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

Teslenko, Y.; Matiychuk, V.S.; Kinzhybalo, V.; Lis, T.; Obushak, M.D.

doi:10.1107/S1600536813005862

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o508

doi:10.1107/S1600536813005862

Open

access

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

Yuriy Teslenko,^a ^* Vasyl S. Matiychuk,^a Vasyl Kinzhybalo,^b Tadeusz Lis ^c and Mykola D. Obushak ^a

^aDepartment of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla and Mefodiya 6, Lviv 79005, Ukraine, ^bInstitute of Low Temperature and Structure Research, Okolna 2, 50-422 Wrocław, Poland, and ^cFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland
^*Correspondence e-mail: dangercorp@gmail.com

(Received 2 February 2013; accepted 28 February 2013; online 9 March 2013)

The title compound, C₁₃H₈INO, was prepared by a condensation reaction of 4-nitrobenzene with phenylacetonitrile in NaOH–ethanol solution. There are two independent molecules 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 interactions.

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_r = 321.10
Monoclinic, P 2₁
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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wrocław, Poland.]$ ) 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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.090
S = 1.00
6015 reflections
289 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.98 e Å⁻³
Δρ_min = −1.01 e Å⁻³
Absolute structure: Flack (1983 ), 1659 Friedel pairs
Flack parameter: 0.00 (3)

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⋯N1Bⁱ	0.95	2.40	3.247 (7)	149
C11A—H11A⋯N1Aⁱⁱ	0.95	2.47	3.339 (8)	152
C4A—I1A⋯Cgⁱⁱⁱ	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) x, y, z-1; (ii) $[-x-1, y-{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wrocław, Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wrocław, Poland.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813005862/gk2554sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813005862/gk2554Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536813005862/gk2554Isup4.cml

checkCIF report

Comment top

Our interest in benzo[c]isoxazoles is concerned with their application as precursors of a variety of bioactive compounds (Angibaud et al., 2003; Walsh et al., 1990; Hester et al., 1989; McEvoy et al., 1968). The title compound will be used in our further investigations as arylation agent in palladium-catalyzed reactions with alkenes and alkynes.

The title compound crystalizes in the noncentrosymmetric monoclinic P2₁ space group with two independent molecules in the asymmetric part (A and B), see Fig. 1. The molecules are almost planar, the dihedral angles between the mean planes of benzoisoxazole and benzene rings being 4.2 (3)° and 4.1 (3)° for A and B, respectively. The geometrical parameters of the molecules are similar and consistent with the previously studied 2,1-benzoxazole derivatives (Teslenko et al., 2008).

Crystal packing is governed by hydrogen bonds of C–H···N type and other intermolecular interactions including C–I···π and C–I···O. Intermolecular interactions C4A–I1A···C_gⁱⁱⁱ (C_g is a centroid of C1B/C6B aromatic ring) and C4B–I1B···O1A connect the molecules into chains propagating in b-axis direction along 2₁ screw axis (see Fig. 2). Hydrogen bond C3A–H3A···N1Bⁱ connects the chains into corrugated layer parallel to the bc-plane. Hydrogen bond C11A–H11A···N1Aⁱⁱ binds successive layers.

Related literature top

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 top

Phenylacetonitrile (1.4 g, 12 mmol) and 5 ml of benzene solution of 4-iodonitrobenene (2.49 g, 10 mmol) were added with stirring to 40 ml of ethanol solution of potassium hydroxide (4 g, 0.1 mole). The mixture was stirred for 4 h at 323 K, then poured into 150 ml of water and acidified with hydrochloric acid. The precipitate was isolated by filtration, washed with water and dried. Recrystallization of crude product from ethanol gave 2.57 g (80% yield) of 5-iodo-3-phenyl-2,1-benzoxazole as pale yellow needles suitable for X-ray analysis, m.p. 390–391 K.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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).

Figures top

	Fig. 1. The asymmetric unit of the title compound with atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound showing intermolecular interactions as dashed lines (molecule A - red, molecule B - green).

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

Crystal data top

C₁₃H₈INO	F(000) = 616
M_r = 321.10	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.046P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
6015 reflections	Δρ_max = 1.98 e Å⁻³
289 parameters	Δρ_min = −1.01 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1659 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Crystal data top

C₁₃H₈INO	V = 1122.2 (10) Å³
M_r = 321.10	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 5.381 (3) Å	µ = 2.83 mm⁻¹
b = 15.225 (7) Å	T = 100 K
c = 13.749 (7) Å	0.25 × 0.08 × 0.03 mm
β = 94.92 (3)°

Data collection top

Kuma KM-4-CCD four-circle diffractometer	6015 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	4621 reflections with I > 2σ(I)
T_min = 0.44, T_max = 0.80	R_int = 0.053
15060 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 1.98 e Å⁻³
S = 1.00	Δρ_min = −1.01 e Å⁻³
6015 reflections	Absolute structure: Flack (1983), 1659 Friedel pairs
289 parameters	Absolute structure parameter: 0.00 (3)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1B–C6B ring.

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)

Symmetry codes: (i) x, y, z−1; (ii) −x−1, y−1/2, −z+1; (iii) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₈INO
M_r	321.10
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	5.381 (3), 15.225 (7), 13.749 (7)
β (°)	94.92 (3)
V (Å³)	1122.2 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.83
Crystal size (mm)	0.25 × 0.08 × 0.03

Data collection
Diffractometer	Kuma KM-4-CCD four-circle diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.44, 0.80
No. of measured, independent and observed [I > 2σ(I)] reflections	15060, 6015, 4621
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.800

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.090, 1.00
No. of reflections	6015
No. of parameters	289
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.98, −1.01
Absolute structure	Flack (1983), 1659 Friedel pairs
Absolute structure parameter	0.00 (3)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1B–C6B ring.

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	2.100 (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) x, y, z−1; (ii) −x−1, y−1/2, −z+1; (iii) −x+1, y−1/2, −z+1.

Acknowledgements

The authors are grateful to the State fund for fundamental research of Ukraine for the financial support (Project F54.3/004).

References

Angibaud, P., Bourdrez, X., Devine, A., End, D. W., Freyne, E., Ligny, Y., Muller, P., Mannens, G., Pilatte, I., Poncelet, V., Skrzat, S., Smets, G., Van Dun, J., Van Remoortere, P., Venet, M. & Wouters, W. (2003). Bioorg. Med. Chem. Lett. 13, 1543–1548. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Davis, R. B. & Pizzini, L. C. (1960). J. Org. Chem. 25, 1884–1888. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hester, J. B., Ludens, J. H., Emmert, D. E. & West, B. E. (1989). J. Med. Chem. 32, 1157–1163. CrossRef CAS PubMed Web of Science Google Scholar
McEvoy, F. J., Greenblatt, E. N., Osterrerg, A. C. & Allen, G. R. Jr (1968). J. Med. Chem. 11, 1248–1250. CrossRef CAS PubMed Web of Science Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wrocław, Poland. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Teslenko, Y., Matiychuk, V., Obushak, M., Kinzhybalo, V. & Ślepokura, K. (2008). Acta Cryst. E64, o2420. Web of Science CSD CrossRef IUCr Journals Google Scholar
Walsh, D. A., Moran, H. W., Shamblee, D. A. & Welstead, W. J. (1990). J. Med. Chem. 33, 2296–2304. CrossRef CAS PubMed Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o508

doi:10.1107/S1600536813005862

Open

access