3-Meth-oxy-4-[3-(2-methyl-4-nitro-1H-imidazol-1-yl)prop-oxy]benzaldehyde.

In the title mol-ecule, C(15)H(17)N(3)O(5), the dihedral angle between the benzene and imidazole rings is 3.69 (2)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds and π-π stacking inter-actions with a centroid-centroid distance of 3.614 (1) Å.

Related literature

For general background to the biological activity of nitro­imidazole and its derivatives, see:Demirayak et al. (1999 ▶); Huang et al. (2007 ▶); Olender et al. (2009 ▶). For the synthetic procedure, see: Khalafi-Nezhad et al. (2005 ▶).

Experimental

Crystal data

C15H17N3O5

M = 319.32

Monoclinic,

a = 9.4885 (14) Å

b = 13.048 (2) Å

c = 12.745 (2) Å

β = 101.120 (3)°

V = 1548.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.28 × 0.24 × 0.2 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.979

7761 measured reflections

3329 independent reflections

2329 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.130

S = 1.03

3329 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.19 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: DIAMOND (Brandenburg & Putz, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031894/lh2876sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031894/lh2876Isup2.hkl

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

C15H17N3O5	F(000) = 672
Mr = 319.32	Dx = 1.370 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3149 reflections
a = 9.4885 (14) Å	θ = 2.3–26.9°
b = 13.048 (2) Å	µ = 0.10 mm−1
c = 12.745 (2) Å	T = 173 K
β = 101.120 (3)°	Block, colorless
V = 1548.3 (4) Å3	0.28 × 0.24 × 0.2 mm
Z = 4

Bruker SMART CCD diffractometer	3329 independent reflections
Radiation source: fine-focus sealed tube	2329 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→12
Tmin = 0.971, Tmax = 0.979	k = −15→16
7761 measured reflections	l = −13→16

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) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.3992P] where P = (Fo2 + 2Fc2)/3
3329 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.19 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
C1	0.2645 (2)	1.03088 (14)	−0.03024 (16)	0.0502 (5)
H1	0.2344	1.0901	0.0028	0.060*
C2	0.21471 (17)	0.93177 (12)	0.00141 (13)	0.0363 (4)
C3	0.25719 (18)	0.84045 (12)	−0.04102 (14)	0.0381 (4)
H3	0.3193	0.8421	−0.0912	0.046*
C4	0.3482 (2)	0.65169 (17)	−0.1102 (2)	0.0691 (7)
H4A	0.3107	0.6882	−0.1769	0.104*
H4B	0.3681	0.5803	−0.1262	0.104*
H4C	0.4370	0.6847	−0.0737	0.104*
C5	0.20870 (17)	0.74857 (12)	−0.00975 (13)	0.0346 (4)
C6	0.11391 (16)	0.74686 (11)	0.06315 (12)	0.0305 (3)
C7	0.07388 (17)	0.83703 (11)	0.10519 (13)	0.0322 (4)
H7	0.0114	0.8359	0.1551	0.039*
C8	0.12529 (17)	0.92983 (12)	0.07433 (13)	0.0347 (4)
H8	0.0985	0.9921	0.1038	0.042*
C9	−0.01627 (18)	0.64126 (12)	0.16566 (14)	0.0360 (4)
H9A	−0.1090	0.6775	0.1440	0.043*
H9B	0.0344	0.6699	0.2346	0.043*
C10	−0.04042 (17)	0.52728 (12)	0.17563 (14)	0.0378 (4)
H10A	−0.1107	0.5152	0.2225	0.045*
H10B	−0.0800	0.4981	0.1043	0.045*
C11	0.0990 (2)	0.47573 (13)	0.2218 (2)	0.0616 (6)
H11A	0.1721	0.4966	0.1802	0.074*
H11B	0.1316	0.4999	0.2962	0.074*
C12	0.16148 (17)	0.29675 (13)	0.16772 (13)	0.0384 (4)
C13	0.2589 (2)	0.33135 (16)	0.09670 (16)	0.0560 (5)
H13A	0.2936	0.2717	0.0624	0.084*
H13B	0.3407	0.3680	0.1390	0.084*
H13C	0.2066	0.3772	0.0417	0.084*
C14	0.01304 (17)	0.30668 (12)	0.28026 (15)	0.0403 (4)
H14	−0.0475	0.3304	0.3264	0.048*
C15	0.04200 (16)	0.20834 (11)	0.25747 (13)	0.0326 (4)
N1	0.09014 (14)	0.36345 (10)	0.22222 (12)	0.0417 (4)
N2	0.13429 (14)	0.20076 (10)	0.18821 (11)	0.0346 (3)
N3	−0.01634 (15)	0.11998 (11)	0.29957 (12)	0.0404 (4)
O1	0.34061 (19)	1.04390 (12)	−0.09476 (13)	0.0758 (5)
O2	0.24432 (13)	0.65445 (9)	−0.04271 (11)	0.0493 (4)
O3	0.06945 (12)	0.65190 (8)	0.08547 (10)	0.0376 (3)
O4	0.02197 (15)	0.03485 (9)	0.27613 (12)	0.0544 (4)
O5	−0.10418 (15)	0.13411 (11)	0.35800 (12)	0.0611 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0631 (12)	0.0379 (10)	0.0515 (11)	−0.0115 (8)	0.0156 (10)	0.0021 (8)
C2	0.0422 (9)	0.0306 (8)	0.0360 (9)	−0.0055 (7)	0.0074 (7)	0.0004 (7)
C3	0.0385 (9)	0.0378 (9)	0.0404 (9)	−0.0086 (7)	0.0139 (7)	−0.0058 (7)
C4	0.0556 (12)	0.0577 (13)	0.1071 (19)	−0.0074 (10)	0.0486 (13)	−0.0360 (13)
C5	0.0327 (8)	0.0294 (8)	0.0427 (9)	−0.0027 (6)	0.0097 (7)	−0.0106 (7)
C6	0.0306 (8)	0.0248 (7)	0.0355 (8)	−0.0027 (6)	0.0046 (6)	−0.0010 (6)
C7	0.0370 (8)	0.0285 (8)	0.0327 (8)	0.0011 (6)	0.0106 (7)	−0.0008 (6)
C8	0.0420 (9)	0.0249 (8)	0.0365 (9)	0.0012 (6)	0.0057 (7)	−0.0022 (6)
C9	0.0391 (9)	0.0279 (8)	0.0435 (9)	−0.0007 (7)	0.0140 (7)	0.0017 (7)
C10	0.0375 (9)	0.0284 (8)	0.0483 (10)	−0.0015 (7)	0.0106 (7)	0.0036 (7)
C11	0.0487 (11)	0.0249 (9)	0.0984 (17)	−0.0025 (8)	−0.0175 (11)	0.0050 (9)
C12	0.0367 (8)	0.0364 (9)	0.0391 (9)	−0.0067 (7)	−0.0004 (7)	0.0046 (7)
C13	0.0567 (12)	0.0595 (12)	0.0517 (12)	−0.0214 (10)	0.0102 (10)	0.0122 (10)
C14	0.0356 (8)	0.0316 (9)	0.0529 (11)	0.0045 (7)	0.0065 (8)	−0.0035 (8)
C15	0.0321 (8)	0.0273 (8)	0.0384 (9)	0.0018 (6)	0.0068 (7)	0.0007 (6)
N1	0.0360 (8)	0.0254 (7)	0.0597 (10)	−0.0008 (6)	−0.0008 (7)	0.0048 (6)
N2	0.0368 (7)	0.0309 (7)	0.0370 (7)	−0.0023 (6)	0.0092 (6)	0.0003 (6)
N3	0.0445 (8)	0.0319 (7)	0.0494 (9)	0.0022 (6)	0.0202 (7)	0.0034 (6)
O1	0.1041 (12)	0.0577 (9)	0.0781 (11)	−0.0285 (9)	0.0487 (10)	0.0027 (8)
O2	0.0480 (7)	0.0329 (7)	0.0749 (9)	−0.0048 (5)	0.0318 (7)	−0.0182 (6)
O3	0.0431 (6)	0.0236 (6)	0.0494 (7)	−0.0037 (5)	0.0176 (5)	−0.0026 (5)
O4	0.0732 (9)	0.0259 (6)	0.0739 (9)	0.0032 (6)	0.0383 (7)	0.0049 (6)
O5	0.0638 (9)	0.0543 (8)	0.0784 (10)	0.0023 (7)	0.0471 (8)	0.0018 (7)

C1—O1	1.207 (2)	C9—H9B	0.9900
C1—C2	1.460 (2)	C10—C11	1.499 (2)
C1—H1	0.9500	C10—H10A	0.9900
C2—C8	1.374 (2)	C10—H10B	0.9900
C2—C3	1.400 (2)	C11—N1	1.468 (2)
C3—C5	1.371 (2)	C11—H11A	0.9900
C3—H3	0.9500	C11—H11B	0.9900
C4—O2	1.428 (2)	C12—N2	1.315 (2)
C4—H4A	0.9800	C12—N1	1.371 (2)
C4—H4B	0.9800	C12—C13	1.483 (2)
C4—H4C	0.9800	C13—H13A	0.9800
C5—O2	1.3615 (18)	C13—H13B	0.9800
C5—C6	1.412 (2)	C13—H13C	0.9800
C6—O3	1.3567 (18)	C14—C15	1.355 (2)
C6—C7	1.376 (2)	C14—N1	1.356 (2)
C7—C8	1.390 (2)	C14—H14	0.9500
C7—H7	0.9500	C15—N2	1.362 (2)
C8—H8	0.9500	C15—N3	1.428 (2)
C9—O3	1.4304 (19)	N3—O4	1.2235 (17)
C9—C10	1.514 (2)	N3—O5	1.2339 (18)
C9—H9A	0.9900
O1—C1—C2	125.53 (19)	C9—C10—H10A	109.7
O1—C1—H1	117.2	C11—C10—H10B	109.7
C2—C1—H1	117.2	C9—C10—H10B	109.7
C8—C2—C3	120.47 (14)	H10A—C10—H10B	108.2
C8—C2—C1	118.55 (15)	N1—C11—C10	113.74 (14)
C3—C2—C1	120.98 (16)	N1—C11—H11A	108.8
C5—C3—C2	119.63 (15)	C10—C11—H11A	108.8
C5—C3—H3	120.2	N1—C11—H11B	108.8
C2—C3—H3	120.2	C10—C11—H11B	108.8
O2—C4—H4A	109.5	H11A—C11—H11B	107.7
O2—C4—H4B	109.5	N2—C12—N1	111.65 (15)
H4A—C4—H4B	109.5	N2—C12—C13	125.48 (17)
O2—C4—H4C	109.5	N1—C12—C13	122.86 (16)
H4A—C4—H4C	109.5	C12—C13—H13A	109.5
H4B—C4—H4C	109.5	C12—C13—H13B	109.5
O2—C5—C3	125.59 (15)	H13A—C13—H13B	109.5
O2—C5—C6	114.59 (14)	C12—C13—H13C	109.5
C3—C5—C6	119.82 (14)	H13A—C13—H13C	109.5
O3—C6—C7	125.37 (14)	H13B—C13—H13C	109.5
O3—C6—C5	114.55 (13)	C15—C14—N1	104.31 (15)
C7—C6—C5	120.08 (14)	C15—C14—H14	127.8
C6—C7—C8	119.74 (14)	N1—C14—H14	127.8
C6—C7—H7	120.1	C14—C15—N2	112.96 (14)
C8—C7—H7	120.1	C14—C15—N3	125.07 (15)
C2—C8—C7	120.23 (14)	N2—C15—N3	121.97 (13)
C2—C8—H8	119.9	C14—N1—C12	107.49 (13)
C7—C8—H8	119.9	C14—N1—C11	125.74 (17)
O3—C9—C10	105.75 (12)	C12—N1—C11	126.73 (16)
O3—C9—H9A	110.6	C12—N2—C15	103.59 (13)
C10—C9—H9A	110.6	O4—N3—O5	123.37 (14)
O3—C9—H9B	110.6	O4—N3—C15	119.10 (13)
C10—C9—H9B	110.6	O5—N3—C15	117.52 (13)
H9A—C9—H9B	108.7	C5—O2—C4	116.73 (14)
C11—C10—C9	109.72 (14)	C6—O3—C9	118.76 (12)
C11—C10—H10A	109.7

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O4i	0.98	2.58	3.415 (3)	144
C8—H8···O4ii	0.95	2.51	3.229 (2)	133
C10—H10B···O2iii	0.99	2.56	3.312 (2)	133
C10—H10A···O1iv	0.99	2.58	3.461 (2)	148
C14—H14···O1iv	0.95	2.29	3.166 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O4i	0.98	2.58	3.415 (3)	144
C8—H8⋯O4ii	0.95	2.51	3.229 (2)	133
C10—H10B⋯O2iii	0.99	2.56	3.312 (2)	133
C10—H10A⋯O1iv	0.99	2.58	3.461 (2)	148
C14—H14⋯O1iv	0.95	2.29	3.166 (2)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .