4
68
J Chem Crystallogr (2008) 38:467–470
it was treated with equivalent mol 6-chloropyridin-3-for-
myl chloride obtained by general procedure to give the
target molecule as shown in Scheme 1, which was sepa-
rated by recrystallization with acetone. m.p.: 220–223 °C.
Table 1 Crystallographic data and structure refinement for the title
compound
Empirical formula
Formula weight
Wavelength
C
11
H
14ClN
255.70
0.71073 A
3 2
O
-
1
1
IR (cm ): 3272 (N–H), 1668, 1694 (C=O). H NMR
˚
(
CDCl ) d: 1.41 (s, 9H, CH ), 7.75–9.32 (m, 3H, Py–H),
3
3
3
Crystal size
0.516 9 0.273 9 0.217 mm
9
.34 (s, 1H, N–H), 10.67 (s, 1H, N–H). Anal. Calcd. (%)
Temperature
293(2) K
Monoclinic
Pn
for C H ClN O : C, 51.67; H, 5.52; N, 16.43. Found (%):
1
1
14
3 2
Crystal system
Space group
C, 51.53; H, 5.58; N, 16.31. Suitable crystal was obtained
by vapor diffusion in a mixed solution of ethanol and
acetone (1:2) at room temperature.
˚
Unit cell dimensions
3
Volume (A )
a = 9.335(3) A, a = 90°
b = 12.715(3) A, b = 95.417(6)°
˚
˚
˚
Z
c = 21.813(6) A, c = 90°
2577.6(12)
Crystal Structure Determinations and Refinements
Density
Absorption coefficient
Index ranges
8
The crystal data, data collection, and refinement parameter
for the title compound is listed in Table 1. The crystal
of title molecule with dimensions of 0.516 9 0.273
3
1.318 Mg/m
-
1
Reflections collected
Independent reflections
0.291 mm
-11 B h B 11, -15 B k B 15,
14 B l B 26
9
0.217 mm was carried on Bruker SMART CCD area-
-
detector diffractometer equipped with a graphite-mono-
˚
Completeness to h = 25.50°
Goodness-of-fit on F
13297
chromatized MoK (k = 0.71073 A) radiation for the data
2
a
6797 [R(int) = 0.1206]
collection at 293(2) K. A total of 13,297 reflections were
Final R indices [I [ 2r(I)]
R indices (all data)
99.9%
0.901
collected in the range of 1.60 B h B 25.50°, of which
6
,797 (Rint = 0.1206) were independent. The structure was
Largest diff. peak and hole
R
R
1
= 0.0953, wR
= 0.1709, Wr
2
= 0.2461
= 0.2848
solved by direct methods. Non-hydrogen atoms were
determined with successive difference Fourier syntheses.
The anisotropic thermal parameters for non-hydrogen
1
2
-3
˚
.677 and -0.395 e A
0
2
atoms were refined on F by full-matrix least-squares.
Hydrogen atoms were inserted in their calculated positions.
All computations were carried out using the SHELXTL
program package [10] on a legend Pentium (IV) computer,
giving a final residual factors R = 0.0953 and wR =
Figure 1 gives perspective view of the compounds with
the atomic labeling systems. All the bond lengths in the
molecule are within normal ranges comparable to those of
the similar compounds [11, 12]. The configuration of title
˚
compound with O(2)–C(8) = 1.160(14) A and an C(7)–
0
.2461 and goodness-of-fit, GOF = 0.901.
N(1)–C(8) angle of 128.2(10)° is similar to that of acylurea
˚
compound with O(3)–C(9) = 1.224(4) A and an C(9)–
Result and Discussion
N(1)–C(8) angle of 128.2(3)° reported by Song et al. [12].
From the crystal data and structure (Fig. 1), all the atoms of
the urea linkage were found to be coplanar giving the
lowest energy for the formation of an intramolecular
hydrogen bond between O(1) and H–N(3). Its hydrogen
bond (Fig. 1) and data (Table 3) reveals that an intramo-
lecular N–HꢀꢀꢀO hydrogen bond forms a six-membered ring
in the central part of the molecule, which may be stabilized
the acylurea bridge. The formed six-membered ring and
pyridine ring in every molecule are nearly coplanar, which
The important intermediate t-butylurea was treated with
6
-chloropyridin-3-formyl chloride in the presence of ace-
tonitrile to give target compound conveniently. The title
molecular structure is shown in Fig. 1. The molecular
packing is shown in Fig. 2. The selected bond lengths and
bond angles are listed in Table 2, hydrogen bond data are
in Table 3, and the torsion angles for the title compound
are shown in Table 4.
Scheme 1 Synthetic route and
reaction conditions
O
OH
O
H2SO4
+
H N
NH2
H N
N
H
2
2
N
O
NEt3
Cl
HN
O
COOH
COCl
CH3CN
HN
SOCl2
Cl
N
Cl
N
1
23