5-(5'-Fluoro-2'-meth-oxy-biphenyl-3-yl)-1,3,4-oxa-diazol-2-amine.

In the title compound, C15H12FN3O2, the dihedral angles between the central benzene ring and the pendant benzene and oxa-diazole rings are 45.05 (13) and 15.60 (14)°, respectively. The C atom of the meth-oxy group is roughly coplanar with its attached ring [displacement = 0.178 (4) Å]. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into [010] chains. Weak C-H⋯π inter-actions are also observed.

Related literature

For background to the title compound, see: Ainsworth (1965 ▶); Paik et al. (2002 ▶); Kulkarni et al. (2004 ▶). For a related structure, see: Zheng et al. (2012 ▶).

Experimental

Crystal data

C15H12FN3O2

M = 285.28

Monoclinic,

a = 12.9105 (9) Å

b = 6.1738 (4) Å

c = 16.9255 (11) Å

β = 90.341 (7)°

V = 1349.05 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.806, T max = 1.000

5027 measured reflections

2650 independent reflections

1382 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.135

S = 1.01

2650 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813031206/hb7155sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031206/hb7155Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031206/hb7155Isup3.cml

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

C15H12FN3O2	F(000) = 592
Mr = 285.28	Dx = 1.405 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1316 reflections
a = 12.9105 (9) Å	θ = 4.1–28.0°
b = 6.1738 (4) Å	µ = 0.11 mm−1
c = 16.9255 (11) Å	T = 293 K
β = 90.341 (7)°	Block, colourless
V = 1349.05 (16) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer	2650 independent reflections
Radiation source: fine-focus sealed tube	1382 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −8→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −7→4
Tmin = 0.806, Tmax = 1.000	l = −17→20
5027 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0316P)2] where P = (Fo2 + 2Fc2)/3
2650 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	0.89022 (14)	0.0443 (3)	0.56943 (11)	0.0411 (5)
C2	0.9336 (2)	0.0508 (4)	0.64301 (15)	0.0357 (7)
N3	0.95451 (18)	−0.1405 (3)	0.67077 (13)	0.0435 (6)
N4	0.92173 (18)	−0.2865 (3)	0.61121 (14)	0.0440 (6)
C5	0.8848 (2)	−0.1745 (4)	0.55387 (16)	0.0361 (7)
N6	0.94739 (18)	0.2434 (3)	0.67575 (14)	0.0522 (7)
H6A	0.9738	0.2534	0.7224	0.063*
H6B	0.9299	0.3586	0.6504	0.063*
C7	0.8429 (2)	−0.2443 (4)	0.47839 (16)	0.0394 (7)
C8	0.8602 (2)	−0.4578 (4)	0.45329 (17)	0.0454 (8)
H8	0.8959	−0.5549	0.4854	0.054*
C9	0.8235 (2)	−0.5213 (4)	0.38043 (18)	0.0480 (8)
H9	0.8363	−0.6615	0.3628	0.058*
C10	0.7682 (2)	−0.3804 (4)	0.33300 (17)	0.0466 (8)
H10	0.7439	−0.4268	0.2840	0.056*
C11	0.7485 (2)	−0.1694 (4)	0.35787 (16)	0.0388 (7)
C12	0.7856 (2)	−0.1043 (4)	0.43139 (16)	0.0405 (7)
H12	0.7718	0.0352	0.4493	0.049*
C13	0.6929 (2)	−0.0182 (4)	0.30377 (17)	0.0411 (7)
C14	0.7207 (2)	−0.0126 (5)	0.22425 (18)	0.0506 (8)
H14	0.7731	−0.1027	0.2059	0.061*
C15	0.6709 (2)	0.1257 (5)	0.17307 (18)	0.0524 (9)
F15	0.70017 (16)	0.1262 (3)	0.09598 (11)	0.0846 (7)
C16	0.5951 (3)	0.2629 (5)	0.19672 (19)	0.0531 (9)
H16	0.5637	0.3574	0.1611	0.064*
C17	0.5654 (2)	0.2585 (5)	0.27592 (17)	0.0517 (9)
H17	0.5122	0.3480	0.2932	0.062*
C18	0.6147 (2)	0.1221 (4)	0.32879 (17)	0.0441 (8)
O19	0.58667 (17)	0.1049 (3)	0.40644 (12)	0.0614 (7)
C20	0.5209 (3)	0.2668 (6)	0.4382 (2)	0.0936 (14)
H20A	0.5506	0.4071	0.4290	0.140*
H20B	0.5134	0.2441	0.4940	0.140*
H20C	0.4541	0.2588	0.4130	0.140*

	U11	U22	U33	U12	U13	U23
O1	0.0593 (13)	0.0289 (9)	0.0351 (11)	0.0003 (9)	−0.0166 (10)	0.0016 (9)
C2	0.0461 (17)	0.0308 (14)	0.0301 (16)	0.0027 (12)	−0.0122 (14)	0.0017 (13)
N3	0.0615 (17)	0.0327 (12)	0.0360 (15)	0.0038 (11)	−0.0156 (13)	0.0011 (12)
N4	0.0553 (16)	0.0352 (13)	0.0412 (15)	0.0026 (11)	−0.0122 (14)	0.0020 (11)
C5	0.0457 (17)	0.0279 (14)	0.0345 (17)	−0.0006 (12)	−0.0035 (14)	−0.0008 (13)
N6	0.0814 (19)	0.0304 (12)	0.0444 (16)	0.0014 (12)	−0.0292 (15)	−0.0041 (12)
C7	0.0481 (17)	0.0339 (15)	0.0362 (18)	−0.0033 (13)	−0.0061 (15)	0.0014 (14)
C8	0.0564 (19)	0.0326 (14)	0.0471 (19)	−0.0002 (14)	−0.0083 (16)	0.0077 (14)
C9	0.061 (2)	0.0363 (15)	0.047 (2)	−0.0004 (14)	−0.0050 (17)	−0.0040 (15)
C10	0.060 (2)	0.0403 (17)	0.0391 (18)	−0.0048 (14)	−0.0127 (16)	−0.0072 (14)
C11	0.0448 (18)	0.0384 (15)	0.0331 (17)	−0.0026 (13)	−0.0104 (15)	−0.0035 (13)
C12	0.0461 (17)	0.0359 (15)	0.0393 (18)	−0.0002 (13)	−0.0103 (15)	−0.0027 (14)
C13	0.0440 (18)	0.0432 (17)	0.0359 (18)	−0.0017 (13)	−0.0122 (15)	−0.0060 (14)
C14	0.0465 (19)	0.058 (2)	0.047 (2)	0.0030 (15)	−0.0033 (16)	0.0008 (17)
C15	0.053 (2)	0.066 (2)	0.0376 (19)	−0.0013 (17)	−0.0043 (17)	0.0113 (17)
F15	0.0898 (16)	0.1211 (17)	0.0430 (12)	0.0135 (13)	0.0050 (12)	0.0220 (12)
C16	0.063 (2)	0.052 (2)	0.044 (2)	−0.0017 (17)	−0.0132 (18)	0.0107 (17)
C17	0.056 (2)	0.0550 (19)	0.044 (2)	0.0098 (16)	−0.0097 (17)	0.0001 (17)
C18	0.0494 (19)	0.0460 (17)	0.0367 (18)	−0.0024 (14)	−0.0126 (16)	0.0019 (15)
O19	0.0755 (17)	0.0654 (15)	0.0433 (14)	0.0219 (12)	−0.0017 (13)	−0.0034 (12)
C20	0.131 (4)	0.092 (3)	0.059 (3)	0.044 (3)	0.005 (3)	−0.012 (2)

O1—C2	1.363 (3)	C11—C13	1.490 (4)
O1—C5	1.378 (3)	C12—H12	0.9300
C2—N3	1.299 (3)	C13—C14	1.396 (4)
C2—N6	1.323 (3)	C13—C18	1.398 (4)
N3—N4	1.415 (3)	C14—C15	1.374 (4)
N4—C5	1.281 (3)	C14—H14	0.9300
C5—C7	1.450 (3)	C15—C16	1.356 (4)
N6—H6A	0.8600	C15—F15	1.361 (3)
N6—H6B	0.8600	C16—C17	1.397 (4)
C7—C12	1.386 (3)	C16—H16	0.9300
C7—C8	1.403 (3)	C17—C18	1.381 (4)
C8—C9	1.375 (4)	C17—H17	0.9300
C8—H8	0.9300	C18—O19	1.369 (3)
C9—C10	1.380 (4)	O19—C20	1.420 (3)
C9—H9	0.9300	C20—H20A	0.9600
C10—C11	1.393 (3)	C20—H20B	0.9600
C10—H10	0.9300	C20—H20C	0.9600
C11—C12	1.390 (3)
C2—O1—C5	102.9 (2)	C7—C12—H12	119.6
N3—C2—N6	129.7 (3)	C11—C12—H12	119.6
N3—C2—O1	112.8 (2)	C14—C13—C18	117.9 (3)
N6—C2—O1	117.5 (2)	C14—C13—C11	118.8 (3)
C2—N3—N4	105.1 (2)	C18—C13—C11	123.3 (3)
C5—N4—N3	107.7 (2)	C15—C14—C13	120.1 (3)
N4—C5—O1	111.5 (2)	C15—C14—H14	120.0
N4—C5—C7	130.0 (2)	C13—C14—H14	120.0
O1—C5—C7	118.6 (2)	C16—C15—F15	119.1 (3)
C2—N6—H6A	120.0	C16—C15—C14	122.6 (3)
C2—N6—H6B	120.0	F15—C15—C14	118.3 (3)
H6A—N6—H6B	120.0	C15—C16—C17	118.3 (3)
C12—C7—C8	119.9 (3)	C15—C16—H16	120.9
C12—C7—C5	121.0 (2)	C17—C16—H16	120.9
C8—C7—C5	119.1 (2)	C18—C17—C16	120.4 (3)
C9—C8—C7	119.0 (3)	C18—C17—H17	119.8
C9—C8—H8	120.5	C16—C17—H17	119.8
C7—C8—H8	120.5	O19—C18—C17	123.1 (3)
C8—C9—C10	121.1 (3)	O19—C18—C13	116.0 (3)
C8—C9—H9	119.5	C17—C18—C13	120.8 (3)
C10—C9—H9	119.5	C18—O19—C20	118.1 (3)
C9—C10—C11	120.6 (3)	O19—C20—H20A	109.5
C9—C10—H10	119.7	O19—C20—H20B	109.5
C11—C10—H10	119.7	H20A—C20—H20B	109.5
C12—C11—C10	118.6 (3)	O19—C20—H20C	109.5
C12—C11—C13	122.1 (2)	H20A—C20—H20C	109.5
C10—C11—C13	119.3 (2)	H20B—C20—H20C	109.5
C7—C12—C11	120.9 (2)
C5—O1—C2—N3	0.6 (3)	C10—C11—C12—C7	1.3 (4)
C5—O1—C2—N6	−178.7 (2)	C13—C11—C12—C7	−175.8 (3)
N6—C2—N3—N4	178.8 (3)	C12—C11—C13—C14	133.5 (3)
O1—C2—N3—N4	−0.4 (3)	C10—C11—C13—C14	−43.7 (4)
C2—N3—N4—C5	0.0 (3)	C12—C11—C13—C18	−45.5 (4)
N3—N4—C5—O1	0.4 (3)	C10—C11—C13—C18	137.3 (3)
N3—N4—C5—C7	178.7 (3)	C18—C13—C14—C15	−0.8 (4)
C2—O1—C5—N4	−0.6 (3)	C11—C13—C14—C15	−179.8 (2)
C2—O1—C5—C7	−179.2 (2)	C13—C14—C15—C16	1.0 (5)
N4—C5—C7—C12	165.3 (3)	C13—C14—C15—F15	−179.9 (3)
O1—C5—C7—C12	−16.4 (4)	F15—C15—C16—C17	179.4 (3)
N4—C5—C7—C8	−14.2 (5)	C14—C15—C16—C17	−1.6 (5)
O1—C5—C7—C8	164.1 (2)	C15—C16—C17—C18	1.9 (5)
C12—C7—C8—C9	2.8 (4)	C16—C17—C18—O19	−177.6 (3)
C5—C7—C8—C9	−177.7 (3)	C16—C17—C18—C13	−1.8 (5)
C7—C8—C9—C10	−1.6 (4)	C14—C13—C18—O19	177.3 (3)
C8—C9—C10—C11	0.3 (4)	C11—C13—C18—O19	−3.7 (4)
C9—C10—C11—C12	−0.1 (4)	C14—C13—C18—C17	1.2 (4)
C9—C10—C11—C13	177.2 (3)	C11—C13—C18—C17	−179.8 (3)
C8—C7—C12—C11	−2.7 (4)	C17—C18—O19—C20	−14.6 (4)
C5—C7—C12—C11	177.8 (3)	C13—C18—O19—C20	169.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N3i	0.86	2.13	2.972 (3)	166
N6—H6B···N4ii	0.86	2.29	3.118 (3)	161
C17—H17···Cg3iii	0.93	2.72	3.53	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯N3i	0.86	2.13	2.972 (3)	166
N6—H6B⋯N4ii	0.86	2.29	3.118 (3)	161
C17—H17⋯Cg3iii	0.93	2.72	3.53	146

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