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(2Z)-3-Hy­dr­oxy-1-(pyridin-2-yl)-3-(pyridin-3-yl)prop-2-en-1-one: crystal structure and Hirshfeld surface analysis

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aFaculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410, Negara Brunei Darussalam, bFaculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Queensland 4558, Australia, cDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380 001, India, and dResearch Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: edwardt@sunway.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 20 May 2016; accepted 21 May 2016; online 27 May 2016)

The title compound, C13H10N2O2 [also called 1-(pyridin-2-yl)-3-(pyridin-3-yl)propane-1,3-dione], features an almost planar (r.m.s. deviation = 0.0095 Å) central C3O2 core consolidated by an intra­molecular hy­droxy-O—H⋯O(carbon­yl) hydrogen bond. Twists are evident in the mol­ecule, as seen in the dihedral angles between the central core and the 2- and pyridin-3-yl rings of 8.91 (7) and 15.88 (6)°, respectively. The conformation about the C=C bond [1.3931 (17) Å] is Z, and the N atoms lie to the same side of the mol­ecule. In the mol­ecular packing, supra­molecular chains along the a axis are mediated by π(pyridin-2-yl)–π(pyridin-3-yl) inter­actions [inter-centroid distance = 3.7662 (9) Å]. The observation that chains pack with no directional inter­actions between them is consistent with the calculated electrostatic potential, which indicates that repulsive inter­actions dominate.

1. Chemical context

The β-diketonates of virtually all metals are known (Lamprey, 1960[Lamprey, H. (1960). Ann. NY Acad. Sci. 88, 519-525.]) because of the stability of the resulting six-membered metallocycle formed from bidentate coordination through the two oxygen atoms and the ability of the ligand to be accommodated within the common octa­hedral, tetra­hedral and square-pyramidal coordination geometries. There has been an inter­est over the last few years to introduce extra donor functionality such as nitrile and pyridyl to this class of ligand to generate heterometallic complexes and novel coordination networks. Dipyridyl β-diketonates, for example, have been used to synthesize mixed-metal–organic frameworks. Burrows and co-workers employed di(pyridin-4-yl)propane-1,3-dione to prepare the corresponding AlIII and GaIII octa­hedral building blocks for network structures linked by AgI ions (Burrows et al., 2010[Burrows, A. D., Frost, C. G., Mahon, M. F., Raithby, P. R., Renouf, C. L., Richardson, C. & Stevenson, A. J. (2010). Chem. Commun. 46, 5067-5069.]). Carlucci and co-workers used the same ligand to make FeIII metalloligands that were again joined by coordination to AgI ions. The type of the resulting two- or three-dimensional coordination polymer depended on the nature of the counter-ion to silver (Carlucci et al., 2011[Carlucci, L., Ciani, G., Proserpio, D. M. & Visconti, M. (2011). CrystEngComm, 13, 5891-5902.]). By comparison, the di(pyridin-2-yl)propane-1,3-dione ligand, which also has extra donor functionality available for coord­ination, is sterically hindered to allow network formation. Tan and co-workers prepared the CdII and CuII complexes from this ligand and did indeed observe chelation through the 2,2′-nitro­gen atoms (Tan et al., 2012[Tan, J.-T., Zhao, W.-J., Chen, S.-P., Li, X., Lu, Y.-L., Feng, X. & Yang, X.-W. (2012). Chem. Pap. 66, 47-53.]). However, they did not observe solid-state network formation from bridging oxygen-atom, μ2-Cl or μ3-Cl donors in the CdII complexes; the CuII complex was a tetra­nuclear oligomer linked via bridging water and acetate counter-ions (Tan et al., 2012[Tan, J.-T., Zhao, W.-J., Chen, S.-P., Li, X., Lu, Y.-L., Feng, X. & Yang, X.-W. (2012). Chem. Pap. 66, 47-53.]). Less work has been performed with the unsymmetrical pyridyl β-diketonates. Zhang and co-workers have made the FeIII salt of 3-(pyridin-4-yl)-2,4-penta­nedione as well as the mixed-MOF with AgNO3 in a two-dimensional honeycomb structure while at higher AgI concentrations, a one-dimensional ladder motif was formed (Zhang et al., 2008[Zhang, Y., Chen, B., Fronczek, F. R. & Maverick, A. W. (2008). Inorg. Chem. 47, 4433-4435.]). This ligand and the symmetrical 4,4′- and 3,3′- variants have been treated with hydrazine to give the corresponding pyrazoles that were used to prepare strongly photoluminescent CuI coordination polymers (Zhan et al., 2011[Zhan, S.-Z., Li, M., Zhou, X.-P., Ni, J., Huang, X.-C. & Li, D. (2011). Inorg. Chem. 50, 8879-8892.]).

[Scheme 1]

All of the mentioned dipyridyl ligands can be conveniently prepared by the Claisen condensation of an acetyl­pyridine with a pyridine carb­oxy­lic ester. The title compound, (I)[link], has not previously been reported, but was prepared in this way from 2-acetyl­pyridine and ethyl nicotinate, and crystals suitable for X-ray crystallography were obtained by recrystallization from a mixture of di­chloro­methane and hexane. Herein, the crystal structure analysis of (I)[link] is described along with a detailed investigation of the mol­ecular packing by a Hirshfeld surface analysis.

2. Structural commentary

In (I)[link], the assignment of carbonyl- versus hy­droxy-O atoms is not readily confirmed by a great disparity in the C1—O1 [1.2871 (14) Å] and C3—O2 [1.3041 (14) Å] bond lengths. The assignment was based on an unrestrained refinement of the H1O atom which resulted in a O2—H1O bond length of 1.090 (18) Å. More certainty is associated with the assignment of the nitro­gen atoms in the pyridyl rings. Thus, the short C5—N1 and C4—N1 [1.3325 (17) and 1.3484 (15) Å] and C10—N2 and C11—N2 [1.3371 (17) and 1.3397 (18) Å] bond lengths cf. the C—C bonds in the rings confirm their assignment. The central C3O2 residual in (I)[link], Fig. 1[link], is essentially planar with the r.m.s. deviation of the five atoms being 0.0095 Å. The syn arrangement of the oxygen atoms enables the formation of an intra­molecular hy­droxy-O—H⋯O(carbon­yl) hydrogen bond, Table 1[link]. The dihedral angles formed between the central plane and the N1- and N2-pyridinyl rings are 8.91 (7) and 15.88 (6)°, respectively, indicating twists in the mol­ecule. The dihedral angle between the pyridyl rings is 7.45 (7)°. The conformation about the C2=C3 [1.3931 (17) Å] is Z, and, to a first approximation, the N1 and N2 atoms lie to the same side of the mol­ecule.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2O⋯O1 0.85 (2) 1.65 (1) 2.4673 (14) 160 (2)
[Figure 1]
Figure 1
The mol­ecular structure of (I)[link], showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.

3. Supra­molecular features

The mol­ecular packing in the crystal is dominated by ππ inter­actions formed between the N1- and N2-pyridinyl rings of translationally related mol­ecules [Cg(N1-pyridin­yl)⋯Cg(N2-pyridin­yl) = 3.7662 (9) Å, angle of inclination = 7.45 (6)° for symmetry operation 1 + x, y, z]. The result is the formation of a linear supra­molecular chain, Fig. 2[link]a. The chains pack with no directional inter­actions between them in accord with the distance criteria in PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Fig. 2[link]b.

[Figure 2]
Figure 2
Mol­ecular packing in (I)[link]: (a) a view of the supra­molecular chain along the a axis sustained by ππ inter­actions and (b) unit-cell contents shown in projection down the a axis. The ππ inter­actions are shown as purple dashed lines.

4. Hirshfeld surface analysis

The program Crystal Explorer 3.1 (Wolff et al., 2012[Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer. The University of Western Australia, Australia.]) was used to generate Hirshfeld surfaces mapped over the electrostatic potential, dnorm, shape-index and curvedness. The electrostatic potential was calculated with TONTO (Spackman et al., 2008[Spackman, M. A., McKinnon, J. J. & Jayatilaka, D. (2008). CrystEngComm, 10, 377-388.]; Jayatilaka et al., 2005[Jayatilaka, D., Grimwood, D. J., Lee, A., Lemay, A., Russel, A. J., Taylo, C., Wolff, S. K., Chenai, C. & Whitton, A. (2005). TONTO - A System for Computational Chemistry. Available at: https:// hirshfeldsurface. net/]), integrated in Crystal Explorer, using the experimental geometry as the input. The electrostatic potentials were mapped on the Hirshfeld surface using the STO-3G basis set at the Hartree–Fock level of theory over a range ±0.06 au. The contact distances di and de from the Hirshfeld surface to the nearest atom inside and outside, respectively, enables the analysis of the inter­molecular inter­actions through the mapping of dnorm. The combination of de and di in the form of a two-dimensional fingerprint plot (McKinnon et al., 2004[McKinnon, J. J., Spackman, M. A. & Mitchell, A. S. (2004). Acta Cryst. B60, 627-668.]) provides a summary of the inter­molecular contacts in the crystal.

From the Hirshfeld surface mapped over electrostatic potential, Fig. 3[link], the negative potentials around the oxygen atoms of the hy­droxy and carbonyl groups as well as about the nitro­gen atoms of pyridyl rings prevent their participation in inter­molecular inter­actions in the crystal of (I)[link] due to the electrostatic repulsion that would eventuate. The presence of a short inter­molecular C⋯C contact between the C5 and C10 atoms [C5⋯C10 = 3.313 (2) Å; symmetry code: −1 + x, y, z], which fall within the ππ contacts between pyridyl rings (Fig. 2[link]a), is viewed as bright-red spots near these atoms on the Hirshfeld surface mapped over dnorm, Fig. 4[link].

[Figure 3]
Figure 3
A view of the Hirshfeld surface mapped over electrostatic potential for (I)[link]. The red and blue regions represent negative and positive electrostatic potentials, respectively.
[Figure 4]
Figure 4
Two views of the Hirshfeld surface mapped over dnorm for (I)[link]: the bright-red spots at (a) C5 and (b) C10 indicate their involvement in short inter­molecular C⋯C contacts.

The overall 2D fingerprint plot, Fig. 5[link]a, and those delin­eated into H⋯H, C⋯C, O⋯H/H⋯O, C⋯H/H⋯C and N⋯H/H⋯N contacts are illustrated in Fig. 5[link]bf, respectively; their relative contributions to the surface are qu­anti­fied in Table 2[link]. The inter­atomic H⋯H contacts (McKinnon et al., 2007[McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814-3816.]) appear as the scattered points over the greater part of the plot shown in Fig. 5[link]b, with a single peak at (de, di) less than the van der Waals separation corresponding to a short H13⋯H13 contact of 2.33 Å (symmetry code: 1 − x, −y, −z). The short inter­atomic C5⋯C10 contact and ππ stacking inter­actions appear as an arrow-like distribution of points with the tip at de + di ∼ 3.3 Å (Fig. 5[link]c). The presence of ππ stacking inter­actions between the pyridyl rings is also apparent from the appearance of red and blue triangle pairs on the Hirshfeld surface mapped with shape-index property identified with arrows in the image of Fig. 6[link], and in the flat region on the Hirshfeld surface mapped over curvedness in Fig. 7[link].

Table 2
Percentage contribution of the different inter­molecular inter­actions to the Hirshfeld surface of (I)

Contact %
H⋯H 36.2
O⋯H/H⋯O 13.2
C⋯H/H⋯C 22.9
N⋯H/H⋯N 14.6
C⋯C 6.1
C⋯O/O⋯C 2.9
C⋯N/N⋯C 2.8
O⋯O 0.9
N⋯N 0.4
[Figure 5]
Figure 5
The two-dimensional fingerprint plots for (I)[link]: (a) all inter­actions, and delineated into (b) H⋯H, (c) C⋯C, (d) O⋯H/H⋯O, (e) C⋯H/H⋯C and (f) N⋯H/H⋯N inter­actions.
[Figure 6]
Figure 6
A view of the Hirshfeld surface mapped with shape-index property for (I)[link]. The red and blue triangles identified with arrows indicate ππ stacking inter­actions.
[Figure 7]
Figure 7
A view of the Hirshfeld surface mapped over curvedness for (I)[link]. The flat regions highlight the involvement of rings in the ππ stacking inter­actions.

The two-dimensional fingerprint plots delineated into O⋯H/H⋯O, C⋯H/H⋯C and N⋯H/H⋯N inter­actions exhibit their usual characteristic features in their respective plots; Fig. 4[link]df. However, the points are distributed at (de, di) distances greater than their respective van der Waals separations. This is consistent with the repulsion between the atoms having electrostatic negative potential dominating the mol­ecular packing, hence the lack of specific inter­molecular inter­actions between supra­molecular chains.

5. Database survey

A survey of the Cambridge Structural Database (Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) revealed that there are two closely related pyridyl-substituted propane-1,3-dione structures in the crystallographic literature. These are the mono-pyridyl derivatives 3-hy­droxy-1-phenyl-3-(pyridin-3-yl)prop-2-en-1-one (II) and 3-hy­droxy-1-phenyl-3-(pyridin-4-yl)prop-2-en-1-one (III), both published by Dudek et al. (2011[Dudek, M., Clegg, J. K., Glasson, C. R. K., Kelly, N., Gloe, K., Gloe, K., Kelling, A., Buschmann, H.-J., Jolliffe, K. A., Lindoy, L. F. & Meehan, G. V. (2011). Cryst. Growth Des. 11, 1697-1704.]). Each structure features a very similar central core with the intra­molecular O—H⋯O hydrogen bond. In each of (II) and (III), the pyridyl ring is connected to the carbon atom bearing the hy­droxy group. As seen from the overlay diagram (Fig. 8[link]) and as qu­anti­fied in Table 3[link], the three structures (I)–(III) have very similar conformations.

Table 3
Dihedral angle (°) data for (I)–(III)

Structure C3O2/n-pyrid­yl C3O2/pyridin-2-yl or phen­yl ring/ring CSD refcodea Reference
(I) n = 3; 15.88 (6) 8.91 (7) 7.45 (7) This work
(II) n = 3; 2.23 (9) 4.20 (8) 4.38 (9) XIOXID Dudek et al. (2011[Dudek, M., Clegg, J. K., Glasson, C. R. K., Kelly, N., Gloe, K., Gloe, K., Kelling, A., Buschmann, H.-J., Jolliffe, K. A., Lindoy, L. F. & Meehan, G. V. (2011). Cryst. Growth Des. 11, 1697-1704.])
(III)b n = 4; 8.10 (5) 11.41 (5) 3.88 (5) BEDREJ Dudek et al. (2011[Dudek, M., Clegg, J. K., Glasson, C. R. K., Kelly, N., Gloe, K., Gloe, K., Kelling, A., Buschmann, H.-J., Jolliffe, K. A., Lindoy, L. F. & Meehan, G. V. (2011). Cryst. Growth Des. 11, 1697-1704.])
Notes: (a) Groom et al. (2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]); (b) isolated as a 1:1 co-crystal with benzoic acid.
[Figure 8]
Figure 8
Overlay diagram of mol­ecules of (I)[link] (red image), (II) (green) and (III) (blue). The mol­ecules have been overlapped so that the central five-membered rings are coincident.

6. Synthesis and crystallization

2-Acetyl­pyridine (3.0562 g, 25.2 mmol) was added to a suspension of NaH (60% dispersion in mineral oil, 2.0058 g, 50.0 mmol) in anhydrous THF (10 ml) at room temperature with stirring. Ethyl nicotinate (7.5675g, 50.1 mmol) in anhydrous THF (10ml) was added dropwise to the mixture over 3 min. The yellow mixture was refluxed under a nitro­gen atmosphere for 1.3 h and then quenched with ice–water (50 ml). Glacial acetic acid was added to adjust the pH to 6–7. The resulting yellow precipitate was collected by filtration, washed with cold water and dried under vacuum. Recrystallization from di­chloro­methane–hexane (1:1 v/v) solution afforded colourless crystals. Yield: 4.03 g (70.7%). M.p: 377–378 K. IR (KBr pellet) νmax/cm−1: 3121 (m), 3053 (m), 2922 (m), 2853 (m), 1611 (s), 1595 (s), 1539 (m), 1458 (m), 1418 (m), 1221 (m), 1188 (m), 1146 (m), 1115 (m), 1067 (m), 1018 (m), 989 (m), 926 (m), 775 (s), 739 (m), 679 (s), 611 (m). Analysis calculated for C13H10N2O2: C, 69.03; H, 4.42; N, 12.19. Found: C, 68.73; H, 4.54; N, 12.16. MS: m/z 226. 1H NMR (400 MHz, d6–DMSO) δ 9.22 (1H, s), 8.82 (2H, m), 8.44 (1H, d, J = 7.9 Hz), 8.17 (1H, d, J = 7.8 Hz), 8.09 (1H, m), 7.70 (1H, m), 7.63 (2H, m).

7. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 4[link]. Carbon-bound H atoms were placed in their calculated positions (C—H = 0.95 Å) and were included in the refinement in the riding-model approximation, with Uiso(H) set to 1.2Ueq(C). The hy­droxy-H atom was located in a difference map and refined with O—H = 0.82±0.01Å, and with Uiso(H) set to 1.5Ueq(O).

Table 4
Experimental details

Crystal data
Chemical formula C13H10N2O2
Mr 226.23
Crystal system, space group Orthorhombic, Pbca
Temperature (K) 273
a, b, c (Å) 7.2124 (9), 14.1782 (19), 20.794 (3)
V3) 2126.4 (5)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.20 × 0.20 × 0.19
 
Data collection
Diffractometer Bruker D8-Quest CCD
Absorption correction Multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.])
Tmin, Tmax 0.981, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections 46632, 2647, 2227
Rint 0.057
(sin θ/λ)max−1) 0.671
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.121, 1.05
No. of reflections 2647
No. of parameters 157
No. of restraints 1
Δρmax, Δρmin (e Å−3) 0.33, −0.24
Computer programs: SMART and SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), QMol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graphics Modell. 19, 557-559.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(2Z)-3-Hydroxy-1-(pyridin-2-yl)-3-(pyridin-3-yl)prop-2-en-1-one top
Crystal data top
C13H10N2O2Dx = 1.413 Mg m3
Mr = 226.23Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9904 reflections
a = 7.2124 (9) Åθ = 3.0–28.3°
b = 14.1782 (19) ŵ = 0.10 mm1
c = 20.794 (3) ÅT = 273 K
V = 2126.4 (5) Å3Block, colourless
Z = 80.20 × 0.20 × 0.19 mm
F(000) = 944
Data collection top
Bruker D8-Quest CCD
diffractometer
2647 independent reflections
Radiation source: sealed tube2227 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 8.366 pixels mm-1θmax = 28.5°, θmin = 3.0°
φ and ω scansh = 89
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1818
Tmin = 0.981, Tmax = 0.982l = 2727
46632 measured reflections
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0588P)2 + 0.9349P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.33 e Å3
2647 reflectionsΔρmin = 0.24 e Å3
157 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.09862 (13)0.14710 (7)0.02692 (4)0.0286 (2)
O20.19541 (13)0.05816 (7)0.02776 (4)0.0276 (2)
H2O0.1025 (19)0.0929 (11)0.0188 (8)0.041*
N10.33075 (15)0.12603 (7)0.17723 (5)0.0246 (2)
N20.43366 (17)0.09680 (9)0.21246 (6)0.0335 (3)
C10.13288 (17)0.11505 (8)0.08360 (6)0.0217 (3)
C20.01053 (16)0.05315 (8)0.11536 (5)0.0214 (3)
H20.04020.02900.15570.026*
C30.15550 (17)0.02859 (8)0.08551 (5)0.0211 (2)
C40.30743 (16)0.14778 (8)0.11462 (5)0.0203 (2)
C50.48525 (19)0.15721 (9)0.20520 (6)0.0286 (3)
H50.50440.14250.24830.034*
C60.61954 (19)0.21046 (9)0.17384 (7)0.0294 (3)
H60.72440.23130.19570.035*
C70.59415 (18)0.23185 (9)0.10951 (7)0.0284 (3)
H70.68190.26690.08710.034*
C80.43511 (18)0.19984 (8)0.07917 (6)0.0245 (3)
H80.41410.21290.03600.029*
C90.29989 (16)0.03006 (8)0.11646 (5)0.0206 (2)
C100.30159 (18)0.04710 (9)0.18265 (6)0.0269 (3)
H100.20550.02250.20730.032*
C110.57090 (19)0.13133 (10)0.17598 (7)0.0315 (3)
H110.66440.16560.19600.038*
C120.58095 (19)0.11875 (9)0.10999 (7)0.0308 (3)
H120.67820.14450.08650.037*
C130.44368 (18)0.06720 (9)0.07980 (6)0.0257 (3)
H130.44740.05750.03560.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0318 (5)0.0325 (5)0.0214 (4)0.0031 (4)0.0021 (3)0.0078 (3)
O20.0272 (5)0.0349 (5)0.0208 (4)0.0036 (4)0.0036 (3)0.0050 (3)
N10.0235 (5)0.0280 (5)0.0224 (5)0.0003 (4)0.0005 (4)0.0020 (4)
N20.0316 (6)0.0394 (6)0.0294 (6)0.0077 (5)0.0005 (5)0.0056 (5)
C10.0229 (6)0.0215 (5)0.0207 (5)0.0035 (4)0.0010 (4)0.0003 (4)
C20.0222 (6)0.0232 (6)0.0188 (5)0.0003 (4)0.0006 (4)0.0020 (4)
C30.0226 (6)0.0211 (5)0.0195 (5)0.0033 (4)0.0009 (4)0.0010 (4)
C40.0225 (6)0.0173 (5)0.0211 (5)0.0022 (4)0.0023 (4)0.0002 (4)
C50.0282 (6)0.0333 (7)0.0243 (6)0.0001 (5)0.0023 (5)0.0003 (5)
C60.0250 (6)0.0277 (6)0.0355 (7)0.0030 (5)0.0034 (5)0.0046 (5)
C70.0275 (6)0.0220 (6)0.0357 (7)0.0049 (5)0.0053 (5)0.0007 (5)
C80.0286 (6)0.0209 (5)0.0240 (6)0.0006 (5)0.0034 (5)0.0013 (4)
C90.0202 (5)0.0191 (5)0.0224 (5)0.0030 (4)0.0001 (4)0.0010 (4)
C100.0247 (6)0.0320 (6)0.0239 (6)0.0044 (5)0.0020 (5)0.0022 (5)
C110.0263 (7)0.0309 (7)0.0373 (7)0.0055 (5)0.0021 (5)0.0043 (5)
C120.0276 (6)0.0279 (6)0.0369 (7)0.0066 (5)0.0059 (5)0.0008 (5)
C130.0284 (6)0.0245 (6)0.0243 (6)0.0005 (5)0.0036 (5)0.0012 (5)
Geometric parameters (Å, º) top
O1—C11.2871 (14)C5—H50.9300
O2—C31.3041 (14)C6—C71.3839 (19)
O2—H2O0.853 (9)C6—H60.9300
N1—C51.3325 (17)C7—C81.3855 (18)
N1—C41.3484 (15)C7—H70.9300
N2—C101.3371 (17)C8—H80.9300
N2—C111.3397 (18)C9—C131.3907 (17)
C1—C21.4090 (16)C9—C101.3975 (16)
C1—C41.4888 (17)C10—H100.9300
C2—C31.3931 (17)C11—C121.386 (2)
C2—H20.9300C11—H110.9300
C3—C91.4800 (16)C12—C131.3815 (18)
C4—C81.3915 (16)C12—H120.9300
C5—C61.3905 (19)C13—H130.9300
C3—O2—H2O102.4 (12)C6—C7—C8118.55 (12)
C5—N1—C4116.73 (11)C6—C7—H7120.7
C10—N2—C11117.16 (12)C8—C7—H7120.7
O1—C1—C2121.93 (11)C7—C8—C4118.71 (11)
O1—C1—C4116.69 (10)C7—C8—H8120.6
C2—C1—C4121.37 (10)C4—C8—H8120.6
C3—C2—C1119.02 (11)C13—C9—C10117.90 (11)
C3—C2—H2120.5C13—C9—C3119.94 (11)
C1—C2—H2120.5C10—C9—C3122.12 (11)
O2—C3—C2121.32 (11)N2—C10—C9123.63 (12)
O2—C3—C9115.20 (10)N2—C10—H10118.2
C2—C3—C9123.47 (10)C9—C10—H10118.2
N1—C4—C8123.38 (11)N2—C11—C12123.53 (12)
N1—C4—C1116.91 (10)N2—C11—H11118.2
C8—C4—C1119.69 (11)C12—C11—H11118.2
N1—C5—C6123.92 (12)C13—C12—C11118.73 (12)
N1—C5—H5118.0C13—C12—H12120.6
C6—C5—H5118.0C11—C12—H12120.6
C7—C6—C5118.69 (12)C12—C13—C9119.05 (12)
C7—C6—H6120.7C12—C13—H13120.5
C5—C6—H6120.7C9—C13—H13120.5
O1—C1—C2—C32.34 (18)N1—C4—C8—C70.49 (18)
C4—C1—C2—C3176.70 (10)C1—C4—C8—C7178.19 (11)
C1—C2—C3—O23.26 (17)O2—C3—C9—C1314.19 (16)
C1—C2—C3—C9175.33 (10)C2—C3—C9—C13167.14 (11)
C5—N1—C4—C80.14 (17)O2—C3—C9—C10163.35 (11)
C5—N1—C4—C1178.58 (11)C2—C3—C9—C1015.33 (18)
O1—C1—C4—N1170.37 (10)C11—N2—C10—C90.2 (2)
C2—C1—C4—N18.72 (17)C13—C9—C10—N20.14 (19)
O1—C1—C4—C88.40 (16)C3—C9—C10—N2177.44 (12)
C2—C1—C4—C8172.51 (10)C10—N2—C11—C120.6 (2)
C4—N1—C5—C60.55 (19)N2—C11—C12—C130.6 (2)
N1—C5—C6—C70.9 (2)C11—C12—C13—C90.27 (19)
C5—C6—C7—C80.48 (19)C10—C9—C13—C120.09 (18)
C6—C7—C8—C40.16 (18)C3—C9—C13—C12177.55 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O10.85 (2)1.65 (1)2.4673 (14)160 (2)
Percentage contribution of the different intermolecular interactions to the Hirshfeld surface of (I) top
Contact%
H···H36.2
O···H/H···O13.2
C···H/H···C22.9
N···H/H···N14.6
C···C6.1
C···O/O···C2.9
C···N/N···C2.8
O···O0.9
N···N0.4
Dihedral angle (°) data for (I)–(III) top
StructureC3O2/n-pyridylC3O2/pyridin-2-yl or phenylring/ringCSD refcodeaReference
(I)n = 3; 15.88 (6)8.91 (7)7.45 (7)This work
(II)n = 3; 2.23 (9)4.20 (8)4.38 (9)XIOXIDDudek et al. (2011)
(III)bn = 4; 8.10 (5)11.41 (5)3.88 (5)BEDREJDudek et al. (2011)
Notes: (a) Groom et al. (2016); (b) isolated as a 1:1 co-crystal with benzoic acid.
 

Footnotes

Additional correspondence author, e-mail: dyoung1@usc.edu.au.

Acknowledgements

We acknowledge the financial support from the Brunei Research Council (BRC) Science and Technology grant (S&T17).

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