organic compounds
(Z)-4-(2-Hydroxyanilino)pent-3-en-2-one
aLaboratoire d'Electrochimie, d'Ingenierie Moléculaire et de Catalyse Redox, Departement de Génie des Procédés, Faculté de Technologie, Université Ferhat Abbas, Sétif, Algeria, and bInstitut de Chimie de Strasbourg, UMR 7177 CNRS-UdS, Service de Radiocristallographie, 1 rue Blaise Pascal, 67008 Strasbourg Cedex, France
*Correspondence e-mail: s_marouani20012002@yahoo.fr
In the title compound, C11H13NO2, the dihedral angle between the planes defined by the 2-hydroxyphenylamino group and the pent-3-en-2-one mean plane [maximum deviations = 0.0275 (19) and 0.054 (2) Å, respectively] is 31.01 (10)°. There are intramolecular bifurcated N—H⋯(O,O) hydrogen bonds involving the amine NH group and the adjacent carbonyl and hydroxy O atoms. In the crystal, molecules are linked via O—H⋯O hydrogen bonds, forming chains propagating along [100].
Related literature
For transition metal complexes of ); Xiong et al. (2007); Basu et al. (2010). For the biological activity of see: Jarrahpour et al. (2007); El-Masry et al. (2000); Singh & Dash (1988). For the use of as intermidiates in many industrial processes, see: Salavati-Niasari & Nezamoddin Mirsattari (2007); Katsuki (1995); Ahamad et al. (2010); Da Silva et al. (2010); Soltani et al. (2010). For the tautomeric properties and conformations of the title compound, see: Kabak et al. (1998). For the of the title compound, see: Parekh et al. (2007), and for its thermochromic properties, see: Moustakali-Mavridis et al. (1978); Hadjoudis et al. (1987). For hydrogen bonding and graph-set notation, see: Bernstein et al. (1995).
see: Salavati-Niasari (2006Experimental
Crystal data
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Data collection
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Refinement
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Data collection: COLLECT (Nonius, 1998); cell DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; 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) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536812027894/su2455sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027894/su2455Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812027894/su2455Isup3.cml
To a ethanol solution (5 ml) of (0.109 g, 1 mmol) of 2-aminophenol was slowly added a ethanol solution (5 ml) of acetylacetone (0.1 g, 1 mmol). The mixture was refluxed with constant stirring under a nitrogen atmosphere for 5 h. The mixture was removed and allowed to cool to rt and the solvent to evaporate slowly. After 20 days yellow crystals of the title compound were obtained. They were washed with ethanol then with diethyl ether.
The OH and NH H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and refined using a riding model: C—H = 0.95 and 0.98 Å for CH and CH3 H atoms, respectively, with Uiso(H) = k × Ueq(C) where k = 1.5 for methyl H atoms and = 1.2 for other H atoms. In the final cycles of
in the absence of significant effects, the Friedel pairs were merged and Δf " set to zero.Schiff bases have played an important role in the development of coordination chemistry. They have a great capacity for complexation of transition metal (Salavati-Niasari, 2006; Xiong et al., 2007; Basu et al., 2010). A literature survey revealed that this kind of compound possesses diverse biological activities such as antimicrobial (Jarrahpour et al., 2007; El-Masry et al., 2000) and antifungal (Singh & Dash, 1988). They also serve as intermediates in many industrial processes (Salavati-Niasari & Nezamoddin Mirsattari, 2007; Katsuki, 1995) and are used as corrosion inhibitors (Ahamad et al., 2010; Da Silva et al., 2010; Soltani et al., 2010). In order to expand this field of research the title compound, a novel Schiff base derived from a non-aromatic aldehyde, has been synthesized and its
is reported herein.The tautomeric properties and conformations of the title compound were investigated by (Kabak et al., 1998). The enol tautomer form of the crystal of the title compound is established by the present
analysis. The positive of this compound has been studied by (Parekh et al., 2007). The crystal exhibits positive and poor NLO responses, and it is photochromic not thermochromic in the solid state (Moustakali-Mavridis et al., 1978; Hadjoudis et al., 1987).The molecular structure of the title molecule is shown in Fig. 1. It was prepared by the condensation of acetylacetone and 2-aminophenol and crystallized in the
P212121.The molecule is not planar and the dihedral angle between the two planes defined by O1,C1-C6,N1 and O2,C7-C11 is equal to 31.01 (10) °. The small value of bond N1—C7 (1.346 (2) A°) in comparison to bond N1—C6 (1.416 (3) A°) results in a significant change in the bond angle C7—N1—C6 of 130.76 (17)°. The difference in the C—N bond distances is assumed to be due to the presence of the carbonyl group located at the C10 position. Shortening of the C7—N1 bond length and the large value of the C7—N1—C6 bond angle leads to the existence of an N1—H1···O2 intramolecular hydrogen bond (Table 1) with an S(6) ring motif (Bernstein et al., 1995). The second intramolecular N1-H1···O1 hydrogen bond gives an S(5) ring motif.
In the crystal, molecules are linked via O-H···O hydrogen bonds to form chains propagating along [100] - see Table 1 and Fig. 2.
For transition metal complexes of
see: Salavati-Niasari (2006); Xiong et al. (2007); Basu et al. (2010). For the biological activity of see: Jarrahpour et al. (2007); El-Masry et al. (2000); Singh & Dash (1988). For the use of as intermidiates in many industrial processes, see: Salavati-Niasari & Nezamoddin Mirsattari (2007); Katsuki (1995); Ahamad et al. (2010); Da Silva et al. (2010); Soltani et al. (2010). For the tautomeric properties and conformations of the title compound, see: Kabak et al. (1998). For the of the title compound, see: Parekh et al. (2007), and for its thermochromic properties, see: Moustakali-Mavridis et al. (1978); Hadjoudis et al. (1987). For hydrogen bonding and graph-set notation, see: Bernstein et al. (1995).Data collection: COLLECT (Nonius, 1998); cell
DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); 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) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C11H13NO2 | F(000) = 408 |
Mr = 191.22 | Dx = 1.244 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4219 reflections |
a = 8.7826 (4) Å | θ = 1.0–27.5° |
b = 10.3999 (5) Å | µ = 0.09 mm−1 |
c = 11.1827 (3) Å | T = 173 K |
V = 1021.41 (7) Å3 | Prism, yellow |
Z = 4 | 0.50 × 0.30 × 0.20 mm |
Nonius KappaCCD diffractometer | 1260 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.105 |
Graphite monochromator | θmax = 27.5°, θmin = 2.7° |
phi and ω scans | h = −10→11 |
7005 measured reflections | k = −12→13 |
1359 independent reflections | l = −14→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0792P)2 + 0.0946P] where P = (Fo2 + 2Fc2)/3 |
1359 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C11H13NO2 | V = 1021.41 (7) Å3 |
Mr = 191.22 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.7826 (4) Å | µ = 0.09 mm−1 |
b = 10.3999 (5) Å | T = 173 K |
c = 11.1827 (3) Å | 0.50 × 0.30 × 0.20 mm |
Nonius KappaCCD diffractometer | 1260 reflections with I > 2σ(I) |
7005 measured reflections | Rint = 0.105 |
1359 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.22 e Å−3 |
1359 reflections | Δρmin = −0.29 e Å−3 |
137 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.58388 (17) | 0.70724 (15) | 0.03852 (14) | 0.0320 (4) | |
O2 | 0.95582 (17) | 0.68677 (15) | 0.15060 (12) | 0.0331 (4) | |
N1 | 0.69854 (19) | 0.57884 (17) | 0.22040 (14) | 0.0248 (4) | |
C1 | 0.4942 (2) | 0.61181 (19) | 0.08258 (17) | 0.0257 (5) | |
C2 | 0.3527 (2) | 0.5805 (2) | 0.03503 (19) | 0.0322 (6) | |
C3 | 0.2679 (3) | 0.4816 (2) | 0.0850 (2) | 0.0387 (7) | |
C4 | 0.3242 (3) | 0.4126 (2) | 0.1812 (2) | 0.0402 (7) | |
C5 | 0.4665 (3) | 0.4415 (2) | 0.2282 (2) | 0.0349 (6) | |
C6 | 0.5510 (2) | 0.54332 (18) | 0.18138 (17) | 0.0256 (5) | |
C7 | 0.7611 (2) | 0.57778 (19) | 0.33025 (16) | 0.0253 (5) | |
C8 | 0.6698 (3) | 0.5315 (3) | 0.43570 (18) | 0.0392 (7) | |
C9 | 0.9069 (2) | 0.6227 (2) | 0.34810 (17) | 0.0276 (5) | |
C10 | 0.9993 (2) | 0.6778 (2) | 0.25800 (17) | 0.0275 (5) | |
C11 | 1.1530 (3) | 0.7300 (3) | 0.2911 (2) | 0.0400 (7) | |
H1 | 0.542 (3) | 0.738 (3) | −0.032 (3) | 0.044 (7)* | |
H1N | 0.762 (3) | 0.619 (3) | 0.162 (2) | 0.033 (6)* | |
H2 | 0.31400 | 0.62690 | −0.03160 | 0.0390* | |
H3 | 0.17070 | 0.46110 | 0.05310 | 0.0460* | |
H4 | 0.26530 | 0.34520 | 0.21510 | 0.0480* | |
H5 | 0.50630 | 0.39190 | 0.29240 | 0.0420* | |
H8A | 0.56570 | 0.56470 | 0.42990 | 0.0590* | |
H8B | 0.71680 | 0.56240 | 0.50980 | 0.0590* | |
H8C | 0.66760 | 0.43730 | 0.43600 | 0.0590* | |
H9 | 0.94840 | 0.61620 | 0.42630 | 0.0330* | |
H11A | 1.23200 | 0.68290 | 0.24730 | 0.0600* | |
H11B | 1.16920 | 0.71960 | 0.37730 | 0.0600* | |
H11C | 1.15810 | 0.82140 | 0.27030 | 0.0600* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0344 (8) | 0.0336 (8) | 0.0281 (7) | −0.0051 (7) | −0.0054 (6) | 0.0101 (6) |
O2 | 0.0357 (7) | 0.0395 (8) | 0.0241 (7) | −0.0059 (7) | 0.0004 (6) | 0.0062 (6) |
N1 | 0.0271 (8) | 0.0257 (8) | 0.0217 (7) | −0.0021 (7) | 0.0009 (6) | 0.0040 (6) |
C1 | 0.0274 (9) | 0.0234 (9) | 0.0263 (9) | 0.0023 (8) | 0.0021 (8) | 0.0009 (7) |
C2 | 0.0305 (10) | 0.0324 (10) | 0.0336 (10) | 0.0031 (10) | −0.0033 (8) | −0.0031 (9) |
C3 | 0.0308 (10) | 0.0342 (11) | 0.0511 (13) | −0.0023 (10) | −0.0051 (10) | −0.0075 (10) |
C4 | 0.0403 (12) | 0.0300 (11) | 0.0503 (14) | −0.0086 (11) | −0.0004 (10) | 0.0027 (10) |
C5 | 0.0407 (12) | 0.0263 (10) | 0.0377 (11) | −0.0044 (10) | −0.0006 (9) | 0.0057 (8) |
C6 | 0.0271 (9) | 0.0236 (9) | 0.0261 (9) | 0.0004 (8) | −0.0002 (7) | −0.0003 (7) |
C7 | 0.0319 (9) | 0.0236 (8) | 0.0205 (9) | 0.0043 (8) | 0.0006 (7) | 0.0043 (7) |
C8 | 0.0406 (12) | 0.0513 (13) | 0.0258 (10) | −0.0059 (12) | 0.0040 (9) | 0.0093 (10) |
C9 | 0.0324 (10) | 0.0281 (10) | 0.0223 (8) | 0.0029 (9) | −0.0028 (8) | 0.0042 (7) |
C10 | 0.0304 (9) | 0.0250 (9) | 0.0272 (9) | 0.0023 (9) | 0.0004 (7) | −0.0007 (7) |
C11 | 0.0374 (11) | 0.0434 (13) | 0.0393 (11) | −0.0088 (12) | −0.0011 (10) | −0.0005 (10) |
O1—C1 | 1.359 (2) | C9—C10 | 1.415 (3) |
O2—C10 | 1.264 (2) | C10—C11 | 1.501 (3) |
O1—H1 | 0.93 (3) | C2—H2 | 0.9500 |
N1—C6 | 1.416 (2) | C3—H3 | 0.9500 |
N1—C7 | 1.346 (2) | C4—H4 | 0.9500 |
N1—H1N | 0.96 (3) | C5—H5 | 0.9500 |
C1—C2 | 1.390 (3) | C8—H8A | 0.9800 |
C1—C6 | 1.406 (3) | C8—H8B | 0.9800 |
C2—C3 | 1.387 (3) | C8—H8C | 0.9800 |
C3—C4 | 1.385 (3) | C9—H9 | 0.9500 |
C4—C5 | 1.389 (4) | C11—H11A | 0.9800 |
C5—C6 | 1.395 (3) | C11—H11B | 0.9800 |
C7—C8 | 1.505 (3) | C11—H11C | 0.9800 |
C7—C9 | 1.378 (3) | ||
C1—O1—H1 | 109.3 (18) | C3—C2—H2 | 120.00 |
C6—N1—C7 | 130.74 (16) | C2—C3—H3 | 120.00 |
C6—N1—H1N | 115.9 (15) | C4—C3—H3 | 120.00 |
C7—N1—H1N | 112.9 (15) | C3—C4—H4 | 120.00 |
O1—C1—C2 | 123.38 (18) | C5—C4—H4 | 120.00 |
O1—C1—C6 | 116.69 (16) | C4—C5—H5 | 120.00 |
C2—C1—C6 | 119.93 (18) | C6—C5—H5 | 120.00 |
C1—C2—C3 | 120.0 (2) | C7—C8—H8A | 109.00 |
C2—C3—C4 | 120.4 (2) | C7—C8—H8B | 109.00 |
C3—C4—C5 | 120.2 (2) | C7—C8—H8C | 109.00 |
C4—C5—C6 | 120.1 (2) | H8A—C8—H8B | 109.00 |
N1—C6—C1 | 115.76 (16) | H8A—C8—H8C | 110.00 |
N1—C6—C5 | 124.68 (18) | H8B—C8—H8C | 109.00 |
C1—C6—C5 | 119.39 (18) | C7—C9—H9 | 118.00 |
C8—C7—C9 | 119.35 (17) | C10—C9—H9 | 118.00 |
N1—C7—C8 | 120.02 (17) | C10—C11—H11A | 109.00 |
N1—C7—C9 | 120.60 (17) | C10—C11—H11B | 109.00 |
C7—C9—C10 | 124.56 (17) | C10—C11—H11C | 109.00 |
O2—C10—C9 | 122.23 (17) | H11A—C11—H11B | 109.00 |
O2—C10—C11 | 118.64 (18) | H11A—C11—H11C | 110.00 |
C9—C10—C11 | 119.12 (17) | H11B—C11—H11C | 110.00 |
C1—C2—H2 | 120.00 | ||
C6—N1—C7—C9 | −177.06 (19) | C1—C2—C3—C4 | −0.8 (3) |
C7—N1—C6—C1 | 148.6 (2) | C2—C3—C4—C5 | −0.3 (3) |
C7—N1—C6—C5 | −36.2 (3) | C3—C4—C5—C6 | 2.3 (3) |
C6—N1—C7—C8 | 0.8 (3) | C4—C5—C6—N1 | −178.26 (19) |
C6—C1—C2—C3 | −0.1 (3) | C4—C5—C6—C1 | −3.2 (3) |
O1—C1—C6—N1 | −2.5 (3) | N1—C7—C9—C10 | 3.0 (3) |
O1—C1—C6—C5 | −177.92 (18) | C8—C7—C9—C10 | −174.9 (2) |
O1—C1—C2—C3 | 179.93 (18) | C7—C9—C10—O2 | −2.2 (3) |
C2—C1—C6—N1 | 177.60 (17) | C7—C9—C10—C11 | 176.5 (2) |
C2—C1—C6—C5 | 2.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.96 (3) | 2.28 (3) | 2.633 (2) | 100.9 (18) |
N1—H1N···O2 | 0.96 (3) | 1.85 (3) | 2.641 (2) | 139 (2) |
O1—H1···O2i | 0.93 (3) | 1.72 (3) | 2.637 (2) | 172 (3) |
Symmetry code: (i) x−1/2, −y+3/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C11H13NO2 |
Mr | 191.22 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 8.7826 (4), 10.3999 (5), 11.1827 (3) |
V (Å3) | 1021.41 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7005, 1359, 1260 |
Rint | 0.105 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.126, 1.07 |
No. of reflections | 1359 |
No. of parameters | 137 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.29 |
Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.96 (3) | 2.28 (3) | 2.633 (2) | 100.9 (18) |
N1—H1N···O2 | 0.96 (3) | 1.85 (3) | 2.641 (2) | 139 (2) |
O1—H1···O2i | 0.93 (3) | 1.72 (3) | 2.637 (2) | 172 (3) |
Symmetry code: (i) x−1/2, −y+3/2, −z. |
Acknowledgements
The authors would like to thank Professor J. P. Gisselbrecht, Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Strasbourg University, France, for his valuable contributions.
References
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Schiff bases have played an important role in the development of coordination chemistry. They have a great capacity for complexation of transition metal (Salavati-Niasari, 2006; Xiong et al., 2007; Basu et al., 2010). A literature survey revealed that this kind of compound possesses diverse biological activities such as antimicrobial (Jarrahpour et al., 2007; El-Masry et al., 2000) and antifungal (Singh & Dash, 1988). They also serve as intermediates in many industrial processes (Salavati-Niasari & Nezamoddin Mirsattari, 2007; Katsuki, 1995) and are used as corrosion inhibitors (Ahamad et al., 2010; Da Silva et al., 2010; Soltani et al., 2010). In order to expand this field of research the title compound, a novel Schiff base derived from a non-aromatic aldehyde, has been synthesized and its crystal structure is reported herein.
The tautomeric properties and conformations of the title compound were investigated by (Kabak et al., 1998). The enol tautomer form of the crystal of the title compound is established by the present crystal structure analysis. The positive photoconductivity of this compound has been studied by (Parekh et al., 2007). The crystal exhibits positive photoconductivity and poor NLO responses, and it is photochromic not thermochromic in the solid state (Moustakali-Mavridis et al., 1978; Hadjoudis et al., 1987).
The molecular structure of the title molecule is shown in Fig. 1. It was prepared by the condensation of acetylacetone and 2-aminophenol and crystallized in the chiral space group P212121.
The molecule is not planar and the dihedral angle between the two planes defined by O1,C1-C6,N1 and O2,C7-C11 is equal to 31.01 (10) °. The small value of bond N1—C7 (1.346 (2) A°) in comparison to bond N1—C6 (1.416 (3) A°) results in a significant change in the bond angle C7—N1—C6 of 130.76 (17)°. The difference in the C—N bond distances is assumed to be due to the presence of the carbonyl group located at the C10 position. Shortening of the C7—N1 bond length and the large value of the C7—N1—C6 bond angle leads to the existence of an N1—H1···O2 intramolecular hydrogen bond (Table 1) with an S(6) ring motif (Bernstein et al., 1995). The second intramolecular N1-H1···O1 hydrogen bond gives an S(5) ring motif.
In the crystal, molecules are linked via O-H···O hydrogen bonds to form chains propagating along [100] - see Table 1 and Fig. 2.