(E)-4-Meth-oxy-2-(o-tolyl-imino-meth-yl)phenol.

In the mol-ecule of the title compound, C(15)H(15)NO(2), the aromatic rings are oriented at a dihedral angle of 15.46 (6)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a nearly planar six-membered ring [maximum deviation of 0.035 (5) Å for the N atom] which is almost coplanar with the adjacent ring, making a dihedral angle of 0.8 (3)°. The title organic mol-ecule is a phenol-imine tautomer, as evidenced by the C-O, C-N and C-C bond lengths. Mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds that generate a C(5) chain. C-H⋯π and π-π inter-actions exist in the structure. The π-π inter-action occurs between the phenol ring and its symmetry equivalent at (1 - x, 1 - y, -z), with a centroid-centroid distance of 3.727 (7) Å and a plane-to-plane separation of 3.383 (5) Å, resulting in an offset angle of 24.82 (1)°.

Related literature

For previous work in our structural study of Schiff bases, see: Özek et al. (2007 ▶); Odabaşoğlu, Arslan et al. (2007 ▶); Odabaşoğlu, Büyükgüngör et al. (2007 ▶). For a related compound, see: Albayrak et al. (2005 ▶).

Experimental

Crystal data

C15H15NO2

M = 241.28

Monoclinic,

a = 13.2889 (6) Å

b = 8.5986 (6) Å

c = 11.6714 (6) Å

β = 113.284 (3)°

V = 1225.03 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.59 × 0.47 × 0.30 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.954, T max = 0.975

6569 measured reflections

2537 independent reflections

2108 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.02

2537 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009192/bv2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009192/bv2115Isup2.hkl

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

C15H15NO2	F(000) = 512
Mr = 241.28	Dx = 1.308 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6569 reflections
a = 13.2889 (6) Å	θ = 1.9–28.0°
b = 8.5986 (6) Å	µ = 0.09 mm−1
c = 11.6714 (6) Å	T = 100 K
β = 113.284 (3)°	Prism, red
V = 1225.03 (12) Å3	0.59 × 0.47 × 0.30 mm
Z = 4

Stoe IPDS II diffractometer	2537 independent reflections
Radiation source: fine-focus sealed tube	2108 reflections with I > 2σ(I)
plane graphite	Rint = 0.039
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.9°
ω scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→10
Tmin = 0.954, Tmax = 0.975	l = −14→13
6569 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.2485P] where P = (Fo2 + 2Fc2)/3
2537 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. 133 frames, detector distance = 80 mm

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 > σ(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.

	x	y	z	Uiso*/Ueq
C1	0.50912 (9)	0.80474 (14)	0.44057 (10)	0.0202 (2)
C2	0.50739 (9)	0.87880 (14)	0.33229 (10)	0.0220 (3)
C3	0.41277 (10)	0.95544 (15)	0.25458 (11)	0.0260 (3)
C4	0.32140 (10)	0.95800 (15)	0.28313 (11)	0.0268 (3)
C5	0.32211 (9)	0.88566 (14)	0.39055 (11)	0.0240 (3)
C6	0.41552 (9)	0.80964 (14)	0.46900 (11)	0.0221 (3)
C7	0.22417 (11)	0.82076 (17)	0.51644 (13)	0.0301 (3)
C8	0.60665 (9)	0.72552 (14)	0.52526 (10)	0.0204 (2)
C9	0.78609 (9)	0.62921 (13)	0.57661 (10)	0.0199 (2)
C10	0.88252 (9)	0.65581 (14)	0.55698 (10)	0.0220 (3)
C11	0.97626 (10)	0.57301 (15)	0.62954 (11)	0.0253 (3)
C12	0.97591 (10)	0.46596 (15)	0.71788 (11)	0.0273 (3)
C13	0.87983 (10)	0.43903 (15)	0.73477 (11)	0.0267 (3)
C14	0.78528 (10)	0.52031 (15)	0.66497 (11)	0.0238 (3)
C15	0.88540 (10)	0.77174 (16)	0.46210 (13)	0.0271 (3)
N1	0.69160 (8)	0.71244 (11)	0.49897 (9)	0.0201 (2)
O1	0.59622 (7)	0.88000 (11)	0.30225 (8)	0.0259 (2)
O2	0.22688 (7)	0.89755 (11)	0.40973 (9)	0.0299 (2)
H1	0.6488 (15)	0.821 (2)	0.3689 (18)	0.052 (5)*
H3	0.4132 (12)	1.0039 (19)	0.1796 (14)	0.034 (4)*
H4	0.2560 (12)	1.0104 (19)	0.2304 (14)	0.034 (4)*
H6	0.4193 (11)	0.7593 (18)	0.5449 (14)	0.027 (3)*
H7A	0.2795 (12)	0.8655 (18)	0.5964 (14)	0.030 (4)*
H7B	0.2372 (13)	0.705 (2)	0.5150 (15)	0.038 (4)*
H8	0.6040 (11)	0.6867 (17)	0.6023 (14)	0.026 (3)*
H11	1.0416 (12)	0.5929 (17)	0.6150 (13)	0.030 (4)*
H12	1.0432 (12)	0.4111 (18)	0.7671 (14)	0.032 (4)*
H13	0.8786 (12)	0.3638 (19)	0.7957 (14)	0.033 (4)*
H14	0.7188 (12)	0.4974 (18)	0.6756 (13)	0.028 (4)*
H15A	0.9547 (15)	0.772 (2)	0.4543 (16)	0.046 (5)*
H15B	0.8291 (13)	0.7525 (19)	0.3784 (15)	0.036 (4)*
H7C	0.1484 (13)	0.838 (2)	0.5114 (15)	0.039 (4)*
H15C	0.8706 (14)	0.879 (2)	0.4830 (16)	0.048 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0214 (5)	0.0197 (6)	0.0185 (5)	−0.0007 (4)	0.0068 (4)	−0.0023 (4)
C2	0.0249 (5)	0.0209 (6)	0.0206 (5)	−0.0010 (5)	0.0093 (4)	−0.0025 (4)
C3	0.0313 (6)	0.0239 (6)	0.0201 (5)	0.0010 (5)	0.0072 (5)	0.0020 (5)
C4	0.0238 (6)	0.0249 (6)	0.0256 (6)	0.0033 (5)	0.0033 (5)	0.0004 (5)
C5	0.0205 (5)	0.0221 (6)	0.0287 (6)	−0.0003 (5)	0.0088 (5)	−0.0041 (5)
C6	0.0242 (6)	0.0211 (6)	0.0212 (5)	0.0006 (5)	0.0091 (4)	−0.0002 (4)
C7	0.0252 (6)	0.0313 (7)	0.0381 (7)	−0.0007 (5)	0.0172 (5)	−0.0039 (6)
C8	0.0234 (5)	0.0203 (6)	0.0179 (5)	−0.0002 (4)	0.0083 (4)	−0.0015 (4)
C9	0.0211 (5)	0.0196 (6)	0.0177 (5)	0.0012 (4)	0.0063 (4)	−0.0034 (4)
C10	0.0235 (5)	0.0193 (6)	0.0223 (5)	−0.0004 (4)	0.0083 (4)	−0.0038 (5)
C11	0.0200 (5)	0.0250 (6)	0.0297 (6)	−0.0005 (5)	0.0086 (5)	−0.0034 (5)
C12	0.0239 (6)	0.0277 (7)	0.0255 (6)	0.0053 (5)	0.0047 (5)	−0.0011 (5)
C13	0.0325 (6)	0.0258 (6)	0.0221 (6)	0.0053 (5)	0.0112 (5)	0.0036 (5)
C14	0.0248 (6)	0.0248 (6)	0.0231 (5)	0.0020 (5)	0.0110 (4)	−0.0002 (5)
C15	0.0240 (6)	0.0274 (7)	0.0326 (7)	0.0012 (5)	0.0139 (5)	0.0033 (5)
N1	0.0209 (5)	0.0197 (5)	0.0194 (4)	0.0007 (4)	0.0076 (4)	−0.0012 (4)
O1	0.0280 (4)	0.0300 (5)	0.0229 (4)	0.0028 (4)	0.0135 (3)	0.0043 (4)
O2	0.0206 (4)	0.0305 (5)	0.0391 (5)	0.0038 (4)	0.0122 (4)	0.0027 (4)

C1—C2	1.4071 (16)	C8—H8	0.973 (15)
C1—C6	1.4091 (16)	C9—C14	1.3961 (17)
C1—C8	1.4519 (16)	C9—C10	1.4068 (16)
C2—O1	1.3579 (14)	C9—N1	1.4179 (14)
C2—C3	1.3916 (17)	C10—C11	1.3934 (16)
C3—C4	1.3805 (18)	C10—C15	1.5017 (17)
C3—H3	0.971 (16)	C11—C12	1.3836 (18)
C4—C5	1.3962 (18)	C11—H11	0.963 (16)
C4—H4	0.956 (16)	C12—C13	1.3862 (18)
C5—O2	1.3734 (15)	C12—H12	0.973 (15)
C5—C6	1.3812 (17)	C13—C14	1.3862 (17)
C6—H6	0.969 (15)	C13—H13	0.966 (16)
C7—O2	1.4226 (17)	C14—H14	0.959 (15)
C7—H7A	1.008 (15)	C15—H15A	0.960 (18)
C7—H7B	1.008 (18)	C15—H15B	0.981 (16)
C7—H7C	0.996 (17)	C15—H15C	0.99 (2)
C8—N1	1.2865 (15)	O1—H1	0.958 (19)
C2—C1—C6	119.70 (10)	C14—C9—C10	120.19 (10)
C2—C1—C8	121.13 (10)	C14—C9—N1	123.17 (10)
C6—C1—C8	119.16 (10)	C10—C9—N1	116.58 (10)
O1—C2—C3	118.81 (11)	C11—C10—C9	118.10 (11)
O1—C2—C1	121.88 (10)	C11—C10—C15	120.67 (11)
C3—C2—C1	119.30 (11)	C9—C10—C15	121.22 (10)
C4—C3—C2	120.30 (11)	C12—C11—C10	121.82 (11)
C4—C3—H3	122.0 (9)	C12—C11—H11	121.2 (9)
C2—C3—H3	117.7 (9)	C10—C11—H11	117.0 (9)
C3—C4—C5	121.02 (11)	C11—C12—C13	119.45 (11)
C3—C4—H4	120.9 (9)	C11—C12—H12	119.3 (9)
C5—C4—H4	118.0 (9)	C13—C12—H12	121.2 (9)
O2—C5—C6	124.87 (11)	C12—C13—C14	120.27 (12)
O2—C5—C4	115.69 (11)	C12—C13—H13	120.1 (9)
C6—C5—C4	119.43 (11)	C14—C13—H13	119.6 (9)
C5—C6—C1	120.25 (11)	C13—C14—C9	120.16 (11)
C5—C6—H6	121.7 (8)	C13—C14—H14	119.2 (9)
C1—C6—H6	118.1 (8)	C9—C14—H14	120.6 (9)
O2—C7—H7A	111.8 (9)	C10—C15—H15A	112.1 (11)
O2—C7—H7B	112.2 (9)	C10—C15—H15B	112.9 (10)
H7A—C7—H7B	108.9 (13)	H15A—C15—H15B	106.8 (14)
O2—C7—H7C	104.7 (9)	C10—C15—H15C	111.7 (10)
H7A—C7—H7C	110.4 (13)	H15A—C15—H15C	108.2 (15)
H7B—C7—H7C	108.8 (13)	H15B—C15—H15C	104.7 (14)
N1—C8—C1	120.66 (10)	C8—N1—C9	122.05 (10)
N1—C8—H8	123.1 (8)	C2—O1—H1	102.5 (11)
C1—C8—H8	116.2 (8)	C5—O2—C7	116.87 (9)
C6—C1—C2—O1	178.64 (11)	N1—C9—C10—C11	−178.42 (10)
C8—C1—C2—O1	−0.16 (17)	C14—C9—C10—C15	179.71 (11)
C6—C1—C2—C3	−0.23 (17)	N1—C9—C10—C15	2.50 (16)
C8—C1—C2—C3	−179.03 (11)	C9—C10—C11—C12	0.70 (18)
O1—C2—C3—C4	−179.26 (11)	C15—C10—C11—C12	179.77 (12)
C1—C2—C3—C4	−0.36 (18)	C10—C11—C12—C13	0.37 (19)
C2—C3—C4—C5	0.67 (19)	C11—C12—C13—C14	−0.92 (19)
C3—C4—C5—O2	179.29 (11)	C12—C13—C14—C9	0.40 (18)
C3—C4—C5—C6	−0.38 (19)	C10—C9—C14—C13	0.69 (17)
O2—C5—C6—C1	−179.85 (11)	N1—C9—C14—C13	177.71 (11)
C4—C5—C6—C1	−0.21 (18)	C1—C8—N1—C9	−176.83 (10)
C2—C1—C6—C5	0.51 (17)	C14—C9—N1—C8	18.82 (17)
C8—C1—C6—C5	179.34 (11)	C10—C9—N1—C8	−164.07 (11)
C2—C1—C8—N1	−4.59 (17)	C6—C5—O2—C7	−2.26 (17)
C6—C1—C8—N1	176.60 (11)	C4—C5—O2—C7	178.09 (11)
C14—C9—C10—C11	−1.22 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.958 (19)	1.68 (2)	2.5794 (13)	154.8 (17)
C8—H8···O1i	0.973 (15)	2.444 (15)	3.4129 (14)	173.5 (12)
C7—H7B···Cg2ii	1.008 (18)	2.903 (17)	3.6727 (16)	134.1 (16)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.958 (19)	1.68 (2)	2.5794 (13)	154.8 (17)
C8—H8⋯O1i	0.973 (15)	2.444 (15)	3.4129 (14)	173.5 (12)
C7—H7B⋯Cg2ii	1.01 (2)	2.90 (2)	3.6727 (16)	134 (2)

Symmetry codes: (i) ; (ii) .