(E)-3-(4-Hy­droxy-3-meth­oxy­phen­yl)-1-(4-hy­droxy­phen­yl)prop-2-en-1-one

Sathya, S.; Reuben Jonathan, D.; Prathebha, K.; Usha, G.; Jovita, J.

doi:10.1107/S1600536814008757

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o593-o594

doi:10.1107/S1600536814008757

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(E)-3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

S. Sathya,^a D. Reuben Jonathan,^b K. Prathebha,^a G. Usha ^a ^* and J. Jovita ^a

^aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^bPG and Research Department of Chemistry, Presidency College, Chennai-5, Tamil Nadu, India
^*Correspondence e-mail: guqmc@yahoo.com

(Received 13 March 2014; accepted 17 April 2014; online 26 April 2014)

In the title compound, C₁₆H₁₄O₄, there is an intramolecular O—H⋯O hydrogen bond. The benzene rings are inclined to one another by 13.89 (9)°. The prop-2-en-1-one group is twisted slightly, the O=C—C_ar—C_ar (ar = aromatic) and C=C—C=O torsion angles being −10.4 (3) and −7.4 (3)°, respectively. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming chains along [100]. These chains are further linked by O—H⋯O hydrogen bonds, forming corrugated sheets lying parallel to (010). There are C—H⋯π interactions present within the sheets.

CCDC reference: 991699

Related literature

For the biological activity of chalcones and chalcone derivatives, see: Marais et al. (2005 ); Di Carlo et al. (1999 ); Troeberg et al. (2000 ); Ni et al. (2004 ). For a related structure, see: Jasinski et al. (2011 ). For the synthesis, see: Sidharthan et al. (2012 ); Chitra et al. (2013 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₄O₄
M_r = 270.27
Orthorhombic, P b c a
a = 16.2808 (8) Å
b = 10.4348 (5) Å
c = 16.2905 (7) Å
V = 2767.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.968, T_max = 0.977
12921 measured reflections
3441 independent reflections
1935 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.128
S = 1.05
3344 reflections
189 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3	0.86 (2)	2.20 (3)	2.655 (2)	113 (2)
O2—H2O⋯O1ⁱ	0.87 (2)	1.87 (2)	2.7349 (18)	173 (2)
O4—H4O⋯O1ⁱⁱ	0.86 (2)	2.22 (2)	2.937 (2)	141 (3)
C16—H16A⋯Cgⁱⁱ	0.96	2.86	3.747 (3)	155
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 991699

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814008757/su2713sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008757/su2713Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814008757/su2713Isup3.cml

checkCIF report

Comment top

Chalcones are known as the precursors of all flavonoid type natural products in biosynthesis (Marais et al., 2005). They are a major class of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based food stuff and have been the subjects of interest for their significant pharmacological activities (Di Carlo et al., 1999). Many chalcones have been described for their high anti-malarial activity, probably as a result of addition of nucleophilic species to the double bond of the enone (Troeberg et al., 2000). A review of anti-infective and anti-inflammatory chalcones and recent advances in therapeutic chalcones have been reported (Ni et al., 2004). To understand the three dimensional features of this class of compounds, we report herein on the crystal structure of the title compound.

The molecular structure of the title molecule is illustrated in Fig. 1. The bond lengths (Allen et al., 1987) and bond angles are within normal values. The bond angles C6—C7—C8 = 119.12 (14) ° and C8═C9—C10 = 127.20 (17) ° are comparable with those in a similar reported structure (E)-3-(3,4-Dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (2E)-3-(3,4-Dimethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (Jasinski et al., 2011). This may be due to the presence of the keto group and associated steric forces. The prop-2-en-1-one group is twisted slightly with torsion angles O1═C7—C8—C9 and C5—C6—C7═O1 being -10.4 (3) and -7.4 (3) °, respectively. These values are comparable with the value of -6.9 (2) and -15.9 (2) ° reported for the above mentioned structure.

In the crystal, molecules are linked by O—H···O hydrogen bonds forming chains propagating along the a axis (Table 1 and Fig. 2). These chains are linked by further O—H···O hydrogen bonds forming corrugated sheets lying parallel to (010). Within the sheets there are C—H···π interactions present (Table 1). In total each molecule is linked to four neighbours by O—H···O hydrogen bonds (Table 1 and Fig. 2). Atom O4 acts as a bifurcated donor forming intra- and inter-molecular O—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the biological activity of chalcones and chalcone derivatives, see: Marais et al. (2005); Di Carlo et al. (1999); Troeberg et al. (2000); Ni et al. (2004). For a related structure, see: Jasinski et al. (2011). For the synthesis, see: Sidharthan et al. (2012); Chitra et al. (2013). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by a published procedure using the acid catalyzed Claisen-Schmidt reaction (Sidharthan et al., 2012; Chitra et al., 2013) Dry HCl gas was passed through a well cooled and stirred solution of 4-hydroxyacetophenone (0.02 mol) and vanillin (0.02 mol) in 125 ml of dry ethanol, placed in a 250 ml round-bottomed flask, for about 1 h. A wine-red coloured solution was formed to which ice cold water was added. Yellow block-like crystals of the title compound separated and were washed with double distilled water and re-crystallized from hot ethanol (Yield 85%; M.p. 454 K).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view along the x axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

(E)-3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₄O₄	F(000) = 1136
M_r = 270.27	D_x = 1.297 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3441 reflections
a = 16.2808 (8) Å	θ = 2.5–28.3°
b = 10.4348 (5) Å	µ = 0.09 mm⁻¹
c = 16.2905 (7) Å	T = 293 K
V = 2767.5 (2) Å³	Block, yellow
Z = 8	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3441 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scan	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→17
T_min = 0.968, T_max = 0.977	k = −13→7
12921 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0473P)² + 0.8783P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.004
3344 reflections	Δρ_max = 0.18 e Å⁻³
189 parameters	Δρ_min = −0.20 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (6)

Crystal data top

C₁₆H₁₄O₄	V = 2767.5 (2) Å³
M_r = 270.27	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.2808 (8) Å	µ = 0.09 mm⁻¹
b = 10.4348 (5) Å	T = 293 K
c = 16.2905 (7) Å	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3441 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1935 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.977	R_int = 0.027
12921 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	2 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.18 e Å⁻³
3344 reflections	Δρ_min = −0.20 e Å⁻³
189 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.21682 (7)	0.58070 (13)	0.26522 (8)	0.0532 (4)
O2	0.59318 (7)	0.69018 (13)	0.32421 (9)	0.0594 (4)
H2O	0.6310 (12)	0.649 (2)	0.2968 (14)	0.089*
O3	0.28796 (9)	0.08570 (16)	−0.06956 (10)	0.0762 (5)
O4	0.13699 (9)	−0.00902 (16)	−0.07979 (10)	0.0708 (5)
H4O	0.1798 (13)	−0.024 (3)	−0.1090 (16)	0.106*
C1	0.43059 (10)	0.50808 (17)	0.22500 (11)	0.0431 (4)
H1	0.4245	0.4397	0.1889	0.052*
C2	0.50835 (10)	0.54733 (17)	0.24660 (11)	0.0445 (4)
H2	0.5541	0.5065	0.2246	0.053*
C3	0.51802 (10)	0.64693 (17)	0.30075 (11)	0.0423 (4)
C4	0.44972 (11)	0.70803 (18)	0.33262 (12)	0.0511 (5)
H4	0.4562	0.7759	0.3690	0.061*
C5	0.37224 (10)	0.66855 (17)	0.31058 (11)	0.0461 (4)
H5	0.3267	0.7097	0.3327	0.055*
C6	0.36105 (9)	0.56830 (15)	0.25593 (10)	0.0366 (4)
C7	0.27741 (10)	0.53112 (17)	0.23093 (10)	0.0400 (4)
C8	0.26703 (10)	0.43695 (18)	0.16605 (11)	0.0453 (4)
H8	0.3133	0.4132	0.1362	0.054*
C9	0.19621 (11)	0.38287 (17)	0.14669 (11)	0.0459 (4)
H9	0.1504	0.4111	0.1755	0.055*
C10	0.18214 (10)	0.28457 (17)	0.08558 (11)	0.0444 (4)
C11	0.10435 (11)	0.2317 (2)	0.07729 (12)	0.0523 (5)
H11	0.0613	0.2625	0.1092	0.063*
C12	0.09021 (12)	0.1337 (2)	0.02206 (12)	0.0570 (5)
H12	0.0378	0.0990	0.0174	0.068*
C13	0.15256 (12)	0.08717 (19)	−0.02586 (11)	0.0505 (5)
C14	0.23128 (11)	0.13987 (18)	−0.01877 (12)	0.0496 (5)
C15	0.24529 (11)	0.23674 (18)	0.03604 (11)	0.0494 (5)
H15	0.2977	0.2714	0.0405	0.059*
C16	0.37141 (14)	0.1250 (3)	−0.0603 (2)	0.1069 (11)
H16A	0.4061	0.0719	−0.0937	0.160*
H16B	0.3873	0.1169	−0.0038	0.160*
H16C	0.3770	0.2128	−0.0772	0.160*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0284 (7)	0.0681 (9)	0.0632 (8)	0.0049 (6)	0.0022 (5)	−0.0101 (7)
O2	0.0294 (7)	0.0634 (9)	0.0855 (10)	−0.0054 (6)	−0.0028 (6)	−0.0207 (8)
O3	0.0523 (9)	0.0907 (12)	0.0856 (11)	−0.0047 (8)	−0.0006 (8)	−0.0401 (9)
O4	0.0661 (10)	0.0756 (10)	0.0707 (10)	−0.0206 (8)	−0.0097 (7)	−0.0194 (8)
C1	0.0338 (9)	0.0456 (10)	0.0500 (10)	0.0044 (7)	−0.0024 (7)	−0.0103 (8)
C2	0.0275 (9)	0.0510 (10)	0.0550 (10)	0.0064 (7)	0.0007 (7)	−0.0087 (9)
C3	0.0290 (9)	0.0447 (10)	0.0530 (10)	−0.0026 (7)	−0.0014 (7)	−0.0011 (8)
C4	0.0373 (10)	0.0531 (11)	0.0629 (12)	−0.0020 (8)	0.0042 (8)	−0.0216 (9)
C5	0.0310 (9)	0.0517 (10)	0.0555 (11)	0.0030 (8)	0.0083 (7)	−0.0108 (9)
C6	0.0287 (8)	0.0403 (9)	0.0407 (9)	0.0004 (7)	0.0005 (6)	0.0004 (8)
C7	0.0303 (9)	0.0444 (9)	0.0452 (9)	0.0018 (7)	0.0005 (7)	0.0033 (8)
C8	0.0307 (9)	0.0561 (11)	0.0491 (10)	0.0000 (8)	−0.0005 (7)	−0.0049 (9)
C9	0.0342 (10)	0.0514 (10)	0.0520 (10)	−0.0002 (8)	−0.0001 (8)	0.0006 (9)
C10	0.0347 (9)	0.0494 (10)	0.0490 (10)	−0.0053 (8)	−0.0055 (8)	0.0043 (8)
C11	0.0390 (10)	0.0655 (12)	0.0524 (11)	−0.0099 (9)	−0.0016 (8)	0.0033 (10)
C12	0.0441 (11)	0.0695 (13)	0.0575 (12)	−0.0221 (10)	−0.0100 (9)	0.0057 (10)
C13	0.0516 (12)	0.0526 (11)	0.0475 (10)	−0.0106 (9)	−0.0139 (9)	0.0030 (9)
C14	0.0426 (11)	0.0545 (11)	0.0518 (10)	−0.0028 (9)	−0.0076 (8)	−0.0008 (9)
C15	0.0361 (9)	0.0552 (11)	0.0568 (11)	−0.0071 (8)	−0.0065 (8)	−0.0035 (9)
C16	0.0457 (14)	0.139 (3)	0.136 (3)	−0.0060 (15)	0.0096 (14)	−0.076 (2)

Geometric parameters (Å, º) top

O1—C7	1.2461 (19)	C7—C8	1.453 (2)
O2—C3	1.359 (2)	C8—C9	1.322 (2)
O2—H2O	0.871 (16)	C8—H8	0.9300
O3—C14	1.362 (2)	C9—C10	1.448 (2)
O3—C16	1.427 (3)	C9—H9	0.9300
O4—C13	1.358 (2)	C10—C11	1.388 (2)
O4—H4O	0.857 (17)	C10—C15	1.399 (2)
C1—C2	1.376 (2)	C11—C12	1.381 (3)
C1—C6	1.389 (2)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.370 (3)
C2—C3	1.372 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.399 (2)
C3—C4	1.383 (2)	C14—C15	1.368 (3)
C4—C5	1.375 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.386 (2)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—C7	1.473 (2)

C3—O2—H2O	109.3 (16)	C8—C9—C10	127.20 (17)
C14—O3—C16	117.46 (16)	C8—C9—H9	116.4
C13—O4—H4O	110 (2)	C10—C9—H9	116.4
C2—C1—C6	121.48 (16)	C11—C10—C15	118.20 (17)
C2—C1—H1	119.3	C11—C10—C9	119.54 (17)
C6—C1—H1	119.3	C15—C10—C9	122.21 (15)
C3—C2—C1	119.68 (16)	C12—C11—C10	120.65 (18)
C3—C2—H2	120.2	C12—C11—H11	119.7
C1—C2—H2	120.2	C10—C11—H11	119.7
O2—C3—C2	122.38 (15)	C13—C12—C11	120.68 (17)
O2—C3—C4	117.73 (16)	C13—C12—H12	119.7
C2—C3—C4	119.88 (15)	C11—C12—H12	119.7
C5—C4—C3	120.11 (17)	O4—C13—C12	119.51 (17)
C5—C4—H4	119.9	O4—C13—C14	120.99 (19)
C3—C4—H4	119.9	C12—C13—C14	119.50 (18)
C4—C5—C6	120.98 (16)	O3—C14—C15	126.17 (17)
C4—C5—H5	119.5	O3—C14—C13	114.04 (17)
C6—C5—H5	119.5	C15—C14—C13	119.79 (18)
C5—C6—C1	117.86 (15)	C14—C15—C10	121.17 (17)
C5—C6—C7	119.86 (15)	C14—C15—H15	119.4
C1—C6—C7	122.26 (15)	C10—C15—H15	119.4
O1—C7—C8	120.98 (15)	O3—C16—H16A	109.5
O1—C7—C6	119.90 (15)	O3—C16—H16B	109.5
C8—C7—C6	119.12 (14)	H16A—C16—H16B	109.5
C9—C8—C7	124.31 (16)	O3—C16—H16C	109.5
C9—C8—H8	117.8	H16A—C16—H16C	109.5
C7—C8—H8	117.8	H16B—C16—H16C	109.5

C6—C1—C2—C3	0.9 (3)	C8—C9—C10—C11	175.35 (19)
C1—C2—C3—O2	−179.82 (17)	C8—C9—C10—C15	−2.2 (3)
C1—C2—C3—C4	−0.7 (3)	C15—C10—C11—C12	0.6 (3)
O2—C3—C4—C5	179.66 (17)	C9—C10—C11—C12	−177.03 (17)
C2—C3—C4—C5	0.5 (3)	C10—C11—C12—C13	−0.3 (3)
C3—C4—C5—C6	−0.5 (3)	C11—C12—C13—O4	−179.87 (18)
C4—C5—C6—C1	0.8 (3)	C11—C12—C13—C14	−0.2 (3)
C4—C5—C6—C7	−177.68 (17)	C16—O3—C14—C15	5.9 (3)
C2—C1—C6—C5	−1.0 (3)	C16—O3—C14—C13	−173.8 (2)
C2—C1—C6—C7	177.44 (16)	O4—C13—C14—O3	−0.3 (3)
C5—C6—C7—O1	−7.4 (3)	C12—C13—C14—O3	−179.98 (18)
C1—C6—C7—O1	174.18 (16)	O4—C13—C14—C15	179.99 (17)
C5—C6—C7—C8	172.36 (16)	C12—C13—C14—C15	0.3 (3)
C1—C6—C7—C8	−6.0 (2)	O3—C14—C15—C10	−179.67 (18)
O1—C7—C8—C9	−10.4 (3)	C13—C14—C15—C10	0.0 (3)
C6—C7—C8—C9	169.82 (17)	C11—C10—C15—C14	−0.5 (3)
C7—C8—C9—C10	−176.97 (17)	C9—C10—C15—C14	177.08 (17)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3	0.86 (2)	2.20 (3)	2.655 (2)	113 (2)
O2—H2O···O1ⁱ	0.87 (2)	1.87 (2)	2.7349 (18)	173 (2)
O4—H4O···O1ⁱⁱ	0.86 (2)	2.22 (2)	2.937 (2)	141 (3)
C16—H16A···Cgⁱⁱ	0.96	2.86	3.747 (3)	155

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3	0.857 (17)	2.20 (3)	2.655 (2)	113 (2)
O2—H2O···O1ⁱ	0.871 (16)	1.868 (16)	2.7349 (18)	173 (2)
O4—H4O···O1ⁱⁱ	0.857 (17)	2.22 (2)	2.937 (2)	141 (3)
C16—H16A···Cgⁱⁱ	0.96	2.86	3.747 (3)	155

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.

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Volume 70| Part 5| May 2014| Pages o593-o594

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