organic compounds
Data collection
program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997);
molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and
MERCURY (Macrae et al., 2006); software used to prepare material
for publication: WinGX (Farrugia, 1999).
Stoe IPDS-II diffractometer
! scan
4368 measured re¯ections
1692 independent re¯ections
1556 re¯ections with I > 2ꢄ(I)
Rint = 0.080
ꢅmax = 26.0ꢀ
Re®nement
The authors acknowledge the Faculty of Arts and Sciences,
Ondokuz Mayõs University, Turkey, for the use of the
diffractometer purchased under grant No. F279 of the
University Research Fund.
Re®nement on F2
R[F2 > 2ꢄ(F2)] = 0.040
wR(F2) = 0.107
S = 1.04
1692 re¯ections
128 parameters
H atoms treated by a mixture of
independent and constrained
re®nement
w = 1/[ꢄ2(F2o) + (0.0683P)2]
where P = (F2o + 2Fc2)/3
(Á/ꢄ)max < 0.001
3
Ê
Áꢆmax = 0.19 e A
3
Ê
0.22 e A
Áꢆmin
=
Extinction correction: SHELXL97
Extinction coef®cient: 0.056 (11)
Absolute structure: Flack (1983),
660 Friedel pairs
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: MY3010). Services for accessing these data are
described at the back of the journal.
Flack parameter: 0 (2)
Table 3
Selected geometric parameters (A, ) for (II).
References
ꢀ
Ê
Allen, F. H. (2002). Acta Cryst. B58, 380±388.
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Int. Ed. Engl. 34, 1555±1573.
Bonte, J. (2000). Eur. J. Cancer, 36, S114.
N4ÐN4A
N2ÐC3
N2ÐN1
1.4081 (18)
1.310 (2)
1.396 (2)
N1ÐC5
C1PÐC5
1.306 (2)
1.474 (2)
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C5ÐN4ÐN4A
125.43 (13)
136.80 (19)
C5ÐN1ÐN2
107.71 (12)
C6PÐC1PÐC5ÐN1
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Table 4
Hydrogen-bond geometry (A, ) for (II).
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
N4AÐH4AAÁ Á ÁN2iv
0.95 (3)
0.92 (2)
2.19 (3)
2.20 (2)
3.078 (2)
3.0411 (19)
156 (2)
151.4 (18)
N4AÐH4ABÁ Á ÁN1i
1
Symmetry codes: (i) x 1; y; z; (iv) x 1; y
;
z 32.
Massa, S., Di Santo, R., Retico, A., Artico, M., Simonetti, N., Fabrizi, G. &
Lamba, D. (1992). Eur. J. Med. Chem. 27, 495±502.
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Dyer, R. D. (1993). J. Med. Chem. 36, 1090±1099.
2
For both compounds, methyl H atoms were located in a difference
Fourier synthesis and then re®ned as rigid rotating groups [CÐH =
Ê
0.96 A and Uiso(H) = 1.5Ueq(C)]. Aromatic H atoms were placed
È
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Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
GoÈttingen, Germany.
Ê
geometrically and re®ned using a riding model [CÐH = 0.93 A and
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Uiso(H) = 1.2Ueq(C)]. Atoms H4AA and H4AB bound to N4A were
re®ned freely.
Ç
Yazõcõ, S., IsËõk, SË., Agar, E., Karaoglu, SË. A., Bekircan, O., Kolaylõ, S., SËenel, I.
Æ
Æ
È
È
È
È
& Buyukgungor, O. (2004). Acta Cryst. E60, o815±o816.
Zachara, J., Madura, I. & Wøostowski, M. (2004). Acta Cryst. C60, o57±o59.
Zhu, D.-R., Xu, Y., Zhang, Y., Wang, T.-W. & You, X.-Z. (2000). Acta Cryst.
C56, 895±896.
For both compounds, data collection: X-AREA (Stoe & Cie, 2002);
cell re®nement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002);
program(s) used to solve structure: SHELXS97 (Sheldrick, 1997);
ꢁ
o646 ËSahin et al. C10H12N4 and C9H10N4
Acta Cryst. (2006). C62, o643±o646