Tetra­aqua­bis(3-fluoro­pyridine-4-carboxyl­ato-κN)zinc(II) dihydrate

Fleming, J.; Kelley, J.; Peterson Jr, L.R.; Smith, M.D.; Loye, H.-C. zur

doi:10.1107/S1600536810003284

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages m244-m245

doi:10.1107/S1600536810003284

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Tetraaquabis(3-fluoropyridine-4-carboxylato-κN)zinc(II) dihydrate

Jonetha Fleming,^a Jennifer Kelley,^a LeRoy Peterson Jr,^a ^* Mark D. Smith ^b and Hans-Conrad zur Loye ^b

^aChemistry Department, Francis Marion University, Florence, South Carolina 29502, USA, and ^bDepartment of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA
^*Correspondence e-mail: lpeterson@fmarion.edu

(Received 1 December 2009; accepted 26 January 2010; online 3 February 2010)

In the title compound, [Zn(C₆H₃FNO₂)₂(H₂O)₄]·2H₂O, the Zn^II atom is octahedrally coordinated in a ZnO₄N₂ environment by two 3-fluoropyridine-4-carboxylate (3-fpy4-cbx) ligands and four water molecules. The [Zn(3-fpy4-cbx)₂(H₂O)₄] molecules form a three-dimensional network through strong O—H⋯O and weak O—H⋯F hydrogen bonds between 3-fpy4-cbx and water molecules. The crystal used for data collection was a twin, with the twin law corresponding to a 180° rotation about the real-space [001] axis. The major twin fraction refined to 0.795 (1).

Related literature

For metal-organic compounds with ligands containing both pyridyl and carboxylate donor groups, see: Ellsworth et al. (2008 ); Erxleben (2003 ); Wang et al. (2006 ). For specific properties exhibited by related metal-organic compounds, see: Chen et al. (2009 ); Evans et al. (1999 ); Xie et al. (2008 ). For typical Zn—O and Zn—N bond distances in similar metal-organic compounds, see: Wang et al. (2006).

Experimental

Crystal data

[Zn(C₆H₃FNO₂)₂(H₂O)₄]·2H₂O
M_r = 453.65
Monoclinic, P 2₁ /n
a = 6.6042 (4) Å
b = 19.1953 (10) Å
c = 6.8697 (4) Å
β = 99.225 (1)°
V = 859.61 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 294 K
0.28 × 0.22 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (TWINABS; Bruker, 2003 ) T_min = 0.890, T_max = 1.000
1734 measured reflections
1740 independent reflections
1605 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.065
S = 1.07
1740 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O3	2.0953 (14)
Zn1—N1	2.1356 (13)
Zn1—O4	2.1504 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.83 (3)	1.86 (3)	2.6892 (18)	174 (2)
O3—H3B⋯O5ⁱⁱ	0.74 (2)	2.01 (2)	2.745 (2)	176 (2)
O4—H4A⋯O2ⁱⁱⁱ	0.79 (3)	2.05 (3)	2.837 (2)	174 (2)
O4—H4B⋯O5^iv	0.82 (2)	1.95 (3)	2.7643 (19)	171 (3)
O5—H5A⋯O2	0.75 (3)	2.05 (3)	2.796 (2)	174 (3)
O5—H5B⋯O1^v	0.79 (2)	1.96 (3)	2.738 (2)	167 (2)
O5—H5B⋯F1^v	0.79 (2)	2.55 (2)	2.9929 (17)	117.2 (18)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) x+1, y, z.

Data collection: SMART-NT (Bruker, 2003); cell refinement: SAINT-Plus-NT (Bruker, 2003); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003284/jj2018sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003284/jj2018Isup2.hkl

checkCIF report

Comment top

Metal-organic compounds based on multifunctional ligands that contain both pyridyl and carboxylate donor atoms have been under study in part because of their diverse coordination modes and because they may exhibit useful properties (Ellsworth et al., 2008; Erxleben, 2003). Within this context, the 3-fluoropyridine-4-carboxylate ligand (3-fpy4-cbx), has attracted our interest as a potential component for the construction of these novel materials. A further motivation is that its nonfluorinated analogue, the isonicotinate ligand (ina), has been successfully utilized to generate metal-organic frameworks having the desirable properties alluded to above (Chen et al., 2009; Evans et al., 1999; Wang et al., 2006; Xie et al.,2008). Hence, we have deemed it worthwhile to also explore the coordinatingproperties of the related 3-fpy4-cbx ligand. This ligand has the additional possibility of C—F···H interactions, in contrast to ina. Herein, we wish to report the crystal structure of the title compound (I), which is a hydrogen bonded, three-dimensional framework.

The asymmetric unit of (I) consists of one-half of the [Zn(3-fpy4-cbx) ₂ (H₂O) ₄] complex and a lattice water. The Zn(II) atom is located on an inversion center through which the other half of the molecular complex and another lattice water are generated from the asymmetric unit, thus completing the formula unit of (I) (Fig. 1).

The Zn(II) atom resides in a distorted ZnO₄N₂ octahedral environment. The equatorial positions are occupied by four O atoms from water molecules and the axial positions are occupied by N atoms from two 3-fpy4-cbx ligands. The Zn—O bond distances fall within the normal range of 2.0953 (14) - 2.1504 (13) Å (Wang et al., 2006), while the Zn—N distances are also normal at 2.1356 (13) Å (Wang et al., 2006). The 3-fpy4-cbx ligand is noticeably noncoplanar, with a dihedral angle of 34.2 (1)° between the mean planes of its carboxylate group and its pyridyl ring.

While the carboxylate group of 3-fpy4-cbx is not coordinated to Zn(II), it does assist in the assembly of the crystal structure by acting as hydrogen bond acceptors for both coordinated and lattice waters. The lattice waters are also involved in weak C—F···H₂O hydrogen bonding with the 3-fpy4-cbx ligand. These interactions create a three-dimensional, hydrogen bonded network (Table 1, Fig. 2).

Related literature top

For metal-organic compounds with ligands containing both pyridyl and carboxylate donor groups, see: Ellsworth et al. (2008); Erxleben (2003); Wang et al. (2006). For specific properties exhibited by related metal-organic compounds, see: Chen et al. (2009); Evans et al. (1999); Xie et al. (2008). For typical Zn—O and Zn—N bond distances in similar metal-organic compounds, see: Wang et al. (2006).

Experimental top

An aqueous solution of sodium 3-fluoropyridine-4-carboxylate (25 ml, 2.0 mmol) was slowly added to an aqueous solution of zinc nitrate hexahydrate (25 ml, 1.0 mmol). Colorless crystals of the title compound were obtained after slow evaporation of the resulting solution under ambient conditions.

Computing details top

Data collection: SMART-NT (Bruker, 2003); cell refinement: SAINT-Plus-NT (Bruker, 2003); data reduction: SAINT-Plus-NT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular complex plus lattice waters with atom-labeling scheme of (I) showing 50% probability ellipsoids for nonhydrogen atoms. All H atoms except for those of water are omitted for clarity. Hydrogen bonds are represented by dashed lines. Primed atoms are generated by the inversion symmetry operation about Zn(II), with symmetry code: 1 - x, 1 - y, 1 - z.
	Fig. 2. Wireframe polyhedral view of the crystal packing in (I) showing the hydrogen bonding scheme. Hydrogen atoms except for those of water have been omitted for clarity. Hydrogen bonds are represented by dashed lines.

Tetraaquabis(3-fluoropyridine-4-carboxylato-κN)zinc(II) dihydrate top

Crystal data top

[Zn(C₆H₃FNO₂)₂(H₂O)₄]·2H₂O	F(000) = 464
M_r = 453.65	D_x = 1.753 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7697 reflections
a = 6.6042 (4) Å	θ = 3.0–25.0°
b = 19.1953 (10) Å	µ = 1.51 mm⁻¹
c = 6.8697 (4) Å	T = 294 K
β = 99.225 (1)°	Block, colorless
V = 859.61 (8) Å³	0.28 × 0.22 × 0.16 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	1740 independent reflections
Radiation source: fine-focus sealed tube	1605 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (TWINABS; Bruker, 2003)	h = −7→7
T_min = 0.890, T_max = 1.000	k = 0→22
1734 measured reflections	l = 0→8

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.023	Hydrogen site location: mixed
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0427P)² + 0.0969P] where P = (F_o² + 2F_c²)/3
1740 reflections	(Δ/σ)_max = 0.001
149 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

[Zn(C₆H₃FNO₂)₂(H₂O)₄]·2H₂O	V = 859.61 (8) Å³
M_r = 453.65	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.6042 (4) Å	µ = 1.51 mm⁻¹
b = 19.1953 (10) Å	T = 294 K
c = 6.8697 (4) Å	0.28 × 0.22 × 0.16 mm
β = 99.225 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	1740 independent reflections
Absorption correction: multi-scan (TWINABS; Bruker, 2003)	1605 reflections with I > 2σ(I)
T_min = 0.890, T_max = 1.000	R_int = 0.031
1734 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.28 e Å⁻³
1740 reflections	Δρ_min = −0.19 e Å⁻³
149 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. R(int) value from TWINABS output.

Cell_now output:

Rotated from first domain by 179.9 degrees about reciprocal axis -0.159 - 0.001 1.000 and real axis -0.001 0.000 1.000

Twin law to convert hkl from first to -1.000 0.000 - 0.317 this domain (SHELXL TWIN matrix): 0.001 - 1.000 0.000 - 0.002 0.000 1.000

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	0.5000	0.5000	0.5000	0.02937 (12)
F1	0.31965 (16)	0.76809 (5)	0.48595 (19)	0.0515 (3)
C1	0.4393 (3)	0.65492 (9)	0.4885 (2)	0.0316 (4)
H1	0.3043	0.6403	0.4833	0.038*
C2	0.4808 (2)	0.72491 (9)	0.4902 (2)	0.0299 (4)
C3	0.6762 (3)	0.75042 (8)	0.4933 (2)	0.0280 (3)
C4	0.8278 (3)	0.69967 (9)	0.4946 (3)	0.0366 (4)
H4	0.9628	0.7131	0.4932	0.044*
C5	0.7798 (3)	0.63022 (9)	0.4979 (3)	0.0356 (4)
H5	0.8850	0.5978	0.5030	0.043*
C6	0.7287 (3)	0.82734 (8)	0.5010 (3)	0.0340 (4)
N1	0.5870 (2)	0.60704 (7)	0.4940 (2)	0.0297 (3)
O1	0.62449 (18)	0.86516 (6)	0.5953 (2)	0.0468 (3)
O2	0.8725 (2)	0.84601 (7)	0.4177 (2)	0.0504 (4)
O3	0.7470 (2)	0.48608 (7)	0.7293 (2)	0.0401 (3)
H3A	0.780 (4)	0.4489 (14)	0.789 (4)	0.068 (8)*
H3B	0.750 (3)	0.5121 (11)	0.809 (3)	0.038 (6)*
O4	0.6983 (2)	0.47337 (8)	0.2917 (2)	0.0413 (3)
H4A	0.686 (4)	0.4385 (13)	0.230 (4)	0.061 (8)*
H4B	0.708 (4)	0.5080 (12)	0.223 (4)	0.058 (8)*
O5	1.2370 (3)	0.92014 (7)	0.5293 (2)	0.0419 (3)
H5A	1.142 (4)	0.8983 (14)	0.505 (4)	0.068 (9)*
H5B	1.340 (4)	0.8988 (11)	0.553 (3)	0.047 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03564 (18)	0.01479 (16)	0.03843 (19)	−0.00133 (10)	0.00817 (12)	0.00005 (10)
F1	0.0358 (6)	0.0230 (5)	0.0947 (9)	0.0041 (4)	0.0078 (6)	−0.0037 (5)
C1	0.0308 (8)	0.0223 (9)	0.0419 (10)	−0.0026 (7)	0.0064 (7)	−0.0002 (7)
C2	0.0315 (9)	0.0201 (9)	0.0383 (9)	0.0039 (6)	0.0062 (7)	−0.0004 (6)
C3	0.0341 (9)	0.0207 (8)	0.0296 (8)	−0.0022 (6)	0.0058 (7)	0.0004 (6)
C4	0.0305 (8)	0.0261 (8)	0.0546 (11)	−0.0031 (7)	0.0114 (8)	−0.0020 (8)
C5	0.0324 (9)	0.0243 (8)	0.0511 (10)	0.0016 (7)	0.0095 (8)	−0.0011 (8)
C6	0.0363 (9)	0.0222 (9)	0.0418 (10)	−0.0036 (7)	0.0011 (8)	0.0018 (7)
N1	0.0362 (8)	0.0174 (7)	0.0364 (8)	−0.0009 (6)	0.0083 (6)	0.0001 (5)
O1	0.0422 (7)	0.0245 (6)	0.0735 (9)	−0.0040 (5)	0.0089 (7)	−0.0150 (6)
O2	0.0570 (8)	0.0287 (7)	0.0701 (9)	−0.0123 (6)	0.0238 (7)	0.0029 (6)
O3	0.0514 (8)	0.0230 (7)	0.0428 (8)	0.0047 (6)	−0.0020 (6)	0.0005 (6)
O4	0.0538 (8)	0.0267 (7)	0.0481 (8)	−0.0046 (6)	0.0220 (6)	−0.0036 (7)
O5	0.0431 (8)	0.0273 (7)	0.0546 (9)	0.0025 (7)	0.0059 (7)	−0.0002 (6)

Geometric parameters (Å, º) top

Zn1—O3	2.0953 (14)	C4—C5	1.371 (2)
Zn1—O3ⁱ	2.0953 (14)	C4—H4	0.9300
Zn1—N1ⁱ	2.1355 (13)	C5—N1	1.345 (2)
Zn1—N1	2.1356 (13)	C5—H5	0.9300
Zn1—O4ⁱ	2.1504 (13)	C6—O2	1.238 (2)
Zn1—O4	2.1504 (13)	C6—O1	1.250 (2)
F1—C2	1.3457 (19)	O3—H3A	0.83 (3)
C1—N1	1.336 (2)	O3—H3B	0.74 (2)
C1—C2	1.371 (2)	O4—H4A	0.79 (3)
C1—H1	0.9300	O4—H4B	0.82 (2)
C2—C3	1.377 (2)	O5—H5A	0.75 (3)
C3—C4	1.396 (2)	O5—H5B	0.79 (2)
C3—C6	1.516 (2)

O3—Zn1—O3ⁱ	180.0	C2—C3—C6	123.74 (15)
O3—Zn1—N1ⁱ	92.42 (5)	C4—C3—C6	121.34 (15)
O3ⁱ—Zn1—N1ⁱ	87.58 (5)	C5—C4—C3	120.75 (16)
O3—Zn1—N1	87.58 (5)	C5—C4—H4	119.6
O3ⁱ—Zn1—N1	92.42 (5)	C3—C4—H4	119.6
N1ⁱ—Zn1—N1	180.00 (8)	N1—C5—C4	122.80 (15)
O3—Zn1—O4ⁱ	90.79 (6)	N1—C5—H5	118.6
O3ⁱ—Zn1—O4ⁱ	89.21 (6)	C4—C5—H5	118.6
N1ⁱ—Zn1—O4ⁱ	91.25 (5)	O2—C6—O1	126.76 (16)
N1—Zn1—O4ⁱ	88.76 (5)	O2—C6—C3	117.00 (15)
O3—Zn1—O4	89.21 (6)	O1—C6—C3	116.21 (15)
O3ⁱ—Zn1—O4	90.79 (6)	C1—N1—C5	117.22 (15)
N1ⁱ—Zn1—O4	88.76 (5)	C1—N1—Zn1	117.71 (11)
N1—Zn1—O4	91.24 (5)	C5—N1—Zn1	125.06 (11)
O4ⁱ—Zn1—O4	180.0	Zn1—O3—H3A	126.1 (17)
N1—C1—C2	121.99 (16)	Zn1—O3—H3B	113.1 (17)
N1—C1—H1	119.0	H3A—O3—H3B	104 (2)
C2—C1—H1	119.0	Zn1—O4—H4A	122.5 (18)
F1—C2—C1	116.55 (14)	Zn1—O4—H4B	107.5 (18)
F1—C2—C3	121.15 (15)	H4A—O4—H4B	113 (3)
C1—C2—C3	122.29 (15)	H5A—O5—H5B	115 (3)
C2—C3—C4	114.90 (15)

N1—C1—C2—F1	−179.40 (14)	C2—C1—N1—C5	−1.1 (2)
N1—C1—C2—C3	1.4 (3)	C2—C1—N1—Zn1	178.06 (12)
F1—C2—C3—C4	−179.08 (16)	C4—C5—N1—C1	−0.6 (3)
C1—C2—C3—C4	0.0 (2)	C4—C5—N1—Zn1	−179.72 (14)
F1—C2—C3—C6	2.6 (2)	O3—Zn1—N1—C1	−133.21 (12)
C1—C2—C3—C6	−178.23 (16)	O3ⁱ—Zn1—N1—C1	46.79 (12)
C2—C3—C4—C5	−1.7 (2)	O4ⁱ—Zn1—N1—C1	−42.37 (12)
C6—C3—C4—C5	176.61 (16)	O4—Zn1—N1—C1	137.63 (12)
C3—C4—C5—N1	2.1 (3)	O3—Zn1—N1—C5	45.92 (14)
C2—C3—C6—O2	−148.22 (17)	O3ⁱ—Zn1—N1—C5	−134.08 (14)
C4—C3—C6—O2	33.6 (2)	O4ⁱ—Zn1—N1—C5	136.77 (14)
C2—C3—C6—O1	33.4 (2)	O4—Zn1—N1—C5	−43.23 (14)
C4—C3—C6—O1	−144.78 (17)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱⁱ	0.83 (3)	1.86 (3)	2.6892 (18)	174 (2)
O3—H3B···O5ⁱⁱⁱ	0.74 (2)	2.01 (2)	2.745 (2)	176 (2)
O4—H4A···O2^iv	0.79 (3)	2.05 (3)	2.837 (2)	174 (2)
O4—H4B···O5^v	0.82 (2)	1.95 (3)	2.7643 (19)	171 (3)
O5—H5A···O2	0.75 (3)	2.05 (3)	2.796 (2)	174 (3)
O5—H5B···O1^vi	0.79 (2)	1.96 (3)	2.738 (2)	167 (2)
O5—H5B···F1^vi	0.79 (2)	2.55 (2)	2.9929 (17)	117.2 (18)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₆H₃FNO₂)₂(H₂O)₄]·2H₂O
M_r	453.65
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	6.6042 (4), 19.1953 (10), 6.8697 (4)
β (°)	99.225 (1)
V (Å³)	859.61 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.28 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (TWINABS; Bruker, 2003)
T_min, T_max	0.890, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	1734, 1740, 1605
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.065, 1.07
No. of reflections	1740
No. of parameters	149
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19

Computer programs: SMART-NT (Bruker, 2003), SAINT-Plus-NT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O3	2.0953 (14)	Zn1—O4	2.1504 (13)
Zn1—N1	2.1356 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.83 (3)	1.86 (3)	2.6892 (18)	174 (2)
O3—H3B···O5ⁱⁱ	0.74 (2)	2.01 (2)	2.745 (2)	176 (2)
O4—H4A···O2ⁱⁱⁱ	0.79 (3)	2.05 (3)	2.837 (2)	174 (2)
O4—H4B···O5^iv	0.82 (2)	1.95 (3)	2.7643 (19)	171 (3)
O5—H5A···O2	0.75 (3)	2.05 (3)	2.796 (2)	174 (3)
O5—H5B···O1^v	0.79 (2)	1.96 (3)	2.738 (2)	167 (2)
O5—H5B···F1^v	0.79 (2)	2.55 (2)	2.9929 (17)	117.2 (18)

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

Acknowledgements

Financial support from the National Science Foundation, awards CHE-0714555 and CHE-0714439, is gratefully acknowledged.

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