1-(2-Methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl acetate.

In the title compound, C9H13N3O4, an ester of the anti-infection drug secnidazole, the dihedral angle between the nitro-imidazole mean plane (r.m.s. deviation = 0.028 Å) and the pendant acetate group is 43.17 (11)°. In the crystal, inversion dimers linked by pairs of C-H⋯O inter-actions generate R 2 (2)(10) loops and further C-H⋯O hydrogen bonds link the dimers into [100] chains. Weak aromatic π-π stacking inter-actions with a centroid-centroid distance of 3.7623 (11) Å are also observed.

Related literature

For background to the anti­bacterial properties of nitro­imidazole and secnidazole-like compounds, see: Mital (2009 ▶); Edwards (1993 ▶); Crozet et al. (2009 ▶). For the crystal structures of related compounds, see: Yousuf et al. (2013 ▶); Tao et al. (2008 ▶);Zeb et al. (2012 ▶).

Experimental

Crystal data

C9H13N3O4

M = 227.22

Monoclinic,

a = 6.1771 (5) Å

b = 8.9928 (7) Å

c = 20.3736 (16) Å

β = 90.978 (2)°

V = 1131.58 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 273 K

0.45 × 0.27 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.954, T max = 0.994

6541 measured reflections

2042 independent reflections

1567 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.02

2042 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.12 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/S1600536814002505/hb7195sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002505/hb7195Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002505/hb7195Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H13N3O4	F(000) = 480
Mr = 227.22	Dx = 1.334 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.1771 (5) Å	Cell parameters from 1751 reflections
b = 8.9928 (7) Å	θ = 2.5–22.3°
c = 20.3736 (16) Å	µ = 0.11 mm−1
β = 90.978 (2)°	T = 273 K
V = 1131.58 (16) Å3	Plate, colourless
Z = 4	0.45 × 0.27 × 0.06 mm

Bruker SMART APEX CCD diffractometer	2042 independent reflections
Radiation source: fine-focus sealed tube	1567 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scan	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.954, Tmax = 0.994	k = −10→10
6541 measured reflections	l = −23→24

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.1628P] where P = (Fo2 + 2Fc2)/3
2042 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.12 e Å−3

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	0.9023 (2)	0.57210 (19)	0.08857 (8)	0.0881 (5)
O2	0.6626 (3)	0.55701 (17)	0.16347 (8)	0.0834 (5)
O3	0.48247 (17)	0.11443 (13)	0.18968 (6)	0.0498 (3)
O4	0.8273 (2)	0.17014 (17)	0.16857 (8)	0.0744 (5)
N2	0.7361 (3)	0.51890 (17)	0.11093 (9)	0.0604 (5)
N3	0.5484 (3)	0.2475 (2)	−0.00606 (8)	0.0658 (5)
N1	0.4442 (2)	0.33433 (15)	0.09081 (7)	0.0476 (4)
C5	0.6300 (3)	0.40876 (19)	0.07274 (9)	0.0497 (5)
C4	0.6890 (3)	0.3540 (2)	0.01383 (10)	0.0599 (5)
H4A	0.8088	0.3851	−0.0095	0.072*
C2	0.4036 (3)	0.2373 (2)	0.04109 (10)	0.0552 (5)
C11	0.2199 (3)	0.1309 (3)	0.03950 (12)	0.0744 (6)
H11A	0.2237	0.0738	−0.0003	0.112*
H11B	0.0859	0.1848	0.0412	0.112*
H11C	0.2312	0.0654	0.0766	0.112*
C6	0.3239 (3)	0.3431 (2)	0.15215 (9)	0.0517 (5)
H6A	0.1826	0.2979	0.1455	0.062*
H6B	0.3018	0.4468	0.1633	0.062*
C7	0.4387 (3)	0.26641 (19)	0.20886 (9)	0.0489 (5)
H7A	0.5748	0.3178	0.2193	0.059*
C8	0.2980 (4)	0.2624 (2)	0.26847 (10)	0.0674 (6)
H8A	0.3741	0.2134	0.3038	0.101*
H8B	0.1670	0.2092	0.2583	0.101*
H8C	0.2633	0.3622	0.2814	0.101*
C9	0.6837 (3)	0.0809 (2)	0.17030 (9)	0.0514 (5)
C10	0.7003 (3)	−0.0780 (2)	0.15128 (12)	0.0731 (6)
H10A	0.8452	−0.0989	0.1377	0.110*
H10B	0.6007	−0.0982	0.1157	0.110*
H10C	0.6658	−0.1395	0.1882	0.110*

	U11	U22	U33	U12	U13	U23
O1	0.0725 (10)	0.0951 (12)	0.0972 (12)	−0.0330 (9)	0.0186 (9)	−0.0015 (10)
O2	0.1073 (12)	0.0620 (9)	0.0817 (11)	−0.0251 (8)	0.0283 (10)	−0.0176 (8)
O3	0.0430 (6)	0.0450 (7)	0.0615 (8)	−0.0013 (5)	0.0057 (6)	0.0015 (6)
O4	0.0452 (7)	0.0801 (10)	0.0982 (12)	−0.0049 (7)	0.0122 (7)	0.0021 (9)
N2	0.0624 (10)	0.0496 (9)	0.0693 (12)	−0.0064 (8)	0.0080 (9)	0.0057 (8)
N3	0.0700 (11)	0.0718 (11)	0.0558 (11)	0.0022 (9)	0.0071 (9)	−0.0034 (9)
N1	0.0473 (8)	0.0420 (7)	0.0536 (9)	0.0043 (6)	0.0056 (7)	0.0033 (7)
C5	0.0488 (9)	0.0452 (10)	0.0551 (12)	0.0015 (8)	0.0040 (9)	0.0065 (8)
C4	0.0565 (11)	0.0639 (12)	0.0595 (13)	0.0037 (10)	0.0109 (10)	0.0096 (10)
C2	0.0551 (11)	0.0536 (11)	0.0570 (12)	0.0043 (8)	0.0002 (9)	−0.0004 (9)
C11	0.0676 (13)	0.0759 (14)	0.0794 (16)	−0.0104 (11)	−0.0022 (12)	−0.0129 (12)
C6	0.0461 (9)	0.0476 (10)	0.0618 (12)	0.0042 (8)	0.0119 (9)	−0.0012 (9)
C7	0.0482 (9)	0.0444 (9)	0.0544 (11)	−0.0031 (8)	0.0073 (8)	−0.0037 (8)
C8	0.0717 (13)	0.0701 (13)	0.0609 (13)	−0.0068 (10)	0.0190 (11)	−0.0045 (10)
C9	0.0445 (9)	0.0612 (11)	0.0486 (11)	0.0040 (9)	0.0015 (8)	0.0070 (9)
C10	0.0706 (13)	0.0668 (13)	0.0820 (16)	0.0185 (11)	0.0043 (12)	−0.0038 (12)

O1—N2	1.2276 (19)	C11—H11B	0.9600
O2—N2	1.219 (2)	C11—H11C	0.9600
O3—C9	1.3447 (19)	C6—C7	1.512 (3)
O3—C7	1.448 (2)	C6—H6A	0.9700
O4—C9	1.197 (2)	C6—H6B	0.9700
N2—C5	1.414 (2)	C7—C8	1.506 (2)
N3—C2	1.327 (2)	C7—H7A	0.9800
N3—C4	1.351 (3)	C8—H8A	0.9600
N1—C2	1.357 (2)	C8—H8B	0.9600
N1—C5	1.384 (2)	C8—H8C	0.9600
N1—C6	1.467 (2)	C9—C10	1.485 (3)
C5—C4	1.353 (3)	C10—H10A	0.9600
C4—H4A	0.9300	C10—H10B	0.9600
C2—C11	1.484 (3)	C10—H10C	0.9600
C11—H11A	0.9600
C9—O3—C7	117.93 (13)	C7—C6—H6A	109.0
O2—N2—O1	122.85 (18)	N1—C6—H6B	109.0
O2—N2—C5	120.29 (15)	C7—C6—H6B	109.0
O1—N2—C5	116.86 (17)	H6A—C6—H6B	107.8
C2—N3—C4	105.66 (17)	O3—C7—C8	107.95 (14)
C2—N1—C5	104.86 (14)	O3—C7—C6	108.15 (14)
C2—N1—C6	125.45 (14)	C8—C7—C6	110.95 (15)
C5—N1—C6	129.44 (15)	O3—C7—H7A	109.9
C4—C5—N1	107.28 (17)	C8—C7—H7A	109.9
C4—C5—N2	127.87 (17)	C6—C7—H7A	109.9
N1—C5—N2	124.84 (16)	C7—C8—H8A	109.5
N3—C4—C5	110.04 (17)	C7—C8—H8B	109.5
N3—C4—H4A	125.0	H8A—C8—H8B	109.5
C5—C4—H4A	125.0	C7—C8—H8C	109.5
N3—C2—N1	112.15 (17)	H8A—C8—H8C	109.5
N3—C2—C11	123.62 (19)	H8B—C8—H8C	109.5
N1—C2—C11	124.23 (17)	O4—C9—O3	123.20 (17)
C2—C11—H11A	109.5	O4—C9—C10	125.65 (18)
C2—C11—H11B	109.5	O3—C9—C10	111.14 (16)
H11A—C11—H11B	109.5	C9—C10—H10A	109.5
C2—C11—H11C	109.5	C9—C10—H10B	109.5
H11A—C11—H11C	109.5	H10A—C10—H10B	109.5
H11B—C11—H11C	109.5	C9—C10—H10C	109.5
N1—C6—C7	112.86 (13)	H10A—C10—H10C	109.5
N1—C6—H6A	109.0	H10B—C10—H10C	109.5
C2—N1—C5—C4	0.4 (2)	C5—N1—C2—N3	−0.6 (2)
C6—N1—C5—C4	174.87 (16)	C6—N1—C2—N3	−175.27 (16)
C2—N1—C5—N2	−178.36 (17)	C5—N1—C2—C11	179.00 (18)
C6—N1—C5—N2	−3.9 (3)	C6—N1—C2—C11	4.3 (3)
O2—N2—C5—C4	179.99 (19)	C2—N1—C6—C7	100.0 (2)
O1—N2—C5—C4	−0.1 (3)	C5—N1—C6—C7	−73.4 (2)
O2—N2—C5—N1	−1.5 (3)	C9—O3—C7—C8	−139.19 (17)
O1—N2—C5—N1	178.41 (17)	C9—O3—C7—C6	100.71 (17)
C2—N3—C4—C5	−0.1 (2)	N1—C6—C7—O3	−55.09 (18)
N1—C5—C4—N3	−0.2 (2)	N1—C6—C7—C8	−173.30 (14)
N2—C5—C4—N3	178.55 (18)	C7—O3—C9—O4	0.4 (3)
C4—N3—C2—N1	0.4 (2)	C7—O3—C9—C10	−178.99 (16)
C4—N3—C2—C11	−179.12 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1i	0.93	2.45	3.369 (2)	168
C6—H6A···O4ii	0.97	2.53	3.460 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1i	0.93	2.45	3.369 (2)	168
C6—H6A⋯O4ii	0.97	2.53	3.460 (2)	161

Symmetry codes: (i) ; (ii) .