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Abstract:

A new polymorph of 9,10-dichloroanthracene (9,10-DCA) namely as γ form, was obtained. The crystal structure of the γ polymorphic system showed an orthorhombic P212121 space group with a = 3.8957(2) Å, b = 15.9383(5) Å, c = 17.3107(7) Å, α = β = γ = 90°, while the other polymorphs, α and β, crystallized in P21/a and P-1 ones, respectively. The intermolecular geometries of γ form were analyzed showing that the crystalline self-assembly of this new polymorph of the 9,10-DCA is stabilized by non-classical C-H⋯Cl hydrogen bonds, π-π stacking interactions, and mainly by Cl⋯Cl interactions. Structural parameters confirmed the halogen⋯halogen contacts correspond to the Type II geometry. Complementary, electronic structure calculations were performed in other to estimate the energetic contribution of the observed intermolecular interactions in the crystal packing of the new system. Density Functional Theory (DFT) considering empirical dispersion corrections (named as DFT-D) and MP2 correlated very well and showed energy values according to previously reported related compounds (e.g., the energy for the Cl⋯Cl is -5.37 and -3.25 kcal mol-1 for MP2/6-31+G** and B2PLYP-D/6-31+G**, respectively). On the other hand, and as expected, DFT using B3LYP as functional was not able to describe properly the studied intermolecular interactions. Moreover, it even predicts repulsive energies for most of the analyzed arrangements. © 2013 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
Autor:Foi, A.; Corrêa, R.S.; Ellena, J.; Doctorovich, F.; Di Salvo, F.
Filiación:Departamento de Química Inorgánica, Analítica, y Química Física, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, Piso 3, C1428EHA Buenos Aires, Argentina
Departamento de Química, Universidade Federal de São Carlos-UFSCar, Rodovia Washington Luis, KM 235 CP 676, CEP 13561-901, São Carlos, SP, Brazil
Instituto de Física de São Carlos, Universidade de São Paulo, CP 369, 13560-970 São Carlos, SP, Brazil
Palabras clave:9,10-Dichloroanthracene; Cl⋯Cl interactions; DFT-D; Halogen-bonding; Molecular conformation; Polymorphism; 9,10-Dichloroanthracene; DFT-D; Dispersion correction; Electronic structure calculations; Halogen bonding; Intermolecular interactions; Molecular conformation; Stacking interaction; Chlorine compounds; Electronic structure; Hydrogen bonds; Polymorphism; Chlorine
Año:2014
Volumen:1059
Número:1
Página de inicio:1
Página de fin:7
DOI: http://dx.doi.org/10.1016/j.molstruc.2013.11.028
Título revista:Journal of Molecular Structure
Título revista abreviado:J. Mol. Struct.
ISSN:00222860
CODEN:JMOSB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1059_n1_p1_Foi

Referencias:

  • Yamamoto, H.M., Yamaura, J., Kato, R., (1998) J. Am. Chem. Soc., 120, p. 5905. , references therein
  • Brammer, L., (2004) Chem. Soc. Rev., 33, p. 476
  • Matsumoto, A., Tanaka, T., Tsubouchi, T., Tashiro, K., Saragai, S., Nakamoto, Sh., (2002) J. Am. Chem. Soc., 124, p. 8891
  • Macgillivray, L.R., Reid, J.L., Ripmeester, J.A., (2000) J. Am. Chem. Soc., 122, p. 7817
  • Macgillivray, L.R., (2002) CrystEngComm, 4, p. 37
  • Fourmigué, M., (2009) Curr. Opin. Solid State Mater. Sci., 13, p. 36
  • Desiraju, G.R., (1989) Crystal Engineering. The Design of Organic Solids, , Elsevier Amsterdam
  • Brammer, L., Mínguez Espallargas, G., Libri, S., (2008) CrystEngComm, 10, p. 1712
  • Metrangolo, P., Pilati, T., Resnati, G., (2006) CrystEngComm, 8, p. 946
  • Rissanen, K., (2008) CrystEngComm, 10, p. 1107
  • Samai, S., Biradha, K., (2009) CrystEngComm, 11, p. 482
  • Metrangolo, P., Pilati, T., Terraneo, G., Biella, S., Resnati, G., (2009) CrystEngComm, 11, p. 1187
  • Desiraju, G.R., Ho, P.S., Kloo, L., Legon, A.C., Marquardt, R., Metrangolo, P., Politzer, P., Rissanen, K., (2013) Pure Appl. Chem., 85, p. 1711
  • Braga, D., Grepioni, F., (1998) New J. Chem., 22, p. 1159
  • Desiraju, G.R., Stiener, T., (1990) The Weak Hydrogen Bond in Structural Chemistry and Biology, , Oxford University Press New York
  • Langley, P.J., Hulliger, J., Thaimattamand, R., Desiraju, G.R., (1998) New J. Chem., 22, p. 1307
  • Desiraju, G.R., Parthasarathy, R., (1989) J. Am. Chem. Soc., 111, p. 8725
  • Jagarlapudi, A.R., Sarma, P., Desiraju, G.R., (1986) Acc. Chem. Res., 19, p. 222
  • Reddy, C.M., Kirchner, M.T., Gundakaram, R.V., Padmanabhan, K.A., Desiraju, G.R., (2006) Chem. Eur. J., 12, p. 2222
  • Nishio, M., (2004) CrystEngComm, 6, p. 130
  • Hunter, C.A., Lawson, K.R., Perkins, J., Urch, C.J., (2001) J. Chem. Soc., Perkin Trans., 2, p. 651
  • Metrangolo, P., Meyer, F., Pilati, T., Resnati, G., Terraneo, G., (2008) Angew. Chem. Int. Ed., 47, p. 6114. , references therein
  • Bondi, A., (1964) J. Phys. Chem., 68, p. 441
  • Sakurai, T., Sundaralingam, M., Jeffrey, G.A., (1963) Acta Crystallogr., 16, p. 354
  • Williams, D.E., Hsu, L.Y., (1985) Acta Crystallogr. Sect. A, 41, p. 296
  • Nyburg, S.C., Wong-Ng, W., (1979) Inorg. Chem., 18, p. 2790
  • Nyburg, S.C., Wong-Ng, W., (1979) Proc. R. Soc. London Sect. A, 367, p. 29
  • Price, S.L., Stone, A.J., Lucas, J., Rowland, R.S., Thornley, A.E., (1994) J. Am. Chem. Soc., 116, p. 4910
  • Day, G.M., Price, S.L., (2003) J. Am. Chem. Soc., 125, p. 16434
  • Awwadi, F.F., Willett, R.D., Peterson, K.A., Twamley, B., (2006) Chem. Eur. J., 12, p. 8952
  • Bui, T.T.T., Dahaoui, S., Lecomte, C., Desiraju, G.R., Espinosa, E., (2009) Angew. Chem. Int. Ed., 48, p. 3838
  • Kitamura, M., (2009) CrystEngComm, 11, p. 949
  • Yu, L., (2007) CrystEngComm, 9, p. 847
  • Men, Y.B., Sun, J., Huang, Z.T., Zheng, Q.Y., (2009) CrystEngComm, 11, p. 978
  • Duggirala, N.K., Kanniah, S.L., Muppidi, V.K., Thaimattam, R., Devarakonda, S., (2009) CrystEngComm, 11, p. 989
  • Bernstein, J., (2007) J. Polymorphism in Molecular Crystals, , Oxford University Press New York
  • Hilifiker, R., (2006) Polymorphism in the Pharmaceutical Industry, , Wiley-VCH Verlag GmbH & Co. Weinheim, Germany
  • Bernstein, J., (1987) Organic Solid State Chemistry, , Elsevier Amsterdam Chapter 14
  • Gavezzotti, A., (2007) J. Pharm. Sci., 96, p. 2232
  • Saltiel, J., Dabestani, R., Sears, Jr.D.F., McGowan, W.M., Hdinski, E.F., (1995) J. Am. Chem. Soc., 117, p. 9129
  • Smothers, W.K., Meyer, M.C., Saltiel, J., (1983) J. Am. Chem. Soc., 105, p. 2795
  • Thakur, S., Smith, J.R., Tillman, E.S., Cohen, N.A., Contrella, N.D., (2008) J. Pol. Sci. A, 46, p. 6016
  • Kuwano, H., Kondo, M., (1966) Bull. Chem. Soc. Jpn., 39, p. 2779
  • Tanaka, J., Shibata, M., (1968) Bull. Chem. Soc. Jpn., 41, p. 34
  • Trotter, J., (1959) Acta Crystallogr., 12, p. 54
  • Trotter, J., (1986) Acta Crystallogr. C., 42, p. 862
  • Burshtein, Z., Hanson, A.W., Ingold, C.F., Williams, D.F., (1978) J. Phys. Chem. Solids, 39, p. 1125
  • Krauss, R., Schulz, H., Nesper, R., Thiemann, K.H., (1979) Acta Cryst. B, 35, p. 1419
  • Li, Q., Hu, C., Haerter, R., Englert, U., (2004) CrystEngComm, 6, p. 83
  • Møller, C., Plesset, M.S., (1934) Phys. Rev., 46, p. 618
  • Grimme, S.J., (2004) Comput. Chem., 25, p. 1463
  • Grimme, S.J., (2006) Comput. Chem., 27, p. 1787
  • Jurecka, P., Cerny, J., Hobza, P., Salahub, D., (2007) J. Comput. Chem., 28, p. 555
  • Barone, V., Biczysko, M., Pavone, M., (2008) Chem. Phys., 346, p. 247
  • Grimme, S., Antony, J., Ehrlich, S., Krieg, H., (2010) J. Chem. Phys., 132, p. 154104
  • Thanthiriwatte, K.S., Hohenstein, E.G., Burns, L.A., Sherrill, C.D., (2011) J. Chem. Theory Comput., 7, p. 88
  • Pedone, A., Presti, D., Menziani, M.C., (2012) Chem. Phys. Lett., 541, p. 12
  • Riley, K., Hobza, P., (2008) J. Chem. Theory Comput., 4, p. 232
  • Asmadi, A., Kendrick, J., Leusen, F.J.J., (2010) Phys. Chem. Chem. Phys., 12, p. 8571
  • Luo, Z., Smith, J.C., Woodward, W.H., Castleman, Jr.W., (2012) J. Phys. Chem. A, 116, p. 1298
  • Bertolotti, F., Curetti, N., Benna, P., Gervasio, G., (2013) J. Mol. Str., 1041, p. 106
  • Enraf-Nonius, , COLLECT. Nonius BV, Delft, The Netherlands, 1997-2000
  • Otwinowski, Z., Minor, W., Processing of X-ray diffraction data collected in oscillation mode (1997) Methods in Enzymology, 276, pp. 307-326. , DOI 10.1016/S0076-6879(97)76066-X
  • Blessing, R.H., (1995) Acta Crystallogr., A51, p. 33
  • Sheldrick, G.M., (1997) SHELXS-97. Program for Crystal Structure Resolution and Analysis, , University of Göttingen Göttingen, Germany
  • Farrugia, L.J., (1997) J. Appl. Cryst., 30, p. 565
  • Macrae, C.F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., Van De Streek, J., (2006) J. Appl. Cryst., 39, p. 453
  • Farrugia, L.J., (1999) J. Appl. Cryst., 32, p. 837
  • Zhang, I.Y., Wu, J., Xu, X., (2010) Chem. Commun., 46, p. 3057
  • Riley, K.E., Pitonak, M., Jurecka, P., Hobza, P., (2010) Chem. Rev., 110, p. 5023
  • Kohn, W., Meir, Y., Makarov, D.E., (1998) Phys. Rev. Lett., 80, p. 4153
  • Dion, M., Rydberg, H., Shroder, E., Langreth, D.C., Lundqvist, B.I., (2004) Phys. Rev. Lett., 92, p. 246401
  • Johnson, E.R., Mackie, I.D., Dilabio, G.A., (2009) J. Phys. Org. Chem., 22, p. 1127
  • Grimme, S., (2011) Wiley. Interdiscip. Rev. Comput. Mol. Sci., 1, p. 211
  • Grimme, S., (2006) J. Chem. Phys., 124, p. 034108
  • Reed, A.E., Curtis, L.A., Weinhold, F., (1988) Chem. Rev., 88, p. 899
  • Neese, F., ORCA 2.9, , http://www.cec.mpg.de/forum/, University of Bonn, Bonn, Germany
  • Francl, M.M., Pietro, W.J., Hehre, W.J., Binkley, J.S., Defrees, D.J., Pople, J.A., Gordon, M.S., (1982) J. Chem. Phys., 77, p. 3654
  • Rassolov, V., Pople, J.A., Ratner, M., Windus, T.L., (1998) J. Chem. Phys., 109, p. 1223
  • Bruno, I.J., Cole, J.C., Kessler, M., Luo, J., Motherwell, W.D.S., Purkis, L.H., Smith, B.R., Orpen, A.G., (2004) J. Chem. Inf. Comput. Sci., 44, p. 2133
  • Allen, F.H., (2002) Acta Crystallogr., B58, p. 380
  • Corrêa, R.S., Graminha, A.E., Ellena, J., Batista, A.A., (2011) Acta Cryst., C67, p. 304
  • Cozzi, F., Bacchi, S., Filippini, G., Pilati, T., Gavezzotti, A., (2007) Chem. Eur. J., 13, p. 7177
  • Corrêa, R.S., Dos Santos, M.H., Nagem, T.J., Ellena, J., (2010) Struct Chem., 21, p. 555
  • Desiraju, G.R., Steiner, T., (2001) The Weak Hydrogen Bond: In Structural Chemistry and Biology, IUCr Monographs on Crystallography, 9. , Oxford University Press New York

Citas:

---------- APA ----------
Foi, A., Corrêa, R.S., Ellena, J., Doctorovich, F. & Di Salvo, F. (2014) . Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene. Journal of Molecular Structure, 1059(1), 1-7.
http://dx.doi.org/10.1016/j.molstruc.2013.11.028
---------- CHICAGO ----------
Foi, A., Corrêa, R.S., Ellena, J., Doctorovich, F., Di Salvo, F. "Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene" . Journal of Molecular Structure 1059, no. 1 (2014) : 1-7.
http://dx.doi.org/10.1016/j.molstruc.2013.11.028
---------- MLA ----------
Foi, A., Corrêa, R.S., Ellena, J., Doctorovich, F., Di Salvo, F. "Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene" . Journal of Molecular Structure, vol. 1059, no. 1, 2014, pp. 1-7.
http://dx.doi.org/10.1016/j.molstruc.2013.11.028
---------- VANCOUVER ----------
Foi, A., Corrêa, R.S., Ellena, J., Doctorovich, F., Di Salvo, F. Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene. J. Mol. Struct. 2014;1059(1):1-7.
http://dx.doi.org/10.1016/j.molstruc.2013.11.028