Bis{(1-methyl-imidazol-2-ylmeth-yl)[2-(2-pyridyl)eth-yl]amine-κN,N',N''}zinc(II) bis-(hexa-fluoridophosphate).

Two tridentate N-heterocyclic ligands chelate the Zn(II) atom in the title compound, [Zn(C(12)H(16)N(4))(2)](PF(6))(2), conferring a fac-octa-hedral 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 = 787.89

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.147

S = 1.04

3655 reflections

219 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.49 e Å−3

Δρmin = −0.71 e Å−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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044419/xu2647Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C12H16N4)2](PF6)2	F(000) = 1600
Mr = 787.89	Dx = 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

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

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(Fo2) + (0.0755P)2 + 5.7073P] where P = (Fo2 + 2Fc2)/3
3655 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 1.49 e Å−3
1 restraint	Δρmin = −0.71 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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)