5-Iodo-3-phenyl-2,1-benzoxazole.

The title compound, C13H8INO, was prepared by a condensation reaction of 4-nitro-benzene with phenyl-acetonitrile in NaOH-ethanol solution. There are two independent mol-ecules in the asymmetric unit, in which the dihedral angles between the benzene ring and the benzoisoxazole unit are 4.2 (3) and 4.1 (3)°. The crystal packing is governed by C-H⋯N, C-I⋯π and C-I⋯O inter-actions.

Related literature

For the biologial activity and applications of benzo[c]isoxazoles, see: McEvoy et al. (1968 ▶); Hester et al. (1989 ▶); Walsh et al. (1990 ▶); Angibaud et al. (2003 ▶). For a related structure, see: Teslenko et al. (2008 ▶). For a general synthetic procedure, see: Davis & Pizzini (1960 ▶).

Experimental

Crystal data

C13H8INO

M = 321.10

Monoclinic,

a = 5.381 (3) Å

b = 15.225 (7) Å

c = 13.749 (7) Å

β = 94.92 (3)°

V = 1122.2 (10) Å3

Z = 4

Mo Kα radiation

μ = 2.83 mm−1

T = 100 K

0.25 × 0.08 × 0.03 mm

Data collection

Kuma KM-4-CCD four-circle diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.44, T max = 0.80

15060 measured reflections

6015 independent reflections

4621 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.090

S = 1.00

6015 reflections

289 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.98 e Å−3

Δρmin = −1.01 e Å−3

Absolute structure: Flack (1983 ▶), 1659 Friedel pairs

Flack parameter: 0.00 (3)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005862/gk2554sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005862/gk2554Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005862/gk2554Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005862/gk2554Isup4.cml

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

C13H8INO	F(000) = 616
Mr = 321.10	Dx = 1.901 Mg m−3
Monoclinic, P21	Melting point = 390–391 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 5.381 (3) Å	Cell parameters from 15060 reflections
b = 15.225 (7) Å	θ = 3.0–34.7°
c = 13.749 (7) Å	µ = 2.83 mm−1
β = 94.92 (3)°	T = 100 K
V = 1122.2 (10) Å3	Needle, pale yellow
Z = 4	0.25 × 0.08 × 0.03 mm

Kuma KM-4-CCD four-circle diffractometer	6015 independent reflections
Radiation source: fine-focus sealed tube	4621 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ω scans	θmax = 34.7°, θmin = 3.0°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −8→7
Tmin = 0.44, Tmax = 0.80	k = −17→23
15060 measured reflections	l = −20→21

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
6015 reflections	Δρmax = 1.98 e Å−3
289 parameters	Δρmin = −1.01 e Å−3
1 restraint	Absolute structure: Flack (1983), 1659 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (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
I1A	0.51472 (6)	0.01154 (2)	0.19512 (2)	0.02514 (9)
O1A	−0.2353 (8)	0.2574 (3)	0.4305 (3)	0.0262 (9)
N1A	−0.0803 (9)	0.3076 (4)	0.3739 (4)	0.0316 (10)
C1A	0.0530 (10)	0.2453 (4)	0.3322 (4)	0.0256 (12)
C2A	0.2425 (11)	0.2686 (4)	0.2666 (5)	0.0303 (13)
H2A	0.2765	0.3276	0.2499	0.036*
C3A	0.3651 (11)	0.2002 (4)	0.2316 (4)	0.0261 (11)
H3A	0.4926	0.2110	0.1894	0.031*
C4A	0.3088 (10)	0.1115 (4)	0.2561 (4)	0.0219 (10)
C5A	0.1314 (10)	0.0903 (4)	0.3171 (4)	0.0204 (10)
H5A	0.0981	0.0309	0.3328	0.024*
C6A	−0.0029 (10)	0.1613 (3)	0.3564 (4)	0.0201 (10)
C7A	−0.1871 (10)	0.1707 (4)	0.4203 (4)	0.0213 (10)
C8A	−0.3335 (10)	0.1101 (4)	0.4753 (4)	0.0204 (10)
C9A	−0.2895 (11)	0.0191 (4)	0.4735 (4)	0.0260 (11)
H9A	−0.1608	−0.0034	0.4373	0.031*
C10A	−0.4324 (12)	−0.0380 (4)	0.5240 (4)	0.0267 (12)
H10A	−0.3982	−0.0992	0.5230	0.032*
C11A	−0.6211 (10)	−0.0080 (4)	0.5750 (4)	0.0296 (14)
H11A	−0.7201	−0.0478	0.6084	0.036*
C12A	−0.6676 (11)	0.0838 (4)	0.5776 (4)	0.0229 (11)
H12A	−0.7973	0.1054	0.6138	0.027*
C13A	−0.5264 (10)	0.1421 (4)	0.5282 (4)	0.0220 (11)
H13A	−0.5597	0.2033	0.5300	0.026*
I1B	−0.05111 (7)	0.30782 (2)	0.66158 (3)	0.02711 (9)
O1B	0.7816 (8)	0.2167 (3)	1.0229 (3)	0.0258 (8)
N1B	0.6242 (9)	0.2844 (3)	1.0482 (4)	0.0270 (10)
C1B	0.4622 (10)	0.2937 (3)	0.9704 (4)	0.0232 (11)
C2B	0.2531 (11)	0.3519 (4)	0.9611 (5)	0.0272 (12)
H2B	0.2166	0.3890	1.0136	0.033*
C3B	0.1074 (11)	0.3530 (4)	0.8749 (4)	0.0249 (11)
H3B	−0.0335	0.3907	0.8673	0.030*
C4B	0.1657 (9)	0.2974 (3)	0.7956 (4)	0.0206 (10)
C5B	0.3589 (10)	0.2384 (4)	0.8030 (4)	0.0220 (11)
H5B	0.3902	0.2010	0.7501	0.026*
C6B	0.5112 (10)	0.2353 (3)	0.8931 (4)	0.0199 (10)
C7B	0.7150 (10)	0.1873 (3)	0.9304 (4)	0.0196 (10)
C8B	0.8618 (10)	0.1135 (4)	0.8959 (4)	0.0216 (10)
C9B	0.8005 (11)	0.0769 (4)	0.8031 (4)	0.0258 (12)
H9B	0.6644	0.0996	0.7621	0.031*
C10B	0.9389 (10)	0.0082 (4)	0.7720 (4)	0.0255 (10)
H10B	0.8969	−0.0158	0.7089	0.031*
C11B	1.1383 (12)	−0.0274 (4)	0.8297 (4)	0.0285 (12)
H11B	1.2315	−0.0753	0.8076	0.034*
C12B	1.1968 (11)	0.0099 (5)	0.9218 (4)	0.0301 (11)
H12B	1.3328	−0.0131	0.9626	0.036*
C13B	1.0630 (11)	0.0790 (4)	0.9549 (4)	0.0253 (11)
H13B	1.1071	0.1032	1.0177	0.030*

	U11	U22	U33	U12	U13	U23
I1A	0.02109 (16)	0.03002 (19)	0.02445 (17)	0.00079 (15)	0.00275 (13)	−0.00571 (15)
O1A	0.028 (2)	0.021 (2)	0.031 (2)	0.0056 (16)	0.0085 (17)	0.0011 (16)
N1A	0.036 (3)	0.024 (2)	0.037 (3)	−0.001 (3)	0.014 (2)	0.007 (2)
C1A	0.010 (2)	0.055 (4)	0.011 (2)	0.000 (2)	−0.0008 (18)	0.000 (2)
C2A	0.029 (3)	0.033 (3)	0.030 (3)	−0.001 (3)	0.006 (2)	0.011 (2)
C3A	0.029 (3)	0.028 (3)	0.022 (3)	0.001 (2)	0.006 (2)	0.004 (2)
C4A	0.021 (3)	0.025 (3)	0.020 (2)	0.006 (2)	−0.0003 (19)	−0.002 (2)
C5A	0.021 (3)	0.015 (2)	0.025 (3)	0.000 (2)	0.001 (2)	−0.0027 (19)
C6A	0.021 (3)	0.018 (3)	0.021 (3)	0.000 (2)	0.001 (2)	0.0002 (19)
C7A	0.020 (3)	0.021 (3)	0.022 (3)	0.001 (2)	−0.003 (2)	0.0008 (19)
C8A	0.021 (2)	0.023 (3)	0.017 (2)	0.001 (2)	0.0032 (19)	−0.0026 (19)
C9A	0.042 (3)	0.018 (3)	0.019 (2)	0.005 (3)	0.005 (2)	−0.001 (2)
C10A	0.039 (3)	0.017 (3)	0.024 (3)	−0.001 (2)	0.000 (2)	0.002 (2)
C11A	0.021 (3)	0.048 (4)	0.020 (3)	−0.012 (2)	0.001 (2)	0.008 (2)
C12A	0.020 (3)	0.026 (3)	0.023 (3)	0.000 (2)	0.000 (2)	−0.003 (2)
C13A	0.020 (3)	0.025 (3)	0.021 (3)	0.003 (2)	0.001 (2)	−0.002 (2)
I1B	0.02550 (18)	0.02499 (18)	0.03013 (19)	0.00099 (17)	−0.00173 (14)	0.00057 (16)
O1B	0.032 (2)	0.028 (2)	0.0171 (19)	−0.0014 (18)	0.0017 (15)	−0.0014 (16)
N1B	0.035 (3)	0.021 (2)	0.025 (2)	−0.0026 (19)	0.004 (2)	0.0006 (17)
C1B	0.030 (3)	0.022 (3)	0.019 (2)	−0.005 (2)	0.007 (2)	0.0006 (18)
C2B	0.027 (3)	0.026 (3)	0.030 (3)	−0.003 (2)	0.012 (2)	0.001 (2)
C3B	0.021 (3)	0.024 (3)	0.032 (3)	0.000 (2)	0.009 (2)	−0.001 (2)
C4B	0.022 (2)	0.018 (3)	0.022 (2)	−0.004 (2)	0.0011 (19)	0.0015 (18)
C5B	0.023 (3)	0.021 (3)	0.022 (3)	−0.004 (2)	0.003 (2)	−0.0012 (19)
C6B	0.021 (3)	0.018 (2)	0.021 (3)	−0.003 (2)	0.005 (2)	−0.0020 (18)
C7B	0.023 (3)	0.017 (2)	0.019 (2)	−0.005 (2)	0.002 (2)	0.0018 (18)
C8B	0.020 (3)	0.019 (2)	0.026 (3)	−0.003 (2)	0.003 (2)	0.003 (2)
C9B	0.024 (3)	0.028 (3)	0.025 (3)	0.000 (2)	0.000 (2)	0.001 (2)
C10B	0.026 (3)	0.025 (3)	0.026 (2)	0.002 (3)	0.0045 (19)	−0.004 (2)
C11B	0.029 (3)	0.026 (3)	0.031 (3)	0.003 (2)	0.009 (2)	0.004 (2)
C12B	0.029 (3)	0.031 (3)	0.029 (3)	0.005 (3)	−0.003 (2)	0.006 (3)
C13B	0.027 (3)	0.028 (3)	0.020 (3)	0.001 (2)	−0.002 (2)	0.002 (2)

I1A—C4A	2.100 (5)	I1B—C4B	2.100 (5)
O1A—C7A	1.354 (6)	O1B—C7B	1.366 (6)
O1A—N1A	1.413 (6)	O1B—N1B	1.397 (6)
N1A—C1A	1.346 (8)	N1B—C1B	1.329 (8)
C1A—C6A	1.361 (8)	C1B—C6B	1.427 (7)
C1A—C2A	1.462 (8)	C1B—C2B	1.430 (8)
C2A—C3A	1.344 (9)	C2B—C3B	1.363 (9)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—C4A	1.430 (8)	C3B—C4B	1.437 (8)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.362 (7)	C4B—C5B	1.371 (8)
C5A—C6A	1.432 (7)	C5B—C6B	1.426 (8)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.387 (7)	C6B—C7B	1.379 (7)
C7A—C8A	1.466 (7)	C7B—C8B	1.475 (8)
C8A—C9A	1.405 (8)	C8B—C13B	1.398 (8)
C8A—C13A	1.405 (7)	C8B—C9B	1.406 (8)
C9A—C10A	1.387 (8)	C9B—C10B	1.374 (8)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—C11A	1.362 (8)	C10B—C11B	1.389 (8)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.420 (9)	C11B—C12B	1.399 (9)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.384 (8)	C12B—C13B	1.374 (9)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
C7A—O1A—N1A	110.0 (4)	C7B—O1B—N1B	110.9 (4)
C1A—N1A—O1A	102.4 (5)	C1B—N1B—O1B	104.3 (4)
N1A—C1A—C6A	114.9 (5)	N1B—C1B—C6B	112.5 (5)
N1A—C1A—C2A	121.2 (6)	N1B—C1B—C2B	126.5 (5)
C6A—C1A—C2A	123.9 (6)	C6B—C1B—C2B	121.0 (5)
C3A—C2A—C1A	115.1 (6)	C3B—C2B—C1B	118.3 (5)
C3A—C2A—H2A	122.5	C3B—C2B—H2B	120.8
C1A—C2A—H2A	122.5	C1B—C2B—H2B	120.8
C2A—C3A—C4A	121.7 (5)	C2B—C3B—C4B	120.4 (5)
C2A—C3A—H3A	119.1	C2B—C3B—H3B	119.8
C4A—C3A—H3A	119.1	C4B—C3B—H3B	119.8
C5A—C4A—C3A	122.9 (5)	C5B—C4B—C3B	122.9 (5)
C5A—C4A—I1A	119.7 (4)	C5B—C4B—I1B	118.4 (4)
C3A—C4A—I1A	117.4 (4)	C3B—C4B—I1B	118.7 (4)
C4A—C5A—C6A	117.1 (5)	C4B—C5B—C6B	117.5 (5)
C4A—C5A—H5A	121.4	C4B—C5B—H5B	121.2
C6A—C5A—H5A	121.4	C6B—C5B—H5B	121.2
C1A—C6A—C7A	104.0 (5)	C7B—C6B—C5B	136.0 (5)
C1A—C6A—C5A	119.2 (5)	C7B—C6B—C1B	104.2 (5)
C7A—C6A—C5A	136.8 (5)	C5B—C6B—C1B	119.8 (5)
O1A—C7A—C6A	108.7 (5)	O1B—C7B—C6B	108.0 (4)
O1A—C7A—C8A	116.4 (5)	O1B—C7B—C8B	116.3 (5)
C6A—C7A—C8A	134.9 (5)	C6B—C7B—C8B	135.6 (5)
C9A—C8A—C13A	119.0 (5)	C13B—C8B—C9B	119.2 (5)
C9A—C8A—C7A	120.9 (5)	C13B—C8B—C7B	120.6 (5)
C13A—C8A—C7A	120.1 (5)	C9B—C8B—C7B	120.2 (5)
C10A—C9A—C8A	120.5 (5)	C10B—C9B—C8B	119.6 (6)
C10A—C9A—H9A	119.8	C10B—C9B—H9B	120.2
C8A—C9A—H9A	119.8	C8B—C9B—H9B	120.2
C11A—C10A—C9A	121.2 (5)	C9B—C10B—C11B	122.1 (6)
C11A—C10A—H10A	119.4	C9B—C10B—H10B	118.9
C9A—C10A—H10A	119.4	C11B—C10B—H10B	118.9
C10A—C11A—C12A	118.9 (5)	C10B—C11B—C12B	117.5 (6)
C10A—C11A—H11A	120.5	C10B—C11B—H11B	121.3
C12A—C11A—H11A	120.5	C12B—C11B—H11B	121.3
C13A—C12A—C11A	120.9 (5)	C13B—C12B—C11B	121.8 (5)
C13A—C12A—H12A	119.6	C13B—C12B—H12B	119.1
C11A—C12A—H12A	119.6	C11B—C12B—H12B	119.1
C12A—C13A—C8A	119.5 (5)	C12B—C13B—C8B	119.8 (5)
C12A—C13A—H13A	120.3	C12B—C13B—H13B	120.1
C8A—C13A—H13A	120.3	C8B—C13B—H13B	120.1

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···N1Bi	0.95	2.40	3.247 (7)	149
C11A—H11A···N1Aii	0.95	2.47	3.339 (8)	152
C4A—I1A···Cgiii	2.10 (1)	3.62 (1)	5.637 (6)	160 (1)
C4B—I1B···O1A	2.10 (1)	3.34 (1)	5.325 (7)	156 (1)

Table 1

Intermolecular interactions (Å, °)

Cg is the centroid of the C1B–C6B ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3A—H3A⋯N1B i	0.95	2.40	3.247 (7)	149
C11A—H11A⋯N1A ii	0.95	2.47	3.339 (8)	152
C4A—I1A⋯Cg iii	2.100 (5)	3.618 (2)	5.637 (6)	160.0 (2)
C4B—I1B⋯O1A	2.100 (5)	3.335 (5)	5.325 (7)	156.3 (2)

Symmetry codes: (i) ; (ii) ; (iii) .