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

The title Schiff base, C(19)H(24)N(2)O(3), exists in the crystal structure in the phenol-imine tautomeric form with an intra-molecular O-H⋯N hydrogen bond. The planes of the aromatic rings form a dihedral angle of 36.8 (8)°. The crystal packing is characterized by C-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid distance = 3.478 (4)Å].

Related literature

Schiff bases of salicyl­aldehyde may exhibit thermochromism or photochromism, depending on the planarity or non-planarity, respectively, of the mol­ecule, see: Amimoto & Kawato (2005 ▶); Schmidt & Cohen (1964 ▶). For similar structures, see: Ha (2011 ▶); Asiri et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H24N2O3

M = 328.40

Monoclinic,

a = 7.2028 (3) Å

b = 9.4423 (5) Å

c = 26.050 (2) Å

β = 91.742 (7)°

V = 1770.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.22 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.933, T max = 1.000

8031 measured reflections

4165 independent reflections

1959 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.164

S = 1.06

4165 reflections

226 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, global. DOI: 10.1107/S160053681201882X/ld2055sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201882X/ld2055Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201882X/ld2055Isup3.cml

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

C19H24N2O3	F(000) = 704
Mr = 328.40	Dx = 1.232 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2028 (3) Å	Cell parameters from 1690 reflections
b = 9.4423 (5) Å	θ = 3.2–29.0°
c = 26.050 (2) Å	µ = 0.08 mm−1
β = 91.742 (7)°	T = 293 K
V = 1770.9 (2) Å3	Block, orange
Z = 4	0.22 × 0.15 × 0.10 mm

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer	4165 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1959 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 16.0454 pixels mm-1	θmax = 29.1°, θmin = 3.2°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −9→11
Tmin = 0.933, Tmax = 1.000	l = −35→33
8031 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.4437P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4165 reflections	Δρmax = 0.16 e Å−3
226 parameters	Δρmin = −0.15 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (6)

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	0.3547 (3)	0.5391 (2)	0.37257 (9)	0.0640 (6)
N1	0.3519 (3)	0.2811 (2)	0.40463 (9)	0.0529 (6)
O3	0.7902 (3)	−0.1820 (2)	0.46150 (9)	0.0732 (7)
C13	−0.1045 (4)	0.6216 (3)	0.31791 (10)	0.0455 (6)
C14	0.0834 (3)	0.6313 (3)	0.33320 (10)	0.0490 (7)
H14	0.1488	0.7136	0.3260	0.059*
O2	0.6402 (3)	0.3076 (2)	0.47090 (8)	0.0650 (6)
C12	−0.1986 (4)	0.4935 (3)	0.32942 (11)	0.0521 (7)
H12	−0.3229	0.4830	0.3195	0.062*
C10	0.0799 (4)	0.3947 (3)	0.37000 (10)	0.0458 (6)
N2	−0.1934 (3)	0.7311 (2)	0.29284 (9)	0.0555 (6)
C15	0.1737 (4)	0.5215 (3)	0.35868 (10)	0.0469 (7)
C11	−0.1092 (4)	0.3860 (3)	0.35480 (10)	0.0502 (7)
H11	−0.1751	0.3043	0.3623	0.060*
C9	0.1748 (4)	0.2768 (3)	0.39315 (10)	0.0505 (7)
H9	0.1083	0.1950	0.4002	0.061*
C7	0.7176 (4)	0.0578 (3)	0.46522 (11)	0.0552 (8)
H7	0.8223	0.0689	0.4866	0.066*
C5	0.4521 (4)	0.1580 (3)	0.41991 (10)	0.0491 (7)
C16	−0.3951 (4)	0.7321 (3)	0.28369 (12)	0.0628 (8)
H16A	−0.4404	0.8283	0.2871	0.075*
H16B	−0.4527	0.6749	0.3097	0.075*
C2	0.6713 (4)	−0.0755 (3)	0.44630 (11)	0.0550 (7)
C4	0.4107 (4)	0.0244 (3)	0.40130 (11)	0.0559 (8)
H4	0.3081	0.0130	0.3791	0.067*
C6	0.6091 (4)	0.1742 (3)	0.45242 (10)	0.0505 (7)
C3	0.5170 (4)	−0.0937 (3)	0.41452 (11)	0.0566 (8)
H3	0.4846	−0.1830	0.4022	0.068*
C18	−0.0953 (4)	0.8577 (3)	0.27682 (12)	0.0652 (9)
H18A	−0.1594	0.8975	0.2469	0.078*
H18B	0.0288	0.8314	0.2669	0.078*
C8	0.7964 (4)	0.3284 (3)	0.50488 (13)	0.0752 (10)
H8A	0.9086	0.3126	0.4867	0.113*
H8B	0.7905	0.2631	0.5330	0.113*
H8C	0.7954	0.4236	0.5178	0.113*
C17	−0.4527 (5)	0.6764 (4)	0.23138 (14)	0.1018 (13)
H17A	−0.3987	0.7341	0.2054	0.153*
H17B	−0.5856	0.6790	0.2274	0.153*
H17C	−0.4103	0.5805	0.2280	0.153*
C19	−0.0808 (5)	0.9695 (3)	0.31823 (14)	0.0801 (11)
H19A	−0.0146	1.0500	0.3056	0.120*
H19B	−0.0154	0.9316	0.3478	0.120*
H19C	−0.2031	0.9981	0.3276	0.120*
C1	0.7411 (5)	−0.3221 (3)	0.44663 (14)	0.0798 (11)
H1A	0.7206	−0.3257	0.4101	0.120*
H1B	0.6296	−0.3496	0.4633	0.120*
H1C	0.8399	−0.3857	0.4565	0.120*
H1	0.388 (5)	0.462 (3)	0.3860 (14)	0.114 (15)*

	U11	U22	U33	U12	U13	U23
O1	0.0442 (12)	0.0605 (14)	0.0867 (17)	−0.0032 (10)	−0.0064 (11)	0.0111 (12)
N1	0.0546 (14)	0.0542 (15)	0.0494 (14)	0.0062 (11)	−0.0060 (12)	0.0042 (11)
O3	0.0689 (14)	0.0558 (13)	0.0934 (17)	0.0147 (11)	−0.0204 (13)	−0.0056 (11)
C13	0.0443 (15)	0.0474 (16)	0.0449 (16)	0.0009 (12)	0.0014 (13)	0.0003 (12)
C14	0.0436 (15)	0.0456 (16)	0.0580 (17)	−0.0044 (12)	0.0028 (13)	0.0070 (13)
O2	0.0654 (13)	0.0550 (13)	0.0735 (15)	0.0015 (10)	−0.0157 (12)	−0.0042 (10)
C12	0.0437 (15)	0.0492 (17)	0.0631 (19)	−0.0033 (13)	−0.0024 (14)	−0.0031 (14)
C10	0.0467 (15)	0.0437 (15)	0.0470 (16)	0.0012 (12)	0.0017 (13)	0.0017 (12)
N2	0.0472 (13)	0.0534 (15)	0.0654 (16)	−0.0001 (11)	−0.0068 (12)	0.0108 (12)
C15	0.0406 (15)	0.0517 (17)	0.0486 (16)	−0.0010 (13)	0.0019 (12)	0.0009 (13)
C11	0.0457 (15)	0.0483 (16)	0.0568 (18)	−0.0046 (13)	0.0029 (14)	0.0003 (13)
C9	0.0490 (16)	0.0515 (17)	0.0509 (17)	−0.0007 (13)	0.0031 (14)	0.0018 (13)
C7	0.0530 (17)	0.0609 (19)	0.0510 (18)	0.0062 (15)	−0.0087 (14)	−0.0018 (14)
C5	0.0474 (16)	0.0502 (17)	0.0493 (17)	0.0055 (13)	−0.0031 (13)	0.0036 (13)
C16	0.0574 (19)	0.0621 (19)	0.068 (2)	0.0029 (15)	−0.0073 (16)	0.0068 (16)
C2	0.0499 (17)	0.0593 (19)	0.0557 (18)	0.0098 (14)	−0.0001 (14)	0.0012 (14)
C4	0.0554 (18)	0.0647 (19)	0.0470 (17)	0.0034 (15)	−0.0088 (14)	0.0001 (14)
C6	0.0524 (16)	0.0502 (17)	0.0487 (17)	0.0023 (14)	−0.0002 (14)	0.0012 (13)
C3	0.0610 (18)	0.0526 (17)	0.0556 (18)	0.0064 (15)	−0.0049 (15)	−0.0051 (14)
C18	0.065 (2)	0.0584 (19)	0.072 (2)	−0.0051 (16)	−0.0003 (17)	0.0217 (16)
C8	0.073 (2)	0.072 (2)	0.080 (2)	−0.0082 (18)	−0.021 (2)	−0.0065 (18)
C17	0.102 (3)	0.118 (3)	0.084 (3)	−0.020 (3)	−0.024 (2)	−0.003 (2)
C19	0.077 (2)	0.060 (2)	0.102 (3)	−0.0080 (18)	−0.012 (2)	0.0009 (19)
C1	0.078 (2)	0.060 (2)	0.101 (3)	0.0154 (18)	−0.006 (2)	−0.0072 (19)

O1—C15	1.352 (3)	C5—C4	1.381 (4)
O1—H1	0.843 (18)	C5—C6	1.401 (3)
N1—C9	1.302 (3)	C16—C17	1.507 (4)
N1—C5	1.418 (3)	C16—H16A	0.9700
O3—C2	1.371 (3)	C16—H16B	0.9700
O3—C1	1.420 (3)	C2—C3	1.376 (4)
C13—N2	1.372 (3)	C4—C3	1.390 (3)
C13—C14	1.403 (3)	C4—H4	0.9300
C13—C12	1.423 (3)	C3—H3	0.9300
C14—C15	1.383 (3)	C18—C19	1.511 (4)
C14—H14	0.9300	C18—H18A	0.9700
O2—C6	1.365 (3)	C18—H18B	0.9700
O2—C8	1.424 (3)	C8—H8A	0.9600
C12—C11	1.362 (3)	C8—H8B	0.9600
C12—H12	0.9300	C8—H8C	0.9600
C10—C11	1.410 (3)	C17—H17A	0.9600
C10—C15	1.410 (3)	C17—H17B	0.9600
C10—C9	1.430 (3)	C17—H17C	0.9600
N2—C18	1.456 (3)	C19—H19A	0.9600
N2—C16	1.465 (3)	C19—H19B	0.9600
C11—H11	0.9300	C19—H19C	0.9600
C9—H9	0.9300	C1—H1A	0.9600
C7—C6	1.384 (3)	C1—H1B	0.9600
C7—C2	1.389 (4)	C1—H1C	0.9600
C7—H7	0.9300
C15—O1—H1	105 (3)	O3—C2—C7	114.9 (2)
C9—N1—C5	121.7 (2)	C3—C2—C7	120.5 (3)
C2—O3—C1	117.1 (2)	C5—C4—C3	122.3 (3)
N2—C13—C14	121.2 (2)	C5—C4—H4	118.8
N2—C13—C12	121.5 (2)	C3—C4—H4	118.8
C14—C13—C12	117.3 (2)	O2—C6—C7	124.2 (2)
C15—C14—C13	121.5 (2)	O2—C6—C5	115.8 (2)
C15—C14—H14	119.2	C7—C6—C5	119.9 (2)
C13—C14—H14	119.2	C2—C3—C4	118.6 (3)
C6—O2—C8	117.7 (2)	C2—C3—H3	120.7
C11—C12—C13	121.0 (2)	C4—C3—H3	120.7
C11—C12—H12	119.5	N2—C18—C19	113.1 (3)
C13—C12—H12	119.5	N2—C18—H18A	109.0
C11—C10—C15	117.1 (2)	C19—C18—H18A	109.0
C11—C10—C9	121.2 (2)	N2—C18—H18B	109.0
C15—C10—C9	121.6 (2)	C19—C18—H18B	109.0
C13—N2—C18	122.2 (2)	H18A—C18—H18B	107.8
C13—N2—C16	121.9 (2)	O2—C8—H8A	109.5
C18—N2—C16	115.8 (2)	O2—C8—H8B	109.5
O1—C15—C14	118.2 (2)	H8A—C8—H8B	109.5
O1—C15—C10	120.8 (2)	O2—C8—H8C	109.5
C14—C15—C10	121.0 (2)	H8A—C8—H8C	109.5
C12—C11—C10	122.1 (3)	H8B—C8—H8C	109.5
C12—C11—H11	119.0	C16—C17—H17A	109.5
C10—C11—H11	119.0	C16—C17—H17B	109.5
N1—C9—C10	121.6 (3)	H17A—C17—H17B	109.5
N1—C9—H9	119.2	C16—C17—H17C	109.5
C10—C9—H9	119.2	H17A—C17—H17C	109.5
C6—C7—C2	120.4 (3)	H17B—C17—H17C	109.5
C6—C7—H7	119.8	C18—C19—H19A	109.5
C2—C7—H7	119.8	C18—C19—H19B	109.5
C4—C5—C6	118.3 (2)	H19A—C19—H19B	109.5
C4—C5—N1	123.2 (2)	C18—C19—H19C	109.5
C6—C5—N1	118.3 (2)	H19A—C19—H19C	109.5
N2—C16—C17	112.9 (3)	H19B—C19—H19C	109.5
N2—C16—H16A	109.0	O3—C1—H1A	109.5
C17—C16—H16A	109.0	O3—C1—H1B	109.5
N2—C16—H16B	109.0	H1A—C1—H1B	109.5
C17—C16—H16B	109.0	O3—C1—H1C	109.5
H16A—C16—H16B	107.8	H1A—C1—H1C	109.5
O3—C2—C3	124.6 (3)	H1B—C1—H1C	109.5
N2—C13—C14—C15	179.7 (3)	C13—N2—C16—C17	−95.4 (3)
C12—C13—C14—C15	−0.4 (4)	C18—N2—C16—C17	88.7 (3)
N2—C13—C12—C11	−179.3 (3)	C1—O3—C2—C3	−5.4 (5)
C14—C13—C12—C11	0.8 (4)	C1—O3—C2—C7	175.1 (3)
C14—C13—N2—C18	5.4 (4)	C6—C7—C2—O3	179.7 (3)
C12—C13—N2—C18	−174.5 (3)	C6—C7—C2—C3	0.1 (5)
C14—C13—N2—C16	−170.3 (3)	C6—C5—C4—C3	1.3 (4)
C12—C13—N2—C16	9.8 (4)	N1—C5—C4—C3	176.3 (3)
C13—C14—C15—O1	−179.5 (2)	C8—O2—C6—C7	1.1 (4)
C13—C14—C15—C10	0.4 (4)	C8—O2—C6—C5	178.9 (3)
C11—C10—C15—O1	179.1 (3)	C2—C7—C6—O2	177.3 (3)
C9—C10—C15—O1	−4.5 (4)	C2—C7—C6—C5	−0.4 (5)
C11—C10—C15—C14	−0.8 (4)	C4—C5—C6—O2	−178.1 (3)
C9—C10—C15—C14	175.6 (3)	N1—C5—C6—O2	6.6 (4)
C13—C12—C11—C10	−1.2 (4)	C4—C5—C6—C7	−0.2 (4)
C15—C10—C11—C12	1.2 (4)	N1—C5—C6—C7	−175.5 (3)
C9—C10—C11—C12	−175.2 (3)	O3—C2—C3—C4	−178.6 (3)
C5—N1—C9—C10	−169.8 (2)	C7—C2—C3—C4	0.9 (5)
C11—C10—C9—N1	176.0 (3)	C5—C4—C3—C2	−1.6 (5)
C15—C10—C9—N1	−0.2 (4)	C13—N2—C18—C19	−86.8 (3)
C9—N1—C5—C4	33.2 (4)	C16—N2—C18—C19	89.1 (3)
C9—N1—C5—C6	−151.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (2)	1.79 (2)	2.575 (3)	153 (4)
C16—H16B···O1i	0.97	2.53	3.491 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84 (2)	1.79 (2)	2.575 (3)	153 (4)
C16—H16B⋯O1i	0.97	2.53	3.491 (4)	172

Symmetry code: (i) .