3-Chloro-methyl-6,7-dimethyl-1,2-benz-oxazole.

In the title compound, C(10)H(10)ClNO, the benzoisoxazole ring is almost planar (r.m.s. deviation = 0.0121 Å) and the chloro substituent in the side chain is anti-clinal relative to the N-C bond of the isoxazole ring. In the crystal, adjacent mol-ecules are linked via a pair of weak C-H⋯N hydrogen bonds, forming dimers through a cyclic R(2) (2)(8) association.

Related literature

For the biological and chemical applications of benzoxazoles, see: Ha et al. (2010 ▶); Kayalvizhi et al. (2011 ▶); Krishnaiah et al. (2009 ▶); Qu et al. (2008 ▶); Raju et al. (2002 ▶); Veerareddy et al. (2011 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H10ClNO

M = 195.64

Monoclinic,

a = 20.4938 (15) Å

b = 4.1237 (3) Å

c = 24.6361 (18) Å

β = 114.151 (3)°

V = 1899.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.36 mm−1

T = 295 K

0.20 × 0.15 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.932, T max = 0.948

8155 measured reflections

1748 independent reflections

1396 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.06

1748 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039700/zs2231sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039700/zs2231Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039700/zs2231Isup3.cml

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

C10H10ClNO	F(000) = 816
Mr = 195.64	Dx = 1.368 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3599 reflections
a = 20.4938 (15) Å	θ = 2.2–25.7°
b = 4.1237 (3) Å	µ = 0.36 mm−1
c = 24.6361 (18) Å	T = 295 K
β = 114.151 (3)°	Block, colourless
V = 1899.8 (2) Å3	0.20 × 0.15 × 0.15 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	1748 independent reflections
Radiation source: fine-focus sealed tube	1396 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −24→24
Tmin = 0.932, Tmax = 0.948	k = −4→4
8155 measured reflections	l = −29→29

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0575P)2 + 1.2791P] where P = (Fo2 + 2Fc2)/3
1748 reflections	(Δ/σ)max < 0.001
120 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl	0.36216 (3)	0.4407 (2)	0.14499 (3)	0.0810 (3)
O1	0.11696 (8)	0.2766 (4)	0.03641 (6)	0.0579 (4)
C3A	0.19031 (10)	0.5502 (5)	0.11668 (8)	0.0449 (4)
C4	0.20916 (11)	0.6941 (5)	0.17240 (9)	0.0535 (5)
H4	0.2530	0.7972	0.1919	0.064*
C7	0.07354 (10)	0.3861 (5)	0.11299 (8)	0.0490 (5)
C7A	0.12460 (10)	0.4049 (5)	0.08966 (8)	0.0464 (5)
C6	0.09376 (11)	0.5243 (5)	0.16895 (9)	0.0529 (5)
C3	0.22228 (11)	0.5014 (5)	0.07591 (9)	0.0492 (5)
C5	0.16064 (12)	0.6770 (5)	0.19698 (9)	0.0560 (5)
H5	0.1723	0.7708	0.2341	0.067*
N2	0.18083 (10)	0.3418 (5)	0.02923 (8)	0.0610 (5)
C8	0.00258 (12)	0.2276 (6)	0.07915 (10)	0.0667 (6)
H8A	−0.0058	0.0668	0.1038	0.100*
H8B	0.0026	0.1261	0.0441	0.100*
H8C	−0.0345	0.3882	0.0679	0.100*
C10	0.29367 (12)	0.6064 (6)	0.08013 (10)	0.0620 (6)
H10A	0.2966	0.8413	0.0816	0.074*
H10B	0.3001	0.5344	0.0452	0.074*
C9	0.04460 (14)	0.5113 (7)	0.20055 (11)	0.0761 (7)
H9A	−0.0006	0.6070	0.1759	0.114*
H9B	0.0656	0.6289	0.2373	0.114*
H9C	0.0374	0.2895	0.2086	0.114*

	U11	U22	U33	U12	U13	U23
Cl	0.0488 (4)	0.1014 (6)	0.0848 (5)	0.0015 (3)	0.0190 (3)	0.0112 (4)
O1	0.0509 (8)	0.0716 (10)	0.0462 (7)	−0.0017 (7)	0.0147 (6)	−0.0086 (7)
C3A	0.0457 (10)	0.0404 (10)	0.0441 (10)	0.0069 (8)	0.0137 (8)	0.0031 (8)
C4	0.0503 (11)	0.0513 (12)	0.0505 (11)	0.0030 (9)	0.0123 (9)	−0.0051 (9)
C7	0.0434 (10)	0.0489 (12)	0.0491 (11)	0.0097 (9)	0.0134 (9)	0.0077 (9)
C7A	0.0471 (10)	0.0449 (11)	0.0403 (9)	0.0087 (8)	0.0107 (8)	0.0016 (8)
C6	0.0528 (12)	0.0534 (12)	0.0510 (11)	0.0142 (9)	0.0196 (9)	0.0066 (9)
C3	0.0498 (11)	0.0469 (11)	0.0497 (11)	0.0075 (9)	0.0191 (9)	0.0045 (9)
C5	0.0624 (13)	0.0571 (13)	0.0445 (10)	0.0093 (10)	0.0178 (10)	−0.0053 (9)
N2	0.0569 (11)	0.0739 (13)	0.0522 (10)	0.0036 (9)	0.0225 (9)	−0.0040 (9)
C8	0.0487 (12)	0.0770 (16)	0.0676 (14)	−0.0030 (11)	0.0170 (10)	0.0022 (12)
C10	0.0605 (13)	0.0608 (14)	0.0678 (14)	0.0006 (11)	0.0295 (11)	0.0058 (11)
C9	0.0754 (16)	0.0931 (19)	0.0708 (15)	0.0116 (14)	0.0411 (13)	0.0039 (13)

Cl—C10	1.776 (2)	C6—C9	1.505 (3)
O1—C7A	1.363 (2)	C3—N2	1.295 (3)
O1—N2	1.417 (2)	C3—C10	1.488 (3)
C3A—C7A	1.372 (3)	C5—H5	0.9300
C3A—C4	1.397 (3)	C8—H8A	0.9600
C3A—C3	1.420 (3)	C8—H8B	0.9600
C4—C5	1.361 (3)	C8—H8C	0.9600
C4—H4	0.9300	C10—H10A	0.9700
C7—C7A	1.387 (3)	C10—H10B	0.9700
C7—C6	1.389 (3)	C9—H9A	0.9600
C7—C8	1.498 (3)	C9—H9B	0.9600
C6—C5	1.406 (3)	C9—H9C	0.9600
C7A—O1—N2	107.37 (15)	C6—C5—H5	118.4
C7A—C3A—C4	118.97 (18)	C3—N2—O1	106.82 (16)
C7A—C3A—C3	103.89 (17)	C7—C8—H8A	109.5
C4—C3A—C3	137.13 (19)	C7—C8—H8B	109.5
C5—C4—C3A	117.15 (19)	H8A—C8—H8B	109.5
C5—C4—H4	121.4	C7—C8—H8C	109.5
C3A—C4—H4	121.4	H8A—C8—H8C	109.5
C7A—C7—C6	114.78 (18)	H8B—C8—H8C	109.5
C7A—C7—C8	121.25 (18)	C3—C10—Cl	110.08 (15)
C6—C7—C8	123.97 (19)	C3—C10—H10A	109.6
O1—C7A—C3A	109.88 (17)	Cl—C10—H10A	109.6
O1—C7A—C7	124.63 (18)	C3—C10—H10B	109.6
C3A—C7A—C7	125.48 (18)	Cl—C10—H10B	109.6
C7—C6—C5	120.40 (19)	H10A—C10—H10B	108.2
C7—C6—C9	120.5 (2)	C6—C9—H9A	109.5
C5—C6—C9	119.09 (19)	C6—C9—H9B	109.5
N2—C3—C3A	112.04 (18)	H9A—C9—H9B	109.5
N2—C3—C10	118.61 (19)	C6—C9—H9C	109.5
C3A—C3—C10	129.35 (19)	H9A—C9—H9C	109.5
C4—C5—C6	123.19 (19)	H9B—C9—H9C	109.5
C4—C5—H5	118.4
C7A—C3A—C4—C5	0.8 (3)	C7A—C7—C6—C9	−177.88 (19)
C3—C3A—C4—C5	−178.2 (2)	C8—C7—C6—C9	2.2 (3)
N2—O1—C7A—C3A	0.2 (2)	C7A—C3A—C3—N2	−0.4 (2)
N2—O1—C7A—C7	−178.95 (17)	C4—C3A—C3—N2	178.7 (2)
C4—C3A—C7A—O1	−179.26 (17)	C7A—C3A—C3—C10	179.5 (2)
C3—C3A—C7A—O1	0.1 (2)	C4—C3A—C3—C10	−1.4 (4)
C4—C3A—C7A—C7	−0.1 (3)	C3A—C4—C5—C6	−0.2 (3)
C3—C3A—C7A—C7	179.25 (18)	C7—C6—C5—C4	−1.2 (3)
C6—C7—C7A—O1	177.83 (18)	C9—C6—C5—C4	178.5 (2)
C8—C7—C7A—O1	−2.3 (3)	C3A—C3—N2—O1	0.5 (2)
C6—C7—C7A—C3A	−1.2 (3)	C10—C3—N2—O1	−179.36 (17)
C8—C7—C7A—C3A	178.7 (2)	C7A—O1—N2—C3	−0.5 (2)
C7A—C7—C6—C5	1.8 (3)	N2—C3—C10—Cl	−121.31 (19)
C8—C7—C6—C5	−178.1 (2)	C3A—C3—C10—Cl	58.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···N2i	0.97	2.55	3.479 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯N2i	0.97	2.55	3.479 (3)	160

Symmetry code: (i) .