1,2-Bis[2-(2-nitro-1H-imidazol-1-yl)eth-oxy]ethane.

In the crystal structure, the title compound, C(12)H(16)N(6)O(6), lies on an inversion centre. The mol-ecule has an anti-periplanar conformation with respect to the C-C bond of the central ethane unit and the two imidazole rings are parallel to each other. The dihedral angle between the imidazole ring and the mean plane of the C and O atoms of the bis-(eth-oxy)ethane group is 76.04 (6)°. The mol-ecules are stacked along the c axis through a weak C-H⋯O inter-action and a π⋯π inter-action between the imidazole rings with a centroid-centroid distance of 3.5162 (6) Å. An intramolecular C-H⋯O hydrogen bond is also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For the applications of nitro­imidazoles, see, for example: Abdel-Jalil et al. (2006 ▶); Kennedy et al. (2006 ▶); Nagasawa et al. (2006 ▶); Nunn et al. (1995 ▶).

Experimental

Crystal data

C12H16N6O6

M = 340.31

Monoclinic,

a = 7.0534 (1) Å

b = 15.5792 (2) Å

c = 6.8069 (1) Å

β = 99.560 (1)°

V = 737.60 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 100.0 (1) K

0.40 × 0.30 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.952, T max = 0.982

11084 measured reflections

2140 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.05

2140 reflections

141 parameters

All H-atom parameters refined

Δρmax = 0.49 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023726/is2317sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023726/is2317Isup2.hkl

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

C12H16N6O6	F000 = 356
Mr = 340.31	Dx = 1.532 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2140 reflections
a = 7.0534 (1) Å	θ = 2.6–30.0º
b = 15.5792 (2) Å	µ = 0.13 mm−1
c = 6.8069 (1) Å	T = 100.0 (1) K
β = 99.560 (1)º	Block, colorless
V = 737.597 (18) Å3	0.40 × 0.30 × 0.15 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	2140 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 2.6º
ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −19→21
Tmin = 0.952, Tmax = 0.982	l = −9→9
11084 measured reflections

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)] = 0.037	All H-atom parameters refined
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0604P)2 + 0.1626P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2140 reflections	Δρmax = 0.50 e Å−3
141 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cryosystem Cobra low-temperature attachment.

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. The highest residual electron density peak is located at 0.76 Å from C6 and the deepest hole is located at 1.04 Å from C1.

	x	y	z	Uiso*/Ueq
O1	−0.11911 (13)	0.21335 (6)	0.31449 (16)	0.0405 (2)
O2	−0.12171 (11)	0.35244 (5)	0.34055 (13)	0.0319 (2)
O3	0.39505 (9)	0.47777 (4)	0.21737 (9)	0.01816 (16)
N1	0.25143 (13)	0.20738 (5)	0.49696 (13)	0.02131 (19)
N2	0.26946 (11)	0.35116 (5)	0.49565 (11)	0.01551 (17)
N3	−0.04022 (13)	0.28202 (6)	0.36307 (14)	0.0243 (2)
C1	0.15885 (13)	0.27986 (6)	0.45100 (14)	0.0183 (2)
C2	0.43305 (14)	0.23267 (6)	0.57559 (14)	0.0209 (2)
C3	0.44699 (13)	0.32065 (6)	0.57493 (13)	0.01808 (19)
C4	0.22148 (14)	0.44265 (6)	0.47476 (13)	0.01791 (19)
C5	0.20547 (13)	0.47446 (6)	0.26222 (13)	0.01829 (19)
C6	0.39581 (14)	0.49935 (6)	0.01416 (13)	0.0190 (2)
H2	0.535 (2)	0.1921 (9)	0.625 (2)	0.024 (3)*
H3	0.5512 (19)	0.3594 (8)	0.6195 (19)	0.020 (3)*
H4A	0.3268 (19)	0.4727 (8)	0.5584 (19)	0.020 (3)*
H4B	0.1055 (19)	0.4504 (8)	0.5245 (19)	0.022 (3)*
H5A	0.1496 (18)	0.5319 (8)	0.2511 (18)	0.020 (3)*
H5B	0.1250 (17)	0.4375 (8)	0.1698 (18)	0.017 (3)*
H6A	0.3216 (18)	0.4569 (8)	−0.0729 (19)	0.021 (3)*
H6B	0.3398 (17)	0.5550 (8)	−0.0139 (18)	0.017 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0272 (4)	0.0366 (5)	0.0539 (6)	−0.0129 (3)	−0.0041 (4)	−0.0045 (4)
O2	0.0186 (4)	0.0345 (4)	0.0408 (5)	0.0023 (3)	−0.0004 (3)	0.0128 (3)
O3	0.0189 (3)	0.0223 (3)	0.0136 (3)	−0.0025 (2)	0.0038 (2)	0.0027 (2)
N1	0.0249 (4)	0.0174 (4)	0.0216 (4)	0.0000 (3)	0.0037 (3)	0.0023 (3)
N2	0.0152 (3)	0.0162 (4)	0.0152 (3)	0.0008 (3)	0.0028 (3)	0.0021 (2)
N3	0.0187 (4)	0.0287 (5)	0.0246 (4)	−0.0047 (3)	0.0009 (3)	0.0043 (3)
C1	0.0166 (4)	0.0198 (4)	0.0183 (4)	−0.0018 (3)	0.0021 (3)	0.0028 (3)
C2	0.0217 (5)	0.0206 (4)	0.0199 (4)	0.0050 (3)	0.0024 (3)	0.0018 (3)
C3	0.0156 (4)	0.0208 (4)	0.0173 (4)	0.0021 (3)	0.0013 (3)	0.0006 (3)
C4	0.0216 (4)	0.0155 (4)	0.0179 (4)	0.0033 (3)	0.0069 (3)	0.0023 (3)
C5	0.0196 (4)	0.0177 (4)	0.0183 (4)	0.0019 (3)	0.0054 (3)	0.0039 (3)
C6	0.0218 (5)	0.0213 (4)	0.0139 (4)	−0.0030 (3)	0.0035 (3)	0.0035 (3)

O1—N3	1.2258 (12)	C2—H2	0.977 (14)
O2—N3	1.2361 (12)	C3—H3	0.961 (13)
O3—C5	1.4211 (11)	C4—C5	1.5156 (12)
O3—C6	1.4243 (10)	C4—H4A	0.977 (13)
N1—C1	1.3160 (12)	C4—H4B	0.943 (13)
N1—C2	1.3620 (13)	C5—H5A	0.976 (12)
N2—C1	1.3623 (11)	C5—H5B	0.964 (12)
N2—C3	1.3641 (11)	C6—C6i	1.5140 (19)
N2—C4	1.4664 (11)	C6—H6A	0.980 (13)
N3—C1	1.4324 (13)	C6—H6B	0.958 (13)
C2—C3	1.3741 (14)
C5—O3—C6	111.88 (7)	N2—C4—H4A	105.6 (7)
C1—N1—C2	104.03 (8)	C5—C4—H4A	109.1 (7)
C1—N2—C3	104.96 (8)	N2—C4—H4B	106.8 (8)
C1—N2—C4	131.03 (8)	C5—C4—H4B	111.7 (8)
C3—N2—C4	123.99 (8)	H4A—C4—H4B	110.5 (11)
O1—N3—O2	124.07 (10)	O3—C5—C4	107.06 (7)
O1—N3—C1	117.50 (9)	O3—C5—H5A	109.4 (7)
O2—N3—C1	118.43 (8)	C4—C5—H5A	109.8 (7)
N1—C1—N2	113.79 (8)	O3—C5—H5B	110.8 (7)
N1—C1—N3	122.19 (8)	C4—C5—H5B	111.7 (7)
N2—C1—N3	124.01 (8)	H5A—C5—H5B	108.1 (11)
N1—C2—C3	110.51 (8)	O3—C6—C6i	106.69 (9)
N1—C2—H2	122.7 (8)	O3—C6—H6A	109.9 (7)
C3—C2—H2	126.7 (8)	C6i—C6—H6A	111.4 (7)
N2—C3—C2	106.70 (8)	O3—C6—H6B	109.8 (7)
N2—C3—H3	120.7 (8)	C6i—C6—H6B	109.8 (7)
C2—C3—H3	132.6 (8)	H6A—C6—H6B	109.2 (11)
N2—C4—C5	112.94 (7)
C2—N1—C1—N2	−0.18 (11)	C1—N1—C2—C3	−0.23 (11)
C2—N1—C1—N3	−179.90 (9)	C1—N2—C3—C2	−0.61 (10)
C3—N2—C1—N1	0.51 (11)	C4—N2—C3—C2	177.86 (8)
C4—N2—C1—N1	−177.81 (8)	N1—C2—C3—N2	0.54 (10)
C3—N2—C1—N3	−179.78 (9)	C1—N2—C4—C5	−77.42 (12)
C4—N2—C1—N3	1.90 (15)	C3—N2—C4—C5	104.54 (10)
O1—N3—C1—N1	−6.49 (16)	C6—O3—C5—C4	174.54 (7)
O2—N3—C1—N1	173.61 (9)	N2—C4—C5—O3	−72.25 (9)
O1—N3—C1—N2	173.82 (9)	C5—O3—C6—C6i	−179.94 (9)
O2—N3—C1—N2	−6.08 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3ii	0.977 (13)	2.404 (13)	3.3707 (11)	170.1 (10)
C4—H4B···O2	0.944 (14)	2.408 (13)	2.8169 (13)	105.9 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O3i	0.977 (13)	2.404 (13)	3.3707 (11)	170.1 (10)
C4—H4B⋯O2	0.944 (14)	2.408 (13)	2.8169 (13)	105.9 (9)

Symmetry code: (i) .