[4-(4-Meth­oxy­phen­yl)-1-methyl-3-nitro­pyrrolidin-3-yl]methanol

Prathebha, K.; Sathya, S.; Usha, G.; Sivakumar, N.; Bakthadoss, M.

doi:10.1107/S1600536813003073

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o372

doi:10.1107/S1600536813003073

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[4-(4-Methoxyphenyl)-1-methyl-3-nitropyrrolidin-3-yl]methanol

K. Prathebha,^a S. Sathya,^a G. Usha,^a ^* N. Sivakumar ^b and M. Bakthadoss ^b

^aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

(Received 20 November 2012; accepted 30 January 2013; online 9 February 2013)

In the title compound, C₁₃H₁₈N₂O₄, the dihedral angle between the benzene and pyrrolidine (all atoms) rings is 70.6 (1)°. The pyrrolidine ring adopts a half-chair conformation. In the crystal, molecules form chains along the c-axis direction linked by O—H⋯N hydrogen bonds, which are then connected by C—H⋯O interactions, forming a sheet parallel to the bc plane.

Related literature

For information on the pyrrolidine ring in biologically active natural compounds, see: Gu et al. (2004 ). For the use of pyrrolidine-containing molecules in the treatment of diseases, see, for example: Horri et al. (1986 ) for diabetes and Karpas et al. (1988 ) for viral infections. For bond lengths in a related structure, see: Jayabharathi et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₈N₂O₄
M_r = 266.29
Monoclinic, P 2₁ /c
a = 11.6827 (10) Å
b = 11.1912 (11) Å
c = 11.1789 (11) Å
β = 109.118 (2)°
V = 1381.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
12464 measured reflections
3407 independent reflections
2282 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.162
S = 1.01
3407 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1ⁱ	0.82	2.01	2.8237 (16)	170
C1—H1A⋯O2ⁱⁱ	0.96	2.51	3.390 (2)	153
C3—H3⋯O3ⁱⁱⁱ	0.93	2.51	3.429 (2)	171
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813003073/nk2193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003073/nk2193Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003073/nk2193Isup3.cml

checkCIF report

Comment top

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

Pyrrolidine ring is present in many biologically active natural compounds and pharmaceuticals (Gu et al., 2004), and find utility in the treatment of diseases such as diabetes (Horri et al.,1986), and viral infections (Karpas et al., 1988).

The bond lengths C8—C13 = 1.525 (2) Å; C13—N1=1.460 (2) Å; C11—N1 = 1.462 (2) Å; C11—C9= 1.520 (2) Å; C8—C9= 1.566 (2) Å are longer than the normal values but are comparable with the values of such distances in the reported structure (Jayabharathi et al., 2009). This may be due to the steric forces caused by the bulky group at C8 and C9 of pyrrolidine moiety. C1—O1 [1.416 (3) Å] is longer than C2—O1 [1.367 (2) Å]; this may be due the end atom C1.The dihedral angle between phenyl and pyrrolidine ring is 70.6 (1)°. The sum of angles around N3 [360°] and N1[329.1 (1)°] indicates sp²and sp³hybridization, respectively. The five membered ring adopts half chair conformation.The crystal structure is stabilized by intermolecular O—H···N and C—H···O type hydrogen bonds.

Related literature top

For information on the pyrrolidine ring in biologically active natural compounds, see: Gu et al. (2004). For the use of pyrrolidine-containing molecules in the treatment of diseases, see, for example: Horri et al. (1986) for diabetes and Karpas et al. (1988) for viral infections. For bond lengths in a related structure, see: Jayabharathi et al. (2009).

Experimental top

Typical Procedure for the synthesis of (E)-3-(4-methoxyphenyl)-2-nitroprop-2-en-1-ol:

To a stirred soln of (E)-1-methoxy-4-(2-nitrovinyl)benzene (10 mmol) in THF (20 mL) at r.t. was added imidazole (1 equiv) followed by anthranilic acid (10 mol%). Aq formaldehyde (38%, 20 mL, excess) was then added and the mixture was stirred at r.t. for the period of 48h. On completion of the reaction (TLC analysis), the mixture was acidified with 5 M HCl (20 mL) and the aqueous layer was extracted with EtOAc (3 × 25 mL). The combined organic layers were washed with brine (50 mL), dried (anhyd Na2SO4), and concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc–hexanes, 0–25%, gradient elution) to afford pure (E)-3-(4-methoxyphenyl)-2-nitroprop-2-en-1-ol in 50% yield as yellow oil.

A mixture of (E)-3-(4-methoxyphenyl)-2-nitroprop-2-en-1-ol (2 mmol,0.42 g), para formaldehyde (12 mmol,0.36 g) and sacrosine (6 mmol,0.53 g) in acetonitrile(8 ml) was refluxed for 8hrs. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (20 ml) and extracted with ethyl acetate (3x10ml) and dried over anhydrous Na₂SO₄.The organic layer was concentrated and purified by column chromatography on silica gel (Acme 100–200 mesh), using ethyl acetate:hexane (3:7) to provide the title compound as a colourless solid in 73% (0.39 g) yield.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the molecules in the crystal structure. The dashed lines indicate the hydrogen bonds.

[4-(4-Methoxyphenyl)-1-methyl-3-nitropyrrolidin-3-yl]methanol top

Crystal data top

C₁₃H₁₈N₂O₄	F(000) = 568
M_r = 266.29	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3407 reflections
a = 11.6827 (10) Å	θ = 1.5–28.3°
b = 11.1912 (11) Å	µ = 0.10 mm⁻¹
c = 11.1789 (11) Å	T = 293 K
β = 109.118 (2)°	Block, colourless
V = 1381.0 (2) Å³	0.22 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2282 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 28.3°, θ_min = 1.8°
ω and ϕ scan	h = −15→15
12464 measured reflections	k = −14→14
3407 independent reflections	l = −14→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3407 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₃H₁₈N₂O₄	V = 1381.0 (2) Å³
M_r = 266.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6827 (10) Å	µ = 0.10 mm⁻¹
b = 11.1912 (11) Å	T = 293 K
c = 11.1789 (11) Å	0.22 × 0.20 × 0.20 mm
β = 109.118 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2282 reflections with I > 2σ(I)
12464 measured reflections	R_int = 0.031
3407 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
3407 reflections	Δρ_min = −0.16 e Å⁻³
172 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
C1	−0.36799 (16)	0.15244 (19)	0.51274 (18)	0.0686 (5)
H1A	−0.4468	0.1772	0.4592	0.103*
H1B	−0.3743	0.0770	0.5509	0.103*
H1C	−0.3151	0.1445	0.4631	0.103*
C2	−0.20810 (13)	0.21887 (15)	0.69433 (15)	0.0481 (4)
C3	−0.13157 (13)	0.12749 (15)	0.68781 (14)	0.0487 (4)
H3	−0.1540	0.0751	0.6195	0.058*
C4	−0.02079 (13)	0.11333 (14)	0.78317 (14)	0.0451 (4)
H4	0.0301	0.0513	0.7772	0.054*
C5	0.01580 (12)	0.18913 (13)	0.88680 (13)	0.0397 (3)
C6	−0.06274 (14)	0.28269 (16)	0.88911 (16)	0.0544 (4)
H6	−0.0407	0.3355	0.9571	0.065*
C7	−0.17096 (15)	0.29922 (17)	0.79468 (17)	0.0589 (5)
H7	−0.2197	0.3641	0.7976	0.071*
C8	0.13415 (12)	0.17615 (13)	0.99434 (12)	0.0388 (3)
H8	0.1198	0.2054	1.0708	0.047*
C9	0.24446 (12)	0.24842 (13)	0.98146 (12)	0.0380 (3)
C10	0.22476 (13)	0.29756 (15)	0.84980 (13)	0.0443 (4)
H10A	0.2056	0.2330	0.7885	0.053*
H10B	0.1576	0.3535	0.8270	0.053*
C11	0.35084 (14)	0.16266 (15)	1.02668 (14)	0.0484 (4)
H11A	0.3672	0.1256	0.9555	0.058*
H11B	0.4232	0.2039	1.0783	0.058*
C12	0.38953 (16)	−0.03316 (17)	1.12644 (17)	0.0643 (5)
H12A	0.4701	−0.0119	1.1783	0.096*
H12B	0.3916	−0.0659	1.0478	0.096*
H12C	0.3573	−0.0915	1.1697	0.096*
C13	0.18708 (14)	0.05085 (15)	1.02428 (15)	0.0481 (4)
H13A	0.1451	0.0054	1.0711	0.058*
H13B	0.1826	0.0079	0.9475	0.058*
N1	0.31240 (11)	0.07359 (12)	1.10121 (11)	0.0433 (3)
N3	0.26471 (14)	0.35622 (12)	1.07021 (12)	0.0509 (4)
O1	−0.32042 (10)	0.23895 (12)	0.60855 (13)	0.0663 (4)
O2	0.33114 (10)	0.35553 (12)	0.84933 (10)	0.0578 (4)
H2	0.3213	0.3832	0.7788	0.087*
O3	0.18039 (14)	0.42471 (12)	1.05376 (14)	0.0740 (4)
O4	0.36032 (15)	0.36987 (16)	1.15196 (15)	0.1019 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0467 (9)	0.0815 (14)	0.0648 (12)	0.0034 (9)	0.0006 (8)	−0.0089 (10)
C2	0.0367 (7)	0.0534 (10)	0.0510 (9)	−0.0001 (7)	0.0101 (7)	0.0014 (7)
C3	0.0456 (8)	0.0500 (9)	0.0461 (8)	−0.0014 (7)	0.0091 (7)	−0.0101 (7)
C4	0.0396 (8)	0.0449 (9)	0.0480 (8)	0.0002 (6)	0.0107 (7)	−0.0060 (6)
C5	0.0366 (7)	0.0443 (8)	0.0403 (7)	−0.0048 (6)	0.0155 (6)	−0.0034 (6)
C6	0.0462 (9)	0.0618 (11)	0.0532 (9)	0.0018 (8)	0.0138 (7)	−0.0168 (8)
C7	0.0485 (9)	0.0589 (11)	0.0675 (11)	0.0111 (8)	0.0164 (9)	−0.0118 (8)
C8	0.0392 (7)	0.0449 (8)	0.0341 (7)	−0.0050 (6)	0.0147 (6)	−0.0028 (6)
C9	0.0385 (7)	0.0426 (8)	0.0312 (7)	−0.0060 (6)	0.0092 (6)	−0.0026 (5)
C10	0.0414 (8)	0.0549 (9)	0.0348 (7)	−0.0099 (7)	0.0098 (6)	0.0016 (6)
C11	0.0406 (8)	0.0611 (10)	0.0440 (8)	0.0002 (7)	0.0148 (7)	0.0069 (7)
C12	0.0694 (12)	0.0594 (12)	0.0626 (11)	0.0198 (9)	0.0196 (9)	0.0076 (8)
C13	0.0489 (8)	0.0451 (9)	0.0473 (8)	−0.0063 (7)	0.0116 (7)	0.0033 (6)
N1	0.0432 (7)	0.0483 (8)	0.0377 (6)	0.0036 (5)	0.0124 (5)	0.0043 (5)
N3	0.0627 (9)	0.0478 (8)	0.0384 (7)	−0.0138 (7)	0.0114 (6)	−0.0022 (6)
O1	0.0463 (7)	0.0686 (9)	0.0692 (8)	0.0104 (6)	−0.0013 (6)	−0.0085 (6)
O2	0.0480 (6)	0.0810 (9)	0.0414 (6)	−0.0216 (6)	0.0105 (5)	0.0112 (5)
O3	0.0861 (10)	0.0537 (8)	0.0824 (9)	0.0001 (7)	0.0281 (8)	−0.0176 (7)
O4	0.0916 (11)	0.0971 (12)	0.0788 (10)	−0.0172 (9)	−0.0244 (9)	−0.0309 (9)

Geometric parameters (Å, º) top

C1—O1	1.415 (2)	C9—C10	1.5165 (19)
C1—H1A	0.9600	C9—C11	1.520 (2)
C1—H1B	0.9600	C9—N3	1.5303 (19)
C1—H1C	0.9600	C10—O2	1.4035 (17)
C2—O1	1.3666 (18)	C10—H10A	0.9700
C2—C3	1.376 (2)	C10—H10B	0.9700
C2—C7	1.392 (2)	C11—N1	1.4610 (19)
C3—C4	1.390 (2)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.386 (2)	C12—N1	1.467 (2)
C4—H4	0.9300	C12—H12A	0.9600
C5—C6	1.398 (2)	C12—H12B	0.9600
C5—C8	1.5130 (19)	C12—H12C	0.9600
C6—C7	1.369 (2)	C13—N1	1.4571 (19)
C6—H6	0.9300	C13—H13A	0.9700
C7—H7	0.9300	C13—H13B	0.9700
C8—C13	1.525 (2)	N3—O4	1.1989 (19)
C8—C9	1.5676 (18)	N3—O3	1.214 (2)
C8—H8	0.9800	O2—H2	0.8200

O1—C1—H1A	109.5	C11—C9—C8	104.53 (12)
O1—C1—H1B	109.5	N3—C9—C8	107.72 (11)
H1A—C1—H1B	109.5	O2—C10—C9	108.55 (11)
O1—C1—H1C	109.5	O2—C10—H10A	110.0
H1A—C1—H1C	109.5	C9—C10—H10A	110.0
H1B—C1—H1C	109.5	O2—C10—H10B	110.0
O1—C2—C3	125.19 (14)	C9—C10—H10B	110.0
O1—C2—C7	115.70 (14)	H10A—C10—H10B	108.4
C3—C2—C7	119.11 (14)	N1—C11—C9	104.48 (11)
C2—C3—C4	120.13 (14)	N1—C11—H11A	110.9
C2—C3—H3	119.9	C9—C11—H11A	110.9
C4—C3—H3	119.9	N1—C11—H11B	110.9
C5—C4—C3	121.74 (14)	C9—C11—H11B	110.9
C5—C4—H4	119.1	H11A—C11—H11B	108.9
C3—C4—H4	119.1	N1—C12—H12A	109.5
C4—C5—C6	116.70 (13)	N1—C12—H12B	109.5
C4—C5—C8	123.84 (13)	H12A—C12—H12B	109.5
C6—C5—C8	119.46 (13)	N1—C12—H12C	109.5
C7—C6—C5	122.22 (15)	H12A—C12—H12C	109.5
C7—C6—H6	118.9	H12B—C12—H12C	109.5
C5—C6—H6	118.9	N1—C13—C8	103.05 (12)
C6—C7—C2	119.99 (15)	N1—C13—H13A	111.2
C6—C7—H7	120.0	C8—C13—H13A	111.2
C2—C7—H7	120.0	N1—C13—H13B	111.2
C5—C8—C13	117.52 (12)	C8—C13—H13B	111.2
C5—C8—C9	116.25 (11)	H13A—C13—H13B	109.1
C13—C8—C9	102.02 (11)	C13—N1—C11	102.69 (11)
C5—C8—H8	106.8	C13—N1—C12	113.98 (14)
C13—C8—H8	106.8	C11—N1—C12	112.41 (12)
C9—C8—H8	106.8	O4—N3—O3	122.84 (16)
C10—C9—C11	113.55 (12)	O4—N3—C9	120.15 (15)
C10—C9—N3	106.59 (12)	O3—N3—C9	117.01 (13)
C11—C9—N3	110.26 (12)	C2—O1—C1	117.86 (14)
C10—C9—C8	114.09 (11)	C10—O2—H2	109.5

O1—C2—C3—C4	−177.74 (15)	C11—C9—C10—O2	−57.84 (17)
C7—C2—C3—C4	2.5 (2)	N3—C9—C10—O2	63.75 (15)
C2—C3—C4—C5	0.3 (2)	C8—C9—C10—O2	−177.49 (12)
C3—C4—C5—C6	−1.7 (2)	C10—C9—C11—N1	−144.62 (12)
C3—C4—C5—C8	178.72 (14)	N3—C9—C11—N1	95.86 (13)
C4—C5—C6—C7	0.4 (2)	C8—C9—C11—N1	−19.66 (14)
C8—C5—C6—C7	179.95 (16)	C5—C8—C13—N1	163.40 (11)
C5—C6—C7—C2	2.4 (3)	C9—C8—C13—N1	35.02 (13)
O1—C2—C7—C6	176.40 (16)	C8—C13—N1—C11	−48.96 (14)
C3—C2—C7—C6	−3.8 (3)	C8—C13—N1—C12	−170.81 (12)
C4—C5—C8—C13	−28.9 (2)	C9—C11—N1—C13	42.62 (14)
C6—C5—C8—C13	151.54 (15)	C9—C11—N1—C12	165.54 (13)
C4—C5—C8—C9	92.35 (17)	C10—C9—N3—O4	−115.56 (17)
C6—C5—C8—C9	−87.21 (17)	C11—C9—N3—O4	8.10 (19)
C5—C8—C9—C10	−13.76 (18)	C8—C9—N3—O4	121.60 (16)
C13—C8—C9—C10	115.42 (13)	C10—C9—N3—O3	64.81 (17)
C5—C8—C9—C11	−138.37 (12)	C11—C9—N3—O3	−171.52 (13)
C13—C8—C9—C11	−9.19 (13)	C8—C9—N3—O3	−58.03 (17)
C5—C8—C9—N3	104.35 (13)	C3—C2—O1—C1	7.2 (3)
C13—C8—C9—N3	−126.47 (12)	C7—C2—O1—C1	−173.08 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	2.01	2.8237 (16)	170
C1—H1A···O2ⁱⁱ	0.96	2.51	3.390 (2)	153
C3—H3···O3ⁱⁱⁱ	0.93	2.51	3.429 (2)	171

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z−1/2; (iii) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₈N₂O₄
M_r	266.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.6827 (10), 11.1912 (11), 11.1789 (11)
β (°)	109.118 (2)
V (Å³)	1381.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12464, 3407, 2282
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.162, 1.01
No. of reflections	3407
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	2.01	2.8237 (16)	170.3
C1—H1A···O2ⁱⁱ	0.96	2.51	3.390 (2)	152.9
C3—H3···O3ⁱⁱⁱ	0.93	2.51	3.429 (2)	171.1

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z−1/2; (iii) −x, y−1/2, −z+3/2.

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.

References

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gu, Y. G., Zhang, X., Clark, R. F., Djuric, S. & Ma, Z. (2004). Tetrahedron Lett. 45, 3051–3053. Web of Science CrossRef CAS Google Scholar
Horri, S., Fukase, H., Matsuo, T., Kameda, Y., Asano, N. & Matsui, K. (1986). J. Med. Chem. 29, 1038–1046. PubMed Web of Science Google Scholar
Jayabharathi, J., Thanikachalam, V. & Saravanan, K. (2009). J. Photochem. Photobiol. A, 208, 13–20. Web of Science CrossRef CAS Google Scholar
Karpas, A., Fleet, G. W. J., Dwek, R. A., Petursson, S., Mamgoong, S. K., Ramsden, N. G., Jacob, G. S. & Rademacher, T. W. (1988). Proc. Natl Acad. Sci. USA, 85, 9229–9233. CrossRef CAS PubMed Web of Science 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