Crystal Growth & Design
Article
Scheme 4. Reaction Sequence for the Synthesis of MCF and TCF
2,6-dichlorophenol and 4,4′-dichlorobenzhydrol was produced by
grinding both the materials in a mortar-pestle. The mixture was
dissolved in acetic acid and conc. H2SO4 (1 mL) were added at
80−90 °C. The remaining procedure was the same as that used for
MCF.
(j) Byrn, S. R.; Pfeiffer, R. R.; Stephenson, G.; Grant, D. J. W.; Gleason,
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Karamertzanis, P. G.; Hulme, A. T.; Tocher, D. A.; Lewis, T. C.; Price, S.
L. J. Pharm. Sci. 2007, 96, 3419−3431.
1H NMR (400 MHz, CDCl3, δ ppm): 7.19 (4H, d, J 8), 7.49 (6H, m).
FT-IR (KBr, cm−1): 2923, 2852, 1624, 1092. m.p.: 227−230 °C.
X-ray Crystallography. X-ray reflections were collected at 100 K
for all crystals, except CMF-d which was collected at 298 K, on Bruker
SMART APEX CCD X-ray diffractometer equipped with a graphite
monochromator and Mo−Kα fine-focus sealed tube (λ = 0.71073 Å).
Data was integrated using SAINT.19 Intensities for absorption were
corrected using SADABS.20 Structure solution and refinement were
carried out in Bruker SHELXTL.21 Hydrogen atoms were refined iso-
tropically and the heavy atoms were refined anisotropically. C−H
hydrogens were fixed using HFIX command in SHELX-TL. The experi-
mental composition of solid-solution crystal structures was determined
by the variable site occupancy of C and Cl atoms in structure-solution
least-squares refinement cycles by using FVAR, EXYZ, and EADP com-
mands in SHELX-TL. Crystallographic .cif files (CCDC Nos. 900385−
or from the author upon request.
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Solid-State UV−vis Spectroscopy. Solid state UV−vis spectra
were recorded on a Thermo Scientific Evolution 300 UV−vis spectro-
photometer. Experiments were carried out by mounting very thin
homogeneous KBr discs with the help of quartz plates. Concentrations
of the samples are ∼0.8% (w/w).
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ASSOCIATED CONTENT
* Supporting Information
Crystallographic data (.cif files) is available free of charge via the
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AUTHOR INFORMATION
Corresponding Author
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Notes
The authors declare no competing financial interest.
(9) (a) Chandran, S. K.; Nath, N. K.; Roy, S.; Nangia, A. Cryst. Growth
Des. 2008, 8, 140−154. (b) Nath, N. K.; Nilapwar, S.; Nangia, A. Cryst.
Growth Des. 2012, 12, 1613−1625.
(10) (a) Desiraju, G. R.; Parthasarathy, R. J. Am. Chem. Soc. 1989, 111,
8725−8726. (b) Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Rae, D. C.;
Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1994, 2353.
(11) Saha, B. K.; Nangia, A.; Nicoud, J.-F. Cryst. Growth Des. 2006, 6,
1278−1281.
(12) (a) Spackman, M. A.; Jayatilaka, D. CrystEngComm 2009, 11, 19−
32. (b) McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Chem. Commun.
2007, 3814−3816. (c) Bernstein, J. Cryst. Growth Des. 2011, 11, 632−
650.
(13) (a) Kitaigorodskii, A. I. In Mixed Crystals, Springer-Verlag: Berlin,
Heidelberg, 1984. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Am. Chem. Soc.
ACKNOWLEDGMENTS
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This research was funded by JC Bose DST Grant SR/S2/JCB-
06/2009. N.K.N. thanks the UGC for fellowship. DST (IRPHA)
and UGC (PURSE grant) are thanked for providing
instrumentation and infrastructure facilities
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