(Z)-2-[(2-Hydr­oxy-1-naphth­yl)methyl­eneamino]benzonitrile

Zhou, J.-C.; Zhang, C.-M.; Li, N.-X.; Zhang, Z.-Y.

doi:10.1107/S1600536809023708

organic compounds

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Volume 65| Part 7| July 2009| Page o1700

doi:10.1107/S1600536809023708

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(Z)-2-[(2-Hydroxy-1-naphthyl)methyleneamino]benzonitrile

Jian-Cheng Zhou,^a ^* Chuan-Ming Zhang,^a Nai-Xu Li ^a and Zheng-Yun Zhang ^a

^aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: jczhou@seu.edu.cn

(Received 4 June 2009; accepted 20 June 2009; online 27 June 2009)

The title compound, C₁₈H₁₂N₂O, 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 intramolecular O—H⋯N hydrogen-bond interaction 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_r = 272.30
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.159
S = 1.10
2706 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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

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.

Supporting information

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

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

checkCIF report

Comment top

Schiff base compounds have received considerable attention for many years because these compounds play an important role in coordination chemistry related to magnetism (Weber et al., 2007) and catalysis (Chen et al., 2008).Our group is interested in the synthesis and preparation of Schiff bases. Here, we report the synthesis and crystal structure of the title compound.

Figure 1 shows an ORTEP plot of the title compound. The molecule adopts the phenol–imine tautomeric form with a strong intramolecular O—H···N hydrogen bond. The C11N1 and C2—O1 bond lengths [1.296 (3) and 1.324 (3) Å, respectively] are comparable to corresponding values observed in a similar phenol–imine tautomeric structures (e.g. Petek et al., 2007), while different geometry is observed in the case of zwitterionic molecules (Elmali et al., 2001; Yüce et al., 2006). Phenyl and naphthalyl rings, A (C12···C17) and B (C1···C10), are, of course, planar, and the dihedral angle between them is 8.98 (9)°. The molecule displays a trans configuration about the central CN imine bond. Molecules are packed in the crystal at van der Waals distances.

Related literature top

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 top

2-Aminobenzonitrile (0.59 g, 5 mmol) and 2-hydroxynaphthalene-1-carbaldehyde (0.861 g, 5 mmol) were dissolved in ethanol (25 ml). The resulting mixture was refluxed for 5 h and cooled to room temperature. The solid product was collected by filtration. Crystals suitable for X-ray diffraction studies were obtained on slow evaporation at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

(Z)-2-[(2-Hydroxy-1-naphthyl)methyleneamino]benzonitrile top

Crystal data top

C₁₈H₁₂N₂O	F(000) = 568
M_r = 272.30	D_x = 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

Data collection top

Rigaku SCXmini diffractometer	2706 independent reflections
Radiation source: fine-focus sealed tube	1803 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 13.6612 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
T_min = 0.973, T_max = 0.979	l = −18→18
12133 measured reflections

Refinement top

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(F_o²) + (0.0672P)² + 0.1372P] where P = (F_o² + 2F_c²)/3
2706 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³
0 constraints

Crystal data top

C₁₈H₁₂N₂O	V = 1380.4 (2) Å³
M_r = 272.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4640 (13) Å	µ = 0.08 mm⁻¹
b = 7.4450 (6) Å	T = 293 K
c = 15.4090 (11) Å	0.20 × 0.20 × 0.20 mm
β = 116.660 (6)°

Data collection top

Rigaku SCXmini diffractometer	2706 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1803 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.979	R_int = 0.056
12133 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.10	Δρ_max = 0.20 e Å⁻³
2706 reflections	Δρ_min = −0.18 e Å⁻³
190 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂O
M_r	272.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.4640 (13), 7.4450 (6), 15.4090 (11)
β (°)	116.660 (6)
V (Å³)	1380.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.973, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	12133, 2706, 1803
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.159, 1.10
No. of reflections	2706
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.82	2.551 (2)	147.3

References

Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170–2171. Web of Science CSD CrossRef PubMed CAS Google Scholar
Elmali, A., Elerman, Y. & Svoboda, I. (2001). Acta Cryst. C57, 485–486. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Petek, H., Albayrak, Ç., Ağar, E., Ískeleli, N. O. & Şenel, İ. (2007). Acta Cryst. E63, o810–o812. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159–1162. Web of Science CSD CrossRef CAS Google Scholar
Yüce, S., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, o389–o393. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1700

doi:10.1107/S1600536809023708

Open

access