Hydrogen Atoms. Hydrogen Atoms

Similar documents
4. Constraints and Hydrogen Atoms

5.067 Crystal Structure Refinement Fall 2007

Refinement of Disorder with SHELXL

The SHELX Package. Data Flow

Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK

Supporting Information

Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK

Sigma Bond Metathesis with Pentamethylcyclopentadienyl Ligands in Sterically. Thomas J. Mueller, Joseph W. Ziller, and William J.

The Abstraction of Iodine from Aromatic Iodides by Alkyl Radicals. Steric and Electronic Effects 1

metal-organic compounds

11/18/2013 SHELX. History SHELXS. .ins File for SHELXS TITL. .ins File Organization

Manganese-Calcium Clusters Supported by Calixarenes

Orthorhombic, Pbca a = (3) Å b = (15) Å c = (4) Å V = (9) Å 3. Data collection. Refinement

Scandium and Yttrium Metallocene Borohydride Complexes: Comparisons of (BH 4 ) 1 vs (BPh 4 ) 1 Coordination and Reactivity

Refine & Validate. In the *.res file, be sure to add the following four commands after the UNIT instruction and before any atoms: ACTA CONF WPDB -2

Model and data. An X-ray structure solution requires a model.

APPENDIX E. Crystallographic Data for TBA Eu(DO2A)(DPA) Temperature Dependence

SHELXL Instruction Summary

Edited for epub/pdf by Joseph H. Reibenspies (Please send any corrections to the editor

Understanding the relationship between crystal structure, plasticity and compaction behavior of theophylline, methyl gallate and their 1:1 cocrystal

CALIFORNIA INSTITUTE OF TECHNOLOGY BECKMAN INSTITUTE X-RAY CRYSTALLOGRAPHY LABORATORY

Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder Reaction: Application to the Total Synthesis of (+)-Dihydrocompactin

Halogen bonding of N-bromosuccinimide by grinding

metal-organic compounds

Alphabetical list of SHELXL instructions

CHAPTER 6 CRYSTAL STRUCTURE OF A DEHYDROACETIC ACID SUBSTITUTED SCHIFF BASE DERIVATIVE

Supplementary Information. Single Crystal X-Ray Diffraction

Entropy rules! Disorder Squeeze

= (8) V = (8) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections

Homework 1 (not graded) X-ray Diffractometry CHE Multiple Choice. 1. One of the methods of reducing exposure to radiation is to minimize.

metal-organic compounds

metal-organic compounds

Advanced Crystallography: Refinement of Disordered Structures. November 13, 2012 Disorder Webinar

Supplementary File. Modification of Boc-protected CAN508 via acylation and Suzuki-Miyaura Coupling

Jack D. Dunitz. X-Ray Analysis and the Structure of Organic Molecules VCHP. (2nd Corrected Reprint) $ Verlag Helvetica Chimica Acta, Basel

electronic reprint 2-Hydroxy-3-methoxybenzaldehyde (o-vanillin) revisited David Shin and Peter Müller

Cages on a plane: a structural matrix for molecular 'sheets'

8. Strategies for Macromolecular Refinement

7. SHELXL Instruction Summary

metal-organic compounds

2-Methoxy-1-methyl-4-nitro-1H-imidazole

Decomposition of Ruthenium Olefin Metathesis. Catalysts

Crystal structure analysis of N,2-diphenylacetamide

Supporting Information

Supporting Information. for. Advanced Functional Materials, adfm Wiley-VCH 2007

OFB Chapter 3 Chemical Periodicity and the Formation of Simple Compounds

organic papers 2-Iodo-4-nitro-N-(trifluoroacetyl)aniline: sheets built from iodo nitro and nitro nitro interactions

organic papers Malonamide: an orthorhombic polymorph Comment

,

Anisotropy in macromolecular crystal structures. Andrea Thorn July 19 th, 2012

shelxl: Refinement of Macromolecular Structures from Neutron Data

ACIDS AND BASES. Note: For most of the acid-base reactions, we will be using the Bronsted-Lowry definitions.

b = (9) Å c = (7) Å = (1) V = (16) Å 3 Z =4 Data collection Refinement

(+-)-3-Carboxy-2-(imidazol-3-ium-1-yl)- propanoate

New Journal of Chemistry. Synthesis and mechanism of novel fluorescent coumarindihydropyrimidinone. multicomponent reaction.

Fast, Intuitive Structure Determination IV: Space Group Determination and Structure Solution

Supporting Information

1 Introduction. Abstract

Reaction Landscape of a Pentadentate N5-Ligated Mn II Complex with O 2

Creating a Pharmacophore Query from a Reference Molecule & Scaffold Hopping in CSD-CrossMiner

metal-organic compounds

metal-organic compounds

= (3) V = (4) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = 1.

3-methoxyanilinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate.

metal-organic compounds

Validation of Experimental Crystal Structures

= mm 1 T = 298 K. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 290 parameters 9 restraints

Ethylene Trimerization Catalysts Based on Chromium Complexes with a. Nitrogen-Bridged Diphosphine Ligand Having ortho-methoxyaryl or

International Journal of Innovative Research in Science, Engineering and Technology. (An ISO 3297: 2007 Certified Organization)

Supporting Information

Scattering Lecture. February 24, 2014

Changing and challenging times for service crystallography. Electronic Supplementary Information

Chemistry 14C Spring 2016 Final Exam Part B Solutions Page 1

addenda and errata [N,N 0 -Bis(4-bromobenzylidene)-2,2-dimethylpropane-j Corrigendum Reza Kia, a Hoong-Kun Fun a * and Hadi Kargar b

ELECTRON BOND POTENTIAL

Supramolecular structure of phellopterin isolated from the roots of heracleum thomsoni: A furanocoumarin

X- ray crystallography. CS/CME/Biophys/BMI 279 Nov. 12, 2015 Ron Dror

CHEMISTRY 110 EXAM 2 Oct. 11, 2010 FORM A

11/6/2013. Refinement. Fourier Methods. Fourier Methods. Difference Map. Difference Map Find H s. Difference Map No C 1

organic papers 2,6-Diamino-3,5-dinitro-1,4-pyrazine 1-oxide Comment

Nuclear Physics Fundamental and Application Prof. H. C. Verma Department of Physics Indian Institute of Technology, Kanpur

Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 92 parameters

CHARACTERIZATION OF WEAK INTRA- AND INTERMOLECULAR INTERACTIONS USING EXPERIMENTAL CHARGE DENSITY DISTRIBUTIONS

Impeller-like dodecameric water clusters in metal organic nanotubes

Synthetic, Structural, and Mechanistic Aspects of an Amine Activation Process Mediated at a Zwitterionic Pd(II) Center

Physical Chemistry Analyzing a Crystal Structure and the Diffraction Pattern Virginia B. Pett The College of Wooster

Crystals, X-rays and Proteins

What's new in SHELXL-2013?

Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 245 parameters 2 restraints

The Crystal and Molecular Structures of Hydrazine Adducts with Isomeric Pyrazine Dicarboxylic Acids

= (1) V = (12) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections

Crystal growth and characterization of solvated organic charge-transfer complexes built on TTF and 9-dicyanomethylenefluorene derivatives

Direct Method. Very few protein diffraction data meet the 2nd condition

SUPPORTING INFORMATION

Selective total encapsulation of the sulfate anion by neutral nano-jars

metal-organic compounds

metal-organic compounds

Handout 13 Interpreting your results. What to make of your atomic coordinates, bond distances and angles

Atoms with a complete outer shell do not react with other atoms. The outer shell is called the valence shell. Its electrons are valence electrons.

Structure of Bis(isobutylammonium) Selenite and its Sesquihydrate

Transcription:

ydrogen Atoms It is electron density that we measure by X-ray diffraction. The heavier an atom is and the more electrons it has, the stronger is its effect on the diffraction pattern. This also means that, especially in the presence of heavy atoms, light atoms are somewhat more difficult to localize. The lightest atom of all is hydrogen: it has only one electron, localized away from the nucleus. Therefore, hydrogen atoms are notoriously difficult to detect with X-ray diffraction methods. Relatively high electron density between the atoms and libration effects make X bonds appear too short. < > X-ray ca. 0.96 Å < > neutron ca. 1.09 Å ourtesy of George Sheldrick. Used with permission. George M. Sheldrick ydrogen Atoms Especially for hydrogen atoms bound to carbon it is frequently possible to calculate the hydrogen positions from the coordinates of the atoms the hydrogen atoms are attached to, as the standard bond lengths and angles are well known. ydrogen atoms of water molecules must be detected in the experimental electron density or else they cannot be included into the model. Even more difficult to detect can be hydrogen atoms in heavy metal hydrides. The sometimes relatively strong Fourier truncation ripples close to heavy atom positions can overpower the rather weak electron density maxima representing the hydrogen atoms. Very accurate and especially complete high quality data and proper scaling are required to distinguish those hydrogen atoms from the background noise. 1

ydrogen Atoms In most cases, the positioning of hydrogen atoms bound to carbon in an atomic model during the refinement of an X-ray crystal structure is done entirely without any or only very little direct information from the diffraction experiment. ydrogen atoms on aromatic carbons,, 2 groups, most 3 groups are easy. 3 in acetonitrile, p* or toluene: torsion angle needs to be determined. R R 160 N 120 80 40 0 0 60 120 180 240 300 Figure by MIT W. ydrogen Atoms in SELXL: FIX ydrogen atoms are placed at calculated positions and refined using a riding model. That means rigid group constraints, in other words AFIX. The FIX command generates both the hydrogen atom positions and the appropriate AFIX lines. This is good mainly for hydrogens bound to carbon, but can also be used for some N- and - situations. ydrogens bound to metal atoms cannot be generated that way. 2

ydrogen Atoms in SELXL: FIX Syntax: FIX mn atomnames m describes the geometry and number of hydrogen atoms. n defines how the hydrogen atoms(s) are refined. The SELX manual has a list of all possible n and m numbers. The book has a list of the most important combinations on page 30-31. atomnames is a list of all atoms that are supposed to get hydrogen atoms. ydrogen Atoms in SELXL: Semi-free refinement Acidic hydrogen atoms could be absent and should be seen in the difference Fourier before they should be placed. Good alternative: semi-free refinement: Take coordinates for hydrogen atoms from peaklist (list of Qs in.res file). Place atom directly under the atom it is attached to. hange atom name (Q Æ ) and atom type (1 Æ 2). hange U-value (0.05 Æ -1.2 or -1.5). Use DFIX to restrain X- and possibly - distances. See.lst file for target distances. This is very elegant and less restrictive than the riding model, but requires good high-resolution low-temperature diffraction data. 3

ydrogen Atoms in SELXL: ydrogen Bonds If the command TAB appears in the header of the.ins file, SELXL performs a search over all polar hydrogen atoms present in the structure and examines hydrogen bonding. The bonds listed in the.lst file are those for which the distance between acceptor and hydrogen atom are smaller than the radius of the acceptor atom plus 2.0 Å, and the angle between the donor atom, the hydrogen and the acceptor atom is larger than 110. nce the hydrogen bonds have been identified, the second form of the TAB command can be used to calculated standard uncertainties: TAB donor-atom acceptor-atom SELXL generates hydrogen bonds with standard uncertainties and, in combination with ATA, the appropriate table in the.cif file. EQIV can be used to specify a symmetry equivalent of the acceptor atom. 4

Atom Type Assignment All Electrons are Blue We measure electron density not atomic number. The accuracy of the electron density depends on correctness of the model, which is equivalent to the interpretation of the electron density function and we are facing a nice atch 22. hemical knowledge, that is geometry of molecules (bond lengths and angles, number of bonds, etc.): u(i) is colorless (II) is blue. arbon makes four single bonds, no more. Pt(II) is usually planar, Pt(IV) is usually octahedrally coordinated. Zr(III) is dark green to black, Zr(IV) pale yellow to colorless. etc. A crystal structure must be chemically sensible or it is wrong! Atom Type Assignment All Electrons are Blue We measure electron density not atomic number. The accuracy of the electron density depends on correctness of the model, which is equivalent to the interpretation of the electron density function and we are facing a nice atch 22. rystallographic knowledge or what does the thermal displacement ellipsoid look like? Too small ellipsoid The true element may be heavier than the one currently in you model. Too large ellipsoid The true element may be lighter than the one currently in you model. Example: finding the oxygen atom in TF by refining all five atoms as. 5

Atom Type Assignment All Electrons are Blue A sphere (or ellipsoid) is drawn around the volume corresponding to 50% of the electrons assumed in the model. If the real atom has more electrons this volume will be below average, if the real atoms has more electrons the volume will be larger than average. 8e- A B Figure by MIT W. Atom Type Assignment All Electrons are Blue N Another example... Si N 6