2-(4,5-Dihydro-1,3-oxazol-2-yl)quinoline.

The title compound, C(12)H(10)N(2)O, is approximately planar. The angle between the quinoline and 4,5-dihydro-oxazole ring systems is 11.91 (12)°. The mol-ecules pack into a herringbone array with no significant π-π inter-actions. The dihydro-oxazole N and O atoms are disordered over two positions, with almost equal site occupancy factors.

Related literature

For related 2-substituted quinoline compounds, see: Mague et al. (1997 ▶); Yang et al. (2001 ▶); Qi et al. (2003 ▶); Xu et al. (2006 ▶). For the synthesis, see: Ishihara & Togo (2007 ▶). For related literature, see: Allen (2002 ▶); Cunico et al. (2006 ▶); Hartline et al. (2005 ▶).

Experimental

Crystal data

C12H10N2O

M = 198.22

Monoclinic,

a = 6.2240 (3) Å

b = 13.6649 (6) Å

c = 11.8186 (6) Å

β = 102.097 (3)°

V = 982.86 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 (2) K

0.24 × 0.21 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶)T min = 0.705, T max = 1 (expected range = 0.697–0.989)

9874 measured reflections

2183 independent reflections

1128 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.143

S = 1.00

2183 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2/COSMO/BIS (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT and SADABS (Bruker, 2006 ▶); program(s) used to solve structure: SHELXTL (Bruker, 2001 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2007 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536807045023/lh2491sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807045023/lh2491Isup2.hkl

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

C12H10N2O	F000 = 416
Mr = 198.22	Dx = 1.34 Mg m−3
Monoclinic, P2(1)/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1185 reflections
a = 6.2240 (3) Å	θ = 6.9–40.4º
b = 13.6649 (6) Å	µ = 0.09 mm−1
c = 11.8186 (6) Å	T = 273 (2) K
β = 102.097 (3)º	Block, colourless
V = 982.86 (8) Å3	0.24 × 0.21 × 0.13 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1128 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 296(2) K	θmax = 27.5º
phi and ω scans	θmin = 3.4º
Absorption correction: multi-scan(SADABS; Bruker, 2006) was used to perform the multi-scan semi-empirical (using intensity measurements) absorption correction and to scale the data.	h = −7→8
Tmin = 0.705, Tmax = 1	k = −16→16
9874 measured reflections	l = −15→15
2183 independent reflections

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.069P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2183 reflections	Δρmax = 0.14 e Å−3
137 parameters	Δρmin = −0.15 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Occ. (<1)
C1	0.0592 (3)	0.64386 (12)	0.61057 (14)	0.0526 (5)
C2	−0.0108 (3)	0.68102 (15)	0.49740 (15)	0.0664 (5)
H2	−0.1414	0.6592	0.4508	0.080*
C3	0.1126 (3)	0.74813 (14)	0.45761 (15)	0.0671 (6)
H3	0.0666	0.7738	0.3836	0.080*
C4	0.3119 (3)	0.77950 (12)	0.52818 (13)	0.0531 (5)
C5	0.4498 (3)	0.85086 (13)	0.49471 (15)	0.0644 (5)
H5	0.4114	0.8792	0.4217	0.077*
C6	0.6375 (4)	0.87843 (14)	0.56788 (18)	0.0701 (6)
H6	0.7272	0.9256	0.5448	0.084*
C7	0.6978 (3)	0.83631 (15)	0.67849 (17)	0.0729 (6)
H7	0.8267	0.8561	0.7283	0.087*
C8	0.5700 (3)	0.76724 (14)	0.71306 (15)	0.0644 (5)
H8	0.6128	0.7392	0.7860	0.077*
C9	0.3723 (3)	0.73727 (12)	0.63946 (13)	0.0514 (5)
C11	−0.0822 (3)	0.57463 (13)	0.65666 (15)	0.0591 (5)
C12	−0.2299 (4)	0.48788 (16)	0.77775 (19)	0.0812 (7)
H12A	−0.3146	0.5189	0.8280	0.097*
H12B	−0.1788	0.4247	0.8099	0.097*
C13	−0.3652 (4)	0.47695 (17)	0.65699 (18)	0.0815 (7)
H13A	−0.3657	0.4096	0.6312	0.098*
H13B	−0.5156	0.4977	0.6533	0.098*
N1	0.2441 (2)	0.67018 (10)	0.67998 (11)	0.0538 (4)
N2	−0.2574 (3)	0.54003 (12)	0.58733 (13)	0.0854 (7)	0.473 (17)
O1	−0.0448 (2)	0.54973 (11)	0.76424 (12)	0.0751 (7)	0.473 (17)
O1A	−0.2574 (3)	0.54003 (12)	0.58733 (13)	0.0854 (7)	0.527 (17)
N2A	−0.0448 (2)	0.54973 (11)	0.76424 (12)	0.0751 (7)	0.527 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0561 (11)	0.0528 (10)	0.0477 (10)	0.0063 (9)	0.0085 (9)	−0.0031 (8)
C2	0.0650 (13)	0.0777 (13)	0.0509 (11)	−0.0018 (11)	−0.0007 (9)	0.0018 (9)
C3	0.0771 (14)	0.0744 (14)	0.0450 (10)	0.0102 (11)	0.0019 (10)	0.0063 (8)
C4	0.0640 (12)	0.0516 (10)	0.0448 (9)	0.0099 (9)	0.0141 (9)	0.0004 (7)
C5	0.0796 (14)	0.0627 (12)	0.0534 (11)	0.0080 (11)	0.0194 (11)	0.0074 (9)
C6	0.0747 (14)	0.0647 (13)	0.0751 (13)	−0.0037 (11)	0.0253 (11)	0.0090 (10)
C7	0.0706 (14)	0.0771 (14)	0.0676 (13)	−0.0116 (11)	0.0071 (11)	0.0052 (10)
C8	0.0699 (14)	0.0682 (13)	0.0515 (10)	−0.0032 (10)	0.0047 (10)	0.0087 (8)
C9	0.0583 (11)	0.0506 (10)	0.0439 (9)	0.0083 (9)	0.0075 (8)	−0.0007 (7)
C11	0.0600 (12)	0.0562 (11)	0.0604 (12)	0.0043 (9)	0.0112 (10)	−0.0050 (9)
C12	0.0734 (15)	0.0889 (15)	0.0850 (15)	−0.0119 (12)	0.0249 (12)	0.0050 (11)
C13	0.0698 (14)	0.0826 (15)	0.0923 (16)	−0.0137 (11)	0.0178 (13)	0.0012 (11)
N1	0.0580 (9)	0.0536 (9)	0.0481 (8)	0.0009 (7)	0.0075 (7)	0.0019 (6)
N2	0.0765 (12)	0.1034 (13)	0.0690 (11)	−0.0272 (9)	−0.0013 (9)	0.0046 (8)
O1	0.0772 (12)	0.0848 (12)	0.0607 (10)	−0.0168 (8)	0.0083 (8)	0.0091 (7)
O1A	0.0765 (12)	0.1034 (13)	0.0690 (11)	−0.0272 (9)	−0.0013 (9)	0.0046 (8)
N2A	0.0772 (12)	0.0848 (12)	0.0607 (10)	−0.0168 (8)	0.0083 (8)	0.0091 (7)

C1—N1	1.315 (2)	C7—H7	0.9300
C1—C2	1.412 (2)	C8—C9	1.411 (2)
C1—C11	1.472 (3)	C8—H8	0.9300
C2—C3	1.343 (3)	C9—N1	1.366 (2)
C2—H2	0.9300	C11—O1	1.289 (2)
C3—C4	1.409 (2)	C11—N2	1.307 (2)
C3—H3	0.9300	C12—O1	1.464 (2)
C4—C5	1.409 (2)	C12—C13	1.505 (3)
C4—C9	1.413 (2)	C12—H12A	0.9700
C5—C6	1.353 (2)	C12—H12B	0.9700
C5—H5	0.9300	C13—N2	1.450 (2)
C6—C7	1.405 (2)	C13—H13A	0.9700
C6—H6	0.9300	C13—H13B	0.9700
C7—C8	1.352 (3)
N1—C1—C2	123.27 (18)	C9—C8—H8	119.7
N1—C1—C11	117.23 (15)	N1—C9—C8	118.48 (15)
C2—C1—C11	119.46 (16)	N1—C9—C4	122.63 (16)
C3—C2—C1	119.45 (17)	C8—C9—C4	118.87 (18)
C3—C2—H2	120.3	O1—C11—N2	118.51 (18)
C1—C2—H2	120.3	O1—C11—C1	122.40 (16)
C2—C3—C4	119.85 (16)	N2—C11—C1	119.03 (16)
C2—C3—H3	120.1	O1—C12—C13	104.53 (16)
C4—C3—H3	120.1	O1—C12—H12A	110.8
C3—C4—C5	123.84 (16)	C13—C12—H12A	110.8
C3—C4—C9	117.14 (18)	O1—C12—H12B	110.8
C5—C4—C9	119.01 (17)	C13—C12—H12B	110.8
C6—C5—C4	120.54 (17)	H12A—C12—H12B	108.9
C6—C5—H5	119.7	N2—C13—C12	104.22 (15)
C4—C5—H5	119.7	N2—C13—H13A	110.9
C5—C6—C7	120.47 (19)	C12—C13—H13A	110.9
C5—C6—H6	119.8	N2—C13—H13B	110.9
C7—C6—H6	119.8	C12—C13—H13B	110.9
C8—C7—C6	120.50 (18)	H13A—C13—H13B	108.9
C8—C7—H7	119.7	C1—N1—C9	117.63 (14)
C6—C7—H7	119.7	C11—N2—C13	106.47 (15)
C7—C8—C9	120.60 (17)	C11—O1—C12	106.02 (16)
C7—C8—H8	119.7
N1—C1—C2—C3	−1.4 (3)	N1—C1—C11—O1	8.9 (3)
C11—C1—C2—C3	176.45 (16)	C2—C1—C11—O1	−169.11 (17)
C1—C2—C3—C4	1.1 (3)	N1—C1—C11—N2	−173.99 (16)
C2—C3—C4—C5	−178.70 (17)	C2—C1—C11—N2	8.0 (3)
C2—C3—C4—C9	0.2 (3)	O1—C12—C13—N2	−4.9 (2)
C3—C4—C5—C6	179.00 (17)	C2—C1—N1—C9	0.3 (2)
C9—C4—C5—C6	0.2 (3)	C11—C1—N1—C9	−177.55 (14)
C4—C5—C6—C7	0.0 (3)	C8—C9—N1—C1	179.31 (15)
C5—C6—C7—C8	0.4 (3)	C4—C9—N1—C1	1.0 (2)
C6—C7—C8—C9	−0.9 (3)	O1—C11—N2—C13	−1.2 (2)
C7—C8—C9—N1	−177.34 (17)	C1—C11—N2—C13	−178.42 (15)
C7—C8—C9—C4	1.1 (3)	C12—C13—N2—C11	3.8 (2)
C3—C4—C9—N1	−1.3 (2)	N2—C11—O1—C12	−2.2 (2)
C5—C4—C9—N1	177.67 (14)	C1—C11—O1—C12	174.98 (16)
C3—C4—C9—C8	−179.57 (15)	C13—C12—O1—C11	4.4 (2)
C5—C4—C9—C8	−0.6 (2)