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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Pages o685-o686
doi:10.1107/S1600536812005399

2-{(E)-1-[2-(4-Nitro­phen­yl)hydrazin-1-yl­­idene]eth­yl}benzene-1,3-diol

R. Alan Howie,a James L. Wardell,b‡ Solange M. S. V. Wardellc and Edward R. T. Tiekinkd*

aDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, bCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Avenida Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, cCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 February 2012; accepted 7 February 2012; online 10 February 2012)

The title compound, C14H13N3O4, is close to planar, the dihedral angle between the terminal benzene rings being 5.80 (16)°; the nitro group is coplanar with the benzene ring to which it is bonded [O—N—C—C torsion angle = −177.3 (3)°]. The hy­droxy group forms an intra­molecular hydrogen bond with the imine N atom, and the conformation about the imine bond is E. In the crystal, layers in the (101) plane with an undulating topology are formed by O—H⋯O and N—H⋯O hydrogen bonds along with C—H⋯O inter­actions. Centrosymmetrically related layers are connected via π–π inter­actions [ring centroid–centroid distance = 3.5739 (19) Å] into double layers.

Related literature

For background on the influence of substituents upon the supra­molecular structures of hydrazones, see: Glidewell et al. (2004[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o19-o23.]); Ferguson et al. (2005[Ferguson, G., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o613-o616.]); Wardell et al. (2007[Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell, C. (2007). Acta Cryst. B63, 879-895.]); Baddeley, de Souza França et al. (2009[Baddeley, T. C., de Souza França, L., Howie, R. A., de Lima, G. M., Skakle, J. M. S., de Souza, J. D., Wardell, J. L. & Wardell, S. M. S. V. (2009). Z. Kristallogr. 224, 213-224.]); Baddeley, Howie et al. (2009[Baddeley, T. C., Howie, R. A., da Silva Lima, C. H., Kaiser, C. R., de Souza, M. V. N., Wardell, J. L. & Wardell, S. M. S. V. (2009). Z. Kristallogr. 224, 506-514.]); de Souza et al. (2010[Souza, M. V. N. de, Howie, R. A., Tiekink, E. R. T., Wardell, J. L., Wardell, S. M. S. V. & Kaiser, C. R. (2010). Acta Cryst. E66, o698-o699.]); Howie, da Silva Lima et al. (2010[Howie, R. A., da Silva Lima, C. H., Kaiser, C. R., de Souza, M. V. N., Wardell, J. L. & Wardell, S. M. S. V. (2010). Z. Kristallogr. 225, 349-358.]); Howie, de Souza et al. (2010[Howie, R. A., de Souza, M. V. N., de Lima Ferreira, M., Kaiser, C. R., Wardell, J. L. & Wardell, S. M. S. V. (2010). Z. Kristallogr. 225, 440-447.]); Nogueira et al. (2011[Nogueira, A., Vasconcelos, T. R. A., Wardell, J. L., Solange, M. S. V. & Wardell, S. M. S. V. (2011). Z. Kristallogr. 226, 846-861.]); Howie et al. (2011[Howie, R. A., de Souza, M. V. N., Pinheiro, A. C., Kaiser, C. R., Wardell, J. L. & Wardell, S. M. S. V. (2011). Z. Kristallogr. 226, 483-491.]).

[Scheme 1]

Experimental

Crystal data

  • C14H13N3O4

  • Mr = 287.27

  • Monoclinic, P 21 /n

  • a = 7.9714 (3) Å

  • b = 13.5021 (7) Å

  • c = 12.1081 (5) Å

  • β = 90.186 (3)°

  • V = 1303.20 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 120 K

  • 0.10 × 0.10 × 0.08 mm
Data collection

  • Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.875, Tmax = 0.991

  • 12144 measured reflections

  • 2984 independent reflections

  • 1987 reflections with I > 2σ(I)

  • Rint = 0.070
Refinement

  • R[F2 > 2σ(F2)] = 0.082

  • wR(F2) = 0.184

  • S = 1.10

  • 2984 reflections

  • 200 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O⋯N1 0.84 (2) 1.79 (3) 2.534 (4) 147 (4)
N2—H2N⋯O3i 0.88 (2) 2.18 (3) 3.039 (4) 167 (2)
O2—H2O⋯O1ii 0.85 (4) 1.99 (4) 2.834 (3) 173 (4)
C14—H14⋯O4i 0.95 2.50 3.326 (4) 146
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). 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: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005399/bt5815sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005399/bt5815Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005399/bt5815Isup3.cml

checkCIF report


Comment top

As a continuation of studies designed to ascertain the influence of substituents upon the supramolecular structures of hydrazones, in particular of those having potential biological activities, the title compound (E)-2,6-dihydroxyacetophenone 4-nitrophenylhydrazone (I) was investigated. Previous systematic investigations have included the study of substituted phenylhydrazines with substituted benzaldehydes (Glidewell et al., 2004; Ferguson et al., 2005) and 2-hydroxyacetophenone (Baddeley, de Souza França et al., 2009). Hydrazones derived from substituted benzaldehydes and (pyrazinecarbonyl)hydrazine (Baddeley, Howie et al., 2009; Howie, da Silva Lima et al., 2010), 2-hydrazinyl-benzothiazole (Nogueira et al., 2011), 7-chloroquinoline-4-hydrazide (Howie, de Souza et al., 2010; de Souza et al., 2010) and 2-hydrazinylacyl-N-isonicotine (Wardell et al., 2007) have also been investigated along with L-serinyl derivatives, (S)-2-hydroxy-1-[N-(benzylidene)-hydrazinylcarbonyl]ethylcarbamate esters (Howie et al., 2011).

In (I), Fig. 1, the dihedral angle between the benzene rings is 5.80 (16)°, indicating a planar molecule. The nitro group is co-planar with the benzene ring to which it is bonded as seen in the value of the O3—N3—C12—C11 torsion angle of -177.3 (3)°. The hydroxy group forms an intramolecular hydrogen bond with the imine-N1 atom, Table 1. The configuration about the N1═C7 imine bond [1.304 (4) Å] is E.

Supramolecular layers with an undulating topology in the (101) plane are formed by O—-H···O and N—H···O hydrogen bonds which are reinforced by C—H···O interactions, Fig. 2 and Table 1. Centrosymmetrically related layers are connected via π–π interactions occurring between the (C1–C6) and (C9–C14)i rings [ring centroid···centroid distance = 3.5739 (19) Å, angle between rings = 5.80 (16)° for i: -x, 1 - y, 1 - z], Fig. 3. Layers stack without specific interactions between them, Fig. 4.

Related literature top

For background on the influence of substituents upon the supramolecular structures of hydrazones, see: Glidewell et al. (2004); Ferguson et al. (2005); Wardell et al. (2007); Baddeley, de Souza França et al. (2009); Baddeley, Howie et al. (2009); de Souza et al. (2010); Howie, da Silva Lima et al. (2010); Howie, de Souza et al. (2010); Nogueira et al. (2011); Howie et al. (2011).

Experimental top

A solution of 4-nitrophenylhydrazine and 2,6-dihydroxyacetophenone (1 mmol each) in ethanol (25 ml) was refluxed for 1 h, rotary evaporated and the residue recrystallized from methanol, M.pt.: 501–503 K. IR (KBr, cm-1): ν 3600–2000 (v br), 3527, 3340, 1625, 1531. Anal. Found: C, 58.81; H, 4.86; N, 14.47. Calculated for C14H13N3O4: C, 58.53; H, 4.56; N, 14.62%.

Refinement top

The C-bound H atoms were geometrically placed (C—H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The O- and N-bound H atoms were located from a difference map and refined with the distance restraints O—H = 0.84±0.01 and N—H = 0.88±0.01 Å, and with Uiso(H) = zUeq(carrier atom); z = 1.5 for O and z = 1.2 for N.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. A plan view of the supramolecular layer in (I) sustained by O—H···O (orange dashed lines), N—H···O (blue dashed lines) and C—H···O (brown dashed lines) interactions.
[Figure 3] Fig. 3. A side-on view of two supramolecular layers in (I) connected by π–π interactions (purple dashed lines).
[Figure 4] Fig. 4. A view in projection down the b axis of the packing of supramolecular layers in (I).
2-{(E)-1-[2-(4-Nitrophenyl)hydrazin-1-ylidene]ethyl}benzene-1,3-diol top
Crystal data top
C14H13N3O4F(000) = 600
Mr = 287.27Dx = 1.464 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8454 reflections
a = 7.9714 (3) Åθ = 2.9–27.5°
b = 13.5021 (7) ŵ = 0.11 mm−1
c = 12.1081 (5) ÅT = 120 K
β = 90.186 (3)°Block, orange
V = 1303.20 (10) Å30.10 × 0.10 × 0.08 mm
Z = 4
Data collection top
Bruker–Nonius Roper CCD camera on κ-goniostat
diffractometer		2984 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode1987 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ and ω scansh = −10→8
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		k = −17→17
Tmin = 0.875, Tmax = 0.991l = −15→15
12144 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.082Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0335P)2 + 2.8837P]
where P = (Fo2 + 2Fc2)/3
2984 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.30 e Å−3
3 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C14H13N3O4V = 1303.20 (10) Å3
Mr = 287.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.9714 (3) ŵ = 0.11 mm−1
b = 13.5021 (7) ÅT = 120 K
c = 12.1081 (5) Å0.10 × 0.10 × 0.08 mm
β = 90.186 (3)°
Data collection top
Bruker–Nonius Roper CCD camera on κ-goniostat
diffractometer		2984 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		1987 reflections with I > 2σ(I)
Tmin = 0.875, Tmax = 0.991Rint = 0.070
12144 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0823 restraints
wR(F2) = 0.184H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.30 e Å−3
2984 reflectionsΔρmin = −0.28 e Å−3
200 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O10.1354 (3)0.71070 (18)0.50069 (19)0.0328 (6)
H1O0.150 (5)0.6502 (11)0.514 (3)0.049*
O2−0.1888 (3)0.68611 (19)0.83331 (18)0.0340 (6)
H2O−0.241 (5)0.721 (3)0.880 (3)0.051*
O30.6044 (3)0.19192 (18)0.30034 (19)0.0360 (6)
O40.6016 (3)0.32888 (19)0.20547 (18)0.0360 (6)
N10.1233 (3)0.5509 (2)0.6101 (2)0.0257 (6)
N20.1909 (4)0.4583 (2)0.6225 (2)0.0276 (6)
H2N0.167 (4)0.423 (2)0.6812 (19)0.033*
N30.5648 (3)0.2804 (2)0.2882 (2)0.0273 (6)
C1−0.0115 (4)0.6950 (2)0.6750 (2)0.0252 (7)
C20.0357 (4)0.7506 (3)0.5807 (3)0.0273 (7)
C3−0.0168 (5)0.8477 (3)0.5650 (3)0.0334 (8)
H30.02140.88450.50310.040*
C4−0.1245 (5)0.8902 (3)0.6400 (3)0.0357 (8)
H4−0.16080.95660.62950.043*
C5−0.1806 (4)0.8372 (3)0.7305 (3)0.0337 (8)
H5−0.25630.86700.78100.040*
C6−0.1266 (4)0.7405 (3)0.7478 (3)0.0279 (7)
C70.0573 (4)0.5945 (2)0.6957 (2)0.0251 (7)
C80.0634 (5)0.5472 (3)0.8079 (3)0.0326 (8)
H8A−0.02720.49840.81410.049*
H8B0.04950.59810.86480.049*
H8C0.17180.51410.81810.049*
C90.2810 (4)0.4167 (2)0.5372 (2)0.0235 (7)
C100.3233 (4)0.4699 (2)0.4419 (2)0.0239 (7)
H100.28650.53630.43290.029*
C110.4188 (4)0.4251 (2)0.3614 (2)0.0248 (7)
H110.44890.46080.29680.030*
C120.4704 (4)0.3281 (2)0.3751 (2)0.0227 (7)
C130.4297 (4)0.2742 (3)0.4688 (3)0.0273 (7)
H130.46590.20760.47680.033*
C140.3360 (4)0.3191 (2)0.5497 (2)0.0260 (7)
H140.30840.28340.61480.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0374 (14)0.0285 (13)0.0327 (13)0.0032 (11)0.0141 (10)0.0013 (11)
O20.0387 (14)0.0374 (15)0.0258 (12)0.0003 (12)0.0129 (10)−0.0060 (11)
O30.0443 (15)0.0266 (13)0.0371 (13)0.0044 (12)0.0125 (11)−0.0032 (11)
O40.0424 (15)0.0411 (15)0.0246 (12)0.0021 (12)0.0121 (10)0.0022 (11)
N10.0265 (15)0.0245 (15)0.0261 (13)−0.0025 (12)0.0036 (11)−0.0012 (11)
N20.0351 (16)0.0240 (15)0.0238 (13)0.0011 (12)0.0106 (11)0.0000 (11)
N30.0250 (14)0.0327 (16)0.0243 (13)0.0006 (12)0.0029 (11)−0.0028 (12)
C10.0226 (16)0.0266 (17)0.0263 (15)−0.0051 (13)0.0035 (12)−0.0053 (13)
C20.0293 (18)0.0277 (18)0.0251 (15)−0.0045 (15)0.0051 (13)−0.0038 (13)
C30.043 (2)0.0268 (19)0.0308 (18)−0.0026 (16)0.0061 (15)0.0012 (14)
C40.042 (2)0.0274 (19)0.0380 (19)0.0026 (16)−0.0010 (16)−0.0075 (15)
C50.034 (2)0.038 (2)0.0289 (17)0.0035 (16)0.0042 (14)−0.0112 (15)
C60.0280 (18)0.0318 (19)0.0239 (15)−0.0044 (15)0.0020 (13)−0.0081 (14)
C70.0245 (17)0.0243 (17)0.0264 (16)−0.0064 (13)0.0061 (13)−0.0061 (13)
C80.045 (2)0.0270 (18)0.0264 (17)−0.0003 (16)0.0109 (15)−0.0036 (14)
C90.0235 (16)0.0247 (17)0.0224 (14)−0.0024 (13)0.0041 (12)−0.0033 (13)
C100.0305 (18)0.0170 (16)0.0244 (15)0.0013 (13)0.0037 (13)0.0008 (12)
C110.0268 (17)0.0288 (18)0.0188 (14)−0.0039 (14)0.0034 (12)0.0004 (13)
C120.0221 (16)0.0246 (16)0.0215 (14)−0.0011 (13)0.0033 (12)−0.0042 (12)
C130.0300 (18)0.0239 (17)0.0281 (16)0.0030 (14)0.0021 (13)0.0009 (13)
C140.0308 (18)0.0259 (17)0.0213 (15)−0.0026 (14)0.0078 (13)0.0033 (13)
Geometric parameters (Å, º) top
O1—C21.366 (4)C4—H40.9500
O1—H1O0.841 (10)C5—C61.390 (5)
O2—C61.364 (4)C5—H50.9500
O2—H2O0.844 (10)C7—C81.503 (4)
O3—N31.244 (4)C8—H8A0.9800
O4—N31.233 (3)C8—H8B0.9800
N1—C71.304 (4)C8—H8C0.9800
N1—N21.369 (4)C9—C141.398 (4)
N2—C91.380 (4)C9—C101.401 (4)
N2—H2N0.880 (10)C10—C111.378 (4)
N3—C121.447 (4)C10—H100.9500
C1—C61.414 (4)C11—C121.383 (4)
C1—C21.418 (4)C11—H110.9500
C1—C71.484 (5)C12—C131.387 (4)
C2—C31.390 (5)C13—C141.375 (4)
C3—C41.377 (5)C13—H130.9500
C3—H30.9500C14—H140.9500
C4—C51.385 (5)
C2—O1—H1O109 (3)N1—C7—C1115.4 (3)
C6—O2—H2O113 (3)N1—C7—C8121.0 (3)
C7—N1—N2119.0 (3)C1—C7—C8123.5 (3)
N1—N2—C9119.7 (3)C7—C8—H8A109.5
N1—N2—H2N120 (2)C7—C8—H8B109.5
C9—N2—H2N120 (2)H8A—C8—H8B109.5
O4—N3—O3123.0 (3)C7—C8—H8C109.5
O4—N3—C12118.7 (3)H8A—C8—H8C109.5
O3—N3—C12118.3 (3)H8B—C8—H8C109.5
C6—C1—C2116.5 (3)N2—C9—C14117.8 (3)
C6—C1—C7122.2 (3)N2—C9—C10122.4 (3)
C2—C1—C7121.4 (3)C14—C9—C10119.7 (3)
O1—C2—C3116.8 (3)C11—C10—C9119.6 (3)
O1—C2—C1121.3 (3)C11—C10—H10120.2
C3—C2—C1122.0 (3)C9—C10—H10120.2
C4—C3—C2119.4 (3)C10—C11—C12119.7 (3)
C4—C3—H3120.3C10—C11—H11120.2
C2—C3—H3120.3C12—C11—H11120.2
C3—C4—C5120.7 (4)C11—C12—C13121.6 (3)
C3—C4—H4119.7C11—C12—N3119.4 (3)
C5—C4—H4119.7C13—C12—N3119.0 (3)
C6—C5—C4120.3 (3)C14—C13—C12118.8 (3)
C6—C5—H5119.9C14—C13—H13120.6
C4—C5—H5119.9C12—C13—H13120.6
O2—C6—C5120.4 (3)C13—C14—C9120.6 (3)
O2—C6—C1118.5 (3)C13—C14—H14119.7
C5—C6—C1121.0 (3)C9—C14—H14119.7
C7—N1—N2—C9−171.3 (3)C6—C1—C7—C8−22.2 (5)
C6—C1—C2—O1−174.7 (3)C2—C1—C7—C8157.6 (3)
C7—C1—C2—O15.5 (5)N1—N2—C9—C14−174.8 (3)
C6—C1—C2—C35.3 (5)N1—N2—C9—C107.6 (5)
C7—C1—C2—C3−174.5 (3)N2—C9—C10—C11177.7 (3)
O1—C2—C3—C4176.7 (3)C14—C9—C10—C110.1 (5)
C1—C2—C3—C4−3.3 (5)C9—C10—C11—C120.6 (5)
C2—C3—C4—C50.1 (5)C10—C11—C12—C13−0.5 (5)
C3—C4—C5—C61.0 (5)C10—C11—C12—N3177.5 (3)
C4—C5—C6—O2−176.3 (3)O4—N3—C12—C112.4 (4)
C4—C5—C6—C11.2 (5)O3—N3—C12—C11−177.3 (3)
C2—C1—C6—O2173.3 (3)O4—N3—C12—C13−179.5 (3)
C7—C1—C6—O2−6.8 (5)O3—N3—C12—C130.9 (4)
C2—C1—C6—C5−4.2 (5)C11—C12—C13—C14−0.2 (5)
C7—C1—C6—C5175.6 (3)N3—C12—C13—C14−178.2 (3)
N2—N1—C7—C1179.4 (3)C12—C13—C14—C90.8 (5)
N2—N1—C7—C83.4 (5)N2—C9—C14—C13−178.5 (3)
C6—C1—C7—N1161.9 (3)C10—C9—C14—C13−0.8 (5)
C2—C1—C7—N1−18.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.84 (2)1.79 (3)2.534 (4)147 (4)
N2—H2N···O3i0.88 (2)2.18 (3)3.039 (4)167 (2)
O2—H2O···O1ii0.85 (4)1.99 (4)2.834 (3)173 (4)
C14—H14···O4i0.952.503.326 (4)146
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H13N3O4
Mr287.27
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)7.9714 (3), 13.5021 (7), 12.1081 (5)
β (°) 90.186 (3)
V (Å3)1303.20 (10)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.10 × 0.10 × 0.08
Data collection
DiffractometerBruker–Nonius Roper CCD camera on κ-goniostat
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.875, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		12144, 2984, 1987
Rint0.070
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.082, 0.184, 1.10
No. of reflections2984
No. of parameters200
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.30, −0.28

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.841 (18)1.79 (3)2.534 (4)147 (4)
N2—H2N···O3i0.88 (2)2.18 (3)3.039 (4)167 (2)
O2—H2O···O1ii0.85 (4)1.99 (4)2.834 (3)173 (4)
C14—H14···O4i0.952.503.326 (4)146
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+3/2, z+1/2.
 

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

First citationBaddeley, T. C., de Souza França, L., Howie, R. A., de Lima, G. M., Skakle, J. M. S., de Souza, J. D., Wardell, J. L. & Wardell, S. M. S. V. (2009). Z. Kristallogr. 224, 213–224.  Web of Science CSD CrossRef CAS Google Scholar
 First citationBaddeley, T. C., Howie, R. A., da Silva Lima, C. H., Kaiser, C. R., de Souza, M. V. N., Wardell, J. L. & Wardell, S. M. S. V. (2009). Z. Kristallogr. 224, 506–514.  Web of Science CrossRef CAS Google Scholar
 First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFerguson, G., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o613–o616.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationGlidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o19–o23.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationHooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationHowie, R. A., da Silva Lima, C. H., Kaiser, C. R., de Souza, M. V. N., Wardell, J. L. & Wardell, S. M. S. V. (2010). Z. Kristallogr. 225, 349–358.  Web of Science CSD CrossRef CAS Google Scholar
 First citationHowie, R. A., de Souza, M. V. N., de Lima Ferreira, M., Kaiser, C. R., Wardell, J. L. & Wardell, S. M. S. V. (2010). Z. Kristallogr. 225, 440–447.  Web of Science CSD CrossRef CAS Google Scholar
 First citationHowie, R. A., de Souza, M. V. N., Pinheiro, A. C., Kaiser, C. R., Wardell, J. L. & Wardell, S. M. S. V. (2011). Z. Kristallogr. 226, 483–491.  Web of Science CSD CrossRef CAS Google Scholar
 First citationNogueira, A., Vasconcelos, T. R. A., Wardell, J. L., Solange, M. S. V. & Wardell, S. M. S. V. (2011). Z. Kristallogr. 226, 846–861.  Web of Science CSD CrossRef CAS 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 citationSheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSouza, M. V. N. de, Howie, R. A., Tiekink, E. R. T., Wardell, J. L., Wardell, S. M. S. V. & Kaiser, C. R. (2010). Acta Cryst. E66, o698–o699.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationWardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell, C. (2007). Acta Cryst. B63, 879–895.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 3| March 2012| Pages o685-o686
doi:10.1107/S1600536812005399
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