organic compounds
Z)-3-benzyloxy-6-[(2-hydroxyanilino)methylidene]cyclohexa-2,4-dien-1-one
of (aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, Algeria
*Correspondence e-mail: nitov2013@hotmail.fr
In the title compound, C20H17NO3, the methylidenecyclohexa-2,4-dienone moiety is approximately planar [maximum deviation = 0.0615 (10) Å] and is oriented at diherdral angles of 69.60 (7) and 1.69 (9)° to the phenyl and hydroxybenzene rings, respectively. The amino group links with the carbonyl O atom via an intramolecular N—H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, the molecules are linked by O—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯π interactions, forming a three-dimensional supramolecular architecture.
Keywords: crystal structure; pharmaceutical applications; industrial applications; azomethines; hydrophilicity; drug properties; hydrogen bonding; C—H⋯π interactions.
CCDC reference: 1033206
1. Related literature
For pharmaceutical and industrial applications of ). For the effect of hydrophilicity on drug properties, see: Lin & Lu (1997).
see: Prakash & Adhikari (20112. Experimental
2.1. Crystal data
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2.2. Data collection
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT; 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 1033206
10.1107/S1600536814024568/xu5827sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814024568/xu5827Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814024568/xu5827Isup3.cml
A mixture of 2-aminophenol (1 mmol), and 4-(benzyloxy)-2-hydroxybenzaldehyde (1 mmol) was added and heated to form a clear solution. To this a few drops of conc. HCL was added as a catalyst and refluxed for 4 h. After cooling the solution, After stirring at 80°C for 45 min the formed precipitate was filtered off and washed with ice ether and ethyl acetate to give pure Schiff base as an Orange solid in an 35% yield. The crude product was dissolved in ethyl acetate and two spoons of
were added. the mixture was filtered and the product was crystallized from an ethyl acetate solution.All hydrogen atoms were fixed geometrically and treated as riding with C—H = 0.93–0.97 Å and N—H = 0.86 Å, Uiso(H) = 1.2Ueq(C,N).
Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).View of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Partial view along the b axis of the crystal packing of the title compound, showing the hydrogen bonds as dashed lines (see Table 1 for details). |
C20H17NO3 | Z = 4 |
Mr = 319.21 | F(000) = 672 |
Monoclinic, P21/c | Dx = 1.286 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 12.890 (5) Å | µ = 0.09 mm−1 |
b = 8.343 (5) Å | T = 293 K |
c = 19.908 (5) Å | Block, orange |
β = 129.616 (15)° | 0.03 × 0.02 × 0.01 mm |
V = 1649.2 (12) Å3 |
Bruker APEXII CCD diffractometer | 2019 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 25.1°, θmin = 2.7° |
phi and ω scans | h = −15→14 |
10996 measured reflections | k = −9→9 |
2845 independent reflections | l = −23→22 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.1282P] where P = (Fo2 + 2Fc2)/3 |
2845 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C20H17NO3 | V = 1649.2 (12) Å3 |
Mr = 319.21 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.890 (5) Å | µ = 0.09 mm−1 |
b = 8.343 (5) Å | T = 293 K |
c = 19.908 (5) Å | 0.03 × 0.02 × 0.01 mm |
β = 129.616 (15)° |
Bruker APEXII CCD diffractometer | 2019 reflections with I > 2σ(I) |
10996 measured reflections | Rint = 0.026 |
2845 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.13 e Å−3 |
2845 reflections | Δρmin = −0.18 e Å−3 |
217 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 e.s.d.'s 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 | 0.08170 (10) | −0.46817 (14) | 0.29489 (8) | 0.0510 (4) | |
O2 | 0.13038 (10) | −0.09947 (13) | 0.24415 (7) | 0.0445 (4) | |
O3 | 0.29081 (10) | 0.34273 (14) | 0.18059 (7) | 0.0497 (4) | |
N1 | 0.29329 (12) | −0.33924 (15) | 0.32821 (8) | 0.0349 (4) | |
C1 | 0.20033 (17) | −0.7115 (2) | 0.37366 (11) | 0.0465 (6) | |
C2 | 0.19333 (15) | −0.56093 (19) | 0.34232 (10) | 0.0368 (5) | |
C3 | 0.30842 (14) | −0.49543 (19) | 0.36000 (9) | 0.0327 (5) | |
C4 | 0.42609 (15) | −0.5832 (2) | 0.40563 (10) | 0.0418 (6) | |
C5 | 0.43154 (17) | −0.7336 (2) | 0.43620 (11) | 0.0469 (6) | |
C6 | 0.31962 (18) | −0.7966 (2) | 0.42096 (12) | 0.0499 (7) | |
C7 | 0.38268 (14) | −0.2492 (2) | 0.33441 (10) | 0.0359 (5) | |
C8 | 0.35558 (14) | −0.09631 (19) | 0.29854 (10) | 0.0334 (5) | |
C9 | 0.22447 (14) | −0.02458 (18) | 0.25091 (10) | 0.0333 (5) | |
C10 | 0.20234 (14) | 0.12504 (19) | 0.21107 (10) | 0.0364 (5) | |
C11 | 0.30365 (15) | 0.2003 (2) | 0.21852 (10) | 0.0373 (5) | |
C12 | 0.43407 (15) | 0.1325 (2) | 0.26765 (11) | 0.0429 (6) | |
C13 | 0.45764 (14) | −0.0112 (2) | 0.30572 (10) | 0.0391 (6) | |
C14 | 0.15921 (15) | 0.4129 (2) | 0.12213 (11) | 0.0459 (6) | |
C15 | 0.16707 (14) | 0.5500 (2) | 0.07665 (10) | 0.0413 (6) | |
C16 | 0.1628 (2) | 0.7053 (2) | 0.09686 (12) | 0.0615 (8) | |
C17 | 0.1699 (2) | 0.8323 (3) | 0.05546 (15) | 0.0794 (9) | |
C18 | 0.1801 (2) | 0.8034 (3) | −0.00759 (15) | 0.0718 (9) | |
C19 | 0.18242 (19) | 0.6501 (3) | −0.02999 (14) | 0.0675 (9) | |
C20 | 0.17652 (16) | 0.5232 (2) | 0.01228 (12) | 0.0550 (7) | |
H1 | 0.12478 | −0.75575 | 0.36294 | 0.0558* | |
H01 | 0.20956 | −0.28801 | 0.29816 | 0.0419* | |
H3 | 0.01953 | −0.51531 | 0.28781 | 0.0765* | |
H4 | 0.50165 | −0.54071 | 0.41573 | 0.0501* | |
H5 | 0.51090 | −0.79264 | 0.46715 | 0.0562* | |
H6 | 0.32429 | −0.89733 | 0.44272 | 0.0599* | |
H7 | 0.46914 | −0.28998 | 0.36450 | 0.0430* | |
H10 | 0.11811 | 0.17324 | 0.17938 | 0.0437* | |
H12 | 0.50254 | 0.18660 | 0.27351 | 0.0515* | |
H13 | 0.54313 | −0.05599 | 0.33761 | 0.0469* | |
H14A | 0.09445 | 0.33409 | 0.07991 | 0.0551* | |
H14B | 0.13102 | 0.45110 | 0.15431 | 0.0551* | |
H16 | 0.15485 | 0.72580 | 0.13934 | 0.0738* | |
H17 | 0.16786 | 0.93702 | 0.07052 | 0.0953* | |
H18 | 0.18538 | 0.88871 | −0.03536 | 0.0861* | |
H19 | 0.18798 | 0.63063 | −0.07361 | 0.0811* | |
H20 | 0.17896 | 0.41865 | −0.00285 | 0.0660* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0330 (6) | 0.0491 (8) | 0.0727 (8) | 0.0009 (5) | 0.0345 (6) | 0.0098 (7) |
O2 | 0.0309 (6) | 0.0414 (7) | 0.0679 (8) | 0.0004 (5) | 0.0346 (6) | 0.0052 (6) |
O3 | 0.0290 (6) | 0.0565 (8) | 0.0542 (8) | 0.0006 (5) | 0.0221 (6) | 0.0197 (6) |
N1 | 0.0274 (7) | 0.0368 (8) | 0.0406 (8) | 0.0005 (6) | 0.0217 (6) | 0.0000 (6) |
C1 | 0.0482 (10) | 0.0438 (11) | 0.0555 (11) | −0.0055 (9) | 0.0368 (9) | −0.0001 (9) |
C2 | 0.0342 (9) | 0.0397 (10) | 0.0399 (9) | 0.0004 (8) | 0.0252 (8) | −0.0017 (8) |
C3 | 0.0319 (8) | 0.0343 (10) | 0.0322 (9) | −0.0013 (7) | 0.0206 (7) | −0.0037 (7) |
C4 | 0.0333 (9) | 0.0445 (11) | 0.0432 (10) | 0.0003 (8) | 0.0224 (8) | −0.0027 (9) |
C5 | 0.0432 (10) | 0.0440 (11) | 0.0450 (10) | 0.0104 (8) | 0.0242 (9) | 0.0048 (9) |
C6 | 0.0596 (12) | 0.0405 (11) | 0.0516 (11) | 0.0026 (9) | 0.0364 (10) | 0.0060 (9) |
C7 | 0.0278 (8) | 0.0434 (11) | 0.0375 (9) | 0.0000 (7) | 0.0213 (7) | −0.0039 (8) |
C8 | 0.0273 (8) | 0.0374 (10) | 0.0363 (9) | −0.0027 (7) | 0.0207 (7) | −0.0038 (8) |
C9 | 0.0276 (8) | 0.0360 (10) | 0.0404 (9) | −0.0048 (7) | 0.0236 (7) | −0.0071 (8) |
C10 | 0.0248 (8) | 0.0411 (10) | 0.0409 (10) | 0.0020 (7) | 0.0198 (7) | 0.0014 (8) |
C11 | 0.0303 (8) | 0.0431 (10) | 0.0368 (9) | −0.0040 (7) | 0.0206 (7) | 0.0023 (8) |
C12 | 0.0282 (9) | 0.0507 (12) | 0.0500 (11) | −0.0048 (8) | 0.0250 (8) | 0.0036 (9) |
C13 | 0.0246 (8) | 0.0464 (11) | 0.0449 (10) | 0.0011 (7) | 0.0215 (7) | 0.0017 (9) |
C14 | 0.0306 (9) | 0.0520 (11) | 0.0459 (10) | 0.0006 (8) | 0.0201 (8) | 0.0089 (9) |
C15 | 0.0266 (8) | 0.0496 (12) | 0.0345 (9) | −0.0029 (8) | 0.0134 (7) | 0.0049 (8) |
C16 | 0.0778 (14) | 0.0555 (14) | 0.0382 (11) | −0.0166 (11) | 0.0309 (10) | −0.0072 (10) |
C17 | 0.1057 (18) | 0.0477 (14) | 0.0607 (15) | −0.0198 (12) | 0.0418 (14) | −0.0049 (12) |
C18 | 0.0623 (13) | 0.0730 (17) | 0.0628 (15) | −0.0103 (12) | 0.0318 (12) | 0.0223 (13) |
C19 | 0.0553 (12) | 0.0960 (19) | 0.0647 (14) | 0.0165 (12) | 0.0445 (11) | 0.0287 (14) |
C20 | 0.0482 (11) | 0.0627 (13) | 0.0620 (12) | 0.0134 (9) | 0.0388 (10) | 0.0119 (11) |
O1—C2 | 1.352 (2) | C15—C20 | 1.381 (3) |
O2—C9 | 1.293 (3) | C15—C16 | 1.368 (3) |
O3—C11 | 1.360 (2) | C16—C17 | 1.381 (3) |
O3—C14 | 1.434 (3) | C17—C18 | 1.364 (4) |
O1—H3 | 0.8200 | C18—C19 | 1.361 (4) |
N1—C7 | 1.314 (3) | C19—C20 | 1.384 (3) |
N1—C3 | 1.407 (2) | C1—H1 | 0.9300 |
N1—H01 | 0.9400 | C4—H4 | 0.9300 |
C1—C6 | 1.382 (3) | C5—H5 | 0.9300 |
C1—C2 | 1.380 (3) | C6—H6 | 0.9300 |
C2—C3 | 1.399 (3) | C7—H7 | 0.9300 |
C3—C4 | 1.380 (3) | C10—H10 | 0.9300 |
C4—C5 | 1.377 (3) | C12—H12 | 0.9300 |
C5—C6 | 1.375 (4) | C13—H13 | 0.9300 |
C7—C8 | 1.393 (2) | C14—H14A | 0.9700 |
C8—C13 | 1.420 (3) | C14—H14B | 0.9700 |
C8—C9 | 1.439 (3) | C16—H16 | 0.9300 |
C9—C10 | 1.407 (2) | C17—H17 | 0.9300 |
C10—C11 | 1.369 (3) | C18—H18 | 0.9300 |
C11—C12 | 1.416 (3) | C19—H19 | 0.9300 |
C12—C13 | 1.346 (2) | C20—H20 | 0.9300 |
C14—C15 | 1.502 (3) | ||
O1···N1 | 2.594 (3) | C10···H14A | 2.6800 |
O1···O2i | 2.563 (3) | C14···H10 | 2.5200 |
O2···C2ii | 3.364 (3) | C15···H13iii | 3.0900 |
O2···N1 | 2.594 (2) | C15···H14Aix | 2.9300 |
O2···O1ii | 2.563 (3) | C16···H14Aix | 2.9300 |
O3···C13iii | 3.309 (3) | C17···H14Aix | 3.0100 |
O1···H18iv | 2.8100 | C18···H14Aix | 3.0700 |
O1···H01 | 2.2000 | C19···H6x | 3.0600 |
O2···H16v | 2.7200 | C19···H14Aix | 3.0400 |
O2···H1ii | 2.8500 | C20···H13iii | 2.9400 |
O2···H3ii | 1.7500 | C20···H14Aix | 2.9700 |
O2···H01 | 1.8100 | H1···H3 | 2.3500 |
O3···H13iii | 2.5300 | H1···O2i | 2.8500 |
N1···O1 | 2.594 (3) | H01···O1 | 2.2000 |
N1···O2 | 2.594 (2) | H01···O2 | 1.8100 |
C1···C10v | 3.528 (3) | H01···C9 | 2.4500 |
C2···O2i | 3.364 (3) | H3···H1 | 2.3500 |
C4···C4vi | 3.248 (3) | H3···O2i | 1.7500 |
C4···C11v | 3.483 (3) | H3···C9i | 2.7200 |
C4···C5vi | 3.592 (3) | H4···C7 | 2.7800 |
C5···C11v | 3.563 (3) | H4···H7 | 2.2500 |
C5···C4vi | 3.592 (3) | H6···C19xi | 3.0600 |
C5···C7vi | 3.559 (3) | H6···H19xi | 2.5000 |
C5···C12v | 3.556 (4) | H7···C4 | 2.7500 |
C6···C10v | 3.481 (3) | H7···H4 | 2.2500 |
C6···C9v | 3.360 (3) | H7···H13 | 2.3800 |
C7···C5vi | 3.559 (3) | H10···C14 | 2.5200 |
C8···C16v | 3.509 (3) | H10···H14A | 2.2500 |
C9···C16v | 3.465 (3) | H10···H14B | 2.4000 |
C9···C6vii | 3.360 (3) | H13···H7 | 2.3800 |
C10···C1vii | 3.528 (3) | H13···O3viii | 2.5300 |
C10···C6vii | 3.481 (3) | H13···C15viii | 3.0900 |
C11···C4vii | 3.483 (3) | H13···C20viii | 2.9400 |
C11···C5vii | 3.563 (3) | H14A···C10 | 2.6800 |
C12···C5vii | 3.556 (4) | H14A···H10 | 2.2500 |
C13···O3viii | 3.309 (3) | H14A···H20 | 2.5900 |
C14···C20ix | 3.377 (4) | H14A···C15ix | 2.9300 |
C14···C19ix | 3.568 (4) | H14A···C16ix | 2.9300 |
C14···C15ix | 3.496 (3) | H14A···C17ix | 3.0100 |
C15···C14ix | 3.496 (3) | H14A···C18ix | 3.0700 |
C15···C15ix | 3.435 (3) | H14A···C19ix | 3.0400 |
C16···C9vii | 3.465 (3) | H14A···C20ix | 2.9700 |
C16···C8vii | 3.509 (3) | H14B···C10 | 2.8600 |
C19···C14ix | 3.568 (4) | H14B···H10 | 2.4000 |
C20···C14ix | 3.377 (4) | H14B···H16 | 2.3600 |
C2···H18iv | 2.8800 | H16···O2vii | 2.7200 |
C4···H7 | 2.7500 | H16···C7vii | 3.0300 |
C7···H4 | 2.7800 | H16···C8vii | 2.9100 |
C7···H16v | 3.0300 | H16···C9vii | 2.7400 |
C8···H16v | 2.9100 | H16···H14B | 2.3600 |
C9···H3ii | 2.7200 | H17···C10vii | 2.9800 |
C9···H16v | 2.7400 | H18···O1xii | 2.8100 |
C9···H01 | 2.4500 | H18···C2xii | 2.8800 |
C10···H17v | 2.9800 | H19···H6x | 2.5000 |
C10···H14B | 2.8600 | H20···H14A | 2.5900 |
C11—O3—C14 | 117.99 (16) | C17—C18—C19 | 120.2 (2) |
C2—O1—H3 | 109.00 | C18—C19—C20 | 119.9 (2) |
C3—N1—C7 | 128.73 (17) | C15—C20—C19 | 120.79 (18) |
C7—N1—H01 | 112.00 | C2—C1—H1 | 120.00 |
C3—N1—H01 | 119.00 | C6—C1—H1 | 120.00 |
C2—C1—C6 | 120.0 (2) | C3—C4—H4 | 120.00 |
C1—C2—C3 | 119.26 (18) | C5—C4—H4 | 120.00 |
O1—C2—C3 | 115.96 (15) | C4—C5—H5 | 120.00 |
O1—C2—C1 | 124.8 (2) | C6—C5—H5 | 120.00 |
C2—C3—C4 | 120.16 (16) | C1—C6—H6 | 120.00 |
N1—C3—C4 | 124.50 (18) | C5—C6—H6 | 120.00 |
N1—C3—C2 | 115.34 (16) | N1—C7—H7 | 118.00 |
C3—C4—C5 | 120.0 (2) | C8—C7—H7 | 118.00 |
C4—C5—C6 | 120.0 (2) | C9—C10—H10 | 120.00 |
C1—C6—C5 | 120.60 (17) | C11—C10—H10 | 120.00 |
N1—C7—C8 | 123.86 (18) | C11—C12—H12 | 120.00 |
C9—C8—C13 | 118.82 (15) | C13—C12—H12 | 120.00 |
C7—C8—C9 | 121.60 (18) | C8—C13—H13 | 119.00 |
C7—C8—C13 | 119.54 (18) | C12—C13—H13 | 119.00 |
O2—C9—C8 | 119.83 (14) | O3—C14—H14A | 110.00 |
O2—C9—C10 | 122.04 (17) | O3—C14—H14B | 110.00 |
C8—C9—C10 | 118.12 (18) | C15—C14—H14A | 110.00 |
C9—C10—C11 | 120.61 (18) | C15—C14—H14B | 110.00 |
C10—C11—C12 | 121.45 (16) | H14A—C14—H14B | 108.00 |
O3—C11—C12 | 113.76 (18) | C15—C16—H16 | 119.00 |
O3—C11—C10 | 124.78 (18) | C17—C16—H16 | 119.00 |
C11—C12—C13 | 119.2 (2) | C16—C17—H17 | 120.00 |
C8—C13—C12 | 121.81 (19) | C18—C17—H17 | 120.00 |
O3—C14—C15 | 107.49 (17) | C17—C18—H18 | 120.00 |
C14—C15—C16 | 120.87 (18) | C19—C18—H18 | 120.00 |
C14—C15—C20 | 121.07 (16) | C18—C19—H19 | 120.00 |
C16—C15—C20 | 118.05 (18) | C20—C19—H19 | 120.00 |
C15—C16—C17 | 121.4 (2) | C15—C20—H20 | 120.00 |
C16—C17—C18 | 119.7 (2) | C19—C20—H20 | 120.00 |
C14—O3—C11—C10 | −6.0 (2) | C13—C8—C9—O2 | −179.46 (15) |
C14—O3—C11—C12 | 173.65 (15) | C13—C8—C9—C10 | 2.1 (2) |
C11—O3—C14—C15 | −169.43 (14) | C7—C8—C13—C12 | 175.87 (16) |
C7—N1—C3—C2 | −179.48 (16) | C9—C8—C13—C12 | −1.5 (2) |
C7—N1—C3—C4 | 0.4 (3) | O2—C9—C10—C11 | −179.13 (15) |
C3—N1—C7—C8 | 178.54 (16) | C8—C9—C10—C11 | −0.7 (2) |
C6—C1—C2—O1 | 179.47 (17) | C9—C10—C11—O3 | 178.27 (15) |
C6—C1—C2—C3 | −0.8 (3) | C9—C10—C11—C12 | −1.3 (3) |
C2—C1—C6—C5 | −0.9 (3) | O3—C11—C12—C13 | −177.70 (15) |
O1—C2—C3—N1 | 1.9 (2) | C10—C11—C12—C13 | 1.9 (3) |
O1—C2—C3—C4 | −177.97 (15) | C11—C12—C13—C8 | −0.5 (3) |
C1—C2—C3—N1 | −177.80 (15) | O3—C14—C15—C16 | −107.2 (2) |
C1—C2—C3—C4 | 2.3 (2) | O3—C14—C15—C20 | 73.9 (2) |
N1—C3—C4—C5 | 178.08 (15) | C14—C15—C16—C17 | −180.0 (2) |
C2—C3—C4—C5 | −2.0 (2) | C20—C15—C16—C17 | −1.1 (3) |
C3—C4—C5—C6 | 0.3 (3) | C14—C15—C20—C19 | 179.4 (2) |
C4—C5—C6—C1 | 1.2 (3) | C16—C15—C20—C19 | 0.4 (3) |
N1—C7—C8—C9 | −0.1 (3) | C15—C16—C17—C18 | 0.6 (4) |
N1—C7—C8—C13 | −177.38 (16) | C16—C17—C18—C19 | 0.4 (4) |
C7—C8—C9—O2 | 3.2 (2) | C17—C18—C19—C20 | −1.0 (4) |
C7—C8—C9—C10 | −175.25 (16) | C18—C19—C20—C15 | 0.6 (4) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y−1/2, z−1/2; (v) x, y−1, z; (vi) −x+1, −y−1, −z+1; (vii) x, y+1, z; (viii) −x+1, y−1/2, −z+1/2; (ix) −x, −y+1, −z; (x) x, −y−3/2, z−3/2; (xi) x, −y−3/2, z−1/2; (xii) x, −y−1/2, z−3/2. |
Cg1 is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H01···O2 | 0.94 | 1.81 | 2.594 (2) | 139 |
O1—H3···O2i | 0.82 | 1.75 | 2.563 (3) | 170 |
C13—H13···O3viii | 0.93 | 2.53 | 3.309 (3) | 141 |
C14—H14A···Cg1ix | 0.97 | 2.66 | 3.406 (3) | 134 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (viii) −x+1, y−1/2, −z+1/2; (ix) −x, −y+1, −z. |
Cg1 is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H01···O2 | 0.94 | 1.81 | 2.594 (2) | 139 |
O1—H3···O2i | 0.82 | 1.75 | 2.563 (3) | 170 |
C13—H13···O3ii | 0.93 | 2.53 | 3.309 (3) | 141 |
C14—H14A···Cg1iii | 0.97 | 2.66 | 3.406 (3) | 134 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, −y+1, −z. |
Acknowledgements
We thank all researchers of the CHEMS Research Unit, University of Constantine 1, Algeria, for their valuable assistance and MESRS (Algeria) for financial support.
References
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Azomethine compounds are extensively incoporated in many pharmaceutical and food industry applications (Prakash & Adhikari, 2011). Elimination of excess drugs from the bloodstream or body is an essential process to protect against potential toxicity. In most cases the more hydrophilic drugs/pharmacophores are the more they are readily excreted by the kidneys in urine (Lin & Lu, 1997). The existence of conjugated double bonds and more hydroxylic groups in bioactive molecules increases not only their hydrophilicity but also the rate of their membrane absorption. Based on such facts we herein report the crystal structure of a potential bioactive hydrophilic azomethine derivative.
A view of the molecular structure of (I) with numbering Scheme is shown in Fig. 1. In the molecule, the methylene-cyclohexa-2,4-dienone moiety is approximately planar [maximum deviation = 0.0615 (10) Å] and its mean plane is oriented with respect to the terminal benzene rings at 69.60 (7) and 1.69 (9)°, respectively. The amino group links with the carbonyl O atom via an intramolecular N—H···O hydrogen bond, forming an S(6) ring motif. In the crystal, the molecules are linked by the intermolecular O—H···O hydrogen bond, weak C—H···O and C—H···π interactions to form the three dimensional supramolecular architecture.