PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1232.
Published online 2009 May 7. doi:  10.1107/S1600536809015773
PMCID: PMC2969689

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

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o1232-scheme1.jpg

Experimental

Crystal data

  • C17H21N3O
  • M r = 283.37
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1232-efi1.jpg
  • a = 6.5904 (13) Å
  • b = 12.703 (3) Å
  • c = 18.538 (4) Å
  • V = 1552.0 (6) 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 [triangle]) T min = 0.973, T max = 0.979
  • 16156 measured reflections
  • 2061 independent reflections
  • 1996 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.176
  • S = 1.04
  • 2061 reflections
  • 194 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.14 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015773/rz2315sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015773/rz2315Isup2.hkl

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

Fig. 1.
The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
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.

Crystal data

C17H21N3OF(000) = 608
Mr = 283.37Dx = 1.213 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1474 reflections
a = 6.5904 (13) Åθ = 3.1–27.8°
b = 12.703 (3) ŵ = 0.08 mm1
c = 18.538 (4) ÅT = 293 K
V = 1552.0 (6) Å3Prism, yellow
Z = 40.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer3566 independent reflections
Radiation source: fine-focus sealed tube1996 reflections with I > 2σ(I)
graphiteRint = 0.063
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
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

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2061 reflections(Δ/σ)max = 0.001
194 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.13 e Å3

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2315).

References

  • Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170–2171. [PubMed]
  • 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. [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem.633, 1159–1162.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography