2-(4-tert-Butyl-phen-yl)-5-p-tolyl-1,3,4-oxadiazole.

In the title compound, C(19)H(20)N(2)O, the dihedral angles between the 1,3,4-oxadiazole ring and the pendant 4-tert-butyl-phenyl and 4-methyl-phenyl rings are 12.53 (17) and 2.14 (17)°, respectively. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds, forming chains.

Related literature

For background to the applications of 1,3,4-oxadiazo­les, see: Jin et al. (2004 ▶).

Experimental

Crystal data

C19H20N2O

M = 292.37

Monoclinic,

a = 9.886 (9) Å

b = 10.613 (9) Å

c = 16.093 (13) Å

β = 99.14 (2)°

V = 1667 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.813, T max = 1.000

17627 measured reflections

3791 independent reflections

3032 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.109

wR(F 2) = 0.223

S = 1.15

3791 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051198/hb5237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051198/hb5237Isup2.hkl

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

C19H20N2O	F(000) = 624
Mr = 292.37	Dx = 1.165 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3230 reflections
a = 9.886 (9) Å	θ = 2.8–27.4°
b = 10.613 (9) Å	µ = 0.07 mm−1
c = 16.093 (13) Å	T = 298 K
β = 99.14 (2)°	Prism, colourless
V = 1667 (2) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	3791 independent reflections
Radiation source: fine-focus sealed tube	3032 reflections with I > 2σ(I)
graphite	Rint = 0.063
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4°, θmin = 3.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.813, Tmax = 1.000	l = −20→20
17627 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)] = 0.109	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.223	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0626P)2 + 1.4014P] where P = (Fo2 + 2Fc2)/3
3791 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.27 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
N1	0.3647 (3)	0.1864 (3)	−0.12566 (17)	0.0697 (9)
N2	0.4425 (3)	0.2831 (3)	−0.15544 (17)	0.0700 (9)
C1	0.0865 (5)	−0.0115 (4)	0.2440 (3)	0.0860 (13)
H1A	0.1464	0.0548	0.2679	0.103*
H1B	0.0160	0.0232	0.2023	0.103*
H1C	0.0455	−0.0511	0.2875	0.103*
C2	0.2791 (4)	−0.1677 (4)	0.2699 (2)	0.0789 (12)
H2A	0.3308	−0.2290	0.2443	0.095*
H2B	0.3394	−0.1025	0.2952	0.095*
H2C	0.2358	−0.2076	0.3123	0.095*
C3	0.0725 (4)	−0.2149 (4)	0.1647 (3)	0.0812 (12)
H3A	0.1234	−0.2768	0.1390	0.097*
H3B	0.0313	−0.2539	0.2084	0.097*
H3C	0.0022	−0.1801	0.1230	0.097*
C4	0.1693 (3)	−0.1097 (3)	0.2024 (2)	0.0553 (8)
C5	0.2384 (3)	−0.0420 (3)	0.13559 (18)	0.0466 (7)
C6	0.2082 (4)	−0.0674 (3)	0.0497 (2)	0.0576 (9)
H6A	0.1482	−0.1327	0.0313	0.069*
C7	0.2645 (4)	0.0019 (3)	−0.0089 (2)	0.0584 (9)
H7A	0.2419	−0.0171	−0.0659	0.070*
C8	0.3550 (3)	0.0996 (3)	0.01657 (18)	0.0451 (7)
C9	0.3904 (3)	0.1238 (3)	0.10244 (18)	0.0497 (7)
H9A	0.4537	0.1866	0.1209	0.060*
C10	0.3322 (3)	0.0545 (3)	0.16006 (18)	0.0515 (8)
H10A	0.3560	0.0729	0.2170	0.062*
C11	0.4060 (3)	0.1801 (3)	−0.04533 (19)	0.0483 (7)
C12	0.5233 (3)	0.3273 (3)	−0.09054 (18)	0.0489 (7)
C13	0.6256 (3)	0.4270 (3)	−0.08675 (18)	0.0467 (7)
C14	0.7057 (3)	0.4607 (3)	−0.01123 (19)	0.0564 (8)
H14A	0.6924	0.4211	0.0384	0.068*
C15	0.8054 (4)	0.5533 (3)	−0.0093 (2)	0.0592 (9)
H15A	0.8589	0.5742	0.0417	0.071*
C16	0.8265 (3)	0.6151 (3)	−0.08216 (19)	0.0487 (7)
C17	0.7452 (3)	0.5817 (3)	−0.1574 (2)	0.0524 (8)
H17A	0.7576	0.6222	−0.2069	0.063*
C18	0.6460 (3)	0.4893 (3)	−0.16024 (19)	0.0522 (8)
H18A	0.5926	0.4685	−0.2113	0.063*
C19	0.9346 (4)	0.7153 (3)	−0.0792 (2)	0.0638 (9)
H19A	0.9803	0.7254	−0.0223	0.077*
H19B	1.0000	0.6909	−0.1144	0.077*
H19C	0.8927	0.7936	−0.0990	0.077*
O1	0.5059 (2)	0.26623 (19)	−0.01819 (12)	0.0487 (5)

	U11	U22	U33	U12	U13	U23
N1	0.079 (2)	0.080 (2)	0.0463 (16)	−0.0276 (17)	−0.0004 (14)	0.0102 (14)
N2	0.079 (2)	0.078 (2)	0.0500 (16)	−0.0269 (17)	−0.0014 (14)	0.0158 (15)
C1	0.099 (3)	0.074 (3)	0.098 (3)	−0.001 (2)	0.058 (3)	0.005 (2)
C2	0.100 (3)	0.080 (3)	0.058 (2)	0.001 (2)	0.018 (2)	0.014 (2)
C3	0.095 (3)	0.078 (3)	0.075 (3)	−0.030 (2)	0.026 (2)	0.006 (2)
C4	0.065 (2)	0.0505 (18)	0.0529 (18)	−0.0047 (16)	0.0184 (16)	0.0028 (15)
C5	0.0499 (17)	0.0459 (17)	0.0452 (16)	0.0006 (14)	0.0107 (13)	0.0006 (13)
C6	0.069 (2)	0.0522 (19)	0.0529 (19)	−0.0228 (17)	0.0126 (16)	−0.0095 (15)
C7	0.074 (2)	0.058 (2)	0.0426 (17)	−0.0145 (17)	0.0085 (15)	−0.0071 (14)
C8	0.0458 (16)	0.0447 (16)	0.0448 (16)	−0.0008 (13)	0.0071 (12)	0.0006 (13)
C9	0.0479 (17)	0.0523 (18)	0.0476 (17)	−0.0092 (14)	0.0039 (13)	0.0010 (14)
C10	0.0572 (19)	0.0575 (19)	0.0382 (15)	−0.0067 (15)	0.0027 (13)	−0.0037 (14)
C11	0.0484 (17)	0.0494 (18)	0.0464 (17)	−0.0052 (14)	0.0054 (13)	0.0013 (13)
C12	0.0515 (17)	0.0518 (18)	0.0428 (16)	0.0034 (15)	0.0058 (13)	0.0090 (13)
C13	0.0454 (16)	0.0481 (17)	0.0459 (16)	0.0006 (14)	0.0048 (13)	0.0048 (13)
C14	0.064 (2)	0.063 (2)	0.0417 (16)	−0.0039 (17)	0.0091 (14)	0.0118 (15)
C15	0.066 (2)	0.062 (2)	0.0460 (18)	−0.0082 (18)	0.0000 (15)	0.0004 (15)
C16	0.0491 (17)	0.0425 (16)	0.0549 (18)	0.0034 (14)	0.0091 (14)	0.0007 (14)
C17	0.0590 (19)	0.0486 (18)	0.0507 (18)	0.0023 (15)	0.0120 (15)	0.0084 (14)
C18	0.0584 (19)	0.0527 (18)	0.0436 (16)	−0.0038 (15)	0.0021 (14)	0.0046 (14)
C19	0.064 (2)	0.057 (2)	0.071 (2)	−0.0054 (17)	0.0116 (18)	−0.0031 (17)
O1	0.0520 (12)	0.0497 (12)	0.0442 (11)	−0.0040 (10)	0.0066 (9)	0.0057 (9)

N1—C11	1.294 (4)	C8—C9	1.395 (4)
N1—N2	1.411 (4)	C8—C11	1.462 (4)
N2—C12	1.298 (4)	C9—C10	1.379 (4)
C1—C4	1.543 (5)	C9—H9A	0.9300
C1—H1A	0.9599	C10—H10A	0.9300
C1—H1B	0.9600	C11—O1	1.365 (4)
C1—H1C	0.9601	C12—O1	1.367 (3)
C2—C4	1.536 (5)	C12—C13	1.458 (4)
C2—H2A	0.9601	C13—C14	1.388 (4)
C2—H2B	0.9600	C13—C18	1.397 (4)
C2—H2C	0.9601	C14—C15	1.389 (4)
C3—C4	1.532 (5)	C14—H14A	0.9300
C3—H3A	0.9599	C15—C16	1.389 (4)
C3—H3B	0.9599	C15—H15A	0.9300
C3—H3C	0.9601	C16—C17	1.389 (4)
C4—C5	1.540 (4)	C16—C19	1.503 (4)
C5—C6	1.394 (4)	C17—C18	1.382 (4)
C5—C10	1.396 (4)	C17—H17A	0.9300
C6—C7	1.381 (4)	C18—H18A	0.9300
C6—H6A	0.9300	C19—H19A	0.9601
C7—C8	1.388 (4)	C19—H19B	0.9599
C7—H7A	0.9302	C19—H19C	0.9599
C11—N1—N2	105.9 (3)	C10—C9—C8	120.2 (3)
C12—N2—N1	106.8 (3)	C10—C9—H9A	119.9
C4—C1—H1A	109.5	C8—C9—H9A	119.9
C4—C1—H1B	109.4	C9—C10—C5	122.1 (3)
H1A—C1—H1B	109.5	C9—C10—H10A	118.9
C4—C1—H1C	109.6	C5—C10—H10A	119.0
H1A—C1—H1C	109.5	N1—C11—O1	112.5 (3)
H1B—C1—H1C	109.5	N1—C11—C8	128.5 (3)
C4—C2—H2A	109.4	O1—C11—C8	118.9 (3)
C4—C2—H2B	109.4	N2—C12—O1	111.7 (3)
H2A—C2—H2B	109.5	N2—C12—C13	129.1 (3)
C4—C2—H2C	109.5	O1—C12—C13	119.3 (3)
H2A—C2—H2C	109.5	C14—C13—C18	118.7 (3)
H2B—C2—H2C	109.5	C14—C13—C12	121.2 (3)
C4—C3—H3A	109.4	C18—C13—C12	120.0 (3)
C4—C3—H3B	109.6	C13—C14—C15	120.4 (3)
H3A—C3—H3B	109.5	C13—C14—H14A	119.8
C4—C3—H3C	109.5	C15—C14—H14A	119.8
H3A—C3—H3C	109.5	C14—C15—C16	121.1 (3)
H3B—C3—H3C	109.5	C14—C15—H15A	119.4
C3—C4—C2	108.4 (3)	C16—C15—H15A	119.5
C3—C4—C5	112.5 (3)	C15—C16—C17	118.1 (3)
C2—C4—C5	109.8 (3)	C15—C16—C19	120.6 (3)
C3—C4—C1	108.9 (3)	C17—C16—C19	121.3 (3)
C2—C4—C1	109.2 (3)	C18—C17—C16	121.3 (3)
C5—C4—C1	108.2 (3)	C18—C17—H17A	119.3
C6—C5—C10	116.7 (3)	C16—C17—H17A	119.4
C6—C5—C4	123.6 (3)	C17—C18—C13	120.3 (3)
C10—C5—C4	119.6 (3)	C17—C18—H18A	119.8
C7—C6—C5	121.9 (3)	C13—C18—H18A	119.9
C7—C6—H6A	119.1	C16—C19—H19A	109.5
C5—C6—H6A	119.0	C16—C19—H19B	109.4
C6—C7—C8	120.4 (3)	H19A—C19—H19B	109.5
C6—C7—H7A	119.8	C16—C19—H19C	109.5
C8—C7—H7A	119.8	H19A—C19—H19C	109.5
C7—C8—C9	118.6 (3)	H19B—C19—H19C	109.5
C7—C8—C11	120.7 (3)	C11—O1—C12	103.2 (2)
C9—C8—C11	120.5 (3)
C11—N1—N2—C12	−0.4 (4)	C9—C8—C11—O1	10.5 (4)
C3—C4—C5—C6	4.5 (5)	N1—N2—C12—O1	0.3 (4)
C2—C4—C5—C6	125.3 (4)	N1—N2—C12—C13	179.2 (3)
C1—C4—C5—C6	−115.7 (4)	N2—C12—C13—C14	−178.7 (3)
C3—C4—C5—C10	−178.5 (3)	O1—C12—C13—C14	0.1 (5)
C2—C4—C5—C10	−57.8 (4)	N2—C12—C13—C18	0.4 (5)
C1—C4—C5—C10	61.2 (4)	O1—C12—C13—C18	179.2 (3)
C10—C5—C6—C7	−2.0 (5)	C18—C13—C14—C15	−1.0 (5)
C4—C5—C6—C7	175.0 (3)	C12—C13—C14—C15	178.1 (3)
C5—C6—C7—C8	0.5 (5)	C13—C14—C15—C16	0.7 (5)
C6—C7—C8—C9	1.8 (5)	C14—C15—C16—C17	−0.1 (5)
C6—C7—C8—C11	−174.8 (3)	C14—C15—C16—C19	179.9 (3)
C7—C8—C9—C10	−2.4 (5)	C15—C16—C17—C18	−0.2 (5)
C11—C8—C9—C10	174.2 (3)	C19—C16—C17—C18	179.8 (3)
C8—C9—C10—C5	0.8 (5)	C16—C17—C18—C13	−0.1 (5)
C6—C5—C10—C9	1.4 (5)	C14—C13—C18—C17	0.7 (5)
C4—C5—C10—C9	−175.8 (3)	C12—C13—C18—C17	−178.4 (3)
N2—N1—C11—O1	0.4 (4)	N1—C11—O1—C12	−0.2 (4)
N2—N1—C11—C8	177.0 (3)	C8—C11—O1—C12	−177.2 (3)
C7—C8—C11—N1	10.5 (5)	N2—C12—O1—C11	−0.1 (3)
C9—C8—C11—N1	−166.0 (3)	C13—C12—O1—C11	−179.1 (3)
C7—C8—C11—O1	−173.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N2i	0.93	2.59	3.456 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯N2i	0.93	2.59	3.456 (5)	155

Symmetry code: (i) .