2-[(4-Meth­oxy­benz­yl)imino­meth­yl]phenol

Phurat, C.; Theerawattananond, T.; Muangsin, N.

doi:10.1107/S1600536810048282

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3298

https://doi.org/10.1107/S1600536810048282

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2-[(4-Methoxybenzyl)iminomethyl]phenol

Chuttree Phurat,^a Thapong Theerawattananond ^a and Nongnuj Muangsin ^a ^*

^aResearch Centre of Bioorganic Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand
^*Correspondence e-mail: nongnuj.j@chula.ac.th

(Received 15 November 2010; accepted 19 November 2010; online 24 November 2010)

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 ); Karthikeyan et al. (2006 ). For related structures, see: Phurat et al. (2010 ); Tariq et al. (2010 ); Khalaji & Simpson (2009 ). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ). For details of the synthesis, see: Phurat et al. (2010); Kannappan et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₅NO₂
M_r = 241.28
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.162
S = 1.13
1573 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.85	2.574 (3)	146
C11—H11⋯O1ⁱ	0.93	2.54	3.464 (4)	175
Symmetry code: (i) $[-x+3, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048282/cv2800Isup2.hkl

checkCIF report

Comment top

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].

Related literature top

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

Experimental top

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.

Structure description top

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

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

Computing details top

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

Figures top

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.

2-[(4-Methoxybenzyl)iminomethyl]phenol top

Crystal data top

C₁₅H₁₅NO₂	F(000) = 512
M_r = 241.28	D_x = 1.228 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.7190 (8) Å	µ = 0.08 mm⁻¹
b = 12.7229 (19) Å	T = 293 K
c = 17.936 (3) Å	Needle, yellow
V = 1305.0 (3) Å³	0.3 × 0.18 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1177 reflections with I > 2σ(I)
Radiation source: Mo Kα	R_int = 0.040
Graphite monochromator	θ_max = 26.5°, θ_min = 2.0°
φ and ω scans	h = −7→7
5776 measured reflections	k = −15→14
1573 independent reflections	l = −20→22

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.162	(Δ/σ)_max < 0.001
S = 1.13	Δρ_max = 0.15 e Å⁻³
1573 reflections	Δρ_min = −0.16 e Å⁻³
164 parameters

Crystal data top

C₁₅H₁₅NO₂	V = 1305.0 (3) Å³
M_r = 241.28	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.7190 (8) Å	µ = 0.08 mm⁻¹
b = 12.7229 (19) Å	T = 293 K
c = 17.936 (3) Å	0.3 × 0.18 × 0.04 mm

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.13	Δρ_max = 0.15 e Å⁻³
1573 reflections	Δρ_min = −0.16 e Å⁻³
164 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.

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

	x	y	z	U_iso*/U_eq
C1	0.7854 (7)	0.1595 (3)	0.54878 (17)	0.0795 (9)
H1	0.642	0.183	0.5308	0.095*
C2	0.8661 (10)	0.0614 (3)	0.5283 (2)	0.1029 (14)
H2	0.7787	0.0191	0.4965	0.123*
C3	1.0749 (9)	0.0274 (3)	0.5552 (3)	0.1095 (15)
H3	1.1283	−0.039	0.5417	0.131*
C4	1.2087 (7)	0.0879 (3)	0.6015 (2)	0.0909 (11)
H4	1.3499	0.0627	0.6199	0.109*
C5	1.1300 (5)	0.1875 (2)	0.62042 (17)	0.0668 (8)
C6	0.9144 (5)	0.2235 (2)	0.59563 (14)	0.0570 (6)
C7	0.8246 (5)	0.3261 (2)	0.61737 (18)	0.0675 (7)
H7	0.6806	0.3482	0.599	0.081*
C8	0.8369 (7)	0.4881 (3)	0.6807 (3)	0.1079 (14)
H8A	0.7999	0.4889	0.7335	0.129*
H8B	0.6929	0.4989	0.6532	0.129*
C9	1.0065 (6)	0.5755 (3)	0.6632 (2)	0.0814 (10)
C10	1.1673 (7)	0.6086 (3)	0.71468 (18)	0.0783 (9)
H10	1.1688	0.5775	0.7616	0.094*
C11	1.3269 (6)	0.6865 (2)	0.69908 (16)	0.0695 (8)
H11	1.4343	0.7077	0.735	0.083*
C12	1.3254 (6)	0.7330 (2)	0.62925 (15)	0.0642 (7)
C13	1.1673 (8)	0.7010 (3)	0.57680 (19)	0.0836 (10)
H13	1.1667	0.7319	0.5298	0.1*
C14	1.0094 (7)	0.6231 (3)	0.5935 (2)	0.0892 (11)
H14	0.9025	0.6018	0.5575	0.107*
C15	1.6382 (7)	0.8487 (3)	0.6610 (2)	0.0891 (10)
H15A	1.73	0.904	0.6394	0.134*
H15B	1.7389	0.7919	0.6754	0.134*
H15C	1.5573	0.8749	0.704	0.134*
N1	0.9379 (4)	0.3862 (2)	0.66067 (15)	0.0790 (7)
O1	1.2662 (4)	0.2479 (2)	0.66466 (15)	0.0979 (8)
H1A	1.1921	0.2997	0.6782	0.147*
O2	1.4738 (5)	0.81229 (18)	0.60808 (11)	0.0847 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.082 (2)	0.070 (2)	0.0865 (18)	−0.0248 (18)	−0.0068 (17)	0.0110 (16)
C2	0.129 (4)	0.069 (2)	0.110 (3)	−0.037 (3)	0.019 (3)	−0.015 (2)
C3	0.138 (4)	0.055 (2)	0.135 (3)	−0.009 (3)	0.063 (3)	−0.006 (2)
C4	0.079 (2)	0.075 (2)	0.119 (3)	0.015 (2)	0.026 (2)	0.031 (2)
C5	0.0600 (15)	0.0640 (17)	0.0764 (16)	−0.0006 (15)	0.0024 (14)	0.0127 (14)
C6	0.0554 (14)	0.0459 (14)	0.0696 (14)	−0.0079 (12)	0.0013 (12)	0.0121 (12)
C7	0.0515 (13)	0.0542 (16)	0.0968 (18)	−0.0058 (14)	0.0057 (14)	0.0154 (15)
C8	0.091 (2)	0.068 (2)	0.165 (3)	−0.010 (2)	0.043 (3)	−0.030 (2)
C9	0.081 (2)	0.0504 (17)	0.113 (2)	0.0010 (16)	0.026 (2)	−0.0255 (18)
C10	0.099 (2)	0.0543 (16)	0.0814 (18)	0.0031 (19)	0.0169 (18)	−0.0043 (15)
C11	0.0839 (19)	0.0552 (16)	0.0694 (16)	0.0009 (16)	−0.0002 (15)	−0.0039 (13)
C12	0.0789 (18)	0.0457 (14)	0.0680 (14)	0.0075 (16)	0.0052 (14)	−0.0091 (12)
C13	0.108 (3)	0.072 (2)	0.0708 (16)	0.004 (2)	−0.0044 (18)	−0.0100 (15)
C14	0.095 (2)	0.073 (2)	0.099 (2)	0.001 (2)	−0.008 (2)	−0.030 (2)
C15	0.097 (2)	0.070 (2)	0.100 (2)	−0.015 (2)	0.008 (2)	−0.0039 (17)
N1	0.0726 (15)	0.0577 (15)	0.1068 (17)	−0.0101 (14)	0.0126 (15)	−0.0071 (14)
O1	0.0699 (13)	0.111 (2)	0.1132 (17)	0.0012 (16)	−0.0258 (14)	0.0017 (16)
O2	0.1129 (18)	0.0647 (13)	0.0765 (12)	−0.0104 (13)	0.0065 (13)	0.0056 (11)

Geometric parameters (Å, º) top

C1—C2	1.381 (6)	C8—H8B	0.97
C1—C6	1.383 (4)	C9—C10	1.369 (5)
C1—H1	0.93	C9—C14	1.390 (5)
C2—C3	1.359 (7)	C10—C11	1.376 (5)
C2—H2	0.93	C10—H10	0.93
C3—C4	1.366 (6)	C11—C12	1.385 (4)
C3—H3	0.93	C11—H11	0.93
C4—C5	1.387 (5)	C12—C13	1.367 (5)
C4—H4	0.93	C12—O2	1.372 (4)
C5—O1	1.352 (4)	C13—C14	1.374 (5)
C5—C6	1.389 (4)	C13—H13	0.93
C6—C7	1.456 (4)	C14—H14	0.93
C7—N1	1.268 (4)	C15—O2	1.413 (4)
C7—H7	0.93	C15—H15A	0.96
C8—N1	1.464 (4)	C15—H15B	0.96
C8—C9	1.509 (5)	C15—H15C	0.96
C8—H8A	0.97	O1—H1A	0.82

C2—C1—C6	121.0 (4)	C10—C9—C14	117.7 (3)
C2—C1—H1	119.5	C10—C9—C8	121.2 (4)
C6—C1—H1	119.5	C14—C9—C8	121.0 (4)
C3—C2—C1	119.1 (4)	C9—C10—C11	122.0 (3)
C3—C2—H2	120.4	C9—C10—H10	119
C1—C2—H2	120.4	C11—C10—H10	119
C2—C3—C4	121.9 (4)	C10—C11—C12	119.2 (3)
C2—C3—H3	119	C10—C11—H11	120.4
C4—C3—H3	119	C12—C11—H11	120.4
C3—C4—C5	118.8 (4)	C13—C12—O2	116.0 (3)
C3—C4—H4	120.6	C13—C12—C11	119.9 (3)
C5—C4—H4	120.6	O2—C12—C11	124.1 (3)
O1—C5—C4	118.5 (3)	C12—C13—C14	120.0 (3)
O1—C5—C6	120.8 (3)	C12—C13—H13	120
C4—C5—C6	120.7 (3)	C14—C13—H13	120
C1—C6—C5	118.3 (3)	C13—C14—C9	121.2 (3)
C1—C6—C7	120.1 (3)	C13—C14—H14	119.4
C5—C6—C7	121.6 (3)	C9—C14—H14	119.4
N1—C7—C6	121.6 (3)	O2—C15—H15A	109.5
N1—C7—H7	119.2	O2—C15—H15B	109.5
C6—C7—H7	119.2	H15A—C15—H15B	109.5
N1—C8—C9	110.4 (3)	O2—C15—H15C	109.5
N1—C8—H8A	109.6	H15A—C15—H15C	109.5
C9—C8—H8A	109.6	H15B—C15—H15C	109.5
N1—C8—H8B	109.6	C7—N1—C8	118.9 (3)
C9—C8—H8B	109.6	C5—O1—H1A	109.5
H8A—C8—H8B	108.1	C12—O2—C15	117.8 (2)

C6—C1—C2—C3	0.5 (5)	C14—C9—C10—C11	0.4 (5)
C1—C2—C3—C4	−0.6 (6)	C8—C9—C10—C11	178.5 (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—C6	2.9 (5)	C10—C11—C12—O2	179.0 (3)
C2—C1—C6—C5	1.3 (4)	O2—C12—C13—C14	−179.0 (3)
C2—C1—C6—C7	−179.2 (3)	C11—C12—C13—C14	0.3 (5)
O1—C5—C6—C1	178.2 (3)	C12—C13—C14—C9	0.0 (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—C7	177.5 (3)	C6—C7—N1—C8	−179.6 (3)
C1—C6—C7—N1	179.4 (3)	C9—C8—N1—C7	−125.6 (4)
C5—C6—C7—N1	−1.0 (4)	C13—C12—O2—C15	179.2 (3)
N1—C8—C9—C10	−89.5 (4)	C11—C12—O2—C15	0.0 (4)
N1—C8—C9—C14	88.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.85	2.574 (3)	146
C11—H11···O1ⁱ	0.93	2.54	3.464 (4)	175

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₂
M_r	241.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	5.7190 (8), 12.7229 (19), 17.936 (3)
V (Å³)	1305.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.3 × 0.18 × 0.04

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5776, 1573, 1177
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.162, 1.13
No. of reflections	1573
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.85	2.574 (3)	146.4
C11—H11···O1ⁱ	0.93	2.54	3.464 (4)	174.8

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

Acknowledgements

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.

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