PMID- 29893027
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20191120
IS  - 1521-3773 (Electronic)
IS  - 1433-7851 (Linking)
VI  - 57
IP  - 30
DP  - 2018 Jul 20
TI  - Probing the Crystal Structure Landscape by Doping: 4-Bromo, 4-Chloro, and 
      4-Methylcinnamic Acids.
PG  - 9279-9283
LID - 10.1002/anie.201801649 [doi]
AB  - Accessing the data points in the crystal structure landscape of a molecule is a 
      challenging task, either experimentally or computationally. We have charted the 
      crystal structure landscape of 4-bromocinnamic acid (4BCA) experimentally and 
      computationally: experimental doping is achieved with 4-methylcinnamic acid 
      (4MCA) to obtain new crystal structures; computational doping is performed with 
      4-chlorocinnamic acid (4CCA) as a model system, because of the difficulties 
      associated in parameterizing the Br atom. The landscape of 4CCA is explored 
      experimentally in turn, also by doping it with 4MCA, and is found to bear a close 
      resemblance to the landscape of 4BCA, justifying the ready miscibility of these 
      two halogenated cinnamic acids to form solid solutions without any change in 
      crystal structure. In effect, 4MCA, 4CCA and 4BCA form a commutable group of 
      crystal structures, which may be realized experimentally or computationally, and 
      constitute the landscape. Unlike the results obtained by Kitaigorodskii, all but 
      two of the multiple solid solutions obtained in the methyl-doping experiments 
      take structures that are different from the hitherto observed crystal forms of 
      the parent compounds. Even granted that the latter might be inherently 
      polymorphic, this unusual observation provokes the suggestion that solid solution 
      formation may be used to probe the crystal structure landscape. The influence of 
      pi⋅⋅⋅pi interactions, weak hydrogen bonds and halogen bonds in directing the 
      formation of these new structures is also seen.
CI  - (c) 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
FAU - Chakraborty, Shaunak
AU  - Chakraborty S
AD  - Solid State and Structural Chemistry Unit, Indian Institute of Science, 
      Bangalore, 560 012, India.
FAU - Joseph, Sumy
AU  - Joseph S
AD  - Solid State and Structural Chemistry Unit, Indian Institute of Science, 
      Bangalore, 560 012, India.
FAU - Desiraju, Gautam R
AU  - Desiraju GR
AUID- ORCID: 0000-0002-7708-9176
AD  - Solid State and Structural Chemistry Unit, Indian Institute of Science, 
      Bangalore, 560 012, India.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20180704
PL  - Germany
TA  - Angew Chem Int Ed Engl
JT  - Angewandte Chemie (International ed. in English)
JID - 0370543
OTO - NOTNLM
OT  - crystal engineering
OT  - crystal structure landscapes
OT  - crystal structure prediction
OT  - doping
OT  - solid solutions
EDAT- 2018/06/13 06:00
MHDA- 2018/06/13 06:01
CRDT- 2018/06/13 06:00
PHST- 2018/02/07 00:00 [received]
PHST- 2018/04/09 00:00 [revised]
PHST- 2018/06/13 06:00 [pubmed]
PHST- 2018/06/13 06:01 [medline]
PHST- 2018/06/13 06:00 [entrez]
AID - 10.1002/anie.201801649 [doi]
PST - ppublish
SO  - Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9279-9283. doi: 
      10.1002/anie.201801649. Epub 2018 Jul 4.