Combined experimental and computational studies of pyrazinamide and nicotinamide in the context of crystal engineering and thermodynamics

Crystal Growth and Design

Volumn 14, Issue 7, 2014, Pages 3453-3465

  Jarzembska, Katarzyna N ^a,b   Hoser, Anna A ^a   Kamiński, Radosław ^a,b   Madsen, Anders Ø ^c   Durka, Krzysztof ^d   Woźniak, Krzysztof ^a,e  

^a UNIVERSITY OF WARSAW   (Poland)

^b UNIVERSITY AT BUFFALO   (United States)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

^d WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^e UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; COMPUTATIONAL METHODS; CRYSTAL ENGINEERING; ELECTROSTATICS; ENTROPY; MOLECULES; QUANTUM THEORY; THERMODYNAMICS;

ATOMIC DISPLACEMENT PARAMETERS; COMPUTATIONAL ANALYSIS; COMPUTATIONAL STUDIES; ELECTROSTATIC POTENTIALS; EXPERIMENTAL CHARGE DENSITY; INTERMOLECULAR INTERACTIONS; MULTIPOLAR REFINEMENTS; QUANTUM THEORY OF ATOMS IN MOLECULES;

AMIDES;

EID: 84903727968     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg500376z     Document Type: Article

References (124)

1. Magel, E. A.; Hillinger, C.; Wagner, T.; Holl, W. Oxidative pentose phosphate pathway and pyridine nucleotides in relation to heartwood formation in Robinia pseudoacacia L Phytochemistry 2001, 57, 1061-1068 (Pubitemid 32625583)
2. Shibata, K. Reparative effect of nicotinamide and nicotinic-acid on the aggravation of tryptophan-nicotinamide metabolism caused by 6-aminonicotinamide Biosci. Biotechnol. Biochem. 1994, 58, 1729-1730
3. Wahlberg, N.; Cichoń, P.; Petriĉek, V.; Madsen, A. Ø. Polymorph stability prediction on the importance of accurate structures: a case study of pyrazinamide Cryst. Growth Des. 2013, 14, 381-388
4. Takaki, Y.; Sasada, Y.; Watanabé, K. The crystal structure of α-pyrazinamide Acta Crystallogr. 1960, 13, 693-702
5. Rø, G.; Sørum, H. The crystal and molecular structure of β-pyrazincarboxamide Acta Crystallogr. 1972, B28, 991-998
6. Rø, G.; Sørum, H. The crystal and molecular structure of -pyrazincarboxamide Acta Crystallogr. 1972, B28, 1677-1684
7. Castro, R. A. E.; Maria, T. M. R.; évora, A. O. L.; Feiteira, J. C.; Silva, M. R.; Beja, A. M.; Canotilho, J.; Eusébio, M. E. S. A new insight into pyrazinamide polymorphic forms and their thermodynamic relationships Cryst. Growth Des. 2010, 10, 274-282
8. Cherukuvada, S.; Thakuria, R.; Nangia, A. Pyrazinamide polymorphs: Relative stability and vibrational spectroscopy Cryst. Growth Des. 2010, 10, 3931-3941
9. Allen, F. H. The Cambridge Structural Database: A quarter of a million crystal structures and rising Acta Crystallogr. 2002, B58, 380-388 (Pubitemid 135702674)
10. Tan, X.; Wang, K.; Li, S.; Yuan, H.; Yan, T.; Liu, J.; Yang, K.; Liu, B.; Zou, G.; Zou, B. Exploration of the pyrazinamide polymorphism at high pressure J. Phys. Chem. B 2012, 116, 14441-14450
11. Li, J.; Bourne, S. A.; Caira, M. R. New polymorphs of isonicotinamide and nicotinamidew Chem. Commun. 2011, 47, 1530-1532
12. Fábián, L.; Hamill, N.; Eccles, K. S.; Moynihan, H. A.; Maguire, A. R.; McCausland, L.; Lawrence, S. E. Cocrystals of fenamic acids with nicotinamide Cryst. Growth Des. 2011, 11, 3522-3528
13. Abourahma, H.; Cocuzza, D. S.; Melendez, J.; Urban, J. M. Pyrazinamide cocrystals and the search for polymorphs CrystEngComm 2011, 13, 6442-6450
14. Adalder, T. K.; Sankolli, R.; Dastidar, P. Homo- or heterosynthon? A crystallographic study on a series of new cocrystals derived from pyrazinecarboxamide and various carboxylic acids equipped with additional hydrogen bonding sites Cryst. Growth Des. 2012, 12, 2533-2542
15. Grobelny, P.; Mukherjee, A.; Desiraju, G. R. Drug-drug co-crystals: Temperature-dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid CrystEngComm 2011, 13, 4358-4364
16. Cherukuvada, S.; Bolla, G.; Sikligar, K.; Nangia, A. 4-Aminosalicylic acid adducts Cryst. Growth Des. 2013, 13, 1551-1557
17. Karki, S.; Friscic, T.; Jones, W. Control and interconversion of cocrystal stoichiometry in grinding: Stepwise mechanism for the formation of a hydrogen-bonded cocrystal CrystEngComm 2009, 11, 470-481
18. Clarke, H. D.; Arora, K. K.; Bass, H.; Kavuru, P.; Ong, T. T.; Pujari, T.; Wojtas, L.; Zaworotko, M. J. Structure-stability relationships in cocrystal hydrates: does the promiscuity of water make crystalline hydrates the nemesis of crystal engineering? Cryst. Growth Des. 2010, 10, 2152-2167
19. Das, B.; Baruah, J. B. Supramolecular synthons and hydrates in stabilization of multicomponent crystals of nicotinamide and isonicotinamide with N-containing aromatic dicarboxylic acids Cryst. Growth Des. 2011, 11, 5522-5532
20. Stilinovic, V.; Kaitner, B. Salts and co-crystals of gentisic acid with pyridine derivatives: the effect of proton transfer on the crystal packing (and vice versa) Cryst. Growth Des. 2012, 12, 5763-5772
21. Lemmerer, A.; Adsmond, D. A.; Bernstein, J. An investigation of the hydrogen-bond preferences and co-crystallization behavior of three didonor compounds Cryst. Growth Des. 2011, 11, 2011-2019
22. Berry, D. J.; Seaton, C. C.; Clegg, W.; Harrington, R. W.; Coles, S. J.; Horton, P. N.; Hursthouse, M. B.; Storey, R.; Jones, W.; Frišč ić, T.; Blagden, N. Applying hot-stage microscopy to co-crystal screening: a study of nicotinamide with seven active pharmaceutical ingredients Cryst. Growth Des. 2008, 8, 1697-1717
23. Orola, L.; Veidis, M. V. Nicotinamide fumaric acid supramolecular cocrystals: Diversity of stoichiometry CrystEngComm 2009, 11, 415-417
24. Hathwar, V. R.; Pal, R.; Guru Row, T. N. Charge density analysis of crystals of nicotinamide with salicylic acid and oxalic acid: an insight into the salt to cocrystal continuum Cryst. Growth Des. 2010, 10, 3306-3310
25. Aree, T.; Chaichit, N. Inclusion complexes of beta-cyclodextrin with pyrazinamide and piperazine: Crystallographic and theoretical studies Supramol. Chem. 2009, 21, 384-393
26. Korkmaz, U.; Ucar, I.; Bulut, A.; Buyukgungor, O. Three forms of squaric acid with pyrazine and pyridine derivatives: An experimental and theoretical study Struct. Chem. 2011, 22, 1249-1259
27. Aakeroy, C. B.; Desper, J.; Helfrich, B. A. Heteromeric intermolecular interactions as synthetic tools for the formation of binary co-crystals CrystEngComm 2004, 6, 19-24 (Pubitemid 40464517)
28. Thakuria, R.; Cherukuvada, S.; Nangia, A. Crystal structures of pyrogallol, its hydrate, and stable multiple Z′ cocrystals with N-heterocycles containing metastable conformers of pyrogallol Cryst. Growth Des. 2012, 12, 3944-3953
29. McMahon, J. A.; Bis, J. A.; Vishweshwar, P.; Shattock, T. R.; McLaughlin, O. L.; Zaworotko, M. J. Crystal engineering of the composition of pharmaceutical phases. 3. Primary amide supramolecular heterosynthons and their role in the design of pharmaceutical co-crystals Z. Kristallogr. 2005, 220, 340-350 (Pubitemid 40515882)
30. Mukherjee, A.; Grobelny, P.; Thakur, T. S.; Desiraju, G. R. Polymorphs, pseudopolymorphs, and co-crystals of orcinol: Exploring the structural landscape with high throughput crystallography Cryst. Growth Des. 2011, 11, 2637-2653
31. Arenas-Garcia, J. I.; Herrera-Ruiz, D.; Mondragon-Vasquez, K.; Morales-Rojas, H.; Hopfl, H. Co-crystals of active pharmaceutical ingredients-Acetazolamide Cryst. Growth Des. 2010, 10, 3732-3742
32. Cheney, M. L.; Shan, N.; Healey, E. R.; Hanna, M.; Wojtas, L.; Zaworotko, M. J.; V. Sava, S. S.; Sanchez-Ramos, J. R. Effects of crystal form on solubility and pharmacokinetics: a crystal engineering case study of lamotrigine Cryst. Growth Des. 2010, 10, 394-405
33. Cherukuvada, S.; Nangia, A. Fast dissolving eutectic compositions of two anti-tubercular drugs CrystEngComm 2012, 14, 2579-2588
34. Beatty, A. M. Hydrogen bonded networks of coordination complexes CrystEngComm 2001, 51, 1-13
35. Prins, F.; Pasca, E.; Jongh, L. J. d.; Kooijman, H.; Spek, A. L.; Tanase, S. Long-range magnetic ordering in a Tb-III-Mo-V cyanido-bridged quasi-one-dimensional complex Angew. Chem., Int. Ed. 2007, 46, 6081-6084 (Pubitemid 47290958)
36. Beatty, A. M. Open-framework coordination complexes from hydrogen-bonded networks: Toward host/guest complexes Coord. Chem. Rev. 2003, 246, 131-143
37. Qin, Z.; Jennings, M. C.; Puddephatt, R. J. Self-assembly of polymer and sheet structures from palladium(II) complexes by hydrogen bonding between carboxamide substituents Inorg. Chem. 2001, 40, 6220-6228 (Pubitemid 33091547)
38. n complex Polyhedron 2000, 19, 601-606
39. Halaška, J.; Pevec, A.; Strauch, P.; Kozlevčar, B.; Koman, M.; Moncol, J. Supramolecular hydrogen-bonding networks constructed from copper(II) chlorobenzoates with nicotinamide: structure and EPR Polyhedron 2013, 61, 20-26
40. Goher, M. A. S.; Mautner, F. A. 2D polymeric copper(I) complexes. Synthesis and characterizations of [Cu(pyza)(2)X](n) (X = CN, NCS and N-3, and pyza = pyrazinecarboxamide) and X-ray crystal structures of the cyano and thiocyanato complexes J. Coord. Chem. 2001, 53, 79-89
41. Ma, Z.; Moulton, B. Mixed-ligand coordination species: a promising approach for "second-generation" drug development Cryst. Growth Des. 2007, 7, 196-198
42. Findoráková, L.; Goryová, K.; Melník, M.; Koman, M.; El-Dien, F. A. N. Crystal structure, spectral and magnetic behavior of copper(II)(5-chlorosalicylato)(2) (aqua)(2) J. Coord. Chem. 2001, 63, 3348-3355
43. Smart, P.; Bejarano-Villafuerte, á.; Brammer, L. Coordination chemistry meets halogen bonding and hydrogen bonding: building networks from 3-iodobenzoate paddlewheel units [Cu-2(3-Ibz)(4)(L)(2)] CrystEngComm 2013, 15, 3151-3159
44. Hansen, N. K.; Coppens, P. Testing aspherical atom refinements on small-molecule data sets Acta Crystallogr. 1978, A34, 909-921
45. Malińska, M.; Jarzembska, K. N.; Goral, A. M.; Kutner, A.; Woźniak, K.; Dominiak, P. M. Sunitinib: From charge-density studies to interaction with proteins Acta Crystallogr. 2014, D70, 1257-1270
46. Jarzembska, K. N.; Kamiński, R.; Wenger, E.; Lecomte, C.; Dominiak, P. M. Interplay between charge density distribution, crystal structure energetic features, and crystal morphology of 6-methyl-2-thiouracil J. Phys. Chem. C 2013, 117, 7764-7775
47. Jarzembska, K. N.; Goral, A. M.; Gajda, R.; Dominiak, P. M. Hoogsteen-Watson-Crick 9-methyladenine:1-methylthymine complex: Charge density study in the context of crystal engineering and nucleic acid base pairing Cryst. Growth Des. 2013, 13, 239-254
48. Jarzembska, K. N.; Kamiński, D.; Hoser, A. A.; Malińska, M.; Senczyna, B.; Woźniak, K.; Gagoś, M. Controlled crystallization, structure, and molecular properties of iodoacetylamphotericin B Cryst. Growth Des. 2012, 12, 2336-2345
49. Hoser, A. A.; Jarzembska, K. N.; Dobrzycki, A.; Gutmann, M. J.; Woźniak, K., Differences in charge density distribution and stability of two polymorphs of benzidine dihydrochloride Cryst. Growth Des. 2012, 12, 3526-3539
50. Vasylyeva, V.; Shishkin, O. V.; Maleev, A. V.; Merz, K. Crystal structures of fluorinated pyridines from geometrical and energetic perspectives Cryst. Growth Des. 2012, 12, 1032-1039
51. Bui, T. T.; Dahaoui, S.; Lecomte, C.; Desiraju, G. R.; Espinosa, E. The nature of halogen⋯halogen interactions: A model derived from experimental charge-density analysis Angew. Chem., Int. Ed. 2009, 48, 3838-3841
52. Civalleri, B.; Doll, K.; Zicovich-Wilson, C. M. Ab initio investigation of structure and cohesive energy of crystalline urea J. Phys. Chem. B 2007, 111, 26-33 (Pubitemid 46277967)
53. Ferrero, M.; Civalleri, B.; Rerat, M.; Orlando, R.; Dovesi, R. The calculation of the static first and second susceptibilities of crystalline urea: A comparison of Hartree-Fock and density functional theory results obtained with the periodic coupled perturbed Hartree-Fock/Kohn-Sham scheme J. Chem. Phys. 2009, 131, 214704
54. Perger, W. F.; Criswell, J.; Civalleri, B.; Dovesi, R. Ab-initio calculation of elastic constants of crystalline systems with the CRYSTAL code Comput. Phys. Commun. 2009, 180, 1753-1759
55. Matta, C. F.; Hernández-Trujillo, J.; Tang, T.-H.; Bader, R. F. W. Hydrogen-hydrogen bonding: A stabilizing interaction in molecules and crystals Chem.-Eur. J. 2003, 9, 1940-1951
56. Madsen, A. Ø.; Larsen, S. Insight into solid-state entropy from diffraction data Angew. Chem., Int. Ed. 2007, 46, 8609-8613 (Pubitemid 350189075)
57. Jarzembska, K. N.; Kubsik, M.; Kamiński, R.; Woźniak, K.; Dominiak, P. M. From a single molecule to molecular crystal architectures: Structural and energetic studies of selected uracil derivatives Cryst. Growth Des. 2012, 12, 2508-2524
58. Bàk, J. M.; Domagała, S.; Hübschle, C.; Jelsch, C.; Dittrich, B.; Dominiak, P. M. Verification of structural and electrostatic properties obtained by the use of different pseudoatom databases Acta Crystallogr. 2011, A67, 141-153
59. Koritsanszky, T.; Volkov, A.; Coppens, P. Aspherical-atom scattering factors from molecular wave functions. 1. Transferability and conformation dependence of atomic electron densities of peptides within the multipole formalism Acta Crystallogr. 2002, A58, 464-472 (Pubitemid 34994181)
60. Volkov, A.; Li, X.; Koritsanszky, T.; Coppens, P. Ab initio quality electrostatic atomic and molecular properties including intermolecular energies from a transferable theoretical pseudoatom databank J. Phys. Chem. A 2004, 108, 4283-4300
61. Dittrich, B.; Hübschle, C. B.; Holstein, J. J.; Fabbiani, F. P. A. Towards extracting the charge density from normalresolution data J. Appl. Crystallogr. 2009, 42, 1110-1121
62. Pröpper, K.; Holstein, J. J.; Hübschle, C. B.; Bond, C. S.; Dittrich, B. Invariom refinement of a new monoclinic solvate of thiostrepton at 0.64 Å resolution Acta Crystallogr. 2013, D69, 1530-1539
63. Dittrich, B.; Koritsanszky, T.; Luger, P. A simple approach to nonspherical electron densities by using invarioms Angew. Chem., Int. Ed. 2004, 43, 2718
64. APEX2; Bruker AXS: Madison, Wisconsin, USA, 2012.
65. Blessing, R. H. Data reduction and error analysis for accurate single crystal diffraction intensities Cryst. Rev. 1987, 1, 3-58
66. Blessing, R. H. DREADD-Data reduction and error analysis for single-crystal diffractometer data J. Appl. Crystallogr. 1989, 22, 396-397
67. Blessing, R. H. An empirical correction for absorption anisotropy Acta Crystallogr. 1995, A51, 33-38
68. Blessing, R. H. Outlier treatment in data merging J. Appl. Crystallogr. 1997, 30, 421-426 (Pubitemid 127477033)
69. Palatinus, L. The charge-flipping algorithm in crystallography Acta Crystallogr. 2013, B69, 1-16
70. Oszlányi, G.; Süto, A. Ab initio structure solution by charge flipping Acta Crystallogr. 2004, A60, 134-141 (Pubitemid 40747284)
71. Oszlányi, G.; Süto, A. Ab initio structure solution by charge flipping. II. Use of weak reflections Acta Crystallogr. 2005, A61, 147-152 (Pubitemid 41623574)
72. Palatinus, L.; Chapuis, G. Superflip-A computer program for the solution of crystal structures by charge flipping in arbitrary dimensions J. Appl. Crystallogr. 2007, 40, 786-790 (Pubitemid 47080274)
73. Petříček, V.; Dušek, M.; Palatinus, L. JANA2006; Institute of Physics: Praha, Czech Republic, 2006.
74. Jelsch, C.; Guillot, B.; Lagoutte, A.; Lecomte, C. Advances in protein and small-molecule charge density refinement methods using MoPro J. Appl. Crystallogr. 2005, 38, 38-54 (Pubitemid 40260748)
75. Guillot, B.; Viry, L.; Guillot, R.; Lecomte, C.; Jelsch, C. Refinement of proteins at subatomic resolution with MoPro J. Appl. Crystallogr. 2001, 34, 214-223 (Pubitemid 32290311)
76. Jarzembska, K. N.; Dominiak, P. M. New version of the theoretical databank of transferable aspherical pseudoatoms, UBDB2011-Towards nucleic acid modelling Acta Crystallogr. 2012, A68, 139-147
77. Kamiński, R.; Domagała, S.; Jarzembska, K. N.; Hoser, A. A.; Sanjuan-Szklarz, W. F.; Gutmann, M. J.; Makal, A.; Malińska, M.; Bàk, J. M.; Woźniak, K. Statistical analysis of multipole-model-derived structural parameters and charge-density properties from high-resolution X-ray diffraction experiments Acta Crystallogr. 2014, A70, 72-91
78. Poulain, A.; Wenger, E.; Durand, P.; Jarzembska, K. N.; Kamiński, R.; Fertey, P.; Kubicki, M.; Lecomte, C. Anharmonicity and isomorphic phase transition: A multi-temperature X-ray single crystal and powder diffraction study of 1-(2′-aminophenyl)-2-methyl-4-nitroimidazole IUCr J. 2014, 1, 110-118
79. Meindl, K.; Henn, J. Foundations of residual-density analysis Acta Crystallogr. 2008, A64, 404-418 (Pubitemid 351563478)
80. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: New York, 1994.
81. Guillot, B. MoProViewer: A molecule viewer for the MoPro charge-density analysis program Acta Crystallogr. 2012, A68, s204
82. Kamiński, R.; Jarzembska, K. N.; Domagała, S. CLUSTERGEN: A program for molecular cluster generation from crystallographic data J. Appl. Crystallogr. 2013, 46, 540-534
83. Stash, A.; Tsirelson, V. WinXPRO: A program for calculating crystal and molecular properties using multipole parameters of the electron density J. Appl. Crystallogr. 2002, 35, 371-373 (Pubitemid 34662867)
84. Stash, A. I.; Tsirelson, V. G. Modern possibilities for calculating some properties of molecules and crystals from the experimental electron density Cryst. Reports 2005, 50, 177-184 (Pubitemid 40537353)
85. Dovesi, R.; Civalleri, B.; Orlando, R.; Roetti, C.; Saunders, V. R. Ab initio quantum simulation in solid state chemistry Rev. Comput. Chem. 2005, 21, 1-125 (Pubitemid 44578717)
86. Dovesi, R.; Saunders, V. R.; Roetti, C.; Orlando, R.; Zicovich-Wilson, C. M.; Pascale, F.; Civalleri, B.; Doll, K.; Harrison, N. M.; Bush, I. J.; DArco, P.; Llunell, M. CRYSTAL09; University of Torino: Torino, Italy, 2009.
87. Becke, A. D. Density-functional exchange-energy approximation with correct asymptotic behavior Phys. Rev. A 1988, 38, 3098-3100
88. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37, 785-789
89. Dunning, T. H. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen J. Chem. Phys. 1989, 90, 1007-1023
90. Schäfer, A.; Huber, C.; Alrichs, R. Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr J. Chem. Phys. 1994, 100, 5829-5835
91. Grimme, S. Accurate description of van der Waals complexes by density functional theory including empirical corrections J. Comput. Chem. 2004, 25, 1463-1473
92. Grimme, S. Semiempirical GGA-type density functional constructed with a long-range dispersion correction J. Comput. Chem. 2006, 27, 1787-1799 (Pubitemid 44672561)
93. Boys, S. F.; Bernardi, F. The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors Mol. Phys. 1970, 19, 553-566
94. Civalleri, B.; Zicovich-Wilson, C. M.; Valenzano, L.; Ugliengo, P. B3LYP augmented with an empirical dispersion term (B3LYP-D) as applied to molecular crystals CrystEngComm 2008, 10, 405-410
95. Gavezzotti, A. Calculation of intermolecular interaction energies by direct numerical integration over electron densities. 2. An improved polarization model and the evaluation of dispersion and repulsion energies J. Phys. Chem. B 2003, 107, 2344-2353
96. Gavezzotti, A. Calculation of intermolecular interaction energies by direct numerical integration over electron densities. I. Electrostatic and polarization energies in molecular crystals J. Phys. Chem. B 2002, 106, 4145-4154 (Pubitemid 35290150)
97. Gavezzotti, A. Towards a realistic model for the quantitative evaluation of intermolecular potentials and for the rationalization of organic crystal structures. Part I. Philosophy CrystEngComm 2003, 5, 429-438 (Pubitemid 40447018)
98. Gavezzotti, A. Quantitative ranking of crystal packing modes by systematic calculations on potential energies and vibrational amplitudes of molecular dimers J. Chem. Theory Comput. 2005, 834-840
99. Møller, C.; Plesset, M. S. Note on an approximation treatment for many-electron systems Phys. Rev. 1934, 46, 618-622
100. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions J. Chem. Phys. 1980, 72, 650-654
101. Aree, T.; Bürgi, H.-B. Specific heat of molecular crystals from atomic mean square displacements with the Einstein, Debye, and Nernst-Lindemann models J. Phys. Chem. B 2006, 110, 26129-26134 (Pubitemid 46133331)
102. Aree, T.; Bürgi, H.-B. Dynamics and thermodynamics of crystalline polymorphs: α-Glycine, Analysis of variable-temperature atomic displacement parameters J. Phys. Chem. A 2012, 116, 8092-8099
103. Bürgi, H.-B.; Capelli, S. C. Dynamics of molecules in crystals from multi-temperature anisotropic displacement parameters. I. Theory Acta Crystallogr. 2000, A56, 403-412
104. 2] Acta Crystallogr. 2000, A56, 413-424
105. Madsen, A. Ø.; Mattson, R.; Larsen, S. Understanding thermodynamic properties at the molecular level: multiple temperature charge density study of ribitol and xylitol J. Phys. Chem. A 2011, 115, 7794-7804
106. Schomaker, V.; Trueblood, K. N. On the rigid-body motion of molecules in crystals Acta Crystallogr. 1968, B24, 63-76
107. Schomaker, V.; Trueblood, K. N. Correlation of internal torsional motion with overall molecular motion in crystals Acta Crystallogr. 1998, B54, 507-514 (Pubitemid 128432751)
108. Cruickshank, D. W. J. The analysis of the anisotropic thermal motion of molecules in crystals Acta Crystallogr. 1956, 9, 754-756
109. Sands, D. E. Vectors and Tensors in Crystallography; Addinson-Wesley Publishing Company: Reading, MA, 1982.
110. Pascale, F.; Zicovich-Wilson, C. M.; Gejo, F. L.; Civalleri, B.; Orlando, R.; Dovesi, R. The calculation of the vibrational frequencies of crystalline compounds and its implementation in the CRYSTAL code J. Comput. Chem. 2004, 25, 888-897
111. Madsen, A. Ø.; Civalleri, B.; Ferrabone, M.; Pascale, F.; Erba, A. Anisotropic displacement parameters for molecular crystals from periodic Hartree-Fock and density functional theory calculations Acta Crystallogr. 2013, A69, 309-321
112. Miwa, Y.; Mizuno, T.; Tsuchida, K.; Tagaa, T.; Iwata, Y. Experimental charge density and electrostatic potential in nicotinamide Acta Crystallogr. 1999, B55, 78-84 (Pubitemid 129551557)
113. Espinosa, E.; Molins, E.; Lecomte, C. Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities Chem. Phys. Lett. 1998, 285, 170-173 (Pubitemid 128180262)
114. Espinosa, E.; Lecomte, C.; Molins, E. Experimental electron density overlapping in hydrogen bonds: Topology vs. energetics Chem. Phys. Lett. 1999, 300, 745-748 (Pubitemid 129549405)
115. Maschio, L.; Civalleri, B.; Ugliengo, P.; Gavezzotti, A. Intermolecular interaction energies in molecular crystals: comparison and agreement of localized Møller-Plesset 2, dispersion-corrected density functional, and classical empirical two-body calculations J. Phys. Chem. A 2011, 115, 11179-11186
116. Spackman, M. A.; Jayatilaka, D. Hirshfeld surface analysis CrystEngComm 2009, 11, 19-32
117. Spackman, M. A.; Byrom, P. G. A novel definition of a molecule in a crystal Chem. Phys. Lett. 1997, 267, 215-220 (Pubitemid 127160799)
118. Spackman, M. A. Molecules in crystals Phys. Scr. 2013, 87, 048103
119. Spackman, M. A.; McKinnon, J. J.; Jayatilaka, D. Electrostatic potentials mapped on Hirshfeld surfaces provide direct insight into intermolecular interactions in crystals CrystEngComm 2008, 10, 377-388
120. Hirshfeld, F. L. Can X-ray data distinguish bonding effects from vibrational smearing? Acta Crystallogr. 1976, A32, 239-244
121. Dittrich, B.; Hübschle, C. B.; Pröpper, K.; Dietrich, F.; Stolper, T.; Holstein, J. J. The generalized invariom database (GID) Acta Crystallogr. 2013, B69, 91-104
122. Domagała, S.; Fournier, B.; Liebschner, D.; Guillot, B.; Jelsch, C. An improved experimental databank of transferable multipolar atom models-ELMAM2. Construction details and applications Acta Crystallogr. 2012, A68, 337-351
123. Bàk, J. M.; Dominiak, P. M.; Wilson, C. C.; Woźniak, K. Experimental charge-density study of paracetamol-Multipole refinement in the presence of a disordered methyl group Acta Crystallogr. 2009, A65, 490-500
124. Dittrich, B.; McKinnon, J. J.; Warren, J. E. Improvement of anisotropic displacement parameters from invariom-model refinements for three l -hydroxylysine structures Acta Crystallogr. 2008, B64, 750-759