3-{[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]amino}pyridinium per-chlorate.

In the title Schiff base salt, C16H13N2O(+)·ClO4 (-), the pyridine ring and the naphthalene ring system are approximately co-planar [making a dihedral angle of 6.05 (12)°] and an intra-molecular O-H⋯N hydrogen bond occurs between the hydroxyl and imino groups. In the crystal, the cations and anions are linked by N-H⋯O and weak C-H⋯O hydrogen bonds, forming the supra-molecular layers parallel to (100). The crystal studied was an inversion twin refined with minor component = 0.43 (13).

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000 ▶); Sriram et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For the coordination chemistry of Schiff bases, see: Ali et al. (2008 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For the crystal structures of related Schiff base compounds, see: Damous et al. (2011 ▶); Fun et al. (2009 ▶); Nadeem et al. (2009 ▶); Eltayeb et al. (2008 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C16H13N2O+·ClO4 −

M = 348.73

Orthorhombic,

a = 6.5043 (9) Å

b = 14.6915 (19) Å

c = 15.398 (3) Å

V = 1471.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 180 K

0.25 × 0.04 × 0.03 mm

Data collection

Agilent Xcalibur (Sapphire1) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.685, T max = 1.000

9582 measured reflections

3369 independent reflections

1695 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.127

S = 0.92

3369 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1362 Friedel pairs

Absolute structure parameter: 0.43 (13)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1012).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023015/xu5730sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023015/xu5730Isup2.hkl

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

C16H13N2O+·ClO4−	Dx = 1.574 Mg m−3
Mr = 348.73	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1867 reflections
a = 6.5043 (9) Å	θ = 3.0–28.4°
b = 14.6915 (19) Å	µ = 0.29 mm−1
c = 15.398 (3) Å	T = 180 K
V = 1471.4 (4) Å3	Needle, red
Z = 4	0.25 × 0.04 × 0.03 mm
F(000) = 720

Agilent Xcalibur (Sapphire1) diffractometer	3369 independent reflections
Radiation source: fine-focus sealed tube	1695 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 8.2632 pixels mm-1	θmax = 28.5°, θmin = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −19→19
Tmin = 0.685, Tmax = 1.000	l = −19→19
9582 measured reflections

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)] = 0.059	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0494P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
3369 reflections	Δρmax = 0.26 e Å−3
218 parameters	Δρmin = −0.28 e Å−3
0 restraints	Absolute structure: Flack (1983), 1362 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.43 (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
Cl1	0.26988 (16)	0.25979 (7)	0.14441 (7)	0.0420 (3)
O1	0.3025 (4)	0.31465 (18)	0.63157 (19)	0.0404 (7)
H1	0.3022	0.3556	0.5954	0.061*
O13	0.3797 (5)	0.2618 (2)	0.0636 (2)	0.0567 (9)
O12	0.2121 (6)	0.1681 (2)	0.1622 (2)	0.0702 (10)
N1	0.2985 (5)	0.3865 (2)	0.4812 (2)	0.0283 (9)
O11	0.4044 (5)	0.2891 (2)	0.2118 (2)	0.0647 (10)
C17	0.2947 (6)	0.1364 (2)	0.4624 (3)	0.0271 (10)
C8	0.2991 (5)	0.2266 (2)	0.5012 (2)	0.0267 (9)
C9	0.3004 (5)	0.2340 (3)	0.5911 (3)	0.0297 (10)
C16	0.2929 (5)	0.1213 (3)	0.3737 (3)	0.0357 (10)
H16	0.2964	0.1707	0.3359	0.043*
C10	0.2994 (6)	0.1562 (3)	0.6438 (3)	0.0366 (10)
H10	0.3015	0.1627	0.7039	0.044*
C12	0.2913 (6)	0.0598 (2)	0.5180 (3)	0.0293 (9)
N5	0.2590 (6)	0.6228 (2)	0.4274 (3)	0.0455 (10)
H5	0.2496	0.6728	0.4562	0.055*
C1	0.2895 (6)	0.4649 (2)	0.4284 (3)	0.0302 (10)
C7	0.2958 (6)	0.3064 (2)	0.4483 (3)	0.0284 (9)
H7	0.2915	0.3	0.3882	0.034*
C11	0.2954 (6)	0.0720 (3)	0.6088 (3)	0.0373 (11)
H11	0.2954	0.0214	0.6451	0.045*
O14	0.0992 (5)	0.3161 (3)	0.1393 (3)	0.1075 (16)
C2	0.2884 (6)	0.4676 (3)	0.3384 (3)	0.0360 (11)
H2	0.2999	0.4138	0.307	0.043*
C13	0.2841 (7)	−0.0278 (3)	0.4825 (3)	0.0390 (11)
H13	0.2807	−0.0781	0.5192	0.047*
C3	0.2706 (7)	0.5487 (3)	0.2955 (3)	0.0405 (11)
H3	0.2684	0.5499	0.2351	0.049*
C4	0.2562 (7)	0.6270 (3)	0.3411 (3)	0.0443 (11)
H4	0.2445	0.6827	0.3127	0.053*
C15	0.2861 (7)	0.0350 (3)	0.3406 (3)	0.0455 (12)
H15	0.2843	0.0265	0.2807	0.055*
C6	0.2756 (7)	0.5459 (2)	0.4712 (3)	0.0374 (11)
H6	0.2778	0.5469	0.5316	0.045*
C14	0.2819 (7)	−0.0405 (3)	0.3954 (3)	0.0471 (12)
H14	0.2777	−0.099	0.3724	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0533 (6)	0.0401 (6)	0.0327 (6)	0.0063 (6)	0.0004 (6)	0.0032 (5)
O1	0.0468 (17)	0.0434 (16)	0.0311 (19)	−0.0026 (14)	0.0021 (18)	−0.0021 (14)
O13	0.078 (2)	0.059 (2)	0.033 (2)	0.0139 (19)	0.0153 (16)	0.0113 (18)
O12	0.106 (3)	0.0500 (19)	0.055 (3)	−0.036 (2)	0.000 (3)	0.0080 (16)
N1	0.027 (2)	0.0273 (17)	0.030 (2)	−0.0024 (16)	0.0026 (17)	−0.0030 (15)
O11	0.089 (2)	0.057 (2)	0.048 (3)	−0.0196 (19)	−0.006 (2)	−0.0124 (19)
C17	0.021 (2)	0.036 (2)	0.024 (3)	−0.0001 (19)	−0.003 (2)	−0.0003 (18)
C8	0.0181 (18)	0.034 (2)	0.028 (2)	0.0023 (18)	0.0019 (18)	0.0030 (18)
C9	0.023 (2)	0.036 (2)	0.030 (3)	−0.003 (2)	0.0009 (18)	−0.0020 (19)
C16	0.040 (2)	0.036 (2)	0.031 (3)	−0.005 (2)	0.004 (2)	0.0080 (18)
C10	0.033 (2)	0.055 (3)	0.022 (2)	−0.001 (2)	0.001 (2)	0.009 (2)
C12	0.023 (2)	0.030 (2)	0.034 (3)	−0.0001 (19)	0.001 (2)	0.0113 (18)
N5	0.056 (3)	0.0278 (19)	0.052 (3)	−0.005 (2)	0.006 (2)	−0.0102 (17)
C1	0.031 (2)	0.025 (2)	0.035 (3)	−0.004 (2)	0.003 (2)	−0.0012 (18)
C7	0.023 (2)	0.033 (2)	0.029 (2)	−0.0020 (19)	0.004 (2)	0.0023 (19)
C11	0.038 (2)	0.039 (2)	0.034 (3)	0.006 (2)	0.003 (2)	0.012 (2)
O14	0.104 (3)	0.128 (3)	0.091 (4)	0.078 (3)	0.039 (3)	0.043 (3)
C2	0.046 (3)	0.031 (2)	0.031 (3)	0.004 (2)	0.008 (2)	0.0033 (19)
C13	0.039 (3)	0.032 (2)	0.047 (3)	−0.003 (2)	0.004 (3)	0.009 (2)
C3	0.050 (3)	0.034 (2)	0.037 (3)	0.002 (3)	0.003 (3)	0.007 (2)
C4	0.049 (3)	0.032 (2)	0.051 (4)	0.001 (2)	0.006 (3)	0.010 (2)
C15	0.060 (3)	0.038 (3)	0.038 (3)	−0.002 (3)	0.002 (3)	−0.008 (2)
C6	0.041 (3)	0.027 (2)	0.044 (3)	−0.002 (2)	0.003 (3)	0.0008 (19)
C14	0.054 (3)	0.032 (2)	0.055 (3)	−0.005 (3)	0.005 (3)	0.000 (2)

Cl1—O14	1.387 (3)	C12—C11	1.411 (5)
Cl1—O11	1.424 (3)	N5—C6	1.321 (5)
Cl1—O12	1.425 (3)	N5—C4	1.331 (5)
Cl1—O13	1.436 (3)	N5—H5	0.86
O1—C9	1.339 (4)	C1—C6	1.363 (5)
O1—H1	0.82	C1—C2	1.386 (5)
N1—C7	1.282 (4)	C7—H7	0.93
N1—C1	1.411 (5)	C11—H11	0.93
C17—C16	1.384 (6)	C2—C3	1.367 (5)
C17—C12	1.414 (5)	C2—H2	0.93
C17—C8	1.455 (5)	C13—C14	1.353 (6)
C8—C9	1.388 (5)	C13—H13	0.93
C8—C7	1.428 (5)	C3—C4	1.351 (5)
C9—C10	1.402 (5)	C3—H3	0.93
C16—C15	1.367 (5)	C4—H4	0.93
C16—H16	0.93	C15—C14	1.394 (5)
C10—C11	1.349 (5)	C15—H15	0.93
C10—H10	0.93	C6—H6	0.93
C12—C13	1.399 (5)	C14—H14	0.93
O14—Cl1—O11	110.6 (3)	C6—C1—N1	115.9 (4)
O14—Cl1—O12	111.3 (3)	C2—C1—N1	126.8 (3)
O11—Cl1—O12	107.9 (2)	N1—C7—C8	121.9 (4)
O14—Cl1—O13	109.7 (2)	N1—C7—H7	119.1
O11—Cl1—O13	108.6 (2)	C8—C7—H7	119.1
O12—Cl1—O13	108.5 (2)	C10—C11—C12	120.9 (4)
C9—O1—H1	109.5	C10—C11—H11	119.6
C7—N1—C1	121.4 (4)	C12—C11—H11	119.6
C16—C17—C12	118.0 (4)	C3—C2—C1	120.6 (4)
C16—C17—C8	123.5 (4)	C3—C2—H2	119.7
C12—C17—C8	118.5 (4)	C1—C2—H2	119.7
C9—C8—C7	120.3 (4)	C14—C13—C12	120.9 (4)
C9—C8—C17	118.8 (3)	C14—C13—H13	119.5
C7—C8—C17	120.9 (4)	C12—C13—H13	119.5
O1—C9—C8	122.2 (3)	C4—C3—C2	119.8 (4)
O1—C9—C10	116.9 (4)	C4—C3—H3	120.1
C8—C9—C10	120.9 (4)	C2—C3—H3	120.1
C15—C16—C17	121.1 (4)	N5—C4—C3	118.6 (4)
C15—C16—H16	119.4	N5—C4—H4	120.7
C17—C16—H16	119.4	C3—C4—H4	120.7
C11—C10—C9	121.1 (4)	C16—C15—C14	120.8 (4)
C11—C10—H10	119.4	C16—C15—H15	119.6
C9—C10—H10	119.4	C14—C15—H15	119.6
C13—C12—C11	120.4 (4)	N5—C6—C1	120.4 (4)
C13—C12—C17	119.7 (4)	N5—C6—H6	119.8
C11—C12—C17	119.9 (4)	C1—C6—H6	119.8
C6—N5—C4	123.4 (4)	C13—C14—C15	119.3 (4)
C6—N5—H5	118.3	C13—C14—H14	120.3
C4—N5—H5	118.3	C15—C14—H14	120.3
C6—C1—C2	117.3 (4)
C16—C17—C8—C9	179.9 (4)	C9—C8—C7—N1	1.6 (6)
C12—C17—C8—C9	0.2 (5)	C17—C8—C7—N1	179.7 (3)
C16—C17—C8—C7	1.8 (6)	C9—C10—C11—C12	−0.2 (6)
C12—C17—C8—C7	−177.9 (4)	C13—C12—C11—C10	−179.0 (4)
C7—C8—C9—O1	−1.3 (5)	C17—C12—C11—C10	1.0 (6)
C17—C8—C9—O1	−179.4 (3)	C6—C1—C2—C3	−1.0 (7)
C7—C8—C9—C10	178.7 (4)	N1—C1—C2—C3	177.3 (4)
C17—C8—C9—C10	0.6 (5)	C11—C12—C13—C14	−179.4 (4)
C12—C17—C16—C15	0.6 (6)	C17—C12—C13—C14	0.5 (6)
C8—C17—C16—C15	−179.2 (4)	C1—C2—C3—C4	0.7 (7)
O1—C9—C10—C11	179.4 (3)	C6—N5—C4—C3	0.1 (8)
C8—C9—C10—C11	−0.6 (6)	C2—C3—C4—N5	−0.2 (7)
C16—C17—C12—C13	−0.7 (6)	C17—C16—C15—C14	−0.3 (6)
C8—C17—C12—C13	179.1 (3)	C4—N5—C6—C1	−0.5 (7)
C16—C17—C12—C11	179.3 (4)	C2—C1—C6—N5	0.9 (7)
C8—C17—C12—C11	−1.0 (6)	N1—C1—C6—N5	−177.6 (4)
C7—N1—C1—C6	174.5 (4)	C12—C13—C14—C15	−0.3 (7)
C7—N1—C1—C2	−3.8 (7)	C16—C15—C14—C13	0.2 (7)
C1—N1—C7—C8	−178.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.545 (4)	147
N5—H5···O13i	0.86	2.09	2.844 (5)	146
C2—H2···O11	0.93	2.44	3.354 (5)	166
C3—H3···O1ii	0.93	2.59	3.260 (5)	129
C13—H13···O12iii	0.93	2.57	3.451 (6)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.545 (4)	147
N5—H5⋯O13i	0.86	2.09	2.844 (5)	146
C2—H2⋯O11	0.93	2.44	3.354 (5)	166
C3—H3⋯O1ii	0.93	2.59	3.260 (5)	129
C13—H13⋯O12iii	0.93	2.57	3.451 (6)	158

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