2-(2-Chloro-pyridin-3-yl)-N-ethyl-4-methyl-1,3-oxazole-5-carboxamide.

In the title compound, C(12)H(12)ClN(3)O(2), the dihedral angle between the aromatic rings is 8.42 (10)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(4) chains propagating in [001].

Related literature

For background to derivatives of oxazolyl carb­oxy­lic acids, see: Takechi et al. (2000 ▶); Lechel et al. (2009 ▶).

Experimental

Crystal data

C12H12ClN3O2

M = 265.70

Monoclinic,

a = 8.2143 (12) Å

b = 14.545 (2) Å

c = 10.4360 (16) Å

β = 97.425 (3)°

V = 1236.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.32 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.908, T max = 0.936

6234 measured reflections

2183 independent reflections

1736 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.07

2183 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045885/hb5697sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045885/hb5697Isup2.hkl

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

C12H12ClN3O2	F(000) = 552
Mr = 265.70	Dx = 1.427 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.2143 (12) Å	Cell parameters from 2185 reflections
b = 14.545 (2) Å	θ = 2.4–25.4°
c = 10.4360 (16) Å	µ = 0.31 mm−1
β = 97.425 (3)°	T = 296 K
V = 1236.4 (3) Å3	Block, colorless
Z = 4	0.32 × 0.28 × 0.22 mm

Bruker SMART CCD diffractometer	2183 independent reflections
Radiation source: fine-focus sealed tube	1736 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.908, Tmax = 0.936	k = −17→17
6234 measured reflections	l = −12→8

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.2339P] where P = (Fo2 + 2Fc2)/3
2183 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 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
Cl1	0.52313 (8)	1.15459 (4)	0.30039 (6)	0.0650 (2)
O1	0.81459 (15)	0.89027 (8)	0.35667 (12)	0.0424 (3)
O2	0.91578 (18)	0.72507 (9)	0.12724 (13)	0.0542 (4)
N1	0.6093 (2)	1.15962 (11)	0.54565 (19)	0.0582 (5)
N2	0.6424 (2)	0.96872 (10)	0.21507 (15)	0.0449 (4)
N3	0.9699 (2)	0.72633 (10)	0.34513 (15)	0.0476 (4)
H3	0.9523	0.7530	0.4156	0.057*
C1	0.6202 (2)	1.10823 (12)	0.4431 (2)	0.0457 (5)
C2	0.6806 (3)	1.12864 (15)	0.6593 (2)	0.0625 (6)
H2	0.6733	1.1642	0.7324	0.075*
C3	0.7641 (3)	1.04702 (15)	0.6739 (2)	0.0636 (6)
H3A	0.8122	1.0278	0.7551	0.076*
C4	0.7752 (3)	0.99428 (13)	0.56647 (19)	0.0525 (5)
H4	0.8320	0.9388	0.5744	0.063*
C5	0.7019 (2)	1.02335 (12)	0.44587 (18)	0.0420 (4)
C6	0.7133 (2)	0.96435 (12)	0.33294 (18)	0.0399 (4)
C7	0.8032 (2)	0.84506 (11)	0.23930 (18)	0.0402 (4)
C8	0.6982 (2)	0.89204 (12)	0.15339 (18)	0.0416 (4)
C9	0.6388 (3)	0.87207 (15)	0.0153 (2)	0.0567 (6)
H9A	0.7179	0.8936	−0.0378	0.085*
H9B	0.5359	0.9027	−0.0091	0.085*
H9C	0.6242	0.8070	0.0038	0.085*
C10	0.9008 (2)	0.76014 (12)	0.23233 (18)	0.0412 (4)
C11	1.0747 (3)	0.64501 (15)	0.3517 (2)	0.0627 (6)
H11A	1.0109	0.5931	0.3149	0.075*
H11B	1.1631	0.6554	0.3001	0.075*
C12	1.1446 (4)	0.6227 (2)	0.4837 (3)	0.0857 (9)
H12A	1.2037	0.6749	0.5220	0.129*
H12B	1.2181	0.5715	0.4827	0.129*
H12C	1.0580	0.6070	0.5333	0.129*

	U11	U22	U33	U12	U13	U23
Cl1	0.0845 (4)	0.0471 (3)	0.0613 (4)	0.0194 (3)	0.0012 (3)	0.0078 (2)
O1	0.0535 (8)	0.0366 (7)	0.0360 (7)	0.0063 (6)	0.0015 (6)	−0.0004 (5)
O2	0.0808 (10)	0.0446 (8)	0.0379 (8)	0.0047 (7)	0.0104 (7)	−0.0043 (6)
N1	0.0718 (12)	0.0405 (9)	0.0626 (12)	0.0066 (8)	0.0098 (10)	−0.0062 (8)
N2	0.0531 (10)	0.0376 (8)	0.0428 (9)	0.0036 (7)	0.0016 (8)	0.0025 (7)
N3	0.0633 (10)	0.0408 (9)	0.0387 (9)	0.0139 (7)	0.0071 (8)	0.0002 (7)
C1	0.0502 (11)	0.0347 (10)	0.0524 (12)	0.0005 (8)	0.0078 (9)	0.0015 (8)
C2	0.0843 (16)	0.0496 (12)	0.0541 (14)	0.0016 (12)	0.0106 (12)	−0.0126 (11)
C3	0.0910 (17)	0.0517 (13)	0.0461 (13)	0.0102 (12)	0.0011 (12)	−0.0032 (10)
C4	0.0688 (14)	0.0396 (10)	0.0481 (12)	0.0090 (9)	0.0034 (10)	−0.0018 (9)
C5	0.0474 (11)	0.0339 (9)	0.0453 (11)	−0.0019 (8)	0.0080 (9)	0.0023 (8)
C6	0.0454 (10)	0.0308 (9)	0.0431 (11)	0.0008 (7)	0.0048 (9)	0.0039 (7)
C7	0.0502 (11)	0.0345 (9)	0.0353 (10)	−0.0022 (8)	0.0029 (8)	−0.0011 (7)
C8	0.0479 (11)	0.0375 (10)	0.0387 (10)	−0.0033 (8)	0.0031 (8)	0.0016 (8)
C9	0.0672 (14)	0.0549 (12)	0.0442 (12)	0.0043 (11)	−0.0069 (10)	−0.0020 (10)
C10	0.0500 (11)	0.0348 (9)	0.0392 (10)	−0.0035 (8)	0.0072 (9)	−0.0006 (8)
C11	0.0796 (16)	0.0500 (13)	0.0578 (14)	0.0237 (11)	0.0068 (12)	0.0004 (10)
C12	0.103 (2)	0.0863 (18)	0.0661 (17)	0.0496 (16)	0.0029 (15)	0.0079 (14)

Cl1—C1	1.733 (2)	C4—C5	1.389 (3)
O1—C6	1.364 (2)	C4—H4	0.9300
O1—C7	1.383 (2)	C5—C6	1.471 (3)
O2—C10	1.230 (2)	C7—C8	1.347 (2)
N1—C1	1.318 (3)	C7—C10	1.479 (3)
N1—C2	1.332 (3)	C8—C9	1.489 (3)
N2—C6	1.293 (2)	C9—H9A	0.9600
N2—C8	1.395 (2)	C9—H9B	0.9600
N3—C10	1.333 (2)	C9—H9C	0.9600
N3—C11	1.459 (2)	C11—C12	1.459 (3)
N3—H3	0.8600	C11—H11A	0.9700
C1—C5	1.404 (3)	C11—H11B	0.9700
C2—C3	1.370 (3)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.372 (3)	C12—H12C	0.9600
C3—H3A	0.9300
C6—O1—C7	104.17 (14)	O1—C7—C10	117.74 (15)
C1—N1—C2	117.59 (18)	C7—C8—N2	108.60 (16)
C6—N2—C8	105.37 (15)	C7—C8—C9	130.30 (18)
C10—N3—C11	121.45 (17)	N2—C8—C9	121.08 (17)
C10—N3—H3	119.3	C8—C9—H9A	109.5
C11—N3—H3	119.3	C8—C9—H9B	109.5
N1—C1—C5	124.39 (19)	H9A—C9—H9B	109.5
N1—C1—Cl1	113.91 (15)	C8—C9—H9C	109.5
C5—C1—Cl1	121.70 (15)	H9A—C9—H9C	109.5
N1—C2—C3	123.3 (2)	H9B—C9—H9C	109.5
N1—C2—H2	118.4	O2—C10—N3	123.63 (17)
C3—C2—H2	118.4	O2—C10—C7	120.50 (17)
C2—C3—C4	118.6 (2)	N3—C10—C7	115.86 (16)
C2—C3—H3A	120.7	C12—C11—N3	112.48 (19)
C4—C3—H3A	120.7	C12—C11—H11A	109.1
C3—C4—C5	120.25 (19)	N3—C11—H11A	109.1
C3—C4—H4	119.9	C12—C11—H11B	109.1
C5—C4—H4	119.9	N3—C11—H11B	109.1
C4—C5—C1	115.87 (18)	H11A—C11—H11B	107.8
C4—C5—C6	118.92 (16)	C11—C12—H12A	109.5
C1—C5—C6	125.21 (17)	C11—C12—H12B	109.5
N2—C6—O1	113.63 (16)	H12A—C12—H12B	109.5
N2—C6—C5	131.78 (17)	C11—C12—H12C	109.5
O1—C6—C5	114.57 (16)	H12A—C12—H12C	109.5
C8—C7—O1	108.22 (15)	H12B—C12—H12C	109.5
C8—C7—C10	134.03 (17)
C2—N1—C1—C5	−0.1 (3)	C4—C5—C6—O1	−7.8 (3)
C2—N1—C1—Cl1	179.87 (17)	C1—C5—C6—O1	172.89 (16)
C1—N1—C2—C3	0.3 (4)	C6—O1—C7—C8	−0.41 (19)
N1—C2—C3—C4	0.0 (4)	C6—O1—C7—C10	179.86 (15)
C2—C3—C4—C5	−0.5 (4)	O1—C7—C8—N2	0.6 (2)
C3—C4—C5—C1	0.6 (3)	C10—C7—C8—N2	−179.76 (19)
C3—C4—C5—C6	−178.8 (2)	O1—C7—C8—C9	−178.03 (19)
N1—C1—C5—C4	−0.3 (3)	C10—C7—C8—C9	1.6 (4)
Cl1—C1—C5—C4	179.72 (15)	C6—N2—C8—C7	−0.5 (2)
N1—C1—C5—C6	179.00 (19)	C6—N2—C8—C9	178.25 (18)
Cl1—C1—C5—C6	−1.0 (3)	C11—N3—C10—O2	1.9 (3)
C8—N2—C6—O1	0.2 (2)	C11—N3—C10—C7	−177.52 (18)
C8—N2—C6—C5	−178.29 (19)	C8—C7—C10—O2	11.7 (3)
C7—O1—C6—N2	0.1 (2)	O1—C7—C10—O2	−168.64 (17)
C7—O1—C6—C5	178.89 (15)	C8—C7—C10—N3	−168.8 (2)
C4—C5—C6—N2	170.7 (2)	O1—C7—C10—N3	10.8 (2)
C1—C5—C6—N2	−8.6 (3)	C10—N3—C11—C12	176.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2i	0.86	2.29	3.115 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2i	0.86	2.29	3.115 (2)	161

Symmetry code: (i) .