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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages m309-m310

Bis(3-amino­pyrazine-2-carboxyl­ato-κ2N1,O)di­aqua­nickel(II) dihydrate

aLaboratoire de Chimie Appliquée et Technologie des Matériaux LCATM, Université Oum El Bouaghi, Algeria, bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, Algeria, and cUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Faculté des Sciences Exactes, Université Constantine 25000, Algeria
*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 29 April 2013; accepted 3 May 2013; online 11 May 2013)

In the title compound, [Ni(C5H4N3O2)2(H2O)2]·2H2O, the NiII ion lies on an inversion center and is coordinated in an slightly distorted octa­hedral environment by two N,O-chelating 3-amino­pyrazine-2-carboxyl­ate (APZC) ligands in the equatorial plane and two trans-axial aqua ligands. In the crystal, O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds involving the solvent water mol­ecules, aqua and APZC ligands form layers parallel to (010). These layers are linked further via O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds involving the axial aqua ligands, amino groups and the carboxyl­ate groups of the APZC ligands, forming a three-dimensional network.

Related literature

For background to hybrid compounds, see: Bouchene et al. (2013[Bouchene, R., Bouacida, S., Berrah, F., Belhouas, R. & Merazig, H. (2013). Acta Cryst. E69, m129-m130.]); Bouacida et al. (2007[Bouacida, S., Merazig, H., Benard-Rocherulle, P. & Rizzoli, C. (2007). Acta Cryst. E63, m379-m381.], 2009[Bouacida, S., Belhouas, R., Kechout, H., Merazig, H. & Bénard-Rocherullé, P. (2009). Acta Cryst. E65, o628-o629.]). For the structure of the non-hydrated analogue, see: Ptasiewicz-Bak & Leciejewicz (1999[Ptasiewicz-Bak, H. & Leciejewicz, J. (1999). Pol. J. Chem. 73, 717-725.]). For 3-amino­pyrazine-2-carboxyl­ate–metal (M) complexes, see: Bouchene et al. (2013[Bouchene, R., Bouacida, S., Berrah, F., Belhouas, R. & Merazig, H. (2013). Acta Cryst. E69, m129-m130.]) [M = Co(II)]; Leciejewicz et al. (1997[Leciejewicz, J., Ptasiewicz-Bak, H. & Paluchowska, B. (1997). Pol. J. Chem. 71, 1339-1364.]) [M = Ca(II)]; Leciejewicz et al. (1998[Leciejewicz, J., Ptasiewicz-Bak, H. & Zachara, J. (1998). Pol. J. Chem. 72, 1994-1998.]) [M = Sr(II)]; Ptasiewicz-Bak & Leciejewicz (1997[Ptasiewicz-Bak, H. & Leciejewicz, J. (1997). Pol. J. Chem. 71, 1350-1358.]) [M = Mg(II)]; Tayebee et al. (2008[Tayebee, R., Amani, V. & Khavasi, H. P. (2008). Chin. J. Chem. 26, 500-504.]) [M = Na(I)]; Ptasiewicz-Bak & Leciejewicz (1999[Ptasiewicz-Bak, H. & Leciejewicz, J. (1999). Pol. J. Chem. 73, 717-725.]). For proprieties and applications of pyrazine-2-carb­oxy­lic acid, see: Zhang & Mitchison (2003[Zhang, Y. & Mitchison, D. A. (2003). Int. J. Tuberc. Lung Dis. 7,6-21.]); Manju & Chaudhary, (2010[Manju, A. & Chaudhary, D. (2010). Asian J. Chem. Environ. Res. 3, 13-17.]); Chanda & Sangeetika (2004[Chanda, S. & Sangeetika, J. (2004). J. Indian Chem. Soc. 81, 203-206.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C5H4N3O2)2(H2O)2]·2H2O

  • Mr = 406.98

  • Monoclinic, P 21 /c

  • a = 9.7939 (15) Å

  • b = 5.1123 (9) Å

  • c = 16.776 (3) Å

  • β = 115.838 (11)°

  • V = 756.0 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.34 mm−1

  • T = 150 K

  • 0.18 × 0.16 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 6200 measured reflections

  • 1326 independent reflections

  • 1121 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.073

  • S = 1.04

  • 1326 reflections

  • 127 parameters

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

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.59 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1A⋯O2Wi 0.83 (3) 1.97 (3) 2.789 (3) 169 (3)
O1W—H1B⋯O1ii 0.75 (3) 1.94 (3) 2.690 (3) 176 (4)
N3—H1N⋯O2Wiii 0.86 2.27 3.117 (3) 168
O2W—H2A⋯O2Wiv 0.77 (3) 2.12 (3) 2.867 (3) 164 (4)
O2W—H2B⋯N2v 0.78 (3) 2.03 (3) 2.792 (3) 168 (3)
N3—H2N⋯O2 0.86 2.10 2.733 (3) 130
N3—H2N⋯O2vi 0.86 2.20 2.871 (3) 135
C5—H5⋯O1Wvii 0.93 2.54 3.377 (4) 150
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2; (iii) -x, -y+1, -z+2; (iv) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (vi) -x, -y, -z+2; (vii) x, y+1, z.

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

The pyrazine-2-carboxylic acid bridging ligand, owing to its ability to act in acidic environments (Zhang & Mitchison, 2003), has been extensively studied for biological applications, such as anti-tubercular (Manju et al., 2010), antipyretic, antitumor, and anticancer (Chanda et al., 2004). An additional amino substitution on 3-amino-2-pyrazine carboxylic acid could be expected to enhance crystal packing through extensive hydrogen bonding. APZC has a large variety of coordination geometries in metal complexes (Leciejewicz et al., 1997, 1998; Ptasiewicz-Bak & Leciejewicz, 1997; Tayebee et al., 2008).

In continuation of our search to enrich the variety of such kinds of hybrid compounds and to investigate the influence of hydrogen bonds on the structural features (Bouacida et al., 2007, 2009), we report here the synthesis and crystal structure of the title compound, (I), as a extention of our earlier work on N,O chelated ligands (Bouchene et al.2013) which can be involved in covalent interactions in metal coordination chemistry.

The asymmetric unit of (I) consists of one-half of the molecule, with the other half generated by a crystallographic inversion center. The molecular structure is shown in Fig. 1. The NiII ion is coordinated by two 3-amino-2-pyrazine carboxylate ligands via N,O-chelating groups in the equatorial plane and two aqua O atoms in the axial sites forming a slightly distorted octahedral coordination environment. The Ni—N, Ni—O and Ni—Oaqua distances are consistent with the reported data for the anhydrous Ni(II)(APZC)2(H2O)2 complex (Ptasiewicz-Bak & Leciejewicz, 1999). In the crystal, the solvent water molecules and complex molecules are involved in intermolecular O—H···O, O—H···N and N—H···O hydrogen bonds forming two-dimensional layers parallel to (010) (Fig.2). Further O—H···O hydrogen bonds (Fig.3) involving the aqua ligands, N—H···.O hydrogen bonds the carboxylate groups of the APZC ligands form a three-dimensional network.

Related literature top

For background to hybrid compounds, see: Bouchene et al. (2013); Bouacida et al. (2007, 2009). For the structure of the non-hydrated analogue, see: Ptasiewicz-Bak & Leciejewicz (1999). For 3-aminopyrazine-2-carboxylate–metal (M) complexes, see: Bouchene et al. (2013) [M = Co(II)]; Leciejewicz et al. (1997) [M = Ca(II)]; Leciejewicz et al. (1998) [M = Sr(II)]; Ptasiewicz-Bak & Leciejewicz (1997) [M = Mg(II)]; Tayebee et al. (2008) [M = Na(I)]; Ptasiewicz-Bak & Leciejewicz (1999). For proprieties and applications of pyrazine-2-carboxylic acid, see: Zhang & Mitchison (2003); Manju & Chaudhary, (2010); Chanda & Sangeetika (2004).

Experimental top

Nickel dichloride hexahydrate (0.2 mmol) and 3-aminopyrazine-2-carboxylic acid (0.02 mmol) were dissolved in acidified water with concentrated hydrogen chloride acid (37%). Light green crystals, suitable for X-ray diffraction study, were obtained from evaporation of obtained solution for three days.

Refinement top

The H atoms bonded to C and N were located in differnce Fourier maps but subsequently introduced in calculated positions and treated as riding on their parent atoms (C or N) with C—H = 0.93 Å and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(C or N). Atoms H1W and H2W were located in a difference Fourier map and refined isotropically wirh Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. Symmetry code: (i)-x+1, -y+1, -z+2.
[Figure 2] Fig. 2. Partial packing plot viewed along the b axis showing the hydrogen bonds (dashed lines) forming layers.
[Figure 3] Fig. 3. Partial packing of (I) showing only the O—H···O hydrogen bonds which connect the layers in Fig. 2 into a three-dimensional network.
Bis(3-aminopyrazine-2-carboxylato-κ2N1,O)diaquanickel(II) dihydrate top
Crystal data top
[Ni(C5H4N3O2)2(H2O)2]·2H2OF(000) = 420
Mr = 406.98Dx = 1.788 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.7939 (15) ÅCell parameters from 2285 reflections
b = 5.1123 (9) Åθ = 2.7–25°
c = 16.776 (3) ŵ = 1.34 mm1
β = 115.838 (11)°T = 150 K
V = 756.0 (2) Å3Cube, white
Z = 20.18 × 0.16 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
1121 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.051
Graphite monochromatorθmax = 25.1°, θmin = 2.7°
ϕ and ω scansh = 1111
6200 measured reflectionsk = 66
1326 independent reflectionsl = 1919
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0363P)2 + 0.4886P]
where P = (Fo2 + 2Fc2)/3
1326 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.59 e Å3
Crystal data top
[Ni(C5H4N3O2)2(H2O)2]·2H2OV = 756.0 (2) Å3
Mr = 406.98Z = 2
Monoclinic, P21/cMo Kα radiation
a = 9.7939 (15) ŵ = 1.34 mm1
b = 5.1123 (9) ÅT = 150 K
c = 16.776 (3) Å0.18 × 0.16 × 0.15 mm
β = 115.838 (11)°
Data collection top
Bruker APEXII CCD
diffractometer
1121 reflections with I > 2σ(I)
6200 measured reflectionsRint = 0.051
1326 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.36 e Å3
1326 reflectionsΔρmin = 0.59 e Å3
127 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
C10.2428 (3)0.2367 (5)0.99519 (16)0.0089 (5)
C20.2750 (3)0.4494 (4)1.06347 (15)0.0079 (5)
C30.1864 (3)0.4915 (5)1.11094 (15)0.0090 (5)
C40.3430 (3)0.8353 (5)1.18295 (16)0.0098 (5)
H40.36920.97111.22390.012*
C50.4304 (3)0.7942 (5)1.13805 (15)0.0097 (5)
H50.51410.89991.14920.012*
N10.3937 (2)0.6010 (4)1.07831 (13)0.0074 (4)
N20.2227 (2)0.6890 (4)1.17019 (13)0.0102 (4)
N30.0696 (2)0.3396 (4)1.10092 (14)0.0125 (5)
H1N0.02020.36891.13160.015*
H2N0.04360.21221.06370.015*
O10.33555 (17)0.2240 (3)0.96010 (11)0.0090 (4)
O20.13487 (18)0.0885 (3)0.97784 (12)0.0137 (4)
O1W0.6426 (2)0.2542 (4)1.10017 (12)0.0102 (4)
H1A0.726 (3)0.312 (6)1.1356 (19)0.015*
H1B0.652 (3)0.124 (6)1.083 (2)0.015*
O2W0.0735 (2)0.6137 (4)0.76616 (12)0.0133 (4)
H2A0.046 (4)0.472 (6)0.754 (2)0.02*
H2B0.104 (3)0.663 (6)0.733 (2)0.02*
Ni10.50.510.00664 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0073 (11)0.0071 (12)0.0116 (12)0.0010 (9)0.0036 (10)0.0014 (10)
C20.0067 (12)0.0078 (12)0.0087 (11)0.0002 (9)0.0029 (10)0.0009 (9)
C30.0078 (11)0.0088 (12)0.0098 (11)0.0029 (10)0.0031 (9)0.0029 (11)
C40.0114 (12)0.0077 (12)0.0105 (12)0.0014 (9)0.0050 (10)0.0024 (10)
C50.0068 (12)0.0089 (12)0.0137 (13)0.0011 (9)0.0048 (10)0.0017 (10)
N10.0040 (10)0.0067 (10)0.0102 (10)0.0004 (8)0.0019 (8)0.0009 (8)
N20.0097 (10)0.0101 (11)0.0123 (10)0.0008 (8)0.0061 (9)0.0001 (8)
N30.0094 (10)0.0139 (11)0.0195 (11)0.0052 (9)0.0113 (9)0.0056 (9)
O10.0069 (8)0.0093 (8)0.0137 (9)0.0018 (7)0.0073 (7)0.0032 (7)
O20.0092 (9)0.0135 (9)0.0213 (10)0.0055 (7)0.0092 (8)0.0059 (8)
O1W0.0077 (9)0.0081 (9)0.0147 (9)0.0015 (7)0.0046 (8)0.0030 (8)
O2W0.0148 (10)0.0129 (9)0.0169 (10)0.0035 (8)0.0115 (8)0.0018 (8)
Ni10.0049 (2)0.0062 (2)0.0106 (2)0.00089 (17)0.00506 (18)0.00108 (18)
Geometric parameters (Å, º) top
C1—O21.228 (3)N1—Ni12.0657 (19)
C1—O11.281 (3)N3—H1N0.86
C1—C21.510 (3)N3—H2N0.86
C2—N11.327 (3)O1—Ni12.0233 (16)
C2—C31.427 (3)O1W—Ni12.0755 (18)
C3—N31.331 (3)O1W—H1A0.83 (3)
C3—N21.351 (3)O1W—H1B0.74 (3)
C4—N21.332 (3)O2W—H2A0.77 (3)
C4—C51.381 (3)O2W—H2B0.78 (3)
C4—H40.93Ni1—O1i2.0233 (16)
C5—N11.340 (3)Ni1—N1i2.066 (2)
C5—H50.93Ni1—O1Wi2.0755 (18)
O2—C1—O1124.7 (2)H1N—N3—H2N120
O2—C1—C2119.8 (2)C1—O1—Ni1115.72 (15)
O1—C1—C2115.5 (2)Ni1—O1W—H1A118 (2)
N1—C2—C3120.2 (2)Ni1—O1W—H1B113 (2)
N1—C2—C1116.0 (2)H1A—O1W—H1B110 (3)
C3—C2—C1123.7 (2)H2A—O2W—H2B108 (3)
N3—C3—N2117.7 (2)O1—Ni1—O1i180
N3—C3—C2122.7 (2)O1—Ni1—N180.54 (7)
N2—C3—C2119.6 (2)O1i—Ni1—N199.46 (7)
N2—C4—C5122.8 (2)O1—Ni1—N1i99.46 (7)
N2—C4—H4118.6O1i—Ni1—N1i80.54 (7)
C5—C4—H4118.6N1—Ni1—N1i180.0000 (10)
N1—C5—C4119.5 (2)O1—Ni1—O1Wi89.81 (7)
N1—C5—H5120.3O1i—Ni1—O1Wi90.19 (7)
C4—C5—H5120.3N1—Ni1—O1Wi90.92 (7)
C2—N1—C5119.9 (2)N1i—Ni1—O1Wi89.08 (7)
C2—N1—Ni1112.20 (15)O1—Ni1—O1W90.19 (7)
C5—N1—Ni1127.92 (16)O1i—Ni1—O1W89.81 (7)
C4—N2—C3117.9 (2)N1—Ni1—O1W89.08 (7)
C3—N3—H1N120N1i—Ni1—O1W90.92 (7)
C3—N3—H2N120O1Wi—Ni1—O1W180.00 (9)
O2—C1—C2—N1180.0 (2)N3—C3—N2—C4177.5 (2)
O1—C1—C2—N11.0 (3)C2—C3—N2—C41.1 (3)
O2—C1—C2—C30.2 (4)O2—C1—O1—Ni1178.74 (18)
O1—C1—C2—C3178.8 (2)C2—C1—O1—Ni12.3 (3)
N1—C2—C3—N3177.5 (2)C1—O1—Ni1—N12.15 (16)
C1—C2—C3—N32.3 (4)C1—O1—Ni1—N1i177.85 (16)
N1—C2—C3—N21.0 (3)C1—O1—Ni1—O1Wi88.81 (16)
C1—C2—C3—N2179.2 (2)C1—O1—Ni1—O1W91.19 (16)
N2—C4—C5—N10.5 (4)C2—N1—Ni1—O11.50 (15)
C3—C2—N1—C50.0 (3)C5—N1—Ni1—O1179.2 (2)
C1—C2—N1—C5179.9 (2)C2—N1—Ni1—O1i178.50 (15)
C3—C2—N1—Ni1179.41 (17)C5—N1—Ni1—O1i0.8 (2)
C1—C2—N1—Ni10.8 (2)C2—N1—Ni1—O1Wi88.16 (16)
C4—C5—N1—C20.7 (3)C5—N1—Ni1—O1Wi91.1 (2)
C4—C5—N1—Ni1178.57 (17)C2—N1—Ni1—O1W91.84 (16)
C5—C4—N2—C30.4 (3)C5—N1—Ni1—O1W88.9 (2)
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O2Wi0.83 (3)1.97 (3)2.789 (3)169 (3)
O1W—H1B···O1ii0.75 (3)1.94 (3)2.690 (3)176 (4)
N3—H1N···O2Wiii0.862.273.117 (3)168
O2W—H2A···O2Wiv0.77 (3)2.12 (3)2.867 (3)164 (4)
O2W—H2B···N2v0.78 (3)2.03 (3)2.792 (3)168 (3)
N3—H2N···O20.862.102.733 (3)130
N3—H2N···O2vi0.862.202.871 (3)135
C5—H5···O1Wvii0.932.543.377 (4)150
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y, z+2; (iii) x, y+1, z+2; (iv) x, y1/2, z+3/2; (v) x, y+3/2, z1/2; (vi) x, y, z+2; (vii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Ni(C5H4N3O2)2(H2O)2]·2H2O
Mr406.98
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)9.7939 (15), 5.1123 (9), 16.776 (3)
β (°) 115.838 (11)
V3)756.0 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.34
Crystal size (mm)0.18 × 0.16 × 0.15
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6200, 1326, 1121
Rint0.051
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.073, 1.04
No. of reflections1326
No. of parameters127
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.36, 0.59

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O2Wi0.83 (3)1.97 (3)2.789 (3)169 (3)
O1W—H1B···O1ii0.75 (3)1.94 (3)2.690 (3)176 (4)
N3—H1N···O2Wiii0.862.273.117 (3)168
O2W—H2A···O2Wiv0.77 (3)2.12 (3)2.867 (3)164 (4)
O2W—H2B···N2v0.78 (3)2.03 (3)2.792 (3)168 (3)
N3—H2N···O20.862.102.733 (3)130
N3—H2N···O2vi0.862.202.871 (3)135
C5—H5···O1Wvii0.932.543.377 (4)150
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y, z+2; (iii) x, y+1, z+2; (iv) x, y1/2, z+3/2; (v) x, y+3/2, z1/2; (vi) x, y, z+2; (vii) x, y+1, z.
 

Acknowledgements

We are grateful to all personal of the LCATM laboratory, Université Oum El Bouaghi, Algeria, for their assistance. Thanks are due to MESRS and ATRST (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Thématique de Recherche en Sciences et Technologie - Algeria) via the PNR programm for financial support.

References

First citationBouacida, S., Belhouas, R., Kechout, H., Merazig, H. & Bénard-Rocherullé, P. (2009). Acta Cryst. E65, o628–o629.  Web of Science CSD CrossRef CAS IUCr Journals
First citationBouacida, S., Merazig, H., Benard-Rocherulle, P. & Rizzoli, C. (2007). Acta Cryst. E63, m379–m381.  Web of Science CSD CrossRef CAS IUCr Journals
First citationBouchene, R., Bouacida, S., Berrah, F., Belhouas, R. & Merazig, H. (2013). Acta Cryst. E69, m129–m130.  CSD CrossRef CAS IUCr Journals
First citationBrandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
First citationBruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.  Web of Science CrossRef CAS IUCr Journals
First citationChanda, S. & Sangeetika, J. (2004). J. Indian Chem. Soc. 81, 203–206.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationLeciejewicz, J., Ptasiewicz-Bak, H. & Paluchowska, B. (1997). Pol. J. Chem. 71, 1339–1364.
First citationLeciejewicz, J., Ptasiewicz-Bak, H. & Zachara, J. (1998). Pol. J. Chem. 72, 1994–1998.  CAS
First citationManju, A. & Chaudhary, D. (2010). Asian J. Chem. Environ. Res. 3, 13–17.  CAS
First citationPtasiewicz-Bak, H. & Leciejewicz, J. (1997). Pol. J. Chem. 71, 1350–1358.  CAS
First citationPtasiewicz-Bak, H. & Leciejewicz, J. (1999). Pol. J. Chem. 73, 717–725.  CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTayebee, R., Amani, V. & Khavasi, H. P. (2008). Chin. J. Chem. 26, 500–504.  Web of Science CSD CrossRef CAS
First citationZhang, Y. & Mitchison, D. A. (2003). Int. J. Tuberc. Lung Dis. 7,6–21.  Web of Science PubMed CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages m309-m310
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds