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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 2| February 2010| Page o449
https://doi.org/10.1107/S1600536810002503

(E)-2-[(2-Ethyl­phen­yl)iminiometh­yl]-6-hy­droxy­phenolate

Serap Yazıcı,a* Çiğdem Albayrak,b İsmail Gümrükçüoğlu,c İsmet Şenela and Orhan Büyükgüngöra

aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit-Samsun, Turkey, bSinop Faculty of Education, Sinop University, TR-57000 Sinop, Turkey, and cDepartment of Chemistry, Ondokuz Mayıs University, TR-55139 Kurupelit-Samsun, Turkey
*Correspondence e-mail: yserap@omu.edu.tr

(Received 18 January 2010; accepted 20 January 2010; online 27 January 2010)

The mol­ecule of the title compound, C15H15NO2, crystallizes in a zwitterionic form, and displays an E configuration about the C=N bond. The dihedral angle between the two aromatic rings is 5.59 (6)°. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, pairs of mol­ecules are linked into centrosymmetric R22(10) dimers by pairs of O—H⋯O hydrogen bonds. Aromatic π–π inter­actions are observed between the benzene rings of adjacent dimers [centroid–centroid distance = 3.4808 (7) Å].

Related literature

For the synthesis, structure and properties of Schiff base complexes, see: Lee et al. (2005[Lee, B. Y., Kwon, H. Y., Lee, S. Y., Na, S. J., Han, S. I., Yun, H., Lee, H. & Park, Y. W. (2005). J. Am. Chem. Soc. 127, 3031-3037.]); Sriram et al. (2006[Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.]); Hao (2009[Hao, Y.-M. (2009). Acta Cryst. E65, o2600.]); Bedia et al. (2006[Bedia, K. K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253-1261.]). For related structures, see: Tüfekçi et al. (2009[Tüfekçi, M., Alpaslan, G., Macit, M. & Erdönmez, A. (2009). Acta Cryst. E65, o2143.]); Yazıcı et al. (2010[Yazıcı, S., Albayrak, Ç., Gümrükçüoğlu, İ., Şenel, İ. & Büyükgüngör, O. (2010). Acta Cryst. E66, o93.]).

[Scheme 1]

Experimental

Crystal data

  • C15H15NO2

  • Mr = 241.28

  • Monoclinic, P 21 /c

  • a = 7.7482 (4) Å

  • b = 10.8713 (7) Å

  • c = 15.4742 (7) Å

  • β = 117.380 (3)°

  • V = 1157.42 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 150 K

  • 0.77 × 0.63 × 0.39 mm
Data collection

  • Stoe IPDS II diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.945, Tmax = 0.967

  • 10088 measured reflections

  • 2655 independent reflections

  • 2384 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.05

  • 2655 reflections

  • 167 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1 0.92 (2) 1.77 (2) 2.5793 (16) 145 (2)
O2—H2⋯O1i 0.82 2.13 2.6993 (12) 127
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810002503/ci5022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002503/ci5022Isup2.hkl

checkCIF report


Comment top

Schiff bases are one of the most prevalent and important mixed-donor ligand in coordination chemistry (Lee et al., 2005). Recently, the synthesis, structure and properties of Schiff base complexes have stimulated much more interest for their noteworthy contributions in pharmaceutical and medicinal activities (Sriram et al., 2006; Hao, 2009; Bedia et al., 2006).

The molecule of the title compound exists in a zwitterionic form, with a strong intramolecular N1—H1···O1 hydrogen bond (Fig. 1). The molecule adopts an E configuration with respect to the amine C═N bond with a C10—C9—N1—C1 torsion angle of 176.29 (10)°. The dihedral angle between the two benzene rings is 5.59 (6)°. The C15—O1 [1.2885 (14) Å], C9—N1 [1.3122 (15) Å] and C9—C10 [1.4071 (16) Å] bond lengths are consistent with corresponding values reported for related zwitterionic compounds (Tüfekçi et al., 2009; Yazıcı et al., 2010).

The crystal packing is stabilized by intermolecular O—H···O hydrogen bonds (Table 1) which link the molecules to form dimers. In addition, π–π interactions are observed between C1–C6 (at x,y,z) and C10–C15 (at 1-x,1-y,1-z) benzene rings [centroid-to-centroid distance = 3.4808 (7) Å].

Related literature top

For the synthesis, structure and properties of Schiff base complexes, see: Lee et al. (2005); Sriram et al. (2006); Hao (2009); Bedia et al. (2006). For related structures, see: Tüfekçi et al. (2009); Yazıcı et al. (2010).

Experimental top

A mixture of 2,3-dihydroxybenzaldehyde (0.5 g, 3.6 mmol) in ethanol (20 ml) and 2-ethylaniline (0.43 g, 3.6 mmol) in ethanol (20 ml) was stirred for 1 h under reflux. Single crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation (yield 85%, m.p. 406-407 K).

Refinement top

Atom H1 was located in a difference map and refined freely. The remaining H atoms were placed in calculated positions and constrained to ride on their parents atoms, with C–H = 0.93-0.97 Å , O–H = 0.82 Å, N–H = 0.92 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O,Cmethyl).

Structure description top

Schiff bases are one of the most prevalent and important mixed-donor ligand in coordination chemistry (Lee et al., 2005). Recently, the synthesis, structure and properties of Schiff base complexes have stimulated much more interest for their noteworthy contributions in pharmaceutical and medicinal activities (Sriram et al., 2006; Hao, 2009; Bedia et al., 2006).

The molecule of the title compound exists in a zwitterionic form, with a strong intramolecular N1—H1···O1 hydrogen bond (Fig. 1). The molecule adopts an E configuration with respect to the amine C═N bond with a C10—C9—N1—C1 torsion angle of 176.29 (10)°. The dihedral angle between the two benzene rings is 5.59 (6)°. The C15—O1 [1.2885 (14) Å], C9—N1 [1.3122 (15) Å] and C9—C10 [1.4071 (16) Å] bond lengths are consistent with corresponding values reported for related zwitterionic compounds (Tüfekçi et al., 2009; Yazıcı et al., 2010).

The crystal packing is stabilized by intermolecular O—H···O hydrogen bonds (Table 1) which link the molecules to form dimers. In addition, π–π interactions are observed between C1–C6 (at x,y,z) and C10–C15 (at 1-x,1-y,1-z) benzene rings [centroid-to-centroid distance = 3.4808 (7) Å].

For the synthesis, structure and properties of Schiff base complexes, see: Lee et al. (2005); Sriram et al. (2006); Hao (2009); Bedia et al. (2006). For related structures, see: Tüfekçi et al. (2009); Yazıcı et al. (2010).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

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. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines
(E)-2-[(2-Ethylphenyl)iminiomethyl]-6-hydroxyphenolate top
Crystal data top
C15H15NO2F(000) = 512
Mr = 241.28Dx = 1.385 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14793 reflections
a = 7.7482 (4) Åθ = 2.4–28.0°
b = 10.8713 (7) ŵ = 0.09 mm−1
c = 15.4742 (7) ÅT = 150 K
β = 117.380 (3)°Prism, red
V = 1157.42 (11) Å30.77 × 0.63 × 0.39 mm
Z = 4
Data collection top
Stoe IPDS II
diffractometer		2655 independent reflections
Radiation source: fine-focus sealed tube2384 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 6.67 pixels mm-1θmax = 27.5°, θmin = 2.4°
ω scanh = −10→10
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −14→14
Tmin = 0.945, Tmax = 0.967l = −20→20
10088 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0624P)2 + 0.418P]
where P = (Fo2 + 2Fc2)/3
2655 reflections(Δ/σ)max = 0.001
167 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.45 e Å−3
Crystal data top
C15H15NO2V = 1157.42 (11) Å3
Mr = 241.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.7482 (4) ŵ = 0.09 mm−1
b = 10.8713 (7) ÅT = 150 K
c = 15.4742 (7) Å0.77 × 0.63 × 0.39 mm
β = 117.380 (3)°
Data collection top
Stoe IPDS II
diffractometer		2655 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		2384 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.967Rint = 0.047
10088 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.39 e Å−3
2655 reflectionsΔρmin = −0.45 e Å−3
167 parameters
Special details top

Experimental. 196 frames, detector distance = 80 mm The beam size = 0.8 mm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C10.36021 (16)0.72765 (10)0.47504 (8)0.0173 (2)
C20.48396 (17)0.81367 (10)0.54271 (8)0.0183 (2)
C30.40045 (18)0.89865 (11)0.57970 (9)0.0220 (3)
H30.47910.95670.62480.026*
C40.20240 (18)0.89846 (11)0.55063 (9)0.0240 (3)
H40.14970.95580.57640.029*
C50.08307 (17)0.81329 (12)0.48342 (9)0.0232 (3)
H5−0.04980.81370.46390.028*
C60.16097 (17)0.72722 (11)0.44512 (9)0.0208 (3)
H60.08100.66980.39990.025*
C70.69934 (17)0.81261 (11)0.57319 (9)0.0221 (3)
H7A0.71750.83220.51680.026*
H7B0.74750.72970.59330.026*
C80.82267 (19)0.90037 (13)0.65481 (10)0.0300 (3)
H8A0.95640.89270.66870.045*
H8B0.80980.88060.71200.045*
H8C0.77980.98330.63530.045*
C90.35682 (16)0.55612 (10)0.37159 (8)0.0182 (2)
H90.22280.54780.34600.022*
C100.45648 (16)0.47823 (10)0.33700 (8)0.0179 (2)
C110.34923 (17)0.39280 (11)0.26133 (9)0.0206 (3)
H110.21510.38720.23670.025*
C120.44263 (18)0.31928 (11)0.22495 (9)0.0231 (3)
H120.37250.26340.17570.028*
C130.64667 (18)0.32805 (11)0.26231 (9)0.0225 (3)
H130.70880.27820.23630.027*
C140.75465 (17)0.40778 (11)0.33558 (8)0.0195 (2)
C150.66399 (16)0.48648 (10)0.37727 (8)0.0176 (2)
N10.44559 (14)0.64003 (9)0.43849 (7)0.0171 (2)
O10.76679 (12)0.56081 (8)0.44695 (6)0.0214 (2)
O20.95018 (12)0.41463 (8)0.36831 (7)0.0246 (2)
H20.99640.46580.41200.037*
H10.578 (3)0.6363 (18)0.4597 (13)0.042 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0190 (5)0.0158 (5)0.0176 (5)0.0033 (4)0.0090 (4)0.0031 (4)
C20.0184 (5)0.0182 (5)0.0183 (5)0.0016 (4)0.0086 (4)0.0026 (4)
C30.0237 (6)0.0198 (6)0.0221 (6)0.0015 (4)0.0102 (5)−0.0015 (4)
C40.0258 (6)0.0234 (6)0.0252 (6)0.0080 (5)0.0138 (5)0.0012 (5)
C50.0173 (5)0.0264 (6)0.0263 (6)0.0049 (4)0.0103 (5)0.0032 (5)
C60.0189 (6)0.0209 (6)0.0211 (6)0.0008 (4)0.0077 (4)0.0008 (4)
C70.0184 (5)0.0241 (6)0.0241 (6)−0.0003 (4)0.0102 (5)−0.0038 (5)
C80.0218 (6)0.0349 (7)0.0311 (7)−0.0053 (5)0.0103 (5)−0.0099 (6)
C90.0166 (5)0.0177 (5)0.0178 (5)0.0004 (4)0.0058 (4)0.0028 (4)
C100.0193 (5)0.0158 (5)0.0165 (5)0.0008 (4)0.0066 (4)0.0016 (4)
C110.0190 (5)0.0193 (5)0.0192 (6)−0.0008 (4)0.0051 (4)0.0007 (4)
C120.0264 (6)0.0192 (5)0.0184 (6)−0.0012 (4)0.0058 (5)−0.0031 (4)
C130.0271 (6)0.0198 (5)0.0201 (6)0.0045 (4)0.0105 (5)−0.0013 (4)
C140.0195 (5)0.0192 (5)0.0186 (5)0.0031 (4)0.0078 (4)0.0026 (4)
C150.0195 (5)0.0149 (5)0.0171 (5)0.0010 (4)0.0072 (4)0.0015 (4)
N10.0161 (5)0.0168 (4)0.0177 (5)0.0017 (3)0.0072 (4)0.0009 (4)
O10.0179 (4)0.0207 (4)0.0221 (4)−0.0007 (3)0.0063 (3)−0.0054 (3)
O20.0190 (4)0.0297 (5)0.0238 (4)0.0026 (3)0.0087 (3)−0.0052 (4)
Geometric parameters (Å, º) top
C1—C61.3929 (16)C8—H8C0.96
C1—C21.4025 (16)C9—N11.3122 (15)
C1—N11.4174 (14)C9—C101.4071 (16)
C2—C31.3930 (16)C9—H90.93
C2—C71.5112 (16)C10—C111.4245 (16)
C3—C41.3864 (17)C10—C151.4352 (15)
C3—H30.93C11—C121.3617 (17)
C4—C51.3818 (18)C11—H110.93
C4—H40.93C12—C131.4149 (17)
C5—C61.3857 (17)C12—H120.93
C5—H50.93C13—C141.3654 (17)
C6—H60.93C13—H130.93
C7—C81.5194 (17)C14—O21.3607 (14)
C7—H7A0.97C14—C151.4346 (16)
C7—H7B0.97C15—O11.2885 (14)
C8—H8A0.96N1—H10.924 (18)
C8—H8B0.96O2—H20.82
C6—C1—C2121.54 (10)H8A—C8—H8C109.5
C6—C1—N1120.96 (10)H8B—C8—H8C109.5
C2—C1—N1117.50 (10)N1—C9—C10122.56 (10)
C3—C2—C1117.50 (11)N1—C9—H9118.7
C3—C2—C7122.13 (11)C10—C9—H9118.7
C1—C2—C7120.37 (10)C9—C10—C11119.36 (10)
C4—C3—C2121.31 (11)C9—C10—C15119.90 (10)
C4—C3—H3119.3C11—C10—C15120.74 (10)
C2—C3—H3119.3C12—C11—C10120.16 (11)
C5—C4—C3120.19 (11)C12—C11—H11119.9
C5—C4—H4119.9C10—C11—H11119.9
C3—C4—H4119.9C11—C12—C13119.87 (11)
C4—C5—C6120.14 (11)C11—C12—H12120.1
C4—C5—H5119.9C13—C12—H12120.1
C6—C5—H5119.9C14—C13—C12121.66 (11)
C5—C6—C1119.32 (11)C14—C13—H13119.2
C5—C6—H6120.3C12—C13—H13119.2
C1—C6—H6120.3O2—C14—C13119.73 (11)
C2—C7—C8115.90 (10)O2—C14—C15119.44 (10)
C2—C7—H7A108.3C13—C14—C15120.81 (11)
C8—C7—H7A108.3O1—C15—C14120.55 (10)
C2—C7—H7B108.3O1—C15—C10122.71 (10)
C8—C7—H7B108.3C14—C15—C10116.74 (10)
H7A—C7—H7B107.4C9—N1—C1127.62 (10)
C7—C8—H8A109.5C9—N1—H1110.1 (12)
C7—C8—H8B109.5C1—N1—H1122.3 (12)
H8A—C8—H8B109.5C14—O2—H2109.5
C7—C8—H8C109.5
C6—C1—C2—C30.44 (17)C15—C10—C11—C12−1.24 (17)
N1—C1—C2—C3−179.08 (10)C10—C11—C12—C13−0.15 (18)
C6—C1—C2—C7−179.48 (11)C11—C12—C13—C140.92 (19)
N1—C1—C2—C70.99 (16)C12—C13—C14—O2−178.98 (11)
C1—C2—C3—C4−0.13 (18)C12—C13—C14—C15−0.28 (18)
C7—C2—C3—C4179.79 (11)O2—C14—C15—O1−1.89 (17)
C2—C3—C4—C5−0.24 (19)C13—C14—C15—O1179.41 (11)
C3—C4—C5—C60.32 (19)O2—C14—C15—C10177.64 (10)
C4—C5—C6—C1−0.02 (18)C13—C14—C15—C10−1.06 (16)
C2—C1—C6—C5−0.37 (17)C9—C10—C15—O12.05 (17)
N1—C1—C6—C5179.14 (10)C11—C10—C15—O1−178.67 (10)
C3—C2—C7—C86.54 (17)C9—C10—C15—C14−177.46 (10)
C1—C2—C7—C8−173.55 (11)C11—C10—C15—C141.81 (16)
N1—C9—C10—C11−177.37 (10)C10—C9—N1—C1176.29 (10)
N1—C9—C10—C151.91 (17)C6—C1—N1—C94.29 (18)
C9—C10—C11—C12178.03 (11)C2—C1—N1—C9−176.19 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.92 (2)1.77 (2)2.5793 (16)145 (2)
O2—H2···O1i0.822.132.6993 (12)127
Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC15H15NO2
Mr241.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)7.7482 (4), 10.8713 (7), 15.4742 (7)
β (°) 117.380 (3)
V (Å3)1157.42 (11)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.77 × 0.63 × 0.39
Data collection
DiffractometerStoe IPDS II
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.945, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections		10088, 2655, 2384
Rint0.047
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.05
No. of reflections2655
No. of parameters167
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.39, −0.45

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.92 (2)1.77 (2)2.5793 (16)145 (2)
O2—H2···O1i0.822.132.6993 (12)127
Symmetry code: (i) −x+2, −y+1, −z+1.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o449
https://doi.org/10.1107/S1600536810002503
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