organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-(1-Benzo­furan-2-yl)ethanone O-(4-chloro­benz­yl)oxime

aDepartment of Organic Chemistry, Ludwik Rydygier Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Torun, ul. A. Jurasza 2, 85-089 Bydgoszcz, Poland, bDepartment of Organic Chemistry, Poznan University of Medical Sciences, ul. Grunwaldzka 6, 60-780 Poznań, Poland, and c, Faculty of Pharmacy, Ludwik Rydygier Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Torun, ul. A. Jurasza 2, 85-089 Bydgoszcz, Poland
*Correspondence e-mail: akgzella@ump.edu.pl

(Received 11 October 2012; accepted 11 October 2012; online 20 October 2012)

In the title compound, C17H14ClNO2, the p-chloro­benz­yloxy 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[Chern, J.-H., Lee, C.-C., Chang, C.-S., Lee, Y.-C., Tai, C. L., Lin, Y.-T., Shia, K.-S., Lee, C.-Y. & Shih, S.-R. (2004). Bioorg. Med. Chem. Lett. 14, 5051-5056.]); Emami et al. (2004[Emami, S., Falahati, M., Banifatemi, A., Amanlou, M. & Shafiee, A. (2004). Bioorg. Med. Chem. 12, 3971-3976.]); Demirayak et al. (2002[Demirayak, S., Uçucu, Ü., Benkli, K., Gündoğdu-Karaburun, N., Karaburun, A., Akar, D., Karabacak, M. & Kiraz, N. (2002). Il Farmaco, 57, 609-612.]); Bhandari et al. (2009[Bhandari, K., Srinivas, N., Keshava, S. & Shukla, P. (2009). Eur. J. Med. Chem. 44, 437-447.]); Jindal et al. (2003[Jindal, D. P., Chattopadhaya, R., Guleria, S. & Gupta, R. (2003). Eur. J. Med. Chem. 38, 1025-1034.]); Karakurt et al. (2001[Karakurt, A., Dalkara, S., Özalp, M., Özbey, S., Kendi, E. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 421-433.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14ClNO2

  • Mr = 299.74

  • Triclinic, [P \overline 1]

  • 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.783, Tmax = 1.000

  • 9366 measured reflections

  • 3407 independent reflections

  • 2817 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The study of free oximes and their ethers have become of much interest in recent years on account of their diverse biological activities. Antienteroviral, antifungal, antibacterial, antineoplastic, anticonvulsant and antimicrobial activities (Chern et al., 2004; Emami et al., 2004; Demirayak et al., 2002; Bhandari et al., 2009; Jindal et al., 2003; Karakurt et al., 2001) are a few among many other activities.

The crystal structure investigation of the title compound was undertaken in order to obtain information about the spatial structure of the molecule.

The molecular structure of the title compound and the atom-labelling scheme is illustrated in Fig. 1.

The nine-membered benzofuran system is almost planar with an r.m.s. deviation of 0.0122 Å. The p-chlorobenzyloxy moiety is in E configuration with respect to the C2 atom of the benzofuran system. This arrangement is confirmed by the torsional angle C2—C10—N12—O13 of 179.91 (17)°. Simultaneously, the torsion angle C10—N12—O13—C14, 173.34 (18)°, reveals an antiperiplanar conformation for atoms C10 and C14. Furthermore, the dihedral angle made by the mean planes of the above mentioned systems amounts to 47.99 (4)°.

The main factor that determines the crystal packing are normal van der Waals interactions.

Related literature top

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).

Refinement top

All H atoms were set to idealized positions and were refined with the riding model approximation: Cmethyl—H = 0.96 Å, Cmethylene—H = 0.97 Å, C(sp2)—H = 0.93 Å; Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H. The methyl group was refined as rigid group which was allowed to rotate.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atomic labelling scheme. Non-H atoms are drawn as 30% probability displacement ellipsoids; H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing of the title compound. H atoms have been omitted for clarity.
1-(1-Benzofuran-2-yl)ethanone O-(4-chlorobenzyl)oxime top
Crystal data top
C17H14ClNO2Z = 2
Mr = 299.74F(000) = 312
Triclinic, P1Dx = 1.404 Mg m3
Hall symbol: -P 1Melting point = 377–378 K
a = 5.8842 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.1173 (6) ÅCell parameters from 3128 reflections
c = 17.2313 (16) Åθ = 2.4–28.9°
α = 93.802 (7)°µ = 0.27 mm1
β = 97.998 (7)°T = 130 K
γ = 95.363 (7)°Lath, colourless
V = 709.19 (10) Å30.50 × 0.40 × 0.05 mm
Data collection top
Agilent Xcalibur Atlas
diffractometer
3407 independent reflections
Radiation source: Enhance (Mo) X-ray Source2817 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 29.0°, θmin = 2.4°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
h = 87
Tmin = 0.783, Tmax = 1.000k = 99
9366 measured reflectionsl = 2223
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-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 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C17H14ClNO2γ = 95.363 (7)°
Mr = 299.74V = 709.19 (10) Å3
Triclinic, P1Z = 2
a = 5.8842 (4) ÅMo Kα radiation
b = 7.1173 (6) ŵ = 0.27 mm1
c = 17.2313 (16) ÅT = 130 K
α = 93.802 (7)°0.50 × 0.40 × 0.05 mm
β = 97.998 (7)°
Data collection top
Agilent Xcalibur Atlas
diffractometer
3407 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
2817 reflections with I > 2σ(I)
Tmin = 0.783, Tmax = 1.000Rint = 0.034
9366 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.10Δρmax = 0.77 e Å3
3407 reflectionsΔρmin = 0.31 e Å3
191 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8938 (2)0.1648 (2)0.67864 (8)0.0185 (3)
C20.6830 (4)0.2349 (3)0.65738 (13)0.0178 (4)
C30.5839 (4)0.2838 (3)0.72112 (13)0.0190 (4)
H30.44040.33500.72100.023*
C40.7371 (4)0.2436 (3)0.78881 (13)0.0188 (4)
C50.7372 (4)0.2580 (3)0.87016 (13)0.0218 (5)
H50.61440.30900.89210.026*
C60.9194 (4)0.1967 (3)0.91800 (13)0.0242 (5)
H60.92090.20540.97330.029*
C71.1032 (4)0.1214 (3)0.88624 (13)0.0228 (5)
H71.22590.07980.92050.027*
C81.1080 (4)0.1070 (3)0.80611 (13)0.0200 (4)
H81.23120.05670.78430.024*
C90.9240 (4)0.1697 (3)0.75924 (12)0.0171 (4)
C100.6054 (4)0.2459 (3)0.57402 (13)0.0190 (4)
C110.3554 (4)0.2650 (4)0.54716 (14)0.0249 (5)
H11A0.34170.38090.52000.037*
H11B0.27320.27120.59280.037*
H11C0.28810.15530.51120.037*
N120.7611 (3)0.2386 (3)0.52841 (10)0.0206 (4)
O130.6618 (3)0.2504 (2)0.44972 (9)0.0224 (4)
C140.8445 (4)0.2641 (3)0.40298 (13)0.0230 (5)
H14A0.92670.14910.40580.028*
H14B0.95640.37510.42310.028*
C150.7438 (4)0.2847 (3)0.31948 (12)0.0188 (4)
C160.5159 (4)0.2194 (3)0.28902 (13)0.0194 (4)
H160.41540.16870.32280.023*
C170.4342 (4)0.2276 (3)0.20982 (13)0.0196 (4)
H170.27900.18250.18930.024*
C180.5821 (4)0.3024 (3)0.16110 (12)0.0205 (4)
C190.8082 (4)0.3733 (3)0.19012 (13)0.0214 (5)
H190.90700.42650.15640.026*
C200.8865 (4)0.3647 (3)0.26924 (13)0.0202 (4)
H201.04030.41410.28980.024*
Cl210.48371 (11)0.30347 (9)0.06126 (3)0.03010 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0128 (7)0.0216 (8)0.0222 (7)0.0061 (6)0.0031 (6)0.0021 (6)
C20.0121 (10)0.0152 (10)0.0266 (11)0.0033 (8)0.0025 (8)0.0025 (8)
C30.0134 (10)0.0183 (10)0.0261 (11)0.0031 (8)0.0039 (8)0.0028 (8)
C40.0146 (10)0.0155 (10)0.0266 (11)0.0015 (8)0.0048 (8)0.0007 (8)
C50.0174 (11)0.0226 (11)0.0263 (11)0.0029 (9)0.0067 (9)0.0006 (9)
C60.0239 (12)0.0281 (12)0.0210 (11)0.0040 (9)0.0033 (9)0.0018 (9)
C70.0176 (11)0.0241 (12)0.0266 (11)0.0037 (9)0.0006 (9)0.0052 (9)
C80.0145 (10)0.0176 (11)0.0283 (11)0.0029 (8)0.0038 (9)0.0020 (8)
C90.0139 (10)0.0148 (10)0.0226 (10)0.0001 (8)0.0045 (8)0.0011 (8)
C100.0164 (10)0.0164 (10)0.0244 (11)0.0037 (8)0.0030 (8)0.0010 (8)
C110.0169 (11)0.0315 (13)0.0267 (11)0.0068 (9)0.0015 (9)0.0032 (9)
N120.0173 (9)0.0251 (10)0.0198 (9)0.0050 (7)0.0011 (7)0.0025 (7)
O130.0158 (8)0.0330 (9)0.0192 (8)0.0062 (6)0.0025 (6)0.0037 (6)
C140.0147 (10)0.0314 (13)0.0239 (11)0.0054 (9)0.0042 (9)0.0021 (9)
C150.0168 (10)0.0170 (11)0.0233 (11)0.0047 (8)0.0036 (8)0.0006 (8)
C160.0159 (10)0.0187 (11)0.0251 (11)0.0037 (8)0.0068 (8)0.0022 (8)
C170.0145 (10)0.0181 (10)0.0259 (11)0.0040 (8)0.0013 (8)0.0003 (8)
C180.0248 (11)0.0174 (11)0.0202 (10)0.0074 (9)0.0041 (9)0.0005 (8)
C190.0206 (11)0.0182 (11)0.0273 (11)0.0027 (8)0.0087 (9)0.0030 (8)
C200.0145 (10)0.0179 (11)0.0278 (11)0.0009 (8)0.0044 (8)0.0014 (8)
Cl210.0352 (4)0.0342 (3)0.0212 (3)0.0077 (3)0.0019 (2)0.0033 (2)
Geometric parameters (Å, º) top
O1—C91.373 (2)C11—H11B0.9800
O1—C21.391 (2)C11—H11C0.9800
C2—C31.354 (3)N12—O131.411 (2)
C2—C101.455 (3)O13—C141.430 (3)
C3—C41.433 (3)C14—C151.500 (3)
C3—H30.9500C14—H14A0.9900
C4—C51.399 (3)C14—H14B0.9900
C4—C91.405 (3)C15—C161.395 (3)
C5—C61.382 (3)C15—C201.399 (3)
C5—H50.9500C16—C171.389 (3)
C6—C71.411 (3)C16—H160.9500
C6—H60.9500C17—C181.386 (3)
C7—C81.382 (3)C17—H170.9500
C7—H70.9500C18—C191.389 (3)
C8—C91.385 (3)C18—Cl211.738 (2)
C8—H80.9500C19—C201.384 (3)
C10—N121.289 (3)C19—H190.9500
C10—C111.501 (3)C20—H200.9500
C11—H11A0.9800
C9—O1—C2105.57 (15)H11A—C11—H11B109.5
C3—C2—O1111.63 (18)C10—C11—H11C109.5
C3—C2—C10130.7 (2)H11A—C11—H11C109.5
O1—C2—C10117.67 (17)H11B—C11—H11C109.5
C2—C3—C4106.82 (19)C10—N12—O13110.10 (17)
C2—C3—H3126.6N12—O13—C14107.89 (15)
C4—C3—H3126.6O13—C14—C15108.84 (17)
C5—C4—C9118.6 (2)O13—C14—H14A109.9
C5—C4—C3135.9 (2)C15—C14—H14A109.9
C9—C4—C3105.50 (19)O13—C14—H14B109.9
C6—C5—C4118.7 (2)C15—C14—H14B109.9
C6—C5—H5120.7H14A—C14—H14B108.3
C4—C5—H5120.7C16—C15—C20118.7 (2)
C5—C6—C7121.3 (2)C16—C15—C14122.46 (19)
C5—C6—H6119.4C20—C15—C14118.80 (19)
C7—C6—H6119.4C17—C16—C15120.7 (2)
C8—C7—C6121.2 (2)C17—C16—H16119.6
C8—C7—H7119.4C15—C16—H16119.6
C6—C7—H7119.4C18—C17—C16119.2 (2)
C7—C8—C9116.6 (2)C18—C17—H17120.4
C7—C8—H8121.7C16—C17—H17120.4
C9—C8—H8121.7C17—C18—C19121.4 (2)
O1—C9—C8125.81 (19)C17—C18—Cl21119.18 (17)
O1—C9—C4110.48 (18)C19—C18—Cl21119.38 (17)
C8—C9—C4123.7 (2)C20—C19—C18118.7 (2)
N12—C10—C2116.27 (19)C20—C19—H19120.7
N12—C10—C11124.8 (2)C18—C19—H19120.7
C2—C10—C11118.90 (18)C19—C20—C15121.3 (2)
C10—C11—H11A109.5C19—C20—H20119.3
C10—C11—H11B109.5C15—C20—H20119.3
C9—O1—C2—C30.5 (2)O1—C2—C10—N1217.9 (3)
C9—O1—C2—C10179.91 (18)C3—C2—C10—C1118.3 (4)
O1—C2—C3—C40.2 (2)O1—C2—C10—C11162.22 (19)
C10—C2—C3—C4179.7 (2)C2—C10—N12—O13179.91 (17)
C2—C3—C4—C5179.0 (2)C11—C10—N12—O130.3 (3)
C2—C3—C4—C90.2 (2)C10—N12—O13—C14173.34 (18)
C9—C4—C5—C60.9 (3)N12—O13—C14—C15177.74 (17)
C3—C4—C5—C6177.7 (2)O13—C14—C15—C1624.9 (3)
C4—C5—C6—C70.2 (3)O13—C14—C15—C20158.05 (19)
C5—C6—C7—C80.3 (4)C20—C15—C16—C172.1 (3)
C6—C7—C8—C90.1 (3)C14—C15—C16—C17174.9 (2)
C2—O1—C9—C8177.8 (2)C15—C16—C17—C180.2 (3)
C2—O1—C9—C40.7 (2)C16—C17—C18—C191.5 (3)
C7—C8—C9—O1178.81 (19)C16—C17—C18—Cl21177.27 (16)
C7—C8—C9—C40.6 (3)C17—C18—C19—C201.3 (3)
C5—C4—C9—O1179.55 (18)Cl21—C18—C19—C20177.53 (16)
C3—C4—C9—O10.6 (2)C18—C19—C20—C150.7 (3)
C5—C4—C9—C81.1 (3)C16—C15—C20—C192.4 (3)
C3—C4—C9—C8177.9 (2)C14—C15—C20—C19174.7 (2)
C3—C2—C10—N12161.5 (2)

Experimental details

Crystal data
Chemical formulaC17H14ClNO2
Mr299.74
Crystal system, space groupTriclinic, P1
Temperature (K)130
a, b, c (Å)5.8842 (4), 7.1173 (6), 17.2313 (16)
α, β, γ (°)93.802 (7), 97.998 (7), 95.363 (7)
V3)709.19 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.50 × 0.40 × 0.05
Data collection
DiffractometerAgilent Xcalibur Atlas
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.783, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
9366, 3407, 2817
Rint0.034
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.137, 1.10
No. of reflections3407
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.77, 0.31

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2009).

 

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
First citationBhandari, K., Srinivas, N., Keshava, S. & Shukla, P. (2009). Eur. J. Med. Chem. 44, 437–447.  Web of Science CrossRef PubMed CAS
First citationChern, J.-H., Lee, C.-C., Chang, C.-S., Lee, Y.-C., Tai, C. L., Lin, Y.-T., Shia, K.-S., Lee, C.-Y. & Shih, S.-R. (2004). Bioorg. Med. Chem. Lett. 14, 5051–5056.  Web of Science CrossRef PubMed CAS
First citationDemirayak, S., Uçucu, Ü., Benkli, K., Gündoğdu-Karaburun, N., Karaburun, A., Akar, D., Karabacak, M. & Kiraz, N. (2002). Il Farmaco, 57, 609–612.  Web of Science CrossRef PubMed CAS
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First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
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First citationKarakurt, A., Dalkara, S., Özalp, M., Özbey, S., Kendi, E. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 421–433.  Web of Science CSD CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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