4-[(2-Hy-droxy-benz-yl)amino]-pyridinium nitrate.

The planes of the aromatic rings in the cation of the title salt, C(12)H(13)N(2)O(+)·NO(3) (-), are twisted along the -CH(2)-NH- single bond by 75.3 (1)°. In the crystal, the phenol O, amine N and pyridinium N atoms are hydrogen-bond donors to the O atoms of the nitrate counter-ions. These hydrogen bonds lead to the formation of a layer in the crystal.

Related literature

For 2-[(pyridin-2-yl­amino)­meth­yl]phenol, see: Gao & Ng (2012 ▶). For 2-[(pyridin-3-yl­amino)­meth­yl]phenol, see: Xu et al. (2011 ▶).

Experimental

Crystal data

C12H13N2O+·NO3 −

M = 263.25

Monoclinic,

a = 13.611 (4) Å

b = 12.687 (3) Å

c = 10.030 (2) Å

β = 132.694 (12)°

V = 1273.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.24 × 0.21 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.975, T max = 0.978

6077 measured reflections

1458 independent reflections

1176 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.08

1458 reflections

184 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031352/xu5582sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031352/xu5582Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031352/xu5582Isup3.cml

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

C12H13N2O+·NO3−	Z = 4
Mr = 263.25	F(000) = 552
Monoclinic, Cc	Dx = 1.374 Mg m−3
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 13.611 (4) Å	µ = 0.11 mm−1
b = 12.687 (3) Å	T = 295 K
c = 10.030 (2) Å	Prism, faint yellow
β = 132.694 (12)°	0.24 × 0.21 × 0.21 mm
V = 1273.0 (5) Å3

Rigaku R-AXIS RAPID IP diffractometer	1458 independent reflections
Radiation source: fine-focus sealed tube	1176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scan	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.975, Tmax = 0.978	k = −16→16
6077 measured reflections	l = −13→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0753P)2] where P = (Fo2 + 2Fc2)/3
1458 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.20 e Å−3
5 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.

	x	y	z	Uiso*/Ueq
O1	0.5006 (2)	0.17761 (17)	0.5005 (3)	0.0795 (6)
O2	0.4295 (3)	0.38568 (15)	0.3747 (3)	0.0882 (7)
O3	0.3096 (2)	0.47126 (17)	0.1249 (3)	0.0817 (6)
O4	0.3075 (2)	0.30247 (17)	0.1215 (3)	0.0816 (6)
N1	0.4372 (3)	−0.37774 (19)	0.4116 (4)	0.0740 (6)
N2	0.6073 (2)	−0.11750 (18)	0.7349 (3)	0.0692 (6)
N3	0.3475 (2)	0.38556 (18)	0.2053 (3)	0.0669 (6)
C1	0.4016 (3)	−0.2829 (3)	0.3359 (4)	0.0739 (7)
H1A	0.3378	−0.2776	0.2101	0.089*
C2	0.4552 (3)	−0.1938 (2)	0.4358 (4)	0.0660 (6)
H2A	0.4293	−0.1284	0.3792	0.079*
C3	0.5510 (2)	−0.2009 (2)	0.6271 (4)	0.0588 (6)
C4	0.5857 (3)	−0.3036 (2)	0.7024 (4)	0.0641 (6)
H4	0.6484	−0.3128	0.8276	0.077*
C5	0.5270 (3)	−0.3885 (2)	0.5910 (4)	0.0720 (7)
H5	0.5501	−0.4557	0.6411	0.086*
C6	0.5830 (3)	−0.0101 (2)	0.6719 (4)	0.0708 (7)
H6A	0.5908	−0.0060	0.5828	0.085*
H6B	0.6522	0.0343	0.7734	0.085*
C7	0.4489 (2)	0.03351 (19)	0.5886 (3)	0.0569 (5)
C8	0.3625 (3)	−0.0166 (2)	0.5960 (4)	0.0650 (6)
H8	0.3879	−0.0800	0.6584	0.078*
C9	0.2390 (3)	0.0260 (3)	0.5123 (5)	0.0784 (8)
H9	0.1825	−0.0078	0.5201	0.094*
C10	0.2006 (3)	0.1180 (3)	0.4180 (6)	0.0834 (9)
H10	0.1164	0.1456	0.3584	0.100*
C11	0.2847 (3)	0.1707 (2)	0.4096 (4)	0.0742 (7)
H11	0.2578	0.2336	0.3456	0.089*
C12	0.4100 (3)	0.12908 (19)	0.4978 (3)	0.0607 (6)
H1	0.477 (4)	0.2368 (14)	0.450 (4)	0.082 (9)*
H2	0.670 (3)	−0.126 (3)	0.8524 (16)	0.081 (10)*
H3	0.400 (3)	−0.4320 (18)	0.337 (4)	0.081 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0804 (12)	0.0576 (10)	0.1069 (16)	0.0045 (9)	0.0660 (12)	0.0162 (10)
O2	0.1108 (18)	0.0634 (12)	0.0670 (14)	−0.0060 (11)	0.0509 (14)	−0.0011 (9)
O3	0.0915 (14)	0.0660 (12)	0.0782 (13)	0.0112 (10)	0.0539 (12)	0.0097 (10)
O4	0.0855 (13)	0.0665 (12)	0.0805 (13)	−0.0092 (10)	0.0514 (12)	−0.0138 (9)
N1	0.0745 (14)	0.0683 (15)	0.0895 (17)	−0.0068 (12)	0.0597 (14)	−0.0155 (13)
N2	0.0629 (13)	0.0570 (13)	0.0657 (14)	0.0038 (9)	0.0349 (12)	0.0069 (10)
N3	0.0683 (12)	0.0654 (15)	0.0713 (14)	0.0001 (10)	0.0490 (12)	−0.0010 (10)
C1	0.0661 (15)	0.0879 (19)	0.0658 (15)	0.0049 (14)	0.0440 (13)	−0.0032 (14)
C2	0.0633 (14)	0.0672 (15)	0.0679 (15)	0.0097 (12)	0.0446 (13)	0.0088 (12)
C3	0.0562 (12)	0.0546 (13)	0.0682 (15)	0.0055 (10)	0.0432 (13)	0.0058 (10)
C4	0.0664 (15)	0.0564 (14)	0.0701 (15)	0.0080 (11)	0.0465 (13)	0.0094 (11)
C5	0.0798 (17)	0.0559 (15)	0.095 (2)	0.0059 (12)	0.0648 (17)	0.0061 (13)
C6	0.0637 (13)	0.0531 (14)	0.0834 (17)	−0.0003 (11)	0.0450 (13)	0.0036 (12)
C7	0.0619 (13)	0.0460 (11)	0.0593 (12)	−0.0046 (9)	0.0397 (11)	−0.0073 (9)
C8	0.0780 (15)	0.0521 (12)	0.0761 (15)	−0.0087 (12)	0.0566 (13)	−0.0094 (11)
C9	0.0841 (18)	0.0707 (18)	0.108 (2)	−0.0118 (14)	0.0759 (19)	−0.0190 (16)
C10	0.0751 (17)	0.075 (2)	0.112 (2)	0.0063 (14)	0.0680 (19)	−0.0095 (17)
C11	0.0767 (16)	0.0611 (15)	0.0868 (19)	0.0102 (12)	0.0562 (16)	0.0047 (12)
C12	0.0665 (13)	0.0504 (13)	0.0675 (14)	−0.0021 (11)	0.0463 (12)	−0.0055 (10)

O1—C12	1.362 (3)	C4—C5	1.354 (4)
O1—H1	0.837 (10)	C4—H4	0.9300
O2—N3	1.250 (3)	C5—H5	0.9300
O3—N3	1.238 (3)	C6—C7	1.505 (4)
O4—N3	1.222 (3)	C6—H6A	0.9700
N1—C1	1.327 (4)	C6—H6B	0.9700
N1—C5	1.330 (4)	C7—C8	1.383 (4)
N1—H3	0.882 (10)	C7—C12	1.388 (3)
N2—C3	1.324 (4)	C8—C9	1.381 (4)
N2—C6	1.443 (3)	C8—H8	0.9300
N2—H2	0.874 (10)	C9—C10	1.364 (5)
C1—C2	1.350 (4)	C9—H9	0.9300
C1—H1A	0.9300	C10—C11	1.376 (5)
C2—C3	1.413 (4)	C10—H10	0.9300
C2—H2A	0.9300	C11—C12	1.387 (4)
C3—C4	1.418 (3)	C11—H11	0.9300
C12—O1—H1	115 (3)	N2—C6—C7	115.0 (2)
C1—N1—C5	120.7 (3)	N2—C6—H6A	108.5
C1—N1—H3	116 (2)	C7—C6—H6A	108.5
C5—N1—H3	123 (2)	N2—C6—H6B	108.5
C3—N2—C6	124.3 (2)	C7—C6—H6B	108.5
C3—N2—H2	120 (2)	H6A—C6—H6B	107.5
C6—N2—H2	116 (2)	C8—C7—C12	118.5 (2)
O4—N3—O3	121.0 (2)	C8—C7—C6	123.8 (2)
O4—N3—O2	120.5 (2)	C12—C7—C6	117.7 (2)
O3—N3—O2	118.5 (2)	C9—C8—C7	121.1 (3)
N1—C1—C2	122.0 (3)	C9—C8—H8	119.5
N1—C1—H1A	119.0	C7—C8—H8	119.5
C2—C1—H1A	119.0	C10—C9—C8	119.5 (3)
C1—C2—C3	119.5 (3)	C10—C9—H9	120.2
C1—C2—H2A	120.3	C8—C9—H9	120.2
C3—C2—H2A	120.3	C9—C10—C11	121.0 (3)
N2—C3—C2	123.3 (2)	C9—C10—H10	119.5
N2—C3—C4	120.1 (2)	C11—C10—H10	119.5
C2—C3—C4	116.7 (2)	C10—C11—C12	119.3 (3)
C5—C4—C3	119.6 (3)	C10—C11—H11	120.3
C5—C4—H4	120.2	C12—C11—H11	120.3
C3—C4—H4	120.2	O1—C12—C11	123.0 (2)
N1—C5—C4	121.5 (3)	O1—C12—C7	116.4 (2)
N1—C5—H5	119.3	C11—C12—C7	120.6 (2)
C4—C5—H5	119.3
C5—N1—C1—C2	0.8 (4)	N2—C6—C7—C12	−169.2 (2)
N1—C1—C2—C3	−0.8 (4)	C12—C7—C8—C9	1.3 (4)
C6—N2—C3—C2	−2.9 (4)	C6—C7—C8—C9	−178.1 (3)
C6—N2—C3—C4	177.4 (2)	C7—C8—C9—C10	1.2 (4)
C1—C2—C3—N2	−179.3 (3)	C8—C9—C10—C11	−2.0 (5)
C1—C2—C3—C4	0.5 (3)	C9—C10—C11—C12	0.3 (5)
N2—C3—C4—C5	179.6 (3)	C10—C11—C12—O1	−178.2 (3)
C2—C3—C4—C5	−0.1 (3)	C10—C11—C12—C7	2.1 (4)
C1—N1—C5—C4	−0.4 (4)	C8—C7—C12—O1	177.4 (2)
C3—C4—C5—N1	0.1 (4)	C6—C7—C12—O1	−3.2 (3)
C3—N2—C6—C7	73.7 (4)	C8—C7—C12—C11	−2.9 (3)
N2—C6—C7—C8	10.2 (4)	C6—C7—C12—C11	176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (2)	1.97 (2)	2.800 (3)	169 (4)
N1—H3···O2i	0.88 (3)	2.33 (2)	3.017 (3)	134 (2)
N1—H3···O3i	0.88 (3)	2.00 (3)	2.860 (4)	165 (3)
N2—H2···O3ii	0.88 (1)	2.36 (2)	3.089 (3)	141 (3)
N2—H2···O4ii	0.88 (1)	2.18 (2)	3.027 (3)	162 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (2)	1.97 (2)	2.800 (3)	169 (4)
N1—H3⋯O2i	0.88 (3)	2.33 (2)	3.017 (3)	134 (2)
N1—H3⋯O3i	0.88 (3)	2.00 (3)	2.860 (4)	165 (3)
N2—H2⋯O3ii	0.88 (1)	2.36 (2)	3.089 (3)	141 (3)
N2—H2⋯O4ii	0.88 (1)	2.18 (2)	3.027 (3)	162 (3)

Symmetry codes: (i) ; (ii) .