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CTURE OF ORGANIC COMPOUNDS

Crystal and Molecular Structure of 2[(4Nitrophenyl)carbonyl]cyclohex1ene1yl 4Nitrobenzoate I. N. Polyakovaa, O. A. Egorovab, V. S. Sergienkoa, L. Yu. Tarasovab, and V. V. Davydovb a

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii pr. 31, Moscow, 119991 Russia email: [email protected] b Peoples’ Friendship University of Russia, ul. MiklukhoMaklaya 6, Moscow, 117198 Russia Received July 13, 2010

Abstract—The crystal structure of 2[(4nitrophenyl)carbonyl]cyclohex1ene1yl 4nitrobenzoate is stud ied (T = 173 K, R1 = 0.0354 for 2713 observed reflections). This crystal is orthorhombic, a = 7.8367(8) Å, b = 9.6082(10) Å, c = 23.856(3) Å, V = 1796.3(3) Å3, space group P212121, and Z = 4. The molecule has a folded configuration, which is stabilized by π–π interactions between its two parts. A system of intermolecu lar C–H···O hydrogen bonds (H···O, 2.44–2.67 Å; CHO angles 122°–169°) and intramolecular C–H···O contacts closing fivemembered cycles (H···O, 2.42–2.59 Å; CHO angles 96°–102°) are formed in the struc ture. DOI: 10.1134/S1063774511020143

In attempting to prepare complexes of 2(4 nitrobenzoyl)cyclohexanone with Со2+ and Ni2+ ions, we isolated 2[(4nitrophenyl)carbonyl]cyclohex1 ene1yl 4nitrobenzoate, which is a product of the addition of the (4nitrophenyl)carbonyl fragment of the starting molecule to the whole molecule.

C11A C12 C11

C10

EXPERIMENTAL Crystals isolated in two experiments differed in color (colorless and yellow) and habit but had identi cal unit cell parameters. A wellfaceted colorless crys tal was chosen for data collection. The main crystal data, the parameters of the exper iment, and the characteristics of structure refinement are summarized in Table 1. A set of intensities of the diffraction reflections was obtained on a Bruker SMART APEX2 automated dif fractometer. The structure was solved by the direct method. The nonhydrogen atoms were refined in the anisotropic approximation. The hydrogen atoms were located from a difference Fourier synthesis and refined in the isotropic approximation without constraints. It was found in the refinement that one of the СН2 groups of the hexene ring is disordered over two positions (C11 and С11А) with a prevailing population of the former position [0.926(10)]. This disordering results in the disordering of the H atoms of the neighboring СН2 groups. The positions of the H atoms of the minor component were calculated, and these atoms were refined within the riding model. The С11А atom was refined in the isotropic approximation with the 270

C13 C8 C9

O1 O2

C14 O3

C7

C15

C1 C2

C16

C20 C19

C6

C17

C3 C5 C4

C18

N1

N2 O4 O7

O5

O6 Fig. 1. Molecular structure of 2[(4nitrophenyl)carbo nyl]cyclohex1ene1yl 4nitrobenzoate. Ellipsoids of thermal vibrations of atoms are shown at the 50% probabil ity level.

CRYSTAL AND MOLECULAR STRUCTURE Table 1. Main crystal data, parameters of data collection, and characteristics of refinement of structur