1-(1-Benzofuran-2-yl)ethanone O-(4-chloro-benz-yl)oxime.

In the title compound, C(17)H(14)ClNO(2), the p-chloro-benz-yloxy residue assumes an E conformation with respect to the benzofuran system. The carbo- and heterocyclic systems make a dihedral angle of 47.99 (4)°. In the crystal, there are no significant intermolecular interactions present.

Related literature

For the biological activity of free oximes and their ethers, see: Chern et al. (2004 ▶); Emami et al. (2004 ▶); Demirayak et al. (2002 ▶); Bhandari et al. (2009 ▶); Jindal et al. (2003 ▶); Karakurt et al. (2001 ▶).

Experimental

Crystal data

C17H14ClNO2

M = 299.74

Triclinic,

a = 5.8842 (4) Å

b = 7.1173 (6) Å

c = 17.2313 (16) Å

α = 93.802 (7)°

β = 97.998 (7)°

γ = 95.363 (7)°

V = 709.19 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 130 K

0.50 × 0.40 × 0.05 mm

Data collection

Agilent Xcalibur Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.783, T max = 1.000

9366 measured reflections

3407 independent reflections

2817 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.137

S = 1.10

3407 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, publication_text. DOI: 10.1107/S1600536812042675/bt6848sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042675/bt6848Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042675/bt6848Isup3.cml

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

C17H14ClNO2	Z = 2
Mr = 299.74	F(000) = 312
Triclinic, P1	Dx = 1.404 Mg m−3
Hall symbol: -P 1	Melting point = 377–378 K
a = 5.8842 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.1173 (6) Å	Cell parameters from 3128 reflections
c = 17.2313 (16) Å	θ = 2.4–28.9°
α = 93.802 (7)°	µ = 0.27 mm−1
β = 97.998 (7)°	T = 130 K
γ = 95.363 (7)°	Lath, colourless
V = 709.19 (10) Å3	0.50 × 0.40 × 0.05 mm

Agilent Xcalibur Atlas diffractometer	3407 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2817 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 29.0°, θmin = 2.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	h = −8→7
Tmin = 0.783, Tmax = 1.000	k = −9→9
9366 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.7613P] where P = (Fo2 + 2Fc2)/3
3407 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −0.31 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	0.8938 (2)	0.1648 (2)	0.67864 (8)	0.0185 (3)
C2	0.6830 (4)	0.2349 (3)	0.65738 (13)	0.0178 (4)
C3	0.5839 (4)	0.2838 (3)	0.72112 (13)	0.0190 (4)
H3	0.4404	0.3350	0.7210	0.023*
C4	0.7371 (4)	0.2436 (3)	0.78881 (13)	0.0188 (4)
C5	0.7372 (4)	0.2580 (3)	0.87016 (13)	0.0218 (5)
H5	0.6144	0.3090	0.8921	0.026*
C6	0.9194 (4)	0.1967 (3)	0.91800 (13)	0.0242 (5)
H6	0.9209	0.2054	0.9733	0.029*
C7	1.1032 (4)	0.1214 (3)	0.88624 (13)	0.0228 (5)
H7	1.2259	0.0798	0.9205	0.027*
C8	1.1080 (4)	0.1070 (3)	0.80611 (13)	0.0200 (4)
H8	1.2312	0.0567	0.7843	0.024*
C9	0.9240 (4)	0.1697 (3)	0.75924 (12)	0.0171 (4)
C10	0.6054 (4)	0.2459 (3)	0.57402 (13)	0.0190 (4)
C11	0.3554 (4)	0.2650 (4)	0.54716 (14)	0.0249 (5)
H11A	0.3417	0.3809	0.5200	0.037*
H11B	0.2732	0.2712	0.5928	0.037*
H11C	0.2881	0.1553	0.5112	0.037*
N12	0.7611 (3)	0.2386 (3)	0.52841 (10)	0.0206 (4)
O13	0.6618 (3)	0.2504 (2)	0.44972 (9)	0.0224 (4)
C14	0.8445 (4)	0.2641 (3)	0.40298 (13)	0.0230 (5)
H14A	0.9267	0.1491	0.4058	0.028*
H14B	0.9564	0.3751	0.4231	0.028*
C15	0.7438 (4)	0.2847 (3)	0.31948 (12)	0.0188 (4)
C16	0.5159 (4)	0.2194 (3)	0.28902 (13)	0.0194 (4)
H16	0.4154	0.1687	0.3228	0.023*
C17	0.4342 (4)	0.2276 (3)	0.20982 (13)	0.0196 (4)
H17	0.2790	0.1825	0.1893	0.024*
C18	0.5821 (4)	0.3024 (3)	0.16110 (12)	0.0205 (4)
C19	0.8082 (4)	0.3733 (3)	0.19012 (13)	0.0214 (5)
H19	0.9070	0.4265	0.1564	0.026*
C20	0.8865 (4)	0.3647 (3)	0.26924 (13)	0.0202 (4)
H20	1.0403	0.4141	0.2898	0.024*
Cl21	0.48371 (11)	0.30347 (9)	0.06126 (3)	0.03010 (18)

	U11	U22	U33	U12	U13	U23
O1	0.0128 (7)	0.0216 (8)	0.0222 (7)	0.0061 (6)	0.0031 (6)	0.0021 (6)
C2	0.0121 (10)	0.0152 (10)	0.0266 (11)	0.0033 (8)	0.0025 (8)	0.0025 (8)
C3	0.0134 (10)	0.0183 (10)	0.0261 (11)	0.0031 (8)	0.0039 (8)	0.0028 (8)
C4	0.0146 (10)	0.0155 (10)	0.0266 (11)	0.0015 (8)	0.0048 (8)	0.0007 (8)
C5	0.0174 (11)	0.0226 (11)	0.0263 (11)	0.0029 (9)	0.0067 (9)	0.0006 (9)
C6	0.0239 (12)	0.0281 (12)	0.0210 (11)	0.0040 (9)	0.0033 (9)	0.0018 (9)
C7	0.0176 (11)	0.0241 (12)	0.0266 (11)	0.0037 (9)	0.0006 (9)	0.0052 (9)
C8	0.0145 (10)	0.0176 (11)	0.0283 (11)	0.0029 (8)	0.0038 (9)	0.0020 (8)
C9	0.0139 (10)	0.0148 (10)	0.0226 (10)	−0.0001 (8)	0.0045 (8)	0.0011 (8)
C10	0.0164 (10)	0.0164 (10)	0.0244 (11)	0.0037 (8)	0.0030 (8)	0.0010 (8)
C11	0.0169 (11)	0.0315 (13)	0.0267 (11)	0.0068 (9)	0.0015 (9)	0.0032 (9)
N12	0.0173 (9)	0.0251 (10)	0.0198 (9)	0.0050 (7)	0.0011 (7)	0.0025 (7)
O13	0.0158 (8)	0.0330 (9)	0.0192 (8)	0.0062 (6)	0.0025 (6)	0.0037 (6)
C14	0.0147 (10)	0.0314 (13)	0.0239 (11)	0.0054 (9)	0.0042 (9)	0.0021 (9)
C15	0.0168 (10)	0.0170 (11)	0.0233 (11)	0.0047 (8)	0.0036 (8)	0.0006 (8)
C16	0.0159 (10)	0.0187 (11)	0.0251 (11)	0.0037 (8)	0.0068 (8)	0.0022 (8)
C17	0.0145 (10)	0.0181 (10)	0.0259 (11)	0.0040 (8)	0.0013 (8)	−0.0003 (8)
C18	0.0248 (11)	0.0174 (11)	0.0202 (10)	0.0074 (9)	0.0041 (9)	0.0005 (8)
C19	0.0206 (11)	0.0182 (11)	0.0273 (11)	0.0027 (8)	0.0087 (9)	0.0030 (8)
C20	0.0145 (10)	0.0179 (11)	0.0278 (11)	0.0009 (8)	0.0044 (8)	−0.0014 (8)
Cl21	0.0352 (4)	0.0342 (3)	0.0212 (3)	0.0077 (3)	0.0019 (2)	0.0033 (2)

O1—C9	1.373 (2)	C11—H11B	0.9800
O1—C2	1.391 (2)	C11—H11C	0.9800
C2—C3	1.354 (3)	N12—O13	1.411 (2)
C2—C10	1.455 (3)	O13—C14	1.430 (3)
C3—C4	1.433 (3)	C14—C15	1.500 (3)
C3—H3	0.9500	C14—H14A	0.9900
C4—C5	1.399 (3)	C14—H14B	0.9900
C4—C9	1.405 (3)	C15—C16	1.395 (3)
C5—C6	1.382 (3)	C15—C20	1.399 (3)
C5—H5	0.9500	C16—C17	1.389 (3)
C6—C7	1.411 (3)	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.386 (3)
C7—C8	1.382 (3)	C17—H17	0.9500
C7—H7	0.9500	C18—C19	1.389 (3)
C8—C9	1.385 (3)	C18—Cl21	1.738 (2)
C8—H8	0.9500	C19—C20	1.384 (3)
C10—N12	1.289 (3)	C19—H19	0.9500
C10—C11	1.501 (3)	C20—H20	0.9500
C11—H11A	0.9800
C9—O1—C2	105.57 (15)	H11A—C11—H11B	109.5
C3—C2—O1	111.63 (18)	C10—C11—H11C	109.5
C3—C2—C10	130.7 (2)	H11A—C11—H11C	109.5
O1—C2—C10	117.67 (17)	H11B—C11—H11C	109.5
C2—C3—C4	106.82 (19)	C10—N12—O13	110.10 (17)
C2—C3—H3	126.6	N12—O13—C14	107.89 (15)
C4—C3—H3	126.6	O13—C14—C15	108.84 (17)
C5—C4—C9	118.6 (2)	O13—C14—H14A	109.9
C5—C4—C3	135.9 (2)	C15—C14—H14A	109.9
C9—C4—C3	105.50 (19)	O13—C14—H14B	109.9
C6—C5—C4	118.7 (2)	C15—C14—H14B	109.9
C6—C5—H5	120.7	H14A—C14—H14B	108.3
C4—C5—H5	120.7	C16—C15—C20	118.7 (2)
C5—C6—C7	121.3 (2)	C16—C15—C14	122.46 (19)
C5—C6—H6	119.4	C20—C15—C14	118.80 (19)
C7—C6—H6	119.4	C17—C16—C15	120.7 (2)
C8—C7—C6	121.2 (2)	C17—C16—H16	119.6
C8—C7—H7	119.4	C15—C16—H16	119.6
C6—C7—H7	119.4	C18—C17—C16	119.2 (2)
C7—C8—C9	116.6 (2)	C18—C17—H17	120.4
C7—C8—H8	121.7	C16—C17—H17	120.4
C9—C8—H8	121.7	C17—C18—C19	121.4 (2)
O1—C9—C8	125.81 (19)	C17—C18—Cl21	119.18 (17)
O1—C9—C4	110.48 (18)	C19—C18—Cl21	119.38 (17)
C8—C9—C4	123.7 (2)	C20—C19—C18	118.7 (2)
N12—C10—C2	116.27 (19)	C20—C19—H19	120.7
N12—C10—C11	124.8 (2)	C18—C19—H19	120.7
C2—C10—C11	118.90 (18)	C19—C20—C15	121.3 (2)
C10—C11—H11A	109.5	C19—C20—H20	119.3
C10—C11—H11B	109.5	C15—C20—H20	119.3
C9—O1—C2—C3	0.5 (2)	O1—C2—C10—N12	−17.9 (3)
C9—O1—C2—C10	−179.91 (18)	C3—C2—C10—C11	−18.3 (4)
O1—C2—C3—C4	−0.2 (2)	O1—C2—C10—C11	162.22 (19)
C10—C2—C3—C4	−179.7 (2)	C2—C10—N12—O13	179.91 (17)
C2—C3—C4—C5	−179.0 (2)	C11—C10—N12—O13	−0.3 (3)
C2—C3—C4—C9	−0.2 (2)	C10—N12—O13—C14	173.34 (18)
C9—C4—C5—C6	−0.9 (3)	N12—O13—C14—C15	−177.74 (17)
C3—C4—C5—C6	177.7 (2)	O13—C14—C15—C16	−24.9 (3)
C4—C5—C6—C7	0.2 (3)	O13—C14—C15—C20	158.05 (19)
C5—C6—C7—C8	0.3 (4)	C20—C15—C16—C17	2.1 (3)
C6—C7—C8—C9	−0.1 (3)	C14—C15—C16—C17	−174.9 (2)
C2—O1—C9—C8	177.8 (2)	C15—C16—C17—C18	−0.2 (3)
C2—O1—C9—C4	−0.7 (2)	C16—C17—C18—C19	−1.5 (3)
C7—C8—C9—O1	−178.81 (19)	C16—C17—C18—Cl21	177.27 (16)
C7—C8—C9—C4	−0.6 (3)	C17—C18—C19—C20	1.3 (3)
C5—C4—C9—O1	179.55 (18)	Cl21—C18—C19—C20	−177.53 (16)
C3—C4—C9—O1	0.6 (2)	C18—C19—C20—C15	0.7 (3)
C5—C4—C9—C8	1.1 (3)	C16—C15—C20—C19	−2.4 (3)
C3—C4—C9—C8	−177.9 (2)	C14—C15—C20—C19	174.7 (2)
C3—C2—C10—N12	161.5 (2)