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Acta Cryst. (2009). E65, m1399-m1400    [ doi:10.1107/S160053680904241X ]

catena-Poly[[(4-formylbenzoato-[kappa]O1)(isonicotinamide-[kappa]N1)zinc(II)]-[mu]-4-formylbenzoato-[kappa]2O1:O1']

T. Hökelek, F. Yilmaz, B. Tercan, M. Sertçelik and H. Necefoglu

Abstract top

In the title compound, [Zn(C8H5O3)2(C6H6N2O)]n, the ZnII ion is tetrahedrally coordinated by two formylbenzoate (FB) and one isonicotinamide (INA) ligands while symmetry-related FB ligands bridge adjacent ZnII ions, forming polymeric chains along the b axis. The carboxylate groups in the two FB ions are twisted away from the attached benzene ring by 9.07 (2) and 26.2 (2)°. The two benzene rings of the FB ions are oriented at a dihedral angle of 81.30 (5)°. In the crystal, adjacent polymeric chains interact via N-H...O and C-H...O hydrogen bonds, [pi]-[pi] contacts between the formylbenzoate rings [centroid-centroid distance = 3.7736 (8) Å] and weak C-H...[pi] interactions, forming a three-dimensional network.

Comment top

As a part of our ongoing investigation on 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 crystal structure of the title compound, each ZnII ion is coordinated by two formylbenzoate (FB) and one isonicotinamide (INA) ligands (Fig. 1), while symmetry related FB ligands bridge the ZnII ions forming polymeric chains along the b axis (Fig.2). The structures of similar complexes of ZnII ion, [Zn2(C10H14N2O)2(C7H5O3)4].2H2O (Hökelek & Necefouglu, 1996) and [Zn(C9H10NO2)2(C6H6N2O)(H2O)2] (Hökelek et al., 2009) have also been reported.

The average Zn—O bond length (Table 1) is 1.9442 (11) Å and the Zn1 atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O3/C8/O4*) by 0.687 (5) Å and 0.703 (2) Å, respectively. The O1/C1/O2 and O3/C8/O4* carboxylate planes form dihedral angles of 9.07 (2)° and 26.2 (2)°, respectively, with benzene rings A(C2-C7) and B(C9-C14), while the angles between rings A, B and C (N1/C15-C19) are A/B = 81.30 (5), A/C = 63.17 (5) and B/C = 46.11 (5)°.

In the crystal structure, N—H···O and C—H···O hydrogen bonds (Table 2) link adjacent chains into a three-dimensional network. In addition, π–π contacts between symmetry related A(C2-C7) formylbenzoate rings at (x, y, z) and (5/2-x, -1/2+y, 1/2-z)/(5/2-x, 1/2+y, 1/2-z) with a centroid-to-centroid distance of 3.7736 (8) Å, and weak C—H···π interaction (Table 2) involving the B(C9-C14) ring stabilize the structure.

Related literature top

For general background to niacin, see: Krishnamachari (1974). For the crystal structure of N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek & Necefouglu (1996); Hökelek et al. (2009). Cg1 is the centroid of the C9–C14 ring.

Experimental top

The title compound was prepared by the reaction of ZnSO4.H2O (0.90 g, 5 mmol) in H2O (25 ml) and INA (1.22 g, 10 mmol) in H2O (40 ml) with sodium 4-formylbenzoate (1.72 g, 10 mmol) in H2O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving colourless single crystals.

Refinement top

Atoms H21 and H22 (for methine) were located in a difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically with N-H = 0.86 Å (for NH2) and C-H = 0.93 Å for aromatic H atoms and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

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 asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of a polymeric chain of the title compound.
catena-Poly[[(4-formylbenzoato-κO1)(isonicotinamide- κN1)zinc(II)]-µ-4-formylbenzoato-κ2O1:O1'] top
Crystal data top
[Zn(C8H5O3)2(C6H6N2O)]F(000) = 992
Mr = 485.74Dx = 1.670 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9448 reflections
a = 13.3143 (2) Åθ = 3.1–28.4°
b = 6.7857 (1) ŵ = 1.32 mm−1
c = 21.3927 (3) ÅT = 100 K
β = 91.458 (1)°Needle, colourless
V = 1932.14 (5) Å30.22 × 0.12 × 0.08 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		4812 independent reflections
Radiation source: fine-focus sealed tube4086 reflections with I > 2σ(I)
graphiteRint = 0.072
φ and ω scansθmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −17→14
Tmin = 0.829, Tmax = 0.903k = −8→9
17841 measured reflectionsl = −28→28
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) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0394P)2 + 0.0092P]
where P = (Fo2 + 2Fc2)/3
4812 reflections(Δ/σ)max = 0.001
297 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.39 e Å−3
Crystal data top
[Zn(C8H5O3)2(C6H6N2O)]V = 1932.14 (5) Å3
Mr = 485.74Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.3143 (2) ŵ = 1.32 mm−1
b = 6.7857 (1) ÅT = 100 K
c = 21.3927 (3) Å0.22 × 0.12 × 0.08 mm
β = 91.458 (1)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		4812 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4086 reflections with I > 2σ(I)
Tmin = 0.829, Tmax = 0.903Rint = 0.072
17841 measured reflectionsθmax = 28.4°
Refinement top
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080Δρmax = 0.47 e Å−3
S = 1.10Δρmin = −0.39 e Å−3
4812 reflectionsAbsolute structure: ?
297 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Zn10.816160 (13)0.51300 (2)0.187880 (8)0.01058 (7)
O10.95052 (8)0.60767 (16)0.20123 (5)0.0149 (2)
O21.00643 (8)0.55706 (16)0.10502 (5)0.0149 (2)
O30.77863 (8)0.37932 (15)0.26575 (5)0.0134 (2)
O40.70741 (8)0.67550 (14)0.15404 (5)0.0137 (2)
O50.83582 (11)−0.07543 (19)−0.07713 (6)0.0312 (3)
O61.49773 (9)0.61367 (17)0.23858 (5)0.0199 (3)
O71.10801 (11)0.97953 (16)0.45862 (6)0.0236 (3)
N10.81632 (9)0.29546 (17)0.12295 (6)0.0112 (3)
N20.91501 (11)−0.28715 (18)−0.01158 (6)0.0182 (3)
H2A0.9269−0.3695−0.04100.022*
H2B0.9348−0.31250.02620.022*
C11.02044 (11)0.5821 (2)0.16202 (7)0.0110 (3)
C21.12564 (11)0.5862 (2)0.18971 (7)0.0109 (3)
C31.14051 (12)0.5879 (2)0.25423 (7)0.0126 (3)
H31.08570.58670.28030.015*
C41.23802 (12)0.5913 (2)0.27978 (7)0.0131 (3)
H41.24870.59060.32290.016*
C51.31866 (11)0.5957 (2)0.24033 (7)0.0122 (3)
C61.30379 (12)0.5942 (2)0.17551 (7)0.0143 (3)
H61.35850.59790.14940.017*
C71.20746 (12)0.5872 (2)0.15043 (7)0.0134 (3)
H71.19710.58320.10730.016*
C80.81930 (11)0.3293 (2)0.31722 (7)0.0115 (3)
C90.89783 (12)0.4527 (2)0.34954 (7)0.0114 (3)
C100.96360 (12)0.3649 (2)0.39317 (7)0.0149 (3)
H100.96030.22990.40040.018*
C111.03354 (13)0.4785 (2)0.42548 (8)0.0162 (3)
H111.07920.41880.45310.019*
C121.03609 (12)0.6823 (2)0.41700 (7)0.0140 (3)
C130.97104 (12)0.7698 (2)0.37288 (7)0.0138 (3)
H130.97300.90530.36660.017*
C140.90409 (12)0.6556 (2)0.33872 (7)0.0122 (3)
H140.86270.71380.30830.015*
C150.86757 (11)0.1289 (2)0.13520 (7)0.0125 (3)
H150.89240.10740.17570.015*
C160.88489 (13)−0.0119 (2)0.09003 (8)0.0139 (3)
H160.9213−0.12510.10000.017*
C170.84719 (12)0.0179 (2)0.02948 (8)0.0126 (3)
C180.79165 (12)0.1872 (2)0.01756 (7)0.0147 (3)
H180.76390.2097−0.02210.018*
C190.77770 (12)0.3220 (2)0.06473 (7)0.0136 (3)
H190.74040.43500.05610.016*
C200.86597 (12)−0.1204 (2)−0.02441 (7)0.0157 (3)
C211.42128 (13)0.6036 (2)0.26818 (8)0.0161 (3)
H211.4266 (13)0.600 (3)0.3157 (9)0.028 (5)*
C221.10601 (13)0.8010 (2)0.45686 (8)0.0188 (4)
H221.1561 (13)0.714 (3)0.4842 (9)0.020 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01001 (11)0.01290 (10)0.00882 (11)0.00080 (6)−0.00023 (7)−0.00111 (6)
O10.0092 (6)0.0225 (6)0.0129 (5)−0.0007 (4)0.0003 (4)−0.0045 (4)
O20.0144 (6)0.0195 (5)0.0106 (5)0.0021 (5)−0.0019 (5)−0.0020 (4)
O30.0120 (6)0.0184 (5)0.0098 (5)−0.0013 (4)−0.0021 (4)0.0016 (4)
O40.0134 (6)0.0141 (5)0.0135 (5)0.0030 (4)−0.0013 (5)−0.0022 (4)
O50.0524 (9)0.0310 (7)0.0097 (6)0.0163 (7)−0.0092 (6)−0.0050 (5)
O60.0130 (6)0.0295 (6)0.0172 (6)−0.0013 (5)−0.0005 (5)0.0005 (5)
O70.0279 (8)0.0248 (6)0.0181 (7)−0.0107 (5)0.0007 (6)−0.0038 (5)
N10.0094 (7)0.0145 (6)0.0096 (6)−0.0011 (5)−0.0002 (5)0.0003 (5)
N20.0256 (8)0.0193 (6)0.0094 (6)0.0055 (6)−0.0018 (6)−0.0037 (5)
C10.0111 (8)0.0103 (6)0.0115 (7)0.0008 (6)−0.0008 (6)−0.0005 (6)
C20.0111 (8)0.0102 (6)0.0113 (7)0.0000 (6)−0.0016 (6)0.0001 (6)
C30.0128 (8)0.0145 (7)0.0106 (7)0.0009 (6)0.0017 (6)0.0001 (6)
C40.0164 (8)0.0143 (7)0.0085 (7)0.0000 (6)−0.0008 (6)−0.0002 (6)
C50.0121 (8)0.0110 (7)0.0135 (8)0.0003 (6)−0.0016 (6)0.0002 (6)
C60.0113 (8)0.0190 (7)0.0127 (7)−0.0008 (6)0.0028 (6)−0.0003 (6)
C70.0143 (8)0.0183 (7)0.0076 (7)0.0006 (6)−0.0008 (6)0.0006 (6)
C80.0096 (8)0.0138 (7)0.0113 (7)0.0029 (6)0.0015 (6)−0.0023 (6)
C90.0098 (8)0.0154 (7)0.0091 (7)−0.0002 (6)0.0015 (6)−0.0020 (6)
C100.0173 (9)0.0137 (7)0.0137 (8)0.0002 (6)−0.0001 (7)−0.0003 (6)
C110.0144 (9)0.0206 (8)0.0134 (8)0.0021 (6)−0.0043 (7)−0.0003 (6)
C120.0113 (8)0.0191 (7)0.0117 (7)−0.0021 (6)−0.0004 (6)−0.0029 (6)
C130.0149 (8)0.0136 (7)0.0129 (7)−0.0015 (6)0.0041 (6)−0.0024 (6)
C140.0111 (8)0.0164 (7)0.0090 (7)0.0020 (6)0.0012 (6)0.0004 (6)
C150.0116 (8)0.0171 (7)0.0087 (7)0.0004 (6)−0.0023 (6)0.0008 (6)
C160.0157 (9)0.0140 (7)0.0120 (8)0.0026 (6)−0.0017 (7)−0.0003 (5)
C170.0147 (8)0.0143 (7)0.0088 (8)−0.0022 (6)0.0006 (6)−0.0003 (5)
C180.0169 (9)0.0176 (7)0.0094 (7)−0.0006 (6)−0.0029 (6)0.0014 (6)
C190.0130 (8)0.0150 (7)0.0128 (7)0.0019 (6)−0.0011 (6)0.0029 (6)
C200.0180 (9)0.0185 (7)0.0106 (7)0.0001 (6)−0.0013 (7)−0.0024 (6)
C210.0173 (9)0.0171 (7)0.0139 (8)0.0003 (6)−0.0024 (7)−0.0003 (6)
C220.0174 (9)0.0260 (8)0.0131 (8)−0.0046 (7)0.0007 (7)−0.0018 (7)
Geometric parameters (Å, °) top
Zn1—O11.9153 (11)C7—C61.378 (2)
Zn1—O31.9723 (11)C7—H70.93
Zn1—O41.9450 (10)C8—O4ii1.2669 (18)
Zn1—N12.0270 (12)C8—C91.495 (2)
O1—C11.2807 (18)C9—C101.397 (2)
O2—C11.2405 (18)C9—C141.3990 (19)
O3—C81.2611 (17)C10—H100.93
O4—C8i1.2669 (18)C11—C101.381 (2)
O5—C201.2261 (18)C11—H110.93
O6—C211.214 (2)C12—C111.395 (2)
O7—C221.2124 (19)C12—C131.397 (2)
N1—C151.3427 (18)C12—C221.484 (2)
N1—C191.3474 (18)C13—C141.377 (2)
N2—C201.332 (2)C13—H130.93
N2—H2A0.86C14—H140.93
N2—H2B0.86C15—H150.93
C2—C11.507 (2)C16—C151.382 (2)
C2—C31.390 (2)C16—C171.392 (2)
C2—C71.393 (2)C16—H160.93
C3—C41.396 (2)C18—C171.386 (2)
C3—H30.93C18—H180.93
C4—H40.93C19—C181.378 (2)
C5—C41.383 (2)C19—H190.93
C5—C61.396 (2)C20—C171.512 (2)
C5—C211.478 (2)C21—H211.018 (19)
C6—H60.93C22—H221.057 (17)
O1—Zn1—O3106.50 (4)C14—C9—C8121.23 (13)
O1—Zn1—O4123.30 (5)C9—C10—H10120.0
O1—Zn1—N1109.22 (5)C11—C10—C9119.95 (14)
O3—Zn1—N1104.39 (5)C11—C10—H10120.0
O4—Zn1—O3111.89 (5)C10—C11—C12120.45 (15)
O4—Zn1—N199.88 (5)C10—C11—H11119.8
C1—O1—Zn1123.27 (10)C12—C11—H11119.8
C8—O3—Zn1138.48 (10)C11—C12—C13119.50 (14)
C8i—O4—Zn1120.13 (10)C11—C12—C22118.70 (15)
C15—N1—Zn1119.26 (10)C13—C12—C22121.77 (14)
C15—N1—C19118.22 (13)C12—C13—H13120.0
C19—N1—Zn1121.95 (10)C14—C13—C12120.09 (14)
C20—N2—H2A120.0C14—C13—H13120.0
C20—N2—H2B120.0C9—C14—H14119.8
H2A—N2—H2B120.0C13—C14—C9120.42 (14)
O1—C1—C2115.07 (13)C13—C14—H14119.8
O2—C1—O1124.67 (14)N1—C15—C16122.57 (14)
O2—C1—C2120.25 (14)N1—C15—H15118.7
C3—C2—C1119.87 (14)C16—C15—H15118.7
C3—C2—C7120.36 (14)C15—C16—C17119.19 (14)
C7—C2—C1119.76 (13)C15—C16—H16120.4
C2—C3—C4119.77 (14)C17—C16—H16120.4
C2—C3—H3120.1C16—C17—C20123.82 (13)
C4—C3—H3120.1C18—C17—C16118.00 (14)
C3—C4—H4120.3C18—C17—C20118.16 (14)
C5—C4—C3119.36 (14)C17—C18—H18120.1
C5—C4—H4120.3C19—C18—C17119.77 (14)
C4—C5—C6120.90 (14)C19—C18—H18120.1
C4—C5—C21118.62 (14)N1—C19—C18122.20 (14)
C6—C5—C21120.48 (14)N1—C19—H19118.9
C5—C6—H6120.2C18—C19—H19118.9
C7—C6—C5119.60 (14)O5—C20—N2123.26 (15)
C7—C6—H6120.2O5—C20—C17119.35 (14)
C2—C7—H7120.0N2—C20—C17117.39 (13)
C6—C7—C2119.98 (14)O6—C21—C5124.78 (15)
C6—C7—H7120.0O6—C21—H21119.0 (11)
O3—C8—O4ii121.72 (14)C5—C21—H21116.3 (11)
O3—C8—C9122.19 (13)O7—C22—C12124.98 (17)
O4ii—C8—C9116.01 (13)O7—C22—H22121.9 (9)
C10—C9—C8119.27 (13)C12—C22—H22113.1 (9)
C10—C9—C14119.45 (14)
O3—Zn1—O1—C1132.27 (11)C21—C5—C4—C3178.69 (13)
O4—Zn1—O1—C1−96.44 (12)C4—C5—C6—C7−0.3 (2)
N1—Zn1—O1—C120.07 (13)C21—C5—C6—C7−179.85 (14)
O1—Zn1—O3—C8−6.56 (15)C4—C5—C21—O6−177.81 (15)
O4—Zn1—O3—C8−143.97 (14)C6—C5—C21—O61.7 (2)
N1—Zn1—O3—C8108.94 (15)C2—C7—C6—C51.5 (2)
O1—Zn1—O4—C8i−60.90 (13)O3—C8—C9—C10−158.23 (15)
O3—Zn1—O4—C8i68.17 (12)O3—C8—C9—C1424.3 (2)
N1—Zn1—O4—C8i178.16 (11)O4ii—C8—C9—C1024.8 (2)
O1—Zn1—N1—C1562.86 (12)O4ii—C8—C9—C14−152.61 (15)
O1—Zn1—N1—C19−108.32 (12)C8—C9—C10—C11−177.06 (15)
O3—Zn1—N1—C15−50.72 (12)C14—C9—C10—C110.4 (2)
O3—Zn1—N1—C19138.10 (12)C8—C9—C14—C13174.28 (14)
O4—Zn1—N1—C15−166.53 (11)C10—C9—C14—C13−3.2 (2)
O4—Zn1—N1—C1922.29 (13)C12—C11—C10—C92.9 (3)
Zn1—O1—C1—O225.4 (2)C13—C12—C11—C10−3.6 (3)
Zn1—O1—C1—C2−155.21 (9)C22—C12—C11—C10174.41 (16)
Zn1—O3—C8—O4ii−147.48 (12)C11—C12—C13—C140.9 (2)
Zn1—O3—C8—C935.8 (2)C22—C12—C13—C14−177.08 (15)
Zn1—N1—C15—C16−169.24 (12)C11—C12—C22—O7−171.97 (17)
C19—N1—C15—C162.3 (2)C13—C12—C22—O76.0 (3)
Zn1—N1—C19—C18169.38 (12)C12—C13—C14—C92.5 (2)
C15—N1—C19—C18−1.9 (2)C17—C16—C15—N1−0.7 (2)
C3—C2—C1—O19.2 (2)C15—C16—C17—C18−1.4 (2)
C3—C2—C1—O2−171.42 (14)C15—C16—C17—C20176.70 (15)
C7—C2—C1—O1−171.18 (13)C19—C18—C17—C161.7 (2)
C7—C2—C1—O28.2 (2)C19—C18—C17—C20−176.45 (14)
C1—C2—C3—C4179.87 (13)N1—C19—C18—C17−0.1 (2)
C7—C2—C3—C40.2 (2)N2—C20—C17—C165.3 (2)
C1—C2—C7—C6178.94 (14)N2—C20—C17—C18−176.65 (15)
C3—C2—C7—C6−1.4 (2)O5—C20—C17—C16−174.85 (17)
C2—C3—C4—C50.9 (2)O5—C20—C17—C183.2 (2)
C6—C5—C4—C3−0.8 (2)
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2iii0.862.082.9242 (17)165
N2—H2B···O2iv0.862.112.9439 (17)163
C4—H4···O5v0.932.413.298 (2)160
C6—H6···O7vi0.932.503.223 (2)135
C15—H15···O6vi0.932.323.2049 (19)159
C16—H16···O2iv0.932.443.3541 (18)169
C3—H3···Cg10.932.733.6332 (17)163
Symmetry codes: (iii) −x+2, −y, −z; (iv) x, y−1, z; (v) x+1/2, −y+1/2, z+1/2; (vi) −x+5/2, y−1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Zn1—O11.9153 (11)Zn1—O41.9450 (10)
Zn1—O31.9723 (11)Zn1—N12.0270 (12)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.082.9242 (17)165
N2—H2B···O2ii0.862.112.9439 (17)163
C4—H4···O5iii0.932.413.298 (2)160
C6—H6···O7iv0.932.503.223 (2)135
C15—H15···O6iv0.932.323.2049 (19)159
C16—H16···O2ii0.932.443.3541 (18)169
C3—H3···Cg10.932.733.6332 (17)163
Symmetry codes: (i) −x+2, −y, −z; (ii) x, y−1, z; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+5/2, y−1/2, −z+1/2.
Acknowledgements top

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. 2009-FEF-03).

references
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