2-[(2,4-Dimethyl-phen-yl)imino-meth-yl]-6-methyl-phenol.

The title compound, C(16)H(17)NO, is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The mol-ecule is almost planar, with a dihedral angle of 4.61 (4)° between the aromatic rings. The molecular structure is stabilized by an intramolecular O-H⋯N hydrogen bond which generates a six membered ring.

Related literature

For background to the properties and uses of Schiff bases, see: Aydoğan et al. (2001 ▶); Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶); Cohen et al. (1964 ▶); Moustakali-Mavridis et al. (1978 ▶); Taggi et al. (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Köysal et al. (2007 ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Monoclinic,

a = 18.1448 (11) Å

b = 4.7141 (3) Å

c = 15.7151 (8) Å

β = 99.646 (4)°

V = 1325.21 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.80 × 0.40 × 0.15 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.963, T max = 0.990

18038 measured reflections

2732 independent reflections

1808 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.01

2732 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.10 e Å−3

Δρmin = −0.14 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/S1600536809033637/fl2259sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033637/fl2259Isup2.hkl

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

C16H17NO	F(000) = 512
Mr = 239.31	Dx = 1.199 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21940 reflections
a = 18.1448 (11) Å	θ = 1.6–28.0°
b = 4.7141 (3) Å	µ = 0.07 mm−1
c = 15.7151 (8) Å	T = 296 K
β = 99.646 (4)°	Prism, yellow
V = 1325.21 (13) Å3	0.80 × 0.40 × 0.15 mm
Z = 4

Stoe IPDS II diffractometer	2732 independent reflections
Radiation source: fine-focus sealed tube	1808 reflections with I > 2σ(I)
graphite	Rint = 0.058
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.3°
rotation method scans	h = −22→22
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −5→5
Tmin = 0.963, Tmax = 0.990	l = −19→19
18038 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0631P)2] where P = (Fo2 + 2Fc2)/3
2732 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.10 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Experimental. 359 frames, detector distance = 100 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	Occ. (<1)
C1	0.35139 (7)	0.4131 (3)	0.57205 (9)	0.0555 (3)
C2	0.33187 (7)	0.3180 (3)	0.64973 (9)	0.0568 (4)
C3	0.37660 (8)	0.1210 (3)	0.70152 (10)	0.0639 (4)
C4	0.43983 (8)	0.0228 (4)	0.67355 (10)	0.0716 (5)
H4	0.4698	−0.1090	0.7072	0.086*
C5	0.46019 (9)	0.1133 (4)	0.59720 (11)	0.0766 (5)
H5	0.5033	0.0436	0.5800	0.092*
C6	0.41638 (8)	0.3062 (4)	0.54709 (10)	0.0704 (4)
H6	0.4300	0.3672	0.4956	0.084*
C7	0.35539 (10)	0.0258 (5)	0.78536 (11)	0.0943 (6)
H7A	0.3059	−0.0532	0.7748	0.113*
H7B	0.3565	0.1851	0.8236	0.113*
H7C	0.3902	−0.1155	0.8113	0.113*
C8	0.30616 (8)	0.6172 (3)	0.51840 (9)	0.0588 (4)
H8	0.3214	0.6770	0.4677	0.071*
C9	0.20053 (7)	0.9169 (3)	0.48548 (8)	0.0538 (3)
C10	0.13929 (8)	1.0247 (3)	0.51850 (9)	0.0573 (4)
C11	0.09298 (8)	1.2164 (3)	0.46860 (9)	0.0614 (4)
H11	0.0522	1.2882	0.4904	0.074*
C12	0.10427 (8)	1.3069 (3)	0.38793 (9)	0.0602 (4)
C13	0.16527 (8)	1.1959 (3)	0.35699 (10)	0.0662 (4)
H13	0.1745	1.2516	0.3030	0.079*
C14	0.21240 (8)	1.0049 (4)	0.40465 (9)	0.0659 (4)
H14	0.2530	0.9335	0.3823	0.079*
C15	0.12371 (9)	0.9339 (4)	0.60573 (10)	0.0764 (5)
H15A	0.1653	0.9843	0.6493	0.092*
H15B	0.1164	0.7322	0.6061	0.092*
H15C	0.0795	1.0274	0.6174	0.092*
C16	0.05261 (9)	1.5162 (4)	0.33607 (10)	0.0731 (4)
H16A	0.0139	1.5690	0.3678	0.110*	0.50
H16B	0.0307	1.4313	0.2822	0.110*	0.50
H16C	0.0803	1.6818	0.3251	0.110*	0.50
H16D	0.0694	1.5524	0.2823	0.110*	0.50
H16E	0.0526	1.6901	0.3678	0.110*	0.50
H16F	0.0029	1.4395	0.3250	0.110*	0.50
N1	0.24618 (6)	0.7186 (3)	0.53786 (7)	0.0577 (3)
O1	0.27017 (6)	0.4153 (3)	0.67706 (8)	0.0781 (4)
H1	0.2494 (11)	0.542 (5)	0.6293 (15)	0.128 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0539 (7)	0.0570 (9)	0.0546 (8)	−0.0013 (6)	0.0063 (6)	−0.0050 (6)
C2	0.0524 (7)	0.0602 (9)	0.0571 (8)	−0.0024 (7)	0.0075 (6)	−0.0035 (7)
C3	0.0651 (8)	0.0648 (10)	0.0588 (8)	0.0001 (7)	0.0017 (7)	−0.0014 (7)
C4	0.0717 (9)	0.0697 (11)	0.0674 (10)	0.0120 (8)	−0.0063 (8)	−0.0044 (8)
C5	0.0661 (9)	0.0924 (13)	0.0707 (10)	0.0237 (9)	0.0096 (7)	−0.0075 (9)
C6	0.0661 (9)	0.0841 (12)	0.0623 (9)	0.0124 (8)	0.0147 (7)	0.0001 (8)
C7	0.0993 (13)	0.1095 (16)	0.0736 (12)	0.0156 (11)	0.0130 (10)	0.0261 (11)
C8	0.0604 (8)	0.0627 (10)	0.0545 (8)	0.0005 (7)	0.0127 (6)	0.0018 (7)
C9	0.0549 (7)	0.0532 (9)	0.0533 (7)	−0.0002 (6)	0.0091 (6)	−0.0012 (6)
C10	0.0584 (8)	0.0607 (9)	0.0533 (8)	−0.0004 (7)	0.0104 (6)	−0.0045 (7)
C11	0.0584 (8)	0.0647 (10)	0.0609 (8)	0.0074 (7)	0.0095 (6)	−0.0068 (7)
C12	0.0645 (8)	0.0519 (9)	0.0614 (8)	−0.0012 (7)	0.0030 (6)	−0.0043 (7)
C13	0.0730 (9)	0.0673 (10)	0.0597 (8)	0.0018 (8)	0.0153 (7)	0.0089 (8)
C14	0.0664 (9)	0.0715 (11)	0.0635 (9)	0.0094 (8)	0.0216 (7)	0.0067 (8)
C15	0.0705 (9)	0.0992 (13)	0.0635 (9)	0.0151 (9)	0.0227 (7)	0.0053 (9)
C16	0.0745 (10)	0.0645 (11)	0.0758 (10)	0.0069 (8)	−0.0003 (8)	0.0042 (8)
N1	0.0568 (7)	0.0583 (8)	0.0587 (7)	0.0037 (5)	0.0120 (5)	0.0013 (6)
O1	0.0692 (6)	0.0967 (9)	0.0732 (7)	0.0176 (6)	0.0263 (5)	0.0192 (7)

C1—C6	1.3975 (19)	C10—C11	1.385 (2)
C1—C2	1.4005 (19)	C10—C15	1.5073 (19)
C1—C8	1.442 (2)	C11—C12	1.385 (2)
C2—O1	1.3452 (17)	C11—H11	0.9300
C2—C3	1.401 (2)	C12—C13	1.384 (2)
C3—C4	1.376 (2)	C12—C16	1.503 (2)
C3—C7	1.502 (2)	C13—C14	1.374 (2)
C4—C5	1.381 (2)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.367 (2)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—H7A	0.9600	C16—H16A	0.9600
C7—H7B	0.9600	C16—H16B	0.9600
C7—H7C	0.9600	C16—H16C	0.9600
C8—N1	1.2720 (17)	C16—H16D	0.9600
C8—H8	0.9300	C16—H16E	0.9600
C9—C14	1.3872 (18)	C16—H16F	0.9600
C9—C10	1.3985 (18)	O1—H1	0.98 (2)
C9—N1	1.4172 (17)
C6—C1—C2	118.54 (13)	C13—C12—C16	121.35 (14)
C6—C1—C8	120.06 (13)	C11—C12—C16	121.60 (14)
C2—C1—C8	121.40 (12)	C14—C13—C12	121.17 (14)
O1—C2—C1	120.98 (13)	C14—C13—H13	119.4
O1—C2—C3	118.21 (13)	C12—C13—H13	119.4
C1—C2—C3	120.80 (13)	C13—C14—C9	121.15 (13)
C4—C3—C2	118.06 (14)	C13—C14—H14	119.4
C4—C3—C7	121.98 (15)	C9—C14—H14	119.4
C2—C3—C7	119.96 (14)	C10—C15—H15A	109.5
C3—C4—C5	122.17 (15)	C10—C15—H15B	109.5
C3—C4—H4	118.9	H15A—C15—H15B	109.5
C5—C4—H4	118.9	C10—C15—H15C	109.5
C6—C5—C4	119.45 (14)	H15A—C15—H15C	109.5
C6—C5—H5	120.3	H15B—C15—H15C	109.5
C4—C5—H5	120.3	C12—C16—H16A	109.5
C5—C6—C1	120.98 (15)	C12—C16—H16B	109.5
C5—C6—H6	119.5	H16A—C16—H16B	109.5
C1—C6—H6	119.5	C12—C16—H16C	109.5
C3—C7—H7A	109.5	H16A—C16—H16C	109.5
C3—C7—H7B	109.5	H16B—C16—H16C	109.5
H7A—C7—H7B	109.5	C12—C16—H16D	109.5
C3—C7—H7C	109.5	H16A—C16—H16D	141.1
H7A—C7—H7C	109.5	H16B—C16—H16D	56.3
H7B—C7—H7C	109.5	H16C—C16—H16D	56.3
N1—C8—C1	122.44 (13)	C12—C16—H16E	109.5
N1—C8—H8	118.8	H16A—C16—H16E	56.3
C1—C8—H8	118.8	H16B—C16—H16E	141.1
C14—C9—C10	119.08 (13)	H16C—C16—H16E	56.3
C14—C9—N1	124.33 (12)	H16D—C16—H16E	109.5
C10—C9—N1	116.59 (12)	C12—C16—H16F	109.5
C11—C10—C9	118.14 (13)	H16A—C16—H16F	56.3
C11—C10—C15	120.79 (13)	H16B—C16—H16F	56.3
C9—C10—C15	121.07 (13)	H16C—C16—H16F	141.1
C10—C11—C12	123.42 (13)	H16D—C16—H16F	109.5
C10—C11—H11	118.3	H16E—C16—H16F	109.5
C12—C11—H11	118.3	C8—N1—C9	123.26 (12)
C13—C12—C11	117.05 (14)	C2—O1—H1	101.3 (12)
C6—C1—C2—O1	179.58 (14)	C14—C9—C10—C11	−0.1 (2)
C8—C1—C2—O1	−0.3 (2)	N1—C9—C10—C11	−179.26 (13)
C6—C1—C2—C3	0.3 (2)	C14—C9—C10—C15	179.56 (15)
C8—C1—C2—C3	−179.57 (13)	N1—C9—C10—C15	0.4 (2)
O1—C2—C3—C4	−179.75 (14)	C9—C10—C11—C12	−0.1 (2)
C1—C2—C3—C4	−0.4 (2)	C15—C10—C11—C12	−179.76 (15)
O1—C2—C3—C7	−0.4 (2)	C10—C11—C12—C13	0.2 (2)
C1—C2—C3—C7	178.92 (15)	C10—C11—C12—C16	−179.85 (14)
C2—C3—C4—C5	0.4 (2)	C11—C12—C13—C14	−0.1 (2)
C7—C3—C4—C5	−178.92 (17)	C16—C12—C13—C14	179.93 (14)
C3—C4—C5—C6	−0.2 (3)	C12—C13—C14—C9	0.0 (3)
C4—C5—C6—C1	0.0 (3)	C10—C9—C14—C13	0.2 (2)
C2—C1—C6—C5	−0.1 (2)	N1—C9—C14—C13	179.27 (14)
C8—C1—C6—C5	179.76 (15)	C1—C8—N1—C9	−179.25 (13)
C6—C1—C8—N1	179.29 (14)	C14—C9—N1—C8	5.4 (2)
C2—C1—C8—N1	−0.9 (2)	C10—C9—N1—C8	−175.44 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.98 (2)	1.65 (2)	2.5883 (16)	157.3 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.98 (2)	1.65 (2)	2.5883 (16)	157.3 (18)