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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 3| March 2010| Page o528
doi:10.1107/S160053681000111X

(E)-2-(4-Di­ethyl­amino-2-hy­droxy­benzyl­­idene­amino)benzo­nitrile

Xing-Cong Wang,a* Hua Xub and Kun Qianc

aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China, bInternational Education College of Jiangxi University of Traditional Chinese Medicine, NanChang 330004, People's Republic of China, and cAcademic Administration of Jiangxi University of Traditional Chinese Medicine, NanChang 330004, People's Republic of China
*Correspondence e-mail: wangxingcong@yahoo.cn

(Received 3 January 2010; accepted 9 January 2010; online 6 February 2010)

The mol­ecule of the title compound, C18H19N3O, 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 intra­molecular O—H⋯N hydrogen bond stabilizes the mol­ecular conformation.

Related literature

For the properties of Schiff bases compounds, see: Weber et al. (2007[Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159-1162.]). Chen et al. (2008[Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170-2171.]). May et al. (2004[May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145-4156.]).

[Scheme 1]

Experimental

Crystal data

  • C18H19N3O

  • Mr = 293.36

  • Monoclinic, P 21 /c

  • 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.984, Tmax = 0.984

  • 16730 measured reflections

  • 3546 independent reflections

  • 2694 reflections with I > 2σ(I)

  • Rint = 0.062
Refinement

  • R[F2 > 2σ(F2)] = 0.072

  • wR(F2) = 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

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)

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

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

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

checkCIF report


Comment top

Schiff bases compounds are of great interest in many fields of chemistry and biochemistry, primarily due to their importance in the development of coordination chemistry related to magnetism (Weber, et al., 2007), catalysis (Chen, et al., 2008) and biological process (May, et al.,2004). Here, we report the synthesis and crystal structure of the title compound, (I).

Fig. 1 shows ORTEP plots of the title compounds. All the bond lengths and angles in the molecules are in the range of normal values. The molecule displays a trans configuration about the central C11=N2 bond and adopts the phenol-imine tautomeric form, with a strong intramolecular O—H···N hydrogen bonding interaction (Table 1). The dihedral angle between the mean planes of the two aromatic rings is 2.62 (11) ° indicating that the Schiff-base ligand adopts a coplanar conformation. In addition, two methyl groups are oriented to the same direction relative to the plane of the adjacent benzene ring. The crystal packing is stabilized by van der Waals interactions.

Related literature top

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

Experimental top

4-aminobenzonitrile (0.590 g, 5 mmol)and 4-(diethylamino)-2-hydroxybenzaldehyde (0.996 g, 5 mmol) were dissolved in ethanol (20 ml). The reaction mixture was stirred for 6 h under reflux, and then cooled to room temperature slowly. The resulting yellow precipitate was filtered off and the yellow crystals of the title compound suitable for X-ray analysis were obtained from acetonitrile solution by slow evaporation.

Refinement top

H atoms (for OH) were located in a difference Fourier map and refined isotropically. The remailing H atoms were located geometrically and treated as riding atoms with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C) for aromatic H atoms or 1.5 Ueq (C) for methyl H atoms.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
(E)-2-(4-Diethylamino-2-hydroxybenzylideneamino)benzonitrile top
Crystal data top
C18H19N3OF(000) = 624
Mr = 293.36Dx = 1.254 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3397 reflections
a = 7.185 (5) Åθ = 2.3–27.6°
b = 12.324 (9) ŵ = 0.08 mm−1
c = 18.490 (12) ÅT = 293 K
β = 108.39 (2)°Prism, yellow
V = 1553.6 (19) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku SCXmini
diffractometer		3546 independent reflections
Radiation source: fine-focus sealed tube2694 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 13.6612 pixels mm-1θmax = 27.4°, θmin = 2.9°
ω scansh = −9→9
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −15→15
Tmin = 0.984, Tmax = 0.984l = −23→23
16730 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H 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 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C18H19N3OV = 1553.6 (19) Å3
Mr = 293.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.185 (5) ŵ = 0.08 mm−1
b = 12.324 (9) ÅT = 293 K
c = 18.490 (12) Å0.20 × 0.20 × 0.20 mm
β = 108.39 (2)°
Data collection top
Rigaku SCXmini
diffractometer		3546 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2694 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.984Rint = 0.062
16730 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0720 restraints
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 0.22 e Å−3
3546 reflectionsΔρmin = −0.20 e Å−3
203 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1−0.0254 (2)0.40112 (14)0.61866 (9)0.0379 (4)
N10.4621 (3)0.58450 (14)0.81676 (10)0.0349 (4)
N20.0535 (2)0.35141 (13)0.49350 (9)0.0269 (4)
N3−0.4028 (3)0.26723 (17)0.48643 (11)0.0424 (5)
C10.2850 (3)0.43963 (16)0.59876 (11)0.0255 (4)
C20.1595 (3)0.44183 (16)0.64441 (11)0.0267 (4)
C30.2210 (3)0.48662 (17)0.71679 (11)0.0292 (5)
H3A0.13700.48510.74610.035*
C40.4072 (3)0.53439 (16)0.74698 (11)0.0289 (5)
C50.5361 (3)0.52898 (17)0.70227 (12)0.0305 (5)
H5A0.66250.55680.72140.037*
C60.4742 (3)0.48286 (16)0.63105 (11)0.0290 (5)
H6A0.56120.48010.60300.035*
C70.6397 (4)0.6504 (2)0.84374 (14)0.0460 (6)
H7A0.61460.71050.87330.055*
H7B0.66810.68060.79990.055*
C80.8184 (4)0.5898 (3)0.89198 (16)0.0615 (8)
H8A0.92800.63860.90780.092*
H8B0.84780.53170.86270.092*
H8C0.79300.56060.93610.092*
C90.3349 (4)0.58173 (19)0.86478 (13)0.0414 (6)
H9A0.20190.59890.83380.050*
H9B0.37720.63730.90370.050*
C100.3350 (4)0.4732 (2)0.90292 (13)0.0492 (7)
H10A0.24880.47620.93340.074*
H10B0.46560.45650.93490.074*
H10C0.29080.41790.86470.074*
C110.2253 (3)0.39466 (16)0.52344 (11)0.0265 (4)
H11A0.31200.39650.49530.032*
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−0.39340.17960.30880.040*
C15−0.1567 (3)0.20773 (17)0.27517 (12)0.0350 (5)
H15A−0.20490.17540.22740.042*
C160.0289 (3)0.25409 (17)0.29866 (12)0.0338 (5)
H16A0.10370.25310.26580.041*
C170.1058 (3)0.30176 (17)0.36960 (11)0.0317 (5)
H17A0.23120.33140.38400.038*
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)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0314 (8)0.0568 (11)0.0272 (8)−0.0084 (7)0.0117 (7)−0.0068 (8)
N10.0439 (11)0.0333 (10)0.0276 (9)−0.0074 (8)0.0116 (8)−0.0066 (8)
N20.0304 (9)0.0274 (9)0.0234 (8)0.0018 (7)0.0091 (7)0.0008 (7)
N30.0390 (11)0.0513 (13)0.0398 (11)0.0015 (9)0.0168 (9)0.0065 (9)
C10.0295 (11)0.0240 (10)0.0239 (10)0.0009 (8)0.0096 (9)0.0030 (8)
C20.0259 (10)0.0274 (11)0.0263 (10)0.0005 (8)0.0078 (9)0.0029 (8)
C30.0331 (11)0.0320 (12)0.0248 (10)0.0018 (9)0.0125 (9)0.0020 (8)
C40.0369 (12)0.0231 (11)0.0260 (10)−0.0001 (9)0.0091 (9)0.0009 (8)
C50.0288 (11)0.0310 (11)0.0301 (11)−0.0037 (9)0.0069 (9)0.0014 (9)
C60.0311 (11)0.0291 (11)0.0292 (10)0.0006 (9)0.0133 (9)0.0028 (8)
C70.0565 (16)0.0399 (14)0.0440 (14)−0.0184 (12)0.0191 (12)−0.0163 (11)
C80.0448 (16)0.081 (2)0.0523 (17)−0.0146 (15)0.0062 (13)−0.0122 (15)
C90.0550 (15)0.0426 (14)0.0287 (11)−0.0043 (11)0.0162 (11)−0.0083 (10)
C100.0609 (17)0.0565 (17)0.0289 (12)−0.0107 (13)0.0121 (12)0.0017 (11)
C110.0309 (11)0.0260 (11)0.0254 (10)0.0042 (8)0.0128 (9)0.0037 (8)
C120.0312 (11)0.0214 (10)0.0246 (10)0.0044 (8)0.0098 (9)0.0023 (8)
C130.0330 (11)0.0233 (10)0.0266 (10)0.0014 (8)0.0104 (9)0.0021 (8)
C140.0376 (12)0.0295 (12)0.0314 (11)−0.0030 (9)0.0079 (10)−0.0014 (9)
C150.0461 (13)0.0280 (12)0.0287 (11)−0.0005 (9)0.0089 (10)−0.0061 (9)
C160.0418 (13)0.0329 (12)0.0303 (11)0.0018 (10)0.0166 (10)−0.0025 (9)
C170.0321 (11)0.0347 (12)0.0294 (11)0.0000 (9)0.0111 (9)−0.0008 (9)
C180.0325 (11)0.0309 (12)0.0303 (11)−0.0025 (9)0.0071 (10)0.0019 (9)
Geometric parameters (Å, º) top
O1—C21.358 (2)C8—H8A0.9600
O1—H1A0.88 (3)C8—H8B0.9600
N1—C41.371 (3)C8—H8C0.9600
N1—C71.461 (3)C9—C101.512 (3)
N1—C91.462 (3)C9—H9A0.9700
N2—C111.297 (3)C9—H9B0.9700
N2—C121.409 (3)C10—H10A0.9600
N3—C181.148 (3)C10—H10B0.9600
C1—C61.406 (3)C10—H10C0.9600
C1—C21.416 (3)C11—H11A0.9300
C1—C111.433 (3)C12—C171.403 (3)
C2—C31.385 (3)C12—C131.409 (3)
C3—C41.406 (3)C13—C141.402 (3)
C3—H3A0.9300C13—C181.439 (3)
C4—C51.424 (3)C14—C151.382 (3)
C5—C61.373 (3)C14—H14A0.9300
C5—H5A0.9300C15—C161.388 (3)
C6—H6A0.9300C15—H15A0.9300
C7—C81.509 (4)C16—C171.383 (3)
C7—H7A0.9700C16—H16A0.9300
C7—H7B0.9700C17—H17A0.9300
C2—O1—H1A107.1 (19)N1—C9—C10113.3 (2)
C4—N1—C7122.16 (19)N1—C9—H9A108.9
C4—N1—C9120.78 (19)C10—C9—H9A108.9
C7—N1—C9116.85 (18)N1—C9—H9B108.9
C11—N2—C12122.03 (17)C10—C9—H9B108.9
C6—C1—C2116.85 (18)H9A—C9—H9B107.7
C6—C1—C11120.79 (18)C9—C10—H10A109.5
C2—C1—C11122.35 (19)C9—C10—H10B109.5
O1—C2—C3117.68 (18)H10A—C10—H10B109.5
O1—C2—C1121.33 (18)C9—C10—H10C109.5
C3—C2—C1120.99 (19)H10A—C10—H10C109.5
C2—C3—C4121.58 (19)H10B—C10—H10C109.5
C2—C3—H3A119.2N2—C11—C1121.77 (18)
C4—C3—H3A119.2N2—C11—H11A119.1
N1—C4—C3121.13 (19)C1—C11—H11A119.1
N1—C4—C5121.4 (2)C17—C12—C13117.61 (19)
C3—C4—C5117.49 (19)C17—C12—N2126.53 (19)
C6—C5—C4120.2 (2)C13—C12—N2115.86 (17)
C6—C5—H5A119.9C14—C13—C12121.52 (19)
C4—C5—H5A119.9C14—C13—C18120.3 (2)
C5—C6—C1122.75 (19)C12—C13—C18118.17 (18)
C5—C6—H6A118.6C15—C14—C13119.7 (2)
C1—C6—H6A118.6C15—C14—H14A120.2
N1—C7—C8114.6 (2)C13—C14—H14A120.2
N1—C7—H7A108.6C14—C15—C16119.1 (2)
C8—C7—H7A108.6C14—C15—H15A120.4
N1—C7—H7B108.6C16—C15—H15A120.4
C8—C7—H7B108.6C17—C16—C15121.9 (2)
H7A—C7—H7B107.6C17—C16—H16A119.1
C7—C8—H8A109.5C15—C16—H16A119.1
C7—C8—H8B109.5C16—C17—C12120.2 (2)
H8A—C8—H8B109.5C16—C17—H17A119.9
C7—C8—H8C109.5C12—C17—H17A119.9
H8A—C8—H8C109.5N3—C18—C13179.8 (3)
H8B—C8—H8C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.88 (3)1.83 (3)2.623 (3)149 (3)

Experimental details

Crystal data
Chemical formulaC18H19N3O
Mr293.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.185 (5), 12.324 (9), 18.490 (12)
β (°) 108.39 (2)
V (Å3)1553.6 (19)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.984, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		16730, 3546, 2694
Rint0.062
(sin θ/λ)max (Å−1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.152, 1.16
No. of reflections3546
No. of parameters203
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.22, −0.20

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.88 (3)1.83 (3)2.623 (3)149 (3)
 

References

First citationChen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170–2171.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationMay, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145–4156.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWeber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159–1162.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 3| March 2010| Page o528
doi:10.1107/S160053681000111X
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