organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593-m1594.]); Liu et al. (2009[Liu, J.-F., Liu, J.-L. & Zhao, G.-L. (2009). Acta Cryst. E65, m1385-m1386.]); Xian et al. (2008[Xian, H.-D., Liu, J.-F., Li, H.-Q. & Zhao, G.-L. (2008). Acta Cryst. E64, m1422.]); Zhao et al. (2007[Zhao, G.-L., Shi, X. & Ng, S. W. (2007). Acta Cryst. E63, m267-m268.]). 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[Zhao, G.-L., Zhang, P.-H. & Feng, Y.-L. (2005). Chin. J. Inorg. Chem. 21, 421-424.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13NO2

  • Mr = 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[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.985

  • 11856 measured reflections

  • 1190 independent reflections

  • 1007 reflections with I > 2σ(I)

  • Rint = 0.081

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.140

  • S = 1.02

  • 1190 reflections

  • 154 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 CN 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.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.96 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C, O) or 1.5Ueq(C) for methyl H atoms. In the absence of significant anomalous scattering effects, 820 Friedel pairs were averaged in the final refinement.

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
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] 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
C14H13NO2F(000) = 480
Mr = 227.25Dx = 1.280 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5745 reflections
a = 6.0882 (4) Åθ = 2.4–25.0°
b = 9.1862 (5) ŵ = 0.09 mm1
c = 21.0800 (12) ÅT = 296 K
V = 1178.95 (12) Å3Block, orange
Z = 40.33 × 0.22 × 0.18 mm
Data collection top
Bruker APEXII area-detector
diffractometer
1190 independent reflections
Radiation source: fine-focus sealed tube1007 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
ϕ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 77
Tmin = 0.978, Tmax = 0.985k = 1010
11856 measured reflectionsl = 2523
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0787P)2 + 0.4631P]
where P = (Fo2 + 2Fc2)/3
1190 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C14H13NO2V = 1178.95 (12) Å3
Mr = 227.25Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.0882 (4) ŵ = 0.09 mm1
b = 9.1862 (5) ÅT = 296 K
c = 21.0800 (12) Å0.33 × 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)
Tmin = 0.978, Tmax = 0.985Rint = 0.081
11856 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.02Δρmax = 0.19 e Å3
1190 reflectionsΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
N10.1467 (5)0.8849 (3)0.19232 (12)0.0471 (6)
O20.0125 (4)1.0344 (2)0.09751 (11)0.0546 (6)
H2B0.11060.99950.10170.066*
C60.1608 (5)0.9260 (3)0.09144 (13)0.0425 (7)
O10.3287 (4)1.0709 (2)0.01403 (10)0.0539 (6)
C10.1531 (6)0.7999 (3)0.12880 (14)0.0466 (7)
C50.3315 (6)0.9420 (3)0.04705 (14)0.0454 (7)
C70.2914 (5)0.8685 (3)0.24514 (15)0.0456 (7)
C100.5867 (6)0.8458 (5)0.34404 (19)0.0637 (10)
H10A0.68700.83780.37710.076*
C40.4870 (6)0.8348 (4)0.03963 (15)0.0537 (8)
H4A0.59990.84680.01040.064*
C120.0067 (6)0.7846 (4)0.17918 (15)0.0496 (8)
H12A0.00820.69930.20290.060*
C20.3120 (6)0.6922 (4)0.12031 (15)0.0551 (9)
H2A0.30690.60850.14510.066*
C80.2343 (6)0.7914 (4)0.30001 (15)0.0510 (8)
H8A0.09700.74770.30340.061*
C130.4930 (7)0.9357 (4)0.24102 (17)0.0548 (8)
H13A0.52900.98990.20520.066*
C30.4755 (7)0.7075 (4)0.07616 (16)0.0581 (9)
H3A0.57830.63380.07040.070*
C140.5226 (7)1.1074 (5)0.0198 (2)0.0693 (11)
H14A0.50261.19920.04080.104*
H14B0.64361.11440.00930.104*
H14C0.55301.03330.05070.104*
C90.3840 (6)0.7807 (4)0.34918 (17)0.0578 (9)
H9A0.34750.72950.38580.069*
C110.6421 (6)0.9225 (4)0.29039 (19)0.0647 (10)
H11A0.77980.96550.28720.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0523 (14)0.0443 (13)0.0446 (14)0.0027 (14)0.0003 (13)0.0060 (11)
O20.0561 (13)0.0449 (13)0.0629 (14)0.0041 (12)0.0041 (12)0.0090 (10)
C60.0494 (16)0.0359 (15)0.0422 (15)0.0024 (16)0.0047 (14)0.0004 (12)
O10.0657 (14)0.0443 (12)0.0516 (12)0.0015 (13)0.0101 (12)0.0121 (10)
C10.0581 (18)0.0405 (16)0.0413 (15)0.0056 (17)0.0016 (15)0.0024 (13)
C50.0549 (17)0.0401 (16)0.0413 (15)0.0055 (16)0.0021 (15)0.0010 (13)
C70.0501 (16)0.0387 (16)0.0479 (17)0.0054 (15)0.0012 (14)0.0004 (13)
C100.060 (2)0.063 (2)0.068 (2)0.007 (2)0.0147 (19)0.009 (2)
C40.0639 (19)0.052 (2)0.0455 (17)0.0025 (18)0.0020 (17)0.0002 (14)
C120.0612 (19)0.0403 (15)0.0473 (17)0.0064 (18)0.0006 (16)0.0073 (13)
C20.075 (2)0.0416 (17)0.0491 (17)0.008 (2)0.0019 (17)0.0076 (14)
C80.0520 (17)0.0504 (19)0.0507 (17)0.0016 (17)0.0033 (15)0.0051 (15)
C130.0557 (16)0.0503 (18)0.058 (2)0.0022 (19)0.0103 (17)0.0031 (16)
C30.066 (2)0.0484 (18)0.060 (2)0.0104 (19)0.0056 (18)0.0030 (16)
C140.069 (2)0.063 (2)0.076 (2)0.007 (2)0.014 (2)0.022 (2)
C90.072 (2)0.050 (2)0.0511 (18)0.007 (2)0.0057 (19)0.0037 (15)
C110.0486 (18)0.059 (2)0.087 (3)0.0045 (19)0.002 (2)0.009 (2)
Geometric parameters (Å, º) top
N1—C121.285 (4)C4—C31.402 (5)
N1—C71.428 (4)C4—H4A0.9300
O2—C61.350 (4)C12—H12A0.9300
O2—H2B0.8200C2—C31.370 (5)
C6—C11.401 (4)C2—H2A0.9300
C6—C51.406 (4)C8—C91.384 (5)
O1—C51.374 (4)C8—H8A0.9300
O1—C141.419 (4)C13—C111.386 (5)
C1—C21.396 (5)C13—H13A0.9300
C1—C121.447 (5)C3—H3A0.9300
C5—C41.375 (5)C14—H14A0.9600
C7—C131.377 (5)C14—H14B0.9600
C7—C81.400 (5)C14—H14C0.9600
C10—C111.374 (6)C9—H9A0.9300
C10—C91.375 (5)C11—H11A0.9300
C10—H10A0.9300
C12—N1—C7120.1 (3)C3—C2—C1121.2 (3)
C6—O2—H2B109.5C3—C2—H2A119.4
O2—C6—C1122.3 (3)C1—C2—H2A119.4
O2—C6—C5118.7 (3)C9—C8—C7119.4 (3)
C1—C6—C5119.0 (3)C9—C8—H8A120.3
C5—O1—C14116.6 (3)C7—C8—H8A120.3
C2—C1—C6119.4 (3)C7—C13—C11119.8 (3)
C2—C1—C12119.4 (3)C7—C13—H13A120.1
C6—C1—C12121.0 (3)C11—C13—H13A120.1
O1—C5—C4124.6 (3)C2—C3—C4119.7 (3)
O1—C5—C6114.7 (3)C2—C3—H3A120.1
C4—C5—C6120.7 (3)C4—C3—H3A120.1
C13—C7—C8120.0 (3)O1—C14—H14A109.5
C13—C7—N1117.0 (3)O1—C14—H14B109.5
C8—C7—N1123.0 (3)H14A—C14—H14B109.5
C11—C10—C9120.5 (4)O1—C14—H14C109.5
C11—C10—H10A119.7H14A—C14—H14C109.5
C9—C10—H10A119.7H14B—C14—H14C109.5
C5—C4—C3120.0 (3)C10—C9—C8120.1 (3)
C5—C4—H4A120.0C10—C9—H9A120.0
C3—C4—H4A120.0C8—C9—H9A120.0
N1—C12—C1122.3 (3)C10—C11—C13120.2 (3)
N1—C12—H12A118.8C10—C11—H11A119.9
C1—C12—H12A118.8C13—C11—H11A119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1i0.932.573.485 (4)168
Symmetry code: (i) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H13NO2
Mr227.25
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)6.0882 (4), 9.1862 (5), 21.0800 (12)
V3)1178.95 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.33 × 0.22 × 0.18
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2006)
Tmin, Tmax0.978, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
11856, 1190, 1007
Rint0.081
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.140, 1.02
No. of reflections1190
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C9—H9A···O1i0.932.573.485 (4)168
Symmetry code: (i) x, y1/2, z+1/2.
 

References

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

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ISSN: 2056-9890
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