PAPER
Synthesis of Benzopyridoiodolium Salts
295
IR (neat, ATR): 3146, 1614, 1490, 1461, 1398, 1337, 1222, 1125,
879, 849, 818, 756, 735, 715, 690 cm–1.
1H NMR (400 MHz, DMSO-d6): d = 11.42 (s, 1 H), 8.35 (d, J = 7.7
Hz, 1 H), 8.28 (s, 1 H), 8.19 (d, J = 8.5 Hz, 1 H), 8.10 (d, J = 7.5
Hz), 7.55 (m, 2 H), 7.63 (m, 2 H), 7.28 (m, 1 H).
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13C NMR (75 MHz, DMSO-d6): d = 145.7, 144.0, 143.4, 132.4,
129.7, 128.7, 127.5, 126.7, 126.0, 124.9, 121.4, 121.0, 119.3, 113.0,
111.5.
+
MS (FD): m/z = 218.1 [C15H10N2 ].
X-ray Crystal Structure Determination of 10
X-ray crystallographic analysis was performed with an Enraf–Non-
ius Turbo-Cad 4 instrument equipped with a rotating anode by using
a colorless plate (Cu-Ka, graphite monochromator; l = 1.54180 Å).
Crystal data: C12H7F3INO3S, M = 429.2 g mol–1, 0.3 × 0.3 × 0.4
mm3, triclinic, space group: P1, T = 193 K, unit cell dimensions:
a = 10.412(4) Å,
b = 12.352(5) Å,
c = 13.336(6) Å,
a = 62.653(10)°, b = 88.205(1)°, g = 65.679(10)°, V = 1361.5(2)
Å3, z = 4, dcalc = 2.094 g cm–3, absorption m = 2.55 mm–1, the q range
for data collection was 2–28°; index ranges were –13 £ h £ 13, –16
£ k £ 16, –17 £ l £ 17. Number of reflections collected: 49739; in-
dependent reflections: 6496 [Rint = 0.0202]. The structure was
solved by direct methods (program SIR 97, refinement by SHELXL
97).29 Structure refinement was performed by full-matrix least
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2008, 64, 6030.
(8) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin
Trans. 1 1999, 1505.
2
squares on 405 parameters, weighted refinement: w = 1/[s2(Fo ) +
(0.0195 P)2 + 0.85 P] with P = [max(Fo ,0) + 2Fo ]/3 and hydrogen
atoms located from difference Fourier synthesis and refined isotro-
pically assuming a riding motion model, non-hydrogen atoms im-
proved with anisotropic temperature factors. Goodness-of-fit on
S = 1.058, maximal range of parameters: 0.001(e.s.d.), final R indi-
ces: R1 = 0.0157, wR2 = 0.0404, the final difference Fourier map
showed minimum and maximum values of 0.64 and –0.53 eÅ–3, re-
spectively. CCDC-828718 (10) contains the supplementary crystal-
lographic data for this paper. These data can be obtained free of
charge from The Cambridge Crystallographic Data Centre via
2
2
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Supporting Information for this article is available online at
Acknowledgment
(13) Letessier, J.; Detert, H.; Schollmeyer, D. Acta Crystallogr.,
Sect. E 2011, E67, o2494.
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C 1986, C42, 1014.
The authors are grateful to H. Kolshorn for invaluable discussions
and NMR spectra and to Dr. D. Schollmeyer for the X-ray crystal
structure analysis.
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Synthesis 2012, 44, 290–296