EXPERIMENTAL
The NMR spectra were recorded on an Avance III Bruker DRX-500 spectrometer (with the operating frequency of
1 13
500.13 MHz for Н, and 125.76 MHz for С, δ-scale) using the following standard programs for the measurement of two-
1 1
dimensional spectra: COSY Н– Н, НМВС, HSQC, Dept.
The IR spectra were recorded on an IR-Fourier Cary 600 Series spectrometer (Agilent Technologies, USA) using
Gladiatr single reflection ATR accessories with a diamond crystal (PIKE, USA). All the measurements were carried out with
–1
the resolution of 4.0 cm ; the number of scanning was 40.
The reaction course was controlled by TLC. Sorbfil plates in the ethyl acetate–hexane system were used for TLC.
Diethyl ether of 2-[(phenyl-(phenyl-o-carboranyl)-methyl]malonic acid 2. Compound 2 is readily soluble in
DMSO, DMFA, chloroform, ethyl acetate, and hexane and poorly soluble in alcohol and water. The melting point is 109.7-
111.9°C (103-104°C [1]).
1
Н NMR (500 MHz, DMSO, δ, ppm, J, Hz): 0.66 (3Н, t, J = 7.0), 1.23 (3H, t, J = 7.0), 3.56 (2Н, quint), 4.23 (2H,
quint), 3.92 (1Н, d, J = 10), 4.12 (1H, d, J = 10), 6.65-7.80 (10H, m).
13
С NMR (125.76 MHz, DMSO): 13.52 (q, C-15), 14.13 (q, C-12), 47.33 (d, C-9), 59.02 (d, C-2), 61.84 (t, C-14),
62.67 (t, C-11), 85.46 (s, C-16), 85.75 (s, C-1), 128.92 (d, C-5, C-7, C-19, C-21), 129.49 (s, C-17), 129.89 (d, C-4, C-8, C-18,
C-22), 132.17 (d, C-6, C-20), 137.13 (s, C-3), 166.94 (s, C-13), 165.62 (s, C-10).
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IR spectrum (KBr, ν, cm ): 3064 (C–Haryl), 2984 (C–Halkyl), 2605 (B–H), 1756 (C=O ester group, intens.), 1725
(C = O), 1496, 1455, 1370, 1341, 1302, 1278, 1249, 1205, 1183, 1143, 1093, 1025, 1007, 977, 864, 754, 723, 694, 633, 578,
540.
Single crystal X-ray diffraction analysis. The unit cell parameters and reflection intensities of the crystal of
compound 2 were measured at 100 K on a SuperNova, Dual, Cu at zero, Atlas diffractometer (Agilent, USA), equipped with
a CCD detector, with MoK (λ = 0.71073 Å) radiation and ω-scanning. The images were integrated using the CrysAlisPro
α
program [5]; the intensities (scale-up, absorption correction and LP corrections) were processed using the Olex2 program [6].
2
The structure was solved by the direct method using the ShelXS program and refined by the least-squares technique on F
using the ShelXL program [7, 8]. Non-hydrogen atoms were refined in the anisotropic approximation; all hydrogen atoms
were placed in the calculated positions and refined in a riding model with isotropic temperature factors, with 1.2U(eq) for the
corresponding carbon atoms and 1.52U(eq) for the methyl groups.
Crystallographic data of compound 2 at T = 100 K. C22H32B10O4, M = 468.58, orthorhombic, space group Pbca
3 3
(no. 61), a = 13.3238(3) Å, b = 15.9244(4) Å, c = 24.5816(5) Å, V = 5215.6(2) Å , Z = 8, T = 100 K, ρcalc = 1.194 g/cm ,
–1
μ(Мо) = 0.072 mm , F(000) = 1968, 30999 reflections measured, 6555 independent reflections (Rint = 0.0543), which were
used in all calculations. The final divergence factors were R1 0.0521 (for 4919 observed reflections with I > 2σ(I)) and wR2
0.137 (for all data).
The results of the X-ray diffraction analysis of the crystal of compound 2 have been deposited with the Cambridge
Crystallographic Data Centre (CCDC 1531811), and can be easily obtained by request via the website:
Cambridge CB2 1EZ, UK; fax: +44-1223-336033; or deposit@ccdc.cam.ac.uk).
Cytotoxic activity. In order to study the cytotoxic activity of compound 2, we have carried out tests by the known
method using brine shrimps Artemia salina [9]. It is found that in all the tested concentrations (1-10 mg/ml) compound 2
exhibits acute lethal toxicity; the larval mortality is 65-70%.
The authors express their gratitude to Dr. M. V. Zdorovets (Laboratory of Engineering Profile, L. N. Gumilyov
Eurasian National University, Republic of Kazakhstan) for his assistance in measuring IR spectra of the sample, to Hercules
Foundation (project Auge/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”), to Research
Foundation – Flanders (FWO) for the financial support, and to Dr. V. V. Butyaikin for his assistance in the synthesis of the
compound.
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