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

Kosmalski, T.; Gzella, A.K.

doi:10.1107/S1600536812042675

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3178

doi:10.1107/S1600536812042675

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

Tomasz Kosmalski ^a and Andrzej K. Gzella ^b,^c ^*

^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 ); 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_r = 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 ) 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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.137
S = 1.10
3407 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks I, publication_text. DOI: 10.1107/S1600536812042675/bt6848sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812042675/bt6848Isup3.cml

checkCIF report

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).

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

	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.
	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

C₁₇H₁₄ClNO₂	Z = 2
M_r = 299.74	F(000) = 312
Triclinic, P1	D_x = 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

Data collection top

Agilent Xcalibur Atlas diffractometer	3407 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2817 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 29.0°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	h = −8→7
T_min = 0.783, T_max = 1.000	k = −9→9
9366 measured reflections	l = −22→23

Refinement top

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(F_o²) + (0.0487P)² + 0.7613P] where P = (F_o² + 2F_c²)/3
3407 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₇H₁₄ClNO₂	γ = 95.363 (7)°
M_r = 299.74	V = 709.19 (10) Å³
Triclinic, P1	Z = 2
a = 5.8842 (4) Å	Mo Kα radiation
b = 7.1173 (6) Å	µ = 0.27 mm⁻¹
c = 17.2313 (16) Å	T = 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)
T_min = 0.783, T_max = 1.000	R_int = 0.034
9366 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.10	Δρ_max = 0.77 e Å⁻³
3407 reflections	Δρ_min = −0.31 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄ClNO₂
M_r	299.74
Crystal system, space group	Triclinic, 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)
V (Å³)	709.19 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.50 × 0.40 × 0.05

Data collection
Diffractometer	Agilent Xcalibur Atlas diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.783, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9366, 3407, 2817
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.137, 1.10
No. of reflections	3407
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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