3-(10-Chloro-9-anthr-yl)-5-[3-(prop-2-yn-yloxy)phenoxy-meth-yl]isoxazole.

In the title mol-ecule, C(27)H(18)ClNO(3), the anthracene mean plane forms dihedral angles of 67.43 (2) and 15.75 (3)° with the isoxazole and benzene rings, respectively. In the crystal structure, C-H⋯π inter-actions link mol-ecules into centrosymmetric dimers, which are further linked by weak inter-molecular C-H⋯N hydrogen bonds into ribbons propagating in the [110] direction.

Related literature

For the preparation of the title compound, see Han et al. (2003 ▶). For pharmaceutical applications of isoxazole and its derivatives, see: De Luca et al. (2001 ▶); Yamamoto et al. (2007 ▶); Reuman et al. (2008 ▶).

Experimental

Crystal data

C27H18ClNO3

M = 439.87

Triclinic,

a = 8.4816 (3) Å

b = 8.6450 (3) Å

c = 16.8606 (6) Å

α = 100.364 (1)°

β = 103.596 (1)°

γ = 94.965 (1)°

V = 1171.25 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 292 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: none

4812 measured reflections

4812 independent reflections

4227 reflections with I > 2σ(I)

R int = 0.0000

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.163

S = 1.06

4812 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019229/cv2557sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019229/cv2557Isup2.hkl

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

C27H18ClNO3	Z = 2
Mr = 439.87	F(000) = 456
Triclinic, P1	Dx = 1.247 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4816 (3) Å	Cell parameters from 6384 reflections
b = 8.6450 (3) Å	θ = 2.5–28.2°
c = 16.8606 (6) Å	µ = 0.19 mm−1
α = 100.364 (1)°	T = 292 K
β = 103.596 (1)°	Block, colourless
γ = 94.965 (1)°	0.30 × 0.20 × 0.10 mm
V = 1171.25 (7) Å3

Bruker SMART 4K CCD area-detector diffractometer	4227 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 26.5°, θmin = 2.4°
φ and ω scans	h = −10→10
4812 measured reflections	k = −10→10
4812 independent reflections	l = 0→21

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0786P)2 + 0.2928P] where P = (Fo2 + 2Fc2)/3
4812 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.39 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
C1	0.2863 (2)	0.3620 (2)	0.91382 (11)	0.0372 (4)
C2	0.1335 (3)	0.4195 (2)	0.91474 (14)	0.0487 (5)
H2	0.0916	0.4184	0.9609	0.058*
C3	0.0490 (3)	0.4751 (3)	0.85017 (16)	0.0566 (5)
H3	−0.0495	0.5128	0.8526	0.068*
C4	0.1087 (3)	0.4767 (3)	0.77859 (15)	0.0534 (5)
H4	0.0487	0.5145	0.7341	0.064*
C5	0.2529 (2)	0.4234 (2)	0.77469 (12)	0.0426 (4)
H5	0.2899	0.4244	0.7270	0.051*
C6	0.3493 (2)	0.36581 (19)	0.84180 (10)	0.0338 (4)
C7	0.4989 (2)	0.30988 (19)	0.83910 (10)	0.0318 (3)
C8	0.5881 (2)	0.2499 (2)	0.90563 (10)	0.0335 (4)
C9	0.7423 (2)	0.1965 (2)	0.90562 (12)	0.0430 (4)
H9	0.7856	0.2003	0.8601	0.052*
C10	0.8275 (3)	0.1400 (3)	0.97066 (14)	0.0543 (5)
H10	0.9282	0.1063	0.9693	0.065*
C11	0.7643 (3)	0.1322 (3)	1.04012 (13)	0.0580 (6)
H11	0.8229	0.0920	1.0840	0.070*
C12	0.6195 (3)	0.1825 (3)	1.04358 (11)	0.0504 (5)
H12	0.5801	0.1767	1.0901	0.060*
C13	0.5254 (2)	0.2444 (2)	0.97749 (10)	0.0369 (4)
C14	0.3769 (2)	0.3003 (2)	0.97840 (11)	0.0393 (4)
C15	0.56449 (19)	0.3098 (2)	0.76469 (10)	0.0313 (3)
C16	0.5831 (2)	0.1769 (2)	0.70657 (11)	0.0372 (4)
H16	0.5563	0.0702	0.7063	0.045*
C17	0.6479 (2)	0.2387 (2)	0.65203 (10)	0.0369 (4)
C18	0.7037 (2)	0.1683 (3)	0.57805 (11)	0.0447 (4)
H18A	0.8181	0.2071	0.5854	0.054*
H18B	0.6918	0.0536	0.5705	0.054*
C19	0.6541 (2)	0.1848 (2)	0.43448 (11)	0.0379 (4)
C20	0.7742 (2)	0.0930 (2)	0.42197 (11)	0.0378 (4)
H20	0.8285	0.0457	0.4640	0.045*
C21	0.8133 (2)	0.0720 (2)	0.34504 (11)	0.0356 (4)
C22	0.7331 (2)	0.1422 (2)	0.28241 (12)	0.0428 (4)
H22	0.7601	0.1289	0.2315	0.051*
C23	0.6120 (2)	0.2329 (2)	0.29685 (12)	0.0444 (4)
H23	0.5571	0.2799	0.2549	0.053*
C24	0.5710 (2)	0.2549 (2)	0.37219 (12)	0.0429 (4)
H24	0.4891	0.3156	0.3810	0.051*
C25	0.9797 (3)	−0.0505 (2)	0.26169 (12)	0.0444 (4)
H25A	0.8811	−0.0784	0.2163	0.053*
H25B	1.0408	−0.1403	0.2597	0.053*
C26	1.0785 (2)	0.0859 (2)	0.24940 (12)	0.0447 (4)
C27	1.1606 (3)	0.1948 (3)	0.24028 (15)	0.0581 (6)
H27	1.2255	0.2809	0.2331	0.070*
Cl1	0.29951 (8)	0.29325 (7)	1.06495 (3)	0.0617 (2)
N1	0.6140 (2)	0.44298 (18)	0.74604 (9)	0.0423 (4)
O1	0.66859 (17)	0.39855 (16)	0.67356 (8)	0.0448 (3)
O2	0.60568 (17)	0.2133 (2)	0.50758 (8)	0.0520 (4)
O3	0.93481 (17)	−0.02142 (17)	0.33887 (8)	0.0473 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0398 (9)	0.0328 (8)	0.0409 (9)	0.0008 (7)	0.0202 (7)	0.0011 (7)
C2	0.0488 (11)	0.0461 (11)	0.0581 (12)	0.0079 (8)	0.0309 (9)	0.0046 (9)
C3	0.0447 (11)	0.0537 (12)	0.0799 (15)	0.0180 (9)	0.0302 (11)	0.0117 (11)
C4	0.0455 (11)	0.0538 (12)	0.0653 (13)	0.0155 (9)	0.0136 (10)	0.0202 (10)
C5	0.0425 (10)	0.0460 (10)	0.0436 (10)	0.0086 (8)	0.0149 (8)	0.0140 (8)
C6	0.0373 (8)	0.0313 (8)	0.0342 (8)	0.0027 (6)	0.0143 (7)	0.0045 (6)
C7	0.0358 (8)	0.0333 (8)	0.0279 (8)	0.0031 (6)	0.0137 (6)	0.0039 (6)
C8	0.0394 (8)	0.0344 (8)	0.0279 (8)	0.0032 (7)	0.0118 (7)	0.0060 (6)
C9	0.0427 (10)	0.0528 (11)	0.0389 (9)	0.0120 (8)	0.0144 (8)	0.0155 (8)
C10	0.0475 (11)	0.0664 (13)	0.0528 (12)	0.0179 (10)	0.0087 (9)	0.0231 (10)
C11	0.0634 (13)	0.0702 (14)	0.0412 (11)	0.0117 (11)	0.0027 (10)	0.0265 (10)
C12	0.0624 (13)	0.0605 (12)	0.0280 (9)	0.0016 (10)	0.0099 (8)	0.0139 (8)
C13	0.0448 (9)	0.0374 (9)	0.0270 (8)	−0.0022 (7)	0.0111 (7)	0.0044 (6)
C14	0.0503 (10)	0.0390 (9)	0.0302 (8)	−0.0030 (7)	0.0218 (7)	0.0007 (7)
C15	0.0296 (7)	0.0390 (9)	0.0278 (8)	0.0065 (6)	0.0101 (6)	0.0093 (6)
C16	0.0433 (9)	0.0375 (9)	0.0343 (9)	0.0070 (7)	0.0165 (7)	0.0070 (7)
C17	0.0393 (9)	0.0444 (10)	0.0300 (8)	0.0106 (7)	0.0117 (7)	0.0089 (7)
C18	0.0493 (10)	0.0601 (12)	0.0309 (9)	0.0190 (9)	0.0174 (8)	0.0106 (8)
C19	0.0392 (9)	0.0472 (10)	0.0286 (8)	0.0072 (7)	0.0124 (7)	0.0051 (7)
C20	0.0406 (9)	0.0464 (10)	0.0302 (8)	0.0099 (7)	0.0109 (7)	0.0131 (7)
C21	0.0376 (9)	0.0397 (9)	0.0333 (8)	0.0067 (7)	0.0143 (7)	0.0097 (7)
C22	0.0448 (10)	0.0568 (11)	0.0339 (9)	0.0111 (8)	0.0163 (7)	0.0175 (8)
C23	0.0453 (10)	0.0555 (11)	0.0389 (9)	0.0154 (8)	0.0110 (8)	0.0217 (8)
C24	0.0405 (9)	0.0523 (11)	0.0391 (9)	0.0161 (8)	0.0117 (8)	0.0110 (8)
C25	0.0513 (10)	0.0448 (10)	0.0430 (10)	0.0123 (8)	0.0252 (8)	0.0039 (8)
C26	0.0413 (9)	0.0553 (11)	0.0408 (10)	0.0135 (8)	0.0154 (8)	0.0089 (8)
C27	0.0500 (11)	0.0662 (14)	0.0636 (14)	0.0066 (10)	0.0203 (10)	0.0206 (11)
Cl1	0.0751 (4)	0.0780 (4)	0.0412 (3)	0.0068 (3)	0.0364 (3)	0.0093 (2)
N1	0.0581 (9)	0.0403 (8)	0.0368 (8)	0.0081 (7)	0.0263 (7)	0.0101 (6)
O1	0.0603 (8)	0.0456 (7)	0.0381 (7)	0.0079 (6)	0.0277 (6)	0.0131 (5)
O2	0.0505 (8)	0.0849 (10)	0.0285 (6)	0.0301 (7)	0.0174 (6)	0.0122 (6)
O3	0.0562 (8)	0.0576 (8)	0.0425 (7)	0.0274 (6)	0.0266 (6)	0.0192 (6)

C1—C14	1.395 (3)	C15—C16	1.416 (2)
C1—C2	1.430 (3)	C16—C17	1.340 (2)
C1—C6	1.441 (2)	C16—H16	0.9300
C2—C3	1.345 (3)	C17—O1	1.349 (2)
C2—H2	0.9300	C17—C18	1.485 (2)
C3—C4	1.416 (3)	C18—O2	1.418 (2)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.355 (3)	C18—H18B	0.9700
C4—H4	0.9300	C19—C20	1.376 (3)
C5—C6	1.427 (2)	C19—O2	1.377 (2)
C5—H5	0.9300	C19—C24	1.386 (3)
C6—C7	1.404 (2)	C20—C21	1.398 (2)
C7—C8	1.406 (2)	C20—H20	0.9300
C7—C15	1.487 (2)	C21—O3	1.374 (2)
C8—C9	1.424 (3)	C21—C22	1.382 (2)
C8—C13	1.440 (2)	C22—C23	1.385 (3)
C9—C10	1.358 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.379 (3)
C10—C11	1.407 (3)	C23—H23	0.9300
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.348 (3)	C25—O3	1.426 (2)
C11—H11	0.9300	C25—C26	1.461 (3)
C12—C13	1.427 (3)	C25—H25A	0.9700
C12—H12	0.9300	C25—H25B	0.9700
C13—C14	1.390 (3)	C26—C27	1.176 (3)
C14—Cl1	1.7434 (17)	C27—H27	0.9300
C15—N1	1.308 (2)	N1—O1	1.4082 (19)
C14—C1—C2	123.58 (17)	C16—C15—C7	127.76 (15)
C14—C1—C6	118.09 (16)	C17—C16—C15	104.87 (16)
C2—C1—C6	118.33 (17)	C17—C16—H16	127.6
C3—C2—C1	121.36 (19)	C15—C16—H16	127.6
C3—C2—H2	119.3	C16—C17—O1	109.76 (16)
C1—C2—H2	119.3	C16—C17—C18	133.60 (18)
C2—C3—C4	120.68 (19)	O1—C17—C18	116.60 (16)
C2—C3—H3	119.7	O2—C18—C17	107.63 (15)
C4—C3—H3	119.7	O2—C18—H18A	110.2
C5—C4—C3	120.19 (19)	C17—C18—H18A	110.2
C5—C4—H4	119.9	O2—C18—H18B	110.2
C3—C4—H4	119.9	C17—C18—H18B	110.2
C4—C5—C6	121.70 (18)	H18A—C18—H18B	108.5
C4—C5—H5	119.1	C20—C19—O2	123.81 (16)
C6—C5—H5	119.1	C20—C19—C24	121.26 (16)
C7—C6—C5	122.69 (16)	O2—C19—C24	114.93 (16)
C7—C6—C1	119.58 (15)	C19—C20—C21	118.90 (16)
C5—C6—C1	117.71 (16)	C19—C20—H20	120.6
C6—C7—C8	120.95 (15)	C21—C20—H20	120.6
C6—C7—C15	120.45 (14)	O3—C21—C22	124.87 (16)
C8—C7—C15	118.59 (15)	O3—C21—C20	114.38 (15)
C7—C8—C9	122.18 (15)	C22—C21—C20	120.76 (17)
C7—C8—C13	119.87 (16)	C21—C22—C23	118.85 (17)
C9—C8—C13	117.94 (15)	C21—C22—H22	120.6
C10—C9—C8	121.44 (18)	C23—C22—H22	120.6
C10—C9—H9	119.3	C24—C23—C22	121.41 (16)
C8—C9—H9	119.3	C24—C23—H23	119.3
C9—C10—C11	120.4 (2)	C22—C23—H23	119.3
C9—C10—H10	119.8	C23—C24—C19	118.82 (17)
C11—C10—H10	119.8	C23—C24—H24	120.6
C12—C11—C10	120.54 (18)	C19—C24—H24	120.6
C12—C11—H11	119.7	O3—C25—C26	112.99 (15)
C10—C11—H11	119.7	O3—C25—H25A	109.0
C11—C12—C13	121.53 (18)	C26—C25—H25A	109.0
C11—C12—H12	119.2	O3—C25—H25B	109.0
C13—C12—H12	119.2	C26—C25—H25B	109.0
C14—C13—C12	123.94 (17)	H25A—C25—H25B	107.8
C14—C13—C8	117.93 (16)	C27—C26—C25	178.8 (2)
C12—C13—C8	118.13 (18)	C26—C27—H27	180.0
C13—C14—C1	123.58 (16)	C15—N1—O1	105.45 (14)
C13—C14—Cl1	118.27 (14)	C17—O1—N1	108.51 (13)
C1—C14—Cl1	118.15 (15)	C19—O2—C18	117.55 (14)
N1—C15—C16	111.40 (15)	C21—O3—C25	117.66 (14)
N1—C15—C7	120.84 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···N1i	0.93	2.57	3.465 (3)	163
C16—H16···Cgii	0.93	2.67	3.431 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯N1i	0.93	2.57	3.465 (3)	163
C16—H16⋯Cgii	0.93	2.67	3.431 (2)	140

Symmetry codes: (i) ; (ii) .