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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 69| Part 7| July 2013| Pages m381-m382

catena-Poly[aqua­bis­­(μ-3-chloro­benzo­ato-κ2O:O′)zinc]

aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, bAksaray University, Department of Physics, 68100, Aksaray, Turkey, cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 3 June 2013; accepted 5 June 2013; online 15 June 2013)

In the polymeric title compound, [Zn(C7H4ClO2)2(H2O)]n, the ZnII cation is located on a twofold rotation axis and is coordinated by carboxylate O atoms of four monodentate chloro­benzoate anions and by one water mol­ecule, located on a twofold rotation axis, in a distorted square-pyramidal geometry. In the anion, the carboxyl­ate group is twisted away from the attached benzene ring by 44.16 (11)°. The chloro­benzoate anion bridges ZnII cations, forming polymeric chains running along the c-axis direction. O—H⋯O hydrogen bonds between coordinating water mol­ecules and carboxyl­ate groups link adjacent chains into layers parallel to the bc plane.

Related literature

For structural functions and coordination relationships of the aryl­carboxyl­ate ion in transition metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981[Nadzhafov, G. N., Shnulin, A. N. & Mamedov, Kh. S. (1981). Zh. Strukt. Khim. 22, 124-128.]); Shnulin et al. (1981[Shnulin, A. N., Nadzhafov, G. N., Amiraslanov, I. R., Usubaliev, B. T. & Mamedov, Kh. S. (1981). Koord. Khim. 7, 1409-1416.]). For applications of transition metal complexes with biochemical mol­ecules in biological systems, see: Antolini et al. (1982[Antolini, L., Battaglia, L. P., Corradi, A. B., Marcotrigiano, G., Menabue, L., Pellacani, G. C. & Saladini, M. (1982). Inorg. Chem. 21, 1391-1395.]). Some benzoic acid derivatives, such as 4-amino­benzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes, see: Chen & Chen (2002[Chen, H. J. & Chen, X. M. (2002). Inorg. Chim. Acta, 329, 13-21.]); Amiraslanov et al. (1979[Amiraslanov, I. R., Mamedov, Kh. S., Movsumov, E. M., Musaev, F. N. & Nadzhafov, G. N. (1979). Zh. Strukt. Khim. 20, 1075-1080.]); Hauptmann et al. (2000[Hauptmann, R., Kondo, M. & Kitagawa, S. (2000). Z. Kristallogr. New Cryst. Struct. 215, 169-172.]). For related structures, see: Aydın et al. (2012[Aydın, Ö., Çaylak Delibaş, N., Necefoğlu, H. & Hökelek, T. (2012). Acta Cryst. E68, m601-m602.]); Hökelek et al. (2009[Hökelek, T., Yılmaz, F., Tercan, B., Sertçelik, M. & Necefoğlu, H. (2009). Acta Cryst. E65, m1399-m1400.], 2010a[Hökelek, T., Dal, H., Tercan, B., Çimen, E. & Necefoğlu, H. (2010a). Acta Cryst. E66, m734-m735.],b[Hökelek, T., Dal, H., Tercan, B., Çimen, E. & Necefoğlu, H. (2010b). Acta Cryst. E66, m953-m954.], 2011[Hökelek, T., Tercan, B., Şahin, E., Aktaş, V. & Necefoğlu, H. (2011). Acta Cryst. E67, m1057-m1058.]); Necefoğlu et al. (2011[Necefoğlu, H., Özbek, F. E., Öztürk, V., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m1003-m1004.]); Zaman et al. (2012[Zaman, İ. G., Çaylak Delibaş, N., Necefoğlu, H. & Hökelek, T. (2012). Acta Cryst. E68, m257-m258.]). 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(C7H4ClO2)2(H2O)]

  • Mr = 394.51

  • Monoclinic, C 2/c

  • a = 31.8553 (8) Å

  • b = 6.1786 (2) Å

  • c = 7.5117 (3) Å

  • β = 96.554 (2)°

  • V = 1468.80 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.06 mm−1

  • T = 294 K

  • 0.35 × 0.25 × 0.15 mm

Data collection
  • Bruker SMART BREEZE CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.545, Tmax = 0.735

  • 13582 measured reflections

  • 1825 independent reflections

  • 1727 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.069

  • S = 1.12

  • 1825 reflections

  • 105 parameters

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

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Selected bond lengths (Å)

Zn1—O1 2.1779 (12)
Zn1—O2 1.9493 (11)
Zn1—O3 1.9664 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H31⋯O1i 0.77 (2) 1.89 (2) 2.6421 (17) 168 (2)
Symmetry code: (i) [x, -y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, as a result they may find applications in biological systems (Antolini et al., 1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes (Chen & Chen, 2002; Amiraslanov et al., 1979; Hauptmann et al., 2000). The title compound was synthesized and its crystal structure is reported herein.

The asymmetric unit of the title compound, (I), contains one-half ZnII cation, one chlorobenzoate (CB) anion and one-half water molecule (Fig. 1). In the crystal, two CB anions bridge adjacent ZnII cations, forming a polymeric chain running along the c axis, while the water molecule coordinate in a monodentate manner to the ZnII cation, completing the distorted square-pyramidal geometry (Fig. 2). As a result of the CB anions bridging of the adjacent ZnII cations, an eight-membered ring is formed where the distances between the symmetry related atoms, Zn1···Zn1b [4.3798 (3) Å], O1···O1b [3.020 (2) Å], O2···O2b [4.337 (2) Å] and C1···C1b [3.975 (2) Å] [symmetry code: (b) - x, - y, 1 - z], may reflect its size.

The crystal structures of some benzoate containing polymeric complexes of MnII, ZnII, PbII and CoII ions, [Mn2(C8H7O2)4(C10H14N2O)2(H2O)]n (Hökelek et al., 2010a), [Mn(C7H4FO2)2(H2O)2]n (Necefoğlu et al., 2011), [Zn(C8H5O3)2(C6H6N2O)]n (Hökelek et al., 2009), [Pb(C8H7O2)2(C6H6N2O)]n (Hökelek et al., 2010b), {[Pb(C9H9O2)2(C6H6N2O)].H2O}n (Hökelek et al., 2011), {[Pb(C7H5O3)2(C6H6N2O)].H2O}n (Zaman et al., 2012) and [Co(C7H4IO2)2(H2O)2]n (Aydın et al., 2012) have also been reported.

In the title compound, the four O atoms (O1, O1a, O2b and O2c) [symmetry codes: (a) - x, y, 1/2 - z, (b) - x, - y, 1 - z, (c) x, - y, - 1/2 + z] in the equatorial plane around the ZnII cation form a distorted square-planar arrangement, while the distorted square-pyramidal geometry is completed by the water O atom (O3) in the axial position. The near equalities of the C1—O1 [1.260 (2) Å] and C1—O2 [1.258 (2) Å] bonds in the carboxylate group indicate delocalized bonding arrangement, rather than localized single and double bonds. The average Zn—O bond length is 2.0636 (12) Å (for benzoate oxygens) and 1.9664 (19) Å (for water oxygen) (Table 1) 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 1.3998 (1) Å. Atoms Cl1, C1 and O1 are -0.0897 (7), -0.0181 (16) and -0.2341 (12) Å away from the mean-plane of the adjacent benzene ring, respectively. The dihedral angle between the planar carboxylate group (O1/C1/O2) and the adjacent benzene ring A (C2—C7) is 44.16 (11)°.

In the crystal, strong O—H···O hydrogen bonds (Table 2) link the water hydrogens to the carboxylate oxygens in the polymeric chains (Fig. 3).

Related literature top

For structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981); Shnulin et al. (1981). For applications of transition metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes, see: Chen & Chen (2002); Amiraslanov et al. (1979); Hauptmann et al. (2000). For related structures, see: Aydın et al. (2012); Hökelek et al. (2009, 2010a,b, 2011); Necefoğlu et al. (2011); Zaman 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 (0.89 g, 5 mmol) in H2O (50 ml) with sodium 3-chlorobenzoate (1.79 g, 10 mmol) in H2O (100 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving colorless single crystals.

Refinement top

Atom H31 (for H2O) was located in a difference Fourier map and was refined freely. The C-bound H-atoms were positioned geometrically with C—H = 0.93 Å for aromatic H-atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the polymeric chain of the title compound.
[Figure 3] Fig. 3. A view along the b axis of the packing of the title compound (a axis horizontal; c axis vertical). Hydrogen bonds are shown as dashed lines.
catena-Poly[aquabis(µ-3-chlorobenzoato-κ2O:O')zinc] top
Crystal data top
[Zn(C7H4ClO2)2(H2O)]F(000) = 792
Mr = 394.51Dx = 1.784 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9983 reflections
a = 31.8553 (8) Åθ = 2.6–28.3°
b = 6.1786 (2) ŵ = 2.06 mm1
c = 7.5117 (3) ÅT = 294 K
β = 96.554 (2)°Block, colorless
V = 1468.80 (8) Å30.35 × 0.25 × 0.15 mm
Z = 4
Data collection top
Bruker SMART BREEZE CCD
diffractometer
1825 independent reflections
Radiation source: fine-focus sealed tube1727 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 4142
Tmin = 0.545, Tmax = 0.735k = 88
13582 measured reflectionsl = 810
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0337P)2 + 1.4314P]
where P = (Fo2 + 2Fc2)/3
1825 reflections(Δ/σ)max = 0.002
105 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
[Zn(C7H4ClO2)2(H2O)]V = 1468.80 (8) Å3
Mr = 394.51Z = 4
Monoclinic, C2/cMo Kα radiation
a = 31.8553 (8) ŵ = 2.06 mm1
b = 6.1786 (2) ÅT = 294 K
c = 7.5117 (3) Å0.35 × 0.25 × 0.15 mm
β = 96.554 (2)°
Data collection top
Bruker SMART BREEZE CCD
diffractometer
1825 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
1727 reflections with I > 2σ(I)
Tmin = 0.545, Tmax = 0.735Rint = 0.036
13582 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.43 e Å3
1825 reflectionsΔρmin = 0.35 e Å3
105 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
Zn11.00000.18233 (4)0.25000.02388 (10)
Cl10.781898 (15)0.05564 (11)0.15745 (9)0.05827 (18)
O10.97446 (4)0.20515 (18)0.03094 (16)0.0286 (3)
O21.05402 (4)0.0674 (2)0.19485 (18)0.0368 (3)
O31.00000.5006 (3)0.25000.0497 (6)
H310.9935 (8)0.573 (4)0.325 (3)0.045 (7)*
C10.94299 (5)0.1000 (3)0.1019 (2)0.0250 (3)
C20.89932 (5)0.1772 (2)0.0796 (2)0.0263 (3)
C30.86489 (5)0.0444 (3)0.1307 (2)0.0306 (3)
H30.86870.09060.18140.037*
C40.82482 (5)0.1162 (3)0.1050 (3)0.0357 (4)
C50.81842 (6)0.3189 (3)0.0349 (3)0.0409 (5)
H50.79130.36600.02050.049*
C60.85288 (6)0.4504 (3)0.0133 (3)0.0411 (4)
H60.84890.58720.06000.049*
C70.89340 (6)0.3808 (3)0.0069 (3)0.0346 (4)
H70.91650.46940.02770.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02038 (13)0.01944 (13)0.03266 (17)0.0000.00670 (10)0.000
Cl10.0262 (2)0.0787 (4)0.0707 (4)0.0071 (2)0.0089 (2)0.0203 (3)
O10.0262 (5)0.0295 (6)0.0302 (6)0.0027 (4)0.0034 (5)0.0041 (4)
O20.0225 (5)0.0460 (7)0.0416 (7)0.0066 (5)0.0027 (5)0.0187 (6)
O30.0973 (18)0.0189 (8)0.0384 (12)0.0000.0312 (12)0.000
C10.0237 (7)0.0287 (7)0.0231 (8)0.0039 (6)0.0049 (6)0.0027 (6)
C20.0241 (7)0.0296 (8)0.0256 (8)0.0060 (5)0.0052 (6)0.0013 (6)
C30.0256 (7)0.0356 (8)0.0310 (9)0.0043 (6)0.0056 (6)0.0034 (7)
C40.0249 (8)0.0485 (10)0.0340 (9)0.0030 (7)0.0046 (7)0.0012 (8)
C50.0302 (9)0.0523 (12)0.0418 (11)0.0169 (8)0.0105 (8)0.0013 (8)
C60.0432 (10)0.0355 (9)0.0459 (11)0.0151 (8)0.0107 (8)0.0036 (8)
C70.0337 (8)0.0311 (8)0.0395 (10)0.0049 (7)0.0062 (7)0.0030 (7)
Geometric parameters (Å, º) top
Zn1—O12.1779 (12)C2—C31.388 (2)
Zn1—O1i2.1779 (12)C2—C71.393 (2)
Zn1—O21.9493 (11)C3—C41.386 (2)
Zn1—O2i1.9493 (11)C3—H30.9300
Zn1—O31.9664 (19)C5—C41.383 (3)
Cl1—C41.740 (2)C5—C61.380 (3)
O1—C11.260 (2)C5—H50.9300
O2—C1ii1.258 (2)C6—H60.9300
O3—H310.77 (2)C7—C61.385 (2)
C1—O2ii1.258 (2)C7—H70.9300
C2—C11.498 (2)
O1—Zn1—O1i172.58 (6)C3—C2—C7120.29 (15)
O2—Zn1—O193.38 (5)C7—C2—C1120.01 (15)
O2i—Zn1—O189.33 (5)C2—C3—H3120.5
O2—Zn1—O1i89.33 (5)C4—C3—C2118.90 (16)
O2i—Zn1—O1i93.38 (5)C4—C3—H3120.5
O2i—Zn1—O2137.26 (8)C3—C4—Cl1119.05 (16)
O2—Zn1—O3111.37 (4)C5—C4—Cl1119.50 (14)
O2i—Zn1—O3111.37 (4)C5—C4—C3121.43 (18)
O3—Zn1—O186.29 (3)C4—C5—H5120.5
O3—Zn1—O1i86.29 (3)C6—C5—C4119.05 (16)
C1—O1—Zn1124.58 (10)C6—C5—H5120.5
C1ii—O2—Zn1122.84 (11)C5—C6—C7120.76 (17)
Zn1—O3—H31125.7 (19)C5—C6—H6119.6
O1—C1—C2119.52 (14)C7—C6—H6119.6
O2ii—C1—O1123.47 (14)C2—C7—H7120.2
O2ii—C1—C2117.00 (14)C6—C7—C2119.54 (18)
C3—C2—C1119.70 (14)C6—C7—H7120.2
O2—Zn1—O1—C1116.58 (13)C7—C2—C1—O2ii168.37 (16)
O2i—Zn1—O1—C120.74 (13)C1—C2—C3—C4178.42 (16)
O3—Zn1—O1—C1132.21 (12)C7—C2—C3—C41.2 (3)
O1—Zn1—O2—C1ii55.67 (14)C1—C2—C7—C6179.91 (17)
O1i—Zn1—O2—C1ii131.24 (14)C3—C2—C7—C60.3 (3)
O2i—Zn1—O2—C1ii36.99 (13)C2—C3—C4—Cl1176.52 (14)
O3—Zn1—O2—C1ii143.01 (13)C2—C3—C4—C52.0 (3)
Zn1—O1—C1—O2ii100.74 (17)C6—C5—C4—Cl1177.28 (16)
Zn1—O1—C1—C280.48 (17)C6—C5—C4—C31.2 (3)
C3—C2—C1—O1169.14 (15)C4—C5—C6—C70.3 (3)
C3—C2—C1—O2ii12.0 (2)C2—C7—C6—C51.1 (3)
C7—C2—C1—O110.5 (2)
Symmetry codes: (i) x+2, y, z+1/2; (ii) x+2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H31···O1iii0.77 (2)1.89 (2)2.6421 (17)168 (2)
Symmetry code: (iii) x, y+1, z+1/2.

Experimental details

Crystal data
Chemical formula[Zn(C7H4ClO2)2(H2O)]
Mr394.51
Crystal system, space groupMonoclinic, C2/c
Temperature (K)294
a, b, c (Å)31.8553 (8), 6.1786 (2), 7.5117 (3)
β (°) 96.554 (2)
V3)1468.80 (8)
Z4
Radiation typeMo Kα
µ (mm1)2.06
Crystal size (mm)0.35 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART BREEZE CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2012)
Tmin, Tmax0.545, 0.735
No. of measured, independent and
observed [I > 2σ(I)] reflections
13582, 1825, 1727
Rint0.036
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.069, 1.12
No. of reflections1825
No. of parameters105
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.35

Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Zn1—O12.1779 (12)Zn1—O31.9664 (19)
Zn1—O21.9493 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H31···O1i0.77 (2)1.89 (2)2.6421 (17)168 (2)
Symmetry code: (i) x, y+1, z+1/2.
 

Acknowledgements

The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
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Volume 69| Part 7| July 2013| Pages m381-m382
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