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Acta Cryst. (2011). E67, m1470    [ doi:10.1107/S1600536811039389 ]

Bis(4-aminobenzoato)-[kappa]2O,O';[kappa]O-(2,2'-bipyridine-[kappa]2N,N')zinc

M.-L. Huang and L.-L. Wang

Abstract top

In the title complex, [Zn(C7H6NO2)2(C10H8N2)], the ZnII cation is coordinated by two aminobenzoate anions and one 2,2'-bipyridine ligand in a distorted trigonal-bipyramidal geometry. The carboxylate group of one aminobenzoate anion coordinates to the ZnII cation in a monodentate manner, whereas the carboxylate group of the other aminobenzoate anion chelates the Zn cation with different Zn-O bond lengths. Intermolecular N-H...N and N-H...O hydrogen bonding is present in the crystal structure.

Comment top

In recent decades, zinc complexes have received much attention because of their interesting with biological ligands to generate stable mixed coordinated complexes, which play a key role in life process such as anti-cancer, antiseptic and anti-inflammatory (Ispir et al., 2006; Chohan & Naseer, 2007; Huang et al., 2006; Lo et al., 2007). 4-Aminobenzoic acid as an important part in the folic acid, which is a constituent of the vitamin B complex and is found in animal and plant tissues, has been shown to be a growth factor in certain microorganisms (Maria et al., 1996). In order to extend further the study of 4-aminobenzoic acid ligand coordinate to zinc ion, we synthesized the title complex and determined the crystal structure.

The asymmetric unit of 1 contains one zinc cation, two 4-aminobenzoic ion, and one 2,2'-bipyridine molecule. The Zn(II) atom is five-coordinated, forming a distorted trigonal-bipyramidal (Table 1). In the coordination polyhedron, the equatorial plane is occupied by two O(O1,O3) atoms from different 4-aba and one N(N4) atom from 2,2'-bipyridine, at the apex is situated one O(O4) atom from 4-aba and one N(N3) atom from 2,2'-bipyridine (Fig 1). The Zn(II) center is coordinated by two types of 4-aba: one behaves in an unsymmetrical chelating mode [Zn—O(3) 1.9704 (18) and Zn—O(4) 2.395 (2) Å]; the other acts as a monodentate ligand through one carboxylate oxygen atom [Zn—O(1) 1.9269 (18) and Zn—O(2) 2.841 Å], which is similar to previously reported complex {[Zn2(4,4'-bipy)2(4-aba)4](H2O)5} (Wang et al., 2005). The dihedral angle between phenyl rings of the two 4-aba is 81.83 (7)°.

Hydrogen bonds are observed between the molecules in the crystal structure (Table 2).

Related literature top

For applications of Zn complexes, see: Chohan & Naseer (2007); Huang et al. (2006); Ispir et al. (2006); Lo et al. (2007); Maria et al. (1996). For a related structure, see: Wang et al. (2005).

Experimental top

An aqueous solution (5 ml) of ZnC4H6O4.2H2O (1 mmol) was added slowly to a mixed solution of 4-aminobenzoic acid (1.5 mmol) in H2O (5 ml) and 2,2'-bipyridine (1 mmol) in ethanol (95%, 5 ml). After refluxing for 3 h, the mixture was filtered off while hot. The colourless single crystals suitable for X-ray analysis were obtained by slow evaporation of the above filtrate at room temperature after a month.

Refinement top

H atoms were placed geometrically and treated as riding, C—H = 0.93 and N—H = 0.88 Å, Uiso(H) = 1.2Ueq(C) and 1.5Ueq(N).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level.
[Figure 2] Fig. 2. Projection showing the two-dimensional structure formed by H-bonding interaction of the compound (I).
Bis(4-aminobenzoato)-κ2O,O';κO- (2,2'-bipyridine-κ2N,N')zinc top
Crystal data top
[Zn(C7H6NO2)2(C10H8N2)]Z = 2
Mr = 493.81F(000) = 508
Triclinic, P1Dx = 1.496 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9499 (14) ÅCell parameters from 2868 reflections
b = 10.7281 (19) Åθ = 2.4–24.9°
c = 13.905 (2) ŵ = 1.16 mm−1
α = 80.499 (2)°T = 295 K
β = 80.921 (2)°Block, colourless
γ = 70.538 (2)°0.42 × 0.23 × 0.08 mm
V = 1096.1 (3) Å3
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		4058 independent reflections
Radiation source: fine-focus sealed tube3419 reflections with I > 2σ(I)
graphiteRint = 0.024
φ and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −9→9
Tmin = 0.643, Tmax = 0.914k = −12→12
8223 measured reflectionsl = −16→16
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0411P)2 + 0.2825P]
where P = (Fo2 + 2Fc2)/3
4058 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
[Zn(C7H6NO2)2(C10H8N2)]γ = 70.538 (2)°
Mr = 493.81V = 1096.1 (3) Å3
Triclinic, P1Z = 2
a = 7.9499 (14) ÅMo Kα radiation
b = 10.7281 (19) ŵ = 1.16 mm−1
c = 13.905 (2) ÅT = 295 K
α = 80.499 (2)°0.42 × 0.23 × 0.08 mm
β = 80.921 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		4058 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3419 reflections with I > 2σ(I)
Tmin = 0.643, Tmax = 0.914Rint = 0.024
8223 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.090Δρmax = 0.31 e Å−3
S = 1.07Δρmin = −0.31 e Å−3
4058 reflectionsAbsolute structure: ?
298 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
Zn10.14918 (4)0.12380 (3)0.19516 (2)0.04021 (12)
O1−0.1044 (2)0.2151 (2)0.21855 (14)0.0528 (5)
O2−0.0311 (3)0.3661 (2)0.27669 (18)0.0732 (7)
O30.3785 (3)0.10054 (19)0.24420 (15)0.0558 (5)
O40.2405 (3)−0.0296 (2)0.33755 (15)0.0663 (6)
N1−0.8907 (3)0.5767 (3)0.3483 (2)0.0678 (7)
H1D−0.92910.62590.39710.102*
H1E−0.96110.53230.33890.102*
N21.0034 (4)−0.2214 (3)0.5101 (2)0.0788 (9)
H2D1.0548−0.16040.51010.118*
H2E0.9810−0.26100.56930.118*
N30.2165 (3)0.1976 (2)0.04781 (16)0.0502 (6)
N40.1805 (3)−0.0382 (2)0.12124 (15)0.0419 (5)
C1−0.3406 (3)0.3914 (2)0.28122 (17)0.0362 (5)
C2−0.4024 (4)0.4919 (3)0.3417 (2)0.0488 (7)
H2−0.32010.51850.36700.059*
C3−0.5831 (4)0.5529 (3)0.3648 (2)0.0537 (7)
H3−0.62110.61960.40570.064*
C4−0.7100 (3)0.5157 (3)0.3275 (2)0.0444 (6)
C5−0.6484 (3)0.4166 (2)0.26597 (19)0.0417 (6)
H5−0.73030.39140.23910.050*
C6−0.4677 (3)0.3554 (2)0.24420 (18)0.0375 (5)
H6−0.42970.28820.20360.045*
C7−0.1451 (3)0.3227 (3)0.25832 (18)0.0423 (6)
C80.5359 (3)−0.0506 (2)0.36920 (17)0.0368 (5)
C90.5508 (4)−0.1572 (3)0.44177 (19)0.0479 (7)
H90.4560−0.19190.45890.058*
C100.7028 (4)−0.2133 (3)0.4894 (2)0.0560 (8)
H100.7105−0.28610.53720.067*
C110.8444 (4)−0.1614 (3)0.4663 (2)0.0495 (7)
C120.8290 (3)−0.0533 (3)0.3952 (2)0.0474 (6)
H120.9222−0.01670.37960.057*
C130.6791 (3)0.0007 (3)0.34731 (18)0.0416 (6)
H130.67230.07300.29920.050*
C140.3746 (3)0.0096 (3)0.3162 (2)0.0456 (6)
C150.2298 (5)0.3190 (3)0.0162 (3)0.0771 (10)
H150.20110.38090.06070.093*
C160.2848 (7)0.3549 (4)−0.0801 (3)0.1001 (14)
H160.29200.4402−0.10060.120*
C170.3286 (6)0.2642 (5)−0.1448 (3)0.0988 (14)
H170.36780.2865−0.21000.119*
C180.3146 (5)0.1395 (4)−0.1135 (2)0.0714 (9)
H180.34370.0765−0.15710.086*
C190.2563 (3)0.1089 (3)−0.01574 (19)0.0479 (7)
C200.2330 (3)−0.0219 (3)0.02410 (19)0.0461 (6)
C210.2580 (5)−0.1217 (3)−0.0330 (2)0.0702 (9)
H210.2929−0.1097−0.10000.084*
C220.2307 (6)−0.2389 (4)0.0103 (3)0.0783 (10)
H220.2470−0.3069−0.02740.094*
C230.1794 (5)−0.2557 (3)0.1088 (2)0.0673 (9)
H230.1607−0.33480.13900.081*
C240.1561 (4)−0.1535 (3)0.1622 (2)0.0534 (7)
H240.1221−0.16480.22930.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03267 (17)0.04633 (19)0.03920 (18)−0.00652 (13)−0.00538 (12)−0.00961 (13)
O10.0335 (9)0.0589 (12)0.0619 (12)−0.0044 (9)−0.0064 (8)−0.0168 (10)
O20.0385 (11)0.0841 (16)0.1075 (19)−0.0255 (11)−0.0096 (11)−0.0263 (14)
O30.0480 (11)0.0515 (12)0.0688 (13)−0.0078 (9)−0.0261 (10)−0.0074 (10)
O40.0385 (11)0.1067 (18)0.0642 (13)−0.0291 (11)−0.0019 (9)−0.0299 (12)
N10.0407 (13)0.0650 (17)0.092 (2)−0.0066 (12)0.0100 (13)−0.0317 (15)
N20.0660 (18)0.0786 (19)0.0765 (19)0.0202 (15)−0.0384 (15)−0.0286 (15)
N30.0525 (14)0.0509 (14)0.0436 (13)−0.0125 (11)−0.0062 (11)−0.0024 (11)
N40.0386 (11)0.0477 (13)0.0367 (12)−0.0080 (10)−0.0058 (9)−0.0080 (10)
C10.0333 (12)0.0379 (13)0.0360 (13)−0.0109 (10)−0.0050 (10)−0.0006 (11)
C20.0466 (16)0.0530 (17)0.0544 (17)−0.0212 (13)−0.0054 (13)−0.0165 (13)
C30.0538 (17)0.0496 (17)0.0607 (18)−0.0152 (14)0.0040 (14)−0.0272 (14)
C40.0370 (13)0.0389 (14)0.0521 (16)−0.0087 (11)0.0046 (12)−0.0069 (12)
C50.0346 (13)0.0412 (14)0.0519 (15)−0.0135 (11)−0.0053 (11)−0.0092 (12)
C60.0361 (13)0.0355 (13)0.0392 (13)−0.0078 (10)−0.0030 (10)−0.0089 (11)
C70.0371 (14)0.0484 (16)0.0369 (14)−0.0096 (12)−0.0068 (11)0.0012 (12)
C80.0330 (12)0.0403 (14)0.0373 (13)−0.0090 (10)−0.0007 (10)−0.0133 (11)
C90.0513 (16)0.0508 (16)0.0463 (15)−0.0246 (13)0.0056 (13)−0.0115 (13)
C100.074 (2)0.0433 (16)0.0413 (15)−0.0070 (15)−0.0095 (14)0.0011 (12)
C110.0436 (15)0.0522 (16)0.0433 (15)0.0072 (13)−0.0117 (12)−0.0200 (13)
C120.0339 (13)0.0607 (18)0.0493 (16)−0.0137 (13)−0.0017 (12)−0.0166 (14)
C130.0380 (14)0.0432 (14)0.0421 (14)−0.0116 (11)−0.0056 (11)−0.0025 (11)
C140.0349 (14)0.0535 (17)0.0504 (16)−0.0071 (12)−0.0044 (12)−0.0270 (14)
C150.111 (3)0.059 (2)0.064 (2)−0.034 (2)−0.013 (2)0.0027 (17)
C160.150 (4)0.081 (3)0.072 (3)−0.056 (3)−0.009 (3)0.021 (2)
C170.128 (4)0.107 (3)0.055 (2)−0.048 (3)0.008 (2)0.013 (2)
C180.083 (2)0.077 (2)0.0436 (17)−0.0196 (19)0.0055 (16)−0.0039 (16)
C190.0380 (14)0.0542 (17)0.0414 (15)−0.0035 (12)−0.0025 (11)−0.0029 (13)
C200.0405 (14)0.0507 (16)0.0413 (15)−0.0034 (12)−0.0083 (11)−0.0093 (12)
C210.095 (3)0.065 (2)0.0431 (17)−0.0107 (19)−0.0063 (17)−0.0166 (15)
C220.114 (3)0.058 (2)0.063 (2)−0.017 (2)−0.016 (2)−0.0232 (17)
C230.090 (2)0.0486 (18)0.066 (2)−0.0206 (17)−0.0171 (18)−0.0092 (16)
C240.0610 (18)0.0525 (17)0.0464 (16)−0.0170 (14)−0.0079 (13)−0.0054 (13)
Geometric parameters (Å, °) top
Zn1—O11.9269 (18)C6—H60.9300
Zn1—O31.9704 (18)C8—C91.381 (4)
Zn1—O42.395 (2)C8—C131.394 (3)
Zn1—N32.124 (2)C8—C141.481 (4)
Zn1—N42.088 (2)C9—C101.377 (4)
Zn1—C142.521 (3)C9—H90.9300
O1—C71.284 (3)C10—C111.387 (4)
O2—C71.223 (3)C10—H100.9300
O3—C141.282 (3)C11—C121.380 (4)
O4—C141.249 (3)C12—C131.364 (3)
N1—C41.372 (3)C12—H120.9300
N1—H1D0.8818C13—H130.9300
N1—H1E0.8820C15—C161.375 (5)
N2—C111.397 (3)C15—H150.9300
N2—H2D0.8798C16—C171.358 (6)
N2—H2E0.8825C16—H160.9300
N3—C191.332 (4)C17—C181.372 (5)
N3—C151.338 (4)C17—H170.9300
N4—C241.335 (3)C18—C191.388 (4)
N4—C201.350 (3)C18—H180.9300
C1—C21.388 (4)C19—C201.481 (4)
C1—C61.388 (3)C20—C211.381 (4)
C1—C71.490 (3)C21—C221.371 (5)
C2—C31.375 (4)C21—H210.9300
C2—H20.9300C22—C231.367 (5)
C3—C41.396 (4)C22—H220.9300
C3—H30.9300C23—C241.371 (4)
C4—C51.386 (4)C23—H230.9300
C5—C61.373 (3)C24—H240.9300
C5—H50.9300
O1—Zn1—O3141.27 (9)C13—C8—C14120.3 (2)
O1—Zn1—N4107.51 (8)C10—C9—C8121.5 (3)
O3—Zn1—N4108.58 (8)C10—C9—H9119.2
O1—Zn1—N3103.23 (9)C8—C9—H9119.2
O3—Zn1—N397.43 (9)C9—C10—C11120.2 (3)
N4—Zn1—N378.22 (9)C9—C10—H10119.9
O1—Zn1—O4108.31 (8)C11—C10—H10119.9
O3—Zn1—O459.37 (8)C12—C11—C10118.6 (2)
N4—Zn1—O488.61 (8)C12—C11—N2120.4 (3)
N3—Zn1—O4148.23 (8)C10—C11—N2120.9 (3)
O1—Zn1—C14129.59 (8)C13—C12—C11121.0 (3)
O3—Zn1—C1430.11 (8)C13—C12—H12119.5
N4—Zn1—C1498.66 (8)C11—C12—H12119.5
N3—Zn1—C14124.19 (9)C12—C13—C8121.2 (2)
O4—Zn1—C1429.29 (8)C12—C13—H13119.4
C7—O1—Zn1114.85 (16)C8—C13—H13119.4
C14—O3—Zn199.43 (16)O4—C14—O3120.2 (3)
C14—O4—Zn180.92 (18)O4—C14—C8121.8 (3)
C4—N1—H1D119.3O3—C14—C8118.0 (2)
C4—N1—H1E115.8O4—C14—Zn169.79 (16)
H1D—N1—H1E115.8O3—C14—Zn150.46 (12)
C11—N2—H2D108.4C8—C14—Zn1167.2 (2)
C11—N2—H2E110.2N3—C15—C16121.9 (4)
H2D—N2—H2E113.1N3—C15—H15119.1
C19—N3—C15119.3 (3)C16—C15—H15119.1
C19—N3—Zn1114.43 (18)C17—C16—C15119.1 (4)
C15—N3—Zn1126.2 (2)C17—C16—H16120.5
C24—N4—C20119.2 (2)C15—C16—H16120.5
C24—N4—Zn1125.67 (18)C16—C17—C18119.6 (3)
C20—N4—Zn1115.14 (18)C16—C17—H17120.2
C2—C1—C6117.6 (2)C18—C17—H17120.2
C2—C1—C7121.3 (2)C17—C18—C19118.9 (3)
C6—C1—C7121.1 (2)C17—C18—H18120.5
C3—C2—C1121.3 (2)C19—C18—H18120.5
C3—C2—H2119.4N3—C19—C18121.2 (3)
C1—C2—H2119.4N3—C19—C20116.1 (2)
C2—C3—C4120.8 (2)C18—C19—C20122.7 (3)
C2—C3—H3119.6N4—C20—C21120.7 (3)
C4—C3—H3119.6N4—C20—C19115.9 (2)
N1—C4—C5120.3 (3)C21—C20—C19123.4 (3)
N1—C4—C3121.7 (3)C22—C21—C20119.3 (3)
C5—C4—C3118.0 (2)C22—C21—H21120.4
C6—C5—C4120.8 (2)C20—C21—H21120.4
C6—C5—H5119.6C23—C22—C21119.9 (3)
C4—C5—H5119.6C23—C22—H22120.0
C5—C6—C1121.6 (2)C21—C22—H22120.0
C5—C6—H6119.2C22—C23—C24118.5 (3)
C1—C6—H6119.2C22—C23—H23120.7
O2—C7—O1122.4 (2)C24—C23—H23120.7
O2—C7—C1122.0 (3)N4—C24—C23122.4 (3)
O1—C7—C1115.6 (2)N4—C24—H24118.8
C9—C8—C13117.5 (2)C23—C24—H24118.8
C9—C8—C14122.2 (2)
O3—Zn1—O1—C726.2 (3)C10—C11—C12—C13−0.9 (4)
N4—Zn1—O1—C7−175.82 (17)N2—C11—C12—C13175.6 (2)
N3—Zn1—O1—C7−94.20 (19)C11—C12—C13—C80.6 (4)
O4—Zn1—O1—C789.73 (19)C9—C8—C13—C120.6 (4)
C14—Zn1—O1—C766.4 (2)C14—C8—C13—C12−179.9 (2)
O1—Zn1—O3—C1483.1 (2)Zn1—O4—C14—O33.2 (2)
N4—Zn1—O3—C14−74.76 (17)Zn1—O4—C14—C8−173.9 (2)
N3—Zn1—O3—C14−154.77 (16)Zn1—O3—C14—O4−3.9 (3)
O4—Zn1—O3—C142.02 (14)Zn1—O3—C14—C8173.36 (18)
O1—Zn1—O4—C14−141.45 (15)C9—C8—C14—O43.2 (4)
O3—Zn1—O4—C14−2.07 (15)C13—C8—C14—O4−176.3 (2)
N4—Zn1—O4—C14110.56 (16)C9—C8—C14—O3−174.0 (2)
N3—Zn1—O4—C1445.8 (2)C13—C8—C14—O36.5 (3)
O1—Zn1—N3—C19−109.74 (19)C9—C8—C14—Zn1−150.2 (7)
O3—Zn1—N3—C19103.24 (19)C13—C8—C14—Zn130.3 (9)
N4—Zn1—N3—C19−4.28 (19)O1—Zn1—C14—O450.15 (19)
O4—Zn1—N3—C1963.2 (3)O3—Zn1—C14—O4176.4 (3)
C14—Zn1—N3—C1988.3 (2)N4—Zn1—C14—O4−71.23 (16)
O1—Zn1—N3—C1573.6 (3)N3—Zn1—C14—O4−152.83 (15)
O3—Zn1—N3—C15−73.4 (3)O1—Zn1—C14—O3−126.29 (17)
N4—Zn1—N3—C15179.1 (3)N4—Zn1—C14—O3112.32 (16)
O4—Zn1—N3—C15−113.5 (3)N3—Zn1—C14—O330.7 (2)
C14—Zn1—N3—C15−88.4 (3)O4—Zn1—C14—O3−176.4 (3)
O1—Zn1—N4—C24−77.9 (2)O1—Zn1—C14—C8−153.8 (8)
O3—Zn1—N4—C2487.8 (2)O3—Zn1—C14—C8−27.5 (8)
N3—Zn1—N4—C24−178.2 (2)N4—Zn1—C14—C884.8 (8)
O4—Zn1—N4—C2430.9 (2)N3—Zn1—C14—C83.2 (9)
C14—Zn1—N4—C2458.5 (2)O4—Zn1—C14—C8156.1 (9)
O1—Zn1—N4—C20103.27 (18)C19—N3—C15—C16−0.5 (5)
O3—Zn1—N4—C20−91.02 (18)Zn1—N3—C15—C16176.0 (3)
N3—Zn1—N4—C202.95 (17)N3—C15—C16—C17−0.7 (7)
O4—Zn1—N4—C20−147.95 (18)C15—C16—C17—C181.0 (7)
C14—Zn1—N4—C20−120.34 (18)C16—C17—C18—C19−0.2 (6)
C6—C1—C2—C30.6 (4)C15—N3—C19—C181.3 (4)
C7—C1—C2—C3−178.3 (2)Zn1—N3—C19—C18−175.6 (2)
C1—C2—C3—C4−0.3 (4)C15—N3—C19—C20−178.2 (3)
C2—C3—C4—N1−178.9 (3)Zn1—N3—C19—C204.9 (3)
C2—C3—C4—C5−0.6 (4)C17—C18—C19—N3−0.9 (5)
N1—C4—C5—C6179.6 (2)C17—C18—C19—C20178.5 (3)
C3—C4—C5—C61.3 (4)C24—N4—C20—C211.3 (4)
C4—C5—C6—C1−1.1 (4)Zn1—N4—C20—C21−179.8 (2)
C2—C1—C6—C50.1 (4)C24—N4—C20—C19179.7 (2)
C7—C1—C6—C5179.0 (2)Zn1—N4—C20—C19−1.4 (3)
Zn1—O1—C7—O22.4 (3)N3—C19—C20—N4−2.4 (3)
Zn1—O1—C7—C1−177.28 (15)C18—C19—C20—N4178.1 (3)
C2—C1—C7—O2−13.1 (4)N3—C19—C20—C21176.0 (3)
C6—C1—C7—O2168.1 (3)C18—C19—C20—C21−3.5 (4)
C2—C1—C7—O1166.6 (2)N4—C20—C21—C22−0.7 (5)
C6—C1—C7—O1−12.2 (3)C19—C20—C21—C22−179.0 (3)
C13—C8—C9—C10−1.5 (4)C20—C21—C22—C230.0 (6)
C14—C8—C9—C10179.0 (2)C21—C22—C23—C240.1 (6)
C8—C9—C10—C111.2 (4)C20—N4—C24—C23−1.2 (4)
C9—C10—C11—C120.0 (4)Zn1—N4—C24—C23−180.0 (2)
C9—C10—C11—N2−176.5 (2)C22—C23—C24—N40.5 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···N2i0.882.333.202 (4)169.
N1—H1E···O2ii0.882.363.181 (4)155.
N2—H2E···O2iii0.882.283.116 (4)159.
Symmetry codes: (i) x−2, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y, −z+1.
Table 1
Selected geometric parameters (Å) top
Zn1—O11.9269 (18)Zn1—N32.124 (2)
Zn1—O31.9704 (18)Zn1—N42.088 (2)
Zn1—O42.395 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···N2i0.882.333.202 (4)169.
N1—H1E···O2ii0.882.363.181 (4)155.
N2—H2E···O2iii0.882.283.116 (4)159.
Symmetry codes: (i) x−2, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y, −z+1.
Acknowledgements top

This work was supported by the Education Department Foundation of Fujian Province of China (grant No. JK2011042).

references
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