supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers buy article online

Acta Cryst. (2007). E63, m1712    [ doi:10.1107/S1600536807023604 ]

Bis(benzimidazole-[kappa]N)bis(4-formylbenzoato-[kappa]O)zinc(II) monohydrate

Z.-P. Deng, S. Gao and S. W. Ng

Abstract top

The zinc center in the title compound, [Zn(C8H5O3)2(C7H6N2)2]·H2O, shows tetrahedral coordination. The molecules are linked by N-H...O and O-H...O hydrogen bonds. One of the two formylbenzoate ligands is disordered, approximately equally, over two positions.

Comment top

Bis(4-formylbenzoato)zinc, which exists as a tetrahedral diaqua compound (Deng et al., 2006a), form a five-coordinate aqua complex with phenathroline (Deng et al., 2006b). The title compound is a 1:2 adduct of Bis(4-formylbenzoato)zinc with benzimidazole, crystallizing with a molecule of water (I). The metal center shows tetrahedral coordination (Fig. 1). Adjacent molecules are linked by hydrogen bonds.

Related literature top

For the diaqua complex, see Deng et al., 2006a, and for the aqua phenanthroline adduct, see Deng et al., 2006b.

Experimental top

Zinc diacetate dihydrate (0.11 g, 0.5 mmol) was added to a 1:1 aqueous-ethanol solution (20 ml) of 4-formylbenzoic acid (0.15 g, 1 mmol) and benzimidazole (0.07 g, 1 mmol). Sodium hydroxide was added to a pH value of about 5. The filtered solution was set aside for the formation of colorless prismatic crystals. CH&N analysis. Calculated for C30H24N4O7Zn: C 58.31, H 3.91, N 9.07%. Found: C 58.28, H 3.93, N 9.04%.

Refinement top

One of the two formylbenzoate anions is disordered over two positions; the occupancy factors refined to 0.535 (5):0.465 (5). For both components, the phenylene ring was refined as a rigid hexagon of 1.39Å sides. The C–C single-bond length was restrained to 1.50±0.01Å and the C=O double-bond distance to 1.25±0.01 Å. The Caliphatic···Cortho distances were restrained to 2.50±0.01 Å and the entire anion was restrained to be planar. As the C8 atom is less than 0.2 Å from C8', the temperature factors were restrained to be identical; those of the O3 and O3' were similarly treated for the same reason. Additionally, the disordered atoms were restrained to be nearly isotropic. A consideration of the hydrogen bonding distances led to pairing the O1w' water molecule with the primed anion.

The carbon- and nitrogen bound H atoms were generated geometrically (C–H 0.93, N–H 0.86 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The water H atoms could were placed in chemically sensible positions on the basis of hydrogen bonding interactions but they were not refined.

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the molecular structure of (I). Only one of the disorder components is shown. Displacement ellipsoids are drawn at the 50% probability level, and H atoms are drawn as spheres of arbitrary radii.
Bis(benzimidazole-κN)bis(4-formylbenzoato-κO)\ zinc(II) monohydrate top
Crystal data top
[Zn(C8H5O3)2(C7H6N2)2].H2OF(000) = 2544
Mr = 617.90Dx = 1.465 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 13980 reflections
a = 13.7968 (8) Åθ = 3.1–27.5°
b = 17.0524 (8) ŵ = 0.93 mm−1
c = 23.848 (1) ÅT = 295 K
β = 92.954 (1)°Prism, colourless
V = 5603.1 (5) Å30.35 × 0.26 × 0.19 mm
Z = 8
Data collection top
Rigaku RAXIS-RAPID IP
diffractometer		6393 independent reflections
Radiation source: fine-focus sealed tube3298 reflections with I > 2σ(I)
graphiteRint = 0.068
ω scanθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −17→17
Tmin = 0.558, Tmax = 0.843k = −21→22
27096 measured reflectionsl = −30→30
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.194 w = 1/[σ2(Fo2) + (0.0884P)2 + 4.8786P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
6393 reflectionsΔρmax = 0.70 e Å−3
453 parametersΔρmin = −0.67 e Å−3
178 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0008 (2)
Crystal data top
[Zn(C8H5O3)2(C7H6N2)2].H2OV = 5603.1 (5) Å3
Mr = 617.90Z = 8
Monoclinic, C2/cMo Kα radiation
a = 13.7968 (8) ŵ = 0.93 mm−1
b = 17.0524 (8) ÅT = 295 K
c = 23.848 (1) Å0.35 × 0.26 × 0.19 mm
β = 92.954 (1)°
Data collection top
Rigaku RAXIS-RAPID IP
diffractometer		6393 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		3298 reflections with I > 2σ(I)
Tmin = 0.558, Tmax = 0.843Rint = 0.068
27096 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.194Δρmax = 0.70 e Å−3
S = 1.09Δρmin = −0.67 e Å−3
6393 reflectionsAbsolute structure: ?
453 parametersFlack parameter: ?
178 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.28971 (4)0.59229 (3)0.38356 (2)0.0525 (2)
N10.2248 (3)0.4871 (2)0.36616 (14)0.0554 (9)
N20.1303 (3)0.4014 (2)0.32177 (19)0.0726 (12)
H2n0.08680.38300.29820.087*
N30.2451 (3)0.6254 (2)0.45870 (14)0.0522 (9)
N40.2390 (3)0.6728 (2)0.54477 (15)0.0606 (10)
H4n0.25870.69090.57700.073*
O40.2136 (3)0.64849 (19)0.32459 (13)0.0658 (9)
O50.2842 (3)0.7626 (2)0.34589 (14)0.0768 (10)
O6−0.0635 (3)0.8200 (3)0.10574 (17)0.1046 (15)
O10.4180 (6)0.5925 (4)0.3560 (4)0.079 (2)0.535 (5)
O20.4492 (6)0.5579 (4)0.4422 (4)0.103 (3)0.535 (5)
O30.9173 (18)0.5162 (7)0.3088 (8)0.098 (2)0.535 (5)
O1w0.4534 (8)0.7360 (6)0.2980 (5)0.141 (4)0.535 (5)
H1w10.45690.69040.31150.169*0.535 (5)
H1w20.40050.75680.30890.169*0.535 (5)
C10.4754 (5)0.5692 (3)0.3940 (4)0.072 (4)0.535 (5)
C20.5795 (4)0.5542 (3)0.3815 (3)0.061 (3)0.535 (5)
C70.6133 (5)0.5658 (3)0.3283 (2)0.054 (3)0.535 (5)
H70.57120.58330.29920.064*0.535 (5)
C60.7101 (5)0.5513 (4)0.3184 (3)0.051 (2)0.535 (5)
H60.73270.55900.28270.061*0.535 (5)
C50.7731 (4)0.5251 (5)0.3618 (4)0.059 (4)0.535 (5)
C40.7393 (5)0.5135 (5)0.4150 (3)0.065 (3)0.535 (5)
H40.78140.49590.44410.078*0.535 (5)
C30.6425 (6)0.5280 (4)0.4249 (2)0.069 (3)0.535 (5)
H30.61990.52020.46060.083*0.535 (5)
C80.8764 (6)0.5092 (6)0.3522 (6)0.078 (2)0.535 (5)
H80.91430.49180.38310.094*0.535 (5)
O1'0.4345 (9)0.5846 (5)0.3997 (5)0.090 (3)0.465 (5)
O2'0.4298 (7)0.6000 (5)0.3094 (5)0.116 (4)0.465 (5)
O3'0.915 (2)0.4944 (9)0.3035 (9)0.098 (2)0.465 (3)
O1w'0.4547 (5)0.8194 (4)0.2757 (3)0.061 (2)0.465 (5)
H1w30.41270.82260.30090.073*0.465 (5)
H1w40.46510.77060.26920.073*0.465 (5)
C1'0.4733 (6)0.5834 (4)0.3539 (4)0.077 (4)0.465 (5)
C2'0.5783 (5)0.5604 (3)0.3534 (4)0.074 (4)0.465 (5)
C7'0.6228 (6)0.5587 (5)0.3025 (3)0.094 (5)0.465 (5)
H7'0.58760.57170.26940.113*0.465 (5)
C6'0.7200 (6)0.5377 (5)0.3009 (4)0.067 (4)0.465 (5)
H6'0.74980.53650.26680.081*0.465 (5)
C5'0.7725 (5)0.5183 (6)0.3502 (5)0.058 (4)0.465 (5)
C4'0.7280 (7)0.5200 (6)0.4011 (4)0.072 (4)0.465 (5)
H4'0.76320.50710.43420.086*0.465 (5)
C3'0.6308 (6)0.5411 (5)0.4028 (3)0.072 (4)0.465 (5)
H3'0.60100.54220.43680.087*0.465 (5)
C8'0.8763 (7)0.4958 (8)0.3482 (7)0.078 (2)0.465
H8'0.91170.48280.38120.094*0.465 (5)
C90.2289 (4)0.7213 (3)0.31636 (18)0.0580 (12)
C100.1726 (3)0.7564 (3)0.26685 (17)0.0531 (11)
C110.1190 (4)0.7085 (3)0.22931 (19)0.0687 (14)
H110.12110.65440.23380.082*
C120.0636 (4)0.7405 (3)0.1862 (2)0.0707 (14)
H120.02910.70810.16100.085*
C130.0587 (4)0.8214 (3)0.17986 (18)0.0588 (12)
C140.1134 (4)0.8688 (3)0.2157 (2)0.0605 (12)
H140.11170.92290.21070.073*
C150.1708 (3)0.8370 (3)0.25929 (18)0.0578 (12)
H150.20790.86950.28330.069*
C16−0.0066 (4)0.8548 (4)0.1356 (2)0.0796 (16)
H16−0.00320.90870.13030.096*
C170.2429 (3)0.4136 (3)0.38937 (17)0.0514 (11)
C180.3076 (4)0.3910 (3)0.4323 (2)0.0693 (14)
H180.34720.42720.45160.083*
C190.3107 (5)0.3118 (4)0.4455 (3)0.094 (2)
H190.35330.29450.47430.113*
C200.2518 (5)0.2577 (4)0.4165 (3)0.096 (2)
H200.25620.20500.42640.115*
C210.1878 (4)0.2798 (3)0.3739 (3)0.0748 (15)
H210.14860.24350.35460.090*
C220.1838 (4)0.3586 (3)0.36096 (19)0.0569 (11)
C230.1566 (4)0.4757 (3)0.3263 (2)0.0722 (15)
H230.12990.51560.30380.087*
C240.1479 (3)0.6321 (3)0.47185 (17)0.0517 (11)
C250.0638 (4)0.6154 (3)0.4404 (2)0.0715 (14)
H250.06560.59640.40390.086*
C26−0.0223 (4)0.6278 (4)0.4648 (2)0.0824 (16)
H26−0.08010.61740.44430.099*
C27−0.0258 (4)0.6556 (4)0.5192 (2)0.0814 (16)
H27−0.08580.66150.53470.098*
C280.0567 (4)0.6746 (3)0.5511 (2)0.0720 (15)
H280.05410.69480.58720.086*
C290.1443 (4)0.6621 (3)0.52625 (17)0.0541 (11)
C300.2954 (4)0.6502 (2)0.50375 (18)0.0559 (11)
H300.36280.65170.50670.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0559 (4)0.0557 (3)0.0447 (3)0.0063 (2)−0.0098 (2)−0.0017 (2)
N10.054 (2)0.061 (2)0.050 (2)0.0063 (18)−0.0054 (17)−0.0018 (18)
N20.072 (3)0.069 (3)0.073 (3)−0.005 (2)−0.024 (2)−0.014 (2)
N30.053 (2)0.054 (2)0.048 (2)0.0027 (17)−0.0162 (16)0.0006 (17)
N40.080 (3)0.059 (2)0.0417 (19)−0.002 (2)−0.0088 (19)−0.0067 (18)
O40.077 (2)0.061 (2)0.0581 (19)0.0088 (17)−0.0127 (16)0.0081 (16)
O50.095 (3)0.079 (2)0.0533 (19)0.006 (2)−0.0263 (18)−0.0135 (18)
O60.092 (3)0.144 (4)0.075 (3)0.020 (3)−0.029 (2)0.024 (3)
O10.071 (5)0.081 (5)0.085 (5)0.008 (4)0.012 (4)0.010 (4)
O20.102 (6)0.109 (5)0.102 (6)0.021 (4)0.035 (5)0.014 (5)
O30.077 (3)0.112 (6)0.103 (4)0.014 (5)0.003 (3)−0.003 (4)
O1w0.129 (7)0.136 (7)0.161 (7)−0.003 (6)0.038 (6)0.018 (6)
C10.090 (8)0.053 (5)0.073 (7)0.003 (5)0.015 (6)−0.004 (5)
C20.060 (6)0.062 (5)0.058 (6)−0.003 (5)−0.014 (5)−0.020 (5)
C70.045 (5)0.044 (4)0.068 (6)−0.006 (4)−0.029 (5)−0.009 (4)
C60.058 (6)0.047 (5)0.045 (5)−0.002 (4)−0.007 (4)−0.014 (4)
C50.048 (7)0.054 (6)0.073 (6)−0.006 (5)−0.017 (5)−0.005 (5)
C40.065 (6)0.067 (6)0.061 (5)−0.010 (5)−0.016 (5)0.003 (5)
C30.073 (7)0.071 (6)0.063 (6)0.002 (5)−0.002 (5)−0.002 (5)
C80.070 (4)0.075 (4)0.089 (4)0.004 (3)−0.009 (3)0.007 (3)
O1'0.093 (7)0.091 (6)0.089 (7)−0.002 (5)0.015 (6)−0.007 (5)
O2'0.078 (6)0.163 (8)0.104 (7)0.030 (5)−0.014 (5)−0.027 (6)
O3'0.077 (3)0.112 (6)0.103 (4)0.014 (5)0.003 (3)−0.003 (4)
O1w'0.055 (4)0.058 (4)0.069 (4)−0.008 (3)0.000 (3)0.000 (3)
C1'0.075 (8)0.079 (7)0.075 (7)0.028 (6)−0.003 (6)−0.014 (6)
C2'0.065 (7)0.069 (7)0.088 (9)0.011 (6)0.000 (7)−0.006 (6)
C7'0.087 (8)0.108 (8)0.086 (8)0.014 (7)−0.002 (7)−0.007 (7)
C6'0.064 (7)0.072 (7)0.065 (7)0.007 (5)−0.002 (5)−0.014 (6)
C5'0.052 (8)0.058 (7)0.063 (6)−0.003 (6)−0.011 (5)−0.001 (6)
C4'0.068 (8)0.069 (7)0.075 (7)−0.006 (6)−0.023 (6)0.009 (6)
C3'0.069 (8)0.077 (7)0.071 (7)−0.026 (6)0.012 (6)−0.003 (6)
C8'0.070 (4)0.075 (4)0.089 (4)0.004 (3)−0.009 (3)0.007 (3)
C90.064 (3)0.065 (3)0.044 (2)0.015 (2)−0.006 (2)−0.006 (2)
C100.060 (3)0.056 (3)0.043 (2)0.013 (2)−0.003 (2)0.000 (2)
C110.091 (4)0.056 (3)0.056 (3)0.013 (3)−0.023 (3)−0.005 (2)
C120.082 (4)0.077 (3)0.051 (3)0.010 (3)−0.023 (2)−0.005 (3)
C130.056 (3)0.076 (3)0.045 (2)0.017 (2)0.003 (2)0.012 (2)
C140.058 (3)0.063 (3)0.061 (3)0.009 (2)0.004 (2)0.014 (2)
C150.057 (3)0.065 (3)0.050 (2)0.000 (2)0.000 (2)0.004 (2)
C160.070 (4)0.105 (5)0.063 (3)0.023 (3)−0.005 (3)0.022 (3)
C170.055 (3)0.058 (3)0.042 (2)0.012 (2)0.0107 (19)0.000 (2)
C180.075 (4)0.076 (3)0.057 (3)0.003 (3)−0.001 (3)0.008 (3)
C190.098 (5)0.096 (5)0.089 (4)0.014 (4)−0.005 (4)0.036 (4)
C200.099 (5)0.072 (4)0.118 (5)0.004 (4)0.024 (4)0.029 (4)
C210.075 (4)0.064 (3)0.087 (4)−0.007 (3)0.023 (3)−0.005 (3)
C220.058 (3)0.060 (3)0.053 (3)−0.002 (2)0.010 (2)−0.009 (2)
C230.085 (4)0.062 (3)0.066 (3)0.004 (3)−0.030 (3)−0.005 (3)
C240.053 (3)0.054 (3)0.047 (2)0.003 (2)−0.009 (2)0.001 (2)
C250.059 (3)0.092 (4)0.062 (3)0.001 (3)−0.006 (3)−0.018 (3)
C260.058 (4)0.108 (4)0.081 (4)0.000 (3)−0.006 (3)−0.012 (3)
C270.072 (4)0.105 (5)0.068 (3)0.003 (3)0.015 (3)−0.003 (3)
C280.086 (4)0.081 (4)0.048 (3)0.011 (3)0.006 (3)0.001 (3)
C290.064 (3)0.056 (3)0.041 (2)0.000 (2)−0.004 (2)−0.001 (2)
C300.067 (3)0.050 (2)0.050 (2)−0.002 (2)−0.014 (2)0.002 (2)
Geometric parameters (Å, °) top
Zn1—O11.919 (9)C7'—H7'0.9300
Zn1—O41.961 (3)C6'—C5'1.3900
Zn1—N32.006 (4)C6'—H6'0.9300
Zn1—O1'2.020 (13)C5'—C4'1.3900
Zn1—N12.038 (4)C5'—C8'1.485 (6)
N1—C231.316 (6)C4'—C3'1.3900
N1—C171.387 (5)C4'—H4'0.9300
N2—C231.321 (6)C3'—H3'0.9300
N2—C221.372 (6)C8'—H8'0.9300
N2—H2n0.8600C9—C101.504 (6)
N3—C301.318 (5)C10—C151.386 (6)
N3—C241.397 (6)C10—C111.395 (6)
N4—C301.338 (6)C11—C121.362 (6)
N4—C291.370 (6)C11—H110.9300
N4—H4n0.8600C12—C131.389 (7)
O4—C91.276 (6)C12—H120.9300
O5—C91.232 (6)C13—C141.374 (7)
O6—C161.190 (7)C13—C161.468 (7)
O1—C11.237 (8)C14—C151.385 (6)
O2—C11.239 (8)C14—H140.9300
O3—C81.209 (8)C15—H150.9300
O1w—H1w10.842C16—H160.9300
O1w—H1w20.864C17—C181.379 (7)
C1—C21.504 (6)C17—C221.396 (6)
C2—C71.3900C18—C191.387 (7)
C2—C31.3900C18—H180.9300
C7—C61.3900C19—C201.389 (9)
C7—H70.9300C19—H190.9300
C6—C51.3900C20—C211.364 (8)
C6—H60.9300C20—H200.9300
C5—C41.3900C21—C221.378 (7)
C5—C81.481 (6)C21—H210.9300
C4—C31.3900C23—H230.9300
C4—H40.9300C24—C251.379 (6)
C3—H30.9300C24—C291.398 (6)
C8—H80.9300C25—C261.366 (8)
O1'—C1'1.241 (9)C25—H250.9300
O2'—C1'1.226 (9)C26—C271.384 (7)
O3'—C8'1.218 (9)C26—H260.9300
O1w'—H1w30.86C27—C281.375 (8)
O1w'—H1w40.86C27—H270.9300
C1'—C2'1.500 (6)C28—C291.389 (7)
C2'—C7'1.3900C28—H280.9300
C2'—C3'1.3900C30—H300.9300
C7'—C6'1.3900
O1—Zn1—O4102.9 (3)C4'—C3'—C2'120.0
O1—Zn1—N3129.5 (3)C4'—C3'—H3'120.0
O4—Zn1—N3108.97 (14)C2'—C3'—H3'120.0
O4—Zn1—O1'131.0 (3)O3'—C8'—C5'119.9 (18)
N3—Zn1—O1'101.2 (3)O3'—C8'—H8'120.0
O1—Zn1—N1109.6 (2)C5'—C8'—H8'120.0
O4—Zn1—N194.03 (14)O5—C9—O4124.7 (4)
N3—Zn1—N1106.12 (15)O5—C9—C10120.1 (4)
O1'—Zn1—N1113.7 (3)O4—C9—C10115.2 (4)
O1—Zn1—C126.9 (2)C15—C10—C11119.4 (4)
O4—Zn1—C1129.3 (2)C15—C10—C9120.1 (4)
N3—Zn1—C1107.7 (2)C11—C10—C9120.4 (4)
N1—Zn1—C1107.95 (15)C12—C11—C10120.5 (5)
C23—N1—C17105.1 (4)C12—C11—H11119.7
C23—N1—Zn1124.6 (3)C10—C11—H11119.7
C17—N1—Zn1130.2 (3)C11—C12—C13120.1 (5)
C23—N2—C22108.6 (4)C11—C12—H12119.9
C23—N2—H2n125.7C13—C12—H12119.9
C22—N2—H2n125.7C14—C13—C12119.7 (4)
C30—N3—C24105.2 (4)C14—C13—C16121.1 (5)
C30—N3—Zn1130.2 (3)C12—C13—C16119.2 (5)
C24—N3—Zn1124.5 (3)C13—C14—C15120.7 (4)
C30—N4—C29107.9 (4)C13—C14—H14119.6
C30—N4—H4n126.1C15—C14—H14119.6
C29—N4—H4n126.1C14—C15—C10119.5 (4)
C9—O4—Zn1119.9 (3)C14—C15—H15120.3
C1—O1—Zn1108.4 (7)C10—C15—H15120.3
H1w1—O1w—H1w2107.3O6—C16—C13126.8 (6)
O1—C1—O2121.5 (9)O6—C16—H16116.6
O1—C1—C2119.5 (7)C13—C16—H16116.6
O2—C1—C2118.9 (7)C18—C17—N1130.2 (5)
C7—C2—C3120.0C18—C17—C22120.8 (4)
C7—C2—C1121.6 (4)N1—C17—C22109.0 (4)
C3—C2—C1118.4 (4)C17—C18—C19116.9 (5)
C2—C7—C6120.0C17—C18—H18121.6
C2—C7—H7120.0C19—C18—H18121.6
C6—C7—H7120.0C18—C19—C20121.6 (6)
C7—C6—C5120.0C18—C19—H19119.2
C7—C6—H6120.0C20—C19—H19119.2
C5—C6—H6120.0C21—C20—C19121.7 (6)
C6—C5—C4120.0C21—C20—H20119.1
C6—C5—C8120.9 (5)C19—C20—H20119.1
C4—C5—C8119.1 (5)C20—C21—C22117.0 (6)
C3—C4—C5120.0C20—C21—H21121.5
C3—C4—H4120.0C22—C21—H21121.5
C5—C4—H4120.0N2—C22—C21133.3 (5)
C4—C3—C2120.0N2—C22—C17104.6 (4)
C4—C3—H3120.0C21—C22—C17122.1 (5)
C2—C3—H3120.0N1—C23—N2112.6 (4)
O3—C8—C5127.5 (16)N1—C23—H23123.7
O3—C8—H8116.2N2—C23—H23123.7
C5—C8—H8116.2C25—C24—N3130.7 (4)
C1'—O1'—Zn1107.5 (9)C25—C24—C29120.7 (5)
H1w3—O1w'—H1w4108.2N3—C24—C29108.6 (4)
O2'—C1'—O1'123.0 (11)C26—C25—C24117.6 (5)
O2'—C1'—C2'118.9 (8)C26—C25—H25121.2
O1'—C1'—C2'118.2 (9)C24—C25—H25121.2
C7'—C2'—C3'120.0C25—C26—C27121.7 (6)
C7'—C2'—C1'118.9 (5)C25—C26—H26119.2
C3'—C2'—C1'121.1 (5)C27—C26—H26119.2
C6'—C7'—C2'120.0C28—C27—C26122.1 (5)
C6'—C7'—H7'120.0C28—C27—H27118.9
C2'—C7'—H7'120.0C26—C27—H27118.9
C7'—C6'—C5'120.0C27—C28—C29116.2 (5)
C7'—C6'—H6'120.0C27—C28—H28121.9
C5'—C6'—H6'120.0C29—C28—H28121.9
C6'—C5'—C4'120.0N4—C29—C28132.7 (4)
C6'—C5'—C8'119.8 (5)N4—C29—C24105.6 (4)
C4'—C5'—C8'120.2 (5)C28—C29—C24121.7 (5)
C3'—C4'—C5'120.0N3—C30—N4112.7 (4)
C3'—C4'—H4'120.0N3—C30—H30123.6
C5'—C4'—H4'120.0N4—C30—H30123.6
O1—Zn1—N1—C23−104.9 (5)O4—C9—C10—C15169.3 (4)
O4—Zn1—N1—C230.3 (4)O5—C9—C10—C11172.2 (5)
N3—Zn1—N1—C23111.4 (4)O4—C9—C10—C11−8.4 (7)
O1'—Zn1—N1—C23−138.3 (5)C15—C10—C11—C12−1.4 (8)
C1—Zn1—N1—C23−133.3 (4)C9—C10—C11—C12176.3 (5)
O1—Zn1—N1—C1771.5 (5)C10—C11—C12—C13−1.1 (8)
O4—Zn1—N1—C17176.7 (4)C11—C12—C13—C142.9 (8)
N3—Zn1—N1—C17−72.2 (4)C11—C12—C13—C16−175.7 (5)
O1'—Zn1—N1—C1738.1 (5)C12—C13—C14—C15−2.2 (7)
C1—Zn1—N1—C1743.1 (4)C16—C13—C14—C15176.5 (4)
O1—Zn1—N3—C30−3.3 (5)C13—C14—C15—C10−0.4 (7)
O4—Zn1—N3—C30−129.4 (4)C11—C10—C15—C142.1 (7)
O1'—Zn1—N3—C3011.5 (5)C9—C10—C15—C14−175.6 (4)
N1—Zn1—N3—C30130.5 (4)C14—C13—C16—O6−172.6 (6)
C1—Zn1—N3—C3015.0 (4)C12—C13—C16—O66.1 (9)
O1—Zn1—N3—C24171.5 (4)C23—N1—C17—C18179.7 (5)
O4—Zn1—N3—C2445.4 (4)Zn1—N1—C17—C182.7 (7)
O1'—Zn1—N3—C24−173.7 (4)C23—N1—C17—C221.0 (5)
N1—Zn1—N3—C24−54.8 (3)Zn1—N1—C17—C22−176.0 (3)
C1—Zn1—N3—C24−170.2 (3)N1—C17—C18—C19−178.5 (5)
O1—Zn1—O4—C9−67.1 (4)C22—C17—C18—C190.1 (7)
N3—Zn1—O4—C973.1 (4)C17—C18—C19—C200.3 (9)
O1'—Zn1—O4—C9−51.7 (5)C18—C19—C20—C21−0.2 (10)
N1—Zn1—O4—C9−178.3 (3)C19—C20—C21—C22−0.2 (9)
C1—Zn1—O4—C9−61.1 (4)C23—N2—C22—C21−178.5 (5)
O4—Zn1—O1—C1169.7 (3)C23—N2—C22—C170.7 (5)
N3—Zn1—O1—C141.4 (4)C20—C21—C22—N2179.7 (5)
O1'—Zn1—O1—C112.5 (6)C20—C21—C22—C170.6 (8)
N1—Zn1—O1—C1−91.2 (3)C18—C17—C22—N2−179.9 (4)
Zn1—O1—C1—O2−7.5 (3)N1—C17—C22—N2−1.0 (5)
Zn1—O1—C1—C2172.5 (3)C18—C17—C22—C21−0.6 (7)
O1—C1—C2—C7−0.03 (7)N1—C17—C22—C21178.3 (4)
O2—C1—C2—C7−179.99 (4)C17—N1—C23—N2−0.5 (6)
Zn1—C1—C2—C718.3 (8)Zn1—N1—C23—N2176.6 (3)
O1—C1—C2—C3180.00 (4)C22—N2—C23—N1−0.1 (6)
O2—C1—C2—C30.04 (7)C30—N3—C24—C25179.3 (5)
Zn1—C1—C2—C3−161.7 (8)Zn1—N3—C24—C253.4 (7)
C6—C5—C8—O30.04 (9)C30—N3—C24—C290.3 (5)
C4—C5—C8—O3−179.97 (5)Zn1—N3—C24—C29−175.6 (3)
O1—Zn1—O1'—C1'−6.3 (5)N3—C24—C25—C26179.9 (5)
O4—Zn1—O1'—C1'−36.2 (5)C29—C24—C25—C26−1.2 (8)
N3—Zn1—O1'—C1'−163.9 (3)C24—C25—C26—C27−0.5 (9)
N1—Zn1—O1'—C1'82.7 (4)C25—C26—C27—C282.2 (10)
C1—Zn1—O1'—C1'43 (3)C26—C27—C28—C29−2.0 (9)
Zn1—O1'—C1'—O2'13.1 (3)C30—N4—C29—C28179.2 (5)
Zn1—O1'—C1'—C2'−166.9 (3)C30—N4—C29—C24−0.2 (5)
O2'—C1'—C2'—C7'−0.03 (7)C27—C28—C29—N4−179.1 (5)
O1'—C1'—C2'—C7'−179.99 (4)C27—C28—C29—C240.3 (7)
O2'—C1'—C2'—C3'180.00 (4)C25—C24—C29—N4−179.1 (4)
O1'—C1'—C2'—C3'0.04 (7)N3—C24—C29—N40.0 (5)
C1'—C2'—C3'—C4'179.97 (5)C25—C24—C29—C281.4 (7)
C6'—C5'—C8'—O3'0.03 (8)N3—C24—C29—C28−179.5 (4)
C4'—C5'—C8'—O3'−179.98 (4)C24—N3—C30—N4−0.5 (5)
Zn1—O4—C9—O5−5.9 (7)Zn1—N3—C30—N4175.1 (3)
Zn1—O4—C9—C10174.8 (3)C29—N4—C30—N30.5 (5)
O5—C9—C10—C15−10.1 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2n···O1w'i0.862.122.907 (8)152
N2—H2n···O1w'ii0.862.172.960 (8)154
N4—H4n···O5iii0.862.112.864 (5)145
O1w—H1w1···O10.842.064 (7)2.87 (1)159
O1w—H1w2···O50.861.873 (4)2.69 (1)157
O1w'—H1w3···O50.862.353 (4)3.112 (8)148
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, y−1/2, z; (iii) −x+1/2, −y+3/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2n···O1w'i0.862.122.907 (8)152
N2—H2n···O1w'ii0.862.172.960 (8)154
N4—H4n···O5iii0.862.112.864 (5)145
O1w—H1w1···O10.842.064 (7)2.87 (1)159
O1w—H1w2···O50.861.873 (4)2.69 (1)157
O1w'—H1w3···O50.862.353 (4)3.112 (8)148
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, y−1/2, z; (iii) −x+1/2, −y+3/2, −z+1.
Acknowledgements top

We thank the Heilongjiang Province Natural Science Foundation (No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (No. 1054 G036) and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Deng, Z.-P., Gao, S., Huo, L.-H. & Zhao, H. (2006a). Acta Cryst. E62, m3524–m3526.

Deng, Z.-P., Gao, S., Huo, L.-H. & Zhao, H. (2006b). Acta Cryst. E62, m3527–m3529.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Rigaku Corporation (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc. The Woodlands, Texas, USA.

Sheldrick, G. M. (1997). SHELXS and SHELXL97. University of Göttingen, Germany.

Westrip, S. P. (2006). publCIF. In preparation.