Crystal structure of poly[[trans-di­aqua­bis­[μ2-trans-4,4′-(diazenedi­yl)dipyridine]­nickel(II)] diiodide ethanol disolvate]

Perles, J.; Cortijo, M.; Herrero, S.

doi:10.1107/S1600536814016158

metal-organic compounds

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Volume 70| Part 9| September 2014| Pages m314-m315

doi:10.1107/S1600536814016158

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Crystal structure of poly[[trans-diaquabis[μ₂-trans-4,4′-(diazenediyl)dipyridine]nickel(II)] diiodide ethanol disolvate]

Josefina Perles,^a ^* Miguel Cortijo ^a and Santiago Herrero ^a

^aDepartamento de Química Inorgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Spain
^*Correspondence e-mail: jperles@quim.ucm.es

Edited by I. Brito, University of Antofagasta, Chile (Received 2 July 2014; accepted 11 July 2014; online 1 August 2014)

In the title compound, {[Ni(C₁₀H₈N₄)₂(H₂O)₂]I₂·2C₂H₅OH}_n, the complex shows an octahedral environment of the Ni²⁺ cation in which it is located on a centre of symmetry, linked to two water molecules and the pyridine-N atoms of four 4,4′-(diazenediyl)dipyridine ligands bridging Ni²⁺ cations along the b- and c-axis directions, giving rise to a two-dimensional arrangement. The Ni—N bond lengths are in the range 2.109 (4)–2.186 (3) Å and the Ni—O bond length is 2.080 (3) Å. The 4,4′-(diazenediyl)dipyridine ligand lies on an inversion centre. An O—H⋯O hydrogen-bond interaction is observed between water and ethanol molecules. The I⁻ ions can be regarded as free anions in the crystal lattice.

Keywords: crystal structure; nickel coordination compound; bidimensional MOF; cationic network.

CCDC reference: 1013422

1. Related literature

For related two-dimensional structures, see: Carlucci et al. (2003 ); Noro et al. (2005 , 2006 ); Li et al. (2007 ); Pan et al. (2010 ); Aijaz et al. (2011 ).

2. Experimental

2.1. Crystal data

[Ni(C₁₀H₈N₄)₂(H₂O)₂]I₂·2C₂H₆O
M_r = 809.09
Monoclinic, P 2₁ /n
a = 8.6367 (11) Å
b = 13.2598 (16) Å
c = 13.4188 (14) Å
β = 101.737 (3)°
V = 1504.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.74 mm⁻¹
T = 100 K
0.12 × 0.08 × 0.06 mm

2.2. Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.77, T_max = 0.85
19224 measured reflections
2741 independent reflections
1948 reflections with I > 2σ(I)
R_int = 0.067

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.097
S = 1.00
2741 reflections
185 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2ⁱ	0.83 (4)	1.91 (4)	2.703 (6)	161 (5)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1013422

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814016158/bx2463sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016158/bx2463Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016158/bx2463Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536814016158/bx2463Isup4.docx

checkCIF report

Related Literature top

A similar laminar structure was found for the compound [Ni(NCS)₂(t-apy)₂]·3toluene (Noro et al., 2006) although in this latter case there is no one-dimensional H-bond chain. For related 2D structures see: Carlucci et al. (2003); Noro et al. (2005 and 2006); Li et al. (2007); Pan et al. (2010); and Aijaz et al. (2011).

Preparation top

Nickel(II) iodide (0.30 g, 1.0 mmol), trans-4,4'-(diazenediyl)dipyridine (0.18 g, 1.0 mmol), ethanol (9 mL), and water (3 mL) were placed into an 85 mL Teflon vessel with a magnetic stirrer. The vessel was sealed with a lid equipped with a temperature sensor and placed in a ETHOS ONE microwave oven. The reaction mixture was heated for 3 hours at 120°C and left to cool afterwards. Slow interdiffusion of diethyl ether in the obtained solution gave rise to red crystals suitable for single-crystal X-ray diffraction after a few days.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

For related 2D structures see: Carlucci et al. (2003); Noro et al. (2005 and 2006); Li et al. (2007); Pan et al. (2010); and Aijaz et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Part of the polymeric structure for the title compound. Symmetry code for compound (i):-x, -y+2, -z+2; (2i): -x-y+1,-z+1;(3i):-x,-y+1,-z+2.
	Fig. 2. Simplified drawing of a layer parallel to (011). Hydrogen atoms have been omitted for clarity.

Poly[[trans-diaquabis[µ₂-trans-4,4'-(diazenediyl)dipyridine]nickel(II)] diiodide ethanol disolvate] top

Crystal data top

[Ni(C₁₀H₈N₄)₂(H₂O)₂]I₂·2C₂H₆O	F(000) = 796
M_r = 809.09	D_x = 1.786 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.6367 (11) Å	Cell parameters from 3456 reflections
b = 13.2598 (16) Å	θ = 2.9–21.6°
c = 13.4188 (14) Å	µ = 2.74 mm⁻¹
β = 101.737 (3)°	T = 100 K
V = 1504.6 (3) Å³	Prismatic, clear orange–red
Z = 2	0.12 × 0.08 × 0.06 mm

Data collection top

Bruker Kappa APEXII diffractometer	2741 independent reflections
Graphite monochromator	1948 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	R_int = 0.067
single crystal scans	θ_max = 25.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.77, T_max = 0.85	k = −15→15
19224 measured reflections	l = −15→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0416P)² + 2.7231P] where P = (F_o² + 2F_c²)/3
2741 reflections	(Δ/σ)_max < 0.001
185 parameters	Δρ_max = 0.95 e Å⁻³
3 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

[Ni(C₁₀H₈N₄)₂(H₂O)₂]I₂·2C₂H₆O	V = 1504.6 (3) Å³
M_r = 809.09	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6367 (11) Å	µ = 2.74 mm⁻¹
b = 13.2598 (16) Å	T = 100 K
c = 13.4188 (14) Å	0.12 × 0.08 × 0.06 mm
β = 101.737 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	2741 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1948 reflections with I > 2σ(I)
T_min = 0.77, T_max = 0.85	R_int = 0.067
19224 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.95 e Å⁻³
2741 reflections	Δρ_min = −0.86 e Å⁻³
185 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

	x	y	z	U_iso*/U_eq
I1	0.01318 (5)	0.80017 (3)	0.33435 (3)	0.05632 (18)
Ni1	0	0.5	1.0	0.0183 (2)
C1	0.1600 (6)	0.4962 (4)	0.8111 (3)	0.0278 (11)
H1	0.2538	0.4945	0.8623	0.033*
C2	0.1749 (6)	0.4983 (4)	0.7105 (3)	0.0304 (12)
H2	0.2763	0.5	0.6934	0.036*
C3	0.0387 (6)	0.4978 (4)	0.6352 (3)	0.0290 (12)
C4	−0.1044 (6)	0.4962 (4)	0.6634 (4)	0.0365 (13)
H4	−0.1996	0.4952	0.6134	0.044*
C5	−0.1092 (6)	0.4962 (4)	0.7655 (3)	0.0363 (13)
H5	−0.2096	0.496	0.784	0.044*
C6	0.1181 (6)	0.7073 (4)	0.9562 (4)	0.0320 (12)
H6	0.1913	0.668	0.9286	0.038*
C7	0.1276 (7)	0.8108 (4)	0.9503 (4)	0.0416 (14)
H7	0.2052	0.842	0.9196	0.05*
C8	0.0228 (7)	0.8671 (4)	0.9897 (4)	0.0402 (15)
C9	−0.0855 (7)	0.8207 (4)	1.0356 (4)	0.0444 (15)
H9	−0.1575	0.8591	1.0651	0.053*
C10	−0.0877 (7)	0.7150 (4)	1.0381 (4)	0.0388 (14)
H10	−0.1634	0.6824	1.0694	0.047*
C11	0.8888 (11)	0.7821 (7)	0.7076 (6)	0.095 (3)
H11A	0.9057	0.8424	0.7508	0.142*
H11B	0.9055	0.7217	0.7504	0.142*
H11C	0.7804	0.7823	0.6675	0.142*
C12	1.0001 (11)	0.7823 (7)	0.6391 (7)	0.093 (3)
H12A	1.1095	0.7802	0.6796	0.112*
H12B	0.9832	0.7214	0.5957	0.112*
N1	0.0212 (5)	0.4964 (3)	0.8404 (3)	0.0226 (9)
N2	0.0617 (5)	0.4987 (3)	0.5323 (3)	0.0345 (10)
N3	0.0113 (5)	0.6588 (3)	0.9985 (3)	0.0240 (9)
N4	0.0347 (6)	0.9783 (4)	0.9742 (4)	0.0490 (13)
O1	0.2450 (4)	0.4913 (3)	1.0428 (2)	0.0263 (8)
H1A	0.305 (5)	0.539 (3)	1.062 (4)	0.039*
H1B	0.293 (6)	0.442 (3)	1.074 (3)	0.039*
O2	0.9803 (5)	0.8708 (3)	0.5759 (3)	0.0568 (12)
H2A	0.9192	0.8576	0.5203	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0540 (3)	0.0502 (3)	0.0633 (3)	−0.0059 (2)	0.0085 (2)	−0.0198 (2)
Ni1	0.0260 (5)	0.0134 (4)	0.0159 (4)	0.0006 (4)	0.0054 (3)	0.0000 (3)
C1	0.025 (3)	0.038 (3)	0.019 (2)	0.001 (2)	0.001 (2)	0.000 (2)
C2	0.028 (3)	0.041 (3)	0.024 (2)	−0.001 (2)	0.011 (2)	−0.001 (2)
C3	0.040 (3)	0.030 (3)	0.017 (2)	0.002 (2)	0.005 (2)	−0.002 (2)
C4	0.024 (3)	0.061 (4)	0.025 (3)	0.002 (3)	0.005 (2)	0.003 (3)
C5	0.030 (3)	0.057 (4)	0.024 (3)	0.000 (3)	0.010 (2)	−0.001 (2)
C6	0.033 (3)	0.024 (3)	0.038 (3)	0.001 (2)	0.007 (2)	0.003 (2)
C7	0.041 (3)	0.024 (3)	0.058 (4)	−0.001 (3)	0.006 (3)	0.009 (3)
C8	0.041 (4)	0.016 (3)	0.055 (3)	−0.009 (3)	−0.010 (3)	0.001 (2)
C9	0.054 (4)	0.027 (3)	0.052 (4)	0.013 (3)	0.008 (3)	−0.011 (3)
C10	0.055 (4)	0.025 (3)	0.038 (3)	0.000 (3)	0.016 (3)	−0.001 (2)
C11	0.103 (7)	0.109 (7)	0.068 (5)	−0.001 (6)	0.008 (5)	0.033 (5)
C12	0.085 (6)	0.091 (7)	0.106 (7)	0.004 (5)	0.025 (5)	0.033 (5)
N1	0.028 (2)	0.019 (2)	0.0208 (19)	−0.0026 (18)	0.0066 (17)	0.0008 (17)
N2	0.038 (3)	0.050 (3)	0.018 (2)	0.000 (2)	0.0098 (16)	0.000 (2)
N3	0.032 (2)	0.019 (2)	0.0202 (19)	−0.0020 (19)	0.0026 (17)	−0.0018 (16)
N4	0.044 (3)	0.050 (3)	0.056 (3)	0.002 (3)	0.017 (2)	−0.008 (2)
O1	0.027 (2)	0.024 (2)	0.0267 (17)	0.0012 (15)	0.0034 (15)	0.0030 (14)
O2	0.056 (3)	0.054 (3)	0.060 (3)	0.006 (2)	0.011 (2)	0.008 (2)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	2.080 (3)	C7—C8	1.360 (8)
Ni1—O1	2.080 (3)	C7—H7	0.95
Ni1—N3	2.109 (4)	C8—C9	1.366 (8)
Ni1—N3ⁱ	2.109 (4)	C8—N4	1.496 (7)
Ni1—N1	2.186 (3)	C9—C10	1.403 (8)
Ni1—N1ⁱ	2.186 (3)	C9—H9	0.95
C1—N1	1.336 (6)	C10—N3	1.324 (7)
C1—C2	1.381 (6)	C10—H10	0.95
C1—H1	0.95	C11—C12	1.458 (12)
C2—C3	1.386 (7)	C11—H11A	0.98
C2—H2	0.95	C11—H11B	0.98
C3—C4	1.365 (7)	C11—H11C	0.98
C3—N2	1.435 (6)	C12—O2	1.437 (9)
C4—C5	1.378 (7)	C12—H12A	0.99
C4—H4	0.95	C12—H12B	0.99
C5—N1	1.348 (6)	N2—N2ⁱⁱ	1.229 (8)
C5—H5	0.95	N4—N4ⁱⁱⁱ	1.156 (9)
C6—N3	1.342 (7)	O1—H1A	0.82 (2)
C6—C7	1.378 (7)	O1—H1B	0.833 (19)
C6—H6	0.95	O2—H2A	0.84

O1ⁱ—Ni1—O1	180.00 (19)	C6—C7—H7	120.9
O1ⁱ—Ni1—N3	89.33 (15)	C7—C8—C9	119.9 (5)
O1—Ni1—N3	90.68 (15)	C7—C8—N4	114.7 (5)
O1ⁱ—Ni1—N3ⁱ	90.67 (15)	C9—C8—N4	125.3 (6)
O1—Ni1—N3ⁱ	89.33 (15)	C8—C9—C10	118.3 (6)
N3—Ni1—N3ⁱ	180.0 (2)	C8—C9—H9	120.9
O1ⁱ—Ni1—N1	90.79 (13)	C10—C9—H9	120.9
O1—Ni1—N1	89.21 (13)	N3—C10—C9	122.7 (5)
N3—Ni1—N1	89.97 (15)	N3—C10—H10	118.7
N3ⁱ—Ni1—N1	90.03 (15)	C9—C10—H10	118.7
O1ⁱ—Ni1—N1ⁱ	89.21 (13)	C12—C11—H11A	109.5
O1—Ni1—N1ⁱ	90.79 (13)	C12—C11—H11B	109.5
N3—Ni1—N1ⁱ	90.03 (15)	H11A—C11—H11B	109.5
N3ⁱ—Ni1—N1ⁱ	89.97 (15)	C12—C11—H11C	109.5
N1—Ni1—N1ⁱ	180.0 (2)	H11A—C11—H11C	109.5
N1—C1—C2	123.7 (4)	H11B—C11—H11C	109.5
N1—C1—H1	118.1	O2—C12—C11	111.0 (7)
C2—C1—H1	118.1	O2—C12—H12A	109.4
C1—C2—C3	118.6 (5)	C11—C12—H12A	109.4
C1—C2—H2	120.7	O2—C12—H12B	109.4
C3—C2—H2	120.7	C11—C12—H12B	109.4
C4—C3—C2	118.7 (4)	H12A—C12—H12B	108.0
C4—C3—N2	125.3 (4)	C1—N1—C5	116.3 (4)
C2—C3—N2	116.0 (5)	C1—N1—Ni1	123.2 (3)
C3—C4—C5	119.2 (5)	C5—N1—Ni1	120.5 (3)
C3—C4—H4	120.4	N2ⁱⁱ—N2—C3	114.1 (5)
C5—C4—H4	120.4	C10—N3—C6	117.1 (4)
N1—C5—C4	123.5 (5)	C10—N3—Ni1	121.6 (4)
N1—C5—H5	118.2	C6—N3—Ni1	121.3 (3)
C4—C5—H5	118.2	N4ⁱⁱⁱ—N4—C8	110.5 (7)
N3—C6—C7	123.7 (5)	Ni1—O1—H1A	126 (4)
N3—C6—H6	118.1	Ni1—O1—H1B	124 (4)
C7—C6—H6	118.1	H1A—O1—H1B	103 (5)
C8—C7—C6	118.2 (5)	C12—O2—H2A	109.5
C8—C7—H7	120.9

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2^iv	0.83 (4)	1.91 (4)	2.703 (6)	161 (5)

Symmetry code: (iv) x−1/2, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.83 (4)	1.91 (4)	2.703 (6)	161 (5)

Symmetry code: (i) x−1/2, −y+3/2, z+1/2.

Acknowledgements

Diffraction data were collected at the SCXRD laboratory from the Servicio Interdepartamental de Investigación (SIdI, UAM). Financial support received from the Spanish Ministerio de Economía y Competitividad (CTQ2011-23066) and the Comunidad de Madrid (S2009/MAT-1467) is gratefully acknowledged.

References

Aijaz, A., Sañudo, E. C. & Bharadwaj, P. K. (2011). Cryst. Growth Des. 11, 1122–1134. Web of Science CSD CrossRef CAS Google Scholar
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