Zwitterionic 1-{(E)-[(2-methyl-phen-yl)iminium-yl]meth-yl}naphthalen-2-olate.

The title Schiff base, C18H15NO, crystallizes in its zwitterionic form and an N-H⋯O hydrogen bond closes an S(6) ring. The dihedral angle between the aromatic ring systems is 36.91 (10)°. Weak aromatic π-π stacking occurs in the crystal [minimum centroid-centroid separation = 3.7771 (15) Å].

Related literature

For background to Schiff bases derived from 2-hy­droxy-1-aromatic aldehydes and n class="Chemical">amines, see: Deneva et al. (2013 ▶); Martınez et al. (2011 ▶). For related structures, see: Albayrak et al. (2010 ▶); Petek et al. (2007 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H15NO

M = 261.31

Orthorhombic,

a = 7.3627 (5) Å

b = 12.4007 (10) Å

c = 14.4365 (12) Å

V = 1318.09 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.57 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.821, T max = 0.995

14320 measured reflections

1721 independent reflections

1439 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.13

1721 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008794/hb7171sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008794/hb7171Isup2.hkl

CCDC reference: 998118

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H15NO	F(000) = 552
Mr = 261.31	Dx = 1.317 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3889 reflections
a = 7.3627 (5) Å	θ = 2.8–26.6°
b = 12.4007 (10) Å	µ = 0.08 mm−1
c = 14.4365 (12) Å	T = 150 K
V = 1318.09 (18) Å3	Rod, yellow
Z = 4	0.57 × 0.08 × 0.06 mm

Bruker APEXII CCD diffractometer	1439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→9
Tmin = 0.821, Tmax = 0.995	k = −16→16
14320 measured reflections	l = −18→18
1721 independent reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.2897P] where P = (Fo2 + 2Fc2)/3
1721 reflections	(Δ/σ)max = 0.004
182 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.19 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
O1	0.9691 (3)	0.33259 (13)	0.36389 (11)	0.0330 (4)
C2	0.9303 (3)	0.23027 (19)	0.36261 (17)	0.0263 (5)
C3	0.9485 (3)	0.1707 (2)	0.27755 (17)	0.0285 (5)
H3	0.9881	0.2069	0.2232	0.034*
C4	0.9106 (3)	0.06523 (19)	0.27381 (16)	0.0278 (5)
H4	0.925	0.0282	0.2167	0.033*
C5	0.8489 (3)	0.00629 (18)	0.35345 (16)	0.0241 (5)
C6	0.8096 (4)	−0.10430 (19)	0.34660 (18)	0.0312 (6)
H6	0.8193	−0.1391	0.288	0.037*
C7	0.7575 (4)	−0.16291 (19)	0.42255 (17)	0.0338 (6)
H7	0.734	−0.238	0.4173	0.041*
C8	0.7395 (4)	−0.11076 (18)	0.50764 (17)	0.0301 (6)
H8	0.7034	−0.151	0.5605	0.036*
C9	0.7730 (3)	−0.00172 (18)	0.51646 (16)	0.0251 (5)
H9	0.7577	0.0322	0.5749	0.03*
C10	0.8301 (3)	0.06008 (17)	0.43913 (15)	0.0215 (5)
C11	0.8716 (3)	0.17464 (18)	0.44429 (16)	0.0220 (5)
C12	0.8560 (3)	0.23193 (18)	0.52831 (16)	0.0234 (5)
H12	0.8199	0.1937	0.5823	0.028*
N13	0.8891 (3)	0.33555 (15)	0.53540 (13)	0.0240 (4)
H13	0.9142	0.3715	0.4844	0.029*
C14	0.8867 (3)	0.39324 (17)	0.62052 (15)	0.0231 (5)
C15	0.9417 (3)	0.34405 (19)	0.70234 (17)	0.0274 (5)
H15	0.98	0.2709	0.7018	0.033*
C16	0.9410 (4)	0.4015 (2)	0.78481 (18)	0.0317 (6)
H16	0.9789	0.368	0.8407	0.038*
C17	0.8846 (4)	0.5081 (2)	0.78508 (18)	0.0331 (6)
H17	0.8822	0.5475	0.8415	0.04*
C18	0.8319 (4)	0.55710 (19)	0.70344 (18)	0.0313 (6)
H18	0.7946	0.6304	0.7046	0.038*
C19	0.8321 (3)	0.50159 (18)	0.61949 (16)	0.0257 (5)
C20	0.7722 (4)	0.55641 (19)	0.53136 (18)	0.0325 (6)
H20A	0.8649	0.5461	0.4834	0.049*
H20B	0.7558	0.6337	0.5429	0.049*
H20C	0.6571	0.5251	0.5105	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0429 (11)	0.0269 (8)	0.0292 (9)	−0.0071 (8)	−0.0015 (8)	0.0044 (7)
C2	0.0240 (13)	0.0271 (11)	0.0278 (12)	−0.0004 (10)	−0.0033 (10)	0.0019 (10)
C3	0.0268 (13)	0.0369 (13)	0.0218 (11)	−0.0019 (11)	0.0004 (10)	0.0019 (10)
C4	0.0273 (13)	0.0356 (13)	0.0206 (11)	0.0033 (10)	−0.0018 (10)	−0.0038 (9)
C5	0.0204 (12)	0.0269 (11)	0.0251 (11)	0.0040 (10)	−0.0032 (9)	−0.0015 (9)
C6	0.0359 (15)	0.0294 (12)	0.0284 (12)	0.0050 (11)	−0.0046 (11)	−0.0042 (10)
C7	0.0405 (16)	0.0231 (11)	0.0378 (14)	−0.0012 (12)	−0.0053 (12)	−0.0001 (10)
C8	0.0313 (14)	0.0263 (11)	0.0328 (13)	−0.0032 (10)	−0.0020 (11)	0.0078 (10)
C9	0.0258 (12)	0.0248 (10)	0.0247 (11)	0.0008 (10)	−0.0004 (10)	0.0003 (9)
C10	0.0174 (12)	0.0234 (10)	0.0236 (11)	0.0021 (9)	−0.0014 (9)	0.0001 (9)
C11	0.0193 (11)	0.0240 (10)	0.0227 (11)	0.0010 (9)	−0.0007 (9)	0.0003 (9)
C12	0.0188 (11)	0.0252 (10)	0.0261 (12)	0.0003 (9)	0.0026 (9)	0.0018 (9)
N13	0.0240 (10)	0.0243 (9)	0.0239 (10)	−0.0020 (8)	0.0003 (8)	0.0011 (8)
C14	0.0191 (11)	0.0262 (11)	0.0239 (12)	−0.0041 (9)	0.0030 (10)	−0.0018 (9)
C15	0.0263 (12)	0.0264 (11)	0.0295 (12)	−0.0035 (10)	−0.0016 (10)	0.0024 (10)
C16	0.0307 (14)	0.0379 (13)	0.0266 (12)	−0.0086 (11)	−0.0042 (11)	0.0023 (10)
C17	0.0348 (14)	0.0380 (13)	0.0266 (12)	−0.0087 (11)	0.0018 (11)	−0.0082 (11)
C18	0.0311 (14)	0.0263 (11)	0.0367 (13)	−0.0020 (10)	0.0026 (12)	−0.0032 (10)
C19	0.0246 (12)	0.0247 (11)	0.0278 (12)	−0.0036 (10)	0.0015 (10)	0.0015 (9)
C20	0.0359 (15)	0.0278 (11)	0.0338 (13)	0.0017 (11)	−0.0001 (12)	0.0042 (10)

O1—C2	1.301 (3)	C12—N13	1.312 (3)
C2—C11	1.433 (3)	C12—H12	0.95
C2—C3	1.439 (3)	N13—C14	1.422 (3)
C3—C4	1.339 (3)	N13—H13	0.88
C3—H3	0.95	C14—C15	1.390 (3)
C4—C5	1.436 (3)	C14—C19	1.403 (3)
C4—H4	0.95	C15—C16	1.387 (3)
C5—C6	1.405 (3)	C15—H15	0.95
C5—C10	1.412 (3)	C16—C17	1.385 (3)
C6—C7	1.370 (3)	C16—H16	0.95
C6—H6	0.95	C17—C18	1.382 (4)
C7—C8	1.395 (3)	C17—H17	0.95
C7—H7	0.95	C18—C19	1.394 (3)
C8—C9	1.380 (3)	C18—H18	0.95
C8—H8	0.95	C19—C20	1.508 (3)
C9—C10	1.418 (3)	C20—H20A	0.98
C9—H9	0.95	C20—H20B	0.98
C10—C11	1.455 (3)	C20—H20C	0.98
C11—C12	1.410 (3)
O1—C2—C11	121.6 (2)	N13—C12—C11	123.1 (2)
O1—C2—C3	119.5 (2)	N13—C12—H12	118.5
C11—C2—C3	118.9 (2)	C11—C12—H12	118.5
C4—C3—C2	121.1 (2)	C12—N13—C14	123.91 (19)
C4—C3—H3	119.5	C12—N13—H13	118
C2—C3—H3	119.5	C14—N13—H13	118
C3—C4—C5	122.1 (2)	C15—C14—C19	120.9 (2)
C3—C4—H4	119	C15—C14—N13	120.7 (2)
C5—C4—H4	119	C19—C14—N13	118.4 (2)
C6—C5—C10	120.2 (2)	C16—C15—C14	120.2 (2)
C6—C5—C4	120.4 (2)	C16—C15—H15	119.9
C10—C5—C4	119.5 (2)	C14—C15—H15	119.9
C7—C6—C5	121.3 (2)	C17—C16—C15	119.6 (2)
C7—C6—H6	119.4	C17—C16—H16	120.2
C5—C6—H6	119.4	C15—C16—H16	120.2
C6—C7—C8	119.0 (2)	C18—C17—C16	120.1 (2)
C6—C7—H7	120.5	C18—C17—H17	120
C8—C7—H7	120.5	C16—C17—H17	120
C9—C8—C7	121.2 (2)	C17—C18—C19	121.6 (2)
C9—C8—H8	119.4	C17—C18—H18	119.2
C7—C8—H8	119.4	C19—C18—H18	119.2
C8—C9—C10	120.7 (2)	C18—C19—C14	117.7 (2)
C8—C9—H9	119.7	C18—C19—C20	120.7 (2)
C10—C9—H9	119.7	C14—C19—C20	121.6 (2)
C5—C10—C9	117.6 (2)	C19—C20—H20A	109.5
C5—C10—C11	119.1 (2)	C19—C20—H20B	109.5
C9—C10—C11	123.3 (2)	H20A—C20—H20B	109.5
C12—C11—C2	119.3 (2)	C19—C20—H20C	109.5
C12—C11—C10	121.2 (2)	H20A—C20—H20C	109.5
C2—C11—C10	119.4 (2)	H20B—C20—H20C	109.5
O1—C2—C3—C4	179.7 (2)	C5—C10—C11—C12	−179.6 (2)
C11—C2—C3—C4	0.4 (4)	C9—C10—C11—C12	−0.4 (3)
C2—C3—C4—C5	0.5 (4)	C5—C10—C11—C2	0.0 (3)
C3—C4—C5—C6	179.7 (2)	C9—C10—C11—C2	179.3 (2)
C3—C4—C5—C10	−1.1 (4)	C2—C11—C12—N13	1.6 (3)
C10—C5—C6—C7	−1.8 (4)	C10—C11—C12—N13	−178.8 (2)
C4—C5—C6—C7	177.4 (2)	C11—C12—N13—C14	−175.4 (2)
C5—C6—C7—C8	1.5 (4)	C12—N13—C14—C15	33.7 (3)
C6—C7—C8—C9	0.0 (4)	C12—N13—C14—C19	−148.0 (2)
C7—C8—C9—C10	−1.1 (4)	C19—C14—C15—C16	0.9 (4)
C6—C5—C10—C9	0.7 (3)	N13—C14—C15—C16	179.2 (2)
C4—C5—C10—C9	−178.5 (2)	C14—C15—C16—C17	0.1 (4)
C6—C5—C10—C11	−180.0 (2)	C15—C16—C17—C18	−0.9 (4)
C4—C5—C10—C11	0.8 (3)	C16—C17—C18—C19	0.6 (4)
C8—C9—C10—C5	0.7 (3)	C17—C18—C19—C14	0.4 (4)
C8—C9—C10—C11	−178.6 (2)	C17—C18—C19—C20	179.4 (3)
O1—C2—C11—C12	−0.2 (4)	C15—C14—C19—C18	−1.2 (3)
C3—C2—C11—C12	179.0 (2)	N13—C14—C19—C18	−179.5 (2)
O1—C2—C11—C10	−179.9 (2)	C15—C14—C19—C20	179.9 (2)
C3—C2—C11—C10	−0.6 (3)	N13—C14—C19—C20	1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···O1	0.88	1.85	2.546 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13⋯O1	0.88	1.85	2.546 (3)	134