(Z)-4-[4-(Dimethyl-amino)benzyl-idene]-3-methyl-isoxazol-5(4H)-one.

The title compound, C(13)H(14)N(2)O(2), an isoxazol-5-one derivative, was synthesized by a one-pot, three-component condensation reaction of methyl acetoacetate, hydroxy-lamine hydro-chloride and 4-(dimethyl-amino)benzaldehyde. All the non-H atoms are co-planar [r.m.s deviation = 0.0039 Å], with a Z configuration about the C=C bond. The dihedral angle between the phenyl ring and the isoxazole ring is 2.58 (19)°.

Related literature

For the biological activity of aryl­methyl­ene isoxazolone deriv­atives, see: Ishioka et al. (2002 ▶); Liu et al. (2005 ▶). For details of the synthesis of related compounds, see: Cocivera et al. (1976 ▶); Zhang et al. (2008 ▶); Villemin et al. (1993 ▶). For related structures, see: Kay et al. (2001 ▶); Wolf et al. (1995 ▶).

Experimental

Crystal data

C13H14N2O2

M = 230.26

Triclinic,

a = 6.4201 (10) Å

b = 7.8239 (12) Å

c = 12.1901 (15) Å

α = 100.272 (2)°

β = 97.319 (1)°

γ = 101.461 (2)°

V = 582.01 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.13 × 0.09 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.988, T max = 0.993

2990 measured reflections

2020 independent reflections

943 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.178

S = 1.03

2020 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904714X/su2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904714X/su2156Isup2.hkl

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

C13H14N2O2	Z = 2
Mr = 230.26	F(000) = 244
Triclinic, P1	Dx = 1.314 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4201 (10) Å	Cell parameters from 607 reflections
b = 7.8239 (12) Å	θ = 2.9–25.1°
c = 12.1901 (15) Å	µ = 0.09 mm−1
α = 100.272 (2)°	T = 298 K
β = 97.319 (1)°	Needle, red
γ = 101.461 (2)°	0.13 × 0.09 × 0.08 mm
V = 582.01 (15) Å3

Bruker SMART CCD area-detector diffractometer	2020 independent reflections
Radiation source: fine-focus sealed tube	943 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.988, Tmax = 0.993	k = −9→6
2990 measured reflections	l = −13→14

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.069P)2 + ] where P = (Fo2 + 2Fc2)/3
2020 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 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
N1	0.7351 (5)	0.6599 (4)	0.8929 (3)	0.0671 (10)
N2	0.3808 (5)	0.8488 (4)	0.1943 (3)	0.0604 (9)
O1	0.9130 (4)	0.7385 (4)	0.8421 (2)	0.0746 (9)
O2	0.9643 (4)	0.8104 (4)	0.6764 (2)	0.0797 (9)
C1	0.8347 (6)	0.7524 (5)	0.7333 (4)	0.0626 (11)
C2	0.6035 (5)	0.6855 (5)	0.7140 (3)	0.0492 (9)
C3	0.5624 (5)	0.6321 (4)	0.8187 (3)	0.0503 (9)
C4	0.3517 (5)	0.5490 (5)	0.8451 (3)	0.0634 (11)
H4A	0.3722	0.5237	0.9195	0.095*
H4B	0.2895	0.4400	0.7907	0.095*
H4C	0.2568	0.6293	0.8423	0.095*
C5	0.4464 (5)	0.6758 (4)	0.6248 (3)	0.0506 (9)
H5	0.3094	0.6266	0.6373	0.061*
C6	0.4428 (5)	0.7234 (4)	0.5171 (3)	0.0458 (9)
C7	0.2412 (5)	0.6921 (5)	0.4469 (3)	0.0546 (10)
H7	0.1181	0.6420	0.4730	0.066*
C8	0.2192 (5)	0.7323 (5)	0.3417 (3)	0.0563 (10)
H8	0.0829	0.7086	0.2980	0.068*
C9	0.4013 (5)	0.8091 (4)	0.2993 (3)	0.0496 (9)
C10	0.6035 (5)	0.8435 (5)	0.3700 (3)	0.0526 (10)
H10	0.7264	0.8965	0.3448	0.063*
C11	0.6244 (5)	0.8012 (4)	0.4750 (3)	0.0507 (9)
H11	0.7605	0.8244	0.5187	0.061*
C12	0.5668 (6)	0.9262 (5)	0.1481 (3)	0.0691 (12)
H12A	0.6721	1.0058	0.2079	0.104*
H12B	0.5224	0.9911	0.0929	0.104*
H12C	0.6287	0.8329	0.1129	0.104*
C13	0.1725 (6)	0.8003 (6)	0.1198 (3)	0.0751 (12)
H13A	0.1191	0.6734	0.1050	0.113*
H13B	0.1886	0.8376	0.0499	0.113*
H13C	0.0725	0.8581	0.1555	0.113*

	U11	U22	U33	U12	U13	U23
N1	0.0601 (19)	0.091 (3)	0.058 (2)	0.0251 (18)	0.0110 (18)	0.027 (2)
N2	0.057 (2)	0.066 (2)	0.057 (2)	0.0083 (16)	0.0014 (17)	0.0214 (18)
O1	0.0534 (16)	0.105 (2)	0.0670 (19)	0.0177 (15)	0.0012 (14)	0.0282 (17)
O2	0.0470 (15)	0.116 (2)	0.075 (2)	0.0066 (15)	0.0082 (14)	0.0298 (18)
C1	0.053 (2)	0.076 (3)	0.058 (3)	0.018 (2)	0.003 (2)	0.012 (2)
C2	0.0429 (19)	0.056 (2)	0.050 (2)	0.0151 (16)	0.0067 (17)	0.0117 (19)
C3	0.051 (2)	0.059 (2)	0.045 (2)	0.0233 (18)	0.0035 (18)	0.0117 (19)
C4	0.067 (2)	0.077 (3)	0.055 (3)	0.020 (2)	0.013 (2)	0.027 (2)
C5	0.0423 (18)	0.049 (2)	0.063 (3)	0.0112 (16)	0.0113 (18)	0.016 (2)
C6	0.046 (2)	0.046 (2)	0.048 (2)	0.0124 (16)	0.0067 (17)	0.0134 (18)
C7	0.044 (2)	0.061 (3)	0.060 (3)	0.0079 (17)	0.0069 (18)	0.021 (2)
C8	0.046 (2)	0.058 (2)	0.062 (3)	0.0066 (18)	0.0001 (18)	0.016 (2)
C9	0.051 (2)	0.047 (2)	0.052 (2)	0.0118 (17)	0.0030 (18)	0.0161 (19)
C10	0.0437 (19)	0.059 (2)	0.055 (2)	0.0097 (17)	0.0045 (18)	0.016 (2)
C11	0.0435 (19)	0.055 (2)	0.054 (2)	0.0119 (17)	0.0021 (17)	0.0155 (19)
C12	0.075 (3)	0.077 (3)	0.060 (3)	0.016 (2)	0.015 (2)	0.027 (2)
C13	0.071 (3)	0.096 (3)	0.059 (3)	0.018 (2)	−0.002 (2)	0.029 (2)

N1—C3	1.294 (4)	C6—C11	1.405 (4)
N1—O1	1.451 (3)	C6—C7	1.409 (5)
N2—C9	1.367 (4)	C7—C8	1.371 (5)
N2—C12	1.455 (4)	C7—H7	0.9300
N2—C13	1.457 (4)	C8—C9	1.407 (4)
O1—C1	1.388 (4)	C8—H8	0.9300
O2—C1	1.220 (4)	C9—C10	1.412 (5)
C1—C2	1.446 (5)	C10—C11	1.375 (4)
C2—C5	1.365 (5)	C10—H10	0.9300
C2—C3	1.451 (4)	C11—H11	0.9300
C3—C4	1.481 (4)	C12—H12A	0.9600
C4—H4A	0.9600	C12—H12B	0.9600
C4—H4B	0.9600	C12—H12C	0.9600
C4—H4C	0.9600	C13—H13A	0.9600
C5—C6	1.426 (4)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C3—N1—O1	106.5 (3)	C8—C7—H7	118.7
C9—N2—C12	121.9 (3)	C6—C7—H7	118.7
C9—N2—C13	120.9 (3)	C7—C8—C9	120.4 (3)
C12—N2—C13	117.0 (3)	C7—C8—H8	119.8
C1—O1—N1	109.2 (3)	C9—C8—H8	119.8
O2—C1—O1	118.0 (3)	N2—C9—C8	120.8 (3)
O2—C1—C2	134.7 (4)	N2—C9—C10	122.0 (3)
O1—C1—C2	107.3 (3)	C8—C9—C10	117.2 (3)
C5—C2—C1	132.2 (3)	C11—C10—C9	122.0 (3)
C5—C2—C3	124.2 (3)	C11—C10—H10	119.0
C1—C2—C3	103.6 (3)	C9—C10—H10	119.0
N1—C3—C2	113.3 (3)	C10—C11—C6	120.9 (3)
N1—C3—C4	119.5 (3)	C10—C11—H11	119.5
C2—C3—C4	127.1 (3)	C6—C11—H11	119.5
C3—C4—H4A	109.5	N2—C12—H12A	109.5
C3—C4—H4B	109.5	N2—C12—H12B	109.5
H4A—C4—H4B	109.5	H12A—C12—H12B	109.5
C3—C4—H4C	109.5	N2—C12—H12C	109.5
H4A—C4—H4C	109.5	H12A—C12—H12C	109.5
H4B—C4—H4C	109.5	H12B—C12—H12C	109.5
C2—C5—C6	135.0 (3)	N2—C13—H13A	109.5
C2—C5—H5	112.5	N2—C13—H13B	109.5
C6—C5—H5	112.5	H13A—C13—H13B	109.5
C11—C6—C7	116.8 (3)	N2—C13—H13C	109.5
C11—C6—C5	125.4 (3)	H13A—C13—H13C	109.5
C7—C6—C5	117.8 (3)	H13B—C13—H13C	109.5
C8—C7—C6	122.7 (3)
C3—N1—O1—C1	−0.9 (4)	C2—C5—C6—C7	−179.7 (4)
N1—O1—C1—O2	−177.5 (3)	C11—C6—C7—C8	0.8 (5)
N1—O1—C1—C2	1.1 (4)	C5—C6—C7—C8	−179.8 (3)
O2—C1—C2—C5	−5.2 (8)	C6—C7—C8—C9	−0.4 (5)
O1—C1—C2—C5	176.5 (4)	C12—N2—C9—C8	−179.2 (3)
O2—C1—C2—C3	177.5 (4)	C13—N2—C9—C8	−4.7 (5)
O1—C1—C2—C3	−0.9 (4)	C12—N2—C9—C10	1.1 (5)
O1—N1—C3—C2	0.4 (4)	C13—N2—C9—C10	175.6 (3)
O1—N1—C3—C4	178.9 (3)	C7—C8—C9—N2	179.7 (3)
C5—C2—C3—N1	−177.3 (3)	C7—C8—C9—C10	−0.6 (5)
C1—C2—C3—N1	0.3 (4)	N2—C9—C10—C11	−179.0 (3)
C5—C2—C3—C4	4.2 (6)	C8—C9—C10—C11	1.3 (5)
C1—C2—C3—C4	−178.2 (3)	C9—C10—C11—C6	−0.9 (5)
C1—C2—C5—C6	0.8 (7)	C7—C6—C11—C10	−0.1 (5)
C3—C2—C5—C6	177.6 (3)	C5—C6—C11—C10	−179.5 (3)
C2—C5—C6—C11	−0.4 (6)