2,10-Bis(3-bromo-phen-yl)-3,7,11,15-tetra-oxa-8,16-diaza-tricyclo-[12.2.1.1]octa-deca-1(16),6(18),8,14(17)-tetra-ene.

The title compound, C(24)H(20)Br(2)N(2)O(4), is an 18-membered tricycle including two isoxazole rings. The asymmetric unit contains one half of the formula unit; a centre of inversion is located at the centroid of the compound. The dihedral angle between adjacent isoxazole and benzene rings is 84.0 (2)°. The compound displays intra- and inter-molecular π-π stacking inter-actions between the isoxazole rings, the shortest centroid-centroid distances being 3.837 (3) and 3.634 (3) Å, respectively. The mol-ecules are stacked in columns along the a axis with short Br⋯Br contacts [3.508 (1) Å].

Related literature

For the biological activity of isoxazole derivatives, see: Kim et al. (1994 ▶, 1997 ▶); Lang & Lin (1984 ▶). For the syntheses of various pyrano[3,4-c]isoxzole derivatives, see: Kim et al. (1999 ▶).

Experimental

Crystal data

C24H20Br2N2O4

M = 560.24

Triclinic,

a = 5.6446 (4) Å

b = 7.3703 (5) Å

c = 13.701 (1) Å

α = 93.735 (1)°

β = 99.564 (1)°

γ = 102.363 (1)°

V = 546.03 (7) Å3

Z = 1

Mo Kα radiation

μ = 3.75 mm−1

T = 200 K

0.34 × 0.26 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.797, T max = 1.000

4051 measured reflections

2645 independent reflections

2040 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.152

S = 1.30

2645 reflections

145 parameters

H-atom parameters constrained

Δρmax = 1.25 e Å−3

Δρmin = −1.87 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028813/ng5004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028813/ng5004Isup2.hkl

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

C24H20Br2N2O4	Z = 1
Mr = 560.24	F(000) = 280
Triclinic, P1	Dx = 1.704 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6446 (4) Å	Cell parameters from 2388 reflections
b = 7.3703 (5) Å	θ = 2.8–28.1°
c = 13.701 (1) Å	µ = 3.75 mm−1
α = 93.735 (1)°	T = 200 K
β = 99.564 (1)°	Plate, colorless
γ = 102.363 (1)°	0.34 × 0.26 × 0.17 mm
V = 546.03 (7) Å3

Bruker SMART 1000 CCD diffractometer	2645 independent reflections
Radiation source: fine-focus sealed tube	2040 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→6
Tmin = 0.797, Tmax = 1.000	k = −9→9
4051 measured reflections	l = −16→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.30	w = 1/[σ2(Fo2) + (0.P)2 + 3.5324P] where P = (Fo2 + 2Fc2)/3
2645 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 1.25 e Å−3
0 restraints	Δρmin = −1.87 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
Br1	0.78777 (12)	0.13416 (10)	0.45968 (6)	0.0464 (2)
O1	−0.0873 (7)	0.2957 (6)	−0.0511 (3)	0.0304 (9)
O2	−0.0557 (7)	−0.0026 (5)	0.2100 (3)	0.0323 (9)
N1	−0.1737 (8)	0.2688 (7)	0.0394 (4)	0.0315 (10)
C1	0.5786 (11)	0.2773 (8)	0.3908 (4)	0.0336 (12)
C2	0.3670 (11)	0.1843 (8)	0.3295 (4)	0.0333 (12)
H2	0.3226	0.0517	0.3216	0.040*
C3	0.2166 (10)	0.2874 (8)	0.2784 (4)	0.0288 (11)
C4	0.2855 (12)	0.4808 (8)	0.2927 (5)	0.0383 (14)
H4	0.1827	0.5521	0.2588	0.046*
C5	0.5037 (13)	0.5714 (9)	0.3561 (5)	0.0443 (16)
H5	0.5493	0.7040	0.3655	0.053*
C6	0.6540 (12)	0.4683 (9)	0.4054 (5)	0.0411 (15)
H6	0.8049	0.5278	0.4482	0.049*
C7	−0.0170 (10)	0.1934 (7)	0.2048 (4)	0.0286 (11)
H7	−0.1606	0.2385	0.2229	0.034*
C8	0.0115 (9)	0.2363 (7)	0.1015 (4)	0.0254 (11)
C9	0.2206 (10)	0.2402 (7)	0.0570 (4)	0.0273 (11)
H9	0.3764	0.2208	0.0867	0.033*
C10	0.1503 (9)	0.2772 (7)	−0.0368 (4)	0.0263 (11)
C11	0.2785 (10)	0.2954 (8)	−0.1230 (4)	0.0303 (12)
H11A	0.4454	0.3774	−0.1016	0.036*
H11B	0.1857	0.3539	−0.1749	0.036*
C12	−0.2998 (10)	−0.1054 (8)	0.1658 (4)	0.0310 (12)
H12A	−0.3729	−0.0385	0.1125	0.037*
H12B	−0.4066	−0.1201	0.2166	0.037*

	U11	U22	U33	U12	U13	U23
Br1	0.0331 (3)	0.0454 (4)	0.0559 (4)	0.0092 (3)	−0.0055 (3)	0.0045 (3)
O1	0.0248 (19)	0.038 (2)	0.031 (2)	0.0108 (16)	0.0029 (16)	0.0109 (17)
O2	0.029 (2)	0.029 (2)	0.032 (2)	−0.0001 (16)	−0.0033 (16)	0.0014 (16)
N1	0.023 (2)	0.040 (3)	0.032 (3)	0.008 (2)	0.0034 (19)	0.005 (2)
C1	0.034 (3)	0.034 (3)	0.033 (3)	0.011 (2)	0.005 (2)	0.006 (2)
C2	0.035 (3)	0.027 (3)	0.035 (3)	0.002 (2)	0.009 (2)	−0.006 (2)
C3	0.031 (3)	0.026 (3)	0.027 (3)	0.004 (2)	0.003 (2)	0.003 (2)
C4	0.042 (3)	0.029 (3)	0.038 (3)	0.007 (3)	−0.006 (3)	0.002 (3)
C5	0.052 (4)	0.026 (3)	0.042 (4)	−0.004 (3)	−0.008 (3)	0.000 (3)
C6	0.033 (3)	0.044 (4)	0.035 (3)	−0.008 (3)	−0.004 (3)	0.002 (3)
C7	0.028 (3)	0.025 (3)	0.031 (3)	0.006 (2)	0.003 (2)	0.000 (2)
C8	0.025 (3)	0.022 (2)	0.030 (3)	0.007 (2)	0.002 (2)	0.002 (2)
C9	0.022 (2)	0.026 (3)	0.034 (3)	0.005 (2)	0.002 (2)	0.004 (2)
C10	0.022 (2)	0.022 (2)	0.032 (3)	0.0018 (19)	0.002 (2)	0.004 (2)
C11	0.029 (3)	0.027 (3)	0.032 (3)	0.002 (2)	0.005 (2)	0.004 (2)
C12	0.023 (3)	0.031 (3)	0.038 (3)	0.003 (2)	0.005 (2)	0.007 (2)

Br1—C1	1.921 (6)	C5—H5	0.9500
O1—C10	1.360 (6)	C6—H6	0.9500
O1—N1	1.416 (6)	C7—C8	1.497 (8)
O2—C7	1.423 (6)	C7—H7	1.0000
O2—C12	1.433 (6)	C8—C9	1.412 (7)
N1—C8	1.308 (7)	C9—C10	1.344 (7)
C1—C2	1.358 (8)	C9—H9	0.9500
C1—C6	1.372 (9)	C10—C11	1.483 (8)
C2—C3	1.391 (8)	C11—C12i	1.520 (8)
C2—H2	0.9500	C11—H11A	0.9900
C3—C4	1.386 (8)	C11—H11B	0.9900
C3—C7	1.521 (7)	C12—C11i	1.520 (8)
C4—C5	1.391 (8)	C12—H12A	0.9900
C4—H4	0.9500	C12—H12B	0.9900
C5—C6	1.381 (9)
C10—O1—N1	107.8 (4)	O2—C7—H7	109.7
C7—O2—C12	114.0 (4)	C8—C7—H7	109.7
C8—N1—O1	105.5 (4)	C3—C7—H7	109.7
C2—C1—C6	123.7 (6)	N1—C8—C9	111.9 (5)
C2—C1—Br1	118.4 (5)	N1—C8—C7	120.4 (5)
C6—C1—Br1	117.9 (5)	C9—C8—C7	127.6 (5)
C1—C2—C3	118.6 (5)	C10—C9—C8	104.7 (5)
C1—C2—H2	120.7	C10—C9—H9	127.6
C3—C2—H2	120.7	C8—C9—H9	127.6
C4—C3—C2	119.1 (5)	C9—C10—O1	110.0 (5)
C4—C3—C7	119.1 (5)	C9—C10—C11	132.4 (5)
C2—C3—C7	121.7 (5)	O1—C10—C11	117.5 (5)
C3—C4—C5	120.7 (6)	C10—C11—C12i	110.7 (5)
C3—C4—H4	119.6	C10—C11—H11A	109.5
C5—C4—H4	119.6	C12i—C11—H11A	109.5
C6—C5—C4	119.8 (6)	C10—C11—H11B	109.5
C6—C5—H5	120.1	C12i—C11—H11B	109.5
C4—C5—H5	120.1	H11A—C11—H11B	108.1
C1—C6—C5	118.0 (6)	O2—C12—C11i	107.4 (4)
C1—C6—H6	121.0	O2—C12—H12A	110.2
C5—C6—H6	121.0	C11i—C12—H12A	110.2
O2—C7—C8	109.7 (4)	O2—C12—H12B	110.2
O2—C7—C3	107.8 (4)	C11i—C12—H12B	110.2
C8—C7—C3	110.1 (5)	H12A—C12—H12B	108.5
C10—O1—N1—C8	0.0 (6)	C2—C3—C7—C8	−113.0 (6)
C6—C1—C2—C3	−0.1 (10)	O1—N1—C8—C9	0.0 (6)
Br1—C1—C2—C3	−179.2 (4)	O1—N1—C8—C7	−177.6 (4)
C1—C2—C3—C4	−0.8 (9)	O2—C7—C8—N1	100.4 (6)
C1—C2—C3—C7	177.1 (6)	C3—C7—C8—N1	−141.0 (5)
C2—C3—C4—C5	0.8 (10)	O2—C7—C8—C9	−76.8 (7)
C7—C3—C4—C5	−177.1 (6)	C3—C7—C8—C9	41.8 (7)
C3—C4—C5—C6	0.1 (11)	N1—C8—C9—C10	0.0 (6)
C2—C1—C6—C5	1.1 (10)	C7—C8—C9—C10	177.4 (5)
Br1—C1—C6—C5	−179.9 (5)	C8—C9—C10—O1	0.0 (6)
C4—C5—C6—C1	−1.0 (11)	C8—C9—C10—C11	−178.2 (5)
C12—O2—C7—C8	−76.1 (6)	N1—O1—C10—C9	0.0 (6)
C12—O2—C7—C3	164.0 (5)	N1—O1—C10—C11	178.6 (4)
C4—C3—C7—O2	−175.5 (5)	C9—C10—C11—C12i	73.1 (7)
C2—C3—C7—O2	6.6 (7)	O1—C10—C11—C12i	−105.0 (5)
C4—C3—C7—C8	64.8 (7)	C7—O2—C12—C11i	147.7 (5)