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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 63| Part 1| January 2007| Pages o42-o44
doi:10.1107/S0108270106050451

3-Nitro­benzaldehyde isonicotinoyl­hydrazone monohydrate redetermined at 120 K: sheets built from O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds

CROSSMARK_Color_square_no_text.svg
Solange M. S. V. Wardell,a James L. Wardell,b John N. Low,c Christopher Glidewelld* and Marcus V. N. de Souzaa

aInstituto de Tecnologia em Fármacos, Far-Manguinhos, FIOCRUZ, 21041-250 Rio de Janeiro, RJ, Brazil, bInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, RJ, Brazil, cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 22 November 2006; accepted 23 November 2006; online 12 December 2006)

In the title compound, C13H10N4O3·H2O, the mol­ecular components are linked into complex sheets by a combination of four types of hydrogen bonds.

Comment

The structure of the title compound, (I)[link], has recently been determined using diffraction data measured at 294 K (Guo et al., 2006[Guo, M.-J., Sun, J.-C., Jing, Z.-L., Yu, M. & Chen, X. (2006). Acta Cryst. E62, o820-o821.]). Although a number of hydrogen bonds were identified and listed in this report, no indication of their action was given beyond the rather terse comment that the water of crystallization inter­acts with the organic mol­ecules through hydrogen bonds. We report here a redetermination of the structure of (I)[link] from diffraction data collected at 120 K,

[Scheme 1]
undertaken as part of a more general study of isonicotin­oyl­hydrazones (Wardell, de Souza, Ferreira et al., 2005[Wardell, S. M. S. V., de Souza, M. V. N., Ferreira, M. de L., Vasconcelos, T. R. A., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o617-o620.]; Wardell, de Souza, Wardell et al., 2005[Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o683-o689.]; Wardell et al., 2006[Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. E62, o3361-o3363.]; Low et al., 2006[Low, J. N., Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L. & Glidewell, C. (2006). Acta Cryst. C62, o444-o446.]) and we provide a full description of the supra­molecular aggregation, along with a brief comparison of the crystal structure of this monohydrate, obtained by crystallization of the anhydrous form from ethanol, with that of the anhydrous compound, (II)[link], crystals of which were obtained from a solution in methanol (Wardell, de Souza, Wardell et al., 2005[Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o683-o689.]).

The space group and unit-cell dimensions at 120 and 294 K indicate that no phase change occurs between these temperatures, although we note a marked difference between the values of b at these two temperatures, while the value of c is in fact larger at 120 K than that reported at 294 K (Guo et al., 2006[Guo, M.-J., Sun, J.-C., Jing, Z.-L., Yu, M. & Chen, X. (2006). Acta Cryst. E62, o820-o821.]). The conformation of the organic component, as defined by the leading torsion angles (Table 1[link]), shows a significant twist about the C14—C17 bond, removing the isonicotinoyl ring from the plane of the central spacer unit, and a modest rotation of the nitro group around the C23—N23 bond, taking it away from the plane of the adjacent aryl ring. We note that the mol­ecular conformation was not mentioned in the earlier report on (I)[link] (Guo et al., 2006[Guo, M.-J., Sun, J.-C., Jing, Z.-L., Yu, M. & Chen, X. (2006). Acta Cryst. E62, o820-o821.]).

The independent mol­ecular components are linked into sheets by four structurally significant hydrogen bonds, one each of types O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O (Table 2[link]). These correspond with the inter­molecular inter­actions reported earlier, although comparison is not eased by the unsystematic atom labelling adopted in the earlier report. There is an N—H⋯O hydrogen bond within the selected asymmetric unit (Fig. 1[link]), and the formation of the hydrogen-bonded sheet is readily analysed in terms of two simple substructures, each one-dimensional. In the first of these substructures, water atom O2 at (x, y, z) acts as a hydrogen-bond donor, via atom H2A, to carbonyl atom O1 at (−[{1\over 2}] + x, y, [{1\over 2}] − z), so forming a C22(6) (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) chain running parallel to the [100] direction and generated by the a-glide plane at z = [{1 \over 4}] (Fig. 2[link]). In the second substructure, water atom O2 at (x, y, z) acts as a hydrogen-bond donor, this time via atom H2B, to pyridyl atom N11 at ([{1\over 2}] − x, 1 − y, [{1\over 2}] + z), so forming a C22(9) chain running parallel to the [001] direction and generated by the 21 screw axis along ([{1 \over 4}], [{1 \over 2}], z) (Fig. 3[link]). The combination of these two motifs then generates a sheet parallel to (010) lying in the domain 0.28 < y < 0.72 (Fig. 4[link]). The sheet formation is modestly reinforced by the C—H⋯O hydrogen bond. A second sheet containing 21 screw axes at y = 0 lies in the domain −0.22 < y < 0.22, but there are no direction-specific inter­actions between adjacent sheets. In particular, C—H⋯π hydrogen bonds and π–π stacking inter­actions are absent.

Although the original report on compound (I)[link] (Guo et al., 2006[Guo, M.-J., Sun, J.-C., Jing, Z.-L., Yu, M. & Chen, X. (2006). Acta Cryst. E62, o820-o821.]) gave no descriptive analysis of the actions of the hydrogen bonds, it did contain a packing diagram. However, this diagram shows an edge-on view of several (010) sheets, such that it is not possible, in the absence of any descriptive text, to discern from this diagram whether the supra­molecular structure is actually composed of chains or of sheets.

In the structure of the anhydrous compound, (II)[link], which crystallizes in the space group P21/c, the mol­ecules are again linked into sheets. However, as the strong hydrogen bonds of types O—H⋯O and N—H⋯O are both absent, their place is taken by the less favourable N—H⋯N and C—H⋯N types, along with a C—H⋯O hydrogen bond.

[Figure 1]
Figure 1
The independent mol­ecular components of compound (I)[link], 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.
[Figure 2]
Figure 2
Part of the crystal structure of compound (I)[link], showing the formation of a hydrogen-bonded C22(6) chain along [100]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (−[{1\over 2}] + x, y, [{1\over 2}] − z) and ([{1\over 2}] + x, y, [{1\over 2}] − z), respectively.
[Figure 3]
Figure 3
Part of the crystal structure of compound (I)[link], showing the formation of a hydrogen-bonded C22(9) chain along [001]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions ([{1\over 2}] − x, 1 − y, [{1\over 2}] + z) and ([{1\over 2}] − x, 1 − y, [-{1\over 2}] + z), respectively.
[Figure 4]
Figure 4
A stereoview of part of the crystal structure of compound (I)[link], showing the formation of a hydrogen-bonded sheet parallel to (010). For the sake of clarity, H atoms bonded to C atoms have been omitted.

Experimental

The anhydrous compound, (II)[link], was obtained as described previously (Wardell, de Souza, Wardell et al., 2005[Wardell, S. M. S. V., de Souza, M. V. N., Ferreira, M. de L., Vasconcelos, T. R. A., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o617-o620.]). The title compound, (I)[link], was obtained by slow evaporation of a solution of (II)[link] in reagent grade ethanol (ethanol–water, 97:3 v/v).

Crystal data

  • C13H10N4O3·H2O

  • Mr = 288.27

  • Orthorhombic, P b c a

  • a = 13.3271 (5) Å

  • b = 12.7054 (5) Å

  • c = 15.7748 (6) Å

  • V = 2671.09 (18) Å3

  • Z = 8

  • Dx = 1.434 Mg m−3

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 120 (2) K

  • Plate, colourless

  • 0.24 × 0.20 × 0.04 mm
Data collection

  • Bruker–Nonius KappaCCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.947, Tmax = 0.996

  • 25385 measured reflections

  • 3036 independent reflections

  • 2037 reflections with I > 2σ(I)

  • Rint = 0.077

  • θmax = 27.5°
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.155

  • S = 1.14

  • 3036 reflections

  • 191 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0547P)2 + 1.8808P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.23 e Å−3

  • Extinction correction: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.])

  • Extinction coefficient: 0.0056 (11)

Table 1
Selected torsion angles (°)

C13—C14—C17—N17 −22.6 (3)
C14—C17—N17—N27 176.80 (18)
C17—N17—N27—C27 179.2 (2)
N17—N27—C27—C21 −179.87 (19)
N27—C27—C21—C22 2.1 (3)
C22—C23—N23—O231 −8.2 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N17—H17⋯O2 0.88 2.00 2.865 (2) 166
O2—H2A⋯O1i 0.83 1.99 2.798 (2) 164
O2—H2B⋯N11ii 0.93 1.93 2.860 (3) 177
C25—H25⋯O232iii 0.95 2.35 3.195 (3) 148
Symmetry codes: (i) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}].

The space group Pbca was uniquely assigned from the systematic absences. All H atoms were located in difference maps and then treated as riding atoms, with distances C—H = 0.95 Å, N—H = 0.88 Å and O—H = 0.83–0.93 Å, and with Uiso(H) = 1.2Ueq(C,N,O).

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270106050451/sk3078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270106050451/sk3078Isup2.hkl


Comment top

The structure of the title compound, (I), has recently been determined using diffraction data measured at 294 K (Guo et al., 2006). Although a number of hydrogen bonds were identified and listed in this report, no indication of their action was given beyond the rather terse comment that the water of crystallization interacts with the organic molecules through hydrogen bonds. Here, we report a redetermination of the structure of (I) from diffraction data collected at 120 K, undertaken as part of a more general study of isonicotinoylhydrazones (Wardell, de Souza, Ferreira et al., 2005; Wardell, de Souza, Wardell et al., 2005; Wardell et al., 2006; Low et al., 2006) and we provide a full description of the supramolecular aggregation, along with a brief comparison of the crystal structure of this monohydrate, obtained by crystallization of the anhydrous form from ethanol, with that of the anhydrous compound, (II), crystals of which were obtained from a solution in methanol (Wardell, de Souza, Wardell et al., 2005).

The space group and unit-cell dimensions at 120 K and 294 K indicate that no phase change occurs between these temperatures, although we note a marked difference between the values of b at these two temperatures, while the value of c is in fact larger at 120 K than that reported at 294 K (Guo et al., 2006). The conformation of the organic component, as defined by the leading torsion angles (Table 1), shows a significant twist about the C14—C17 bond, removing the isonicotinoyl ring from the plane of the central spacer unit, and a modest rotation of the nitro group around the C23—N23 bond, taking it away from the plane of the adjacent aryl ring. We note that the molecular conformation was not mentioned in the earlier report on (I) (Guo et al., 2006).

The independent molecular components are linked into sheets by four structurally significant hydrogen bonds, one each of types O—H···O, O—H···N, N—H···O and C—H···O (Table 2). These correspond with the intermolecular interactions reported earlier, although comparison is not eased by the unsystematic atom labelling adopted in the earlier report. There is an N—H···O hydrogen bond within the selected asymmetric unit (Fig. 1), and the formation of the hydrogen-bonded sheet is readily analysed in terms of two simple sub-structures, each one-dimensional. In the first of these sub-structures, water atom O2 at (x, y, z) acts as a hydrogen-bond donor, via atom H2A, to the carbonyl atom O1 at (−1/2 + x, y, 1/2 − z), so forming a C22(6) (Bernstein et al., 1995) chain running parallel to the [100] direction and generated by the a-glide plane at z = 1/4 (Fig. 2). In the second sub-structure, water atom O2 at (x, y, z) acts as a hydrogen-bond donor, this time via atom H2B, to the pyridyl atom N11 at (1/2 − x, 1 − y, 1/2 + z), so forming a C22(9) chain running parallel to the [001] direction and generated by the 21 screw axis along (1/4, 1/2, z) (Fig. 3). The combination of these two motifs then generates a sheet parallel to (010) lying in the domain 0.28 < y < 0.72 (Fig. 4). The sheet formation is modestly reinforced by the C—H···O hydrogen bond. A second sheet containing 21 screw axes at y = 0 lies in the domain −0.22 < y < 0.22, but there are no direction-specific interactions between adjacent sheets. In particular, C—H···π hydrogen bonds and π–π stacking interactions are absent.

Although the original report on compound (I) (Guo et al., 2006) gave no descriptive analysis of the actions of the hydrogen bonds, it did contain a packing diagram. However, this diagram shows an edge-on view of several (010) sheets, such that it is not possible, in the absence of any descriptive text, to discern from this diagram whether the supramolecular structure is actually composed of chains or of sheets.

In the structure of the anhydrous compound, (II), which crystallizes in space group P21/c, the molecules are again linked into sheets. However, as the strong hydrogen bonds of types O—H.·O and N—H···O are both absent, their place is taken by the less favourable N—H···N and C—H···N types, along with a C—H···O hydrogen bond.

Experimental top

The anhydrous compound, (II), was obtained as described previously (Wardell, de Souza, Wardell et al., 2005). The title compound, (I), was obtained by slow evaporation of a solution of (II) in ethanol. [Source of water molecule?]

Refinement top

The space group Pbca was uniquely assigned from the systematic absences. All H atoms were located in difference maps and then treated as riding atoms, with distances C—H = 0.95 Å, N—H = 0.88 Å and O—H = 0.83–0.93 Å, and with Uiso(H) = 1.2Ueq(C,N,O).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The independent molecular components of compound (I), 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.
[Figure 2] Fig. 2. Part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded C22(6) chain along [100]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (−1/2 + x, y, 1/2 − z) and (1/2 + x, y, 1/2 − z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded C22(9) chain along [001]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (1/2 − x, 1 − y, 1/2 + z) and (1/2 − x, 1 − y,- 1/2 + z), respectively.
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded sheet parallel to (010). For the sake of clarity, H atoms bonded to [Text missing?] atoms have been omitted.
3-Nitrobenzaldehyde isonicotinoylhydrazone monohydrate top
Crystal data top
C13H10N4O3·H2OF(000) = 1200
Mr = 288.27Dx = 1.434 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3036 reflections
a = 13.3271 (5) Åθ = 2.6–27.5°
b = 12.7054 (5) ŵ = 0.11 mm−1
c = 15.7748 (6) ÅT = 120 K
V = 2671.09 (18) Å3Plate, colourless
Z = 80.24 × 0.20 × 0.04 mm
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer		3036 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2037 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.6°
ϕ and ω scansh = −17→15
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −16→14
Tmin = 0.947, Tmax = 0.996l = −20→17
25385 measured reflections
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) = 0.155 w = 1/[σ2(Fo2) + (0.0547P)2 + 1.8808P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
3036 reflectionsΔρmax = 0.23 e Å−3
191 parametersΔρmin = −0.23 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0056 (11)
Crystal data top
C13H10N4O3·H2OV = 2671.09 (18) Å3
Mr = 288.27Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.3271 (5) ŵ = 0.11 mm−1
b = 12.7054 (5) ÅT = 120 K
c = 15.7748 (6) Å0.24 × 0.20 × 0.04 mm
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer		3036 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2037 reflections with I > 2σ(I)
Tmin = 0.947, Tmax = 0.996Rint = 0.077
25385 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.14Δρmax = 0.23 e Å−3
3036 reflectionsΔρmin = −0.23 e Å−3
191 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.59192 (11)0.46569 (13)0.25135 (11)0.0367 (4)
O20.24327 (11)0.45409 (14)0.37125 (11)0.0388 (5)
O2310.81277 (12)0.30884 (14)0.55770 (14)0.0458 (5)
O2320.80418 (13)0.28086 (16)0.69298 (14)0.0537 (6)
N110.31790 (15)0.55232 (17)0.04499 (14)0.0403 (5)
N170.45206 (13)0.43701 (15)0.33013 (13)0.0302 (5)
N230.76519 (15)0.29666 (16)0.62361 (16)0.0390 (6)
N270.50754 (13)0.40251 (15)0.39867 (13)0.0314 (5)
C120.27977 (17)0.4947 (2)0.10811 (16)0.0366 (6)
C130.33378 (16)0.46409 (19)0.17870 (16)0.0328 (6)
C140.43307 (16)0.49597 (17)0.18589 (17)0.0308 (6)
C150.47309 (17)0.55755 (19)0.12166 (17)0.0374 (6)
C160.41381 (18)0.5825 (2)0.05293 (18)0.0418 (7)
C170.50010 (16)0.46530 (16)0.25819 (16)0.0301 (5)
C210.50702 (15)0.34108 (18)0.54147 (16)0.0294 (5)
C220.61178 (16)0.33407 (17)0.54532 (16)0.0302 (5)
C230.65486 (16)0.30217 (17)0.62007 (17)0.0319 (6)
C240.60063 (18)0.27562 (18)0.69141 (17)0.0360 (6)
C250.49693 (18)0.28148 (18)0.68657 (18)0.0377 (6)
C260.45101 (16)0.31444 (18)0.61238 (17)0.0340 (6)
C270.45683 (16)0.37857 (17)0.46439 (16)0.0305 (5)
H120.21160.47350.10420.044*
H130.30360.42210.22150.039*
H150.54030.58210.12500.045*
H160.44250.62340.00870.050*
H170.38620.44050.33330.036*
H270.38580.38510.46350.037*
H220.65200.35090.49750.036*
H240.63320.25410.74210.043*
H250.45720.26280.73430.045*
H260.37990.31890.61010.041*
H2A0.19060.45670.34320.047*
H2B0.22170.45030.42750.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0284 (10)0.0388 (12)0.0536 (14)0.0031 (9)−0.0011 (10)0.0106 (10)
C120.0223 (11)0.0392 (14)0.0483 (15)−0.0016 (10)−0.0007 (11)0.0013 (12)
C130.0232 (11)0.0322 (13)0.0430 (15)−0.0029 (9)0.0006 (10)0.0024 (11)
C140.0211 (10)0.0232 (11)0.0482 (15)0.0007 (9)0.0007 (10)−0.0017 (10)
C150.0220 (11)0.0304 (12)0.0597 (17)−0.0016 (9)0.0002 (11)0.0079 (12)
C160.0306 (12)0.0346 (14)0.0603 (18)0.0008 (10)0.0035 (12)0.0135 (13)
C170.0209 (10)0.0233 (12)0.0462 (15)−0.0011 (9)0.0005 (10)−0.0040 (11)
O10.0174 (8)0.0383 (10)0.0544 (11)−0.0002 (7)0.0001 (7)−0.0014 (8)
N170.0171 (8)0.0306 (10)0.0428 (12)0.0002 (7)−0.0029 (8)−0.0025 (9)
N270.0222 (9)0.0262 (10)0.0458 (12)0.0009 (8)−0.0047 (9)−0.0040 (9)
C270.0186 (10)0.0243 (11)0.0487 (15)−0.0008 (9)−0.0019 (10)−0.0040 (10)
C210.0201 (10)0.0222 (11)0.0460 (14)−0.0005 (8)−0.0008 (10)−0.0049 (10)
C220.0213 (10)0.0239 (11)0.0454 (14)−0.0007 (9)0.0007 (10)−0.0055 (10)
C230.0200 (10)0.0218 (11)0.0539 (16)0.0008 (9)−0.0033 (10)−0.0040 (11)
N230.0241 (10)0.0274 (11)0.0656 (16)0.0004 (8)−0.0092 (11)−0.0049 (10)
O2310.0222 (8)0.0415 (10)0.0737 (14)0.0019 (7)0.0029 (9)−0.0063 (9)
O2320.0349 (10)0.0533 (13)0.0729 (14)−0.0014 (9)−0.0226 (10)0.0032 (10)
C240.0336 (12)0.0246 (12)0.0498 (16)0.0016 (10)−0.0051 (12)0.0023 (11)
C250.0319 (12)0.0270 (12)0.0540 (17)0.0017 (10)0.0060 (11)0.0057 (11)
C260.0203 (10)0.0249 (12)0.0569 (16)0.0014 (9)0.0015 (11)0.0000 (11)
O20.0195 (7)0.0505 (11)0.0465 (11)0.0016 (7)−0.0011 (7)−0.0095 (9)
Geometric parameters (Å, º) top
N11—C121.337 (3)C27—H270.95
N11—C161.340 (3)C21—C261.387 (3)
C12—C131.382 (3)C21—C221.400 (3)
C12—H120.95C22—C231.373 (3)
C13—C141.389 (3)C22—H220.95
C13—H130.95C23—C241.379 (3)
C14—C151.387 (3)C23—N231.473 (3)
C14—C171.500 (3)N23—O2311.227 (3)
C15—C161.379 (4)N23—O2321.228 (3)
C15—H150.95C24—C251.386 (3)
C16—H160.95C24—H240.95
C17—O11.228 (3)C25—C261.385 (4)
C17—N171.352 (3)C25—H250.95
N17—N271.381 (3)C26—H260.95
N17—H170.88O2—H2A0.83
N27—C271.274 (3)O2—H2B0.93
C27—C211.467 (3)
C12—N11—C16116.7 (2)N27—C27—H27119.7
N11—C12—C13123.8 (2)C21—C27—H27119.7
N11—C12—H12118.1C26—C21—C22119.1 (2)
C13—C12—H12118.1C26—C21—C27120.15 (19)
C12—C13—C14118.7 (2)C22—C21—C27120.7 (2)
C12—C13—H13120.6C23—C22—C21118.2 (2)
C14—C13—H13120.6C23—C22—H22120.9
C15—C14—C13118.1 (2)C21—C22—H22120.9
C15—C14—C17118.2 (2)C22—C23—C24123.6 (2)
C13—C14—C17123.6 (2)C22—C23—N23117.7 (2)
C16—C15—C14119.0 (2)C24—C23—N23118.7 (2)
C16—C15—H15120.5O231—N23—O232123.8 (2)
C14—C15—H15120.5O231—N23—C23118.5 (2)
N11—C16—C15123.6 (2)O232—N23—C23117.6 (2)
N11—C16—H16118.2C23—C24—C25117.7 (2)
C15—C16—H16118.2C23—C24—H24121.2
O1—C17—N17123.1 (2)C25—C24—H24121.2
O1—C17—C14121.7 (2)C26—C25—C24120.2 (2)
N17—C17—C14115.17 (19)C26—C25—H25119.9
C17—N17—N27119.21 (18)C24—C25—H25119.9
C17—N17—H17120.4C25—C26—C21121.2 (2)
N27—N17—H17120.4C25—C26—H26119.4
C27—N27—N17115.38 (18)C21—C26—H26119.4
N27—C27—C21120.65 (19)H2A—O2—H2B104.4
C16—N11—C12—C13−1.1 (4)N27—C27—C21—C26−179.5 (2)
N11—C12—C13—C141.1 (4)N27—C27—C21—C222.1 (3)
C12—C13—C14—C150.2 (3)C26—C21—C22—C23−0.8 (3)
C12—C13—C14—C17−178.2 (2)C27—C21—C22—C23177.6 (2)
C13—C14—C15—C16−1.4 (4)C21—C22—C23—C240.7 (4)
C17—C14—C15—C16177.2 (2)C21—C22—C23—N23−179.1 (2)
C12—N11—C16—C15−0.2 (4)C22—C23—N23—O231−8.2 (3)
C14—C15—C16—N111.4 (4)C24—C23—N23—O231172.0 (2)
C15—C14—C17—O1−21.4 (3)C22—C23—N23—O232171.2 (2)
C13—C14—C17—O1157.0 (2)C24—C23—N23—O232−8.6 (3)
C15—C14—C17—N17159.0 (2)C22—C23—C24—C250.2 (4)
C13—C14—C17—N17−22.6 (3)N23—C23—C24—C25180.0 (2)
O1—C17—N17—N27−2.8 (3)C23—C24—C25—C26−0.9 (4)
C14—C17—N17—N27176.80 (18)C24—C25—C26—C210.7 (4)
C17—N17—N27—C27179.2 (2)C22—C21—C26—C250.2 (3)
N17—N27—C27—C21−179.87 (19)C27—C21—C26—C25−178.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O20.882.002.865 (2)166
O2—H2A···O1i0.831.992.798 (2)164
O2—H2B···N11ii0.931.932.860 (3)177
C25—H25···O232iii0.952.353.195 (3)148
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x+1/2, −y+1, z+1/2; (iii) x−1/2, y, −z+3/2.

Experimental details

Crystal data
Chemical formulaC13H10N4O3·H2O
Mr288.27
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)120
a, b, c (Å)13.3271 (5), 12.7054 (5), 15.7748 (6)
V (Å3)2671.09 (18)
Z8
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.24 × 0.20 × 0.04
Data collection
DiffractometerBruker Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.947, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections		25385, 3036, 2037
Rint0.077
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.155, 1.14
No. of reflections3036
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.23

Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected torsion angles (º) top
C13—C14—C17—N17−22.6 (3)N17—N27—C27—C21−179.87 (19)
C14—C17—N17—N27176.80 (18)N27—C27—C21—C222.1 (3)
C17—N17—N27—C27179.2 (2)C22—C23—N23—O231−8.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O20.882.002.865 (2)166
O2—H2A···O1i0.831.992.798 (2)164
O2—H2B···N11ii0.931.932.860 (3)177
C25—H25···O232iii0.952.353.195 (3)148
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x+1/2, −y+1, z+1/2; (iii) x−1/2, y, −z+3/2.
 

Acknowledgements

The X-ray data were collected at the EPSRC National Crystallography Service, University of Southampton, England; the authors thank the staff of the Service for all their help and advice. JLW thanks CNPq and FAPERJ for financial support.

References

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 First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
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 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
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 First citationWardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o683–o689.  CSD CrossRef CAS IUCr Journals Google Scholar
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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 63| Part 1| January 2007| Pages o42-o44
doi:10.1107/S0108270106050451
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