l = −25→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3
2791 reflections	(Δ/σ)max = 0.001
111 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.4327 (3)	0.15225 (17)	0.90563 (9)	0.0212 (4)
C2	0.2258 (3)	0.23416 (18)	0.91199 (10)	0.0251 (4)
H2	0.0979	0.2342	0.8721	0.030*
C3	0.2140 (3)	0.31609 (19)	0.97933 (10)	0.0280 (4)
H3	0.0752	0.3705	0.9843	0.034*
C4	0.4025 (3)	0.31936 (17)	1.03941 (10)	0.0261 (4)
C5	0.6101 (3)	0.23714 (18)	1.03075 (9)	0.0265 (4)
H5	0.7396	0.2386	1.0701	0.032*
C6	0.6249 (3)	0.15283 (17)	0.96364 (9)	0.0239 (4)
H6	0.7629	0.0979	0.9583	0.029*
C7	0.3867 (4)	0.4121 (2)	1.11156 (10)	0.0347 (5)
H7A	0.4333	0.5184	1.1044	0.052*
H7B	0.4911	0.3670	1.1539	0.052*
H7C	0.2257	0.4099	1.1222	0.052*
N1	0.4466 (2)	0.06544 (14)	0.83447 (7)	0.0236 (3)
H1A	0.5927	0.0263	0.8361	0.035*
H1B	0.4147	0.1296	0.7945	0.035*
H1C	0.3409	−0.0122	0.8298	0.035*
N2	0.5736 (3)	0.35591 (15)	0.71667 (8)	0.0249 (3)
O1	0.7537 (2)	0.31274 (13)	0.75970 (7)	0.0311 (3)
O2	0.5852 (2)	0.45260 (13)	0.66347 (7)	0.0339 (3)
O3	0.3676 (2)	0.30432 (13)	0.72457 (7)	0.0295 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0282 (9)	0.0117 (7)	0.0233 (9)	−0.0041 (7)	0.0031 (7)	0.0006 (6)
C2	0.0245 (9)	0.0180 (8)	0.0312 (10)	−0.0018 (7)	−0.0012 (7)	0.0002 (7)
C3	0.0290 (10)	0.0182 (8)	0.0373 (11)	0.0018 (7)	0.0066 (8)	−0.0007 (7)
C4	0.0381 (10)	0.0130 (7)	0.0285 (10)	−0.0053 (7)	0.0095 (8)	0.0016 (7)
C5	0.0333 (10)	0.0207 (8)	0.0241 (10)	−0.0042 (7)	0.0001 (8)	0.0029 (7)
C6	0.0261 (9)	0.0167 (8)	0.0291 (10)	0.0000 (7)	0.0051 (7)	0.0036 (7)
C7	0.0524 (12)	0.0222 (8)	0.0305 (11)	−0.0023 (8)	0.0097 (9)	−0.0023 (7)
N1	0.0277 (8)	0.0166 (6)	0.0260 (8)	−0.0014 (6)	0.0022 (6)	0.0002 (6)
N2	0.0290 (8)	0.0169 (7)	0.0279 (8)	0.0011 (6)	0.0018 (7)	−0.0022 (6)
O1	0.0276 (7)	0.0305 (7)	0.0326 (7)	0.0051 (6)	−0.0038 (6)	0.0023 (6)
O2	0.0354 (7)	0.0252 (6)	0.0397 (8)	−0.0020 (6)	0.0008 (6)	0.0139 (6)
O3	0.0277 (7)	0.0267 (6)	0.0338 (7)	−0.0015 (5)	0.0041 (5)	0.0052 (5)

C1—C6	1.376 (2)	C6—H6	0.9300
C1—C2	1.386 (2)	C7—H7A	0.9600
C1—N1	1.470 (2)	C7—H7B	0.9600
C2—C3	1.388 (2)	C7—H7C	0.9600
C2—H2	0.9300	N1—H1A	0.8900
C3—C4	1.385 (2)	N1—H1B	0.8900
C3—H3	0.9300	N1—H1C	0.8900
C4—C5	1.399 (2)	N2—O1	1.2325 (17)
C4—C7	1.513 (2)	N2—O2	1.2592 (16)
C5—C6	1.398 (2)	N2—O3	1.2759 (17)
C5—H5	0.9300
C6—C1—C2	121.53 (15)	C5—C6—H6	120.4
C6—C1—N1	119.74 (14)	C4—C7—H7A	109.5
C2—C1—N1	118.73 (14)	C4—C7—H7B	109.5
C1—C2—C3	118.41 (16)	H7A—C7—H7B	109.5
C1—C2—H2	120.8	C4—C7—H7C	109.5
C3—C2—H2	120.8	H7A—C7—H7C	109.5
C4—C3—C2	122.09 (16)	H7B—C7—H7C	109.5
C4—C3—H3	119.0	C1—N1—H1A	109.5
C2—C3—H3	119.0	C1—N1—H1B	109.5
C3—C4—C5	118.08 (16)	H1A—N1—H1B	109.5
C3—C4—C7	121.01 (16)	C1—N1—H1C	109.5
C5—C4—C7	120.90 (17)	H1A—N1—H1C	109.5
C6—C5—C4	120.75 (16)	H1B—N1—H1C	109.5
C6—C5—H5	119.6	O1—N2—O2	121.47 (14)
C4—C5—H5	119.6	O1—N2—O3	121.07 (14)
C1—C6—C5	119.14 (16)	O2—N2—O3	117.45 (14)
C1—C6—H6	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3	0.89	1.93	2.8032 (17)	167
N1—H1A···O2i	0.89	1.93	2.8208 (18)	177
N1—H1C···O3ii	0.89	2.11	2.9461 (17)	157
N1—H1C···O2ii	0.89	2.46	3.1726 (18)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O3	0.89	1.93	2.8032 (17)	167
N1—H1A⋯O2i	0.89	1.93	2.8208 (18)	177
N1—H1C⋯O3ii	0.89	2.11	2.9461 (17)	157
N1—H1C⋯O2ii	0.89	2.46	3.1726 (18)	138

Symmetry codes: (i) ; (ii) .