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13 W. H. Ojala, J. M. Smieja, J. M. Spude, T. M. Arola, M. K. Kuspa,
N. Herrera and C. R. Ojala, Acta Crystallogr., Sect. B: Struct. Sci.,
2007, 63, 485–496.
14 W. H. Ojala, K. M. Lystad, T. L. Deal, J. E. Engebretson,
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15 S. I. V. Judge and C. T. Bever, Pharmacol. Ther., 2006, 111, 224–
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16 D. T. Smith, R. Shi, R. B. Borgens, J. M. McBride, K. Jackson and
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18 C. Ge, H. Kou, Z. Ni, Y. Jiang and A. Cui, Inorg. Chim. Acta, 2006,
359, 541–547.
three 5-Cl-NxxM structures are reported together with NmpFM,
a crystalline solid solution comprising a 50 : 50 mixture of
NmpM and NmpF.11
Three NppM, NpoM and NmoM isomers aggregate via amideN–
H/O]C hydrogen bonding whereas NpmM, NmpM and
NmmM interact via amideN–H/Npyridine interactions. All three
NoxM display intramolecular amideN–H/Npyridine hydrogen
bonds with aggregation by C–H/O]C interactions (NomM has
intermolecular N–H/O]C interactions). For the 5-Cl-NoxM
triad, only 5-Cl-NomM aggregates via amideN–H/O]C (shorter
N/O than NomM); this effect is seen with lower melting points
and crystallisation difficulties.
The NmpM structure uses a similar primary hydrogen bonding
pattern as NmpF11 but via catemeric chains instead of tetra-
mers.11 A mixture of NmpM and NmpF gives NmpFM, a crys-
talline solid solution with 50 : 50% F/CH3 occupancy and with
N–H/N/C–H/N hydrogen bonding forming catemeric chains.
Of particular note is NmmM which is isomorphous and iso-
structural with Mmm10 and is a rare case of isostructuralism
between bridge-flipped isomers.13,14
19 W. Jacob and R. Mukherjee, Inorg. Chim. Acta, 2006, 359, 4565–
4573.
20 J. Y. Qi, H. X. Ma, X. J. Li, Z. Y. Zhou, M. C. K. Choi, A. S. C. Chan
and Q. Y. Yang, Chem. Commun., 2003, 1294–1295.
21 A. Das, S. M. Peng, G. H. Lee and S. Bhattacharya, New J. Chem.,
2004, 28, 712–717.
22 S. Nag, R. J. Butcher and S. Bhattacharya, Eur. J. Inorg. Chem., 2007,
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23 M. Dasgupta, H. Tadesse, A. J. Blake and S. Bhattacharya, J.
Organomet. Chem., 2008, 693, 3281–3288.
Conformational analyses on gas phase and solvation models
have enabled comparisons of optimised geometries with solid
state molecular structures, highlighting unusual solid state
conformations and relations with the aggregation processes.
Future research will finalise the four fluoro/methyl benzamide/
pyridinecarboxamide series of 3 ꢀ 3 isomer grids, as well as
explore related n ꢀ m isomer grids by introducing other func-
tional groups/atoms and/or linker backbone using approaches
similar to those reported previously.10,11
24 T. Yang, J. Y. Zhang, C. Tu, J. Lin, Q. Liu and Z. J. Guo, Chin. J.
Inorg. Chem., 2003, 19, 45–48.
25 W. Jacob and R. Mukherjee, J. Chem. Sci., 2008, 120, 447–453.
26 J. Y. Qi, Y. M. Li, Z. Y. Zhou, C. M. Che, C. H. Yeung and
A. S. C. Chan, Adv. Synth. Catal., 2005, 347, 45–49.
27 J. Y. Zhang, Q. Liu, C. Y. Duan, Y. Shao, J. Ding, Z. H. Miao,
X. Z. You and Z. J. Guo, J. Chem. Soc., Dalton Trans., 2002, 591–597.
28 ABSFAC and CrysAlisPro CCD/RED, Version 1. 171.33.55, Oxford
Diffraction, Abingdon, Oxfordshire, UK, 2010.
29 G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008,
64, 112–122.
30 P. McArdle, J. Appl. Crystallogr., 1995, 28, 65–65.
31 A. L. Spek, J. Appl. Crystallogr., 2003, 36, 7–13.
32 I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae,
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Acknowledgements
The authors thank Dublin City University and the Irish
33 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria,
M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone,
B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li,
H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng,
J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda,
J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao,
H. Nakai, T. Vreven, J. A. Montgomery,Jr, J. E. Peralta,
F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin,
V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand,
K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar,
J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox,
J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts,
R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli,
J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski,
G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich,
A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski
and D. J. Fox, Gaussian 09, Revision B. 01, Gaussian, Inc.,
Wallingford, CT, 2010.
ꢂ
Government for postgraduate funding for Mr Pavle Mocilac
under the PRTLI-4 T3 initiative and Dr Neal Lemon (DCU) for
managing the PRTLI-4 T3 programme. Dr A. M. Elena and Dr
J.-C. Desplat from the Irish Centre for High End Computing
(ICHEC) are thanked for assistance.
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