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Acta Cryst. (2007). E63, m1797    [ doi:10.1107/S1600536807026037 ]

{[N,N'-Bis(4-methoxybenzyl)ethane-1,2-diyldiimino]diacetato-[kappa]4O,N,N',O'}bis(1H-imidazole-[kappa]N3)zinc(II)

M. Zhang, H.-L. Weng, B. Hu and X.-M. Xu

Abstract top

In the title complex, [Zn(C22H26N2O6)(C3H4N2)2], the ZnII atom is in a distorted octahedral coordination environment defined by the bond lengths and angles formed by an N4O2 donor set. In the crystal structure, intermolecular N-H...O hydrogen bonds link molecules into chains of rings. The atoms of one 4-methoxybenzyl group are disordered over two sites in approximately a 0.7:0.3 ratio.

Comment top

This work is a part of a study of the synthesis and structural characterization of metal complexes with the [N,N'-bis(4-methoxybenzyl) ethane-1,2-diyldiimino]diacetate ligand. In this paper, we report the structure of a new Zn(II) complex, Zn(La)(Lb)2(La=[N,N'-bis(4-methoxybenzyl) ethane-1,2-diyldiimino]diacetate, Lb=imidazole)(1). In (1) (Fig 1), the ZnII atom is in a distorted octahedral coordination environment defined by a N4O2 donor set, from two amine N atoms (N1,N2), two carboxyl O atoms (O2,O5), and two imidazole N atoms (N3, N5). In the crystal structure (Fig 2), C—H···O and N—H···O hydrogen bonds (Table 2) consolidate the crystal packing into a chain of rings.

Related literature top

We have recently determined the structure of the NiII analog of the title compound (Zhang et al., 2007).

For related literature, see: Suresh et al. (2006).

Experimental top

The title complex was prepared according to the literature method (Zhang et al., 2007). Crystals were obtained by slow evaporation (one month) of a methanol solution (15 ml) of the title complex (0.06 g,0.1 mmol).

Refinement top

H atoms bound to C atoms were placed in calculated positions and refined in the riding-model approximation, with C—H = 0.93–97Å and Uiso(H) = 1.2Ueq(C) or C—H = 0.96Å and Uiso (H) = 1.5Ueq(C) for the methyl groups. Similarly H atoms bonded to N atoms were refined with N—H = 0.86 Å, and Uiso(H) = 1.2Ueq(N). The atoms of the 4-methoxybenzyl group were refined as disordered over two sites with refined occupancies 0.706 (8) and 0.294 (4) for the major and minor components. The largest peak in the final difference Fourier of 1.278 e A°−3 is located 1.87Å from atom H11B. During the refinement of the structure, electron density peaks were located that were believed to be highly disordered solvent molecules (possibly methanol). Attempts made to model the solvent molecule were not successful. The SQUEEZE option in PLATON (Spek, 2003) indicated there was a solvent cavity of volume 98 Å3 containing approximately 18 electrons. In the final cycles of refinement, this contribution to the electron density was removed from the observed data. The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003). A similar treatment of disordered solvent molecules was carried out by (Suresh et al., 2006; and references cited threin)

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound. Dashed lines denote hydrogen bonds.
{[N,N'-Bis(4-methoxybenzyl)ethane-1,2-diyldiimino]diacetato- κ4O,N,N',O'}bis(1H-imidazole-κN3)zinc(II) top
Crystal data top
[Zn(C22H26N2O6)(C3H4N2)2]F000 = 2576
Mr = 615.98Dx = 1.309 Mg m−3
Orthorhombic, PcabMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2bc 2acCell parameters from 9349 reflections
a = 15.3277 (6) Åθ = 2.5–23.3º
b = 16.3989 (6) ŵ = 0.83 mm−1
c = 24.8735 (10) ÅT = 299 (2) K
V = 6252.1 (4) Å3Block, colorless
Z = 80.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD
diffractometer		6826 independent reflections
Radiation source: fine-focus sealed tube3459 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.098
T = 299(2) Kθmax = 27.0º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −19→19
Tmin = 0.851, Tmax = 0.921k = −20→20
67264 measured reflectionsl = −31→31
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)] = 0.054H-atom parameters constrained
wR(F2) = 0.147  w = 1/[σ2(Fo2) + (0.0892P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.86(Δ/σ)max = 0.002
6826 reflectionsΔρmax = 1.28 e Å−3
424 parametersΔρmin = −0.45 e Å−3
53 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Zn(C22H26N2O6)(C3H4N2)2]V = 6252.1 (4) Å3
Mr = 615.98Z = 8
Orthorhombic, PcabMo Kα
a = 15.3277 (6) ŵ = 0.83 mm−1
b = 16.3989 (6) ÅT = 299 (2) K
c = 24.8735 (10) Å0.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD
diffractometer		6826 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3459 reflections with I > 2σ(I)
Tmin = 0.851, Tmax = 0.921Rint = 0.098
67264 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05453 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 0.86Δρmax = 1.28 e Å−3
6826 reflectionsΔρmin = −0.45 e Å−3
424 parameters
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*/UeqOcc. (<1)
Zn10.872846 (19)0.15880 (2)0.249200 (12)0.05098 (14)
O11.0598 (3)−0.2030 (3)0.4822 (2)0.1087 (18)0.706 (8)
C11.1068 (5)−0.2738 (5)0.4709 (3)0.126 (3)0.706 (8)
H1A1.0758−0.30550.44470.188*0.706 (8)
H1B1.1138−0.30510.50320.188*0.706 (8)
H1C1.1631−0.25940.45690.188*0.706 (8)
C21.0426 (3)−0.1459 (3)0.4402 (2)0.0715 (17)0.706 (8)
C31.0004 (4)−0.0748 (3)0.45597 (16)0.108 (3)0.706 (8)
H30.9875−0.06610.49210.130*0.706 (8)
C40.9776 (5)−0.0166 (3)0.4178 (2)0.102 (3)0.706 (8)
H40.94940.03100.42840.122*0.706 (8)
C50.9970 (4)−0.0296 (3)0.36391 (19)0.061 (2)0.706 (8)
C61.0391 (3)−0.1007 (3)0.34812 (17)0.0608 (14)0.706 (8)
H61.0521−0.10940.31200.073*0.706 (8)
C71.0619 (3)−0.1589 (2)0.3863 (2)0.0652 (17)0.706 (8)
H71.0901−0.20650.37570.078*0.706 (8)
O1'1.0884 (9)−0.2337 (7)0.4386 (5)0.152 (6)0.294 (8)
C1'1.1133 (19)−0.220 (2)0.4934 (7)0.170 (12)0.294 (8)
H1'11.1421−0.16780.49620.254*0.294 (8)
H1'21.1522−0.26200.50500.254*0.294 (8)
H1'31.0622−0.21960.51580.254*0.294 (8)
C2'1.0549 (7)−0.1642 (5)0.4130 (5)0.063 (5)0.294 (8)
C3'1.0248 (9)−0.0965 (7)0.4410 (4)0.075 (4)0.294 (8)
H3'1.0174−0.09910.47810.091*0.294 (8)
C4'1.0059 (10)−0.0248 (6)0.4136 (5)0.076 (5)0.294 (8)
H4'0.98580.02060.43240.091*0.294 (8)
C5'1.0169 (11)−0.0208 (7)0.3582 (5)0.050 (4)0.294 (8)
C6'1.0470 (11)−0.0886 (9)0.3302 (4)0.124 (8)0.294 (8)
H6'1.0543−0.08590.29320.148*0.294 (8)
C7'1.0659 (8)−0.1603 (6)0.3576 (5)0.092 (6)0.294 (8)
H7'1.0860−0.20560.33890.110*0.294 (8)
C80.98219 (17)0.04199 (18)0.32373 (13)0.0644 (8)
H8A1.00130.09240.34040.077*
H8B1.01810.03300.29210.077*
C90.83192 (19)0.07064 (18)0.35121 (12)0.0628 (8)
H9A0.86300.10460.37670.075*
H9B0.81570.02060.36940.075*
C100.74994 (19)0.11460 (19)0.33311 (13)0.0581 (7)
C110.8554 (2)−0.01970 (18)0.27802 (14)0.0645 (8)
H11A0.7923−0.01970.28020.077*
H11B0.8765−0.06880.29550.077*
C120.88233 (19)−0.02103 (18)0.21974 (14)0.0663 (9)
H12A0.9454−0.02520.21750.080*
H12B0.8576−0.06880.20250.080*
C130.76025 (17)0.04746 (19)0.17132 (12)0.0609 (8)
H13A0.72310.03750.20220.073*
H13B0.74420.10030.15680.073*
C140.74011 (17)−0.01576 (18)0.12971 (12)0.0576 (7)
C150.70541 (19)−0.09060 (19)0.14364 (12)0.0625 (8)
H150.6956−0.10220.17970.075*
C160.68473 (18)−0.14911 (18)0.10515 (13)0.0650 (8)
H160.6611−0.19910.11530.078*
C170.6999 (2)−0.1316 (2)0.05166 (13)0.0669 (8)
C180.7343 (2)−0.0585 (2)0.03745 (13)0.0862 (11)
H180.7452−0.04710.00140.103*
C190.7529 (2)−0.0013 (2)0.07575 (13)0.0797 (10)
H190.77490.04900.06500.096*
C200.6471 (3)−0.2624 (3)0.02183 (18)0.1185 (16)
H20A0.6910−0.29610.03810.178*
H20B0.6273−0.2875−0.01080.178*
H20C0.5989−0.25640.04610.178*
C210.91426 (18)0.06929 (18)0.14722 (12)0.0636 (8)
H21A0.88700.10590.12160.076*
H21B0.92790.01880.12870.076*
C220.9984 (2)0.1077 (2)0.16797 (13)0.0632 (8)
C231.00997 (18)0.26933 (18)0.29940 (11)0.0565 (7)
H231.04770.25660.27130.068*
C240.89875 (19)0.27488 (18)0.35004 (12)0.0595 (7)
H240.84320.26620.36390.071*
C250.9610 (2)0.32244 (17)0.37273 (12)0.0644 (8)
H250.95630.35210.40440.077*
C260.73884 (17)0.27658 (18)0.20333 (11)0.0549 (7)
H260.70330.26740.23300.066*
C270.84577 (19)0.27410 (18)0.14814 (11)0.0585 (7)
H270.89950.26220.13260.070*
C280.7846 (2)0.32259 (17)0.12664 (12)0.0625 (8)
H280.78790.34980.09390.075*
N10.88931 (14)0.05132 (14)0.30650 (9)0.0537 (6)
N20.85342 (14)0.05256 (14)0.19088 (9)0.0531 (6)
N30.93063 (14)0.24140 (13)0.30321 (9)0.0503 (6)
N41.03098 (16)0.31812 (15)0.34020 (10)0.0626 (7)
H4A1.08010.34240.34490.075*
N50.81647 (14)0.24446 (13)0.19703 (8)0.0494 (6)
N60.71714 (15)0.32427 (14)0.16178 (10)0.0604 (6)
H6A0.66930.35100.15810.072*
O20.75060 (12)0.15092 (11)0.28925 (7)0.0597 (5)
O30.68863 (15)0.11563 (16)0.36534 (9)0.0894 (8)
O40.68267 (16)−0.18484 (16)0.01018 (9)0.0913 (7)
O50.99491 (11)0.14794 (12)0.21076 (8)0.0614 (5)
O61.06393 (15)0.09949 (16)0.13974 (10)0.0995 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0416 (2)0.0579 (2)0.0534 (2)−0.00057 (15)−0.00030 (14)−0.00093 (15)
O10.109 (4)0.127 (4)0.090 (4)0.042 (3)0.007 (3)0.034 (3)
C10.141 (6)0.131 (7)0.104 (6)0.053 (6)−0.015 (5)0.045 (5)
C20.078 (4)0.075 (4)0.062 (4)0.025 (3)−0.005 (3)−0.011 (4)
C30.149 (7)0.109 (5)0.066 (4)0.074 (5)−0.015 (4)−0.007 (4)
C40.113 (7)0.106 (5)0.086 (5)0.057 (4)−0.051 (4)−0.012 (4)
C50.030 (4)0.054 (4)0.100 (6)−0.005 (3)−0.011 (3)0.002 (3)
C60.035 (2)0.055 (3)0.093 (4)0.007 (2)0.009 (2)0.007 (3)
C70.044 (3)0.068 (4)0.084 (6)0.020 (2)0.005 (3)0.006 (3)
O1'0.176 (12)0.123 (10)0.157 (13)0.057 (9)0.035 (11)0.066 (10)
C1'0.166 (14)0.178 (15)0.164 (14)0.014 (10)0.001 (9)0.017 (9)
C2'0.067 (7)0.054 (7)0.067 (9)0.009 (6)0.000 (6)−0.005 (6)
C3'0.096 (8)0.058 (7)0.072 (7)0.044 (6)0.002 (6)−0.029 (6)
C4'0.078 (8)0.074 (8)0.075 (8)0.047 (6)−0.010 (6)−0.018 (7)
C5'0.027 (6)0.055 (7)0.069 (7)−0.019 (5)0.002 (5)−0.003 (6)
C6'0.121 (11)0.108 (11)0.142 (11)0.014 (8)0.015 (8)0.018 (8)
C7'0.090 (8)0.095 (8)0.091 (8)0.008 (6)−0.002 (6)−0.002 (6)
C80.0454 (17)0.067 (2)0.081 (2)0.0041 (15)−0.0143 (15)0.0021 (17)
C90.0549 (19)0.073 (2)0.0608 (19)0.0061 (15)0.0032 (16)0.0126 (16)
C100.0509 (18)0.0616 (19)0.062 (2)0.0048 (14)0.0054 (15)0.0128 (16)
C110.0653 (19)0.0550 (19)0.073 (2)−0.0045 (15)−0.0095 (16)0.0015 (17)
C120.062 (2)0.065 (2)0.072 (2)0.0006 (16)−0.0128 (16)−0.0070 (17)
C130.0399 (15)0.074 (2)0.0686 (19)−0.0006 (14)−0.0069 (14)−0.0111 (16)
C140.0423 (16)0.071 (2)0.0596 (19)−0.0053 (15)−0.0056 (14)−0.0067 (16)
C150.0515 (17)0.084 (2)0.0520 (18)−0.0102 (16)−0.0007 (14)−0.0027 (16)
C160.0485 (17)0.073 (2)0.074 (2)−0.0130 (15)−0.0007 (16)−0.0053 (17)
C170.0559 (19)0.084 (2)0.061 (2)−0.0030 (17)−0.0037 (15)−0.0150 (18)
C180.102 (3)0.106 (3)0.0504 (19)−0.037 (2)−0.0023 (19)−0.001 (2)
C190.091 (3)0.081 (2)0.066 (2)−0.0291 (19)−0.0129 (19)0.0095 (19)
C200.155 (4)0.097 (3)0.104 (4)−0.035 (3)−0.018 (3)−0.025 (3)
C210.0512 (18)0.073 (2)0.067 (2)−0.0071 (15)0.0017 (15)−0.0204 (16)
C220.0516 (19)0.071 (2)0.067 (2)−0.0018 (16)0.0056 (16)−0.0123 (17)
C230.0519 (18)0.0651 (19)0.0526 (18)−0.0026 (15)0.0053 (14)−0.0067 (15)
C240.0548 (17)0.0640 (19)0.0597 (19)0.0039 (16)0.0062 (15)−0.0003 (16)
C250.073 (2)0.065 (2)0.0554 (19)0.0057 (17)0.0048 (17)−0.0060 (15)
C260.0473 (17)0.0606 (18)0.0568 (18)−0.0018 (14)0.0042 (14)0.0077 (15)
C270.0533 (17)0.0663 (19)0.0558 (19)−0.0067 (16)0.0095 (15)−0.0013 (15)
C280.067 (2)0.070 (2)0.0514 (18)−0.0135 (16)−0.0019 (16)0.0087 (15)
N10.0449 (13)0.0547 (14)0.0616 (15)−0.0004 (11)−0.0081 (12)0.0006 (12)
N20.0444 (13)0.0610 (15)0.0540 (14)−0.0020 (11)0.0007 (11)−0.0074 (12)
N30.0420 (13)0.0561 (14)0.0530 (14)0.0007 (11)0.0013 (11)−0.0030 (11)
N40.0559 (15)0.0636 (16)0.0684 (17)−0.0061 (12)−0.0052 (13)−0.0045 (13)
N50.0448 (13)0.0556 (14)0.0478 (14)−0.0018 (11)−0.0008 (11)0.0030 (10)
N60.0473 (14)0.0643 (16)0.0694 (17)−0.0009 (12)−0.0029 (12)0.0085 (13)
O20.0492 (11)0.0718 (13)0.0581 (12)0.0055 (9)0.0036 (9)0.0159 (10)
O30.0672 (15)0.1196 (19)0.0814 (17)0.0266 (14)0.0225 (13)0.0384 (14)
O40.106 (2)0.1000 (18)0.0676 (15)−0.0186 (16)−0.0063 (13)−0.0219 (14)
O50.0448 (11)0.0736 (14)0.0658 (13)−0.0060 (9)0.0019 (9)−0.0164 (11)
O60.0589 (14)0.135 (2)0.105 (2)−0.0228 (14)0.0235 (14)−0.0598 (16)
Geometric parameters (Å, °) top
Zn1—N52.099 (2)C11—H11A0.9700
Zn1—N32.103 (2)C11—H11B0.9700
Zn1—O52.1086 (18)C12—N21.472 (4)
Zn1—O22.1261 (18)C12—H12A0.9700
Zn1—N12.281 (2)C12—H12B0.9700
Zn1—N22.287 (2)C13—C141.497 (4)
O1—C11.395 (7)C13—N21.511 (3)
O1—C21.428 (5)C13—H13A0.9700
C1—H1A0.9600C13—H13B0.9700
C1—H1B0.9600C14—C191.377 (4)
C1—H1C0.9600C14—C151.382 (4)
C2—C31.3900C15—C161.392 (4)
C2—C71.3900C15—H150.9300
C3—C41.3900C16—C171.381 (4)
C3—H30.9300C16—H160.9300
C4—C51.3900C17—C181.357 (4)
C4—H40.9300C17—O41.377 (4)
C5—C61.3900C18—C191.366 (4)
C5—C81.558 (4)C18—H180.9300
C6—C71.3900C19—H190.9300
C6—H60.9300C20—O41.414 (4)
C7—H70.9300C20—H20A0.9600
O1'—C2'1.402 (8)C20—H20B0.9600
O1'—C1'1.435 (10)C20—H20C0.9600
C1'—H1'10.9600C21—N21.458 (3)
C1'—H1'20.9600C21—C221.525 (4)
C1'—H1'30.9600C21—H21A0.9700
C2'—C3'1.3900C21—H21B0.9700
C2'—C7'1.3900C22—O61.233 (3)
C3'—C4'1.3900C22—O51.253 (3)
C3'—H3'0.9300C23—N31.303 (3)
C4'—C5'1.3900C23—N41.332 (3)
C4'—H4'0.9300C23—H230.9300
C5'—C6'1.3900C24—C251.355 (4)
C5'—C81.443 (7)C24—N31.377 (3)
C6'—C7'1.3900C24—H240.9300
C6'—H6'0.9300C25—N41.346 (4)
C7'—H7'0.9300C25—H250.9300
C8—N11.495 (3)C26—N51.311 (3)
C8—H8A0.9700C26—N61.338 (3)
C8—H8B0.9700C26—H260.9300
C9—N11.453 (3)C27—C281.341 (4)
C9—C101.517 (4)C27—N51.384 (3)
C9—H9A0.9700C27—H270.9300
C9—H9B0.9700C28—N61.354 (3)
C10—O31.235 (3)C28—H280.9300
C10—O21.243 (3)N4—H4A0.8600
C11—N11.459 (4)N6—H6A0.8600
C11—C121.507 (5)
N5—Zn1—N397.89 (9)C11—C12—H12B109.2
N5—Zn1—O598.14 (8)H12A—C12—H12B107.9
N3—Zn1—O588.30 (8)C14—C13—N2117.1 (2)
N5—Zn1—O288.14 (8)C14—C13—H13A108.0
N3—Zn1—O296.37 (8)N2—C13—H13A108.0
O5—Zn1—O2171.62 (8)C14—C13—H13B108.0
N5—Zn1—N1161.68 (8)N2—C13—H13B108.0
N3—Zn1—N192.98 (8)H13A—C13—H13B107.3
O5—Zn1—N196.89 (8)C19—C14—C15116.9 (3)
O2—Zn1—N175.98 (7)C19—C14—C13121.7 (3)
N5—Zn1—N293.68 (8)C15—C14—C13121.4 (3)
N3—Zn1—N2161.94 (8)C14—C15—C16121.8 (3)
O5—Zn1—N276.32 (7)C14—C15—H15119.1
O2—Zn1—N297.83 (8)C16—C15—H15119.1
N1—Zn1—N279.75 (9)C17—C16—C15118.7 (3)
C1—O1—C2119.5 (6)C17—C16—H16120.6
C3—C2—C7120.0C15—C16—H16120.6
C3—C2—O1115.4 (4)C18—C17—O4116.1 (3)
C7—C2—O1124.5 (4)C18—C17—C16120.0 (3)
C4—C3—C2120.0O4—C17—C16123.9 (3)
C4—C3—H3120.0C17—C18—C19120.4 (3)
C2—C3—H3120.0C17—C18—H18119.8
C3—C4—C5120.0C19—C18—H18119.8
C3—C4—H4120.0C18—C19—C14122.1 (3)
C5—C4—H4120.0C18—C19—H19118.9
C4—C5—C6120.0C14—C19—H19118.9
C4—C5—C8118.2 (3)O4—C20—H20A109.5
C6—C5—C8121.2 (3)O4—C20—H20B109.5
C7—C6—C5120.0H20A—C20—H20B109.5
C7—C6—H6120.0O4—C20—H20C109.5
C5—C6—H6120.0H20A—C20—H20C109.5
C6—C7—C2120.0H20B—C20—H20C109.5
C6—C7—H7120.0N2—C21—C22111.5 (2)
C2—C7—H7120.0N2—C21—H21A109.3
C2'—O1'—C1'113.5 (19)C22—C21—H21A109.3
O1'—C1'—H1'1109.5N2—C21—H21B109.3
O1'—C1'—H1'2109.5C22—C21—H21B109.3
H1'1—C1'—H1'2109.5H21A—C21—H21B108.0
O1'—C1'—H1'3109.5O6—C22—O5125.1 (3)
H1'1—C1'—H1'3109.5O6—C22—C21116.8 (3)
H1'2—C1'—H1'3109.5O5—C22—C21118.0 (3)
C3'—C2'—C7'120.0N3—C23—N4112.4 (2)
C3'—C2'—O1'122.9 (10)N3—C23—H23123.8
C7'—C2'—O1'116.3 (10)N4—C23—H23123.8
C2'—C3'—C4'120.0C25—C24—N3109.4 (3)
C2'—C3'—H3'120.0C25—C24—H24125.3
C4'—C3'—H3'120.0N3—C24—H24125.3
C5'—C4'—C3'120.0N4—C25—C24106.3 (3)
C5'—C4'—H4'120.0N4—C25—H25126.9
C3'—C4'—H4'120.0C24—C25—H25126.9
C4'—C5'—C6'120.0N5—C26—N6111.6 (2)
C4'—C5'—C8125.3 (10)N5—C26—H26124.2
C6'—C5'—C8113.3 (10)N6—C26—H26124.2
C5'—C6'—C7'120.0C28—C27—N5109.4 (3)
C5'—C6'—H6'120.0C28—C27—H27125.3
C7'—C6'—H6'120.0N5—C27—H27125.3
C6'—C7'—C2'120.0C27—C28—N6106.8 (3)
C6'—C7'—H7'120.0C27—C28—H28126.6
C2'—C7'—H7'120.0N6—C28—H28126.6
C5'—C8—N1126.5 (7)C9—N1—C11109.3 (2)
N1—C8—C5113.6 (3)C9—N1—C8112.3 (2)
C5'—C8—H8A104.0C11—N1—C8113.4 (2)
N1—C8—H8A108.9C9—N1—Zn1104.05 (17)
C5—C8—H8A108.9C11—N1—Zn1105.91 (17)
C5'—C8—H8B99.5C8—N1—Zn1111.33 (17)
N1—C8—H8B108.9C21—N2—C12109.0 (2)
C5—C8—H8B108.9C21—N2—C13112.0 (2)
H8A—C8—H8B107.7C12—N2—C13113.3 (2)
N1—C9—C10112.2 (2)C21—N2—Zn1104.23 (16)
N1—C9—H9A109.2C12—N2—Zn1106.03 (17)
C10—C9—H9A109.2C13—N2—Zn1111.68 (16)
N1—C9—H9B109.2C23—N3—C24104.6 (2)
C10—C9—H9B109.2C23—N3—Zn1124.95 (19)
H9A—C9—H9B107.9C24—N3—Zn1130.35 (19)
O3—C10—O2124.7 (3)C23—N4—C25107.3 (2)
O3—C10—C9116.4 (3)C23—N4—H4A126.4
O2—C10—C9118.8 (3)C25—N4—H4A126.4
N1—C11—C12112.4 (2)C26—N5—C27105.0 (2)
N1—C11—H11A109.1C26—N5—Zn1124.67 (19)
C12—C11—H11A109.1C27—N5—Zn1130.1 (2)
N1—C11—H11B109.1C26—N6—C28107.3 (2)
C12—C11—H11B109.1C26—N6—H6A126.4
H11A—C11—H11B107.9C28—N6—H6A126.4
N2—C12—C11112.0 (2)C10—O2—Zn1116.58 (18)
N2—C12—H12A109.2C17—O4—C20119.4 (3)
C11—C12—H12A109.2C22—O5—Zn1117.84 (18)
N2—C12—H12B109.2
C1—O1—C2—C3−175.9 (6)N3—Zn1—N1—C8−54.73 (19)
C1—O1—C2—C76.7 (8)O5—Zn1—N1—C833.9 (2)
C7—C2—C3—C40.0O2—Zn1—N1—C8−150.6 (2)
O1—C2—C3—C4−177.5 (5)N2—Zn1—N1—C8108.6 (2)
C2—C3—C4—C50.0C22—C21—N2—C12−76.9 (3)
C3—C4—C5—C60.0C22—C21—N2—C13156.9 (2)
C3—C4—C5—C8−171.6 (5)C22—C21—N2—Zn136.0 (3)
C4—C5—C6—C70.0C11—C12—N2—C21151.0 (2)
C8—C5—C6—C7171.3 (5)C11—C12—N2—C13−83.5 (3)
C5—C6—C7—C20.0C11—C12—N2—Zn139.4 (3)
C3—C2—C7—C60.0C14—C13—N2—C2159.1 (3)
O1—C2—C7—C6177.3 (5)C14—C13—N2—C12−64.7 (3)
C1'—O1'—C2'—C3'−18 (2)C14—C13—N2—Zn1175.6 (2)
C1'—O1'—C2'—C7'152.0 (17)N5—Zn1—N2—C2169.48 (18)
C7'—C2'—C3'—C4'0.0N3—Zn1—N2—C21−60.4 (4)
O1'—C2'—C3'—C4'169.5 (13)O5—Zn1—N2—C21−28.01 (17)
C2'—C3'—C4'—C5'0.0O2—Zn1—N2—C21158.10 (17)
C3'—C4'—C5'—C6'0.0N1—Zn1—N2—C21−127.76 (18)
C3'—C4'—C5'—C8165.5 (14)N5—Zn1—N2—C12−175.58 (17)
C4'—C5'—C6'—C7'0.0N3—Zn1—N2—C1254.6 (3)
C8—C5'—C6'—C7'−167.1 (13)O5—Zn1—N2—C1286.93 (17)
C5'—C6'—C7'—C2'0.0O2—Zn1—N2—C12−86.96 (17)
C3'—C2'—C7'—C6'0.0N1—Zn1—N2—C12−12.82 (17)
O1'—C2'—C7'—C6'−170.1 (12)N5—Zn1—N2—C13−51.68 (19)
C4'—C5'—C8—N1−74.9 (12)N3—Zn1—N2—C13178.5 (2)
C6'—C5'—C8—N191.5 (9)O5—Zn1—N2—C13−149.2 (2)
C4'—C5'—C8—C5−61 (3)O2—Zn1—N2—C1336.94 (19)
C6'—C5'—C8—C5105 (3)N1—Zn1—N2—C13111.07 (19)
C4—C5—C8—C5'111 (3)N4—C23—N3—C24−0.1 (3)
C6—C5—C8—C5'−60 (3)N4—C23—N3—Zn1−177.41 (18)
C4—C5—C8—N1−80.7 (4)C25—C24—N3—C230.2 (3)
C6—C5—C8—N1107.9 (4)C25—C24—N3—Zn1177.30 (19)
N1—C9—C10—O3162.8 (3)N5—Zn1—N3—C23−91.8 (2)
N1—C9—C10—O2−21.7 (4)O5—Zn1—N3—C236.2 (2)
N1—C11—C12—N2−58.1 (3)O2—Zn1—N3—C23179.2 (2)
N2—C13—C14—C19−84.7 (4)N1—Zn1—N3—C23103.0 (2)
N2—C13—C14—C1597.2 (3)N2—Zn1—N3—C2337.5 (4)
C19—C14—C15—C160.4 (4)N5—Zn1—N3—C2491.6 (2)
C13—C14—C15—C16178.6 (3)O5—Zn1—N3—C24−170.4 (2)
C14—C15—C16—C170.3 (4)O2—Zn1—N3—C242.6 (2)
C15—C16—C17—C18−0.1 (5)N1—Zn1—N3—C24−73.6 (2)
C15—C16—C17—O4179.5 (3)N2—Zn1—N3—C24−139.1 (3)
O4—C17—C18—C19179.4 (3)N3—C23—N4—C250.0 (3)
C16—C17—C18—C19−1.0 (5)C24—C25—N4—C230.2 (3)
C17—C18—C19—C141.8 (6)N6—C26—N5—C270.1 (3)
C15—C14—C19—C18−1.4 (5)N6—C26—N5—Zn1−175.02 (17)
C13—C14—C19—C18−179.7 (3)C28—C27—N5—C26−0.3 (3)
N2—C21—C22—O6156.1 (3)C28—C27—N5—Zn1174.41 (19)
N2—C21—C22—O5−26.9 (4)N3—Zn1—N5—C26−87.8 (2)
N3—C24—C25—N4−0.2 (3)O5—Zn1—N5—C26−177.2 (2)
N5—C27—C28—N60.4 (3)O2—Zn1—N5—C268.4 (2)
C10—C9—N1—C11−77.8 (3)N1—Zn1—N5—C2638.0 (4)
C10—C9—N1—C8155.5 (2)N2—Zn1—N5—C26106.1 (2)
C10—C9—N1—Zn135.0 (3)N3—Zn1—N5—C2798.3 (2)
C12—C11—N1—C9153.2 (2)O5—Zn1—N5—C278.9 (2)
C12—C11—N1—C8−80.7 (3)O2—Zn1—N5—C27−165.5 (2)
C12—C11—N1—Zn141.7 (3)N1—Zn1—N5—C27−135.8 (3)
C5'—C8—N1—C966.0 (8)N2—Zn1—N5—C27−67.8 (2)
C5—C8—N1—C962.6 (4)N5—C26—N6—C280.2 (3)
C5'—C8—N1—C11−58.5 (8)C27—C28—N6—C26−0.4 (3)
C5—C8—N1—C11−61.9 (4)O3—C10—O2—Zn1167.9 (3)
C5'—C8—N1—Zn1−177.8 (8)C9—C10—O2—Zn1−7.2 (4)
C5—C8—N1—Zn1178.8 (3)N5—Zn1—O2—C10−168.1 (2)
N5—Zn1—N1—C9−60.0 (3)N3—Zn1—O2—C10−70.4 (2)
N3—Zn1—N1—C966.46 (18)N1—Zn1—O2—C1021.1 (2)
O5—Zn1—N1—C9155.10 (17)N2—Zn1—O2—C1098.4 (2)
O2—Zn1—N1—C9−29.37 (17)C18—C17—O4—C20179.7 (3)
N2—Zn1—N1—C9−130.20 (18)C16—C17—O4—C200.2 (5)
N5—Zn1—N1—C1155.2 (3)O6—C22—O5—Zn1176.3 (3)
N3—Zn1—N1—C11−178.36 (18)C21—C22—O5—Zn1−0.4 (4)
O5—Zn1—N1—C11−89.71 (18)N5—Zn1—O5—C22−75.3 (2)
O2—Zn1—N1—C1185.81 (18)N3—Zn1—O5—C22−173.1 (2)
N2—Zn1—N1—C11−15.02 (18)N1—Zn1—O5—C2294.2 (2)
N5—Zn1—N1—C8178.8 (2)N2—Zn1—O5—C2216.5 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O3i0.861.872.722 (3)171
N6—H6A···O6ii0.861.862.716 (3)171
C23—H23···O50.932.472.979 (4)115
C26—H26···O20.932.482.974 (3)114
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1/2, −y+1/2, z.
Table 1
Selected geometric parameters (Å, °) top
Zn1—N52.099 (2)Zn1—O22.1261 (18)
Zn1—N32.103 (2)Zn1—N12.281 (2)
Zn1—O52.1086 (18)Zn1—N22.287 (2)
N5—Zn1—N397.89 (9)O5—Zn1—N196.89 (8)
N5—Zn1—O598.14 (8)O2—Zn1—N175.98 (7)
N3—Zn1—O588.30 (8)N5—Zn1—N293.68 (8)
N5—Zn1—O288.14 (8)N3—Zn1—N2161.94 (8)
N3—Zn1—O296.37 (8)O5—Zn1—N276.32 (7)
O5—Zn1—O2171.62 (8)O2—Zn1—N297.83 (8)
N5—Zn1—N1161.68 (8)N1—Zn1—N279.75 (9)
N3—Zn1—N192.98 (8)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O3i0.861.872.722 (3)171
N6—H6A···O6ii0.861.862.716 (3)171
C23—H23···O50.932.472.979 (4)115
C26—H26···O20.932.482.974 (3)114
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1/2, −y+1/2, z.
references
References top

Bruker (2001). or (2000?) SMART (Version ?) and SAINT-Plus (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA. SAINT-Plus or just SAINT as above?

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Suresh, J., Alex Raja, V. P., Perumal, S. & Natarajan, S. (2006). Acta Cryst. E62, o3307–o3309.

Zhang, M., Weng, H.-L. & Xu, X.-M. (2007). Acta Cryst. E63, m1465–m1466.