2-[(4-Meth-oxy-benz-yl)imino-meth-yl]phenol.

In the title Schiff base compound, C(15)H(15)NO(2), prepared from 4-meth-oxy-benzyl-amine and salicyl-aldehyde, an intra-molecular O-H⋯N hydrogen bonds influences the mol-ecular conformation; the two aromatic rings form a dihedral angle of 73.5 (1)°. In the crystal, weak inter-molecular C-H⋯O inter-actions link the mol-ecules 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 n class="Chemical">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 = 241.28

Orthorhombic,

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 ▶); cell refinement: SAIn class="Chemical">NT (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 ▶).

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

C15H15NO2	F(000) = 512
Mr = 241.28	Dx = 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

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

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.15 e Å−3
1573 reflections	Δρmin = −0.16 e Å−3
164 parameters

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .