Crystal structure of 2-{[(naphthalen-1-yl)oxy]meth-yl}-5-(2,4,5-tri-fluoro-phen-yl)-1,3,4-oxa-diazole.

In the title compound C19H11F3N2O2, the oxa-diazole ring and the naphthalene ring system are approximately planar (r.m.s. deviations of 0.001 and 0.020 Å, respectively) and the oxa-diazole ring makes dihedral angles of 13.11 (1) and 7.59 (1)° with the naphthalene ring system and the tri-fluoro-phenyl ring, respectively. In the crystal, C-H⋯N hydrogen bonds link mol-ecules into chains along the a-axis direction, while C-H⋯F contacts form additional chains along the ac diagonal. These contacts generate sheets of mol-ecules approximately parallel to the (011) plane.

Related literature

For the biological activity and other applications of triazole derivatives, see: Desai et al. (2014 ▸); Bhat et al. (2011 ▸); Katrin et al. (2005 ▸); Shailaja et al. (2010 ▸).

Experimental

Crystal data

C19H11F3N2O2

M = 356.30

Triclinic,

a = 7.4817 (5) Å

b = 7.5928 (5) Å

c = 15.7908 (10) Å

α = 78.673 (3)°

β = 78.404 (3)°

γ = 65.370 (3)°

V = 792.36 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.970, T max = 0.988

11539 measured reflections

3330 independent reflections

2402 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.140

S = 1.04

3330 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.31 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: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015003205/sj5445sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015003205/sj5445Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015003205/sj5445Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015003205/sj5445fig1.tif

The mol­ecular structure of the title compound, showing the atomic numbering with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015003205/sj5445fig2.tif

Crystal packing of the title compound viewed along the a axis H-atoms not involved in H-bonds have been excluded for clarity.

CCDC reference: 1049573

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

C19H11F3N2O2	Z = 2
Mr = 356.30	F(000) = 364
Triclinic, P1	Dx = 1.493 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4817 (5) Å	Cell parameters from 3330 reflections
b = 7.5928 (5) Å	θ = 1.3–26.8°
c = 15.7908 (10) Å	µ = 0.12 mm−1
α = 78.673 (3)°	T = 293 K
β = 78.404 (3)°	Block, colourless
γ = 65.370 (3)°	0.25 × 0.15 × 0.10 mm
V = 792.36 (9) Å3

Bruker SMART APEXII area-detector diffractometer	3330 independent reflections
Radiation source: fine-focus sealed tube	2402 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 26.8°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.970, Tmax = 0.988	k = −9→9
11539 measured reflections	l = −19→19

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) = 0.140	w = 1/[σ2(Fo2) + (0.062P)2 + 0.2065P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3330 reflections	Δρmax = 0.22 e Å−3
236 parameters	Δρmin = −0.31 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: 0.006 (2)

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
C1	0.4888 (3)	0.3315 (3)	0.37814 (13)	0.0588 (5)
H1	0.5114	0.2802	0.4354	0.071*
C2	0.6415 (3)	0.3567 (3)	0.31604 (15)	0.0691 (6)
H2	0.7656	0.3212	0.3326	0.083*
C3	0.6121 (3)	0.4313 (3)	0.23273 (14)	0.0673 (5)
H3	0.7168	0.4439	0.1925	0.081*
C4	0.4239 (3)	0.4907 (3)	0.20584 (12)	0.0543 (5)
C5	0.3867 (3)	0.5717 (3)	0.12011 (13)	0.0670 (5)
H5	0.4891	0.5862	0.0789	0.080*
C6	0.2045 (4)	0.6293 (3)	0.09616 (14)	0.0744 (6)
H6	0.1830	0.6829	0.0390	0.089*
C7	0.0489 (3)	0.6080 (3)	0.15737 (14)	0.0699 (6)
H7	−0.0759	0.6483	0.1406	0.084*
C8	0.0783 (3)	0.5289 (3)	0.24135 (13)	0.0578 (5)
H8	−0.0265	0.5158	0.2814	0.069*
C9	0.2666 (3)	0.4668 (2)	0.26779 (11)	0.0474 (4)
C10	0.3070 (3)	0.3827 (2)	0.35414 (11)	0.0483 (4)
C11	0.1842 (3)	0.2579 (3)	0.49334 (11)	0.0540 (4)
H11A	0.2063	0.3365	0.5285	0.065*
H11B	0.2998	0.1361	0.4898	0.065*
C12	0.0033 (3)	0.2197 (2)	0.53195 (11)	0.0491 (4)
C13	−0.1893 (3)	0.1278 (2)	0.63030 (12)	0.0516 (4)
C14	−0.2556 (3)	0.0518 (3)	0.71692 (12)	0.0595 (5)
C15	−0.1309 (4)	−0.0186 (3)	0.78032 (14)	0.0767 (6)
H15	−0.0047	−0.0168	0.7679	0.092*
C16	−0.1951 (6)	−0.0916 (4)	0.86218 (16)	0.1020 (10)
C17	−0.3818 (6)	−0.0941 (4)	0.88135 (19)	0.1061 (12)
C18	−0.5058 (5)	−0.0245 (4)	0.8207 (2)	0.1034 (11)
H18	−0.6323	−0.0254	0.8342	0.124*
C19	−0.4444 (4)	0.0477 (3)	0.73917 (17)	0.0761 (7)
N1	−0.1442 (3)	0.2435 (2)	0.49547 (10)	0.0622 (4)
N2	−0.2727 (2)	0.1818 (2)	0.56086 (11)	0.0620 (4)
O1	0.14915 (18)	0.35881 (19)	0.40929 (8)	0.0582 (4)
O2	−0.01186 (18)	0.14762 (17)	0.61719 (7)	0.0520 (3)
F1	−0.0726 (4)	−0.1601 (3)	0.92306 (11)	0.1607 (9)
F2	−0.4342 (4)	−0.1687 (3)	0.96228 (11)	0.1684 (11)
F3	−0.5703 (2)	0.1171 (3)	0.68014 (13)	0.1095 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0581 (11)	0.0638 (11)	0.0548 (11)	−0.0257 (9)	−0.0118 (9)	0.0004 (9)
C2	0.0548 (11)	0.0827 (14)	0.0737 (14)	−0.0332 (10)	−0.0113 (10)	−0.0018 (11)
C3	0.0564 (11)	0.0796 (13)	0.0672 (13)	−0.0357 (10)	0.0033 (10)	−0.0038 (10)
C4	0.0632 (11)	0.0516 (9)	0.0494 (10)	−0.0280 (8)	0.0000 (8)	−0.0044 (8)
C5	0.0804 (14)	0.0697 (12)	0.0523 (11)	−0.0389 (11)	0.0030 (10)	−0.0017 (9)
C6	0.0996 (18)	0.0763 (14)	0.0483 (11)	−0.0395 (13)	−0.0165 (11)	0.0081 (10)
C7	0.0737 (13)	0.0743 (13)	0.0643 (13)	−0.0317 (11)	−0.0240 (11)	0.0069 (10)
C8	0.0586 (11)	0.0608 (11)	0.0557 (11)	−0.0285 (9)	−0.0075 (9)	0.0000 (8)
C9	0.0538 (10)	0.0431 (8)	0.0461 (9)	−0.0215 (7)	−0.0049 (7)	−0.0038 (7)
C10	0.0498 (10)	0.0478 (9)	0.0468 (10)	−0.0212 (7)	−0.0020 (8)	−0.0047 (7)
C11	0.0594 (11)	0.0543 (10)	0.0452 (10)	−0.0225 (8)	−0.0082 (8)	0.0021 (8)
C12	0.0587 (10)	0.0461 (9)	0.0404 (9)	−0.0205 (8)	−0.0072 (8)	−0.0006 (7)
C13	0.0597 (11)	0.0440 (9)	0.0495 (10)	−0.0213 (8)	−0.0028 (8)	−0.0049 (7)
C14	0.0797 (13)	0.0438 (9)	0.0496 (11)	−0.0250 (9)	0.0047 (9)	−0.0061 (8)
C15	0.1047 (18)	0.0658 (12)	0.0487 (12)	−0.0290 (12)	−0.0033 (11)	−0.0001 (9)
C16	0.170 (3)	0.0668 (14)	0.0494 (13)	−0.0327 (17)	−0.0085 (17)	0.0005 (11)
C17	0.174 (3)	0.0633 (14)	0.0662 (17)	−0.0576 (18)	0.047 (2)	−0.0151 (12)
C18	0.130 (3)	0.0742 (16)	0.100 (2)	−0.0583 (17)	0.0498 (19)	−0.0246 (15)
C19	0.0887 (16)	0.0575 (12)	0.0788 (15)	−0.0364 (11)	0.0182 (13)	−0.0137 (11)
N1	0.0677 (10)	0.0713 (10)	0.0480 (9)	−0.0315 (8)	−0.0122 (8)	0.0060 (7)
N2	0.0668 (10)	0.0677 (10)	0.0549 (10)	−0.0327 (8)	−0.0108 (8)	0.0020 (8)
O1	0.0534 (7)	0.0692 (8)	0.0444 (7)	−0.0241 (6)	−0.0046 (5)	0.0083 (6)
O2	0.0606 (8)	0.0538 (7)	0.0410 (7)	−0.0243 (6)	−0.0080 (5)	0.0010 (5)
F1	0.249 (3)	0.1436 (16)	0.0596 (10)	−0.0549 (17)	−0.0400 (13)	0.0235 (10)
F2	0.303 (3)	0.1016 (12)	0.0759 (11)	−0.1005 (16)	0.0777 (14)	−0.0141 (9)
F3	0.0853 (10)	0.1222 (13)	0.1295 (14)	−0.0566 (9)	0.0005 (10)	−0.0139 (11)

C1—C10	1.361 (3)	C11—C12	1.487 (3)
C1—C2	1.401 (3)	C11—H11A	0.9700
C1—H1	0.9300	C11—H11B	0.9700
C2—C3	1.349 (3)	C12—N1	1.277 (2)
C2—H2	0.9300	C12—O2	1.351 (2)
C3—C4	1.415 (3)	C13—N2	1.283 (2)
C3—H3	0.9300	C13—O2	1.368 (2)
C4—C5	1.404 (3)	C13—C14	1.451 (3)
C4—C9	1.421 (2)	C14—C15	1.381 (3)
C5—C6	1.355 (3)	C14—C19	1.398 (3)
C5—H5	0.9300	C15—C16	1.378 (3)
C6—C7	1.400 (3)	C15—H15	0.9300
C6—H6	0.9300	C16—F1	1.340 (4)
C7—C8	1.364 (3)	C16—C17	1.376 (5)
C7—H7	0.9300	C17—F2	1.344 (3)
C8—C9	1.410 (3)	C17—C18	1.344 (5)
C8—H8	0.9300	C18—C19	1.366 (4)
C9—C10	1.422 (2)	C18—H18	0.9300
C10—O1	1.375 (2)	C19—F3	1.334 (3)
C11—O1	1.411 (2)	N1—N2	1.413 (2)
C10—C1—C2	119.51 (18)	C12—C11—H11A	110.5
C10—C1—H1	120.2	O1—C11—H11B	110.5
C2—C1—H1	120.2	C12—C11—H11B	110.5
C3—C2—C1	121.32 (19)	H11A—C11—H11B	108.7
C3—C2—H2	119.3	N1—C12—O2	113.26 (16)
C1—C2—H2	119.3	N1—C12—C11	129.06 (16)
C2—C3—C4	120.79 (18)	O2—C12—C11	117.67 (15)
C2—C3—H3	119.6	N2—C13—O2	112.38 (16)
C4—C3—H3	119.6	N2—C13—C14	129.71 (19)
C5—C4—C3	122.47 (18)	O2—C13—C14	117.91 (17)
C5—C4—C9	118.68 (18)	C15—C14—C19	118.1 (2)
C3—C4—C9	118.85 (18)	C15—C14—C13	120.0 (2)
C6—C5—C4	121.36 (19)	C19—C14—C13	122.0 (2)
C6—C5—H5	119.3	C16—C15—C14	119.4 (3)
C4—C5—H5	119.3	C16—C15—H15	120.3
C5—C6—C7	120.0 (2)	C14—C15—H15	120.3
C5—C6—H6	120.0	F1—C16—C17	120.4 (3)
C7—C6—H6	120.0	F1—C16—C15	118.9 (3)
C8—C7—C6	120.7 (2)	C17—C16—C15	120.7 (3)
C8—C7—H7	119.6	F2—C17—C18	121.7 (4)
C6—C7—H7	119.6	F2—C17—C16	117.6 (4)
C7—C8—C9	120.36 (18)	C18—C17—C16	120.7 (3)
C7—C8—H8	119.8	C17—C18—C19	119.4 (3)
C9—C8—H8	119.8	C17—C18—H18	120.3
C8—C9—C4	118.84 (17)	C19—C18—H18	120.3
C8—C9—C10	123.12 (16)	F3—C19—C18	118.4 (3)
C4—C9—C10	118.04 (16)	F3—C19—C14	119.9 (2)
C1—C10—O1	124.10 (16)	C18—C19—C14	121.7 (3)
C1—C10—C9	121.46 (16)	C12—N1—N2	105.99 (15)
O1—C10—C9	114.45 (15)	C13—N2—N1	106.01 (15)
O1—C11—C12	106.06 (14)	C10—O1—C11	117.48 (14)
O1—C11—H11A	110.5	C12—O2—C13	102.37 (13)
C10—C1—C2—C3	0.2 (3)	C13—C14—C15—C16	−179.59 (18)
C1—C2—C3—C4	1.4 (3)	C14—C15—C16—F1	179.8 (2)
C2—C3—C4—C5	179.02 (19)	C14—C15—C16—C17	−0.3 (4)
C2—C3—C4—C9	−1.2 (3)	F1—C16—C17—F2	−0.6 (4)
C3—C4—C5—C6	−179.3 (2)	C15—C16—C17—F2	179.5 (2)
C9—C4—C5—C6	0.9 (3)	F1—C16—C17—C18	179.6 (2)
C4—C5—C6—C7	−0.2 (3)	C15—C16—C17—C18	−0.3 (4)
C5—C6—C7—C8	−0.3 (3)	F2—C17—C18—C19	−179.3 (2)
C6—C7—C8—C9	−0.1 (3)	C16—C17—C18—C19	0.6 (4)
C7—C8—C9—C4	0.9 (3)	C17—C18—C19—F3	−179.6 (2)
C7—C8—C9—C10	−179.79 (17)	C17—C18—C19—C14	−0.2 (4)
C5—C4—C9—C8	−1.3 (3)	C15—C14—C19—F3	179.00 (19)
C3—C4—C9—C8	178.98 (17)	C13—C14—C19—F3	−0.7 (3)
C5—C4—C9—C10	179.36 (16)	C15—C14—C19—C18	−0.4 (3)
C3—C4—C9—C10	−0.4 (2)	C13—C14—C19—C18	179.84 (19)
C2—C1—C10—O1	178.07 (17)	O2—C12—N1—N2	−0.3 (2)
C2—C1—C10—C9	−1.9 (3)	C11—C12—N1—N2	178.92 (17)
C8—C9—C10—C1	−177.39 (17)	O2—C13—N2—N1	−0.1 (2)
C4—C9—C10—C1	2.0 (2)	C14—C13—N2—N1	179.94 (17)
C8—C9—C10—O1	2.7 (2)	C12—N1—N2—C13	0.2 (2)
C4—C9—C10—O1	−177.99 (14)	C1—C10—O1—C11	−6.4 (3)
O1—C11—C12—N1	9.7 (3)	C9—C10—O1—C11	173.59 (14)
O1—C11—C12—O2	−171.20 (14)	C12—C11—O1—C10	−169.31 (14)
N2—C13—C14—C15	172.59 (19)	N1—C12—O2—C13	0.18 (19)
O2—C13—C14—C15	−7.3 (3)	C11—C12—O2—C13	−179.10 (14)
N2—C13—C14—C19	−7.7 (3)	N2—C13—O2—C12	−0.01 (19)
O2—C13—C14—C19	172.39 (16)	C14—C13—O2—C12	179.92 (14)
C19—C14—C15—C16	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2i	0.93	2.61	3.449 (3)	151
C5—H5···F2ii	0.93	2.51	3.290 (3)	141

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C1H1N2i	0.93	2.61	3.449(3)	151
C5H5F2ii	0.93	2.51	3.290(3)	141

Symmetry codes: (i) ; (ii) .