4-(2-{2-[2-(2-Nitro-1H-imidazol-1-yl)ethoxy]eth-oxy}eth-oxy)benzaldehyde.

In the mol-ecule of the title compound, C(16)H(19)N(3)O(6), the imidazole ring is essentially planar [maximum deviation = 0.002 (2) Å] and forms a dihedral angle of 5.08 (14)° with the nitro group. In the crystal structure, adjacent mol-ecules are connected via inter-molecular C-H⋯O hydrogen bonds into columns parallel to the a axis.

Related literature

For details and applications of nitro­imidazole, see: Abdel-Jalil et al. (2006 ▶); Kennedy et al. (2006 ▶); Nagasawa et al. (2006 ▶); Nunn et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H19N3O6

M = 349.34

Orthorhombic,

a = 4.4403 (3) Å

b = 11.4686 (8) Å

c = 31.2763 (19) Å

V = 1592.72 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

1.00 × 0.10 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.895, T max = 0.990

11825 measured reflections

2763 independent reflections

2243 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.094

S = 1.03

2763 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014322/rz2583sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014322/rz2583Isup2.hkl

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

C16H19N3O6	F(000) = 736
Mr = 349.34	Dx = 1.457 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3196 reflections
a = 4.4403 (3) Å	θ = 2.6–27.4°
b = 11.4686 (8) Å	µ = 0.11 mm−1
c = 31.2763 (19) Å	T = 100 K
V = 1592.72 (18) Å3	Needle, colourless
Z = 4	1.00 × 0.10 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	2763 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 30.2°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→5
Tmin = 0.895, Tmax = 0.990	k = −12→16
11825 measured reflections	l = −37→43

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0349P)2 + 0.4321P] where P = (Fo2 + 2Fc2)/3
2763 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.9164 (4)	0.80126 (13)	0.06764 (4)	0.0200 (4)
O2	1.0360 (4)	0.59396 (12)	0.11489 (4)	0.0195 (3)
O3	0.9292 (4)	0.36579 (13)	0.15473 (4)	0.0219 (4)
O4	0.0201 (4)	1.14948 (13)	−0.02814 (5)	0.0258 (4)
O5	0.3451 (4)	0.06021 (15)	0.17441 (5)	0.0295 (4)
O6	0.5051 (5)	−0.10825 (14)	0.19678 (5)	0.0339 (5)
N1	0.7409 (5)	0.17301 (15)	0.22943 (5)	0.0195 (4)
N2	0.8668 (5)	−0.00344 (17)	0.25495 (6)	0.0243 (5)
N3	0.5073 (5)	−0.00129 (17)	0.19754 (5)	0.0243 (4)
C1	0.6176 (6)	0.87874 (18)	0.01331 (7)	0.0193 (5)
H1A	0.6778	0.8169	−0.0039	0.023*
C2	0.4203 (6)	0.96061 (18)	−0.00235 (7)	0.0193 (5)
H2A	0.3471	0.9536	−0.0301	0.023*
C3	0.3288 (5)	1.05450 (19)	0.02312 (7)	0.0190 (5)
C4	0.4436 (6)	1.06324 (19)	0.06456 (7)	0.0210 (5)
H4A	0.3840	1.1252	0.0818	0.025*
C5	0.6446 (6)	0.98164 (19)	0.08066 (7)	0.0201 (5)
H5A	0.7222	0.9893	0.1081	0.024*
C6	0.7279 (5)	0.88797 (18)	0.05488 (7)	0.0178 (5)
C7	1.0208 (6)	0.80108 (18)	0.11112 (6)	0.0202 (5)
H7A	0.8515	0.7973	0.1307	0.024*
H7B	1.1339	0.8716	0.1171	0.024*
C8	1.2175 (6)	0.69626 (19)	0.11638 (7)	0.0207 (5)
H8A	1.3665	0.6940	0.0937	0.025*
H8B	1.3226	0.7002	0.1435	0.025*
C9	1.2191 (6)	0.4924 (2)	0.11083 (7)	0.0214 (5)
H9A	1.3631	0.4893	0.1341	0.026*
H9B	1.3299	0.4952	0.0841	0.026*
C10	1.0220 (6)	0.38626 (18)	0.11178 (6)	0.0202 (5)
H10A	0.8471	0.3982	0.0937	0.024*
H10B	1.1322	0.3193	0.1011	0.024*
C11	0.7292 (6)	0.27044 (19)	0.15794 (7)	0.0224 (5)
H11A	0.8336	0.1984	0.1514	0.027*
H11B	0.5644	0.2797	0.1378	0.027*
C12	0.6082 (7)	0.26698 (19)	0.20368 (7)	0.0243 (6)
H12A	0.6493	0.3411	0.2174	0.029*
H12B	0.3914	0.2568	0.2028	0.029*
C13	0.9408 (6)	0.1895 (2)	0.26212 (7)	0.0242 (5)
H13A	1.0129	0.2605	0.2721	0.029*
C14	1.0146 (7)	0.0807 (2)	0.27736 (7)	0.0264 (5)
H14A	1.1469	0.0666	0.2998	0.032*
C15	0.7066 (6)	0.05487 (19)	0.22695 (6)	0.0204 (5)
C16	0.1127 (6)	1.14220 (19)	0.00810 (7)	0.0213 (5)
H16A	0.0418	1.1961	0.0279	0.026*

	U11	U22	U33	U12	U13	U23
O1	0.0253 (9)	0.0186 (7)	0.0161 (7)	0.0025 (8)	0.0000 (7)	−0.0003 (6)
O2	0.0184 (8)	0.0159 (7)	0.0243 (7)	−0.0011 (7)	0.0010 (8)	0.0014 (6)
O3	0.0291 (10)	0.0198 (7)	0.0168 (7)	−0.0051 (8)	−0.0008 (7)	−0.0001 (6)
O4	0.0266 (10)	0.0266 (8)	0.0242 (8)	0.0009 (8)	−0.0027 (8)	0.0016 (6)
O5	0.0294 (10)	0.0345 (9)	0.0245 (8)	−0.0009 (9)	−0.0035 (8)	0.0016 (7)
O6	0.0496 (13)	0.0188 (8)	0.0333 (9)	−0.0068 (9)	0.0004 (11)	−0.0028 (7)
N1	0.0239 (11)	0.0163 (9)	0.0184 (9)	0.0011 (8)	0.0026 (9)	0.0005 (7)
N2	0.0337 (12)	0.0194 (9)	0.0200 (9)	0.0019 (10)	0.0030 (9)	0.0025 (7)
N3	0.0303 (12)	0.0233 (9)	0.0193 (8)	−0.0045 (10)	0.0044 (10)	0.0002 (8)
C1	0.0225 (12)	0.0159 (10)	0.0195 (10)	−0.0018 (10)	0.0037 (10)	−0.0024 (8)
C2	0.0185 (12)	0.0220 (10)	0.0174 (9)	−0.0025 (10)	0.0001 (9)	0.0003 (8)
C3	0.0175 (11)	0.0182 (10)	0.0214 (10)	−0.0024 (10)	0.0023 (10)	0.0005 (8)
C4	0.0235 (12)	0.0179 (10)	0.0216 (10)	0.0008 (11)	0.0004 (10)	−0.0033 (8)
C5	0.0243 (13)	0.0197 (10)	0.0165 (9)	−0.0024 (10)	−0.0008 (10)	−0.0018 (8)
C6	0.0182 (11)	0.0148 (10)	0.0205 (10)	−0.0016 (10)	0.0034 (10)	0.0027 (8)
C7	0.0245 (13)	0.0191 (10)	0.0170 (9)	−0.0026 (11)	0.0000 (11)	0.0004 (8)
C8	0.0198 (12)	0.0200 (10)	0.0222 (10)	−0.0042 (10)	−0.0006 (11)	0.0005 (9)
C9	0.0224 (12)	0.0190 (10)	0.0227 (10)	0.0035 (11)	−0.0003 (11)	−0.0009 (9)
C10	0.0251 (13)	0.0157 (10)	0.0199 (10)	0.0021 (10)	−0.0012 (11)	−0.0002 (8)
C11	0.0300 (14)	0.0151 (10)	0.0220 (11)	−0.0005 (10)	−0.0028 (12)	0.0028 (9)
C12	0.0314 (15)	0.0157 (10)	0.0258 (11)	0.0037 (11)	0.0012 (11)	0.0029 (9)
C13	0.0268 (13)	0.0272 (11)	0.0185 (10)	−0.0019 (12)	0.0027 (11)	−0.0034 (9)
C14	0.0333 (14)	0.0273 (11)	0.0185 (10)	0.0009 (12)	0.0006 (12)	0.0000 (9)
C15	0.0270 (13)	0.0169 (10)	0.0174 (10)	−0.0017 (10)	0.0027 (10)	−0.0010 (8)
C16	0.0193 (12)	0.0172 (10)	0.0274 (11)	−0.0024 (10)	0.0010 (11)	0.0005 (9)

O1—C6	1.360 (3)	C4—H4A	0.9300
O1—C7	1.437 (2)	C5—C6	1.393 (3)
O2—C8	1.424 (3)	C5—H5A	0.9300
O2—C9	1.426 (3)	C7—C8	1.495 (3)
O3—C11	1.412 (3)	C7—H7A	0.9700
O3—C10	1.425 (2)	C7—H7B	0.9700
O4—C16	1.209 (3)	C8—H8A	0.9700
O5—N3	1.241 (3)	C8—H8B	0.9700
O6—N3	1.227 (2)	C9—C10	1.500 (3)
N1—C15	1.366 (3)	C9—H9A	0.9700
N1—C13	1.367 (3)	C9—H9B	0.9700
N1—C12	1.469 (3)	C10—H10A	0.9700
N2—C15	1.312 (3)	C10—H10B	0.9700
N2—C14	1.361 (3)	C11—C12	1.529 (3)
N3—C15	1.429 (3)	C11—H11A	0.9700
C1—C2	1.374 (3)	C11—H11B	0.9700
C1—C6	1.393 (3)	C12—H12A	0.9700
C1—H1A	0.9300	C12—H12B	0.9700
C2—C3	1.400 (3)	C13—C14	1.375 (3)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.396 (3)	C14—H14A	0.9300
C3—C16	1.467 (3)	C16—H16A	0.9300
C4—C5	1.388 (3)
C6—O1—C7	118.52 (17)	C7—C8—H8B	109.8
C8—O2—C9	110.66 (17)	H8A—C8—H8B	108.3
C11—O3—C10	112.10 (16)	O2—C9—C10	109.2 (2)
C15—N1—C13	104.60 (19)	O2—C9—H9A	109.8
C15—N1—C12	130.7 (2)	C10—C9—H9A	109.8
C13—N1—C12	124.70 (19)	O2—C9—H9B	109.8
C15—N2—C14	104.12 (19)	C10—C9—H9B	109.8
O6—N3—O5	123.5 (2)	H9A—C9—H9B	108.3
O6—N3—C15	117.9 (2)	O3—C10—C9	108.74 (17)
O5—N3—C15	118.57 (18)	O3—C10—H10A	109.9
C2—C1—C6	120.3 (2)	C9—C10—H10A	109.9
C2—C1—H1A	119.8	O3—C10—H10B	109.9
C6—C1—H1A	119.8	C9—C10—H10B	109.9
C1—C2—C3	120.5 (2)	H10A—C10—H10B	108.3
C1—C2—H2A	119.7	O3—C11—C12	107.91 (18)
C3—C2—H2A	119.7	O3—C11—H11A	110.1
C4—C3—C2	118.5 (2)	C12—C11—H11A	110.1
C4—C3—C16	119.1 (2)	O3—C11—H11B	110.1
C2—C3—C16	122.4 (2)	C12—C11—H11B	110.1
C5—C4—C3	121.5 (2)	H11A—C11—H11B	108.4
C5—C4—H4A	119.2	N1—C12—C11	113.03 (19)
C3—C4—H4A	119.2	N1—C12—H12A	109.0
C4—C5—C6	118.7 (2)	C11—C12—H12A	109.0
C4—C5—H5A	120.6	N1—C12—H12B	109.0
C6—C5—H5A	120.6	C11—C12—H12B	109.0
O1—C6—C5	123.9 (2)	H12A—C12—H12B	107.8
O1—C6—C1	115.77 (19)	N1—C13—C14	106.8 (2)
C5—C6—C1	120.3 (2)	N1—C13—H13A	126.6
O1—C7—C8	107.08 (17)	C14—C13—H13A	126.6
O1—C7—H7A	110.3	N2—C14—C13	110.5 (2)
C8—C7—H7A	110.3	N2—C14—H14A	124.8
O1—C7—H7B	110.3	C13—C14—H14A	124.8
C8—C7—H7B	110.3	N2—C15—N1	114.0 (2)
H7A—C7—H7B	108.6	N2—C15—N3	122.39 (19)
O2—C8—C7	109.2 (2)	N1—C15—N3	123.6 (2)
O2—C8—H8A	109.8	O4—C16—C3	124.7 (2)
C7—C8—H8A	109.8	O4—C16—H16A	117.6
O2—C8—H8B	109.9	C3—C16—H16A	117.6
C6—C1—C2—C3	0.3 (3)	C15—N1—C12—C11	−69.6 (3)
C1—C2—C3—C4	0.3 (3)	C13—N1—C12—C11	108.9 (2)
C1—C2—C3—C16	−178.4 (2)	O3—C11—C12—N1	−105.5 (2)
C2—C3—C4—C5	0.1 (3)	C15—N1—C13—C14	0.0 (3)
C16—C3—C4—C5	178.9 (2)	C12—N1—C13—C14	−178.9 (2)
C3—C4—C5—C6	−1.2 (3)	C15—N2—C14—C13	−0.3 (3)
C7—O1—C6—C5	4.4 (3)	N1—C13—C14—N2	0.2 (3)
C7—O1—C6—C1	−175.6 (2)	C14—N2—C15—N1	0.3 (3)
C4—C5—C6—O1	−178.2 (2)	C14—N2—C15—N3	−177.8 (2)
C4—C5—C6—C1	1.9 (3)	C13—N1—C15—N2	−0.1 (3)
C2—C1—C6—O1	178.6 (2)	C12—N1—C15—N2	178.6 (2)
C2—C1—C6—C5	−1.4 (3)	C13—N1—C15—N3	177.9 (2)
C6—O1—C7—C8	179.05 (18)	C12—N1—C15—N3	−3.3 (4)
C9—O2—C8—C7	167.89 (17)	O6—N3—C15—N2	−5.4 (3)
O1—C7—C8—O2	−70.0 (2)	O5—N3—C15—N2	174.2 (2)
C8—O2—C9—C10	176.92 (17)	O6—N3—C15—N1	176.7 (2)
C11—O3—C10—C9	176.86 (19)	O5—N3—C15—N1	−3.7 (3)
O2—C9—C10—O3	−75.8 (2)	C4—C3—C16—O4	172.9 (2)
C10—O3—C11—C12	−171.84 (19)	C2—C3—C16—O4	−8.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O4i	0.97	2.56	3.335 (3)	137.
C10—H10A···O4ii	0.97	2.57	3.461 (3)	152.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O4i	0.97	2.56	3.335 (3)	137
C10—H10A⋯O4ii	0.97	2.57	3.461 (3)	152

Symmetry codes: (i) ; (ii) .