5-(3-Nitro­benz­yl)-1,3,4-thia­diazol-2-amine

Carvalho, S.A.; Feitosa, L.O. de; Silva, E.F. da; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536809049654

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3200-o3201

doi:10.1107/S1600536809049654

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5-(3-Nitrobenzyl)-1,3,4-thiadiazol-2-amine

Samir A. Carvalho,^a,^b Larisse O. de Feitosa,^a Edson F. da Silva,^a Edward R. T. Tiekink,^c ^* James L. Wardell ^d ‡ and Solange M. S. V. Wardell ^e

^aFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos - Far-Manguinhos, Laboratório de Síntese IV, 21041-250 Rio de Janeiro, RJ, Brazil, ^bInstituto de Química, Universidade Federal do Rio de Janeiro, 21949-900 Rio de Janeiro, RJ, Brazil, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil, and ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 17 November 2009; accepted 19 November 2009; online 25 November 2009)

In the title molecule, C₉H₈N₄O₂S, the dihedral angle between the thiadiazole and benzene rings is 73.92 (8)° and the thiadiazole group S atom is orientated towards the benzene ring, the central S—C—C—C torsion angle being 45.44 (18)°. In the crystal, supramolecular tapes mediated by N—H⋯N hydrogen bonds and comprising alternating eight-membered {⋯HNCN}₂ and 10-membered {⋯HNH⋯NN}₂ synthons are formed along [010]. The tapes are consolidated into a three-dimensional network by a combination of C—H⋯O, C—H⋯S and C—H⋯π interactions

Related literature

For background to the biological interest of 1,3,4-thiadiazoles, see: Thomasco et al. (2003 ); Oruç et al. (2004 ); Moise et al. (2009 ); Amir et al. (2009 ). For the development of anti-trypanosomal compounds, see: Carvalho et al. (2004 ); Boechat et al. (2006 ); Boechat et al. (2008 ); Carvalho et al. (2008 ); Poorrajab et al. (2009 ) Riente et al. (2009 ). For the synthesis, see: Turner et al. (1988 ).

Experimental

Crystal data

C₉H₈N₄O₂S
M_r = 236.26
Triclinic, $[P \overline 1]$
a = 5.0878 (2) Å
b = 5.6213 (3) Å
c = 17.8035 (9) Å
α = 80.980 (3)°
β = 85.677 (3)°
γ = 79.855 (3)°
V = 494.42 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 120 K
0.38 × 0.20 × 0.09 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.639, T_max = 0.746
9074 measured reflections
2256 independent reflections
1973 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.086
S = 1.05
2256 reflections
151 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1n⋯N2ⁱ	0.88	2.25	3.0828 (19)	157
N3—H2n⋯N1ⁱⁱ	0.88	2.12	3.003 (2)	175
C3—H3a⋯N2ⁱⁱⁱ	0.99	2.60	3.552 (2)	162
C3—H3b⋯S1^iv	0.99	2.85	3.6687 (17)	141
C7—H7⋯O2^v	0.95	2.53	3.355 (2)	145
C9—H9⋯O1^vi	0.95	2.51	3.446 (2)	168
C5—H5⋯Cgⁱⁱⁱ	0.95	2.86	3.7708 (17)	160
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+2, -z+1; (iii) x-1, y, z; (iv) x, y+1, z; (v) -x, -y+1, -z+2; (vi) x+1, y+1, z. Cg is the centroid of the S1/N1/N2/C1/C2 ring.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049654/lh2958sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049654/lh2958Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazoles have attracted much attention due to their biological activities (Thomasco et al., 2003; Oruç et al., 2004; Moise et al., 2009; Amir et al., 2009), with particular attention being paid to the anti-trypanosomal activities of Megazol, and related compounds (Carvalho et al., 2004, 2008; Riente et al., 2009: Poorrajab et al., 2009). In continuation of our interests in 1,3,4-thiadiazoles (Boechat et al., 2006, 2008; Carvalho et al., 2004, 2008), we now report the structure of the title compound, (I), obtained by modification of a general procedure (Turner et al., 1988).

In the molecular structure of (I) atom S1 is orientated towards the benzene ring, Fig. 1. The dihedral angle between the thiadiazole (r.m.s. deviation = 0.005 Å) and benzene (r.m.s. deviation = 0.004 Å) rings of 73.92 (8) ° indicates a twist between planes as seen in the S1–C2–C3–C4 torsion angle of 45.44 (18) °. The nitro group is effectively co-planar with the benzene ring to which it is attached as seen in the O1–N4–C6–C5 torsion angle of 6.3 (2) °.

The crystal packing is dominated by N—H···N hydrogen bonds. Each of the amine-H atoms connects to a centrosymmetrically related molecule leading to eight-membered {···HNCN}₂ and 10-membered {···HNH···NN}₂ synthons. Each synthon is planar and alternate in a supramolecular tape orientated along [010], Table 1 and Fig. 2. Chains are consolidated into a 3-D network by a combination of C—H···O, C—H···S and C—H···π interactions, Table 1 and Fig. 3.

Related literature top

For background to the biological interest of 1,3,4-thiadiazoles, see: Thomasco et al. (2003); Oruç et al. (2004); Moise et al. (2009); Amir et al. (2009). For the development of anti-trypanosomal compounds, see: Carvalho et al. (2004); Boechat et al. (2006); Boechat et al. (2008); Carvalho et al. (2008); Poorrajab et al. (2009) Riente et al. (2009). For the synthesis, see: Turner et al. (1988). Cg is the centroid of the S1/N1/N2/C1/C2 ring.

Experimental top

A finely ground mixture of 2-nitrophenylacetic acid (0.49 g, 2.7 mmol) and thiosemicarbazide (0.25 g, 2.7 mmol) was added in portions over 0.5 h to polyphosphoric acid (5 g) at 353 K. The reaction mixture was maintained at 353 K for 5 h and cooled, water/ice was added, and the mixture was finally basified with NaOH 30% (aq.). The solids isolated by filtration were washed with water and air-dried to give (I), which was recrystallized from EtOH, m.p. 471–473 K; yield 72%. The sample used in the structure determination was obtained after a further recrystallization from EtOH. ¹H NMR (d₆-DMSO) δ: 4.47 (s, 2H, CH₂), 7.05 (s, 2H, NH₂), 7.55 (m, 2H, H4 and H5), 7.72 (m, 1H, H6), 8.03 (d, 1H, J = 8.0 Hz) p.p.m. ¹³C NMR (d₆-DMSO) δ: 32.8, 124.7, 128.6, 132.0, 132.6, 133.8, 148.5, 155.1, 168.7 p.p.m.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular chain along [010] in (I) mediated by N–H···N hydrogen bonds (blue dashed lines). Colour code: S, yellow; O, red; N, blue; C, grey; and H, green.
	Fig. 3. Unit-cell contents for (I) viewed in projection down the a axis. The N–H···N (blue), C—H···O (orange) and C—H···S (green) contacts are shown as dashed lines. Colour code: S, yellow; O, red; N, blue; C, grey; and H, green.

5-(3-Nitrobenzyl)-1,3,4-thiadiazol-2-amine top

Crystal data top

C₉H₈N₄O₂S	Z = 2
M_r = 236.26	F(000) = 244
Triclinic, P1	D_x = 1.587 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0878 (2) Å	Cell parameters from 11753 reflections
b = 5.6213 (3) Å	θ = 2.9–27.5°
c = 17.8035 (9) Å	µ = 0.32 mm⁻¹
α = 80.980 (3)°	T = 120 K
β = 85.677 (3)°	Block, colourless
γ = 79.855 (3)°	0.38 × 0.20 × 0.09 mm
V = 494.42 (4) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	2256 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1973 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.040
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.5°
ϕ and ω scans	h = −6→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −7→7
T_min = 0.639, T_max = 0.746	l = −23→23
9074 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0347P)² + 0.3167P] where P = (F_o² + 2F_c²)/3
2256 reflections	(Δ/σ)_max = 0.001
151 parameters	Δρ_max = 0.29 e Å⁻³
2 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₉H₈N₄O₂S	γ = 79.855 (3)°
M_r = 236.26	V = 494.42 (4) Å³
Triclinic, P1	Z = 2
a = 5.0878 (2) Å	Mo Kα radiation
b = 5.6213 (3) Å	µ = 0.32 mm⁻¹
c = 17.8035 (9) Å	T = 120 K
α = 80.980 (3)°	0.38 × 0.20 × 0.09 mm
β = 85.677 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2256 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1973 reflections with I > 2σ(I)
T_min = 0.639, T_max = 0.746	R_int = 0.040
9074 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
2256 reflections	Δρ_min = −0.33 e Å⁻³
151 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.39352 (8)	0.87897 (7)	0.63466 (2)	0.01803 (12)
O1	−0.3420 (3)	0.5966 (2)	0.79836 (7)	0.0282 (3)
O2	−0.2766 (3)	0.4981 (2)	0.91883 (7)	0.0326 (3)
N1	0.7365 (3)	1.1393 (2)	0.56903 (8)	0.0187 (3)
N2	0.5591 (3)	1.2890 (2)	0.61221 (8)	0.0185 (3)
N3	0.8153 (3)	0.7356 (2)	0.54139 (8)	0.0198 (3)
H1N	0.7552	0.5959	0.5485	0.030*
H2N	0.9445	0.7652	0.5073	0.030*
N4	−0.2396 (3)	0.6204 (2)	0.85639 (8)	0.0218 (3)
C1	0.6754 (3)	0.9177 (3)	0.57569 (9)	0.0160 (3)
C2	0.3731 (3)	1.1810 (3)	0.64921 (9)	0.0161 (3)
C3	0.1583 (3)	1.2978 (3)	0.70123 (9)	0.0189 (3)
H3A	−0.0131	1.3369	0.6754	0.023*
H3B	0.2049	1.4528	0.7116	0.023*
C4	0.1235 (3)	1.1329 (3)	0.77600 (9)	0.0167 (3)
C5	−0.0430 (3)	0.9582 (3)	0.78225 (9)	0.0164 (3)
H5	−0.1411	0.9442	0.7403	0.020*
C6	−0.0634 (3)	0.8046 (3)	0.85083 (9)	0.0180 (3)
C7	0.0726 (3)	0.8188 (3)	0.91408 (10)	0.0231 (4)
H7	0.0545	0.7117	0.9604	0.028*
C8	0.2360 (3)	0.9947 (3)	0.90746 (10)	0.0249 (4)
H8	0.3309	1.0096	0.9500	0.030*
C9	0.2626 (3)	1.1498 (3)	0.83935 (10)	0.0208 (3)
H9	0.3766	1.2684	0.8358	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0196 (2)	0.0135 (2)	0.0218 (2)	−0.00748 (15)	0.00547 (15)	−0.00271 (14)
O1	0.0321 (7)	0.0250 (6)	0.0306 (7)	−0.0141 (5)	−0.0028 (5)	−0.0022 (5)
O2	0.0328 (7)	0.0306 (7)	0.0307 (7)	−0.0112 (6)	0.0028 (6)	0.0113 (5)
N1	0.0184 (7)	0.0156 (6)	0.0228 (7)	−0.0061 (5)	0.0044 (5)	−0.0039 (5)
N2	0.0186 (7)	0.0152 (6)	0.0225 (7)	−0.0061 (5)	0.0034 (5)	−0.0036 (5)
N3	0.0206 (7)	0.0140 (6)	0.0252 (8)	−0.0067 (5)	0.0064 (5)	−0.0036 (5)
N4	0.0193 (7)	0.0170 (7)	0.0271 (8)	−0.0029 (5)	0.0029 (6)	0.0012 (6)
C1	0.0156 (7)	0.0165 (7)	0.0162 (8)	−0.0058 (6)	−0.0008 (6)	0.0001 (6)
C2	0.0188 (7)	0.0130 (7)	0.0174 (8)	−0.0060 (6)	−0.0006 (6)	−0.0014 (6)
C3	0.0214 (8)	0.0131 (7)	0.0225 (8)	−0.0052 (6)	0.0035 (6)	−0.0024 (6)
C4	0.0143 (7)	0.0145 (7)	0.0210 (8)	−0.0018 (6)	0.0046 (6)	−0.0049 (6)
C5	0.0156 (7)	0.0163 (7)	0.0170 (8)	−0.0020 (6)	0.0006 (6)	−0.0033 (6)
C6	0.0150 (7)	0.0156 (7)	0.0226 (8)	−0.0024 (6)	0.0025 (6)	−0.0020 (6)
C7	0.0226 (8)	0.0262 (9)	0.0174 (8)	0.0002 (7)	0.0019 (6)	−0.0001 (7)
C8	0.0228 (9)	0.0325 (9)	0.0209 (9)	−0.0032 (7)	−0.0041 (7)	−0.0085 (7)
C9	0.0173 (8)	0.0220 (8)	0.0254 (9)	−0.0052 (6)	0.0017 (6)	−0.0096 (7)

Geometric parameters (Å, º) top

S1—C1	1.7373 (16)	C3—H3A	0.9900
S1—C2	1.7412 (15)	C3—H3B	0.9900
O1—N4	1.2271 (19)	C4—C5	1.393 (2)
O2—N4	1.2321 (18)	C4—C9	1.400 (2)
N1—C1	1.321 (2)	C5—C6	1.389 (2)
N1—N2	1.3949 (19)	C5—H5	0.9500
N2—C2	1.297 (2)	C6—C7	1.385 (2)
N3—C1	1.342 (2)	C7—C8	1.386 (2)
N3—H1N	0.8800	C7—H7	0.9500
N3—H2N	0.8799	C8—C9	1.391 (2)
N4—C6	1.472 (2)	C8—H8	0.9500
C2—C3	1.506 (2)	C9—H9	0.9500
C3—C4	1.516 (2)

C1—S1—C2	87.36 (7)	H3A—C3—H3B	107.9
C1—N1—N2	111.82 (13)	C5—C4—C9	118.89 (15)
C2—N2—N1	113.45 (12)	C5—C4—C3	120.45 (14)
C1—N3—H1N	117.3	C9—C4—C3	120.64 (14)
C1—N3—H2N	119.9	C6—C5—C4	118.95 (14)
H1N—N3—H2N	122.0	C6—C5—H5	120.5
O1—N4—O2	123.37 (14)	C4—C5—H5	120.5
O1—N4—C6	118.11 (13)	C7—C6—C5	122.94 (15)
O2—N4—C6	118.52 (14)	C7—C6—N4	118.81 (14)
N1—C1—N3	124.39 (14)	C5—C6—N4	118.25 (14)
N1—C1—S1	113.68 (12)	C6—C7—C8	117.65 (15)
N3—C1—S1	121.93 (11)	C6—C7—H7	121.2
N2—C2—C3	124.72 (13)	C8—C7—H7	121.2
N2—C2—S1	113.68 (12)	C9—C8—C7	120.82 (15)
C3—C2—S1	121.59 (11)	C9—C8—H8	119.6
C2—C3—C4	112.03 (13)	C7—C8—H8	119.6
C2—C3—H3A	109.2	C8—C9—C4	120.74 (15)
C4—C3—H3A	109.2	C8—C9—H9	119.6
C2—C3—H3B	109.2	C4—C9—H9	119.6
C4—C3—H3B	109.2

C1—N1—N2—C2	−0.19 (19)	C3—C4—C5—C6	177.85 (14)
N2—N1—C1—N3	−178.79 (14)	C4—C5—C6—C7	0.8 (2)
N2—N1—C1—S1	0.65 (17)	C4—C5—C6—N4	−179.81 (13)
C2—S1—C1—N1	−0.70 (12)	O1—N4—C6—C7	−174.26 (14)
C2—S1—C1—N3	178.76 (14)	O2—N4—C6—C7	5.7 (2)
N1—N2—C2—C3	178.85 (14)	O1—N4—C6—C5	6.3 (2)
N1—N2—C2—S1	−0.36 (17)	O2—N4—C6—C5	−173.78 (14)
C1—S1—C2—N2	0.59 (12)	C5—C6—C7—C8	−0.2 (2)
C1—S1—C2—C3	−178.64 (14)	N4—C6—C7—C8	−179.63 (15)
N2—C2—C3—C4	−133.70 (16)	C6—C7—C8—C9	−0.4 (3)
S1—C2—C3—C4	45.44 (18)	C7—C8—C9—C4	0.5 (3)
C2—C3—C4—C5	−85.79 (18)	C5—C4—C9—C8	0.1 (2)
C2—C3—C4—C9	92.73 (17)	C3—C4—C9—C8	−178.44 (15)
C9—C4—C5—C6	−0.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1n···N2ⁱ	0.88	2.25	3.0828 (19)	157
N3—H2n···N1ⁱⁱ	0.88	2.12	3.003 (2)	175
C3—H3a···N2ⁱⁱⁱ	0.99	2.60	3.552 (2)	162
C3—H3b···S1^iv	0.99	2.85	3.6687 (17)	141
C7—H7···O2^v	0.95	2.53	3.355 (2)	145
C9—H9···O1^vi	0.95	2.51	3.446 (2)	168
C5—H5···Cgⁱⁱⁱ	0.95	2.86	3.7708 (17)	160

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

Experimental details

Crystal data
Chemical formula	C₉H₈N₄O₂S
M_r	236.26
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	5.0878 (2), 5.6213 (3), 17.8035 (9)
α, β, γ (°)	80.980 (3), 85.677 (3), 79.855 (3)
V (Å³)	494.42 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.38 × 0.20 × 0.09

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.639, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	9074, 2256, 1973
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.05
No. of reflections	2256
No. of parameters	151
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.33

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1n···N2ⁱ	0.88	2.25	3.0828 (19)	157
N3—H2n···N1ⁱⁱ	0.88	2.12	3.003 (2)	175
C3—H3a···N2ⁱⁱⁱ	0.99	2.60	3.552 (2)	162
C3—H3b···S1^iv	0.99	2.85	3.6687 (17)	141
C7—H7···O2^v	0.95	2.53	3.355 (2)	145
C9—H9···O1^vi	0.95	2.51	3.446 (2)	168
C5—H5···Cgⁱⁱⁱ	0.95	2.86	3.7708 (17)	160

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

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

Amir, M., Kumar, A., Ali, A. & Khan, A. S. (2009). J. Ind. Chem. Sect. B, 48, 1288–1293. Google Scholar
Boechat, N., Ferreira, S. B., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, S. M. S. V. (2006). Acta Cryst. C62, o42–o44. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Boechat, N., Kover, W. B., Bastos, M. M., Pinto, A. C., Maciel, L. C. L., Mayer, L. M. U., da Silva, F. S. Q., Sá, P. M., Mendonça, J. S., Wardell, S. M. S. V. & Arruda, M. S. L. (2008). J. Braz. Chem. Soc. 19, 445–457. Web of Science CSD CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Carvalho, S. A., da Silva, E. F., Santa-Rita, R. M., de Castro, S. L. & Fraga, C. A. M. (2004). Bioorg. Med. Chem. Lett. 14, 5967–5970. Web of Science CrossRef PubMed CAS Google Scholar
Carvalho, S. A., Lopes, F. A. S., Salomão, K., Romeiro, N. C., Wardell, S. M. S. V., de Castro, S. L., da Silva, E. F. & Fraga, C. A. M. (2008). Bioorg. Med. Chem. 16, 413–421. Web of Science CSD CrossRef PubMed CAS Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Moise, M., Sunel, V., Profire, L., Popa, M., Desbrieres, J. & Peptu, C. (2009). Molecules, 14, 2621–2631. Web of Science CrossRef PubMed Google Scholar
Oruç, E. E., Rollas, S., Kandemirli, F. N., Shvets, N. & Dimoglo, A. S. (2004). J. Med. Chem. 47, 6760–6767. Web of Science PubMed Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Poorrajab, F., Ardestani, S. K., Emami, S., Behrouzi-Fardmoghadam, M., Shafiee, A. & Foroumadi, A. (2009). Eur. J. Med. Chem. 44, 1758–1762. Web of Science CrossRef PubMed CAS Google Scholar
Riente, R. R., Souza, V. P., Carvalho, S. A., Kaiser, M., Brum, R. & Silva, E. F. (2009). J. Med. Chem. 4, 392–397. CrossRef Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomasco, M. L., Godwood, C. R., Weaver, A. E., Ochoada, M. J. & Ford, W. C. (2003). Bioorg. Med. Chem. 13, 4193–4197. CrossRef CAS Google Scholar
Turner, S., Myers, M., Gadie, B., Nelson, A. J., Pape, R., Saville, J. F., Doxey, J. C. & Berridge, T. L. (1988). J. Med. Chem. 31, 902–906. CrossRef CAS PubMed Web of Science Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar