3-Diethyl-amino-6-[(Z)-(4-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dienone.

In the mol-ecule of the title compound, C(17)H(20)N(2)O(2), the aromatic rings are oriented at a dihedral angle of 6.23 (22)°. Intra-molecular N-H⋯O hydrogen bonding involving the amine H atom and the carbonyl O atom affects the conformation of the mol-ecule. One of the ethyl arms is disordered over two conformations, with occupancies of 0.59 (2) and 0.41 (2). The crystal packing is stabilized by inter-molecular C-H⋯O and O-H⋯O hydrogen bonds, and weak C-H⋯π inter-actions.

Related literature

For general background to Schiff bases, see: Odabaşoğlu et al. (2004 ▶); Hadjoudis et al. (1987 ▶); Hodnett & Dunn (1970 ▶); Misra et al. (1981 ▶); Agarwal et al. (1983 ▶); Varma et al. (1986 ▶); Singh & Dash (1988 ▶); Pandey et al. (1999 ▶); El-Masry et al. (2000 ▶); Samadhiya & Halve (2001 ▶); Xu et al. (1994 ▶); Calligaris et al. (1972 ▶); Cohen et al. (1964 ▶); Moustakali-Mavridis et al. (1978 ▶). For related strucures: Ersanlı et al. (2003 ▶); Şahin et al. (2005 ▶).

Experimental

Crystal data

C17H20N2O2

M = 284.35

Monoclinic,

a = 8.2648 (4) Å

b = 11.8968 (4) Å

c = 16.6149 (7) Å

β = 112.400 (3)°

V = 1510.39 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.54 × 0.44 × 0.26 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.957, T max = 0.979

18967 measured reflections

3143 independent reflections

2416 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.189

S = 1.06

3143 reflections

208 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.27 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/S1600536810045939/si2307sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045939/si2307Isup2.hkl

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

C17H20N2O2	F(000) = 608
Mr = 284.35	Dx = 1.250 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18967 reflections
a = 8.2648 (4) Å	θ = 1.7–28.0°
b = 11.8968 (4) Å	µ = 0.08 mm−1
c = 16.6149 (7) Å	T = 296 K
β = 112.400 (3)°	Prism, brown
V = 1510.39 (11) Å3	0.54 × 0.44 × 0.26 mm
Z = 4

Stoe IPDS 2 diffractometer	3143 independent reflections
Radiation source: fine-focus sealed tube	2416 reflections with I > 2σ(I)
graphite	Rint = 0.067
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.2°
rotation method scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.957, Tmax = 0.979	l = −20→20
18967 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0969P)2 + 0.3716P] where P = (Fo2 + 2Fc2)/3
3143 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.37 e Å−3
13 restraints	Δρmin = −0.27 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	Occ. (<1)
C1	0.8028 (2)	0.31443 (16)	0.65717 (13)	0.0483 (5)
C2	0.9660 (3)	0.35845 (19)	0.70654 (14)	0.0549 (5)
H3	1.0126	0.4163	0.6844	0.066*
C3	1.0587 (3)	0.31624 (19)	0.78840 (14)	0.0581 (5)
H2	1.1680	0.3463	0.8212	0.070*
C4	0.9927 (3)	0.22989 (19)	0.82301 (13)	0.0550 (5)
C5	0.8278 (3)	0.1876 (2)	0.77383 (16)	0.0627 (6)
H6	0.7800	0.1309	0.7963	0.075*
C6	0.7352 (3)	0.22939 (19)	0.69203 (15)	0.0593 (6)
H5	0.6253	0.2001	0.6595	0.071*
C7	0.7361 (2)	0.42738 (17)	0.52483 (13)	0.0501 (5)
H7	0.8386	0.4689	0.5495	0.060*
C8	0.6253 (2)	0.44989 (16)	0.43902 (12)	0.0470 (5)
C9	0.6675 (3)	0.53469 (18)	0.39085 (14)	0.0536 (5)
H9	0.7688	0.5766	0.4180	0.064*
C10	0.5666 (3)	0.55735 (19)	0.30686 (14)	0.0567 (5)
H10	0.6000	0.6134	0.2774	0.068*
C11	0.4090 (3)	0.49573 (19)	0.26311 (13)	0.0556 (5)
C12	0.3648 (3)	0.41193 (19)	0.30976 (13)	0.0552 (5)
H12	0.2638	0.3701	0.2816	0.066*
C13	0.4654 (2)	0.38791 (17)	0.39687 (12)	0.0473 (5)
C14	0.1382 (4)	0.4570 (2)	0.13497 (16)	0.0802 (8)
H15A	0.0600	0.5023	0.0875	0.096*
H15B	0.0819	0.4447	0.1759	0.096*
C15	0.3476 (4)	0.6042 (3)	0.12686 (17)	0.0855 (8)
H14A	0.4063	0.6671	0.1634	0.103*
H14B	0.2416	0.6319	0.0815	0.103*
C16A	0.4682 (17)	0.5521 (6)	0.0854 (7)	0.096 (3)	0.59 (2)
H16A	0.4960	0.6078	0.0508	0.144*	0.59 (2)
H16B	0.4097	0.4900	0.0491	0.144*	0.59 (2)
H16C	0.5741	0.5262	0.1304	0.144*	0.59 (2)
C16B	0.388 (3)	0.5630 (9)	0.0567 (10)	0.097 (4)	0.41 (2)
H16D	0.4141	0.6249	0.0267	0.145*	0.41 (2)
H16E	0.2888	0.5224	0.0171	0.145*	0.41 (2)
H16F	0.4868	0.5137	0.0785	0.145*	0.41 (2)
C17	0.1651 (5)	0.3472 (3)	0.1001 (2)	0.1033 (11)
H17A	0.0543	0.3102	0.0725	0.155*
H17B	0.2406	0.3013	0.1468	0.155*
H17C	0.2177	0.3588	0.0583	0.155*
N1	0.7013 (2)	0.35026 (14)	0.57193 (11)	0.0500 (4)
H1B	0.597 (3)	0.316 (2)	0.5437 (17)	0.066 (7)*
N2	0.3028 (3)	0.51988 (19)	0.17918 (12)	0.0712 (6)
O1	1.0820 (2)	0.18478 (17)	0.90278 (11)	0.0723 (5)
H1A	1.193 (5)	0.197 (3)	0.919 (3)	0.131 (14)*
O2	0.41712 (18)	0.31201 (13)	0.43958 (9)	0.0573 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0409 (9)	0.0490 (11)	0.0465 (10)	0.0055 (8)	0.0073 (8)	−0.0005 (8)
C2	0.0445 (10)	0.0592 (12)	0.0530 (12)	−0.0014 (9)	0.0097 (9)	0.0059 (10)
C3	0.0429 (10)	0.0648 (13)	0.0548 (12)	0.0007 (9)	0.0053 (9)	−0.0002 (10)
C4	0.0488 (10)	0.0650 (13)	0.0471 (11)	0.0128 (9)	0.0135 (9)	0.0064 (9)
C5	0.0546 (11)	0.0642 (14)	0.0655 (14)	0.0015 (10)	0.0185 (11)	0.0146 (11)
C6	0.0444 (10)	0.0603 (13)	0.0619 (13)	−0.0036 (9)	0.0076 (9)	0.0058 (10)
C7	0.0429 (9)	0.0485 (10)	0.0525 (11)	0.0005 (8)	0.0109 (8)	−0.0046 (9)
C8	0.0449 (9)	0.0468 (10)	0.0456 (10)	0.0028 (8)	0.0129 (8)	−0.0024 (8)
C9	0.0497 (10)	0.0532 (11)	0.0560 (12)	−0.0039 (9)	0.0178 (9)	−0.0026 (9)
C10	0.0634 (12)	0.0543 (12)	0.0568 (12)	−0.0037 (10)	0.0279 (10)	0.0028 (10)
C11	0.0632 (12)	0.0575 (12)	0.0430 (10)	0.0009 (10)	0.0167 (9)	0.0002 (9)
C12	0.0554 (11)	0.0583 (12)	0.0428 (10)	−0.0078 (9)	0.0086 (9)	−0.0013 (9)
C13	0.0471 (10)	0.0473 (10)	0.0433 (10)	0.0010 (8)	0.0125 (8)	−0.0015 (8)
C14	0.0868 (16)	0.0904 (19)	0.0479 (13)	−0.0054 (12)	0.0081 (12)	0.0082 (12)
C15	0.119 (2)	0.0810 (18)	0.0530 (14)	−0.0084 (16)	0.0290 (15)	0.0098 (13)
C16A	0.097 (3)	0.096 (3)	0.096 (3)	−0.0016 (10)	0.0374 (14)	0.0005 (10)
C16B	0.097 (4)	0.097 (4)	0.096 (4)	−0.0010 (10)	0.0381 (18)	0.0011 (10)
C17	0.138 (3)	0.095 (2)	0.0714 (19)	−0.017 (2)	0.0339 (19)	−0.0090 (17)
N1	0.0400 (8)	0.0524 (10)	0.0467 (9)	−0.0004 (7)	0.0044 (7)	−0.0006 (7)
N2	0.0859 (13)	0.0756 (13)	0.0445 (10)	−0.0067 (10)	0.0161 (9)	0.0084 (9)
O1	0.0591 (10)	0.0981 (14)	0.0537 (9)	0.0155 (9)	0.0147 (8)	0.0213 (9)
O2	0.0523 (8)	0.0624 (9)	0.0452 (8)	−0.0123 (6)	0.0050 (6)	0.0069 (7)

C1—C6	1.385 (3)	C12—C13	1.397 (3)
C1—C2	1.387 (3)	C12—H12	0.9300
C1—N1	1.409 (3)	C13—O2	1.301 (2)
C2—C3	1.377 (3)	C14—N2	1.479 (3)
C2—H3	0.9300	C14—C17	1.481 (4)
C3—C4	1.387 (3)	C14—H15A	0.9700
C3—H2	0.9300	C14—H15B	0.9700
C4—O1	1.358 (3)	C15—C16B	1.415 (9)
C4—C5	1.389 (3)	C15—N2	1.465 (3)
C5—C6	1.374 (3)	C15—C16A	1.541 (8)
C5—H6	0.9300	C15—H14A	0.9700
C6—H5	0.9300	C15—H14B	0.9700
C7—N1	1.307 (3)	C16A—H16A	0.9600
C7—C8	1.396 (3)	C16A—H16B	0.9600
C7—H7	0.9300	C16A—H16C	0.9600
C8—C9	1.412 (3)	C16B—H16D	0.9600
C8—C13	1.441 (3)	C16B—H16E	0.9600
C9—C10	1.352 (3)	C16B—H16F	0.9600
C9—H9	0.9300	C17—H17A	0.9600
C10—C11	1.429 (3)	C17—H17B	0.9600
C10—H10	0.9300	C17—H17C	0.9600
C11—N2	1.366 (3)	N1—H1B	0.90 (3)
C11—C12	1.394 (3)	O1—H1A	0.87 (4)
C6—C1—C2	119.00 (19)	N2—C14—H15A	108.9
C6—C1—N1	117.45 (17)	C17—C14—H15A	108.9
C2—C1—N1	123.54 (19)	N2—C14—H15B	108.9
C3—C2—C1	119.8 (2)	C17—C14—H15B	108.9
C3—C2—H3	120.1	H15A—C14—H15B	107.8
C1—C2—H3	120.1	C16B—C15—N2	116.3 (5)
C2—C3—C4	121.39 (19)	N2—C15—C16A	110.1 (4)
C2—C3—H2	119.3	C16B—C15—H14A	124.5
C4—C3—H2	119.3	N2—C15—H14A	109.6
O1—C4—C3	123.0 (2)	C16A—C15—H14A	109.6
O1—C4—C5	118.5 (2)	C16B—C15—H14B	84.4
C3—C4—C5	118.50 (19)	N2—C15—H14B	109.6
C6—C5—C4	120.2 (2)	C16A—C15—H14B	109.6
C6—C5—H6	119.9	H14A—C15—H14B	108.2
C4—C5—H6	119.9	C15—C16A—H16A	109.5
C5—C6—C1	121.10 (19)	C15—C16A—H16B	109.5
C5—C6—H5	119.4	H16A—C16A—H16B	109.5
C1—C6—H5	119.4	C15—C16A—H16C	109.5
N1—C7—C8	122.57 (18)	H16A—C16A—H16C	109.5
N1—C7—H7	118.7	H16B—C16A—H16C	109.5
C8—C7—H7	118.7	C15—C16B—H16D	109.5
C7—C8—C9	120.58 (18)	C15—C16B—H16E	109.5
C7—C8—C13	121.43 (18)	H16D—C16B—H16E	109.5
C9—C8—C13	118.00 (17)	C15—C16B—H16F	109.5
C10—C9—C8	122.60 (19)	H16D—C16B—H16F	109.5
C10—C9—H9	118.7	H16E—C16B—H16F	109.5
C8—C9—H9	118.7	C14—C17—H17A	109.5
C9—C10—C11	120.5 (2)	C14—C17—H17B	109.5
C9—C10—H10	119.8	H17A—C17—H17B	109.5
C11—C10—H10	119.8	C14—C17—H17C	109.5
N2—C11—C12	121.0 (2)	H17A—C17—H17C	109.5
N2—C11—C10	121.2 (2)	H17B—C17—H17C	109.5
C12—C11—C10	117.73 (19)	C7—N1—C1	129.19 (18)
C11—C12—C13	122.95 (19)	C7—N1—H1B	112.7 (16)
C11—C12—H12	118.5	C1—N1—H1B	118.1 (16)
C13—C12—H12	118.5	C11—N2—C15	122.7 (2)
O2—C13—C12	121.47 (18)	C11—N2—C14	120.8 (2)
O2—C13—C8	120.34 (17)	C15—N2—C14	116.4 (2)
C12—C13—C8	118.20 (19)	C4—O1—H1A	111 (3)
N2—C14—C17	113.2 (3)
C6—C1—C2—C3	0.9 (3)	C11—C12—C13—O2	177.4 (2)
N1—C1—C2—C3	−178.06 (19)	C11—C12—C13—C8	−2.5 (3)
C1—C2—C3—C4	0.1 (3)	C7—C8—C13—O2	2.8 (3)
C2—C3—C4—O1	178.7 (2)	C9—C8—C13—O2	−177.25 (18)
C2—C3—C4—C5	−1.3 (3)	C7—C8—C13—C12	−177.39 (19)
O1—C4—C5—C6	−178.5 (2)	C9—C8—C13—C12	2.6 (3)
C3—C4—C5—C6	1.5 (3)	C8—C7—N1—C1	176.75 (18)
C4—C5—C6—C1	−0.5 (4)	C6—C1—N1—C7	−179.4 (2)
C2—C1—C6—C5	−0.7 (3)	C2—C1—N1—C7	−0.5 (3)
N1—C1—C6—C5	178.3 (2)	C12—C11—N2—C15	−177.6 (2)
N1—C7—C8—C9	179.48 (18)	C10—C11—N2—C15	4.1 (4)
N1—C7—C8—C13	−0.5 (3)	C12—C11—N2—C14	−0.5 (4)
C7—C8—C9—C10	178.19 (19)	C10—C11—N2—C14	−178.9 (2)
C13—C8—C9—C10	−1.8 (3)	C16B—C15—N2—C11	110.8 (10)
C8—C9—C10—C11	0.7 (3)	C16A—C15—N2—C11	83.7 (6)
C9—C10—C11—N2	177.9 (2)	C16B—C15—N2—C14	−66.3 (10)
C9—C10—C11—C12	−0.4 (3)	C16A—C15—N2—C14	−93.5 (6)
N2—C11—C12—C13	−177.0 (2)	C17—C14—N2—C11	−81.1 (3)
C10—C11—C12—C13	1.4 (3)	C17—C14—N2—C15	96.1 (3)

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.90 (3)	1.80 (3)	2.574 (2)	142 (2)
O1—H1A···O2i	0.87 (4)	1.75 (4)	2.599 (2)	165 (4)
C16A—H16A···O2ii	0.96	2.52	3.306 (7)	139
C5—H6···Cg1iii	0.93	2.93	3.799 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2	0.90 (3)	1.80 (3)	2.574 (2)	142 (2)
O1—H1A⋯O2i	0.87 (4)	1.75 (4)	2.599 (2)	165 (4)
C16A—H16A⋯O2ii	0.96	2.52	3.306 (7)	139
C5—H6⋯Cg1iii	0.93	2.93	3.799 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) .