3-(3-Methyl-phen-yl)-5-(quinolin-8-yl-meth-oxy)-1,2,4-oxa-diazole monohydrate.

In the title compound, C19H15N3O2·H2O, the oxa-diazole ring and the quinoline unit are almost coplanar, making a dihedral angle of 7.66 (8)°. The dihedral angle between the benzene ring and the quinoline system is 25.95 (8)° while that between the benzene and the oxa-diazole rings is 18.88 (9)°. The water mol-ecule is hydrogen bonded to an oxa-diazole N atom and to the quinoline N atom. In the crystal, these units are linked via C-H⋯O hydrogen bonds, forming two-dimensional net-works lying parallel to the ab plane.

Related literature

For the preparation of the title compound, see: Chiou & Shine (1989 ▶). For the biological activity of 1,2,4-oxa­diazole derivatives, see: Street et al. (1990 ▶). For metal complexes of related compounds, see: da Silva et al. (1999 ▶); Pibiri et al. (2010 ▶); Terenzi et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H15N3O2·H2O

M = 335.36

Triclinic,

a = 7.2070 (14) Å

b = 7.6200 (15) Å

c = 15.109 (3) Å

α = 92.62 (3)°

β = 90.19 (3)°

γ = 92.15 (3)°

V = 828.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.973, T max = 0.991

3302 measured reflections

3039 independent reflections

1949 reflections with I > 2σ(I)

R int = 0.015

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.162

S = 1.00

3039 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.18 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) D, I. DOI: 10.1107/S160053681302477X/im2428sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302477X/im2428Isup2.hkl

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

C19H15N3O2·H2O	Z = 2
Mr = 335.36	F(000) = 352
Triclinic, P1	Dx = 1.345 Mg m−3
Hall symbol: -P 1	Melting point: 342 K
a = 7.2070 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6200 (15) Å	Cell parameters from 25 reflections
c = 15.109 (3) Å	θ = 9–13°
α = 92.62 (3)°	µ = 0.09 mm−1
β = 90.19 (3)°	T = 293 K
γ = 92.15 (3)°	Block, yellow
V = 828.3 (3) Å3	0.30 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1949 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.4°, θmin = 1.4°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.973, Tmax = 0.991	l = −18→18
3302 measured reflections	3 standard reflections every 200 reflections
3039 independent reflections	intensity decay: 1%

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.097P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3039 reflections	Δρmax = 0.24 e Å−3
233 parameters	Δρmin = −0.18 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: 0.033 (7)

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
O1	0.0819 (2)	0.7951 (2)	0.99656 (11)	0.0571 (5)
N1	−0.1889 (3)	0.6301 (2)	1.08273 (13)	0.0522 (5)
C1	0.2813 (3)	0.8077 (3)	1.12657 (18)	0.0596 (7)
H1B	0.3763	0.8670	1.0974	0.071*
N2	0.0057 (3)	0.8438 (2)	0.81930 (13)	0.0511 (5)
O2	0.2873 (2)	0.9553 (2)	0.80096 (12)	0.0695 (6)
C2	0.3046 (4)	0.7675 (4)	1.21478 (19)	0.0667 (7)
H2B	0.4155	0.8005	1.2437	0.080*
C3	0.1700 (4)	0.6819 (4)	1.25913 (18)	0.0656 (7)
H3A	0.1894	0.6553	1.3178	0.079*
N3	0.2016 (3)	0.9460 (3)	0.71676 (15)	0.0714 (7)
C4	−0.0008 (3)	0.6320 (3)	1.21701 (17)	0.0551 (6)
C5	−0.1489 (4)	0.5465 (3)	1.25918 (18)	0.0642 (7)
H5A	−0.1374	0.5179	1.3181	0.077*
C6	−0.3092 (4)	0.5051 (3)	1.21418 (19)	0.0653 (7)
H6A	−0.4084	0.4483	1.2416	0.078*
C7	−0.3218 (3)	0.5497 (3)	1.12629 (18)	0.0594 (7)
H7A	−0.4323	0.5206	1.0962	0.071*
C8	−0.0273 (3)	0.6721 (3)	1.12723 (16)	0.0475 (6)
C9	0.1196 (3)	0.7605 (3)	1.08256 (16)	0.0486 (6)
C10	0.2240 (3)	0.8842 (3)	0.94993 (17)	0.0557 (6)
H10A	0.3386	0.8219	0.9528	0.067*
H10B	0.2460	1.0022	0.9757	0.067*
C11	0.1608 (3)	0.8911 (3)	0.85698 (17)	0.0511 (6)
C12	0.0369 (3)	0.8783 (3)	0.73185 (16)	0.0535 (6)
C13	−0.0981 (3)	0.8373 (3)	0.66076 (16)	0.0553 (6)
C14	−0.2843 (4)	0.8113 (3)	0.67896 (17)	0.0617 (7)
H14A	−0.3249	0.8161	0.7374	0.074*
C15	−0.4105 (4)	0.7784 (4)	0.61087 (18)	0.0687 (7)
H15A	−0.5356	0.7628	0.6245	0.082*
C16	−0.3573 (4)	0.7677 (3)	0.52325 (17)	0.0677 (8)
C17	−0.1699 (5)	0.7904 (4)	0.50615 (19)	0.0847 (9)
H17A	−0.1291	0.7826	0.4478	0.102*
C18	−0.0424 (4)	0.8242 (4)	0.57307 (19)	0.0814 (9)
H18A	0.0828	0.8385	0.5594	0.098*
C19	−0.4974 (5)	0.7358 (4)	0.45006 (19)	0.0905 (10)
H19A	−0.4352	0.7339	0.3940	0.136*
H19B	−0.5845	0.8282	0.4523	0.136*
H19C	−0.5622	0.6250	0.4571	0.136*
OW	−0.3313 (2)	0.7299 (3)	0.91840 (14)	0.0733 (6)
HWB	−0.236 (5)	0.757 (4)	0.8819 (19)	0.088*
HWA	−0.274 (4)	0.682 (4)	0.967 (2)	0.088*

	U11	U22	U33	U12	U13	U23
O1	0.0383 (8)	0.0683 (11)	0.0639 (11)	−0.0106 (8)	−0.0065 (8)	0.0075 (8)
N1	0.0400 (10)	0.0500 (11)	0.0661 (13)	−0.0038 (9)	−0.0033 (10)	0.0013 (9)
C1	0.0387 (13)	0.0624 (16)	0.0769 (19)	0.0010 (11)	−0.0102 (12)	−0.0030 (13)
N2	0.0425 (11)	0.0550 (12)	0.0551 (12)	−0.0019 (9)	0.0074 (9)	−0.0021 (9)
O2	0.0450 (10)	0.0884 (13)	0.0744 (13)	−0.0133 (9)	0.0078 (9)	0.0081 (10)
C2	0.0498 (15)	0.0751 (18)	0.0742 (19)	0.0041 (13)	−0.0197 (14)	−0.0088 (14)
C3	0.0634 (17)	0.0752 (18)	0.0579 (16)	0.0075 (14)	−0.0165 (14)	−0.0034 (13)
N3	0.0556 (13)	0.0913 (17)	0.0670 (15)	−0.0103 (12)	0.0084 (12)	0.0106 (12)
C4	0.0528 (14)	0.0486 (13)	0.0640 (16)	0.0094 (11)	−0.0032 (12)	−0.0022 (11)
C5	0.0694 (18)	0.0598 (16)	0.0643 (17)	0.0119 (14)	0.0029 (14)	0.0052 (13)
C6	0.0580 (16)	0.0608 (16)	0.0773 (19)	−0.0011 (13)	0.0091 (14)	0.0079 (14)
C7	0.0457 (14)	0.0567 (15)	0.0753 (18)	−0.0028 (12)	−0.0016 (13)	0.0017 (13)
C8	0.0405 (12)	0.0420 (12)	0.0595 (15)	0.0032 (10)	−0.0053 (11)	−0.0046 (10)
C9	0.0370 (12)	0.0478 (13)	0.0607 (15)	0.0047 (10)	−0.0081 (11)	−0.0021 (11)
C10	0.0327 (11)	0.0617 (15)	0.0713 (17)	−0.0062 (11)	0.0050 (11)	−0.0053 (12)
C11	0.0351 (12)	0.0505 (13)	0.0668 (16)	−0.0005 (10)	0.0058 (11)	−0.0041 (11)
C12	0.0478 (13)	0.0534 (14)	0.0592 (16)	0.0016 (11)	0.0118 (11)	0.0019 (11)
C13	0.0573 (15)	0.0544 (14)	0.0540 (15)	0.0009 (12)	0.0074 (12)	0.0002 (11)
C14	0.0577 (15)	0.0757 (17)	0.0516 (15)	0.0001 (13)	0.0060 (12)	0.0021 (12)
C15	0.0590 (15)	0.0846 (19)	0.0623 (18)	−0.0007 (14)	−0.0003 (13)	0.0034 (14)
C16	0.085 (2)	0.0642 (17)	0.0536 (17)	0.0042 (15)	−0.0039 (14)	0.0020 (13)
C17	0.090 (2)	0.112 (3)	0.0512 (17)	−0.0007 (19)	0.0109 (16)	−0.0037 (16)
C18	0.0700 (18)	0.111 (2)	0.0616 (18)	−0.0049 (17)	0.0182 (16)	−0.0037 (16)
C19	0.111 (3)	0.100 (2)	0.0606 (18)	0.003 (2)	−0.0170 (18)	0.0006 (17)
OW	0.0446 (10)	0.1012 (15)	0.0735 (13)	−0.0152 (10)	−0.0081 (9)	0.0147 (11)

O1—C9	1.366 (3)	C7—H7A	0.9300
O1—C10	1.415 (3)	C8—C9	1.422 (3)
N1—C7	1.313 (3)	C10—C11	1.479 (4)
N1—C8	1.363 (3)	C10—H10A	0.9700
C1—C9	1.368 (3)	C10—H10B	0.9700
C1—C2	1.392 (4)	C12—C13	1.462 (3)
C1—H1B	0.9300	C13—C14	1.380 (4)
N2—C11	1.285 (3)	C13—C18	1.386 (4)
N2—C12	1.376 (3)	C14—C15	1.379 (4)
O2—C11	1.340 (3)	C14—H14A	0.9300
O2—N3	1.410 (3)	C15—C16	1.379 (4)
C2—C3	1.346 (4)	C15—H15A	0.9300
C2—H2B	0.9300	C16—C17	1.381 (4)
C3—C4	1.415 (3)	C16—C19	1.501 (4)
C3—H3A	0.9300	C17—C18	1.373 (4)
N3—C12	1.301 (3)	C17—H17A	0.9300
C4—C5	1.400 (4)	C18—H18A	0.9300
C4—C8	1.418 (3)	C19—H19A	0.9600
C5—C6	1.358 (4)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.389 (4)	OW—HWB	0.91 (3)
C6—H6A	0.9300	OW—HWA	0.94 (3)
C9—O1—C10	116.60 (18)	O1—C10—H10B	110.3
C7—N1—C8	117.4 (2)	C11—C10—H10B	110.3
C9—C1—C2	120.5 (2)	H10A—C10—H10B	108.5
C9—C1—H1B	119.8	N2—C11—O2	113.4 (2)
C2—C1—H1B	119.8	N2—C11—C10	131.4 (2)
C11—N2—C12	103.1 (2)	O2—C11—C10	115.16 (19)
C11—O2—N3	105.97 (17)	N3—C12—N2	114.0 (2)
C3—C2—C1	121.4 (2)	N3—C12—C13	122.2 (2)
C3—C2—H2B	119.3	N2—C12—C13	123.9 (2)
C1—C2—H2B	119.3	C14—C13—C18	118.2 (3)
C2—C3—C4	120.4 (3)	C14—C13—C12	121.0 (2)
C2—C3—H3A	119.8	C18—C13—C12	120.8 (2)
C4—C3—H3A	119.8	C15—C14—C13	120.2 (2)
C12—N3—O2	103.59 (19)	C15—C14—H14A	119.9
C5—C4—C3	123.8 (3)	C13—C14—H14A	119.9
C5—C4—C8	117.1 (2)	C14—C15—C16	122.2 (3)
C3—C4—C8	119.0 (2)	C14—C15—H15A	118.9
C6—C5—C4	120.1 (3)	C16—C15—H15A	118.9
C6—C5—H5A	120.0	C15—C16—C17	116.9 (3)
C4—C5—H5A	120.0	C15—C16—C19	121.3 (3)
C5—C6—C7	118.5 (3)	C17—C16—C19	121.8 (3)
C5—C6—H6A	120.7	C18—C17—C16	121.7 (3)
C7—C6—H6A	120.7	C18—C17—H17A	119.2
N1—C7—C6	124.6 (2)	C16—C17—H17A	119.2
N1—C7—H7A	117.7	C17—C18—C13	120.8 (3)
C6—C7—H7A	117.7	C17—C18—H18A	119.6
N1—C8—C4	122.3 (2)	C13—C18—H18A	119.6
N1—C8—C9	119.1 (2)	C16—C19—H19A	109.5
C4—C8—C9	118.7 (2)	C16—C19—H19B	109.5
O1—C9—C1	125.1 (2)	H19A—C19—H19B	109.5
O1—C9—C8	114.81 (19)	C16—C19—H19C	109.5
C1—C9—C8	120.1 (2)	H19A—C19—H19C	109.5
O1—C10—C11	107.17 (18)	H19B—C19—H19C	109.5
O1—C10—H10A	110.3	HWB—OW—HWA	104 (3)
C11—C10—H10A	110.3
C9—C1—C2—C3	0.0 (4)	C12—N2—C11—O2	0.9 (3)
C1—C2—C3—C4	−0.8 (4)	C12—N2—C11—C10	−177.9 (2)
C11—O2—N3—C12	−0.1 (3)	N3—O2—C11—N2	−0.5 (3)
C2—C3—C4—C5	−178.5 (2)	N3—O2—C11—C10	178.5 (2)
C2—C3—C4—C8	0.6 (4)	O1—C10—C11—N2	5.4 (4)
C3—C4—C5—C6	179.2 (2)	O1—C10—C11—O2	−173.34 (19)
C8—C4—C5—C6	0.1 (4)	O2—N3—C12—N2	0.7 (3)
C4—C5—C6—C7	0.0 (4)	O2—N3—C12—C13	−177.1 (2)
C8—N1—C7—C6	0.1 (4)	C11—N2—C12—N3	−1.0 (3)
C5—C6—C7—N1	−0.1 (4)	C11—N2—C12—C13	176.7 (2)
C7—N1—C8—C4	0.0 (3)	N3—C12—C13—C14	−162.3 (3)
C7—N1—C8—C9	−179.5 (2)	N2—C12—C13—C14	20.1 (4)
C5—C4—C8—N1	−0.1 (3)	N3—C12—C13—C18	17.4 (4)
C3—C4—C8—N1	−179.2 (2)	N2—C12—C13—C18	−160.1 (3)
C5—C4—C8—C9	179.4 (2)	C18—C13—C14—C15	−1.8 (4)
C3—C4—C8—C9	0.3 (3)	C12—C13—C14—C15	177.9 (2)
C10—O1—C9—C1	1.1 (3)	C13—C14—C15—C16	0.9 (4)
C10—O1—C9—C8	179.53 (19)	C14—C15—C16—C17	0.4 (4)
C2—C1—C9—O1	179.3 (2)	C14—C15—C16—C19	−178.6 (3)
C2—C1—C9—C8	0.9 (4)	C15—C16—C17—C18	−0.7 (5)
N1—C8—C9—O1	0.0 (3)	C19—C16—C17—C18	178.2 (3)
C4—C8—C9—O1	−179.54 (19)	C16—C17—C18—C13	−0.2 (5)
N1—C8—C9—C1	178.5 (2)	C14—C13—C18—C17	1.5 (5)
C4—C8—C9—C1	−1.1 (3)	C12—C13—C18—C17	−178.2 (3)
C9—O1—C10—C11	174.34 (18)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWB···N2	0.91 (3)	2.09 (3)	2.980 (3)	169 (3)
OW—HWA···N1	0.94 (3)	1.91 (3)	2.830 (3)	165 (3)
C7—H7A···OWi	0.93	2.51	3.272 (3)	139
C10—H10A···OWii	0.97	2.55	3.482 (3)	160
C10—H10B···OWiii	0.97	2.59	3.534 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWB⋯N2	0.91 (3)	2.09 (3)	2.980 (3)	169 (3)
OW—HWA⋯N1	0.94 (3)	1.91 (3)	2.830 (3)	165 (3)
C7—H7A⋯OW i	0.93	2.51	3.272 (3)	139
C10—H10A⋯OW ii	0.97	2.55	3.482 (3)	160
C10—H10B⋯OW iii	0.97	2.59	3.534 (3)	164

Symmetry codes: (i) ; (ii) ; (iii) .