electronic reprint
Acta Crystallographica Section E

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Editors: W.T. A. Harrison, J. Simpson and
M. WeilN -(1,10-Phenanthrolin-5-yl)-4-(2-pyridyl)benzamide
monohydrate
Masayuki Kobayashi, Shigeyuki Masaoka and Ken Sakai

Acta Cryst. (2008). E64, o1979

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Acta Cryst. (2008). E64, o1979

Kobayashi et al. · C24 H16 N4 O·H2 O

organic compounds= 73.638 (3)= 82.883 (4)= 64.695 (3)V = 924.7 (5) Å3
Z=2

Acta Crystallographica Section E

Structure Reports
OnlineISSN 1600-5368

N-(1,10-Phenanthrolin-5-yl)-4(2-pyridyl)benzamide monohydrate
Masayuki Kobayashi, Shigeyuki Masaoka and Ken Sakai*
Department of Chemistry, Faculty of Science, Kyushu University, Hakozaki 6-10-1,
Higashi-ku, Fukuoka 812-8581, Japan
Correspondence e-mail: ksakai@chem.kyushu-univ.jp
Received 18 August 2008; accepted 17 September 2008

Mo K radiation
 = 0.09 mm 1
T = 296 (2) K
0.13  0.05  0.05 mm

Data collection
Bruker SMART APEX CCDdetector diffractometer
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)
Tmin = 0.992, Tmax = 0.995

8821 measured reﬂections
3222 independent reﬂections
2284 reﬂections with I > 2(I)Rint = 0.036

Reﬁnement
R[F 2 > 2(F 2)] = 0.047
wR(F 2) = 0.114
S = 1.03
3222 reﬂections
279 parameters

H atoms treated by a mixture ofindependent and constrained
reﬁnementmax = 0.30 e Å 3
min = 0.23 e Å 3

Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.003 Å;
R factor = 0.047; wR factor = 0.114; data-to-parameter ratio = 11.5.

Table 1

Hydrogen-bond geometry (Å,  ).

In the title molecule, C24H16N4OH2O, the benzene ring of the
1,10-phenanthroline group and that of the 2-phenylpyridine
group are respectively twisted by 67.9 (1) and 15.3 (3) fromthe carbamoyl group deﬁned by the plane of the O C—N
group of atoms. The water molecule is hydrogen bonded to
one of the phenanthroline N atoms. In the crystal structure,signiﬁcant – stacking interactions occur, with centroid-tocentroid separations in the range 3.567–3.681 (2) Å.

Related literature
For background information, see: Ozawa & Sakai (2007);
Ozawa et al. (2006, 2007); Sakai & Ozawa (2007).

D—H  A

D—H

H  AD  A

D—H  A

O2—H1S  N2

0.92 (4)2.01 (4)2.905 (2)163 (3)

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 in part supported by a Grant-in-Aid for
Scientiﬁc Research (A) (No. 17205008), a Grant-in-Aid forSpecially Promoted Research (No. 18002016), and a Grant-inAid for the Global COE Program (‘Science for Future
Molecular Systems’) from the Ministry of Education, Culture,
Sports, Science and Technology of Japan.
Supplementary data and ﬁgures for this paper are available from the
IUCr electronic archives (Reference: LH2685).

References
Bruker (2004). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National
Laboratory, Tennessee, USA.
Molecular Structure Corporation (2001). TEXSAN. MSC, The Woodlands,
Texas, USA.
Ozawa, H., Haga, M. & Sakai, K. (2006). J. Am. Chem. Soc. 128, 4926–927.
Ozawa, H. & Sakai, K. (2007). Chem. Lett. 36, 920–921.
Ozawa, H., Yokoyama, Y., Haga, M. & Sakai, K. (2007). Dalton Trans. pp.
1197–1206.
Sakai, K. (2004). KENX. Kyushu University, Japan.
Sakai, K. & Ozawa, H. (2007). Coord. Chem. Rev. 251, 2753–2766.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Experimental
Crystal data
C24H16N4OH2O
Mr = 394.42
Triclinic, P1
Acta Cryst. (2008). E64, o1979

a = 8.226 (2) Å
b = 9.357 (3) Å
c = 13.849 (4) Ådoi:10.1107/S1600536808029851

electronic reprint

Kobayashi et al.

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