C System
Resume:
Journal of Structural Chemistry, Vol. **, No. *, pp. 509-517, 2004
Original Russian Text Copyright 2004 by K. M. Beketov, J. T. Welch, P. Toskano, L. A. Kayukova, A. L. Akhelova, and K. D. Praliev
CRYSTAL AND MOLECULAR STRUCTURE OF
-PIPERIDINOPROPIOAMIDOXIME MONOCHLOROACETATE
AND HYDROCHLORIDES OF ITS -BENZOYLATION PRODUCTS
K. M. Beketov,1 J. T. Welch,2 P. Toskano,2 UDC 548.737
L. A. Kayukova,1 A. L. Akhelova,1 and K. D. Praliev1
-para-toluyl- -
The structures of -piperidinopropioamidoxime monochloroacetate and -benzoyl- and
piperidinopropioamidoxime hydrochlorides have been determined. The geometry of these compounds is
analyzed. The N O bond is in the syn-planar position in -piperidinopropioamidoxime monochloroacetate,
but adopts an anti-orientation relative to the (2) (3) bond of the propioamidoxime fragment in the other
two compounds. In -piperidinopropioamidoxime monochloroacetate crystals, the cation-anion pairs are
joined by intermolecular hydrogen bonds into chains; the latter are linked by van der Waals contacts. The
-para-toluyl- -piperidinopropioamidoxime hydrochlorides are
crystals of the -benzoyl- and
characterized by the same system of hydrogen bonds; the cations and anions are linked by hydrogen bonds
into layers, and the latter make van der Waals contacts in the structure.
-para-toluyl- -piperidinopropioamidoximes,
Keywords: -piperidinopropioamidoxime, -benzoyl- and
crystal structure, hydrogen bonds.
INTRODUCTION
Aminoacids and their derivatives are of major importance in all metabolic processes [1]. Primary -
aminopropioamidoximes can be considered as an analogs of -aminoacids. The presence of the primary amidoxime group
having three reactive centers (oxime nitrogen and oxygen atoms and amino nitrogen atom) in -aminopropioamidoximes
makes these compounds highly promising as ambident synthons for the preparation of biologically active compounds. Thus
several -aminopropioamidoximes show local anesthetic, antiarrhythmic [2, 3], and antituberculous activities [4, 5]. We have
-para-toluyl- -piperidinopropio-
synthesized -piperidinopropioamidoxime monochloroacetate (1) and -benzoyl- (2) and
amidoxime (3). The present contribution reports the crystal structure of these compounds.
EXPERIMENTAL
Interaction of -piperidinopropioamidoxime with monochloroacetic acid (1). A solution of monochloroacetic
acid (0.16 g, 0.0017 mol) in ethylacetate (5 ml) was added to the solution of -piperidinopropioamidoxime (0.30 g,
0.0017 mol) in ethylacetate (20 ml). The reaction mixture was stirred for one day, and piperidinopropioamidoxime
monochloroacetate (1) was separated by filtration; the product was recrystallized from isopropanol to yield crystalline powder
1
A. B. Bekturov Institute of Chemical Sciences, Republic of Kazakhstan; *.*******@******.**. 2Albany University,
New York, USA. Translated from Zhurnal Strukturnoi Khimii, Vol. 45, No. 3, pp. 535-543, May-June 2004. Original article
submitted May 13, 2003.
0022-4766/04/450*-****-**** Springer Science+Business Media, Inc. 509
TABLE 1. Crystal Data and Details of Experiment for 1, 2, and 3
Parameter 1 2 3
Formula C10H20ClN3O3 C15H22ClN3O2 C16H24ClN3O2
Molecular weight 265.74 311.8 325.8
Crystal size, mm 0.20 0.25 0.50 0.20 0.35 0.60 0.25 0.35 0.70
Space group, Z P21/c, 4 P21/c, 4 P21/c, 4
a, 12.444(2) 13.656(14) 14.192(6)
b, 8.308(2) 14.127(10) 13.982(4)
c, 12.504(3) 8.990(8) 9.031(3)
99.48(3) 107.92(7) 104.20(3), deg
V, 3 1275.1(5) 1650(2) 1737(1)
3
1.384 1.255 1.246
calc, g/cm
1
3.02 2.39 2.30, cm
No. of reflections 930*-****-****
Independent reflections 323*-****-****
No. of reflections with F 4 (F )
0.0401, 0.1050 0.0450, 0.0581 0.0398, 0.0505
R1, wR2 for F 4 (F )
GOOF 1.102 1.74 1.52
with a yield of 0.42 g (94%), mp 128 .
-para-toluyl- -piperidinopropioamidoxime (3). A solution of benzoyl choride
Syntheses of -benzoyl- (2) and
(0.23 ml, 0.002 mol) in dry benzene (5 ml) was added dropwise with stirring to the solution of -piperidinopropioamidoxime
(0.34 g, 0.002 mol) in dry benzene (20 ml) at room temperature. The reaction mixture was stirred for 20 h at room temperature.
The reaction product was filtered off and recrystallized from isopropanol; yield 0.61 g (98%) of -benzoyl- -piperidino-
. The reaction of para-toluyl chloride with
propioamidoxime (2), mp 119 C - 122 -piperidinopropioamidoxime was
-para-toluyl- -piperidinopropioamido-
performed in a similar way. After recrystallization from isopropanol, the yield of
xime hydrochloride (3) is 94%; mp 152 .
X-ray diffraction study. The intensity data were collected on a KUMA/OXFORD KM4 diffractometer for
compound 1 and on a SIEMENS (BRUKER) R3m diffractometer for compounds 2 and 3 at room temperature ( /2 and /2
scan modes, graphite-monochromated MoK radiation, = 0.71073 ). The unit cell parameters and details of experiment are
given in Table 1. The structures were solved by direct methods and refined anisotropically (isotropically for hydrogen atoms)
using the least-squares technique implemented in the SHELX-97 package [6] for 1 and Siemens SHELXTL PLUS package
[7] for 2 and 3. For 1, all hydrogen atoms were localized by difference syntheses; for 2 and 3, the hydrogen atoms (except
those at the nitrogen atoms) were set into idealized positions.
RESULTS AND DISCUSSION
The positional and thermal parameters of atoms are given in Table 2; the bond lengths and angles are presented in
Table 3. The molecular and crystal structures of compounds 1, 2, and 3 are shown in Figs. 1 and 2.
The geometrical characteristics (bond lengths and bond and torsion angles) of the -piperidinopropioamidoxime
fragment (which is common to the three compounds) are almost the same, the only exception being the orientation of the
amidoxime group. In 2 and 3, this group is significantly rotated around the (2) (1) bond due to presence of the -benzoyl
and -para-toluyl substituents. As a result, the N(1) atom adopts a syn-orientation relative to the (3) atom in the
propioamidoxime fragment in 1 and an anti-orientation in 2 and 3; the N(1) C(1) C(2) C(3) torsion angles are 9.4, 119.8,
and 114.5 in crystals 1, 2, and 3, respectively. The average C O, C=O, C N, C=N, and N O bond lengths, as well as the
510
TABLE 2. Positional ( 104) and Thermal Parameters ( eq for non-hydrogen atoms and for hydrogen
iso
atoms 2 103) for 1, 2, and 3
x y z y z B
Atom Atom
1
1(1 ) 10675(1) 847(1) 3548(1) 48(1) H(2N) 5582(15) 7158(23) 2333(15) 42(5)
N(1) 4800(1) 4481(1) 1703(1) 32(1) H(3N) 6640(15) 7033(22) 1960(14) 40(4)
N(2) 5965(1) 6713(2) 1938(1) 38(1) (41) 7271(15) 2542(23) 1008(16) 46(5)
N(3) 7016(1) 1607(1) 393(1) 24(1) (42) 8032(14) 3345(22) 16(14) 41(4)
O(2) 4149(1) 5552(1) 2229(1) 40(1) (51) 9070(16) 1642(24) 940(16) 52(5)
(1) 5706(1) 5179(2) 1622(1) 27(1) (52) 9108(17) 1022(23) 238(16) 49(5)
(2) 6538(1) 4274(2) 1109(1) 34(1) (61) 8827(17) 1212(25) 883(15) 52(5)
(3) 6109(1) 2708(2) 582(1) 28(1) (62) 7838(16) 362(23) 1594(16) 47(5)
(4) 7729(1) 2304(2) 346(1) 34(1) (71) 7853(15) 1440(24) 558(16) 46(5)
(5) 8652(1) 1150(2) 458(1) 41(1) (72) 7114(17) 2186(26) 483(17) 58(6)
(6) 8221(1) 483(2) 875(1) 44(1) (81) 6106(14) 351(21) 477(14) 38(4)
(7) 7450(1) 1168(2) 165(1) 40(1) (82) 6118(15) 245(22) 691(15) 40(4)
(8) 6555(1) 11(2) 29(1) 32(1) (31) 5717(14) 2160(21) 1019(14) 37(4)
(1 ) 8535(1) 2(2) 2721(1) 29(1) (32) 5653(15) 2909(23) 95(15) 43(5)
(2 ) 9602(1) 597(2) 3373(1) 35(1) (21) 6790(18) 4941(28) 574(18) 65(6)
O(1 ) 8499(1) 1313(1) 2237(1) 41(1) (22) 7152(16) 4087(20) 1625(15) 40(5)
O(2 ) 7758(1) 947(1) 2731(1) 48(1) (20) 3608(19) 5019(29) 2249(18) 65(6)
H(1N) 7437(14) 1417(21) 1038(14) 37(4) (22 ) 9492(17) 876(24) 4077(18) 56(6)
(21 ) 9867(18) 1479(27) 3053(17) 61(6)
2
1(1) 46(1) 889(1) 2008(1) 63(1) (7) 1549(3) 4256(4) 1129(6) 77(2)
O(1) 3844(3) 1189(2) 847(5) 85(2) (8) 650(3) 3712(3) 1346(5) 60(2)
O(2) 3554(2) 2351(2) 2578(3) 57(1) (9) 4032(3) 1572(3) 1921(6) 50(2)
N(1) 2816(3) 2713(2) 1848(4) 52(1) (10) 4820(3) 1263(3) 2589(5) 47(2)
N(2) 2065(3) 3275(3) 4385(5) 56(2) (11) 5137(3) 1807(4) 3602(6) 71(2)
N(3) 605(2) 3811(2) 2940(4) 42(1) (12) 5887(4) 1488(4) 4198(7) 98(3)
C(1) 2126(3) 3172(3) 2905(6) 44(2) (13) 6308(4) 604(5) 3813(8) 98(3)
(2) 1322(3) 3642(3) 2338(5) 46(2) (14) 5996(4) 52(4) 2810(7) 83(3)
(3) 263(3) 3262(3) 3212(5) 46(2) (15) 5256(3) 371(3) 2190(5) 64(2)
(4) 1601(3) 3525(3) 4115(6) 62(2) H(1N) 453(27) 4416(27) 3090(40) 44(12)
(5) 2495(3) 4056(4) 3885(6) 76(2) H(2N) 2565(33) 2965(29) 4814(46) 64(13)
(6) 2558(4) 3949(4) 2271(6) 82(2) H(3N) 1565(43) 3546(35) 5103(58) 85(19)
3
1(1) 9914(1) 9124(1) 1846(1) 53(1) (7) 11425(3) 10701(3) 5024(4) 60(2)
O(1) 6380(2) 13917(2) 520(3) 81(1) (8) 10549(2) 11252(3) 4132(3) 49(1)
O(2) 6549(2) 12570(2) 692(3) 59(1) (9) 6152(3) 13422(3) 579(4) 49(1)
N(1) 7259(2) 12279(2) 684(3) 55(1) (10) 5387(2) 13640(3) 1978(4) 44(1)
N(2) 7940(3) 11578(3) 1172(4) 58(1) (11) 5076(3) 12983(3) 3130(4) 60(2)
N(3) 10500(2) 11241(2) 2464(3) 34(1) (12) 4366(3) 13225(3) 4425(4) 67(2)
C(1) 7899(2) 11774(2) 261(4) 41(1) (13) 3965(3) 14125(3) 4591(4) 59(2)
(2) 8677(2) 11362(3) 1541(4) 46(1) (14) 4275(3) 14776(3) 3440(5) 62(2)
(3) 9655(2) 11793(2) 1538(3) 40(1) (15) 4974(3) 14535(3) 2149(4) 57(2)
(4) 11415(2) 11613(3) 2149(4) 50(1) (16) 3194(3) 14363(4) 5988(5) 98(2)
(5) 12302(3) 11086(3) 3043(4) 59(2) H(1N) 10390(23) 10594(25) 2074(36) 52(10)
(6) 12356(3) 11096(3) 4745(4) 62(2) H(2N) 7562(28) 11841(28) 1984(44) 68(13)
H(3N) 8414(28) 11264(27) 1415(38) 60(12)
511
TABLE 3. Bond Lengths d and Angles (deg) for 1, 2, and 3
d
d d
Bond Bond Bond
1 2 3 4 5 6
1
1(1 ) (2 ) 1.781(2) N(3) C(3) 1.501(2) (5) (6) 1.520(2)
N(1) C(1) 1.287(2) N(3) C(8) 1.505(2) (6) (7) 1.520(2)
N(1) O(2) 1.4340(14) N(3) H(1N) 0.90(2) (7) (8) 1.514(2)
N(2) C(1) 1.357(2) O(2) H(20) 0.81(2) (1 ) O(1 ) 1.243(2)
N(2) H(2N) 0.83(2) (1) (2) 1.506(2) (1 ) O(2 ) 1.249(2)
N(2) H(3N) 0.88(2) (2) (3) 1.515(2) (1 ) (2 ) 1.523(2)
N(3) C(4) 1.499(2) (4) (5) 1.520(2)
Angle Angle Angle
C(1) N(1) O(2) 108.97(10) C(8) N(3) H(1N) 107.0(11) (6) (5) (4) 111.43(13)
C(1) N(2) H(2N) 117.4(13) N(1) O(2) H(2O) 102(2) (5) (6) (7) 110.80(13)
C(1) N(2) H(3N) 118.3(12) N(1) C(1) N(2) 124.72(12) (8) (7) 111.72(13)
H(2N) N(2) H(3N) 119(2) N(1) C(1) C(2) 118.77(11) N(3) C(8) C(7) 111.40(11)
C(4) N(3) C(3) 113.44(10) N(2) C(1) C(2) 116.47(11) O(1 ) (1 ) O(2 ) 126.34(13)
C(4) N(3) C(8) 110.75(10) C(1) C(2) C(3) 113.34(11) O(1 ) (1 ) (2 ) 120.29(12)
C(3) N(3) C(8) 109.82(9) N(3) C(3) C(2) 111.81(10) O(2 ) (1 ) (2 ) 113.36(12)
C(4) N(3) H(1N) 107.7(11) N(3) C(4) C(5) 110.25(11) (1 ) (2 ) 1(1 ) 114.54(10)
C(3) N(3) H(1N) 107.9(11)
2
d d d
Bond Bond Bond
O(1) (9) 1.202(7) (7) (8) 1.511(7) N(3) C(8) 1.460(6)
O(2) (9) 1.322(5) (10) (11) 1.361(7) (1) (2) 1.500(7)
N(2) C(1) 1.316(7) (11) (12) 1.370(9) (4) (5) 1.500(7)
N(2) H(3N) 0.871 (45) (13) (14) 1.355(10) (6) (7) 1.507(6)
N(3) C(4) 1.498(5) O(2) N(1) 1.454(5) (9) (10) 1.452(7)
N(3) H(1N) 0.899 (39) N(1) C(1) 1.288(5) (10) (15) 1.392(6)
C(2) C(3) 1.516(5) N(2) H(2N) 0.984(48) (12) (13) 1.374(9)
(5) (6) 1.487(8) N(3) C(3) 1.499(6) (14) (15) 1.373(8)
Angle Angle Angle
N(1) O(2) C(9) 114.0(4) O(1) C(9) C(10) 124.4(4) N(2) C(1) C(2) 118.0(4)
C(1) N(2) H(2N) 120.8(23) (9) (10) (11) 122.4(4) N(3) C(3) C(2) 114.1(3)
H(2N) N(2) H(3N) 112.6(47) (11) (10) (15) 119.1(5) (4) (5) (6) 112.2(4)
C(3) N(3) C(8) 112.6(3) (11) (12) (13) 120.4(6) (6) (7) (8) 112.0(4)
C(3) N(3) H(1N) 103.7(26) (13) (14) (15) 120.2(5) O(1) (9) O(2) 122.4(5)
C(8) N(3) H(1N) 108.7(24) O(2) N(1) C(1) 107.2(4) O(2) (9) (10) 113.1(4)
N(1) C(1) C(2) 114.8(4) C(1) N(2) H(3N) 126.2(42) (9) (10) (15) 118.6(4)
C(1) C(2) C(3) 110.4(3) C(3) N(3) C(4) 109.7(3) (10) (11) (12) 120.4(5)
N(3) C(4) C(5) 111.6(4) C(4) N(3) C(8) 111.3(4) (12) (13) (14) 119.8(6)
C(5) C(6) C(7) 108.7(4) C(4) N(3) H(1N) 110.6(19) (10) (15) (14) 120.1(5)
N(3) C(8) C(7) 111.0(3) N(1) C(1) N(2) 127.3(5)
512
TABLE 3 (Continued)
1 2 3 4 5 6
3
d d d
Bond Bond Bond
1.504(4)
O(1) (9) 1.189(5) (10) (11) 1.376(5) (1) (2)
1.510(5)
O(2) (9) 1.332(5) (11) (12) 1.385(5) (4) (5)
1.509(6)
N(2) C(1) 1.338(5) (13) (14) 1.370(6) (6) (7)
1.481(4)
N(2) H(3N) 0.875(42) (14) (15) 1.374(5) (9) (10)
1.375(5)
N(3) C(4) 1.489(5) O(2) N(1) 1.453(3) (10) (15)
1.374(7)
N(3) H(1N) 0.970 (35) N(1) C(1) 1.280(5) (12) (13)
1.491(5)
C(2) C(3) 1.515(5) N(2) H(2N) 0.876(36) (13) (16)
(5) (6) 1.520(5) N(3) C(3) 1.497(4)
(7) (8) 1.515(5) N(3) C(8) 1.491(4)
Angle Angle Angle
117.9(3)
N(1) O(2) C(9) 113.8(2) C(9) C(10) C(11) 122.6(3) N(2) C(1) C(2)
113.7(3)
C(1) N(2) H(2N) 124.2(28) C(11) C(10) C(15) 118.2(3) N(3) C(3) C(2)
111.4(3)
H(2N) N(2) H(3N) 110.5(35) C(11) C(12) C(13) 120.8(4) (4) (5) (6)
111.3(3)
C(3) N(3) C(8) 113.0(3) C(12) C(13) C(16) 119.7(4) (6) (7) (8)
123.5(3)
C(3) N(3) H(1N) 104.1(17) C(13) C(14) C(15) 120.8(4) O(1) (9) O(2)
110.7(3)
C(8) N(3) H(1N) 109.9(20) O(2) N(1) C(1) 107.1(3) O(2) (9) (10)
119.1(3)
N(1) C(1) C(2) 115.0(3) C(1) N(2) H(3N) 124.3(21) (9) (10) (15)
120.5(4)
C(1) C(2) C(3) 110.3(3) C(3) N(3) C(4) 109.2(3) (10) (11) (12)
118.5(3)
N(3) C(4) C(5) 112.3(3) C(4) N(3) C(8) 111.2(2) (12) (13) (14)
121.8(4)
C(5) C(6) C(7) 109.7(3) C(4) N(3) H(1N) 109.0(21) (14) (13) (16)
121.2(4)
N(3) C(8) C(7) 111.1(3) N(1) C(1) N(2) 127.1(3) (10) (15) (14)
O(1) C(9) C(10) 125.8(4)
geometry of these bonds, are in good agreement with each other and have standard values [8]. The piperidine cycle has a
slightly distorted chair conformation. The (6) and N(3) atoms deviate from the mean square plane of the other four atoms of
the ring by 0.65 and 0.67 for 1, 0.67 and 0.63 for 2, and 0.67 and 0.64 for 3. The substituents at the N(3) atom occupy
the equatorial positions.
The N(2) H(2N) O(2) intramolecular hydrogen bond observed in the amidoxime group is characteristic for all
three compounds (Table 4). As a result, a five-membered C(1) N(1) O(2) H(2N) N(2) pseudocycle is formed, which
makes a dihedral angle with the benzoyl group (141.8 and 138.3 in 2 and 3, respectively).
In the title compounds, 1:1 saltlike complexes are formed. The cations and anions are linked by the N(3)
H(1N) O(1 ) intermolecular hydrogen bond in 1 and by the N(3) H(1N) Cl bond in 2 and 3 (Fig. 1). The parameters of
the hydrogen bonds are given in Table 4.
A system of donor-acceptor intermolecular interactions is present in the crystal structure of 1. The (2 ) atom of
the monochloroacetate ion acts as a double proton acceptor. It interacts with the N(2) and (2) atoms of the cation of base 1
through N(2) H(3N) O(2A) and O(2) H(2O) O(2A) hydrogen bonds. The cations of base 1 are also involved in
intermolecular interactions by means of N(2) H(2N) N(1) and C(3) H(31) O(2) hydrogen bonds (Table 4). This system
of intermolecular interactions results in the formation of infinite chains of cation-anion pairs running along the b axis in the
structure of 1 (Fig. 2a). The chains are involved in van der Waals interactions.
513
Fig. 1. Molecular structure of 1 (a), 2 (b), and 3 (c).
Compound 3 differs from 2 only in the presence of the methyl group in the para-position of the benzoyl function.
This does not affect the nature of intermolecular interactions, and these compounds have the same system of hydrogen bonds
(Table 4). In the crystal structures of 2 and 3, the Cl ion is involved in interactions in which it behaves as an acceptor in
addition to cation-anion interactions. It interacts with the N(2) and (3) atoms by means of N(2) H(3N) Cl(1), C(3)
H(3A) Cl(1), and C(3) H(3B) Cl(1) hydrogen bonds. The cations of the base form N(2) H(2N) N(1) and N(2)
H(2N) O(1) hydrogen bonds with each other (Table 4). This system of interactions gives rise to layers of cation-anion pairs
parallel to the b plane in 2 and 3 (Fig. 2b). The interactions between the layers are van der Waals interactions.
514
515
Fig. 2. Crystal structure of 1 (a), 2 (b), and 3 (c).
TABLE 4. Parameters of Hydrogen Bonds (, deg)
Bond D H D A Angle Symmetry codes
1 2 3 4 5 6
1
x, y, z
N(2) H(2N) O(2) 0.83(2) 2.21(2) 2.538(2) 103(1)
x, y, z
N(3) H(1N) O(1A) 0.90(2) 1.83(2) 2.716(2) 168(2)
x, 1 + y, z
N(2) H(3N) O(2A) 0.88(2) 2.29(2) 3.002(2) 138(1)
1 x, 0.5 + y, 0.5 z
O(2) (20) O(2 ) 0.81(2) 1.88(2) 2.687(2) 172(1)
1 x, 0.5 + y, 0.5 z
N(2) H(2N) N(1) 0.83(2) 2.36(2) 3.101(2) 149(2)
1 x, 0.5 + y, 0.5 z
(3) (31) O(2) 0.91(2) 2.55(2) 3.331(2) 144(1)
2
x, y, z
N(2) H(2N) O(2) 0.98(4) 2.22(4) 2.539(4) 97(4)
x, y, z
N(3) H(1N) C1(1) 0.90(4) 2.18(4) 3.072(5) 169(4)
x, 1 y, 1 z
N(2) H(3N) C1(1) 0.87(5) 2.47(4) 3.329(6) 170(5)
516
TABLE 4 (Continued)
1 2 3 4 5 6
x, 0.5 + y, 0.5 z
C(3) H(3A) C1(1) 0.96 2.63 3.587(5) 175
x, 1 y, 1 z
C(3) H(3B) C1(1) 0.96 2.62 3.518(4) 155
x, 0.5 y, 0.5 + z
N(2) H(2N) O(1) 0.98(5) 2.52(5) 3.189(6) 125(5)
x, 0.5 y, 0.5 + z
N(2) H(2N) N(1) 0.98(5) 2.18(5) 3.050(6) 146(5)
3
x, y, z
N(2) H(2N) O(2) 0.88(3) 2.30(4) 2.535(4) 95(4)
x, y, z
N(3) H(1N) C1(1) 0.97(3) 2.16(4) 3.088(4) 160(4)
2 x, 2 y, z
N(2) H(3N) C1(1) 0.87(4) 2.55(5) 3.394(4) 161(4)
2 x, 0.5 + y, 0.5 z
C(3) H(3A) C1(1) 0.96 2.61 3.562(3) 170
2 x, 2 y, z
C(3) H(3B) C1(1) 0.96 2.66 3.504(3) 147
x, 2.5 y, z
N(2) H(2N) O(1) 0.88(4) 2.68(4) 3.326(4) 131(4)
x, 2.5 y, z
N(2) H(2N) N(1) 0.88(4) 2.38(5) 3.194(4) 146(4)
CONCLUSIONS
Thus we have determined the molecular and crystal structure of -piperidinopropioamidoximes (saltlike complex
-para-toluyl- -piperidinopropioamidoxime (compounds 2
with monochloroacetic acid, compound 1) and -benzoyl- and
and 3), which show promise as physiologically active compounds. The conformation of the -piperidinopropioamidoxime
group does not change except that the N O group has a syn-orientation with respect to the C(3) atom in 1 but anti-orientation
in 2 and 3 because of the presence of bulky substituents. In crystals 1, the cation-anion pairs are linked by hydrogen bonds,
forming chains packed in the structure by means of van der Waals contacts. In crystals 2 and 3, identical systems of hydrogen
bonds link the cations and anions into layers. The layers form van der Waals contacts with each other.
This study was supported by CRDF grant No. KB2-2314-AL-02 for FSU countries.
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Original Russian Text Copyright © 2004 by K. M. Beketov, J. T. Welch, P. Toskano, L. A. Ka
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