organic compounds
728 frames were collected with a ' scan and 893 frames with !
scans. The crystal-to-detector distance was 40 mm, the rotation angle
was 0.5ꢀ per frame and the exposure time was 20 s per frame. The
re®nement was performed in a non-reduced setting of space group
P21 in order to align the twin axis parallel to the crystallographic
a* axis. In the reduced setting, the twin axis would be parallel to
a face diagonal. The cell parameters of the reduced setting are
Experimental
2,3-Diphenylbuta-1,3-diene was synthesized by a double Wittig
reaction of benzil with methyltriphenylphosphonium bromide.
Details of the synthesis will be published elsewhere (van Walree et al.,
2005). Crystals were grown by sublimation at 20 mm Hg pressure with
gentle heating. During sublimation, the cold ®nger was cooled with an
ice±salt mixture.
Ê
Ê
Ê
a = 8.5791 (12) A, b = 5.7966 (3) A, c = 12.1575 (14) A and ꢁ =
109.344 (9)ꢀ, and the transformation matrix from the present setting
to the reduced setting is (100/010/101). The absolute structure could
not be determined reliably. Therefore, an arbitrary absolute structure
was chosen and Friedel pairs were merged prior to the re®nement
using the program MERGEHKLF5 (Schreurs, 2003), which also
merged the redundant data taking the twin relationship into account.
All H atoms were located in a difference Fourier map and were
constrained to ride on their parent atoms, with Uiso(H) values of
Crystal data
3
C16H14
Dx = 1.201 Mg m
Mo Kꢂ radiation
Cell parameters from 290
re¯ections
Mr = 206.27
Monoclinic, P21
a = 8.5791 (12) A
Ê
b = 5.7966 (3) A
ꢃ = 4.0±27.1ꢀ
ꢄ = 0.07 mm
T = 150 (2) K
Ê
1
Ê
c = 12.3414 (17) A
ꢁ = 111.645 (10)ꢀ
Ê
V = 570.46 (12) A
Z = 2
3
Needle, colourless
0.48 Â 0.24 Â 0.24 mm
Ê
1.2Ueq(C) and CÐH distances of 0.95 A.
Data collection: COLLECT (Nonius, 1999); cell re®nement:
DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisen-
berg et al., 2003); program(s) used to solve structure: SIR97 (Alto-
mare et al., 1999); program(s) used to re®ne structure: SHELXL97
(Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); soft-
ware used to prepare material for publication: SHELXL97.
Data collection
Nonius KappaCCD diffractometer
' and ! scans
14 083 measured re¯ections
1444 independent re¯ections
1355 re¯ections with I > 2ꢅ(I)
Rint = 0.041
ꢃmax = 27.7ꢀ
h = 11 ! 11
k = 7 ! 7
l = 16 ! 16
Re®nement
This work was supported by the Council for Chemical
Sciences of the Netherlands Organization for Scienti®c
Research (CW±NWO).
Re®nement on F2
R[F2 > 2ꢅ(F2)] = 0.031
wR(F2) = 0.080
S = 1.08
1444 re¯ections
w = 1/[ꢅ2(F2o) + (0.042P)2
+ 0.0638P]
where P = (F2o + 2Fc2)/3
(Á/ꢅ)max < 0.001
3
Ê
Áꢆmax = 0.17 e A
3
Ê
0.16 e A
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: FG1830). Services for accessing these data are
described at the back of the journal.
146 parameters
H-atom parameters constrained
Áꢆmin
=
Table 1
Selected geometric parameters (A, ).
ꢀ
References
Ê
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C.,
Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J.
Appl. Cryst. 32, 115±119.
Cannas, M., Carta, G. & Marongiu, G. (1972). Acta Cryst. A28, 497±501.
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92±96.
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst. 36, 220±229.
C11ÐC12
C12ÐC13
C12ÐC22
1.329 (3)
1.491 (2)
1.492 (2)
C21ÐC22
C22ÐC23
1.335 (3)
1.486 (2)
C11ÐC12ÐC13ÐC18
C11ÐC12ÐC22ÐC21
17.0 (3)
55.6 (2)
C21ÐC22ÐC23ÐC28
19.3 (3)
Herbst-Irmer, R. & Sheldrick, G. M. (1998). Acta Cryst. B54, 443±449.
Le Page, Y. (2002). J. Appl. Cryst. 35, 175±181.
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Pilati, T. & Forni, A. (1998). J. Appl. Cryst. 31, 503±504.
Roth, W. R., Adamczak, O., Breuckmann, R., Lennartz, H.-W. & Boese, R.
(1991). Chem. Ber. 124, 2499±2521.
Table 2
Hydrogen-bond geometry (A, ).
ꢀ
Ê
Schreurs, A. M. M. (2003). MERGEHKLF5. Utrecht University, The
Netherlands.
Cg1 and Cg2 are the centroids of rings C13±C18 and C23±C28, respectively.
È
Sheldrick, G. M. (1997). SHELXL97. University of Gottingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7±13.
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
Walree, C. A. van, van der Wiel, B. C., Jenneskens, L. W., Lutz, M., Spek, A. L.
& van Lenthe, J. (2005). J. Am. Chem. Soc. In preparation.
Wiel, B. C. van der, Williams, R. M. & van Walree, C. A. (2004). Org. Biomol.
Chem. 2, 3432±3433.
C11ÐH11AÁ Á ÁCg1i
0.95
0.95
3.05
2.90
3.96
3.75
161
149
C21ÐH21AÁ Á ÁCg2ii
1
Symmetry codes: (i) x; y
;
z; (ii) x; y 12; z 1.
2
ꢁ
o302 Lutz et al. C16H14
Acta Cryst. (2005). C61, o300±o302