Ethyl 2-(6-amino-5-cyano-3,4-dimethyl-2H,4H-pyrano[2,3-c]pyrazol-4-yl)acetate

Kannan, M.; Kumaravel, K.; Vasuki, G.; Krishna, R.

doi:10.1107/S1600536810015540

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1242

https://doi.org/10.1107/S1600536810015540

Open

access

Ethyl 2-(6-amino-5-cyano-3,4-dimethyl-2H,4H-pyrano[2,3-c]pyrazol-4-yl)acetate

M. Kannan,^a Kandhasamy Kumaravel,^b Gnanasambandam Vasuki ^b and R. Krishna ^a ^*

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

(Received 19 April 2010; accepted 27 April 2010; online 30 April 2010)

In he title compound, C₁₃H₁₆N₄O₃, the pyrazole ring is planar (r.m.s. deviation = 0.054 Å). The pyran ring is not planar; the mean plane makes a dihedral angle of 1.9 (1)° with the pyrazole ring. In the crystal structure, intermolecular N—H⋯N and N—H⋯O interactions lead to a linear chain motif.

Related literature

For biological applications of pyrazole and pyranopyrazole derivatives, see: Wamhoff et al. (1993 ).; Velaparthi et al. (2008 ); Magedov et al. (2007 ); Rovnyak et al. (1982 ). For the synthesis, see: Vasuki & Kumaravel (2008 ).

Experimental

Crystal data

C₁₃H₁₆N₄O₃
M_r = 276.30
Triclinic, $[P \overline 1]$
a = 6.961 (5) Å
b = 7.373 (5) Å
c = 14.535 (5) Å
α = 86.405 (5)°
β = 85.183 (5)°
γ = 65.726 (5)°
V = 677.3 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2004 ) T_min = 0.976, T_max = 0.981
12811 measured reflections
2385 independent reflections
2130 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.117
S = 1.02
2378 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	2.55	3.274 (2)	142
N2—H2⋯N1ⁱⁱ	0.86	2.37	2.956 (2)	126
N3—H3A⋯N4ⁱⁱⁱ	0.86	2.19	3.012 (2)	160
N3—H3B⋯O3^iv	0.86	2.40	3.192 (2)	154
Symmetry codes: (i) -x, -y+2, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x+1, -y+1, -z+1; (iv) x+1, y, z.

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: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810015540/ng2761sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015540/ng2761Isup2.hkl

checkCIF report

Comment top

Pyrazole, Pyranopyrazoles and its derivates possess antimicrobial (Velaparthi et al.,2008),anticancer (Magedov et al.,2007) and anti-inflammatory (Rovnyak et al.,1982) properties,which made them to be used as a medicines and as biodegradable agrochemiclas (Wamhoff et al., 1993).Wide variety of biological importances of these molecules made the quest for their crystal study and accordingly we have synthesized the title compound by multi-component reaction which compiles with the principles of green chemistry and reported the crystal structure of the title compound.

The compound was crystallized by slow evaporation technique using ethanol as solvent at room temperature. The title compound, (I) was centrosymmetric and it has triclinic crystal system with the space group of P-1. The pyrazole groups are essentially planar, with a mean deviation of 0.0542 Å from the least square plane defined by the five atoms (N1 to C1). The pyran ring deviates significantly from the plane and it has dihedral angle of 1.93 (0.06)° with pyrazole ring. The ethyl acetate group has dihedral angle of 49.99 (0.07)° with pyran ring to which it is attached (Fig. 1). The intermolecular hydrogen bond was formed between N2···N1, N3···N4, N2—H···O2 and N3—H···O3 with distance of 2.956 (2), 3.012 (2), 3.274 (2) and 3.192 (2) Å respectively (Table.1). These intermolecular interactions help in theformation three-dimensional network and crystal packing (Fig. 2) of (I).

Related literature top

For biological applications of pyrazole and pyranopyrazole derivatives, see: Wamhoff et al. (1993).; Velaparthi et al. (2008); Magedov et al. (2007); Rovnyak et al. (1982). For the synthesis, see: Vasuki & Kumaravel (2008).

Experimental top

The titled compound was prepared bythe successive addition of malononitrile (0.132 g, 2 mmol) and piperidine (5 mol%) to a stirred aqueous mixture of hydrazine hydrate 96% 1 (0.107 g, 2 mmol)and ethyl acetoacetate 2 (0.520 g, 4 mmol) at room temperature under an openatmosphere with vigorous stirring for 5–10 min. The precipitated solid wasfiltered, washed with water and then with a mixture of ethyl acetate/hexane(20:80) (Vasuki & Kumaravel, 2008). The product obtained was pure by TLCand ¹H NMR spectroscopy. However, the products were further purifiedby recrystallization from ethanol. Analysis calculated for ethyl2-(6-amino-5-cyano-3,4-dimethyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl) acetate showed that it has C₁₃, H₁₆,N₄, O₃.

Structure description top

For biological applications of pyrazole and pyranopyrazole derivatives, see: Wamhoff et al. (1993).; Velaparthi et al. (2008); Magedov et al. (2007); Rovnyak et al. (1982). For the synthesis, see: Vasuki & Kumaravel (2008).

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. : The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. : The crystal packing of (I), showing intermolecular hydrogen bonding interactions as dashed lines.

Ethyl 2-(6-amino-5-cyano-3,4-dimethyl-2H,4H- pyrano[2,3-c]pyrazol-4-yl)acetate top

Crystal data top

C₁₃H₁₆N₄O₃	Z = 2
M_r = 276.30	F(000) = 292
Triclinic, P1	D_x = 1.355 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.961 (5) Å	Cell parameters from 7682 reflections
b = 7.373 (5) Å	θ = 2.8–32.8°
c = 14.535 (5) Å	µ = 0.10 mm⁻¹
α = 86.405 (5)°	T = 293 K
β = 85.183 (5)°	Block, colourless
γ = 65.726 (5)°	0.25 × 0.20 × 0.20 mm
V = 677.3 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2385 independent reflections
Radiation source: fine-focus sealed tube	2130 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.8°
ω and φ scan	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker 2004)	k = −8→8
T_min = 0.976, T_max = 0.981	l = −17→17
12811 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0655P)² + 0.2561P] where P = (F_o² + 2F_c²)/3
2378 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₃H₁₆N₄O₃	γ = 65.726 (5)°
M_r = 276.30	V = 677.3 (7) Å³
Triclinic, P1	Z = 2
a = 6.961 (5) Å	Mo Kα radiation
b = 7.373 (5) Å	µ = 0.10 mm⁻¹
c = 14.535 (5) Å	T = 293 K
α = 86.405 (5)°	0.25 × 0.20 × 0.20 mm
β = 85.183 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2385 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	2130 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.981	R_int = 0.020
12811 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
2378 reflections	Δρ_min = −0.26 e Å⁻³
184 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

Some "bad" relections were omitted in the refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.4375 (2)	0.8266 (2)	0.84125 (10)	0.0288 (3)
C2	0.3125 (2)	0.7231 (2)	0.86328 (9)	0.0271 (3)
C3	0.2551 (2)	0.6151 (2)	0.79351 (9)	0.0271 (3)
C4	0.3682 (2)	0.6404 (2)	0.70213 (9)	0.0282 (3)
C5	0.4908 (2)	0.7439 (2)	0.68793 (10)	0.0306 (3)
C6	0.0126 (2)	0.7009 (2)	0.78369 (10)	0.0329 (3)
H6A	−0.0164	0.6276	0.7375	0.040*
H6B	−0.0563	0.6818	0.8420	0.040*
C7	−0.0780 (2)	0.9167 (2)	0.75667 (11)	0.0378 (4)
C8	−0.1525 (3)	1.1488 (3)	0.62848 (17)	0.0654 (6)
H8A	−0.2528	1.2402	0.6724	0.078*
H8B	−0.2217	1.1636	0.5715	0.078*
C9	0.0317 (5)	1.1990 (4)	0.6104 (3)	0.1088 (12)
H9A	0.0887	1.2023	0.6679	0.163*
H9B	−0.0109	1.3271	0.5794	0.163*
H9C	0.1375	1.1003	0.5722	0.163*
C10	0.2672 (2)	0.7477 (2)	0.95731 (10)	0.0320 (3)
C11	0.1408 (3)	0.6754 (3)	1.02539 (11)	0.0487 (5)
H11A	0.2177	0.5356	1.0380	0.073*
H11B	0.0091	0.6978	1.0006	0.073*
H11C	0.1140	0.7461	1.0816	0.073*
C12	0.3282 (3)	0.3931 (2)	0.82003 (11)	0.0385 (4)
H12A	0.4780	0.3351	0.8261	0.058*
H12B	0.2951	0.3270	0.7729	0.058*
H12C	0.2574	0.3782	0.8777	0.058*
C13	0.3419 (2)	0.5481 (2)	0.62484 (10)	0.0354 (4)
N1	0.4738 (2)	0.9108 (2)	0.91081 (8)	0.0351 (3)
N2	0.3649 (2)	0.8596 (2)	0.98199 (8)	0.0357 (3)
H2	0.3589	0.8954	1.0377	0.043*
N3	0.5923 (2)	0.7662 (2)	0.60839 (9)	0.0474 (4)
H3A	0.5831	0.7114	0.5594	0.057*
H3B	0.6667	0.8352	0.6064	0.057*
N4	0.3189 (3)	0.4715 (3)	0.56322 (10)	0.0555 (4)
O1	0.52556 (17)	0.84545 (17)	0.75515 (7)	0.0367 (3)
O2	−0.1338 (2)	1.0482 (2)	0.81014 (10)	0.0659 (4)
O3	−0.08990 (18)	0.94621 (17)	0.66504 (8)	0.0450 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0306 (7)	0.0354 (7)	0.0243 (7)	−0.0169 (6)	−0.0013 (5)	−0.0047 (6)
C2	0.0271 (7)	0.0322 (7)	0.0246 (7)	−0.0142 (6)	−0.0018 (5)	−0.0038 (5)
C3	0.0277 (7)	0.0322 (7)	0.0250 (7)	−0.0153 (6)	−0.0012 (5)	−0.0050 (5)
C4	0.0269 (7)	0.0353 (7)	0.0253 (7)	−0.0148 (6)	−0.0007 (5)	−0.0071 (6)
C5	0.0307 (7)	0.0399 (8)	0.0245 (7)	−0.0172 (6)	−0.0006 (6)	−0.0069 (6)
C6	0.0291 (7)	0.0450 (8)	0.0312 (8)	−0.0213 (6)	0.0005 (6)	−0.0068 (6)
C7	0.0250 (7)	0.0454 (9)	0.0434 (9)	−0.0128 (6)	−0.0036 (6)	−0.0124 (7)
C8	0.0592 (12)	0.0478 (11)	0.0810 (15)	−0.0144 (9)	−0.0116 (11)	0.0124 (10)
C9	0.096 (2)	0.0740 (17)	0.171 (3)	−0.0526 (16)	−0.029 (2)	0.0415 (19)
C10	0.0376 (8)	0.0365 (8)	0.0267 (7)	−0.0196 (6)	−0.0016 (6)	−0.0048 (6)
C11	0.0692 (12)	0.0637 (11)	0.0298 (8)	−0.0450 (10)	0.0083 (8)	−0.0090 (8)
C12	0.0481 (9)	0.0344 (8)	0.0364 (8)	−0.0197 (7)	−0.0038 (7)	−0.0028 (6)
C13	0.0362 (8)	0.0488 (9)	0.0289 (8)	−0.0255 (7)	0.0042 (6)	−0.0088 (7)
N1	0.0430 (7)	0.0457 (7)	0.0273 (6)	−0.0284 (6)	−0.0011 (5)	−0.0067 (5)
N2	0.0487 (8)	0.0459 (7)	0.0224 (6)	−0.0286 (6)	−0.0015 (5)	−0.0069 (5)
N3	0.0591 (9)	0.0738 (10)	0.0300 (7)	−0.0484 (8)	0.0114 (6)	−0.0162 (7)
N4	0.0675 (10)	0.0859 (12)	0.0357 (8)	−0.0534 (9)	0.0097 (7)	−0.0243 (8)
O1	0.0446 (6)	0.0537 (7)	0.0266 (6)	−0.0350 (5)	0.0047 (4)	−0.0106 (5)
O2	0.0652 (9)	0.0518 (8)	0.0677 (9)	−0.0048 (7)	−0.0160 (7)	−0.0270 (7)
O3	0.0440 (7)	0.0432 (6)	0.0457 (7)	−0.0163 (5)	−0.0008 (5)	−0.0005 (5)

Geometric parameters (Å, º) top

C1—N1	1.3125 (19)	C8—H8A	0.9700
C1—O1	1.3714 (18)	C8—H8B	0.9700
C1—C2	1.383 (2)	C9—H9A	0.9600
C2—C10	1.383 (2)	C9—H9B	0.9600
C2—C3	1.5006 (19)	C9—H9C	0.9600
C3—C4	1.527 (2)	C10—N2	1.346 (2)
C3—C12	1.535 (2)	C10—C11	1.487 (2)
C3—C6	1.556 (2)	C11—H11A	0.9600
C4—C5	1.356 (2)	C11—H11B	0.9600
C4—C13	1.411 (2)	C11—H11C	0.9600
C5—N3	1.341 (2)	C12—H12A	0.9600
C5—O1	1.3616 (17)	C12—H12B	0.9600
C6—C7	1.490 (2)	C12—H12C	0.9600
C6—H6A	0.9700	C13—N4	1.144 (2)
C6—H6B	0.9700	N1—N2	1.3572 (18)
C7—O2	1.195 (2)	N2—H2	0.8600
C7—O3	1.340 (2)	N3—H3A	0.8600
C8—O3	1.452 (2)	N3—H3B	0.8600
C8—C9	1.474 (4)

N1—C1—O1	118.81 (13)	H8A—C8—H8B	108.0
N1—C1—C2	115.28 (13)	C8—C9—H9A	109.5
O1—C1—C2	125.90 (13)	C8—C9—H9B	109.5
C1—C2—C10	103.21 (13)	H9A—C9—H9B	109.5
C1—C2—C3	123.21 (13)	C8—C9—H9C	109.5
C10—C2—C3	133.58 (13)	H9A—C9—H9C	109.5
C2—C3—C4	105.90 (12)	H9B—C9—H9C	109.5
C2—C3—C12	111.39 (12)	N2—C10—C2	106.01 (13)
C4—C3—C12	109.91 (12)	N2—C10—C11	122.04 (14)
C2—C3—C6	112.12 (11)	C2—C10—C11	131.95 (14)
C4—C3—C6	110.22 (12)	C10—C11—H11A	109.5
C12—C3—C6	107.33 (12)	C10—C11—H11B	109.5
C5—C4—C13	116.78 (13)	H11A—C11—H11B	109.5
C5—C4—C3	126.29 (13)	C10—C11—H11C	109.5
C13—C4—C3	116.93 (13)	H11A—C11—H11C	109.5
N3—C5—C4	126.98 (14)	H11B—C11—H11C	109.5
N3—C5—O1	109.58 (13)	C3—C12—H12A	109.5
C4—C5—O1	123.44 (13)	C3—C12—H12B	109.5
C7—C6—C3	112.62 (12)	H12A—C12—H12B	109.5
C7—C6—H6A	109.1	C3—C12—H12C	109.5
C3—C6—H6A	109.1	H12A—C12—H12C	109.5
C7—C6—H6B	109.1	H12B—C12—H12C	109.5
C3—C6—H6B	109.1	N4—C13—C4	178.79 (17)
H6A—C6—H6B	107.8	C1—N1—N2	101.70 (12)
O2—C7—O3	123.82 (17)	C10—N2—N1	113.80 (12)
O2—C7—C6	124.23 (16)	C10—N2—H2	123.1
O3—C7—C6	111.94 (13)	N1—N2—H2	123.1
O3—C8—C9	111.08 (18)	C5—N3—H3A	120.0
O3—C8—H8A	109.4	C5—N3—H3B	120.0
C9—C8—H8A	109.4	H3A—N3—H3B	120.0
O3—C8—H8B	109.4	C5—O1—C1	115.14 (12)
C9—C8—H8B	109.4	C7—O3—C8	117.56 (15)

N1—C1—C2—C10	0.13 (17)	C12—C3—C6—C7	−179.24 (12)
O1—C1—C2—C10	179.38 (13)	C3—C6—C7—O2	−85.9 (2)
N1—C1—C2—C3	−179.36 (12)	C3—C6—C7—O3	94.18 (15)
O1—C1—C2—C3	−0.1 (2)	C1—C2—C10—N2	0.13 (16)
C1—C2—C3—C4	2.14 (18)	C3—C2—C10—N2	179.54 (14)
C10—C2—C3—C4	−177.17 (15)	C1—C2—C10—C11	−179.84 (17)
C1—C2—C3—C12	121.60 (15)	C3—C2—C10—C11	−0.4 (3)
C10—C2—C3—C12	−57.7 (2)	C5—C4—C13—N4	169 (9)
C1—C2—C3—C6	−118.10 (15)	C3—C4—C13—N4	−11 (9)
C10—C2—C3—C6	62.6 (2)	O1—C1—N1—N2	−179.63 (12)
C2—C3—C4—C5	−1.37 (19)	C2—C1—N1—N2	−0.32 (17)
C12—C3—C4—C5	−121.80 (16)	C2—C10—N2—N1	−0.35 (17)
C6—C3—C4—C5	120.10 (16)	C11—C10—N2—N1	179.63 (15)
C2—C3—C4—C13	178.97 (12)	C1—N1—N2—C10	0.41 (17)
C12—C3—C4—C13	58.54 (17)	N3—C5—O1—C1	−177.10 (12)
C6—C3—C4—C13	−59.56 (17)	C4—C5—O1—C1	3.8 (2)
C13—C4—C5—N3	−0.9 (2)	N1—C1—O1—C5	176.23 (12)
C3—C4—C5—N3	179.41 (14)	C2—C1—O1—C5	−3.0 (2)
C13—C4—C5—O1	178.03 (13)	O2—C7—O3—C8	7.0 (2)
C3—C4—C5—O1	−1.6 (2)	C6—C7—O3—C8	−173.07 (14)
C2—C3—C6—C7	58.13 (16)	C9—C8—O3—C7	87.2 (3)
C4—C3—C6—C7	−59.57 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.55	3.274 (2)	142
N2—H2···N1ⁱⁱ	0.86	2.37	2.956 (2)	126
N3—H3A···N4ⁱⁱⁱ	0.86	2.19	3.012 (2)	160
N3—H3B···O3^iv	0.86	2.40	3.192 (2)	154

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₄O₃
M_r	276.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.961 (5), 7.373 (5), 14.535 (5)
α, β, γ (°)	86.405 (5), 85.183 (5), 65.726 (5)
V (Å³)	677.3 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker 2004)
T_min, T_max	0.976, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	12811, 2385, 2130
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.02
No. of reflections	2378
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.26

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.55	3.274 (2)	142.1
N2—H2···N1ⁱⁱ	0.86	2.37	2.956 (2)	126.0
N3—H3A···N4ⁱⁱⁱ	0.86	2.19	3.012 (2)	159.6
N3—H3B···O3^iv	0.86	2.40	3.192 (2)	154.3

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

Acknowledgements

The authors acknowledge the Centre of Excellence in Bioinformatics, Pondicherry University, for providing the facilities and GV thanks the Department of Science and Technology, New Delhi, Government of India, (No. SR/S5/GC-22/2007) for financial support.

References

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Magedov, I. V., Manpadi, M., Vanslambrouck, S., Steelant, W. F. A., Rozhkova, E., Przhevalskii, N. M., Rogelj, S. & Kornienko, A. (2007). J. Med. Chem. 50, 5183–5192. Web of Science CrossRef PubMed CAS Google Scholar
Rovnyak, G. C., Millonig, R. C., Schwartz, J. & Shu, V. (1982). J. Med. Chem. 25, 1482–1488. 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
Vasuki, G. & Kumaravel, K. (2008). Tetrahedron Lett. 49, 5636–5638. Web of Science CSD CrossRef CAS Google Scholar
Velaparthi, S., Brunsteiner, M., Uddin, R., Wan, B., Franzblau, S. G. & Petukhov, P. A. (2008). J. Med. Chem. 51, 1999–2002. Web of Science CrossRef PubMed CAS Google Scholar
Wamhoff, H., Kroth, E. & Strauch, K. (1993). Synthesis, 11, 1129. CrossRef Google Scholar