2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-propyloxime.

In the mol-ecule of the title compound, C(16)H(17)N(3)O(2), the planar benzimidazole ring system [maximum deviation = 0.013 (1) Å] is oriented at a dihedral angle of 75.32 (4)° with respect to the furan ring. An intra-molecular C-H⋯O inter-action results in the formation of a planar six-membered ring [maximum deviation = 0.019 (15) Å], which is oriented at a dihedral angle of 1.91 (3)° with respect to the adjacent 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 the imidazole rings [centroid-centroid distance = 3.5307 (8) Å] and weak C-H⋯π inter-actions.

Related literature

Several compounds containing an oxime or an oxime ether function have been reported to exhibit anti­microbial activity, see: Baji et al. (1995 ▶); Bhandari et al. (2009 ▶); Emami et al. (2002 ▶, 2004 ▶); Milanese et al. (2007 ▶); Polak (1982 ▶); Poretta et al. (1993 ▶); Ramalingan et al. (2006 ▶); Rosello et al. (2002 ▶). For related structures, see: Özel Güven et al. (2007a ▶,b ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H17N3O2

M = 283.33

Monoclinic,

a = 8.4164 (2) Å

b = 18.2524 (3) Å

c = 10.2246 (2) Å

β = 111.354 (1)°

V = 1462.87 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.50 × 0.35 × 0.35 mm

Data collection

Bruker–Nonius Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.958, T max = 0.960

19714 measured reflections

3344 independent reflections

2755 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.114

S = 1.14

3344 reflections

259 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.36 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO nd COLLECT; 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/S1600536809020844/ci2817sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020844/ci2817Isup2.hkl

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

C16H17N3O2	F(000) = 600
Mr = 283.33	Dx = 1.286 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3395 reflections
a = 8.4164 (2) Å	θ = 2.9–27.5°
b = 18.2524 (3) Å	µ = 0.09 mm−1
c = 10.2246 (2) Å	T = 120 K
β = 111.354 (1)°	Block, pale yellow
V = 1462.87 (5) Å3	0.50 × 0.35 × 0.35 mm
Z = 4

Bruker–Nonius Kappa CCD diffractometer	3344 independent reflections
Radiation source: fine-focus sealed tube	2755 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.9°
φ & ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −23→23
Tmin = 0.958, Tmax = 0.960	l = −13→13
19714 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)] = 0.043	All H-atom parameters refined
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.2758P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
3344 reflections	Δρmax = 0.37 e Å−3
259 parameters	Δρmin = −0.36 e Å−3
0 restraints	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.065 (5)

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	0.43354 (11)	0.47469 (5)	0.69234 (9)	0.0210 (2)
O2	0.62124 (10)	0.35487 (5)	0.44862 (9)	0.0215 (2)
N1	0.81649 (13)	0.45397 (6)	0.87655 (10)	0.0191 (2)
N2	0.81640 (14)	0.44200 (6)	1.09515 (11)	0.0234 (3)
N3	0.73483 (13)	0.39962 (6)	0.55091 (11)	0.0203 (2)
C1	0.75737 (16)	0.47823 (7)	0.97642 (13)	0.0226 (3)
H1	0.680 (2)	0.5192 (8)	0.9590 (16)	0.025 (4)*
C2	0.92279 (15)	0.38916 (7)	1.07227 (12)	0.0196 (3)
C3	1.01939 (16)	0.33471 (7)	1.16205 (13)	0.0229 (3)
H3	1.016 (2)	0.3284 (9)	1.2569 (17)	0.034 (4)*
C4	1.11688 (16)	0.28954 (7)	1.11299 (14)	0.0250 (3)
H4	1.185 (2)	0.2500 (9)	1.1699 (17)	0.035 (4)*
C5	1.11963 (16)	0.29780 (7)	0.97705 (14)	0.0249 (3)
H5	1.192 (2)	0.2655 (9)	0.9461 (16)	0.033 (4)*
C6	1.02292 (16)	0.35075 (7)	0.88540 (13)	0.0223 (3)
H6	1.0243 (19)	0.3573 (8)	0.7909 (16)	0.026 (4)*
C7	0.92492 (15)	0.39601 (6)	0.93600 (12)	0.0180 (3)
C8	0.77611 (17)	0.48381 (7)	0.73516 (13)	0.0209 (3)
H81	0.8843 (18)	0.4894 (8)	0.7176 (14)	0.018 (3)*
H82	0.7235 (19)	0.5324 (8)	0.7319 (15)	0.021 (4)*
C9	0.65977 (15)	0.43432 (6)	0.62241 (12)	0.0177 (3)
C10	0.48021 (15)	0.42984 (6)	0.60389 (12)	0.0176 (3)
C11	0.34138 (16)	0.39130 (7)	0.52080 (13)	0.0195 (3)
H11	0.3406 (18)	0.3571 (8)	0.4478 (15)	0.024 (4)*
C12	0.20149 (17)	0.41338 (7)	0.55880 (14)	0.0228 (3)
H12	0.081 (2)	0.3957 (8)	0.5195 (16)	0.027 (4)*
C13	0.26348 (17)	0.46348 (7)	0.66207 (13)	0.0233 (3)
H13	0.2152 (18)	0.4915 (8)	0.7179 (15)	0.021 (3)*
C14	0.71245 (17)	0.31673 (8)	0.37379 (15)	0.0269 (3)
H141	0.813 (2)	0.2925 (9)	0.4441 (17)	0.032 (4)*
H142	0.749 (2)	0.3531 (9)	0.3176 (17)	0.034 (4)*
C15	0.59066 (18)	0.26057 (8)	0.28123 (14)	0.0278 (3)
H151	0.650 (2)	0.2349 (10)	0.2257 (17)	0.040 (4)*
H152	0.493 (2)	0.2866 (9)	0.2113 (18)	0.040 (5)*
C16	0.52829 (18)	0.20602 (8)	0.36374 (15)	0.0287 (3)
H161	0.624 (2)	0.1794 (10)	0.4348 (19)	0.048 (5)*
H162	0.468 (2)	0.2317 (9)	0.4205 (16)	0.036 (4)*
H163	0.449 (2)	0.1687 (10)	0.3015 (19)	0.047 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0239 (5)	0.0207 (4)	0.0187 (4)	0.0014 (3)	0.0082 (4)	−0.0027 (3)
O2	0.0178 (4)	0.0252 (5)	0.0212 (4)	−0.0019 (3)	0.0069 (4)	−0.0078 (4)
N1	0.0206 (5)	0.0191 (5)	0.0163 (5)	−0.0009 (4)	0.0052 (4)	−0.0009 (4)
N2	0.0248 (6)	0.0258 (6)	0.0187 (5)	0.0015 (4)	0.0066 (4)	−0.0034 (4)
N3	0.0201 (5)	0.0212 (5)	0.0169 (5)	−0.0026 (4)	0.0036 (4)	−0.0013 (4)
C1	0.0234 (6)	0.0223 (6)	0.0213 (6)	0.0001 (5)	0.0070 (5)	−0.0053 (5)
C2	0.0179 (6)	0.0221 (6)	0.0173 (6)	−0.0037 (5)	0.0047 (5)	−0.0036 (5)
C3	0.0202 (6)	0.0275 (7)	0.0185 (6)	−0.0021 (5)	0.0041 (5)	0.0012 (5)
C4	0.0191 (6)	0.0252 (7)	0.0261 (7)	0.0017 (5)	0.0026 (5)	0.0025 (5)
C5	0.0187 (6)	0.0264 (7)	0.0293 (7)	0.0016 (5)	0.0083 (5)	−0.0036 (5)
C6	0.0200 (6)	0.0266 (6)	0.0212 (6)	−0.0027 (5)	0.0086 (5)	−0.0022 (5)
C7	0.0155 (5)	0.0188 (6)	0.0178 (6)	−0.0035 (4)	0.0036 (5)	−0.0016 (4)
C8	0.0238 (6)	0.0200 (6)	0.0165 (6)	−0.0042 (5)	0.0045 (5)	0.0009 (5)
C9	0.0206 (6)	0.0161 (6)	0.0150 (6)	−0.0009 (4)	0.0050 (5)	0.0029 (4)
C10	0.0229 (6)	0.0157 (5)	0.0146 (5)	0.0013 (4)	0.0074 (5)	0.0010 (4)
C11	0.0219 (6)	0.0185 (6)	0.0181 (6)	−0.0005 (5)	0.0073 (5)	−0.0001 (5)
C12	0.0216 (6)	0.0240 (6)	0.0237 (6)	0.0010 (5)	0.0093 (5)	0.0018 (5)
C13	0.0235 (6)	0.0257 (6)	0.0235 (6)	0.0045 (5)	0.0116 (5)	0.0020 (5)
C14	0.0212 (7)	0.0350 (7)	0.0277 (7)	0.0011 (6)	0.0128 (6)	−0.0079 (6)
C15	0.0249 (7)	0.0354 (8)	0.0232 (6)	0.0032 (6)	0.0087 (6)	−0.0095 (6)
C16	0.0258 (7)	0.0267 (7)	0.0305 (7)	0.0041 (6)	0.0067 (6)	−0.0070 (6)

O1—C10	1.3787 (14)	C6—H6	0.978 (15)
O1—C13	1.3652 (16)	C8—H81	0.996 (14)
O2—N3	1.3952 (13)	C8—H82	0.987 (15)
O2—C14	1.4447 (15)	C9—C8	1.5105 (16)
N1—C1	1.3625 (16)	C9—C10	1.4553 (16)
N1—C7	1.3847 (15)	C11—C10	1.3635 (17)
N1—C8	1.4643 (15)	C11—C12	1.4257 (17)
N2—C1	1.3110 (17)	C11—H11	0.971 (15)
N2—C2	1.3927 (16)	C12—H12	0.999 (16)
N3—C9	1.2927 (16)	C13—C12	1.3499 (19)
C1—H1	0.963 (15)	C13—H13	0.959 (15)
C2—C3	1.3956 (18)	C14—H141	0.994 (16)
C2—C7	1.4055 (17)	C14—H142	0.999 (17)
C3—H3	0.987 (16)	C15—C14	1.5136 (19)
C4—C3	1.3800 (18)	C15—C16	1.517 (2)
C4—C5	1.4066 (19)	C15—H151	0.999 (17)
C4—H4	0.973 (17)	C15—H152	0.994 (18)
C5—H5	0.982 (16)	C16—H161	0.993 (19)
C6—C5	1.3854 (18)	C16—H162	1.015 (17)
C6—C7	1.3933 (17)	C16—H163	1.001 (19)
C13—O1—C10	106.73 (9)	N3—C9—C10	126.66 (11)
N3—O2—C14	109.14 (9)	N3—C9—C8	114.21 (11)
C1—N1—C7	106.35 (10)	C10—C9—C8	119.13 (10)
C1—N1—C8	127.02 (11)	C11—C10—O1	109.32 (10)
C7—N1—C8	126.62 (10)	C11—C10—C9	136.37 (11)
C1—N2—C2	104.12 (10)	O1—C10—C9	114.31 (10)
C9—N3—O2	111.61 (10)	C10—C11—C12	106.84 (11)
N1—C1—H1	121.3 (9)	C10—C11—H11	125.1 (9)
N2—C1—N1	114.29 (11)	C12—C11—H11	128.0 (9)
N2—C1—H1	124.4 (9)	C13—C12—C11	106.40 (11)
N2—C2—C3	129.71 (11)	C13—C12—H12	125.5 (9)
N2—C2—C7	110.24 (11)	C11—C12—H12	128.1 (9)
C3—C2—C7	120.05 (11)	C12—C13—O1	110.70 (11)
C4—C3—C2	117.87 (11)	C12—C13—H13	134.4 (9)
C4—C3—H3	121.4 (10)	O1—C13—H13	114.9 (9)
C2—C3—H3	120.7 (10)	O2—C14—C15	106.74 (10)
C3—C4—C5	121.40 (12)	O2—C14—H142	108.7 (9)
C3—C4—H4	121.7 (9)	C15—C14—H142	111.9 (9)
C5—C4—H4	116.9 (9)	O2—C14—H141	108.0 (9)
C6—C5—C4	121.75 (12)	C15—C14—H141	110.9 (9)
C6—C5—H5	118.9 (9)	H142—C14—H141	110.5 (13)
C4—C5—H5	119.4 (9)	C14—C15—C16	112.93 (11)
C5—C6—C7	116.36 (11)	C14—C15—H151	107.9 (10)
C5—C6—H6	122.6 (9)	C16—C15—H151	110.7 (10)
C7—C6—H6	121.1 (9)	C14—C15—H152	108.7 (10)
N1—C7—C6	132.42 (11)	C16—C15—H152	110.5 (10)
N1—C7—C2	105.01 (10)	H151—C15—H152	105.7 (13)
C6—C7—C2	122.57 (11)	C15—C16—H161	112.0 (10)
N1—C8—C9	112.58 (9)	C15—C16—H162	111.2 (9)
N1—C8—H81	108.5 (8)	H161—C16—H162	104.4 (13)
C9—C8—H81	107.8 (8)	C15—C16—H163	112.1 (10)
N1—C8—H82	108.0 (8)	H161—C16—H163	107.8 (15)
C9—C8—H82	110.7 (9)	H162—C16—H163	108.8 (14)
H81—C8—H82	109.2 (12)
C13—O1—C10—C11	−0.29 (13)	N2—C2—C7—N1	−0.36 (13)
C13—O1—C10—C9	−179.60 (10)	C3—C2—C7—N1	179.63 (11)
C10—O1—C13—C12	0.20 (13)	N2—C2—C7—C6	179.04 (11)
C14—O2—N3—C9	−179.10 (10)	C3—C2—C7—C6	−0.97 (18)
N3—O2—C14—C15	171.16 (10)	C5—C4—C3—C2	0.06 (19)
C7—N1—C1—N2	0.07 (15)	C3—C4—C5—C6	−1.0 (2)
C8—N1—C1—N2	−179.00 (11)	C7—C6—C5—C4	0.93 (18)
C1—N1—C7—C6	−179.14 (13)	C5—C6—C7—N1	179.26 (12)
C8—N1—C7—C6	−0.1 (2)	C5—C6—C7—C2	0.05 (18)
C1—N1—C7—C2	0.18 (13)	N3—C9—C8—N1	−106.07 (12)
C8—N1—C7—C2	179.25 (11)	C10—C9—C8—N1	73.98 (14)
C1—N1—C8—C9	−107.61 (14)	N3—C9—C10—C11	2.8 (2)
C7—N1—C8—C9	73.51 (15)	C8—C9—C10—C11	−177.25 (13)
C2—N2—C1—N1	−0.28 (14)	N3—C9—C10—O1	−178.13 (11)
C1—N2—C2—C3	−179.59 (13)	C8—C9—C10—O1	1.81 (15)
C1—N2—C2—C7	0.39 (13)	C12—C11—C10—O1	0.26 (13)
O2—N3—C9—C10	−0.07 (16)	C12—C11—C10—C9	179.35 (13)
O2—N3—C9—C8	179.98 (9)	C10—C11—C12—C13	−0.13 (14)
N2—C2—C3—C4	−179.13 (12)	O1—C13—C12—C11	−0.04 (14)
C7—C2—C3—C4	0.89 (18)	C16—C15—C14—O2	−59.43 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2	0.97 (2)	2.359 (16)	2.7930 (17)	106 (1)
C13—H13···N2i	0.96 (2)	2.360 (15)	3.2872 (17)	162 (1)
C14—H141···Cg1ii	0.99 (2)	2.968 (17)	3.8346 (16)	146 (1)
C16—H161···Cg2ii	0.99 (2)	2.685 (18)	3.5644 (16)	148 (1)
C16—H163···Cg3ii	1.00 (2)	2.643 (18)	3.5901 (15)	157 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2	0.97 (2)	2.359 (16)	2.7930 (17)	106 (1)
C13—H13⋯N2i	0.96 (2)	2.360 (15)	3.2872 (17)	162 (1)
C14—H141⋯Cg1ii	0.99 (2)	2.968 (17)	3.8346 (16)	146 (1)
C16—H161⋯Cg2ii	0.99 (2)	2.685 (18)	3.5644 (16)	148 (1)
C16—H163⋯Cg3ii	1.00 (2)	2.643 (18)	3.5901 (15)	157 (1)

Symmetry codes: (i) ; (ii) . Cg1, Cg2 and Cg3 are the centroids of the C2–C7, N1/N2/C1/C2/C7 and O1/C10–C13 rings, respectively.