organic compounds
(E)-2-[(2,4,6-Trimethoxybenzylidene)amino]phenol1
aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, cFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and eDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
*Correspondence e-mail: suchada.c@psu.ac.th
There are two independent molecules in the 16H17NO4, with similar conformations but some differences in their bond angles. Each molecule adopts a trans configuration with respect to the methylidene C=N bond and is twisted with a dihedral angle between the two substituted benzene rings of 80.52 (7)° in one molecule and 83.53 (7)° in the other. All methoxy groups are approximately coplanar with the attached benzene rings, with Cmethyl—O—C—C torsion angles ranging from −6.7 (2) to 5.07 (19)°. In the crystal, independent molecules are linked together by O—H⋯N and O—H⋯O hydrogen bonds and a π–π interaction [centroid–centroid distance of 3.6030 (9) Å], forming a dimer. The dimers are further linked by weak C—H⋯O interactions and another π–π interaction [centroid–centroid distance of 3.9452 (9) Å] into layers lying parallel to the ab plane.
of the title compound, CCCDC reference: 975348
Related literature
For organic bond-length data, see: Allen et al. (1987). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For background to and application of aza-stilbene, see: Cheng et al. (2010); da Silva et al. (2011); Fujita et al. (2012); Lu et al. (2012); Tamizh et al. (2012). For related structures, see: Kaewmanee et al. (2013); Sun et al. (2011).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 975348
https://doi.org/10.1107/S1600536813032996/is5324sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032996/is5324Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813032996/is5324Isup3.cml
The title compound (I) was prepared by mixing 1:1 molar ratio solutions of 2-aminophenol (2.5 mmol, 0.25 g) in toluene (20 ml) and 2,4,6-trimethoxybenzaldehyde (2.5 mmol, 0.50 g) in toluene (20 ml). The reaction mixture was refluxed for around 4 h, yielding white solids , which was collected by filtration, washed with cold ethanol and dried in air. Colorless block-shaped single crystals suitable for X-ray
were recrystalized from methanol by slow evaporation of the solvent at room temperature after several days (m.p. 450–452 K).Hydroxy H atom was located in a difference map and refined freely. The remaining H atoms were fixed geometrically and allowed to ride on their parent atoms, with d(C—H) = 0.95 Å for aromatic and CH, and 0.98 Å for CH3 atoms. The Uiso(H) values were constrained to be 1.5Ueq of the
for water and methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.Aza-stilbenes are a special group of compounds in the Schiff base family which can be synthesized by the reaction of aldehyde with aniline. Aza-stilbenes have been shown to possess potent biological properties such as antibacterial (Tamizh et al., 2012), antioxidant (Cheng et al., 2010; Lu et al., 2012), antifungal (da Silva et al., 2011) and antiproliferative (Fujita et al., 2012) activities. The interesting biological activities of aza-stilbenes have led us to synthesize the title compound (I) and study its antibacterial and antioxidant activities. Our antibacterial assay have shown that (I) possesses moderate to weak antibacterial activity against B. subtilis, S. aureus, P. aeruginosa, S. typhi and S.sonnei with the MIC values in the range of 37.5 to 150 µg/ml. In addition (I) also shows interesting antioxidant activity by DPPH assay with the IC50 value of 0.080 ± 0.0004 µg/ml. We report here the
of the title compound.There are two independent molecules, A and B in the ═N1 double bond [1.2868 (13) and 1.2823 (19) Å for molecules A and B, respectively] and with the torsion angle C8—N1—C7—C1 = -175.58 (13)° for molecule A [177.48 (13)° for molecule B]. The molecule is twisted with the dihedral angle between the two substituted benzene rings being 80.52 (7)° in molecule A and 83.53 (7)° in molecule B. In both molecules, the three methoxy groups are co-planar with their bound benzene rings with the C14—O1—C2—C3 = -3.2 (2)°, C15—O2—C4—C3 = -6.7 (2)° and C16—O3—C6—C5 = -1.5 (2)° in molecule A, and the corresponding values are 5.07 (19), 1.86 (19) and -1.7 (2)° in molecule B. In each molecule, an intramolecular O—H···N hydrogen bond (Fig. 1 and Table 1) generates an S(5) ring motif (Bernstein et al., 1995). The bond distances are in normal ranges (Allen et al., 1987) and are comparable with the related structures (Kaewmanee et al., 2013; Sun et al., 2011).
of the title compound, with similar conformations but some differences in bond angles (Fig. 1). The molecular structure exists in a trans configuration with respect to the methylidene C7In the π–π interactions with Cg1···Cg3 and Cg1···Cg3iv distances of 3.6030 (9) and 3.9452 (9) Å, respectively (Fig. 2) [symmetry code: (iv) = -1 + x, y, z]; Cg1 and Cg3 are the centroids of C1A–C6A and C1B–C6B rings, respectively.]
the molecules are linked into dimers by O—H···N and O—H···O hydrogen bonds (Table 1) which form two R21(6) ring motifs and an R22(10) ring motif (Fig. 2). These dimers are further linked by C—H···O interactions (Table1) into chains along the b direction which arranged into sheets parallel to the ab plane (Fig. 3). There areFor organic bond-length data, see: Allen et al. (1987). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For background to and application of aza-stilbene, see: Cheng et al. (2010); da Silva et al. (2011); Fujita et al. (2012); Lu et al. (2012); Tamizh et al. (2012). For related structures, see: Kaewmanee et al. (2013); Sun et al. (2011).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).Fig. 1. The asymmetric unit of the title compound showing 40% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular hydrogen bonds are drawn as dashed lines. | |
Fig. 2. R21(6) and R21(10) ring motifs and a π–π interaction in the crystal of the title compound. | |
Fig. 3. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are drawn as dashed lines. |
C16H17NO4 | Z = 4 |
Mr = 287.31 | F(000) = 608 |
Triclinic, P1 | Dx = 1.367 Mg m−3 |
Hall symbol: -P 1 | Melting point = 450–452 K |
a = 7.3819 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.7036 (9) Å | Cell parameters from 8129 reflections |
c = 16.4373 (13) Å | θ = 2.5–30.0° |
α = 89.469 (2)° | µ = 0.10 mm−1 |
β = 85.616 (2)° | T = 100 K |
γ = 80.456 (2)° | Block, colourless |
V = 1396.34 (19) Å3 | 0.49 × 0.16 × 0.16 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 8129 independent reflections |
Radiation source: fine-focus sealed tube | 5872 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 2.5° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −16→16 |
Tmin = 0.954, Tmax = 0.985 | l = −23→23 |
29313 measured reflections |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0788P)2 + 0.2397P] where P = (Fo2 + 2Fc2)/3 |
8129 reflections | (Δ/σ)max = 0.001 |
393 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C16H17NO4 | γ = 80.456 (2)° |
Mr = 287.31 | V = 1396.34 (19) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.3819 (6) Å | Mo Kα radiation |
b = 11.7036 (9) Å | µ = 0.10 mm−1 |
c = 16.4373 (13) Å | T = 100 K |
α = 89.469 (2)° | 0.49 × 0.16 × 0.16 mm |
β = 85.616 (2)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 8129 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 5872 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.985 | Rint = 0.048 |
29313 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.41 e Å−3 |
8129 reflections | Δρmin = −0.32 e Å−3 |
393 parameters |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.21415 (16) | 0.83067 (9) | 0.10628 (6) | 0.0249 (2) | |
O2A | 0.19684 (16) | 0.59610 (10) | 0.34830 (7) | 0.0292 (3) | |
O3A | 0.27544 (15) | 0.98999 (9) | 0.36114 (6) | 0.0221 (2) | |
O4A | 0.58266 (14) | 1.21472 (9) | 0.13823 (6) | 0.0210 (2) | |
H1O4 | 0.597 (3) | 1.164 (2) | 0.1779 (13) | 0.043 (6)* | |
N1A | 0.29206 (16) | 1.11109 (10) | 0.21219 (7) | 0.0180 (2) | |
C1A | 0.23748 (19) | 0.91116 (12) | 0.23397 (8) | 0.0174 (3) | |
C2A | 0.21676 (19) | 0.81294 (12) | 0.18822 (8) | 0.0187 (3) | |
C3A | 0.2025 (2) | 0.70672 (12) | 0.22379 (9) | 0.0205 (3) | |
H3AA | 0.1881 | 0.6424 | 0.1915 | 0.025* | |
C4A | 0.20979 (19) | 0.69651 (13) | 0.30743 (9) | 0.0206 (3) | |
C5A | 0.2352 (2) | 0.78998 (13) | 0.35564 (9) | 0.0206 (3) | |
H5AA | 0.2417 | 0.7813 | 0.4129 | 0.025* | |
C6A | 0.25065 (19) | 0.89475 (12) | 0.31884 (8) | 0.0181 (3) | |
C7A | 0.23176 (19) | 1.01974 (12) | 0.19062 (8) | 0.0184 (3) | |
H7AA | 0.1768 | 1.0241 | 0.1400 | 0.022* | |
C8A | 0.2556 (2) | 1.20881 (12) | 0.16002 (8) | 0.0175 (3) | |
C9A | 0.40463 (19) | 1.25893 (12) | 0.12645 (8) | 0.0179 (3) | |
C10A | 0.3708 (2) | 1.35666 (13) | 0.07741 (8) | 0.0212 (3) | |
H10A | 0.4711 | 1.3905 | 0.0541 | 0.025* | |
C11A | 0.1919 (2) | 1.40519 (13) | 0.06215 (9) | 0.0227 (3) | |
H11A | 0.1706 | 1.4718 | 0.0286 | 0.027* | |
C12A | 0.0448 (2) | 1.35683 (13) | 0.09567 (9) | 0.0231 (3) | |
H12A | −0.0776 | 1.3907 | 0.0857 | 0.028* | |
C13A | 0.0767 (2) | 1.25830 (13) | 0.14406 (9) | 0.0216 (3) | |
H13A | −0.0244 | 1.2245 | 0.1664 | 0.026* | |
C14A | 0.2055 (2) | 0.73234 (14) | 0.05636 (9) | 0.0283 (4) | |
H14A | 0.2138 | 0.7546 | −0.0013 | 0.042* | |
H14B | 0.0886 | 0.7047 | 0.0698 | 0.042* | |
H14C | 0.3082 | 0.6705 | 0.0664 | 0.042* | |
C15A | 0.1543 (2) | 0.50165 (14) | 0.30235 (12) | 0.0311 (4) | |
H15A | 0.1412 | 0.4364 | 0.3389 | 0.047* | |
H15B | 0.2539 | 0.4776 | 0.2600 | 0.047* | |
H15C | 0.0387 | 0.5264 | 0.2767 | 0.047* | |
C16A | 0.2807 (3) | 0.97923 (15) | 0.44755 (9) | 0.0296 (4) | |
H16A | 0.2969 | 1.0533 | 0.4708 | 0.044* | |
H16B | 0.3838 | 0.9192 | 0.4602 | 0.044* | |
H16C | 0.1650 | 0.9578 | 0.4710 | 0.044* | |
O1B | 0.72943 (15) | 0.80124 (9) | 0.39270 (6) | 0.0223 (2) | |
O2B | 0.67530 (15) | 0.56611 (9) | 0.15954 (6) | 0.0231 (2) | |
O3B | 0.73981 (16) | 0.96203 (9) | 0.13077 (6) | 0.0249 (2) | |
O4B | 0.38451 (14) | 1.24458 (9) | 0.33850 (6) | 0.0221 (2) | |
H2O4 | 0.389 (3) | 1.186 (2) | 0.3050 (14) | 0.053 (7)* | |
N1B | 0.69329 (16) | 1.09095 (10) | 0.27678 (7) | 0.0186 (2) | |
C1B | 0.73499 (19) | 0.88062 (12) | 0.26160 (8) | 0.0178 (3) | |
C6B | 0.72703 (19) | 0.86652 (13) | 0.17664 (8) | 0.0187 (3) | |
C5B | 0.7097 (2) | 0.76005 (13) | 0.14376 (8) | 0.0202 (3) | |
H5BA | 0.7063 | 0.7512 | 0.0865 | 0.024* | |
C4B | 0.69737 (19) | 0.66679 (12) | 0.19584 (8) | 0.0182 (3) | |
C3B | 0.70674 (19) | 0.67617 (12) | 0.27957 (8) | 0.0183 (3) | |
H3BA | 0.7005 | 0.6115 | 0.3144 | 0.022* | |
C2B | 0.72559 (19) | 0.78316 (13) | 0.31088 (8) | 0.0176 (3) | |
C7B | 0.74811 (19) | 0.98811 (12) | 0.30235 (8) | 0.0182 (3) | |
H7BA | 0.8028 | 0.9816 | 0.3530 | 0.022* | |
C8B | 0.71474 (19) | 1.18242 (12) | 0.32963 (8) | 0.0175 (3) | |
C9B | 0.5554 (2) | 1.26007 (12) | 0.35589 (8) | 0.0178 (3) | |
C10B | 0.5708 (2) | 1.35514 (13) | 0.40419 (8) | 0.0206 (3) | |
H10B | 0.4644 | 1.4100 | 0.4201 | 0.025* | |
C11B | 0.7414 (2) | 1.36955 (13) | 0.42898 (9) | 0.0246 (3) | |
H11B | 0.7507 | 1.4335 | 0.4627 | 0.030* | |
C12B | 0.8977 (2) | 1.29117 (14) | 0.40481 (9) | 0.0252 (3) | |
H12B | 1.0138 | 1.3007 | 0.4226 | 0.030* | |
C13B | 0.8846 (2) | 1.19849 (14) | 0.35456 (9) | 0.0219 (3) | |
H13B | 0.9924 | 1.1457 | 0.3371 | 0.026* | |
C14B | 0.7287 (2) | 0.70361 (14) | 0.44500 (9) | 0.0257 (3) | |
H14D | 0.7280 | 0.7283 | 0.5018 | 0.039* | |
H14E | 0.8390 | 0.6461 | 0.4311 | 0.039* | |
H14F | 0.6185 | 0.6692 | 0.4380 | 0.039* | |
C15B | 0.6564 (2) | 0.47040 (13) | 0.21263 (9) | 0.0249 (3) | |
H15D | 0.6355 | 0.4043 | 0.1805 | 0.037* | |
H15E | 0.5516 | 0.4926 | 0.2528 | 0.037* | |
H15F | 0.7691 | 0.4488 | 0.2409 | 0.037* | |
C16B | 0.7402 (3) | 0.95075 (15) | 0.04466 (9) | 0.0343 (4) | |
H16D | 0.7459 | 1.0261 | 0.0190 | 0.051* | |
H16E | 0.6274 | 0.9236 | 0.0312 | 0.051* | |
H16F | 0.8477 | 0.8947 | 0.0245 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0414 (6) | 0.0140 (5) | 0.0205 (5) | −0.0081 (5) | −0.0030 (4) | −0.0023 (4) |
O2A | 0.0367 (6) | 0.0142 (5) | 0.0373 (6) | −0.0064 (5) | −0.0023 (5) | 0.0087 (5) |
O3A | 0.0320 (6) | 0.0150 (5) | 0.0194 (5) | −0.0032 (4) | −0.0044 (4) | −0.0008 (4) |
O4A | 0.0235 (5) | 0.0143 (5) | 0.0247 (5) | −0.0016 (4) | −0.0030 (4) | 0.0060 (4) |
N1A | 0.0231 (6) | 0.0106 (6) | 0.0204 (5) | −0.0027 (5) | −0.0029 (4) | 0.0024 (4) |
C1A | 0.0199 (6) | 0.0114 (6) | 0.0209 (6) | −0.0033 (5) | −0.0005 (5) | 0.0003 (5) |
C2A | 0.0215 (7) | 0.0139 (7) | 0.0206 (6) | −0.0032 (5) | −0.0008 (5) | −0.0006 (5) |
C3A | 0.0216 (7) | 0.0107 (7) | 0.0291 (7) | −0.0023 (5) | −0.0009 (5) | 0.0000 (5) |
C4A | 0.0183 (6) | 0.0122 (7) | 0.0306 (7) | −0.0015 (5) | 0.0004 (5) | 0.0058 (5) |
C5A | 0.0219 (7) | 0.0172 (7) | 0.0217 (6) | −0.0004 (6) | −0.0011 (5) | 0.0044 (5) |
C6A | 0.0177 (6) | 0.0134 (7) | 0.0225 (6) | −0.0007 (5) | −0.0010 (5) | −0.0006 (5) |
C7A | 0.0229 (7) | 0.0135 (7) | 0.0187 (6) | −0.0026 (5) | −0.0013 (5) | −0.0005 (5) |
C8A | 0.0265 (7) | 0.0102 (6) | 0.0159 (6) | −0.0028 (5) | −0.0032 (5) | 0.0002 (5) |
C9A | 0.0245 (7) | 0.0102 (6) | 0.0186 (6) | −0.0006 (5) | −0.0033 (5) | −0.0010 (5) |
C10A | 0.0307 (7) | 0.0126 (7) | 0.0204 (6) | −0.0044 (6) | −0.0022 (5) | 0.0024 (5) |
C11A | 0.0354 (8) | 0.0124 (7) | 0.0197 (6) | −0.0002 (6) | −0.0058 (6) | 0.0028 (5) |
C12A | 0.0281 (7) | 0.0180 (7) | 0.0217 (7) | 0.0029 (6) | −0.0065 (5) | 0.0003 (5) |
C13A | 0.0252 (7) | 0.0178 (7) | 0.0214 (6) | −0.0023 (6) | −0.0030 (5) | −0.0003 (5) |
C14A | 0.0417 (9) | 0.0196 (8) | 0.0251 (7) | −0.0108 (7) | 0.0011 (6) | −0.0073 (6) |
C15A | 0.0290 (8) | 0.0124 (7) | 0.0527 (10) | −0.0054 (6) | −0.0043 (7) | 0.0068 (7) |
C16A | 0.0450 (9) | 0.0232 (8) | 0.0199 (7) | −0.0011 (7) | −0.0070 (6) | −0.0005 (6) |
O1B | 0.0351 (6) | 0.0147 (5) | 0.0166 (5) | −0.0032 (4) | −0.0006 (4) | 0.0012 (4) |
O2B | 0.0333 (6) | 0.0137 (5) | 0.0229 (5) | −0.0053 (4) | −0.0017 (4) | −0.0016 (4) |
O3B | 0.0439 (6) | 0.0113 (5) | 0.0179 (5) | −0.0004 (5) | −0.0014 (4) | 0.0026 (4) |
O4B | 0.0219 (5) | 0.0165 (5) | 0.0274 (5) | −0.0010 (4) | −0.0028 (4) | −0.0063 (4) |
N1B | 0.0225 (6) | 0.0125 (6) | 0.0197 (5) | 0.0002 (5) | −0.0013 (4) | −0.0018 (4) |
C1B | 0.0196 (6) | 0.0121 (7) | 0.0204 (6) | 0.0005 (5) | −0.0006 (5) | 0.0005 (5) |
C6B | 0.0211 (6) | 0.0139 (7) | 0.0195 (6) | 0.0010 (5) | −0.0004 (5) | 0.0011 (5) |
C5B | 0.0253 (7) | 0.0155 (7) | 0.0182 (6) | 0.0012 (6) | −0.0014 (5) | −0.0007 (5) |
C4B | 0.0187 (6) | 0.0132 (7) | 0.0219 (6) | −0.0006 (5) | −0.0002 (5) | −0.0016 (5) |
C3B | 0.0204 (6) | 0.0123 (6) | 0.0214 (6) | −0.0012 (5) | 0.0008 (5) | 0.0013 (5) |
C2B | 0.0183 (6) | 0.0158 (7) | 0.0174 (6) | 0.0007 (5) | 0.0003 (5) | −0.0003 (5) |
C7B | 0.0217 (6) | 0.0143 (7) | 0.0181 (6) | −0.0011 (5) | −0.0010 (5) | 0.0000 (5) |
C8B | 0.0242 (7) | 0.0118 (6) | 0.0162 (6) | −0.0017 (5) | −0.0020 (5) | 0.0014 (5) |
C9B | 0.0241 (7) | 0.0121 (6) | 0.0170 (6) | −0.0026 (5) | −0.0019 (5) | 0.0015 (5) |
C10B | 0.0304 (7) | 0.0128 (7) | 0.0181 (6) | −0.0033 (6) | 0.0007 (5) | 0.0004 (5) |
C11B | 0.0374 (8) | 0.0169 (7) | 0.0218 (7) | −0.0106 (6) | −0.0037 (6) | −0.0002 (5) |
C12B | 0.0300 (8) | 0.0232 (8) | 0.0250 (7) | −0.0103 (7) | −0.0070 (6) | 0.0045 (6) |
C13B | 0.0237 (7) | 0.0182 (7) | 0.0236 (7) | −0.0034 (6) | −0.0020 (5) | 0.0037 (5) |
C14B | 0.0392 (9) | 0.0195 (8) | 0.0185 (7) | −0.0050 (7) | −0.0030 (6) | 0.0042 (6) |
C15B | 0.0310 (8) | 0.0165 (7) | 0.0288 (7) | −0.0086 (6) | −0.0019 (6) | 0.0007 (6) |
C16B | 0.0635 (12) | 0.0194 (8) | 0.0185 (7) | −0.0026 (8) | −0.0030 (7) | 0.0031 (6) |
O1A—C2A | 1.3620 (17) | O1B—C2B | 1.3665 (16) |
O1A—C14A | 1.4324 (16) | O1B—C14B | 1.4240 (18) |
O2A—C4A | 1.3616 (18) | O2B—C4B | 1.3647 (16) |
O2A—C15A | 1.4345 (19) | O2B—C15B | 1.4321 (18) |
O3A—C6A | 1.3641 (16) | O3B—C6B | 1.3547 (17) |
O3A—C16A | 1.4276 (17) | O3B—C16B | 1.4225 (17) |
O4A—C9A | 1.3579 (17) | O4B—C9B | 1.3555 (17) |
O4A—H1O4 | 0.88 (2) | O4B—H2O4 | 0.87 (2) |
N1A—C7A | 1.2868 (17) | N1B—C7B | 1.2823 (19) |
N1A—C8A | 1.4251 (18) | N1B—C8B | 1.4213 (17) |
C1A—C6A | 1.4149 (19) | C1B—C2B | 1.401 (2) |
C1A—C2A | 1.4149 (18) | C1B—C6B | 1.4145 (19) |
C1A—C7A | 1.447 (2) | C1B—C7B | 1.4514 (19) |
C2A—C3A | 1.385 (2) | C6B—C5B | 1.3918 (19) |
C3A—C4A | 1.383 (2) | C5B—C4B | 1.392 (2) |
C3A—H3AA | 0.9500 | C5B—H5BA | 0.9500 |
C4A—C5A | 1.402 (2) | C4B—C3B | 1.3894 (19) |
C5A—C6A | 1.380 (2) | C3B—C2B | 1.3903 (19) |
C5A—H5AA | 0.9500 | C3B—H3BA | 0.9500 |
C7A—H7AA | 0.9500 | C7B—H7BA | 0.9500 |
C8A—C13A | 1.395 (2) | C8B—C13B | 1.390 (2) |
C8A—C9A | 1.405 (2) | C8B—C9B | 1.4040 (19) |
C9A—C10A | 1.393 (2) | C9B—C10B | 1.3977 (18) |
C10A—C11A | 1.388 (2) | C10B—C11B | 1.389 (2) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.382 (2) | C11B—C12B | 1.385 (2) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.393 (2) | C12B—C13B | 1.390 (2) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—H14A | 0.9800 | C14B—H14D | 0.9800 |
C14A—H14B | 0.9800 | C14B—H14E | 0.9800 |
C14A—H14C | 0.9800 | C14B—H14F | 0.9800 |
C15A—H15A | 0.9800 | C15B—H15D | 0.9800 |
C15A—H15B | 0.9800 | C15B—H15E | 0.9800 |
C15A—H15C | 0.9800 | C15B—H15F | 0.9800 |
C16A—H16A | 0.9800 | C16B—H16D | 0.9800 |
C16A—H16B | 0.9800 | C16B—H16E | 0.9800 |
C16A—H16C | 0.9800 | C16B—H16F | 0.9800 |
C2A—O1A—C14A | 117.14 (12) | C2B—O1B—C14B | 117.47 (11) |
C4A—O2A—C15A | 117.14 (12) | C4B—O2B—C15B | 116.49 (11) |
C6A—O3A—C16A | 117.32 (12) | C6B—O3B—C16B | 117.65 (12) |
C9A—O4A—H1O4 | 114.6 (14) | C9B—O4B—H2O4 | 111.6 (15) |
C7A—N1A—C8A | 115.68 (12) | C7B—N1B—C8B | 115.77 (12) |
C6A—C1A—C2A | 116.46 (13) | C2B—C1B—C6B | 117.29 (13) |
C6A—C1A—C7A | 126.30 (12) | C2B—C1B—C7B | 117.12 (12) |
C2A—C1A—C7A | 117.12 (12) | C6B—C1B—C7B | 125.57 (13) |
O1A—C2A—C3A | 122.60 (12) | O3B—C6B—C5B | 123.26 (12) |
O1A—C2A—C1A | 114.70 (12) | O3B—C6B—C1B | 115.65 (12) |
C3A—C2A—C1A | 122.69 (13) | C5B—C6B—C1B | 121.09 (14) |
C4A—C3A—C2A | 118.44 (13) | C4B—C5B—C6B | 119.10 (13) |
C4A—C3A—H3AA | 120.8 | C4B—C5B—H5BA | 120.4 |
C2A—C3A—H3AA | 120.8 | C6B—C5B—H5BA | 120.4 |
O2A—C4A—C3A | 123.05 (13) | O2B—C4B—C3B | 122.34 (13) |
O2A—C4A—C5A | 115.53 (13) | O2B—C4B—C5B | 115.84 (12) |
C3A—C4A—C5A | 121.40 (13) | C3B—C4B—C5B | 121.83 (13) |
C6A—C5A—C4A | 119.17 (13) | C4B—C3B—C2B | 117.98 (13) |
C6A—C5A—H5AA | 120.4 | C4B—C3B—H3BA | 121.0 |
C4A—C5A—H5AA | 120.4 | C2B—C3B—H3BA | 121.0 |
O3A—C6A—C5A | 122.97 (12) | O1B—C2B—C3B | 121.90 (13) |
O3A—C6A—C1A | 115.27 (12) | O1B—C2B—C1B | 115.37 (12) |
C5A—C6A—C1A | 121.75 (12) | C3B—C2B—C1B | 122.69 (12) |
N1A—C7A—C1A | 127.95 (13) | N1B—C7B—C1B | 126.50 (13) |
N1A—C7A—H7AA | 116.0 | N1B—C7B—H7BA | 116.7 |
C1A—C7A—H7AA | 116.0 | C1B—C7B—H7BA | 116.7 |
C13A—C8A—C9A | 119.40 (13) | C13B—C8B—C9B | 119.66 (13) |
C13A—C8A—N1A | 121.91 (13) | C13B—C8B—N1B | 123.03 (13) |
C9A—C8A—N1A | 118.64 (13) | C9B—C8B—N1B | 117.30 (12) |
O4A—C9A—C10A | 117.89 (13) | O4B—C9B—C10B | 118.09 (12) |
O4A—C9A—C8A | 122.80 (13) | O4B—C9B—C8B | 122.48 (12) |
C10A—C9A—C8A | 119.30 (13) | C10B—C9B—C8B | 119.40 (13) |
C11A—C10A—C9A | 120.70 (14) | C11B—C10B—C9B | 120.17 (14) |
C11A—C10A—H10A | 119.6 | C11B—C10B—H10B | 119.9 |
C9A—C10A—H10A | 119.6 | C9B—C10B—H10B | 119.9 |
C12A—C11A—C10A | 120.20 (14) | C12B—C11B—C10B | 120.32 (13) |
C12A—C11A—H11A | 119.9 | C12B—C11B—H11B | 119.8 |
C10A—C11A—H11A | 119.9 | C10B—C11B—H11B | 119.8 |
C11A—C12A—C13A | 119.72 (14) | C11B—C12B—C13B | 119.90 (14) |
C11A—C12A—H12A | 120.1 | C11B—C12B—H12B | 120.1 |
C13A—C12A—H12A | 120.1 | C13B—C12B—H12B | 120.1 |
C12A—C13A—C8A | 120.66 (14) | C12B—C13B—C8B | 120.49 (14) |
C12A—C13A—H13A | 119.7 | C12B—C13B—H13B | 119.8 |
C8A—C13A—H13A | 119.7 | C8B—C13B—H13B | 119.8 |
O1A—C14A—H14A | 109.5 | O1B—C14B—H14D | 109.5 |
O1A—C14A—H14B | 109.5 | O1B—C14B—H14E | 109.5 |
H14A—C14A—H14B | 109.5 | H14D—C14B—H14E | 109.5 |
O1A—C14A—H14C | 109.5 | O1B—C14B—H14F | 109.5 |
H14A—C14A—H14C | 109.5 | H14D—C14B—H14F | 109.5 |
H14B—C14A—H14C | 109.5 | H14E—C14B—H14F | 109.5 |
O2A—C15A—H15A | 109.5 | O2B—C15B—H15D | 109.5 |
O2A—C15A—H15B | 109.5 | O2B—C15B—H15E | 109.5 |
H15A—C15A—H15B | 109.5 | H15D—C15B—H15E | 109.5 |
O2A—C15A—H15C | 109.5 | O2B—C15B—H15F | 109.5 |
H15A—C15A—H15C | 109.5 | H15D—C15B—H15F | 109.5 |
H15B—C15A—H15C | 109.5 | H15E—C15B—H15F | 109.5 |
O3A—C16A—H16A | 109.5 | O3B—C16B—H16D | 109.5 |
O3A—C16A—H16B | 109.5 | O3B—C16B—H16E | 109.5 |
H16A—C16A—H16B | 109.5 | H16D—C16B—H16E | 109.5 |
O3A—C16A—H16C | 109.5 | O3B—C16B—H16F | 109.5 |
H16A—C16A—H16C | 109.5 | H16D—C16B—H16F | 109.5 |
H16B—C16A—H16C | 109.5 | H16E—C16B—H16F | 109.5 |
C14A—O1A—C2A—C3A | −3.2 (2) | C16B—O3B—C6B—C5B | −1.7 (2) |
C14A—O1A—C2A—C1A | 176.06 (13) | C16B—O3B—C6B—C1B | 177.43 (14) |
C6A—C1A—C2A—O1A | −176.76 (12) | C2B—C1B—C6B—O3B | −178.87 (12) |
C7A—C1A—C2A—O1A | 6.93 (18) | C7B—C1B—C6B—O3B | 2.5 (2) |
C6A—C1A—C2A—C3A | 2.5 (2) | C2B—C1B—C6B—C5B | 0.3 (2) |
C7A—C1A—C2A—C3A | −173.82 (13) | C7B—C1B—C6B—C5B | −178.30 (13) |
O1A—C2A—C3A—C4A | 178.87 (13) | O3B—C6B—C5B—C4B | −179.96 (13) |
C1A—C2A—C3A—C4A | −0.3 (2) | C1B—C6B—C5B—C4B | 0.9 (2) |
C15A—O2A—C4A—C3A | −6.7 (2) | C15B—O2B—C4B—C3B | 1.86 (19) |
C15A—O2A—C4A—C5A | 174.54 (13) | C15B—O2B—C4B—C5B | −178.03 (12) |
C2A—C3A—C4A—O2A | 179.90 (13) | C6B—C5B—C4B—O2B | 178.19 (12) |
C2A—C3A—C4A—C5A | −1.5 (2) | C6B—C5B—C4B—C3B | −1.7 (2) |
O2A—C4A—C5A—C6A | 179.65 (12) | O2B—C4B—C3B—C2B | −178.70 (12) |
C3A—C4A—C5A—C6A | 0.9 (2) | C5B—C4B—C3B—C2B | 1.2 (2) |
C16A—O3A—C6A—C5A | −1.5 (2) | C14B—O1B—C2B—C3B | 5.07 (19) |
C16A—O3A—C6A—C1A | 177.08 (13) | C14B—O1B—C2B—C1B | −177.21 (12) |
C4A—C5A—C6A—O3A | 179.96 (13) | C4B—C3B—C2B—O1B | 177.67 (13) |
C4A—C5A—C6A—C1A | 1.4 (2) | C4B—C3B—C2B—C1B | 0.1 (2) |
C2A—C1A—C6A—O3A | 178.33 (12) | C6B—C1B—C2B—O1B | −178.54 (12) |
C7A—C1A—C6A—O3A | −5.7 (2) | C7B—C1B—C2B—O1B | 0.18 (18) |
C2A—C1A—C6A—C5A | −3.0 (2) | C6B—C1B—C2B—C3B | −0.8 (2) |
C7A—C1A—C6A—C5A | 172.89 (14) | C7B—C1B—C2B—C3B | 177.88 (13) |
C8A—N1A—C7A—C1A | −175.58 (13) | C8B—N1B—C7B—C1B | 177.48 (13) |
C6A—C1A—C7A—N1A | 23.4 (2) | C2B—C1B—C7B—N1B | −152.97 (14) |
C2A—C1A—C7A—N1A | −160.71 (14) | C6B—C1B—C7B—N1B | 25.6 (2) |
C7A—N1A—C8A—C13A | 58.87 (17) | C7B—N1B—C8B—C13B | 59.30 (19) |
C7A—N1A—C8A—C9A | −123.60 (14) | C7B—N1B—C8B—C9B | −121.81 (14) |
C13A—C8A—C9A—O4A | −178.98 (12) | C13B—C8B—C9B—O4B | −175.24 (13) |
N1A—C8A—C9A—O4A | 3.44 (19) | N1B—C8B—C9B—O4B | 5.8 (2) |
C13A—C8A—C9A—C10A | −0.43 (19) | C13B—C8B—C9B—C10B | 2.5 (2) |
N1A—C8A—C9A—C10A | −178.01 (12) | N1B—C8B—C9B—C10B | −176.43 (12) |
O4A—C9A—C10A—C11A | 179.19 (12) | O4B—C9B—C10B—C11B | 174.92 (13) |
C8A—C9A—C10A—C11A | 0.6 (2) | C8B—C9B—C10B—C11B | −2.9 (2) |
C9A—C10A—C11A—C12A | 0.0 (2) | C9B—C10B—C11B—C12B | 1.2 (2) |
C10A—C11A—C12A—C13A | −0.8 (2) | C10B—C11B—C12B—C13B | 0.9 (2) |
C11A—C12A—C13A—C8A | 0.9 (2) | C11B—C12B—C13B—C8B | −1.3 (2) |
C9A—C8A—C13A—C12A | −0.3 (2) | C9B—C8B—C13B—C12B | −0.4 (2) |
N1A—C8A—C13A—C12A | 177.19 (12) | N1B—C8B—C13B—C12B | 178.47 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4A—H1O4···O3B | 0.88 (2) | 2.53 (2) | 2.9924 (15) | 114.0 (17) |
O4A—H1O4···N1B | 0.88 (2) | 1.96 (2) | 2.7897 (15) | 158 (2) |
O4B—H2O4···N1A | 0.88 (2) | 2.00 (2) | 2.8013 (16) | 151 (2) |
O4B—H2O4···N1B | 0.88 (2) | 2.35 (2) | 2.7891 (16) | 111.1 (18) |
C13B—H13B···O3Ai | 0.95 | 2.59 | 3.4639 (19) | 154 |
C15B—H15D···O4Aii | 0.98 | 2.43 | 3.3847 (18) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4A—H1O4···O3B | 0.88 (2) | 2.53 (2) | 2.9924 (15) | 114.0 (17) |
O4A—H1O4···N1B | 0.88 (2) | 1.96 (2) | 2.7897 (15) | 158 (2) |
O4B—H2O4···N1A | 0.88 (2) | 2.00 (2) | 2.8013 (16) | 151 (2) |
O4B—H2O4···N1B | 0.88 (2) | 2.35 (2) | 2.7891 (16) | 111.1 (18) |
C13B—H13B···O3Ai | 0.95 | 2.59 | 3.4639 (19) | 154 |
C15B—H15D···O4Aii | 0.98 | 2.43 | 3.3847 (18) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z. |
Footnotes
1This paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand on the occasion of his 86th birthday, which fell on December 5th, 2013.
‡Thomson Reuters ResearcherID: A-5085-2009.
§Additional correspondence author, e-mail: hfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.
Acknowledgements
NK thanks the Center of Excellence for Innovation in Chemistry (PERCH–CIC), Commission on Higher Education, Ministry of Education, and the Graduate School, Prince of Songkla University, for financial support. The authors extend their appreciation to the Malaysian Government and Universiti Sains Malaysia for APEX DE2012 grant No.1002/PFIZIK/910323, and the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University.
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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.
Aza-stilbenes are a special group of compounds in the Schiff base family which can be synthesized by the reaction of aldehyde with aniline. Aza-stilbenes have been shown to possess potent biological properties such as antibacterial (Tamizh et al., 2012), antioxidant (Cheng et al., 2010; Lu et al., 2012), antifungal (da Silva et al., 2011) and antiproliferative (Fujita et al., 2012) activities. The interesting biological activities of aza-stilbenes have led us to synthesize the title compound (I) and study its antibacterial and antioxidant activities. Our antibacterial assay have shown that (I) possesses moderate to weak antibacterial activity against B. subtilis, S. aureus, P. aeruginosa, S. typhi and S.sonnei with the MIC values in the range of 37.5 to 150 µg/ml. In addition (I) also shows interesting antioxidant activity by DPPH assay with the IC50 value of 0.080 ± 0.0004 µg/ml. We report here the crystal structure of the title compound.
There are two independent molecules, A and B in the asymmetric unit of the title compound, with similar conformations but some differences in bond angles (Fig. 1). The molecular structure exists in a trans configuration with respect to the methylidene C7═N1 double bond [1.2868 (13) and 1.2823 (19) Å for molecules A and B, respectively] and with the torsion angle C8—N1—C7—C1 = -175.58 (13)° for molecule A [177.48 (13)° for molecule B]. The molecule is twisted with the dihedral angle between the two substituted benzene rings being 80.52 (7)° in molecule A and 83.53 (7)° in molecule B. In both molecules, the three methoxy groups are co-planar with their bound benzene rings with the C14—O1—C2—C3 = -3.2 (2)°, C15—O2—C4—C3 = -6.7 (2)° and C16—O3—C6—C5 = -1.5 (2)° in molecule A, and the corresponding values are 5.07 (19), 1.86 (19) and -1.7 (2)° in molecule B. In each molecule, an intramolecular O—H···N hydrogen bond (Fig. 1 and Table 1) generates an S(5) ring motif (Bernstein et al., 1995). The bond distances are in normal ranges (Allen et al., 1987) and are comparable with the related structures (Kaewmanee et al., 2013; Sun et al., 2011).
In the crystal structure, the molecules are linked into dimers by O—H···N and O—H···O hydrogen bonds (Table 1) which form two R21(6) ring motifs and an R22(10) ring motif (Fig. 2). These dimers are further linked by C—H···O interactions (Table1) into chains along the b direction which arranged into sheets parallel to the ab plane (Fig. 3). There are π–π interactions with Cg1···Cg3 and Cg1···Cg3iv distances of 3.6030 (9) and 3.9452 (9) Å, respectively (Fig. 2) [symmetry code: (iv) = -1 + x, y, z]; Cg1 and Cg3 are the centroids of C1A–C6A and C1B–C6B rings, respectively.]