4-(2-Hydroxy­benzyl­idene­amino)­benzonitrile

Gong, X.-X.; Xu, H.-J.

doi:10.1107/S160053680801564X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1188

doi:10.1107/S160053680801564X

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4-(2-Hydroxybenzylideneamino)benzonitrile

Xing-Xuan Gong ^a and Hai-Jun Xu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: xuhj@seu.edu.cn

(Received 26 April 2008; accepted 24 May 2008; online 7 June 2008)

The molecule of the title compound, C₁₄H₁₀N₂O, is nearly planar. There is a strong intramolecular O—H⋯N hydrogen bond between the imine and hydroxy groups. The configuration with respect to the C=N double bond is anti (1E).

Related literature

For related literature, see: Allen et al. (1987 ); Chen et al. (2008 ); Cheng et al. (2005 , 2006 ); Elmah et al. (1999 ); May et al. (2004 ); Weber et al. (2007 ); Xu et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₀N₂O
M_r = 222.24
Monoclinic, C 2/c
a = 28.071 (6) Å
b = 5.8471 (12) Å
c = 14.687 (3) Å
β = 109.91 (3)°
V = 2266.6 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.12 × 0.11 × 0.03 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.915, T_max = 1.00 (expected range = 0.913–0.997)
9782 measured reflections
2223 independent reflections
971 reflections with I > 2σ(I)
R_int = 0.132

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.176
S = 0.97
2223 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.18 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—H1B⋯N1	0.82	1.88	2.609 (4)	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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801564X/dn2347sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801564X/dn2347Isup2.hkl

checkCIF report

Comment top

The Schiff base compounds have received considerable attention for several decades, primarily due to their importance in the development of coordination chemistry related to magnetism (Weber et al., 2007), catalysis (Chen et al., 2008) and biological process (May et al.,2004). Recently, we have reported a Schiff base compound (Xu et al., 2008). As an extention of our work on the structural characterization of Schiff base compounds, the title compound has been synthesized.

The molecule of the title compound is nearly planar, the two aromatic rings are only twisted by a dihedral angle 3.28 (18) ° (Fig. 1), As expected, the molecule displays a trans configuration about the central C7=N1 imine double bond. Bond lengths and bond angles in the compound are within normal ranges (Allen et al., 1987). The C7=N1 bond length of 1.280 (4) Å indicates a high degree of double-bond character comparable with the corresponding bond lengths in other Schiff bases (1.280 (2) Å; Elmah et al., 1999).

A strong O–H···N intramolecular hydrogen-bond interaction is observed in the molecular structure (Table 1 ) as also found in previous reports (Xu et al., 2008; Cheng et al., 2006, 2005).

Related literature top

For related literature, see: Allen et al. (1987); Chen et al. (2008); Cheng et al. (2005, 2006); Elmah et al. (1999); May et al. (2004); Weber et al. (2007); Xu et al. (2008).

Experimental top

All chemicals were obtained from commercial sources and used without further purification except for salicylaldehyde which is distilled under reduced pressure before use. 4-aminobenzonitrile (1.18 g, 10 mmol) and salicylaldehyde (1.22 g, 10 mmol) were dissolved in ethanol (20 ml). The mixture was heated to reflux for 4 h, then cooled to room temperature overnight then large amounts of a yellow precipitate were formed. Yellow crystals were obtained by recrystallization from ethyl alcohol(yield: 81%). ¹H-NMR(CDCl₃, 300 MHz): δ6.98 (t, 1 H), 7.04 (d, 1 H), 7.34(d, 2 H), 7.43 (t, 2 H), 7.72 (d, 2H), 8.61 (s, 1 H). ¹³C-NMR (CDCl₃)δ110.1, 117.4, 118.6, 118.7, 119.4, 122.1, 132.8, 133.5, 134.3, 152.4, 161.2, 165.0. Esi-MS: calcd for C₁₄H₉N₂O – H m/z 221.24, found 221.34. Suitable single crystals of the title compound were obtained after one week by slow evaporation from an ethyl alcohol solution.

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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

4-(2-Hydroxybenzylideneamino)benzonitrile top

Crystal data top

C₁₄H₁₀N₂O	F(000) = 928
M_r = 222.24	D_x = 1.303 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7031 reflections
a = 28.071 (6) Å	θ = 3.1–29.0°
b = 5.8471 (12) Å	µ = 0.08 mm⁻¹
c = 14.687 (3) Å	T = 293 K
β = 109.91 (3)°	Block, yellow
V = 2266.6 (9) Å³	0.12 × 0.11 × 0.03 mm
Z = 8

Data collection top

Rigaku Mercury2 (2x2 bin mode) diffractometer	2223 independent reflections
Radiation source: fine-focus sealed tube	971 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.132
Detector resolution: 13.6612 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −34→34
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→7
T_min = 0.915, T_max = 1.00	l = −18→18
9782 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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0584P)²] where P = (F_o² + 2F_c²)/3
2223 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₄H₁₀N₂O	V = 2266.6 (9) Å³
M_r = 222.24	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.071 (6) Å	µ = 0.08 mm⁻¹
b = 5.8471 (12) Å	T = 293 K
c = 14.687 (3) Å	0.12 × 0.11 × 0.03 mm
β = 109.91 (3)°

Data collection top

Rigaku Mercury2 (2x2 bin mode) diffractometer	2223 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	971 reflections with I > 2σ(I)
T_min = 0.915, T_max = 1.00	R_int = 0.132
9782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 0.97	Δρ_max = 0.18 e Å⁻³
2223 reflections	Δρ_min = −0.19 e Å⁻³
154 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C13	0.34671 (13)	0.0317 (6)	0.9348 (3)	0.0487 (10)
H14A	0.3362	−0.0983	0.9592	0.058*
C7	0.22581 (13)	0.3041 (6)	0.8582 (2)	0.0466 (10)
H13A	0.2331	0.4471	0.8385	0.056*
N1	0.26153 (10)	0.1571 (4)	0.8889 (2)	0.0443 (8)
C3	0.11223 (12)	0.0032 (6)	0.8792 (3)	0.0504 (10)
H12A	0.1038	−0.1343	0.9017	0.061*
C10	0.37793 (13)	0.4177 (6)	0.8639 (3)	0.0527 (11)
H11A	0.3889	0.5492	0.8414	0.063*
C11	0.41195 (13)	0.2453 (7)	0.9055 (3)	0.0479 (10)
C8	0.31195 (12)	0.1997 (6)	0.8920 (2)	0.0396 (9)
C9	0.32765 (13)	0.3953 (6)	0.8557 (3)	0.0485 (10)
H8A	0.3045	0.5095	0.8262	0.058*
O1	0.19746 (9)	−0.1128 (4)	0.92932 (18)	0.0630 (8)
H1B	0.2253	−0.0677	0.9302	0.095*
C2	0.16187 (13)	0.0481 (6)	0.8873 (3)	0.0439 (9)
C1	0.17471 (12)	0.2547 (6)	0.8532 (2)	0.0384 (9)
C6	0.13639 (13)	0.4125 (6)	0.8116 (3)	0.0497 (10)
H5A	0.1444	0.5505	0.7888	0.060*
C14	0.46381 (14)	0.2676 (6)	0.9108 (3)	0.0591 (12)
C12	0.39627 (13)	0.0523 (6)	0.9420 (3)	0.0522 (10)
H3A	0.4193	−0.0625	0.9713	0.063*
C4	0.07550 (14)	0.1627 (7)	0.8377 (3)	0.0545 (11)
H2A	0.0422	0.1319	0.8323	0.065*
C5	0.08702 (14)	0.3697 (7)	0.8034 (3)	0.0602 (12)
H1A	0.0618	0.4769	0.7754	0.072*
N2	0.50503 (13)	0.2785 (6)	0.9144 (3)	0.0899 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C13	0.052 (2)	0.041 (2)	0.055 (3)	0.0006 (19)	0.020 (2)	0.0061 (19)
C7	0.058 (3)	0.045 (2)	0.038 (2)	−0.009 (2)	0.0190 (19)	0.0019 (18)
N1	0.0419 (17)	0.0436 (18)	0.048 (2)	−0.0016 (15)	0.0161 (15)	0.0017 (15)
C3	0.051 (2)	0.051 (2)	0.051 (3)	−0.007 (2)	0.019 (2)	0.003 (2)
C10	0.055 (2)	0.052 (2)	0.056 (3)	−0.011 (2)	0.026 (2)	0.001 (2)
C11	0.042 (2)	0.055 (2)	0.049 (2)	−0.005 (2)	0.0189 (19)	0.001 (2)
C8	0.038 (2)	0.046 (2)	0.036 (2)	−0.0043 (18)	0.0143 (17)	−0.0006 (18)
C9	0.049 (2)	0.046 (2)	0.051 (3)	0.0014 (19)	0.0181 (19)	0.0106 (19)
O1	0.0538 (17)	0.0503 (16)	0.087 (2)	0.0003 (13)	0.0273 (15)	0.0197 (14)
C2	0.042 (2)	0.045 (2)	0.044 (2)	0.0030 (19)	0.0135 (19)	0.0047 (18)
C1	0.038 (2)	0.042 (2)	0.035 (2)	−0.0046 (18)	0.0124 (17)	−0.0021 (17)
C6	0.049 (2)	0.050 (2)	0.053 (3)	−0.001 (2)	0.0212 (19)	0.009 (2)
C14	0.045 (3)	0.061 (3)	0.070 (3)	0.002 (2)	0.017 (2)	0.009 (2)
C12	0.044 (2)	0.050 (2)	0.062 (3)	0.0027 (19)	0.017 (2)	0.005 (2)
C4	0.042 (2)	0.069 (3)	0.056 (3)	−0.003 (2)	0.021 (2)	0.003 (2)
C5	0.054 (3)	0.065 (3)	0.063 (3)	0.014 (2)	0.021 (2)	0.010 (2)
N2	0.050 (2)	0.097 (3)	0.124 (4)	0.002 (2)	0.033 (2)	0.029 (3)

Geometric parameters (Å, º) top

C13—C12	1.364 (4)	C11—C14	1.437 (5)
C13—C8	1.376 (4)	C8—C9	1.395 (4)
C13—H14A	0.9300	C9—H8A	0.9300
C7—N1	1.280 (4)	O1—C2	1.358 (4)
C7—C1	1.440 (4)	O1—H1B	0.8200
C7—H13A	0.9300	C2—C1	1.401 (4)
N1—C8	1.422 (4)	C1—C6	1.391 (4)
C3—C4	1.370 (4)	C6—C5	1.373 (4)
C3—C2	1.383 (4)	C6—H5A	0.9300
C3—H12A	0.9300	C14—N2	1.142 (4)
C10—C11	1.380 (5)	C12—H3A	0.9300
C10—C9	1.381 (4)	C4—C5	1.391 (5)
C10—H11A	0.9300	C4—H2A	0.9300
C11—C12	1.384 (4)	C5—H1A	0.9300

C12—C13—C8	121.2 (3)	C8—C9—H8A	120.3
C12—C13—H14A	119.4	C2—O1—H1B	109.5
C8—C13—H14A	119.4	O1—C2—C3	118.1 (3)
N1—C7—C1	122.0 (3)	O1—C2—C1	121.4 (3)
N1—C7—H13A	119.0	C3—C2—C1	120.5 (3)
C1—C7—H13A	119.0	C6—C1—C2	118.3 (3)
C7—N1—C8	123.0 (3)	C6—C1—C7	119.8 (3)
C4—C3—C2	119.5 (3)	C2—C1—C7	121.8 (3)
C4—C3—H12A	120.2	C5—C6—C1	121.6 (3)
C2—C3—H12A	120.2	C5—C6—H5A	119.2
C11—C10—C9	120.1 (3)	C1—C6—H5A	119.2
C11—C10—H11A	119.9	N2—C14—C11	178.0 (5)
C9—C10—H11A	119.9	C13—C12—C11	119.5 (3)
C10—C11—C12	120.2 (3)	C13—C12—H3A	120.3
C10—C11—C14	119.5 (3)	C11—C12—H3A	120.3
C12—C11—C14	120.2 (4)	C3—C4—C5	121.4 (3)
C13—C8—C9	119.5 (3)	C3—C4—H2A	119.3
C13—C8—N1	115.6 (3)	C5—C4—H2A	119.3
C9—C8—N1	124.9 (3)	C6—C5—C4	118.6 (3)
C10—C9—C8	119.4 (3)	C6—C5—H1A	120.7
C10—C9—H8A	120.3	C4—C5—H1A	120.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1	0.82	1.88	2.609 (4)	147

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O
M_r	222.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.071 (6), 5.8471 (12), 14.687 (3)
β (°)	109.91 (3)
V (Å³)	2266.6 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.12 × 0.11 × 0.03

Data collection
Diffractometer	Rigaku Mercury2 (2x2 bin mode) diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.915, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	9782, 2223, 971
R_int	0.132
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.176, 0.97
No. of reflections	2223
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

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—H1B···N1	0.82	1.88	2.609 (4)	146.6

Acknowledgements

Hai-Jun Xu acknowledges a Start-up Grant from Southeast University, People's Republic of China.

References

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