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OnlineISSN 1600-5368

Editors: W. Clegg and D. G. Watson

4-[(3-Formyl-4-hydroxyphenyl)diazenyl]-N -(pyrimidin-2yl)benzenesulfonamide
Hoda El-Ghamry, Raafat Issa, Kamal El-Baradie, Keiko Isagai, Shigeyuki
Masaoka and Ken Sakai

Acta Cryst. (2008). E64, o1673–o1674

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ISSN 1600-5368

Volume 61
Part 11
November 2005

Acta Crystallographica Section E

Structure Reports
OnlineEditors: W. Clegg and D. G. Watson

Inorganic compounds

Metal-organic compounds

Organic compounds

Acta Crystallographica Section E: Structure Reports Online is the IUCr’s highly popular open-access structural journal. It provides a simple and easily accessible publication
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Acta Cryst. (2008). E64, o1673–o1674

El-Ghamry et al. · C17 H13 N5 O4 S

organic compounds
Acta Crystallographica Section E

Data collection

Structure Reports
OnlineISSN 1600-5368

Bruker SMART APEXII CCD
diffractometer
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)
Tmin = 0.934, Tmax = 0.977

4-[(3-Formyl-4-hydroxyphenyl)diazenyl]N-(pyrimidin-2-yl)benzenesulfonamide

Reﬁnement

Hoda El-Ghamry,a* Raafat Issa,a Kamal El-Baradie,a Keiko
Isagai,b Shigeyuki Masaokab and Ken Sakaib

17304 measured reﬂections
3560 independent reﬂections
3277 reﬂections with I > 2(I)Rint = 0.017

R[F 2 > 2(F 2)] = 0.034
wR(F 2) = 0.097
S = 1.05
3560 reﬂections

245 parameters
H-atom parameters constrainedmax = 0.42 e Å3
min = 0.37 e Å3a

Department of Chemistry, Faculty of Science, Tanta University, Tanta, Egypt, andDepartment of Chemistry, Faculty of Science, Kyushu University, Hakozaki 6-10-1,
Higashi-ku, Fukuoka 812-8581, Japan
Correspondence e-mail: helghamrymo@yahoo.combReceived 24 July 2008; accepted 30 July 2008
Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 Å;
R factor = 0.035; wR factor = 0.098; data-to-parameter ratio = 14.5.

The title molecule, C17H13N5O4S, has a trans conﬁguration
with respect to the diazenyl (azo) group. The pyrimidine ringand the terminal benzene ring are inclined at angles of
89.38 (4) and 1.6 (6) , respectively, with respect to the central
benzene ring. The conformation of the molecule is in partstabilized by an intramolecular O—H  O hydrogen bond. In
the crystal structure, molecules related through inversion
centers form hydrogen-bonded dimers involving the sulfonamide N—H group and the N atom of the pyrimidine ring.

Related literature
For related literature, see: Gaber et al. (2008 and references
therein); Kakoti et al. (1993); La Roche & Co (1967a,b); Misra
et al. (1998); Mubarak et al. (2007); Nagaraja et al. (2002);
Santra & Lahiri (1997); Vaichulis (1977). For bond-length
data, see: Allen et al. (1987).

Table 1

Hydrogen-bond geometry (Å,  ).
D—H  A

D—H

H  AD  A

D—H  A

O2—H1  O1
N3—H10  N5i

0.84
0.88

1.90
1.98

2.6269 (17)2.8574 (17)

145
179

Symmetry code: (i) x þ 1; y þ 2; z þ 1.

Data collection: APEX2 (Bruker, 2006); cell reﬁnement: SAINT(Bruker, 2004); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to reﬁne
structure: SHELXL97 (Sheldrick, 2008); molecular graphics: KENX
(Sakai, 2004); software used to prepare material for publication:
SHELXL97, TEXSAN (Molecular Structure Corporation, 2001),
KENX and ORTEPII (Johnson, 1976).

This work was supported by a Grant-in-Aid for Specially
Promoted Research (No. 18002016) from the Ministry of
Education, Culture, Sports, Science, and Technology of Japan.
HE acknowledges the Egyptian Channel System for ﬁnancial
support to promote the joint research project between Tanta
and Kyushu Universities.

Supplementary data and ﬁgures for this paper are available from the
IUCr electronic archives (Reference: LH2668).

References

Experimental
Crystal data
C17H13N5O4S
Mr = 383.39
Monoclinic, P21 =c
a = 18.579 (2) Å
b = 5.7731 (7) Å
c = 17.372 (2) Å = 115.99 (1)Acta Cryst. (2008). E64, o1673–o1674

V = 1674.73 Å3
Z=4
Mo K radiation
 = 0.23 mm1
T = 100 (2) K
0.30  0.20  0.10 mm

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Open, A. G. & Taylor,
R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Bruker (2004). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Gaber, M., El-Baradie, K. & El-Sayed, Y. (2008). Spectrochim. Acta (A), 69,
543–541.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National
Laboratory, Tennessee, USA.
Kakoti, M., Choudhury, S., Deb, A. K. & Goswami, S. (1993). Polyhedron, 12,
783–789.
La Roche, H. & Co, A. G. (1967a). Chem. Abstr. 67, 73323r.
La Roche, H. & Co, A. G. (1967b). Swiss Patent, Neth. Apt. 66610, 566 (Cl. CO
7d). 31.
Misra, T. K., Das, D., Sinha, C., Ghosh, P. & Pal, C. K. (1998). Inorg. Chem. 37,
8, 1672–1678.
Molecular Structure Corporation (2001). TEXSAN. MSC, The Woodlands,
Texas, USA.

doi:10.1107/S1600536808024239

electronic reprint

El-Ghamry et al.

o1673

organic compounds
Mubarak, A. T., El-Sonbati, A. Z. & Ahmed, S. M. (2007). J. Coord. Chem. 60,
17, 1877–1890.
Nagaraja, P., Sunith, K., Vasantha, R. & Yathirajan, H. (2002). Eur. J. Pharm.
Biopharm. 53, 187–192.
Sakai, K. (2004). KENX. Kyushu University, Japan.

o1674

El-Ghamry et al.  C17H13N5O4S

Santra, B. K. & Lahiri, G. K. (1997). J. Chem. Soc. Dalton Trans. pp. 1883–
1888.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Vaichulis, A. J. (1977). US Patent 8 273 352 .

electronic reprint

Acta Cryst. (2008). E64, o1673–o1674

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