Benznidazole.

THE CONFORMATION OF THE TITLE COMPOUND [SYSTEMATIC NAME: N-benzyl-2-(2-nitro-imidazol-1-yl)acetamide], C(12)H(12)N(4)O(3), can be described in terms of the relative orientation of three planar fragments, the imidazol group (A), benzyl group (B), and the acetamide fragment (C), with corresponding dihedral angles: A/C = 88.17 (4), B/C = 67.12 (5) and A/B = 21.11 (4)°. The crystal packing is enhanced by a network of strong inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Coura & Castro (2002 ▶); Lamas et al. (2006 ▶); Morilla et al. (2004 ▶); Silva et al. (2007 ▶).

Experimental

Crystal data

C12H12N4O3

M = 260.26

Monoclinic,

a = 4.65560 (10) Å

b = 10.9113 (2) Å

c = 11.7681 (3) Å

β = 90.6680 (10)°

V = 597.76 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 (2) K

0.34 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.861, T max = 0.987

11597 measured reflections

1287 independent reflections

1216 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.066

S = 1.08

1287 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005023/om2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005023/om2213Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 3

C12H12N4O3	F000 = 272
Mr = 260.26	Dx = 1.446 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.7107 Å
Hall symbol: P 2yb	Cell parameters from 1992 reflections
a = 4.65560 (10) Å	θ = 3.0–28.3º
b = 10.9113 (2) Å	µ = 0.11 mm−1
c = 11.7681 (3) Å	T = 100 (2) K
β = 90.6680 (10)º	Prism, colourless
V = 597.76 (2) Å3	0.34 × 0.16 × 0.12 mm
Z = 2

Bruker APEXII CCD diffractometer	1287 independent reflections
Radiation source: fine-focus sealed tube	1216 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.012
T = 100(2) K	θmax = 26.4º
ω and φ scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −5→5
Tmin = 0.861, Tmax = 0.987	k = −13→13
11597 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.0782P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1287 reflections	Δρmax = 0.14 e Å−3
176 parameters	Δρmin = −0.22 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
C1	0.4003 (3)	0.40584 (12)	0.08674 (11)	0.0161 (3)
C2	0.2787 (3)	0.42354 (13)	−0.02020 (12)	0.0185 (3)
H2	0.3368	0.4915	−0.0649	0.022*
C3	0.0725 (3)	0.34290 (15)	−0.06277 (12)	0.0228 (3)
H3	−0.0096	0.3558	−0.1361	0.027*
C4	−0.0126 (3)	0.24393 (15)	0.00205 (14)	0.0249 (3)
H4	−0.1559	0.1896	−0.0263	0.03*
C5	0.1101 (3)	0.22366 (13)	0.10809 (13)	0.0245 (3)
H5	0.0536	0.1548	0.1518	0.029*
C6	0.3162 (3)	0.30441 (13)	0.15048 (12)	0.0199 (3)
H6	0.4003	0.2904	0.2233	0.024*
C7	0.6208 (3)	0.49433 (14)	0.13271 (12)	0.0183 (3)
H7A	0.7996	0.4494	0.1521	0.022*
H7B	0.6664	0.5558	0.0737	0.022*
N8	0.5145 (3)	0.55688 (11)	0.23428 (10)	0.0162 (3)
H8	0.338 (4)	0.5619 (16)	0.2452 (14)	0.019 (4)*
C9	0.6898 (3)	0.62199 (12)	0.30060 (11)	0.0136 (3)
O10	0.94844 (19)	0.63427 (9)	0.28473 (8)	0.0174 (2)
C11	0.5490 (3)	0.67480 (13)	0.40651 (12)	0.0169 (3)
H11A	0.3579	0.7085	0.3859	0.02*
H11B	0.5211	0.6087	0.4629	0.02*
N12	0.7269 (2)	0.77163 (10)	0.45668 (9)	0.0155 (2)
C13	0.7665 (3)	0.89028 (13)	0.42442 (11)	0.0173 (3)
N14	0.9577 (3)	0.94933 (12)	0.48657 (10)	0.0212 (3)
C15	1.0495 (3)	0.86385 (13)	0.56313 (12)	0.0202 (3)
H15	1.1901	0.8781	0.6208	0.024*
C16	0.9113 (3)	0.75456 (13)	0.54557 (11)	0.0178 (3)
H16	0.939	0.681	0.5875	0.021*
N17	0.6082 (3)	0.94740 (12)	0.33348 (10)	0.0239 (3)
O18	0.4426 (2)	0.88404 (11)	0.27695 (9)	0.0306 (3)
O19	0.6452 (3)	1.05789 (11)	0.31808 (11)	0.0419 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0137 (6)	0.0156 (7)	0.0191 (6)	0.0026 (6)	0.0028 (5)	−0.0051 (5)
C2	0.0202 (7)	0.0166 (7)	0.0187 (7)	0.0025 (6)	0.0021 (5)	−0.0016 (5)
C3	0.0208 (7)	0.0276 (8)	0.0199 (7)	0.0040 (7)	−0.0040 (6)	−0.0089 (6)
C4	0.0191 (7)	0.0216 (8)	0.0340 (8)	−0.0045 (6)	0.0008 (6)	−0.0137 (6)
C5	0.0251 (8)	0.0152 (8)	0.0333 (8)	−0.0025 (6)	0.0055 (6)	−0.0029 (6)
C6	0.0212 (7)	0.0192 (8)	0.0193 (7)	−0.0006 (6)	0.0004 (5)	−0.0023 (6)
C7	0.0161 (7)	0.0196 (7)	0.0193 (7)	−0.0006 (6)	0.0030 (5)	−0.0047 (6)
N8	0.0106 (6)	0.0182 (6)	0.0198 (6)	−0.0003 (5)	0.0016 (4)	−0.0057 (5)
C9	0.0153 (7)	0.0096 (6)	0.0159 (6)	0.0013 (5)	0.0000 (5)	0.0008 (5)
O10	0.0134 (5)	0.0189 (5)	0.0198 (4)	−0.0008 (4)	0.0010 (4)	−0.0031 (4)
C11	0.0160 (6)	0.0155 (7)	0.0194 (7)	−0.0036 (6)	0.0012 (5)	−0.0059 (5)
N12	0.0168 (6)	0.0139 (6)	0.0159 (5)	−0.0011 (5)	0.0020 (4)	−0.0024 (5)
C13	0.0221 (7)	0.0133 (7)	0.0164 (6)	0.0005 (6)	−0.0001 (5)	−0.0013 (5)
N14	0.0281 (7)	0.0169 (6)	0.0187 (6)	−0.0036 (6)	−0.0021 (5)	−0.0029 (5)
C15	0.0236 (8)	0.0176 (7)	0.0194 (7)	0.0005 (6)	−0.0037 (6)	−0.0044 (5)
C16	0.0210 (7)	0.0153 (7)	0.0171 (6)	0.0029 (6)	−0.0014 (5)	−0.0014 (5)
N17	0.0325 (8)	0.0211 (7)	0.0179 (6)	0.0008 (6)	−0.0037 (5)	0.0002 (5)
O18	0.0347 (6)	0.0323 (7)	0.0244 (5)	−0.0023 (5)	−0.0114 (5)	−0.0012 (5)
O19	0.0699 (10)	0.0196 (6)	0.0358 (6)	−0.0031 (6)	−0.0180 (6)	0.0077 (5)

O10—C9	1.2281 (16)	C15—C16	1.370 (2)
N17—O18	1.2260 (17)	C15—H15	0.95
N17—O19	1.2316 (18)	C4—C3	1.383 (2)
N17—C13	1.4348 (18)	C4—C5	1.384 (2)
N12—C16	1.3581 (18)	C4—H4	0.95
N12—C13	1.3622 (19)	C5—C6	1.391 (2)
N12—C11	1.4628 (17)	C5—H5	0.95
N8—C9	1.3286 (17)	C3—H3	0.95
N8—C7	1.4675 (17)	C7—C1	1.505 (2)
N8—H8	0.836 (18)	C7—H7A	0.99
C9—C11	1.5278 (18)	C7—H7B	0.99
C2—C1	1.3875 (19)	C1—C6	1.396 (2)
C2—C3	1.391 (2)	C11—H11A	0.99
C2—H2	0.95	C11—H11B	0.99
N14—C13	1.3144 (19)	C16—H16	0.95
N14—C15	1.3620 (19)	C6—H6	0.95
O18—N17—O19	124.07 (13)	C4—C3—H3	120.1
O18—N17—C13	118.30 (12)	C2—C3—H3	120.1
O19—N17—C13	117.62 (13)	N8—C7—C1	110.86 (11)
C16—N12—C13	104.99 (12)	N8—C7—H7A	109.5
C16—N12—C11	124.17 (12)	C1—C7—H7A	109.5
C13—N12—C11	130.67 (12)	N8—C7—H7B	109.5
C9—N8—C7	121.09 (12)	C1—C7—H7B	109.5
C9—N8—H8	118.2 (12)	H7A—C7—H7B	108.1
C7—N8—H8	119.9 (11)	C2—C1—C6	118.93 (13)
O10—C9—N8	124.46 (12)	C2—C1—C7	120.41 (13)
O10—C9—C11	120.91 (12)	C6—C1—C7	120.65 (12)
N8—C9—C11	114.48 (11)	N12—C11—C9	110.81 (11)
C1—C2—C3	120.75 (13)	N12—C11—H11A	109.5
C1—C2—H2	119.6	C9—C11—H11A	109.5
C3—C2—H2	119.6	N12—C11—H11B	109.5
C13—N14—C15	103.74 (12)	C9—C11—H11B	109.5
N14—C15—C16	110.69 (12)	H11A—C11—H11B	108.1
N14—C15—H15	124.7	N12—C16—C15	106.76 (13)
C16—C15—H15	124.7	N12—C16—H16	126.6
C3—C4—C5	120.29 (14)	C15—C16—H16	126.6
C3—C4—H4	119.9	C5—C6—C1	120.41 (13)
C5—C4—H4	119.9	C5—C6—H6	119.8
C4—C5—C6	119.86 (14)	C1—C6—H6	119.8
C4—C5—H5	120.1	N14—C13—N12	113.81 (12)
C6—C5—H5	120.1	N14—C13—N17	122.74 (13)
C4—C3—C2	119.74 (13)	N12—C13—N17	123.42 (12)
C7—N8—C9—O10	−1.0 (2)	C11—N12—C16—C15	176.45 (12)
C7—N8—C9—C11	−176.53 (13)	N14—C15—C16—N12	−0.46 (16)
C13—N14—C15—C16	0.00 (16)	C4—C5—C6—C1	0.0 (2)
C3—C4—C5—C6	1.1 (2)	C2—C1—C6—C5	−1.1 (2)
C5—C4—C3—C2	−1.1 (2)	C7—C1—C6—C5	179.30 (13)
C1—C2—C3—C4	0.0 (2)	C15—N14—C13—N12	0.48 (16)
C9—N8—C7—C1	167.75 (12)	C15—N14—C13—N17	178.56 (13)
C3—C2—C1—C6	1.1 (2)	C16—N12—C13—N14	−0.77 (16)
C3—C2—C1—C7	−179.29 (13)	C11—N12—C13—N14	−176.13 (13)
N8—C7—C1—C2	116.20 (14)	C16—N12—C13—N17	−178.83 (13)
N8—C7—C1—C6	−64.20 (17)	C11—N12—C13—N17	5.8 (2)
C16—N12—C11—C9	−97.72 (15)	O18—N17—C13—N14	177.06 (14)
C13—N12—C11—C9	76.86 (17)	O19—N17—C13—N14	−3.8 (2)
O10—C9—C11—N12	20.40 (18)	O18—N17—C13—N12	−5.0 (2)
N8—C9—C11—N12	−163.87 (11)	O19—N17—C13—N12	174.08 (14)
C13—N12—C16—C15	0.70 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O10i	0.835 (19)	2.037 (18)	2.837 (2)	160.2 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O10i	0.835 (19)	2.037 (18)	2.837 (2)	160.2 (17)

Symmetry code: (i) .