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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 66| Part 9| September 2010| Pages o2433-o2434
https://doi.org/10.1107/S1600536810032903

2,6-Di­amino­pyridinium 2-carb­­oxy­benzoate

Mohammad T. M. Al-Dajani,a Hassan H. Abdallah,b Nornisah Mohamed,a‡ Mohd Mustaqim Roslic and Hoong-Kun Func*§

aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 17 July 2010; accepted 16 August 2010; online 28 August 2010)

In the crystal of the title mol­ecular salt, C5H8N3+·C8H5O4−, the diamino­pyridine cation and the phthalate anion are linked by a pair of N—H⋯O hydrogen bonds. Within the phthalate anion, an almost symmetrical O—H⋯O hydrogen bond is observed. The ion pairs are linked by further N—H⋯O hydrogen bonds, generating a two-dimensional network lying parallel to (10[\overline{1}]).

Related literature

For background to 2,6-diamino­pyridines, see: Abu Zuhri & Cox (1989[Abu Zuhri, A. Z. & Cox, J. A. (1989). Mikrochim. Acta, 11, 277-283.]); Inuzuka & Fujimoto (1990[Inuzuka, K. & Fujimoto, A. (1990). Bull. Chem. Soc. Jpn, 63, 216-220.]); El-Mossalamy (2001[El-Mossalamy, E. H. (2001). Pigm. Resin Technol. 30, 164-168.]). For background and the biological activity of phthalic acid, see: Brike et al. (2002[Brike, G., Hirsch, M. & Franz, V. (2002). US Patent No. 636 838 9B1.]); Yamamoto et al. (1990[Yamamoto, S., Nakadate, T., Aizu, E. & Kato, R. (1990). Carcinogenesis, 11, 749-754.]). For related structures: see: Büyükgüngör & Odabąsoğlu (2006[Büyükgüngör, O. & Odabąsoğlu, M. (2006). Acta Cryst. E62, o3816-o3818.]); Al-Dajani et al. (2009[Al-Dajani, M. T. M., Salhin, A., Mohamed, N., Loh, W.-S. & Fun, H.-K. (2009). Acta Cryst. E65, o2931-o2932.]); Raissi Shabari et al. (2010[Raissi Shabari, A., Safaeimovahed, M. & Pourayoubi, M. (2010). Acta Cryst. E66, o551.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C5H8N3+·C8H5O4−

  • Mr = 275.26

  • Monoclinic, C 2/c

  • a = 32.332 (11) Å

  • b = 3.7246 (14) Å

  • c = 24.184 (8) Å

  • β = 123.036 (6)°

  • V = 2441.5 (15) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.47 × 0.10 × 0.03 mm
Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.948, Tmax = 0.996

  • 5492 measured reflections

  • 2757 independent reflections

  • 1869 reflections with I > 2σ(I)

  • Rint = 0.041
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.197

  • S = 1.06

  • 2757 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H1O2⋯O3 1.18 1.29 2.437 (3) 162
N1—H1A⋯O3 0.86 1.98 2.828 (3) 167
N2—H2A⋯O4 0.86 1.98 2.834 (3) 177
N2—H2B⋯O4i 0.86 2.10 2.851 (3) 145
N3—H3A⋯O2ii 0.86 2.35 3.042 (3) 138
N3—H3B⋯O1iii 0.86 2.01 2.858 (3) 171
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y+1, z; (iii) [-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032903/hb5557sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032903/hb5557Isup2.hkl

checkCIF report


Comment top

Phthalic acid is an aromatic dicarboxylic acid which can be used for the preparation of many organic and inorganic compounds such as dyes, perfumes and phthalates(Brike et al. 2002). Some of its derivatives have anti-tumor promoting action (Yamamoto et al. 1990). The diaminopyridine have an important role in the preparation of aromatic azo dyes (Abu Zuhri & Cox, 1989; Inuzuka & Fujimoto, 1990) and in many polarographic investigations (El-Mossalamy, 2001).

All geometrical parameters in the title compound, C5H8N3+.C8H5O4-,(I), are within normal ranges and are comparable with the related structures (Büyükgüngör & Odabąsoǧlu, 2006; Al-Dajani et al., 2009; Shabari et al., 2010). In the crystal structure, the anion and the cation were linked by N1—H1A···O3 and N2—H2A···O4 interactions. In the phthalate anion, a strong intramolecular interaction of O2—H1O2···O3 was observed. Intermolecular N—H···O hydrogen bonds (Table 1) further contribute to the stabilization of crystal structure, forming an infinite two-dimensional network parallel to the (101) plane.

Related literature top

For background to 2,6-diaminopyridines, see: Abu Zuhri & Cox (1989); Inuzuka & Fujimoto (1990); El-Mossalamy (2001). For background and the biological activity of phthalic acid, see: Brike et al. (2002); Yamamoto et al. (1990). For related structures: see: Büyükgüngör & Odabąsoğlu (2006); Al-Dajani et al. (2009); Shabari et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

In a round bottom flask, 25ml of THF was mixed with 2,6-diaminopyridine (0.01 mol, 1.1 g) with stirring. Phthalic anhydrate (0.01 mol, 1.5 g) was dissolved in THF and then added in small portions into the round bottom flask and refluxed for 2 hours. The gray precipitate formed was filtrated and washed with THF. Brown plates of (I) were formed by dissolving the precipitate in hot water and letting it to cool at room temperature. The crystals was then filtered and dried at 60°C.

Refinement top

O-bound H atoms were located from a difference Fourier map and refined as riding with Uiso(H) = 1.5Ueq(O).The remaining H atoms were positioned geometrically [N–H = 0.86Å, C–H = 0.93 Å and refined using a riding model, with Uiso(H) = 1.2Ueq(N,C)].

Structure description top

Phthalic acid is an aromatic dicarboxylic acid which can be used for the preparation of many organic and inorganic compounds such as dyes, perfumes and phthalates(Brike et al. 2002). Some of its derivatives have anti-tumor promoting action (Yamamoto et al. 1990). The diaminopyridine have an important role in the preparation of aromatic azo dyes (Abu Zuhri & Cox, 1989; Inuzuka & Fujimoto, 1990) and in many polarographic investigations (El-Mossalamy, 2001).

All geometrical parameters in the title compound, C5H8N3+.C8H5O4-,(I), are within normal ranges and are comparable with the related structures (Büyükgüngör & Odabąsoǧlu, 2006; Al-Dajani et al., 2009; Shabari et al., 2010). In the crystal structure, the anion and the cation were linked by N1—H1A···O3 and N2—H2A···O4 interactions. In the phthalate anion, a strong intramolecular interaction of O2—H1O2···O3 was observed. Intermolecular N—H···O hydrogen bonds (Table 1) further contribute to the stabilization of crystal structure, forming an infinite two-dimensional network parallel to the (101) plane.

For background to 2,6-diaminopyridines, see: Abu Zuhri & Cox (1989); Inuzuka & Fujimoto (1990); El-Mossalamy (2001). For background and the biological activity of phthalic acid, see: Brike et al. (2002); Yamamoto et al. (1990). For related structures: see: Büyükgüngör & Odabąsoğlu (2006); Al-Dajani et al. (2009); Shabari et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius. Dashed lines indicate the intermolecular hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of (I) viewed down the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
2,6-Diaminopyridinium 2-carboxybenzoate top
Crystal data top
C5H8N3+·C8H5O4−F(000) = 1152
Mr = 275.26Dx = 1.498 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 975 reflections
a = 32.332 (11) Åθ = 3.8–28.1°
b = 3.7246 (14) ŵ = 0.11 mm−1
c = 24.184 (8) ÅT = 100 K
β = 123.036 (6)°Plate, brown
V = 2441.5 (15) Å30.47 × 0.10 × 0.03 mm
Z = 8
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		2757 independent reflections
Radiation source: fine-focus sealed tube1869 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −36→42
Tmin = 0.948, Tmax = 0.996k = −4→4
5492 measured reflectionsl = −31→27
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1138P)2]
where P = (Fo2 + 2Fc2)/3
2757 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Crystal data top
C5H8N3+·C8H5O4−V = 2441.5 (15) Å3
Mr = 275.26Z = 8
Monoclinic, C2/cMo Kα radiation
a = 32.332 (11) ŵ = 0.11 mm−1
b = 3.7246 (14) ÅT = 100 K
c = 24.184 (8) Å0.47 × 0.10 × 0.03 mm
β = 123.036 (6)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		2757 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		1869 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.996Rint = 0.041
5492 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.197H-atom parameters constrained
S = 1.06Δρmax = 0.41 e Å−3
2757 reflectionsΔρmin = −0.40 e Å−3
181 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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 > 2sigma(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
N10.09892 (7)0.9810 (6)0.16036 (9)0.0153 (5)
H1A0.11090.89740.13880.018*
N20.02334 (7)0.8089 (7)0.07262 (10)0.0195 (5)
H2A0.03810.73290.05420.023*
H2B−0.00820.78820.05260.023*
N30.17839 (7)1.1355 (7)0.24299 (10)0.0210 (5)
H3A0.18831.04870.21920.025*
H3B0.19931.22680.28100.025*
C10.04920 (8)0.9585 (7)0.13210 (11)0.0158 (5)
C20.02953 (9)1.0896 (8)0.16702 (11)0.0179 (6)
H2C−0.00421.07540.14940.021*
C30.06092 (9)1.2402 (8)0.22794 (12)0.0191 (6)
H3C0.04781.33090.25100.023*
C40.11140 (9)1.2624 (8)0.25640 (11)0.0169 (5)
H4A0.13191.36360.29800.020*
C50.13083 (8)1.1287 (7)0.22106 (11)0.0153 (5)
O10.26121 (6)−0.0595 (6)0.12827 (8)0.0228 (5)
O20.21888 (6)0.2628 (6)0.15685 (7)0.0191 (4)
H1O20.18160.41810.12250.029*
O30.14264 (6)0.6094 (5)0.10279 (8)0.0193 (5)
O40.06986 (6)0.5317 (6)0.01065 (9)0.0272 (5)
C60.18695 (8)0.1875 (7)0.03925 (11)0.0148 (5)
C70.20221 (9)0.0642 (8)−0.00144 (12)0.0170 (5)
H7A0.2336−0.03360.01790.020*
C80.17220 (9)0.0825 (8)−0.06960 (12)0.0193 (6)
H8A0.18360.0045−0.09550.023*
C90.12537 (9)0.2173 (8)−0.09827 (11)0.0195 (6)
H9A0.10450.2259−0.14400.023*
C100.10903 (9)0.3408 (7)−0.05943 (11)0.0159 (5)
H10A0.07720.4316−0.07970.019*
C110.13903 (8)0.3330 (7)0.00959 (11)0.0145 (5)
C120.11507 (8)0.4977 (7)0.04302 (11)0.0161 (5)
C130.22537 (8)0.1262 (7)0.11219 (11)0.0154 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0160 (10)0.0203 (12)0.0105 (9)0.0010 (9)0.0079 (8)−0.0016 (9)
N20.0140 (9)0.0278 (13)0.0146 (9)−0.0007 (10)0.0066 (8)−0.0046 (10)
N30.0140 (9)0.0340 (15)0.0135 (9)−0.0008 (10)0.0064 (8)−0.0042 (10)
C10.0162 (11)0.0156 (13)0.0147 (10)0.0007 (10)0.0079 (9)0.0025 (10)
C20.0162 (11)0.0185 (14)0.0181 (11)0.0005 (11)0.0089 (10)0.0018 (11)
C30.0236 (12)0.0207 (14)0.0175 (11)0.0051 (12)0.0141 (10)0.0020 (11)
C40.0196 (11)0.0175 (13)0.0136 (11)−0.0001 (11)0.0091 (10)−0.0004 (11)
C50.0170 (11)0.0148 (13)0.0111 (10)−0.0031 (10)0.0057 (9)−0.0006 (10)
O10.0190 (9)0.0286 (11)0.0184 (8)0.0056 (9)0.0085 (7)0.0023 (9)
O20.0170 (8)0.0274 (11)0.0127 (8)0.0010 (8)0.0078 (7)−0.0007 (8)
O30.0155 (8)0.0272 (11)0.0151 (8)0.0011 (8)0.0084 (7)−0.0045 (8)
O40.0152 (9)0.0409 (13)0.0235 (9)−0.0007 (9)0.0092 (7)−0.0105 (10)
C60.0147 (10)0.0162 (13)0.0134 (10)−0.0004 (10)0.0076 (9)0.0005 (10)
C70.0161 (11)0.0185 (13)0.0184 (11)−0.0018 (11)0.0107 (9)−0.0010 (11)
C80.0261 (13)0.0192 (14)0.0191 (11)−0.0028 (12)0.0166 (10)−0.0008 (11)
C90.0209 (12)0.0205 (14)0.0126 (10)−0.0037 (11)0.0062 (9)−0.0003 (11)
C100.0141 (10)0.0156 (13)0.0162 (11)−0.0024 (10)0.0072 (9)−0.0013 (10)
C110.0153 (10)0.0127 (12)0.0162 (11)−0.0016 (10)0.0090 (9)−0.0017 (10)
C120.0159 (11)0.0176 (14)0.0161 (11)−0.0023 (11)0.0095 (9)−0.0015 (11)
C130.0141 (10)0.0166 (13)0.0161 (11)−0.0004 (10)0.0086 (9)0.0020 (10)
Geometric parameters (Å, º) top
N1—C11.364 (3)O2—C131.310 (3)
N1—C51.368 (3)O2—H1O21.1764
N1—H1A0.8600O3—C121.285 (3)
N2—C11.329 (3)O3—H1O21.2919
N2—H2A0.8600O4—C121.232 (3)
N2—H2B0.8600C6—C71.397 (3)
N3—C51.326 (3)C6—C111.413 (3)
N3—H3A0.8600C6—C131.522 (3)
N3—H3B0.8600C7—C81.385 (3)
C1—C21.393 (3)C7—H7A0.9300
C2—C31.373 (3)C8—C91.372 (3)
C2—H2C0.9300C8—H8A0.9300
C3—C41.386 (3)C9—C101.383 (3)
C3—H3C0.9300C9—H9A0.9300
C4—C51.399 (3)C10—C111.401 (3)
C4—H4A0.9300C10—H10A0.9300
O1—C131.217 (3)C11—C121.521 (3)
C1—N1—C5123.8 (2)C12—O3—H1O2100.1
C1—N1—H1A118.1C7—C6—C11118.6 (2)
C5—N1—H1A118.1C7—C6—C13112.8 (2)
C1—N2—H2A120.0C11—C6—C13128.5 (2)
C1—N2—H2B120.0C8—C7—C6122.3 (2)
H2A—N2—H2B120.0C8—C7—H7A118.8
C5—N3—H3A120.0C6—C7—H7A118.8
C5—N3—H3B120.0C9—C8—C7118.9 (2)
H3A—N3—H3B120.0C9—C8—H8A120.5
N2—C1—N1116.2 (2)C7—C8—H8A120.5
N2—C1—C2125.2 (2)C8—C9—C10120.2 (2)
N1—C1—C2118.5 (2)C8—C9—H9A119.9
C3—C2—C1118.6 (2)C10—C9—H9A119.9
C3—C2—H2C120.7C9—C10—C11122.0 (2)
C1—C2—H2C120.7C9—C10—H10A119.0
C2—C3—C4122.6 (2)C11—C10—H10A119.0
C2—C3—H3C118.7C10—C11—C6117.9 (2)
C4—C3—H3C118.7C10—C11—C12113.7 (2)
C3—C4—C5118.3 (2)C6—C11—C12128.3 (2)
C3—C4—H4A120.8O4—C12—O3122.4 (2)
C5—C4—H4A120.8O4—C12—C11118.4 (2)
N3—C5—N1118.0 (2)O3—C12—C11119.1 (2)
N3—C5—C4123.9 (2)O1—C13—O2120.6 (2)
N1—C5—C4118.1 (2)O1—C13—C6119.3 (2)
C13—O2—H1O299.9O2—C13—C6120.0 (2)
C5—N1—C1—N2179.6 (2)C9—C10—C11—C6−1.2 (4)
C5—N1—C1—C2−0.7 (4)C9—C10—C11—C12177.1 (2)
N2—C1—C2—C3−179.5 (3)C7—C6—C11—C100.9 (4)
N1—C1—C2—C30.9 (4)C13—C6—C11—C10−175.8 (2)
C1—C2—C3—C4−0.9 (4)C7—C6—C11—C12−177.1 (3)
C2—C3—C4—C50.7 (4)C13—C6—C11—C126.2 (4)
C1—N1—C5—N3−179.8 (2)C10—C11—C12—O419.0 (4)
C1—N1—C5—C40.5 (4)C6—C11—C12—O4−162.9 (3)
C3—C4—C5—N3179.8 (3)C10—C11—C12—O3−158.2 (2)
C3—C4—C5—N1−0.4 (4)C6—C11—C12—O319.9 (4)
C11—C6—C7—C80.5 (4)C7—C6—C13—O1−9.9 (3)
C13—C6—C7—C8177.8 (3)C11—C6—C13—O1167.0 (3)
C6—C7—C8—C9−1.8 (4)C7—C6—C13—O2172.4 (2)
C7—C8—C9—C101.6 (4)C11—C6—C13—O2−10.8 (4)
C8—C9—C10—C11−0.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O31.181.292.437 (3)162
N1—H1A···O30.861.982.828 (3)167
N2—H2A···O40.861.982.834 (3)177
N2—H2B···O4i0.862.102.851 (3)145
N3—H3A···O2ii0.862.353.042 (3)138
N3—H3B···O1iii0.862.012.858 (3)171
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) −x+1/2, y+3/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC5H8N3+·C8H5O4−
Mr275.26
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)32.332 (11), 3.7246 (14), 24.184 (8)
β (°) 123.036 (6)
V (Å3)2441.5 (15)
Z8
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.47 × 0.10 × 0.03
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.948, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections		5492, 2757, 1869
Rint0.041
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.197, 1.06
No. of reflections2757
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O31.181.292.437 (3)162
N1—H1A···O30.861.982.828 (3)167
N2—H2A···O40.861.982.834 (3)177
N2—H2B···O4i0.862.102.851 (3)145
N3—H3A···O2ii0.862.353.042 (3)138
N3—H3B···O1iii0.862.012.858 (3)171
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) −x+1/2, y+3/2, −z+1/2.
 

Footnotes

‡Additional correspondence author, e-mail: nornisah@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NM gratefully acknowledges funding from Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815025) and HHA gratefully acknowledges funding from Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PKIMIA/811142). HKF thanks Universiti Sains Malaysia for the Research University Golden Goose grant (No. 1001/PFIZIK/811012).

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Pages o2433-o2434
https://doi.org/10.1107/S1600536810032903
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