(E)-N′-[5-Chloro-3-methoxy-2-(4-methylphenylsulfonyloxy)benzyl-idene] isonicotinohydrazide acetic acid solvate: Hydrogen-bonded network of alternating R 4 4(42), R 5 5(33) and R 6 6(40) rin

Article abstract of DOI:10.1107/S010827010705281X

In the title compound, C21H18ClN3O5S·C2H4O2, a combination of O - H...O, N - H...O, C - H...O and C - H...N hydrogen bonds links the components into a complex network containing alternating R 4 ⁴(42), R 5 ⁵(33) and R 6 ⁶(4

Full text of DOI:10.1107/S010827010705281X

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
Within the hydrazine component in (I), both N atoms (N17
and N27) have effectively planar coordination, and the NÐN
bond distance (Table 1) is typical of the value in hydrazines
with both N atoms having a planar coordination (the mean
ISSN 0108-2701
Ê
value is 1.401 A; Allen et al., 1987). In addition, the central
spacer unit between atoms C17 and C21 (Fig. 1) adopts a
nearly planar all-trans conformation, as shown by the key
torsion angles (Table 1).
(E)-N0-[5-Chloro-3-methoxy-2-(4-
methylphenylsulfonyloxy)benzyl-
idene]isonicotinohydrazide acetic acid
solvate: hydrogen-bonded network of
alternating R44(42), R55(33) and R66(40)
rings
In (I) (Fig. 1), the acetic acid molecule is effectively teth-
ered to the hydrazine±carbonyl component by a combination
of two independent hydrogen bonds, one of OÐHÁ Á ÁO and
one of NÐHÁ Á ÁO type (Fig. 2 and Table 2). Acetic acid atom
O41 acts as a hydrogen-bond donor to carbonyl atom O17. At
the same time, hydrazine atom N17 in the molecule at (x, y, z)
acts as a hydrogen-bond donor to acetic acid atom O42 in the
molecule at (2 x, 1 y, 12 + z). In addition, atom C33 in the
molecule at (x, y, z) acts as a hydrogen-bond donor to atom
O25 in the molecule at (x, y, 1 + z), so generating by trans-
lation a C22(8)C(9)R55(33) chain of fused rings (Bernstein et al.,
1995) running parallel to the [001] direction.
Chun-Hua Diao,* Zhi Fan and Xin Chen
College of Sciences, Tianjin University of Science and Technology, Tianjin 300222,
People's Republic of China
Correspondence e-mail: diao_chunhua@163.com
Atom C24 in the molecule at (1 + x, y, z) acts as a hydrogen-
bond donor to pyridyl atom N11 in the molecule at (x, y, z), so
forming a C(13) chain running parallel to the [100] direction.
In addition, atom C33 in the molecule at (x, y, 1 + z) in turn
acts as a hydrogen-bond donor to atom O25 in the molecule at
(x, y, z), so forming a C(9) chain running parallel to the [001]
direction. The combination of the [100] and [001] chains then
generate a sheet parallel to (010) containing R44(42) rings
(Fig. 3). In combination with the C22(8)C(9)R55(33) chain of
rings (Fig. 2), these hydrogen bonds then generate a complex
network containing alternating R44(42), R55(33) and R66(40)
rings (Fig. 4).
Received 24 September 2007
Accepted 24 October 2007
Online 14 November 2007
In the title compound, C21H18ClN3O5SÁC2H4O2, a combina-
tion of OÐHÁ Á ÁO, NÐHÁ Á ÁO, CÐHÁ Á ÁO and CÐHÁ Á ÁN
hydrogen bonds links the components into a complex network
containing alternating R44(42), R55(33) and R66(40) rings.
Comment
There has been a steady growth of interest in the structure and
reactivity of Schiff bases owing to their potential biological
activities, such as antibacterial and antitumor (Kahwa et al.,
1986; Santos et al., 2001). Isonicotinohydrazide forms a variety
of Schiff bases with aldehydes, and the synthesis and crystal
structures of some of them have been reported (Wardell, de
Souza, Ferreira et al., 2005; Wardell, de Souza, Wardell et al.,
2005; Wardell et al., 2006; Low et al., 2006). In order to obtain
more detailed information on the structural conformation of
the molecule, which may be of value in structure±activity
analysis, we report here the synthesis and structure of the title
compound, (I).
Figure 1
The independent components of (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
Acta Cryst. (2007). C63, o717±o719
DOI: 10.1107/S010827010705281X
# 2007 International Union of Crystallography o717

organic compounds
Figure 2
Part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of rings along [001]. For the sake of clarity, H atoms not involved in
the motifs shown have been omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions (2 x, 1 y,
1
1
+ z), (2 x, 1 y,
+ z) and (x, y, 1 + z), respectively.
2
2
Figure 3
Part of the crystal structure of (I), showing the formation of a hydrogen-bonded (010) sheet. For the sake of clarity, H atoms not involved in the motifs
shown have been omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions (1 + x, y, z), (x, y, 1 + z)
and (1 + x, y, 1 + z), respectively.
Experimental
An anhydrous ethanol solution (50 ml) of 4-chloro-2-formyl-6-
methoxyphenyl 4-methylbenzenesulfonate (3.41 g, 10 mmol) was
added to an anhydrous ethanol solution (50 ml) of isonicotino-
hydrazide (1.37 g, 10 mmol) and the mixture was stirred at 350 K for
3 h under N2, giving a white precipitate. The product was isolated,
recrystallized from ethanol and then dried in a vacuum to give pure
compound (I) in 72% yield. Colourless single crystals of (I) suitable
for X-ray analysis were obtained by slow evaporation of a solution in
ethanol and acetic acid (80:20 v/v).
Crystal data
3
Ê
C21H18ClN3O5SÁC2H4O2
V = 2438.5 (8) A
Z = 4
Mr = 519.96
Orthorhombic, Pna21
Figure 4
Mo Kꢀ radiation
1
Ê
Part of the crystal structure of (I), showing the complex network
containing alternating R44(42), R55(33) and R66(40) rings. For the sake of
clarity, H atoms not involved in the motifs shown have been omitted.
a = 14.886 (3) A
ꢁ = 0.29 mm
T = 294 (2) K
Ê
b = 23.190 (4) A
Ê
c = 7.0638 (14) A
0.26 Â 0.20 Â 0.16 mm
ꢀ
o718 Diao et al. C21H18ClN3O5SÁC2H4O2
Acta Cryst. (2007). C63, o717±o719

organic compounds
Data collection
H atoms were included in calculated positions and re®ned using a
riding-model approximation [constrained CÐH and NÐH bond
Bruker SMART APEX CCD area-
detector diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.912, Tmax = 0.955
13425 measured re¯ections
4793 independent re¯ections
2849 re¯ections with I > 2ꢂ(I)
Rint = 0.069
2
lengths and Uiso(H) parameters: 0.93 A and 1.2Ueq(C) for Csp H
Ê
Ê
Ê
atoms, 0.96 A and 1.5Ueq(C) for methyl H atoms, 0.82 A and
Ê
1.5Ueq(O) for the hydroxy H atom, and 0.86 A and 1.2Ueq(N) for the
imine H atom].
Re®nement
Data collection: SMART (Bruker, 1999); cell re®nement: SAINT
(Bruker, 1999); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 1997a); program(s) used to re®ne
structure: SHELXL97 (Sheldrick, 1997a); molecular graphics:
PLATON (Spek, 2003); software used to prepare material for
publication: SHELXTL (Sheldrick, 1997b).
R[F2 > 2ꢂ(F2)] = 0.048
wR(F2) = 0.092
S = 0.97
4793 re¯ections
322 parameters
1 restraint
H-atom parameters constrained
3
Ê
Áꢃmax = 0.20 e A
3
Ê
0.20 e A
Áꢃmin
=
Absolute structure: Flack (1983),
2080 Friedel pairs
Flack parameter: 0.01 (7)
Table 1
Selected geometric parameters (A, ).
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: GD3153). Services for accessing these data are
described at the back of the journal.
ꢁ
Ê
N17ÐN27
1.377 (3)
References
O1ÐS1ÐO2
O1ÐS1ÐO26
O2ÐS1ÐO26
O1ÐS1ÐC31
O2ÐS1ÐC31
O26ÐS1ÐC31
120.13 (15)
102.53 (17)
107.68 (13)
110.46 (16)
109.27 (19)
105.61 (14)
C17ÐN17ÐN27
C26ÐO26ÐS1
C27ÐN27ÐN17
N27ÐC27ÐC21
O17ÐC17ÐN17
118.9 (3)
118.4 (2)
115.9 (3)
120.0 (3)
123.3 (3)
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O1ÐS1ÐO26ÐC26
O2ÐS1ÐO26ÐC26
C31ÐS1ÐO26ÐC26
C17ÐN17ÐN27ÐC27
N17ÐN27ÐC27ÐC21
174.7 (2)
47.0 (2)
69.6 (2)
174.6 (3)
179.3 (3)
C26ÐC21ÐC27ÐN27
C22ÐC21ÐC27ÐN27
N27ÐN17ÐC17ÐO17
N27ÐN17ÐC17ÐC14
164.9 (3)
14.5 (5)
5.1 (6)
173.3 (3)
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001).
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È
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Table 2
Hydrogen-bond geometry (A, ).
È
Gottingen, Germany.
ꢁ
Ê
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AXS Inc., Madison, Wisconsin, USA.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7±13.
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
Wardell, S. M. S. V., de Souza, M. V. N., Ferreira, M. de L., Vasconcelos, T. R.
A., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o617±o620.
Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell,
C. (2005). Acta Cryst. C61, o683±o689.
Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell,
C. (2006). Acta Cryst. E62, o3361±o3363.
O41ÐH41Á Á ÁO17
N17ÐH17Á Á ÁO42i
C33ÐH33Á Á ÁO25ii
C24ÐH24Á Á ÁN11iii
0.82
0.86
0.93
0.93
1.83
2.16
2.50
2.59
2.649 (3)
2.992 (4)
3.378 (6)
3.521 (4)
177
163
157
178
Symmetry codes: (i) x ‡ 2; y ‡ 1; z 12; (ii) x; y; z ‡ 1; (iii) x 1; y; z.
ꢀ
Acta Cryst. (2007). C63, o717±o719
Diao et al. C21H18ClN3O5SÁC2H4O2 o719