5-Methyl-3-[1-(2-pyridylmeth-yl)-1H-benzimidazol-2-ylmeth-yl]isoxazole.

The title compound, C(18)H(16)N(4)O, is built up from fused six- and five-membered rings linked to a five-membered isoxazole ring and to a six-membered pyridine ring through a CH(2) group. The fused-ring system is essentially planar, with a maximum deviation of 0.019 (1) Å. It forms inter-planar angles of 70.03 (7)° with the isoxazole ring and 81.68 (7)° with the pyridine ring; the two latter rings are also planar, the maximum deviations from the mean planes being 0.0028 (15) and 0.0047 (12) Å, respectively. In the crystal, weak inter-molecular non-classical C-H⋯N hydrogen bonds link the mol-ecules, forming a zigzag-like chain parallel to the b axis. A weak intra-molecular C-H⋯N hydrogen bond may help to define the conformation of the mol-ecule.

Related literature

Isoxazoles and their derivatives are key inter­mediates for the preparation of products which mimics natural compounds, see: Baraldi et al. (1987 ▶). For their biological activity, see: Boros et al. (2006 ▶); Desai & Desai (2006 ▶); Eddington et al. (2002 ▶); Kang et al. (2000 ▶); Ko et al. (1998 ▶); Lee & Kim (2002 ▶); Sbai et al. (2003 ▶).

Experimental

Crystal data

C18H16N4O

M = 304.35

Monoclinic,

a = 11.0761 (2) Å

b = 8.6535 (1) Å

c = 16.5920 (3) Å

β = 103.136 (1)°

V = 1548.68 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.28 × 0.16 × 0.06 mm

Data collection

Bruker X8 Kappa APEX II diffractometer

Absorption correction: none

29777 measured reflections

3567 independent reflections

2460 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.01

3567 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040100/dn2494sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040100/dn2494Isup2.hkl

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

C18H16N4O	F(000) = 640
Mr = 304.35	Dx = 1.305 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3567 reflections
a = 11.0761 (2) Å	θ = 2.5–27.5°
b = 8.6535 (1) Å	µ = 0.09 mm−1
c = 16.5920 (3) Å	T = 298 K
β = 103.136 (1)°	Block, white
V = 1548.68 (4) Å3	0.28 × 0.16 × 0.06 mm
Z = 4

Bruker X8 APEX Diffractometer	2460 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
graphite	θmax = 27.5°, θmin = 2.5°
φ and ω scans	h = −14→14
29777 measured reflections	k = −11→11
3567 independent reflections	l = −21→17

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.2578P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3567 reflections	Δρmax = 0.15 e Å−3
214 parameters	Δρmin = −0.14 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: 0.0099 (13)

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	0.35108 (10)	−0.03671 (13)	0.02360 (6)	0.0584 (3)
N1	0.28238 (12)	0.07631 (17)	0.05503 (8)	0.0587 (4)
N2	0.14275 (11)	0.00694 (14)	0.28340 (7)	0.0462 (3)
N3	0.02122 (11)	0.07134 (13)	0.16088 (7)	0.0421 (3)
N4	−0.03858 (11)	0.38647 (14)	0.14258 (7)	0.0472 (3)
C1	0.41164 (13)	−0.12534 (17)	0.08719 (9)	0.0461 (4)
C2	0.38459 (14)	−0.07581 (17)	0.15741 (9)	0.0467 (4)
H2	0.4130	−0.1163	0.2102	0.056*
C3	0.30411 (13)	0.05044 (16)	0.13448 (9)	0.0438 (3)
C4	0.24511 (14)	0.15139 (17)	0.18861 (9)	0.0519 (4)
H4B	0.3067	0.1774	0.2384	0.061 (5)*
H4A	0.2178	0.2469	0.1595	0.067 (5)*
C5	0.13705 (13)	0.07608 (15)	0.21254 (8)	0.0414 (3)
C6	0.02351 (13)	−0.04756 (15)	0.27876 (8)	0.0428 (3)
C7	−0.02328 (16)	−0.13135 (18)	0.33632 (10)	0.0559 (4)
H7	0.0275	−0.1608	0.3866	0.067*
C8	−0.14703 (17)	−0.1693 (2)	0.31653 (11)	0.0655 (5)
H8	−0.1803	−0.2249	0.3543	0.079*
C9	−0.22337 (16)	−0.1265 (2)	0.24140 (11)	0.0657 (5)
H9	−0.3067	−0.1538	0.2302	0.079*
C10	−0.17938 (14)	−0.04485 (19)	0.18304 (10)	0.0553 (4)
H10	−0.2307	−0.0165	0.1327	0.066*
C11	−0.05416 (13)	−0.00683 (15)	0.20323 (8)	0.0416 (3)
C12	−0.01820 (15)	0.13746 (17)	0.07846 (8)	0.0469 (4)
H12A	−0.0812	0.0708	0.0458	0.052 (4)*
H12B	0.0521	0.1375	0.0526	0.056 (4)*
C13	−0.06934 (12)	0.29955 (15)	0.07513 (7)	0.0380 (3)
C14	−0.08168 (16)	0.53187 (18)	0.13659 (10)	0.0568 (4)
H14	−0.0619	0.5940	0.1835	0.068*
C15	−0.15277 (16)	0.5944 (2)	0.06597 (11)	0.0610 (4)
H15	−0.1801	0.6961	0.0650	0.073*
C16	−0.18271 (15)	0.5037 (2)	−0.00321 (10)	0.0600 (4)
H16	−0.2305	0.5428	−0.0524	0.072*
C17	−0.14106 (13)	0.35385 (18)	0.00120 (9)	0.0496 (4)
H17	−0.1608	0.2897	−0.0449	0.060*
C18	0.48944 (16)	−0.2503 (2)	0.06534 (11)	0.0633 (4)
H18A	0.4381	−0.3218	0.0286	0.095*
H18B	0.5309	−0.3033	0.1147	0.095*
H18C	0.5499	−0.2068	0.0386	0.095*

	U11	U22	U33	U12	U13	U23
O1	0.0632 (7)	0.0749 (8)	0.0368 (6)	0.0062 (6)	0.0106 (5)	0.0119 (5)
N1	0.0609 (8)	0.0670 (9)	0.0474 (8)	0.0091 (7)	0.0107 (6)	0.0143 (6)
N2	0.0487 (7)	0.0438 (7)	0.0433 (7)	0.0026 (5)	0.0050 (5)	0.0042 (5)
N3	0.0491 (7)	0.0372 (6)	0.0381 (6)	0.0050 (5)	0.0062 (5)	0.0019 (5)
N4	0.0572 (7)	0.0463 (7)	0.0355 (6)	0.0096 (6)	0.0050 (5)	−0.0026 (5)
C1	0.0454 (8)	0.0521 (9)	0.0390 (8)	−0.0074 (7)	0.0056 (6)	0.0096 (6)
C2	0.0527 (8)	0.0491 (8)	0.0355 (7)	−0.0054 (7)	0.0040 (6)	0.0085 (6)
C3	0.0440 (8)	0.0443 (8)	0.0414 (8)	−0.0110 (6)	0.0059 (6)	0.0065 (6)
C4	0.0578 (9)	0.0440 (8)	0.0526 (9)	−0.0097 (7)	0.0100 (7)	−0.0012 (7)
C5	0.0484 (8)	0.0321 (7)	0.0420 (8)	0.0014 (6)	0.0068 (6)	−0.0029 (6)
C6	0.0475 (8)	0.0373 (7)	0.0432 (8)	0.0054 (6)	0.0096 (6)	−0.0002 (6)
C7	0.0647 (10)	0.0542 (9)	0.0504 (9)	0.0019 (8)	0.0161 (8)	0.0061 (7)
C8	0.0718 (12)	0.0661 (11)	0.0664 (11)	−0.0091 (9)	0.0321 (9)	−0.0011 (9)
C9	0.0516 (10)	0.0804 (12)	0.0689 (11)	−0.0106 (9)	0.0216 (9)	−0.0147 (10)
C10	0.0481 (9)	0.0634 (10)	0.0520 (9)	0.0048 (7)	0.0063 (7)	−0.0097 (8)
C11	0.0475 (8)	0.0354 (7)	0.0419 (8)	0.0058 (6)	0.0100 (6)	−0.0044 (6)
C12	0.0575 (9)	0.0478 (8)	0.0337 (7)	0.0062 (7)	0.0068 (6)	−0.0024 (6)
C13	0.0392 (7)	0.0435 (8)	0.0306 (7)	0.0010 (6)	0.0067 (5)	0.0019 (6)
C14	0.0714 (11)	0.0463 (9)	0.0523 (9)	0.0088 (8)	0.0136 (8)	−0.0049 (7)
C15	0.0641 (10)	0.0475 (9)	0.0717 (12)	0.0137 (8)	0.0164 (9)	0.0134 (8)
C16	0.0548 (9)	0.0641 (10)	0.0551 (10)	0.0061 (8)	0.0001 (7)	0.0237 (8)
C17	0.0514 (9)	0.0563 (9)	0.0365 (8)	−0.0040 (7)	0.0004 (6)	0.0035 (7)
C18	0.0676 (11)	0.0635 (10)	0.0621 (10)	0.0020 (8)	0.0216 (9)	0.0026 (8)

O1—C1	1.3526 (17)	C7—H7	0.9300
O1—N1	1.4100 (17)	C8—C9	1.388 (2)
N1—C3	1.3044 (17)	C8—H8	0.9300
N2—C5	1.3079 (17)	C9—C10	1.374 (2)
N2—C6	1.3880 (18)	C9—H9	0.9300
N3—C5	1.3720 (17)	C10—C11	1.390 (2)
N3—C11	1.3840 (18)	C10—H10	0.9300
N3—C12	1.4548 (16)	C12—C13	1.5090 (19)
N4—C13	1.3270 (16)	C12—H12A	0.9700
N4—C14	1.3414 (19)	C12—H12B	0.9700
C1—C2	1.338 (2)	C13—C17	1.3833 (18)
C1—C18	1.478 (2)	C14—C15	1.366 (2)
C2—C3	1.407 (2)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.368 (2)
C3—C4	1.504 (2)	C15—H15	0.9300
C4—C5	1.494 (2)	C16—C17	1.372 (2)
C4—H4B	0.9700	C16—H16	0.9300
C4—H4A	0.9700	C17—H17	0.9300
C6—C7	1.390 (2)	C18—H18A	0.9600
C6—C11	1.3945 (19)	C18—H18B	0.9600
C7—C8	1.375 (2)	C18—H18C	0.9600
C1—O1—N1	108.57 (11)	C10—C9—H9	119.0
C3—N1—O1	105.28 (11)	C8—C9—H9	119.0
C5—N2—C6	104.75 (11)	C9—C10—C11	116.48 (15)
C5—N3—C11	106.49 (11)	C9—C10—H10	121.8
C5—N3—C12	127.86 (12)	C11—C10—H10	121.8
C11—N3—C12	125.63 (12)	N3—C11—C10	132.63 (13)
C13—N4—C14	116.77 (12)	N3—C11—C6	105.05 (12)
C2—C1—O1	109.15 (13)	C10—C11—C6	122.32 (14)
C2—C1—C18	134.95 (14)	N3—C12—C13	115.46 (11)
O1—C1—C18	115.90 (13)	N3—C12—H12A	108.4
C1—C2—C3	105.48 (12)	C13—C12—H12A	108.4
C1—C2—H2	127.3	N3—C12—H12B	108.4
C3—C2—H2	127.3	C13—C12—H12B	108.4
N1—C3—C2	111.51 (13)	H12A—C12—H12B	107.5
N1—C3—C4	119.88 (13)	N4—C13—C17	122.74 (13)
C2—C3—C4	128.61 (13)	N4—C13—C12	118.28 (11)
C5—C4—C3	112.85 (12)	C17—C13—C12	118.90 (12)
C5—C4—H4B	109.0	N4—C14—C15	124.12 (15)
C3—C4—H4B	109.0	N4—C14—H14	117.9
C5—C4—H4A	109.0	C15—C14—H14	117.9
C3—C4—H4A	109.0	C14—C15—C16	118.38 (15)
H4B—C4—H4A	107.8	C14—C15—H15	120.8
N2—C5—N3	113.28 (12)	C16—C15—H15	120.8
N2—C5—C4	124.10 (13)	C15—C16—C17	118.87 (14)
N3—C5—C4	122.62 (12)	C15—C16—H16	120.6
N2—C6—C7	129.63 (13)	C17—C16—H16	120.6
N2—C6—C11	110.42 (12)	C16—C17—C13	119.12 (14)
C7—C6—C11	119.95 (14)	C16—C17—H17	120.4
C8—C7—C6	117.89 (15)	C13—C17—H17	120.4
C8—C7—H7	121.1	C1—C18—H18A	109.5
C6—C7—H7	121.1	C1—C18—H18B	109.5
C7—C8—C9	121.43 (16)	H18A—C18—H18B	109.5
C7—C8—H8	119.3	C1—C18—H18C	109.5
C9—C8—H8	119.3	H18A—C18—H18C	109.5
C10—C9—C8	121.93 (16)	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4i	0.93	2.52	3.385 (2)	155
C12—H12B···N1	0.97	2.60	3.479 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N4i	0.93	2.52	3.385 (2)	155
C12—H12B⋯N1	0.97	2.60	3.479 (2)	151

Symmetry code: (i) .