3-(4-Chloro­phen­yl)-2,1-benzisoxazole-5-carbonyl chloride

Teslenko, Y.; Matiychuk, V.; Obushak, M.; Kinzhybalo, V.; Ślepokura, K.

doi:10.1107/S1600536808037872

organic compounds

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Volume 64| Part 12| December 2008| Page o2420

doi:10.1107/S1600536808037872

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3-(4-Chlorophenyl)-2,1-benzisoxazole-5-carbonyl chloride

Yuriy Teslenko,^a ^* Vasyl Matiychuk,^a Mykola Obushak,^a Vasyl Kinzhybalo ^b and Katarzyna Ślepokura ^b

^aDepartment of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla and Mefodiya 6, Lviv, 79005, Ukraine, and ^bFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland
^*Correspondence e-mail: dangercorp@gmail.com

(Received 29 October 2008; accepted 14 November 2008; online 22 November 2008)

The molecule of the title compound, C₁₄H₇Cl₂NO₂, is not planar; the dihedral angle between the mean planes of the chlorophenyl and benzisoxazole rings is 20.32 (7)°. The carbonyl chloride group is twisted with respect to the benzisoxazole ring by 2.5 (1)°. The molecular conformation is stabilized by an intramolecular C—H⋯Cl hydrogen bond. In the crystal packing, adjacent molecules are linked into dimers by intermolecular C—H⋯O hydrogen bonds. The dimers are further stacked into columns along the unique axis direction by π–π stacking interactions, with a centroid⋯centroid distance of 3.828 (5) Å. Other weak intermolecular C—H⋯O and C—H⋯Cl interactions are also present.

Related literature

For the applications and biological activities of benzo[c]isoxazoles, see: McEvoy et al. (1968 ); Hester et al. (1989 ); Walsh et al. (1990 ); Angibaud et al. (2003 ). For details of the synthesis, see: Davis & Pizzini (1960 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₇Cl₂NO₂
M_r = 292.11
Monoclinic, C 2/c
a = 30.337 (6) Å
b = 3.828 (1) Å
c = 21.000 (4) Å
β = 100.67 (3)°
V = 2396.6 (9) Å³
Z = 8
Cu Kα radiation
μ = 4.85 mm⁻¹
T = 100 (2) K
0.80 × 0.15 × 0.12 mm

Data collection

Oxford Xcalibur PX κ-geometry diffractometer with Onyx CCD camera
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ) T_min = 0.21, T_max = 0.66
9609 measured reflections
2413 independent reflections
2131 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.126
S = 1.05
2413 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cl1	0.95	2.58	3.015 (2)	108
C6—H6⋯O1ⁱ	0.95	2.53	3.378 (2)	149
C9—H9⋯Cl1ⁱⁱ	0.95	2.96	3.813 (2)	150
C13—H13⋯O2ⁱⁱⁱ	0.95	2.69	3.492 (2)	142
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808037872/rz2265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037872/rz2265Isup2.hkl

checkCIF report

Comment top

Our interest in benzo[c]isoxazoles is concerned with their biological activity and their application as precursors of the variety of bioactive compounds (Angibaud et al., 2003; Walsh et al., 1990; Hester et al., 1989; McEvoy et al., 1968). The title compound will be used in our further investigations as a building block for modifications by nucleophiles.

The asymmetric unit of the title compound is shown in Figure 1. The planarity of the molecule is disturbed by intramolecular attractive and repulsive interactions of the C–H···Cl, C–H···O and C–H···H–C types. The dihedral angle between the least-square mean planes of the chlorophenyl and benzisoxazole rings is 20.32 (7)°. The carbonyl chloride group is rotated by 2.5 (1)° with respect to the benzisoxazole ring. An intramolecular C—H···Cl hydrogen bonding interactions is observed (Table 1). The crystal packing (Fig. 2) is governed by intermolecular interactions of the C–H..O type and by π-π stacking interactions. The C–H···O type hydrogen bonds connect adjacent molecules into dimers, forming ten-membered rings of graph set motif R²₂(10) (Bernstein et al., 1995). The dimers are further linked along the unique axis direction by π-π stacking interactions: Cg1···Cg1ⁱ = Cg2···Cg2ⁱ = 3.828 (5) Å (Cg1 and Cg2 are the centroids of the C1/C2/C4–C7 and C8–C13 aromatic rings, respectively; symmetry code: (i) x, 1+y, z); the corresponding perpendicular interplanar distances are 3.429 (4) and 3.475 (4) Å, respectively, and the centroid-centroid offsets are 1.702 (4) and 1.605 (3) Å, respectively. Additionally, two weak C–H···O and C—H···Cl interactions are present in the structure (shown as dotted lines in Figure 2).

Related literature top

For the applications and biological activities of benzo[c]isoxazoles, see: McEvoy et al. (1968); Hester et al. (1989); Walsh et al. (1990); Angibaud et al. (2003). For details of the synthesis, see: Davis & Pizzini (1960). For related literature, see: Bernstein et al. (1995).

Experimental top

To 40 ml of an ethanol solution of potassium hydroxide (4 g, 0.1 mol) p-nitrobenzoic acid (1.67 g, 10 mmol) was added with stirring. Then 5 ml of an ethanol solution of 4-chlorophenylacetonitrile (1.82 g, 12 mmol) was added to the reaction mixture. The suspension was stirred for 4 h at 323 K and left overnight at room temperature. The reaction mixture was poured into 150 ml of water and acidified with hydrochloric acid. The precipitate was isolated by filtration, washed with water and dried. Crude acid was added to a solution of thionyl chloride (1.19 ml, 20 mmol) in benzene (15 ml) and heated under reflux until a clear solution was obtained. Yellow needles of the title compound were obtained by slow cooling of the reaction solution (m.p. 453–454 K; 2 g, yield 70%).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of the title compound viewed along the b axis, showing intermolecular hydrogen bonds (dashed lines) and weak hydrogen interactions (dotted lines). Symmetry codes are as in Table 1.

3-(4-Chlorophenyl)-2,1-benzisoxazole-5-carbonyl chloride top

Crystal data top

C₁₄H₇Cl₂NO₂	F(000) = 1184
M_r = 292.11	D_x = 1.619 Mg m⁻³
Monoclinic, C2/c	Melting point: 453-454 K K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54180 Å
a = 30.337 (6) Å	Cell parameters from 9042 reflections
b = 3.828 (1) Å	θ = 2.2–76.9°
c = 21.000 (4) Å	µ = 4.85 mm⁻¹
β = 100.67 (3)°	T = 100 K
V = 2396.6 (9) Å³	Needle, yellow
Z = 8	0.80 × 0.15 × 0.12 mm

Data collection top

Xcalibur PX κ-geometry diffractometer with CCD Onyx camera	2413 independent reflections
Radiation source: fine-focus sealed tube	2131 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ω and ϕ scans	θ_max = 76.7°, θ_min = 4.3°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −38→21
T_min = 0.21, T_max = 0.66	k = −4→4
9609 measured reflections	l = −20→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.1002P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2413 reflections	Δρ_max = 0.30 e Å⁻³
173 parameters	Δρ_min = −0.60 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00084 (17)

Crystal data top

C₁₄H₇Cl₂NO₂	V = 2396.6 (9) Å³
M_r = 292.11	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 30.337 (6) Å	µ = 4.85 mm⁻¹
b = 3.828 (1) Å	T = 100 K
c = 21.000 (4) Å	0.80 × 0.15 × 0.12 mm
β = 100.67 (3)°

Data collection top

Xcalibur PX κ-geometry diffractometer with CCD Onyx camera	2413 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	2131 reflections with I > 2σ(I)
T_min = 0.21, T_max = 0.66	R_int = 0.068
9609 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
2413 reflections	Δρ_min = −0.60 e Å⁻³
173 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
Cl1	0.226537 (14)	0.66461 (14)	0.17672 (2)	0.0394 (2)
Cl2	0.440884 (15)	0.22145 (13)	0.50018 (2)	0.0379 (2)
O2	0.44488 (4)	0.9282 (4)	0.21086 (6)	0.0344 (3)
O1	0.22228 (5)	0.9426 (5)	0.06384 (7)	0.0531 (4)
N1	0.43252 (5)	1.0756 (5)	0.14821 (8)	0.0373 (4)
C3	0.40860 (5)	0.8178 (5)	0.23358 (8)	0.0276 (4)
C1	0.38838 (6)	1.0480 (5)	0.13517 (8)	0.0305 (4)
C2	0.37105 (5)	0.8870 (5)	0.18709 (8)	0.0272 (4)
C7	0.35923 (6)	1.1558 (5)	0.07744 (9)	0.0348 (4)
H7	0.3706	1.2660	0.0433	0.042*
C6	0.31470 (6)	1.0960 (5)	0.07275 (8)	0.0341 (4)
H6	0.2946	1.1668	0.0347	0.041*
C5	0.29704 (5)	0.9272 (5)	0.12426 (8)	0.0286 (4)
C4	0.32426 (5)	0.8258 (5)	0.18041 (8)	0.0277 (4)
H4	0.3122	0.7171	0.2141	0.033*
C8	0.41646 (5)	0.6636 (5)	0.29788 (8)	0.0277 (4)
C9	0.38161 (5)	0.6433 (5)	0.33305 (8)	0.0312 (4)
H9	0.3526	0.7261	0.3143	0.037*
C10	0.38894 (5)	0.5044 (5)	0.39469 (8)	0.0325 (4)
H10	0.3652	0.4905	0.4183	0.039*
C11	0.43141 (6)	0.3854 (5)	0.42168 (8)	0.0297 (4)
C12	0.46655 (5)	0.3991 (5)	0.38806 (8)	0.0316 (4)
H12	0.4954	0.3148	0.4072	0.038*
C13	0.45895 (5)	0.5378 (5)	0.32618 (8)	0.0314 (4)
H13	0.4828	0.5478	0.3026	0.038*
C15	0.24813 (6)	0.8697 (5)	0.11157 (9)	0.0338 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0264 (2)	0.0502 (4)	0.0408 (3)	−0.00458 (17)	0.00416 (19)	0.00756 (19)
Cl2	0.0379 (3)	0.0451 (3)	0.0291 (3)	0.00141 (18)	0.00193 (19)	0.00423 (17)
O2	0.0246 (6)	0.0479 (8)	0.0318 (6)	−0.0032 (5)	0.0085 (5)	0.0005 (5)
O1	0.0335 (7)	0.0836 (13)	0.0381 (8)	−0.0006 (8)	−0.0038 (6)	0.0134 (8)
N1	0.0319 (8)	0.0487 (10)	0.0329 (8)	−0.0029 (7)	0.0102 (6)	0.0036 (7)
C3	0.0230 (7)	0.0322 (9)	0.0288 (8)	−0.0031 (6)	0.0074 (6)	−0.0050 (6)
C1	0.0315 (8)	0.0325 (9)	0.0296 (8)	−0.0017 (7)	0.0112 (7)	−0.0012 (7)
C2	0.0268 (8)	0.0288 (9)	0.0268 (8)	−0.0006 (6)	0.0069 (6)	−0.0022 (6)
C7	0.0394 (9)	0.0377 (10)	0.0292 (9)	0.0014 (7)	0.0116 (7)	0.0045 (7)
C6	0.0373 (9)	0.0380 (10)	0.0268 (8)	0.0056 (7)	0.0050 (7)	0.0033 (7)
C5	0.0275 (8)	0.0311 (9)	0.0271 (8)	0.0003 (6)	0.0045 (6)	−0.0016 (7)
C4	0.0250 (8)	0.0327 (9)	0.0256 (8)	−0.0003 (6)	0.0054 (6)	0.0001 (6)
C8	0.0228 (7)	0.0328 (9)	0.0270 (8)	−0.0023 (6)	0.0035 (6)	−0.0034 (6)
C9	0.0211 (7)	0.0429 (10)	0.0293 (8)	0.0034 (7)	0.0037 (6)	−0.0020 (7)
C10	0.0232 (7)	0.0445 (11)	0.0298 (8)	0.0001 (7)	0.0051 (6)	−0.0034 (7)
C11	0.0290 (8)	0.0323 (9)	0.0268 (8)	−0.0007 (7)	0.0028 (6)	−0.0023 (7)
C12	0.0231 (7)	0.0381 (10)	0.0320 (8)	0.0036 (7)	0.0006 (6)	−0.0013 (7)
C13	0.0197 (7)	0.0416 (10)	0.0331 (8)	−0.0006 (7)	0.0054 (6)	−0.0041 (7)
C15	0.0293 (8)	0.0410 (10)	0.0296 (8)	0.0010 (7)	0.0016 (7)	0.0007 (8)

Geometric parameters (Å, º) top

Cl1—C15	1.803 (2)	C6—H6	0.9500
Cl2—C11	1.7373 (18)	C5—C4	1.365 (2)
O2—C3	1.3461 (19)	C5—C15	1.475 (2)
O2—N1	1.417 (2)	C4—H4	0.9500
O1—C15	1.186 (2)	C8—C9	1.400 (2)
N1—C1	1.320 (2)	C8—C13	1.401 (2)
C3—C2	1.382 (2)	C9—C10	1.379 (3)
C3—C8	1.452 (2)	C9—H9	0.9500
C1—C7	1.423 (3)	C10—C11	1.385 (2)
C1—C2	1.434 (2)	C10—H10	0.9500
C2—C4	1.420 (2)	C11—C12	1.384 (2)
C7—C6	1.356 (3)	C12—C13	1.383 (2)
C7—H7	0.9500	C12—H12	0.9500
C6—C5	1.446 (2)	C13—H13	0.9500

C3—O2—N1	111.15 (13)	C2—C4—H4	120.9
C1—N1—O2	104.15 (13)	C9—C8—C13	118.86 (16)
O2—C3—C2	108.11 (15)	C9—C8—C3	120.21 (15)
O2—C3—C8	116.92 (15)	C13—C8—C3	120.92 (15)
C2—C3—C8	134.97 (15)	C10—C9—C8	120.70 (16)
N1—C1—C7	126.85 (16)	C10—C9—H9	119.6
N1—C1—C2	112.17 (16)	C8—C9—H9	119.6
C7—C1—C2	120.98 (15)	C9—C10—C11	119.16 (16)
C3—C2—C4	135.77 (16)	C9—C10—H10	120.4
C3—C2—C1	104.42 (14)	C11—C10—H10	120.4
C4—C2—C1	119.77 (16)	C12—C11—C10	121.64 (16)
C6—C7—C1	117.82 (16)	C12—C11—Cl2	119.33 (14)
C6—C7—H7	121.1	C10—C11—Cl2	119.02 (13)
C1—C7—H7	121.1	C13—C12—C11	118.92 (15)
C7—C6—C5	121.57 (17)	C13—C12—H12	120.5
C7—C6—H6	119.2	C11—C12—H12	120.5
C5—C6—H6	119.2	C12—C13—C8	120.72 (15)
C4—C5—C6	121.66 (15)	C12—C13—H13	119.6
C4—C5—C15	122.78 (16)	C8—C13—H13	119.6
C6—C5—C15	115.56 (16)	O1—C15—C5	127.12 (18)
C5—C4—C2	118.18 (15)	O1—C15—Cl1	117.88 (15)
C5—C4—H4	120.9	C5—C15—Cl1	115.00 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1	0.95	2.58	3.015 (2)	108
C6—H6···O1ⁱ	0.95	2.53	3.378 (2)	149
C9—H9···Cl1ⁱⁱ	0.95	2.96	3.813 (2)	150
C13—H13···O2ⁱⁱⁱ	0.95	2.69	3.492 (2)	142

Symmetry codes: (i) −x+1/2, −y+5/2, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₇Cl₂NO₂
M_r	292.11
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	30.337 (6), 3.828 (1), 21.000 (4)
β (°)	100.67 (3)
V (Å³)	2396.6 (9)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	4.85
Crystal size (mm)	0.80 × 0.15 × 0.12

Data collection
Diffractometer	Xcalibur PX κ-geometry diffractometer with CCD Onyx camera
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.21, 0.66
No. of measured, independent and observed [I > 2σ(I)] reflections	9609, 2413, 2131
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.126, 1.05
No. of reflections	2413
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.60

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2005), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1	0.95	2.58	3.015 (2)	108.2
C6—H6···O1ⁱ	0.95	2.53	3.378 (2)	149.2
C9—H9···Cl1ⁱⁱ	0.95	2.96	3.813 (2)	149.5
C13—H13···O2ⁱⁱⁱ	0.95	2.69	3.492 (2)	142.3

Symmetry codes: (i) −x+1/2, −y+5/2, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, y, −z+1/2.

References

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doi:10.1107/S1600536808037872

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