1-(1-Benzo-furan-2-yl)ethanone O-(2,6-di-fluoro-benz-yl)oxime.

In the title compound, C17H13F2NO2, the 2,2-di-fluoro-benz-yloxy residue assumes an E configuration with respect to the benzo-furan system. The benzene ring makes a dihedral angle of 61.70 (4)° with the fused ring system (r.m.s. deviation = 0.008 Å). In the crystal, mol-ecules are connected by weak C-H⋯F hydrogen bonds into chains extending parallel to the b-axis direction.

Related literature

For background to anti­fungal agents, see: Benedetti & Bani (1999 ▶); Sheehan et al. (1999 ▶). For the biological activity of oximes and their ethers, see: Attia et al. (2013 ▶); De Luca (2006 ▶); Emami et al. (2004 ▶); Karakurt et al. (2001 ▶); Massolini et al. (1993 ▶); Mixich & Thiele (1985 ▶). For the synthesis of the title compound, see: Demirayak et al. (2002 ▶).

Experimental

Crystal data

C17H13F2NO2

M = 301.28

Monoclinic,

a = 7.36652 (17) Å

b = 17.0314 (4) Å

c = 11.2047 (2) Å

β = 90.020 (2)°

V = 1405.76 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 130 K

0.35 × 0.15 × 0.12 mm

Data collection

Agilent Xcalibur Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.992, T max = 1.000

24335 measured reflections

3548 independent reflections

2887 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.099

S = 1.03

3548 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, publication_text. DOI: 10.1107/S1600536813034090/zs2281sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034090/zs2281Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034090/zs2281Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H13F2NO2	F(000) = 624
Mr = 301.28	Dx = 1.424 Mg m−3
Monoclinic, P21/n	Melting point = 346–348 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.36652 (17) Å	Cell parameters from 10469 reflections
b = 17.0314 (4) Å	θ = 2.2–29.1°
c = 11.2047 (2) Å	µ = 0.11 mm−1
β = 90.020 (2)°	T = 130 K
V = 1405.76 (5) Å3	Indefinite, colourless
Z = 4	0.35 × 0.15 × 0.12 mm

Agilent Xcalibur Atlas diffractometer	3548 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2887 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10.3088 pixels mm-1	θmax = 29.1°, θmin = 2.2°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −23→22
Tmin = 0.992, Tmax = 1.000	l = −14→15
24335 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.5216P] where P = (Fo2 + 2Fc2)/3
3548 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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
O1	0.16108 (11)	0.14365 (5)	0.55614 (7)	0.0225 (2)
C2	0.01949 (16)	0.13157 (7)	0.47691 (11)	0.0202 (2)
C3	0.05125 (18)	0.16689 (7)	0.37076 (11)	0.0246 (3)
H3	−0.0245	0.1667	0.3044	0.030*
C4	0.22538 (17)	0.20490 (7)	0.38062 (11)	0.0228 (3)
C5	0.3345 (2)	0.25081 (8)	0.30607 (12)	0.0292 (3)
H5	0.2964	0.2639	0.2295	0.035*
C6	0.50053 (19)	0.27631 (8)	0.34892 (13)	0.0302 (3)
H6	0.5750	0.3065	0.3001	0.036*
C7	0.55844 (18)	0.25753 (8)	0.46421 (13)	0.0294 (3)
H7	0.6711	0.2753	0.4902	0.035*
C8	0.45207 (18)	0.21312 (8)	0.54084 (13)	0.0268 (3)
H8	0.4893	0.2009	0.6179	0.032*
C9	0.28652 (16)	0.18797 (7)	0.49543 (11)	0.0208 (3)
C10	−0.13574 (16)	0.08676 (7)	0.52060 (11)	0.0199 (2)
C11	−0.27542 (17)	0.05873 (8)	0.43335 (11)	0.0246 (3)
H11A	−0.2468	0.0062	0.4088	0.037*
H11B	−0.2761	0.0926	0.3649	0.037*
H11C	−0.3929	0.0594	0.4704	0.037*
N12	−0.13799 (14)	0.07490 (6)	0.63388 (9)	0.0226 (2)
O13	−0.29434 (11)	0.03251 (5)	0.66817 (8)	0.0240 (2)
C14	−0.28904 (17)	0.02743 (9)	0.79613 (11)	0.0275 (3)
H14A	−0.2683	0.0789	0.8305	0.033*
H14B	−0.1917	−0.0072	0.8213	0.033*
C15	−0.46849 (16)	−0.00434 (7)	0.83627 (10)	0.0200 (2)
C16	−0.62337 (17)	0.04170 (7)	0.83715 (11)	0.0222 (3)
C17	−0.79223 (18)	0.01540 (9)	0.87023 (12)	0.0287 (3)
H17	−0.8924	0.0486	0.8687	0.034*
C18	−0.80877 (19)	−0.06188 (9)	0.90588 (12)	0.0316 (3)
H18	−0.9222	−0.0813	0.9272	0.038*
C19	−0.6595 (2)	−0.11065 (8)	0.91027 (12)	0.0332 (3)
H19	−0.6704	−0.1624	0.9358	0.040*
C20	−0.49296 (19)	−0.08056 (7)	0.87563 (11)	0.0252 (3)
F21	−0.60530 (12)	0.11776 (5)	0.80385 (8)	0.0363 (2)
F22	−0.34453 (13)	−0.12699 (5)	0.88276 (8)	0.0428 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0189 (4)	0.0270 (5)	0.0216 (4)	−0.0037 (3)	0.0001 (3)	0.0006 (3)
C2	0.0188 (6)	0.0209 (6)	0.0209 (6)	0.0000 (4)	−0.0008 (5)	−0.0047 (4)
C3	0.0256 (6)	0.0270 (6)	0.0211 (6)	−0.0050 (5)	−0.0012 (5)	−0.0009 (5)
C4	0.0255 (6)	0.0196 (6)	0.0234 (6)	−0.0031 (5)	0.0016 (5)	−0.0029 (4)
C5	0.0362 (8)	0.0257 (6)	0.0257 (7)	−0.0078 (6)	0.0016 (6)	0.0011 (5)
C6	0.0326 (7)	0.0229 (6)	0.0350 (7)	−0.0088 (5)	0.0080 (6)	−0.0012 (5)
C7	0.0219 (6)	0.0255 (6)	0.0407 (8)	−0.0061 (5)	0.0002 (6)	−0.0051 (5)
C8	0.0231 (6)	0.0277 (7)	0.0295 (7)	−0.0016 (5)	−0.0023 (5)	−0.0006 (5)
C9	0.0207 (6)	0.0174 (5)	0.0244 (6)	−0.0004 (4)	0.0041 (5)	−0.0018 (4)
C10	0.0188 (6)	0.0203 (6)	0.0206 (6)	0.0013 (4)	0.0020 (5)	−0.0028 (4)
C11	0.0253 (6)	0.0271 (6)	0.0213 (6)	−0.0052 (5)	−0.0005 (5)	−0.0023 (5)
N12	0.0160 (5)	0.0292 (6)	0.0225 (5)	−0.0043 (4)	0.0033 (4)	−0.0012 (4)
O13	0.0174 (4)	0.0369 (5)	0.0178 (4)	−0.0076 (4)	0.0023 (3)	0.0005 (4)
C14	0.0184 (6)	0.0468 (8)	0.0173 (6)	−0.0052 (5)	−0.0012 (5)	0.0029 (5)
C15	0.0181 (6)	0.0286 (6)	0.0134 (5)	−0.0020 (5)	−0.0008 (4)	0.0004 (4)
C16	0.0231 (6)	0.0243 (6)	0.0194 (6)	−0.0022 (5)	−0.0023 (5)	0.0030 (4)
C17	0.0185 (6)	0.0426 (8)	0.0249 (7)	−0.0001 (5)	0.0006 (5)	−0.0031 (6)
C18	0.0271 (7)	0.0467 (8)	0.0209 (6)	−0.0161 (6)	0.0027 (5)	−0.0005 (6)
C19	0.0520 (9)	0.0264 (7)	0.0212 (6)	−0.0149 (6)	−0.0030 (6)	0.0039 (5)
C20	0.0317 (7)	0.0261 (6)	0.0179 (6)	0.0044 (5)	−0.0037 (5)	−0.0015 (5)
F21	0.0375 (5)	0.0264 (4)	0.0449 (5)	0.0016 (3)	−0.0033 (4)	0.0099 (3)
F22	0.0504 (6)	0.0360 (5)	0.0421 (5)	0.0204 (4)	−0.0081 (4)	−0.0012 (4)

O1—C9	1.3736 (14)	C11—H11B	0.9600
O1—C2	1.3848 (15)	C11—H11C	0.9600
C2—C3	1.3534 (17)	N12—O13	1.4127 (13)
C2—C10	1.4594 (17)	O13—C14	1.4369 (15)
C3—C4	1.4410 (18)	C14—C15	1.4977 (17)
C3—H3	0.9300	C14—H14A	0.9700
C4—C9	1.3929 (18)	C14—H14B	0.9700
C4—C5	1.3986 (18)	C15—C20	1.3828 (18)
C5—C6	1.384 (2)	C15—C16	1.3844 (17)
C5—H5	0.9300	C16—F21	1.3547 (14)
C6—C7	1.397 (2)	C16—C17	1.3732 (18)
C6—H6	0.9300	C17—C18	1.381 (2)
C7—C8	1.3870 (19)	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.379 (2)
C8—C9	1.3890 (18)	C18—H18	0.9300
C8—H8	0.9300	C19—C20	1.385 (2)
C10—N12	1.2853 (16)	C19—H19	0.9300
C10—C11	1.4972 (17)	C20—F22	1.3517 (15)
C11—H11A	0.9600
C9—O1—C2	105.72 (9)	H11A—C11—H11B	109.5
C3—C2—O1	111.52 (11)	C10—C11—H11C	109.5
C3—C2—C10	131.52 (11)	H11A—C11—H11C	109.5
O1—C2—C10	116.92 (10)	H11B—C11—H11C	109.5
C2—C3—C4	106.64 (11)	C10—N12—O13	111.08 (10)
C2—C3—H3	126.7	N12—O13—C14	106.28 (9)
C4—C3—H3	126.7	O13—C14—C15	107.32 (10)
C9—C4—C5	118.79 (12)	O13—C14—H14A	110.3
C9—C4—C3	105.39 (11)	C15—C14—H14A	110.3
C5—C4—C3	135.82 (13)	O13—C14—H14B	110.3
C6—C5—C4	118.45 (13)	C15—C14—H14B	110.3
C6—C5—H5	120.8	H14A—C14—H14B	108.5
C4—C5—H5	120.8	C20—C15—C16	114.96 (11)
C5—C6—C7	121.23 (12)	C20—C15—C14	123.38 (12)
C5—C6—H6	119.4	C16—C15—C14	121.67 (11)
C7—C6—H6	119.4	F21—C16—C17	118.38 (12)
C8—C7—C6	121.65 (12)	F21—C16—C15	117.30 (11)
C8—C7—H7	119.2	C17—C16—C15	124.32 (12)
C6—C7—H7	119.2	C16—C17—C18	117.97 (13)
C7—C8—C9	115.95 (13)	C16—C17—H17	121.0
C7—C8—H8	122.0	C18—C17—H17	121.0
C9—C8—H8	122.0	C19—C18—C17	120.94 (12)
O1—C9—C8	125.36 (12)	C19—C18—H18	119.5
O1—C9—C4	110.72 (10)	C17—C18—H18	119.5
C8—C9—C4	123.92 (12)	C18—C19—C20	118.26 (12)
N12—C10—C2	115.07 (11)	C18—C19—H19	120.9
N12—C10—C11	125.85 (11)	C20—C19—H19	120.9
C2—C10—C11	119.08 (11)	F22—C20—C15	117.55 (12)
C10—C11—H11A	109.5	F22—C20—C19	118.92 (12)
C10—C11—H11B	109.5	C15—C20—C19	123.51 (12)
C9—O1—C2—C3	−0.51 (13)	O1—C2—C10—C11	−168.36 (10)
C9—O1—C2—C10	−178.77 (10)	C2—C10—N12—O13	178.89 (9)
O1—C2—C3—C4	−0.06 (14)	C11—C10—N12—O13	−1.33 (17)
C10—C2—C3—C4	177.86 (12)	C10—N12—O13—C14	−176.13 (10)
C2—C3—C4—C9	0.60 (14)	N12—O13—C14—C15	170.08 (10)
C2—C3—C4—C5	−179.29 (15)	O13—C14—C15—C20	105.09 (13)
C9—C4—C5—C6	1.18 (19)	O13—C14—C15—C16	−75.36 (15)
C3—C4—C5—C6	−178.95 (14)	C20—C15—C16—F21	177.47 (11)
C4—C5—C6—C7	−0.5 (2)	C14—C15—C16—F21	−2.12 (17)
C5—C6—C7—C8	−0.4 (2)	C20—C15—C16—C17	−2.02 (18)
C6—C7—C8—C9	0.70 (19)	C14—C15—C16—C17	178.39 (12)
C2—O1—C9—C8	−179.21 (12)	F21—C16—C17—C18	−178.97 (11)
C2—O1—C9—C4	0.91 (13)	C15—C16—C17—C18	0.5 (2)
C7—C8—C9—O1	−179.90 (11)	C16—C17—C18—C19	1.2 (2)
C7—C8—C9—C4	−0.03 (19)	C17—C18—C19—C20	−1.3 (2)
C5—C4—C9—O1	178.96 (11)	C16—C15—C20—F22	−176.55 (11)
C3—C4—C9—O1	−0.95 (13)	C14—C15—C20—F22	3.03 (18)
C5—C4—C9—C8	−0.92 (19)	C16—C15—C20—C19	1.93 (18)
C3—C4—C9—C8	179.17 (12)	C14—C15—C20—C19	−178.49 (12)
C3—C2—C10—N12	−166.39 (13)	C18—C19—C20—F22	178.09 (12)
O1—C2—C10—N12	11.44 (16)	C18—C19—C20—C15	−0.4 (2)
C3—C2—C10—C11	13.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F22i	0.93	2.54	3.3537 (16)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯F22i	0.93	2.54	3.3537 (16)	147

Symmetry code: (i) .