organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 1| January 2014| Pages o62-o63

(E)-2-[(2,4,6-Tri­meth­­oxy­benzyl­­idene)amino]­phenol

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

(Received 29 November 2013; accepted 5 December 2013; online 14 December 2013)

There are two independent mol­ecules in the asymmetric unit of the title compound, C16H17NO4, 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 ππ 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 ππ inter­action [centroid–centroid distance of 3.9452 (9) Å] into layers lying parallel to the ab plane.

Related literature

For organic bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For background to and application of aza-stilbene, see: Cheng et al. (2010[Cheng, L.-X., Tang, J.-J., Luo, H., Jin, X.-L., Dai, F., Yang, J., Qian, Y.-P., Li, X.-Z. & Zhou, B. (2010). Bioorg. Med. Chem. Lett. 20, 2417-2420.]); da Silva et al. (2011[Silva, C. M. da, da Silva, D. L., Martins, C. V. B., de Resende, M. A., Dias, E. S., Magalhaes, T. F. F., Rodrigues, L. P., Sabino, A. A., Alves, R. B. & de Fatima, A. (2011). Chem. Biol. Drug Des. 78, 810-815.]); Fujita et al. (2012[Fujita, Y., Islam, R., Sakai, K., Kaneda, H., Kudo, K., Tamura, D., Aomatsu, K., Nagai, T., Kimura, H., Matsumoto, K., de Velasco, M. A., Arao, T., Okawara, T. & Nishio, K. (2012). Invest. New Drugs, 30, 1878-1886.]); Lu et al. (2012[Lu, J., Li, C., Chai, Y.-F., Yang, D.-Y. & Sun, C.-R. (2012). Bioorg. Med. Chem. Lett. 22, 5744-5747.]); Tamizh et al. (2012[Tamizh, M. M., Kesavan, D., Sivakumar, P. M., Mereiter, K., Deepa, M., Kirchner, K., Doble, M. & Karvembu, R. (2012). Chem. Biol. Drug Des. 79, 177-185.]). For related structures, see: Kaewmanee et al. (2013[Kaewmanee, N., Chantrapromma, S., Boonnak, N. & Fun, H.-K. (2013). Acta Cryst. E69, o903-o904.]); Sun et al. (2011[Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011). Acta Cryst. E67, o1578.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17NO4

  • Mr = 287.31

  • Triclinic, [P \overline 1]

  • a = 7.3819 (6) Å

  • b = 11.7036 (9) Å

  • c = 16.4373 (13) Å

  • α = 89.469 (2)°

  • β = 85.616 (2)°

  • γ = 80.456 (2)°

  • V = 1396.34 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.49 × 0.16 × 0.16 mm

Data collection
  • Bruker SMART APEX2 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.985

  • 29313 measured reflections

  • 8129 independent reflections

  • 5872 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.148

  • S = 1.02

  • 8129 reflections

  • 393 parameters

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

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

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 C7N1 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 ππ 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.]

Related literature top

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 top

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 structure determination were recrystalized from methanol by slow evaporation of the solvent at room temperature after several days (m.p. 450–452 K).

Refinement top

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 carrier atom for water and methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. R21(6) and R21(10) ring motifs and a ππ interaction in the crystal of the title compound.
[Figure 3] Fig. 3. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are drawn as dashed lines.
(E)-2-[(2,4,6-Trimethoxybenzylidene)amino]phenol top
Crystal data top
C16H17NO4Z = 4
Mr = 287.31F(000) = 608
Triclinic, P1Dx = 1.367 Mg m3
Hall symbol: -P 1Melting point = 450–452 K
a = 7.3819 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.7036 (9) ÅCell parameters from 8129 reflections
c = 16.4373 (13) Åθ = 2.5–30.0°
α = 89.469 (2)°µ = 0.10 mm1
β = 85.616 (2)°T = 100 K
γ = 80.456 (2)°Block, colourless
V = 1396.34 (19) Å30.49 × 0.16 × 0.16 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
8129 independent reflections
Radiation source: fine-focus sealed tube5872 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.5°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1616
Tmin = 0.954, Tmax = 0.985l = 2323
29313 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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H 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 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C16H17NO4γ = 80.456 (2)°
Mr = 287.31V = 1396.34 (19) Å3
Triclinic, P1Z = 4
a = 7.3819 (6) ÅMo Kα radiation
b = 11.7036 (9) ŵ = 0.10 mm1
c = 16.4373 (13) ÅT = 100 K
α = 89.469 (2)°0.49 × 0.16 × 0.16 mm
β = 85.616 (2)°
Data collection top
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 = 0.985Rint = 0.048
29313 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.41 e Å3
8129 reflectionsΔρmin = 0.32 e Å3
393 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.21415 (16)0.83067 (9)0.10628 (6)0.0249 (2)
O2A0.19684 (16)0.59610 (10)0.34830 (7)0.0292 (3)
O3A0.27544 (15)0.98999 (9)0.36114 (6)0.0221 (2)
O4A0.58266 (14)1.21472 (9)0.13823 (6)0.0210 (2)
H1O40.597 (3)1.164 (2)0.1779 (13)0.043 (6)*
N1A0.29206 (16)1.11109 (10)0.21219 (7)0.0180 (2)
C1A0.23748 (19)0.91116 (12)0.23397 (8)0.0174 (3)
C2A0.21676 (19)0.81294 (12)0.18822 (8)0.0187 (3)
C3A0.2025 (2)0.70672 (12)0.22379 (9)0.0205 (3)
H3AA0.18810.64240.19150.025*
C4A0.20979 (19)0.69651 (13)0.30743 (9)0.0206 (3)
C5A0.2352 (2)0.78998 (13)0.35564 (9)0.0206 (3)
H5AA0.24170.78130.41290.025*
C6A0.25065 (19)0.89475 (12)0.31884 (8)0.0181 (3)
C7A0.23176 (19)1.01974 (12)0.19062 (8)0.0184 (3)
H7AA0.17681.02410.14000.022*
C8A0.2556 (2)1.20881 (12)0.16002 (8)0.0175 (3)
C9A0.40463 (19)1.25893 (12)0.12645 (8)0.0179 (3)
C10A0.3708 (2)1.35666 (13)0.07741 (8)0.0212 (3)
H10A0.47111.39050.05410.025*
C11A0.1919 (2)1.40519 (13)0.06215 (9)0.0227 (3)
H11A0.17061.47180.02860.027*
C12A0.0448 (2)1.35683 (13)0.09567 (9)0.0231 (3)
H12A0.07761.39070.08570.028*
C13A0.0767 (2)1.25830 (13)0.14406 (9)0.0216 (3)
H13A0.02441.22450.16640.026*
C14A0.2055 (2)0.73234 (14)0.05636 (9)0.0283 (4)
H14A0.21380.75460.00130.042*
H14B0.08860.70470.06980.042*
H14C0.30820.67050.06640.042*
C15A0.1543 (2)0.50165 (14)0.30235 (12)0.0311 (4)
H15A0.14120.43640.33890.047*
H15B0.25390.47760.26000.047*
H15C0.03870.52640.27670.047*
C16A0.2807 (3)0.97923 (15)0.44755 (9)0.0296 (4)
H16A0.29691.05330.47080.044*
H16B0.38380.91920.46020.044*
H16C0.16500.95780.47100.044*
O1B0.72943 (15)0.80124 (9)0.39270 (6)0.0223 (2)
O2B0.67530 (15)0.56611 (9)0.15954 (6)0.0231 (2)
O3B0.73981 (16)0.96203 (9)0.13077 (6)0.0249 (2)
O4B0.38451 (14)1.24458 (9)0.33850 (6)0.0221 (2)
H2O40.389 (3)1.186 (2)0.3050 (14)0.053 (7)*
N1B0.69329 (16)1.09095 (10)0.27678 (7)0.0186 (2)
C1B0.73499 (19)0.88062 (12)0.26160 (8)0.0178 (3)
C6B0.72703 (19)0.86652 (13)0.17664 (8)0.0187 (3)
C5B0.7097 (2)0.76005 (13)0.14376 (8)0.0202 (3)
H5BA0.70630.75120.08650.024*
C4B0.69737 (19)0.66679 (12)0.19584 (8)0.0182 (3)
C3B0.70674 (19)0.67617 (12)0.27957 (8)0.0183 (3)
H3BA0.70050.61150.31440.022*
C2B0.72559 (19)0.78316 (13)0.31088 (8)0.0176 (3)
C7B0.74811 (19)0.98811 (12)0.30235 (8)0.0182 (3)
H7BA0.80280.98160.35300.022*
C8B0.71474 (19)1.18242 (12)0.32963 (8)0.0175 (3)
C9B0.5554 (2)1.26007 (12)0.35589 (8)0.0178 (3)
C10B0.5708 (2)1.35514 (13)0.40419 (8)0.0206 (3)
H10B0.46441.41000.42010.025*
C11B0.7414 (2)1.36955 (13)0.42898 (9)0.0246 (3)
H11B0.75071.43350.46270.030*
C12B0.8977 (2)1.29117 (14)0.40481 (9)0.0252 (3)
H12B1.01381.30070.42260.030*
C13B0.8846 (2)1.19849 (14)0.35456 (9)0.0219 (3)
H13B0.99241.14570.33710.026*
C14B0.7287 (2)0.70361 (14)0.44500 (9)0.0257 (3)
H14D0.72800.72830.50180.039*
H14E0.83900.64610.43110.039*
H14F0.61850.66920.43800.039*
C15B0.6564 (2)0.47040 (13)0.21263 (9)0.0249 (3)
H15D0.63550.40430.18050.037*
H15E0.55160.49260.25280.037*
H15F0.76910.44880.24090.037*
C16B0.7402 (3)0.95075 (15)0.04466 (9)0.0343 (4)
H16D0.74591.02610.01900.051*
H16E0.62740.92360.03120.051*
H16F0.84770.89470.02450.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0414 (6)0.0140 (5)0.0205 (5)0.0081 (5)0.0030 (4)0.0023 (4)
O2A0.0367 (6)0.0142 (5)0.0373 (6)0.0064 (5)0.0023 (5)0.0087 (5)
O3A0.0320 (6)0.0150 (5)0.0194 (5)0.0032 (4)0.0044 (4)0.0008 (4)
O4A0.0235 (5)0.0143 (5)0.0247 (5)0.0016 (4)0.0030 (4)0.0060 (4)
N1A0.0231 (6)0.0106 (6)0.0204 (5)0.0027 (5)0.0029 (4)0.0024 (4)
C1A0.0199 (6)0.0114 (6)0.0209 (6)0.0033 (5)0.0005 (5)0.0003 (5)
C2A0.0215 (7)0.0139 (7)0.0206 (6)0.0032 (5)0.0008 (5)0.0006 (5)
C3A0.0216 (7)0.0107 (7)0.0291 (7)0.0023 (5)0.0009 (5)0.0000 (5)
C4A0.0183 (6)0.0122 (7)0.0306 (7)0.0015 (5)0.0004 (5)0.0058 (5)
C5A0.0219 (7)0.0172 (7)0.0217 (6)0.0004 (6)0.0011 (5)0.0044 (5)
C6A0.0177 (6)0.0134 (7)0.0225 (6)0.0007 (5)0.0010 (5)0.0006 (5)
C7A0.0229 (7)0.0135 (7)0.0187 (6)0.0026 (5)0.0013 (5)0.0005 (5)
C8A0.0265 (7)0.0102 (6)0.0159 (6)0.0028 (5)0.0032 (5)0.0002 (5)
C9A0.0245 (7)0.0102 (6)0.0186 (6)0.0006 (5)0.0033 (5)0.0010 (5)
C10A0.0307 (7)0.0126 (7)0.0204 (6)0.0044 (6)0.0022 (5)0.0024 (5)
C11A0.0354 (8)0.0124 (7)0.0197 (6)0.0002 (6)0.0058 (6)0.0028 (5)
C12A0.0281 (7)0.0180 (7)0.0217 (7)0.0029 (6)0.0065 (5)0.0003 (5)
C13A0.0252 (7)0.0178 (7)0.0214 (6)0.0023 (6)0.0030 (5)0.0003 (5)
C14A0.0417 (9)0.0196 (8)0.0251 (7)0.0108 (7)0.0011 (6)0.0073 (6)
C15A0.0290 (8)0.0124 (7)0.0527 (10)0.0054 (6)0.0043 (7)0.0068 (7)
C16A0.0450 (9)0.0232 (8)0.0199 (7)0.0011 (7)0.0070 (6)0.0005 (6)
O1B0.0351 (6)0.0147 (5)0.0166 (5)0.0032 (4)0.0006 (4)0.0012 (4)
O2B0.0333 (6)0.0137 (5)0.0229 (5)0.0053 (4)0.0017 (4)0.0016 (4)
O3B0.0439 (6)0.0113 (5)0.0179 (5)0.0004 (5)0.0014 (4)0.0026 (4)
O4B0.0219 (5)0.0165 (5)0.0274 (5)0.0010 (4)0.0028 (4)0.0063 (4)
N1B0.0225 (6)0.0125 (6)0.0197 (5)0.0002 (5)0.0013 (4)0.0018 (4)
C1B0.0196 (6)0.0121 (7)0.0204 (6)0.0005 (5)0.0006 (5)0.0005 (5)
C6B0.0211 (6)0.0139 (7)0.0195 (6)0.0010 (5)0.0004 (5)0.0011 (5)
C5B0.0253 (7)0.0155 (7)0.0182 (6)0.0012 (6)0.0014 (5)0.0007 (5)
C4B0.0187 (6)0.0132 (7)0.0219 (6)0.0006 (5)0.0002 (5)0.0016 (5)
C3B0.0204 (6)0.0123 (6)0.0214 (6)0.0012 (5)0.0008 (5)0.0013 (5)
C2B0.0183 (6)0.0158 (7)0.0174 (6)0.0007 (5)0.0003 (5)0.0003 (5)
C7B0.0217 (6)0.0143 (7)0.0181 (6)0.0011 (5)0.0010 (5)0.0000 (5)
C8B0.0242 (7)0.0118 (6)0.0162 (6)0.0017 (5)0.0020 (5)0.0014 (5)
C9B0.0241 (7)0.0121 (6)0.0170 (6)0.0026 (5)0.0019 (5)0.0015 (5)
C10B0.0304 (7)0.0128 (7)0.0181 (6)0.0033 (6)0.0007 (5)0.0004 (5)
C11B0.0374 (8)0.0169 (7)0.0218 (7)0.0106 (6)0.0037 (6)0.0002 (5)
C12B0.0300 (8)0.0232 (8)0.0250 (7)0.0103 (7)0.0070 (6)0.0045 (6)
C13B0.0237 (7)0.0182 (7)0.0236 (7)0.0034 (6)0.0020 (5)0.0037 (5)
C14B0.0392 (9)0.0195 (8)0.0185 (7)0.0050 (7)0.0030 (6)0.0042 (6)
C15B0.0310 (8)0.0165 (7)0.0288 (7)0.0086 (6)0.0019 (6)0.0007 (6)
C16B0.0635 (12)0.0194 (8)0.0185 (7)0.0026 (8)0.0030 (7)0.0031 (6)
Geometric parameters (Å, º) top
O1A—C2A1.3620 (17)O1B—C2B1.3665 (16)
O1A—C14A1.4324 (16)O1B—C14B1.4240 (18)
O2A—C4A1.3616 (18)O2B—C4B1.3647 (16)
O2A—C15A1.4345 (19)O2B—C15B1.4321 (18)
O3A—C6A1.3641 (16)O3B—C6B1.3547 (17)
O3A—C16A1.4276 (17)O3B—C16B1.4225 (17)
O4A—C9A1.3579 (17)O4B—C9B1.3555 (17)
O4A—H1O40.88 (2)O4B—H2O40.87 (2)
N1A—C7A1.2868 (17)N1B—C7B1.2823 (19)
N1A—C8A1.4251 (18)N1B—C8B1.4213 (17)
C1A—C6A1.4149 (19)C1B—C2B1.401 (2)
C1A—C2A1.4149 (18)C1B—C6B1.4145 (19)
C1A—C7A1.447 (2)C1B—C7B1.4514 (19)
C2A—C3A1.385 (2)C6B—C5B1.3918 (19)
C3A—C4A1.383 (2)C5B—C4B1.392 (2)
C3A—H3AA0.9500C5B—H5BA0.9500
C4A—C5A1.402 (2)C4B—C3B1.3894 (19)
C5A—C6A1.380 (2)C3B—C2B1.3903 (19)
C5A—H5AA0.9500C3B—H3BA0.9500
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C13A1.395 (2)C8B—C13B1.390 (2)
C8A—C9A1.405 (2)C8B—C9B1.4040 (19)
C9A—C10A1.393 (2)C9B—C10B1.3977 (18)
C10A—C11A1.388 (2)C10B—C11B1.389 (2)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.382 (2)C11B—C12B1.385 (2)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.393 (2)C12B—C13B1.390 (2)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
C14A—H14A0.9800C14B—H14D0.9800
C14A—H14B0.9800C14B—H14E0.9800
C14A—H14C0.9800C14B—H14F0.9800
C15A—H15A0.9800C15B—H15D0.9800
C15A—H15B0.9800C15B—H15E0.9800
C15A—H15C0.9800C15B—H15F0.9800
C16A—H16A0.9800C16B—H16D0.9800
C16A—H16B0.9800C16B—H16E0.9800
C16A—H16C0.9800C16B—H16F0.9800
C2A—O1A—C14A117.14 (12)C2B—O1B—C14B117.47 (11)
C4A—O2A—C15A117.14 (12)C4B—O2B—C15B116.49 (11)
C6A—O3A—C16A117.32 (12)C6B—O3B—C16B117.65 (12)
C9A—O4A—H1O4114.6 (14)C9B—O4B—H2O4111.6 (15)
C7A—N1A—C8A115.68 (12)C7B—N1B—C8B115.77 (12)
C6A—C1A—C2A116.46 (13)C2B—C1B—C6B117.29 (13)
C6A—C1A—C7A126.30 (12)C2B—C1B—C7B117.12 (12)
C2A—C1A—C7A117.12 (12)C6B—C1B—C7B125.57 (13)
O1A—C2A—C3A122.60 (12)O3B—C6B—C5B123.26 (12)
O1A—C2A—C1A114.70 (12)O3B—C6B—C1B115.65 (12)
C3A—C2A—C1A122.69 (13)C5B—C6B—C1B121.09 (14)
C4A—C3A—C2A118.44 (13)C4B—C5B—C6B119.10 (13)
C4A—C3A—H3AA120.8C4B—C5B—H5BA120.4
C2A—C3A—H3AA120.8C6B—C5B—H5BA120.4
O2A—C4A—C3A123.05 (13)O2B—C4B—C3B122.34 (13)
O2A—C4A—C5A115.53 (13)O2B—C4B—C5B115.84 (12)
C3A—C4A—C5A121.40 (13)C3B—C4B—C5B121.83 (13)
C6A—C5A—C4A119.17 (13)C4B—C3B—C2B117.98 (13)
C6A—C5A—H5AA120.4C4B—C3B—H3BA121.0
C4A—C5A—H5AA120.4C2B—C3B—H3BA121.0
O3A—C6A—C5A122.97 (12)O1B—C2B—C3B121.90 (13)
O3A—C6A—C1A115.27 (12)O1B—C2B—C1B115.37 (12)
C5A—C6A—C1A121.75 (12)C3B—C2B—C1B122.69 (12)
N1A—C7A—C1A127.95 (13)N1B—C7B—C1B126.50 (13)
N1A—C7A—H7AA116.0N1B—C7B—H7BA116.7
C1A—C7A—H7AA116.0C1B—C7B—H7BA116.7
C13A—C8A—C9A119.40 (13)C13B—C8B—C9B119.66 (13)
C13A—C8A—N1A121.91 (13)C13B—C8B—N1B123.03 (13)
C9A—C8A—N1A118.64 (13)C9B—C8B—N1B117.30 (12)
O4A—C9A—C10A117.89 (13)O4B—C9B—C10B118.09 (12)
O4A—C9A—C8A122.80 (13)O4B—C9B—C8B122.48 (12)
C10A—C9A—C8A119.30 (13)C10B—C9B—C8B119.40 (13)
C11A—C10A—C9A120.70 (14)C11B—C10B—C9B120.17 (14)
C11A—C10A—H10A119.6C11B—C10B—H10B119.9
C9A—C10A—H10A119.6C9B—C10B—H10B119.9
C12A—C11A—C10A120.20 (14)C12B—C11B—C10B120.32 (13)
C12A—C11A—H11A119.9C12B—C11B—H11B119.8
C10A—C11A—H11A119.9C10B—C11B—H11B119.8
C11A—C12A—C13A119.72 (14)C11B—C12B—C13B119.90 (14)
C11A—C12A—H12A120.1C11B—C12B—H12B120.1
C13A—C12A—H12A120.1C13B—C12B—H12B120.1
C12A—C13A—C8A120.66 (14)C12B—C13B—C8B120.49 (14)
C12A—C13A—H13A119.7C12B—C13B—H13B119.8
C8A—C13A—H13A119.7C8B—C13B—H13B119.8
O1A—C14A—H14A109.5O1B—C14B—H14D109.5
O1A—C14A—H14B109.5O1B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
O1A—C14A—H14C109.5O1B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
O2A—C15A—H15A109.5O2B—C15B—H15D109.5
O2A—C15A—H15B109.5O2B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
O2A—C15A—H15C109.5O2B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
O3A—C16A—H16A109.5O3B—C16B—H16D109.5
O3A—C16A—H16B109.5O3B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
O3A—C16A—H16C109.5O3B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
C14A—O1A—C2A—C3A3.2 (2)C16B—O3B—C6B—C5B1.7 (2)
C14A—O1A—C2A—C1A176.06 (13)C16B—O3B—C6B—C1B177.43 (14)
C6A—C1A—C2A—O1A176.76 (12)C2B—C1B—C6B—O3B178.87 (12)
C7A—C1A—C2A—O1A6.93 (18)C7B—C1B—C6B—O3B2.5 (2)
C6A—C1A—C2A—C3A2.5 (2)C2B—C1B—C6B—C5B0.3 (2)
C7A—C1A—C2A—C3A173.82 (13)C7B—C1B—C6B—C5B178.30 (13)
O1A—C2A—C3A—C4A178.87 (13)O3B—C6B—C5B—C4B179.96 (13)
C1A—C2A—C3A—C4A0.3 (2)C1B—C6B—C5B—C4B0.9 (2)
C15A—O2A—C4A—C3A6.7 (2)C15B—O2B—C4B—C3B1.86 (19)
C15A—O2A—C4A—C5A174.54 (13)C15B—O2B—C4B—C5B178.03 (12)
C2A—C3A—C4A—O2A179.90 (13)C6B—C5B—C4B—O2B178.19 (12)
C2A—C3A—C4A—C5A1.5 (2)C6B—C5B—C4B—C3B1.7 (2)
O2A—C4A—C5A—C6A179.65 (12)O2B—C4B—C3B—C2B178.70 (12)
C3A—C4A—C5A—C6A0.9 (2)C5B—C4B—C3B—C2B1.2 (2)
C16A—O3A—C6A—C5A1.5 (2)C14B—O1B—C2B—C3B5.07 (19)
C16A—O3A—C6A—C1A177.08 (13)C14B—O1B—C2B—C1B177.21 (12)
C4A—C5A—C6A—O3A179.96 (13)C4B—C3B—C2B—O1B177.67 (13)
C4A—C5A—C6A—C1A1.4 (2)C4B—C3B—C2B—C1B0.1 (2)
C2A—C1A—C6A—O3A178.33 (12)C6B—C1B—C2B—O1B178.54 (12)
C7A—C1A—C6A—O3A5.7 (2)C7B—C1B—C2B—O1B0.18 (18)
C2A—C1A—C6A—C5A3.0 (2)C6B—C1B—C2B—C3B0.8 (2)
C7A—C1A—C6A—C5A172.89 (14)C7B—C1B—C2B—C3B177.88 (13)
C8A—N1A—C7A—C1A175.58 (13)C8B—N1B—C7B—C1B177.48 (13)
C6A—C1A—C7A—N1A23.4 (2)C2B—C1B—C7B—N1B152.97 (14)
C2A—C1A—C7A—N1A160.71 (14)C6B—C1B—C7B—N1B25.6 (2)
C7A—N1A—C8A—C13A58.87 (17)C7B—N1B—C8B—C13B59.30 (19)
C7A—N1A—C8A—C9A123.60 (14)C7B—N1B—C8B—C9B121.81 (14)
C13A—C8A—C9A—O4A178.98 (12)C13B—C8B—C9B—O4B175.24 (13)
N1A—C8A—C9A—O4A3.44 (19)N1B—C8B—C9B—O4B5.8 (2)
C13A—C8A—C9A—C10A0.43 (19)C13B—C8B—C9B—C10B2.5 (2)
N1A—C8A—C9A—C10A178.01 (12)N1B—C8B—C9B—C10B176.43 (12)
O4A—C9A—C10A—C11A179.19 (12)O4B—C9B—C10B—C11B174.92 (13)
C8A—C9A—C10A—C11A0.6 (2)C8B—C9B—C10B—C11B2.9 (2)
C9A—C10A—C11A—C12A0.0 (2)C9B—C10B—C11B—C12B1.2 (2)
C10A—C11A—C12A—C13A0.8 (2)C10B—C11B—C12B—C13B0.9 (2)
C11A—C12A—C13A—C8A0.9 (2)C11B—C12B—C13B—C8B1.3 (2)
C9A—C8A—C13A—C12A0.3 (2)C9B—C8B—C13B—C12B0.4 (2)
N1A—C8A—C13A—C12A177.19 (12)N1B—C8B—C13B—C12B178.47 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4A—H1O4···O3B0.88 (2)2.53 (2)2.9924 (15)114.0 (17)
O4A—H1O4···N1B0.88 (2)1.96 (2)2.7897 (15)158 (2)
O4B—H2O4···N1A0.88 (2)2.00 (2)2.8013 (16)151 (2)
O4B—H2O4···N1B0.88 (2)2.35 (2)2.7891 (16)111.1 (18)
C13B—H13B···O3Ai0.952.593.4639 (19)154
C15B—H15D···O4Aii0.982.433.3847 (18)164
Symmetry codes: (i) x+1, y, z; (ii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4A—H1O4···O3B0.88 (2)2.53 (2)2.9924 (15)114.0 (17)
O4A—H1O4···N1B0.88 (2)1.96 (2)2.7897 (15)158 (2)
O4B—H2O4···N1A0.88 (2)2.00 (2)2.8013 (16)151 (2)
O4B—H2O4···N1B0.88 (2)2.35 (2)2.7891 (16)111.1 (18)
C13B—H13B···O3Ai0.952.593.4639 (19)154
C15B—H15D···O4Aii0.982.433.3847 (18)164
Symmetry codes: (i) x+1, y, z; (ii) x, y1, z.
 

Footnotes

This 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.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCheng, L.-X., Tang, J.-J., Luo, H., Jin, X.-L., Dai, F., Yang, J., Qian, Y.-P., Li, X.-Z. & Zhou, B. (2010). Bioorg. Med. Chem. Lett. 20, 2417–2420.  Web of Science CrossRef CAS PubMed
First citationFujita, Y., Islam, R., Sakai, K., Kaneda, H., Kudo, K., Tamura, D., Aomatsu, K., Nagai, T., Kimura, H., Matsumoto, K., de Velasco, M. A., Arao, T., Okawara, T. & Nishio, K. (2012). Invest. New Drugs, 30, 1878–1886.  Web of Science CrossRef CAS PubMed
First citationKaewmanee, N., Chantrapromma, S., Boonnak, N. & Fun, H.-K. (2013). Acta Cryst. E69, o903–o904.  CSD CrossRef CAS IUCr Journals
First citationLu, J., Li, C., Chai, Y.-F., Yang, D.-Y. & Sun, C.-R. (2012). Bioorg. Med. Chem. Lett. 22, 5744–5747.  Web of Science CrossRef CAS PubMed
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSilva, C. M. da, da Silva, D. L., Martins, C. V. B., de Resende, M. A., Dias, E. S., Magalhaes, T. F. F., Rodrigues, L. P., Sabino, A. A., Alves, R. B. & de Fatima, A. (2011). Chem. Biol. Drug Des. 78, 810–815.  Web of Science PubMed
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationSun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011). Acta Cryst. E67, o1578.  Web of Science CSD CrossRef IUCr Journals
First citationTamizh, M. M., Kesavan, D., Sivakumar, P. M., Mereiter, K., Deepa, M., Kirchner, K., Doble, M. & Karvembu, R. (2012). Chem. Biol. Drug Des. 79, 177–185.  Web of Science CSD CrossRef CAS PubMed
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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Volume 70| Part 1| January 2014| Pages o62-o63
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