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Acta Cryst. (2009). E65, o1232    [ doi:10.1107/S1600536809015773 ]

2-[(E)-(2-Aminophenyl)iminomethyl]-5-(dimethylamino)phenol

Y.-H. Yu and K. Qian

Abstract top

The molecule of the title compound, C17H21N3O, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the planes of the two benzene rings is 50.96 (11)° and a strong intramolecular O-H...N hydrogen bond is present. An intermolecular N-H...O hydrogen-bonding interaction stabilizes the crystal structure.

Comment top

Schiff base compounds have received considerable attention for many years, 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 processes (May et al.,2004). Our group is interested in the synthesis and preparation of Schiff bases. Here, we report the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the mean planes of the two aromatic rings is 50.96 (11)°, indicating that the Schiff-base ligand adopts a non-planar conformation. As expected, the molecule displays a trans configuration about the central C11═N2 bond. Bond lengths and angles observed in the structure are in normal ranges and comparable with those of a related Schiff base compound (Elmah et al., 1999). The hydroxy group is involved as donor in a strong intramolecular O—H···N hydrogen bond (Table 1) and as acceptor in an weak intermolecular N—H···O hydrogen interaction (Fig. 2, Table 1).

Related literature top

For general background to the properties of Schiff base compounds, see: Weber et al. (2007); Chen et al. (2008); May et al. (2004). For the structure of a related compound, see: Elmah et al. (1999).

Experimental top

Benzene-1,2-diamine (0.59 g, 5 mmol) and 4-(diethylamino)-2-hydroxybenzaldehyde (0.965 g, 5 mmol) were dissolved in methanol (15 ml). The mixture was heated to reflux for 6 h, then cooled to room temperature, then the solution was filtered and dried (yield 84%). Crystals of the title compound suitable for X-ray diffraction analysis were grown by slow evaporation of an ethanol solution. Esi-MS: calcd for C17H21N3O + H m/z 283.37, found 284.72.

Refinement top

The H atom of the hydroxy group was found in a difference Fourier map and refined freely. The other H atoms were placed geometrically and treated as riding atoms, with N—H =0.86 Å, C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(C) for methyl H atoms. In the absence of significant anomalous scattering effects, 1505 Friedel pairs were merged in the final refinement.

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. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound, showing the structure along the a axis. Intermolecular N—H···O hydrogen bonds are shown as dashed lines.
2-[(E)-(2-Aminophenyl)iminomethyl]-5-(dimethylamino)phenol top
Crystal data top
C17H21N3OF000 = 608
Mr = 283.37Dx = 1.213 Mg m−3
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1474 reflections
a = 6.5904 (13) Åθ = 3.1–27.8º
b = 12.703 (3) ŵ = 0.08 mm−1
c = 18.538 (4) ÅT = 293 K
V = 1552.0 (6) Å3Prism, yellow
Z = 40.20 × 0.20 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer		3566 independent reflections
Radiation source: fine-focus sealed tube1996 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293 Kθmin = 3.2º
ω scansh = −8→8
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −16→16
Tmin = 0.973, Tmax = 0.979l = −24→24
16156 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.176  w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2061 reflectionsΔρmax = 0.13 e Å−3
194 parametersΔρmin = −0.13 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C17H21N3OV = 1552.0 (6) Å3
Mr = 283.37Z = 4
Orthorhombic, P212121Mo Kα
a = 6.5904 (13) ŵ = 0.08 mm−1
b = 12.703 (3) ÅT = 293 K
c = 18.538 (4) Å0.20 × 0.20 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer		3566 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		1996 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.979Rint = 0.063
16156 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058Δρmax = 0.13 e Å−3
wR(F2) = 0.176Δρmin = −0.13 e Å−3
S = 1.04Absolute structure: ?
2061 reflectionsFlack parameter: ?
194 parametersRogers parameter: ?
H atoms treated by a mixture of
independent and constrained refinement
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
C10.2951 (5)0.8186 (2)0.07623 (17)0.0481 (8)
O1−0.0143 (4)0.8354 (2)0.14362 (14)0.0690 (8)
N20.3009 (5)0.7252 (2)0.18825 (15)0.0600 (8)
C30.0114 (5)0.9219 (3)0.03213 (18)0.0532 (8)
H3A−0.11960.94710.03890.064*
C40.1183 (5)0.9498 (2)−0.03042 (18)0.0528 (8)
C20.0966 (5)0.8582 (3)0.08329 (17)0.0508 (8)
C110.3911 (6)0.7562 (2)0.13124 (19)0.0569 (9)
H11A0.52640.73740.12490.068*
C60.3994 (5)0.8473 (2)0.01367 (17)0.0543 (8)
H6A0.53090.82250.00720.065*
N10.0326 (4)1.0119 (3)−0.08228 (15)0.0627 (8)
C50.3174 (5)0.9101 (3)−0.03833 (17)0.0535 (8)
H5A0.39280.9270−0.07920.064*
C120.4162 (5)0.6759 (3)0.24289 (18)0.0555 (9)
C90.1458 (6)1.0453 (3)−0.1467 (2)0.0724 (11)
H9A0.04961.0655−0.18390.087*
H9B0.22280.9858−0.16480.087*
N30.1521 (5)0.5451 (3)0.25389 (18)0.0844 (11)
H3B0.10480.48910.27390.101*
H3C0.08710.57430.21900.101*
C130.3329 (6)0.5880 (3)0.27784 (19)0.0619 (10)
C140.4406 (7)0.5432 (3)0.3335 (2)0.0773 (12)
H14A0.38690.48490.35710.093*
C160.7079 (7)0.6677 (3)0.3207 (2)0.0798 (12)
H16A0.83290.69430.33520.096*
C170.6027 (6)0.7135 (3)0.2645 (2)0.0660 (10)
H17A0.65890.77100.24060.079*
C7−0.1687 (6)1.0581 (3)−0.0710 (2)0.0727 (11)
H7A−0.25851.0041−0.05220.087*
H7B−0.22231.0804−0.11730.087*
C100.2883 (6)1.1352 (3)−0.1340 (3)0.0871 (13)
H10A0.35661.1524−0.17820.131*
H10B0.38661.1155−0.09820.131*
H10C0.21331.1952−0.11750.131*
C150.6240 (8)0.5819 (4)0.3550 (2)0.0818 (13)
H15A0.69290.55020.39300.098*
C8−0.1708 (7)1.1508 (4)−0.0202 (3)0.0933 (14)
H8A−0.30701.1767−0.01540.140*
H8B−0.08541.2055−0.03900.140*
H8C−0.12131.12910.02620.140*
H1A0.067 (7)0.796 (4)0.168 (2)0.098 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0444 (16)0.0430 (16)0.0570 (19)0.0037 (14)0.0031 (16)−0.0112 (15)
O10.0518 (14)0.0809 (18)0.0742 (17)0.0140 (14)0.0173 (13)0.0094 (15)
N20.0612 (17)0.0546 (16)0.0643 (18)0.0097 (15)0.0110 (15)0.0026 (15)
C30.0384 (16)0.0548 (19)0.067 (2)0.0022 (15)0.0021 (16)−0.0071 (17)
C40.0463 (17)0.0486 (17)0.064 (2)−0.0065 (15)−0.0084 (16)−0.0116 (16)
C20.0469 (17)0.0475 (17)0.0581 (19)−0.0039 (16)0.0080 (17)−0.0092 (16)
C110.056 (2)0.0458 (18)0.069 (2)0.0095 (16)0.0007 (19)−0.0099 (17)
C60.0449 (16)0.0517 (19)0.066 (2)0.0060 (16)0.0064 (17)−0.0112 (16)
N10.0488 (16)0.0772 (19)0.0622 (17)0.0011 (15)−0.0072 (15)0.0005 (16)
C50.0438 (17)0.0570 (18)0.060 (2)−0.0009 (16)0.0015 (17)−0.0088 (17)
C120.0560 (19)0.0485 (18)0.062 (2)0.0119 (17)0.0056 (18)−0.0012 (17)
C90.068 (2)0.080 (3)0.069 (2)0.004 (2)−0.014 (2)0.004 (2)
N30.077 (2)0.084 (2)0.093 (2)−0.0138 (19)0.008 (2)0.012 (2)
C130.062 (2)0.056 (2)0.067 (2)0.0106 (19)0.010 (2)−0.0010 (18)
C140.084 (3)0.067 (2)0.080 (3)0.019 (2)0.020 (2)0.012 (2)
C160.066 (2)0.083 (3)0.090 (3)0.019 (2)−0.004 (2)0.000 (3)
C170.063 (2)0.059 (2)0.076 (2)0.010 (2)0.005 (2)0.0051 (19)
C70.051 (2)0.088 (3)0.079 (2)0.002 (2)−0.017 (2)0.008 (2)
C100.075 (3)0.083 (3)0.102 (3)−0.011 (3)−0.016 (3)0.014 (2)
C150.091 (3)0.078 (3)0.076 (3)0.029 (3)0.000 (3)0.017 (2)
C80.076 (3)0.098 (3)0.106 (3)0.024 (3)−0.001 (3)−0.005 (3)
Geometric parameters (Å, °) top
C1—C61.397 (4)C9—H9B0.9700
C1—C21.407 (4)N3—C131.383 (5)
C1—C111.438 (4)N3—H3B0.8600
O1—C21.367 (4)N3—H3C0.8600
O1—H1A0.86 (5)C13—C141.376 (5)
N2—C111.275 (4)C14—C151.365 (6)
N2—C121.413 (4)C14—H14A0.9300
C3—C21.367 (4)C16—C151.377 (6)
C3—C41.402 (5)C16—C171.380 (5)
C3—H3A0.9300C16—H16A0.9300
C4—N11.366 (4)C17—H17A0.9300
C4—C51.413 (5)C7—C81.509 (5)
C11—H11A0.9300C7—H7A0.9700
C6—C51.363 (4)C7—H7B0.9700
C6—H6A0.9300C10—H10A0.9600
N1—C71.465 (5)C10—H10B0.9600
N1—C91.471 (4)C10—H10C0.9600
C5—H5A0.9300C15—H15A0.9300
C12—C171.378 (5)C8—H8A0.9600
C12—C131.403 (5)C8—H8B0.9600
C9—C101.497 (5)C8—H8C0.9600
C9—H9A0.9700
C6—C1—C2116.2 (3)C13—N3—H3C120.0
C6—C1—C11121.1 (3)H3B—N3—H3C120.0
C2—C1—C11122.7 (3)C14—C13—N3121.4 (4)
C2—O1—H1A103 (3)C14—C13—C12118.3 (4)
C11—N2—C12118.7 (3)N3—C13—C12120.2 (3)
C2—C3—C4121.1 (3)C15—C14—C13121.8 (4)
C2—C3—H3A119.4C15—C14—H14A119.1
C4—C3—H3A119.4C13—C14—H14A119.1
N1—C4—C3121.4 (3)C15—C16—C17118.7 (4)
N1—C4—C5121.1 (3)C15—C16—H16A120.6
C3—C4—C5117.5 (3)C17—C16—H16A120.6
O1—C2—C3118.2 (3)C12—C17—C16121.4 (4)
O1—C2—C1119.8 (3)C12—C17—H17A119.3
C3—C2—C1121.9 (3)C16—C17—H17A119.3
N2—C11—C1123.5 (3)N1—C7—C8114.2 (3)
N2—C11—H11A118.2N1—C7—H7A108.7
C1—C11—H11A118.2C8—C7—H7A108.7
C5—C6—C1123.0 (3)N1—C7—H7B108.7
C5—C6—H6A118.5C8—C7—H7B108.7
C1—C6—H6A118.5H7A—C7—H7B107.6
C4—N1—C7120.3 (3)C9—C10—H10A109.5
C4—N1—C9121.9 (3)C9—C10—H10B109.5
C7—N1—C9117.4 (3)H10A—C10—H10B109.5
C6—C5—C4120.2 (3)C9—C10—H10C109.5
C6—C5—H5A119.9H10A—C10—H10C109.5
C4—C5—H5A119.9H10B—C10—H10C109.5
C17—C12—C13119.4 (3)C14—C15—C16120.4 (4)
C17—C12—N2122.3 (3)C14—C15—H15A119.8
C13—C12—N2118.3 (3)C16—C15—H15A119.8
N1—C9—C10114.2 (3)C7—C8—H8A109.5
N1—C9—H9A108.7C7—C8—H8B109.5
C10—C9—H9A108.7H8A—C8—H8B109.5
N1—C9—H9B108.7C7—C8—H8C109.5
C10—C9—H9B108.7H8A—C8—H8C109.5
H9A—C9—H9B107.6H8B—C8—H8C109.5
C13—N3—H3B120.0
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O1i0.862.553.395 (4)167
O1—H1A···N20.86 (5)1.82 (5)2.638 (4)157 (4)
Symmetry codes: (i) −x, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O1i0.862.553.395 (4)167
O1—H1A···N20.86 (5)1.82 (5)2.638 (4)157 (4)
Symmetry codes: (i) −x, y−1/2, −z+1/2.
references
References top

Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170–2171.

Elmah, A., Kabak, M. & Elerman, Y. (1999). J. Mol. Struct. 484, 229–234.

May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145–4156.

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159–1162.