organic compounds
Data collection
For (I), the space group P21/n was uniquely assigned from the
systematic absences. For (II), the systematic absences permitted Cc
and C2/c as possible space groups; C2/c was selected and con®rmed
by the subsequent structure analysis. All H atoms were located in
difference maps and then treated as riding atoms. H atoms bonded to
C atoms were allowed to ride in geometrically idealized positions,
Bruker±Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.951, Tmax = 0.980
37526 measured re¯ections
3597 independent re¯ections
2266 re¯ections with I > 2ꢃ(I)
Rint = 0.057
Ê
with CÐH distances of 0.95 (aromatic and pyrazole) or 0.98 A
Re®nement
R[F2 > 2ꢃ(F2)] = 0.056
wR(F2) = 0.178
S = 1.08
227 parameters
H-atom parameters constrained
(methyl), and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl
groups and 1.2 for all other H atoms bonded to C atoms. H atoms
bonded to N atoms were permitted to ride at the positions deduced
Ê
from difference maps, all giving NÐH distances of 0.87 A, with
Uiso(H) = 1.2Ueq(N).
3
Ê
Áꢄmax = 0.33 e A
3
Ê
0.39 e A
3597 re¯ections
Áꢄmin
=
Table 1
Hydrogen-bond geometry (A, ) for (I).
ꢁ
Ê
For both compounds, data collection: COLLECT (Hooft, 1999);
cell re®nement: DIRAX/LSQ (Duisenberg et al., 2000); data reduc-
tion: EVALCCD (Duisenberg et al., 2003); program(s) used to solve
structure: SIR2004 (Burla et al., 2005) and WinGX (Farrugia, 1999);
program(s) used to re®ne structure: OSCAIL (McArdle, 2003) and
SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek,
2003); software used to prepare material for publication: SHELXL97
and PRPKAPPA (Ferguson, 1999).
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
N5ÐH5AÁ Á ÁN2i
0.87
0.87
0.95
2.33
2.18
2.39
3.131 (3)
3.024 (3)
3.304 (3)
154
163
161
N5ÐH5BÁ Á ÁO141ii
C16ÐH16Á Á ÁO121i
Symmetry codes: (i) x 32; y 21; z 21; (ii) x
;
y 32; z
.
1
2
1
2
Compound (II)
Â
The authors thank `Servicios Tecnicos de Investigacion' of
the Universidad de Jaen and the staff for data collection. JC
Â
Â
Crystal data
3
Ê
Â
Â
thanks the Consejerõa de Innovacion, Ciencia y Empresa
C17H14N4O4
Mr = 338.32
Monoclinic, C2=c
V = 2988.1 (7) A
Z = 8
Â
Â
(Junta de Andalucõa, Spain) and the Universidad de Jaen
for ®nancial support. JP thanks COLCIENCIAS and
UNIVALLE (Universidad del Valle, Colombia) for ®nancial
support that has also supported a short stay at Instituto de
Quõmica Organica de Sõntesis, Universidad Nacional de
Rosario, Argentina. EGM thanks CONICETand Universidad
Nacional de Rosario for ®nancial support.
Mo Kꢁ radiation
1
Ê
a = 31.0506 (4) A
ꢂ = 0.11 mm
T = 120 (2) K
Ê
b = 5.4210 (11) A
Ê
c = 20.7251 (12) A
0.50 Â 0.29 Â 0.28 mm
ꢀ = 121.071 (6)ꢁ
Â
Â
Â
Data collection
Bruker±Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.947, Tmax = 0.967
33526 measured re¯ections
3420 independent re¯ections
2488 re¯ections with I > 2ꢃ(I)
Rint = 0.044
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SK3149). Services for accessing these data are
described at the back of the journal.
Re®nement
R[F2 > 2ꢃ(F2)] = 0.048
wR(F2) = 0.134
S = 1.11
227 parameters
H-atom parameters constrained
References
3
Ê
Áꢄmax = 0.28 e A
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,
R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1±19.
3
Ê
0.36 e A
3420 re¯ections
Áꢄmin
=
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555±1573.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De
Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38,
381±388.
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000).
J. Appl. Cryst. 33, 893±898.
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst. 36, 220±229.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837±838.
Table 2
Selected bond lengths (A) for (II).
Ê
C51ÐN5
C51ÐC52
C52ÐC53
C53ÐC54
C54ÐC55
1.364 (2)
1.425 (2)
1.391 (2)
1.378 (3)
1.404 (2)
C55ÐC56
C56ÐC51
C52ÐN52
N52ÐO521
N52ÐO522
1.370 (3)
1.419 (3)
1.448 (2)
1.2522 (19)
1.2262 (19)
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography
Centre, Chemistry Department, NUI Galway, Ireland.
Portilla, J., Mata, E. G., Nogueras, M., Cobo, J., Low, J. N. & Glidewell, C.
(2007). Acta Cryst. C63, o38±o41.
Table 3
Hydrogen-bond geometry (A, ) for (II).
ꢁ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
È
Sheldrick, G. M. (1997). SHELXL97. University of Gottingen, Germany.
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Gottingen,
N5ÐH5Á Á ÁO521
N2ÐH2Á Á ÁO541i
C36ÐH36Á Á ÁO541i
C53ÐH53Á Á ÁO522ii
0.87
0.87
0.95
0.95
1.89
1.96
2.36
2.54
2.600 (2)
2.828 (2)
3.266 (3)
3.487 (2)
137
171
159
173
È
Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7±13.
Tachibana, K. & Kaneko, Y. (1989). Japanese Kokai Tokkyo Koho, Japanese
Patent 01003187A2. Japanese Patent Application 87-159281 (1987).
Symmetry codes: (i) x 1; y 2; z 1; (ii) x 1; y; z 12.
ꢀ
Acta Cryst. (2007). C63, o510±o513
Portilla et al. C17H14N4O4 o513