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

The title compound, C20H15FN2O2, adopts an almost planar conformation. The oxa-diazole ring makes dihedral angles of 13.90 (1) and 7.93 (1)° with the naphthalene ring system and benzene ring, respectively, while the naphthalene ring system and benzene ring are inclined to one another by 6.35 (1)°. In the crystal, adjacent mol-ecules are linked via C-H⋯N hydrogen bonds, forming chains propagating along [100]. There are also π-π inter-actions present [inter-centroid distances = 3.5754 (9) and 3.7191 (12) Å], linking the chains to form ribbons lying parallel to (011).

Related literature

For the biological activities of triazole derivatives, see: Desai et al. (2014 ▸), Khalilullah et al. (2012 ▸), Bethge et al. (2005 ▸); Saha et al. (2013 ▸); Shailaja et al. (2010 ▸); Sun et al. (2013 ▸).

Experimental

Crystal data

C20H15FN2O2

M = 334.34

Triclinic,

a = 7.4236 (4) Å

b = 7.5062 (4) Å

c = 16.3519 (8) Å

α = 77.092 (3)°

β = 77.494 (3)°

γ = 66.734 (3)°

V = 807.51 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.981, T max = 0.990

11476 measured reflections

3368 independent reflections

2306 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.134

S = 1.05

3368 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.22 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/S2056989015004144/su5076sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015004144/su5076Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015004144/su5076Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015004144/su5076fig1.tif

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015004144/su5076fig2.tif

The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details). H atoms not involved in hydrogen bonds have been omitted for clarity.

CCDC reference: 1051477

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

C20H15FN2O2	Z = 2
Mr = 334.34	F(000) = 348
Triclinic, P1	Dx = 1.375 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4236 (4) Å	Cell parameters from 3368 reflections
b = 7.5062 (4) Å	θ = 1.3–26.6°
c = 16.3519 (8) Å	µ = 0.10 mm−1
α = 77.092 (3)°	T = 293 K
β = 77.494 (3)°	Block, colourless
γ = 66.734 (3)°	0.20 × 0.15 × 0.10 mm
V = 807.51 (7) Å3

Bruker SMART APEXII area-detector diffractometer	3368 independent reflections
Radiation source: fine-focus sealed tube	2306 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 26.6°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.981, Tmax = 0.990	k = −9→9
11476 measured reflections	l = −20→20

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) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1875P] where P = (Fo2 + 2Fc2)/3
3368 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.22 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
C1	0.2815 (2)	0.9674 (2)	0.27299 (10)	0.0380 (4)
C2	0.0947 (3)	1.0312 (3)	0.24700 (11)	0.0458 (4)
H2	−0.0126	1.0179	0.2860	0.055*
C3	0.0698 (3)	1.1126 (3)	0.16502 (12)	0.0559 (5)
H3	−0.0549	1.1560	0.1486	0.067*
C4	0.2302 (3)	1.1315 (3)	0.10517 (12)	0.0585 (5)
H4	0.2119	1.1853	0.0492	0.070*
C5	0.4113 (3)	1.0721 (3)	0.12833 (11)	0.0542 (5)
H5	0.5162	1.0865	0.0881	0.065*
C6	0.4443 (3)	0.9883 (3)	0.21265 (11)	0.0443 (4)
C7	0.6314 (3)	0.9262 (3)	0.23862 (12)	0.0550 (5)
H7	0.7384	0.9387	0.1993	0.066*
C8	0.6573 (3)	0.8484 (3)	0.32022 (13)	0.0572 (5)
H8	0.7817	0.8093	0.3363	0.069*
C9	0.4991 (3)	0.8257 (3)	0.38106 (11)	0.0486 (4)
H9	0.5184	0.7738	0.4371	0.058*
C10	0.3179 (2)	0.8801 (2)	0.35759 (10)	0.0400 (4)
C11	0.1845 (3)	0.7566 (3)	0.49454 (10)	0.0460 (4)
H11A	0.2094	0.8342	0.5279	0.055*
H11B	0.2968	0.6338	0.4921	0.055*
C12	0.0001 (3)	0.7192 (2)	0.53259 (10)	0.0427 (4)
C13	−0.1993 (3)	0.6253 (2)	0.62939 (11)	0.0430 (4)
C14	−0.2765 (3)	0.5508 (2)	0.71406 (11)	0.0444 (4)
C15	−0.4706 (3)	0.5567 (3)	0.72898 (13)	0.0577 (5)
H15	−0.5487	0.6074	0.6857	0.069*
C16	−0.5456 (3)	0.4863 (3)	0.80897 (15)	0.0678 (6)
H16	−0.6747	0.4885	0.8203	0.081*
C17	−0.4279 (4)	0.4138 (3)	0.87090 (13)	0.0653 (6)
C18	−0.2365 (4)	0.4046 (3)	0.85990 (12)	0.0590 (5)
C19	−0.1633 (3)	0.4763 (3)	0.77889 (11)	0.0505 (5)
H19	−0.0341	0.4736	0.7683	0.061*
C20	−0.1144 (4)	0.3226 (4)	0.93077 (13)	0.0871 (8)
H20A	−0.1727	0.4033	0.9747	0.131*
H20B	0.0176	0.3204	0.9098	0.131*
H20C	−0.1096	0.1915	0.9533	0.131*
F1	−0.5067 (3)	0.3450 (2)	0.94919 (8)	0.0999 (6)
N1	−0.1472 (2)	0.7432 (2)	0.49750 (9)	0.0555 (4)
N2	−0.2797 (2)	0.6806 (2)	0.56191 (9)	0.0545 (4)
O1	0.15466 (17)	0.86032 (18)	0.41174 (7)	0.0494 (3)
O2	−0.01882 (18)	0.64483 (17)	0.61616 (7)	0.0440 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0433 (10)	0.0364 (8)	0.0348 (8)	−0.0165 (7)	−0.0051 (7)	−0.0032 (6)
C2	0.0467 (11)	0.0496 (10)	0.0438 (10)	−0.0229 (9)	−0.0085 (8)	−0.0004 (8)
C3	0.0602 (13)	0.0593 (12)	0.0522 (11)	−0.0256 (10)	−0.0218 (9)	0.0038 (9)
C4	0.0791 (15)	0.0614 (12)	0.0368 (10)	−0.0317 (11)	−0.0148 (9)	0.0066 (8)
C5	0.0635 (13)	0.0584 (12)	0.0397 (10)	−0.0297 (10)	−0.0001 (9)	0.0012 (8)
C6	0.0482 (11)	0.0431 (9)	0.0416 (9)	−0.0203 (8)	−0.0020 (8)	−0.0040 (7)
C7	0.0457 (11)	0.0655 (12)	0.0529 (11)	−0.0267 (10)	0.0010 (8)	−0.0028 (9)
C8	0.0449 (11)	0.0699 (13)	0.0590 (12)	−0.0262 (10)	−0.0115 (9)	−0.0007 (10)
C9	0.0493 (11)	0.0568 (11)	0.0413 (9)	−0.0225 (9)	−0.0141 (8)	0.0024 (8)
C10	0.0416 (10)	0.0428 (9)	0.0353 (8)	−0.0175 (8)	−0.0043 (7)	−0.0026 (7)
C11	0.0509 (11)	0.0511 (10)	0.0330 (9)	−0.0198 (9)	−0.0069 (7)	0.0028 (7)
C12	0.0540 (11)	0.0421 (9)	0.0311 (8)	−0.0189 (8)	−0.0070 (7)	−0.0003 (7)
C13	0.0476 (11)	0.0390 (9)	0.0421 (10)	−0.0176 (8)	−0.0045 (8)	−0.0043 (7)
C14	0.0532 (11)	0.0383 (9)	0.0402 (9)	−0.0188 (8)	0.0002 (8)	−0.0055 (7)
C15	0.0552 (12)	0.0541 (11)	0.0633 (13)	−0.0235 (10)	−0.0006 (9)	−0.0088 (9)
C16	0.0651 (14)	0.0620 (13)	0.0748 (15)	−0.0338 (12)	0.0202 (12)	−0.0167 (11)
C17	0.0882 (17)	0.0523 (12)	0.0489 (12)	−0.0346 (12)	0.0231 (11)	−0.0099 (9)
C18	0.0824 (16)	0.0473 (11)	0.0391 (10)	−0.0205 (11)	0.0018 (9)	−0.0066 (8)
C19	0.0581 (12)	0.0486 (10)	0.0405 (10)	−0.0197 (9)	0.0009 (8)	−0.0057 (8)
C20	0.123 (2)	0.0851 (17)	0.0403 (12)	−0.0314 (16)	−0.0105 (13)	0.0024 (11)
F1	0.1377 (14)	0.0909 (10)	0.0602 (8)	−0.0597 (10)	0.0404 (8)	−0.0094 (7)
N1	0.0603 (11)	0.0690 (11)	0.0386 (8)	−0.0302 (9)	−0.0109 (7)	0.0055 (7)
N2	0.0563 (10)	0.0671 (10)	0.0434 (9)	−0.0298 (9)	−0.0114 (7)	0.0031 (7)
O1	0.0425 (7)	0.0639 (8)	0.0348 (6)	−0.0199 (6)	−0.0047 (5)	0.0066 (5)
O2	0.0510 (8)	0.0498 (7)	0.0314 (6)	−0.0222 (6)	−0.0061 (5)	0.0010 (5)

C1—C2	1.405 (2)	C11—H11B	0.9700
C1—C6	1.422 (2)	C12—N1	1.276 (2)
C1—C10	1.426 (2)	C12—O2	1.3552 (19)
C2—C3	1.363 (2)	C13—N2	1.277 (2)
C2—H2	0.9300	C13—O2	1.371 (2)
C3—C4	1.401 (3)	C13—C14	1.456 (2)
C3—H3	0.9300	C14—C19	1.376 (3)
C4—C5	1.349 (3)	C14—C15	1.393 (3)
C4—H4	0.9300	C15—C16	1.381 (3)
C5—C6	1.412 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.359 (3)
C6—C7	1.408 (3)	C16—H16	0.9300
C7—C8	1.354 (3)	C17—F1	1.367 (2)
C7—H7	0.9300	C17—C18	1.368 (3)
C8—C9	1.405 (3)	C18—C19	1.393 (3)
C8—H8	0.9300	C18—C20	1.497 (3)
C9—C10	1.357 (2)	C19—H19	0.9300
C9—H9	0.9300	C20—H20A	0.9600
C10—O1	1.376 (2)	C20—H20B	0.9600
C11—O1	1.418 (2)	C20—H20C	0.9600
C11—C12	1.482 (2)	N1—N2	1.412 (2)
C11—H11A	0.9700
C2—C1—C6	119.18 (15)	H11A—C11—H11B	108.7
C2—C1—C10	123.22 (15)	N1—C12—O2	113.17 (16)
C6—C1—C10	117.60 (16)	N1—C12—C11	129.27 (15)
C3—C2—C1	120.36 (17)	O2—C12—C11	117.55 (15)
C3—C2—H2	119.8	N2—C13—O2	112.28 (15)
C1—C2—H2	119.8	N2—C13—C14	128.39 (17)
C2—C3—C4	120.63 (19)	O2—C13—C14	119.32 (15)
C2—C3—H3	119.7	C19—C14—C15	119.73 (17)
C4—C3—H3	119.7	C19—C14—C13	121.76 (17)
C5—C4—C3	120.33 (17)	C15—C14—C13	118.51 (18)
C5—C4—H4	119.8	C16—C15—C14	119.1 (2)
C3—C4—H4	119.8	C16—C15—H15	120.4
C4—C5—C6	121.17 (17)	C14—C15—H15	120.4
C4—C5—H5	119.4	C17—C16—C15	119.0 (2)
C6—C5—H5	119.4	C17—C16—H16	120.5
C7—C6—C5	122.32 (17)	C15—C16—H16	120.5
C7—C6—C1	119.36 (16)	C16—C17—F1	117.4 (2)
C5—C6—C1	118.31 (17)	C16—C17—C18	124.44 (19)
C8—C7—C6	120.77 (17)	F1—C17—C18	118.2 (2)
C8—C7—H7	119.6	C17—C18—C19	115.8 (2)
C6—C7—H7	119.6	C17—C18—C20	121.8 (2)
C7—C8—C9	121.02 (18)	C19—C18—C20	122.3 (2)
C7—C8—H8	119.5	C14—C19—C18	121.9 (2)
C9—C8—H8	119.5	C14—C19—H19	119.0
C10—C9—C8	119.62 (17)	C18—C19—H19	119.0
C10—C9—H9	120.2	C18—C20—H20A	109.5
C8—C9—H9	120.2	C18—C20—H20B	109.5
C9—C10—O1	124.18 (15)	H20A—C20—H20B	109.5
C9—C10—C1	121.59 (16)	C18—C20—H20C	109.5
O1—C10—C1	114.23 (14)	H20A—C20—H20C	109.5
O1—C11—C12	106.29 (14)	H20B—C20—H20C	109.5
O1—C11—H11A	110.5	C12—N1—N2	105.94 (14)
C12—C11—H11A	110.5	C13—N2—N1	106.37 (15)
O1—C11—H11B	110.5	C10—O1—C11	117.26 (13)
C12—C11—H11B	110.5	C12—O2—C13	102.25 (13)
C6—C1—C2—C3	−0.1 (2)	O2—C13—C14—C15	171.45 (15)
C10—C1—C2—C3	−179.64 (16)	C19—C14—C15—C16	−0.3 (3)
C1—C2—C3—C4	0.8 (3)	C13—C14—C15—C16	179.90 (16)
C2—C3—C4—C5	−1.1 (3)	C14—C15—C16—C17	0.2 (3)
C3—C4—C5—C6	0.6 (3)	C15—C16—C17—F1	−179.84 (17)
C4—C5—C6—C7	−179.61 (19)	C15—C16—C17—C18	−0.1 (3)
C4—C5—C6—C1	0.2 (3)	C16—C17—C18—C19	0.2 (3)
C2—C1—C6—C7	179.40 (16)	F1—C17—C18—C19	179.88 (16)
C10—C1—C6—C7	−1.1 (2)	C16—C17—C18—C20	−179.9 (2)
C2—C1—C6—C5	−0.4 (2)	F1—C17—C18—C20	−0.2 (3)
C10—C1—C6—C5	179.18 (15)	C15—C14—C19—C18	0.3 (3)
C5—C6—C7—C8	179.28 (18)	C13—C14—C19—C18	−179.86 (16)
C1—C6—C7—C8	−0.5 (3)	C17—C18—C19—C14	−0.3 (3)
C6—C7—C8—C9	0.6 (3)	C20—C18—C19—C14	179.80 (18)
C7—C8—C9—C10	0.9 (3)	O2—C12—N1—N2	0.0 (2)
C8—C9—C10—O1	178.61 (16)	C11—C12—N1—N2	178.53 (17)
C8—C9—C10—C1	−2.5 (3)	O2—C13—N2—N1	−0.2 (2)
C2—C1—C10—C9	−177.89 (17)	C14—C13—N2—N1	178.90 (16)
C6—C1—C10—C9	2.6 (2)	C12—N1—N2—C13	0.1 (2)
C2—C1—C10—O1	1.1 (2)	C9—C10—O1—C11	−7.4 (2)
C6—C1—C10—O1	−178.44 (14)	C1—C10—O1—C11	173.68 (14)
O1—C11—C12—N1	10.3 (3)	C12—C11—O1—C10	−168.05 (14)
O1—C11—C12—O2	−171.25 (13)	N1—C12—O2—C13	−0.12 (19)
N2—C13—C14—C19	172.65 (18)	C11—C12—O2—C13	−178.81 (14)
O2—C13—C14—C19	−8.3 (2)	N2—C13—O2—C12	0.17 (18)
N2—C13—C14—C15	−7.5 (3)	C14—C13—O2—C12	−178.98 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N2i	0.93	2.60	3.447 (2)	152

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C9H9N2i	0.93	2.60	3.447(2)	152

Symmetry code: (i) .