N,N-Dimethyl-3-phenyl-isoxazole-5-carbox-amide.

In the title compound, C12H12N2O2, synthesized by ammonolysis of 3-phenyl-isoxazole-5-carbonyl chloride in di-chloro-methane, the dihedral angle between the isoxazole ring and the phenyl ring is 14.05 (7)°. In the crystal, centrosym-metrically related mol-ecules are linked into dimers by pairs of C-H⋯O hydrogen bonds, generating rings of graph-set motif R 2 (2)(10).

Related literature

For the biological activity of isoxazole derivatives, see: Lopes et al. (2011 ▶). For the synthesis and structure of a related compound, see: Wang et al. (2013 ▶).

Experimental

Crystal data

C12H12N2O2

M = 216.24

Monoclinic,

a = 7.596 (3) Å

b = 12.377 (6) Å

c = 12.123 (6) Å

β = 102.964 (8)°

V = 1110.7 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.36 × 0.25 × 0.13 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.970, T max = 0.989

5434 measured reflections

1977 independent reflections

1373 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.128

S = 1.03

1977 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813033199/rz5100sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033199/rz5100Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033199/rz5100Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H12N2O2	Z = 4
Mr = 216.24	F(000) = 456
Monoclinic, P21/c	Dx = 1.287 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.596 (3) Å	θ = 2.4–25.1°
b = 12.377 (6) Å	µ = 0.09 mm−1
c = 12.123 (6) Å	T = 296 K
β = 102.964 (8)°	Block, colourless
V = 1110.7 (9) Å3	0.36 × 0.25 × 0.13 mm

Bruker APEXII CCD area detector diffractometer	1977 independent reflections
Radiation source: fine-focus sealed tube	1373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
phi and ω scans	θmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −5→9
Tmin = 0.970, Tmax = 0.989	k = −14→14
5434 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0624P)2 + 0.0693P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1977 reflections	Δρmax = 0.14 e Å−3
148 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.007 (2)

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	0.4029 (3)	0.01587 (14)	0.33843 (15)	0.0628 (6)
O1	0.3706 (2)	0.11427 (10)	0.27668 (12)	0.0616 (5)
O2	0.1335 (2)	0.15233 (11)	−0.00766 (12)	0.0643 (5)
C1	0.3700 (3)	−0.19723 (17)	0.43043 (18)	0.0575 (6)
H1	0.4227	−0.1441	0.4815	0.069*
C2	0.3675 (3)	−0.30437 (19)	0.4660 (2)	0.0659 (7)
H2	0.4206	−0.3224	0.5405	0.079*
C3	0.2870 (3)	−0.38412 (18)	0.3915 (2)	0.0654 (7)
H3	0.2847	−0.4552	0.4160	0.078*
C4	0.2103 (3)	−0.35728 (18)	0.2807 (2)	0.0654 (7)
H4	0.1563	−0.4108	0.2305	0.079*
C5	0.2126 (3)	−0.25108 (17)	0.24309 (18)	0.0538 (6)
H5	0.1606	−0.2341	0.1681	0.065*
C6	0.2930 (3)	−0.16985 (15)	0.31781 (16)	0.0448 (5)
C7	0.2953 (3)	−0.05662 (15)	0.27653 (16)	0.0431 (5)
C8	0.1948 (3)	−0.00969 (15)	0.17427 (16)	0.0470 (5)
H8	0.1123	−0.0440	0.1166	0.056*
C9	0.2449 (3)	0.09524 (15)	0.17905 (16)	0.0440 (5)
C10	0.1868 (3)	0.18267 (15)	0.09211 (17)	0.0460 (5)
N2	0.1934 (2)	0.28752 (12)	0.12311 (13)	0.0493 (5)
C12	0.1405 (4)	0.36960 (17)	0.03430 (19)	0.0701 (7)
H12A	0.1469	0.3393	−0.0376	0.105*
H12B	0.2209	0.4303	0.0506	0.105*
H12C	0.0192	0.3929	0.0319	0.105*
C13	0.2324 (3)	0.32936 (17)	0.23967 (17)	0.0613 (6)
H13A	0.2315	0.2708	0.2915	0.092*
H13B	0.1421	0.3814	0.2472	0.092*
H13C	0.3491	0.3632	0.2564	0.092*

	U11	U22	U33	U12	U13	U23
N1	0.0738 (13)	0.0460 (10)	0.0568 (12)	−0.0028 (9)	−0.0101 (10)	0.0042 (8)
O1	0.0719 (10)	0.0442 (8)	0.0564 (9)	−0.0073 (7)	−0.0118 (8)	−0.0004 (7)
O2	0.0872 (12)	0.0580 (9)	0.0411 (9)	−0.0080 (8)	0.0000 (8)	−0.0026 (7)
C1	0.0584 (14)	0.0616 (13)	0.0488 (13)	−0.0027 (11)	0.0040 (11)	0.0037 (11)
C2	0.0668 (15)	0.0713 (16)	0.0552 (14)	0.0036 (12)	0.0048 (12)	0.0208 (12)
C3	0.0724 (16)	0.0536 (14)	0.0705 (17)	0.0020 (12)	0.0169 (13)	0.0148 (12)
C4	0.0806 (17)	0.0477 (13)	0.0657 (16)	−0.0039 (11)	0.0117 (13)	−0.0004 (11)
C5	0.0626 (14)	0.0483 (12)	0.0475 (12)	0.0016 (10)	0.0060 (11)	0.0026 (10)
C6	0.0430 (11)	0.0442 (11)	0.0458 (11)	0.0019 (9)	0.0073 (9)	0.0020 (9)
C7	0.0422 (11)	0.0431 (11)	0.0421 (12)	0.0000 (9)	0.0052 (9)	−0.0049 (9)
C8	0.0517 (12)	0.0461 (12)	0.0394 (11)	−0.0049 (9)	0.0017 (10)	−0.0041 (9)
C9	0.0457 (11)	0.0465 (11)	0.0368 (11)	−0.0007 (9)	0.0031 (9)	−0.0055 (9)
C10	0.0497 (12)	0.0449 (11)	0.0425 (12)	−0.0056 (9)	0.0087 (10)	−0.0027 (9)
N2	0.0597 (11)	0.0432 (9)	0.0425 (10)	−0.0016 (8)	0.0060 (8)	0.0020 (8)
C12	0.0889 (18)	0.0525 (13)	0.0637 (16)	−0.0034 (12)	0.0059 (14)	0.0114 (11)
C13	0.0781 (16)	0.0486 (12)	0.0551 (14)	−0.0018 (11)	0.0107 (12)	−0.0078 (11)

N1—C7	1.327 (2)	C6—C7	1.490 (3)
N1—O1	1.422 (2)	C7—C8	1.425 (3)
O1—C9	1.364 (2)	C8—C9	1.351 (3)
O2—C10	1.244 (2)	C8—H8	0.9300
C1—C2	1.396 (3)	C9—C10	1.506 (3)
C1—C6	1.401 (3)	C10—N2	1.349 (2)
C1—H1	0.9300	N2—C12	1.469 (2)
C2—C3	1.384 (3)	N2—C13	1.471 (2)
C2—H2	0.9300	C12—H12A	0.9600
C3—C4	1.380 (3)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
C4—C5	1.393 (3)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.399 (3)	C13—H13C	0.9600
C5—H5	0.9300
C7—N1—O1	105.64 (16)	C9—C8—H8	127.4
C9—O1—N1	108.28 (14)	C7—C8—H8	127.4
C2—C1—C6	119.9 (2)	C8—C9—O1	109.81 (16)
C2—C1—H1	120.0	C8—C9—C10	128.71 (18)
C6—C1—H1	120.0	O1—C9—C10	121.42 (16)
C3—C2—C1	120.7 (2)	O2—C10—N2	123.01 (18)
C3—C2—H2	119.6	O2—C10—C9	116.34 (17)
C1—C2—H2	119.6	N2—C10—C9	120.64 (17)
C4—C3—C2	119.4 (2)	C10—N2—C12	118.31 (17)
C4—C3—H3	120.3	C10—N2—C13	126.38 (16)
C2—C3—H3	120.3	C12—N2—C13	115.05 (16)
C3—C4—C5	120.8 (2)	N2—C12—H12A	109.5
C3—C4—H4	119.6	N2—C12—H12B	109.5
C5—C4—H4	119.6	H12A—C12—H12B	109.5
C4—C5—C6	120.2 (2)	N2—C12—H12C	109.5
C4—C5—H5	119.9	H12A—C12—H12C	109.5
C6—C5—H5	119.9	H12B—C12—H12C	109.5
C5—C6—C1	118.91 (18)	N2—C13—H13A	109.5
C5—C6—C7	119.67 (18)	N2—C13—H13B	109.5
C1—C6—C7	121.42 (18)	H13A—C13—H13B	109.5
N1—C7—C8	110.98 (17)	N2—C13—H13C	109.5
N1—C7—C6	119.88 (17)	H13A—C13—H13C	109.5
C8—C7—C6	129.14 (17)	H13B—C13—H13C	109.5
C9—C8—C7	105.29 (17)
C7—N1—O1—C9	−0.6 (2)	N1—C7—C8—C9	−1.2 (2)
C6—C1—C2—C3	−1.1 (3)	C6—C7—C8—C9	179.07 (19)
C1—C2—C3—C4	0.7 (4)	C7—C8—C9—O1	0.8 (2)
C2—C3—C4—C5	−0.1 (4)	C7—C8—C9—C10	177.71 (19)
C3—C4—C5—C6	−0.1 (3)	N1—O1—C9—C8	−0.1 (2)
C4—C5—C6—C1	−0.2 (3)	N1—O1—C9—C10	−177.31 (16)
C4—C5—C6—C7	179.77 (19)	C8—C9—C10—O2	−24.5 (3)
C2—C1—C6—C5	0.8 (3)	O1—C9—C10—O2	152.16 (19)
C2—C1—C6—C7	−179.19 (19)	C8—C9—C10—N2	155.4 (2)
O1—N1—C7—C8	1.1 (2)	O1—C9—C10—N2	−27.9 (3)
O1—N1—C7—C6	−179.12 (15)	O2—C10—N2—C12	−2.0 (3)
C5—C6—C7—N1	−165.58 (19)	C9—C10—N2—C12	178.11 (18)
C1—C6—C7—N1	14.4 (3)	O2—C10—N2—C13	171.7 (2)
C5—C6—C7—C8	14.1 (3)	C9—C10—N2—C13	−8.2 (3)
C1—C6—C7—C8	−165.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.43	3.340 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.43	3.340 (3)	165

Symmetry code: (i) .