275:
63:
351:
267:
206:
106:
97:, who in 1988 defined crystal engineering as "the understanding of intermolecular interactions in the context of crystal packing and the utilization of such understanding in the design of new solids with desired physical and chemical properties." Since many of the bulk properties of molecular materials are dictated by the manner in which the molecules are ordered in the solid state, it is clear that an ability to control this ordering would afford control over these properties.
225:(CSP) is a computational approach to generate energetically feasible crystal structures (with corresponding space group and positional parameters) from a given molecular structure. The CSP exercise is considered most challenging as "experimental" crystal structures are very often kinetic structures and therefore are very difficult to predict. In this regard, many protocols have been proposed and are tested through several blind tests organized by
144:
181:
term (2D) supramolecular engineering a more accurate term. Specifically, supramolecular engineering refers to "(The) design (of) molecular units in such way that a predictable structure is obtained" or as "the design, synthesis and self-assembly of well defined molecular modules into tailor-made supramolecular architectures".
198:, the phenomenon wherein the same chemical compound exists in more than one crystal forms, is relevant commercially because polymorphic forms of drugs may be entitled to independent patent protection. The importance of crystal engineering to the pharmaceutical industry is expected to grow exponentially.
214:
possibilities within a small energy window. As a result, multiple crystal structures can be obtained with the same molecule but in different conformations. The rarest form of polymorphism arises from the differences in the primary synthon and this type of polymorphism is called as synthon polymorphism.
180:
depending on its deposition process) of such architectures lies in the use of solid interfaces to create adsorbed monolayers. Such monolayers may feature spatial crystallinity. However the dynamic and wide range of monolayer morphologies ranging from amorphous to network structures have made of the
233:
Apart from the ability of predicting crystal structures, CSP also gives computed energy landscapes of crystal structures where many structures lie within a narrow energy window. This kind of computed landscapes lend insights into the study on polymorphism, design of new structures and also help to
229:
since 2002. A major advance in the CSP happened in 2007 while a hybrid method based on tailor made force fields and density functional theory (DFT) was introduced. In the first step, this method employs tailor made force fields to decide upon the ranking of the structures followed by a dispersion
201:
Polymorphism arises due to the competition between kinetic and thermodynamic factors during crystallization. While long-range strong intermolecular interactions dictate the formation of kinetic crystals, the close packing of molecules generally drives the thermodynamic outcome. Understanding this
257:
The design of crystal structures with desired properties is the ultimate goal of crystal engineering. Crystal engineering principles have been applied to the design of non-linear optical materials, especially those with second harmonic generation (SHG) properties. Using supramolecular synthons,
213:
In organic molecules, three types of polymorphism are mainly observed. Packing polymorphism arises when molecules pack in different ways to give different structures. Conformational polymorphism, on the other hand is mostly seen in flexible molecules where molecules have multiple conformational
564:
in crystal engineering is that these surface maps are embedded with information about a molecular and its neighbors. The insight into molecular neighbors can be applied to assessment or prediction of molecular properties. An emerging method for topography and
357:
Slip planes associated with layered or columnar architectural features in crystalline materials. Red dotted and black dashed lines represent the direction of the weakest and strongest intermolecular interactions, respectively, which influences the slip plane.
243:
342:
molecules form due to the hydrogen bond donors and acceptors that flank the benzene ring. The weaker interactions between the chains or layers of acetaminophen required less energy to break than the hydrogen bonds. As a result, a
159:
is most often achieved with strong heteromolecular interactions. The main relevance of multi-component crystals is focused upon designing pharmaceutical cocrystals. Pharmaceutical cocrystals are generally composed of one API
1673:
520:
of the sample. Raman spectroscopy is a method that uses light scattering to interact with bonds in a sample. This technique provides information about chemical bonds, intermolecular interactions, and crystallinity.
85:
The term 'crystal engineering' was first used in 1955 by R. Pepinsky but the starting point is often credited to
Gerhard Schmidt in connection with photodimerization reactions in crystalline
1726:"Rationalizing Distinct Mechanical Properties of Three Polymorphs of a Drug Adduct by Nanoindentation and Energy Frameworks Analysis: Role of Slip Layer Topology and Weak Interactions"
1662:
1056:
Supramolecular
Synthons in Designing Low Molecular Mass Gelling Agents: L-Amino Acid Methyl Ester Cinnamate Salts and their Anti-Solvent-Induced Instant Gelation Chem
917:
Supramolecular
Crystal Engineering at the Solid– Liquid Interface from First Principles: Toward Unraveling the Thermodynamics of 2D Self- Assembly, Adv. Mat.
389:
alters the mechanism or degree of molecular movement, thereby changing the mechanical properties of the material. Examples of point imperfections include
805:
Janeta, Mateusz; Szafert, SĹ‚awomir (2017-10-01). "Synthesis, characterization and thermal properties of T8 type amido-POSS with p-halophenyl end-group".
168:). Various properties (such as solubility, bioavailability, permeability) of an API can be modulated through the formation of pharmaceutical cocrystals.
282:
Designing a crystalline material with targeted properties requires an understanding of the material's molecular and crystal features in relation to its
270:
Four mechanical properties of crystalline materials: shear strength, plasticity, elasticity, and brittleness. Information adapted from Saha et al. 2018.
135:. "Supramolecular synthons" are building blocks that are common to many structures and hence can be used to order specific groups in the solid state.
362:
Example of the strongest (hydrogen bonds) and weakest (van der Waals) interactions in acetaminophen structure that influences the crystal structure.
967:
Towards
Supramolecular Engineering of Functional Nanomaterials: PreProgramming MultiComponent 2D SelfAssembly at Solid Liquid Interfaces, Adv. Mat.
1724:
Raju, K. Bal; Ranjan, Subham; Vishnu, V. S.; Bhattacharya, Manjima; Bhattacharya, Biswajit; Mukhopadhyay, Anoop K.; Reddy, C. Malla (2018-07-05).
663:
Braga, D.; Desiraju, Gautam R.; Miller, Joel S.; Orpen, A. Guy; Price, Sarah (Sally) L.; et al. (2002), "Innovation in
Crystal Engineering",
226:
131:
is at the heart of crystal engineering, and it typically involves an interaction between complementary hydrogen bonding faces or a metal and a
274:
1996:
1552:
1141:
385:, such as point defects, tilt boundaries, or dislocations, create imperfections in crystal architecture and topology. Any disruption to the
883:
Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines?
532:
is a standard and widely-accepted method for measuring mechanical properties within the crystal engineering field. The method quantifies
246:
A resorcinol based templating strategy described by
Macgillivray and co workers to illustrate the control of photodimerization outcome,
2006:
482:
278:
Designing a material with targeted mechanical properties requires command over complex structures across a range of length scales.
591:
545:
195:
695:; Pilati, Tullio; Liantonio, Rosalba; Meyer, Franck; et al. (2007), "Engineering Functional Materials by Halogen Bonding",
62:
366:
A supramolecular synthon is a pair of molecules that form relatively strong intermolecular interactions in the early phases of
350:
176:
2D architectures (i.e., molecularly thick architectures) is a branch of crystal engineering. The formation (often referred as
2001:
454:
1986:
601:
222:
94:
266:
89:. Since this initial use, the meaning of the term has broadened considerably to include many aspects of solid state
1991:
1249:
Gupta, Poonam; Rather, Sumair A.; Saha, Binoy K.; Panda, Tamas; Karothu, Durga Prasad; Nath, Naba K. (2020-05-06).
612:
1578:"New opportunities in crystal engineering – the role of atomic force microscopy in studies of molecular crystals"
628:
202:
dichotomy between the kinetics and thermodynamics constitutes the focus of research related to the polymorphism.
184:
165:
114:
33:
studies the design and synthesis of solid-state structures with desired properties through deliberate control of
2011:
1022:
Computed
Crystal Energy Landscapes for Understanding and Predicting Organic Crystal Structures and Polymorphism
633:
566:
344:
90:
1854:"Computational Techniques for Predicting Mechanical Properties of Organic Crystals: A Systematic Evaluation"
1337:"Computational Techniques for Predicting Mechanical Properties of Organic Crystals: A Systematic Evaluation"
643:
382:
177:
128:
934:
Molecular and
Supramolecular Networks on Surfaces: From Two Dimensional Crystal Engineering to Reactivity,
310:
Manipulation of the intermolecular interaction network is a means for controlling bulk properties. During
117:
to achieve the organization of molecules and ions in the solid state. Much of the initial work on purely
586:
561:
549:
283:
164:) with other molecular substances that are considered safe according to the guidelines provided by WHO (
147:
A five component crystal was designed by
Desiraju and co workers by a rational retrosynthetic strategy (
570:
1624:
1823:
704:
557:
537:
450:
335:
331:
315:
291:
287:
34:
446:
394:
38:
1889:
1811:
1773:"Nanoindentation in Crystal Engineering: Quantifying Mechanical Properties of Molecular Crystals"
1753:
1372:
1278:
1112:
442:
1470:"Designer crystals: intermolecular interactions, network structures and supramolecular synthons"
1077:"From Molecules to Interactions to Crystal Engineering: Mechanical Properties of Organic Solids"
1699:
Nanoindentation in
Crystal Engineering: Quantifying Mechanical Properties of Molecular Crystals
1251:"Mechanical Flexibility of Molecular Crystals Achieved by Exchanging Hydrogen Bonding Synthons"
55:
and coordination bonding. These may be understood with key concepts such as the supramolecular
1935:
1927:
1881:
1873:
1792:
1771:
Varughese, Sunil; Kiran, M. S. R. N.; Ramamurty, Upadrasta; Desiraju, Gautam R. (2013-03-04).
1745:
1644:
1605:
1597:
1558:
1548:
1516:
1450:
1411:
1364:
1356:
1317:
1270:
1228:
1220:
1178:
1137:
1131:
1104:
1096:
822:
618:
574:
498:
434:
430:
426:
422:
386:
205:
161:
118:
72:
1853:
1336:
1919:
1865:
1831:
1784:
1737:
1636:
1589:
1508:
1477:
1442:
1403:
1348:
1309:
1262:
1212:
1170:
1088:
814:
712:
692:
674:
553:
509:
486:
105:
67:
1075:
Saha, Subhankar; Mishra, Manish Kumar; Reddy, C. Malla; Desiraju, Gautam R. (2018-11-20).
596:
529:
470:
438:
402:
371:
367:
311:
1827:
1431:"Supramolecular Synthons: Validation and Ranking of Intermolecular Interaction Energies"
1076:
708:
513:
458:
398:
390:
299:
143:
41:
1912:"Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces"
1869:
1640:
1352:
1298:"Establishing a Hierarchy of Halogen Bonding by Engineering Crystals without Disorder"
990:(Ed. W. M. Hosseini), Springer Berlin Heidelberg, Berlin, Heidelberg, 2009, pp. 87-95.
1980:
1757:
1282:
818:
638:
623:
517:
319:
86:
48:
1893:
1376:
1116:
1725:
1391:
1250:
665:
606:
122:
52:
17:
841:
Halogen Bonding Based Recognition Processes:  A World Parallel to Hydrogen Bonding
1835:
1663:"Analysis of crystal polymorphism by Raman Spectroscopy for Medicine Development"
1092:
465:
of a material. Ultimately, these methods elaborate on the growth and assembly of
478:
474:
466:
462:
410:
406:
339:
295:
1544:
Advanced electrical and electronics materials : processes and applications
1772:
541:
1931:
1877:
1749:
1648:
1601:
1562:
1520:
1454:
1430:
1415:
1360:
1321:
1297:
1274:
1224:
1200:
1182:
1100:
826:
209:
The pathways to kinetically favoured and thermodynamically favoured crystals.
1741:
1407:
1392:"Building upon Supramolecular Synthons: Some Aspects of Crystal Engineering"
1266:
242:
156:
1939:
1885:
1796:
1788:
1609:
1368:
1232:
1108:
1971:
1542:
437:
creating a unique pattern after X-rays are diffracted through the crystal
1512:
1496:
1174:
1158:
533:
490:
370:; these molecule pairs are the basic structural motif found in a crystal
109:
Br···O halogen bonds observed in crystal structure of 3D silsesquioxanes.
1810:
Mishra, Manish Kumar; Ramamurty, Upadrasta; Desiraju, Gautam R. (2016).
286:. Four mechanical properties are of interest for crystalline materials:
121:
systems focused on the use of hydrogen bonds, although coordination and
1593:
1577:
1296:
Aakeröy, Christer B.; Chopade, Prashant D.; Desper, John (2013-09-04).
1201:"Hydrogen Bridges in Crystal Engineering: Interactions without Borders"
716:
506:
502:
494:
56:
1446:
1313:
1216:
862:
Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis
1923:
1911:
1481:
1469:
678:
132:
516:
of the crystalline material, which can be used to determine percent
1961:
1697:
S. Varughese, M. S. R. N. Kiran, U. Ramamurty and G. R. Desiraju,
900:
Engineering atomic and molecular nanostructures at surfaces, Nature
1910:
McKinnon, Joshua J.; Jayatilaka, Dylan; Spackman, Mark A. (2007).
1576:
Chow, Ernest H. H.; Bučar, Dejan-Krešimir; Jones, William (2012).
230:
corrected DFT method to calculate the lattice energies precisely.
556:
at a specific isosurface that aid in visualizing and quantifying
1956:
1966:
1497:"Lattice imperfections in organic solids. Part 1.—Anthracene"
1133:
Elements of Structures and Defects of Crystalline Materials
338:
form the slip plane. For example, long chains or layers of
429:
of a material by quantifying distances between atoms. The
1625:"The measurement of the crystallinity of polymers by DSC"
954:
Design of molecular materials: supramolecular engineering
839:
P. Metrangolo, H. Neukirch, T. Pilati and G. Resnati,
577:
that depict interaction energies as pillars or beams.
1335:
Wang, Chenguang; Sun, Changquan Calvin (April 2019).
334:
form the molecular layers or columns and the weakest
318:
form according to an electrostatic hierarchy. Strong
47:
The main engineering strategies currently in use are
44:, bridging solid-state and supramolecular chemistry.
1816:
Current Opinion in Solid State and Materials Science
1054:
P. Sahoo, D. K. Kumar, S. R. Raghavan, P. Dastidar.
1043:
Supramolecular gelling agents: can they be designed?
751:
Crystal Engineering - New Concept in Crystallography
187:
enable visualization of two dimensional assemblies.
473:, which can be used to rationalize the movement of
322:are the primary director for crystal organization.
27:
Designing solid structures with tailored properties
1157:Aakeröy, Christer B.; Seddon, Kenneth R. (1993).
982:D. Braga, F. Grepioni, L. Maini and M. Polito in
965:A. Ciesielski, C.A. Palma, M. Bonini, P. Samori,
793:Crystal Engineering: The design of Organic Solids
93:. A useful modern definition is that provided by
1812:"Mechanical property design of molecular solids"
999:M. A. Neumann, F. J. J. Leusen and J. Kendrick,
1852:Wang, Chenguang; Sun, Changquan Calvin (2019).
1001:A Major Advance in Crystal Structure Prediction
984:Crystal Polymorphism and Multiple Crystal Forms
489:in order to quantify the associated changes in
915:C.A. Palma, M. Bonini, T. Breiner, P. Samori,
262:Mechanical properties of crystalline materials
125:provide additional control in crystal design.
8:
1429:Dunitz, J. D.; Gavezzotti, A. (2012-12-05).
932:J. A. A. W. Elemans, S.B. Lei S. De Feyter,
1159:"The hydrogen bond and crystal engineering"
405:. Examples of line imperfections include
349:
273:
265:
258:supramolecular gels have been designed.
241:
204:
142:
104:
66:An example of crystal engineering using
61:
1777:Angewandte Chemie International Edition
1495:Williams, J. O.; Thomas, J. M. (1967).
655:
1536:
1534:
1532:
1530:
1244:
1242:
1194:
1192:
1070:
1068:
1066:
1064:
898:J. V. Barth, G. Constantini, K. Kern,
1905:
1903:
1847:
1845:
1719:
1717:
1715:
185:scanning probe microscopic techniques
7:
772:Photodimerization in the solid state
730:Crystal Engineering: A Holistic View
697:J. Polym. Sci., Part A: Polym. Chem.
234:design crystallization experiments.
1623:Kong, Y.; Hay, J. N. (2002-06-01).
881:O. Almarsson and M. J. Zaworotko,
807:Journal of Organometallic Chemistry
70:reported by Wuest and coworkers in
421:Crystallographic methods, such as
139:Design of multi-component crystals
25:
1870:10.1021/acs.molpharmaceut.9b00082
1353:10.1021/acs.molpharmaceut.9b00082
483:differential scanning calorimetry
433:technique relies on a particular
101:Non-covalent control of structure
59:and the secondary building unit.
1967:Acta Crystallographica Section B
1547:. Gupta, Nishu. Hoboken: Wiley.
1390:Mukherjee, Arijit (2015-06-03).
819:10.1016/j.jorganchem.2017.05.044
477:in response to an applied load.
162:Active Pharmaceutical Ingredient
1679:from the original on 2022-03-03
525:Assessing mechanical properties
457:, can be used to visualize the
441:. Microscopic methods, such as
1130:Fang, Tsang-Tse (2018-01-25).
1045:Chem. Soc. Rev. 2008, 37, 2699
592:crystal nets (periodic graphs)
113:Crystal engineering relies on
1:
1972:Cambridge Structural Database
1641:10.1016/S0032-3861(02)00235-5
1205:Accounts of Chemical Research
1081:Accounts of Chemical Research
1058:. Asian J. 2011, 6, 1038–1047
455:scanning tunneling microscopy
393:, substitutional impurities,
155:The intentional synthesis of
1997:Chemical product engineering
1836:10.1016/j.cossms.2016.05.011
1468:Desiraju, Gautam R. (1997).
1199:Desiraju, Gautam R. (2002).
1093:10.1021/acs.accounts.8b00425
602:Laser-heated pedestal growth
425:, are used to elucidate the
223:Crystal structure prediction
218:Crystal structure prediction
1730:Crystal Growth & Design
1435:Crystal Growth & Design
1396:Crystal Growth & Design
1302:Crystal Growth & Design
1255:Crystal Growth & Design
795:, Elsevier, 1989, Amsterdam
613:Crystal Growth & Design
558:intermolecular interactions
548:of a crystalline material.
417:Assessing Crystal Structure
336:intermolecular interactions
332:intermolecular interactions
316:intermolecular interactions
306:Intermolecular interactions
35:intermolecular interactions
2028:
1957:Crystal Growth and Design
629:Molecular design software
330:Typically, the strongest
166:World Health Organization
2007:Supramolecular chemistry
634:Supramolecular chemistry
560:. An advantage to using
378:Defects or imperfections
91:supramolecular chemistry
1916:Chemical Communications
1858:Molecular Pharmaceutics
1742:10.1021/acs.cgd.8b00261
1582:Chemical Communications
1474:Chemical Communications
1408:10.1021/acs.cgd.5b00242
1341:Molecular Pharmaceutics
1267:10.1021/acs.cgd.9b01530
644:Molecular self-assembly
395:interstitial impurities
253:, 2000, 122, 7817-7818.
178:molecular self-assembly
129:Molecular self-assembly
1789:10.1002/anie.201205002
1670:Jasco Application Note
952:J. Simon, P. Bassoul,
573:, which are models of
363:
279:
271:
254:
210:
152:
110:
77:
2002:Solid-state chemistry
1703:Angew. Chem. Int. Ed.
1541:Gupta, K. M. (2015).
1005:Angew. Chem. Int. Ed.
937:Angew. Chem. Int. Ed.
866:Angew. Chem. Int. Ed.
734:Angew. Chem. Int. Ed.
587:Coordination polymers
552:are visual models of
512:are dependent on the
353:
284:mechanical properties
277:
269:
245:
208:
146:
108:
65:
1513:10.1039/TF9676301720
1175:10.1039/CS9932200397
461:, imperfections, or
326:Crystal architecture
1987:Crystal engineering
1828:2016COSSM..20..361M
709:2007JPoSA..45....1M
151:, 2016, 3, 96–101).
115:noncovalent bonding
31:Crystal engineering
18:Crystal Engineering
1594:10.1039/c2cc32678g
1501:Trans. Faraday Soc
770:G. M. J. Schmidt,
717:10.1002/pola.21725
562:Hirshfeld surfaces
550:Hirshfeld surfaces
499:Gibb's free energy
411:screw dislocations
403:Schottky’s defects
364:
280:
272:
255:
211:
153:
111:
78:
76:, 2007, 4306–4322.
1992:Materials science
1918:(37): 3814–3816.
1783:(10): 2701–2712.
1635:(14): 3873–3878.
1588:(74): 9210–9226.
1554:978-1-118-99858-8
1476:(16): 1475–1482.
1447:10.1021/cg301293r
1441:(12): 5873–5877.
1314:10.1021/cg400988m
1217:10.1021/ar010054t
1143:978-0-12-814269-1
1087:(11): 2957–2967.
860:G. R. Desiraju,
693:Resnati, Giuseppe
619:CrystEngCommunity
571:energy frameworks
510:phase transitions
487:phase transitions
481:methods, such as
435:crystal structure
431:X-ray diffraction
427:crystal structure
423:X-ray diffraction
399:Frenkel’s defects
387:crystal structure
172:In two dimensions
73:J. Am. Chem. Soc.
39:interdisciplinary
16:(Redirected from
2019:
1944:
1943:
1924:10.1039/b704980c
1907:
1898:
1897:
1864:(4): 1732–1741.
1849:
1840:
1839:
1807:
1801:
1800:
1768:
1762:
1761:
1736:(7): 3927–3937.
1721:
1710:
1695:
1689:
1688:
1686:
1684:
1678:
1667:
1659:
1653:
1652:
1620:
1614:
1613:
1573:
1567:
1566:
1538:
1525:
1524:
1492:
1486:
1485:
1482:10.1039/a607149j
1465:
1459:
1458:
1426:
1420:
1419:
1402:(6): 3076–3085.
1387:
1381:
1380:
1347:(4): 1732–1741.
1332:
1326:
1325:
1308:(9): 4145–4150.
1293:
1287:
1286:
1261:(5): 2847–2852.
1246:
1237:
1236:
1196:
1187:
1186:
1154:
1148:
1147:
1127:
1121:
1120:
1072:
1059:
1052:
1046:
1039:
1033:
1018:
1012:
997:
991:
980:
974:
963:
957:
950:
944:
930:
924:
913:
907:
896:
890:
879:
873:
858:
852:
837:
831:
830:
802:
796:
791:G. R. Desiraju,
789:
783:
776:Pure Appl. Chem.
768:
762:
755:Physical Review
747:
741:
728:G. R. Desiraju,
726:
720:
719:
691:Metrangolo, P.;
688:
682:
681:
679:10.1039/b207466b
660:
554:electron density
68:hydrogen bonding
21:
2027:
2026:
2022:
2021:
2020:
2018:
2017:
2016:
2012:Crystallography
1977:
1976:
1953:
1948:
1947:
1909:
1908:
1901:
1851:
1850:
1843:
1809:
1808:
1804:
1770:
1769:
1765:
1723:
1722:
1713:
1696:
1692:
1682:
1680:
1676:
1665:
1661:
1660:
1656:
1622:
1621:
1617:
1575:
1574:
1570:
1555:
1540:
1539:
1528:
1494:
1493:
1489:
1467:
1466:
1462:
1428:
1427:
1423:
1389:
1388:
1384:
1334:
1333:
1329:
1295:
1294:
1290:
1248:
1247:
1240:
1198:
1197:
1190:
1156:
1155:
1151:
1144:
1129:
1128:
1124:
1074:
1073:
1062:
1053:
1049:
1040:
1036:
1026:Acc. Chem. Res.
1019:
1015:
998:
994:
981:
977:
964:
960:
956:, 2000 WileyVCH
951:
947:
931:
927:
914:
910:
897:
893:
889:2004, 1889-1896
880:
876:
859:
855:
845:Acc. Chem. Res.
838:
834:
804:
803:
799:
790:
786:
769:
765:
748:
744:
727:
723:
690:
689:
685:
673:(83): 500–509,
662:
661:
657:
652:
597:Crystallography
583:
575:crystal packing
569:analysis using
530:Nanoindentation
527:
471:crystallization
419:
383:Lattice defects
380:
368:crystallization
328:
312:crystallization
308:
264:
240:
238:Property design
220:
193:
174:
141:
103:
95:Gautam Desiraju
83:
81:History of term
53:halogen bonding
28:
23:
22:
15:
12:
11:
5:
2025:
2023:
2015:
2014:
2009:
2004:
1999:
1994:
1989:
1979:
1978:
1975:
1974:
1969:
1964:
1959:
1952:
1951:External links
1949:
1946:
1945:
1899:
1841:
1822:(6): 361–370.
1802:
1763:
1711:
1690:
1654:
1615:
1568:
1553:
1526:
1487:
1460:
1421:
1382:
1327:
1288:
1238:
1211:(7): 565–573.
1188:
1169:(6): 397–407.
1163:Chem. Soc. Rev
1149:
1142:
1122:
1060:
1047:
1034:
1013:
992:
975:
958:
945:
925:
908:
891:
874:
853:
832:
797:
784:
763:
742:
721:
683:
654:
653:
651:
648:
647:
646:
641:
636:
631:
626:
621:
616:
609:
604:
599:
594:
589:
582:
579:
526:
523:
514:lattice energy
459:microstructure
418:
415:
379:
376:
327:
324:
320:hydrogen bonds
307:
304:
300:shear strength
263:
260:
239:
236:
219:
216:
192:
189:
173:
170:
140:
137:
102:
99:
87:cinnamic acids
82:
79:
42:academic field
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2024:
2013:
2010:
2008:
2005:
2003:
2000:
1998:
1995:
1993:
1990:
1988:
1985:
1984:
1982:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1954:
1950:
1941:
1937:
1933:
1929:
1925:
1921:
1917:
1913:
1906:
1904:
1900:
1895:
1891:
1887:
1883:
1879:
1875:
1871:
1867:
1863:
1859:
1855:
1848:
1846:
1842:
1837:
1833:
1829:
1825:
1821:
1817:
1813:
1806:
1803:
1798:
1794:
1790:
1786:
1782:
1778:
1774:
1767:
1764:
1759:
1755:
1751:
1747:
1743:
1739:
1735:
1731:
1727:
1720:
1718:
1716:
1712:
1708:
1704:
1700:
1694:
1691:
1675:
1671:
1664:
1658:
1655:
1650:
1646:
1642:
1638:
1634:
1630:
1626:
1619:
1616:
1611:
1607:
1603:
1599:
1595:
1591:
1587:
1583:
1579:
1572:
1569:
1564:
1560:
1556:
1550:
1546:
1545:
1537:
1535:
1533:
1531:
1527:
1522:
1518:
1514:
1510:
1507:: 1720–1729.
1506:
1502:
1498:
1491:
1488:
1483:
1479:
1475:
1471:
1464:
1461:
1456:
1452:
1448:
1444:
1440:
1436:
1432:
1425:
1422:
1417:
1413:
1409:
1405:
1401:
1397:
1393:
1386:
1383:
1378:
1374:
1370:
1366:
1362:
1358:
1354:
1350:
1346:
1342:
1338:
1331:
1328:
1323:
1319:
1315:
1311:
1307:
1303:
1299:
1292:
1289:
1284:
1280:
1276:
1272:
1268:
1264:
1260:
1256:
1252:
1245:
1243:
1239:
1234:
1230:
1226:
1222:
1218:
1214:
1210:
1206:
1202:
1195:
1193:
1189:
1184:
1180:
1176:
1172:
1168:
1164:
1160:
1153:
1150:
1145:
1139:
1135:
1134:
1126:
1123:
1118:
1114:
1110:
1106:
1102:
1098:
1094:
1090:
1086:
1082:
1078:
1071:
1069:
1067:
1065:
1061:
1057:
1051:
1048:
1044:
1041:P. Dastidar,
1038:
1035:
1031:
1027:
1023:
1020:S. L. Price,
1017:
1014:
1010:
1006:
1002:
996:
993:
989:
985:
979:
976:
972:
968:
962:
959:
955:
949:
946:
942:
938:
935:
929:
926:
922:
918:
912:
909:
905:
901:
895:
892:
888:
887:Chem. Commun.
884:
878:
875:
871:
867:
863:
857:
854:
850:
846:
842:
836:
833:
828:
824:
820:
816:
812:
808:
801:
798:
794:
788:
785:
781:
777:
773:
767:
764:
760:
756:
752:
749:R. Pepinsky,
746:
743:
739:
735:
731:
725:
722:
718:
714:
710:
706:
702:
698:
694:
687:
684:
680:
676:
672:
668:
667:
659:
656:
649:
645:
642:
640:
639:Self-assembly
637:
635:
632:
630:
627:
625:
624:Hydrogen bond
622:
620:
617:
615:
614:
610:
608:
605:
603:
600:
598:
595:
593:
590:
588:
585:
584:
580:
578:
576:
572:
568:
563:
559:
555:
551:
547:
543:
539:
535:
531:
524:
522:
519:
518:crystallinity
515:
511:
508:
504:
500:
496:
492:
488:
485:, use induce
484:
480:
476:
472:
468:
464:
460:
456:
452:
448:
444:
440:
436:
432:
428:
424:
416:
414:
412:
408:
404:
400:
396:
392:
388:
384:
377:
375:
373:
369:
361:
356:
352:
348:
346:
341:
340:acetaminophen
337:
333:
325:
323:
321:
317:
313:
305:
303:
301:
297:
293:
289:
285:
276:
268:
261:
259:
252:
249:
244:
237:
235:
231:
228:
224:
217:
215:
207:
203:
199:
197:
190:
188:
186:
182:
179:
171:
169:
167:
163:
158:
150:
145:
138:
136:
134:
130:
126:
124:
123:halogen bonds
120:
116:
107:
100:
98:
96:
92:
88:
80:
75:
74:
69:
64:
60:
58:
54:
50:
45:
43:
40:
37:. It is an
36:
32:
19:
1962:CrystEngComm
1915:
1861:
1857:
1819:
1815:
1805:
1780:
1776:
1766:
1733:
1729:
1709:, 2701-2712.
1706:
1702:
1698:
1693:
1681:. Retrieved
1669:
1657:
1632:
1628:
1618:
1585:
1581:
1571:
1543:
1504:
1500:
1490:
1473:
1463:
1438:
1434:
1424:
1399:
1395:
1385:
1344:
1340:
1330:
1305:
1301:
1291:
1258:
1254:
1208:
1204:
1166:
1162:
1152:
1136:. Elsevier.
1132:
1125:
1084:
1080:
1055:
1050:
1042:
1037:
1029:
1025:
1021:
1016:
1011:, 2427-2430.
1008:
1004:
1000:
995:
987:
983:
978:
973:, 3506–3520.
970:
966:
961:
953:
948:
940:
936:
933:
928:
920:
916:
911:
903:
899:
894:
886:
882:
877:
872:, 2311-2327.
869:
865:
861:
856:
848:
844:
840:
835:
810:
806:
800:
792:
787:
779:
775:
771:
766:
758:
754:
750:
745:
740:, 8342–8356.
737:
733:
729:
724:
700:
696:
686:
670:
666:CrystEngComm
664:
658:
611:
607:CrystEngComm
546:polymorphism
528:
479:Calorimetric
475:crystallites
467:crystallites
463:dislocations
420:
381:
365:
359:
354:
347:is formed.
329:
309:
281:
256:
250:
247:
232:
221:
212:
200:
196:Polymorphism
194:
191:Polymorphism
183:
175:
154:
148:
127:
112:
84:
71:
46:
30:
29:
1683:23 February
943:, 7298–7332
923:, 1383–1386
813:: 173–183.
703:(1): 1–14,
296:brittleness
1981:Categories
1032:, 117–126.
906:, 671–679.
851:, 386-395.
650:References
567:slip plane
542:anisotropy
540:, packing
538:elasticity
345:slip plane
292:elasticity
288:plasticity
251:Chem. Soc.
157:cocrystals
1932:1359-7345
1878:1543-8384
1758:102536532
1750:1528-7483
1649:0032-3861
1602:1359-7345
1563:904405330
1521:0014-7672
1455:1528-7483
1416:1528-7483
1361:1543-8384
1322:1528-7483
1283:216290100
1275:1528-7483
1225:0001-4842
1183:0306-0012
1101:0001-4842
827:0022-328X
451:field ion
391:vacancies
49:hydrogen-
1940:18217656
1894:73502360
1886:30835128
1797:23315913
1674:Archived
1610:22822481
1377:73502360
1369:30835128
1233:12118996
1117:53028955
1109:30351918
969:, 2010,
939:, 2009,
919:, 2009,
902:, 2005,
778:, 1971,
757:, 1955,
581:See also
534:hardness
491:enthalpy
447:electron
1824:Bibcode
1629:Polymer
705:Bibcode
503:melting
495:entropy
469:during
443:optical
439:lattice
372:lattice
119:organic
57:synthon
1938:
1930:
1892:
1884:
1876:
1795:
1756:
1748:
1705:2013,
1647:
1608:
1600:
1561:
1551:
1519:
1453:
1414:
1375:
1367:
1359:
1320:
1281:
1273:
1231:
1223:
1181:
1140:
1115:
1107:
1099:
1028:2009,
1007:2008,
868:1995,
847:2005,
825:
782:, 647.
761:, 971.
736:2007,
544:, and
507:fusion
501:. The
497:, and
453:, and
401:, and
298:, and
248:J. Am.
133:ligand
1890:S2CID
1754:S2CID
1677:(PDF)
1666:(PDF)
1373:S2CID
1279:S2CID
1113:S2CID
149:IUCrJ
1936:PMID
1928:ISSN
1882:PMID
1874:ISSN
1793:PMID
1746:ISSN
1685:2021
1645:ISSN
1606:PMID
1598:ISSN
1559:OCLC
1549:ISBN
1517:ISSN
1451:ISSN
1412:ISSN
1365:PMID
1357:ISSN
1318:ISSN
1271:ISSN
1229:PMID
1221:ISSN
1179:ISSN
1138:ISBN
1105:PMID
1097:ISSN
988:Vol.
823:ISSN
505:and
409:and
407:edge
227:CCDC
51:and
1920:doi
1866:doi
1832:doi
1785:doi
1738:doi
1637:doi
1590:doi
1509:doi
1478:doi
1443:doi
1404:doi
1349:doi
1310:doi
1263:doi
1213:doi
1171:doi
1089:doi
904:437
815:doi
811:847
759:100
713:doi
675:doi
302:).
1983::
1934:.
1926:.
1914:.
1902:^
1888:.
1880:.
1872:.
1862:16
1860:.
1856:.
1844:^
1830:.
1820:20
1818:.
1814:.
1791:.
1781:52
1779:.
1775:.
1752:.
1744:.
1734:18
1732:.
1728:.
1714:^
1707:52
1701:,
1672:.
1668:.
1643:.
1633:43
1631:.
1627:.
1604:.
1596:.
1586:48
1584:.
1580:.
1557:.
1529:^
1515:.
1505:63
1503:.
1499:.
1472:.
1449:.
1439:12
1437:.
1433:.
1410:.
1400:15
1398:.
1394:.
1371:.
1363:.
1355:.
1345:16
1343:.
1339:.
1316:.
1306:13
1304:.
1300:.
1277:.
1269:.
1259:20
1257:.
1253:.
1241:^
1227:.
1219:.
1209:35
1207:.
1203:.
1191:^
1177:.
1167:22
1165:.
1161:.
1111:.
1103:.
1095:.
1085:51
1083:.
1079:.
1063:^
1030:42
1024:,
1009:47
1003:,
986:,
971:22
941:48
921:21
885:,
870:34
864:,
849:38
843:,
821:.
809:.
780:27
774:,
753:,
738:46
732:,
711:,
701:45
699:,
669:,
536:,
493:,
449:,
445:,
413:.
397:,
374:.
360:B.
355:A.
314:,
294:,
290:,
1942:.
1922::
1896:.
1868::
1838:.
1834::
1826::
1799:.
1787::
1760:.
1740::
1687:.
1651:.
1639::
1612:.
1592::
1565:.
1523:.
1511::
1484:.
1480::
1457:.
1445::
1418:.
1406::
1379:.
1351::
1324:.
1312::
1285:.
1265::
1235:.
1215::
1185:.
1173::
1146:.
1119:.
1091::
829:.
817::
715::
707::
677::
671:4
160:(
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
