2-[(E)-(2,3-Dimethyl-phen-yl)imino-meth-yl]phenol.

In the title compound, C(15)H(15)NO, the almost planar 2,3-dimethyl-aniline unit and the salicyl-aldehyde group (r.m.s. deviations of 0.0156 and 0.0109 Å, respectively) are oriented at a dihedral angle of 43.69 (9)° with respect to each other. An S(6) ring motif is formed due to intra-molecular O-H⋯N hydrogen bonding. In the crystal, C-H⋯π inter-actions occur between the 2,3-dimethyl-aniline unit and the salicyl-aldehyde group, where the CH is from the o-methyl group.

Related literature

For background to Schiff bases synthesized from 2,3-dimethyl­aniline and for related structures, see: Tahir et al. (2010a ▶,b ▶); Tariq et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Orthorhombic,

a = 7.5641 (7) Å

b = 12.5889 (13) Å

c = 13.0643 (14) Å

V = 1244.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.32 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.985

9729 measured reflections

1316 independent reflections

687 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.157

S = 1.11

1316 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033398/bq2232sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033398/bq2232Isup2.hkl

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

C15H15NO	F(000) = 480
Mr = 225.28	Dx = 1.203 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 687 reflections
a = 7.5641 (7) Å	θ = 2.3–25.2°
b = 12.5889 (13) Å	µ = 0.08 mm−1
c = 13.0643 (14) Å	T = 296 K
V = 1244.0 (2) Å3	Needle, colorless
Z = 4	0.32 × 0.12 × 0.10 mm

Bruker Kappa APEXII CCD diffractometer	1316 independent reflections
Radiation source: fine-focus sealed tube	687 reflections with I > 2σ(I)
graphite	Rint = 0.085
Detector resolution: 8.1 pixels mm-1	θmax = 25.2°, θmin = 2.3°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.980, Tmax = 0.985	l = −15→15
9729 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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0624P)2] where P = (Fo2 + 2Fc2)/3
1316 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	−0.1515 (5)	0.5069 (3)	0.2310 (3)	0.0897 (19)
N1	−0.0156 (5)	0.3687 (4)	0.1080 (3)	0.0627 (17)
C1	0.0128 (6)	0.3279 (4)	0.0080 (4)	0.056 (2)
C2	0.0758 (6)	0.3945 (5)	−0.0690 (5)	0.059 (2)
C3	0.0952 (6)	0.3556 (5)	−0.1668 (4)	0.065 (2)
C4	0.0551 (7)	0.2503 (6)	−0.1881 (5)	0.077 (3)
C5	−0.0066 (7)	0.1849 (5)	−0.1113 (5)	0.083 (3)
C6	−0.0298 (7)	0.2231 (5)	−0.0142 (5)	0.072 (2)
C7	0.1219 (8)	0.5080 (4)	−0.0424 (5)	0.088 (3)
C8	0.1642 (9)	0.4236 (5)	−0.2532 (4)	0.106 (3)
C9	0.0214 (6)	0.3121 (4)	0.1866 (4)	0.064 (2)
C10	−0.0210 (7)	0.3453 (4)	0.2888 (4)	0.061 (2)
C11	0.0197 (8)	0.2804 (5)	0.3715 (4)	0.081 (2)
C12	−0.0244 (10)	0.3084 (6)	0.4696 (5)	0.095 (3)
C13	−0.1103 (10)	0.4022 (7)	0.4868 (6)	0.097 (3)
C14	−0.1526 (7)	0.4687 (5)	0.4063 (6)	0.088 (3)
C15	−0.1088 (7)	0.4403 (5)	0.3083 (5)	0.068 (3)
H1	−0.11767	0.48168	0.17655	0.1075*
H4	0.06981	0.22390	−0.25406	0.0926*
H5	−0.03254	0.11425	−0.12564	0.0997*
H6	−0.07406	0.17895	0.03678	0.0859*
H7A	0.24802	0.51622	−0.04157	0.1311*
H7B	0.07492	0.52507	0.02387	0.1311*
H7C	0.07187	0.55492	−0.09262	0.1311*
H8A	0.08868	0.48428	−0.26179	0.1586*
H8B	0.16581	0.38290	−0.31528	0.1586*
H8C	0.28187	0.44699	−0.23737	0.1586*
H9	0.07767	0.24716	0.17715	0.0767*
H11	0.07817	0.21654	0.36011	0.0969*
H12	0.00398	0.26397	0.52398	0.1147*
H13	−0.14067	0.42136	0.55328	0.1166*
H14	−0.21052	0.53261	0.41862	0.1054*

	U11	U22	U33	U12	U13	U23
O1	0.084 (3)	0.075 (3)	0.110 (4)	0.023 (3)	0.003 (3)	−0.009 (3)
N1	0.049 (3)	0.061 (3)	0.078 (3)	−0.008 (2)	0.003 (3)	−0.001 (3)
C1	0.038 (3)	0.050 (4)	0.081 (4)	−0.001 (3)	−0.005 (3)	−0.001 (3)
C2	0.045 (3)	0.057 (4)	0.075 (4)	−0.002 (3)	−0.009 (3)	0.010 (4)
C3	0.052 (3)	0.071 (5)	0.073 (4)	0.001 (3)	−0.015 (3)	0.018 (4)
C4	0.071 (4)	0.083 (5)	0.077 (4)	0.005 (3)	−0.009 (3)	−0.015 (4)
C5	0.078 (4)	0.071 (5)	0.101 (5)	−0.011 (4)	0.004 (4)	−0.010 (4)
C6	0.071 (4)	0.063 (4)	0.081 (4)	−0.012 (3)	0.009 (3)	0.005 (3)
C7	0.084 (4)	0.057 (4)	0.122 (5)	−0.011 (4)	−0.007 (4)	0.015 (4)
C8	0.118 (6)	0.113 (6)	0.086 (5)	−0.006 (5)	−0.005 (4)	0.019 (4)
C9	0.049 (3)	0.056 (4)	0.087 (4)	0.001 (3)	0.005 (3)	−0.003 (4)
C10	0.055 (3)	0.057 (4)	0.071 (4)	−0.003 (3)	0.004 (3)	−0.005 (3)
C11	0.090 (4)	0.066 (4)	0.086 (4)	−0.004 (4)	−0.002 (4)	−0.007 (4)
C12	0.114 (6)	0.089 (6)	0.083 (5)	−0.024 (5)	0.003 (4)	−0.003 (4)
C13	0.084 (5)	0.112 (7)	0.096 (5)	−0.030 (5)	0.019 (4)	−0.031 (5)
C14	0.067 (4)	0.078 (5)	0.118 (6)	−0.001 (3)	0.003 (4)	−0.018 (5)
C15	0.054 (3)	0.065 (5)	0.085 (5)	−0.003 (3)	0.005 (3)	−0.006 (4)

O1—C15	1.352 (7)	C13—C14	1.382 (11)
O1—H1	0.8200	C14—C15	1.370 (10)
N1—C1	1.420 (7)	C4—H4	0.9300
N1—C9	1.281 (7)	C5—H5	0.9300
C1—C6	1.389 (8)	C6—H6	0.9300
C1—C2	1.394 (8)	C7—H7A	0.9600
C2—C7	1.511 (8)	C7—H7B	0.9600
C2—C3	1.376 (8)	C7—H7C	0.9600
C3—C4	1.388 (10)	C8—H8A	0.9600
C3—C8	1.510 (8)	C8—H8B	0.9600
C4—C5	1.379 (9)	C8—H8C	0.9600
C5—C6	1.368 (9)	C9—H9	0.9300
C9—C10	1.435 (7)	C11—H11	0.9300
C10—C15	1.392 (8)	C12—H12	0.9300
C10—C11	1.389 (8)	C13—H13	0.9300
C11—C12	1.370 (9)	C14—H14	0.9300
C12—C13	1.366 (11)
O1···N1	2.582 (6)	H1···H7B	2.5300
O1···H8Ci	2.8900	H4···H8B	2.2700
N1···O1	2.582 (6)	H5···C8v	3.0400
N1···H1	1.8500	H5···H8Av	2.2400
N1···H7B	2.3600	H6···C9	2.6800
C1···C6ii	3.520 (7)	H6···H9	2.3300
C2···C6ii	3.503 (8)	H6···C2iii	2.8400
C6···C2iii	3.503 (8)	H6···C3iii	3.0600
C6···C1iii	3.520 (7)	H7A···C8	3.0700
C1···H1	3.0900	H7A···C12vii	3.0400
C2···H6ii	2.8400	H7A···C13vii	2.9500
C2···H14iv	2.9200	H7B···N1	2.3600
C3···H6ii	3.0600	H7B···H1	2.5300
C5···H8Av	3.0800	H7C···C8	2.7600
C6···H9	2.6500	H7C···H8A	2.3900
C7···H8A	2.8900	H8A···C7	2.8900
C7···H8C	2.9200	H8A···H7C	2.3900
C8···H7A	3.0700	H8A···C5vi	3.0800
C8···H7C	2.7600	H8A···H5vi	2.2400
C8···H5vi	3.0400	H8B···H4	2.2700
C9···H1	2.3800	H8C···C7	2.9200
C9···H6	2.6800	H8C···O1vii	2.8900
C12···H7Ai	3.0400	H8C···C15vii	2.9100
C13···H7Ai	2.9500	H9···C6	2.6500
C15···H8Ci	2.9100	H9···H6	2.3300
H1···N1	1.8500	H9···H11	2.4200
H1···C1	3.0900	H11···H9	2.4200
H1···C9	2.3800	H14···C2viii	2.9200
C15—O1—H1	109.00	C4—C5—H5	120.00
C1—N1—C9	120.2 (5)	C6—C5—H5	120.00
N1—C1—C2	119.9 (5)	C1—C6—H6	120.00
C2—C1—C6	120.0 (5)	C5—C6—H6	120.00
N1—C1—C6	120.0 (5)	C2—C7—H7A	110.00
C1—C2—C3	119.5 (6)	C2—C7—H7B	109.00
C1—C2—C7	118.8 (5)	C2—C7—H7C	109.00
C3—C2—C7	121.7 (6)	H7A—C7—H7B	109.00
C2—C3—C4	120.2 (5)	H7A—C7—H7C	109.00
C2—C3—C8	122.0 (5)	H7B—C7—H7C	109.00
C4—C3—C8	117.9 (5)	C3—C8—H8A	109.00
C3—C4—C5	119.9 (6)	C3—C8—H8B	109.00
C4—C5—C6	120.5 (6)	C3—C8—H8C	109.00
C1—C6—C5	119.9 (6)	H8A—C8—H8B	109.00
N1—C9—C10	122.3 (5)	H8A—C8—H8C	109.00
C9—C10—C15	121.8 (5)	H8B—C8—H8C	110.00
C11—C10—C15	118.0 (5)	N1—C9—H9	119.00
C9—C10—C11	120.2 (5)	C10—C9—H9	119.00
C10—C11—C12	121.5 (6)	C10—C11—H11	119.00
C11—C12—C13	119.5 (7)	C12—C11—H11	119.00
C12—C13—C14	120.6 (7)	C11—C12—H12	120.00
C13—C14—C15	119.8 (6)	C13—C12—H12	120.00
O1—C15—C14	118.6 (5)	C12—C13—H13	120.00
C10—C15—C14	120.7 (6)	C14—C13—H13	120.00
O1—C15—C10	120.7 (5)	C13—C14—H14	120.00
C3—C4—H4	120.00	C15—C14—H14	120.00
C5—C4—H4	120.00
C9—N1—C1—C2	−141.7 (5)	C3—C4—C5—C6	0.4 (8)
C9—N1—C1—C6	41.3 (7)	C4—C5—C6—C1	−1.5 (8)
C1—N1—C9—C10	−173.7 (4)	N1—C9—C10—C11	179.1 (5)
N1—C1—C2—C7	3.3 (7)	N1—C9—C10—C15	1.5 (8)
C6—C1—C2—C3	0.0 (7)	C9—C10—C11—C12	−177.8 (6)
C6—C1—C2—C7	−179.7 (5)	C15—C10—C11—C12	−0.1 (9)
N1—C1—C6—C5	178.3 (5)	C9—C10—C15—O1	−2.5 (8)
C2—C1—C6—C5	1.2 (8)	C9—C10—C15—C14	178.0 (5)
N1—C1—C2—C3	−177.0 (4)	C11—C10—C15—O1	179.8 (5)
C1—C2—C3—C4	−1.1 (7)	C11—C10—C15—C14	0.3 (8)
C7—C2—C3—C4	178.7 (5)	C10—C11—C12—C13	0.0 (10)
C7—C2—C3—C8	0.2 (8)	C11—C12—C13—C14	−0.1 (11)
C1—C2—C3—C8	−179.5 (5)	C12—C13—C14—C15	0.3 (10)
C2—C3—C4—C5	0.9 (8)	C13—C14—C15—O1	−179.9 (6)
C8—C3—C4—C5	179.3 (5)	C13—C14—C15—C10	−0.4 (9)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.582 (6)	148
C7—H7A···Cg1vii	0.96	2.92	3.782 (6)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.582 (6)	148
C7—H7A⋯Cg1i	0.96	2.92	3.782 (6)	150

Symmetry code: (i) .