2,5-Dimethyl-anilinium nitrate.

In the title salt, C(8)H(12)N(+)·NO(3) (-), all non-H atoms of the cation lie on mirror planes. The nitrate counteranion has m symmetry and acts as a hydrogen-bond acceptor of N-H⋯O hydrogen bonds, connecting the cations and anions into layers running parallel to the ab plane.

Related literature

Inorganic–organic hybrid materials display a great variety of structural topologies, see: Xiao et al. (2005 ▶). For comparative geometrical data in structures containing the same organic groups, see: Smirani & Rzaigui (2009 ▶); Souissi et al. (2009 ▶).

Experimental

Crystal data

C8H12N+·NO3 −

M = 184.20

Orthorhombic,

a = 6.762 (3) Å

b = 7.942 (3) Å

c = 17.137 (5) Å

V = 920.4 (6) Å3

Z = 4

Ag Kα radiation

μ = 0.06 mm−1

T = 293 K

0.50 × 0.45 × 0.40 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: none

4249 measured reflections

2365 independent reflections

822 reflections with I > 2σ(I)

R int = 0.056

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

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.156

S = 0.92

2365 reflections

86 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027718/hg2534sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027718/hg2534Isup2.hkl

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

C8H12N+·NO3−	F(000) = 392
Mr = 184.20	Dx = 1.329 Mg m−3
Orthorhombic, Pmcn	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -P 2n 2a	Cell parameters from 25 reflections
a = 6.762 (3) Å	θ = 9.0–10.5°
b = 7.942 (3) Å	µ = 0.06 mm−1
c = 17.137 (5) Å	T = 293 K
V = 920.4 (6) Å3	Block, colorless
Z = 4	0.50 × 0.45 × 0.40 mm

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.056
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.2°
graphite	h = −8→11
Non–profiled ω scans	k = 0→13
4249 measured reflections	l = 0→28
2365 independent reflections	2 standard reflections every 120 min
822 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: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0632P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
2365 reflections	Δρmax = 0.20 e Å−3
86 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.166 (13)

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	Occ. (<1)
H1A	0.135 (3)	0.372 (3)	0.2106 (10)	0.086 (7)*
H2A	0.2500	0.209 (4)	0.2009 (14)	0.068 (8)*
C6	0.2500	0.4899 (2)	0.07043 (11)	0.0405 (5)
N1	0.2500	0.3185 (3)	0.18968 (10)	0.0427 (4)
C1	0.2500	0.3315 (2)	0.10432 (10)	0.0349 (4)
C2	0.2500	0.1853 (3)	0.06089 (12)	0.0432 (5)
H2	0.2500	0.0817	0.0862	0.052*
C5	0.2500	0.4935 (3)	−0.01074 (13)	0.0507 (6)
H5	0.2500	0.5971	−0.0361	0.061*
C3	0.2500	0.1907 (3)	−0.01996 (12)	0.0452 (5)
C4	0.2500	0.3481 (3)	−0.05467 (12)	0.0499 (6)
H4	0.2500	0.3559	−0.1088	0.060*
C7	0.2500	0.6490 (3)	0.11749 (13)	0.0550 (6)
H7A	0.3818	0.6722	0.1353	0.083*	0.50
H7B	0.1638	0.6361	0.1616	0.083*	0.50
H7C	0.2044	0.7406	0.0857	0.083*	0.50
C8	0.2500	0.0315 (3)	−0.06851 (15)	0.0685 (7)
H8A	0.1164	0.0016	−0.0814	0.103*	0.50
H8B	0.3098	−0.0582	−0.0393	0.103*	0.50
H8C	0.3238	0.0501	−0.1156	0.103*	0.50
N2	0.2500	0.9146 (2)	0.26822 (9)	0.0425 (4)
O1	0.09203 (15)	0.98204 (16)	0.24632 (7)	0.0604 (4)
O2	0.2500	0.7900 (2)	0.30947 (10)	0.0672 (5)

	U11	U22	U33	U12	U13	U23
C6	0.0373 (10)	0.0419 (11)	0.0424 (10)	0.000	0.000	0.0018 (9)
N1	0.0501 (10)	0.0419 (11)	0.0360 (9)	0.000	0.000	0.0017 (8)
C1	0.0330 (9)	0.0399 (10)	0.0318 (9)	0.000	0.000	0.0012 (8)
C2	0.0458 (11)	0.0363 (11)	0.0476 (11)	0.000	0.000	0.0020 (9)
C5	0.0620 (15)	0.0427 (11)	0.0474 (12)	0.000	0.000	0.0089 (10)
C3	0.0411 (11)	0.0505 (13)	0.0440 (11)	0.000	0.000	−0.0092 (10)
C4	0.0506 (12)	0.0630 (15)	0.0361 (10)	0.000	0.000	0.0019 (10)
C7	0.0642 (14)	0.0425 (12)	0.0584 (13)	0.000	0.000	−0.0034 (11)
C8	0.0796 (19)	0.0673 (16)	0.0586 (14)	0.000	0.000	−0.0229 (13)
N2	0.0476 (10)	0.0425 (10)	0.0374 (9)	0.000	0.000	−0.0025 (8)
O1	0.0435 (6)	0.0667 (9)	0.0708 (7)	0.0079 (5)	0.0007 (6)	0.0138 (6)
O2	0.0868 (13)	0.0550 (10)	0.0598 (10)	0.000	0.000	0.0189 (9)

C6—C1	1.385 (3)	C3—C8	1.514 (3)
C6—C5	1.391 (3)	C4—H4	0.9300
C6—C7	1.499 (3)	C7—H7A	0.9600
N1—C1	1.467 (2)	C7—H7B	0.9600
N1—H1A	0.95 (2)	C7—H7C	0.9600
N1—H2A	0.89 (3)	C8—H8A	0.9600
C1—C2	1.379 (3)	C8—H8B	0.9600
C2—C3	1.386 (3)	C8—H8C	0.9600
C2—H2	0.9300	N2—O2	1.216 (2)
C5—C4	1.379 (3)	N2—O1	1.2525 (14)
C5—H5	0.9300	N2—O1i	1.2525 (14)
C3—C4	1.384 (3)
C1—C6—C5	115.98 (18)	C5—C4—C3	121.46 (19)
C1—C6—C7	122.67 (18)	C5—C4—H4	119.3
C5—C6—C7	121.35 (19)	C3—C4—H4	119.3
C1—N1—H1A	110.2 (11)	C6—C7—H7A	109.5
C1—N1—H2A	106.6 (16)	C6—C7—H7B	109.5
H1A—N1—H2A	110.6 (14)	H7A—C7—H7B	109.5
C2—C1—C6	122.56 (17)	C6—C7—H7C	109.5
C2—C1—N1	118.60 (18)	H7A—C7—H7C	109.5
C6—C1—N1	118.84 (17)	H7B—C7—H7C	109.5
C1—C2—C3	120.9 (2)	C3—C8—H8A	109.5
C1—C2—H2	119.6	C3—C8—H8B	109.5
C3—C2—H2	119.6	H8A—C8—H8B	109.5
C4—C5—C6	121.9 (2)	C3—C8—H8C	109.5
C4—C5—H5	119.1	H8A—C8—H8C	109.5
C6—C5—H5	119.1	H8B—C8—H8C	109.5
C4—C3—C2	117.2 (2)	O2—N2—O1	121.48 (9)
C4—C3—C8	121.2 (2)	O2—N2—O1i	121.48 (9)
C2—C3—C8	121.6 (2)	O1—N2—O1i	117.04 (17)
C5—C6—C1—C2	0.0	C7—C6—C5—C4	180.0
C7—C6—C1—C2	180.0	C1—C2—C3—C4	0.0
C5—C6—C1—N1	180.0	C1—C2—C3—C8	180.0
C7—C6—C1—N1	0.0	C6—C5—C4—C3	0.0
C6—C1—C2—C3	0.0	C2—C3—C4—C5	0.0
N1—C1—C2—C3	180.0	C8—C3—C4—C5	180.0
C1—C6—C5—C4	0.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.95 (2)	1.92 (3)	2.870 (2)	179 (3)
N1—H2A···O1iii	0.89 (3)	2.24 (3)	3.037 (3)	150 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.95 (2)	1.92 (3)	2.870 (2)	179 (3)
N1—H2A⋯O1ii	0.89 (3)	2.24 (3)	3.037 (3)	149.7 (8)

Symmetry codes: (i) ; (ii) .