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

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ISSN: 2056-9890

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

aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China, and bAcademic Administration of JiangXi University of Traditional Chinese Medicine, Nanchang 330047, People's Republic of China
*Correspondence e-mail: yuyanhong001@yahoo.com.cn

(Received 24 April 2009; accepted 28 April 2009; online 7 May 2009)

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[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.]). For the structure of a related compound, see: Elmah et al. (1999[Elmah, A., Kabak, M. & Elerman, Y. (1999). J. Mol. Struct. 484, 229-234.]).

[Scheme 1]

Experimental

Crystal data
  • C17H21N3O

  • Mr = 283.37

  • Orthorhombic, P 21 21 21

  • 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.973, Tmax = 0.979

  • 16156 measured reflections

  • 2061 independent reflections

  • 1996 reflections with I > 2σ(I)

  • Rint = 0.063

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3B⋯O1i 0.86 2.55 3.395 (4) 167
O1—H1A⋯N2 0.86 (5) 1.82 (5) 2.638 (4) 157 (4)
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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


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 C11N2 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
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 top
Rigaku SCXmini
diffractometer
3566 independent reflections
Radiation source: fine-focus sealed tube1996 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 88
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1616
Tmin = 0.973, Tmax = 0.979l = 2424
16156 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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 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 = 0.14 e Å3
Crystal data top
C17H21N3OV = 1552.0 (6) Å3
Mr = 283.37Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.5904 (13) ŵ = 0.08 mm1
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)] = 0.0580 restraints
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.13 e Å3
2061 reflectionsΔρmin = 0.14 e Å3
194 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
C10.2951 (5)0.8186 (2)0.07623 (17)0.0481 (8)
O10.0143 (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)
H3A0.11960.94710.03890.064*
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)
H5A0.39280.92700.07920.064*
C120.4162 (5)0.6759 (3)0.24289 (18)0.0555 (9)
C90.1458 (6)1.0453 (3)0.1467 (2)0.0724 (11)
H9A0.04961.06550.18390.087*
H9B0.22280.98580.16480.087*
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*
C70.1687 (6)1.0581 (3)0.0710 (2)0.0727 (11)
H7A0.25851.00410.05220.087*
H7B0.22231.08040.11730.087*
C100.2883 (6)1.1352 (3)0.1340 (3)0.0871 (13)
H10A0.35661.15240.17820.131*
H10B0.38661.11550.09820.131*
H10C0.21331.19520.11750.131*
C150.6240 (8)0.5819 (4)0.3550 (2)0.0818 (13)
H15A0.69290.55020.39300.098*
C80.1708 (7)1.1508 (4)0.0202 (3)0.0933 (14)
H8A0.30701.17670.01540.140*
H8B0.08541.20550.03900.140*
H8C0.12131.12910.02620.140*
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, º) 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, º) 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 code: (i) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H21N3O
Mr283.37
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)6.5904 (13), 12.703 (3), 18.538 (4)
V3)1552.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.973, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
16156, 3566, 1996
Rint0.063
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.176, 1.04
No. of reflections2061
No. of parameters194
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.13, 0.14

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
N3—H3B···O1i0.862.553.395 (4)167.3
O1—H1A···N20.86 (5)1.82 (5)2.638 (4)157 (4)
Symmetry code: (i) x, y1/2, z+1/2.
 

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

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