3-Anilinomethyl-5-chloro-1,3--benzoxazol-2(3H)-one.

In the title compound, C(14)H(11)ClN(2)O(2), the 2,3-dihydro-1,3-benzoxazole ring system is essentially planar [maximum deviation = 0.009 (2) Å] and makes a dihedral angle of 79.15 (7)° with the phenyl ring. Inter-molecular N-H⋯O and weak C-H⋯Cl hydrogen bonds occur in the crystal structure.

Related literature

For the synthesis and biological activity of compounds with a benzoxazolone nucleus, see; Varma & Nobles (1968 ▶); Courtois et al. (2004 ▶); Deng et al. (2006 ▶); Ivanova et al. (2007 ▶); Koksal et al. (2002 ▶, 2005 ▶); Onkol et al. (2001 ▶); Soyer et al. (2005 ▶); Ucar et al. (1998 ▶); Unlu et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Aydın et al. (2004 ▶).

Experimental

Crystal data

C14H11ClN2O2

M = 274.70

Monoclinic,

a = 9.7379 (5) Å

b = 12.4797 (7) Å

c = 10.2392 (7) Å

β = 93.129 (5)°

V = 1242.48 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.80 × 0.48 × 0.26 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.837, T max = 0.924

20574 measured reflections

3051 independent reflections

2544 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.106

S = 1.07

3051 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017709/xu5511sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017709/xu5511Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017709/xu5511Isup3.cml

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

C14H11ClN2O2	F(000) = 568
Mr = 274.70	Dx = 1.469 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 27572 reflections
a = 9.7379 (5) Å	θ = 2.1–28.6°
b = 12.4797 (7) Å	µ = 0.31 mm−1
c = 10.2392 (7) Å	T = 296 K
β = 93.129 (5)°	Prism, colourless
V = 1242.48 (13) Å3	0.80 × 0.48 × 0.26 mm
Z = 4

Stoe IPDS 2 diffractometer	3051 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2544 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.046
Detector resolution: 6.67 pixels mm-1	θmax = 28.2°, θmin = 2.6°
ω scans	h = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −16→16
Tmin = 0.837, Tmax = 0.924	l = −13→13
20574 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.2748P] where P = (Fo2 + 2Fc2)/3
3051 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.37199 (5)	0.42730 (6)	−0.40607 (5)	0.0887 (2)
O1	0.61747 (10)	0.34298 (10)	0.11087 (11)	0.0535 (3)
O2	0.52561 (13)	0.24080 (12)	0.26644 (11)	0.0679 (4)
N1	0.41738 (11)	0.26396 (10)	0.06103 (11)	0.0428 (4)
N2	0.16989 (12)	0.24829 (12)	0.04683 (12)	0.0508 (4)
C1	0.45104 (13)	0.32285 (11)	−0.04809 (13)	0.0392 (4)
C2	0.38425 (14)	0.33757 (13)	−0.16827 (14)	0.0454 (4)
C3	0.45056 (16)	0.40463 (14)	−0.25277 (15)	0.0520 (5)
C4	0.57449 (16)	0.45354 (13)	−0.22095 (18)	0.0553 (5)
C5	0.64095 (15)	0.43708 (13)	−0.09935 (17)	0.0539 (5)
C6	0.57568 (14)	0.37153 (12)	−0.01549 (15)	0.0447 (4)
C7	0.51813 (15)	0.27708 (13)	0.15798 (15)	0.0495 (5)
C8	0.29647 (15)	0.19414 (13)	0.06944 (15)	0.0479 (5)
C9	0.11468 (13)	0.31842 (12)	0.13447 (13)	0.0422 (4)
C10	0.17189 (15)	0.33453 (13)	0.26004 (14)	0.0475 (4)
C11	0.10954 (17)	0.40404 (15)	0.34387 (16)	0.0565 (5)
C12	−0.00743 (18)	0.45947 (15)	0.30515 (19)	0.0624 (6)
C13	−0.06427 (19)	0.44406 (16)	0.1809 (2)	0.0659 (6)
C14	−0.00497 (17)	0.37461 (15)	0.09612 (16)	0.0567 (5)
H2	0.30060	0.30500	−0.19140	0.0550*
H2A	0.12430	0.23690	−0.02610	0.0610*
H4	0.61400	0.49800	−0.28140	0.0660*
H5	0.72520	0.46880	−0.07610	0.0650*
H8A	0.30210	0.13680	0.00590	0.0580*
H8B	0.29860	0.16180	0.15570	0.0580*
H10	0.25200	0.29870	0.28780	0.0570*
H11	0.14770	0.41340	0.42830	0.0680*
H12	−0.04750	0.50670	0.36210	0.0750*
H13	−0.14370	0.48100	0.15370	0.0790*
H14	−0.04490	0.36490	0.01240	0.0680*

	U11	U22	U33	U12	U13	U23
Cl1	0.0635 (3)	0.1420 (6)	0.0602 (3)	0.0059 (3)	−0.0005 (2)	0.0431 (3)
O1	0.0397 (5)	0.0669 (7)	0.0528 (6)	−0.0022 (5)	−0.0074 (4)	−0.0061 (5)
O2	0.0674 (8)	0.0890 (9)	0.0457 (6)	0.0034 (7)	−0.0112 (5)	0.0084 (6)
N1	0.0373 (6)	0.0508 (7)	0.0399 (6)	−0.0004 (5)	−0.0007 (4)	0.0013 (5)
N2	0.0387 (6)	0.0736 (9)	0.0397 (6)	−0.0032 (6)	−0.0006 (5)	−0.0068 (6)
C1	0.0332 (6)	0.0416 (7)	0.0429 (7)	0.0030 (5)	0.0039 (5)	−0.0028 (6)
C2	0.0337 (6)	0.0572 (9)	0.0452 (7)	0.0012 (6)	0.0011 (5)	0.0028 (6)
C3	0.0433 (7)	0.0645 (10)	0.0486 (8)	0.0091 (7)	0.0050 (6)	0.0111 (7)
C4	0.0468 (8)	0.0528 (9)	0.0678 (10)	0.0010 (7)	0.0166 (7)	0.0096 (8)
C5	0.0391 (7)	0.0515 (9)	0.0716 (10)	−0.0055 (6)	0.0082 (7)	−0.0054 (8)
C6	0.0353 (6)	0.0478 (8)	0.0507 (8)	0.0027 (6)	0.0002 (6)	−0.0068 (6)
C7	0.0431 (7)	0.0582 (9)	0.0464 (8)	0.0066 (7)	−0.0044 (6)	−0.0024 (7)
C8	0.0477 (8)	0.0487 (8)	0.0476 (8)	−0.0050 (6)	0.0049 (6)	0.0000 (6)
C9	0.0365 (6)	0.0503 (8)	0.0400 (7)	−0.0100 (6)	0.0033 (5)	0.0036 (6)
C10	0.0385 (7)	0.0609 (9)	0.0427 (7)	−0.0069 (6)	−0.0008 (5)	0.0020 (7)
C11	0.0523 (9)	0.0708 (11)	0.0463 (8)	−0.0130 (8)	0.0010 (6)	−0.0104 (8)
C12	0.0565 (9)	0.0612 (10)	0.0704 (11)	−0.0046 (8)	0.0110 (8)	−0.0156 (9)
C13	0.0523 (9)	0.0667 (11)	0.0778 (12)	0.0099 (8)	−0.0039 (8)	−0.0028 (9)
C14	0.0493 (8)	0.0695 (11)	0.0501 (8)	0.0016 (7)	−0.0081 (7)	0.0007 (8)

Cl1—C3	1.7315 (16)	C9—C14	1.398 (2)
O1—C6	1.3817 (19)	C9—C10	1.388 (2)
O1—C7	1.3769 (19)	C10—C11	1.384 (2)
O2—C7	1.198 (2)	C11—C12	1.373 (2)
N1—C1	1.3914 (18)	C12—C13	1.373 (3)
N1—C7	1.3669 (19)	C13—C14	1.376 (3)
N1—C8	1.4711 (19)	C2—H2	0.9300
N2—C8	1.414 (2)	C4—H4	0.9300
N2—C9	1.3831 (19)	C5—H5	0.9300
N2—H2A	0.8600	C8—H8A	0.9700
C1—C2	1.3725 (19)	C8—H8B	0.9700
C1—C6	1.3818 (19)	C10—H10	0.9300
C2—C3	1.388 (2)	C11—H11	0.9300
C3—C4	1.376 (2)	C12—H12	0.9300
C4—C5	1.387 (2)	C13—H13	0.9300
C5—C6	1.368 (2)	C14—H14	0.9300
C6—O1—C7	107.78 (11)	C9—C10—C11	119.87 (14)
C1—N1—C7	109.19 (11)	C10—C11—C12	121.47 (16)
C1—N1—C8	125.75 (11)	C11—C12—C13	118.90 (17)
C7—N1—C8	124.99 (12)	C12—C13—C14	120.73 (17)
C8—N2—C9	124.23 (12)	C9—C14—C13	120.73 (15)
C9—N2—H2A	118.00	C1—C2—H2	122.00
C8—N2—H2A	118.00	C3—C2—H2	122.00
N1—C1—C6	106.29 (12)	C3—C4—H4	120.00
N1—C1—C2	132.05 (12)	C5—C4—H4	120.00
C2—C1—C6	121.65 (13)	C4—C5—H5	122.00
C1—C2—C3	115.20 (13)	C6—C5—H5	122.00
Cl1—C3—C4	118.73 (13)	N1—C8—H8A	109.00
Cl1—C3—C2	117.77 (12)	N1—C8—H8B	109.00
C2—C3—C4	123.49 (15)	N2—C8—H8A	109.00
C3—C4—C5	120.48 (15)	N2—C8—H8B	109.00
C4—C5—C6	116.25 (14)	H8A—C8—H8B	108.00
C1—C6—C5	122.93 (14)	C9—C10—H10	120.00
O1—C6—C5	128.24 (13)	C11—C10—H10	120.00
O1—C6—C1	108.83 (12)	C10—C11—H11	119.00
O1—C7—N1	107.90 (12)	C12—C11—H11	119.00
O1—C7—O2	122.84 (14)	C11—C12—H12	121.00
O2—C7—N1	129.27 (15)	C13—C12—H12	121.00
N1—C8—N2	113.63 (13)	C12—C13—H13	120.00
N2—C9—C10	122.83 (13)	C14—C13—H13	120.00
C10—C9—C14	118.29 (14)	C9—C14—H14	120.00
N2—C9—C14	118.87 (13)	C13—C14—H14	120.00
C7—O1—C6—C5	179.00 (16)	N1—C1—C2—C3	179.08 (15)
C6—O1—C7—O2	−178.94 (16)	C6—C1—C2—C3	−0.3 (2)
C7—O1—C6—C1	−0.57 (16)	N1—C1—C6—O1	0.04 (16)
C6—O1—C7—N1	0.88 (16)	C2—C1—C6—C5	0.0 (2)
C7—N1—C1—C2	−178.96 (16)	C1—C2—C3—Cl1	−179.79 (12)
C8—N1—C1—C2	3.9 (2)	C1—C2—C3—C4	0.2 (2)
C1—N1—C7—O1	−0.86 (16)	C2—C3—C4—C5	0.3 (3)
C8—N1—C7—O1	176.31 (13)	Cl1—C3—C4—C5	−179.75 (13)
C1—N1—C7—O2	178.93 (17)	C3—C4—C5—C6	−0.6 (2)
C8—N1—C7—O2	−3.9 (3)	C4—C5—C6—C1	0.5 (2)
C1—N1—C8—N2	−59.57 (18)	C4—C5—C6—O1	−179.03 (15)
C7—N1—C8—N2	123.72 (15)	N2—C9—C10—C11	−178.47 (15)
C8—N1—C1—C6	−176.64 (13)	C14—C9—C10—C11	0.6 (2)
C7—N1—C1—C6	0.51 (16)	N2—C9—C14—C13	179.13 (16)
C8—N2—C9—C10	−6.8 (2)	C10—C9—C14—C13	0.0 (2)
C9—N2—C8—N1	−72.99 (18)	C9—C10—C11—C12	−1.1 (3)
C8—N2—C9—C14	174.17 (15)	C10—C11—C12—C13	0.9 (3)
C2—C1—C6—O1	179.57 (13)	C11—C12—C13—C14	−0.3 (3)
N1—C1—C6—C5	−179.55 (14)	C12—C13—C14—C9	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.30	3.1296 (17)	162
C11—H11···Cl1ii	0.93	2.70	3.5295 (17)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.30	3.1296 (17)	162
C11—H11⋯Cl1ii	0.93	2.70	3.5295 (17)	150

Symmetry codes: (i) ; (ii) .