Aqua­(dipicolinato-κ3O,N,O′)(1,10-phenanthroline-κ2N,N′)zinc(II) monohydrate

Harrison, W.T.A.; Ramadevi, P.; Kumaresan, S.

doi:10.1107/S160053680600420X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 3| March 2006| Pages m513-m515

https://doi.org/10.1107/S160053680600420X

Aqua(dipicolinato-κ³O,N,O′)(1,10-phenanthroline-κ²N,N′)zinc(II) monohydrate

William T. A. Harrison,^a ^* Palani Ramadevi ^b and Sudalaiandi Kumaresan ^b

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and ^bDepartment of Chemistry, Manonmaniam Sundaranar University, Abishekapatti, Tirunelveli 627 012, Tamilnadu, India
^*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 1 February 2006; accepted 3 February 2006; online 15 February 2006)

The title compound, [Zn(C₇H₃NO₄)(C₁₂H₈N₂)(H₂O)]·H₂O, is isostructural with the manganese(II) analogue. The Zn atom is coordinated by a tridentate dipicolinate dianion, a bidentate 1,10-phenanthroline molecule and a water molecule, resulting in a substantially distorted ZnO₃N₃ octahedral grouping. The crystal packing is consolidated by O—H⋯O hydrogen bonds and probable π–π stacking.

Comment

The title compound, (I), arose during our exploratory synthetic studies of coordination polymers containing divalent cations, the dipicolinate (dipic) dianion and multi-functional nitrogen-containing ligands such as 4,4-bipyridine (bipy) and 1,10-phenanthroline (phen). Compound (I) is isostructural with the manganese(II) analogue (Ma et al., 2002 ).

The asymmetric unit of (I) contains a neutral aqua(dipicolinato)(1,10-phenanthroline)zinc(II) molecule accompanied by one water molecule of crystallization (Fig. 1). The dipic dianion bonds to zinc in an O,N,O′-tridentate mode and the phen is N,N′-bidentate. The distorted octahedral ZnO₃N₃ coordination (Table 1) is completed by a water molecule. The substantial deviations of the bond angles from ideal octahedral values [range of cis angles = 73.99 (4)–122.56 (4)° and range of trans angles = 150.12 (4)–161.00 (5)°] may be correlated with the geometrical constraints imposed by the chelating ligands. The Zn—O_d (d = dipic) bond lengths are distinctly different; both are substantially longer than the Zn—O_w (w = water) bond. Very similar equivalent geometric values arose for the isostructural manganese complex (Ma et al., 2002). Considered in isolation, the ZnO₃N₃ grouping in (I) adopts the mer geometric isomer. The dipic dianion is close to planar (for the non-H atoms, r.m.s. deviation from the mean plane = 0.028 Å) and the bipy molecule, as expected, is essentially flat (r.m.s. deviation from the mean plane = 0.036 Å). The zinc cation deviates from the dipic and bipy mean planes by 0.0828 (9) and 0.0232 (11) Å, respectively. The dihedral angle between the dipic and bipy planes is 80.08 (2)° [equivalent value for the Mn congener = 81.5 (1)°].

The packing in (I) involves a network of O—H⋯O hydrogen bonds (Table 2) and probable π–π stacking interactions (Fig. 2) involving the phen ring systems. The shortest π–π ring-centroid separation of 3.4981 (9) Å involves the centroid, Cg1, of the N1/C1–C4/C12 phen ring and its inversion-generated partner, Cg1ⁱ [symmetry code: (i) 1 − x, 1 − y, z]. In the crystal structure, the solvent water molecules connect complex molecules via O—H⋯O hydrogen bonds, forming centrosymmetric clusters (Fig. 3). In addition, intermolecular O—H⋯O hydrogen bonds involving the coordinated water molecules connect these clusters into a three-dimensional network (Fig. 4 and Table 2), as in the Mn analogue (Ma et al., 2002).

Compound (I) complements a number of previously described dipicolinate complexes of zinc which show a wide variety of metal–ligand binding modes. For example, in (C₃H₅N₂)₂[Zn(dipic)₂]·2H₂O (MacDonald et al., 2000 ), two dipic dianions bond to zinc and the resulting overall dianion is charge-balanced by two imidazolinium cations. In Zn(Hdipic)₂·3H₂O (Håkansson et al., 1993 ), two Hdipic monoanions chelate the zinc cation, resulting in a neutral molecule. In Zn₂(dipic)₂(H₂O)₅·2H₂O (Håkansson et al., 1993), a dipic ligand acts as a bridge between two Zn centres (one coordinated by two tridentate dipic anions and one coordinated by a monodentate dipic O atom and five water molecules). In (C₅H₈N₃)[Zn(dipic)(Hdipic)]·3H₂O (Ranjbar et al., 2002 ), one dipic dianion and one Hdipic anion bind to zinc, with 2,6-diaminopyridinium serving as the charge-balancing cation. The complex formula of [Zn(phen)₃]₄(NO₃)₇·Hdipic·26H₂O (Moghimi et al., 2005 ) corresponds to a crystal structure in which the Hdipic anion does not bond to Zn. Finally, a novel variant to (I) is provided by [Zn(bipy)₂(H₂O)₂][Zn(dipic)₂]·7H₂O (Moghimi et al., 2005), in which the bipy molecules and dipic dianions complex separate zinc centres, resulting in a molecular salt.

Figure 1
View of (I)

, showing 50% displacement ellipsoids and arbitrary spheres for the H atoms. The hydrogen bond is indicated by a dashed line.

Figure 2
Detail of (I)

showing probable π–π stacking interactions shorter than 3.8 Å (as dashed lines) linking the centroids (pink circles) of the phen rings. The Zn1* molecule is generated by the symmetry operation (1 − x, 1 − y, z) and Zn1% by (1 + x, y, z). H atoms have been omitted.

Figure 3
Detail of (I)

showing the water-bridged dimeric entity. All H atoms except those of the non-coordinated water molecule have been omitted for clarity. The symmetry code is as in Table 2

. Dashed lines indicate hydrogen bonds.

Figure 4
The packing of (I)

, viewed along [100]. Only H atoms involved in hydrogen bonds (dashed lines) are shown.

Experimental

A mixture of Zn(OAc)₂·2H₂O (27 mg), pyridine-2,6-dicarboxylic acid (20 mg), 1,10-phenanthroline monohydrate (24 mg) and water (2.0 ml) (molar ratio = ca 1:1:1:9300) was sealed in a 23 ml Teflon-lined stainless steel bomb and kept at 423 K under autogenous pressure for 72 h. After slowly cooling (10 K h⁻¹) to room temperature, needle-shaped colourless crystals of (I) were obtained by filtration and rinsing with water and diethyl ether (yield 72%). Analysis calculated for C₁₉H₁₇N₃O₇Zn: C 49.6, H 2.71, N 9.16%; found: C 50.71, H 2.72, N 9.46%. Thermogravimetric analysis for (I) (ramp at 10 K min⁻¹ under N₂) revealed a weight loss of 6.7% between 463 and 468 K, probably corresponding to the loss of both coordinated and non-coordinated water molecules (calculated 8.5%). The dipic and phen ligands decompose slowly (weight loss = 44.8%) over the broad temperature range 493–1173 K. IR (KBr, cm⁻¹): 3445, 1637, 1583, 640, 430.

Crystal data

[Zn(C₇H₃NO₄)(C₁₂H₈N₂)(H₂O)]·H₂O
M_r = 446.71
Monoclinic, P 2₁ /c
a = 7.5199 (3) Å
b = 20.9079 (8) Å
c = 11.5755 (4) Å
β = 100.135 (1)°
V = 1791.56 (12) Å³
Z = 4
D_x = 1.656 Mg m⁻³
Mo Kα radiation
Cell parameters from 7488 reflections
θ = 2.7–32.0°
μ = 1.42 mm⁻¹
T = 293 (2) K
Block, colourless
0.21 × 0.20 × 0.20 mm

Data collection

Bruker SMART1000 CCD diffractometer
ω scans
Absorption correction: multi-scan(SADABS; Bruker, 2003 )T_min = 0.747, T_max = 0.757
21156 measured reflections
6439 independent reflections
4678 reflections with I > 2σ(I)
R_int = 0.025
θ_max = 32.5°
h = −10 → 11
k = −31 → 31
l = −13 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 0.97
6439 reflections
263 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0439P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.003
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.0020 (5)

Table 1
Selected bond lengths (Å)

Zn1—O5	2.0513 (11)
Zn1—N3	2.0540 (11)
Zn1—N2	2.1168 (11)
Zn1—O3	2.1941 (11)
Zn1—N1	2.2071 (12)
Zn1—O1	2.2651 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4ⁱ	0.84	1.79	2.6058 (17)	162
O5—H52⋯O2ⁱⁱ	0.83	1.90	2.7162 (15)	167
O6—H61⋯O2ⁱⁱⁱ	0.90	1.98	2.8461 (18)	161
O6—H62⋯O1	0.83	2.14	2.9356 (16)	160
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) -x, -y+1, -z+1.

The water H atoms were located in difference maps and refined as riding in their as-found relative positions. The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding. The constraint U_iso(H) = 1.2U_eq(carrier) was applied in all cases.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680600420X/lh6593sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680600420X/lh6593Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Aqua(dipicolinato-κ³O,N,O')(1,10-phenanthroline-κ²N,N)zinc(II) monohydrate top

Crystal data top

[Zn(C₇H₃NO₄)(C₁₂H₈N₂)(H₂O)]·H₂O	F(000) = 912
M_r = 446.71	D_x = 1.656 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7488 reflections
a = 7.5199 (3) Å	θ = 2.7–32.0°
b = 20.9079 (8) Å	µ = 1.42 mm⁻¹
c = 11.5755 (4) Å	T = 293 K
β = 100.135 (1)°	Block, colourless
V = 1791.56 (12) Å³	0.21 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART1000 CCD diffractometer	6439 independent reflections
Radiation source: fine-focus sealed tube	4678 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 32.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→11
T_min = 0.747, T_max = 0.757	k = −31→31
21156 measured reflections	l = −13→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0439P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.003
6439 reflections	Δρ_max = 0.33 e Å⁻³
263 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (5)

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

	x	y	z	U_iso*/U_eq
Zn1	0.33893 (2)	0.623507 (7)	0.237913 (15)	0.03005 (6)
C1	0.1319 (2)	0.60512 (7)	−0.02782 (14)	0.0364 (3)
H1	0.0961	0.6476	−0.0244	0.044*
C2	0.0793 (2)	0.57113 (8)	−0.13292 (14)	0.0403 (4)
H2	0.0102	0.5909	−0.1976	0.048*
C3	0.1306 (2)	0.50902 (8)	−0.13923 (14)	0.0404 (4)
H3	0.0968	0.4861	−0.2085	0.049*
C4	0.2347 (2)	0.47943 (7)	−0.04095 (14)	0.0334 (3)
C5	0.2931 (2)	0.41444 (8)	−0.03885 (16)	0.0427 (4)
H5	0.2646	0.3897	−0.1064	0.051*
C6	0.3888 (2)	0.38816 (7)	0.05892 (17)	0.0431 (4)
H6	0.4217	0.3453	0.0586	0.052*
C7	0.4409 (2)	0.42541 (7)	0.16389 (15)	0.0358 (3)
C8	0.5440 (2)	0.40106 (8)	0.26720 (17)	0.0450 (4)
H8	0.5773	0.3582	0.2717	0.054*
C9	0.5954 (2)	0.44054 (9)	0.36141 (16)	0.0459 (4)
H9	0.6635	0.4248	0.4304	0.055*
C10	0.5442 (2)	0.50485 (8)	0.35248 (14)	0.0379 (3)
H10	0.5813	0.5315	0.4165	0.046*
C11	0.39179 (18)	0.49022 (6)	0.16361 (13)	0.0286 (3)
C12	0.28227 (18)	0.51734 (6)	0.06063 (12)	0.0279 (3)
N1	0.23076 (16)	0.57902 (5)	0.06708 (11)	0.0301 (2)
N2	0.44485 (15)	0.52953 (5)	0.25652 (11)	0.0303 (2)
C13	−0.00108 (18)	0.62823 (6)	0.34393 (12)	0.0277 (3)
C14	0.00259 (18)	0.68935 (6)	0.27386 (12)	0.0275 (3)
C15	−0.1326 (2)	0.73519 (7)	0.25645 (16)	0.0410 (4)
H15	−0.2344	0.7311	0.2913	0.049*
C16	−0.1125 (2)	0.78746 (8)	0.18575 (18)	0.0504 (4)
H16	−0.2017	0.8187	0.1722	0.061*
C17	0.0402 (3)	0.79284 (7)	0.13578 (16)	0.0455 (4)
H17	0.0562	0.8280	0.0894	0.055*
C18	0.1689 (2)	0.74519 (7)	0.15580 (13)	0.0331 (3)
C19	0.3407 (2)	0.74316 (7)	0.10289 (15)	0.0403 (4)
N3	0.14862 (15)	0.69489 (5)	0.22351 (11)	0.0270 (2)
O1	0.13117 (14)	0.59104 (5)	0.34531 (10)	0.0343 (2)
O2	−0.13240 (14)	0.61879 (5)	0.39422 (11)	0.0406 (3)
O3	0.44372 (15)	0.69665 (5)	0.13165 (11)	0.0438 (3)
O4	0.3601 (2)	0.78820 (7)	0.03632 (14)	0.0706 (4)
O5	0.51776 (15)	0.65501 (7)	0.38119 (11)	0.0517 (3)
H51	0.4890	0.6765	0.4369	0.062*
H52	0.6293	0.6496	0.3895	0.062*
O6	0.1270 (2)	0.45365 (6)	0.39703 (12)	0.0675 (4)
H61	0.1122	0.4382	0.4676	0.081*
H62	0.1229	0.4933	0.3996	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02840 (9)	0.02932 (9)	0.03322 (10)	0.00121 (6)	0.00758 (6)	−0.00367 (6)
C1	0.0365 (8)	0.0359 (7)	0.0356 (8)	−0.0011 (6)	0.0026 (6)	0.0014 (6)
C2	0.0397 (8)	0.0489 (9)	0.0304 (8)	−0.0058 (7)	0.0009 (6)	0.0023 (6)
C3	0.0398 (8)	0.0518 (9)	0.0299 (8)	−0.0124 (7)	0.0066 (6)	−0.0098 (7)
C4	0.0307 (7)	0.0372 (7)	0.0343 (8)	−0.0080 (5)	0.0115 (6)	−0.0084 (6)
C5	0.0448 (9)	0.0384 (8)	0.0478 (10)	−0.0078 (7)	0.0159 (7)	−0.0168 (7)
C6	0.0452 (9)	0.0294 (7)	0.0584 (12)	−0.0002 (6)	0.0191 (8)	−0.0088 (7)
C7	0.0331 (7)	0.0308 (7)	0.0466 (9)	0.0018 (5)	0.0154 (6)	0.0011 (6)
C8	0.0435 (9)	0.0368 (8)	0.0570 (11)	0.0098 (7)	0.0153 (8)	0.0104 (7)
C9	0.0425 (9)	0.0519 (9)	0.0435 (10)	0.0109 (7)	0.0082 (7)	0.0154 (8)
C10	0.0349 (8)	0.0462 (8)	0.0323 (8)	0.0029 (6)	0.0044 (6)	0.0031 (6)
C11	0.0258 (6)	0.0300 (6)	0.0320 (7)	−0.0007 (5)	0.0108 (5)	−0.0010 (5)
C12	0.0261 (6)	0.0297 (6)	0.0295 (7)	−0.0038 (5)	0.0098 (5)	−0.0030 (5)
N1	0.0303 (6)	0.0293 (5)	0.0306 (6)	−0.0012 (4)	0.0053 (5)	−0.0013 (4)
N2	0.0284 (6)	0.0336 (6)	0.0294 (6)	0.0014 (4)	0.0067 (5)	−0.0007 (5)
C13	0.0253 (6)	0.0286 (6)	0.0296 (7)	−0.0032 (5)	0.0059 (5)	0.0008 (5)
C14	0.0266 (6)	0.0261 (6)	0.0302 (7)	−0.0011 (5)	0.0061 (5)	−0.0001 (5)
C15	0.0320 (8)	0.0363 (8)	0.0562 (11)	0.0061 (6)	0.0115 (7)	0.0057 (7)
C16	0.0444 (9)	0.0373 (8)	0.0687 (13)	0.0108 (7)	0.0074 (9)	0.0118 (8)
C17	0.0581 (10)	0.0305 (7)	0.0473 (10)	0.0015 (7)	0.0079 (8)	0.0118 (7)
C18	0.0424 (8)	0.0281 (6)	0.0301 (8)	−0.0053 (5)	0.0101 (6)	−0.0003 (5)
C19	0.0545 (10)	0.0337 (7)	0.0378 (9)	−0.0149 (7)	0.0220 (7)	−0.0065 (6)
N3	0.0304 (6)	0.0245 (5)	0.0275 (6)	−0.0028 (4)	0.0085 (4)	−0.0001 (4)
O1	0.0318 (5)	0.0315 (5)	0.0415 (6)	0.0048 (4)	0.0116 (4)	0.0084 (4)
O2	0.0311 (5)	0.0464 (6)	0.0479 (7)	0.0020 (4)	0.0172 (5)	0.0117 (5)
O3	0.0432 (6)	0.0425 (6)	0.0522 (7)	−0.0105 (5)	0.0261 (6)	−0.0087 (5)
O4	0.0981 (12)	0.0538 (8)	0.0732 (10)	−0.0133 (8)	0.0514 (9)	0.0159 (7)
O5	0.0281 (5)	0.0790 (9)	0.0480 (7)	0.0034 (5)	0.0072 (5)	−0.0315 (6)
O6	0.1085 (12)	0.0482 (7)	0.0422 (8)	−0.0068 (8)	0.0035 (8)	0.0062 (6)

Geometric parameters (Å, º) top

Zn1—O5	2.0513 (11)	C10—N2	1.3290 (19)
Zn1—N3	2.0540 (11)	C10—H10	0.9300
Zn1—N2	2.1168 (11)	C11—N2	1.3566 (18)
Zn1—O3	2.1941 (11)	C11—C12	1.441 (2)
Zn1—N1	2.2071 (12)	C12—N1	1.3522 (17)
Zn1—O1	2.2651 (10)	C13—O2	1.2471 (17)
C1—N1	1.3304 (19)	C13—O1	1.2602 (16)
C1—C2	1.404 (2)	C13—C14	1.5165 (18)
C1—H1	0.9300	C14—N3	1.3357 (17)
C2—C3	1.360 (2)	C14—C15	1.3857 (19)
C2—H2	0.9300	C15—C16	1.389 (2)
C3—C4	1.406 (2)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.378 (3)
C4—C12	1.411 (2)	C16—H16	0.9300
C4—C5	1.427 (2)	C17—C18	1.380 (2)
C5—C6	1.347 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—N3	1.3364 (18)
C6—C7	1.438 (2)	C18—C19	1.524 (2)
C6—H6	0.9300	C19—O4	1.241 (2)
C7—C8	1.402 (2)	C19—O3	1.251 (2)
C7—C11	1.4043 (19)	O5—H51	0.8444
C8—C9	1.368 (3)	O5—H52	0.8348
C8—H8	0.9300	O6—H61	0.9036
C9—C10	1.397 (2)	O6—H62	0.8296
C9—H9	0.9300

O5—Zn1—N3	100.40 (5)	C9—C10—H10	118.6
O5—Zn1—N2	91.97 (5)	N2—C11—C7	122.84 (13)
N3—Zn1—N2	157.96 (5)	N2—C11—C12	117.59 (12)
O5—Zn1—O3	88.88 (5)	C7—C11—C12	119.57 (13)
N3—Zn1—O3	76.23 (4)	N1—C12—C4	123.27 (13)
N2—Zn1—O3	122.56 (4)	N1—C12—C11	117.21 (12)
O5—Zn1—N1	161.00 (5)	C4—C12—C11	119.52 (13)
N3—Zn1—N1	95.27 (5)	C1—N1—C12	118.00 (13)
N2—Zn1—N1	76.86 (4)	C1—N1—Zn1	129.14 (10)
O3—Zn1—N1	84.46 (4)	C12—N1—Zn1	112.79 (9)
O5—Zn1—O1	94.01 (5)	C10—N2—C11	118.10 (13)
N3—Zn1—O1	73.99 (4)	C10—N2—Zn1	126.27 (10)
N2—Zn1—O1	87.11 (4)	C11—N2—Zn1	115.39 (9)
O3—Zn1—O1	150.12 (4)	O2—C13—O1	125.76 (13)
N1—Zn1—O1	100.63 (4)	O2—C13—C14	118.26 (12)
N1—C1—C2	122.61 (14)	O1—C13—C14	115.98 (12)
N1—C1—H1	118.7	N3—C14—C15	120.99 (13)
C2—C1—H1	118.7	N3—C14—C13	113.59 (11)
C3—C2—C1	119.37 (15)	C15—C14—C13	125.36 (13)
C3—C2—H2	120.3	C14—C15—C16	118.47 (15)
C1—C2—H2	120.3	C14—C15—H15	120.8
C2—C3—C4	119.96 (14)	C16—C15—H15	120.8
C2—C3—H3	120.0	C17—C16—C15	119.76 (15)
C4—C3—H3	120.0	C17—C16—H16	120.1
C3—C4—C12	116.78 (14)	C15—C16—H16	120.1
C3—C4—C5	123.97 (14)	C16—C17—C18	118.83 (15)
C12—C4—C5	119.24 (15)	C16—C17—H17	120.6
C6—C5—C4	121.35 (15)	C18—C17—H17	120.6
C6—C5—H5	119.3	N3—C18—C17	121.16 (14)
C4—C5—H5	119.3	N3—C18—C19	113.96 (13)
C5—C6—C7	120.97 (14)	C17—C18—C19	124.86 (14)
C5—C6—H6	119.5	O4—C19—O3	128.30 (16)
C7—C6—H6	119.5	O4—C19—C18	115.38 (16)
C8—C7—C11	117.27 (15)	O3—C19—C18	116.32 (13)
C8—C7—C6	123.47 (14)	C14—N3—C18	120.77 (12)
C11—C7—C6	119.23 (15)	C14—N3—Zn1	121.07 (9)
C9—C8—C7	119.82 (15)	C18—N3—Zn1	118.01 (10)
C9—C8—H8	120.1	C13—O1—Zn1	115.29 (9)
C7—C8—H8	120.1	C19—O3—Zn1	115.10 (9)
C8—C9—C10	119.08 (16)	Zn1—O5—H51	124.6
C8—C9—H9	120.5	Zn1—O5—H52	123.5
C10—C9—H9	120.5	H51—O5—H52	111.8
N2—C10—C9	122.86 (16)	H61—O6—H62	108.3
N2—C10—H10	118.6

N1—C1—C2—C3	0.0 (3)	O5—Zn1—N2—C11	−167.15 (10)
C1—C2—C3—C4	0.2 (2)	N3—Zn1—N2—C11	68.34 (17)
C2—C3—C4—C12	−0.6 (2)	O3—Zn1—N2—C11	−77.22 (11)
C2—C3—C4—C5	179.33 (15)	N1—Zn1—N2—C11	−2.68 (9)
C3—C4—C5—C6	−178.27 (16)	O1—Zn1—N2—C11	98.94 (10)
C12—C4—C5—C6	1.7 (2)	O2—C13—C14—N3	−179.99 (13)
C4—C5—C6—C7	−2.1 (3)	O1—C13—C14—N3	−0.28 (18)
C5—C6—C7—C8	−178.44 (16)	O2—C13—C14—C15	−2.8 (2)
C5—C6—C7—C11	−0.4 (2)	O1—C13—C14—C15	176.89 (14)
C11—C7—C8—C9	−1.3 (2)	N3—C14—C15—C16	−0.4 (2)
C6—C7—C8—C9	176.75 (16)	C13—C14—C15—C16	−177.33 (15)
C7—C8—C9—C10	−0.2 (3)	C14—C15—C16—C17	−0.5 (3)
C8—C9—C10—N2	1.0 (3)	C15—C16—C17—C18	1.1 (3)
C8—C7—C11—N2	2.2 (2)	C16—C17—C18—N3	−0.8 (3)
C6—C7—C11—N2	−175.90 (14)	C16—C17—C18—C19	177.52 (16)
C8—C7—C11—C12	−178.55 (13)	N3—C18—C19—O4	177.62 (15)
C6—C7—C11—C12	3.3 (2)	C17—C18—C19—O4	−0.8 (2)
C3—C4—C12—N1	0.9 (2)	N3—C18—C19—O3	−2.3 (2)
C5—C4—C12—N1	−179.06 (13)	C17—C18—C19—O3	179.21 (15)
C3—C4—C12—C11	−178.80 (13)	C15—C14—N3—C18	0.6 (2)
C5—C4—C12—C11	1.2 (2)	C13—C14—N3—C18	177.94 (12)
N2—C11—C12—N1	−4.18 (18)	C15—C14—N3—Zn1	−174.88 (11)
C7—C11—C12—N1	176.57 (13)	C13—C14—N3—Zn1	2.42 (16)
N2—C11—C12—C4	175.54 (12)	C17—C18—N3—C14	0.0 (2)
C7—C11—C12—C4	−3.7 (2)	C19—C18—N3—C14	−178.55 (12)
C2—C1—N1—C12	0.2 (2)	C17—C18—N3—Zn1	175.63 (12)
C2—C1—N1—Zn1	177.03 (11)	C19—C18—N3—Zn1	−2.91 (16)
C4—C12—N1—C1	−0.7 (2)	O5—Zn1—N3—C14	−93.69 (11)
C11—C12—N1—C1	179.00 (13)	N2—Zn1—N3—C14	29.46 (19)
C4—C12—N1—Zn1	−178.02 (11)	O3—Zn1—N3—C14	−179.93 (11)
C11—C12—N1—Zn1	1.69 (15)	N1—Zn1—N3—C14	97.10 (11)
O5—Zn1—N1—C1	−121.17 (18)	O1—Zn1—N3—C14	−2.47 (10)
N3—Zn1—N1—C1	24.41 (13)	O5—Zn1—N3—C18	90.68 (11)
N2—Zn1—N1—C1	−176.46 (14)	N2—Zn1—N3—C18	−146.17 (12)
O3—Zn1—N1—C1	−51.16 (13)	O3—Zn1—N3—C18	4.44 (10)
O1—Zn1—N1—C1	99.07 (13)	N1—Zn1—N3—C18	−78.54 (11)
O5—Zn1—N1—C12	55.8 (2)	O1—Zn1—N3—C18	−178.10 (11)
N3—Zn1—N1—C12	−158.65 (9)	O2—C13—O1—Zn1	178.00 (12)
N2—Zn1—N1—C12	0.48 (9)	C14—C13—O1—Zn1	−1.69 (15)
O3—Zn1—N1—C12	125.78 (10)	O5—Zn1—O1—C13	101.89 (10)
O1—Zn1—N1—C12	−83.98 (9)	N3—Zn1—O1—C13	2.21 (10)
C9—C10—N2—C11	−0.1 (2)	N2—Zn1—O1—C13	−166.33 (10)
C9—C10—N2—Zn1	173.96 (12)	O3—Zn1—O1—C13	7.16 (15)
C7—C11—N2—C10	−1.5 (2)	N1—Zn1—O1—C13	−90.28 (10)
C12—C11—N2—C10	179.24 (13)	O4—C19—O3—Zn1	−173.96 (16)
C7—C11—N2—Zn1	−176.25 (11)	C18—C19—O3—Zn1	5.98 (17)
C12—C11—N2—Zn1	4.53 (16)	O5—Zn1—O3—C19	−106.75 (11)
O5—Zn1—N2—C10	18.64 (13)	N3—Zn1—O3—C19	−5.75 (11)
N3—Zn1—N2—C10	−105.88 (16)	N2—Zn1—O3—C19	161.63 (11)
O3—Zn1—N2—C10	108.56 (12)	N1—Zn1—O3—C19	91.06 (11)
N1—Zn1—N2—C10	−176.90 (13)	O1—Zn1—O3—C19	−10.66 (16)
O1—Zn1—N2—C10	−75.28 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ⁱ	0.84	1.79	2.6058 (17)	162
O5—H52···O2ⁱⁱ	0.83	1.90	2.7162 (15)	167
O6—H61···O2ⁱⁱⁱ	0.90	1.98	2.8461 (18)	161
O6—H62···O1	0.83	2.14	2.9356 (16)	160

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x, −y+1, −z+1.

References

Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. App. Cryst. 30, 565. CrossRef Google Scholar
Håkansson, K., Lindahl, M., Svensson, G. & Albertsson, J. (1993). Acta Chem. Scand. 47, 449–455. Google Scholar
MacDonald, J. C., Dorrestein, P. C., Pilley, M. M., Foote, M. M., Lundberg, J. L., Henning, R. W., Schultz, A. J. & Manson , J. L. (2000). J. Am. Chem. Soc. 122, 11692–11702. Web of Science CSD CrossRef CAS Google Scholar
Ma, C., Fan, C., Chen, C. & Liu, Q. (2002). Acta Cryst. C58, m553–m555. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Moghimi, A., Sheshmani, S., Shokrollahi, A., Shamsipur, M., Kickelbick, G. & Aghabozorg, H. (2005). Z. Anorg. Allg. Chem. 631, 160–169. Web of Science CSD CrossRef CAS Google Scholar
Ranjbar, M., Moghimi, A., Aghabozorg, H. & Yap, G. Y. A. (2002). Anal. Sci. 18, 219–220. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar

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Volume 62| Part 3| March 2006| Pages m513-m515

https://doi.org/10.1107/S160053680600420X

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