3-[Chloro-(phen-yl)meth-yl]-6-methyl-1,2-benzoxazole.

The title compound, C(15)H(12)ClNO, is a functionalized 1,2-benzoxazole with a chloro-(phen-yl)methyl substituent. The mol-ecule is V-shaped, the dihedral angle between the mean plane of the 1,2-benzoxazole system [maximum deviation = 0.023 (3) Å for the N atom] and the phenyl ring being 70.33 (14)°. There are no hydrogen-bonding inter-actions in the crystal structure, which is stabilized by van der Waals inter-actions only.

Related literature

For the synthesis of the title compound, see: Veerareddy et al. (2011 ▶). For related structures, see: Atovmyan & Aliev (1994 ▶); Hu et al. (2009 ▶); Korlyukov et al. (2003 ▶).

Experimental

Crystal data

C15H12ClNO

M = 257.71

Monoclinic,

a = 13.2075 (8) Å

b = 6.5888 (4) Å

c = 15.1224 (8) Å

β = 103.738 (3)°

V = 1278.33 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.919, T max = 0.945

10507 measured reflections

2087 independent reflections

1621 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.125

S = 1.06

2087 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 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 ▶) and Mercury (Macrae et al., 2008) ▶; software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042462/su2326sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042462/su2326Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042462/su2326Isup3.cml

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

C15H12ClNO	F(000) = 536
Mr = 257.71	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.2075 (8) Å	θ = 20–30°
b = 6.5888 (4) Å	µ = 0.29 mm−1
c = 15.1224 (8) Å	T = 293 K
β = 103.738 (3)°	Block, colourless
V = 1278.33 (13) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2087 independent reflections
Radiation source: fine-focus sealed tube	1621 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scan	θmax = 24.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.919, Tmax = 0.945	k = −5→7
10507 measured reflections	l = −17→17

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) = 0.125	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.7285P] where P = (Fo2 + 2Fc2)/3
2087 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
C14	0.3858 (2)	0.3538 (4)	0.10340 (19)	0.0625 (7)
H14	0.3663	0.4825	0.0803	0.075*
C15	0.33247 (19)	0.2630 (4)	0.16026 (17)	0.0514 (6)
H15	0.2771	0.3303	0.1756	0.062*
C10	0.36083 (17)	0.0718 (3)	0.19482 (15)	0.0426 (6)
C11	0.44364 (18)	−0.0247 (4)	0.17192 (16)	0.0512 (6)
H11	0.4639	−0.1530	0.1953	0.061*
C12	0.4965 (2)	0.0676 (5)	0.11477 (18)	0.0614 (7)
H12	0.5521	0.0012	0.0995	0.074*
C13	0.4678 (2)	0.2562 (5)	0.08037 (18)	0.0637 (8)
H13	0.5035	0.3181	0.0416	0.076*
C9	0.30211 (18)	−0.0408 (4)	0.25392 (16)	0.0499 (6)
H9	0.3434	−0.1605	0.2783	0.060*
C3	0.19728 (18)	−0.1135 (3)	0.20317 (16)	0.0453 (6)
C3A	0.10029 (17)	−0.0106 (3)	0.17045 (15)	0.0407 (5)
C4	0.05889 (18)	0.1827 (4)	0.17530 (16)	0.0474 (6)
H4	0.0998	0.2874	0.2060	0.057*
C5	−0.04334 (19)	0.2133 (4)	0.13360 (17)	0.0512 (6)
H5	−0.0716	0.3417	0.1366	0.061*
C6	−0.10804 (18)	0.0600 (4)	0.08627 (16)	0.0486 (6)
C7	−0.06762 (19)	−0.1303 (4)	0.08068 (17)	0.0526 (6)
H7	−0.1082	−0.2348	0.0494	0.063*
C7A	0.03587 (19)	−0.1596 (3)	0.12364 (17)	0.0476 (6)
C8	−0.2204 (2)	0.1048 (5)	0.0429 (2)	0.0708 (8)
H8A	−0.2352	0.2441	0.0536	0.106*
H8B	−0.2642	0.0181	0.0687	0.106*
H8C	−0.2336	0.0809	−0.0215	0.106*
N2	0.19137 (18)	−0.3037 (3)	0.17984 (18)	0.0657 (6)
O1	0.08903 (15)	−0.3377 (3)	0.12767 (15)	0.0693 (6)
Cl	0.28938 (6)	0.11252 (13)	0.34931 (5)	0.0704 (3)

	U11	U22	U33	U12	U13	U23
C14	0.0699 (18)	0.0508 (17)	0.0611 (16)	−0.0066 (14)	0.0044 (14)	0.0094 (13)
C15	0.0511 (14)	0.0432 (15)	0.0587 (15)	0.0055 (11)	0.0106 (11)	0.0002 (12)
C10	0.0392 (12)	0.0423 (14)	0.0416 (12)	0.0019 (10)	0.0006 (9)	−0.0024 (10)
C11	0.0486 (14)	0.0475 (15)	0.0531 (14)	0.0081 (12)	0.0031 (11)	−0.0021 (12)
C12	0.0488 (15)	0.079 (2)	0.0567 (16)	0.0005 (14)	0.0144 (12)	−0.0122 (15)
C13	0.0619 (17)	0.078 (2)	0.0519 (15)	−0.0193 (15)	0.0139 (13)	0.0000 (15)
C9	0.0551 (15)	0.0430 (14)	0.0513 (14)	0.0105 (11)	0.0120 (11)	0.0057 (11)
C3	0.0534 (14)	0.0350 (13)	0.0504 (13)	0.0023 (10)	0.0179 (11)	0.0070 (10)
C3A	0.0484 (13)	0.0326 (12)	0.0441 (12)	−0.0027 (10)	0.0169 (10)	0.0027 (10)
C4	0.0526 (14)	0.0376 (14)	0.0511 (14)	−0.0020 (11)	0.0103 (11)	−0.0060 (11)
C5	0.0556 (15)	0.0424 (15)	0.0569 (14)	0.0056 (12)	0.0158 (12)	−0.0026 (12)
C6	0.0458 (13)	0.0564 (17)	0.0450 (13)	−0.0035 (12)	0.0137 (10)	0.0013 (11)
C7	0.0540 (15)	0.0498 (16)	0.0560 (15)	−0.0153 (12)	0.0173 (12)	−0.0054 (12)
C7A	0.0579 (15)	0.0313 (13)	0.0572 (14)	−0.0044 (11)	0.0207 (12)	0.0029 (11)
C8	0.0540 (16)	0.080 (2)	0.0760 (19)	−0.0010 (14)	0.0105 (14)	−0.0066 (16)
N2	0.0642 (15)	0.0356 (13)	0.0970 (18)	0.0053 (10)	0.0186 (13)	0.0041 (12)
O1	0.0672 (12)	0.0324 (10)	0.1063 (16)	−0.0036 (9)	0.0168 (11)	−0.0070 (10)
Cl	0.0770 (5)	0.0849 (6)	0.0506 (4)	−0.0038 (4)	0.0177 (3)	−0.0093 (3)

C14—C15	1.371 (4)	C3—C3A	1.430 (3)
C14—C13	1.374 (4)	C3A—C7A	1.380 (3)
C14—H14	0.9300	C3A—C4	1.395 (3)
C15—C10	1.381 (3)	C4—C5	1.363 (3)
C15—H15	0.9300	C4—H4	0.9300
C10—C11	1.378 (3)	C5—C6	1.404 (4)
C10—C9	1.510 (3)	C5—H5	0.9300
C11—C12	1.375 (4)	C6—C7	1.374 (4)
C11—H11	0.9300	C6—C8	1.502 (4)
C12—C13	1.365 (4)	C7—C7A	1.380 (3)
C12—H12	0.9300	C7—H7	0.9300
C13—H13	0.9300	C7A—O1	1.361 (3)
C9—C3	1.494 (3)	C8—H8A	0.9600
C9—Cl	1.801 (2)	C8—H8B	0.9600
C9—H9	0.9800	C8—H8C	0.9600
C3—N2	1.299 (3)	N2—O1	1.412 (3)
C15—C14—C13	120.5 (3)	C7A—C3A—C4	118.4 (2)
C15—C14—H14	119.7	C7A—C3A—C3	103.5 (2)
C13—C14—H14	119.7	C4—C3A—C3	138.2 (2)
C14—C15—C10	120.1 (2)	C5—C4—C3A	118.0 (2)
C14—C15—H15	119.9	C5—C4—H4	121.0
C10—C15—H15	119.9	C3A—C4—H4	121.0
C11—C10—C15	119.1 (2)	C4—C5—C6	123.0 (2)
C11—C10—C9	118.2 (2)	C4—C5—H5	118.5
C15—C10—C9	122.7 (2)	C6—C5—H5	118.5
C12—C11—C10	120.3 (3)	C7—C6—C5	119.3 (2)
C12—C11—H11	119.8	C7—C6—C8	120.7 (2)
C10—C11—H11	119.8	C5—C6—C8	120.0 (2)
C13—C12—C11	120.4 (2)	C6—C7—C7A	117.0 (2)
C13—C12—H12	119.8	C6—C7—H7	121.5
C11—C12—H12	119.8	C7A—C7—H7	121.5
C12—C13—C14	119.6 (3)	O1—C7A—C3A	110.0 (2)
C12—C13—H13	120.2	O1—C7A—C7	125.8 (2)
C14—C13—H13	120.2	C3A—C7A—C7	124.3 (2)
C3—C9—C10	113.4 (2)	C6—C8—H8A	109.5
C3—C9—Cl	109.88 (16)	C6—C8—H8B	109.5
C10—C9—Cl	110.95 (17)	H8A—C8—H8B	109.5
C3—C9—H9	107.5	C6—C8—H8C	109.5
C10—C9—H9	107.5	H8A—C8—H8C	109.5
Cl—C9—H9	107.5	H8B—C8—H8C	109.5
N2—C3—C3A	111.9 (2)	C3—N2—O1	107.0 (2)
N2—C3—C9	116.0 (2)	C7A—O1—N2	107.68 (18)
C3A—C3—C9	132.1 (2)
C13—C14—C15—C10	−0.1 (4)	C9—C3—C3A—C4	−5.6 (5)
C14—C15—C10—C11	0.5 (4)	C7A—C3A—C4—C5	0.2 (3)
C14—C15—C10—C9	−176.9 (2)	C3—C3A—C4—C5	−178.3 (2)
C15—C10—C11—C12	−0.6 (3)	C3A—C4—C5—C6	−0.1 (4)
C9—C10—C11—C12	176.9 (2)	C4—C5—C6—C7	−0.3 (4)
C10—C11—C12—C13	0.3 (4)	C4—C5—C6—C8	179.3 (2)
C11—C12—C13—C14	0.2 (4)	C5—C6—C7—C7A	0.6 (3)
C15—C14—C13—C12	−0.3 (4)	C8—C6—C7—C7A	−179.0 (2)
C11—C10—C9—C3	−106.5 (2)	C4—C3A—C7A—O1	−178.9 (2)
C15—C10—C9—C3	71.0 (3)	C3—C3A—C7A—O1	0.1 (3)
C11—C10—C9—Cl	129.31 (19)	C4—C3A—C7A—C7	0.2 (4)
C15—C10—C9—Cl	−53.2 (3)	C3—C3A—C7A—C7	179.1 (2)
C10—C9—C3—N2	100.1 (3)	C6—C7—C7A—O1	178.3 (2)
Cl—C9—C3—N2	−135.1 (2)	C6—C7—C7A—C3A	−0.6 (4)
C10—C9—C3—C3A	−76.4 (3)	C3A—C3—N2—O1	1.3 (3)
Cl—C9—C3—C3A	48.4 (3)	C9—C3—N2—O1	−175.9 (2)
N2—C3—C3A—C7A	−0.9 (3)	C3A—C7A—O1—N2	0.7 (3)
C9—C3—C3A—C7A	175.7 (2)	C7—C7A—O1—N2	−178.4 (2)
N2—C3—C3A—C4	177.7 (3)	C3—N2—O1—C7A	−1.2 (3)