(E)-3-(2-Hydr­oxy-3-methoxy­benzyl­idene­amino)benzonitrile

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

doi:10.1107/S1600536809029225

organic compounds

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Volume 65| Part 8| August 2009| Page o2017

doi:10.1107/S1600536809029225

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(E)-3-(2-Hydroxy-3-methoxybenzylideneamino)benzonitrile

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

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

(Received 17 July 2009; accepted 23 July 2009; online 29 July 2009)

The molecule of the title compound, C₁₅H₁₂N₂O₂, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 30.46 (14)°. A strong intramolecular O—H⋯O hydrogen bond stabilizes the molecular structure.

Related literature

For the magnetic and biological properties of Schiff bases, see: May et al. (2004 ); Weber et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₂N₂O₂
M_r = 252.27
Monoclinic, C c
a = 15.476 (5) Å
b = 5.9927 (19) Å
c = 15.413 (7) Å
β = 116.127 (3)°
V = 1283.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.973, T_max = 0.991
5235 measured reflections
1470 independent reflections
1808 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.124
S = 1.03
1470 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	2.18	2.645 (4)	117

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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/S1600536809029225/rz2356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029225/rz2356Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have received considerable attention for many years because these compounds play important role in coordination chemistry related to magnetism (Weber, et al., 2007) and biological process (May, et al.,2004). Our group is interested in the synthesis and characterization of Schiff base ligands. Here, we report the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The molecule displays a trans configuration about the central C=N double bond and adopts the phenol–imine tautomeric form, with a strong intramolecular O—H···O hydrogen bond (Table 1). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angle between two benzene rings is 30.46 (14)°. The crystal packing is stabilized only by van der Waals interactions.

Related literature top

For the magnetic and biological properties of Schiff bases, see: May et al. (2004); Weber et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

3-Aminobenzonitrile (0.59 g, 5 mmol) and 2-hydroxynaphthalene-1-carbaldehyde (0.760 g, 5 mmol) were dissolved in ethanol (25 ml). The resulting mixture was heated to reflux for 5 h, then cooled to room temperature. The solid obtained product was collected by filtration. Crystals suitable for X-ray diffraction studies were obtained on slow evaporation of the solvent at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. The displacement ellipsoids are drawn at the 30% probability level.

(E)-3-(2-Hydroxy-3-methoxybenzylideneamino)benzonitrile top

Crystal data top

C₁₅H₁₂N₂O₂	F(000) = 528
M_r = 252.27	D_x = 1.306 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1698 reflections
a = 15.476 (5) Å	θ = 3.1–27.3°
b = 5.9927 (19) Å	µ = 0.09 mm⁻¹
c = 15.413 (7) Å	T = 293 K
β = 116.127 (3)°	Block, yellow
V = 1283.5 (8) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1470 independent reflections
Radiation source: fine-focus sealed tube	1808 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker,2000)	k = −7→7
T_min = 0.973, T_max = 0.991	l = −19→19
5235 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0766P)²] where P = (F_o² + 2F_c²)/3
1470 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O₂	V = 1283.5 (8) Å³
M_r = 252.27	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 15.476 (5) Å	µ = 0.09 mm⁻¹
b = 5.9927 (19) Å	T = 293 K
c = 15.413 (7) Å	0.20 × 0.20 × 0.10 mm
β = 116.127 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1470 independent reflections
Absorption correction: multi-scan (SADABS; Bruker,2000)	1808 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.991	R_int = 0.022
5235 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
1470 reflections	Δρ_min = −0.21 e Å⁻³
172 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
N1	0.49736 (19)	0.0595 (4)	0.27600 (18)	0.0540 (6)
C2	0.3732 (2)	−0.3128 (5)	0.1960 (2)	0.0509 (7)
O1	0.37225 (17)	−0.2232 (4)	0.27625 (16)	0.0617 (6)
H1A	0.3362	−0.2959	0.2915	0.093*
C1	0.4293 (2)	−0.2203 (5)	0.1547 (2)	0.0516 (8)
C3	0.3177 (2)	−0.5039 (6)	0.1545 (2)	0.0549 (7)
C8	0.4899 (2)	−0.0288 (5)	0.1971 (2)	0.0538 (7)
H8A	0.5244	0.0322	0.1664	0.065*
C6	0.4292 (3)	−0.3209 (6)	0.0714 (2)	0.0607 (8)
H6A	0.4662	−0.2602	0.0433	0.073*
C4	0.3194 (2)	−0.5982 (6)	0.0740 (2)	0.0613 (9)
H4A	0.2830	−0.7252	0.0468	0.074*
O2	0.26595 (18)	−0.5821 (4)	0.20096 (17)	0.0703 (7)
C9	0.5623 (2)	0.2388 (5)	0.3193 (2)	0.0497 (7)
C11	0.5989 (2)	0.5663 (5)	0.4178 (2)	0.0536 (8)
C10	0.5378 (2)	0.3913 (5)	0.3722 (2)	0.0520 (7)
H10A	0.4803	0.3758	0.3770	0.062*
C12	0.6857 (3)	0.5916 (6)	0.4126 (3)	0.0623 (8)
H12A	0.7267	0.7099	0.4434	0.075*
C5	0.3752 (2)	−0.5055 (7)	0.0327 (2)	0.0663 (9)
H5A	0.3754	−0.5709	−0.0219	0.080*
C7	0.2045 (3)	−0.7693 (6)	0.1576 (3)	0.0754 (11)
H7A	0.1716	−0.8094	0.1955	0.113*
H7B	0.2425	−0.8933	0.1549	0.113*
H7C	0.1583	−0.7309	0.0934	0.113*
C13	0.7098 (3)	0.4369 (6)	0.3605 (2)	0.0641 (9)
H13A	0.7678	0.4513	0.3565	0.077*
C14	0.6495 (2)	0.2616 (6)	0.3144 (2)	0.0583 (8)
H14A	0.6670	0.1583	0.2800	0.070*
C15	0.5744 (3)	0.7276 (6)	0.4731 (2)	0.0616 (9)
N2	0.5552 (3)	0.8546 (6)	0.5162 (3)	0.0899 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0569 (15)	0.0522 (14)	0.0546 (13)	0.0032 (12)	0.0259 (11)	−0.0012 (11)
C2	0.0500 (17)	0.0543 (17)	0.0498 (16)	0.0108 (14)	0.0231 (14)	−0.0003 (13)
O1	0.0663 (14)	0.0705 (14)	0.0604 (12)	−0.0002 (11)	0.0389 (11)	−0.0077 (11)
C1	0.0483 (17)	0.0575 (19)	0.0494 (16)	0.0080 (13)	0.0218 (14)	−0.0031 (13)
C3	0.0488 (18)	0.0570 (19)	0.0581 (18)	0.0041 (15)	0.0226 (14)	−0.0006 (15)
C8	0.0562 (18)	0.0572 (18)	0.0514 (16)	0.0041 (15)	0.0266 (14)	−0.0009 (14)
C6	0.0557 (18)	0.076 (2)	0.0547 (17)	−0.0003 (17)	0.0283 (15)	−0.0140 (16)
C4	0.057 (2)	0.059 (2)	0.0614 (19)	0.0009 (16)	0.0197 (16)	−0.0090 (15)
O2	0.0728 (16)	0.0706 (16)	0.0700 (14)	−0.0105 (13)	0.0336 (12)	−0.0020 (11)
C9	0.0571 (19)	0.0498 (18)	0.0434 (14)	0.0009 (14)	0.0234 (14)	0.0012 (12)
C11	0.062 (2)	0.0524 (18)	0.0500 (16)	0.0002 (14)	0.0278 (15)	0.0015 (12)
C10	0.0583 (19)	0.0550 (18)	0.0480 (15)	−0.0007 (15)	0.0281 (14)	0.0001 (13)
C12	0.061 (2)	0.066 (2)	0.0612 (18)	−0.0053 (18)	0.0280 (16)	0.0001 (16)
C5	0.063 (2)	0.078 (2)	0.0588 (18)	0.0064 (19)	0.0274 (17)	−0.0169 (17)
C7	0.067 (2)	0.061 (2)	0.087 (3)	−0.0073 (19)	0.023 (2)	0.0085 (19)
C13	0.055 (2)	0.077 (2)	0.0641 (19)	0.0004 (18)	0.0303 (17)	0.0022 (17)
C14	0.062 (2)	0.061 (2)	0.0599 (18)	0.0086 (16)	0.0333 (17)	−0.0002 (14)
C15	0.069 (2)	0.062 (2)	0.0601 (18)	−0.0129 (16)	0.0340 (17)	−0.0106 (16)
N2	0.103 (3)	0.091 (2)	0.097 (2)	−0.026 (2)	0.063 (2)	−0.037 (2)

Geometric parameters (Å, º) top

N1—C8	1.284 (4)	C9—C10	1.383 (4)
N1—C9	1.421 (4)	C9—C14	1.391 (5)
C2—O1	1.354 (4)	C11—C10	1.379 (4)
C2—C1	1.397 (4)	C11—C12	1.389 (5)
C2—C3	1.405 (5)	C11—C15	1.445 (5)
O1—H1A	0.8200	C10—H10A	0.9300
C1—C6	1.418 (4)	C12—C13	1.381 (5)
C1—C8	1.444 (5)	C12—H12A	0.9300
C3—O2	1.371 (4)	C5—H5A	0.9300
C3—C4	1.374 (5)	C7—H7A	0.9600
C8—H8A	0.9300	C7—H7B	0.9600
C6—C5	1.356 (5)	C7—H7C	0.9600
C6—H6A	0.9300	C13—C14	1.377 (5)
C4—C5	1.393 (5)	C13—H13A	0.9300
C4—H4A	0.9300	C14—H14A	0.9300
O2—C7	1.432 (4)	C15—N2	1.134 (4)

C8—N1—C9	120.4 (3)	C10—C11—C15	120.7 (3)
O1—C2—C1	121.2 (3)	C12—C11—C15	118.2 (3)
O1—C2—C3	119.3 (3)	C9—C10—C11	119.9 (3)
C1—C2—C3	119.5 (3)	C9—C10—H10A	120.0
C2—O1—H1A	109.5	C11—C10—H10A	120.0
C2—C1—C6	119.4 (3)	C13—C12—C11	118.4 (3)
C2—C1—C8	121.3 (3)	C13—C12—H12A	120.8
C6—C1—C8	119.3 (3)	C11—C12—H12A	120.8
O2—C3—C4	125.4 (3)	C6—C5—C4	120.7 (3)
O2—C3—C2	114.9 (3)	C6—C5—H5A	119.7
C4—C3—C2	119.7 (3)	C4—C5—H5A	119.7
N1—C8—C1	121.7 (3)	O2—C7—H7A	109.5
N1—C8—H8A	119.2	O2—C7—H7B	109.5
C1—C8—H8A	119.2	H7A—C7—H7B	109.5
C5—C6—C1	120.0 (3)	O2—C7—H7C	109.5
C5—C6—H6A	120.0	H7A—C7—H7C	109.5
C1—C6—H6A	120.0	H7B—C7—H7C	109.5
C3—C4—C5	120.7 (3)	C14—C13—C12	121.1 (3)
C3—C4—H4A	119.7	C14—C13—H13A	119.5
C5—C4—H4A	119.7	C12—C13—H13A	119.5
C3—O2—C7	116.4 (3)	C13—C14—C9	120.1 (3)
C10—C9—C14	119.4 (3)	C13—C14—H14A	120.0
C10—C9—N1	117.1 (3)	C9—C14—H14A	120.0
C14—C9—N1	123.4 (3)	N2—C15—C11	179.8 (4)
C10—C11—C12	121.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	2.18	2.645 (4)	117

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O₂
M_r	252.27
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	15.476 (5), 5.9927 (19), 15.413 (7)
β (°)	116.127 (3)
V (Å³)	1283.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker,2000)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	5235, 1470, 1808
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.124, 1.03
No. of reflections	1470
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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···O2	0.82	2.18	2.645 (4)	116.5

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145–4156. Web of Science CrossRef PubMed CAS 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

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2017

doi:10.1107/S1600536809029225

Open

access