2-[(3-Oxo-1-benzofuran-6-yl)-oxy]aceto-nitrile.

The mol-ecule of the title compound, C11H8O3, is essentially planar [r.m.s. deviation = 0.025 (2) Å]. In the crystal, mol-ecules are stacked along [110] but no short π-π contacts are observed. Weak C-H⋯O inter-actions link the mol-ecules into chains along [101].

Related literature

For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004 ▶). For the synthesis of the title compound, see: Hoogendoorn et al. (2011 ▶).

Experimental

Crystal data

C11H8O3

M = 188.17

Monoclinic,

a = 16.8785 (5) Å

b = 5.4202 (2) Å

c = 19.6107 (6) Å

β = 91.469 (2)°

V = 1793.49 (10) Å3

Z = 8

Cu Kα radiation

μ = 0.85 mm−1

T = 100 K

0.19 × 0.15 × 0.11 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.855, T max = 0.912

10685 measured reflections

1545 independent reflections

1451 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.076

S = 1.04

1545 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048441/ld2084sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048441/ld2084Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048441/ld2084Isup3.cml

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

C11H8O3	F(000) = 784
Mr = 188.17	Dx = 1.394 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 6173 reflections
a = 16.8785 (5) Å	θ = 6.8–65.7°
b = 5.4202 (2) Å	µ = 0.85 mm−1
c = 19.6107 (6) Å	T = 100 K
β = 91.469 (2)°	Cube, yellow
V = 1793.49 (10) Å3	0.19 × 0.15 × 0.11 mm
Z = 8

Bruker APEX DUO 4K CCD diffractometer	1545 independent reflections
Incoatec Quazar Multilayer Mirror monochromator	1451 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1	Rint = 0.026
φ and ω scans	θmax = 66.2°, θmin = 6.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −19→18
Tmin = 0.855, Tmax = 0.912	k = −6→6
10685 measured reflections	l = −22→23

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0326P)2 + 1.2605P] where P = (Fo2 + 2Fc2)/3
1545 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 5 s/frame. A total of 2405 frames were collected with a frame width of 1° covering up to θ = 66.21° with 98.0% completeness accomplished.

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
C1	0.33402 (7)	−0.0134 (2)	0.16647 (6)	0.0301 (3)
H1A	0.3908	0.0177	0.1582	0.036*
H1B	0.33	−0.1366	0.2035	0.036*
C2	0.29260 (7)	0.2247 (2)	0.18581 (6)	0.0275 (3)
C3	0.22985 (7)	0.2558 (2)	0.13478 (6)	0.0258 (3)
C4	0.23445 (6)	0.0603 (2)	0.08957 (6)	0.0252 (3)
C5	0.18383 (6)	0.0313 (2)	0.03363 (6)	0.0256 (3)
H5	0.188	−0.1042	0.0032	0.031*
C6	0.12641 (6)	0.2130 (2)	0.02471 (6)	0.0253 (3)
C7	0.12021 (7)	0.4147 (2)	0.06963 (6)	0.0275 (3)
H7	0.0802	0.5354	0.0618	0.033*
C8	0.17159 (7)	0.4373 (2)	0.12444 (6)	0.0277 (3)
H8A	0.1678	0.5731	0.1548	0.033*
C9	0.07331 (7)	0.0050 (2)	−0.07344 (6)	0.0281 (3)
H9A	0.0623	−0.1496	−0.0485	0.034*
H9B	0.1263	−0.009	−0.0936	0.034*
C10	0.01328 (7)	0.0443 (2)	−0.12691 (6)	0.0295 (3)
C11	−0.03534 (7)	0.0700 (2)	−0.17094 (6)	0.0340 (3)
H11	−0.0744	0.0906	−0.2063	0.041*
O1	0.31189 (5)	0.35618 (16)	0.23405 (4)	0.0328 (2)
O2	0.29422 (5)	−0.10199 (15)	0.10488 (4)	0.0296 (2)
O3	0.07151 (5)	0.21196 (15)	−0.02749 (4)	0.0289 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0269 (6)	0.0336 (7)	0.0295 (6)	0.0015 (5)	−0.0041 (5)	0.0012 (5)
C2	0.0270 (6)	0.0289 (6)	0.0265 (6)	−0.0038 (5)	0.0012 (5)	0.0022 (5)
C3	0.0264 (6)	0.0253 (6)	0.0257 (6)	−0.0028 (5)	0.0015 (4)	0.0019 (5)
C4	0.0226 (5)	0.0245 (6)	0.0285 (6)	0.0000 (4)	0.0032 (4)	0.0043 (5)
C5	0.0262 (6)	0.0246 (6)	0.0261 (6)	−0.0008 (5)	0.0029 (4)	−0.0001 (5)
C6	0.0243 (6)	0.0269 (6)	0.0248 (6)	−0.0023 (5)	0.0010 (4)	0.0040 (5)
C7	0.0288 (6)	0.0236 (6)	0.0303 (6)	0.0022 (5)	−0.0001 (5)	0.0025 (5)
C8	0.0313 (6)	0.0232 (6)	0.0288 (6)	−0.0003 (5)	0.0018 (5)	−0.0001 (5)
C9	0.0276 (6)	0.0295 (6)	0.0273 (6)	0.0010 (5)	0.0016 (5)	−0.0016 (5)
C10	0.0279 (6)	0.0311 (6)	0.0296 (6)	−0.0003 (5)	0.0047 (5)	−0.0010 (5)
C11	0.0297 (6)	0.0418 (7)	0.0304 (6)	0.0012 (5)	−0.0018 (5)	−0.0021 (5)
O1	0.0324 (5)	0.0349 (5)	0.0307 (5)	−0.0012 (4)	−0.0048 (3)	−0.0026 (4)
O2	0.0273 (4)	0.0297 (5)	0.0316 (4)	0.0052 (3)	−0.0036 (3)	−0.0019 (3)
O3	0.0288 (4)	0.0298 (4)	0.0278 (4)	0.0034 (3)	−0.0046 (3)	−0.0026 (3)

C1—O2	1.4489 (14)	C6—O3	1.3631 (13)
C1—C2	1.5206 (17)	C6—C7	1.4095 (16)
C1—H1A	0.99	C7—C8	1.3691 (17)
C1—H1B	0.99	C7—H7	0.95
C2—O1	1.2220 (14)	C8—H8A	0.95
C2—C3	1.4481 (16)	C9—O3	1.4396 (14)
C3—C4	1.3851 (16)	C9—C10	1.4551 (16)
C3—C8	1.4021 (17)	C9—H9A	0.99
C4—O2	1.3661 (14)	C9—H9B	0.99
C4—C5	1.3822 (16)	C10—C11	1.1840 (17)
C5—C6	1.3896 (16)	C11—H11	0.95
C5—H5	0.95
O2—C1—C2	106.42 (9)	O3—C6—C7	114.37 (10)
O2—C1—H1A	110.4	C5—C6—C7	122.25 (10)
C2—C1—H1A	110.4	C8—C7—C6	120.30 (11)
O2—C1—H1B	110.4	C8—C7—H7	119.8
C2—C1—H1B	110.4	C6—C7—H7	119.8
H1A—C1—H1B	108.6	C7—C8—C3	118.58 (11)
O1—C2—C3	129.99 (11)	C7—C8—H8A	120.7
O1—C2—C1	124.96 (11)	C3—C8—H8A	120.7
C3—C2—C1	105.04 (9)	O3—C9—C10	108.15 (9)
C4—C3—C8	119.66 (10)	O3—C9—H9A	110.1
C4—C3—C2	107.53 (10)	C10—C9—H9A	110.1
C8—C3—C2	132.81 (11)	O3—C9—H9B	110.1
O2—C4—C5	122.62 (10)	C10—C9—H9B	110.1
O2—C4—C3	113.91 (10)	H9A—C9—H9B	108.4
C5—C4—C3	123.47 (11)	C11—C10—C9	178.27 (13)
C4—C5—C6	115.74 (11)	C10—C11—H11	180
C4—C5—H5	122.1	C4—O2—C1	107.09 (9)
C6—C5—H5	122.1	C6—O3—C9	116.64 (9)
O3—C6—C5	123.37 (10)
O2—C1—C2—O1	−177.45 (10)	C4—C5—C6—C7	0.20 (16)
O2—C1—C2—C3	1.34 (12)	O3—C6—C7—C8	179.74 (10)
O1—C2—C3—C4	177.78 (12)	C5—C6—C7—C8	−0.07 (17)
C1—C2—C3—C4	−0.93 (12)	C6—C7—C8—C3	−0.23 (17)
O1—C2—C3—C8	−1.2 (2)	C4—C3—C8—C7	0.40 (16)
C1—C2—C3—C8	−179.91 (12)	C2—C3—C8—C7	179.28 (11)
C8—C3—C4—O2	179.30 (10)	C5—C4—O2—C1	−179.70 (10)
C2—C3—C4—O2	0.16 (13)	C3—C4—O2—C1	0.73 (12)
C8—C3—C4—C5	−0.27 (17)	C2—C1—O2—C4	−1.26 (12)
C2—C3—C4—C5	−179.41 (10)	C5—C6—O3—C9	2.07 (15)
O2—C4—C5—C6	−179.56 (10)	C7—C6—O3—C9	−177.74 (9)
C3—C4—C5—C6	−0.03 (16)	C10—C9—O3—C6	−177.25 (9)
C4—C5—C6—O3	−179.59 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.95	2.24	3.1676 (15)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.95	2.24	3.1676 (15)	165

Symmetry code: (i) .