3-Benzyl-1-{[3-(4-chloro-phen-yl)isoxazol-5-yl]meth-yl}-1H-benzimidazol-2(3H)-one.

In the title compound, C24H18ClN3O2, the benzimidazole plane is nearly perpendicular to the phenyl ring and to the isoxazole ring, making dihedral angles of 75.95 (7) and 73.04 (8)°, respectively, but the two residues point in opposite directions with respect to the benzimidazole plane. The dihedral angle between the chloro-phenyl and isoxazole rings is 7.95 (8)°. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into inversion dimers.

Related literature

For the biological activity of isoxazoline derivatives, see: Sakuma et al. (2011 ▶); Hu et al. (2010 ▶); Wang et al. (2010 ▶). For benzimidazol-2-one derivatives, see: Belaziz et al. (2012 ▶).

Experimental

Crystal data

C24H18ClN3O2

M = 415.86

Triclinic,

a = 8.5427 (2) Å

b = 9.8290 (2) Å

c = 13.2658 (3) Å

α = 81.133 (1)°

β = 78.763 (1)°

γ = 64.343 (1)°

V = 981.73 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.60 × 0.39 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.688, T max = 0.746

70806 measured reflections

5994 independent reflections

4622 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.143

S = 1.03

5994 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; 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: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681302299X/bt6928sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302299X/bt6928Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302299X/bt6928Isup3.cml

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

C24H18ClN3O2	Z = 2
Mr = 415.86	F(000) = 432
Triclinic, P1	Dx = 1.407 Mg m−3
Hall symbol: -P 1	Melting point: 467 K
a = 8.5427 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8290 (2) Å	Cell parameters from 9881 reflections
c = 13.2658 (3) Å	θ = 2.7–29.9°
α = 81.133 (1)°	µ = 0.22 mm−1
β = 78.763 (1)°	T = 296 K
γ = 64.343 (1)°	Prism, colourless
V = 981.73 (4) Å3	0.60 × 0.39 × 0.13 mm

Bruker APEXII CCD diffractometer	5994 independent reflections
Radiation source: fine-focus sealed tube	4622 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 30.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.688, Tmax = 0.746	k = −14→14
70806 measured reflections	l = −18→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.2335P] where P = (Fo2 + 2Fc2)/3
5994 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.96270 (18)	0.07935 (15)	1.15305 (10)	0.0408 (3)
C2	1.0111 (2)	0.19835 (18)	1.13183 (12)	0.0491 (3)
H2	1.0951	0.2011	1.1658	0.059*
C3	0.9335 (2)	0.31396 (17)	1.05931 (11)	0.0466 (3)
H3	0.9659	0.3947	1.0446	0.056*
C4	0.80752 (16)	0.31087 (14)	1.00813 (9)	0.0362 (2)
C5	0.75890 (19)	0.19111 (17)	1.03279 (11)	0.0445 (3)
H5	0.6728	0.1890	1.0004	0.053*
C6	0.8363 (2)	0.07437 (17)	1.10491 (12)	0.0468 (3)
H6	0.8035	−0.0061	1.1206	0.056*
C7	0.73329 (17)	0.42911 (14)	0.92671 (9)	0.0362 (2)
C8	0.62184 (18)	0.43492 (16)	0.85805 (10)	0.0422 (3)
H8	0.5746	0.3661	0.8565	0.051*
C9	0.59949 (17)	0.56105 (15)	0.79592 (10)	0.0400 (3)
C10	0.50513 (19)	0.63221 (18)	0.70493 (11)	0.0480 (3)
H10A	0.4119	0.5997	0.7084	0.058*
H10B	0.4520	0.7414	0.7069	0.058*
C11	0.6890 (2)	0.68917 (17)	0.54875 (11)	0.0461 (3)
C12	0.79140 (18)	0.47023 (16)	0.47125 (10)	0.0436 (3)
C13	0.8769 (2)	0.35197 (19)	0.40860 (12)	0.0562 (4)
H13	0.9492	0.3597	0.3478	0.067*
C14	0.8507 (3)	0.2209 (2)	0.43976 (15)	0.0669 (5)
H14	0.9087	0.1387	0.3996	0.080*
C15	0.7409 (3)	0.20923 (19)	0.52889 (14)	0.0628 (4)
H15	0.7239	0.1208	0.5465	0.075*
C16	0.6556 (2)	0.32735 (18)	0.59249 (12)	0.0522 (3)
H16	0.5825	0.3196	0.6529	0.063*
C17	0.68346 (18)	0.45689 (16)	0.56272 (10)	0.0423 (3)
C18	0.8719 (2)	0.68311 (19)	0.37749 (12)	0.0511 (3)
H18A	0.9817	0.6069	0.3471	0.061*
H18B	0.8978	0.7582	0.4019	0.061*
C19	0.75256 (18)	0.75806 (16)	0.29623 (10)	0.0425 (3)
C20	0.6070 (2)	0.89424 (17)	0.31390 (11)	0.0463 (3)
H20	0.5858	0.9388	0.3750	0.056*
C21	0.4936 (2)	0.96400 (18)	0.24177 (12)	0.0511 (3)
H21	0.3960	1.0546	0.2547	0.061*
C22	0.5253 (2)	0.8988 (2)	0.15014 (12)	0.0541 (4)
H22	0.4493	0.9457	0.1014	0.065*
C23	0.6691 (2)	0.7652 (2)	0.13163 (12)	0.0570 (4)
H23	0.6909	0.7219	0.0699	0.068*
C24	0.7823 (2)	0.69410 (19)	0.20462 (12)	0.0519 (3)
H24	0.8788	0.6029	0.1918	0.062*
Cl1	1.06618 (6)	−0.06917 (5)	1.24013 (3)	0.05818 (13)
N1	0.7736 (2)	0.54512 (15)	0.90688 (11)	0.0558 (3)
N2	0.62261 (16)	0.59181 (13)	0.60857 (8)	0.0439 (3)
N3	0.79299 (16)	0.61217 (14)	0.46473 (9)	0.0460 (3)
O1	0.68832 (17)	0.63109 (13)	0.82270 (9)	0.0573 (3)
O2	0.66140 (18)	0.81529 (13)	0.56718 (9)	0.0607 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0437 (6)	0.0438 (6)	0.0331 (6)	−0.0174 (5)	−0.0066 (5)	0.0017 (5)
C2	0.0552 (8)	0.0538 (8)	0.0485 (8)	−0.0288 (7)	−0.0227 (6)	0.0051 (6)
C3	0.0585 (8)	0.0477 (7)	0.0469 (7)	−0.0324 (6)	−0.0205 (6)	0.0059 (6)
C4	0.0397 (6)	0.0411 (6)	0.0304 (5)	−0.0194 (5)	−0.0054 (4)	−0.0021 (4)
C5	0.0482 (7)	0.0530 (7)	0.0425 (7)	−0.0304 (6)	−0.0137 (5)	0.0045 (6)
C6	0.0534 (8)	0.0501 (7)	0.0465 (7)	−0.0320 (6)	−0.0106 (6)	0.0061 (6)
C7	0.0397 (6)	0.0404 (6)	0.0302 (5)	−0.0181 (5)	−0.0046 (4)	−0.0033 (4)
C8	0.0461 (7)	0.0499 (7)	0.0370 (6)	−0.0251 (6)	−0.0112 (5)	0.0008 (5)
C9	0.0389 (6)	0.0455 (7)	0.0324 (6)	−0.0146 (5)	−0.0045 (5)	−0.0037 (5)
C10	0.0426 (7)	0.0542 (8)	0.0364 (6)	−0.0096 (6)	−0.0093 (5)	−0.0002 (6)
C11	0.0496 (7)	0.0452 (7)	0.0376 (6)	−0.0130 (6)	−0.0134 (5)	0.0017 (5)
C12	0.0442 (7)	0.0445 (7)	0.0364 (6)	−0.0102 (5)	−0.0162 (5)	0.0010 (5)
C13	0.0591 (9)	0.0556 (9)	0.0421 (7)	−0.0096 (7)	−0.0122 (6)	−0.0073 (6)
C14	0.0808 (12)	0.0497 (9)	0.0620 (10)	−0.0106 (8)	−0.0250 (9)	−0.0130 (8)
C15	0.0821 (12)	0.0489 (8)	0.0619 (10)	−0.0252 (8)	−0.0306 (9)	0.0021 (7)
C16	0.0599 (9)	0.0520 (8)	0.0465 (8)	−0.0227 (7)	−0.0213 (7)	0.0069 (6)
C17	0.0436 (6)	0.0438 (7)	0.0355 (6)	−0.0116 (5)	−0.0174 (5)	0.0027 (5)
C18	0.0454 (7)	0.0613 (9)	0.0436 (7)	−0.0219 (7)	−0.0084 (6)	0.0060 (6)
C19	0.0439 (7)	0.0489 (7)	0.0364 (6)	−0.0232 (6)	−0.0040 (5)	0.0018 (5)
C20	0.0536 (8)	0.0479 (7)	0.0382 (6)	−0.0217 (6)	−0.0083 (6)	−0.0015 (5)
C21	0.0522 (8)	0.0506 (8)	0.0506 (8)	−0.0212 (6)	−0.0133 (6)	0.0026 (6)
C22	0.0599 (9)	0.0698 (10)	0.0467 (8)	−0.0390 (8)	−0.0180 (7)	0.0053 (7)
C23	0.0686 (10)	0.0752 (11)	0.0416 (7)	−0.0425 (9)	−0.0045 (7)	−0.0115 (7)
C24	0.0528 (8)	0.0564 (8)	0.0448 (7)	−0.0226 (7)	0.0005 (6)	−0.0091 (6)
Cl1	0.0641 (2)	0.0540 (2)	0.0521 (2)	−0.02165 (18)	−0.01949 (17)	0.01336 (16)
N1	0.0801 (9)	0.0523 (7)	0.0520 (7)	−0.0390 (7)	−0.0331 (7)	0.0130 (6)
N2	0.0495 (6)	0.0440 (6)	0.0317 (5)	−0.0131 (5)	−0.0093 (4)	0.0009 (4)
N3	0.0494 (6)	0.0461 (6)	0.0368 (6)	−0.0158 (5)	−0.0077 (5)	0.0022 (5)
O1	0.0810 (8)	0.0494 (6)	0.0542 (6)	−0.0357 (6)	−0.0315 (6)	0.0140 (5)
O2	0.0779 (8)	0.0466 (6)	0.0534 (6)	−0.0220 (6)	−0.0090 (6)	−0.0044 (5)

C1—C2	1.375 (2)	C12—C17	1.400 (2)
C1—C6	1.378 (2)	C13—C14	1.389 (3)
C1—Cl1	1.7342 (13)	C13—H13	0.9300
C2—C3	1.384 (2)	C14—C15	1.382 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.3928 (18)	C15—C16	1.386 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.3845 (18)	C16—C17	1.380 (2)
C4—C7	1.4701 (17)	C16—H16	0.9300
C5—C6	1.386 (2)	C17—N2	1.3882 (18)
C5—H5	0.9300	C18—N3	1.4610 (19)
C6—H6	0.9300	C18—C19	1.509 (2)
C7—N1	1.3037 (18)	C18—H18A	0.9700
C7—C8	1.4192 (17)	C18—H18B	0.9700
C8—C9	1.3394 (19)	C19—C24	1.383 (2)
C8—H8	0.9300	C19—C20	1.391 (2)
C9—O1	1.3449 (18)	C20—C21	1.381 (2)
C9—C10	1.4922 (18)	C20—H20	0.9300
C10—N2	1.4527 (18)	C21—C22	1.386 (2)
C10—H10A	0.9700	C21—H21	0.9300
C10—H10B	0.9700	C22—C23	1.371 (3)
C11—O2	1.2124 (19)	C22—H22	0.9300
C11—N3	1.3772 (19)	C23—C24	1.390 (2)
C11—N2	1.388 (2)	C23—H23	0.9300
C12—C13	1.379 (2)	C24—H24	0.9300
C12—N3	1.3902 (19)	N1—O1	1.4088 (16)
C2—C1—C6	121.31 (13)	C15—C14—H14	119.1
C2—C1—Cl1	119.23 (11)	C13—C14—H14	119.1
C6—C1—Cl1	119.44 (11)	C14—C15—C16	121.02 (17)
C1—C2—C3	119.24 (13)	C14—C15—H15	119.5
C1—C2—H2	120.4	C16—C15—H15	119.5
C3—C2—H2	120.4	C17—C16—C15	117.41 (16)
C2—C3—C4	120.78 (13)	C17—C16—H16	121.3
C2—C3—H3	119.6	C15—C16—H16	121.3
C4—C3—H3	119.6	C16—C17—N2	131.99 (14)
C5—C4—C3	118.59 (12)	C16—C17—C12	121.66 (14)
C5—C4—C7	120.80 (11)	N2—C17—C12	106.35 (13)
C3—C4—C7	120.56 (12)	N3—C18—C19	111.88 (12)
C4—C5—C6	121.11 (12)	N3—C18—H18A	109.2
C4—C5—H5	119.4	C19—C18—H18A	109.2
C6—C5—H5	119.4	N3—C18—H18B	109.2
C1—C6—C5	118.94 (13)	C19—C18—H18B	109.2
C1—C6—H6	120.5	H18A—C18—H18B	107.9
C5—C6—H6	120.5	C24—C19—C20	118.70 (13)
N1—C7—C8	110.87 (12)	C24—C19—C18	121.82 (14)
N1—C7—C4	120.56 (11)	C20—C19—C18	119.47 (13)
C8—C7—C4	128.52 (12)	C21—C20—C19	120.76 (14)
C9—C8—C7	105.03 (12)	C21—C20—H20	119.6
C9—C8—H8	127.5	C19—C20—H20	119.6
C7—C8—H8	127.5	C20—C21—C22	119.91 (15)
C8—C9—O1	109.84 (12)	C20—C21—H21	120.0
C8—C9—C10	133.67 (14)	C22—C21—H21	120.0
O1—C9—C10	116.44 (13)	C23—C22—C21	119.81 (15)
N2—C10—C9	111.65 (11)	C23—C22—H22	120.1
N2—C10—H10A	109.3	C21—C22—H22	120.1
C9—C10—H10A	109.3	C22—C23—C24	120.32 (14)
N2—C10—H10B	109.3	C22—C23—H23	119.8
C9—C10—H10B	109.3	C24—C23—H23	119.8
H10A—C10—H10B	108.0	C19—C24—C23	120.49 (15)
O2—C11—N3	127.39 (15)	C19—C24—H24	119.8
O2—C11—N2	127.01 (14)	C23—C24—H24	119.8
N3—C11—N2	105.60 (13)	C7—N1—O1	105.96 (11)
C13—C12—N3	132.02 (15)	C17—N2—C11	110.57 (12)
C13—C12—C17	120.70 (15)	C17—N2—C10	126.87 (13)
N3—C12—C17	107.24 (12)	C11—N2—C10	122.56 (13)
C12—C13—C14	117.41 (16)	C11—N3—C12	110.25 (12)
C12—C13—H13	121.3	C11—N3—C18	122.37 (13)
C14—C13—H13	121.3	C12—N3—C18	126.95 (13)
C15—C14—C13	121.78 (16)	C9—O1—N1	108.30 (11)
C6—C1—C2—C3	−1.2 (2)	C24—C19—C20—C21	0.4 (2)
Cl1—C1—C2—C3	177.46 (12)	C18—C19—C20—C21	−178.77 (14)
C1—C2—C3—C4	0.1 (2)	C19—C20—C21—C22	−0.6 (2)
C2—C3—C4—C5	1.3 (2)	C20—C21—C22—C23	0.1 (2)
C2—C3—C4—C7	−176.27 (13)	C21—C22—C23—C24	0.5 (3)
C3—C4—C5—C6	−1.6 (2)	C20—C19—C24—C23	0.3 (2)
C7—C4—C5—C6	175.95 (13)	C18—C19—C24—C23	179.41 (15)
C2—C1—C6—C5	0.9 (2)	C22—C23—C24—C19	−0.7 (3)
Cl1—C1—C6—C5	−177.76 (11)	C8—C7—N1—O1	−0.27 (17)
C4—C5—C6—C1	0.5 (2)	C4—C7—N1—O1	177.18 (12)
C5—C4—C7—N1	176.96 (14)	C16—C17—N2—C11	179.49 (14)
C3—C4—C7—N1	−5.6 (2)	C12—C17—N2—C11	0.00 (15)
C5—C4—C7—C8	−6.1 (2)	C16—C17—N2—C10	−0.9 (2)
C3—C4—C7—C8	171.39 (14)	C12—C17—N2—C10	179.61 (12)
N1—C7—C8—C9	0.37 (17)	O2—C11—N2—C17	−179.88 (14)
C4—C7—C8—C9	−176.82 (12)	N3—C11—N2—C17	−0.18 (15)
C7—C8—C9—O1	−0.32 (15)	O2—C11—N2—C10	0.5 (2)
C7—C8—C9—C10	177.14 (14)	N3—C11—N2—C10	−179.80 (12)
C8—C9—C10—N2	−96.06 (19)	C9—C10—N2—C17	78.91 (18)
O1—C9—C10—N2	81.27 (16)	C9—C10—N2—C11	−101.52 (15)
N3—C12—C13—C14	177.73 (15)	O2—C11—N3—C12	179.99 (15)
C17—C12—C13—C14	0.3 (2)	N2—C11—N3—C12	0.29 (15)
C12—C13—C14—C15	1.2 (3)	O2—C11—N3—C18	−7.1 (2)
C13—C14—C15—C16	−1.7 (3)	N2—C11—N3—C18	173.20 (12)
C14—C15—C16—C17	0.6 (2)	C13—C12—N3—C11	−178.00 (15)
C15—C16—C17—N2	−178.55 (14)	C17—C12—N3—C11	−0.30 (15)
C15—C16—C17—C12	0.9 (2)	C13—C12—N3—C18	9.5 (2)
C13—C12—C17—C16	−1.4 (2)	C17—C12—N3—C18	−172.80 (13)
N3—C12—C17—C16	−179.37 (12)	C19—C18—N3—C11	−89.12 (17)
C13—C12—C17—N2	178.19 (13)	C19—C18—N3—C12	82.55 (18)
N3—C12—C17—N2	0.18 (14)	C8—C9—O1—N1	0.17 (16)
N3—C18—C19—C24	−104.54 (17)	C10—C9—O1—N1	−177.78 (12)
N3—C18—C19—C20	74.59 (18)	C7—N1—O1—C9	0.07 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2i	0.93	2.53	3.1949 (19)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2i	0.93	2.53	3.1949 (19)	129

Symmetry code: (i) .