(Z)-3-(1-Hy­droxy-3-oxobut-1-en­yl)-6-nitro-2H-chromen-2-one

Topno, N.S.; Tangeti, V.; Rao, H.S.P.; Krishna, R.

doi:10.1107/S1600536812051872

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o284

doi:10.1107/S1600536812051872

Open

access

(Z)-3-(1-Hydroxy-3-oxobut-1-enyl)-6-nitro-2H-chromen-2-one

Nishith Saurav Topno,^a Venkataswamy Tangeti,^b H. Surya Prakash Rao ^b ‡ and R. Krishna ^a ^*

^aCentre for Bioinformatics, School of Life Sciences, Pondicherry University, Puducherry 605 014, India, and ^bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
^*Correspondence e-mail: krishstrucbio@gmail.com

(Received 17 December 2012; accepted 26 December 2012; online 23 January 2013)

In the title compound, C₁₃H₉NO₆, the coumarin system has the benzene ring aligned at 0.61 (18)° with respect to the pyrone ring. An intramolecular O—H⋯O hydrogen bond stabilizes the molecular conformation and a C—H⋯O contact also occurs. In the crystal, weak C—H⋯O interactions link the molecules, forming inversion dimers.

Related literature

For the biological importance of flavinoids and coumarins, see: Murry et al. (1982 ); Andersen et al. (2006 ); Murakami et al. (2001 ); Wu et al. (2003 ). For their use as fluorescent probes and triplet sensitisers, see: Wagner (2009 ); Takadate et al. (1995 ). For a related structure, see: Da & Quan (2010 ).

Experimental

Crystal data

C₁₃H₉NO₆
M_r = 275.21
Triclinic, $[P \overline 1]$
a = 7.4591 (13) Å
b = 8.2178 (19) Å
c = 10.0087 (18) Å
α = 85.202 (17)°
β = 77.346 (15)°
γ = 89.278 (17)°
V = 596.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.4 × 0.32 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.917, T_max = 1.000
4789 measured reflections
2093 independent reflections
1395 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.170
S = 0.93
2093 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4	0.82	1.78	2.510 (2)	147
C11—H11⋯O2	0.93	2.24	2.870 (3)	125
C3—H3⋯O5ⁱ	0.93	2.58	3.308 (3)	136
C7—H7⋯O4ⁱⁱ	0.93	2.39	3.304 (3)	166
Symmetry codes: (i) -x+2, -y, -z; (ii) x, y-1, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051872/sj5289sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051872/sj5289Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051872/sj5289Isup3.cml

checkCIF report

Comment top

Coumarins are heterocyclic compounds belonging to the benzopyrone chemical class, well known to exhibit varied biological activities (Murry et al., 1982; Andersen et al., 2006). In the technological and medicinal fields, coumarins and flavones, independently, find extensive use (Murakami et al., 2001) (Wu et al., 2003), with activities reported for anti-HIV, anti-tumor, anti-cancer, anti-hypertension, anti-arrhythmia, anti-inflammatory, anti-osteoporosis, antiseptic, and analgesic uses. They are also known to be used as fluorescent probes and as triplet sensitizers, especially those having electronic push-pull characteristics (Wagner, 2009; Takadate et al., 1995). Considering the importance of coumarin derivatives, we report here the structure of the title compound. A structure related to the title compound has also been reported (Da & Quan, 2010).

The molecular structure of the title compound is shown in Fig.1. The pyrone ring and the benzene ring are essentially co-planar with a dihedral angle of 0.61 (18)° between them. The benzene ring orients in a (-)-anti-periplanar conformation with respect to the pyrone ring. The crystal packing is stabilized by intermolecular C₃—H₃···O₅, C₃—H₃···O₅ and C₇—H₇···O₄ bonds as shown in Fig.2 and Fig.3.

Related literature top

For the biological importance of flavinoids and coumarins, see: Murry et al. (1982); Andersen et al. (2006); Murakami et al. (2001); Wu et al. (2003). For their use as fluorescent probes and triplet sensitisers, see: Wagner (2009); Takadate et al. (1995). For a related structure, see: Da & Quan (2010).

Experimental top

A solution of 4-hydroxy-6-methyl-3-(2-(methylamino)-3,6-dinitro-4H-chromen-4-yl)-2H-pyran-2-one (0.010 g, 0.266 mmol) in ethanol (15 ml) was heated to reflux for 25 min by which time the reaction was complete (TLC; hexanes: EtOAc, 6:4). The compound was crystallized and separated by filtration with the help of cold ethanol (5 ml) to yield 93% of the product, a yellow crystalline solid, mp 121.6 °C; IR (KBr) υ_max cm^-1; ¹H NMR (400 MHz, DMSO-D₆) δ 15.71 (s, 1H), 8.70 (s, 1H), 8.58 (s, 1H), 8.49 (d, J = 9.0 Hz, 1H), 7.51 (d, J = 9.12 Hz, 1H), 6.98 (s, 1H), 2.29 (s, 3H) p.p.m.; ¹³C NMR (100 MHz, DMSO-D₆) δ 200.2, 171.1, 157.5, 153.3, 144.0, 136.6, 131.6, 121.8, 120.1, 118.4, 117.6, 102.0, 27.8 p.p.m..

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. View showing the weak C–H···O intermolecular interactions in compound (I).
	Fig. 3. Packing diagram of the title compound (I).

(Z)-3-(1-Hydroxy-3-oxobut-1-enyl)-6-nitro-2H-chromen-2-one top

Crystal data top

C₁₃H₉NO₆	Z = 2
M_r = 275.21	F(000) = 284
Triclinic, P1	D_x = 1.532 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4591 (13) Å	Cell parameters from 2257 reflections
b = 8.2178 (19) Å	θ = 3.1–29.1°
c = 10.0087 (18) Å	µ = 0.12 mm⁻¹
α = 85.202 (17)°	T = 293 K
β = 77.346 (15)°	Plate, colorless
γ = 89.278 (17)°	0.4 × 0.32 × 0.2 mm
V = 596.5 (2) Å³

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2093 independent reflections
Radiation source: fine-focus sealed tube	1395 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 15.9821 pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→8
T_min = 0.917, T_max = 1.000	l = −11→11
4789 measured reflections

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2093 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₃H₉NO₆	γ = 89.278 (17)°
M_r = 275.21	V = 596.5 (2) Å³
Triclinic, P1	Z = 2
a = 7.4591 (13) Å	Mo Kα radiation
b = 8.2178 (19) Å	µ = 0.12 mm⁻¹
c = 10.0087 (18) Å	T = 293 K
α = 85.202 (17)°	0.4 × 0.32 × 0.2 mm
β = 77.346 (15)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2093 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1395 reflections with I > 2σ(I)
T_min = 0.917, T_max = 1.000	R_int = 0.033
4789 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 0.93	Δρ_max = 0.18 e Å⁻³
2093 reflections	Δρ_min = −0.20 e Å⁻³
183 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	0.25449 (19)	0.17075 (18)	0.16604 (16)	0.0422 (5)
C4	0.5804 (3)	0.1391 (2)	0.1024 (2)	0.0306 (5)
C2	0.4261 (3)	0.3162 (2)	−0.0432 (2)	0.0318 (5)
C5	0.7376 (3)	0.0665 (2)	0.1335 (2)	0.0350 (6)
H5	0.8525	0.0887	0.0766	0.042*
C3	0.5812 (3)	0.2510 (2)	−0.0161 (2)	0.0329 (5)
H3	0.6927	0.2791	−0.0757	0.040*
C9	0.4119 (3)	0.1020 (3)	0.1911 (2)	0.0337 (5)
O3	0.6017 (2)	0.4703 (2)	−0.23192 (17)	0.0497 (5)
H3A	0.5984	0.5364	−0.2974	0.075*
O4	0.4619 (3)	0.6406 (2)	−0.40237 (18)	0.0584 (6)
C11	0.2837 (3)	0.4849 (3)	−0.2152 (2)	0.0417 (6)
H11	0.1660	0.4551	−0.1668	0.050*
C6	0.7191 (3)	−0.0382 (3)	0.2494 (2)	0.0367 (6)
C8	0.3959 (3)	−0.0051 (3)	0.3076 (2)	0.0402 (6)
H8	0.2815	−0.0284	0.3648	0.048*
O2	0.1007 (2)	0.3272 (2)	0.04475 (19)	0.0620 (6)
C10	0.4319 (3)	0.4287 (2)	−0.1671 (2)	0.0344 (6)
N1	0.8848 (3)	−0.1149 (2)	0.2826 (2)	0.0474 (6)
C7	0.5514 (3)	−0.0762 (3)	0.3373 (2)	0.0393 (6)
H7	0.5444	−0.1485	0.4149	0.047*
C1	0.2494 (3)	0.2775 (3)	0.0523 (2)	0.0394 (6)
O6	0.8773 (3)	−0.1692 (3)	0.3998 (2)	0.0900 (8)
O5	1.0203 (2)	−0.1232 (2)	0.1907 (2)	0.0639 (6)
C13	0.1405 (4)	0.6402 (4)	−0.3939 (3)	0.0728 (9)
H13A	0.1784	0.6891	−0.4863	0.109*
H13B	0.0716	0.7180	−0.3369	0.109*
H13C	0.0651	0.5462	−0.3932	0.109*
C12	0.3071 (4)	0.5893 (3)	−0.3397 (3)	0.0474 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0340 (9)	0.0494 (10)	0.0382 (10)	0.0047 (7)	−0.0036 (7)	0.0134 (7)
C4	0.0345 (12)	0.0279 (12)	0.0291 (12)	−0.0022 (8)	−0.0071 (9)	0.0012 (8)
C2	0.0367 (12)	0.0279 (12)	0.0297 (13)	−0.0012 (9)	−0.0064 (10)	0.0017 (9)
C5	0.0315 (12)	0.0373 (13)	0.0348 (13)	−0.0012 (9)	−0.0054 (10)	0.0014 (10)
C3	0.0332 (12)	0.0324 (12)	0.0302 (12)	−0.0031 (9)	−0.0022 (9)	0.0024 (9)
C9	0.0344 (12)	0.0354 (12)	0.0308 (12)	0.0018 (9)	−0.0076 (9)	0.0013 (9)
O3	0.0494 (11)	0.0562 (12)	0.0381 (11)	−0.0036 (8)	−0.0053 (8)	0.0177 (8)
O4	0.0770 (13)	0.0554 (12)	0.0395 (11)	−0.0030 (9)	−0.0123 (9)	0.0143 (8)
C11	0.0491 (15)	0.0397 (14)	0.0365 (14)	0.0011 (10)	−0.0135 (11)	0.0062 (10)
C6	0.0406 (13)	0.0361 (13)	0.0363 (13)	0.0046 (9)	−0.0156 (10)	−0.0016 (9)
C8	0.0383 (13)	0.0486 (14)	0.0295 (13)	−0.0025 (10)	−0.0022 (10)	0.0068 (10)
O2	0.0348 (10)	0.0816 (14)	0.0625 (13)	0.0106 (8)	−0.0080 (8)	0.0261 (10)
C10	0.0436 (13)	0.0297 (12)	0.0287 (12)	−0.0019 (9)	−0.0059 (10)	0.0003 (9)
N1	0.0478 (13)	0.0527 (13)	0.0445 (13)	0.0056 (9)	−0.0198 (10)	0.0041 (10)
C7	0.0482 (14)	0.0403 (13)	0.0283 (13)	0.0022 (10)	−0.0089 (10)	0.0049 (9)
C1	0.0409 (13)	0.0405 (14)	0.0342 (13)	0.0030 (10)	−0.0066 (10)	0.0065 (10)
O6	0.0764 (15)	0.142 (2)	0.0506 (13)	0.0326 (14)	−0.0257 (11)	0.0264 (13)
O5	0.0431 (11)	0.0806 (14)	0.0632 (14)	0.0153 (9)	−0.0091 (9)	0.0125 (10)
C13	0.090 (2)	0.078 (2)	0.0564 (19)	0.0096 (16)	−0.0389 (17)	0.0148 (15)
C12	0.0694 (18)	0.0401 (14)	0.0362 (14)	0.0019 (12)	−0.0209 (13)	0.0022 (11)

Geometric parameters (Å, º) top

O1—C9	1.360 (3)	C11—C12	1.432 (3)
O1—C1	1.385 (3)	C11—H11	0.9300
C4—C9	1.391 (3)	C6—C7	1.384 (3)
C4—C5	1.392 (3)	C6—N1	1.470 (3)
C4—C3	1.438 (3)	C8—C7	1.370 (3)
C2—C3	1.341 (3)	C8—H8	0.9300
C2—C1	1.470 (3)	O2—O2	0.0000
C2—C10	1.476 (3)	O2—C1	1.192 (3)
C5—C6	1.368 (3)	N1—O6	1.210 (3)
C5—H5	0.9300	N1—O5	1.214 (2)
C3—H3	0.9300	C7—H7	0.9300
C9—C8	1.385 (3)	C1—O2	1.192 (3)
O3—C10	1.325 (3)	C13—C12	1.502 (4)
O3—H3A	0.8200	C13—H13A	0.9600
O4—O4	0.000 (5)	C13—H13B	0.9600
O4—C12	1.247 (3)	C13—H13C	0.9600
C11—C10	1.361 (3)	C12—O4	1.247 (3)

C9—O1—C1	123.35 (17)	O3—C10—C11	121.5 (2)
C9—C4—C5	118.4 (2)	O3—C10—C2	112.69 (18)
C9—C4—C3	117.68 (19)	C11—C10—C2	125.8 (2)
C5—C4—C3	123.93 (19)	O6—N1—O5	123.5 (2)
C3—C2—C1	119.73 (19)	O6—N1—C6	118.0 (2)
C3—C2—C10	120.49 (19)	O5—N1—C6	118.4 (2)
C1—C2—C10	119.77 (18)	C8—C7—C6	118.7 (2)
C6—C5—C4	118.5 (2)	C8—C7—H7	120.7
C6—C5—H5	120.8	C6—C7—H7	120.7
C4—C5—H5	120.8	O2—C1—O2	0.00 (18)
C2—C3—C4	121.97 (19)	O2—C1—O1	115.3 (2)
C2—C3—H3	119.0	O2—C1—O1	115.3 (2)
C4—C3—H3	119.0	O2—C1—C2	128.1 (2)
O1—C9—C8	117.09 (19)	O2—C1—C2	128.1 (2)
O1—C9—C4	120.68 (19)	O1—C1—C2	116.55 (18)
C8—C9—C4	122.2 (2)	C12—C13—H13A	109.5
C10—O3—H3A	109.5	C12—C13—H13B	109.5
O4—O4—C12	0 (10)	H13A—C13—H13B	109.5
C10—C11—C12	120.7 (2)	C12—C13—H13C	109.5
C10—C11—H11	119.7	H13A—C13—H13C	109.5
C12—C11—H11	119.7	H13B—C13—H13C	109.5
C5—C6—C7	123.2 (2)	O4—C12—O4	0.0 (2)
C5—C6—N1	118.6 (2)	O4—C12—C11	121.4 (2)
C7—C6—N1	118.2 (2)	O4—C12—C11	121.4 (2)
C7—C8—C9	119.0 (2)	O4—C12—C13	119.6 (2)
C7—C8—H8	120.5	O4—C12—C13	119.6 (2)
C9—C8—H8	120.5	C11—C12—C13	119.0 (3)
O2—O2—C1	0 (10)

C9—C4—C5—C6	0.2 (3)	C7—C6—N1—O6	−20.2 (4)
C3—C4—C5—C6	180.0 (2)	C5—C6—N1—O5	−21.4 (3)
C1—C2—C3—C4	2.1 (3)	C7—C6—N1—O5	158.3 (2)
C10—C2—C3—C4	−179.02 (19)	C9—C8—C7—C6	0.0 (4)
C9—C4—C3—C2	−1.2 (3)	C5—C6—C7—C8	−0.4 (4)
C5—C4—C3—C2	178.94 (19)	N1—C6—C7—C8	179.8 (2)
C1—O1—C9—C8	−178.8 (2)	O2—O2—C1—O1	0.00 (3)
C1—O1—C9—C4	1.2 (3)	O2—O2—C1—C2	0.00 (10)
C5—C4—C9—O1	179.40 (19)	C9—O1—C1—O2	179.87 (19)
C3—C4—C9—O1	−0.4 (3)	C9—O1—C1—O2	179.87 (19)
C5—C4—C9—C8	−0.6 (3)	C9—O1—C1—C2	−0.4 (3)
C3—C4—C9—C8	179.6 (2)	C3—C2—C1—O2	178.4 (2)
C4—C5—C6—C7	0.3 (4)	C10—C2—C1—O2	−0.5 (4)
C4—C5—C6—N1	−179.93 (18)	C3—C2—C1—O2	178.4 (2)
O1—C9—C8—C7	−179.48 (18)	C10—C2—C1—O2	−0.5 (4)
C4—C9—C8—C7	0.5 (4)	C3—C2—C1—O1	−1.2 (3)
C12—C11—C10—O3	1.0 (4)	C10—C2—C1—O1	179.84 (19)
C12—C11—C10—C2	−177.7 (2)	O4—O4—C12—C11	0.00 (14)
C3—C2—C10—O3	−8.2 (3)	O4—O4—C12—C13	0.00 (10)
C1—C2—C10—O3	170.69 (19)	C10—C11—C12—O4	−4.9 (4)
C3—C2—C10—C11	170.6 (2)	C10—C11—C12—O4	−4.9 (4)
C1—C2—C10—C11	−10.5 (3)	C10—C11—C12—C13	176.3 (2)
C5—C6—N1—O6	160.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.78	2.510 (2)	147
C11—H11···O2	0.93	2.24	2.870 (3)	125
C3—H3···O5ⁱ	0.93	2.58	3.308 (3)	136
C7—H7···O4ⁱⁱ	0.93	2.39	3.304 (3)	166

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

Experimental details

Crystal data
Chemical formula	C₁₃H₉NO₆
M_r	275.21
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4591 (13), 8.2178 (19), 10.0087 (18)
α, β, γ (°)	85.202 (17), 77.346 (15), 89.278 (17)
V (Å³)	596.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.4 × 0.32 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.917, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4789, 2093, 1395
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.170, 0.93
No. of reflections	2093
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.78	2.510 (2)	147.3
C11—H11···O2	0.93	2.24	2.870 (3)	124.5
C3—H3···O5ⁱ	0.93	2.58	3.308 (3)	135.7
C7—H7···O4ⁱⁱ	0.93	2.39	3.304 (3)	165.9

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

Footnotes

‡Additional correspondence author, e-mail: hspr@yahoo.com.

Acknowledgements

RK thanks the Department of Biotechnology and the Department of Information Technology, Government of India, New Delhi, for their financial support of the Centre for Bioinformatics, Pondicherry University, Puducherry. NST [No. F. 14–2(ST)/2010 (SA-III)] thanks the UGC for a Rajiv Gandhi National Fellowship to pursue his PhD degree. HSPR and VT thank the Council for Scientific and Industrial Research (CSIR), New Delhi, for financial support.

References

Andersen, M. & Markham, K. R. (2006). In Flavonoids: Chemistry, Biochemistry and Applications. Boca Raton: CRC Press. Google Scholar
Da, Y.-X. & Quan, Z.-J. (2010). Acta Cryst. E66, o2872. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Murakami, A., Yamayoshi, A., Iwase, R., Nishida, J., Yamaoka, T. & Wake, N. (2001). Eur. J. Pharm. Sci. 13, 25–34. Web of Science CrossRef PubMed CAS Google Scholar
Murry, R. D. H., Mendez, J. & Brown, S. A. (1982). In The Natural Coumarins: Occurrence, Chemistry and Biochemistry. New York: John Wiley & Sons. Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takadate, A., Masuda, T., Murata, C., Tanaka, T., Irikura, M. & Goya, S. (1995). Anal. Sci. 11, 97–101. CrossRef CAS Web of Science Google Scholar
Wagner, B. D. (2009). Molecules, 14, 210–237. Web of Science CrossRef PubMed CAS Google Scholar
Wu, J. Y., Fong, W. F., Zhang, J. X., Leung, C. H., Kwong, H. L. & Yang, M. S. (2003). Eur. J. Pharmacol. 473, 9–17. Web of Science CrossRef PubMed CAS Google Scholar