2-(1H-Benzimidazol-1-yl)-1-(2-fur-yl)ethanone O-ethyl-oxime.

In the mol-ecule of the title compound, C(15)H(15)N(3)O(2), the planar benzimidazole ring system [maximum deviation = 0.023 (2) Å] is oriented at a dihedral angle of 74.21 (5)° with respect to the furan ring. In the crystal structure, inter-molecular C-H⋯N inter-actions link the mol-ecules into centrosymmetric R(2) (2)(18) dimers. In addition, the structure is stabilized by π-π contacts between parallel imidazole rings [centroid-centroid distance = 3.726 (1) Å] and a weak C-H⋯π inter-action.

Related literature

For general background to oximes and oxime ethers and their biological activity, see: Baji et al. (1995 ▶); Bhandari et al. (2009 ▶); Emami et al. (2002 ▶, 2004 ▶); Milanese et al. (2007 ▶); Polak (1982 ▶); Porretta et al. (1993 ▶); Ramalingan et al. (2006 ▶); Rossello et al. (2002 ▶). For related structures, see: Özel Güven et al. (2007a ▶,b ▶, 2009a ▶,b ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H15N3O2

M = 269.30

Monoclinic,

a = 8.4448 (5) Å

b = 17.6345 (11) Å

c = 10.3147 (6) Å

β = 110.755 (2)°

V = 1436.38 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.40 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.967, T max = 0.979

16676 measured reflections

3742 independent reflections

2291 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.140

S = 1.03

3742 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022892/xu2539sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022892/xu2539Isup2.hkl

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

C15H15N3O2	F(000) = 568
Mr = 269.30	Dx = 1.245 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1232 reflections
a = 8.4448 (5) Å	θ = 2.3–28.8°
b = 17.6345 (11) Å	µ = 0.09 mm−1
c = 10.3147 (6) Å	T = 296 K
β = 110.755 (2)°	Block, yellow
V = 1436.38 (15) Å3	0.40 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3742 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 28.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→7
Tmin = 0.967, Tmax = 0.979	k = −23→19
16676 measured reflections	l = −12→13

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) = 0.140	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.249P] where P = (Fo2 + 2Fc2)/3
3742 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 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	−0.07624 (14)	0.47405 (6)	0.69126 (11)	0.0587 (3)
O2	0.12331 (14)	0.34870 (6)	0.45867 (12)	0.0620 (3)
N1	0.30309 (17)	0.45287 (7)	0.87568 (13)	0.0525 (3)
N2	0.2926 (2)	0.43475 (9)	1.08660 (15)	0.0735 (5)
N3	0.23041 (17)	0.39663 (8)	0.55862 (13)	0.0544 (3)
C1	0.2331 (2)	0.47207 (11)	0.97034 (18)	0.0672 (5)
H1	0.1494	0.5089	0.9538	0.081*
C2	0.4123 (2)	0.38660 (10)	1.06784 (16)	0.0561 (4)
C3	0.5178 (2)	0.33399 (11)	1.15764 (18)	0.0691 (5)
H3	0.5126	0.3257	1.2451	0.083*
C4	0.6289 (3)	0.29490 (12)	1.1144 (2)	0.0752 (5)
H4	0.7002	0.2594	1.1732	0.090*
C5	0.6378 (2)	0.30710 (12)	0.9839 (2)	0.0756 (5)
H5	0.7168	0.2802	0.9583	0.091*
C6	0.5329 (2)	0.35802 (10)	0.89142 (19)	0.0629 (4)
H6	0.5373	0.3655	0.8035	0.076*
C7	0.42077 (19)	0.39732 (8)	0.93684 (15)	0.0489 (4)
C8	0.2629 (2)	0.48404 (9)	0.73688 (16)	0.0545 (4)
H8A	0.3672	0.4931	0.7200	0.065*
H8B	0.2060	0.5324	0.7313	0.065*
C9	0.15179 (19)	0.43200 (8)	0.62662 (14)	0.0461 (3)
C10	−0.02592 (19)	0.42668 (8)	0.60758 (15)	0.0460 (3)
C11	−0.1609 (2)	0.38634 (9)	0.52731 (17)	0.0564 (4)
H11	−0.1616	0.3501	0.4616	0.068*
C12	−0.3007 (2)	0.40962 (11)	0.5621 (2)	0.0674 (5)
H12	−0.4112	0.3918	0.5237	0.081*
C13	−0.2438 (2)	0.46193 (11)	0.6602 (2)	0.0679 (5)
H13	−0.3102	0.4869	0.7020	0.081*
C14	0.2185 (2)	0.31439 (13)	0.3830 (2)	0.0813 (6)
H14A	0.3135	0.2863	0.4460	0.098*
H14B	0.2625	0.3534	0.3386	0.098*
C15	0.1095 (3)	0.26391 (19)	0.2798 (3)	0.1340 (12)
H15A	0.1742	0.2382	0.2331	0.201*
H15B	0.0206	0.2926	0.2136	0.201*
H15C	0.0610	0.2273	0.3238	0.201*

	U11	U22	U33	U12	U13	U23
O1	0.0639 (7)	0.0630 (7)	0.0511 (6)	0.0017 (5)	0.0226 (5)	−0.0089 (5)
O2	0.0581 (7)	0.0677 (7)	0.0577 (7)	0.0012 (6)	0.0173 (5)	−0.0193 (6)
N1	0.0589 (8)	0.0543 (7)	0.0408 (7)	−0.0030 (6)	0.0136 (6)	−0.0069 (6)
N2	0.0865 (11)	0.0894 (11)	0.0453 (8)	0.0104 (9)	0.0241 (8)	−0.0082 (8)
N3	0.0554 (7)	0.0591 (8)	0.0453 (7)	−0.0013 (6)	0.0136 (6)	−0.0042 (6)
C1	0.0761 (12)	0.0722 (11)	0.0518 (10)	0.0112 (9)	0.0210 (9)	−0.0116 (9)
C2	0.0597 (9)	0.0634 (10)	0.0400 (8)	−0.0069 (8)	0.0112 (7)	−0.0092 (7)
C3	0.0748 (12)	0.0795 (12)	0.0429 (9)	−0.0053 (10)	0.0083 (8)	0.0017 (8)
C4	0.0676 (11)	0.0768 (12)	0.0647 (12)	0.0044 (10)	0.0029 (10)	0.0055 (10)
C5	0.0636 (11)	0.0796 (13)	0.0809 (14)	0.0112 (10)	0.0222 (10)	−0.0037 (11)
C6	0.0611 (10)	0.0722 (11)	0.0578 (10)	−0.0017 (9)	0.0239 (8)	−0.0043 (9)
C7	0.0477 (8)	0.0516 (8)	0.0420 (8)	−0.0091 (7)	0.0094 (6)	−0.0069 (6)
C8	0.0619 (10)	0.0515 (9)	0.0470 (9)	−0.0101 (7)	0.0153 (7)	−0.0003 (7)
C9	0.0551 (9)	0.0438 (7)	0.0374 (8)	−0.0002 (6)	0.0141 (6)	0.0044 (6)
C10	0.0577 (9)	0.0420 (7)	0.0389 (8)	0.0011 (6)	0.0180 (6)	0.0014 (6)
C11	0.0615 (10)	0.0527 (9)	0.0552 (9)	−0.0061 (7)	0.0210 (8)	−0.0052 (7)
C12	0.0580 (10)	0.0751 (11)	0.0709 (12)	−0.0095 (9)	0.0252 (9)	−0.0033 (10)
C13	0.0632 (11)	0.0810 (12)	0.0684 (12)	0.0060 (9)	0.0342 (9)	0.0004 (10)
C14	0.0680 (12)	0.0984 (15)	0.0776 (13)	0.0098 (11)	0.0257 (10)	−0.0302 (12)
C15	0.0854 (16)	0.165 (3)	0.138 (2)	0.0083 (17)	0.0234 (16)	−0.097 (2)

O1—C10	1.3723 (17)	C7—C6	1.382 (2)
O1—C13	1.352 (2)	C8—H8A	0.9700
O2—N3	1.3909 (16)	C8—H8B	0.9700
O2—C14	1.438 (2)	C9—N3	1.285 (2)
N1—C1	1.351 (2)	C9—C8	1.503 (2)
N1—C7	1.379 (2)	C9—C10	1.446 (2)
N1—C8	1.457 (2)	C10—C11	1.350 (2)
N2—C1	1.303 (2)	C11—C12	1.411 (2)
C1—H1	0.9300	C11—H11	0.9300
C2—N2	1.385 (2)	C12—H12	0.9300
C2—C3	1.388 (2)	C13—C12	1.328 (3)
C3—C4	1.361 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.442 (3)
C4—H4	0.9300	C14—H14A	0.9700
C5—C4	1.391 (3)	C14—H14B	0.9700
C5—H5	0.9300	C15—H15A	0.9600
C6—C5	1.379 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C2	1.391 (2)
C13—O1—C10	106.63 (13)	C9—C8—H8A	109.2
N3—O2—C14	108.44 (12)	C9—C8—H8B	109.2
C1—N1—C7	106.03 (13)	H8A—C8—H8B	107.9
C1—N1—C8	127.31 (15)	N3—C9—C8	113.87 (14)
C7—N1—C8	126.65 (13)	N3—C9—C10	127.33 (14)
C1—N2—C2	104.09 (14)	C10—C9—C8	118.81 (13)
C9—N3—O2	111.93 (13)	O1—C10—C9	114.39 (13)
N1—C1—H1	122.8	C11—C10—O1	108.92 (13)
N2—C1—N1	114.46 (16)	C11—C10—C9	136.69 (14)
N2—C1—H1	122.8	C10—C11—C12	106.94 (15)
N2—C2—C3	130.09 (16)	C10—C11—H11	126.5
N2—C2—C7	110.10 (15)	C12—C11—H11	126.5
C3—C2—C7	119.80 (16)	C11—C12—H12	126.7
C2—C3—H3	120.9	C13—C12—C11	106.65 (16)
C4—C3—C2	118.29 (17)	C13—C12—H12	126.7
C4—C3—H3	120.9	O1—C13—H13	124.6
C3—C4—C5	121.26 (18)	C12—C13—O1	110.85 (16)
C3—C4—H4	119.4	C12—C13—H13	124.6
C5—C4—H4	119.4	O2—C14—C15	109.09 (17)
C4—C5—H5	119.1	O2—C14—H14A	109.9
C6—C5—C4	121.86 (18)	O2—C14—H14B	109.9
C6—C5—H5	119.1	C15—C14—H14A	109.9
C5—C6—C7	116.19 (17)	C15—C14—H14B	109.9
C5—C6—H6	121.9	H14A—C14—H14B	108.3
C7—C6—H6	121.9	C14—C15—H15A	109.5
N1—C7—C6	132.10 (15)	C14—C15—H15B	109.5
N1—C7—C2	105.31 (14)	C14—C15—H15C	109.5
C6—C7—C2	122.57 (15)	H15A—C15—H15B	109.5
N1—C8—C9	112.26 (12)	H15A—C15—H15C	109.5
N1—C8—H8A	109.2	H15B—C15—H15C	109.5
N1—C8—H8B	109.2
C13—O1—C10—C9	179.95 (13)	C7—C6—C5—C4	1.3 (3)
C13—O1—C10—C11	−0.15 (17)	N1—C7—C2—N2	−0.25 (18)
C10—O1—C13—C12	0.1 (2)	N1—C7—C2—C3	−179.41 (14)
C14—O2—N3—C9	177.14 (15)	C6—C7—C2—N2	178.33 (15)
N3—O2—C14—C15	179.4 (2)	C6—C7—C2—C3	−0.8 (2)
C7—N1—C1—N2	−0.1 (2)	N1—C7—C6—C5	177.93 (16)
C8—N1—C1—N2	179.70 (15)	C2—C7—C6—C5	−0.2 (2)
C1—N1—C7—C2	0.23 (17)	C8—C9—N3—O2	179.48 (11)
C1—N1—C7—C6	−178.15 (17)	C10—C9—N3—O2	−0.6 (2)
C8—N1—C7—C2	−179.61 (14)	N3—C9—C8—N1	−104.67 (16)
C8—N1—C7—C6	2.0 (3)	C10—C9—C8—N1	75.41 (17)
C1—N1—C8—C9	−102.12 (19)	N3—C9—C10—O1	−177.03 (14)
C7—N1—C8—C9	77.69 (19)	N3—C9—C10—C11	3.1 (3)
C2—N2—C1—N1	0.0 (2)	C8—C9—C10—O1	2.88 (18)
C3—C2—N2—C1	179.21 (18)	C8—C9—C10—C11	−176.98 (17)
C7—C2—N2—C1	0.16 (19)	O1—C10—C11—C12	0.16 (18)
N2—C2—C3—C4	−178.13 (18)	C9—C10—C11—C12	−179.97 (17)
C7—C2—C3—C4	0.8 (3)	C10—C11—C12—C13	−0.1 (2)
C2—C3—C4—C5	0.2 (3)	O1—C13—C12—C11	0.0 (2)
C6—C5—C4—C3	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2i	0.93	2.54	3.328 (2)	143
C14—H14A···Cg2ii	0.97	2.88	3.768 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N2i	0.93	2.54	3.328 (2)	143
C14—H14A⋯Cg2ii	0.97	2.88	3.768 (2)	153

Symmetry codes: (i) ; (ii) .Cg2 is the centroid of the C2–C7 ring.