3-Methyl-anilinium nitrate.

In the title compound, C(7)H(10)N(+)·NO(3) (-), the 3-methyl-anilinium cations inter-act with the nitrate anions through strong bifurcated N(+)-H⋯(O,O) hydrogen bonds, forming a two-dimensional hydrogen-bonded network.

Related literature

For related structures, see: Benali-Cherif et al. (2007 ▶, 2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H10N+·NO3 −

M = 170.17

Orthorhombic,

a = 10.6599 (14) Å

b = 9.7800 (13) Å

c = 16.401 (2) Å

V = 1709.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.40 × 0.32 × 0.05 mm

Data collection

Bruker (Siemens) P4 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.968, T max = 0.988

8520 measured reflections

1659 independent reflections

1211 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.135

S = 1.06

1659 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020738/kj2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020738/kj2146Isup2.hkl

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

C7H10N+·NO3−	F(000) = 720
Mr = 170.17	Dx = 1.322 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3320 reflections
a = 10.6599 (14) Å	θ = 2.5–26.0°
b = 9.7800 (13) Å	µ = 0.11 mm−1
c = 16.401 (2) Å	T = 293 K
V = 1709.9 (4) Å3	Plate, colourless
Z = 8	0.40 × 0.32 × 0.05 mm

Bruker (Siemens) P4 diffractometer	1659 independent reflections
Radiation source: fine-focus sealed tube	1211 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→7
Tmin = 0.968, Tmax = 0.988	k = −9→11
8520 measured reflections	l = −18→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0693P)2 + 0.2901P] where P = (Fo2 + 2Fc2)/3
1659 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.14 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
N2	0.86066 (14)	0.20637 (15)	0.24233 (8)	0.0590 (4)
C4	0.62873 (17)	0.1314 (2)	0.08553 (12)	0.0704 (5)
H4	0.6324	0.1346	0.1421	0.084*
O2	0.95202 (13)	0.13478 (15)	0.22538 (9)	0.0824 (5)
C2	0.67695 (17)	0.01475 (19)	−0.03889 (11)	0.0659 (5)
H2	0.7116	−0.0593	−0.0665	0.079*
C6	0.57062 (16)	0.23133 (16)	−0.04117 (10)	0.0573 (4)
H6	0.5344	0.3018	−0.0711	0.069*
C5	0.57263 (16)	0.23767 (18)	0.04363 (11)	0.0619 (5)
C3	0.67905 (19)	0.0215 (2)	0.04542 (12)	0.0774 (6)
H3	0.7150	−0.0494	0.0751	0.093*
C7	0.5124 (3)	0.3551 (2)	0.08774 (13)	0.0914 (7)
H7A	0.4233	0.3413	0.0899	0.137*
H7B	0.5303	0.4387	0.0594	0.137*
H7C	0.5452	0.3603	0.1422	0.137*
O3	0.77282 (13)	0.15739 (14)	0.28406 (8)	0.0733 (4)
O1	0.85544 (14)	0.32743 (14)	0.22016 (8)	0.0765 (4)
N1	0.61546 (14)	0.11602 (14)	−0.17012 (8)	0.0608 (4)
H1A	0.5376	0.1350	−0.1862	0.091*
H1B	0.6366	0.0328	−0.1872	0.091*
H1C	0.6681	0.1772	−0.1911	0.091*
C1	0.62205 (14)	0.12107 (16)	−0.08055 (10)	0.0516 (4)

	U11	U22	U33	U12	U13	U23
N2	0.0751 (10)	0.0567 (8)	0.0453 (7)	−0.0010 (7)	−0.0051 (7)	0.0024 (6)
C4	0.0682 (12)	0.0909 (14)	0.0520 (10)	−0.0142 (10)	−0.0053 (8)	0.0093 (9)
O2	0.0812 (10)	0.0760 (9)	0.0899 (11)	0.0165 (7)	0.0129 (7)	0.0099 (7)
C2	0.0653 (11)	0.0612 (10)	0.0712 (11)	0.0056 (8)	−0.0008 (9)	0.0071 (9)
C6	0.0678 (10)	0.0511 (9)	0.0531 (10)	−0.0049 (8)	0.0013 (7)	0.0044 (7)
C5	0.0663 (11)	0.0669 (11)	0.0524 (10)	−0.0152 (9)	0.0062 (8)	−0.0010 (8)
C3	0.0746 (12)	0.0840 (14)	0.0735 (12)	0.0043 (10)	−0.0102 (10)	0.0241 (11)
C7	0.1199 (18)	0.0888 (14)	0.0655 (12)	−0.0031 (13)	0.0233 (12)	−0.0117 (11)
O3	0.0808 (9)	0.0699 (8)	0.0692 (8)	−0.0048 (7)	0.0138 (7)	0.0074 (6)
O1	0.0983 (10)	0.0568 (8)	0.0746 (9)	0.0046 (7)	0.0019 (7)	0.0138 (6)
N1	0.0742 (10)	0.0545 (8)	0.0537 (8)	−0.0009 (7)	0.0008 (7)	−0.0042 (6)
C1	0.0550 (9)	0.0499 (9)	0.0501 (9)	−0.0075 (7)	−0.0011 (7)	0.0005 (7)

N2—O2	1.2312 (19)	C6—H6	0.9300
N2—O1	1.2398 (19)	C5—C7	1.501 (3)
N2—O3	1.2550 (18)	C3—H3	0.9300
C4—C3	1.370 (3)	C7—H7A	0.9600
C4—C5	1.382 (3)	C7—H7B	0.9600
C4—H4	0.9300	C7—H7C	0.9600
C2—C1	1.375 (2)	N1—C1	1.472 (2)
C2—C3	1.385 (3)	N1—H1A	0.8900
C2—H2	0.9300	N1—H1B	0.8900
C6—C1	1.371 (2)	N1—H1C	0.8900
C6—C5	1.392 (2)
O2—N2—O1	120.82 (16)	C2—C3—H3	119.7
O2—N2—O3	119.76 (15)	C5—C7—H7A	109.5
O1—N2—O3	119.40 (16)	C5—C7—H7B	109.5
C3—C4—C5	121.40 (18)	H7A—C7—H7B	109.5
C3—C4—H4	119.3	C5—C7—H7C	109.5
C5—C4—H4	119.3	H7A—C7—H7C	109.5
C1—C2—C3	117.87 (17)	H7B—C7—H7C	109.5
C1—C2—H2	121.1	C1—N1—H1A	109.5
C3—C2—H2	121.1	C1—N1—H1B	109.5
C1—C6—C5	119.96 (16)	H1A—N1—H1B	109.5
C1—C6—H6	120.0	C1—N1—H1C	109.5
C5—C6—H6	120.0	H1A—N1—H1C	109.5
C4—C5—C6	118.03 (17)	H1B—N1—H1C	109.5
C4—C5—C7	121.37 (18)	C6—C1—C2	122.05 (16)
C6—C5—C7	120.59 (17)	C6—C1—N1	118.52 (14)
C4—C3—C2	120.68 (18)	C2—C1—N1	119.41 (15)
C4—C3—H3	119.7
C3—C4—C5—C6	−1.2 (3)	C1—C2—C3—C4	−0.5 (3)
C3—C4—C5—C7	177.24 (19)	C5—C6—C1—C2	−0.2 (2)
C1—C6—C5—C4	0.8 (2)	C5—C6—C1—N1	178.47 (14)
C1—C6—C5—C7	−177.68 (17)	C3—C2—C1—C6	0.1 (3)
C5—C4—C3—C2	1.1 (3)	C3—C2—C1—N1	−178.60 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.89	2.05	2.943 (2)	178
N1—H1A···O2i	0.89	2.51	3.130 (2)	127
N1—H1B···O3ii	0.89	2.15	3.0221 (19)	167
N1—H1B···O2ii	0.89	2.37	3.078 (2)	136
N1—H1C···O3iii	0.89	2.01	2.879 (2)	166
N1—H1C···O1iii	0.89	2.47	3.176 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.89	2.05	2.943 (2)	178
N1—H1A⋯O2i	0.89	2.51	3.130 (2)	127
N1—H1B⋯O3ii	0.89	2.15	3.0221 (19)	167
N1—H1B⋯O2ii	0.89	2.37	3.078 (2)	136
N1—H1C⋯O3iii	0.89	2.01	2.879 (2)	166
N1—H1C⋯O1iii	0.89	2.47	3.176 (2)	137

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