2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-fluoro-benzoate.

In the title compound, C(13)H(12)FN(3)O(4), the dihedral angle between the benzene and imidazole rings is 32.77 (12)°. In the crystal, mol-ecules are linked into a three-dimensional network by C-H⋯O hydrogen bonds.

Related literature

For biological activities of metronidazole derivatives, see: Atia (2009 ▶); Beena et al. (2009 ▶); Bowden & Izadi (1998 ▶); Dubey et al. (2009 ▶); Mao et al. (2009 ▶); Qian et al. (2010 ▶).

Experimental

Crystal data

C13H12FN3O4

M = 293.26

Monoclinic,

a = 8.9669 (12) Å

b = 18.784 (2) Å

c = 7.8288 (10) Å

β = 99.684 (3)°

V = 1299.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 273 K

0.50 × 0.29 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.941, T max = 0.981

3782 measured reflections

1186 independent reflections

1150 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.06

1186 reflections

192 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006319/is5064sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006319/is5064Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006319/is5064Isup3.cml

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

C13H12FN3O4	F(000) = 608
Mr = 293.26	Dx = 1.498 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 8.9669 (12) Å	Cell parameters from 2305 reflections
b = 18.784 (2) Å	θ = 2.6–28.0°
c = 7.8288 (10) Å	µ = 0.12 mm−1
β = 99.684 (3)°	T = 273 K
V = 1299.9 (3) Å3	Block, colourless
Z = 4	0.50 × 0.29 × 0.16 mm

Bruker SMART APEX CCD diffractometer	1186 independent reflections
Radiation source: fine-focus sealed tube	1150 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.941, Tmax = 0.981	k = −22→22
3782 measured reflections	l = −9→8

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.2616P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1186 reflections	Δρmax = 0.15 e Å−3
192 parameters	Δρmin = −0.11 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (15)

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
O1	−0.1173 (2)	0.24543 (13)	−0.1523 (3)	0.0625 (6)
O2	0.0800 (2)	0.27301 (10)	0.0543 (2)	0.0534 (5)
O3	0.0473 (3)	0.48885 (12)	0.3047 (4)	0.0795 (8)
O4	0.2371 (3)	0.50643 (12)	0.5096 (4)	0.0726 (7)
N1	0.0456 (2)	0.34305 (11)	0.3929 (3)	0.0405 (5)
N2	0.1729 (3)	0.29745 (13)	0.6362 (3)	0.0532 (6)
N3	0.1392 (3)	0.46795 (12)	0.4283 (3)	0.0516 (6)
C1	0.1985 (3)	0.13945 (15)	0.0541 (3)	0.0454 (6)
H1A	0.2496	0.1741	0.1262	0.054*
C2	0.2552 (3)	0.07076 (17)	0.0578 (4)	0.0539 (7)
H2B	0.3442	0.0587	0.1312	0.065*
C3	0.1764 (3)	0.02112 (15)	−0.0496 (4)	0.0533 (7)
C4	0.0462 (3)	0.03555 (17)	−0.1617 (4)	0.0554 (7)
H4A	−0.0035	0.0004	−0.2335	0.066*
C5	−0.0093 (3)	0.10470 (15)	−0.1646 (4)	0.0481 (6)
H5A	−0.0978	0.1163	−0.2397	0.058*
C6	0.0659 (3)	0.15675 (14)	−0.0565 (3)	0.0408 (6)
C7	−0.0021 (3)	0.22884 (14)	−0.0609 (3)	0.0429 (6)
C8	0.0198 (4)	0.34362 (15)	0.0713 (4)	0.0569 (7)
H8A	−0.0514	0.3554	−0.0323	0.068*
H8B	0.1013	0.3781	0.0840	0.068*
C9	−0.0587 (3)	0.34704 (14)	0.2269 (4)	0.0474 (6)
H9A	−0.1153	0.3912	0.2230	0.057*
H9B	−0.1304	0.3081	0.2208	0.057*
C10	0.1340 (3)	0.39608 (14)	0.4807 (4)	0.0454 (6)
C11	0.2095 (3)	0.36676 (16)	0.6288 (4)	0.0535 (7)
H11A	0.2764	0.3909	0.7126	0.064*
C12	0.0761 (3)	0.28463 (14)	0.4928 (4)	0.0435 (6)
C13	0.0081 (4)	0.21350 (15)	0.4469 (4)	0.0579 (8)
H13A	0.0472	0.1798	0.5353	0.087*
H13B	0.0332	0.1984	0.3381	0.087*
H13C	−0.0998	0.2165	0.4376	0.087*
F1	0.2301 (3)	−0.04671 (11)	−0.0425 (3)	0.0827 (7)

	U11	U22	U33	U12	U13	U23
O1	0.0549 (11)	0.0618 (12)	0.0642 (14)	0.0139 (10)	−0.0092 (10)	0.0027 (11)
O2	0.0660 (12)	0.0480 (11)	0.0422 (11)	0.0104 (9)	−0.0022 (9)	−0.0033 (8)
O3	0.0938 (17)	0.0483 (12)	0.0877 (18)	0.0064 (12)	−0.0103 (15)	0.0188 (12)
O4	0.0740 (14)	0.0472 (11)	0.0926 (18)	−0.0096 (11)	0.0026 (13)	−0.0116 (12)
N1	0.0454 (10)	0.0358 (10)	0.0395 (12)	0.0050 (8)	0.0048 (9)	−0.0012 (9)
N2	0.0660 (14)	0.0472 (12)	0.0429 (14)	0.0034 (11)	−0.0012 (11)	0.0026 (10)
N3	0.0562 (12)	0.0392 (11)	0.0598 (15)	0.0043 (10)	0.0113 (11)	−0.0010 (11)
C1	0.0473 (13)	0.0508 (14)	0.0371 (14)	0.0048 (11)	0.0039 (11)	0.0013 (11)
C2	0.0525 (15)	0.0622 (18)	0.0451 (15)	0.0134 (13)	0.0028 (12)	0.0075 (13)
C3	0.0732 (19)	0.0435 (15)	0.0463 (17)	0.0125 (13)	0.0193 (14)	0.0061 (12)
C4	0.0673 (17)	0.0485 (14)	0.0510 (17)	−0.0084 (13)	0.0119 (14)	−0.0089 (13)
C5	0.0475 (13)	0.0529 (15)	0.0424 (15)	−0.0014 (11)	0.0033 (11)	−0.0002 (11)
C6	0.0417 (11)	0.0455 (13)	0.0359 (14)	0.0014 (10)	0.0088 (10)	0.0009 (10)
C7	0.0454 (13)	0.0484 (15)	0.0347 (14)	0.0049 (10)	0.0064 (10)	0.0034 (11)
C8	0.085 (2)	0.0412 (15)	0.0427 (16)	0.0099 (13)	0.0049 (14)	0.0064 (11)
C9	0.0532 (14)	0.0419 (13)	0.0427 (15)	0.0073 (11)	−0.0049 (11)	−0.0005 (11)
C10	0.0480 (12)	0.0395 (13)	0.0474 (16)	0.0047 (10)	0.0043 (11)	−0.0050 (10)
C11	0.0553 (14)	0.0476 (14)	0.0531 (17)	0.0011 (12)	−0.0038 (12)	−0.0071 (13)
C12	0.0517 (13)	0.0381 (12)	0.0406 (15)	0.0044 (11)	0.0079 (11)	0.0033 (10)
C13	0.082 (2)	0.0397 (14)	0.0501 (18)	−0.0051 (14)	0.0053 (15)	0.0026 (13)
F1	0.1168 (17)	0.0497 (11)	0.0819 (15)	0.0242 (11)	0.0175 (13)	0.0035 (10)

O1—C7	1.195 (3)	C3—C4	1.364 (4)
O2—C7	1.349 (3)	C4—C5	1.390 (4)
O2—C8	1.447 (3)	C4—H4A	0.9300
O3—N3	1.225 (3)	C5—C6	1.391 (4)
O4—N3	1.229 (4)	C5—H5A	0.9300
N1—C12	1.349 (3)	C6—C7	1.483 (3)
N1—C10	1.382 (3)	C8—C9	1.507 (4)
N1—C9	1.470 (4)	C8—H8A	0.9700
N2—C12	1.321 (4)	C8—H8B	0.9700
N2—C11	1.346 (4)	C9—H9A	0.9700
N3—C10	1.414 (4)	C9—H9B	0.9700
C1—C2	1.385 (4)	C10—C11	1.357 (4)
C1—C6	1.387 (3)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.487 (4)
C2—C3	1.370 (4)	C13—H13A	0.9600
C2—H2B	0.9300	C13—H13B	0.9600
C3—F1	1.360 (3)	C13—H13C	0.9600
C7—O2—C8	117.1 (2)	O2—C7—C6	111.7 (2)
C12—N1—C10	104.7 (2)	O2—C8—C9	110.2 (2)
C12—N1—C9	126.2 (2)	O2—C8—H8A	109.6
C10—N1—C9	129.0 (2)	C9—C8—H8A	109.6
C12—N2—C11	105.6 (2)	O2—C8—H8B	109.6
O3—N3—O4	123.2 (3)	C9—C8—H8B	109.6
O3—N3—C10	119.0 (2)	H8A—C8—H8B	108.1
O4—N3—C10	117.8 (3)	N1—C9—C8	113.4 (2)
C2—C1—C6	120.3 (3)	N1—C9—H9A	108.9
C2—C1—H1A	119.9	C8—C9—H9A	108.9
C6—C1—H1A	119.9	N1—C9—H9B	108.9
C3—C2—C1	118.2 (3)	C8—C9—H9B	108.9
C3—C2—H2B	120.9	H9A—C9—H9B	107.7
C1—C2—H2B	120.9	C11—C10—N1	107.1 (2)
F1—C3—C4	118.1 (3)	C11—C10—N3	126.8 (3)
F1—C3—C2	118.1 (3)	N1—C10—N3	126.0 (2)
C4—C3—C2	123.8 (3)	N2—C11—C10	109.9 (3)
C3—C4—C5	117.5 (3)	N2—C11—H11A	125.1
C3—C4—H4A	121.3	C10—C11—H11A	125.1
C5—C4—H4A	121.3	N2—C12—N1	112.6 (2)
C4—C5—C6	120.7 (3)	N2—C12—C13	123.6 (2)
C4—C5—H5A	119.6	N1—C12—C13	123.8 (3)
C6—C5—H5A	119.6	C12—C13—H13A	109.5
C1—C6—C5	119.5 (2)	C12—C13—H13B	109.5
C1—C6—C7	122.3 (2)	H13A—C13—H13B	109.5
C5—C6—C7	118.2 (2)	C12—C13—H13C	109.5
O1—C7—O2	124.0 (2)	H13A—C13—H13C	109.5
O1—C7—C6	124.2 (3)	H13B—C13—H13C	109.5
C6—C1—C2—C3	−0.3 (4)	O2—C8—C9—N1	70.0 (3)
C1—C2—C3—F1	−178.3 (2)	C12—N1—C10—C11	−1.2 (3)
C1—C2—C3—C4	0.8 (4)	C9—N1—C10—C11	179.3 (3)
F1—C3—C4—C5	178.4 (3)	C12—N1—C10—N3	−178.8 (3)
C2—C3—C4—C5	−0.6 (4)	C9—N1—C10—N3	1.7 (4)
C3—C4—C5—C6	−0.1 (4)	O3—N3—C10—C11	−168.7 (3)
C2—C1—C6—C5	−0.4 (4)	O4—N3—C10—C11	11.5 (4)
C2—C1—C6—C7	177.9 (2)	O3—N3—C10—N1	8.4 (4)
C4—C5—C6—C1	0.6 (4)	O4—N3—C10—N1	−171.3 (3)
C4—C5—C6—C7	−177.8 (2)	C12—N2—C11—C10	0.3 (3)
C8—O2—C7—O1	2.6 (4)	N1—C10—C11—N2	0.6 (3)
C8—O2—C7—C6	−175.7 (2)	N3—C10—C11—N2	178.2 (3)
C1—C6—C7—O1	−178.7 (3)	C11—N2—C12—N1	−1.1 (3)
C5—C6—C7—O1	−0.4 (4)	C11—N2—C12—C13	179.0 (3)
C1—C6—C7—O2	−0.4 (3)	C10—N1—C12—N2	1.4 (3)
C5—C6—C7—O2	177.9 (2)	C9—N1—C12—N2	−179.0 (2)
C7—O2—C8—C9	99.1 (3)	C10—N1—C12—C13	−178.6 (2)
C12—N1—C9—C8	−99.5 (3)	C9—N1—C12—C13	0.9 (4)
C10—N1—C9—C8	79.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.93	2.45	3.378 (3)	172
C2—H2B···O3ii	0.93	2.46	3.356 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.93	2.45	3.378 (3)	172
C2—H2B⋯O3ii	0.93	2.46	3.356 (4)	162

Symmetry codes: (i) ; (ii) .