5-Diethyl-amino-2-[(E)-(4-eth-oxy-phen-yl)imino-meth-yl]phenol.

The title compound, C(19)H(24)N(2)O(2), adopts the phenol-imine tautomeric form. An intra-molecular O-H⋯N hydrogen bond results in the formation of a six-membered ring. The aromatic rings are oriented at a dihedral angle of 17.33 (16)°. Inter-molecular C-H⋯π inter-actions occur in the crystal.

Related literature

For general background to Schiff bases, see: Hadjoudis et al. (1987 ▶); Hodnett & Dunn (1970 ▶); Misra et al. (1981 ▶); Agarwal et al. (1983 ▶); Varma et al. (1986 ▶); Singh & Dash (1988 ▶); Pandeya et al. (1999 ▶); El-Masry et al. (2000 ▶); Cohen et al. (1964 ▶); Moustakali-Mavridis et al. (1978 ▶) Kaitner & Pavlovic (1996 ▶); Yıldız et al. (1998 ▶). For related structures, see: Odabaşoğlu et al. (2003 ▶); Hökelek et al. (2000 ▶); Bingöl Alpaslan et al. (2010 ▶).

Experimental

Crystal data

C19H24N2O2

M = 312.40

Monoclinic,

a = 29.4936 (13) Å

b = 7.8546 (2) Å

c = 16.7146 (7) Å

β = 115.093 (3)°

V = 3506.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.76 × 0.59 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.944, T max = 0.979

22701 measured reflections

3625 independent reflections

2383 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.260

S = 1.10

3625 reflections

208 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.28 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (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/S1600536811004533/fj2390sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004533/fj2390Isup2.hkl

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

C19H24N2O2	F(000) = 1344
Mr = 312.40	Dx = 1.183 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 18643 reflections
a = 29.4936 (13) Å	θ = 1.5–28.0°
b = 7.8546 (2) Å	µ = 0.08 mm−1
c = 16.7146 (7) Å	T = 296 K
β = 115.093 (3)°	Prism, yellow
V = 3506.7 (2) Å3	0.76 × 0.59 × 0.28 mm
Z = 8

Stoe IPDS 2 diffractometer	3625 independent reflections
Radiation source: fine-focus sealed tube	2383 reflections with I > 2σ(I)
graphite	Rint = 0.073
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.5°
rotation method scans	h = −36→36
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.944, Tmax = 0.979	l = −20→20
22701 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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.260	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.1257P)2 + 1.7422P] where P = (Fo2 + 2Fc2)/3
3625 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.56 e Å−3
4 restraints	Δρmin = −0.28 e Å−3

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	0.55509 (10)	0.2708 (3)	0.09804 (16)	0.0622 (7)
C2	0.59206 (13)	0.3870 (4)	0.14442 (19)	0.0790 (9)
H2	0.6032	0.4636	0.1143	0.095*
C3	0.61234 (13)	0.3892 (4)	0.23535 (19)	0.0788 (9)
H3	0.6374	0.4677	0.2658	0.095*
C4	0.59672 (10)	0.2789 (4)	0.28250 (17)	0.0633 (7)
C5	0.55981 (11)	0.1594 (4)	0.23483 (18)	0.0700 (7)
H5	0.5489	0.0815	0.2648	0.084*
C6	0.53963 (10)	0.1569 (4)	0.14410 (17)	0.0688 (7)
H6	0.5152	0.0770	0.1133	0.083*
C7	0.60388 (11)	0.2229 (4)	0.42580 (18)	0.0677 (7)
H7	0.5730	0.1684	0.3999	0.081*
C8	0.62939 (10)	0.2270 (3)	0.52080 (17)	0.0634 (7)
C9	0.60954 (11)	0.1486 (4)	0.57326 (18)	0.0734 (8)
H9	0.5786	0.0950	0.5459	0.088*
C10	0.63345 (11)	0.1467 (4)	0.66328 (18)	0.0706 (8)
H10	0.6190	0.0904	0.6957	0.085*
C11	0.68015 (11)	0.2300 (4)	0.70765 (17)	0.0663 (7)
C12	0.69978 (11)	0.3123 (4)	0.65580 (18)	0.0737 (8)
H12	0.7299	0.3706	0.6832	0.088*
C13	0.67567 (11)	0.3099 (4)	0.56443 (17)	0.0668 (7)
C14	0.68851 (12)	0.1161 (5)	0.85131 (19)	0.0863 (10)
H14A	0.7178	0.0829	0.9037	0.104*
H14B	0.6739	0.0137	0.8179	0.104*
C15	0.65140 (15)	0.1970 (5)	0.8787 (3)	0.1017 (12)
H15A	0.6427	0.1182	0.9139	0.153*
H15B	0.6219	0.2272	0.8271	0.153*
H15C	0.6658	0.2975	0.9127	0.153*
C16	0.74589 (14)	0.3596 (6)	0.8467 (2)	0.1112 (14)
H16A	0.7407	0.4619	0.8114	0.133*
H16B	0.7453	0.3906	0.9024	0.133*
C17	0.79396 (19)	0.2842 (7)	0.8626 (3)	0.1395 (18)
H17A	0.8202	0.3645	0.8931	0.209*
H17B	0.7944	0.2546	0.8073	0.209*
H17C	0.7990	0.1836	0.8981	0.209*
C18	0.54784 (14)	0.3722 (5)	−0.04086 (19)	0.0911 (10)
H18A	0.5835	0.3629	−0.0240	0.109*
H18B	0.5406	0.4877	−0.0293	0.109*
C19	0.51921 (17)	0.3309 (6)	−0.1370 (2)	0.1181 (15)
H19A	0.5286	0.4088	−0.1716	0.177*
H19B	0.4840	0.3409	−0.1531	0.177*
H19C	0.5267	0.2167	−0.1478	0.177*
N1	0.62123 (9)	0.2895 (3)	0.37583 (14)	0.0701 (6)
N2	0.70399 (10)	0.2291 (4)	0.79754 (15)	0.0912 (9)
O1	0.69745 (9)	0.3886 (3)	0.51884 (14)	0.1011 (9)
H1	0.6798	0.3787	0.4658	0.152*
O2	0.53303 (8)	0.2546 (3)	0.00831 (12)	0.0780 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0630 (15)	0.0717 (16)	0.0496 (13)	0.0059 (13)	0.0218 (11)	−0.0012 (11)
C2	0.100 (2)	0.0798 (19)	0.0593 (16)	−0.0170 (17)	0.0355 (16)	0.0001 (13)
C3	0.093 (2)	0.0834 (19)	0.0564 (15)	−0.0248 (17)	0.0281 (14)	−0.0084 (14)
C4	0.0642 (15)	0.0705 (16)	0.0532 (14)	0.0001 (13)	0.0230 (12)	−0.0035 (11)
C5	0.0692 (16)	0.0829 (18)	0.0597 (15)	−0.0066 (14)	0.0291 (13)	0.0031 (13)
C6	0.0581 (15)	0.0851 (19)	0.0577 (15)	−0.0057 (13)	0.0191 (12)	−0.0052 (13)
C7	0.0663 (16)	0.0733 (17)	0.0603 (15)	−0.0030 (13)	0.0237 (13)	−0.0049 (13)
C8	0.0670 (16)	0.0653 (15)	0.0553 (14)	0.0001 (12)	0.0232 (12)	−0.0032 (11)
C9	0.0678 (17)	0.088 (2)	0.0616 (16)	−0.0118 (15)	0.0251 (13)	−0.0030 (14)
C10	0.0711 (17)	0.0843 (19)	0.0556 (14)	−0.0087 (14)	0.0260 (13)	0.0004 (13)
C11	0.0744 (17)	0.0709 (16)	0.0517 (14)	−0.0023 (13)	0.0249 (13)	−0.0013 (12)
C12	0.0741 (18)	0.0820 (19)	0.0599 (16)	−0.0155 (15)	0.0234 (14)	−0.0037 (14)
C13	0.0798 (18)	0.0651 (15)	0.0578 (15)	−0.0106 (13)	0.0315 (14)	−0.0003 (12)
C14	0.085 (2)	0.109 (2)	0.0555 (15)	−0.0049 (18)	0.0209 (15)	0.0098 (16)
C15	0.124 (3)	0.105 (3)	0.089 (2)	−0.011 (2)	0.058 (2)	0.000 (2)
C16	0.088 (2)	0.166 (4)	0.0653 (19)	−0.036 (2)	0.0193 (17)	0.011 (2)
C17	0.133 (4)	0.130 (4)	0.129 (4)	0.008 (3)	0.030 (3)	0.023 (3)
C18	0.109 (3)	0.106 (2)	0.0574 (16)	−0.002 (2)	0.0342 (17)	0.0046 (16)
C19	0.136 (3)	0.154 (4)	0.0554 (18)	−0.009 (3)	0.031 (2)	0.001 (2)
N1	0.0841 (16)	0.0725 (14)	0.0520 (12)	−0.0050 (12)	0.0273 (12)	−0.0018 (10)
N2	0.0797 (16)	0.137 (2)	0.0484 (13)	−0.0196 (15)	0.0187 (11)	0.0094 (13)
O1	0.1140 (18)	0.1272 (19)	0.0608 (12)	−0.0550 (16)	0.0358 (12)	−0.0062 (12)
O2	0.0849 (14)	0.0925 (14)	0.0498 (10)	−0.0046 (11)	0.0220 (9)	0.0006 (9)

C1—O2	1.364 (3)	C12—H12	0.9300
C1—C6	1.378 (4)	C13—O1	1.338 (3)
C1—C2	1.381 (4)	C14—N2	1.467 (4)
C2—C3	1.377 (4)	C14—C15	1.495 (5)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.375 (4)	C14—H14B	0.9700
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.402 (4)	C15—H15B	0.9600
C4—N1	1.417 (3)	C15—H15C	0.9600
C5—C6	1.374 (4)	C16—C17	1.453 (5)
C5—H5	0.9300	C16—N2	1.547 (5)
C6—H6	0.9300	C16—H16A	0.9700
C7—N1	1.263 (4)	C16—H16B	0.9700
C7—C8	1.441 (4)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—C9	1.388 (4)	C17—H17C	0.9600
C8—C13	1.405 (4)	C18—O2	1.423 (4)
C9—C10	1.364 (4)	C18—C19	1.499 (4)
C9—H9	0.9300	C18—H18A	0.9700
C10—C11	1.417 (4)	C18—H18B	0.9700
C10—H10	0.9300	C19—H19A	0.9600
C11—N2	1.362 (3)	C19—H19B	0.9600
C11—C12	1.389 (4)	C19—H19C	0.9600
C12—C13	1.385 (4)	O1—H1	0.8200
O2—C1—C6	115.9 (2)	C15—C14—H14A	109.0
O2—C1—C2	125.0 (3)	N2—C14—H14B	109.0
C6—C1—C2	119.0 (2)	C15—C14—H14B	109.0
C3—C2—C1	119.9 (3)	H14A—C14—H14B	107.8
C3—C2—H2	120.1	C14—C15—H15A	109.5
C1—C2—H2	120.1	C14—C15—H15B	109.5
C4—C3—C2	122.0 (3)	H15A—C15—H15B	109.5
C4—C3—H3	119.0	C14—C15—H15C	109.5
C2—C3—H3	119.0	H15A—C15—H15C	109.5
C3—C4—C5	117.7 (2)	H15B—C15—H15C	109.5
C3—C4—N1	117.1 (2)	C17—C16—N2	109.0 (4)
C5—C4—N1	125.2 (3)	C17—C16—H16A	109.9
C6—C5—C4	120.4 (3)	N2—C16—H16A	109.9
C6—C5—H5	119.8	C17—C16—H16B	109.9
C4—C5—H5	119.8	N2—C16—H16B	109.9
C5—C6—C1	121.1 (3)	H16A—C16—H16B	108.3
C5—C6—H6	119.5	C16—C17—H17A	109.5
C1—C6—H6	119.5	C16—C17—H17B	109.5
N1—C7—C8	123.4 (3)	H17A—C17—H17B	109.5
N1—C7—H7	118.3	C16—C17—H17C	109.5
C8—C7—H7	118.3	H17A—C17—H17C	109.5
C9—C8—C13	117.1 (2)	H17B—C17—H17C	109.5
C9—C8—C7	121.6 (3)	O2—C18—C19	107.9 (3)
C13—C8—C7	121.4 (3)	O2—C18—H18A	110.1
C10—C9—C8	122.8 (3)	C19—C18—H18A	110.1
C10—C9—H9	118.6	O2—C18—H18B	110.1
C8—C9—H9	118.6	C19—C18—H18B	110.1
C9—C10—C11	120.3 (3)	H18A—C18—H18B	108.4
C9—C10—H10	119.8	C18—C19—H19A	109.5
C11—C10—H10	119.8	C18—C19—H19B	109.5
N2—C11—C12	122.3 (3)	H19A—C19—H19B	109.5
N2—C11—C10	120.5 (3)	C18—C19—H19C	109.5
C12—C11—C10	117.3 (2)	H19A—C19—H19C	109.5
C13—C12—C11	121.8 (3)	H19B—C19—H19C	109.5
C13—C12—H12	119.1	C7—N1—C4	122.9 (3)
C11—C12—H12	119.1	C11—N2—C14	122.0 (3)
O1—C13—C12	118.4 (3)	C11—N2—C16	120.3 (3)
O1—C13—C8	120.9 (2)	C14—N2—C16	117.5 (2)
C12—C13—C8	120.7 (3)	C13—O1—H1	109.5
N2—C14—C15	112.9 (3)	C1—O2—C18	117.0 (2)
N2—C14—H14A	109.0
O2—C1—C2—C3	−178.6 (3)	C11—C12—C13—C8	1.7 (5)
C6—C1—C2—C3	−1.0 (5)	C9—C8—C13—O1	179.9 (3)
C1—C2—C3—C4	−0.4 (5)	C7—C8—C13—O1	0.3 (4)
C2—C3—C4—C5	1.5 (5)	C9—C8—C13—C12	−0.2 (4)
C2—C3—C4—N1	178.2 (3)	C7—C8—C13—C12	−179.8 (3)
C3—C4—C5—C6	−1.3 (4)	C8—C7—N1—C4	177.4 (3)
N1—C4—C5—C6	−177.8 (3)	C3—C4—N1—C7	164.5 (3)
C4—C5—C6—C1	0.0 (5)	C5—C4—N1—C7	−19.0 (5)
O2—C1—C6—C5	179.0 (3)	C12—C11—N2—C14	−167.9 (3)
C2—C1—C6—C5	1.1 (4)	C10—C11—N2—C14	12.7 (5)
N1—C7—C8—C9	−178.4 (3)	C12—C11—N2—C16	17.2 (5)
N1—C7—C8—C13	1.2 (5)	C10—C11—N2—C16	−162.2 (3)
C13—C8—C9—C10	−1.4 (4)	C15—C14—N2—C11	−92.0 (4)
C7—C8—C9—C10	178.3 (3)	C15—C14—N2—C16	83.0 (4)
C8—C9—C10—C11	1.4 (5)	C17—C16—N2—C11	−93.3 (4)
C9—C10—C11—N2	179.6 (3)	C17—C16—N2—C14	91.6 (4)
C9—C10—C11—C12	0.2 (4)	C6—C1—O2—C18	179.2 (3)
N2—C11—C12—C13	178.9 (3)	C2—C1—O2—C18	−3.1 (4)
C10—C11—C12—C13	−1.7 (5)	C19—C18—O2—C1	179.9 (3)
C11—C12—C13—O1	−178.4 (3)

Cg1 is the centroid of C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.610 (3)	148
C2—H2···Cg1i	0.93	2.85	3.681 (4)	149
C17—H17A···Cg1ii	0.96	2.97	3.763 (6)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.610 (3)	148
C2—H2⋯Cg1i	0.93	2.85	3.681 (4)	149
C17—H17A⋯Cg1ii	0.96	2.97	3.763 (6)	140

Symmetry codes: (i) ; (ii) .