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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 62| Part 1| January 2006| Pages o47-o49
doi:10.1107/S0108270105040230

Pyrrole-2-carbaldehyde isonicotinoylhydrazone monohydrate redetermined at 120 K

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

aFundação Oswaldo Cruz, Far Manguinhos, Rua Sizenando Nabuco, 100 Manguinhos, 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 1 December 2005; accepted 2 December 2005; online 24 December 2005)

In the title compound, C11H10N4O·H2O, there are five independent hydrogen bonds, of O—H⋯O, O—H⋯N and N—H⋯O types, which link the components into complex sheets parallel to (001).

Similar articles

Comment

As part of a study of isonicotinoylhydrazones, we have investigated the title compound, (I)[link]. The structure of this monohydrate was recently reported based on diffraction data collected at ambient temperature (Safoklov et al., 2002[Safoklov, B. B., Atovmyan, E. G., Nikonova, L. A., Tkachev, V. V. & Aldoshin, S. M. (2002). Russ. Chem. Bull. 51, 2224-2229.]), and it is clear from the unit-cell dimensions and space group that no phase change has occurred between ambient temperature and 120 K. The authors identified five independent hydrogen bonds in the structure but, although the coordinates of the H atoms were all refined, no s.u. values were quoted for the hydrogen-bond parameters and the symmetry-equivalent components involved in the hydrogen bonds were not identified. Similarly, the resulting supramolecular structure was not analysed in detail and, in particular, its dimensionality was not

[Scheme 1]
specified. We have now taken the opportunity to redetermine the structure of compound (I)[link] using diffraction data collected at 120 K, and we report here a full descriptive analysis of the supramolecular structure thus established.

Within the substituted hydrazone component, there is a clear distinction between single and double bonds (Table 1[link]) within the spacer unit between the rings. This unit adopts an all-trans configuration. In the pyrrole ring, however, the C—C distances vary rather little, consistent with the aromatic character of this ring. The intrachain bond angles in the spacer unit are all well below 120°, while the torsion angles indicate near planarity of the mol­ecule, apart from the pyridyl ring, which is rotated significantly out of the plane of the rest of the mol­ecule, possibly driven by repulsive inter­actions between the H atoms bonded to atoms C13 and N17 (Fig. 1[link]). Mol­ecules of the organic component of (I)[link] have no inter­nal symmetry and hence are chiral and, in the absence of inversion twinning, each crystal will contain only one enanti­omer.

There are five hydrogen bonds in the structure of (I)[link], two each of the O—H⋯O and N—H⋯O types and one of the O—H⋯O type (Table 2[link]). Three of these occur within the selected asymmetric unit (Fig. 1[link]), such that the water mol­ecule is effectively tethered to the organic component. The three-centre O—H⋯(N,O) system involving atom H2A is almost planar. There are thus two hydrogen bonds available to link these two-mol­ecule aggregates, and the resulting sheet structure is readily analysed in terms of two independent one-dimensional substructures.

Amide atom N17 at (x, y, z) acts as a hydrogen-bond donor to water atom O2 at (−1 + x, y, z), so generating by translation a C22(5)[R12(5)][R22(7)] chain of rings (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) running parallel to the [100] direction (Fig. 2[link]). In addition, water atom O2 at (x, y, z) acts as hydrogen-bond donor to pyridyl atom N11 at (1 − x, −[{1\over 2}] + y, [{3\over 2}] − z), so forming a C22(9) chain running parallel to the [010] direction and generated by the 21 screw axis along ([{1 \over 2}], y, [{3 \over 4}]) (Fig. 3[link]). Water atom O2 thus acts both as a double acceptor and as a triple donor of hydrogen bonds.

The combination of these two rather elaborate substructures then generates a complex and deeply puckered (001) sheet (Fig. 3[link]) lying in the domain 0.41 < z < 1.09 and containing R66(23) rings, in addition to the R12(5) and R22(7) rings within the asymmetric unit (Fig. 1[link]). A second similar sheet, generated by the 21 axes at z = [{1 \over 4}], lies in the domain −0.09 < z < 0.59. However, there are no direction-specific inter­actions between adjacent sheets. In particular, X—H⋯π(pyridine) and X—H⋯π(pyrrole) hydrogen bonds (X = O, N or C) and π–π stacking inter­actions are all absent.

[Figure 1]
Figure 1
The independent mol­ecular components of (I), showing the atom-labelling scheme and the hydrogen bonds within the selected asymmetric unit (dashed lines). 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 (I), showing the formation of a chain of rings 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 + x, y, z) and (1 + x, y, z), respectively.
[Figure 3]
Figure 3
A stereoview of part of the crystal structure of (I), showing the formation of an (001) sheet by the combination of [100] and [010] chains. For the sake of clarity, H atoms bonded to C atoms have been omitted.

Experimental

Equimolar quanti­ties (2 mmol) of pyrrole-2-carbaldehyde and isoniazid (isonicotinoylhydrazine) in tetra­hydro­furan (20 ml) were heated under reflux under a dinitro­gen atmosphere for 6 h. The resulting mixture was then concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a hexane–ethyl acetate gradient. Recrystallization from ethanol provided crystals of the title compound suitable for single-crystal X-ray diffraction (yield 78%, m.p. 507–509 K). MS (m/z): 214 (M+). 1H NMR (DMSO-d6): δ 11.78 (1H, s, NH), 11.64 (1H, s, NH), 8.78 (2H, d, J = 5.5 Hz), 8.31 (1H, s, C=N—H), 7.82 (2H, d, J = 5.5 Hz), 6.96 (1H, s), 6.55 (1H, s), 6.17 (1H, d, J = 2.5 Hz); 13C NMR (DMSO-d6): δ 160.9, 150.2, 141.8, 140.7, 126.6, 122.9, 121.4, 113.9, 109.3; IR (KBr, ν, cm−1): 3213 (NH), 1647 (CO).

Crystal data

  • C11H10N4O·H2O

  • Mr = 232.25

  • Orthorhombic, P 21 21 21

  • a = 6.4224 (3) Å

  • b = 7.2115 (5) Å

  • c = 23.6073 (16) Å

  • V = 1093.38 (12) Å3

  • Z = 4

  • Dx = 1.411 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 1237 reflections

  • θ = 3.0–26.5°

  • μ = 0.10 mm−1

  • T = 120 (2) K

  • Needle, yellow

  • 0.44 × 0.06 × 0.06 mm
Data collection

  • 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 = 0.967, Tmax = 0.994

  • 5095 measured reflections

  • 1279 independent reflections

  • 1157 reflections with I > 2σ(I)

  • Rint = 0.054

  • θmax = 26.5°

  • h = −7 → 7

  • k = −8 → 8

  • l = −17 → 29
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.148

  • S = 1.17

  • 1279 reflections

  • 155 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0372P)2 + 2.0901P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.41 e Å−3

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

  • Extinction coefficient: 0.031 (6)

Table 1
Selected geometric parameters (Å, °)[link]

C14—C17 1.497 (6)
C17—N17 1.345 (5)
N17—N27 1.393 (5)
N27—C26 1.289 (5)
C26—C22 1.442 (6)
N21—C22 1.365 (6)
C22—C23 1.393 (6)
C23—C24 1.397 (7)
C24—C25 1.382 (7)
C25—N21 1.366 (5)
C14—C17—N17 116.8 (4)
C17—N17—N27 116.2 (4)
N17—N27—C26 116.5 (4)
N27—C26—C22 117.9 (4)
C13—C14—C17—N17 −32.6 (6)
C14—C17—N17—N27 −169.2 (4)
C17—N17—N27—C26 −178.9 (4)
N17—N27—C26—C22 −172.1 (4)
N27—C26—C22—C23 179.3 (4)

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2A⋯O1 0.84 2.18 2.934 (5) 150
O2—H2A⋯N27 0.84 2.38 3.011 (5) 133
N21—H21⋯O2 0.88 2.07 2.950 (5) 174
N17—H17⋯O2i 0.88 1.95 2.822 (5) 173
O2—H2B⋯N11ii 0.84 2.03 2.832 (5) 159
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

The space group P212121 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 = 0.84 Å, and with Uiso(H) = 1.2Ueq(C,N,O). In the absence of significant anomalous scattering, the Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) parameter was indeterminate (Flack & Bernardinelli, 2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]). Accordingly, Friedel equivalent reflections were merged prior to the final refinement. It was therefore not possible to establish the absolute configuration of the mol­ecules in the crystal selected for data collection, but this has no chemical significance.

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/S0108270105040230/sk1894sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105040230/sk1894Isup2.hkl


Comment top

As part of a study of isonicotinoylhydrazones, we have investigated the title compound, (I). The structure of this monohydrate was recently reported based on diffraction data collected at ambient temperature (Safoklov et al., 2002), and it is clear from the unit-cell dimensions and space group that no phase change has occurred between ambient temperature and 120 K. The authors identified five independent hydrogen bonds in the structure but, although the coordinates of the H atoms were all refined, no s.u.s were quoted for the hydrogen-bond parameters and the symmetry-equivalent components involved in the hydrogen bonds were not identified. Similarly, the resulting supramolecular structure was not analysed in detail and, in particular, its dimensionality was not specified. We have now taken the opportunity to redetermine the structure of compound (I) using diffraction data collected at 120 K, and here we report a full descriptive analysis of the supramolecular structure thus established.

Within the substituted hydrazone component, there is a clear distinction between single and double bonds (Table 1) within the spacer unit between the rings. This unit adopts an all-trans configuration. In the pyrrole ring, however, the C—C distances vary rather little, consistent with the aromatic character of this ring. The intra-chain bond angles in the spacer unit are all well below 120°, while the torsion angles indicate near planarity of the molecule, apart from the pyridyl ring, which is rotated significantly out of the plane of the rest of the molecule, possibly driven by repulsive interactions between the H atoms bonded to atoms C13 and N17 (Fig. 1). Molecules of the organic component of (I) have no internal symmetry and hence are chiral and, in the absence of inversion twinning, each crystal will contain only one enantiomer.

There are five hydrogen bonds in the structure of (I), two each of O—H···O and N—H···O types and one of O—H···O type (Table 2). Three of these occur within the selected asymmetric unit (Fig. 1), such that the water molecule is effectively tethered to the organic component. The three-centre O—H····(N,O) system involving atom H2A is almost planar. There are thus two hydrogen bonds available to link these two-molecule aggregates, and the resulting sheet structure is readily analysed in terms of two independent one-dimensional substructures.

The amido atom N17 at (x, y, z) acts as hydrogen-bond donor to water atom O2 at (-1 + x, y, z), so generating by translation a C22(5)[R12(5)][R22(7))] chain of rings (Bernstein et al., 1995) running parallel to the [100] direction (Fig. 2). In addition, the water atom O2 at (x, y, z) acts as hydrogen-bond donor to pyridyl atom N11 at (1 - x, -1/2 + y, 3/2 - z), so forming a C22(9) chain running parallel to the [010] direction and generated by the 21 screw axis along (1/2, y, 3/4) (Fig. 3). The water atom O2 thus acts both as a double acceptor and as a triple donor of hydrogen bonds.

The combination of these two rather elaborate substructures then generates a complex and deeply puckered (001) sheet (Fig. 3) lying in the domain 0.41 < z < 1.09 and containing R66(23) rings, in addition to the R12(5) and R22(7) rings within the asymmetric unit (Fig. 1). A second similar sheet, generated by the 21 axes at z = 1/4, lies in the domain -0.09 < z < 0.59. However, there are no direction-specific interactions between adjacent sheets. In particular, X—H···π(pyridine) and X—H···π(pyrrole) hydrogen bonds (X = O, N or C) and π–π stacking interactions are all absent.

Experimental top

Equimolar quantities (2 mmol) of pyrrole-2-carboxaldehyde and isoniazid (isonicotinoylhydrazine) in tetrahydrofuran (20 ml) were heated under reflux in a dinitrogen atmosphere for 6 h. The resulting mixture was then concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with hexane–ethyl acetate gradient. Recrystallization from ethanol provided crystals of the title compound suitable for single-crystal X-ray diffraction (yield 78%, m.p. 507–509 K). MS, m/z: 214 (M+). Spectroscopic analysis: 1H NMR (DMSO-d6, δ, p.p.m.): 11.78 (1H, s, NH), 11.64 (1H, s, NH), 8.78 (2H, d, J = 5.5 Hz), 8.31 (1H, s, C═N—H), 7.82 (2H, d, J = 5.5 Hz), 6.96 (1H, s), 6.55 (1H, s), 6.17 (1H, d, J = 2.5 Hz); 13C NMR (DMSO-d6, δ, p.p.m.): 160.9, 150.2, 141.8, 140.7, 126.6, 122.9, 121.4, 113.9, 109.3; IR (KBr, ν, cm-1): 3213 (NH), 1647 (CO).

Refinement top

The space group P212121 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 = 0.84 Å, and with Uiso(H) = 1.2Ueq(C,N,O). In the absence of significant anomalous scattering, the Flack parameter (Flack, 1983) was indeterminate (Flack & Bernardinelli, 2000). Accordingly, Friedel-equivalent reflections were merged prior to the final refinement. It was therefore not possible to establish the absolute configuration of the molecules in the crystal selected for data collection, but this has no chemical significance.

Structure description top

As part of a study of isonicotinoylhydrazones, we have investigated the title compound, (I). The structure of this monohydrate was recently reported based on diffraction data collected at ambient temperature (Safoklov et al., 2002), and it is clear from the unit-cell dimensions and space group that no phase change has occurred between ambient temperature and 120 K. The authors identified five independent hydrogen bonds in the structure but, although the coordinates of the H atoms were all refined, no s.u.s were quoted for the hydrogen-bond parameters and the symmetry-equivalent components involved in the hydrogen bonds were not identified. Similarly, the resulting supramolecular structure was not analysed in detail and, in particular, its dimensionality was not specified. We have now taken the opportunity to redetermine the structure of compound (I) using diffraction data collected at 120 K, and here we report a full descriptive analysis of the supramolecular structure thus established.

Within the substituted hydrazone component, there is a clear distinction between single and double bonds (Table 1) within the spacer unit between the rings. This unit adopts an all-trans configuration. In the pyrrole ring, however, the C—C distances vary rather little, consistent with the aromatic character of this ring. The intra-chain bond angles in the spacer unit are all well below 120°, while the torsion angles indicate near planarity of the molecule, apart from the pyridyl ring, which is rotated significantly out of the plane of the rest of the molecule, possibly driven by repulsive interactions between the H atoms bonded to atoms C13 and N17 (Fig. 1). Molecules of the organic component of (I) have no internal symmetry and hence are chiral and, in the absence of inversion twinning, each crystal will contain only one enantiomer.

There are five hydrogen bonds in the structure of (I), two each of O—H···O and N—H···O types and one of O—H···O type (Table 2). Three of these occur within the selected asymmetric unit (Fig. 1), such that the water molecule is effectively tethered to the organic component. The three-centre O—H····(N,O) system involving atom H2A is almost planar. There are thus two hydrogen bonds available to link these two-molecule aggregates, and the resulting sheet structure is readily analysed in terms of two independent one-dimensional substructures.

The amido atom N17 at (x, y, z) acts as hydrogen-bond donor to water atom O2 at (-1 + x, y, z), so generating by translation a C22(5)[R12(5)][R22(7))] chain of rings (Bernstein et al., 1995) running parallel to the [100] direction (Fig. 2). In addition, the water atom O2 at (x, y, z) acts as hydrogen-bond donor to pyridyl atom N11 at (1 - x, -1/2 + y, 3/2 - z), so forming a C22(9) chain running parallel to the [010] direction and generated by the 21 screw axis along (1/2, y, 3/4) (Fig. 3). The water atom O2 thus acts both as a double acceptor and as a triple donor of hydrogen bonds.

The combination of these two rather elaborate substructures then generates a complex and deeply puckered (001) sheet (Fig. 3) lying in the domain 0.41 < z < 1.09 and containing R66(23) rings, in addition to the R12(5) and R22(7) rings within the asymmetric unit (Fig. 1). A second similar sheet, generated by the 21 axes at z = 1/4, lies in the domain -0.09 < z < 0.59. However, there are no direction-specific interactions between adjacent sheets. In particular, X—H···π(pyridine) and X—H···π(pyrrole) hydrogen bonds (X = O, N or C) and π–π stacking interactions are all absent.

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, and the hydrogen bonds within the selected asymmetric unit (dashed lines). 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 chain of rings 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 + x, y, z) and (1 + x, y, z), respectively.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (I), showing the formation of an (001) sheet by the combination of [100] and [010] chains. For the sake of clarity, H atoms bonded to C atoms have been omitted.
Pyrrole-2-carbaldehyde isonicotinoylhydrazone monohydrate top
Crystal data top
C11H10N4O·H2OF(000) = 488
Mr = 232.25Dx = 1.411 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1237 reflections
a = 6.4224 (3) Åθ = 3.0–26.5°
b = 7.2115 (5) ŵ = 0.10 mm−1
c = 23.6073 (16) ÅT = 120 K
V = 1093.38 (12) Å3Needle, yellow
Z = 40.44 × 0.06 × 0.06 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer		1279 independent reflections
Radiation source: Bruker Nonius FR91 rotating anode1157 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 9.091 pixels mm-1θmax = 26.5°, θmin = 3.0°
φ and ω scansh = −7→7
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −8→8
Tmin = 0.967, Tmax = 0.994l = −17→29
5095 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)] = 0.054H-atom parameters constrained
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0372P)2 + 2.0901P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max < 0.001
1279 reflectionsΔρmax = 0.35 e Å−3
155 parametersΔρmin = −0.41 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: 0.031 (6)
Crystal data top
C11H10N4O·H2OV = 1093.38 (12) Å3
Mr = 232.25Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.4224 (3) ŵ = 0.10 mm−1
b = 7.2115 (5) ÅT = 120 K
c = 23.6073 (16) Å0.44 × 0.06 × 0.06 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer		1279 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		1157 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.994Rint = 0.054
5095 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 1.17Δρmax = 0.35 e Å−3
1279 reflectionsΔρmin = −0.41 e Å−3
155 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6865 (6)0.2980 (5)0.66359 (13)0.0284 (8)
N110.1197 (7)0.3659 (6)0.80686 (15)0.0246 (9)
N170.4058 (7)0.2053 (5)0.61219 (13)0.0210 (9)
N210.7902 (6)−0.0358 (5)0.49180 (14)0.0204 (9)
N270.5395 (6)0.1447 (5)0.56955 (14)0.0195 (8)
C120.0430 (8)0.3915 (6)0.75496 (18)0.0225 (10)
C130.1532 (7)0.3589 (6)0.70543 (17)0.0186 (10)
C140.3577 (7)0.3029 (6)0.70943 (17)0.0159 (9)
C150.4432 (8)0.2752 (6)0.76360 (17)0.0239 (11)
C160.3173 (9)0.3077 (7)0.81000 (18)0.0281 (12)
C170.4967 (7)0.2699 (6)0.65957 (17)0.0188 (9)
C220.5847 (7)−0.0004 (6)0.48168 (17)0.0175 (9)
C230.5351 (8)−0.0775 (6)0.42930 (18)0.0223 (10)
C240.7161 (8)−0.1591 (6)0.40792 (18)0.0229 (11)
C250.8724 (8)−0.1323 (6)0.44730 (18)0.0227 (11)
C260.4532 (8)0.0856 (6)0.52368 (16)0.0214 (10)
O20.9913 (5)0.0839 (4)0.59806 (12)0.0215 (8)
H12−0.09610.43490.75170.027*
H130.08900.37490.66950.022*
H150.58320.23550.76820.029*
H160.37470.28740.84660.034*
H170.27410.17220.61030.025*
H210.8591−0.00170.52230.024*
H230.4027−0.07500.41140.029*
H240.7293−0.22180.37270.030*
H251.0123−0.17370.44400.030*
H260.30760.09820.51770.026*
H2A0.88690.15110.60420.026*
H2B0.98240.00060.62280.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0255 (19)0.0358 (19)0.0238 (16)0.0008 (18)0.0024 (16)−0.0079 (15)
N110.027 (2)0.028 (2)0.0193 (18)−0.002 (2)0.0027 (16)−0.0031 (16)
N170.026 (2)0.0214 (18)0.0153 (17)0.0001 (18)0.0024 (15)−0.0037 (15)
N210.027 (2)0.0187 (19)0.0155 (16)0.0018 (17)0.0005 (16)−0.0006 (15)
N270.025 (2)0.0180 (17)0.0158 (16)0.0027 (17)0.0038 (16)−0.0022 (14)
C120.028 (3)0.018 (2)0.022 (2)0.003 (2)0.000 (2)−0.0032 (18)
C130.017 (2)0.022 (2)0.018 (2)0.0004 (19)−0.0024 (18)−0.0005 (17)
C140.014 (2)0.0151 (19)0.0182 (19)0.0006 (18)0.0014 (17)−0.0020 (16)
C150.029 (3)0.022 (2)0.020 (2)0.001 (2)−0.002 (2)−0.0006 (18)
C160.037 (3)0.034 (3)0.014 (2)0.003 (3)−0.001 (2)0.0036 (19)
C170.018 (2)0.019 (2)0.019 (2)0.0025 (19)−0.0003 (18)−0.0008 (17)
C220.019 (2)0.017 (2)0.0168 (19)0.0012 (19)0.0001 (18)0.0005 (16)
C230.026 (3)0.023 (2)0.018 (2)−0.004 (2)−0.001 (2)−0.0003 (17)
C240.033 (3)0.020 (2)0.016 (2)0.000 (2)0.006 (2)−0.0024 (18)
C250.028 (3)0.018 (2)0.022 (2)0.004 (2)0.007 (2)−0.0009 (18)
C260.028 (3)0.021 (2)0.016 (2)0.000 (2)−0.0001 (19)0.0018 (16)
O20.0223 (18)0.0231 (15)0.0192 (14)0.0020 (14)0.0010 (14)0.0013 (13)
Geometric parameters (Å, º) top
N11—C121.333 (6)C17—O11.240 (6)
N11—C161.339 (7)N17—H170.88
C12—C131.387 (6)N21—C221.365 (6)
C12—H120.95C22—C231.393 (6)
C13—C141.377 (6)C23—C241.397 (7)
C13—H130.95C24—C251.382 (7)
C14—C151.406 (6)C25—N211.366 (5)
C14—C171.497 (6)N21—H210.88
C17—N171.345 (5)C23—H230.95
N17—N271.393 (5)C24—H240.95
N27—C261.289 (5)C25—H250.95
C26—C221.442 (6)C26—H260.95
C15—C161.382 (6)O2—H2A0.84
C15—H150.95O2—H2B0.84
C16—H160.95
C12—N11—C16116.4 (4)N27—N17—H17118.0
N11—C12—C13124.3 (4)N17—N27—C26116.5 (4)
N11—C12—H12117.9C22—N21—C25109.5 (4)
C13—C12—H12117.9C22—N21—H21125.2
C14—C13—C12118.6 (4)C25—N21—H21125.2
C14—C13—H13120.7N21—C22—C23107.5 (4)
C12—C13—H13120.7N21—C22—C26121.7 (4)
C13—C14—C15118.5 (4)C23—C22—C26130.4 (4)
C13—C14—C17124.2 (4)C22—C23—C24107.4 (4)
C15—C14—C17117.4 (4)C22—C23—H23126.3
C16—C15—C14117.9 (4)C24—C23—H23126.3
C16—C15—H15121.0C25—C24—C23107.6 (4)
C14—C15—H15121.0C25—C24—H24126.2
N11—C16—C15124.3 (4)C23—C24—H24126.2
N11—C16—H16117.8N21—C25—C24108.0 (4)
C15—C16—H16117.8N21—C25—H25126.0
O1—C17—N17123.2 (4)C24—C25—H25126.0
O1—C17—C14120.0 (4)N27—C26—C22117.9 (4)
C14—C17—N17116.8 (4)N27—C26—H26121.1
C17—N17—N27116.2 (4)C22—C26—H26121.1
C17—N17—H17123.6H2A—O2—H2B103.7
C16—N11—C12—C131.1 (7)C14—C17—N17—N27−169.2 (4)
N11—C12—C13—C14−2.5 (7)C17—N17—N27—C26−178.9 (4)
C12—C13—C14—C152.1 (6)C25—N21—C22—C230.2 (5)
C12—C13—C14—C17−177.6 (4)C25—N21—C22—C26174.5 (4)
C13—C14—C15—C16−0.6 (6)N21—C22—C23—C24−0.4 (5)
C17—C14—C15—C16179.1 (4)C26—C22—C23—C24−174.0 (4)
C12—N11—C16—C150.6 (7)C22—C23—C24—C250.4 (5)
C14—C15—C16—N11−0.8 (7)C22—N21—C25—C240.0 (5)
C13—C14—C17—O1149.0 (5)C23—C24—C25—N21−0.2 (5)
C15—C14—C17—O1−30.7 (6)N17—N27—C26—C22−172.1 (4)
C13—C14—C17—N17−32.6 (6)N21—C22—C26—N276.4 (6)
C15—C14—C17—N17147.6 (4)N27—C26—C22—C23179.3 (4)
O1—C17—N17—N279.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.842.182.934 (5)150
O2—H2A···N270.842.383.011 (5)133
N21—H21···O20.882.072.950 (5)174
N17—H17···O2i0.881.952.822 (5)173
O2—H2B···N11ii0.842.032.832 (5)159
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC11H10N4O·H2O
Mr232.25
Crystal system, space groupOrthorhombic, P212121
Temperature (K)120
a, b, c (Å)6.4224 (3), 7.2115 (5), 23.6073 (16)
V (Å3)1093.38 (12)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.44 × 0.06 × 0.06
Data collection
DiffractometerNonius KappaCCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.967, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections		5095, 1279, 1157
Rint0.054
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.148, 1.17
No. of reflections1279
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.35, −0.41

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 geometric parameters (Å, º) top
C14—C171.497 (6)N21—C221.365 (6)
C17—N171.345 (5)C22—C231.393 (6)
N17—N271.393 (5)C23—C241.397 (7)
N27—C261.289 (5)C24—C251.382 (7)
C26—C221.442 (6)C25—N211.366 (5)
C14—C17—N17116.8 (4)N17—N27—C26116.5 (4)
C17—N17—N27116.2 (4)N27—C26—C22117.9 (4)
C13—C14—C17—N17−32.6 (6)N17—N27—C26—C22−172.1 (4)
C14—C17—N17—N27−169.2 (4)N27—C26—C22—C23179.3 (4)
C17—N17—N27—C26−178.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.842.182.934 (5)150
O2—H2A···N270.842.383.011 (5)133
N21—H21···O20.882.072.950 (5)174
N17—H17···O2i0.881.952.822 (5)173
O2—H2B···N11ii0.842.032.832 (5)159
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2.
 

Acknowledgements

The X-ray data were collected at the EPSRC X-Ray Crystallographic 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

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
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 First citationNonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 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 citationSafoklov, B. B., Atovmyan, E. G., Nikonova, L. A., Tkachev, V. V. & Aldoshin, S. M. (2002). Russ. Chem. Bull. 51, 2224–2229.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 62| Part 1| January 2006| Pages o47-o49
doi:10.1107/S0108270105040230
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