(E)-4-[(4-Diethyl-amino-2-hy-droxy-benzyl-idene)amino]-benzonitrile.

The title compound, C(18)H(19)N(3)O, displays an E conformation with respect to the C=N double bond. The dihedral angle between the mean planes of the two benzene rings is 24.49 (3)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by nonclassical inter-molecular C-H⋯O hydrogen bonds to form an infinite one-dimensional chain along [010], generating a C(8) motif.

Related literature

For the preparation of the title compound, see: Shirinian et al. (2010 ▶). For the applications of proton transfer dyes, see: Chen & Pang (2010 ▶); Chuang et al. (2011 ▶); Han et al. (2010 ▶); Helal et al. (2010 ▶); Ikeda et al. (2010 ▶); Ito et al. (2011 ▶); Lim et al. (2011 ▶); Lins et al. (2010 ▶); Maupin et al. (2011 ▶); Santos et al. (2011 ▶); Tang et al. (2011 ▶). For related structures, see: Blagus & Kaitner (2011 ▶); Chen et al. (2011 ▶); Guo (2010 ▶); Manvizhi et al. (2011 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

C18H19N3O

M = 293.36

Monoclinic,

a = 15.361 (3) Å

b = 12.118 (2) Å

c = 8.7317 (14) Å

β = 100.717 (4)°

V = 1597.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.42 × 0.35 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2001 ▶) T min = 0.436, T max = 1.000

8867 measured reflections

3136 independent reflections

1405 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.171

S = 1.02

3136 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812008082/rk2339sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008082/rk2339Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008082/rk2339Isup3.cml

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

C18H19N3O	F(000) = 624
Mr = 293.36	Dx = 1.220 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1646 reflections
a = 15.361 (3) Å	θ = 2.2–22.6°
b = 12.118 (2) Å	µ = 0.08 mm−1
c = 8.7317 (14) Å	T = 295 K
β = 100.717 (4)°	Parallelepiped, yellow
V = 1597.0 (5) Å3	0.42 × 0.35 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	3136 independent reflections
Radiation source: fine-focus sealed tube	1405 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 26.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker 2001)	h = −18→18
Tmin = 0.436, Tmax = 1.000	k = −14→14
8867 measured reflections	l = −7→10

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3
3136 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O	−0.12526 (16)	−0.02917 (13)	0.1327 (2)	0.0914 (6)
H0A	−0.0756	−0.0162	0.1827	0.137 (16)*
N1	0.3699 (2)	0.1233 (3)	0.8181 (4)	0.1306 (11)
N2	0.01778 (14)	0.08093 (15)	0.2272 (3)	0.0735 (6)
N3	−0.34058 (17)	0.11544 (19)	−0.2774 (3)	0.0937 (6)
C1	0.3116 (2)	0.1190 (2)	0.7158 (4)	0.0969 (9)
C2	0.23844 (18)	0.1117 (2)	0.5869 (3)	0.0811 (7)
C3	0.20738 (19)	0.2036 (2)	0.4999 (4)	0.0871 (8)
H3A	0.2351	0.2714	0.5233	0.105*
C4	0.13636 (18)	0.1961 (2)	0.3796 (3)	0.0810 (8)
H4A	0.1161	0.2590	0.3230	0.097*
C5	0.09401 (18)	0.09504 (19)	0.3410 (3)	0.0702 (7)
C6	0.1265 (2)	0.0040 (2)	0.4290 (3)	0.0865 (8)
H6A	0.0992	−0.0641	0.4061	0.104*
C7	0.1975 (2)	0.0111 (2)	0.5485 (3)	0.0896 (8)
H7A	0.2185	−0.0518	0.6043	0.107*
C8	−0.00756 (15)	0.14955 (19)	0.1149 (3)	0.0701 (5)
H8A	0.0292	0.2083	0.1014	0.084*
C9	−0.08947 (16)	0.13804 (18)	0.0117 (3)	0.0701 (5)
C10	−0.11940 (19)	0.21569 (19)	−0.1058 (3)	0.0776 (8)
H10A	−0.0825	0.2744	−0.1187	0.093*
C11	−0.1997 (2)	0.2089 (2)	−0.2014 (3)	0.0807 (8)
H11A	−0.2159	0.2620	−0.2784	0.097*
C12	−0.25904 (18)	0.1226 (2)	−0.1858 (3)	0.0749 (7)
C13	−0.23028 (19)	0.04469 (19)	−0.0681 (3)	0.0778 (7)
H13A	−0.2681	−0.0127	−0.0535	0.093*
C14	−0.14852 (19)	0.05040 (18)	0.0257 (3)	0.0706 (7)
C15	−0.3678 (2)	0.1867 (3)	−0.4140 (3)	0.1043 (10)
H15A	−0.4051	0.1449	−0.4956	0.125*
H15B	−0.3156	0.2101	−0.4532	0.125*
C16	−0.4175 (2)	0.2868 (3)	−0.3755 (4)	0.1351 (13)
H16A	−0.4337	0.3316	−0.4670	0.203*
H16B	−0.3805	0.3287	−0.2954	0.203*
H16C	−0.4700	0.2639	−0.3394	0.203*
C17	−0.40588 (19)	0.0308 (2)	−0.2501 (3)	0.0937 (6)
H17A	−0.4654	0.0586	−0.2864	0.112*
H17B	−0.3990	0.0167	−0.1392	0.112*
C18	−0.3941 (3)	−0.0743 (3)	−0.3325 (5)	0.1237 (12)
H18A	−0.3371	−0.1052	−0.2905	0.164 (17)*
H18B	−0.3979	−0.0598	−0.4417	0.20 (2)*
H18C	−0.4396	−0.1255	−0.3185	0.187 (17)*

	U11	U22	U33	U12	U13	U23
O	0.1181 (17)	0.0591 (11)	0.0989 (14)	−0.0112 (10)	0.0253 (13)	0.0149 (10)
N1	0.110 (2)	0.132 (3)	0.143 (3)	0.0031 (19)	0.005 (2)	0.009 (2)
N2	0.0928 (16)	0.0518 (12)	0.0824 (15)	0.0057 (11)	0.0329 (13)	−0.0054 (11)
N3	0.1002 (14)	0.0906 (14)	0.0938 (13)	−0.0076 (10)	0.0270 (11)	0.0048 (11)
C1	0.089 (2)	0.091 (2)	0.115 (3)	0.0063 (19)	0.030 (2)	0.008 (2)
C2	0.0857 (19)	0.0719 (18)	0.093 (2)	0.0088 (16)	0.0367 (16)	0.0002 (16)
C3	0.097 (2)	0.0649 (17)	0.104 (2)	−0.0063 (15)	0.0315 (18)	−0.0012 (16)
C4	0.099 (2)	0.0546 (15)	0.094 (2)	0.0036 (14)	0.0300 (18)	0.0045 (14)
C5	0.0879 (18)	0.0504 (15)	0.0823 (18)	0.0087 (13)	0.0416 (15)	−0.0015 (13)
C6	0.113 (2)	0.0522 (16)	0.099 (2)	0.0024 (15)	0.0320 (19)	−0.0009 (15)
C7	0.114 (2)	0.0623 (18)	0.097 (2)	0.0123 (16)	0.031 (2)	0.0082 (15)
C8	0.0912 (13)	0.0506 (9)	0.0793 (14)	−0.0041 (10)	0.0439 (10)	−0.0043 (10)
C9	0.0912 (13)	0.0506 (9)	0.0793 (14)	−0.0041 (10)	0.0439 (10)	−0.0043 (10)
C10	0.107 (2)	0.0544 (15)	0.0822 (18)	−0.0098 (14)	0.0462 (17)	0.0021 (14)
C11	0.109 (2)	0.0652 (16)	0.0757 (18)	−0.0014 (16)	0.0364 (17)	0.0059 (13)
C12	0.0949 (19)	0.0610 (15)	0.0773 (18)	−0.0038 (15)	0.0380 (16)	−0.0025 (13)
C13	0.099 (2)	0.0571 (15)	0.0863 (19)	−0.0138 (14)	0.0393 (16)	−0.0013 (14)
C14	0.100 (2)	0.0471 (13)	0.0736 (17)	0.0011 (14)	0.0384 (16)	0.0006 (12)
C15	0.119 (2)	0.116 (3)	0.079 (2)	−0.010 (2)	0.0204 (18)	0.0069 (18)
C16	0.160 (3)	0.121 (3)	0.126 (3)	0.040 (3)	0.032 (2)	0.031 (2)
C17	0.1002 (14)	0.0906 (14)	0.0938 (13)	−0.0076 (10)	0.0270 (11)	0.0048 (11)
C18	0.134 (4)	0.110 (3)	0.135 (4)	−0.024 (3)	0.048 (3)	−0.024 (2)

O—C14	1.344 (3)	C9—C10	1.405 (3)
O—H0A	0.8200	C9—C14	1.417 (3)
N1—C1	1.143 (4)	C10—C11	1.357 (3)
N2—C8	1.290 (3)	C10—H10A	0.9300
N2—C5	1.398 (3)	C11—C12	1.410 (3)
N3—C12	1.358 (3)	C11—H11A	0.9300
N3—C17	1.484 (3)	C12—C13	1.405 (3)
N3—C15	1.469 (3)	C13—C14	1.368 (3)
C1—C2	1.437 (4)	C13—H13A	0.9300
C2—C3	1.383 (3)	C15—C16	1.504 (4)
C2—C7	1.383 (3)	C15—H15A	0.9700
C3—C4	1.369 (3)	C15—H15B	0.9700
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.398 (3)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.384 (3)	C17—C18	1.490 (4)
C6—C7	1.365 (3)	C17—H17A	0.9700
C6—H6A	0.9300	C17—H17B	0.9700
C7—H7A	0.9300	C18—H18A	0.9600
C8—C9	1.412 (3)	C18—H18B	0.9600
C8—H8A	0.9300	C18—H18C	0.9600
C14—O—H0A	109.5	C12—C11—H11A	119.5
C8—N2—C5	123.8 (2)	N3—C12—C13	121.2 (2)
C12—N3—C17	121.8 (2)	N3—C12—C11	122.2 (3)
C12—N3—C15	122.2 (2)	C13—C12—C11	116.6 (3)
C17—N3—C15	116.0 (2)	C14—C13—C12	122.2 (2)
N1—C1—C2	179.0 (4)	C14—C13—H13A	118.9
C3—C2—C7	118.8 (3)	C12—C13—H13A	118.9
C3—C2—C1	121.3 (3)	O—C14—C13	118.4 (2)
C7—C2—C1	119.9 (3)	O—C14—C9	120.4 (3)
C2—C3—C4	120.8 (3)	C13—C14—C9	121.2 (2)
C2—C3—H3A	119.6	N3—C15—C16	111.8 (2)
C4—C3—H3A	119.6	N3—C15—H15A	109.2
C3—C4—C5	120.8 (3)	C16—C15—H15A	109.2
C3—C4—H4A	119.6	N3—C15—H15B	109.2
C5—C4—H4A	119.6	C16—C15—H15B	109.2
N2—C5—C6	117.7 (2)	H15A—C15—H15B	107.9
N2—C5—C4	124.7 (2)	C15—C16—H16A	109.5
C6—C5—C4	117.5 (3)	C15—C16—H16B	109.5
C5—C6—C7	121.9 (3)	H16A—C16—H16B	109.5
C5—C6—H6A	119.1	C15—C16—H16C	109.5
C7—C6—H6A	119.1	H16A—C16—H16C	109.5
C2—C7—C6	120.3 (3)	H16B—C16—H16C	109.5
C2—C7—H7A	119.9	N3—C17—C18	111.5 (2)
C6—C7—H7A	119.9	N3—C17—H17A	109.3
N2—C8—C9	121.9 (2)	C18—C17—H17A	109.3
N2—C8—H8A	119.0	N3—C17—H17B	109.3
C9—C8—H8A	119.0	C18—C17—H17B	109.3
C10—C9—C14	115.9 (3)	H17A—C17—H17B	108.0
C10—C9—C8	122.1 (2)	C17—C18—H18A	109.5
C14—C9—C8	121.9 (2)	C17—C18—H18B	109.5
C11—C10—C9	123.0 (2)	H18A—C18—H18B	109.5
C11—C10—H10A	118.5	C17—C18—H18C	109.5
C9—C10—H10A	118.5	H18A—C18—H18C	109.5
C10—C11—C12	121.0 (2)	H18B—C18—H18C	109.5
C10—C11—H11A	119.5
C7—C2—C3—C4	1.2 (4)	C17—N3—C12—C13	4.9 (4)
C1—C2—C3—C4	−178.5 (2)	C15—N3—C12—C13	−171.7 (2)
C2—C3—C4—C5	−0.6 (4)	C17—N3—C12—C11	−173.9 (2)
C8—N2—C5—C6	−163.3 (2)	C15—N3—C12—C11	9.5 (4)
C8—N2—C5—C4	21.3 (3)	C10—C11—C12—N3	178.3 (2)
C3—C4—C5—N2	175.6 (2)	C10—C11—C12—C13	−0.5 (3)
C3—C4—C5—C6	0.2 (4)	N3—C12—C13—C14	−179.8 (2)
N2—C5—C6—C7	−176.2 (2)	C11—C12—C13—C14	−1.0 (3)
C4—C5—C6—C7	−0.5 (4)	C12—C13—C14—O	−178.2 (2)
C3—C2—C7—C6	−1.5 (4)	C12—C13—C14—C9	2.1 (4)
C1—C2—C7—C6	178.2 (2)	C10—C9—C14—O	178.8 (2)
C5—C6—C7—C2	1.1 (4)	C8—C9—C14—O	−4.4 (3)
C5—N2—C8—C9	−173.49 (19)	C10—C9—C14—C13	−1.5 (3)
N2—C8—C9—C10	176.6 (2)	C8—C9—C14—C13	175.3 (2)
N2—C8—C9—C14	0.0 (3)	C12—N3—C15—C16	−95.1 (3)
C14—C9—C10—C11	0.0 (3)	C17—N3—C15—C16	88.1 (3)
C8—C9—C10—C11	−176.8 (2)	C12—N3—C17—C18	−87.4 (3)
C9—C10—C11—C12	1.0 (4)	C15—N3—C17—C18	89.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N2	0.82	1.84	2.572 (3)	148
C4—H4A···Oi	0.93	2.60	3.334 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H0A⋯N2	0.82	1.84	2.572 (3)	148
C4—H4A⋯Oi	0.93	2.60	3.334 (3)	137

Symmetry code: (i) .