4-Methyl-benzyl-ammonium nitrate.

In the title salt, C8H12N(+)·NO3 (-), the N atom of the 4-methyl-benzyl-ammonium cation is displaced by 1.366 (2) Å from the mean plane of the other atoms. In the crystal, the cations are connected to the anions by N-H⋯O and N-H⋯(O,O) hydrogen bonds, generating a layered network parallel to (100). A weak C-H⋯O inter-action also occurs.

Related literature

For related structures, see: Kefi et al. (2011 ▶); Rahmouni et al. (2011 ▶). For a discussion on hydrogen bonding, see: Brown (1976 ▶); Blessing (1986 ▶). For aromatic π–π stacking inter­actions, see: Janiak (2000 ▶). For graph-set notation of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H12N+·NO3 −

M = 184.20

Monoclinic,

a = 15.097 (2) Å

b = 5.8121 (10) Å

c = 10.486 (2) Å

β = 99.75 (2)°

V = 906.8 (3) Å3

Z = 4

Ag Kα radiation

λ = 0.56083 Å

μ = 0.06 mm−1

T = 293 K

0.40 × 0.35 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

6579 measured reflections

4430 independent reflections

2415 reflections with I > 2σ(I)

R int = 0.033

2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.216

S = 0.96

4430 reflections

122 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.17 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, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813022836/hb7131sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022836/hb7131Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022836/hb7131Isup3.cml

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

C8H12N+·NO3−	F(000) = 392
Mr = 184.20	Dx = 1.349 Mg m−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56083 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 15.097 (2) Å	θ = 9–11°
b = 5.8121 (10) Å	µ = 0.06 mm−1
c = 10.486 (2) Å	T = 293 K
β = 99.75 (2)°	Prism, colorless
V = 906.8 (3) Å3	0.40 × 0.35 × 0.30 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.2°
Graphite monochromator	h = −2→25
non–profiled ω scans	k = −9→2
6579 measured reflections	l = −17→17
4430 independent reflections	2 standard reflections every 120 min
2415 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0879P)2] where P = (Fo2 + 2Fc2)/3
4430 reflections	(Δ/σ)max = 0.011
122 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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
O3	0.42764 (9)	0.7571 (2)	0.58898 (11)	0.0491 (4)
N2	0.40982 (10)	0.7432 (3)	0.70119 (15)	0.0495 (4)
N1	0.40818 (11)	1.2425 (3)	0.52659 (18)	0.0576 (5)
H1A	0.4136	1.3250	0.5990	0.086*
H1B	0.4500	1.2859	0.4811	0.086*
H1C	0.4151	1.0940	0.5464	0.086*
C6	0.20891 (13)	1.2197 (3)	0.60241 (18)	0.0485 (5)
H6	0.2267	1.3600	0.6411	0.058*
C2	0.11570 (12)	0.8824 (3)	0.59300 (17)	0.0455 (5)
C7	0.14446 (13)	1.0904 (4)	0.64823 (18)	0.0510 (5)
H7	0.1198	1.1447	0.7180	0.061*
C5	0.24736 (12)	1.1432 (3)	0.49952 (16)	0.0420 (4)
C4	0.21981 (13)	0.9329 (3)	0.44485 (18)	0.0494 (5)
H4	0.2453	0.8768	0.3763	0.059*
C8	0.31895 (14)	1.2799 (4)	0.44969 (19)	0.0538 (5)
H8A	0.3200	1.2369	0.3606	0.065*
H8B	0.3042	1.4423	0.4511	0.065*
C3	0.15502 (13)	0.8059 (3)	0.49093 (19)	0.0517 (5)
H3	0.1373	0.6654	0.4525	0.062*
O1	0.39214 (12)	0.5519 (3)	0.74280 (15)	0.0818 (6)
O2	0.41003 (13)	0.9155 (3)	0.76752 (16)	0.0859 (6)
C1	0.04360 (14)	0.7443 (4)	0.6414 (2)	0.0632 (6)
H1D	0.0477	0.7676	0.7329	0.095*
H1E	0.0516	0.5840	0.6244	0.095*
H1F	−0.0144	0.7933	0.5977	0.095*

	U11	U22	U33	U12	U13	U23
O3	0.0556 (8)	0.0473 (8)	0.0478 (7)	0.0014 (6)	0.0184 (6)	0.0008 (6)
N2	0.0483 (9)	0.0536 (10)	0.0499 (9)	0.0024 (8)	0.0175 (7)	−0.0024 (8)
N1	0.0558 (10)	0.0390 (9)	0.0870 (12)	−0.0007 (8)	0.0379 (9)	0.0063 (9)
C6	0.0555 (11)	0.0418 (10)	0.0504 (10)	−0.0018 (9)	0.0157 (9)	−0.0056 (9)
C2	0.0400 (9)	0.0471 (11)	0.0494 (10)	0.0003 (9)	0.0073 (8)	0.0096 (9)
C7	0.0523 (11)	0.0537 (12)	0.0506 (10)	0.0038 (10)	0.0197 (9)	−0.0026 (9)
C5	0.0471 (10)	0.0377 (9)	0.0428 (9)	−0.0005 (9)	0.0117 (8)	0.0029 (8)
C4	0.0628 (12)	0.0432 (11)	0.0459 (10)	0.0024 (10)	0.0195 (9)	−0.0029 (8)
C8	0.0662 (13)	0.0471 (12)	0.0531 (10)	−0.0053 (10)	0.0245 (10)	0.0021 (9)
C3	0.0607 (12)	0.0409 (11)	0.0541 (11)	−0.0055 (9)	0.0116 (10)	−0.0006 (9)
O1	0.1100 (14)	0.0670 (11)	0.0772 (11)	−0.0136 (10)	0.0413 (10)	0.0139 (9)
O2	0.1169 (15)	0.0737 (12)	0.0739 (10)	0.0027 (11)	0.0353 (10)	−0.0280 (9)
C1	0.0542 (12)	0.0675 (15)	0.0705 (13)	−0.0100 (11)	0.0178 (11)	0.0083 (12)

O3—N2	1.2533 (19)	C2—C1	1.508 (3)
N2—O2	1.219 (2)	C7—H7	0.9300
N2—O1	1.240 (2)	C5—C4	1.384 (3)
N1—C8	1.464 (3)	C5—C8	1.505 (2)
N1—H1A	0.8900	C4—C3	1.376 (3)
N1—H1B	0.8900	C4—H4	0.9300
N1—H1C	0.8900	C8—H8A	0.9700
C6—C7	1.379 (3)	C8—H8B	0.9700
C6—C5	1.383 (2)	C3—H3	0.9300
C6—H6	0.9300	C1—H1D	0.9600
C2—C7	1.378 (3)	C1—H1E	0.9600
C2—C3	1.382 (3)	C1—H1F	0.9600
O2—N2—O1	121.05 (17)	C4—C5—C8	120.39 (16)
O2—N2—O3	120.18 (18)	C3—C4—C5	120.63 (17)
O1—N2—O3	118.77 (17)	C3—C4—H4	119.7
C8—N1—H1A	109.5	C5—C4—H4	119.7
C8—N1—H1B	109.5	N1—C8—C5	112.22 (16)
H1A—N1—H1B	109.5	N1—C8—H8A	109.2
C8—N1—H1C	109.5	C5—C8—H8A	109.2
H1A—N1—H1C	109.5	N1—C8—H8B	109.2
H1B—N1—H1C	109.5	C5—C8—H8B	109.2
C7—C6—C5	120.72 (18)	H8A—C8—H8B	107.9
C7—C6—H6	119.6	C4—C3—C2	121.56 (19)
C5—C6—H6	119.6	C4—C3—H3	119.2
C7—C2—C3	117.47 (17)	C2—C3—H3	119.2
C7—C2—C1	121.30 (18)	C2—C1—H1D	109.5
C3—C2—C1	121.2 (2)	C2—C1—H1E	109.5
C2—C7—C6	121.50 (18)	H1D—C1—H1E	109.5
C2—C7—H7	119.3	C2—C1—H1F	109.5
C6—C7—H7	119.3	H1D—C1—H1F	109.5
C6—C5—C4	118.11 (17)	H1E—C1—H1F	109.5
C6—C5—C8	121.48 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.89	2.07	2.936 (3)	164
N1—H1A···O3i	0.89	2.52	3.065 (2)	120
N1—H1B···O3ii	0.89	2.12	2.9378 (19)	153
N1—H1C···O3	0.89	2.01	2.900 (2)	179
N1—H1C···O2	0.89	2.55	3.158 (3)	126
C8—H8A···O1iii	0.97	2.45	3.234 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.89	2.07	2.936 (3)	164
N1—H1A⋯O3i	0.89	2.52	3.065 (2)	120
N1—H1B⋯O3ii	0.89	2.12	2.9378 (19)	153
N1—H1C⋯O3	0.89	2.01	2.900 (2)	179
N1—H1C⋯O2	0.89	2.55	3.158 (3)	126
C8—H8A⋯O1iii	0.97	2.45	3.234 (2)	138

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