J Chem Crystallogr (2011) 41:1707–1711
1709
˚
Table 2 Distances (A) and angles (°) involving hydrogen bonding of
the compounds
D–HꢀꢀꢀA
d(D–H) d(HꢀꢀꢀA) d(DꢀꢀꢀA) Angle
˚ ˚ ˚
(A)
(A)
(A)
(D–HꢀꢀꢀA) (°)
1
O(5)–H(5B)ꢀꢀꢀN(2)
O(5)–H(5B)ꢀꢀꢀO(1)
0.84(1) 2.55(3) 3.144(3) 128(3)
0.84(1) 2.07(2) 2.858(3) 156(3)
O(5)–H(5A)ꢀꢀꢀO(1)i 0.85(1) 2.07(1) 2.914(3) 178(3)
N(1)–H(1)ꢀꢀꢀO(5)ii
O(2)–H(2)ꢀꢀꢀO(4)
2
0.89(1) 2.04(1) 2.909(3) 164(3)
0.82
1.89
2.588(3) 142
Fig. 1 View of the molecular structure of 1, showing the atom
labeling scheme. Displacement ellipsoids are drawn at the 30%
probability level for non-H atoms. Hydrogen bonds are indicated as
dashed lines
O(3)–H(3)ꢀꢀꢀO(4)
N(1)–H(1)ꢀꢀꢀO(3)iii
0.82
1.80
2.608(2) 168
0.90(1) 2.20(1) 3.071(2) 162(2)
O(4)–H(4B)ꢀꢀꢀO(1)iv 0.85(1) 1.93(1) 2.764(2) 168(2)
O(4)–H(4A)ꢀꢀꢀO(1)v 0.84(1) 2.15(2) 2.922(2) 153(2)
O(4)–H(4A)ꢀꢀꢀN(2)v 0.84(1) 2.47(2) 3.129(2) 135(2)
Symmetry codes: (i) x, 1 ? y, z; (ii) x, 3/2 - y, 1/2 ? z; (iii) 1 ? x,
3/2 - y, 1/2 ? z;(iv)1 - x, -1/2 ? y, 3/2 - z;(v)x, 3/2 - y, -1/2 ? z
hydrogen bonds (Table 2), to form 2D sheets parallel to the
bc plane (Fig. 3). In the crystal structure of 2, adjacent two
benzohydrazide molecules are linked by two water mole-
cules through two O(4)–H(4B)ꢀꢀꢀO(1)iv, two O(4)–
H(4A)ꢀꢀꢀO(1)v, and two O(4)–H(4A)ꢀꢀꢀN(2)v [symmetry
codes for iv: 1 - x, -1/2 ? y, 3/2 - z; for v: x, 3/2 - y,
-1/2 ? z] hydrogen bonds (Table 2), to form a dimer. The
dimers are further linked through O(3)–H(3)ꢀꢀꢀO(4) and
N(1)–H(1)ꢀꢀꢀO(3)iii [symmetry code for iii: 1 ? x, 3/2 - y,
1/2 ? z] hydrogen bonds (Table 2), to form a 3D network
(Fig. 4).
Fig. 2 View of the molecular structure of 2, showing the atom
labeling scheme. Displacement ellipsoids are drawn at the 30%
probability level for non-H atoms
and within normal ranges [9–13]. The water molecules
are linked to the hydrazone molecules through hydrogen
bonds. In 1, there exists an intramolecular O(2)–
H(2)ꢀꢀꢀO(4) hydrogen bond, which made the nitro group
located nearly coplanar with the C(9)–C(14) benzene
ring. The dihedral angle between the nitro group with the
benzene ring is 4.6(3)°. In the benzohydrazide molecules,
During the search of literature, it can be seen that the
crystal packing modes of the hydrated and unhydrated
hydrazide compounds are distinct different from each
other. Considering the hydrogen-riched water molecules
are readily participate in the formation of hydrogen bonds,
the crystal packing of the hydrazide compounds containing
water molecules are more complicated than those with no
water molecules [9, 14–18].
˚
the bond lengths of C(8)–N(2) are 1.272(3) A for 1 and
˚
1.280(2) A for 2, indicating them as typical double
bonds. The distances between atoms C(7) and N(1)
˚
˚
[1.352(3) A for 1 and 1.344(3) A for 2] are intermediate
between single and double bonds, due to the conjugation
effects of the whole molecules. In the benzohydrazide
molecules, the dihedral angles between the C(1)–C(6)
and C(9)–C(14) benzene rings are 29.1(2)° for 1 and
13.0(2)° for 2.
Supplementary Material
CCDC—821976 for 1 and 821977 for 2 contain the sup-
plementary crystallographic data for this paper. These data
Crystallographic Data Centre (CCDC), 12 Union Road,
Cambridge CB2 1EZ, UK; fax: ?44(0)1223-336033 or
e-mail: data_request@ccdc.cam.ac.uk.
In the crystal structure of 1, the adjacent benzohydrazide
molecules are linked by water molecules through the O(5)–
H(5B)ꢀꢀꢀO(1), O(5)–H(5B)ꢀꢀꢀN(2), and O(5)–H(5A)ꢀꢀꢀO(1)i
[symmetry code for i: x, 1 ? y, z] hydrogen bonds
(Table 2), to form chains along the b axis. The chains are
further linked by the water molecules through the N(1)–
H(1)ꢀꢀꢀO(5)ii [symmetry code for ii: x, 3/2 - y, 1/2 ? z]
123
Lei, Yan
