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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Pages m1067-m1068
https://doi.org/10.1107/S1600536812031200

Di­aqua­bis­­(N,N-di­ethyl­nicotinamide-κN1)bis­­(4-formyl­benzoato-κO1)zinc

Mustafa Sertçelik,a Nagihan Çaylak Delibaş,b Hacali Necefoğlua and Tuncer Hökelekc*

aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, bDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 27 June 2012; accepted 9 July 2012; online 14 July 2012)

In the title complex, [Zn(C8H5O3)2(C10H14N2O)2(H2O)2], the ZnII cation is located on an inversion center and is coordinated by two 4-formyl­benzoate anions, two N,N-diethyl­nicotinamide (DENA) ligands and two water mol­ecules. The four O atoms in the equatorial plane around the ZnII cation form a slightly distorted square-planar arrangement, while the slightly distorted octa­hedral coordination is completed by the two N atoms of the DENA ligands in the axial positions. The dihedral angle between the carboxyl­ate group and the adjacent benzene ring is 2.96 (11)°, while the pyridine ring and the benzene ring are oriented at a dihedral angle of 79.26 (4)°. The coordinating water mol­ecule links with the carboxyl­ate group via an intra­molecular O—H⋯O hydrogen bond. In the crystal, O—H⋯O and weak C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional supra­molecular network. A π–π contact between the parallel pyridine rings of adjacent mol­ecules may further stabilize the crystal structure [centroid–centroid distance = 3.5654 (8) Å].

Related literature

For literature on niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For information on the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972[Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.]). For related structures, see: Aydın et al. (2012[Aydın, Ö., Çaylak Delibaş, N., Necefoğlu, H. & Hökelek, T. (2012). Acta Cryst. E68, m521-m522.]); Hökelek et al. (1996[Hökelek, T., Gündüz, H. & Necefoğlu, H. (1996). Acta Cryst. C52, 2470-2473.], 2009a[Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H. (2009a). Acta Cryst. E65, m466-m467.],b[Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H. (2009b). Acta Cryst. E65, m607-m608.]); Hökelek & Necefoğlu (2007[Hökelek, T. & Necefoğlu, H. (2007). Acta Cryst. E63, m821-m823.], 1998[Hökelek, T. & Necefoğlu, H. (1998). Acta Cryst. C54, 1242-1244.]); Necefoğlu, Özbek et al. (2011[Necefoğlu, H., Özbek, F. E., Öztürk, V., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m900-m901.]); Necefoğlu, Maracı et al. (2011[Necefoğlu, H., Maracı, A., Özbek, F. E., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m619-m620.]); Sertçelik et al. (2012[Sertçelik, M., Çaylak Delibaş, N., Necefoğlu, H. & Hökelek, T. (2012). Acta Cryst. E68, m946-m947.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C8H5O3)2(C10H14N2O)2(H2O)2]

  • Mr = 756.13

  • Triclinic, [P \overline 1]

  • a = 7.1988 (2) Å

  • b = 8.5347 (2) Å

  • c = 15.9719 (4) Å

  • α = 85.435 (3)°

  • β = 78.010 (3)°

  • γ = 67.846 (2)°

  • V = 889.03 (4) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.75 mm−1

  • T = 100 K

  • 0.27 × 0.24 × 0.21 mm
Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.816, Tmax = 0.854

  • 16164 measured reflections

  • 4409 independent reflections

  • 4128 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.025

  • wR(F2) = 0.081

  • S = 1.16

  • 4409 reflections

  • 246 parameters

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

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5—H51⋯O4i 0.80 (2) 1.97 (2) 2.7591 (15) 169 (2)
O5—H52⋯O1ii 0.85 (2) 1.81 (2) 2.6494 (14) 166 (2)
C4—H4⋯O1iii 0.93 2.36 3.1975 (19) 150
C7—H7⋯O3iv 0.93 2.60 3.406 (2) 145
C11—H11⋯O1v 0.93 2.40 3.3068 (17) 166
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y, -z; (iii) x+1, y, z; (iv) x-1, y, z; (v) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812031200/xu5586sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031200/xu5586Isup2.hkl

checkCIF report


Comment top

As a part of our ongoing investigations of transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

In the title mononuclear complex, ZnII cation is located on an inversion center and is coordinated by two 4-formylbenzoate (FB) anions, two N,N-diethylnicotinamide (DENA) ligands and two water molecules, all ligands coordinating in a monodentate manner (Fig. 1). The crystal structures of similar complexes of CuII, CoII, NiII, MnII and ZnII ions, [Cu(C7H5O2)2(C10H14N2O)2] (Hökelek et al., 1996), [Cu(C7H4BrO2)2(C6H6N2O)2(H2O)2] (Necefoğlu, Özbek et al., 2011), [Co(C6H6N2O)2(C7H4NO4)2(H2O)2] (Hökelek & Necefoğlu, 1998), [Co(C9H9O2)2(C10H14N2O)2(H2O)2] (Necefoğlu, Maracı et al., 2011), [Co(C7H4IO2)2(C6H6N2O)2(H2O)2] (Aydın et al., 2012), [Ni(C7H4ClO2)2(C6H6N2O)2(H2O)2] (Hökelek et al., 2009a), [Ni(C5H5O3)2(C6H6N2O)2(H2O)2] (Sertçelik et al., 2012), [Mn(C9H10NO2)2(H2O)4].2H2O (Hökelek & Necefoğlu, 2007) and [Zn(C7H4BrO2)2(C6H6N2O)2(H2O)2] (Hökelek et al., 2009b) have also been reported. In the copper(II) complex mentioned above the two benzoate ions coordinate to the CuII atom as bidentate ligands, while in the other structures all the ligands coordinate in a monodentate manner.

In the title complex, the four symmetry related O atoms (O2, O2', O5 and O5') in the equatorial plane around the ZnII ion form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two symmetry related N atoms of the DENA ligands (N1 and N1') in the axial positions. The near equalities of the C1—O1 [1.2533 (16) Å] and C1—O2 [1.2623 (16) Å] bonds in the carboxylate group indicate delocalized bonding arrangement, rather than localized single and double bonds. The Zn—O bond lengths are 2.1128 (9) Å (for benzoate oxygens) and 2.1289 (10) Å (for water oxygens), and the Cu—N bond length is 2.1452 (11) Å, close to standard values (Allen et al., 1987). The Zn atom is displaced out of the mean-plane of the carboxylate group (O1/C1/O2) by 0.8455 (1) Å. The dihedral angle between the planar carboxylate group and the adjacent benzene ring A (C2—C7) is 2.96 (11)°. The benzene A (C2—C7) and the pyridine B (N1/C9—C13) rings are oriented at a dihedral angle of A/B = 79.26 (4)°. The coordinating water molecule links with the carboxylate group via an O—H···O hydrogen bond (Table 1).

In the crystal, intermolecular O—H···O and weak C—H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional supramolecular network, in which they may be effective in the stabilization of the structure. The π–π contact between the pyridine rings, Cg2—Cg2i [symmetry code: (i) 1 - x, 1 - y, -z, where Cg2 is the centroid of the ring B (N1/C9-C13)] may further stabilize the structure, with centroid-centroid distance of 3.5654 (8) Å].

Related literature top

For literature on niacin, see: Krishnamachari (1974). For information on the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Aydın et al. (2012); Hökelek et al. (1996, 2009a,b); Hökelek & Necefoğlu (2007, 1998); Necefoğlu, Özbek et al. (2011); Necefoğlu, Maracı et al. (2011); Sertçelik et al. (2012). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of ZnSO4.H2O (0.90 g, 5 mmol) in H2O (30 ml) and DENA (1.78 g, 10 mmol) in H2O (10 ml) with sodium 4-formylbenzoate (1.72 g, 10 mmol) in H2O (100 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving colorless single crystals.

Refinement top

Atoms H8 (for CH) and H51 and H52 (for H2O) were located in a difference Fourier map and were refined freely. The C-bound H-atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å, for aromatic, methylene and methyl H-atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = k × Ueq(C), where k = 1.5 for methyl H-atoms and k = 1.2 for all other H-atoms.

Structure description top

As a part of our ongoing investigations of transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

In the title mononuclear complex, ZnII cation is located on an inversion center and is coordinated by two 4-formylbenzoate (FB) anions, two N,N-diethylnicotinamide (DENA) ligands and two water molecules, all ligands coordinating in a monodentate manner (Fig. 1). The crystal structures of similar complexes of CuII, CoII, NiII, MnII and ZnII ions, [Cu(C7H5O2)2(C10H14N2O)2] (Hökelek et al., 1996), [Cu(C7H4BrO2)2(C6H6N2O)2(H2O)2] (Necefoğlu, Özbek et al., 2011), [Co(C6H6N2O)2(C7H4NO4)2(H2O)2] (Hökelek & Necefoğlu, 1998), [Co(C9H9O2)2(C10H14N2O)2(H2O)2] (Necefoğlu, Maracı et al., 2011), [Co(C7H4IO2)2(C6H6N2O)2(H2O)2] (Aydın et al., 2012), [Ni(C7H4ClO2)2(C6H6N2O)2(H2O)2] (Hökelek et al., 2009a), [Ni(C5H5O3)2(C6H6N2O)2(H2O)2] (Sertçelik et al., 2012), [Mn(C9H10NO2)2(H2O)4].2H2O (Hökelek & Necefoğlu, 2007) and [Zn(C7H4BrO2)2(C6H6N2O)2(H2O)2] (Hökelek et al., 2009b) have also been reported. In the copper(II) complex mentioned above the two benzoate ions coordinate to the CuII atom as bidentate ligands, while in the other structures all the ligands coordinate in a monodentate manner.

In the title complex, the four symmetry related O atoms (O2, O2', O5 and O5') in the equatorial plane around the ZnII ion form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two symmetry related N atoms of the DENA ligands (N1 and N1') in the axial positions. The near equalities of the C1—O1 [1.2533 (16) Å] and C1—O2 [1.2623 (16) Å] bonds in the carboxylate group indicate delocalized bonding arrangement, rather than localized single and double bonds. The Zn—O bond lengths are 2.1128 (9) Å (for benzoate oxygens) and 2.1289 (10) Å (for water oxygens), and the Cu—N bond length is 2.1452 (11) Å, close to standard values (Allen et al., 1987). The Zn atom is displaced out of the mean-plane of the carboxylate group (O1/C1/O2) by 0.8455 (1) Å. The dihedral angle between the planar carboxylate group and the adjacent benzene ring A (C2—C7) is 2.96 (11)°. The benzene A (C2—C7) and the pyridine B (N1/C9—C13) rings are oriented at a dihedral angle of A/B = 79.26 (4)°. The coordinating water molecule links with the carboxylate group via an O—H···O hydrogen bond (Table 1).

In the crystal, intermolecular O—H···O and weak C—H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional supramolecular network, in which they may be effective in the stabilization of the structure. The π–π contact between the pyridine rings, Cg2—Cg2i [symmetry code: (i) 1 - x, 1 - y, -z, where Cg2 is the centroid of the ring B (N1/C9-C13)] may further stabilize the structure, with centroid-centroid distance of 3.5654 (8) Å].

For literature on niacin, see: Krishnamachari (1974). For information on the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Aydın et al. (2012); Hökelek et al. (1996, 2009a,b); Hökelek & Necefoğlu (2007, 1998); Necefoğlu, Özbek et al. (2011); Necefoğlu, Maracı et al. (2011); Sertçelik et al. (2012). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry code: (') -x, -y, -z].
Diaquabis(N,N-diethylnicotinamide-κN1)bis(4- formylbenzoato-κO1)zinc top
Crystal data top
[Zn(C8H5O3)2(C10H14N2O)2(H2O)2]Z = 1
Mr = 756.13F(000) = 396
Triclinic, P1Dx = 1.412 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1988 (2) ÅCell parameters from 9726 reflections
b = 8.5347 (2) Åθ = 2.6–28.3°
c = 15.9719 (4) ŵ = 0.75 mm−1
α = 85.435 (3)°T = 100 K
β = 78.010 (3)°Block, colorless
γ = 67.846 (2)°0.27 × 0.24 × 0.21 mm
V = 889.03 (4) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		4409 independent reflections
Radiation source: fine-focus sealed tube4128 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −9→9
Tmin = 0.816, Tmax = 0.854k = −10→11
16164 measured reflectionsl = −21→21
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.0442P)2 + 0.2368P]
where P = (Fo2 + 2Fc2)/3
4409 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
[Zn(C8H5O3)2(C10H14N2O)2(H2O)2]γ = 67.846 (2)°
Mr = 756.13V = 889.03 (4) Å3
Triclinic, P1Z = 1
a = 7.1988 (2) ÅMo Kα radiation
b = 8.5347 (2) ŵ = 0.75 mm−1
c = 15.9719 (4) ÅT = 100 K
α = 85.435 (3)°0.27 × 0.24 × 0.21 mm
β = 78.010 (3)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		4409 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4128 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.854Rint = 0.022
16164 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 0.46 e Å−3
4409 reflectionsΔρmin = −0.33 e Å−3
246 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.

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
Zn10.00000.00000.00000.01115 (7)
O1−0.25853 (15)0.12741 (13)0.19910 (6)0.0168 (2)
O20.02518 (14)0.11856 (12)0.10604 (6)0.01404 (19)
O30.44445 (18)0.18906 (16)0.45766 (7)0.0274 (2)
O40.73443 (15)−0.33358 (13)0.12604 (6)0.0173 (2)
O50.28172 (15)0.01887 (14)−0.06344 (6)0.01568 (19)
H510.282 (3)0.112 (3)−0.0758 (13)0.027 (5)*
H520.295 (3)−0.030 (3)−0.1102 (15)0.037 (6)*
N10.18033 (16)−0.23838 (14)0.04858 (7)0.0129 (2)
N20.61125 (17)−0.42797 (14)0.25277 (7)0.0148 (2)
C1−0.0800 (2)0.12606 (16)0.18050 (8)0.0128 (2)
C20.02005 (19)0.13218 (16)0.25409 (8)0.0128 (2)
C30.2155 (2)0.13794 (17)0.23866 (8)0.0142 (2)
H30.28640.13480.18270.017*
C40.3048 (2)0.14827 (17)0.30598 (8)0.0157 (3)
H40.43460.15290.29540.019*
C50.1978 (2)0.15163 (17)0.38982 (8)0.0158 (3)
C60.0046 (2)0.14231 (17)0.40557 (8)0.0164 (3)
H6−0.06500.14290.46160.020*
C7−0.0845 (2)0.13219 (17)0.33800 (8)0.0150 (3)
H7−0.21330.12540.34870.018*
C80.2874 (2)0.1654 (2)0.46331 (9)0.0211 (3)
H80.198 (3)0.153 (2)0.5225 (11)0.016 (4)*
C90.32059 (19)−0.24272 (16)0.09356 (8)0.0127 (2)
H90.3407−0.14320.10000.015*
C100.43636 (19)−0.38948 (16)0.13075 (8)0.0125 (2)
C110.4100 (2)−0.53987 (17)0.11979 (8)0.0141 (2)
H110.4850−0.64010.14440.017*
C120.2696 (2)−0.53643 (17)0.07137 (8)0.0151 (3)
H120.2503−0.63490.06200.018*
C130.1585 (2)−0.38386 (17)0.03717 (8)0.0139 (2)
H130.0643−0.38230.00480.017*
C140.6039 (2)−0.38178 (16)0.17105 (8)0.0130 (2)
C150.4557 (2)−0.47566 (18)0.31161 (9)0.0182 (3)
H15A0.5213−0.58620.33560.022*
H15B0.3592−0.48450.27970.022*
C160.3398 (3)−0.3501 (2)0.38430 (11)0.0314 (4)
H16A0.2364−0.38490.41920.047*
H16B0.2768−0.23980.36100.047*
H16C0.4330−0.34630.41850.047*
C170.7881 (2)−0.42804 (18)0.28570 (9)0.0186 (3)
H17A0.9113−0.48000.24350.022*
H17B0.8000−0.49700.33710.022*
C180.7743 (3)−0.2522 (2)0.30647 (10)0.0243 (3)
H18A0.8950−0.26110.32620.036*
H18B0.6563−0.20180.35030.036*
H18C0.7627−0.18300.25600.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01120 (11)0.01159 (11)0.01099 (11)−0.00424 (8)−0.00333 (7)0.00145 (7)
O10.0131 (4)0.0207 (5)0.0165 (4)−0.0058 (4)−0.0033 (3)−0.0007 (4)
O20.0156 (4)0.0149 (5)0.0123 (4)−0.0065 (4)−0.0029 (3)0.0005 (3)
O30.0292 (6)0.0390 (7)0.0226 (5)−0.0199 (5)−0.0102 (4)0.0023 (5)
O40.0159 (5)0.0197 (5)0.0190 (5)−0.0096 (4)−0.0041 (4)0.0028 (4)
O50.0165 (5)0.0164 (5)0.0161 (5)−0.0082 (4)−0.0034 (4)0.0005 (4)
N10.0124 (5)0.0132 (5)0.0126 (5)−0.0043 (4)−0.0025 (4)0.0004 (4)
N20.0164 (5)0.0150 (5)0.0156 (5)−0.0073 (4)−0.0064 (4)0.0012 (4)
C10.0144 (6)0.0086 (6)0.0148 (6)−0.0028 (4)−0.0045 (5)0.0006 (4)
C20.0148 (6)0.0097 (6)0.0134 (6)−0.0035 (5)−0.0038 (5)0.0001 (4)
C30.0149 (6)0.0143 (6)0.0132 (6)−0.0058 (5)−0.0013 (5)−0.0002 (5)
C40.0151 (6)0.0164 (6)0.0165 (6)−0.0067 (5)−0.0035 (5)0.0006 (5)
C50.0188 (6)0.0152 (6)0.0148 (6)−0.0069 (5)−0.0053 (5)0.0008 (5)
C60.0183 (6)0.0176 (7)0.0121 (6)−0.0065 (5)−0.0012 (5)0.0004 (5)
C70.0134 (6)0.0151 (6)0.0164 (6)−0.0054 (5)−0.0024 (5)0.0003 (5)
C80.0237 (7)0.0267 (8)0.0154 (6)−0.0111 (6)−0.0059 (5)0.0008 (5)
C90.0137 (6)0.0116 (6)0.0136 (5)−0.0053 (5)−0.0027 (4)−0.0007 (4)
C100.0113 (5)0.0142 (6)0.0114 (5)−0.0044 (5)−0.0015 (4)0.0000 (4)
C110.0147 (6)0.0126 (6)0.0146 (6)−0.0041 (5)−0.0037 (5)0.0012 (5)
C120.0170 (6)0.0135 (6)0.0168 (6)−0.0077 (5)−0.0035 (5)−0.0001 (5)
C130.0133 (6)0.0163 (6)0.0131 (6)−0.0064 (5)−0.0029 (4)−0.0002 (5)
C140.0137 (6)0.0098 (6)0.0149 (6)−0.0031 (5)−0.0039 (5)−0.0007 (4)
C150.0219 (7)0.0198 (7)0.0145 (6)−0.0099 (5)−0.0035 (5)0.0015 (5)
C160.0314 (9)0.0381 (10)0.0255 (8)−0.0166 (7)0.0045 (6)−0.0117 (7)
C170.0208 (7)0.0174 (7)0.0216 (7)−0.0076 (5)−0.0126 (5)0.0031 (5)
C180.0308 (8)0.0215 (7)0.0273 (7)−0.0128 (6)−0.0145 (6)0.0010 (6)
Geometric parameters (Å, º) top
Zn1—O22.1128 (9)C7—C21.3940 (18)
Zn1—O2i2.1128 (9)C7—H70.9300
Zn1—O52.1289 (10)C8—C51.4834 (19)
Zn1—O5i2.1289 (10)C8—H81.049 (17)
Zn1—N12.1452 (11)C9—C101.3843 (18)
Zn1—N1i2.1452 (11)C9—H90.9300
O1—C11.2533 (16)C11—C101.3954 (18)
O2—C11.2623 (16)C11—C121.3857 (18)
O3—C81.2057 (19)C11—H110.9300
O4—C141.2382 (17)C12—H120.9300
O5—H510.81 (2)C13—C121.3843 (19)
O5—H520.85 (2)C13—H130.9300
N1—C91.3439 (16)C14—C101.5040 (18)
N1—C131.3397 (17)C15—C161.521 (2)
N2—C141.3390 (17)C15—H15A0.9700
N2—C151.4655 (18)C15—H15B0.9700
N2—C171.4747 (17)C16—H16A0.9600
C1—C21.5143 (17)C16—H16B0.9600
C3—C21.3958 (18)C16—H16C0.9600
C3—C41.3866 (18)C17—C181.525 (2)
C3—H30.9300C17—H17A0.9700
C4—C51.3957 (19)C17—H17B0.9700
C4—H40.9300C18—H18A0.9600
C6—C51.3926 (19)C18—H18B0.9600
C6—C71.3885 (19)C18—H18C0.9600
C6—H60.9300
O2—Zn1—O2i180.00 (8)O3—C8—C5125.06 (14)
O2—Zn1—O587.26 (4)O3—C8—H8122.2 (10)
O2i—Zn1—O592.74 (4)C5—C8—H8112.7 (10)
O2—Zn1—O5i92.74 (4)N1—C9—C10122.57 (12)
O2i—Zn1—O5i87.26 (4)N1—C9—H9118.7
O2—Zn1—N188.47 (4)C10—C9—H9118.7
O2i—Zn1—N191.53 (4)C9—C10—C11118.95 (12)
O2—Zn1—N1i91.53 (4)C9—C10—C14117.31 (12)
O2i—Zn1—N1i88.47 (4)C11—C10—C14123.23 (11)
O5—Zn1—O5i180.00 (8)C10—C11—H11120.8
O5—Zn1—N186.62 (4)C12—C11—C10118.50 (12)
O5i—Zn1—N193.38 (4)C12—C11—H11120.8
O5—Zn1—N1i93.38 (4)C11—C12—H12120.6
O5i—Zn1—N1i86.62 (4)C13—C12—C11118.86 (12)
N1i—Zn1—N1180.00 (10)C13—C12—H12120.6
C1—O2—Zn1125.27 (9)N1—C13—C12123.03 (12)
Zn1—O5—H51117.4 (14)N1—C13—H13118.5
Zn1—O5—H5298.3 (15)C12—C13—H13118.5
H52—O5—H51107 (2)O4—C14—N2121.65 (12)
C9—N1—Zn1118.79 (9)O4—C14—C10117.88 (12)
C13—N1—Zn1123.15 (9)N2—C14—C10120.47 (12)
C13—N1—C9118.05 (11)N2—C15—C16113.09 (12)
C14—N2—C15124.84 (11)N2—C15—H15A109.0
C14—N2—C17117.10 (12)N2—C15—H15B109.0
C15—N2—C17118.06 (11)C16—C15—H15A109.0
O1—C1—O2126.07 (12)C16—C15—H15B109.0
O1—C1—C2117.12 (11)H15A—C15—H15B107.8
O2—C1—C2116.81 (11)C15—C16—H16A109.5
C3—C2—C1120.65 (11)C15—C16—H16B109.5
C7—C2—C1119.54 (12)C15—C16—H16C109.5
C7—C2—C3119.81 (12)H16A—C16—H16B109.5
C2—C3—H3119.7H16A—C16—H16C109.5
C4—C3—C2120.65 (12)H16B—C16—H16C109.5
C4—C3—H3119.7N2—C17—C18113.79 (12)
C3—C4—C5119.31 (13)N2—C17—H17A108.8
C3—C4—H4120.3N2—C17—H17B108.8
C5—C4—H4120.3C18—C17—H17A108.8
C4—C5—C8120.74 (13)C18—C17—H17B108.8
C6—C5—C4120.23 (12)H17A—C17—H17B107.7
C6—C5—C8119.03 (12)C17—C18—H18A109.5
C5—C6—H6119.8C17—C18—H18B109.5
C7—C6—C5120.31 (12)C17—C18—H18C109.5
C7—C6—H6119.8H18A—C18—H18B109.5
C2—C7—H7120.2H18A—C18—H18C109.5
C6—C7—C2119.67 (12)H18B—C18—H18C109.5
C6—C7—H7120.2
O5—Zn1—O2—C1−166.52 (10)O1—C1—C2—C3−177.42 (12)
O5i—Zn1—O2—C113.48 (10)O1—C1—C2—C72.52 (18)
N1—Zn1—O2—C1−79.84 (10)O2—C1—C2—C33.18 (18)
N1i—Zn1—O2—C1100.16 (10)O2—C1—C2—C7−176.87 (12)
O2—Zn1—N1—C9−30.48 (10)C4—C3—C2—C1178.20 (12)
O2i—Zn1—N1—C9149.52 (10)C4—C3—C2—C7−1.7 (2)
O2—Zn1—N1—C13148.70 (10)C2—C3—C4—C50.5 (2)
O2i—Zn1—N1—C13−31.30 (10)C3—C4—C5—C60.9 (2)
O5—Zn1—N1—C956.87 (10)C3—C4—C5—C8−179.00 (13)
O5i—Zn1—N1—C9−123.13 (10)C7—C6—C5—C4−1.0 (2)
O5—Zn1—N1—C13−123.96 (10)C7—C6—C5—C8178.92 (13)
O5i—Zn1—N1—C1356.04 (10)C5—C6—C7—C2−0.3 (2)
Zn1—O2—C1—O1−29.35 (18)C6—C7—C2—C1−178.30 (12)
Zn1—O2—C1—C2149.99 (9)C6—C7—C2—C31.6 (2)
Zn1—N1—C9—C10176.76 (9)O3—C8—C5—C46.7 (2)
C13—N1—C9—C10−2.46 (19)O3—C8—C5—C6−173.20 (15)
Zn1—N1—C13—C12−177.44 (10)N1—C9—C10—C111.38 (19)
C9—N1—C13—C121.74 (19)N1—C9—C10—C14173.43 (12)
C15—N2—C14—O4175.78 (12)C12—C11—C10—C90.49 (19)
C15—N2—C14—C10−5.06 (19)C12—C11—C10—C14−171.08 (12)
C17—N2—C14—O4−3.29 (19)C10—C11—C12—C13−1.16 (19)
C17—N2—C14—C10175.87 (11)N1—C13—C12—C110.1 (2)
C14—N2—C15—C16−112.92 (15)O4—C14—C10—C9−55.69 (17)
C17—N2—C15—C1666.14 (17)O4—C14—C10—C11116.00 (14)
C14—N2—C17—C1877.07 (16)N2—C14—C10—C9125.13 (13)
C15—N2—C17—C18−102.06 (14)N2—C14—C10—C11−63.18 (18)
Symmetry code: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H51···O4ii0.80 (2)1.97 (2)2.7591 (15)169 (2)
O5—H52···O1i0.85 (2)1.81 (2)2.6494 (14)166 (2)
C4—H4···O1iii0.932.363.1975 (19)150
C7—H7···O3iv0.932.603.406 (2)145
C11—H11···O1v0.932.403.3068 (17)166
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z; (iii) x+1, y, z; (iv) x−1, y, z; (v) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula[Zn(C8H5O3)2(C10H14N2O)2(H2O)2]
Mr756.13
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.1988 (2), 8.5347 (2), 15.9719 (4)
α, β, γ (°)85.435 (3), 78.010 (3), 67.846 (2)
V (Å3)889.03 (4)
Z1
Radiation typeMo Kα
µ (mm−1)0.75
Crystal size (mm)0.27 × 0.24 × 0.21
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.816, 0.854
No. of measured, independent and
observed [I > 2σ(I)] reflections		16164, 4409, 4128
Rint0.022
(sin θ/λ)max (Å−1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.081, 1.16
No. of reflections4409
No. of parameters246
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.46, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H51···O4i0.80 (2)1.97 (2)2.7591 (15)169 (2)
O5—H52···O1ii0.85 (2)1.81 (2)2.6494 (14)166 (2)
C4—H4···O1iii0.932.363.1975 (19)150
C7—H7···O3iv0.932.603.406 (2)145
C11—H11···O1v0.932.403.3068 (17)166
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) x+1, y, z; (iv) x−1, y, z; (v) x+1, y−1, z.
 

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2012-FEF-12).

References

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Pages m1067-m1068
https://doi.org/10.1107/S1600536812031200
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