2-(2,6-Dimethoxy­phen­yl)-5-hydr­oxy-7-meth­oxy-4H-1-benzopyran-4-one

Ravi Kumar, R.; Krishnaiah, M.; Jagadesh Kumar, N.; Gunasekhar Reddy, D.; Puranik, V.G.

doi:10.1107/S1600536809032383

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2262

doi:10.1107/S1600536809032383

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2-(2,6-Dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one

R. Ravi Kumar,^a M. Krishnaiah,^a N. Jagadesh Kumar,^a D. Gunasekhar Reddy ^b and V. G. Puranik ^c ^*

^aDepartment of Physics, S. V. University, Tirupati 517 502, India, ^bDepartment of Chemistry, S. V. University, Tirupati 517 502, India, and ^cCentre of Material Characterisation, National Chemical Laboratory, Pune 411 008, India
^*Correspondence e-mail: mkphysvu@yahoo.co.in

(Received 6 July 2009; accepted 15 August 2009; online 29 August 2009)

In the title compound, C₁₈H₁₆O₆, the dimethoxyphenyl ring is rotated by 61.8 (1)° from the plane of the benzopyran system. The molecule is stabilized by an intramolecular O—H⋯O hydrogen bond.

Related literature

The title compound, along with a terpinoid and six other flavonoids, was isolated from the roots and the aerial parts of Andrographis peniculata Nees (Reddy et al., 2003 ), a herb widely distributed in the plains of India and Sri Lanka (Gamble, 1956 ). In traditional Indian medicine, the whole plant of A. peniculata is extensively used in the treatment of dyspepsia, dysentery, malaria, respiratory infections and as an antidote for snake bites, see: Kirtikar & Basu (1975 ); Chopra et al. (1980 ).

Experimental

Crystal data

C₁₈H₁₆O₆
M_r = 328.31
Monoclinic, P 2₁ /n
a = 11.003 (7) Å
b = 11.015 (7) Å
c = 13.734 (9) Å
β = 113.159 (10)°
V = 1530.4 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.69 × 0.37 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.929, T_max = 0.969
7431 measured reflections
2675 independent reflections
2300 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 1.04
2675 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O4	0.82	1.82	2.560 (2)	149

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002 ); data reduction: SAINT; 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, 1999 ); software used to prepare material for publication: enCIFer (Allen et al., 2004 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032383/hg2533sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032383/hg2533Isup2.hkl

checkCIF report

Comment top

The title compound along with a terpinoid and six other flavonoids were isolated from the roots and the aerial parts of Andrographis peniculata Nees (Reddy et al., 2003), an erect herb widely distributed in the plains throughout India and Srilanka (Gamble, 1956). In traditional Indian medicine the whole plant of A. peniculata is extensively used in the treatment of dyspepsia, dysentery, malaria, respiratory infections and as an antidote for snake bites (Kirtikar & Basu, 1975; Chopra et al., 1980). As a part of our ongoing investigation on medicinal plants, we report the structure of the title compound (I) (Fig.1).

The benzopyran ring is slightly planar with a maximum deviation from the plane of 0.034 (1) Å. The dihedral angle between the least-squares planes of the phenyl ring and the benzopyran moiety is 61.8 (1)°. The non planarity of the phenolic ring is due to the presence of the steric hindrance caused by 2',6' dioxygenation resulting the decrease in the conjugation of the phenyl ring with the carbonyl group. The absence of conjugation means that there will be more delocalization of π-electrons in C2, C3, C4, and O4 unit. The C2–C1' bond length (1.475 (2)Å) is within the 3σ of the average 4sp²-4sp³ bond distance of 1.48 Å.

Related literature top

The title compound, along with a terpinoid and six other flavonoids, was isolated from the roots and the aerial parts of Andrographis peniculata Nees (Reddy et al., 2003), a herb widely distributed in the plains of India and Sri Lanka (Gamble, 1956). In traditional Indian medicine, the whole plant of A. peniculata is extensively used in the treatment of dyspepsia, dysentery, malaria, respiratory infections and as an antidote for snake bites, see: Kirtikar & Basu (1975); Chopra et al. (1980).

Experimental top

The shade dried and powdered roots of whole plant of A. paniculata Nees (3 kg) was successively extracted with n-hexane, Me₂CO and MeOH. The acetone extract on purification over a silica gel column using n-hexane EtoAc step gradients yielded 18 mg of the title compound with a m.p. of 196–198°C and recrystalized by slow evaporation from a hexane solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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, 1999); software used to prepare material for publication: enCIFer (Allen et al., 2004) and PARST (Nardelli, 1995).

Figures top

Fig. 1. View of the molecule showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary radius.

2-(2,6-Dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one top

Crystal data top

C₁₈H₁₆O₆	F(000) = 688
M_r = 328.31	D_x = 1.425 Mg m⁻³ D_m = 1.42 Mg m⁻³ D_m measured by none
Monoclinic, P2₁/n	Melting point: 469 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.003 (7) Å	Cell parameters from 25 reflections
b = 11.015 (7) Å	θ = 2–25°
c = 13.734 (9) Å	µ = 0.11 mm⁻¹
β = 113.159 (10)°	T = 295 K
V = 1530.4 (17) Å³	Needle, colourless
Z = 4	0.69 × 0.37 × 0.36 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2675 independent reflections
Radiation source: fine-focus sealed tube	2300 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
ω scans	h = −7→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −13→13
T_min = 0.929, T_max = 0.969	l = −16→16
7431 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0462P)² + 0.3516P] where P = (F_o² + 2F_c²)/3
2675 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₁₆O₆	V = 1530.4 (17) Å³
M_r = 328.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.003 (7) Å	µ = 0.11 mm⁻¹
b = 11.015 (7) Å	T = 295 K
c = 13.734 (9) Å	0.69 × 0.37 × 0.36 mm
β = 113.159 (10)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2675 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2300 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.969	R_int = 0.023
7431 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
2675 reflections	Δρ_min = −0.18 e Å⁻³
221 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 ?t 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	0.95634 (9)	0.63933 (8)	0.16154 (8)	0.0376 (3)
C2	0.97394 (14)	0.75775 (13)	0.14376 (12)	0.0361 (3)
C3	1.06401 (15)	0.79404 (13)	0.10773 (12)	0.0412 (4)
H3	1.0720	0.8764	0.0967	0.049*
C4	1.14884 (15)	0.71009 (13)	0.08555 (12)	0.0391 (3)
O4	1.23188 (12)	0.74190 (10)	0.04933 (10)	0.0526 (3)
C5	1.13251 (14)	0.58600 (13)	0.10870 (11)	0.0350 (3)
C6	1.21312 (15)	0.49245 (14)	0.09621 (12)	0.0393 (3)
O6	1.30566 (12)	0.52024 (11)	0.05872 (11)	0.0560 (3)
H6	1.3026	0.5931	0.0458	0.084*
C7	1.19766 (16)	0.37579 (14)	0.12164 (12)	0.0436 (4)
H7	1.2524	0.3151	0.1146	0.052*
C8	1.09978 (15)	0.34760 (13)	0.15815 (12)	0.0403 (3)
O8	1.09338 (12)	0.22951 (9)	0.18118 (10)	0.0537 (3)
C9	1.01709 (14)	0.43571 (13)	0.16945 (11)	0.0375 (3)
H9	0.9506	0.4162	0.1926	0.045*
C5A	1.03645 (13)	0.55351 (13)	0.14532 (11)	0.0333 (3)
C10	0.9930 (2)	0.19296 (17)	0.21541 (17)	0.0638 (5)
H10A	1.0044	0.2346	0.2798	0.096*
H10B	0.9987	0.1070	0.2278	0.096*
H10C	0.9080	0.2125	0.1618	0.096*
C1'	0.88314 (14)	0.83990 (13)	0.16728 (12)	0.0376 (3)
C2'	0.88837 (14)	0.85308 (13)	0.26936 (12)	0.0396 (4)
O2'	0.97735 (11)	0.78129 (10)	0.34356 (8)	0.0467 (3)
C3'	0.80767 (16)	0.93686 (15)	0.28990 (14)	0.0479 (4)
H3'	0.8119	0.9467	0.3584	0.057*
C4'	0.72169 (17)	1.00504 (15)	0.20869 (15)	0.0521 (4)
H4'	0.6680	1.0613	0.2231	0.063*
C5'	0.71262 (16)	0.99273 (14)	0.10730 (14)	0.0493 (4)
H5'	0.6523	1.0388	0.0530	0.059*
C6'	0.79435 (15)	0.91074 (14)	0.08648 (13)	0.0426 (4)
O6'	0.79624 (13)	0.89242 (11)	−0.00985 (9)	0.0594 (3)
C12	0.70572 (18)	0.95611 (16)	−0.09779 (14)	0.0551 (4)
H12A	0.6172	0.9317	−0.1097	0.083*
H12B	0.7232	0.9381	−0.1595	0.083*
H12C	0.7152	1.0418	−0.0840	0.083*
C11	0.99169 (19)	0.79582 (17)	0.44992 (13)	0.0557 (5)
H11A	1.0145	0.8785	0.4713	0.084*
H11B	1.0603	0.7430	0.4947	0.084*
H11C	0.9100	0.7757	0.4558	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0400 (6)	0.0327 (5)	0.0456 (6)	0.0029 (4)	0.0227 (5)	−0.0012 (4)
C2	0.0384 (8)	0.0313 (7)	0.0373 (8)	0.0008 (6)	0.0135 (6)	−0.0020 (6)
C3	0.0455 (9)	0.0317 (8)	0.0498 (9)	0.0011 (6)	0.0223 (7)	0.0006 (7)
C4	0.0404 (8)	0.0408 (8)	0.0390 (8)	−0.0015 (7)	0.0187 (7)	−0.0003 (7)
O4	0.0583 (7)	0.0444 (6)	0.0717 (8)	−0.0006 (5)	0.0435 (7)	0.0037 (6)
C5	0.0362 (7)	0.0364 (8)	0.0322 (7)	0.0005 (6)	0.0132 (6)	−0.0025 (6)
C6	0.0388 (8)	0.0418 (8)	0.0404 (8)	0.0018 (6)	0.0188 (7)	−0.0038 (7)
O6	0.0579 (7)	0.0495 (7)	0.0795 (8)	0.0053 (6)	0.0474 (7)	0.0004 (6)
C7	0.0447 (9)	0.0378 (8)	0.0496 (9)	0.0081 (7)	0.0200 (7)	−0.0040 (7)
C8	0.0442 (8)	0.0336 (8)	0.0394 (8)	0.0001 (7)	0.0127 (7)	−0.0025 (7)
O8	0.0639 (8)	0.0317 (6)	0.0708 (8)	0.0032 (5)	0.0323 (7)	0.0043 (5)
C9	0.0387 (8)	0.0360 (8)	0.0395 (8)	−0.0017 (6)	0.0172 (7)	−0.0011 (6)
C5A	0.0340 (7)	0.0334 (7)	0.0317 (7)	0.0024 (6)	0.0120 (6)	−0.0037 (6)
C10	0.0678 (12)	0.0427 (10)	0.0818 (13)	−0.0062 (9)	0.0305 (11)	0.0124 (10)
C1'	0.0361 (8)	0.0315 (7)	0.0463 (8)	−0.0001 (6)	0.0176 (7)	−0.0041 (7)
C2'	0.0389 (8)	0.0347 (8)	0.0493 (9)	−0.0009 (6)	0.0217 (7)	0.0001 (7)
O2'	0.0522 (6)	0.0483 (7)	0.0443 (6)	0.0107 (5)	0.0242 (5)	0.0017 (5)
C3'	0.0542 (10)	0.0445 (9)	0.0574 (10)	0.0042 (8)	0.0353 (9)	−0.0015 (8)
C4'	0.0529 (10)	0.0408 (9)	0.0753 (12)	0.0102 (8)	0.0388 (10)	0.0004 (9)
C5'	0.0445 (9)	0.0408 (9)	0.0623 (11)	0.0094 (7)	0.0207 (8)	0.0033 (8)
C6'	0.0418 (8)	0.0356 (8)	0.0487 (9)	0.0010 (7)	0.0162 (7)	−0.0045 (7)
O6'	0.0695 (8)	0.0590 (8)	0.0417 (6)	0.0255 (6)	0.0131 (6)	−0.0009 (6)
C12	0.0575 (10)	0.0465 (10)	0.0509 (10)	0.0044 (8)	0.0101 (8)	0.0066 (8)
C11	0.0676 (11)	0.0585 (11)	0.0481 (10)	0.0069 (9)	0.0301 (9)	0.0014 (8)

Geometric parameters (Å, º) top

O1—C2	1.3549 (19)	C10—H10B	0.9600
O1—C5A	1.3692 (17)	C10—H10C	0.9600
C2—C3	1.331 (2)	C1'—C2'	1.388 (2)
C2—C1'	1.475 (2)	C1'—C6'	1.394 (2)
C3—C4	1.429 (2)	C2'—O2'	1.3555 (19)
C3—H3	0.9300	C2'—C3'	1.384 (2)
C4—O4	1.2500 (18)	O2'—C11	1.415 (2)
C4—C5	1.431 (2)	C3'—C4'	1.369 (2)
C5—C5A	1.384 (2)	C3'—H3'	0.9300
C5—C6	1.413 (2)	C4'—C5'	1.363 (3)
C6—O6	1.3445 (18)	C4'—H4'	0.9300
C6—C7	1.360 (2)	C5'—C6'	1.381 (2)
O6—H6	0.8200	C5'—H5'	0.9300
C7—C8	1.390 (2)	C6'—O6'	1.346 (2)
C7—H7	0.9300	O6'—C12	1.413 (2)
C8—O8	1.347 (2)	C12—H12A	0.9600
C8—C9	1.380 (2)	C12—H12B	0.9600
O8—C10	1.418 (2)	C12—H12C	0.9600
C9—C5A	1.376 (2)	C11—H11A	0.9600
C9—H9	0.9300	C11—H11B	0.9600
C10—H10A	0.9600	C11—H11C	0.9600

C2—O1—C5A	119.25 (11)	H10A—C10—H10C	109.5
C3—C2—O1	122.42 (13)	H10B—C10—H10C	109.5
C3—C2—C1'	124.37 (14)	C2'—C1'—C6'	118.90 (13)
O1—C2—C1'	113.21 (12)	C2'—C1'—C2	121.52 (13)
C2—C3—C4	121.93 (14)	C6'—C1'—C2	119.49 (13)
C2—C3—H3	119.0	O2'—C2'—C3'	124.56 (14)
C4—C3—H3	119.0	O2'—C2'—C1'	115.41 (13)
O4—C4—C3	122.98 (14)	C3'—C2'—C1'	120.03 (14)
O4—C4—C5	122.11 (13)	C2'—O2'—C11	117.66 (12)
C3—C4—C5	114.91 (13)	C4'—C3'—C2'	119.54 (15)
C5A—C5—C6	117.44 (13)	C4'—C3'—H3'	120.2
C5A—C5—C4	120.55 (13)	C2'—C3'—H3'	120.2
C6—C5—C4	122.00 (13)	C5'—C4'—C3'	121.82 (15)
O6—C6—C7	120.24 (13)	C5'—C4'—H4'	119.1
O6—C6—C5	119.10 (14)	C3'—C4'—H4'	119.1
C7—C6—C5	120.66 (14)	C4'—C5'—C6'	118.98 (16)
C6—O6—H6	109.5	C4'—C5'—H5'	120.5
C6—C7—C8	119.78 (14)	C6'—C5'—H5'	120.5
C6—C7—H7	120.1	O6'—C6'—C5'	124.35 (15)
C8—C7—H7	120.1	O6'—C6'—C1'	114.93 (13)
O8—C8—C9	123.71 (14)	C5'—C6'—C1'	120.72 (15)
O8—C8—C7	114.82 (13)	C6'—O6'—C12	119.16 (13)
C9—C8—C7	121.46 (14)	O6'—C12—H12A	109.5
C8—O8—C10	118.13 (13)	O6'—C12—H12B	109.5
C5A—C9—C8	117.69 (14)	H12A—C12—H12B	109.5
C5A—C9—H9	121.2	O6'—C12—H12C	109.5
C8—C9—H9	121.2	H12A—C12—H12C	109.5
O1—C5A—C9	116.19 (13)	H12B—C12—H12C	109.5
O1—C5A—C5	120.86 (13)	O2'—C11—H11A	109.5
C9—C5A—C5	122.94 (13)	O2'—C11—H11B	109.5
O8—C10—H10A	109.5	H11A—C11—H11B	109.5
O8—C10—H10B	109.5	O2'—C11—H11C	109.5
H10A—C10—H10B	109.5	H11A—C11—H11C	109.5
O8—C10—H10C	109.5	H11B—C11—H11C	109.5

C5A—O1—C2—C3	2.1 (2)	C6—C5—C5A—O1	178.64 (12)
C5A—O1—C2—C1'	−178.43 (12)	C4—C5—C5A—O1	−0.9 (2)
O1—C2—C3—C4	−0.2 (2)	C6—C5—C5A—C9	0.0 (2)
C1'—C2—C3—C4	−179.53 (14)	C4—C5—C5A—C9	−179.56 (14)
C2—C3—C4—O4	178.26 (15)	C3—C2—C1'—C2'	−115.93 (18)
C2—C3—C4—C5	−2.2 (2)	O1—C2—C1'—C2'	64.66 (18)
O4—C4—C5—C5A	−177.77 (14)	C3—C2—C1'—C6'	60.8 (2)
C3—C4—C5—C5A	2.7 (2)	O1—C2—C1'—C6'	−118.64 (15)
O4—C4—C5—C6	2.7 (2)	C6'—C1'—C2'—O2'	−179.85 (13)
C3—C4—C5—C6	−176.84 (14)	C2—C1'—C2'—O2'	−3.1 (2)
C5A—C5—C6—O6	178.63 (13)	C6'—C1'—C2'—C3'	−1.0 (2)
C4—C5—C6—O6	−1.8 (2)	C2—C1'—C2'—C3'	175.73 (14)
C5A—C5—C6—C7	−1.4 (2)	C3'—C2'—O2'—C11	−2.1 (2)
C4—C5—C6—C7	178.17 (15)	C1'—C2'—O2'—C11	176.67 (14)
O6—C6—C7—C8	−178.61 (14)	O2'—C2'—C3'—C4'	179.69 (15)
C5—C6—C7—C8	1.4 (2)	C1'—C2'—C3'—C4'	0.9 (2)
C6—C7—C8—O8	−179.87 (14)	C2'—C3'—C4'—C5'	0.2 (3)
C6—C7—C8—C9	0.0 (2)	C3'—C4'—C5'—C6'	−1.2 (3)
C9—C8—O8—C10	2.3 (2)	C4'—C5'—C6'—O6'	−178.63 (15)
C7—C8—O8—C10	−177.86 (15)	C4'—C5'—C6'—C1'	1.2 (2)
O8—C8—C9—C5A	178.53 (14)	C2'—C1'—C6'—O6'	179.76 (13)
C7—C8—C9—C5A	−1.3 (2)	C2—C1'—C6'—O6'	3.0 (2)
C2—O1—C5A—C9	177.17 (13)	C2'—C1'—C6'—C5'	−0.1 (2)
C2—O1—C5A—C5	−1.57 (19)	C2—C1'—C6'—C5'	−176.86 (14)
C8—C9—C5A—O1	−177.40 (12)	C5'—C6'—O6'—C12	−2.9 (2)
C8—C9—C5A—C5	1.3 (2)	C1'—C6'—O6'—C12	177.24 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O4	0.82	1.82	2.560 (2)	149

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆O₆
M_r	328.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	11.003 (7), 11.015 (7), 13.734 (9)
β (°)	113.159 (10)
V (Å³)	1530.4 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.69 × 0.37 × 0.36

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.929, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	7431, 2675, 2300
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.04
No. of reflections	2675
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999), enCIFer (Allen et al., 2004) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O4	0.82	1.82	2.560 (2)	148.8

Acknowledgements

MK thanks the University Grants Commission, New Delhi, for financial support as a major project.

References

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