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Acta Cryst. (2007). E63, o3930    [ doi:10.1107/S1600536807042134 ]

2-(Benzyliminomethyl)-6-methoxyphenol

Z.-F. Li, S.-W. Wang, Q. Zhang and X.-J. Yu

Abstract top

In the title Schiff base compound, C15H15NO2, the C=N and C-N bond lengths are 1.277 (4) and 1.453 (5) Å, respectively, while the C-O bond length of the hydroxyl group is 1.334 (3) Å. The molecule exhibits an intramolecular O-H...N hydrogen bond with an O...N distance of 2.548 (3) Å.

Comment top

Schiff bases have been utilized as ligands for a long time due to their straightforward synthesis and versatility in metal complexes. They therefore play an important role in the development of coordination chemistry as well as inorganic biochemistry, catalysis, optical materials and so on (Garnovskii et al., 1993; Huang et al., 2002). Considerable attention has been focused on the syntheses and structures of copper(II) and nickel(II) complexes. The nickel complexes with multidentate Schiff-base ligands have aroused particular interest because this metal can exhibit several oxidation states and may provide the basis for models of active sites of biological systems. The main attention with optically active Schiff-base complexes is concentrated on their catalytic abilities in stereo-selective synthesis (Bhadbhade & Srinivas, 1993; Bunce et al., 1998). As part of our research aiming to understand the molecular properties of chiral Schiff-base complexes, we describe here the synthesis and crystal structure of the title Schiff-base ligand (Figure 1).

Related literature top

For related literature, see: Bhadbhade & Srinivas (1993); Bunce et al. (1998); Garnovskii et al. (1993); Huang et al. (2002).

Experimental top

A mixture of benzylamine (5.00 mmol) and o-vanillin (5.00 mmol) in methanol (40 ml) was refluxed with stirring for one hour to give an orange precipitate which was filtered and washed with methanol to give the title compound in 86% yield. Elemental analysis calculated: C 74.69, H 6.22, N 5.81%; found: C 74.66, H 6.12, N 5.79%.

Refinement top

H atoms were positioned geometrically with O—H = 0.82 Å and C—H = 0.93 or 0.96 Å, then constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms.
2-(Benzyliminomethyl)-6-methoxyphenol top
Crystal data top
C15H15NO2F000 = 512
Mr = 241.28Dx = 1.309 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2958 reflections
a = 8.9236 (2) Åθ = 2.3–28.1º
b = 5.7681 (1) ŵ = 0.09 mm−1
c = 23.8006 (2) ÅT = 293 (2) K
β = 92.432 (2)ºBlock, colourless
V = 1223.97 (4) Å30.26 × 0.24 × 0.12 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		2958 independent reflections
Radiation source: fine-focus sealed tube1876 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 293(2) Kθmax = 28.1º
φ and ω scansθmin = 2.3º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −10→11
Tmin = 0.978, Tmax = 0.990k = −7→7
8962 measured reflectionsl = −31→31
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.202  w = 1/[σ2(Fo2) + (0.1284P)2 + 0.1359P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.003
2958 reflectionsΔρmax = 0.45 e Å−3
165 parametersΔρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C15H15NO2V = 1223.97 (4) Å3
Mr = 241.28Z = 4
Monoclinic, P21/cMo Kα
a = 8.9236 (2) ŵ = 0.09 mm−1
b = 5.7681 (1) ÅT = 293 (2) K
c = 23.8006 (2) Å0.26 × 0.24 × 0.12 mm
β = 92.432 (2)º
Data collection top
Bruker APEXII CCD
diffractometer		2958 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1876 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.990Rint = 0.020
8962 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058165 parameters
wR(F2) = 0.202H-atom parameters constrained
S = 1.00Δρmax = 0.45 e Å−3
2958 reflectionsΔρmin = −0.39 e Å−3
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 > 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
C10.2240 (3)0.5473 (5)−0.01082 (11)0.0597 (7)
C20.2308 (3)0.3654 (5)−0.04596 (12)0.0640 (7)
H110.28680.2332−0.03730.077*
C30.1488 (4)0.3901 (8)−0.09541 (16)0.0889 (11)
H180.15010.2699−0.12140.107*
C40.0667 (4)0.5786 (8)−0.10837 (15)0.0832 (10)
H150.01160.5850−0.14240.100*
C50.0631 (4)0.7614 (7)−0.07204 (15)0.0821 (10)
H170.00740.8934−0.08110.098*
C60.1428 (4)0.7460 (6)−0.02230 (13)0.0705 (8)
H140.14250.86720.00350.085*
C70.3131 (4)0.5078 (7)0.04205 (13)0.0771 (9)
H12A0.27760.36820.05990.093*
H12B0.41720.48370.03340.093*
C80.4167 (3)0.8313 (7)0.09167 (11)0.0698 (9)
H70.50430.80250.07300.084*
C90.4159 (3)1.0214 (6)0.13121 (11)0.0627 (8)
C100.2909 (3)1.0611 (5)0.16243 (10)0.0561 (7)
C110.2914 (3)1.2476 (5)0.20011 (11)0.0597 (7)
C120.1536 (4)1.4678 (7)0.26392 (15)0.0782 (9)
H13A0.23061.46170.29330.117*
H13B0.05701.46760.28020.117*
H13C0.16481.60680.24230.117*
C130.4141 (3)1.3927 (6)0.20707 (13)0.0690 (8)
H90.41301.51440.23270.083*
C140.5364 (3)1.3557 (7)0.17609 (15)0.0773 (9)
H160.61901.45350.18010.093*
C150.5382 (3)1.1745 (7)0.13892 (13)0.0753 (10)
H80.62281.15170.11810.090*
N10.3035 (3)0.7008 (5)0.08094 (9)0.0697 (7)
O10.1661 (2)1.2709 (4)0.22824 (9)0.0730 (7)
O20.1710 (2)0.9237 (4)0.15680 (8)0.0670 (6)
H20.18520.82560.13270.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0579 (15)0.0649 (17)0.0569 (14)0.0073 (12)0.0109 (11)0.0053 (12)
C20.0709 (17)0.0586 (16)0.0630 (15)0.0114 (13)0.0089 (13)−0.0047 (13)
C30.088 (2)0.101 (3)0.078 (2)−0.012 (2)0.0095 (18)−0.023 (2)
C40.067 (2)0.116 (3)0.0658 (18)−0.012 (2)−0.0051 (14)0.0036 (19)
C50.074 (2)0.093 (3)0.078 (2)0.0119 (17)−0.0122 (16)0.0131 (18)
C60.0740 (18)0.0723 (19)0.0648 (16)0.0136 (15)−0.0014 (14)0.0005 (15)
C70.082 (2)0.088 (2)0.0613 (17)0.0314 (18)0.0042 (14)0.0068 (16)
C80.0531 (15)0.106 (2)0.0503 (13)0.0250 (16)0.0068 (11)0.0195 (15)
C90.0455 (13)0.095 (2)0.0476 (13)0.0132 (13)0.0032 (10)0.0198 (13)
C100.0406 (12)0.0800 (18)0.0477 (12)0.0038 (11)0.0003 (9)0.0160 (12)
C110.0477 (13)0.0786 (19)0.0530 (13)0.0035 (12)0.0028 (10)0.0137 (13)
C120.0698 (18)0.100 (3)0.0659 (17)0.0036 (17)0.0089 (14)−0.0046 (17)
C130.0538 (15)0.085 (2)0.0675 (16)−0.0037 (14)−0.0020 (12)0.0145 (15)
C140.0515 (15)0.102 (3)0.0781 (19)−0.0111 (16)0.0025 (13)0.0179 (19)
C150.0411 (13)0.119 (3)0.0662 (17)0.0057 (15)0.0086 (11)0.0276 (19)
N10.0616 (14)0.0969 (19)0.0508 (12)0.0196 (13)0.0033 (10)0.0071 (12)
O10.0525 (11)0.0963 (17)0.0711 (12)−0.0048 (10)0.0131 (9)−0.0105 (11)
O20.0489 (10)0.0910 (16)0.0617 (11)−0.0020 (9)0.0083 (8)−0.0016 (10)
Geometric parameters (Å, °) top
C1—C21.345 (4)C8—H70.930
C1—C61.378 (4)C9—C101.386 (4)
C1—C71.477 (4)C9—C151.409 (5)
C2—C31.367 (5)C10—O21.334 (3)
C2—H110.930C10—C111.401 (4)
C3—C41.340 (6)C11—O11.334 (3)
C3—H180.930C11—C131.383 (4)
C4—C51.365 (5)C12—O11.425 (4)
C4—H150.930C12—H13A0.960
C5—C61.357 (5)C12—H13B0.960
C5—H170.930C12—H13C0.960
C6—H140.930C13—C141.360 (4)
C7—N11.453 (5)C13—H90.930
C7—H12A0.970C14—C151.370 (5)
C7—H12B0.970C14—H160.930
C8—N11.277 (4)C15—H80.930
C8—C91.445 (5)O2—H20.820
C2—C1—C6124.3 (3)C10—C9—C15117.6 (3)
C2—C1—C7111.9 (3)C10—C9—C8120.0 (3)
C6—C1—C7123.8 (3)C15—C9—C8122.4 (3)
C1—C2—C3114.7 (3)O2—C10—C9120.6 (3)
C1—C2—H11122.7O2—C10—C11120.1 (2)
C3—C2—H11122.7C9—C10—C11119.3 (3)
C4—C3—C2123.4 (3)O1—C11—C13123.8 (3)
C4—C3—H18118.3O1—C11—C10114.7 (2)
C2—C3—H18118.3C13—C11—C10121.5 (2)
C3—C4—C5120.5 (3)O1—C12—H13A109.5
C3—C4—H15119.7O1—C12—H13B109.5
C5—C4—H15119.7H13A—C12—H13B109.5
C6—C5—C4118.5 (3)O1—C12—H13C109.5
C6—C5—H17120.8H13A—C12—H13C109.5
C4—C5—H17120.8H13B—C12—H13C109.5
C5—C6—C1118.6 (3)C14—C13—C11119.3 (3)
C5—C6—H14120.7C14—C13—H9120.3
C1—C6—H14120.7C11—C13—H9120.3
N1—C7—C1112.4 (3)C13—C14—C15120.1 (3)
N1—C7—H12A109.1C13—C14—H16120.0
C1—C7—H12A109.1C15—C14—H16120.0
N1—C7—H12B109.1C14—C15—C9122.2 (3)
C1—C7—H12B109.1C14—C15—H8118.9
H12A—C7—H12B107.9C9—C15—H8118.9
N1—C8—C9123.5 (3)C8—N1—C7120.8 (3)
N1—C8—H7118.2C11—O1—C12117.9 (2)
C9—C8—H7118.2C10—O2—H2109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.812.548 (3)150
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.812.548 (3)150
Acknowledgements top

The authors thank Shandong University of Technology for financial support.

references
References top

Bhadbhade, M. M. & Srinivas, D. (1993). Inorg. Chem. 32, 6122–6130.

Bruker (2000). SADABS. Version 2.03. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2001). SAINT-Plus and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Bunce, S., Cross, R. J., Farrugia, L. J., Kunchandy, S., Meason, L. L., Muir, K. W., Donnell, M., Peacock, R. D., Stirling, D. & Teat, S. J. (1998). Polyhedron, 17, 4179–4187.

Garnovskii, A. D., Nivorozkhin, A. L. & Minkin, V. (1993). Coord. Chem. Rev. 126, 1–69.

Huang, D. G., Zhu, H. P., Chen, C. N., Chen, F. & Liu, Q. T. (2002). Chin. J. Struct. Chem. 21, 64–66.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.