(E)-2-[2-(1-Naphthyl)­vinyl]-3-tosyl-2,3-di­hydro-1,3-benzo­thia­zole

The title compound, C₂₆H₂₁NO₂S₂, which consists of a benzo­thia­zole skeleton with [alpha]-naphthyl­vinyl and tosyl groups at positions 2 and 3, respectively, was prepared by palladium-copper-catalyzed heteroannulation. The E configuration of the mol­ecule about the vinyl C=C bond is established by the benzothiazole-naphthyl C-C-C-C torsion angle of 177.5 (4)°. The five-membered heterocyclic ring adopts an envelope conformation with the Csp³ atom 0.380 (6) Å from the C₂NS plane. The two S-C [1.751 (4) and 1.838 (4) Å] and two N-C [1.426 (5) and 1.482 (5) Å] bond lengths in the thia­zole ring differ significantly.

S1. Comment

The benzothiazole system, (I), containing a heterocyclic ring with sulfur and nitrogen as heteroatoms, is often used as an antihypertensive, an anticoagulant and a calcium agonist (Yamamoto et al., 1998). Substituted benzothiazolines find wide-ranging applications as efficient anticonvulsant, vasodilator and blood platelet aggregation inhibitors (Ucar et al., 1998) and as antifungal agents (Kanoongo et al., 1990). As part of our ongoing program on the synthesis and characterization of new heterocyclic compounds of biological importance (Kundu et al., 1999; Nandi et al., 2000) and to build up a hierarchy for such systems, the structure determination of (E)-2-[2-(1-naphthyl)vinyl]-3-tosyl-2,3-dihydro-1H-benzothiazole, (II), was undertaken.

The E configuration of the molecule of (II), which contains a benzothiazole moiety (A) with α-naphthylvinyl (B) and tosyl (C) substituents at the 2 and 3 positions, respectively, is established by the torsion angle C14—C15—C16—C17 of 177.5 (4)°. The five-membered thiazole ring (N, C8, C13, S2 and C14) displays an envelope conformation with the C14 atom 0.380 (6) Å from the least-squares plane through the remaining endocyclic atoms (r.m.s deviation 0.006 Å). The dihedral angles between the planar parts of A (atoms N, C8–C13 and S2), B (atoms C17–C26) and C (atoms C1—C7) are A/B 82 (1), A/C 112 (1) and B/C 131.5 (4)°. The maximum deviation for an in-plane atom (C9) from the corresponding least-squares plane is 0.04 (8) Å. The bond lengths and angles observed for the heterocyclic ring in (II) are similar to those reported for related structures (Miler-Srenger, 1973; Yeap et al., 1999). The C13—S2—C14 angle of 91.0 (2)° indicates that the S2 atom uses only the p orbital to form bonds with the C13 and C14 atoms, of which C13 is a part of an aromatic ring and C14 is sp³ hybridized. Consequently, the S—C bond distances in the heterocyclic ring [S2—C13 1.751 (4) and S2—C14 1.838 (4) Å] differ significantly. The asymmetric nature of bonding of the C atoms (C8 and C14) is also reflected in the difference between the two N—C distances; N—C8 1.426 (5) and N—C14 1.482 (5) Å. The bond distances and angles for the tosyl and α-naphthylvinyl groups are within expected ranges (Chiaroni et al., 1994; Dobson et al., 1996). A comparison of the geometrical parameters of various heterocyclic derivatives (Table 3) reveals that the conformation of the five-membered C₃NS ring has a profound influence on the molecular dimensions. In compounds with a non-planar C₃NS ring, the S—C and N—C bond distances show greater assymmetry compared with those having a planar C₃NS ring.

Both sulfonyl-O atoms are involved in weak (C—H···O) intermolecular hydrogen bonds with benzothiazole and naphthyl C atoms (Table 2). In the solid state, the crystal packing is stabilized by van der Waals interactions and a weak intermolecular hydrogen bond.

S2. Experimental

A mixture of 3-(2-aminophenylthio)prop-1-yne (3.67 mmol) and 1-iodonaphthalene (4.4 mmol) in acetonitrile (5 ml) was stirred at room temperature for 24 h under a nitrogen atmosphere in the presence of (PPh₃)₂PdCl₂ (0.11 mmol), CuI (0.22 mmol) and triethylamine (14.68 mmol). The resultant product after tosylation with p-TsCl (1.2 equivalents) in the presence of pyridine (2.0 equivalents) in dichloromethane was cyclized with CuI (40 mole %) in triethylamine (4 equivalents) by refluxing in tetrahydrofuran (10 ml) for 36 h under an argon atmosphere to afford (II), which was purified by column chromatography on silica gel (60–120 mesh) using 5% ethylacetate as eluant in light petroleum (333–353 K) in 63% yield (m.p. 452–453 K). Single crystals suitable for X-ray analysis were obtained by slow crystallization from a solution of (II) in a light petroleum (333–353 K) and ether mixture (3:1).

S3. Refinement

The H atoms were refined using a riding model and their isotropic displacement parameters were set to 1.2 times (1.5 times for CH₃ groups) the equivalent displacement parameters of their parent atoms.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: MULTAN88 (Debaerdemaeker et al., 1988); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. ZORTEP (Zsolnai, 1995) view (50% probability level) of (II).

(E)-2-(2-α-Naphthyl)vinyl-3-p-tosyl benzothiazoline

Crystal data

C26H21NO2S2	F(000) = 928
Mr = 443.56	Dx = 1.336 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
a = 10.006 (4) Å	Cell parameters from 20 reflections
b = 8.543 (3) Å	θ = 14.4–16.4°
c = 26.09 (1) Å	µ = 2.37 mm^−1
β = 98.52 (4)°	T = 296 K
V = 2205 (1) Å^3	Prismatic, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

Rigaku AFC-5R diffractometer	2609 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.039
Graphite monochromator	θmax = 78.3°, θmin = 3.4°
ω–2θ scans	h = −12→11
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = −8→10
Tmin = 0.537, Tmax = 0.649	l = −33→32
4742 measured reflections	3 standard reflections every 150 reflections
4476 independent reflections	intensity decay: 4.2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.225	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.130P)^2] where P = (Fo^2 + 2Fc^2)/3
4476 reflections	(Δ/σ)max = 0.021
282 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.70 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.68306 (12)	0.12191 (12)	0.13897 (4)	0.0418 (3)
S2	0.72636 (13)	−0.31393 (14)	0.19327 (4)	0.0487 (3)
N	0.6235 (4)	−0.0549 (4)	0.14712 (12)	0.0394 (8)
O1	0.5988 (4)	0.1867 (4)	0.09521 (12)	0.0561 (9)
O2	0.6927 (4)	0.1978 (4)	0.18794 (12)	0.0545 (9)
C1	0.9521 (6)	0.0613 (7)	0.1587 (2)	0.0624 (14)
H1	0.9382	0.0418	0.1926	0.075*
C2	1.0811 (6)	0.0500 (7)	0.1455 (3)	0.0713 (16)
H2	1.1525	0.0200	0.1706	0.086*
C3	1.1052 (7)	0.0822 (7)	0.0964 (3)	0.0737 (17)
C4	1.2456 (7)	0.0734 (10)	0.0824 (3)	0.118 (4)
H4A	1.291 (3)	0.161 (6)	0.093 (2)	0.176*
H4B	1.2406 (8)	0.064 (8)	0.0478 (19)	0.176*
H4C	1.289 (3)	−0.010 (6)	0.098 (2)	0.176*
C5	0.9983 (8)	0.1224 (9)	0.0605 (3)	0.093 (2)
H5	1.0134	0.1440	0.0269	0.112*
C6	0.8674 (6)	0.1325 (8)	0.0720 (2)	0.0724 (17)
H6	0.7962	0.1597	0.0464	0.087*
C7	0.8447 (5)	0.1014 (5)	0.12186 (16)	0.0425 (10)
C8	0.6233 (4)	−0.1704 (5)	0.10762 (14)	0.0367 (9)
C9	0.5751 (5)	−0.1500 (6)	0.05554 (16)	0.0518 (12)
H9	0.5357	−0.0558	0.0435	0.062*
C10	0.5865 (6)	−0.2721 (6)	0.02197 (17)	0.0591 (14)
H10	0.5562	−0.2595	−0.0132	0.071*
C11	0.6420 (5)	−0.4117 (6)	0.0399 (2)	0.0568 (13)
H11	0.6507	−0.4920	0.0165	0.068*
C12	0.6859 (5)	−0.4355 (6)	0.09261 (19)	0.0500 (12)
H12	0.7204	−0.5318	0.1048	0.060*
C13	0.6767 (4)	−0.3126 (5)	0.12603 (15)	0.0369 (9)
C14	0.6411 (4)	−0.1258 (5)	0.19956 (16)	0.0395 (10)
H14	0.6991	−0.0583	0.2238	0.047*
C15	0.5076 (5)	−0.1458 (6)	0.21776 (16)	0.0453 (11)
H15	0.4398	−0.1988	0.1964	0.054*
C16	0.4810 (5)	−0.0932 (6)	0.26178 (17)	0.0460 (11)
H16	0.5524	−0.0446	0.2827	0.055*
C17	0.3535 (5)	−0.1002 (5)	0.28294 (17)	0.0429 (10)
C18	0.2433 (5)	−0.1782 (7)	0.2576 (2)	0.0590 (13)
H18	0.2516	−0.2322	0.2273	0.071*
C19	0.1185 (5)	−0.1788 (7)	0.2760 (2)	0.0661 (15)
H19	0.0449	−0.2302	0.2574	0.079*
C20	0.1049 (6)	−0.1052 (7)	0.3207 (2)	0.0632 (14)
H20	0.0220	−0.1073	0.3327	0.076*
C21	0.2130 (5)	−0.0261 (6)	0.3491 (2)	0.0515 (12)
C22	0.2014 (7)	0.0518 (7)	0.3966 (2)	0.0725 (17)
H22	0.1190	0.0510	0.4090	0.087*
C23	0.3057 (7)	0.1254 (9)	0.4234 (2)	0.088 (2)
H23	0.2951	0.1747	0.4543	0.106*
C24	0.4305 (7)	0.1304 (9)	0.4062 (2)	0.090 (2)
H24	0.5029	0.1813	0.4258	0.108*
C25	0.4465 (6)	0.0597 (7)	0.3602 (2)	0.0630 (15)
H25	0.5296	0.0666	0.3485	0.076*
C26	0.3403 (5)	−0.0231 (5)	0.33032 (17)	0.0422 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0519 (7)	0.0315 (5)	0.0425 (6)	0.0052 (5)	0.0091 (5)	0.0003 (4)
S2	0.0608 (8)	0.0507 (7)	0.0350 (5)	0.0172 (6)	0.0087 (5)	0.0079 (5)
N	0.054 (2)	0.0349 (18)	0.0311 (17)	0.0020 (16)	0.0113 (16)	0.0013 (14)
O1	0.066 (2)	0.0441 (18)	0.0560 (19)	0.0105 (17)	0.0009 (17)	0.0132 (16)
O2	0.074 (2)	0.0434 (18)	0.0487 (18)	0.0032 (17)	0.0161 (17)	−0.0155 (14)
C1	0.059 (4)	0.071 (4)	0.058 (3)	0.000 (3)	0.013 (3)	0.002 (3)
C2	0.053 (4)	0.081 (4)	0.079 (4)	0.005 (3)	0.008 (3)	−0.005 (3)
C3	0.070 (4)	0.068 (4)	0.089 (5)	−0.016 (3)	0.033 (4)	−0.021 (3)
C4	0.082 (5)	0.128 (7)	0.158 (8)	−0.024 (5)	0.069 (5)	−0.031 (6)
C5	0.099 (5)	0.123 (6)	0.068 (4)	−0.013 (5)	0.048 (4)	0.003 (4)
C6	0.079 (4)	0.094 (4)	0.049 (3)	0.000 (4)	0.022 (3)	0.011 (3)
C7	0.049 (3)	0.042 (2)	0.039 (2)	−0.006 (2)	0.014 (2)	−0.0035 (19)
C8	0.042 (2)	0.040 (2)	0.0288 (18)	−0.0053 (19)	0.0054 (17)	−0.0001 (17)
C9	0.068 (3)	0.049 (3)	0.036 (2)	−0.003 (2)	0.002 (2)	0.004 (2)
C10	0.079 (4)	0.066 (4)	0.031 (2)	−0.015 (3)	0.005 (2)	−0.006 (2)
C11	0.061 (3)	0.056 (3)	0.054 (3)	−0.013 (3)	0.013 (2)	−0.026 (2)
C12	0.054 (3)	0.041 (2)	0.057 (3)	−0.001 (2)	0.013 (2)	−0.007 (2)
C13	0.042 (2)	0.036 (2)	0.0335 (19)	−0.0030 (19)	0.0072 (17)	−0.0002 (17)
C14	0.044 (3)	0.036 (2)	0.040 (2)	−0.0005 (19)	0.0126 (19)	0.0006 (18)
C15	0.047 (3)	0.051 (3)	0.038 (2)	−0.001 (2)	0.008 (2)	−0.0041 (19)
C16	0.043 (3)	0.053 (3)	0.044 (2)	−0.008 (2)	0.013 (2)	−0.007 (2)
C17	0.041 (3)	0.044 (2)	0.046 (2)	−0.002 (2)	0.015 (2)	0.000 (2)
C18	0.049 (3)	0.069 (3)	0.062 (3)	−0.015 (3)	0.017 (2)	−0.011 (3)
C19	0.044 (3)	0.076 (4)	0.079 (4)	−0.021 (3)	0.012 (3)	−0.003 (3)
C20	0.052 (3)	0.065 (3)	0.078 (4)	−0.009 (3)	0.024 (3)	0.001 (3)
C21	0.052 (3)	0.050 (3)	0.058 (3)	0.001 (2)	0.027 (2)	0.007 (2)
C22	0.078 (4)	0.085 (4)	0.065 (4)	0.001 (3)	0.046 (3)	−0.005 (3)
C23	0.103 (5)	0.104 (5)	0.068 (4)	−0.012 (5)	0.046 (4)	−0.030 (4)
C24	0.081 (4)	0.119 (6)	0.076 (4)	−0.029 (4)	0.032 (3)	−0.050 (4)
C25	0.057 (3)	0.079 (4)	0.059 (3)	−0.006 (3)	0.028 (3)	−0.017 (3)
C26	0.042 (3)	0.045 (2)	0.043 (2)	−0.002 (2)	0.017 (2)	0.0029 (19)

Geometric parameters (Å, º)

S1—O2	1.423 (3)	C11—C12	1.396 (7)
S1—O1	1.426 (3)	C11—H11	0.9300
S1—N	1.649 (4)	C12—C13	1.377 (6)
S1—C7	1.750 (5)	C12—H12	0.9300
S2—C13	1.751 (4)	C14—C15	1.492 (6)
S2—C14	1.838 (4)	C14—H14	0.9800
N—C8	1.426 (5)	C15—C16	1.297 (6)
N—C14	1.482 (5)	C15—H15	0.9300
C1—C7	1.375 (7)	C16—C17	1.465 (6)
C1—C2	1.388 (7)	C16—H16	0.9300
C1—H1	0.9300	C17—C18	1.371 (6)
C2—C3	1.365 (9)	C17—C26	1.424 (6)
C2—H2	0.9300	C18—C19	1.403 (7)
C3—C5	1.357 (9)	C18—H18	0.9300
C3—C4	1.506 (9)	C19—C20	1.349 (7)
C4—H4A	0.8987	C19—H19	0.9300
C4—H4B	0.8987	C20—C21	1.392 (7)
C4—H4C	0.8987	C20—H20	0.9300
C5—C6	1.389 (9)	C21—C22	1.425 (7)
C5—H5	0.9300	C21—C26	1.431 (6)
C6—C7	1.379 (6)	C22—C23	1.326 (8)
C6—H6	0.9300	C22—H22	0.9300
C8—C9	1.384 (5)	C23—C24	1.388 (8)
C8—C13	1.384 (6)	C23—H23	0.9300
C9—C10	1.378 (7)	C24—C25	1.374 (7)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.368 (7)	C25—C26	1.412 (7)
C10—H10	0.9300	C25—H25	0.9300
O2—S1—O1	119.7 (2)	C13—C12—H12	120.9
O2—S1—N	106.2 (2)	C11—C12—H12	120.9
O1—S1—N	106.1 (2)	C12—C13—C8	120.6 (4)
O2—S1—C7	109.4 (2)	C12—C13—S2	126.4 (4)
O1—S1—C7	107.1 (2)	C8—C13—S2	113.0 (3)
N—S1—C7	107.9 (2)	N—C14—C15	110.5 (4)
C13—S2—C14	91.0 (2)	N—C14—S2	105.5 (3)
C8—N—C14	111.8 (3)	C15—C14—S2	112.2 (3)
C8—N—S1	120.1 (3)	N—C14—H14	109.5
C14—N—S1	119.8 (3)	C15—C14—H14	109.5
C7—C1—C2	120.2 (5)	S2—C14—H14	109.5
C7—C1—H1	119.9	C16—C15—C14	123.6 (4)
C2—C1—H1	119.9	C16—C15—H15	118.2
C3—C2—C1	121.3 (6)	C14—C15—H15	118.2
C3—C2—H2	119.4	C15—C16—C17	128.6 (4)
C1—C2—H2	119.4	C15—C16—H16	115.7
C5—C3—C2	117.9 (6)	C17—C16—H16	115.7
C5—C3—C4	120.8 (7)	C18—C17—C26	118.2 (4)
C2—C3—C4	121.3 (7)	C18—C17—C16	121.4 (4)
C3—C4—H4A	109.5	C26—C17—C16	120.4 (4)
C3—C4—H4B	109.5	C17—C18—C19	122.0 (5)
H4A—C4—H4B	109.5	C17—C18—H18	119.0
C3—C4—H4C	109.5	C19—C18—H18	119.0
H4A—C4—H4C	109.5	C20—C19—C18	120.2 (5)
H4B—C4—H4C	109.5	C20—C19—H19	119.9
C3—C5—C6	122.6 (6)	C18—C19—H19	119.9
C3—C5—H5	118.7	C19—C20—C21	121.1 (5)
C6—C5—H5	118.7	C19—C20—H20	119.4
C7—C6—C5	118.9 (6)	C21—C20—H20	119.4
C7—C6—H6	120.6	C20—C21—C22	122.2 (5)
C5—C6—H6	120.6	C20—C21—C26	119.1 (5)
C1—C7—C6	119.2 (5)	C22—C21—C26	118.7 (5)
C1—C7—S1	120.2 (4)	C23—C22—C21	121.4 (5)
C6—C7—S1	120.6 (4)	C23—C22—H22	119.3
C9—C8—C13	120.8 (4)	C21—C22—H22	119.3
C9—C8—N	125.8 (4)	C22—C23—C24	121.3 (6)
C13—C8—N	113.4 (3)	C22—C23—H23	119.3
C10—C9—C8	118.6 (5)	C24—C23—H23	119.3
C10—C9—H9	120.7	C25—C24—C23	119.7 (6)
C8—C9—H9	120.7	C25—C24—H24	120.2
C11—C10—C9	120.7 (4)	C23—C24—H24	120.2
C11—C10—H10	119.7	C24—C25—C26	121.8 (5)
C9—C10—H10	119.7	C24—C25—H25	119.1
C10—C11—C12	121.1 (4)	C26—C25—H25	119.1
C10—C11—H11	119.4	C25—C26—C17	123.5 (4)
C12—C11—H11	119.4	C25—C26—C21	117.0 (4)
C13—C12—C11	118.2 (4)	C17—C26—C21	119.4 (4)
O2—S1—N—C8	−169.4 (3)	N—C8—C13—S2	1.5 (5)
O1—S1—N—C8	62.3 (4)	C14—S2—C13—C12	−168.6 (4)
C7—S1—N—C8	−52.2 (4)	C14—S2—C13—C8	11.0 (3)
O2—S1—N—C14	−23.4 (4)	C8—N—C14—C15	−97.6 (4)
O1—S1—N—C14	−151.8 (3)	S1—N—C14—C15	113.9 (4)
C7—S1—N—C14	93.8 (3)	C8—N—C14—S2	23.9 (4)
C7—C1—C2—C3	1.8 (9)	S1—N—C14—S2	−124.6 (3)
C1—C2—C3—C5	−1.4 (10)	C13—S2—C14—N	−19.3 (3)
C1—C2—C3—C4	178.6 (6)	C13—S2—C14—C15	101.1 (3)
C2—C3—C5—C6	0.3 (11)	N—C14—C15—C16	−127.0 (5)
C4—C3—C5—C6	−179.7 (7)	S2—C14—C15—C16	115.5 (5)
C3—C5—C6—C7	0.4 (11)	C14—C15—C16—C17	177.5 (4)
C2—C1—C7—C6	−1.0 (8)	C15—C16—C17—C18	4.5 (8)
C2—C1—C7—S1	−177.9 (4)	C15—C16—C17—C26	−174.3 (5)
C5—C6—C7—C1	0.0 (9)	C26—C17—C18—C19	2.3 (8)
C5—C6—C7—S1	176.8 (5)	C16—C17—C18—C19	−176.5 (5)
O2—S1—C7—C1	40.1 (5)	C17—C18—C19—C20	−2.0 (9)
O1—S1—C7—C1	171.2 (4)	C18—C19—C20—C21	0.6 (9)
N—S1—C7—C1	−75.0 (4)	C19—C20—C21—C22	−179.6 (6)
O2—S1—C7—C6	−136.8 (4)	C19—C20—C21—C26	0.1 (8)
O1—S1—C7—C6	−5.6 (5)	C20—C21—C22—C23	179.4 (6)
N—S1—C7—C6	108.1 (5)	C26—C21—C22—C23	−0.4 (9)
C14—N—C8—C9	162.1 (4)	C21—C22—C23—C24	0.3 (11)
S1—N—C8—C9	−49.4 (6)	C22—C23—C24—C25	0.9 (12)
C14—N—C8—C13	−17.4 (5)	C23—C24—C25—C26	−2.1 (11)
S1—N—C8—C13	131.0 (3)	C24—C25—C26—C17	−178.8 (6)
C13—C8—C9—C10	−2.7 (7)	C24—C25—C26—C21	2.0 (8)
N—C8—C9—C10	177.8 (4)	C18—C17—C26—C25	179.4 (5)
C8—C9—C10—C11	1.2 (8)	C16—C17—C26—C25	−1.7 (7)
C9—C10—C11—C12	1.4 (8)	C18—C17—C26—C21	−1.5 (7)
C10—C11—C12—C13	−2.5 (7)	C16—C17—C26—C21	177.4 (4)
C11—C12—C13—C8	1.0 (7)	C20—C21—C26—C25	179.4 (5)
C11—C12—C13—S2	−179.4 (4)	C22—C21—C26—C25	−0.8 (7)
C9—C8—C13—C12	1.6 (7)	C20—C21—C26—C17	0.3 (7)
N—C8—C13—C12	−178.9 (4)	C22—C21—C26—C17	−179.9 (5)
C9—C8—C13—S2	−178.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1^i	0.93	2.53	3.411 (6)	159
C12—H12···O1^ii	0.93	2.69	3.346 (6)	128
C20—H20···O2^iii	0.93	2.71	3.399 (6)	132

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