6-Amino-3,4-dimethyl-4-phenyl-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile

Topno, N.S.; Kumaravel, K.; Kannan, M.; Vasuki, G.; Krishna, R.

doi:10.1107/S1600536811009354

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o956

doi:10.1107/S1600536811009354

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6-Amino-3,4-dimethyl-4-phenyl-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile

Nishith Saurav Topno,^a Kandhasamy Kumaravel,^b M. Kannan,^a 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 16 February 2011; accepted 11 March 2011; online 23 March 2011)

In the title compound, C₁₅H₁₄N₄O, the pyrazole ring is aligned at 88.23 (4)° with respect to the aromatic ring and at 3.75 (4)° with respect to the pyran ring. In the crystal, N—H⋯N hydrogen bonds link adjacent molecules into a linear chain motif. C—H⋯N interactions are also observed.

Related literature

For the synthesis, see: Vasuki & Kumaravel (2008 ). For the use of related compounds in organic synthesis, see: Liang et al. (2009 ). For related structures, see: Kannan et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₄N₄O
M_r = 266.3
Triclinic, $[P \overline 1]$
a = 6.682 (5) Å
b = 9.347 (5) Å
c = 11.078 (5) Å
α = 99.213 (5)°
β = 102.740 (5)°
γ = 97.767 (5)°
V = 655.6 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.16 mm

Data collection

Bruker APEXII Kappa CCD detector diffractometer
18424 measured reflections
4996 independent reflections
3169 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.173
S = 0.99
4996 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1ⁱ	0.86	2.27	3.129 (2)	173
N3—H3B⋯N4ⁱⁱ	0.86	2.26	3.087 (2)	160
C10—H10⋯N4ⁱⁱⁱ	0.93	2.53	3.455 (3)	172
C14—H14A⋯N1^iv	0.96	2.59	3.522 (3)	163
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) -x+2, -y+2, -z+2; (iv) -x+1, -y+1, -z+1.

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 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009354/ng5120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009354/ng5120Isup2.hkl

checkCIF report

Comment top

The pyrano pyrazole derivatives are widely used as organic intermediates (Liang et al., 2009) and are well known for their biological contribution as ChK1 inhibitors. In view of the growing importance of the pyrano pyrazole derivatives, we have synthesized the title compound by Rapid four-component reactions in water (Vasuki & Kumaravel, 2008) and the single-crystal structure analysis was undertaken.

In the title compound, the attached benzyl ring makes the dihedral angle of 88.23 (4) ° and orient in (+)-syn-clinal conforamtion with pyrazole ring, whereas the fused pyrazole ring makes 3.75 (4) ° dihedral angle and orient by an (+)-syn-periplanar conformation with respect to the pyran ring (Fig. 1). The methyl group is attached to C6 atom of pyran with an angle of 109.29 (11) °. Two N—H···N and C—H···N intermolecular hydrogen bond interactions (Fig. 2) are observed for maintaining the crystal packing (Fig. 3), in which the N3—H···N4 intermolecular interaction are observed to form R₂² (12) ring motifs (Fig. 4). The weak N—H···π intermolecular interaction is also observed for the stabilization of the crystal packing, with a bond distance of 3.382 (3) Å (Fig. 5).

Related literature top

For the synthesis, see: Vasuki & Kumaravel (2008). For the use of related compounds in organic synthesis, see: Liang et al. (2009). For related structures, see: Kannan et al. (2010).

Experimental top

The title compound was prepared by the successive addition of acetophenone 2 (0.240 g, 2 mmol), 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, 2 mmol) at room temperature under an open atmosphere with vigorous stirring for 5–10 min. The precipitated solid was then filtered, followed by washing with water and then with a mixture of ethyl acetate/hexane (20:80). The product obtained was pure by TLC and 1H NMR spectroscopy. Nevertheless, the products were further purified by recrystallization from ethanol. Analysis calculated for 6-amino-3,4-dimethyl-4-phenyl-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile showed that it has C₁₅H₁₄N₄O.

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 (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 50% probability level.
	Fig. 2. The crystal packing of (I), showing intermolecular hydrogen bonding interactions as dashed lines.
	Fig. 3. The crystal packing of Compound (I) viewed down the XO-axis, showing intermolecular hydrogen bonding interactions as dashed lines.
	Fig. 4. A view of R₂ ² (12) ring motifs formed by N—H···N interaction between two molecules. The ring forming atoms are shown in ball and stick model and the Hydrogen bond are shown in green dashed lines.
	Fig. 5. The molecular interaction showing the weak N—H···pi interaction in Compound (I). Cg is a centroid of C₈—C₁₃ ring.

6-Amino-3,4-dimethyl-4-phenyl-2H,4H-pyrano[2,3-c]pyrazole- 5-carbonitrile top

Crystal data top

C₁₅H₁₄N₄O	Z = 2
M_r = 266.3	F(000) = 280
Triclinic, P1	D_x = 1.349 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.682 (5) Å	Cell parameters from 4350 reflections
b = 9.347 (5) Å	θ = 1.9–33.3°
c = 11.078 (5) Å	µ = 0.09 mm⁻¹
α = 99.213 (5)°	T = 293 K
β = 102.740 (5)°	Prism, colourless
γ = 97.767 (5)°	0.22 × 0.20 × 0.16 mm
V = 655.6 (7) Å³

Data collection top

Bruker APEXII Kappa CCD-detector diffractometer	3169 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 33.3°, θ_min = 1.9°
Detector resolution: 0 pixels mm^-1	h = −10→9
ω and ϕ scans	k = −14→14
18424 measured reflections	l = −17→16
4996 independent 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0847P)² + 0.1309P] where P = (F_o² + 2F_c²)/3
4996 reflections	(Δ/σ)_max = 0.014
183 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₅H₁₄N₄O	γ = 97.767 (5)°
M_r = 266.3	V = 655.6 (7) Å³
Triclinic, P1	Z = 2
a = 6.682 (5) Å	Mo Kα radiation
b = 9.347 (5) Å	µ = 0.09 mm⁻¹
c = 11.078 (5) Å	T = 293 K
α = 99.213 (5)°	0.22 × 0.20 × 0.16 mm
β = 102.740 (5)°

Data collection top

Bruker APEXII Kappa CCD-detector diffractometer	3169 reflections with I > 2σ(I)
18424 measured reflections	R_int = 0.036
4996 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 0.99	Δρ_max = 0.30 e Å⁻³
4996 reflections	Δρ_min = −0.29 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	0.22065 (13)	0.57205 (11)	0.58851 (9)	0.0380 (2)
C2	0.52515 (18)	0.74174 (14)	0.57658 (11)	0.0306 (3)
N1	0.23543 (18)	0.67259 (14)	0.41251 (11)	0.0406 (3)
C6	0.64969 (18)	0.74989 (14)	0.70869 (12)	0.0304 (2)
C5	0.52503 (19)	0.63581 (14)	0.76101 (12)	0.0315 (3)
C7	0.6205 (2)	0.60943 (15)	0.88018 (13)	0.0377 (3)
C4	0.32984 (19)	0.55767 (14)	0.70373 (12)	0.0315 (3)
C3	0.32497 (19)	0.66098 (15)	0.52808 (12)	0.0320 (3)
C8	0.6664 (2)	0.90474 (14)	0.78630 (12)	0.0332 (3)
N3	0.21879 (18)	0.45814 (14)	0.74817 (12)	0.0439 (3)
H3A	0.0968	0.4142	0.7044	0.053*
H3B	0.2692	0.4379	0.8206	0.053*
N2	0.38757 (19)	0.76374 (15)	0.38430 (11)	0.0432 (3)
H2	0.3736	0.7912	0.3129	0.052*
N4	0.7004 (2)	0.59058 (17)	0.97741 (14)	0.0571 (4)
C1	0.5621 (2)	0.80702 (16)	0.47848 (13)	0.0376 (3)
C14	0.8640 (2)	0.70915 (18)	0.70847 (16)	0.0438 (3)
H14A	0.8467	0.6116	0.6599	0.066*
H14B	0.9397	0.7124	0.7936	0.066*
H14C	0.9401	0.7779	0.6718	0.066*
C13	0.4882 (2)	0.95084 (17)	0.81184 (15)	0.0442 (3)
H13	0.3617	0.8859	0.7841	0.053*
C9	0.8513 (3)	1.00406 (18)	0.82993 (17)	0.0517 (4)
H9	0.9738	0.9768	0.8150	0.062*
C10	0.8558 (3)	1.1452 (2)	0.89631 (18)	0.0639 (5)
H10	0.9817	1.2109	0.9251	0.077*
C15	0.7477 (3)	0.9053 (2)	0.46603 (16)	0.0536 (4)
H15A	0.8448	0.8469	0.4411	0.080*
H15B	0.8130	0.9701	0.5456	0.080*
H15C	0.7051	0.9625	0.4033	0.080*
C12	0.4943 (3)	1.0905 (2)	0.87732 (17)	0.0568 (4)
H12	0.3727	1.1186	0.8930	0.068*
C11	0.6797 (4)	1.18818 (19)	0.91953 (16)	0.0595 (5)
H11	0.6843	1.2826	0.9635	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0256 (4)	0.0500 (6)	0.0318 (5)	−0.0082 (4)	−0.0019 (3)	0.0142 (4)
C2	0.0260 (5)	0.0314 (6)	0.0302 (6)	−0.0015 (4)	0.0032 (4)	0.0049 (4)
N1	0.0346 (6)	0.0480 (7)	0.0319 (6)	−0.0072 (5)	−0.0007 (4)	0.0116 (5)
C6	0.0233 (5)	0.0309 (6)	0.0322 (6)	−0.0011 (4)	0.0012 (4)	0.0056 (4)
C5	0.0272 (5)	0.0296 (6)	0.0320 (6)	−0.0019 (4)	−0.0014 (4)	0.0073 (5)
C7	0.0308 (6)	0.0350 (7)	0.0397 (7)	−0.0061 (5)	−0.0026 (5)	0.0109 (5)
C4	0.0266 (5)	0.0338 (6)	0.0303 (6)	0.0004 (4)	0.0013 (4)	0.0072 (5)
C3	0.0273 (5)	0.0362 (6)	0.0290 (6)	−0.0015 (4)	0.0029 (4)	0.0073 (5)
C8	0.0330 (6)	0.0318 (6)	0.0286 (6)	−0.0033 (5)	−0.0005 (5)	0.0066 (5)
N3	0.0331 (6)	0.0509 (7)	0.0396 (6)	−0.0111 (5)	−0.0038 (5)	0.0191 (5)
N2	0.0415 (6)	0.0517 (7)	0.0308 (6)	−0.0082 (5)	0.0030 (5)	0.0144 (5)
N4	0.0472 (7)	0.0635 (9)	0.0477 (8)	−0.0143 (6)	−0.0114 (6)	0.0260 (7)
C1	0.0327 (6)	0.0407 (7)	0.0352 (7)	−0.0031 (5)	0.0057 (5)	0.0075 (5)
C14	0.0271 (6)	0.0477 (8)	0.0529 (9)	0.0045 (5)	0.0052 (6)	0.0076 (7)
C13	0.0464 (8)	0.0385 (8)	0.0450 (8)	0.0025 (6)	0.0122 (6)	0.0034 (6)
C9	0.0384 (7)	0.0422 (8)	0.0600 (10)	−0.0085 (6)	−0.0025 (7)	0.0016 (7)
C10	0.0682 (12)	0.0430 (9)	0.0577 (11)	−0.0165 (8)	−0.0087 (9)	−0.0007 (8)
C15	0.0450 (8)	0.0609 (10)	0.0498 (9)	−0.0142 (7)	0.0090 (7)	0.0193 (8)
C12	0.0746 (12)	0.0457 (9)	0.0514 (10)	0.0136 (8)	0.0213 (9)	0.0032 (7)
C11	0.0922 (14)	0.0371 (8)	0.0405 (8)	0.0039 (9)	0.0083 (9)	−0.0001 (6)

Geometric parameters (Å, º) top

O1—C4	1.3602 (16)	N2—C1	1.3465 (19)
O1—C3	1.3611 (16)	N2—H2	0.8600
C2—C1	1.3799 (19)	C1—C15	1.486 (2)
C2—C3	1.3885 (18)	C14—H14A	0.9600
C2—C6	1.5001 (18)	C14—H14B	0.9600
N1—C3	1.3164 (17)	C14—H14C	0.9600
N1—N2	1.3595 (17)	C13—C12	1.379 (2)
C6—C5	1.5289 (18)	C13—H13	0.9300
C6—C14	1.531 (2)	C9—C10	1.397 (3)
C6—C8	1.5369 (19)	C9—H9	0.9300
C5—C4	1.3661 (18)	C10—C11	1.357 (3)
C5—C7	1.4091 (19)	C10—H10	0.9300
C7—N4	1.1440 (19)	C15—H15A	0.9600
C4—N3	1.3340 (17)	C15—H15B	0.9600
C8—C9	1.380 (2)	C15—H15C	0.9600
C8—C13	1.390 (2)	C12—C11	1.374 (3)
N3—H3A	0.8600	C12—H12	0.9300
N3—H3B	0.8600	C11—H11	0.9300

C4—O1—C3	115.59 (10)	N2—C1—C2	106.17 (12)
C1—C2—C3	103.33 (11)	N2—C1—C15	122.22 (14)
C1—C2—C6	133.30 (11)	C2—C1—C15	131.61 (13)
C3—C2—C6	123.33 (11)	C6—C14—H14A	109.5
C3—N1—N2	101.74 (11)	C6—C14—H14B	109.5
C2—C6—C5	105.36 (10)	H14A—C14—H14B	109.5
C2—C6—C14	110.78 (11)	C6—C14—H14C	109.5
C5—C6—C14	109.28 (12)	H14A—C14—H14C	109.5
C2—C6—C8	109.09 (10)	H14B—C14—H14C	109.5
C5—C6—C8	109.98 (11)	C12—C13—C8	121.64 (15)
C14—C6—C8	112.12 (10)	C12—C13—H13	119.2
C4—C5—C7	116.92 (12)	C8—C13—H13	119.2
C4—C5—C6	126.31 (11)	C8—C9—C10	120.50 (17)
C7—C5—C6	116.77 (11)	C8—C9—H9	119.8
N4—C7—C5	178.69 (15)	C10—C9—H9	119.8
N3—C4—O1	110.00 (11)	C11—C10—C9	121.11 (17)
N3—C4—C5	127.07 (12)	C11—C10—H10	119.4
O1—C4—C5	122.93 (12)	C9—C10—H10	119.4
N1—C3—O1	119.33 (11)	C1—C15—H15A	109.5
N1—C3—C2	114.94 (12)	C1—C15—H15B	109.5
O1—C3—C2	125.71 (12)	H15A—C15—H15B	109.5
C9—C8—C13	117.40 (14)	C1—C15—H15C	109.5
C9—C8—C6	123.01 (13)	H15A—C15—H15C	109.5
C13—C8—C6	119.57 (11)	H15B—C15—H15C	109.5
C4—N3—H3A	120.0	C11—C12—C13	120.16 (18)
C4—N3—H3B	120.0	C11—C12—H12	119.9
H3A—N3—H3B	120.0	C13—C12—H12	119.9
C1—N2—N1	113.80 (12)	C10—C11—C12	119.19 (17)
C1—N2—H2	123.1	C10—C11—H11	120.4
N1—N2—H2	123.1	C12—C11—H11	120.4

C1—C2—C6—C5	−173.79 (14)	C6—C2—C3—N1	176.69 (12)
C3—C2—C6—C5	8.91 (17)	C1—C2—C3—O1	177.46 (13)
C1—C2—C6—C14	−55.7 (2)	C6—C2—C3—O1	−4.6 (2)
C3—C2—C6—C14	126.98 (14)	C2—C6—C8—C9	−111.80 (15)
C1—C2—C6—C8	68.17 (18)	C5—C6—C8—C9	133.10 (14)
C3—C2—C6—C8	−109.13 (14)	C14—C6—C8—C9	11.29 (19)
C2—C6—C5—C4	−7.33 (18)	C2—C6—C8—C13	66.30 (15)
C14—C6—C5—C4	−126.40 (15)	C5—C6—C8—C13	−48.80 (16)
C8—C6—C5—C4	110.12 (15)	C14—C6—C8—C13	−170.61 (13)
C2—C6—C5—C7	173.06 (12)	C3—N1—N2—C1	−0.42 (17)
C14—C6—C5—C7	53.99 (16)	N1—N2—C1—C2	−0.34 (18)
C8—C6—C5—C7	−69.50 (15)	N1—N2—C1—C15	179.23 (15)
C4—C5—C7—N4	−158 (8)	C3—C2—C1—N2	0.91 (15)
C6—C5—C7—N4	21 (8)	C6—C2—C1—N2	−176.77 (14)
C3—O1—C4—N3	−174.36 (12)	C3—C2—C1—C15	−178.61 (17)
C3—O1—C4—C5	5.24 (19)	C6—C2—C1—C15	3.7 (3)
C7—C5—C4—N3	−0.2 (2)	C9—C8—C13—C12	0.5 (2)
C6—C5—C4—N3	−179.80 (13)	C6—C8—C13—C12	−177.74 (14)
C7—C5—C4—O1	−179.72 (12)	C13—C8—C9—C10	−0.4 (2)
C6—C5—C4—O1	0.7 (2)	C6—C8—C9—C10	177.75 (15)
N2—N1—C3—O1	−177.77 (12)	C8—C9—C10—C11	0.0 (3)
N2—N1—C3—C2	1.06 (17)	C8—C13—C12—C11	−0.2 (3)
C4—O1—C3—N1	175.29 (12)	C9—C10—C11—C12	0.3 (3)
C4—O1—C3—C2	−3.4 (2)	C13—C12—C11—C10	−0.2 (3)
C1—C2—C3—N1	−1.29 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1ⁱ	0.86	2.27	3.129 (2)	173
N3—H3B···N4ⁱⁱ	0.86	2.26	3.087 (2)	160
C10—H10···N4ⁱⁱⁱ	0.93	2.53	3.455 (3)	172
C14—H14A···N1^iv	0.96	2.59	3.522 (3)	163

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₄O
M_r	266.3
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.682 (5), 9.347 (5), 11.078 (5)
α, β, γ (°)	99.213 (5), 102.740 (5), 97.767 (5)
V (Å³)	655.6 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.20 × 0.16

Data collection
Diffractometer	Bruker APEXII Kappa CCD-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18424, 4996, 3169
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.771

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.173, 0.99
No. of reflections	4996
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1ⁱ	0.86	2.27	3.129 (2)	172.6
N3—H3B···N4ⁱⁱ	0.86	2.26	3.087 (2)	160.2
C10—H10···N4ⁱⁱⁱ	0.93	2.53	3.455 (3)	172.2
C14—H14A···N1^iv	0.96	2.59	3.522 (3)	162.6

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

Acknowledgements

The authors acknowledge the Centre of Excellence in Bioinformatics, Pondicherry University, for providing the facilities for carrying out this work. RK and MK thank the University Grant Commission for providing a Major Research Project and Rajiv Gandhi National Fellowship, respectively. GV thanks the Department of Science and Technology, New Delhi, Government of India (grant No. SR/S5/GC-22/2007) for financial support.

References

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