Crystal and Molecular Structure of 7-Diethylamino-[1',3′,3′-trimethyl-4-((1,3,3-trimethyl-1,3-dihydro-2H-indole-2-ylidene)methyl)-1',3,3′,4-tetrahydrospiro[chromene-2,2'-indole]]: A Dicondensation Product From the Reaction of 4-Diethylaminosalicylaldehyde with Fischer’s Base
Mohamed Ashraf A , Graeme J. Gainsford A B and Andrew J. Kay AA Photonics, Industrial Research Ltd, PO Box 31-310, Lower Hutt 5040, New Zealand.
B Corresponding author. Email: g.gainsford@irl.cri.nz
Australian Journal of Chemistry 65(7) 779-784 https://doi.org/10.1071/CH11499
Submitted: 21 December 2011 Accepted: 2 February 2012 Published: 8 March 2012
Abstract
The novel molecule, 7-diethylamino-[1′,3′,3′-trimethyl-4-((1,3,3-trimethyl-1,3-dihydro-2H-indole-2-ylidene)methyl)-1′,3,3′,4-tetrahydrospiro[chromene-2,2′-indole]], was isolated as the product from the condensation of diethylaminosalicylaldehyde with two equivalents of Fischer’s base and its crystal structure determined, initially using MoKα radiation. The diffraction data at higher theta angles (d < 0.9 Å) was notably weak so a further dataset was collected using CuKα to determine the cause. Although a different crystal batch and larger crystal was used and a better dataset obtained (with significantly improved atomic resolution) the comparison shows that the essential molecular features and weak intermolecular binding are duplicated in the refinement with the latter data. Comparison is made with a closely related structure. Consistent with observations for this related structure it is proposed that the product is formed through the interception of an intermediate carbinol by Fischer’s base.
References
[1] R. J. Byrne, S. E. Stitzel, D. Diamond, J. Mater. Chem. 2006, 16, 1332.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XivFShsr0%3D&md5=8a629d99572264a3892f456afba68441CAS |
[2] J. C. Crano, T. Flood, D. Knowles, A. Kumar, B. Van Gemert, Pure Appl. Chem. 1996, 68, 1395.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XkvValurw%3D&md5=1ec040b72bcb02d2ffd50241ff0a17dfCAS |
[3] A. S. Dvornikov, J. Malkin, P. M. Rentzepis, J. Phys. Chem. 1994, 98, 6746.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXkvFGks74%3D&md5=14dd7590fe8d5c3a764838a741158b41CAS |
[4] I. Willner, S. Rubin, R. Shatzmiller, T. Zor, J. Am. Chem. Soc. 1993, 115, 8690.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXnt1eqsQ%3D%3D&md5=767ffd56602989ec490c7b9ba25ad9bcCAS |
[5] J. D. Winkler, K. Deshayes, B. Shao, J. Am. Chem. Soc. 1989, 111, 769.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXotlWjsw%3D%3D&md5=10e0dfd5684233b7e113c30feab7cfa2CAS |
[6] G. E. Collins, R. E. Morris, J.-F. Wei, M. Smith, M. H. Hammond, V. Michelet, J. D. Winkler, P. M. Serino, Y. Guo, Energy Fuels 2002, 16, 1054.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xlt1equrY%3D&md5=c7e7dc33768fdcd7b4f9d4132f1466f3CAS |
[7] V. I. Minkin, Chem. Rev. 2004, 104, 2751.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhslClt7k%3D&md5=06b3697e80988333a714e9bc02f2a054CAS |
[8] H. Görner, A. K. Chibisov, J. Chem. Soc., Faraday Trans. 1998, 94, 2557.
| Crossref | GoogleScholarGoogle Scholar |
[9] B.-L. Henri, D. Heinz, IUPAC Tech. Rep. 2003, 73, 639.
[10] (a) K. Uchida, M. Saito, A. Murakami, T. Kobayashi, S. Nakamura, M. Irie, Chem. – Eur. J. 2005, 11, 534.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXnvFSmug%3D%3D&md5=bc23840a3fea9f946481557ee39720eeCAS |
(b) T. Ikeda, O. Tsutsumi, Science 1995, 268, 1873.
| Crossref | GoogleScholarGoogle Scholar |
[11] S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. – Eur. J. 1995, 1, 275.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXns1aktb4%3D&md5=b9bc2d3f3eb47c9b1bb98014a07beb81CAS |
[12] G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev. 2000, 100, 1741.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXhsFyhtr8%3D&md5=9a40d4185fc532ba539b70982bae0275CAS |
[13] S.-R. Keum, B.-S. Ku, J.-T. Shin, J. J. Ko, E. Buncel, Tetrahedron 2005, 61, 6720.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltlentL0%3D&md5=0f9a72d2963da6e1a51335e8667a3117CAS |
[14] F. H. Allen, Acta Crystallogr. 2002, B58, 380.
| 1:CAS:528:DC%2BD38XktVOqu74%3D&md5=8dbd5afdf7403121f413a4cfdc717319CAS |
[15] D. Cremer, J. A. Pople, J. Am. Chem. Soc. 1975, 97, 1354.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2MXhsFGis7c%3D&md5=a5a53481b46db3948bdc4e56f962c12dCAS |
[16] G. J. Gainsford, J. Anderson, M. D. H. Bhuiyan, A. J. Kay, Acta Crystallogr. 2011, E67, o3046 and references therein.and references therein
[17] J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem., Int. Ed. 1995, 34, 1555.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXns1altLk%3D&md5=2ba98f313b6b89447d17ee3be8fee113CAS |
[18] G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112.
| 1:CAS:528:DC%2BD2sXhsVGhurzO&md5=9b979ddbd87a78d6c18caa3d7e8cf709CAS |
[19] G. M. Sheldrick, SADABS 1995 (University of Gottingen: Gottingen).
[20] Rigaku Corporation, Process-Auto 1998 (Rigaku Corporation: Tokyo).
[21] A. L. Spek, J. Appl. Cryst. 2003, 36, 7.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXltlChtw%3D%3D&md5=1f80ec285a5e9701cccf4ab79694aea5CAS |
[22] L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXnt1KgsLg%3D&md5=631f2e5f27cc94401b67d1297e3db297CAS |
[23] C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodiguez-Monge, R. Taylor, J. van de Streek, P. A. Wood, J. Appl. Cryst. 2008, 41, 466.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjt1Gmtb0%3D&md5=243f1bf9f461546db78ba2861361a0a9CAS |
