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In the title compound, C23H19N5O6·H2O, the two components are linked into complex chains by a combination of two independent O—H...O and two independent N—H...O hydrogen bonds. The complex chains are linked into a two-dimensional sheet network via π–π stacking inter­actions and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107021920/av3088sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107021920/av3088Isup2.hkl
Contains datablock I

CCDC reference: 652525

Comment top

As part of our synthetic study of Schiff base systems, we are now focusing on the synthesis of propeller-shaped amido-containing organic compounds, which are important multidentate ligands for the construction of coordination complexes with metal centres (Wang et al., 2005). In 1985, Paolucci and co-workers first reported the 5-H-substituted 2,6-bis(salicylidenehydrazinocarbonyl)pyridine as a potential mono-, di- and tri-nucleating ligand towards uranyl ions (Paolucci et al., 1985). More recently, Chen and co-workers reported a series of 5-substituted 2,6-bis(salicylidenehydrazinocarbonyl)pyridine ligands (see scheme) and their copper(II) complexes (Chen et al., 1996; Chen et al., 1997). However, the researchers only paid attention to the synthesis of their coordination complexes, and did not report the crystal structures of the organic ligands. In this report, we have synthesized the title 3-methoxy derivative compound with a propeller shape, (I), and describe its crystal structure. For convenience, we denote the benzene ring containing atom C8 as B, the benzene ring containing atom C17 as C and the pyridine ring as A.

In compound (I), the two hydrazine components (N2 and N3, and N4 and N5) have essentially planar coordination, and the N—N bond distances (Table 1) have values typical for hydrazine, with both N atoms having planar coordination [mean value 1.401 (3) Å; Allen et al., 1987]. The fragments C5—C6(O1)—N2—N3, C1—C15(O4)—N4—N5, C8—C7—N3—N2 and C17—C16—N5—N4 are essentially planar, as shown by the key torsion angles. The dihedral angles between pyridine ring A and the two benzene rings, B and C, are 17.6 (1) and 17.72 (9)°, respectively. The dihedral angle between two benzene rings is 33.48 (9)°.

Within the selected asymmetric unit (Fig. 1), two hydroxyl O atoms (O2 and O5) act as hydrogen-bond donors, via atoms H2 and H5, respectively, to atoms N3 and N5, thereby generating intramolecular hydrogen bonds of R11(6) motif (Bernstein et al., 1995). Hydrazine atoms N2 and N4 act as hydrogen-bond acceptors, forming intermolecular hydrogen bonds of R11(10) motifs to water atom O7. The solvent water molecule O7 also donates two H atoms to carboxyl atoms O1 and O4 of two different molecules to form relatively strong O—H···O hydrogen bonds.

Through the two intermolecular O—H···O hydrogen bonds and two N—H···O hydrogen bonds to water molecules, compound (I) is linked into a one-dimensional chain along the [010] direction (Fig. 2). It is noteworthy that ππ stacking interactions play an important role in building the one-dimensional chains into two-dimensional layers parallel to (100) (Fig. 3). In the chains, the molecules are antiparallel to each other and the pyridine ring A at (x, y, z) is sandwiched by benzene rings B at (1 - x, -y, 1 - z) and C at (1 - x, 1 - y, 1 - z). The mean interplanar distances are 3.697 (3) and 3.749 (3) Å, respectievly, indicating efficient ππ stacking interactions. Between adjacent chains, the benzene ring plane C at (x, y, z) is antiparallel to the benzene ring C at (1 - x, 1 - y, -z), with an interplanar distance of 3.492 (3) Å. Additional C—H···O hydrogen bonds (Table 2) help to stabilize the layer structure.

Related literature top

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Chen et al. (1996, 1997); Paolucci et al. (1985); Wang et al. (2005).

Experimental top

The ligand 2,6-bis(hydrazinocarbonyl)pyridine was prepared by the following reaction. Diethyl-2,6-pyridinecarboxylate ester (1.95 g, 10 mmol) and hydrazine hydrate (10 ml, 85%) were reacted in a 100 ml reaction flask in chloroform (Volume?). The product was recrystallized from a large amount of water as colourless needles (75% yield).

The ligand 2,6-bis[(2-hydroxy-3-methoxybenzylidene)hydrazinecarbonyl]pyridine was synthesized as follows. 2,6-Bis(hydrazinocarbonyl)pyridine (1.95 g, 10 mmol), 2-hydroxy-3-methoxybenzaldehyde (3.04 g, 20 mmol) and p-toluenesulfonic acid as catalyst were added to a 100 ml reaction flask with ethanol (60 ml). The mixture was stirred magnetically and refluxed for about 3 h. After filtration, and removal of the ethanol by rotary evaporation, the crude product was obtained and was recrystallized from methanol (85% yield).

Refinement top

C-bound H atoms were positioned geometrically, with C—H = 0.93–0.96 Å, and refined as riding, with Uiso(H) = 1.2Ueq(C), or 1.2Ueq(methyl C). N-bound H atoms were found in difference maps, relocated in idealized positions with N—H = 0.89 Å, and refined as riding, with Uiso(H) = 1.2Ueq(N). Water and hydroxyl H atoms were found in difference maps, relocated in idealized positions with O—H = 0.82 Å, and refined as riding atoms with Uiso(H) = 1.2Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The one-dimensional chain structure of (I). Dashed lines indicate hydrogen bonds.
[Figure 3] Fig. 3. The two-dimensional layer structure of (I). Dashed lines indicate hydrogen bonds. H atoms attached to C atoms have been omitted for clarity.
2,6-Bis[(2-hydroxy-3-methoxybenzylidene)hydrazinocarbonyl]pyridine monohydrate top
Crystal data top
C23H21N5O6·H2OZ = 2
Mr = 481.46F(000) = 504
Triclinic, P1Dx = 1.424 Mg m3
Hall symbol: -p 1Mo Kα radiation, λ = 0.71073 Å
a = 10.184 (2) ÅCell parameters from 102 reflections
b = 10.842 (1) Åθ = 1.9–27.1°
c = 11.034 (2) ŵ = 0.11 mm1
α = 98.72 (3)°T = 291 K
β = 110.42 (2)°Block, colourless
γ = 92.42 (3)°0.30 × 0.20 × 0.20 mm
V = 1122.6 (4) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5177 independent reflections
Radiation source: fine-focus sealed tube4150 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.003
ϕ and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1313
Tmin = 0.968, Tmax = 0.973k = 014
5277 measured reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0715P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.007
5177 reflectionsΔρmax = 0.21 e Å3
317 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0098 (18)
Crystal data top
C23H21N5O6·H2Oγ = 92.42 (3)°
Mr = 481.46V = 1122.6 (4) Å3
Triclinic, P1Z = 2
a = 10.184 (2) ÅMo Kα radiation
b = 10.842 (1) ŵ = 0.11 mm1
c = 11.034 (2) ÅT = 291 K
α = 98.72 (3)°0.30 × 0.20 × 0.20 mm
β = 110.42 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5177 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
4150 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.973Rint = 0.003
5277 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.01Δρmax = 0.21 e Å3
5177 reflectionsΔρmin = 0.20 e Å3
317 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.19884 (18)0.34160 (17)0.4560 (2)0.0381 (6)
C20.0625 (2)0.3316 (2)0.4553 (2)0.0507 (7)
H2A0.00140.39030.42370.061*
C30.0192 (2)0.2335 (2)0.5023 (2)0.0612 (8)
H30.07200.22450.50250.073*
C40.11283 (19)0.1481 (2)0.5493 (2)0.0485 (6)
H4A0.08620.08060.58150.058*
C50.24745 (18)0.16595 (18)0.54719 (19)0.0364 (5)
C60.35072 (19)0.07563 (18)0.5996 (2)0.0383 (5)
C70.71717 (19)0.09205 (19)0.70697 (19)0.0421 (6)
H7A0.73320.17190.69060.051*
C80.83587 (19)0.02501 (18)0.76564 (19)0.0386 (6)
C90.9736 (2)0.0783 (2)0.7935 (2)0.0504 (7)
H90.98760.15710.77380.060*
C101.0867 (2)0.0165 (2)0.8489 (2)0.0550 (7)
H101.17700.05390.86750.066*
C111.0688 (2)0.1017 (2)0.8780 (2)0.0535 (7)
H111.14670.14370.91480.064*
C120.9351 (2)0.15635 (19)0.8522 (2)0.0433 (6)
C130.81783 (18)0.09329 (19)0.79588 (19)0.0387 (6)
C141.0176 (2)0.3454 (2)0.9237 (3)0.0809 (9)
H14A0.98180.42470.93450.121*
H14B1.08200.30151.00700.121*
H14C1.06560.35900.86260.121*
C150.24496 (19)0.44445 (19)0.3995 (2)0.0421 (6)
C160.5142 (2)0.49243 (19)0.2783 (2)0.0439 (6)
H160.57210.43370.31550.053*
C170.55434 (19)0.56697 (18)0.1965 (2)0.0396 (6)
C180.6858 (2)0.5582 (2)0.1820 (2)0.0514 (7)
H180.74690.50520.22690.062*
C190.7251 (2)0.6259 (2)0.1037 (2)0.0550 (7)
H190.81310.61980.09660.066*
C200.6339 (2)0.7040 (2)0.0344 (2)0.0541 (7)
H200.66030.74910.02010.065*
C210.5040 (2)0.7146 (2)0.0463 (2)0.0454 (6)
C220.46500 (18)0.64702 (18)0.1278 (2)0.0390 (6)
C230.4325 (3)0.8464 (2)0.1146 (3)0.0858 (9)
H23A0.35520.89270.15380.103*
H23B0.44340.78400.18120.103*
H23C0.51740.90270.07390.103*
N10.29100 (15)0.26075 (14)0.50166 (15)0.0356 (4)
N20.48504 (16)0.11625 (14)0.62165 (17)0.0415 (5)
H2B0.50270.18830.59790.050*
N30.59051 (16)0.04457 (15)0.67688 (16)0.0412 (5)
N40.36241 (16)0.42826 (14)0.37266 (17)0.0416 (5)
H4B0.41610.36850.40190.050*
N50.39901 (16)0.50634 (15)0.30027 (17)0.0421 (5)
O10.31393 (14)0.02534 (13)0.62118 (15)0.0538 (4)
O20.68928 (13)0.15184 (13)0.77465 (14)0.0486 (4)
H20.62810.10740.74190.073*
O30.90350 (14)0.27240 (14)0.87475 (16)0.0599 (5)
O40.18031 (14)0.53748 (13)0.38126 (17)0.0587 (5)
O50.33579 (13)0.66089 (13)0.13551 (14)0.0518 (4)
H50.32290.61680.18530.078*
O60.40564 (16)0.78740 (16)0.01889 (16)0.0710 (5)
O70.60588 (14)0.26205 (13)0.46378 (16)0.0578 (5)
H7B0.63430.19890.43450.069*
H7C0.68320.30080.50650.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0374 (9)0.0329 (10)0.0390 (12)0.0007 (9)0.0106 (9)0.0002 (9)
C20.0402 (10)0.0493 (12)0.0642 (15)0.0075 (10)0.0181 (10)0.0158 (11)
C30.0391 (10)0.0674 (15)0.0832 (17)0.0024 (11)0.0263 (11)0.0219 (13)
C40.0459 (10)0.0436 (12)0.0612 (14)0.0032 (10)0.0243 (10)0.0153 (11)
C50.0392 (9)0.0341 (10)0.0369 (11)0.0024 (8)0.0165 (8)0.0046 (9)
C60.0461 (10)0.0345 (11)0.0393 (11)0.0036 (9)0.0211 (8)0.0075 (9)
C70.0506 (10)0.0400 (11)0.0380 (12)0.0027 (9)0.0175 (9)0.0097 (9)
C80.0521 (10)0.0406 (11)0.0349 (11)0.0028 (9)0.0148 (8)0.0074 (9)
C90.0531 (11)0.0449 (13)0.0529 (14)0.0023 (10)0.0197 (10)0.0081 (11)
C100.0368 (10)0.0601 (15)0.0636 (15)0.0041 (11)0.0162 (10)0.0045 (12)
C110.0393 (10)0.0637 (15)0.0518 (14)0.0098 (10)0.0100 (10)0.0070 (12)
C120.0448 (10)0.0425 (12)0.0405 (12)0.0056 (10)0.0119 (9)0.0087 (10)
C130.0442 (9)0.0446 (12)0.0365 (12)0.0023 (9)0.0131 (8)0.0050 (9)
C140.0741 (14)0.0699 (15)0.095 (2)0.0361 (12)0.0131 (14)0.0396 (14)
C150.0360 (10)0.0385 (11)0.0488 (13)0.0014 (9)0.0116 (9)0.0081 (10)
C160.0406 (11)0.0346 (11)0.0402 (13)0.0024 (9)0.0089 (9)0.0081 (10)
C170.0416 (10)0.0365 (11)0.0378 (12)0.0022 (9)0.0132 (9)0.0020 (10)
C180.0432 (10)0.0523 (13)0.0577 (15)0.0076 (10)0.0177 (10)0.0074 (12)
C190.0432 (11)0.0585 (15)0.0664 (16)0.0019 (11)0.0248 (10)0.0090 (12)
C200.0588 (12)0.0526 (14)0.0533 (14)0.0021 (11)0.0273 (10)0.0047 (12)
C210.0520 (10)0.0440 (12)0.0463 (12)0.0045 (10)0.0240 (9)0.0051 (10)
C220.0412 (9)0.0358 (11)0.0412 (12)0.0029 (9)0.0179 (9)0.0034 (9)
C230.1134 (17)0.0934 (18)0.0901 (17)0.0406 (15)0.0655 (13)0.0558 (14)
N10.0401 (8)0.0302 (8)0.0361 (9)0.0001 (7)0.0137 (7)0.0049 (7)
N20.0422 (8)0.0338 (9)0.0503 (10)0.0065 (7)0.0152 (7)0.0151 (8)
N30.0444 (8)0.0391 (9)0.0410 (10)0.0111 (8)0.0137 (7)0.0116 (8)
N40.0415 (8)0.0346 (9)0.0534 (10)0.0062 (7)0.0172 (7)0.0208 (8)
N50.0439 (8)0.0351 (9)0.0487 (10)0.0021 (7)0.0201 (7)0.0106 (8)
O10.0604 (7)0.0417 (8)0.0726 (10)0.0074 (7)0.0346 (7)0.0234 (7)
O20.0378 (7)0.0493 (8)0.0623 (9)0.0065 (6)0.0173 (6)0.0219 (7)
O30.0537 (8)0.0516 (9)0.0729 (11)0.0121 (7)0.0138 (8)0.0265 (8)
O40.0478 (7)0.0402 (8)0.0532 (12)0.0057 (6)0.0209 (7)0.0202 (8)
O50.0485 (7)0.0568 (8)0.0641 (9)0.0165 (6)0.0302 (6)0.0254 (7)
O60.0794 (9)0.0835 (11)0.0773 (11)0.0287 (8)0.0452 (8)0.0485 (9)
O70.0470 (7)0.0436 (8)0.0820 (11)0.0088 (7)0.0210 (7)0.0133 (8)
Geometric parameters (Å, º) top
C1—N11.333 (2)C14—H14C0.9600
C1—C21.386 (3)C15—O41.232 (2)
C1—C151.491 (3)C15—N41.341 (3)
C2—C31.371 (3)C16—N51.288 (3)
C2—H2A0.9300C16—C171.445 (3)
C3—C41.382 (3)C16—H160.9300
C3—H30.9300C17—C221.393 (3)
C4—C51.385 (3)C17—C181.407 (3)
C4—H4A0.9300C18—C191.362 (3)
C5—N11.334 (3)C18—H180.9300
C5—C61.495 (3)C19—C201.390 (3)
C6—O11.226 (2)C19—H190.9300
C6—N21.345 (2)C20—C211.382 (3)
C7—N31.278 (2)C20—H200.9300
C7—C81.442 (3)C21—O61.371 (3)
C7—H7A0.9300C21—C221.389 (3)
C8—C131.394 (3)C22—O51.361 (2)
C8—C91.404 (3)C23—O61.411 (3)
C9—C101.359 (3)C23—H23A0.9600
C9—H90.9300C23—H23B0.9600
C10—C111.387 (3)C23—H23C0.9600
C10—H100.9300N2—N31.373 (2)
C11—C121.377 (3)N2—H2B0.8913
C11—H110.9300N4—N51.371 (3)
C12—O31.366 (3)N4—H4B0.8904
C12—C131.400 (3)O2—H20.8200
C13—O21.357 (2)O5—H50.8200
C14—O31.427 (3)O7—H7B0.8198
C14—H14A0.9600O7—H7C0.8193
C14—H14B0.9600
N1—C1—C2122.9 (2)O4—C15—N4123.2 (2)
N1—C1—C15117.72 (17)O4—C15—C1121.95 (19)
C2—C1—C15119.32 (17)N4—C15—C1114.84 (17)
C3—C2—C1118.86 (19)N5—C16—C17120.79 (19)
C3—C2—H2A120.6N5—C16—H16119.6
C1—C2—H2A120.6C17—C16—H16119.6
C2—C3—C4119.1 (2)C22—C17—C18117.9 (2)
C2—C3—H3120.5C22—C17—C16121.88 (18)
C4—C3—H3120.5C18—C17—C16120.16 (19)
C3—C4—C5118.2 (2)C19—C18—C17121.3 (2)
C3—C4—H4A120.9C19—C18—H18119.3
C5—C4—H4A120.9C17—C18—H18119.3
N1—C5—C4123.41 (17)C18—C19—C20120.0 (2)
N1—C5—C6117.74 (17)C18—C19—H19120.0
C4—C5—C6118.85 (19)C20—C19—H19120.0
O1—C6—N2124.09 (17)C21—C20—C19120.1 (2)
O1—C6—C5121.92 (17)C21—C20—H20119.9
N2—C6—C5113.99 (17)C19—C20—H20119.9
N3—C7—C8121.70 (19)O6—C21—C20124.8 (2)
N3—C7—H7A119.1O6—C21—C22115.44 (19)
C8—C7—H7A119.1C20—C21—C22119.7 (2)
C13—C8—C9118.32 (18)O5—C22—C21117.21 (18)
C13—C8—C7121.47 (18)O5—C22—C17121.9 (2)
C9—C8—C7120.20 (19)C21—C22—C17120.85 (18)
C10—C9—C8121.0 (2)O6—C23—H23A109.5
C10—C9—H9119.5O6—C23—H23B109.5
C8—C9—H9119.5H23A—C23—H23B109.5
C9—C10—C11120.7 (2)O6—C23—H23C109.5
C9—C10—H10119.6H23A—C23—H23C109.5
C11—C10—H10119.6H23B—C23—H23C109.5
C12—C11—C10119.67 (19)C1—N1—C5117.51 (17)
C12—C11—H11120.2C6—N2—N3119.38 (17)
C10—C11—H11120.2C6—N2—H2B118.8
O3—C12—C11125.31 (18)N3—N2—H2B121.8
O3—C12—C13114.57 (18)C7—N3—N2117.11 (17)
C11—C12—C13120.1 (2)C15—N4—N5118.69 (16)
O2—C13—C8122.79 (17)C15—N4—H4B120.7
O2—C13—C12117.05 (19)N5—N4—H4B120.6
C8—C13—C12120.16 (18)C16—N5—N4118.21 (17)
O3—C14—H14A109.5C13—O2—H2109.5
O3—C14—H14B109.5C12—O3—C14117.50 (17)
H14A—C14—H14B109.5C22—O5—H5109.5
O3—C14—H14C109.5C21—O6—C23117.85 (18)
H14A—C14—H14C109.5H7B—O7—H7C97.2
H14B—C14—H14C109.5
N1—C1—C2—C30.8 (3)N5—C16—C17—C18174.76 (18)
C15—C1—C2—C3177.2 (2)C22—C17—C18—C190.1 (3)
C1—C2—C3—C40.3 (3)C16—C17—C18—C19178.87 (19)
C2—C3—C4—C50.2 (3)C17—C18—C19—C201.1 (3)
C3—C4—C5—N10.3 (3)C18—C19—C20—C211.0 (3)
C3—C4—C5—C6179.1 (2)C19—C20—C21—O6179.0 (2)
N1—C5—C6—O1166.65 (19)C19—C20—C21—C220.0 (3)
C4—C5—C6—O113.9 (3)O6—C21—C22—O50.7 (3)
N1—C5—C6—N214.1 (3)C20—C21—C22—O5179.83 (18)
C4—C5—C6—N2165.28 (18)O6—C21—C22—C17178.19 (17)
N3—C7—C8—C132.0 (3)C20—C21—C22—C170.9 (3)
N3—C7—C8—C9177.9 (2)C18—C17—C22—O5179.72 (17)
C13—C8—C9—C100.2 (3)C16—C17—C22—O51.0 (3)
C7—C8—C9—C10179.9 (2)C18—C17—C22—C210.9 (3)
C8—C9—C10—C110.7 (4)C16—C17—C22—C21177.85 (18)
C9—C10—C11—C120.9 (4)C2—C1—N1—C50.7 (3)
C10—C11—C12—O3179.2 (2)C15—C1—N1—C5177.36 (17)
C10—C11—C12—C130.5 (3)C4—C5—N1—C10.1 (3)
C9—C8—C13—O2178.94 (19)C6—C5—N1—C1179.50 (17)
C7—C8—C13—O21.2 (3)O1—C6—N2—N32.9 (3)
C9—C8—C13—C120.2 (3)C5—C6—N2—N3176.31 (17)
C7—C8—C13—C12179.7 (2)C8—C7—N3—N2179.90 (18)
O3—C12—C13—O22.0 (3)C6—N2—N3—C7173.80 (19)
C11—C12—C13—O2179.14 (19)O4—C15—N4—N512.1 (3)
O3—C12—C13—C8178.76 (19)C1—C15—N4—N5168.92 (16)
C11—C12—C13—C80.1 (3)C17—C16—N5—N4176.45 (16)
N1—C1—C15—O4164.14 (18)C15—N4—N5—C16177.98 (17)
C2—C1—C15—O417.7 (3)C11—C12—O3—C142.9 (3)
N1—C1—C15—N414.9 (3)C13—C12—O3—C14175.8 (2)
C2—C1—C15—N4163.24 (18)C20—C21—O6—C236.4 (3)
N5—C16—C17—C226.6 (3)C22—C21—O6—C23172.66 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N30.821.902.613 (2)146
N2—H2B···O70.892.303.035 (2)139
N4—H4B···O70.892.253.097 (2)160
O5—H5···N50.821.872.593 (2)146
O7—H7B···O1i0.822.042.848 (2)170
O7—H7C···O4ii0.822.122.875 (2)154
C14—H14B···O5iii0.962.563.258 (3)130
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y1, z+1.

Experimental details

Crystal data
Chemical formulaC23H21N5O6·H2O
Mr481.46
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)10.184 (2), 10.842 (1), 11.034 (2)
α, β, γ (°)98.72 (3), 110.42 (2), 92.42 (3)
V3)1122.6 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.968, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
5277, 5177, 4150
Rint0.003
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.139, 1.01
No. of reflections5177
No. of parameters317
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.20

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.

Selected geometric parameters (Å, º) top
N2—N31.373 (2)N4—N51.371 (3)
C5—C6—N2—N3176.31 (17)C1—C15—N4—N5168.92 (16)
C8—C7—N3—N2179.90 (18)C17—C16—N5—N4176.45 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N30.821.902.613 (2)146
N2—H2B···O70.892.303.035 (2)139
N4—H4B···O70.892.253.097 (2)160
O5—H5···N50.821.872.593 (2)146
O7—H7B···O1i0.822.042.848 (2)170
O7—H7C···O4ii0.822.122.875 (2)154
C14—H14B···O5iii0.962.563.258 (3)130
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y1, z+1.
 

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