6-Meth­oxy-2-[(E)-phenyl­imino­meth­yl]phenol

Yu, Y.-Y.

doi:10.1107/S1600536811009135

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o889

doi:10.1107/S1600536811009135

Open

access

6-Methoxy-2-[(E)-phenyliminomethyl]phenol

Yu-Ye Yu ^a ^*

^aJinhua College of Vocation and Technology, Jinhua, Zhejiang 321017, People's Republic of China
^*Correspondence e-mail: jhyuyy@sina.com

(Received 23 February 2011; accepted 10 March 2011; online 15 March 2011)

The title compound, C₁₄H₁₃NO₂, was obtained by the condensation reaction of o-vanillin and aniline in ethanol. The molecule adopts the phenol–imine tautomeric form and an E conformation with respect to the azomethine C=N bond. The dihedral angle between the aromatic rings is 30.57 (10)°. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds into zigzag chains parallel to the b axis.

Related literature

For related metal complexes with Schiff base ligands derived from o-vanillin and aniline, see: Li et al. (2008 ); Liu et al. (2009 ); Xian et al. (2008 ); Zhao et al. (2007 ). For the syntheses and antibacterial activities of rare earth complexes with Schiff base ligands derived from o-vanillin and adamantaneamine, see: Zhao et al. (2005 ).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.0882 (4) Å
b = 9.1862 (5) Å
c = 21.0800 (12) Å
V = 1178.95 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.33 × 0.22 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.978, T_max = 0.985
11856 measured reflections
1190 independent reflections
1007 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.140
S = 1.02
1190 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1ⁱ	0.93	2.57	3.485 (4)	168
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); 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/S1600536811009135/rz2565sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009135/rz2565Isup2.hkl

checkCIF report

Comment top

For many years, there has been considerable interest in the study of Schiff base compounds due to their biological activity (Zhao et al., 2005). Recently, we have reported the crystal structure of some Schiff bases metal complexes (Zhao et al., 2007; Xian et al. 2008; Li et al. 2008; Liu et al. 2009). As an extention of our work in the structural characterization of Schiff base compounds, we synthesized the title compound and report its crystal structure herein.

In the molecule of the title compound (Fig. 1), the C—O bond lengths range from 1.350 (4) to 1.419 (4) Å. The C—N and C═N bond lengths are 1.428 (3) and 1.285 (4) Å, respectively. The molecule is not planar, with the dihedral angle between the two aromatic rings of 30.57 (10)°. In the crystal structure (Fig. 2), intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains parallel to the b axis.

Related literature top

For related metal complexes with Schiff base ligands derived from o-vanillin and aniline, see: Li et al. (2008); Liu et al. (2009); Xian et al. (2008); Zhao et al. (2007). For the syntheses and antibacterial activities of rare earth complexes with Schiff base ligands derived from o-vanillin and adamantaneamine, see: Zhao et al. (2005).

Experimental top

Reagents and solvents used were of commercially available quality and were not purified before using. A mixture of o-vanillin (0.152 g, 1.0 mmol) and aniline (0.093 g, 1.0 mmol) in absolute ethanol (30 ml) was stirred and refluxed for 4 h. The solution was then cooled to room temperature. Orange single crystals suitable for X-ray diffraction were obtained by slow evaporation of the solvent after about 5 d.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound compound viewed approximately along the a axis. Intermolecular hydrogen bonds are drawn as dashed lines.

6-Methoxy-2-[(E)-phenyliminomethyl]phenol top

Crystal data top

C₁₄H₁₃NO₂	F(000) = 480
M_r = 227.25	D_x = 1.280 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5745 reflections
a = 6.0882 (4) Å	θ = 2.4–25.0°
b = 9.1862 (5) Å	µ = 0.09 mm⁻¹
c = 21.0800 (12) Å	T = 296 K
V = 1178.95 (12) Å³	Block, orange
Z = 4	0.33 × 0.22 × 0.18 mm

Data collection top

Bruker APEXII area-detector diffractometer	1190 independent reflections
Radiation source: fine-focus sealed tube	1007 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −7→7
T_min = 0.978, T_max = 0.985	k = −10→10
11856 measured reflections	l = −25→23

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0787P)² + 0.4631P] where P = (F_o² + 2F_c²)/3
1190 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₁₃NO₂	V = 1178.95 (12) Å³
M_r = 227.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.0882 (4) Å	µ = 0.09 mm⁻¹
b = 9.1862 (5) Å	T = 296 K
c = 21.0800 (12) Å	0.33 × 0.22 × 0.18 mm

Data collection top

Bruker APEXII area-detector diffractometer	1190 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	1007 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.985	R_int = 0.081
11856 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
1190 reflections	Δρ_min = −0.25 e Å⁻³
154 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.1467 (5)	0.8849 (3)	0.19232 (12)	0.0471 (6)
O2	−0.0125 (4)	1.0344 (2)	0.09751 (11)	0.0546 (6)
H2B	0.1106	0.9995	0.1017	0.066*
C6	−0.1608 (5)	0.9260 (3)	0.09144 (13)	0.0425 (7)
O1	−0.3287 (4)	1.0709 (2)	0.01403 (10)	0.0539 (6)
C1	−0.1531 (6)	0.7999 (3)	0.12880 (14)	0.0466 (7)
C5	−0.3315 (6)	0.9420 (3)	0.04705 (14)	0.0454 (7)
C7	0.2914 (5)	0.8685 (3)	0.24514 (15)	0.0456 (7)
C10	0.5867 (6)	0.8458 (5)	0.34404 (19)	0.0637 (10)
H10A	0.6870	0.8378	0.3771	0.076*
C4	−0.4870 (6)	0.8348 (4)	0.03963 (15)	0.0537 (8)
H4A	−0.5999	0.8468	0.0104	0.064*
C12	0.0067 (6)	0.7846 (4)	0.17918 (15)	0.0496 (8)
H12A	0.0082	0.6993	0.2029	0.060*
C2	−0.3120 (6)	0.6922 (4)	0.12031 (15)	0.0551 (9)
H2A	−0.3069	0.6085	0.1451	0.066*
C8	0.2343 (6)	0.7914 (4)	0.30001 (15)	0.0510 (8)
H8A	0.0970	0.7477	0.3034	0.061*
C13	0.4930 (7)	0.9357 (4)	0.24102 (17)	0.0548 (8)
H13A	0.5290	0.9899	0.2052	0.066*
C3	−0.4755 (7)	0.7075 (4)	0.07616 (16)	0.0581 (9)
H3A	−0.5783	0.6338	0.0704	0.070*
C14	−0.5226 (7)	1.1074 (5)	−0.0198 (2)	0.0693 (11)
H14A	−0.5026	1.1992	−0.0408	0.104*
H14B	−0.6436	1.1144	0.0093	0.104*
H14C	−0.5530	1.0333	−0.0507	0.104*
C9	0.3840 (6)	0.7807 (4)	0.34918 (17)	0.0578 (9)
H9A	0.3475	0.7295	0.3858	0.069*
C11	0.6421 (6)	0.9225 (4)	0.29039 (19)	0.0647 (10)
H11A	0.7798	0.9655	0.2872	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0523 (14)	0.0443 (13)	0.0446 (14)	0.0027 (14)	0.0003 (13)	0.0060 (11)
O2	0.0561 (13)	0.0449 (13)	0.0629 (14)	−0.0041 (12)	−0.0041 (12)	0.0090 (10)
C6	0.0494 (16)	0.0359 (15)	0.0422 (15)	0.0024 (16)	0.0047 (14)	0.0004 (12)
O1	0.0657 (14)	0.0443 (12)	0.0516 (12)	0.0015 (13)	−0.0101 (12)	0.0121 (10)
C1	0.0581 (18)	0.0405 (16)	0.0413 (15)	0.0056 (17)	0.0016 (15)	0.0024 (13)
C5	0.0549 (17)	0.0401 (16)	0.0413 (15)	0.0055 (16)	0.0021 (15)	0.0010 (13)
C7	0.0501 (16)	0.0387 (16)	0.0479 (17)	0.0054 (15)	0.0012 (14)	0.0004 (13)
C10	0.060 (2)	0.063 (2)	0.068 (2)	0.007 (2)	−0.0147 (19)	−0.009 (2)
C4	0.0639 (19)	0.052 (2)	0.0455 (17)	−0.0025 (18)	−0.0020 (17)	0.0002 (14)
C12	0.0612 (19)	0.0403 (15)	0.0473 (17)	0.0064 (18)	0.0006 (16)	0.0073 (13)
C2	0.075 (2)	0.0416 (17)	0.0491 (17)	−0.008 (2)	−0.0019 (17)	0.0076 (14)
C8	0.0520 (17)	0.0504 (19)	0.0507 (17)	0.0016 (17)	0.0033 (15)	0.0051 (15)
C13	0.0557 (16)	0.0503 (18)	0.058 (2)	−0.0022 (19)	0.0103 (17)	0.0031 (16)
C3	0.066 (2)	0.0484 (18)	0.060 (2)	−0.0104 (19)	−0.0056 (18)	0.0030 (16)
C14	0.069 (2)	0.063 (2)	0.076 (2)	0.007 (2)	−0.014 (2)	0.022 (2)
C9	0.072 (2)	0.050 (2)	0.0511 (18)	0.007 (2)	−0.0057 (19)	0.0037 (15)
C11	0.0486 (18)	0.059 (2)	0.087 (3)	−0.0045 (19)	0.002 (2)	−0.009 (2)

Geometric parameters (Å, º) top

N1—C12	1.285 (4)	C4—C3	1.402 (5)
N1—C7	1.428 (4)	C4—H4A	0.9300
O2—C6	1.350 (4)	C12—H12A	0.9300
O2—H2B	0.8200	C2—C3	1.370 (5)
C6—C1	1.401 (4)	C2—H2A	0.9300
C6—C5	1.406 (4)	C8—C9	1.384 (5)
O1—C5	1.374 (4)	C8—H8A	0.9300
O1—C14	1.419 (4)	C13—C11	1.386 (5)
C1—C2	1.396 (5)	C13—H13A	0.9300
C1—C12	1.447 (5)	C3—H3A	0.9300
C5—C4	1.375 (5)	C14—H14A	0.9600
C7—C13	1.377 (5)	C14—H14B	0.9600
C7—C8	1.400 (5)	C14—H14C	0.9600
C10—C11	1.374 (6)	C9—H9A	0.9300
C10—C9	1.375 (5)	C11—H11A	0.9300
C10—H10A	0.9300

C12—N1—C7	120.1 (3)	C3—C2—C1	121.2 (3)
C6—O2—H2B	109.5	C3—C2—H2A	119.4
O2—C6—C1	122.3 (3)	C1—C2—H2A	119.4
O2—C6—C5	118.7 (3)	C9—C8—C7	119.4 (3)
C1—C6—C5	119.0 (3)	C9—C8—H8A	120.3
C5—O1—C14	116.6 (3)	C7—C8—H8A	120.3
C2—C1—C6	119.4 (3)	C7—C13—C11	119.8 (3)
C2—C1—C12	119.4 (3)	C7—C13—H13A	120.1
C6—C1—C12	121.0 (3)	C11—C13—H13A	120.1
O1—C5—C4	124.6 (3)	C2—C3—C4	119.7 (3)
O1—C5—C6	114.7 (3)	C2—C3—H3A	120.1
C4—C5—C6	120.7 (3)	C4—C3—H3A	120.1
C13—C7—C8	120.0 (3)	O1—C14—H14A	109.5
C13—C7—N1	117.0 (3)	O1—C14—H14B	109.5
C8—C7—N1	123.0 (3)	H14A—C14—H14B	109.5
C11—C10—C9	120.5 (4)	O1—C14—H14C	109.5
C11—C10—H10A	119.7	H14A—C14—H14C	109.5
C9—C10—H10A	119.7	H14B—C14—H14C	109.5
C5—C4—C3	120.0 (3)	C10—C9—C8	120.1 (3)
C5—C4—H4A	120.0	C10—C9—H9A	120.0
C3—C4—H4A	120.0	C8—C9—H9A	120.0
N1—C12—C1	122.3 (3)	C10—C11—C13	120.2 (3)
N1—C12—H12A	118.8	C10—C11—H11A	119.9
C1—C12—H12A	118.8	C13—C11—H11A	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1ⁱ	0.93	2.57	3.485 (4)	168

Symmetry code: (i) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.0882 (4), 9.1862 (5), 21.0800 (12)
V (Å³)	1178.95 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.978, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	11856, 1190, 1007
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.140, 1.02
No. of reflections	1190
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), 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
C9—H9A···O1ⁱ	0.93	2.57	3.485 (4)	168

Symmetry code: (i) −x, y−1/2, −z+1/2.

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594. Web of Science CrossRef IUCr Journals Google Scholar
Liu, J.-F., Liu, J.-L. & Zhao, G.-L. (2009). Acta Cryst. E65, m1385–m1386. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xian, H.-D., Liu, J.-F., Li, H.-Q. & Zhao, G.-L. (2008). Acta Cryst. E64, m1422. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, G.-L., Shi, X. & Ng, S. W. (2007). Acta Cryst. E63, m267–m268. CSD CrossRef IUCr Journals Google Scholar
Zhao, G.-L., Zhang, P.-H. & Feng, Y.-L. (2005). Chin. J. Inorg. Chem. 21, 421–424. CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o889

doi:10.1107/S1600536811009135

Open

access