M. Mazik, A. Hartmann, P. G. Jones
FULL PAPER
Table 2. C–H···Y and C–Cl···Y distances and angles in the crystal structures of 1·H
2
O·CHCl
3
(Y = O, Cl, Cphenyl or Ph–center).
C–H···Y/C–Cl···Y interaction
CH···Y/CCl···Y [Å] C···Y [Å] C–H···Y/C–Cl···Y angle [°]
Figure[f]
a]
Cl
Cl
Cl
Cl
Cl
3
3
2
2
2
C–H···O=C (a)[
1.89
2.15
3.09
3.15
3.29–3.58
2.93
2.87
2.61
2.89
3.30
2.94
3.11
4.82
4.82
4.85–5.18
4.01
161
148
167
161
138–170
178
Figure 2a
Figure 2a
Figure 2a
[
a]
C–H···O=C (b)
[
a]
HC–Cl···O=C (c)
HC–Cl···Ph-center (d)[a]
HC–Cl···Cphenyl
Figures 2b, 3
phenanthroline-C3–H···Cl–CHCl
phenanthroline-C6–H···Cl–CHCl
phenanthroline-C8–H···Cl–CHCl
2
2
2
(e)[a]
Figure 3
3.91
3.68
172
171
[a]
Cl
Cl
3
C–H···Cl–CHCl
2
(f)
3.69
132
A
A
B
B
(g)[a]
[b]
[d]
2
HC –Cl ···Cl –C HCl
2
5.03
4
171
Figure 3
Figure 3
.51[
c]
123
[e]
a] Noncovalent interaction shown in Figures 2 and 3. [b] C ···Cl distance (C–H distances normalized to 1.08 Å). [c] Cl ···CB distance.
A
B
A
[
[
8
A
A
B
A
B
B
d] θ
1 2
(C –Cl ···Cl angle), see Figure 3. [e] θ (Cl ···Cl –C angle). [f] Two of the three chloroform molecules are slightly disordered (ca.
6:14). Packing diagrams and discussion are based only on the major components.
ganic solvents were removed in vacuo, and the resulting solid was
purified by column chromatography (chloroform/methanol, 10:1).
uente, F. Mota, Chem. Phys. Lett. 1998, 290, 519–525; e) D.
Braga, F. Grepioni, New J. Chem. 1998, 22, 1159–1161; f) G. R.
Desiraju, Acc. Chem. Res. 1997, 30, 441–449; g) B. P. Klaholz,
D. Moras, Structure 2002, 10, 1197–1204.
Yield: 0.36 g (68%). M.p. 151–152 °C. R
f
= 0.58 (silica gel; chloro-
form/methanol, 10:1). H NMR (400 MHz, CDCl ): δ = 1.40 (t, J
7.5 Hz, 9 H), 3.07 (q, J = 7.5 Hz, 6 H), 4.92 (d, J = 4.3 Hz, 6
H), 6.83 (dd, J = 8.1, 4.4 Hz, 3 H), 7.75 (d, J = 8.8 Hz, 3 H), 7.81
d, J = 8.8 Hz, 3 H), 7.83 (dd, J = 4.4, 1.5 Hz, 3 H), 8.07 (dd, J =
.1, 1.5 Hz, 3 H), 8.34 (d, J = 8.3 Hz, 3 H), 8.61 (d, J = 8.3 Hz, 3
1
3
[
5] For examples of CH···N hydrogen bonds, see: a) R. Taylor, O.
Kennard, J. Am. Chem. Soc. 1982, 104, 5063–5070; b) M. Ma-
zik, D. Bläser, R. Boese, Tetrahedron Lett. 2000, 41, 5827–5831;
c) M. Mazik, D. Bläser, R. Boese, Tetrahedron 2001, 57, 5791–
5797; d) V. R. Thalladi, A. Gehrke, R. Boese, New J. Chem.
2000, 24, 463–470; e) V. R. Thalladi, T. Smolka, A. Gehrke, R.
Boese, R. Sustmann, New J. Chem. 2000, 24, 143–147; f) D. S.
Reddy, D. C. Craig, G. R. Desiraju, J. Am. Chem. Soc. 1996,
=
(
8
13
H), 10.03 (t, J = 3.8 Hz, 3 H) ppm. C NMR (100 MHz, CDCl
δ = 16.0, 23.6, 38.6, 122.1, 122.4, 126.9, 127.1, 128.7, 129.1, 131.4,
36.2, 137.2, 144.1, 144.7, 145.2, 148.7, 150.8, 164.7 ppm. HRMS
ESI): calcd. for C54 Na 890.3543; found 890.3539.
3
):
1
1
18, 4090; g) G. R. Desiraju, Crystal Engineering: The Design
(
45 9 3
H N O
of Organic Solids, Elsevier, Amsterdam, 1989, pp. 166–167.
CCDC-739268 contains the supplementary crystallographic data
for this paper. These data can be obtained free of charge from The
Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/
data_request/cif.
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[
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[
8] For reviews on halogen bonding, see: a) P. Metrangolo, H.
Neukirch, T. Pilati, G. Resnati, Acc. Chem. Res. 2005, 38, 386–
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[
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[
[
[
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