(Z)-2-[(2-Hydr-oxy-1-naphth-yl)methyl-eneamino]benzonitrile.

The title compound, C(18)H(12)N(2)O, crystallizes in a phenol-imine tautomeric form with a Z conformation for the imine functionality. The dihedral angle between the aromatic rings is 8.98 (9)°. A strong intra-molecular O-H⋯N hydrogen-bond inter-action between the hydroxyl group and imine N atom occurs.

Related literature

For general properties of Schiff base compounds, see: Weber et al. (2007 ▶); Chen et al. (2008 ▶). For related structures, see: Elmali et al. (2001 ▶); Yüce et al. (2006 ▶); Petek et al. (2007 ▶).

Experimental

Crystal data

C18H12N2O

M = 272.30

Monoclinic,

a = 13.4640 (13) Å

b = 7.4450 (6) Å

c = 15.4090 (11) Å

β = 116.660 (6)°

V = 1380.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.973, T max = 0.979

12133 measured reflections

2706 independent reflections

1803 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.159

S = 1.10

2706 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023708/bh2232sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023708/bh2232Isup2.hkl

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

C18H12N2O	F(000) = 568
Mr = 272.30	Dx = 1.310 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2198 reflections
a = 13.4640 (13) Å	θ = 2.7–27.5°
b = 7.4450 (6) Å	µ = 0.08 mm−1
c = 15.4090 (11) Å	T = 293 K
β = 116.660 (6)°	Block, pale yellow
V = 1380.4 (2) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2706 independent reflections
Radiation source: fine-focus sealed tube	1803 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.973, Tmax = 0.979	l = −18→18
12133 measured 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.1372P] where P = (Fo2 + 2Fc2)/3
2706 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
O1	0.22890 (15)	0.5907 (3)	−0.07648 (12)	0.0792 (6)
H1A	0.1718	0.6436	−0.0852	0.119*
N1	0.07487 (14)	0.7038 (2)	−0.03712 (12)	0.0490 (5)
N2	0.0188 (2)	0.7966 (4)	−0.27347 (16)	0.0894 (8)
C1	0.24373 (17)	0.5812 (3)	0.08450 (16)	0.0465 (5)
C11	0.13677 (17)	0.6610 (3)	0.05282 (16)	0.0459 (5)
H11A	0.1105	0.6831	0.0983	0.055*
C12	−0.03185 (17)	0.7809 (3)	−0.07090 (15)	0.0439 (5)
C13	−0.08320 (18)	0.8360 (3)	−0.16755 (16)	0.0500 (6)
C10	0.30954 (17)	0.5267 (3)	0.18411 (16)	0.0477 (6)
C6	0.4729 (2)	0.3710 (3)	0.3064 (2)	0.0674 (7)
H6A	0.5381	0.3068	0.3228	0.081*
C5	0.41020 (19)	0.4302 (3)	0.21022 (18)	0.0550 (6)
C9	0.2793 (2)	0.5638 (3)	0.25909 (17)	0.0582 (6)
H9A	0.2150	0.6290	0.2451	0.070*
C2	0.2839 (2)	0.5440 (3)	0.01600 (18)	0.0569 (6)
C17	−0.08801 (19)	0.8058 (3)	−0.01468 (16)	0.0528 (6)
H17A	−0.0552	0.7709	0.0502	0.063*
C16	−0.1922 (2)	0.8823 (3)	−0.05539 (18)	0.0579 (6)
H16A	−0.2292	0.8983	−0.0175	0.069*
C14	−0.1883 (2)	0.9135 (3)	−0.20763 (18)	0.0596 (7)
H14A	−0.2216	0.9502	−0.2722	0.072*
C15	−0.2426 (2)	0.9355 (3)	−0.15123 (19)	0.0605 (7)
H15A	−0.3133	0.9862	−0.1776	0.073*
C4	0.4449 (2)	0.3949 (3)	0.1372 (2)	0.0664 (7)
H4A	0.5105	0.3316	0.1537	0.080*
C3	0.3859 (2)	0.4500 (4)	0.0453 (2)	0.0684 (8)
H3A	0.4121	0.4264	−0.0001	0.082*
C18	−0.0262 (2)	0.8130 (4)	−0.22658 (17)	0.0624 (7)
C8	0.3432 (2)	0.5053 (4)	0.35194 (19)	0.0716 (8)
H8A	0.3218	0.5322	0.4001	0.086*
C7	0.4394 (2)	0.4064 (4)	0.3755 (2)	0.0749 (8)
H7A	0.4808	0.3647	0.4386	0.090*

	U11	U22	U33	U12	U13	U23
O1	0.0708 (12)	0.1177 (17)	0.0570 (11)	0.0071 (11)	0.0359 (10)	−0.0072 (11)
N1	0.0484 (11)	0.0551 (12)	0.0439 (11)	−0.0048 (9)	0.0211 (9)	−0.0043 (9)
N2	0.0851 (17)	0.134 (2)	0.0598 (15)	0.0022 (16)	0.0421 (14)	0.0019 (14)
C1	0.0461 (12)	0.0447 (12)	0.0530 (14)	−0.0078 (10)	0.0259 (11)	−0.0084 (10)
C11	0.0498 (13)	0.0447 (12)	0.0473 (13)	−0.0059 (10)	0.0256 (11)	−0.0057 (10)
C12	0.0428 (12)	0.0450 (12)	0.0449 (12)	−0.0070 (10)	0.0205 (10)	−0.0072 (10)
C13	0.0498 (13)	0.0542 (14)	0.0475 (13)	−0.0075 (11)	0.0232 (11)	−0.0025 (11)
C10	0.0461 (12)	0.0406 (12)	0.0559 (14)	−0.0069 (10)	0.0224 (11)	−0.0025 (10)
C6	0.0505 (14)	0.0529 (15)	0.083 (2)	0.0003 (12)	0.0163 (15)	0.0074 (14)
C5	0.0471 (13)	0.0417 (12)	0.0716 (17)	−0.0036 (11)	0.0227 (13)	−0.0049 (12)
C9	0.0552 (14)	0.0652 (16)	0.0542 (15)	0.0035 (12)	0.0244 (12)	0.0035 (12)
C2	0.0525 (14)	0.0638 (16)	0.0570 (15)	−0.0058 (12)	0.0269 (12)	−0.0093 (12)
C17	0.0563 (14)	0.0571 (15)	0.0495 (13)	−0.0069 (12)	0.0278 (11)	−0.0025 (11)
C16	0.0577 (15)	0.0566 (15)	0.0701 (17)	−0.0052 (12)	0.0383 (13)	−0.0092 (13)
C14	0.0609 (15)	0.0595 (15)	0.0537 (15)	−0.0002 (12)	0.0214 (13)	0.0031 (12)
C15	0.0502 (14)	0.0540 (15)	0.0726 (18)	0.0010 (11)	0.0233 (13)	−0.0023 (13)
C4	0.0489 (14)	0.0572 (16)	0.092 (2)	0.0015 (12)	0.0304 (15)	−0.0130 (14)
C3	0.0612 (16)	0.0731 (19)	0.084 (2)	−0.0025 (14)	0.0443 (15)	−0.0200 (15)
C18	0.0610 (15)	0.0807 (19)	0.0448 (14)	−0.0019 (14)	0.0231 (12)	0.0029 (13)
C8	0.0692 (17)	0.085 (2)	0.0578 (16)	0.0000 (16)	0.0261 (14)	0.0081 (14)
C7	0.0678 (18)	0.0729 (19)	0.0686 (18)	0.0019 (14)	0.0169 (15)	0.0185 (15)

O1—C2	1.324 (3)	C5—C4	1.423 (3)
O1—H1A	0.8200	C9—C8	1.368 (3)
N1—C11	1.296 (3)	C9—H9A	0.9300
N1—C12	1.412 (3)	C2—C3	1.423 (3)
N2—C18	1.139 (3)	C17—C16	1.377 (3)
C1—C2	1.412 (3)	C17—H17A	0.9300
C1—C11	1.426 (3)	C16—C15	1.378 (3)
C1—C10	1.444 (3)	C16—H16A	0.9300
C11—H11A	0.9300	C14—C15	1.374 (3)
C12—C17	1.394 (3)	C14—H14A	0.9300
C12—C13	1.393 (3)	C15—H15A	0.9300
C13—C14	1.390 (3)	C4—C3	1.340 (4)
C13—C18	1.439 (3)	C4—H4A	0.9300
C10—C9	1.414 (3)	C3—H3A	0.9300
C10—C5	1.423 (3)	C8—C7	1.390 (4)
C6—C7	1.355 (4)	C8—H8A	0.9300
C6—C5	1.408 (3)	C7—H7A	0.9300
C6—H6A	0.9300
C2—O1—H1A	109.5	O1—C2—C3	117.6 (2)
C11—N1—C12	123.63 (18)	C1—C2—C3	119.9 (2)
C2—C1—C11	119.5 (2)	C16—C17—C12	119.8 (2)
C2—C1—C10	118.8 (2)	C16—C17—H17A	120.1
C11—C1—C10	121.64 (19)	C12—C17—H17A	120.1
N1—C11—C1	122.3 (2)	C15—C16—C17	121.3 (2)
N1—C11—H11A	118.8	C15—C16—H16A	119.4
C1—C11—H11A	118.8	C17—C16—H16A	119.4
C17—C12—C13	118.5 (2)	C15—C14—C13	119.6 (2)
C17—C12—N1	124.8 (2)	C15—C14—H14A	120.2
C13—C12—N1	116.66 (19)	C13—C14—H14A	120.2
C14—C13—C12	121.0 (2)	C14—C15—C16	119.8 (2)
C14—C13—C18	119.6 (2)	C14—C15—H15A	120.1
C12—C13—C18	119.4 (2)	C16—C15—H15A	120.1
C9—C10—C5	117.0 (2)	C3—C4—C5	122.0 (2)
C9—C10—C1	123.3 (2)	C3—C4—H4A	119.0
C5—C10—C1	119.6 (2)	C5—C4—H4A	119.0
C7—C6—C5	120.9 (3)	C4—C3—C2	121.0 (2)
C7—C6—H6A	119.6	C4—C3—H3A	119.5
C5—C6—H6A	119.6	C2—C3—H3A	119.5
C6—C5—C4	121.4 (2)	N2—C18—C13	179.3 (3)
C6—C5—C10	120.0 (2)	C9—C8—C7	121.1 (3)
C4—C5—C10	118.6 (2)	C9—C8—H8A	119.4
C8—C9—C10	121.1 (2)	C7—C8—H8A	119.4
C8—C9—H9A	119.5	C6—C7—C8	119.8 (3)
C10—C9—H9A	119.5	C6—C7—H7A	120.1
O1—C2—C1	122.4 (2)	C8—C7—H7A	120.1

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.82	2.551 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.82	2.551 (2)	147