organic compounds
1-{(Z)-[(2,3-Dihydroxypropyl)amino]methylidene}naphthalen-2(1H)-one
aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt, and eDepartment of Chemistry, Sohag University, 82524 Sohag, Egypt
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the title molecule, C14H15NO3, the ring system is essentially planar, with an r.m.s. deviation of 0.003 Å. The atoms of the ethane-1,2-diol group were refined as disordered over two sets of sites in a ratio of 0.815 (3):0.185 (3). The molecular conformation is stabilized in part by an intramolecular N—H⋯O hydrogen bond, which forms an S(6) ring. In the crystal, molecules are connected by N—H⋯O and O—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100). The network also features weak C—H⋯O hydrogen bonds. Weak C—H⋯π interactions also observed.
Related literature
For pharmaceutical and industrial applications of ). For the effect of hydrophilicity on drug properties, see: Lin & Lu (1997). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).
see: Prakash & Adhikari (2011Experimental
Crystal data
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Refinement
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Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.
Supporting information
https://doi.org/10.1107/S1600536812051070/lh5572sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812051070/lh5572Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812051070/lh5572Isup3.cml
A mixture of 1 mmol (172 mg) 2-hydroxynaphthalene-1-carbaldehyde and 1 mmol (91 mg) 3-aminopropane-1,2-diol in 40 ml ethanol was refluxed and monitored by TLC till completion after 12 h. On cooling of the reaction mixture at room temperature a quantitaive solid product was deposited, filtered and washed with cold ethanol. The crude product was crystallized from ethanol to afford x-ray quality yellow plates (m.p 505 K) in an excellent yield (90.6%) on a slow evaporation at room temperature for 24 h.
All H-atoms were placed in calculated positions and refined by using a riding model with O—H = 0.84 Å, N—H = 0.88 Å, C—H = 0.95 Å (aromatic), 0.99 Å (methylene) and 1.00 Å (methine), and with Uiso(H) = 1.5Ueq(O) for hydroxyl and Uiso(H) = 1.2Ueq(C) for the other atoms. The atoms of the ethane-1,2-diol group are disordered over two sets of sites with occupancies 0.815 (3) and 0.185 (3).
Azomethine compounds, which were named as Schiff's bases in 1864 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 existance 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
of a potential bioactive hydrophilic azomethine derivative.The molecluar structure of the title compound (I) is shown in Fig. 1. The naphthalene ring system (C1—C10) is essentially planar with an r.m.s. deviation of 0.003Å. The bond lengths (Allen et al., 1987) and angles are within normal ranges. In the crystal, molecules are connected by N—H···O and O—H···O hydrogen bonds to form a two-dimensional network parallel to (100). The network is further stabilized by weak C—H···O hydrogen bonds. Weak C—H···π interactions also observed. The O—H groups of the minor component of disorder are not considered in the description of the hydrogen bonding.
For pharmaceutical and industrial applications of
see: Prakash & Adhikari (2011). For the effect of hydrophilicity on drug properties, see: Lin & Lu (1997). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell
CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound with ellipsoids drawn at the 50% probability level. Only the major components of disorder are shown. | |
Fig. 2. Crystal packing of (I) viewed along the b axis. Only the major component of disorder is shown. The hydrogen atoms not involved in the hydrogen bonds have been omitted for clarity. |
C14H15NO3 | F(000) = 520 |
Mr = 245.27 | Dx = 1.377 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 2698 reflections |
a = 23.452 (16) Å | θ = 2.4–27.6° |
b = 5.809 (4) Å | µ = 0.10 mm−1 |
c = 8.739 (6) Å | T = 100 K |
β = 96.445 (7)° | Sheet, yellow |
V = 1183.0 (14) Å3 | 0.27 × 0.14 × 0.01 mm |
Z = 4 |
Rigaku AFC12 (Right) diffractometer | 2650 independent reflections |
Radiation source: Rotating Anode | 2438 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.025 |
profile data from ω–scans | θmax = 27.5°, θmin = 3.5° |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012) | h = −30→30 |
Tmin = 0.974, Tmax = 0.999 | k = −7→7 |
8146 measured reflections | l = −11→9 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0733P)2 + 0.7284P] where P = (Fo2 + 2Fc2)/3 |
2650 reflections | (Δ/σ)max < 0.001 |
184 parameters | Δρmax = 0.67 e Å−3 |
81 restraints | Δρmin = −0.26 e Å−3 |
C14H15NO3 | V = 1183.0 (14) Å3 |
Mr = 245.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 23.452 (16) Å | µ = 0.10 mm−1 |
b = 5.809 (4) Å | T = 100 K |
c = 8.739 (6) Å | 0.27 × 0.14 × 0.01 mm |
β = 96.445 (7)° |
Rigaku AFC12 (Right) diffractometer | 2650 independent reflections |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012) | 2438 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.999 | Rint = 0.025 |
8146 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 81 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.67 e Å−3 |
2650 reflections | Δρmin = −0.26 e Å−3 |
184 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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | Occ. (<1) | |
O1 | 0.30508 (5) | 0.3921 (2) | 0.50408 (16) | 0.0291 (4) | |
O2A | 0.37874 (6) | 1.0576 (3) | 0.45655 (17) | 0.0239 (5) | 0.815 (3) |
O3A | 0.42610 (7) | 1.3999 (3) | 0.6847 (2) | 0.0333 (5) | 0.815 (3) |
N1 | 0.32519 (6) | 0.7647 (3) | 0.65713 (18) | 0.0236 (4) | |
C1 | 0.23196 (7) | 0.5877 (3) | 0.62006 (19) | 0.0194 (5) | |
C2 | 0.25288 (7) | 0.4010 (3) | 0.5343 (2) | 0.0222 (5) | |
C3 | 0.21329 (8) | 0.2228 (3) | 0.4789 (2) | 0.0252 (5) | |
C4 | 0.15774 (8) | 0.2281 (3) | 0.5059 (2) | 0.0249 (5) | |
C5 | 0.13503 (7) | 0.4101 (3) | 0.59118 (19) | 0.0211 (5) | |
C6 | 0.07683 (7) | 0.4098 (3) | 0.6178 (2) | 0.0255 (5) | |
C7 | 0.05463 (7) | 0.5851 (3) | 0.6992 (2) | 0.0277 (5) | |
C8 | 0.09095 (7) | 0.7645 (3) | 0.7572 (2) | 0.0257 (5) | |
C9 | 0.14798 (7) | 0.7680 (3) | 0.7335 (2) | 0.0211 (5) | |
C10 | 0.17201 (7) | 0.5925 (3) | 0.64858 (19) | 0.0191 (5) | |
C11 | 0.27077 (7) | 0.7636 (3) | 0.67604 (19) | 0.0205 (5) | |
C12 | 0.36595 (7) | 0.9416 (3) | 0.7169 (2) | 0.0252 (5) | |
C13A | 0.40851 (18) | 0.9966 (7) | 0.6026 (5) | 0.0238 (8) | 0.815 (3) |
C14A | 0.4511 (3) | 1.1822 (11) | 0.6651 (7) | 0.0321 (10) | 0.815 (3) |
O2B | 0.4314 (4) | 0.8181 (15) | 0.5357 (10) | 0.043 (2)* | 0.185 (3) |
O3B | 0.4728 (6) | 1.153 (3) | 0.8021 (16) | 0.082 (4)* | 0.185 (3) |
C13B | 0.4028 (10) | 1.008 (3) | 0.591 (2) | 0.028 (3)* | 0.185 (3) |
C14B | 0.4461 (17) | 1.192 (5) | 0.653 (3) | 0.032 (3)* | 0.185 (3) |
H4 | 0.13300 | 0.10710 | 0.46700 | 0.0300* | |
H6 | 0.05260 | 0.28710 | 0.57900 | 0.0310* | |
H7 | 0.01530 | 0.58460 | 0.71590 | 0.0330* | |
H8 | 0.07590 | 0.88560 | 0.81380 | 0.0310* | |
H9 | 0.17170 | 0.89070 | 0.77500 | 0.0250* | |
H11 | 0.25630 | 0.88810 | 0.73060 | 0.0250* | |
H12A | 0.38710 | 0.88780 | 0.81480 | 0.0300* | 0.815 (3) |
H12B | 0.34480 | 1.08320 | 0.73870 | 0.0300* | 0.815 (3) |
H13A | 0.43090 | 0.85330 | 0.58790 | 0.0290* | 0.815 (3) |
H14A | 0.47050 | 1.13040 | 0.76570 | 0.0380* | 0.815 (3) |
H14B | 0.48070 | 1.19870 | 0.59380 | 0.0380* | 0.815 (3) |
H1 | 0.33820 | 0.65070 | 0.60460 | 0.0280* | |
H2A | 0.35380 | 1.15760 | 0.46900 | 0.0360* | 0.815 (3) |
H3 | 0.22650 | 0.09830 | 0.42190 | 0.0300* | |
H3A | 0.41610 | 1.40930 | 0.77390 | 0.0500* | 0.815 (3) |
H2B | 0.45860 | 0.77900 | 0.60140 | 0.0640* | 0.185 (3) |
H3B | 0.50210 | 1.07090 | 0.79770 | 0.1230* | 0.185 (3) |
H12C | 0.39200 | 0.87960 | 0.80430 | 0.0300* | 0.185 (3) |
H12D | 0.34520 | 1.07520 | 0.75410 | 0.0300* | 0.185 (3) |
H13B | 0.37720 | 1.07550 | 0.50300 | 0.0330* | 0.185 (3) |
H14C | 0.47610 | 1.20420 | 0.58210 | 0.0390* | 0.185 (3) |
H14D | 0.42600 | 1.34240 | 0.65150 | 0.0390* | 0.185 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0279 (7) | 0.0284 (7) | 0.0328 (8) | 0.0057 (5) | 0.0117 (5) | −0.0005 (5) |
O2A | 0.0279 (8) | 0.0233 (8) | 0.0218 (8) | 0.0035 (6) | 0.0084 (6) | −0.0008 (6) |
O3A | 0.0305 (9) | 0.0319 (9) | 0.0388 (10) | −0.0010 (7) | 0.0096 (7) | −0.0029 (7) |
N1 | 0.0210 (7) | 0.0253 (7) | 0.0253 (8) | −0.0004 (6) | 0.0056 (6) | 0.0002 (6) |
C1 | 0.0219 (8) | 0.0192 (8) | 0.0174 (8) | 0.0022 (6) | 0.0038 (6) | 0.0024 (6) |
C2 | 0.0258 (8) | 0.0234 (8) | 0.0182 (8) | 0.0032 (6) | 0.0054 (6) | 0.0038 (6) |
C3 | 0.0363 (10) | 0.0202 (8) | 0.0193 (9) | 0.0047 (7) | 0.0044 (7) | −0.0015 (6) |
C4 | 0.0339 (9) | 0.0191 (8) | 0.0209 (9) | −0.0028 (7) | −0.0003 (7) | −0.0004 (6) |
C5 | 0.0246 (8) | 0.0212 (8) | 0.0172 (8) | −0.0013 (6) | 0.0008 (6) | 0.0025 (6) |
C6 | 0.0240 (8) | 0.0267 (9) | 0.0252 (9) | −0.0056 (7) | −0.0002 (7) | 0.0005 (7) |
C7 | 0.0208 (8) | 0.0346 (10) | 0.0274 (10) | −0.0030 (7) | 0.0021 (6) | 0.0023 (8) |
C8 | 0.0233 (8) | 0.0271 (9) | 0.0272 (9) | 0.0042 (7) | 0.0046 (7) | −0.0018 (7) |
C9 | 0.0206 (8) | 0.0201 (8) | 0.0222 (8) | −0.0007 (6) | 0.0009 (6) | −0.0013 (6) |
C10 | 0.0212 (8) | 0.0194 (8) | 0.0163 (8) | 0.0006 (6) | 0.0006 (6) | 0.0029 (6) |
C11 | 0.0219 (8) | 0.0215 (8) | 0.0186 (8) | 0.0022 (6) | 0.0040 (6) | 0.0033 (6) |
C12 | 0.0212 (8) | 0.0295 (9) | 0.0251 (9) | −0.0027 (7) | 0.0032 (6) | −0.0002 (7) |
C13A | 0.0181 (13) | 0.0256 (12) | 0.0287 (14) | 0.0030 (9) | 0.0065 (12) | 0.0002 (9) |
C14A | 0.0221 (19) | 0.0333 (15) | 0.0417 (19) | −0.0031 (13) | 0.0076 (12) | −0.0039 (13) |
O1—C2 | 1.282 (2) | C9—C10 | 1.415 (3) |
O2A—C13A | 1.429 (5) | C12—C13B | 1.52 (2) |
O2B—C13B | 1.41 (2) | C12—C13A | 1.523 (5) |
O3A—C14A | 1.412 (7) | C13A—C14A | 1.528 (8) |
O3B—C14B | 1.40 (3) | C13B—C14B | 1.53 (4) |
O2A—H2A | 0.8400 | C3—H3 | 0.9500 |
O2B—H2B | 0.8400 | C4—H4 | 0.9500 |
O3A—H3A | 0.8400 | C6—H6 | 0.9500 |
O3B—H3B | 0.8400 | C7—H7 | 0.9500 |
N1—C12 | 1.460 (3) | C8—H8 | 0.9500 |
N1—C11 | 1.305 (2) | C9—H9 | 0.9500 |
N1—H1 | 0.8800 | C11—H11 | 0.9500 |
C1—C11 | 1.418 (3) | C12—H12C | 0.9900 |
C1—C2 | 1.436 (3) | C12—H12D | 0.9900 |
C1—C10 | 1.455 (3) | C12—H12A | 0.9900 |
C2—C3 | 1.438 (3) | C12—H12B | 0.9900 |
C3—C4 | 1.350 (3) | C13A—H13A | 1.0000 |
C4—C5 | 1.430 (3) | C13B—H13B | 1.0000 |
C5—C10 | 1.424 (3) | C14A—H14A | 0.9900 |
C5—C6 | 1.410 (3) | C14A—H14B | 0.9900 |
C6—C7 | 1.377 (3) | C14B—H14C | 0.9900 |
C7—C8 | 1.404 (3) | C14B—H14D | 0.9900 |
C8—C9 | 1.376 (3) | ||
C13A—O2A—H2A | 109.00 | C3—C4—H4 | 119.00 |
C13B—O2B—H2B | 109.00 | C5—C4—H4 | 119.00 |
C14A—O3A—H3A | 109.00 | C7—C6—H6 | 120.00 |
C14B—O3B—H3B | 109.00 | C5—C6—H6 | 120.00 |
C11—N1—C12 | 124.65 (16) | C6—C7—H7 | 120.00 |
C12—N1—H1 | 118.00 | C8—C7—H7 | 120.00 |
C11—N1—H1 | 118.00 | C9—C8—H8 | 119.00 |
C2—C1—C10 | 119.81 (15) | C7—C8—H8 | 119.00 |
C10—C1—C11 | 121.46 (15) | C10—C9—H9 | 119.00 |
C2—C1—C11 | 118.72 (15) | C8—C9—H9 | 119.00 |
C1—C2—C3 | 118.30 (15) | C1—C11—H11 | 118.00 |
O1—C2—C1 | 121.88 (15) | N1—C11—H11 | 118.00 |
O1—C2—C3 | 119.81 (16) | N1—C12—H12C | 110.00 |
C2—C3—C4 | 121.61 (16) | N1—C12—H12A | 109.00 |
C3—C4—C5 | 122.07 (16) | N1—C12—H12B | 109.00 |
C6—C5—C10 | 120.34 (15) | C13A—C12—H12B | 109.00 |
C4—C5—C6 | 120.60 (16) | H12A—C12—H12B | 108.00 |
C4—C5—C10 | 119.06 (15) | C13B—C12—H12C | 107.00 |
C5—C6—C7 | 120.88 (16) | C13B—C12—H12D | 112.00 |
C6—C7—C8 | 119.08 (15) | H12C—C12—H12D | 108.00 |
C7—C8—C9 | 121.13 (16) | N1—C12—H12D | 110.00 |
C8—C9—C10 | 121.29 (16) | C13A—C12—H12A | 109.00 |
C5—C10—C9 | 117.27 (15) | O2A—C13A—H13A | 108.00 |
C1—C10—C9 | 123.57 (15) | C14A—C13A—H13A | 108.00 |
C1—C10—C5 | 119.15 (15) | C12—C13A—H13A | 108.00 |
N1—C11—C1 | 123.96 (16) | O2B—C13B—H13B | 108.00 |
N1—C12—C13B | 108.8 (7) | C12—C13B—H13B | 108.00 |
N1—C12—C13A | 111.4 (2) | C14B—C13B—H13B | 108.00 |
O2A—C13A—C14A | 112.2 (4) | H14A—C14A—H14B | 108.00 |
O2A—C13A—C12 | 110.3 (3) | C13A—C14A—H14B | 109.00 |
C12—C13A—C14A | 111.3 (4) | O3A—C14A—H14A | 109.00 |
C12—C13B—C14B | 109.2 (15) | O3A—C14A—H14B | 109.00 |
O2B—C13B—C14B | 110 (2) | C13A—C14A—H14A | 109.00 |
O2B—C13B—C12 | 112.4 (12) | O3B—C14B—H14C | 109.00 |
O3A—C14A—C13A | 114.3 (5) | O3B—C14B—H14D | 108.00 |
O3B—C14B—C13B | 115 (2) | C13B—C14B—H14C | 109.00 |
C2—C3—H3 | 119.00 | C13B—C14B—H14D | 108.00 |
C4—C3—H3 | 119.00 | H14C—C14B—H14D | 107.00 |
C12—N1—C11—C1 | −178.57 (16) | C3—C4—C5—C6 | −179.74 (17) |
C11—N1—C12—C13A | −141.4 (2) | C4—C5—C6—C7 | −179.69 (16) |
C10—C1—C2—O1 | 178.69 (16) | C4—C5—C10—C9 | −179.45 (16) |
C11—C1—C2—C3 | 179.61 (16) | C10—C5—C6—C7 | 0.1 (3) |
C10—C1—C2—C3 | 0.0 (2) | C4—C5—C10—C1 | −0.5 (2) |
C11—C1—C2—O1 | −1.7 (3) | C6—C5—C10—C9 | 0.8 (2) |
C11—C1—C10—C5 | −179.31 (16) | C6—C5—C10—C1 | 179.68 (16) |
C11—C1—C10—C9 | −0.5 (3) | C5—C6—C7—C8 | −0.6 (3) |
C2—C1—C11—N1 | −1.4 (3) | C6—C7—C8—C9 | 0.2 (3) |
C10—C1—C11—N1 | 178.20 (16) | C7—C8—C9—C10 | 0.7 (3) |
C2—C1—C10—C5 | 0.3 (2) | C8—C9—C10—C5 | −1.1 (3) |
C2—C1—C10—C9 | 179.17 (16) | C8—C9—C10—C1 | 180.00 (16) |
O1—C2—C3—C4 | −178.79 (17) | N1—C12—C13A—O2A | 54.6 (3) |
C1—C2—C3—C4 | −0.1 (3) | N1—C12—C13A—C14A | 179.9 (3) |
C2—C3—C4—C5 | −0.2 (3) | O2A—C13A—C14A—O3A | 58.8 (5) |
C3—C4—C5—C10 | 0.5 (3) | C12—C13A—C14A—O3A | −65.4 (5) |
Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.88 | 1.87 | 2.560 (3) | 135 |
N1—H1···O3Ai | 0.88 | 2.56 | 3.166 (3) | 127 |
O2A—H2A···O1ii | 0.84 | 1.83 | 2.663 (3) | 175 |
O3A—H3A···O2Aiii | 0.84 | 1.91 | 2.744 (3) | 169 |
C12—H12B···O1iv | 0.99 | 2.60 | 3.174 (3) | 117 |
C4—H4···Cg2v | 0.95 | 2.79 | 3.491 (3) | 132 |
C9—H9···Cg1iv | 0.95 | 2.77 | 3.510 (3) | 135 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x, −y+5/2, z+1/2; (iv) x, −y+3/2, z+1/2; (v) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H15NO3 |
Mr | 245.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 23.452 (16), 5.809 (4), 8.739 (6) |
β (°) | 96.445 (7) |
V (Å3) | 1183.0 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.27 × 0.14 × 0.01 |
Data collection | |
Diffractometer | Rigaku AFC12 (Right) |
Absorption correction | Multi-scan (CrystalClear-SM Expert; Rigaku, 2012) |
Tmin, Tmax | 0.974, 0.999 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8146, 2650, 2438 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.156, 1.11 |
No. of reflections | 2650 |
No. of parameters | 184 |
No. of restraints | 81 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.26 |
Computer programs: CrystalClear-SM Expert (Rigaku, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.88 | 1.87 | 2.560 (3) | 135 |
N1—H1···O3Ai | 0.88 | 2.56 | 3.166 (3) | 127 |
O2A—H2A···O1ii | 0.84 | 1.83 | 2.663 (3) | 175 |
O3A—H3A···O2Aiii | 0.84 | 1.91 | 2.744 (3) | 169 |
C12—H12B···O1iv | 0.99 | 2.60 | 3.174 (3) | 117 |
C4—H4···Cg2v | 0.95 | 2.79 | 3.491 (3) | 132 |
C9—H9···Cg1iv | 0.95 | 2.77 | 3.510 (3) | 135 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x, −y+5/2, z+1/2; (iv) x, −y+3/2, z+1/2; (v) x, −y+1/2, z−1/2. |
Acknowledgements
This work was supported by the Ministry of Higher Education of Egypt under the collaporative PhD program 2012. The EPSRC National Crystallography Service is gratefully acknowledged for the X-ray diffraction measurementss. The authors are thankful to Manchester Metropolitan University, Sohag University and Erciyes Universitry for supporting this study.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Azomethine compounds, which were named as Schiff's bases in 1864 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 existance 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.
The molecluar structure of the title compound (I) is shown in Fig. 1. The naphthalene ring system (C1—C10) is essentially planar with an r.m.s. deviation of 0.003Å. The bond lengths (Allen et al., 1987) and angles are within normal ranges. In the crystal, molecules are connected by N—H···O and O—H···O hydrogen bonds to form a two-dimensional network parallel to (100). The network is further stabilized by weak C—H···O hydrogen bonds. Weak C—H···π interactions also observed. The O—H groups of the minor component of disorder are not considered in the description of the hydrogen bonding.