organic compounds
Table 1
Selected geometric parameters (A, ).
distance from the centre of gravity of each ring to the plane of
Ê
the opposing ring is 3.50 A, with a slippage from the centroid
ꢀ
Ê
Ê
of the opposing ring of 0.85 A.
N1ÐC16
N1ÐC12
N1ÐC13
N2ÐC17
1.465 (3)
1.461 (3)
1.467 (3)
1.414 (3)
N2ÐC14
N2ÐC15
C13ÐC14
C15ÐC16
1.452 (2)
1.466 (3)
1.496 (3)
1.505 (3)
Experimental
The synthesis of (I) was performed according to the method of Jain et
al. (1967). A mixture of 7-bromoethoxy-4-methylcoumarin (566 mg,
2 mmol), 1-(4-methoxyphenyl)piperazine (457 mg, 2 mmol) and
anhydrous K2CO3 (276 mg, 2 mmol) was stirred at re¯ux in acetone
(5 ml) and anhydrous ethanol (5 ml) for 48 h. The precipitate was
®ltered off and washed with fresh chloroform. The solvent was
evaporated under reduced pressure from the combined ®ltrate and
washings. The residue was chromatographed on a silica-gel column by
eluting with a cyclohexane/acetone mixture (8:1 v/v) to give a
colorless solid (170 mg, 21%, m.p. 511 K). 1H NMR (500 MHz,
CDCl3): ꢃ 7.51 (d, 1H, H-5, J = 8.91 Hz), 6.95 (m, 4H, Ph), 6.86 (dd,
1H, H-6, J = 8.80 and 2.60 Hz), 6.82 (d, 1H, H-8, J = 2.60 Hz), 6.15 (s,
1H, H-3), 4.10 (t, 2H, CH2O, J = 6.30 Hz), 3.77 (s, 3H, OCH3), 3.10 [m,
4H, N4 (CH2)2], 2.85 [m, 4H, (CH2)2N1], 2.60 (m, 2H, N1CH2), 2.38
(s, 3H, CH3). A crystal suitable for diffraction analysis was obtained
by slow evaporation of a solution of (I) in a mixture of ethanol and
ethyl acetate (1:1 v/v) at room temperature.
C16ÐN1ÐC12
C16ÐN1ÐC13
C12ÐN1ÐC13
C17ÐN2ÐC14
C17ÐN2ÐC15
111.81 (17)
108.22 (17)
109.31 (16)
116.81 (15)
116.63 (16)
C14ÐN2ÐC15
N1ÐC13ÐC14
N2ÐC14ÐC13
N2ÐC15ÐC16
N1ÐC16ÐC15
109.19 (16)
112.53 (17)
111.34 (17)
111.45 (17)
111.33 (17)
N1ÐC13ÐC14ÐN2
N2ÐC15ÐC16ÐN1
57.7 (2)
58.4 (2)
C23ÐO4ÐC20ÐC19
C23ÐO4ÐC20ÐC21
2.7 (3)
177.91 (19)
Table 2
Hydrogen-bond geometry (A, ).
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
O5ÐH5AÁ Á ÁN1
O5ÐH5BÁ Á ÁO2i
C6ÐH6Á Á ÁO5ii
0.88
0.87
0.93
0.96
2.08
2.19
2.61
2.63
2.955 (3)
2.989 (3)
3.369 (3)
3.579 (4)
172
152
139
170
C23ÐH23BÁ Á ÁO5iii
Symmetry codes: (i) x 2; y 1; z; (ii) x 1; y 1; z; (iii) x 12, y 21,
z 12.
Crystal data
3
C23H26N2O4ÁH2O
Dx = 1.305 Mg m
Mo Kꢁ radiation
Cell parameters from 2841
re¯ections
Mr = 412.47
Monoclinic, P21=n
SHELXTL (Bruker, 2000); software used to prepare material for
publication: SHELXTL and WinGX (Version 1.7; Farrugia, 1999).
Ê
a = 10.776 (7) A
ꢂ = 2.2±24.1ꢀ
ꢅ = 0.09 mm
T = 298 (2) K
Ê
b = 7.483 (5) A
1
Ê
c = 26.381 (18) A
ꢄ = 99.406 (10)ꢀ
The use of the Bruker X-ray Crystallographic Service at
Liaocheng University and the valuable assistance of Professor
Daqi Wang there are gratefully acknowledged.
3
Ê
V = 2099 (2) A
Z = 4
Prism, colorless
0.53 Â 0.48 Â 0.27 mm
Data collection
Bruker SMART CCD area-detector
diffractometer
' and ! scans
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
Tmin = 0.962, Tmax = 0.985
10516 measured re¯ections
3684 independent re¯ections
2296 re¯ections with I > 2ꢆ(I)
Rint = 0.038
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: LN1189). Services for accessing these data are
described at the back of the journal.
ꢂmax = 25.0ꢀ
h = 12 ! 10
k = 8 ! 8
References
l = 31 ! 31
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Re®nement
Re®nement on F2
R[F2 > 2ꢆ(F2)] = 0.046
wR(F2) = 0.124
S = 1.03
3684 re¯ections
w = 1/[ꢆ2(Fo2) + (0.055P)2
+ 0.28P]
where P = (Fo2 + 2Fc2)/3
(Á/ꢆ)max < 0.001
3
Ê
Áꢇmax = 0.17 e A
3
Ê
0.22 e A
273 parameters
H-atom parameters constrained
Áꢇmin
=
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Â
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The positions of the H atoms of the water molecule were found
initially in a difference Fourier map and then constrained to ride on
the parent O atom, with Uiso(H) values of 1.5Ueq(O). The methyl H
atoms were constrained to an ideal geometry, with CÐH distances of
Ê
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freely about the CÐC bonds. All remaining H atoms were placed in
Ê
geometrically idealized positions (CÐH = 0.93±0.97 A) and con-
Â
Estrada, E., Gonzalez, J. C., Santana, L., Uriarte, E. & CastinÄeiras, A. (2000).
Struct. Chem. 11, 249±255.
strained to ride on their parent atoms [Uiso(H) = 1.2Ueq(C)].
Data collection: SMART (Bruker, 2000); cell re®nement: SMART;
data reduction: SAINT (Bruker, 2000); program(s) used to solve
structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne
structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837±838.
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ꢁ
o60 Zhou et al. C23H26N2O4ÁH2O
Acta Cryst. (2006). C62, o58±o61