{4-[5-(4-tert-Butyl-phen-yl)-1,3,4-oxa-diazol-2-yl]phen-yl}methanol.

In the title compound, C(19)H(20)N(2)O(2), the 1,3,4-oxadiazole ring is almost coplanar with the two neighboring benzene rings [dihedral angles = 3.76 (4) and 5.49 (4)°]. In the crystal, mol-ecules are connected by strong inter-molecular O-H⋯N hydrogen bonds, forming chains parallel to the c axis.

Related literature

For the properties and applications of 1,3,4-oxadiazole derivatives, see: Hughes & Bryce (2005 ▶); Kim & Lee (2007 ▶); Kulkarni et al. (2004 ▶); Liang et al. (2003 ▶); Liou et al. (2006 ▶); Strukelj et al. (1995 ▶). For the biological activity of compounds containing the 1,3,4-oxadiazole moiety, see: Cacic et al. (2006 ▶); Mansour et al. (2003 ▶); Yar et al. (2007 ▶); Zhang et al. (2007 ▶). For synthesis of the inter­mediate, see Mashraqui et al. (2007 ▶).

Experimental

Crystal data

C19H20N2O2

M = 308.37

Monoclinic,

a = 16.3958 (18) Å

b = 6.0654 (7) Å

c = 16.7206 (19) Å

β = 102.289 (2)°

V = 1624.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 185 K

0.32 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.974, T max = 0.993

8995 measured reflections

2886 independent reflections

1805 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.122

S = 0.98

2886 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052967/pk2290sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052967/pk2290Isup2.hkl

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

C19H20N2O2	F(000) = 656
Mr = 308.37	Dx = 1.261 Mg m−3
Monoclinic, P21/c	Melting point = 381–383 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.3958 (18) Å	Cell parameters from 1372 reflections
b = 6.0654 (7) Å	θ = 2.5–23.3°
c = 16.7206 (19) Å	µ = 0.08 mm−1
β = 102.289 (2)°	T = 185 K
V = 1624.7 (3) Å3	Block, colorless
Z = 4	0.32 × 0.14 × 0.09 mm

Bruker SMART APEX CCD diffractometer	2886 independent reflections
Radiation source: sealed tube	1805 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→19
Tmin = 0.974, Tmax = 0.993	k = −7→7
8995 measured reflections	l = −19→19

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0608P)2] where P = (Fo2 + 2Fc2)/3
2886 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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	0.11403 (11)	−0.3479 (3)	0.77257 (10)	0.0481 (5)
H1	0.1306	−0.2304	0.7974	0.072*
O2	0.21110 (9)	0.1173 (2)	0.41106 (9)	0.0363 (4)
N1	0.12828 (12)	0.3966 (3)	0.42308 (11)	0.0396 (5)
N2	0.16872 (13)	0.4399 (3)	0.35861 (11)	0.0405 (5)
C1	0.04959 (16)	−0.2996 (4)	0.70351 (14)	0.0423 (6)
H1A	0.0045	−0.2187	0.7219	0.051*
H1B	0.0259	−0.4397	0.6784	0.051*
C2	0.07960 (15)	−0.1632 (4)	0.63943 (13)	0.0358 (6)
C3	0.13751 (15)	−0.2496 (4)	0.59808 (14)	0.0388 (6)
H3	0.1603	−0.3919	0.6119	0.047*
C4	0.16207 (15)	−0.1294 (4)	0.53697 (13)	0.0375 (6)
H4	0.2006	−0.1915	0.5081	0.045*
C5	0.13098 (15)	0.0811 (3)	0.51743 (13)	0.0334 (6)
C6	0.07323 (15)	0.1692 (4)	0.55888 (13)	0.0373 (6)
H6	0.0512	0.3127	0.5458	0.045*
C7	0.04808 (15)	0.0471 (4)	0.61911 (13)	0.0386 (6)
H7	0.0086	0.1077	0.6471	0.046*
C8	0.15439 (14)	0.2058 (4)	0.45132 (13)	0.0335 (6)
C9	0.21555 (15)	0.2722 (4)	0.35340 (13)	0.0346 (6)
C10	0.26874 (14)	0.2326 (4)	0.29488 (13)	0.0338 (6)
C11	0.30966 (17)	0.0348 (4)	0.29253 (16)	0.0514 (7)
H11	0.3055	−0.0775	0.3311	0.062*
C12	0.35681 (17)	−0.0006 (4)	0.23410 (16)	0.0546 (8)
H12	0.3847	−0.1377	0.2336	0.066*
C13	0.36454 (15)	0.1577 (4)	0.17643 (14)	0.0366 (6)
C14	0.32332 (15)	0.3538 (4)	0.18029 (14)	0.0422 (6)
H14	0.3276	0.4666	0.1420	0.051*
C15	0.27591 (15)	0.3921 (4)	0.23804 (14)	0.0424 (6)
H15	0.2481	0.5293	0.2386	0.051*
C16	0.41390 (15)	0.1098 (4)	0.10994 (14)	0.0393 (6)
C17	0.49387 (17)	−0.0160 (5)	0.14583 (17)	0.0589 (8)
H17A	0.5287	0.0726	0.1890	0.088*
H17B	0.5245	−0.0455	0.1026	0.088*
H17C	0.4798	−0.1559	0.1689	0.088*
C18	0.4366 (2)	0.3210 (4)	0.06978 (19)	0.0703 (10)
H18A	0.4693	0.4174	0.1117	0.105*
H18B	0.3854	0.3971	0.0427	0.105*
H18C	0.4696	0.2839	0.0292	0.105*
C19	0.35905 (17)	−0.0327 (4)	0.04458 (15)	0.0532 (7)
H19A	0.3890	−0.0653	0.0011	0.080*
H19B	0.3074	0.0466	0.0214	0.080*
H19C	0.3456	−0.1708	0.0693	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0561 (13)	0.0525 (10)	0.0353 (10)	−0.0063 (9)	0.0085 (9)	0.0032 (8)
O2	0.0408 (11)	0.0420 (9)	0.0285 (9)	0.0023 (7)	0.0127 (8)	0.0020 (7)
N1	0.0450 (14)	0.0458 (12)	0.0301 (11)	0.0014 (10)	0.0128 (10)	0.0014 (9)
N2	0.0427 (13)	0.0494 (12)	0.0323 (12)	0.0062 (10)	0.0144 (10)	0.0039 (9)
C1	0.0477 (18)	0.0502 (15)	0.0292 (14)	−0.0063 (12)	0.0088 (13)	−0.0010 (11)
C2	0.0388 (16)	0.0416 (14)	0.0275 (13)	−0.0080 (11)	0.0084 (11)	−0.0043 (10)
C3	0.0436 (16)	0.0367 (13)	0.0373 (14)	−0.0020 (11)	0.0114 (13)	−0.0019 (11)
C4	0.0393 (16)	0.0422 (13)	0.0340 (13)	−0.0038 (11)	0.0146 (12)	−0.0061 (11)
C5	0.0374 (15)	0.0375 (13)	0.0252 (12)	−0.0056 (11)	0.0067 (11)	−0.0041 (10)
C6	0.0421 (16)	0.0405 (13)	0.0298 (13)	−0.0031 (11)	0.0090 (12)	−0.0046 (10)
C7	0.0427 (16)	0.0475 (14)	0.0282 (13)	−0.0042 (12)	0.0134 (12)	−0.0102 (11)
C8	0.0345 (15)	0.0411 (13)	0.0252 (13)	−0.0011 (11)	0.0074 (11)	−0.0064 (10)
C9	0.0385 (16)	0.0407 (13)	0.0255 (13)	−0.0017 (12)	0.0085 (12)	0.0040 (10)
C10	0.0326 (15)	0.0410 (13)	0.0281 (13)	0.0004 (11)	0.0068 (11)	0.0021 (10)
C11	0.067 (2)	0.0444 (15)	0.0515 (17)	0.0111 (13)	0.0313 (16)	0.0150 (12)
C12	0.071 (2)	0.0421 (14)	0.0606 (19)	0.0167 (14)	0.0354 (17)	0.0115 (13)
C13	0.0366 (15)	0.0410 (13)	0.0342 (14)	−0.0008 (11)	0.0119 (12)	0.0010 (11)
C14	0.0444 (17)	0.0446 (14)	0.0416 (15)	0.0044 (12)	0.0180 (13)	0.0120 (12)
C15	0.0427 (16)	0.0417 (13)	0.0456 (15)	0.0108 (12)	0.0156 (13)	0.0097 (12)
C16	0.0382 (16)	0.0424 (13)	0.0411 (14)	0.0012 (12)	0.0166 (13)	−0.0005 (11)
C17	0.0458 (19)	0.0787 (19)	0.0555 (18)	0.0067 (15)	0.0181 (15)	−0.0091 (15)
C18	0.096 (3)	0.0512 (17)	0.085 (2)	−0.0044 (16)	0.066 (2)	0.0018 (15)
C19	0.0552 (19)	0.0661 (18)	0.0408 (16)	0.0017 (14)	0.0158 (14)	−0.0035 (13)

O1—C1	1.420 (3)	C10—C15	1.379 (3)
O1—H1	0.8400	C11—C12	1.386 (3)
O2—C9	1.359 (2)	C11—H11	0.9500
O2—C8	1.368 (2)	C12—C13	1.386 (3)
N1—C8	1.288 (3)	C12—H12	0.9500
N1—N2	1.405 (2)	C13—C14	1.377 (3)
N2—C9	1.289 (3)	C13—C16	1.536 (3)
C1—C2	1.516 (3)	C14—C15	1.382 (3)
C1—H1A	0.9900	C14—H14	0.9500
C1—H1B	0.9900	C15—H15	0.9500
C2—C7	1.391 (3)	C16—C17	1.525 (3)
C2—C3	1.391 (3)	C16—C19	1.527 (3)
C3—C4	1.383 (3)	C16—C18	1.528 (3)
C3—H3	0.9500	C17—H17A	0.9800
C4—C5	1.388 (3)	C17—H17B	0.9800
C4—H4	0.9500	C17—H17C	0.9800
C5—C6	1.394 (3)	C18—H18A	0.9800
C5—C8	1.457 (3)	C18—H18B	0.9800
C6—C7	1.382 (3)	C18—H18C	0.9800
C6—H6	0.9500	C19—H19A	0.9800
C7—H7	0.9500	C19—H19B	0.9800
C9—C10	1.463 (3)	C19—H19C	0.9800
C10—C11	1.379 (3)
C1—O1—H1	109.5	C10—C11—H11	119.9
C9—O2—C8	102.87 (16)	C12—C11—H11	119.9
C8—N1—N2	105.96 (17)	C11—C12—C13	122.1 (2)
C9—N2—N1	106.82 (17)	C11—C12—H12	119.0
O1—C1—C2	113.0 (2)	C13—C12—H12	119.0
O1—C1—H1A	109.0	C14—C13—C12	116.6 (2)
C2—C1—H1A	109.0	C14—C13—C16	122.48 (19)
O1—C1—H1B	109.0	C12—C13—C16	120.9 (2)
C2—C1—H1B	109.0	C13—C14—C15	122.2 (2)
H1A—C1—H1B	107.8	C13—C14—H14	118.9
C7—C2—C3	118.78 (19)	C15—C14—H14	118.9
C7—C2—C1	120.89 (19)	C10—C15—C14	120.4 (2)
C3—C2—C1	120.3 (2)	C10—C15—H15	119.8
C4—C3—C2	120.4 (2)	C14—C15—H15	119.8
C4—C3—H3	119.8	C17—C16—C19	108.9 (2)
C2—C3—H3	119.8	C17—C16—C18	108.8 (2)
C3—C4—C5	120.6 (2)	C19—C16—C18	108.7 (2)
C3—C4—H4	119.7	C17—C16—C13	110.55 (19)
C5—C4—H4	119.7	C19—C16—C13	107.72 (18)
C4—C5—C6	119.35 (19)	C18—C16—C13	111.99 (18)
C4—C5—C8	120.90 (19)	C16—C17—H17A	109.5
C6—C5—C8	119.7 (2)	C16—C17—H17B	109.5
C7—C6—C5	119.8 (2)	H17A—C17—H17B	109.5
C7—C6—H6	120.1	C16—C17—H17C	109.5
C5—C6—H6	120.1	H17A—C17—H17C	109.5
C6—C7—C2	121.1 (2)	H17B—C17—H17C	109.5
C6—C7—H7	119.4	C16—C18—H18A	109.5
C2—C7—H7	119.4	C16—C18—H18B	109.5
N1—C8—O2	112.30 (18)	H18A—C18—H18B	109.5
N1—C8—C5	128.60 (19)	C16—C18—H18C	109.5
O2—C8—C5	119.09 (19)	H18A—C18—H18C	109.5
N2—C9—O2	112.03 (17)	H18B—C18—H18C	109.5
N2—C9—C10	128.56 (19)	C16—C19—H19A	109.5
O2—C9—C10	119.41 (19)	C16—C19—H19B	109.5
C11—C10—C15	118.5 (2)	H19A—C19—H19B	109.5
C11—C10—C9	121.64 (19)	C16—C19—H19C	109.5
C15—C10—C9	119.8 (2)	H19A—C19—H19C	109.5
C10—C11—C12	120.2 (2)	H19B—C19—H19C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.84	2.07	2.906 (3)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.84	2.07	2.906 (3)	179

Symmetry code: (i) .