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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3298.
Published online 2010 November 24. doi:  10.1107/S1600536810048282
PMCID: PMC3011435

2-[(4-Meth­oxy­benz­yl)imino­meth­yl]phenol

Abstract

In the title Schiff base compound, C15H15NO2, prepared from 4-meth­oxy­benzyl­amine and salicyl­aldehyde, an intra­molecular O—H(...)N hydrogen bonds influences the mol­ecular conformation; the two aromatic rings form a dihedral angle of 73.5 (1)°. In the crystal, weak inter­molecular C—H(...)O inter­actions link the mol­ecules into chains propagating in [010].

Related literature

For background to Schiff base ligands and their biological activity, see: Adsule et al. (2006 [triangle]); Karthikeyan et al. (2006 [triangle]). For related structures, see: Phurat et al. (2010 [triangle]); Tariq et al. (2010 [triangle]); Khalaji & Simpson (2009 [triangle]). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 [triangle]). For details of the synthesis, see: Phurat et al. (2010 [triangle]); Kannappan et al. (2005 [triangle]).

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Object name is e-66-o3298-scheme1.jpg

Experimental

Crystal data

  • C15H15NO2
  • M r = 241.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3298-efi1.jpg
  • a = 5.7190 (8) Å
  • b = 12.7229 (19) Å
  • c = 17.936 (3) Å
  • V = 1305.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.3 × 0.18 × 0.04 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • 5776 measured reflections
  • 1573 independent reflections
  • 1177 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.162
  • S = 1.13
  • 1573 reflections
  • 164 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048282/cv2800sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048282/cv2800Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the 90th Anniversary of Chulalongkorn University Fund (Ratchadaphisek Somphot Endowment Fund) to CP, the Research Funds from the Faculty of Science (A1B1), the Thailand Research Fund (TRF) to NM, and the Thai Government Stimulus Package 2 (TKK2555) under the Project for Establishment of Comprehensive Center for Innovative Food, Health Products and Agrigulture and Center for Petroleum Petrochemicals and Advanced Materials.

supplementary crystallographic information

Comment

Schiff base complexes have gained importance from physiological and pharmacological activities point of view (Adsule et al., 2006; Karthikeyan et al., 2006). As a part of our research focused on the area of transition metal complex-based anticancer agents, the title compound (I) has been prepared as a ligand by Schiff base reaction between 4-methoxybenzylamine and salicylaldehyde.

The molecule of (I) (Fig. 1) adopts a V-shape structure. The dihedral angle between the methoxybenzene ring and 2-methyliminophenol moiety is 73.5 (1)°. The 2-methyliminophenol (C1 to C7, N1 and O1) moiety is nearly planar (r.m.s. deviation = 0.021 Å). The methoxybenzene and 2-methyliminophenol groups are located on the opposite side of the C=N bond, showing an E configuration. The bond lengths and angles in (I) are normal and comparable with those observed in the related compounds (Phurat et al., 2010; Tariq et al., 2010; Khalaji & Simpson, 2009). Intramolecular O—H···N hydrogen bond (Table 1) generates a S(6) ring (Bernstein et al., 1995).

In the crystal structure, weak intermolecular C—H···O interactions (Table 1) link the molecules into chains propagated in direction [010].

Experimental

The title compound was prepared according to the method reported in the literature (Kannappan et al., 2005; Phurat et al., 2010). 4-Methoxybenzylamine (2.50 ml.2.63 g, 0.02 mol) was added to a stirred ethanol solution of salicylaldehyde (2.50 ml, 2.86 g, 0.02 mol). The reaction mixture was stirred at reflux for 2 h and then the mixture was allowed to stand at room temperature for 1 week to give yellow cystals suitable for X-ray diffraction analysis.

Refinement

H-atoms were geometrically positioned (C—H 0.93-0.97 Å, O—H 0.82 Å) and refined using a riding model, with Uiso= 1.2-1.5 Ueq of the parent atom. The absolute structure could not be determined and therefore 1,086 Friedel opposites were merged.

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. Hydrogen bond is shown as a dashed line.

Crystal data

C15H15NO2F(000) = 512
Mr = 241.28Dx = 1.228 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 5.7190 (8) ŵ = 0.08 mm1
b = 12.7229 (19) ÅT = 293 K
c = 17.936 (3) ÅNeedle, yellow
V = 1305.0 (3) Å30.3 × 0.18 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer1177 reflections with I > 2σ(I)
Radiation source: Mo KαRint = 0.040
graphiteθmax = 26.5°, θmin = 2.0°
[var phi] and ω scansh = −7→7
5776 measured reflectionsk = −15→14
1573 independent reflectionsl = −20→22

Refinement

Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162(Δ/σ)max < 0.001
S = 1.13Δρmax = 0.15 e Å3
1573 reflectionsΔρmin = −0.16 e Å3
164 parameters

Special details

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.

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

xyzUiso*/Ueq
C10.7854 (7)0.1595 (3)0.54878 (17)0.0795 (9)
H10.6420.1830.53080.095*
C20.8661 (10)0.0614 (3)0.5283 (2)0.1029 (14)
H20.77870.01910.49650.123*
C31.0749 (9)0.0274 (3)0.5552 (3)0.1095 (15)
H31.1283−0.0390.54170.131*
C41.2087 (7)0.0879 (3)0.6015 (2)0.0909 (11)
H41.34990.06270.61990.109*
C51.1300 (5)0.1875 (2)0.62042 (17)0.0668 (8)
C60.9144 (5)0.2235 (2)0.59563 (14)0.0570 (6)
C70.8246 (5)0.3261 (2)0.61737 (18)0.0675 (7)
H70.68060.34820.5990.081*
C80.8369 (7)0.4881 (3)0.6807 (3)0.1079 (14)
H8A0.79990.48890.73350.129*
H8B0.69290.49890.65320.129*
C91.0065 (6)0.5755 (3)0.6632 (2)0.0814 (10)
C101.1673 (7)0.6086 (3)0.71468 (18)0.0783 (9)
H101.16880.57750.76160.094*
C111.3269 (6)0.6865 (2)0.69908 (16)0.0695 (8)
H111.43430.70770.7350.083*
C121.3254 (6)0.7330 (2)0.62925 (15)0.0642 (7)
C131.1673 (8)0.7010 (3)0.57680 (19)0.0836 (10)
H131.16670.73190.52980.1*
C141.0094 (7)0.6231 (3)0.5935 (2)0.0892 (11)
H140.90250.60180.55750.107*
C151.6382 (7)0.8487 (3)0.6610 (2)0.0891 (10)
H15A1.730.9040.63940.134*
H15B1.73890.79190.67540.134*
H15C1.55730.87490.7040.134*
N10.9379 (4)0.3862 (2)0.66067 (15)0.0790 (7)
O11.2662 (4)0.2479 (2)0.66466 (15)0.0979 (8)
H1A1.19210.29970.67820.147*
O21.4738 (5)0.81229 (18)0.60808 (11)0.0847 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.082 (2)0.070 (2)0.0865 (18)−0.0248 (18)−0.0068 (17)0.0110 (16)
C20.129 (4)0.069 (2)0.110 (3)−0.037 (3)0.019 (3)−0.015 (2)
C30.138 (4)0.055 (2)0.135 (3)−0.009 (3)0.063 (3)−0.006 (2)
C40.079 (2)0.075 (2)0.119 (3)0.015 (2)0.026 (2)0.031 (2)
C50.0600 (15)0.0640 (17)0.0764 (16)−0.0006 (15)0.0024 (14)0.0127 (14)
C60.0554 (14)0.0459 (14)0.0696 (14)−0.0079 (12)0.0013 (12)0.0121 (12)
C70.0515 (13)0.0542 (16)0.0968 (18)−0.0058 (14)0.0057 (14)0.0154 (15)
C80.091 (2)0.068 (2)0.165 (3)−0.010 (2)0.043 (3)−0.030 (2)
C90.081 (2)0.0504 (17)0.113 (2)0.0010 (16)0.026 (2)−0.0255 (18)
C100.099 (2)0.0543 (16)0.0814 (18)0.0031 (19)0.0169 (18)−0.0043 (15)
C110.0839 (19)0.0552 (16)0.0694 (16)0.0009 (16)−0.0002 (15)−0.0039 (13)
C120.0789 (18)0.0457 (14)0.0680 (14)0.0075 (16)0.0052 (14)−0.0091 (12)
C130.108 (3)0.072 (2)0.0708 (16)0.004 (2)−0.0044 (18)−0.0100 (15)
C140.095 (2)0.073 (2)0.099 (2)0.001 (2)−0.008 (2)−0.030 (2)
C150.097 (2)0.070 (2)0.100 (2)−0.015 (2)0.008 (2)−0.0039 (17)
N10.0726 (15)0.0577 (15)0.1068 (17)−0.0101 (14)0.0126 (15)−0.0071 (14)
O10.0699 (13)0.111 (2)0.1132 (17)0.0012 (16)−0.0258 (14)0.0017 (16)
O20.1129 (18)0.0647 (13)0.0765 (12)−0.0104 (13)0.0065 (13)0.0056 (11)

Geometric parameters (Å, °)

C1—C21.381 (6)C8—H8B0.97
C1—C61.383 (4)C9—C101.369 (5)
C1—H10.93C9—C141.390 (5)
C2—C31.359 (7)C10—C111.376 (5)
C2—H20.93C10—H100.93
C3—C41.366 (6)C11—C121.385 (4)
C3—H30.93C11—H110.93
C4—C51.387 (5)C12—C131.367 (5)
C4—H40.93C12—O21.372 (4)
C5—O11.352 (4)C13—C141.374 (5)
C5—C61.389 (4)C13—H130.93
C6—C71.456 (4)C14—H140.93
C7—N11.268 (4)C15—O21.413 (4)
C7—H70.93C15—H15A0.96
C8—N11.464 (4)C15—H15B0.96
C8—C91.509 (5)C15—H15C0.96
C8—H8A0.97O1—H1A0.82
C2—C1—C6121.0 (4)C10—C9—C14117.7 (3)
C2—C1—H1119.5C10—C9—C8121.2 (4)
C6—C1—H1119.5C14—C9—C8121.0 (4)
C3—C2—C1119.1 (4)C9—C10—C11122.0 (3)
C3—C2—H2120.4C9—C10—H10119
C1—C2—H2120.4C11—C10—H10119
C2—C3—C4121.9 (4)C10—C11—C12119.2 (3)
C2—C3—H3119C10—C11—H11120.4
C4—C3—H3119C12—C11—H11120.4
C3—C4—C5118.8 (4)C13—C12—O2116.0 (3)
C3—C4—H4120.6C13—C12—C11119.9 (3)
C5—C4—H4120.6O2—C12—C11124.1 (3)
O1—C5—C4118.5 (3)C12—C13—C14120.0 (3)
O1—C5—C6120.8 (3)C12—C13—H13120
C4—C5—C6120.7 (3)C14—C13—H13120
C1—C6—C5118.3 (3)C13—C14—C9121.2 (3)
C1—C6—C7120.1 (3)C13—C14—H14119.4
C5—C6—C7121.6 (3)C9—C14—H14119.4
N1—C7—C6121.6 (3)O2—C15—H15A109.5
N1—C7—H7119.2O2—C15—H15B109.5
C6—C7—H7119.2H15A—C15—H15B109.5
N1—C8—C9110.4 (3)O2—C15—H15C109.5
N1—C8—H8A109.6H15A—C15—H15C109.5
C9—C8—H8A109.6H15B—C15—H15C109.5
N1—C8—H8B109.6C7—N1—C8118.9 (3)
C9—C8—H8B109.6C5—O1—H1A109.5
H8A—C8—H8B108.1C12—O2—C15117.8 (2)
C6—C1—C2—C30.5 (5)C14—C9—C10—C110.4 (5)
C1—C2—C3—C4−0.6 (6)C8—C9—C10—C11178.5 (3)
C2—C3—C4—C5−1.1 (6)C9—C10—C11—C12−0.1 (5)
C3—C4—C5—O1−178.3 (3)C10—C11—C12—C13−0.3 (4)
C3—C4—C5—C62.9 (5)C10—C11—C12—O2179.0 (3)
C2—C1—C6—C51.3 (4)O2—C12—C13—C14−179.0 (3)
C2—C1—C6—C7−179.2 (3)C11—C12—C13—C140.3 (5)
O1—C5—C6—C1178.2 (3)C12—C13—C14—C90.0 (5)
C4—C5—C6—C1−3.0 (4)C10—C9—C14—C13−0.3 (5)
O1—C5—C6—C7−1.3 (4)C8—C9—C14—C13−178.4 (3)
C4—C5—C6—C7177.5 (3)C6—C7—N1—C8−179.6 (3)
C1—C6—C7—N1179.4 (3)C9—C8—N1—C7−125.6 (4)
C5—C6—C7—N1−1.0 (4)C13—C12—O2—C15179.2 (3)
N1—C8—C9—C10−89.5 (4)C11—C12—O2—C150.0 (4)
N1—C8—C9—C1488.6 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.852.574 (3)146
C11—H11···O1i0.932.543.464 (4)175

Symmetry codes: (i) −x+3, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2800).

References

  • Adsule, S., Barve, V., Chen, D., Ahmed, F., Dou, Q. P., Padhye, S. & Sarkar, F. H. (2006). J. Med. Chem.49, 7242–7246. [PubMed]
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  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Kannappan, R., Tanase, S., Mutikainen, I., Turpeinen, U. & Reedijk, J. (2005). Inorg. Chim. Acta, 358, 383–388.
  • Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem.14, 7482–7489. [PubMed]
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