2,6-Dimethyl-4-(1,3,4-oxadiazol-2-yl)quinoline.

The title compound, C(13)H(11)N(3)O, a potential chemotherapeutic agent, contains a essential planar [maximum deviation = 0.0144 (14) Å] quinoline moiety. The quinoline ring system and the five-membered heterocycle form a dihedral angle of 7.81 (6)°. In the crystal, inter-molecular non-classical C-H⋯N hydrogen bonding is present.

Related literature

For general background to the use of compounds containing a quinoline fragment as chemotherapeutical agents, see: Kaila et al. (2007 ▶); Vaitilingam et al. (2004 ▶).

Experimental

Crystal data

C13H11N3O

M = 225.25

Monoclinic,

a = 15.5372 (14) Å

b = 9.7546 (7) Å

c = 7.3984 (5) Å

β = 100.64 (1)°

V = 1102.02 (15) Å3

Z = 4

Cu Kα radiation

μ = 0.73 mm−1

T = 295 K

0.20 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: refined from ΔF (Walker & Stuart, 1983 ▶) T min = 0.391, T max = 0.865

2236 measured reflections

2236 independent reflections

1855 reflections with I > 2σ(I)

1 standard reflections every 60 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.130

S = 1.07

2236 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048683/ds2065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048683/ds2065Isup2.hkl

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

C13H11N3O	F(000) = 472
Mr = 225.25	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Melting point = 448–449 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 15.5372 (14) Å	Cell parameters from 25 reflections
b = 9.7546 (7) Å	θ = 36.3–39.9°
c = 7.3984 (5) Å	µ = 0.73 mm−1
β = 100.64 (1)°	T = 295 K
V = 1102.02 (15) Å3	Prism, colourless
Z = 4	0.20 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	1855 reflections with I > 2σ(I)
Radiation source: Fine-focus sealed tube	Rint = 0.0000
Graphite	θmax = 74.9°, θmin = 2.9°
Non–profiled ω scans	h = 0→19
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	k = 0→12
Tmin = 0.391, Tmax = 0.865	l = −8→9
2236 measured reflections	1 standard reflections every 60 min
2236 independent reflections	intensity decay: 1%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.1662P] where P = (Fo2 + 2Fc2)/3
2236 reflections	(Δ/σ)max = 0.005
156 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.39891 (8)	0.63577 (13)	0.05252 (18)	0.0557 (3)
C2	0.36926 (10)	0.75870 (16)	0.0823 (2)	0.0549 (4)
C21	0.42870 (12)	0.87852 (19)	0.0735 (3)	0.0720 (5)
H21A	0.4875	0.8464	0.0781	0.108*
H21B	0.4271	0.9383	0.1758	0.108*
H21C	0.4096	0.9276	−0.0393	0.108*
C3	0.28466 (10)	0.77894 (16)	0.1206 (2)	0.0537 (4)
H3	0.2663	0.8673	0.1417	0.064*
C4	0.22912 (9)	0.67122 (14)	0.12717 (19)	0.0479 (3)
C5	0.25819 (9)	0.53629 (15)	0.09414 (18)	0.0468 (3)
C6	0.20838 (9)	0.41454 (15)	0.09503 (19)	0.0505 (3)
H6	0.1513	0.4206	0.1158	0.061*
C7	0.24197 (10)	0.28864 (15)	0.0662 (2)	0.0532 (4)
C71	0.19028 (12)	0.15983 (16)	0.0748 (3)	0.0656 (4)
H71A	0.1315	0.1829	0.0868	0.098*
H71B	0.2171	0.1062	0.1789	0.098*
H71C	0.1891	0.1078	−0.0358	0.098*
C8	0.32817 (11)	0.28112 (16)	0.0302 (2)	0.0599 (4)
H8	0.3515	0.1959	0.0097	0.072*
C9	0.37777 (10)	0.39518 (17)	0.0249 (2)	0.0587 (4)
H9	0.4340	0.3871	−0.0003	0.070*
C10	0.34470 (9)	0.52589 (15)	0.0574 (2)	0.0508 (3)
C11	0.14273 (9)	0.69987 (15)	0.1721 (2)	0.0500 (3)
O12	0.11965 (7)	0.83379 (11)	0.18110 (16)	0.0631 (3)
C13	0.03932 (11)	0.8249 (2)	0.2255 (3)	0.0688 (5)
H13	0.0057	0.9013	0.2419	0.083*
N14	0.01403 (9)	0.70333 (17)	0.2429 (2)	0.0739 (4)
N15	0.08253 (9)	0.61910 (15)	0.2072 (2)	0.0651 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0469 (6)	0.0603 (8)	0.0626 (8)	−0.0012 (5)	0.0168 (5)	0.0026 (6)
C2	0.0506 (8)	0.0585 (9)	0.0568 (8)	−0.0052 (6)	0.0135 (6)	0.0015 (6)
C21	0.0661 (10)	0.0651 (10)	0.0887 (13)	−0.0142 (8)	0.0241 (9)	0.0008 (9)
C3	0.0542 (8)	0.0518 (8)	0.0570 (9)	0.0007 (6)	0.0150 (6)	−0.0010 (6)
C4	0.0464 (7)	0.0516 (8)	0.0468 (8)	0.0019 (6)	0.0117 (6)	0.0008 (6)
C5	0.0456 (7)	0.0520 (8)	0.0442 (7)	0.0029 (6)	0.0119 (5)	0.0018 (5)
C6	0.0472 (7)	0.0558 (8)	0.0508 (8)	0.0007 (6)	0.0150 (6)	0.0008 (6)
C7	0.0561 (8)	0.0517 (8)	0.0532 (8)	0.0012 (6)	0.0134 (6)	0.0002 (6)
C71	0.0701 (10)	0.0550 (9)	0.0745 (11)	−0.0045 (8)	0.0207 (8)	−0.0047 (7)
C8	0.0602 (9)	0.0530 (8)	0.0695 (10)	0.0098 (7)	0.0195 (7)	0.0008 (7)
C9	0.0491 (8)	0.0616 (9)	0.0693 (10)	0.0082 (7)	0.0209 (7)	0.0009 (7)
C10	0.0463 (7)	0.0557 (8)	0.0522 (8)	0.0019 (6)	0.0142 (6)	0.0033 (6)
C11	0.0501 (7)	0.0510 (8)	0.0506 (8)	0.0051 (6)	0.0138 (6)	−0.0015 (6)
O12	0.0570 (6)	0.0550 (6)	0.0804 (8)	0.0078 (5)	0.0207 (5)	−0.0039 (5)
C13	0.0575 (9)	0.0735 (11)	0.0795 (12)	0.0173 (8)	0.0235 (8)	−0.0056 (9)
N14	0.0573 (8)	0.0778 (10)	0.0940 (11)	0.0120 (7)	0.0337 (7)	0.0009 (8)
N15	0.0538 (7)	0.0647 (8)	0.0840 (10)	0.0053 (6)	0.0315 (7)	0.0014 (7)

N1—C2	1.3177 (19)	C7—C8	1.415 (2)
N1—C10	1.3677 (18)	C7—C71	1.499 (2)
C2—C3	1.408 (2)	C71—H71A	0.9600
C2—C21	1.499 (2)	C71—H71B	0.9600
C21—H21A	0.9600	C71—H71C	0.9600
C21—H21B	0.9600	C8—C9	1.358 (2)
C21—H21C	0.9600	C8—H8	0.9300
C3—C4	1.366 (2)	C9—C10	1.412 (2)
C3—H3	0.9300	C9—H9	0.9300
C4—C5	1.4271 (19)	C11—N15	1.286 (2)
C4—C11	1.4680 (19)	C11—O12	1.3596 (17)
C5—C6	1.4182 (19)	O12—C13	1.3508 (19)
C5—C10	1.4233 (19)	C13—N14	1.263 (2)
C6—C7	1.366 (2)	C13—H13	0.9300
C6—H6	0.9300	N14—N15	1.4075 (18)
C2—N1—C10	118.21 (12)	C7—C71—H71A	109.5
N1—C2—C3	121.95 (14)	C7—C71—H71B	109.5
N1—C2—C21	117.71 (14)	H71A—C71—H71B	109.5
C3—C2—C21	120.33 (14)	C7—C71—H71C	109.5
C2—C21—H21A	109.5	H71A—C71—H71C	109.5
C2—C21—H21B	109.5	H71B—C71—H71C	109.5
H21A—C21—H21B	109.5	C9—C8—C7	121.66 (14)
C2—C21—H21C	109.5	C9—C8—H8	119.2
H21A—C21—H21C	109.5	C7—C8—H8	119.2
H21B—C21—H21C	109.5	C8—C9—C10	120.58 (13)
C4—C3—C2	121.23 (14)	C8—C9—H9	119.7
C4—C3—H3	119.4	C10—C9—H9	119.7
C2—C3—H3	119.4	N1—C10—C9	117.26 (13)
C3—C4—C5	118.75 (13)	N1—C10—C5	123.86 (13)
C3—C4—C11	118.15 (13)	C9—C10—C5	118.88 (13)
C5—C4—C11	123.09 (12)	N15—C11—O12	111.76 (13)
C6—C5—C10	118.46 (13)	N15—C11—C4	131.21 (14)
C6—C5—C4	125.54 (12)	O12—C11—C4	117.03 (12)
C10—C5—C4	116.00 (13)	C13—O12—C11	102.38 (12)
C7—C6—C5	121.84 (13)	N14—C13—O12	113.79 (14)
C7—C6—H6	119.1	N14—C13—H13	123.1
C5—C6—H6	119.1	O12—C13—H13	123.1
C6—C7—C8	118.56 (14)	C13—N14—N15	105.60 (13)
C6—C7—C71	121.59 (13)	C11—N15—N14	106.47 (14)
C8—C7—C71	119.84 (14)
C10—N1—C2—C3	0.7 (2)	C2—N1—C10—C5	−0.4 (2)
C10—N1—C2—C21	−178.99 (14)	C8—C9—C10—N1	179.04 (14)
N1—C2—C3—C4	−0.4 (2)	C8—C9—C10—C5	−0.6 (2)
C21—C2—C3—C4	179.24 (15)	C6—C5—C10—N1	179.88 (13)
C2—C3—C4—C5	−0.1 (2)	C4—C5—C10—N1	−0.1 (2)
C2—C3—C4—C11	178.58 (13)	C6—C5—C10—C9	−0.5 (2)
C3—C4—C5—C6	−179.61 (13)	C4—C5—C10—C9	179.53 (13)
C11—C4—C5—C6	1.8 (2)	C3—C4—C11—N15	−171.28 (16)
C3—C4—C5—C10	0.3 (2)	C5—C4—C11—N15	7.4 (3)
C11—C4—C5—C10	−178.28 (13)	C3—C4—C11—O12	8.1 (2)
C10—C5—C6—C7	1.6 (2)	C5—C4—C11—O12	−173.22 (12)
C4—C5—C6—C7	−178.43 (14)	N15—C11—O12—C13	0.07 (17)
C5—C6—C7—C8	−1.6 (2)	C4—C11—O12—C13	−179.46 (13)
C5—C6—C7—C71	177.53 (14)	C11—O12—C13—N14	0.0 (2)
C6—C7—C8—C9	0.4 (2)	O12—C13—N14—N15	−0.1 (2)
C71—C7—C8—C9	−178.70 (15)	O12—C11—N15—N14	−0.13 (18)
C7—C8—C9—C10	0.7 (3)	C4—C11—N15—N14	179.32 (15)
C2—N1—C10—C9	179.94 (13)	C13—N14—N15—C11	0.14 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N15i	0.93	2.59	3.523 (2)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N15i	0.93	2.59	3.523 (2)	178

Symmetry code: (i) .