(E)-2-(4-Diethyl-amino-2-hydroxy-benzyl-idene-amino)benzonitrile.

The mol-ecule of the title compound, C(18)H(19)N(3)O, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the planes of the two benzene rings is 2.62 (11)°. A strong intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation.

Related literature

For the properties of Schiff bases compounds, see: Weber et al. (2007 ▶). Chen et al. (2008 ▶). May et al. (2004 ▶).

Experimental

Crystal data

C18H19N3O

M = 293.36

Monoclinic,

a = 7.185 (5) Å

b = 12.324 (9) Å

c = 18.490 (12) Å

β = 108.39 (2)°

V = 1553.6 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.984, T max = 0.984

16730 measured reflections

3546 independent reflections

2694 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.152

S = 1.16

3546 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000111X/bx2261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000111X/bx2261Isup2.hkl

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

C18H19N3O	F(000) = 624
Mr = 293.36	Dx = 1.254 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3397 reflections
a = 7.185 (5) Å	θ = 2.3–27.6°
b = 12.324 (9) Å	µ = 0.08 mm−1
c = 18.490 (12) Å	T = 293 K
β = 108.39 (2)°	Prism, yellow
V = 1553.6 (19) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	3546 independent reflections
Radiation source: fine-focus sealed tube	2694 reflections with I > 2σ(I)
graphite	Rint = 0.062
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4°, θmin = 2.9°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.984, Tmax = 0.984	l = −23→23
16730 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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.4099P] where P = (Fo2 + 2Fc2)/3
3546 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.20 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
O1	−0.0254 (2)	0.40112 (14)	0.61866 (9)	0.0379 (4)
N1	0.4621 (3)	0.58450 (14)	0.81676 (10)	0.0349 (4)
N2	0.0535 (2)	0.35141 (13)	0.49350 (9)	0.0269 (4)
N3	−0.4028 (3)	0.26723 (17)	0.48643 (11)	0.0424 (5)
C1	0.2850 (3)	0.43963 (16)	0.59876 (11)	0.0255 (4)
C2	0.1595 (3)	0.44183 (16)	0.64441 (11)	0.0267 (4)
C3	0.2210 (3)	0.48662 (17)	0.71679 (11)	0.0292 (5)
H3A	0.1370	0.4851	0.7461	0.035*
C4	0.4072 (3)	0.53439 (16)	0.74698 (11)	0.0289 (5)
C5	0.5361 (3)	0.52898 (17)	0.70227 (12)	0.0305 (5)
H5A	0.6625	0.5568	0.7214	0.037*
C6	0.4742 (3)	0.48286 (16)	0.63105 (11)	0.0290 (5)
H6A	0.5612	0.4801	0.6030	0.035*
C7	0.6397 (4)	0.6504 (2)	0.84374 (14)	0.0460 (6)
H7A	0.6146	0.7105	0.8733	0.055*
H7B	0.6681	0.6806	0.7999	0.055*
C8	0.8184 (4)	0.5898 (3)	0.89198 (16)	0.0615 (8)
H8A	0.9280	0.6386	0.9078	0.092*
H8B	0.8478	0.5317	0.8627	0.092*
H8C	0.7930	0.5606	0.9361	0.092*
C9	0.3349 (4)	0.58173 (19)	0.86478 (13)	0.0414 (6)
H9A	0.2019	0.5989	0.8338	0.050*
H9B	0.3772	0.6373	0.9037	0.050*
C10	0.3350 (4)	0.4732 (2)	0.90292 (13)	0.0492 (7)
H10A	0.2488	0.4762	0.9334	0.074*
H10B	0.4656	0.4565	0.9349	0.074*
H10C	0.2908	0.4179	0.8647	0.074*
C11	0.2253 (3)	0.39466 (16)	0.52344 (11)	0.0265 (4)
H11A	0.3120	0.3965	0.4953	0.032*
C12	−0.0049 (3)	0.30557 (15)	0.41992 (11)	0.0255 (4)
C13	−0.1936 (3)	0.25907 (16)	0.39549 (11)	0.0274 (4)
C14	−0.2688 (3)	0.21019 (17)	0.32369 (12)	0.0335 (5)
H14A	−0.3934	0.1796	0.3088	0.040*
C15	−0.1567 (3)	0.20773 (17)	0.27517 (12)	0.0350 (5)
H15A	−0.2049	0.1754	0.2274	0.042*
C16	0.0289 (3)	0.25409 (17)	0.29866 (12)	0.0338 (5)
H16A	0.1037	0.2531	0.2658	0.041*
C17	0.1058 (3)	0.30176 (17)	0.36960 (11)	0.0317 (5)
H17A	0.2312	0.3314	0.3840	0.038*
C18	−0.3098 (3)	0.26378 (17)	0.44614 (12)	0.0319 (5)
H1A	−0.044 (4)	0.378 (2)	0.5719 (17)	0.071 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0314 (8)	0.0568 (11)	0.0272 (8)	−0.0084 (7)	0.0117 (7)	−0.0068 (8)
N1	0.0439 (11)	0.0333 (10)	0.0276 (9)	−0.0074 (8)	0.0116 (8)	−0.0066 (8)
N2	0.0304 (9)	0.0274 (9)	0.0234 (8)	0.0018 (7)	0.0091 (7)	0.0008 (7)
N3	0.0390 (11)	0.0513 (13)	0.0398 (11)	0.0015 (9)	0.0168 (9)	0.0065 (9)
C1	0.0295 (11)	0.0240 (10)	0.0239 (10)	0.0009 (8)	0.0096 (9)	0.0030 (8)
C2	0.0259 (10)	0.0274 (11)	0.0263 (10)	0.0005 (8)	0.0078 (9)	0.0029 (8)
C3	0.0331 (11)	0.0320 (12)	0.0248 (10)	0.0018 (9)	0.0125 (9)	0.0020 (8)
C4	0.0369 (12)	0.0231 (11)	0.0260 (10)	−0.0001 (9)	0.0091 (9)	0.0009 (8)
C5	0.0288 (11)	0.0310 (11)	0.0301 (11)	−0.0037 (9)	0.0069 (9)	0.0014 (9)
C6	0.0311 (11)	0.0291 (11)	0.0292 (10)	0.0006 (9)	0.0133 (9)	0.0028 (8)
C7	0.0565 (16)	0.0399 (14)	0.0440 (14)	−0.0184 (12)	0.0191 (12)	−0.0163 (11)
C8	0.0448 (16)	0.081 (2)	0.0523 (17)	−0.0146 (15)	0.0062 (13)	−0.0122 (15)
C9	0.0550 (15)	0.0426 (14)	0.0287 (11)	−0.0043 (11)	0.0162 (11)	−0.0083 (10)
C10	0.0609 (17)	0.0565 (17)	0.0289 (12)	−0.0107 (13)	0.0121 (12)	0.0017 (11)
C11	0.0309 (11)	0.0260 (11)	0.0254 (10)	0.0042 (8)	0.0128 (9)	0.0037 (8)
C12	0.0312 (11)	0.0214 (10)	0.0246 (10)	0.0044 (8)	0.0098 (9)	0.0023 (8)
C13	0.0330 (11)	0.0233 (10)	0.0266 (10)	0.0014 (8)	0.0104 (9)	0.0021 (8)
C14	0.0376 (12)	0.0295 (12)	0.0314 (11)	−0.0030 (9)	0.0079 (10)	−0.0014 (9)
C15	0.0461 (13)	0.0280 (12)	0.0287 (11)	−0.0005 (9)	0.0089 (10)	−0.0061 (9)
C16	0.0418 (13)	0.0329 (12)	0.0303 (11)	0.0018 (10)	0.0166 (10)	−0.0025 (9)
C17	0.0321 (11)	0.0347 (12)	0.0294 (11)	0.0000 (9)	0.0111 (9)	−0.0008 (9)
C18	0.0325 (11)	0.0309 (12)	0.0303 (11)	−0.0025 (9)	0.0071 (10)	0.0019 (9)

O1—C2	1.358 (2)	C8—H8A	0.9600
O1—H1A	0.88 (3)	C8—H8B	0.9600
N1—C4	1.371 (3)	C8—H8C	0.9600
N1—C7	1.461 (3)	C9—C10	1.512 (3)
N1—C9	1.462 (3)	C9—H9A	0.9700
N2—C11	1.297 (3)	C9—H9B	0.9700
N2—C12	1.409 (3)	C10—H10A	0.9600
N3—C18	1.148 (3)	C10—H10B	0.9600
C1—C6	1.406 (3)	C10—H10C	0.9600
C1—C2	1.416 (3)	C11—H11A	0.9300
C1—C11	1.433 (3)	C12—C17	1.403 (3)
C2—C3	1.385 (3)	C12—C13	1.409 (3)
C3—C4	1.406 (3)	C13—C14	1.402 (3)
C3—H3A	0.9300	C13—C18	1.439 (3)
C4—C5	1.424 (3)	C14—C15	1.382 (3)
C5—C6	1.373 (3)	C14—H14A	0.9300
C5—H5A	0.9300	C15—C16	1.388 (3)
C6—H6A	0.9300	C15—H15A	0.9300
C7—C8	1.509 (4)	C16—C17	1.383 (3)
C7—H7A	0.9700	C16—H16A	0.9300
C7—H7B	0.9700	C17—H17A	0.9300
C2—O1—H1A	107.1 (19)	N1—C9—C10	113.3 (2)
C4—N1—C7	122.16 (19)	N1—C9—H9A	108.9
C4—N1—C9	120.78 (19)	C10—C9—H9A	108.9
C7—N1—C9	116.85 (18)	N1—C9—H9B	108.9
C11—N2—C12	122.03 (17)	C10—C9—H9B	108.9
C6—C1—C2	116.85 (18)	H9A—C9—H9B	107.7
C6—C1—C11	120.79 (18)	C9—C10—H10A	109.5
C2—C1—C11	122.35 (19)	C9—C10—H10B	109.5
O1—C2—C3	117.68 (18)	H10A—C10—H10B	109.5
O1—C2—C1	121.33 (18)	C9—C10—H10C	109.5
C3—C2—C1	120.99 (19)	H10A—C10—H10C	109.5
C2—C3—C4	121.58 (19)	H10B—C10—H10C	109.5
C2—C3—H3A	119.2	N2—C11—C1	121.77 (18)
C4—C3—H3A	119.2	N2—C11—H11A	119.1
N1—C4—C3	121.13 (19)	C1—C11—H11A	119.1
N1—C4—C5	121.4 (2)	C17—C12—C13	117.61 (19)
C3—C4—C5	117.49 (19)	C17—C12—N2	126.53 (19)
C6—C5—C4	120.2 (2)	C13—C12—N2	115.86 (17)
C6—C5—H5A	119.9	C14—C13—C12	121.52 (19)
C4—C5—H5A	119.9	C14—C13—C18	120.3 (2)
C5—C6—C1	122.75 (19)	C12—C13—C18	118.17 (18)
C5—C6—H6A	118.6	C15—C14—C13	119.7 (2)
C1—C6—H6A	118.6	C15—C14—H14A	120.2
N1—C7—C8	114.6 (2)	C13—C14—H14A	120.2
N1—C7—H7A	108.6	C14—C15—C16	119.1 (2)
C8—C7—H7A	108.6	C14—C15—H15A	120.4
N1—C7—H7B	108.6	C16—C15—H15A	120.4
C8—C7—H7B	108.6	C17—C16—C15	121.9 (2)
H7A—C7—H7B	107.6	C17—C16—H16A	119.1
C7—C8—H8A	109.5	C15—C16—H16A	119.1
C7—C8—H8B	109.5	C16—C17—C12	120.2 (2)
H8A—C8—H8B	109.5	C16—C17—H17A	119.9
C7—C8—H8C	109.5	C12—C17—H17A	119.9
H8A—C8—H8C	109.5	N3—C18—C13	179.8 (3)
H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.88 (3)	1.83 (3)	2.623 (3)	149 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2	0.88 (3)	1.83 (3)	2.623 (3)	149 (3)