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Title: Analysis of rapidly synthesized guest-filled porous complexes with synchrotron radiation: Practical guidelines for the crystalline sponge method

Journal Article · · Acta Crystallographica. Section A, Foundations and Advances (Online)
 [1];  [2];  [3];  [1]
  1. Harvard Medical School, Boston, MA (United States)
  2. Harvard Univ., Cambridge, MA (United States)
  3. Argonne National Lab. (ANL), Argonne, IL (United States)

A detailed set of synthetic and crystallographic guidelines for the crystalline sponge method based upon the analysis of expediently synthesized crystal sponges using third-generation synchrotron radiation are reported. The procedure for the synthesis of the zinc-based metal–organic framework used in initial crystal sponge reports has been modified to yield competent crystals in 3 days instead of 2 weeks. These crystal sponges were tested on some small molecules, with two being unexpectedly difficult cases for analysis with in-house diffractometers in regard to data quality and proper space-group determination. These issues were easily resolved by the use of synchrotron radiation using data-collection times of less than an hour. One of these guests induced a single-crystal-to-single-crystal transformation to create a larger unit cell with over 500 non-H atoms in the asymmetric unit. This led to a non-trivial refinement scenario that afforded the best Flack x absolute stereochemical determination parameter to date for these systems. The structures did not require the use of PLATON/SQUEEZE or other solvent-masking programs, and are the highest-quality crystalline sponge systems reported to date where the results are strongly supported by the data. A set of guidelines for the entire crystallographic process were developed through these studies. In particular, the refinement guidelines include strategies to refine the host framework, locate guests and determine occupancies, discussion of the proper use of geometric and anisotropic displacement parameter restraints and constraints, and whether to perform solvent squeezing/masking. The single-crystal-to-single-crystal transformation process for the crystal sponges is also discussed. The presented general guidelines will be invaluable for researchers interested in using the crystalline sponge method at in-house diffraction or synchrotron facilities, will facilitate the collection and analysis of reliable high-quality data, and will allow construction of chemically and physically sensible models for guest structural determination.

Research Organization:
Argonne National Laboratory (ANL), Argonne, IL (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
Grant/Contract Number:
AC02-06CH11357
OSTI ID:
1168849
Journal Information:
Acta Crystallographica. Section A, Foundations and Advances (Online), Vol. 71, Issue 1; ISSN 2053-2733
Publisher:
International Union of CrystallographyCopyright Statement
Country of Publication:
United States
Language:
ENGLISH
Citation Metrics:
Cited by: 73 works
Citation information provided by
Web of Science

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In Situ Observation of Thiol Michael Addition to a Reversible Covalent Drug in a Crystalline Sponge journal March 2016
Structural Elucidation of Trace Amounts of Volatile Compounds Using the Crystalline Sponge Method journal May 2017
Undeniable Confirmation of the syn -Addition Mechanism for Metal-Free Diboration by Using the Crystalline Sponge Method journal February 2016
X-ray Structure Analysis of N-Containing Nucleophilic Compounds by the Crystalline Sponge Method journal October 2017
The Crystalline Sponge Method in Water journal October 2019
Natural Products as a Foundation for Drug Discovery journal August 2019
Cycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method journal January 2017
The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds journal January 2017
Determination of the absolute configuration of compounds bearing chiral quaternary carbon centers using the crystalline sponge method journal January 2017
A high throughput screening method for the nano-crystallization of salts of organic cations journal January 2018
DSR : enhanced modelling and refinement of disordered structures with SHELXL journal April 2015
From the source: student-centred guest lecturing in a chemical crystallography class journal April 2018
The crystalline sponge method updated journal February 2016
Crystalline Sponges as a Sensitive and Fast Method for Metabolite Identification: Application to Gemfibrozil and its Phase I and II Metabolites journal May 2020
Coordinative alignment of molecules in chiral metal-organic frameworks journal August 2016
Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination journal September 2019
Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone journal January 2017
In Situ Observation of Thiol Michael Addition to a Reversible Covalent Drug in a Crystalline Sponge journal March 2016
Where is the Oxygen? Structural Analysis of α-Humulene Oxidation Products by the Crystalline Sponge Method journal June 2015
The Crystalline Sponge Method in Water posted_content July 2019
A high throughput screening method for the nano-crystallization of salts of organic cations text January 2018
Natural Products as a Foundation for Drug Discovery journal September 2009
The Crystalline Sponge Method in Water posted_content February 2019