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Acta Cryst. (2009). E65, m1365-m1366    [ doi:10.1107/S1600536809041208 ]

Bis(isonicotinamide-[kappa]N1)bis[4-(methylamino)benzoato]zinc(II) monohydrate

T. Hökelek, H. Dal, B. Tercan, Ö. Aybirdi and H. Necefoglu

Abstract top

In the title ZnII complex, [Zn(C8H8NO2)2(C6H6N2O)2]·H2O, the Zn atom is coordinated by two 4-methylaminobenzoate (MAB) and two isonicotinamide (INA) ligands in a distorted trigonal-bipyramidal geometry; one of the MAB ions acts as a bidentate ligand while the other MAB and the two INA are monodentate ligands. The dihedral angles between the carboxyl groups and the adjacent benzene rings are 8.52 (22) and 5.10 (14)°. In the crystal, intermolecular O-H...O and N-H...O hydrogen bonding links the molecules into a supramolecular structure. Weak intermolecular C-H...O interactions are also present.

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.

The title compound, (I), is a monomeric complex, where the ZnII ion is surrounded by two methylaminobenzoate (MAB) and two isonicotinamide (INA) ligands. One of the MAB ions acts as a bidentate ligand, while the other MAB and two INA are monodentate ligands. The structures of similar complexes of ZnII ion, [Zn2(C10H14N2O)2(C7H5O3)4].2H2O, (II) (Hökelek & Necefoğlu, 1996) and [Zn(C9H10NO2)2(C6H6N2O)(H2O)2], (III) (Hökelek et al., 2009) have also been determined.

In the title compound (Fig. 1), the average Zn—O bond length (Table 1) is 2.095 (2) Å and the Zn atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O3/C8/O4) by 0.0717 (3) Å and 0.2813 (3) Å, respectively. The dihedral angle between the planar carboxylate groups and the adjacent benzene rings A (C2—C7) and B (C9—C14) are 8.52 (22)° and 5.10 (14)°, respectively, while those between rings A, B, C (N1/C15—C19) and D (N2/C20—C24) are A/B = 71.82 (7), A/C = 14.44 (6), A/D = 84.05 (8), B/C = 72.21 (7), B/D = 47.00 (8) and C/D = 74.92 (7) °. The intramolecular O—H···O hydrogen bond (Table 2) links the water molecule to the carboxylate group (O1/C1/O2). In (I), the O1—Zn1—O2 angle is 59.02 (8)°. The corresponding O—M—O (where M is a metal) angles are 58.3 (3)° in (II), 60.03 (6)° in (III) and 55.2 (1)° in [Cu(Asp)2(py)2] (where Asp is acetylsalicylate and py is pyridine) [(IV); Greenaway et al., 1984].

In the crystal structure, intramolecular O—H···O and intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds (Table 2) link the molecules into a supramolecular structure, in which they may be effective in the stabilization of the structure.

Related literature top

For niacin, see: Krishnamachari (1974) and for the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Greenaway et al. (1984); Hökelek & Necefoğlu (1996); Hökelek et al. (2009).

Experimental top

The title compound was prepared by the reaction of ZnSO4.H2O (0.9 g, 5 mmol) in H2O (30 ml) and INA (1.22 g, 10 mmol) in H2O (20 ml) with sodium 4-methylaminobenzoate (1.74 g, 10 mmol) in H2O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving yellow single crystals.

Refinement top

Atoms H71 and H72 (for H2O) were located in difference Fourier map and refined isotropically, with restrains of O7—H71 = 0.88 (4), O7—H72 = 0.88 (5) Å and H71—O7—H72 = 106 (4)°. The remaining H atoms were positioned geometrically with N—H = 0.86 Å (for NH and NH2) and C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed line indicates the hydrogen-bonding.
Bis(isonicotinamide-κN1)bis[4-(methylamino)benzoato]zinc(II) monohydrate top
Crystal data top
[Zn(C8H8NO2)2(C6H6N2O)2]·H2OF(000) = 1304
Mr = 627.95Dx = 1.437 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6603 reflections
a = 8.1323 (8) Åθ = 2.7–25.3°
b = 13.2098 (12) ŵ = 0.90 mm−1
c = 27.219 (3) ÅT = 294 K
β = 96.949 (6)°Block, yellow
V = 2902.6 (5) Å30.55 × 0.45 × 0.35 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		7249 independent reflections
Radiation source: fine-focus sealed tube5243 reflections with I > 2σ(I)
graphiteRint = 0.047
φ and ω scansθmax = 28.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −10→10
Tmin = 0.618, Tmax = 0.725k = −17→17
27836 measured reflectionsl = −27→36
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.046P)2 + 0.981P]
where P = (Fo2 + 2Fc2)/3
7249 reflections(Δ/σ)max < 0.001
389 parametersΔρmax = 0.62 e Å−3
3 restraintsΔρmin = −0.32 e Å−3
Crystal data top
[Zn(C8H8NO2)2(C6H6N2O)2]·H2OV = 2902.6 (5) Å3
Mr = 627.95Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1323 (8) ŵ = 0.90 mm−1
b = 13.2098 (12) ÅT = 294 K
c = 27.219 (3) Å0.55 × 0.45 × 0.35 mm
β = 96.949 (6)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		7249 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		5243 reflections with I > 2σ(I)
Tmin = 0.618, Tmax = 0.725Rint = 0.047
27836 measured reflectionsθmax = 28.5°
Refinement top
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110Δρmax = 0.62 e Å−3
S = 1.02Δρmin = −0.32 e Å−3
7249 reflectionsAbsolute structure: ?
389 parametersFlack parameter: ?
3 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
Zn10.38843 (3)0.14401 (2)0.382846 (9)0.03967 (9)
O10.6266 (3)0.19218 (15)0.37937 (9)0.0729 (6)
O20.4834 (3)0.29273 (19)0.41966 (8)0.0767 (6)
O30.3923 (2)0.00547 (13)0.35943 (7)0.0563 (5)
O40.5680 (2)−0.04606 (13)0.42345 (6)0.0530 (4)
O5−0.1909 (2)0.20940 (16)0.54876 (6)0.0642 (5)
O60.0275 (3)0.41634 (17)0.17505 (9)0.0875 (7)
O70.7484 (4)0.0760 (2)0.30434 (10)0.0854 (7)
H710.817 (5)0.028 (3)0.3165 (17)0.138 (19)*
H720.739 (10)0.118 (4)0.3290 (18)0.29 (4)*
N10.2088 (2)0.13652 (13)0.42983 (6)0.0379 (4)
N20.2637 (2)0.20452 (15)0.31803 (7)0.0414 (4)
N3−0.3353 (3)0.09359 (16)0.50163 (7)0.0474 (5)
H3A−0.41750.09710.51870.057*
H3B−0.33930.05310.47680.057*
N4−0.0387 (3)0.2613 (2)0.14760 (8)0.0648 (6)
H4A−0.08680.28370.11980.078*
H4B−0.03500.19730.15340.078*
N51.1355 (3)0.5607 (2)0.42313 (12)0.0793 (8)
H5A1.11840.61590.43850.095*
N60.5279 (4)−0.43347 (18)0.28178 (9)0.0701 (7)
H6A0.4608−0.44270.25520.084*
C10.6150 (4)0.2730 (2)0.40298 (10)0.0565 (7)
C20.7569 (3)0.34465 (18)0.40946 (9)0.0465 (6)
C30.8948 (3)0.3316 (2)0.38584 (11)0.0561 (7)
H30.90310.27430.36640.067*
C41.0221 (3)0.4018 (2)0.39029 (11)0.0596 (7)
H41.11430.39120.37380.072*
C51.0136 (3)0.4877 (2)0.41909 (11)0.0535 (6)
C60.8760 (3)0.4990 (2)0.44393 (10)0.0557 (6)
H60.86830.55500.46420.067*
C70.7507 (3)0.4289 (2)0.43909 (10)0.0523 (6)
H70.65960.43830.45620.063*
C80.4882 (3)−0.06043 (17)0.38227 (8)0.0409 (5)
C90.4992 (3)−0.15862 (16)0.35668 (8)0.0379 (5)
C100.6074 (3)−0.23362 (18)0.37532 (8)0.0454 (6)
H100.6740−0.22260.40510.055*
C110.6197 (3)−0.32501 (19)0.35091 (9)0.0492 (6)
H110.6943−0.37400.36420.059*
C120.5205 (3)−0.34305 (18)0.30670 (9)0.0463 (6)
C130.4099 (3)−0.2684 (2)0.28777 (9)0.0513 (6)
H130.3418−0.27970.25830.062*
C140.4007 (3)−0.17839 (19)0.31230 (9)0.0451 (5)
H140.3267−0.12920.29890.054*
C150.0795 (3)0.07424 (17)0.41887 (8)0.0393 (5)
H150.08240.02850.39300.047*
C16−0.0571 (3)0.07462 (16)0.44399 (8)0.0377 (5)
H16−0.14500.03080.43490.045*
C17−0.0624 (3)0.14121 (16)0.48315 (7)0.0368 (5)
C180.0745 (3)0.20295 (19)0.49524 (9)0.0474 (6)
H180.07740.24710.52190.057*
C190.2050 (3)0.19921 (19)0.46815 (9)0.0467 (6)
H190.29480.24200.47670.056*
C200.1486 (3)0.1521 (2)0.29058 (10)0.0546 (7)
H200.12080.08840.30160.066*
C210.0679 (3)0.1870 (2)0.24650 (10)0.0562 (7)
H21−0.01320.14770.22860.067*
C220.1084 (3)0.28063 (18)0.22918 (8)0.0438 (5)
C230.2258 (4)0.3356 (2)0.25815 (10)0.0563 (7)
H230.25480.39980.24820.068*
C240.3005 (3)0.2961 (2)0.30173 (10)0.0538 (6)
H240.38000.33460.32080.065*
C250.0290 (3)0.3249 (2)0.18116 (10)0.0536 (6)
C26−0.2036 (3)0.15014 (18)0.51356 (8)0.0421 (5)
C271.2895 (4)0.5493 (3)0.40301 (19)0.1095 (15)
H27A1.35650.60840.41040.164*
H27B1.26820.54080.36780.164*
H27C1.34690.49090.41740.164*
C280.6406 (5)−0.5118 (2)0.29771 (13)0.0799 (10)
H28A0.6176−0.57010.27690.120*
H28B0.6288−0.52940.33130.120*
H28C0.7517−0.48920.29570.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03984 (15)0.03946 (15)0.03854 (14)0.00064 (12)−0.00003 (10)−0.00057 (11)
O10.0594 (12)0.0508 (12)0.1023 (17)−0.0087 (10)−0.0158 (11)−0.0037 (11)
O20.0548 (12)0.1030 (18)0.0720 (13)−0.0330 (12)0.0069 (11)0.0000 (12)
O30.0581 (11)0.0415 (9)0.0678 (12)0.0058 (8)0.0019 (9)−0.0055 (9)
O40.0616 (11)0.0534 (10)0.0436 (9)−0.0119 (9)0.0054 (8)−0.0142 (8)
O50.0619 (12)0.0890 (15)0.0424 (9)−0.0183 (11)0.0093 (8)−0.0312 (10)
O60.0969 (17)0.0636 (14)0.0910 (16)−0.0088 (12)−0.0338 (13)0.0343 (12)
O70.0896 (18)0.0896 (18)0.0740 (15)0.0117 (15)−0.0021 (13)0.0119 (14)
N10.0399 (10)0.0368 (10)0.0360 (9)−0.0024 (8)0.0005 (8)−0.0004 (8)
N20.0444 (11)0.0430 (11)0.0362 (9)0.0032 (9)0.0022 (8)0.0038 (8)
N30.0493 (12)0.0569 (13)0.0367 (10)−0.0133 (10)0.0086 (9)−0.0088 (9)
N40.0757 (16)0.0712 (16)0.0428 (12)0.0031 (13)−0.0126 (11)0.0135 (11)
N50.0610 (15)0.0601 (15)0.120 (2)−0.0228 (13)0.0253 (16)−0.0080 (15)
N60.099 (2)0.0504 (14)0.0573 (14)0.0041 (13)−0.0066 (13)−0.0171 (11)
C10.0561 (16)0.0532 (16)0.0541 (15)−0.0097 (13)−0.0185 (13)0.0166 (13)
C20.0429 (12)0.0447 (13)0.0494 (13)−0.0023 (11)−0.0047 (11)0.0112 (11)
C30.0574 (16)0.0388 (13)0.0714 (18)0.0053 (12)0.0052 (14)0.0010 (12)
C40.0484 (15)0.0549 (16)0.0784 (19)0.0017 (13)0.0194 (14)0.0010 (15)
C50.0462 (14)0.0456 (14)0.0680 (17)−0.0064 (12)0.0038 (12)0.0059 (13)
C60.0540 (15)0.0538 (15)0.0583 (15)−0.0052 (13)0.0026 (13)−0.0087 (13)
C70.0421 (13)0.0636 (16)0.0512 (14)−0.0058 (12)0.0058 (11)−0.0014 (13)
C80.0411 (12)0.0401 (12)0.0434 (12)−0.0090 (10)0.0124 (10)−0.0036 (10)
C90.0391 (11)0.0383 (12)0.0363 (11)−0.0043 (10)0.0049 (9)−0.0004 (9)
C100.0498 (14)0.0471 (13)0.0372 (12)−0.0017 (11)−0.0037 (10)−0.0028 (10)
C110.0554 (15)0.0437 (13)0.0471 (13)0.0074 (11)0.0007 (11)0.0014 (11)
C120.0565 (14)0.0412 (13)0.0416 (12)−0.0066 (11)0.0070 (11)−0.0027 (10)
C130.0555 (15)0.0549 (15)0.0408 (12)−0.0049 (12)−0.0058 (11)−0.0071 (11)
C140.0478 (13)0.0459 (13)0.0400 (12)0.0020 (11)−0.0011 (10)−0.0005 (10)
C150.0476 (13)0.0364 (11)0.0327 (10)−0.0043 (10)0.0000 (9)−0.0051 (9)
C160.0425 (12)0.0356 (11)0.0332 (10)−0.0059 (10)−0.0027 (9)−0.0021 (9)
C170.0423 (11)0.0380 (11)0.0281 (9)−0.0024 (10)−0.0034 (8)0.0026 (9)
C180.0518 (14)0.0511 (14)0.0380 (11)−0.0115 (12)0.0005 (11)−0.0147 (11)
C190.0454 (13)0.0498 (14)0.0438 (12)−0.0127 (11)0.0016 (11)−0.0120 (11)
C200.0638 (16)0.0461 (14)0.0501 (14)−0.0102 (13)−0.0092 (12)0.0121 (12)
C210.0577 (16)0.0540 (15)0.0519 (14)−0.0137 (13)−0.0137 (12)0.0094 (12)
C220.0408 (12)0.0489 (14)0.0410 (12)0.0050 (11)0.0017 (10)0.0080 (10)
C230.0637 (17)0.0475 (15)0.0547 (15)−0.0075 (13)−0.0042 (13)0.0120 (12)
C240.0596 (16)0.0493 (15)0.0490 (14)−0.0086 (13)−0.0081 (12)0.0054 (12)
C250.0438 (13)0.0593 (16)0.0553 (15)0.0013 (12)−0.0036 (12)0.0173 (13)
C260.0459 (12)0.0500 (13)0.0290 (10)−0.0034 (11)−0.0005 (9)−0.0014 (10)
C270.061 (2)0.091 (3)0.181 (5)−0.025 (2)0.035 (3)0.004 (3)
C280.119 (3)0.0436 (16)0.078 (2)0.0090 (18)0.013 (2)−0.0122 (15)
Geometric parameters (Å, °) top
Zn1—O12.051 (2)C8—C91.480 (3)
Zn1—O22.296 (2)C9—C101.380 (3)
Zn1—O31.9394 (17)C9—C141.391 (3)
Zn1—N12.0569 (18)C10—H100.9300
Zn1—N22.0850 (18)C11—C101.388 (3)
O1—C11.256 (4)C11—H110.9300
O3—C81.279 (3)C12—N61.379 (3)
O5—C261.232 (3)C12—C111.386 (3)
O6—C251.219 (3)C13—C121.391 (4)
O7—H710.88 (4)C13—H130.9300
O7—H720.88 (5)C14—C131.370 (3)
N1—C151.340 (3)C14—H140.9300
N1—C191.335 (3)C15—H150.9300
N2—C201.321 (3)C16—C151.373 (3)
N2—C241.335 (3)C16—H160.9300
N3—C261.314 (3)C17—C161.387 (3)
N3—H3A0.8600C17—C261.499 (3)
N3—H3B0.8600C18—C171.387 (3)
N4—H4A0.8600C18—H180.9300
N4—H4B0.8600C19—C181.365 (3)
N5—C271.434 (4)C19—H190.9300
N5—H5A0.8600C20—C211.376 (3)
N6—C281.415 (4)C20—H200.9300
N6—H6A0.8600C21—C221.378 (3)
C1—O21.240 (4)C21—H210.9300
C1—C21.486 (4)C22—C231.371 (3)
C2—C31.369 (4)C22—C251.504 (3)
C2—C71.378 (4)C23—C241.369 (3)
C3—C41.385 (4)C23—H230.9300
C3—H30.9300C24—H240.9300
C4—C51.386 (4)C25—N41.312 (4)
C4—H40.9300C27—H27A0.9600
C5—N51.377 (3)C27—H27B0.9600
C5—C61.384 (4)C27—H27C0.9600
C6—C71.372 (4)C28—H28A0.9600
C6—H60.9300C28—H28B0.9600
C7—H70.9300C28—H28C0.9600
C8—O41.240 (3)
O1—Zn1—O259.02 (8)C9—C10—C11121.9 (2)
O1—Zn1—N1142.08 (8)C9—C10—H10119.1
O1—Zn1—N2101.97 (8)C11—C10—H10119.1
O3—Zn1—O1102.97 (8)C10—C11—H11120.1
O3—Zn1—O2158.87 (8)C12—C11—C10119.8 (2)
O3—Zn1—N1101.54 (8)C12—C11—H11120.1
O3—Zn1—N296.27 (8)N6—C12—C11121.4 (2)
O3—Zn1—C1131.97 (9)N6—C12—C13119.8 (2)
N1—Zn1—O289.80 (7)C11—C12—C13118.8 (2)
N1—Zn1—N2103.61 (7)C12—C13—H13119.8
N1—Zn1—C1116.91 (9)C14—C13—C12120.4 (2)
N2—Zn1—O298.32 (8)C14—C13—H13119.8
N2—Zn1—C1101.11 (8)C9—C14—H14119.1
C1—O1—Zn196.36 (19)C13—C14—C9121.8 (2)
C1—O2—Zn185.43 (18)C13—C14—H14119.1
C8—O3—Zn1121.05 (16)N1—C15—C16123.2 (2)
H71—O7—H72106 (4)N1—C15—H15118.4
C15—N1—Zn1119.23 (14)C16—C15—H15118.4
C19—N1—Zn1122.76 (15)C15—C16—C17119.2 (2)
C19—N1—C15117.6 (2)C15—C16—H16120.4
C20—N2—Zn1121.09 (16)C17—C16—H16120.4
C20—N2—C24117.3 (2)C16—C17—C18117.2 (2)
C24—N2—Zn1121.55 (17)C16—C17—C26124.8 (2)
C26—N3—H3A120.0C18—C17—C26117.97 (19)
C26—N3—H3B120.0C17—C18—H18119.8
H3A—N3—H3B120.0C19—C18—C17120.3 (2)
C25—N4—H4A120.0C19—C18—H18119.8
C25—N4—H4B120.0N1—C19—C18122.5 (2)
H4A—N4—H4B120.0N1—C19—H19118.7
C5—N5—C27123.3 (3)C18—C19—H19118.7
C5—N5—H5A118.3N2—C20—C21123.3 (2)
C27—N5—H5A118.3N2—C20—H20118.4
C12—N6—C28123.3 (2)C21—C20—H20118.4
C12—N6—H6A118.4C20—C21—C22119.4 (2)
C28—N6—H6A118.4C20—C21—H21120.3
O1—C1—Zn153.97 (14)C22—C21—H21120.3
O1—C1—C2119.8 (3)C21—C22—C25123.5 (2)
O2—C1—Zn165.22 (15)C23—C22—C21117.2 (2)
O2—C1—O1119.2 (3)C23—C22—C25119.3 (2)
O2—C1—C2121.0 (3)C22—C23—H23119.9
C3—C2—C1122.2 (3)C24—C23—C22120.1 (2)
C3—C2—C7117.8 (2)C24—C23—H23119.9
C7—C2—C1120.0 (2)N2—C24—C23122.7 (2)
C2—C3—C4121.4 (3)N2—C24—H24118.7
C2—C3—H3119.3C23—C24—H24118.7
C4—C3—H3119.3O6—C25—N4122.9 (3)
C3—C4—C5120.7 (3)O6—C25—C22120.0 (3)
C3—C4—H4119.6N4—C25—C22117.1 (2)
C5—C4—H4119.6O5—C26—N3122.9 (2)
N5—C5—C4122.3 (3)O5—C26—C17118.8 (2)
N5—C5—C6120.2 (3)N3—C26—C17118.34 (19)
C6—C5—C4117.6 (2)N5—C27—H27A109.5
C5—C6—H6119.5N5—C27—H27B109.5
C7—C6—C5121.0 (3)N5—C27—H27C109.5
C7—C6—H6119.5H27A—C27—H27B109.5
C2—C7—H7119.2H27A—C27—H27C109.5
C6—C7—C2121.5 (2)H27B—C27—H27C109.5
C6—C7—H7119.2N6—C28—H28A109.5
O3—C8—C9115.8 (2)N6—C28—H28B109.5
O4—C8—O3123.8 (2)N6—C28—H28C109.5
O4—C8—C9120.3 (2)H28A—C28—H28B109.5
C10—C9—C8121.9 (2)H28A—C28—H28C109.5
C10—C9—C14117.3 (2)H28B—C28—H28C109.5
C14—C9—C8120.8 (2)
O2—Zn1—O1—C1−1.11 (15)O2—C1—C2—C77.5 (4)
O3—Zn1—O1—C1−169.11 (16)C1—C2—C3—C4176.6 (2)
N1—Zn1—O1—C1−40.1 (2)C7—C2—C3—C4−1.8 (4)
N2—Zn1—O1—C191.48 (17)C1—C2—C7—C6−176.8 (2)
O1—Zn1—O2—C11.12 (15)C3—C2—C7—C61.7 (4)
O3—Zn1—O2—C135.3 (3)C2—C3—C4—C50.2 (4)
N1—Zn1—O2—C1158.38 (16)C3—C4—C5—N5−177.9 (3)
N2—Zn1—O2—C1−97.89 (16)C3—C4—C5—C61.6 (4)
O1—Zn1—O3—C860.91 (19)C4—C5—N5—C27−7.6 (5)
O2—Zn1—O3—C831.3 (3)C6—C5—N5—C27173.0 (3)
N1—Zn1—O3—C8−89.93 (18)N5—C5—C6—C7177.8 (3)
N2—Zn1—O3—C8164.76 (18)C4—C5—C6—C7−1.7 (4)
C1—Zn1—O3—C853.7 (2)C5—C6—C7—C20.1 (4)
O1—Zn1—N1—C15−163.70 (16)O3—C8—C9—C10175.0 (2)
O1—Zn1—N1—C1924.0 (2)O3—C8—C9—C14−4.4 (3)
O2—Zn1—N1—C15163.68 (17)O4—C8—C9—C10−5.6 (3)
O2—Zn1—N1—C19−8.64 (19)O4—C8—C9—C14175.0 (2)
O3—Zn1—N1—C15−34.28 (18)C8—C9—C10—C11−178.9 (2)
O3—Zn1—N1—C19153.40 (18)C14—C9—C10—C110.5 (4)
N2—Zn1—N1—C1565.17 (17)C8—C9—C14—C13179.4 (2)
N2—Zn1—N1—C19−107.15 (19)C10—C9—C14—C130.0 (4)
C1—Zn1—N1—C15175.36 (16)C12—C11—C10—C9−0.5 (4)
C1—Zn1—N1—C193.0 (2)C11—C12—N6—C28−3.0 (4)
O1—Zn1—N2—C20139.6 (2)C13—C12—N6—C28177.9 (3)
O1—Zn1—N2—C24−38.2 (2)N6—C12—C11—C10−179.2 (2)
O2—Zn1—N2—C20−160.5 (2)C13—C12—C11—C10−0.1 (4)
O2—Zn1—N2—C2421.8 (2)C14—C13—C12—N6179.7 (2)
O3—Zn1—N2—C2034.9 (2)C14—C13—C12—C110.6 (4)
O3—Zn1—N2—C24−142.9 (2)C9—C14—C13—C12−0.6 (4)
N1—Zn1—N2—C20−68.7 (2)C17—C16—C15—N1−1.0 (3)
N1—Zn1—N2—C24113.6 (2)C18—C17—C16—C15−1.2 (3)
C1—Zn1—N2—C20169.9 (2)C26—C17—C16—C15179.7 (2)
C1—Zn1—N2—C24−7.9 (2)C16—C17—C26—O5177.1 (2)
Zn1—O1—C1—O22.0 (3)C16—C17—C26—N3−2.4 (3)
Zn1—O1—C1—C2−176.46 (19)C18—C17—C26—O5−2.0 (3)
Zn1—O3—C8—O49.7 (3)C18—C17—C26—N3178.4 (2)
Zn1—O3—C8—C9−170.82 (14)C19—C18—C17—C162.1 (3)
Zn1—N1—C15—C16−170.49 (17)C19—C18—C17—C26−178.7 (2)
C19—N1—C15—C162.2 (3)N1—C19—C18—C17−0.8 (4)
Zn1—N1—C19—C18171.13 (19)N2—C20—C21—C220.7 (5)
C15—N1—C19—C18−1.3 (4)C20—C21—C22—C23−1.7 (4)
Zn1—N2—C20—C21−177.2 (2)C20—C21—C22—C25179.2 (3)
C24—N2—C20—C210.6 (4)C21—C22—C23—C241.5 (4)
Zn1—N2—C24—C23176.9 (2)C25—C22—C23—C24−179.4 (3)
C20—N2—C24—C23−0.9 (4)C21—C22—C25—O6156.3 (3)
O1—C1—O2—Zn1−1.8 (2)C21—C22—C25—N4−22.6 (4)
C2—C1—O2—Zn1176.7 (2)C23—C22—C25—O6−22.7 (4)
O1—C1—C2—C37.5 (4)C23—C22—C25—N4158.3 (3)
O1—C1—C2—C7−174.1 (2)C22—C23—C24—N2−0.2 (4)
O2—C1—C2—C3−170.9 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O4i0.862.213.011 (3)154
N3—H3B···O4ii0.862.032.854 (3)160
N4—H4A···O5iii0.862.022.848 (3)162
N5—H5A···O5iv0.862.403.151 (3)147
N6—H6A···O7v0.862.223.047 (4)162
O7—H71···O6v0.88 (4)1.94 (4)2.799 (3)165 (4)
O7—H72···O10.88 (5)1.99 (6)2.828 (4)157 (7)
C15—H15···O6vi0.932.453.332 (3)157
C16—H16···O4ii0.932.533.426 (3)162
Symmetry codes: (i) −x, −y, −z+1; (ii) x−1, y, z; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) −x, y−1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Zn1—O12.051 (2)Zn1—N12.0569 (18)
Zn1—O22.296 (2)Zn1—N22.0850 (18)
Zn1—O31.9394 (17)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O4i0.862.213.011 (3)154
N3—H3B···O4ii0.862.032.854 (3)160
N4—H4A···O5iii0.862.022.848 (3)162
N5—H5A···O5iv0.862.403.151 (3)147
N6—H6A···O7v0.862.223.047 (4)162
O7—H71···O6v0.88 (4)1.94 (4)2.799 (3)165 (4)
O7—H72···O10.88 (5)1.99 (6)2.828 (4)157 (7)
C15—H15···O6vi0.932.453.332 (3)157
C16—H16···O4ii0.932.533.426 (3)162
Symmetry codes: (i) −x, −y, −z+1; (ii) x−1, y, z; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) −x, 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 X-ray diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2009-FEF-03).

references
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