3-(4-Chloro-phen-yl)-2,1-benzisoxazole-5-carbonyl chloride.

The molecule of the title compound, C(14)H(7)Cl(2)NO(2), is not planar; the dihedral angle between the mean planes of the chloro-phenyl and benzisoxazole rings is 20.32 (7)°. The carbonyl chloride group is twisted with respect to the benzisoxazole ring by 2.5 (1)°. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯Cl hydrogen bond. In the crystal packing, adjacent mol-ecules are linked into dimers by inter-molecular C-H⋯O hydrogen bonds. The dimers are further stacked into columns along the unique axis direction by π-π stacking inter-actions, with a centroid⋯centroid distance of 3.828 (5) Å. Other weak inter-molecular C-H⋯O and C-H⋯Cl inter-actions 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 = 292.11

Monoclinic,

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 (; Oxford Diffraction, 2006 ▶) 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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.126

S = 1.05

2413 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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 ▶).

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

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

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

C14H7Cl2NO2	F000 = 1184
Mr = 292.11	Dx = 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 = 3.8280 (10) Å	θ = 2.2–76.9º
c = 21.000 (4) Å	µ = 4.85 mm−1
β = 100.67 (3)º	T = 100 (2) K
V = 2396.6 (9) Å3	Needle, yellow
Z = 8	0.80 × 0.15 × 0.12 mm

Xcalibur PX κ-geometry diffractometer with CCD Onyx camera	2413 independent reflections
Radiation source: fine-focus sealed tube	2131 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.068
T = 100(2) K	θmax = 76.7º
ω and φ scans	θmin = 4.3º
Absorption correction: analytical(CrysAlis RED; Oxford Diffraction, 2006)	h = −38→21
Tmin = 0.21, Tmax = 0.66	k = −4→4
9609 measured reflections	l = −20→26

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.1002P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.30 e Å−3
2413 reflections	Δρmin = −0.60 e Å−3
173 parameters	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)
Secondary atom site location: difference Fourier map

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
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)

	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)

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)

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

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) ; (ii) ; (iii) .