Bis{(1-methyl­imidazol-2-ylmeth­yl)[2-(2-pyridyl)eth­yl]amine-κ3N,N′,N′′}zinc(II) bis­(hexa­fluoridophosphate)

Wu, A.-Z.; Ng, S.W.

doi:10.1107/S1600536809044419

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1479

https://doi.org/10.1107/S1600536809044419

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Bis{(1-methylimidazol-2-ylmethyl)[2-(2-pyridyl)ethyl]amine-κ³N,N′,N′′}zinc(II) bis(hexafluoridophosphate)

Ai-Zhi Wu ^a ^* and Seik Weng Ng ^b

^aSchool of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou 510006, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: wuaizhi@gzhtcm.edu.cn

(Received 19 October 2009; accepted 26 October 2009; online 31 October 2009)

Two tridentate N-heterocyclic ligands chelate the Zn^II atom in the title compound, [Zn(C₁₂H₁₆N₄)₂](PF₆)₂, conferring a fac-octahedral geometry. The Zn^II atom lies on a center of inversion. The cation is linked to the anion by an N—H⋯F hydrogen bond.

Related literature

No crystal structure studies of metal complexes with the N-heterocyclic ligand have been reported. For the synthesis of the ligand, see: Greatti et al. (2008 ).

Experimental

Crystal data

[Zn(C₁₂H₁₆N₄)₂](PF₆)₂
M_r = 787.89
Orthorhombic, P b c a
a = 13.3147 (5) Å
b = 11.8147 (4) Å
c = 20.3359 (6) Å
V = 3199.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 100 K
0.40 × 0.38 × 0.35 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.698, T_max = 0.728
18287 measured reflections
3655 independent reflections
2740 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.147
S = 1.04
3655 reflections
219 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.49 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—N1	2.188 (3)
Zn1—N2	2.095 (3)
Zn1—N4	2.298 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯F1	0.88 (1)	2.21 (1)	3.083 (4)	179 (3)

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809044419/xu2647sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044419/xu2647Isup2.hkl

checkCIF report

Related literature top

No crystal structure studies of metal complexes with the N-heterocyclic ligand have been reported. For the synthesis of the ligand, see: Greatti et al. (2008).

Experimental top

(1-Methylimidazol-2-ylmethyl)(pyridin-2-ylethyl)amine was synthesized according to a literature method (Greatti et al., 2008).

The ligand (1 mmol, 0.26 g) dissolved in methanol (5 ml) was reacted with zinc hexafluorophosphat (1 mmol, 0.36 g) dissolved in water (5 ml). The mixture was filtered and the solution set aside for the growth of colorless block-shaped crystals that formed after several days in 60% yield. CH&N elemental analysis. Found: C 36.24, H 4.07, N 13.36%; calculated: C 36.55, H 4.06, N 14.22%.

Structure description top

No crystal structure studies of metal complexes with the N-heterocyclic ligand have been reported. For the synthesis of the ligand, see: Greatti et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Zn(C₁₂H₁₆N₄)₂] 2[PF₆] at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Bis{(1-methylimidazol-2-ylmethyl)[2-(2-pyridyl)ethyl]amine- κ³N,N',N''}zinc(II) bis(hexafluoridophosphate) top

Crystal data top

[Zn(C₁₂H₁₆N₄)₂](PF₆)₂	F(000) = 1600
M_r = 787.89	D_x = 1.636 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4790 reflections
a = 13.3147 (5) Å	θ = 2.5–28.2°
b = 11.8147 (4) Å	µ = 0.97 mm⁻¹
c = 20.3359 (6) Å	T = 100 K
V = 3199.0 (2) Å³	Block, colorless
Z = 4	0.40 × 0.38 × 0.35 mm

Data collection top

Bruker APEXII diffractometer	3655 independent reflections
Radiation source: fine-focus sealed tube	2740 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→17
T_min = 0.698, T_max = 0.728	k = −13→15
18287 measured reflections	l = −22→26

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0755P)² + 5.7073P] where P = (F_o² + 2F_c²)/3
3655 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 1.49 e Å⁻³
1 restraint	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Zn(C₁₂H₁₆N₄)₂](PF₆)₂	V = 3199.0 (2) Å³
M_r = 787.89	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 13.3147 (5) Å	µ = 0.97 mm⁻¹
b = 11.8147 (4) Å	T = 100 K
c = 20.3359 (6) Å	0.40 × 0.38 × 0.35 mm

Data collection top

Bruker APEXII diffractometer	3655 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2740 reflections with I > 2σ(I)
T_min = 0.698, T_max = 0.728	R_int = 0.048
18287 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.49 e Å⁻³
3655 reflections	Δρ_min = −0.71 e Å⁻³
219 parameters

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	0.02098 (16)
P1	0.38657 (6)	0.83958 (7)	0.68434 (4)	0.0251 (2)
F1	0.47058 (17)	0.7507 (2)	0.66130 (14)	0.0524 (7)
F2	0.47025 (19)	0.9039 (2)	0.72513 (13)	0.0563 (7)
F3	0.30477 (18)	0.9306 (2)	0.70513 (12)	0.0540 (7)
F4	0.30581 (18)	0.7775 (2)	0.63902 (15)	0.0586 (7)
F5	0.3608 (2)	0.7641 (3)	0.74431 (16)	0.0840 (11)
F6	0.4135 (2)	0.9157 (2)	0.62167 (13)	0.0588 (7)
N1	0.40722 (19)	0.5353 (2)	0.58640 (13)	0.0231 (6)
H1	0.424 (3)	0.5969 (18)	0.6075 (15)	0.027 (9)*
N2	0.48361 (19)	0.3368 (2)	0.53888 (14)	0.0248 (6)
N3	0.4460 (2)	0.2326 (2)	0.62505 (14)	0.0282 (6)
N4	0.3548 (2)	0.4794 (2)	0.44007 (14)	0.0267 (6)
C1	0.4281 (3)	0.4463 (3)	0.63589 (16)	0.0274 (7)
H1A	0.3690	0.4358	0.6648	0.033*
H1B	0.4861	0.4685	0.6635	0.033*
C2	0.4510 (2)	0.3384 (3)	0.60004 (16)	0.0243 (7)
C3	0.4784 (3)	0.1600 (3)	0.57608 (19)	0.0326 (8)
H3	0.4838	0.0800	0.5790	0.039*
C4	0.5009 (2)	0.2245 (3)	0.5236 (2)	0.0294 (7)
H4	0.5248	0.1972	0.4825	0.035*
C5	0.4136 (3)	0.1995 (3)	0.69075 (18)	0.0372 (9)
H5A	0.3915	0.2667	0.7150	0.056*
H5B	0.4697	0.1638	0.7141	0.056*
H5C	0.3578	0.1457	0.6874	0.056*
C6	0.2980 (2)	0.5415 (3)	0.57167 (17)	0.0254 (7)
H6A	0.2621	0.5715	0.6106	0.031*
H6B	0.2724	0.4643	0.5629	0.031*
C7	0.2758 (2)	0.6170 (3)	0.51236 (17)	0.0292 (7)
H7A	0.2092	0.6529	0.5181	0.035*
H7B	0.3267	0.6778	0.5099	0.035*
C8	0.2766 (2)	0.5506 (3)	0.44925 (17)	0.0277 (7)
C9	0.1977 (3)	0.5560 (4)	0.40485 (19)	0.0391 (9)
H9	0.1448	0.6087	0.4116	0.047*
C10	0.1957 (3)	0.4854 (4)	0.3511 (2)	0.0498 (11)
H10	0.1425	0.4895	0.3201	0.060*
C11	0.2727 (3)	0.4086 (4)	0.34328 (19)	0.0449 (10)
H11	0.2724	0.3564	0.3078	0.054*
C12	0.3505 (3)	0.4095 (3)	0.38849 (17)	0.0330 (8)
H12	0.4040	0.3573	0.3825	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0169 (3)	0.0213 (3)	0.0247 (3)	−0.00221 (18)	0.00329 (19)	0.00056 (19)
P1	0.0221 (4)	0.0233 (4)	0.0299 (5)	0.0017 (3)	−0.0017 (3)	−0.0007 (3)
F1	0.0394 (12)	0.0431 (13)	0.0747 (18)	0.0150 (11)	−0.0061 (12)	−0.0213 (12)
F2	0.0428 (13)	0.0550 (15)	0.0710 (18)	0.0110 (12)	−0.0256 (12)	−0.0275 (13)
F3	0.0449 (13)	0.0636 (16)	0.0534 (15)	0.0283 (12)	−0.0118 (11)	−0.0196 (12)
F4	0.0410 (13)	0.0396 (13)	0.095 (2)	−0.0040 (10)	−0.0220 (13)	−0.0184 (13)
F5	0.0588 (18)	0.106 (3)	0.087 (2)	0.0105 (17)	0.0142 (15)	0.069 (2)
F6	0.0594 (16)	0.0596 (16)	0.0573 (17)	−0.0066 (13)	−0.0012 (13)	0.0243 (13)
N1	0.0209 (12)	0.0230 (12)	0.0253 (15)	−0.0035 (10)	0.0010 (10)	−0.0006 (11)
N2	0.0218 (13)	0.0216 (12)	0.0309 (16)	−0.0020 (10)	0.0017 (11)	0.0006 (11)
N3	0.0248 (13)	0.0270 (14)	0.0328 (16)	−0.0074 (11)	−0.0075 (11)	0.0064 (12)
N4	0.0197 (13)	0.0328 (14)	0.0277 (15)	−0.0047 (11)	0.0012 (11)	0.0005 (11)
C1	0.0271 (15)	0.0277 (16)	0.0273 (18)	−0.0017 (13)	0.0014 (13)	0.0013 (13)
C2	0.0196 (14)	0.0218 (15)	0.0317 (18)	−0.0034 (12)	−0.0024 (12)	0.0040 (13)
C3	0.0272 (16)	0.0223 (15)	0.048 (2)	−0.0028 (13)	−0.0097 (15)	0.0008 (15)
C4	0.0221 (15)	0.0250 (16)	0.041 (2)	−0.0027 (12)	−0.0029 (14)	−0.0050 (14)
C5	0.043 (2)	0.0341 (18)	0.035 (2)	−0.0167 (16)	−0.0106 (16)	0.0121 (15)
C6	0.0171 (14)	0.0282 (15)	0.0310 (18)	−0.0024 (12)	0.0061 (12)	−0.0010 (13)
C7	0.0164 (14)	0.0285 (16)	0.043 (2)	0.0007 (12)	0.0027 (13)	0.0011 (14)
C8	0.0176 (14)	0.0335 (17)	0.0321 (19)	−0.0035 (12)	0.0036 (13)	0.0048 (14)
C9	0.0227 (17)	0.057 (2)	0.037 (2)	0.0016 (16)	−0.0007 (15)	0.0107 (18)
C10	0.0278 (19)	0.087 (3)	0.034 (2)	−0.006 (2)	−0.0050 (16)	0.003 (2)
C11	0.0316 (19)	0.076 (3)	0.027 (2)	−0.012 (2)	0.0021 (15)	−0.0128 (19)
C12	0.0235 (16)	0.044 (2)	0.031 (2)	−0.0061 (15)	0.0052 (13)	−0.0049 (15)

Geometric parameters (Å, º) top

Zn1—N1	2.188 (3)	C1—H1A	0.9900
Zn1—N1ⁱ	2.188 (3)	C1—H1B	0.9900
Zn1—N2ⁱ	2.095 (3)	C3—C4	1.345 (5)
Zn1—N2	2.095 (3)	C3—H3	0.9500
Zn1—N4	2.298 (3)	C4—H4	0.9500
Zn1—N4ⁱ	2.298 (3)	C5—H5A	0.9800
P1—F5	1.549 (3)	C5—H5B	0.9800
P1—F2	1.583 (2)	C5—H5C	0.9800
P1—F3	1.588 (2)	C6—C7	1.529 (5)
P1—F4	1.595 (2)	C6—H6A	0.9900
P1—F6	1.601 (3)	C6—H6B	0.9900
P1—F1	1.605 (2)	C7—C8	1.504 (5)
N1—C1	1.482 (4)	C7—H7A	0.9900
N1—C6	1.486 (4)	C7—H7B	0.9900
N1—H1	0.875 (10)	C8—C9	1.386 (5)
N2—C2	1.317 (4)	C9—C10	1.375 (6)
N2—C4	1.382 (4)	C9—H9	0.9500
N3—C2	1.351 (4)	C10—C11	1.378 (6)
N3—C3	1.383 (5)	C10—H10	0.9500
N3—C5	1.457 (4)	C11—C12	1.385 (5)
N4—C12	1.336 (4)	C11—H11	0.9500
N4—C8	1.352 (4)	C12—H12	0.9500
C1—C2	1.500 (4)

N2ⁱ—Zn1—N2	180.00 (6)	C2—C1—H1A	110.1
N2ⁱ—Zn1—N1	100.73 (10)	N1—C1—H1B	110.1
N2—Zn1—N1	79.27 (10)	C2—C1—H1B	110.1
N2ⁱ—Zn1—N1ⁱ	79.27 (10)	H1A—C1—H1B	108.4
N2—Zn1—N1ⁱ	100.73 (10)	N2—C2—N3	111.0 (3)
N1—Zn1—N1ⁱ	180.0	N2—C2—C1	122.5 (3)
N2ⁱ—Zn1—N4	89.13 (10)	N3—C2—C1	126.4 (3)
N2—Zn1—N4	90.87 (10)	C4—C3—N3	106.8 (3)
N1—Zn1—N4	88.35 (10)	C4—C3—H3	126.6
N1ⁱ—Zn1—N4	91.65 (9)	N3—C3—H3	126.6
N2ⁱ—Zn1—N4ⁱ	90.87 (10)	C3—C4—N2	109.2 (3)
N2—Zn1—N4ⁱ	89.13 (10)	C3—C4—H4	125.4
N1—Zn1—N4ⁱ	91.65 (9)	N2—C4—H4	125.4
N1ⁱ—Zn1—N4ⁱ	88.35 (10)	N3—C5—H5A	109.5
N4—Zn1—N4ⁱ	180.0	N3—C5—H5B	109.5
F5—P1—F2	91.12 (18)	H5A—C5—H5B	109.5
F5—P1—F3	91.64 (17)	N3—C5—H5C	109.5
F2—P1—F3	91.04 (13)	H5A—C5—H5C	109.5
F5—P1—F4	92.36 (18)	H5B—C5—H5C	109.5
F2—P1—F4	176.28 (17)	N1—C6—C7	112.2 (2)
F3—P1—F4	90.16 (13)	N1—C6—H6A	109.2
F5—P1—F6	179.05 (19)	C7—C6—H6A	109.2
F2—P1—F6	89.42 (16)	N1—C6—H6B	109.2
F3—P1—F6	89.12 (15)	C7—C6—H6B	109.2
F4—P1—F6	87.08 (15)	H6A—C6—H6B	107.9
F5—P1—F1	90.41 (17)	C8—C7—C6	111.6 (3)
F2—P1—F1	88.66 (13)	C8—C7—H7A	109.3
F3—P1—F1	177.93 (16)	C6—C7—H7A	109.3
F4—P1—F1	90.02 (13)	C8—C7—H7B	109.3
F6—P1—F1	88.83 (15)	C6—C7—H7B	109.3
C1—N1—C6	110.8 (2)	H7A—C7—H7B	108.0
C1—N1—Zn1	107.68 (19)	N4—C8—C9	121.5 (3)
C6—N1—Zn1	113.6 (2)	N4—C8—C7	116.6 (3)
C1—N1—H1	102 (2)	C9—C8—C7	121.8 (3)
C6—N1—H1	108 (2)	C10—C9—C8	120.3 (4)
Zn1—N1—H1	114 (2)	C10—C9—H9	119.8
C2—N2—C4	106.3 (3)	C8—C9—H9	119.8
C2—N2—Zn1	112.2 (2)	C9—C10—C11	118.5 (4)
C4—N2—Zn1	141.4 (2)	C9—C10—H10	120.8
C2—N3—C3	106.7 (3)	C11—C10—H10	120.8
C2—N3—C5	127.4 (3)	C10—C11—C12	118.3 (4)
C3—N3—C5	125.9 (3)	C10—C11—H11	120.8
C12—N4—C8	117.4 (3)	C12—C11—H11	120.8
C12—N4—Zn1	121.2 (2)	N4—C12—C11	123.9 (4)
C8—N4—Zn1	120.6 (2)	N4—C12—H12	118.0
N1—C1—C2	108.1 (3)	C11—C12—H12	118.0
N1—C1—H1A	110.1

N2ⁱ—Zn1—N1—C1	−152.89 (19)	Zn1—N2—C2—C1	0.5 (4)
N2—Zn1—N1—C1	27.11 (19)	C3—N3—C2—N2	0.4 (4)
N4—Zn1—N1—C1	118.3 (2)	C5—N3—C2—N2	−180.0 (3)
N4ⁱ—Zn1—N1—C1	−61.7 (2)	C3—N3—C2—C1	−176.9 (3)
N2ⁱ—Zn1—N1—C6	84.0 (2)	C5—N3—C2—C1	2.7 (5)
N2—Zn1—N1—C6	−96.0 (2)	N1—C1—C2—N2	23.2 (4)
N4—Zn1—N1—C6	−4.8 (2)	N1—C1—C2—N3	−159.8 (3)
N4ⁱ—Zn1—N1—C6	175.2 (2)	C2—N3—C3—C4	−0.4 (4)
N1—Zn1—N2—C2	−15.5 (2)	C5—N3—C3—C4	179.9 (3)
N1ⁱ—Zn1—N2—C2	164.5 (2)	N3—C3—C4—N2	0.3 (4)
N4—Zn1—N2—C2	−103.7 (2)	C2—N2—C4—C3	−0.1 (4)
N4ⁱ—Zn1—N2—C2	76.3 (2)	Zn1—N2—C4—C3	175.0 (3)
N1—Zn1—N2—C4	169.6 (4)	C1—N1—C6—C7	−169.8 (3)
N1ⁱ—Zn1—N2—C4	−10.4 (4)	Zn1—N1—C6—C7	−48.4 (3)
N4—Zn1—N2—C4	81.4 (4)	N1—C6—C7—C8	90.1 (3)
N4ⁱ—Zn1—N2—C4	−98.6 (4)	C12—N4—C8—C9	−3.8 (5)
N2ⁱ—Zn1—N4—C12	109.5 (3)	Zn1—N4—C8—C9	165.9 (3)
N2—Zn1—N4—C12	−70.5 (3)	C12—N4—C8—C7	171.8 (3)
N1—Zn1—N4—C12	−149.8 (3)	Zn1—N4—C8—C7	−18.5 (4)
N1ⁱ—Zn1—N4—C12	30.2 (3)	C6—C7—C8—N4	−47.0 (4)
N2ⁱ—Zn1—N4—C8	−59.9 (2)	C6—C7—C8—C9	128.7 (3)
N2—Zn1—N4—C8	120.1 (2)	N4—C8—C9—C10	2.3 (6)
N1—Zn1—N4—C8	40.9 (2)	C7—C8—C9—C10	−173.1 (3)
N1ⁱ—Zn1—N4—C8	−139.1 (2)	C8—C9—C10—C11	1.0 (6)
C6—N1—C1—C2	92.0 (3)	C9—C10—C11—C12	−2.6 (6)
Zn1—N1—C1—C2	−32.7 (3)	C8—N4—C12—C11	2.2 (5)
C4—N2—C2—N3	−0.2 (3)	Zn1—N4—C12—C11	−167.5 (3)
Zn1—N2—C2—N3	−176.9 (2)	C10—C11—C12—N4	1.1 (6)
C4—N2—C2—C1	177.2 (3)

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
N1—H1···F1	0.88 (1)	2.21 (1)	3.083 (4)	179 (3)

Experimental details

Crystal data
Chemical formula	[Zn(C₁₂H₁₆N₄)₂](PF₆)₂
M_r	787.89
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	13.3147 (5), 11.8147 (4), 20.3359 (6)
V (Å³)	3199.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.40 × 0.38 × 0.35

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.698, 0.728
No. of measured, independent and observed [I > 2σ(I)] reflections	18287, 3655, 2740
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.147, 1.04
No. of reflections	3655
No. of parameters	219
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.49, −0.71

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Zn1—N1	2.188 (3)	Zn1—N4	2.298 (3)
Zn1—N2	2.095 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···F1	0.88 (1)	2.21 (1)	3.083 (4)	179 (3)

Acknowledgements

We thank Guangzhou University of Chinese Medicine and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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