“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
_______________________________________________________________
Supporting Information 1
Block-like crystal specimen of H(2,4-diClPhCO) in the Cryoloop© prior to the
X-ray experiment.

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
_______________________________________________________________
Supporting Information 2
Face indexed crystal specimen of H(2,4-diCl-PhCO); obtained crystal dimensions were used in numerical absorption correction procedure by
SADABS.

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 3
Measurements of the partitioning coefficient.
In potentiometric experiments with Log P where P is partition coefficient between water and n-octanol.
It corresponds to K in the permeability formula. K is a partition coefficient between hydrophilic exterior and lipophilic membrane.
For a given n-octanol/water ratio, the size of the pKa shift increases as Log K increases.
The fundamental equation describing passive drug transport through the membranes is based on Fick’s first law: J = P · Caq.
The permeability coefficient is defined as: P = D · K/h, where K is a partition coefficient of the compound of interest from the aqueous exterior into the membrane. J
– the compound’s flux through a membrane (mass/area/time); P - permeability coefficient through the lipophilic membrane; C
– the compound’s concentration at the aqueous exterior; D
– diffusion coefficient within the membrane; K
– partition coefficient from the aqueous exterior into the membrane; h is a membrane thickness.

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 4
Experimental data for the partitioning measurements.

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 5
Experimental data for the partitioning measurements (continued).

N
C
“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 6
Resonance forms in anionic 2,4-dichlorophenyl-cyanoxime showing charge delocalization throughout the anion.
Cl Cl Cl
N
C N
O
Cl
N
C
Cl
N
O
Cl
N
C N
O
Cl
Cl
N
O
Cl
N
C N
O
Cl
Cl
N
C N
O
Cl
Cl
N
C N
O
Cl

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 7
UV spectra of deprotonated (as KL) and protonated HL cyanoxime: data of three independent and consecutive measurements.
Sample Wavelength (nm) Absorbance Molarity (mol/L)

(cm -1 M -1 )
KL :
1
2
3
229
298
229
298
229
298
1.174
1.581
1.215
1.593
1.137
1.523
9.85 X 10 -4
9.84 X 10 -4
9.80 X 10 -4
1.12 X 10 4
1.61 X 10 4
1.23 X 10 4
1.62 X 10 4
1.16 X 10 4
1.55 X 10 4
HL
1
2
3
:
218
262
261
262
0.939
1.599
0.862
0.176
9.85 X 10 -4
9.84 X 10 -4
9.80 X 10 -4
3.04 X 10
9.50 X 10
8.76 X 10
8.80 X 10
4
3
3
3
______________________________________________________________________

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 8
Observed linear correlations between the energy of n →p* transition in the nitroso- chromophore of anionic cyanoxime in several alcohols ROH.
Blue: pKa of the solvent and energy of transition. Red: specific solvation energy by solvent ROH and energy of transition.

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 9
The 1 H NMR spectrum of the H(2,4-diCl-PhCO) in dmso-d
6
at 293 K.

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 10
The 13 C{ 1 H} NMR spectrum of the H(2,4-diCl-PhCO) in dmso-d
6
at 293 K.

“Synthesis, Properties and Crystal Structure of 2,4-dichlorophenyl-cyanoxime – a powerful carbonyl reductase inhibitor”
By Michael Hilton, Nikolay Gerasimchuk, Svitlana Silchenko and Henry A. Charlier
______________________________________________________________________
Supporting Information 11
The unit cell content: wo orthogonal views of the structure of H(2,4-diCl-PhCO) showing
H bonding ( A ) and

-stacking ( B ) between chains of molecules.
A
B