2,3-Xylidinium nitrate.

In the crystal structure of the title compound, C8H12N(+)·NO3 (-), the 2,3-xylidinium (2,3-di-methyl-anilinium) cations are connected to the nitrate anions through bifurcated N-H⋯(O,O) and weak C-H⋯O hydrogen bonds, generating corrugated layers parallel to (001) at z = 0.25 and 0.75. These layers are connected via C-H⋯O inter-actions, giving rise to a three-dimensional network.

Related literature

For related structures, see: Marouani et al. (2010 ▶, 2012 ▶). For graph-set notation of hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H12N+·NO3 −

M = 184.20

Orthorhombic,

a = 10.889 (2) Å

b = 10.110 (2) Å

c = 17.010 (3) Å

V = 1872.5 (6) Å3

Z = 8

Ag Kα radiation

λ = 0.56083 Å

μ = 0.06 mm−1

T = 293 K

0.4 × 0.3 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

8719 measured reflections

4541 independent reflections

1933 reflections with I > 2σ(I)

R int = 0.056

2 standard reflections every 120 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.178

S = 0.86

4541 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 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/S1600536813023465/pv2645sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023465/pv2645Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023465/pv2645Isup3.cml

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

C8H12N+·NO3−	F(000) = 784
Mr = 184.20	Dx = 1.307 Mg m−3
Orthorhombic, Pbca	Ag Kα radiation, λ = 0.56083 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 10.889 (2) Å	θ = 8–10°
b = 10.110 (2) Å	µ = 0.06 mm−1
c = 17.010 (3) Å	T = 293 K
V = 1872.5 (6) Å3	Prism, pink
Z = 8	0.4 × 0.3 × 0.2 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.056
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.4°
Graphite monochromator	h = −18→3
non–profiled ω scans	k = −5→16
8719 measured reflections	l = −2→28
4541 independent reflections	2 standard reflections every 120 min
1933 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 0.86	w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3
4541 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.15 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
N1	0.10288 (17)	0.74955 (19)	0.26311 (10)	0.0625 (5)
O2	0.01325 (15)	0.68356 (15)	0.24486 (9)	0.0858 (6)
O3	0.18890 (15)	0.69932 (14)	0.30086 (10)	0.0812 (5)
O1	0.11018 (16)	0.86708 (16)	0.24375 (10)	0.0992 (6)
C2	0.22220 (17)	0.44029 (17)	0.46097 (12)	0.0523 (5)
C1	0.12753 (19)	0.39756 (18)	0.41282 (12)	0.0517 (5)
N2	0.13609 (14)	0.42040 (15)	0.32795 (10)	0.0613 (5)
H2A	0.1490	0.5060	0.3189	0.092*
H2B	0.0663	0.3956	0.3050	0.092*
H2C	0.1981	0.3735	0.3084	0.092*
C3	0.2094 (2)	0.4186 (2)	0.54217 (13)	0.0629 (6)
C6	0.0239 (2)	0.33705 (19)	0.44060 (15)	0.0668 (6)
H6	−0.0381	0.3111	0.4063	0.080*
C7	0.33189 (17)	0.5102 (2)	0.42887 (14)	0.0669 (6)
H7A	0.3361	0.4968	0.3731	0.100*
H7B	0.4048	0.4756	0.4531	0.100*
H7C	0.3254	0.6030	0.4398	0.100*
C4	0.1061 (2)	0.3555 (2)	0.56938 (15)	0.0788 (7)
H4	0.0986	0.3394	0.6230	0.095*
C5	0.0131 (2)	0.3153 (2)	0.51969 (16)	0.0792 (8)
H5	−0.0564	0.2738	0.5398	0.095*
C8	0.3045 (2)	0.4673 (3)	0.59902 (15)	0.0933 (8)
H8A	0.3094	0.5619	0.5962	0.140*
H8B	0.3828	0.4297	0.5859	0.140*
H8C	0.2821	0.4413	0.6514	0.140*

	U11	U22	U33	U12	U13	U23
N1	0.0656 (11)	0.0694 (12)	0.0525 (10)	0.0014 (12)	0.0011 (10)	0.0037 (10)
O2	0.0669 (10)	0.1033 (14)	0.0872 (12)	−0.0192 (10)	−0.0084 (9)	0.0135 (9)
O3	0.0770 (10)	0.0763 (11)	0.0902 (12)	0.0059 (9)	−0.0291 (10)	0.0099 (9)
O1	0.1262 (15)	0.0573 (9)	0.1142 (14)	−0.0031 (11)	−0.0345 (13)	0.0181 (10)
C2	0.0550 (13)	0.0402 (11)	0.0615 (13)	0.0111 (10)	−0.0002 (10)	0.0052 (10)
C1	0.0564 (12)	0.0385 (10)	0.0601 (13)	0.0065 (10)	0.0027 (11)	0.0020 (9)
N2	0.0620 (11)	0.0539 (10)	0.0681 (12)	0.0002 (9)	−0.0070 (9)	−0.0017 (9)
C3	0.0766 (16)	0.0531 (13)	0.0590 (14)	0.0207 (12)	0.0058 (12)	0.0057 (11)
C6	0.0624 (14)	0.0465 (12)	0.0915 (17)	−0.0005 (12)	0.0080 (13)	−0.0024 (12)
C7	0.0590 (13)	0.0721 (14)	0.0696 (14)	−0.0010 (12)	−0.0089 (11)	0.0076 (12)
C4	0.104 (2)	0.0593 (15)	0.0731 (16)	0.0218 (15)	0.0272 (17)	0.0126 (13)
C5	0.0821 (18)	0.0518 (15)	0.104 (2)	0.0026 (13)	0.0325 (16)	0.0089 (14)
C8	0.111 (2)	0.103 (2)	0.0656 (15)	0.0249 (18)	−0.0158 (15)	−0.0014 (14)

N1—O2	1.222 (2)	C3—C8	1.500 (3)
N1—O1	1.236 (2)	C6—C5	1.368 (3)
N1—O3	1.244 (2)	C6—H6	0.9300
C2—C1	1.386 (3)	C7—H7A	0.9600
C2—C3	1.406 (3)	C7—H7B	0.9600
C2—C7	1.491 (3)	C7—H7C	0.9600
C1—C6	1.368 (3)	C4—C5	1.381 (3)
C1—N2	1.465 (2)	C4—H4	0.9300
N2—H2A	0.8900	C5—H5	0.9300
N2—H2B	0.8900	C8—H8A	0.9600
N2—H2C	0.8900	C8—H8B	0.9600
C3—C4	1.373 (3)	C8—H8C	0.9600
O2—N1—O1	120.6 (2)	C5—C6—H6	120.6
O2—N1—O3	120.63 (19)	C2—C7—H7A	109.5
O1—N1—O3	118.80 (19)	C2—C7—H7B	109.5
C1—C2—C3	117.3 (2)	H7A—C7—H7B	109.5
C1—C2—C7	121.81 (19)	C2—C7—H7C	109.5
C3—C2—C7	120.9 (2)	H7A—C7—H7C	109.5
C6—C1—C2	123.3 (2)	H7B—C7—H7C	109.5
C6—C1—N2	117.6 (2)	C3—C4—C5	122.1 (2)
C2—C1—N2	119.08 (18)	C3—C4—H4	118.9
C1—N2—H2A	109.5	C5—C4—H4	118.9
C1—N2—H2B	109.5	C6—C5—C4	119.4 (2)
H2A—N2—H2B	109.5	C6—C5—H5	120.3
C1—N2—H2C	109.5	C4—C5—H5	120.3
H2A—N2—H2C	109.5	C3—C8—H8A	109.5
H2B—N2—H2C	109.5	C3—C8—H8B	109.5
C4—C3—C2	119.0 (2)	H8A—C8—H8B	109.5
C4—C3—C8	120.0 (2)	C3—C8—H8C	109.5
C2—C3—C8	120.9 (2)	H8A—C8—H8C	109.5
C1—C6—C5	118.9 (2)	H8B—C8—H8C	109.5
C1—C6—H6	120.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.89	2.03	2.915 (2)	177
N2—H2A···O2	0.89	2.64	3.296 (2)	131
N2—H2B···O1i	0.89	2.11	2.995 (2)	171
N2—H2B···O2i	0.89	2.46	3.148 (2)	134
N2—H2C···O3ii	0.89	2.15	2.973 (2)	153
N2—H2C···O1ii	0.89	2.36	3.158 (2)	149
C4—H4···O2iii	0.93	2.57	3.439 (3)	156
C7—H7A···O1ii	0.96	2.63	3.522 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.89	2.03	2.915 (2)	177
N2—H2A⋯O2	0.89	2.64	3.296 (2)	131
N2—H2B⋯O1i	0.89	2.11	2.995 (2)	171
N2—H2B⋯O2i	0.89	2.46	3.148 (2)	134
N2—H2C⋯O3ii	0.89	2.15	2.973 (2)	153
N2—H2C⋯O1ii	0.89	2.36	3.158 (2)	149
C4—H4⋯O2iii	0.93	2.57	3.439 (3)	156
C7—H7A⋯O1ii	0.96	2.63	3.522 (3)	155

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