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

In the mol-ecule of the title compound, C(16)H(17)N(3)O(2), the planar benzimidazole ring system [maximum deviation = 0.015 (2) Å] is oriented at a dihedral angle of 72.17 (4)° with respect to the furan ring. An intra-molecular C-H⋯O inter-action results in the formation of a six-membered ring having an envelope conformation. In the crystal structure, inter-molecular C-H⋯N inter-actions link the mol-ecules into centrosymmetric R(2) (2)(18) dimers.

Related literature

For general background to oximes and oxime ethers, including their biological 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 ▶, 2009 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H17N3O2

M = 283.33

Monoclinic,

a = 8.4290 (2) Å

b = 17.7606 (3) Å

c = 10.6017 (2) Å

β = 111.882 (1)°

V = 1472.77 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.966, T max = 0.979

20597 measured reflections

3356 independent reflections

2803 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.111

S = 1.12

3356 reflections

259 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and 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/S1600536809022302/im2123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022302/im2123Isup2.hkl

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

C16H17N3O2	F(000) = 600
Mr = 283.33	Dx = 1.278 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3444 reflections
a = 8.4290 (2) Å	θ = 2.9–27.5°
b = 17.7606 (3) Å	µ = 0.09 mm−1
c = 10.6017 (2) Å	T = 120 K
β = 111.882 (1)°	Plate, yellow
V = 1472.77 (5) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker–Nonius KappaCCD diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	2803 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.1°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −23→23
Tmin = 0.966, Tmax = 0.979	l = −13→12
20597 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)] = 0.042	All H-atom parameters refined
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.2982P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
3356 reflections	Δρmax = 0.27 e Å−3
259 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.091 (6)

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	0.58682 (11)	0.47550 (5)	0.80555 (8)	0.0252 (2)
O2	0.41827 (11)	0.33276 (5)	1.02341 (8)	0.0247 (2)
N1	0.19899 (13)	0.45752 (5)	0.64047 (9)	0.0205 (2)
N2	0.18669 (14)	0.44880 (6)	0.42568 (10)	0.0278 (3)
N3	0.30106 (13)	0.38505 (6)	0.94150 (10)	0.0226 (2)
C1	0.25496 (17)	0.48323 (7)	0.54285 (12)	0.0244 (3)
H1	0.3367 (18)	0.5250 (8)	0.5619 (14)	0.025 (3)*
C2	0.07716 (15)	0.39595 (7)	0.44673 (12)	0.0241 (3)
C3	−0.03026 (17)	0.34334 (8)	0.35695 (13)	0.0318 (3)
H3	−0.032 (2)	0.3408 (9)	0.2646 (17)	0.038 (4)*
C4	−0.12897 (19)	0.29830 (9)	0.40499 (15)	0.0386 (4)
H4	−0.203 (2)	0.2612 (11)	0.3450 (18)	0.051 (5)*
C5	−0.12247 (18)	0.30444 (8)	0.53863 (15)	0.0360 (3)
H5	−0.196 (2)	0.2724 (10)	0.5696 (17)	0.045 (5)*
C6	−0.01575 (16)	0.35542 (7)	0.62975 (14)	0.0282 (3)
H6	−0.0111 (19)	0.3597 (8)	0.7232 (16)	0.031 (4)*
C7	0.08317 (14)	0.40074 (6)	0.58065 (11)	0.0212 (3)
C8	0.25028 (16)	0.48361 (7)	0.78092 (12)	0.0222 (3)
H81	0.3035 (17)	0.5328 (8)	0.7868 (13)	0.022 (3)*
H82	0.1471 (19)	0.4885 (8)	0.8028 (14)	0.026 (4)*
C9	0.37140 (15)	0.42870 (6)	0.87967 (11)	0.0197 (3)
C10	0.54860 (15)	0.42703 (6)	0.89174 (11)	0.0198 (3)
C11	0.69233 (16)	0.38863 (7)	0.96787 (12)	0.0236 (3)
H11	0.6964 (19)	0.3507 (9)	1.0364 (15)	0.030 (4)*
C12	0.82605 (17)	0.41455 (7)	0.92724 (13)	0.0289 (3)
H12	0.941 (2)	0.3979 (9)	0.9589 (17)	0.040 (4)*
C13	0.75635 (17)	0.46619 (8)	0.82951 (13)	0.0296 (3)
H13	0.799 (2)	0.4959 (9)	0.7728 (16)	0.037 (4)*
C14	0.33484 (16)	0.28212 (7)	1.08724 (13)	0.0265 (3)
H14	0.219 (2)	0.2716 (9)	1.0207 (15)	0.031 (4)*
C15	0.3264 (3)	0.31843 (10)	1.21285 (18)	0.0463 (4)
H151	0.446 (3)	0.3321 (12)	1.281 (2)	0.061 (6)*
H152	0.254 (3)	0.3634 (12)	1.189 (2)	0.060 (6)*
H153	0.272 (3)	0.2848 (11)	1.2585 (19)	0.060 (5)*
C16	0.44161 (18)	0.21125 (8)	1.11657 (14)	0.0316 (3)
H161	0.446 (2)	0.1863 (10)	1.0273 (18)	0.048 (5)*
H162	0.398 (2)	0.1768 (10)	1.1676 (18)	0.048 (5)*
H163	0.559 (2)	0.2239 (9)	1.1768 (17)	0.040 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0290 (5)	0.0255 (4)	0.0222 (4)	−0.0023 (3)	0.0109 (4)	0.0052 (3)
O2	0.0236 (5)	0.0258 (4)	0.0235 (4)	−0.0009 (3)	0.0075 (3)	0.0090 (3)
N1	0.0244 (5)	0.0197 (5)	0.0171 (5)	0.0029 (4)	0.0074 (4)	0.0016 (4)
N2	0.0345 (6)	0.0279 (5)	0.0204 (5)	0.0050 (4)	0.0098 (4)	0.0049 (4)
N3	0.0253 (5)	0.0231 (5)	0.0179 (5)	0.0015 (4)	0.0063 (4)	0.0020 (4)
C1	0.0310 (7)	0.0213 (6)	0.0212 (6)	0.0025 (5)	0.0100 (5)	0.0049 (4)
C2	0.0236 (6)	0.0251 (6)	0.0200 (6)	0.0078 (5)	0.0038 (5)	0.0027 (4)
C3	0.0300 (7)	0.0332 (7)	0.0227 (6)	0.0077 (6)	−0.0012 (5)	−0.0023 (5)
C4	0.0270 (7)	0.0369 (7)	0.0388 (8)	−0.0018 (6)	−0.0029 (6)	−0.0080 (6)
C5	0.0258 (7)	0.0353 (7)	0.0435 (8)	−0.0040 (6)	0.0088 (6)	0.0002 (6)
C6	0.0240 (6)	0.0307 (6)	0.0310 (7)	0.0018 (5)	0.0115 (5)	0.0023 (5)
C7	0.0189 (6)	0.0212 (5)	0.0209 (6)	0.0057 (4)	0.0043 (4)	0.0007 (4)
C8	0.0288 (7)	0.0197 (6)	0.0185 (6)	0.0030 (5)	0.0092 (5)	−0.0010 (4)
C9	0.0259 (6)	0.0182 (5)	0.0146 (5)	−0.0004 (4)	0.0069 (4)	−0.0026 (4)
C10	0.0272 (6)	0.0175 (5)	0.0149 (5)	−0.0032 (4)	0.0082 (4)	−0.0014 (4)
C11	0.0274 (6)	0.0226 (6)	0.0203 (6)	−0.0002 (5)	0.0082 (5)	0.0004 (4)
C12	0.0260 (7)	0.0323 (7)	0.0289 (7)	−0.0009 (5)	0.0110 (5)	0.0000 (5)
C13	0.0282 (7)	0.0340 (7)	0.0297 (7)	−0.0046 (5)	0.0144 (5)	0.0010 (5)
C14	0.0251 (6)	0.0283 (6)	0.0252 (6)	−0.0067 (5)	0.0082 (5)	0.0061 (5)
C15	0.0648 (12)	0.0454 (9)	0.0409 (9)	−0.0056 (9)	0.0340 (9)	0.0029 (7)
C16	0.0288 (7)	0.0292 (7)	0.0306 (7)	−0.0061 (5)	0.0039 (6)	0.0094 (5)

O1—C10	1.3782 (13)	C6—H6	0.980 (15)
O1—C13	1.3650 (16)	C8—C9	1.5142 (16)
O2—N3	1.3976 (12)	C8—H81	0.973 (14)
O2—C14	1.4547 (14)	C8—H82	0.984 (15)
N1—C1	1.3661 (15)	C9—C10	1.4511 (17)
N1—C7	1.3823 (15)	C10—C11	1.3621 (17)
N1—C8	1.4625 (15)	C11—C12	1.4247 (18)
N2—C1	1.3096 (16)	C11—H11	0.981 (15)
N2—C2	1.3917 (17)	C12—H12	0.948 (17)
N3—C9	1.2929 (15)	C13—C12	1.3440 (19)
C1—H1	0.981 (15)	C13—H13	0.964 (17)
C2—C3	1.3988 (18)	C14—C15	1.505 (2)
C2—C7	1.4043 (17)	C14—H14	0.988 (16)
C3—C4	1.381 (2)	C15—H151	1.02 (2)
C3—H3	0.974 (16)	C15—H152	0.98 (2)
C4—H4	0.966 (19)	C15—H153	0.98 (2)
C5—C4	1.402 (2)	C16—C14	1.5107 (19)
C5—H5	0.983 (17)	C16—H161	1.057 (18)
C6—C5	1.3836 (19)	C16—H163	0.982 (17)
C6—C7	1.3919 (18)	C16—H162	0.973 (19)
C13—O1—C10	106.74 (9)	N3—C9—C10	126.47 (10)
N3—O2—C14	110.34 (9)	N3—C9—C8	114.73 (11)
C1—N1—C7	106.29 (10)	C10—C9—C8	118.73 (10)
C1—N1—C8	127.66 (10)	C11—C10—O1	109.24 (10)
C7—N1—C8	126.05 (10)	C11—C10—C9	136.17 (11)
C1—N2—C2	104.24 (10)	O1—C10—C9	114.58 (10)
C9—N3—O2	111.22 (9)	C10—C11—C12	106.75 (11)
N2—C1—N1	114.13 (11)	C10—C11—H11	124.1 (9)
N2—C1—H1	125.1 (8)	C12—C11—H11	129.2 (9)
N1—C1—H1	120.7 (8)	C13—C12—C11	106.61 (12)
N2—C2—C3	129.89 (12)	C13—C12—H12	125.5 (10)
N2—C2—C7	110.19 (10)	C11—C12—H12	127.8 (10)
C3—C2—C7	119.91 (12)	C12—C13—O1	110.65 (11)
C4—C3—C2	117.53 (13)	C12—C13—H13	134.2 (10)
C4—C3—H3	123.9 (10)	O1—C13—H13	115.1 (9)
C2—C3—H3	118.6 (10)	O2—C14—C15	109.71 (11)
C3—C4—C5	121.71 (13)	O2—C14—C16	104.87 (10)
C3—C4—H4	118.9 (10)	C15—C14—C16	113.33 (12)
C5—C4—H4	119.4 (10)	O2—C14—H14	107.9 (9)
C6—C5—C4	121.81 (14)	C15—C14—H14	110.6 (9)
C6—C5—H5	118.2 (10)	C16—C14—H14	110.2 (9)
C4—C5—H5	120.0 (10)	C14—C15—H151	111.3 (11)
C5—C6—C7	116.20 (12)	C14—C15—H152	110.8 (12)
C5—C6—H6	121.9 (9)	H151—C15—H152	109.8 (17)
C7—C6—H6	121.9 (9)	C14—C15—H153	111.1 (11)
N1—C7—C6	132.02 (11)	H151—C15—H153	108.3 (15)
N1—C7—C2	105.14 (10)	H152—C15—H153	105.3 (16)
C6—C7—C2	122.83 (11)	C14—C16—H161	112.4 (9)
N1—C8—C9	111.54 (9)	C14—C16—H163	108.7 (10)
N1—C8—H82	108.4 (8)	H161—C16—H163	108.5 (14)
C9—C8—H82	108.8 (8)	C14—C16—H162	108.6 (11)
N1—C8—H81	107.7 (8)	H161—C16—H162	112.2 (14)
C9—C8—H81	111.0 (8)	H163—C16—H162	106.1 (14)
H82—C8—H81	109.4 (12)
C13—O1—C10—C11	0.18 (12)	C7—C2—C3—C4	0.80 (18)
C13—O1—C10—C9	−179.51 (10)	N2—C2—C7—N1	−0.13 (13)
C10—O1—C13—C12	−0.41 (14)	C3—C2—C7—N1	−179.70 (10)
C14—O2—N3—C9	−177.47 (9)	N2—C2—C7—C6	178.84 (11)
N3—O2—C14—C15	−82.98 (13)	C3—C2—C7—C6	−0.73 (18)
N3—O2—C14—C16	155.00 (9)	C2—C3—C4—C5	−0.2 (2)
C7—N1—C1—N2	0.10 (14)	C6—C5—C4—C3	−0.6 (2)
C8—N1—C1—N2	179.73 (11)	C7—C6—C5—C4	0.7 (2)
C1—N1—C7—C6	−178.81 (12)	C5—C6—C7—N1	178.63 (12)
C8—N1—C7—C6	1.55 (19)	C5—C6—C7—C2	−0.03 (18)
C1—N1—C7—C2	0.03 (12)	N1—C8—C9—N3	−100.58 (12)
C8—N1—C7—C2	−179.62 (10)	N1—C8—C9—C10	76.58 (13)
C1—N1—C8—C9	−104.20 (13)	N3—C9—C10—C11	−5.0 (2)
C7—N1—C8—C9	75.38 (14)	C8—C9—C10—C11	178.23 (12)
C2—N2—C1—N1	−0.17 (14)	N3—C9—C10—O1	174.60 (10)
C1—N2—C2—C3	179.70 (12)	C8—C9—C10—O1	−2.19 (14)
C1—N2—C2—C7	0.18 (13)	O1—C10—C11—C12	0.10 (13)
O2—N3—C9—C10	−1.02 (15)	C9—C10—C11—C12	179.69 (12)
O2—N3—C9—C8	175.89 (9)	C10—C11—C12—C13	−0.34 (14)
N2—C2—C3—C4	−178.67 (12)	O1—C13—C12—C11	0.46 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2	0.98 (2)	2.32 (2)	2.772 (2)	107 (1)
C13—H13···N2i	0.96 (2)	2.37 (2)	3.286 (2)	159 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2	0.98 (2)	2.32 (2)	2.772 (2)	107 (1)
C13—H13⋯N2i	0.96 (2)	2.37 (2)	3.286 (2)	159 (1)

Symmetry code: (i) .