catena-Poly[[diaqua­bis­(formato-κO)nickel(II)]-μ-2,4,6-tris­(4-pyrid­yl)-1,3,5-triazine-κ2N2:N4]

Feng, M.; Tian, H.-J.; Mi, H.-F.; Hu, T.-L.

doi:10.1107/S1600536811012281

metal-organic compounds

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Volume 67| Part 5| May 2011| Page m563

doi:10.1107/S1600536811012281

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catena-Poly[[diaquabis(formato-κO)nickel(II)]-μ-2,4,6-tris(4-pyridyl)-1,3,5-triazine-κ²N²:N⁴]

Miao Feng,^a Hui-Juan Tian,^a Huai-Feng Mi ^a ^* and Tong-Liang Hu ^b

^aBiochemical Section of Key Laboratory of Functional Polymer Materials, The Ministry of Education of China, Chemical School of Nankai University, 300071 Tianjin, People's Republic of China, and ^bDepartment of Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: hfmi@nankai.edu.cn

(Received 19 March 2011; accepted 2 April 2011; online 13 April 2011)

In the title compound, [Ni(CHO₂)₂(C₁₈H₁₂N₆)(H₂O)₂]_n, the Ni^II ion, lying on a crystallographic inversion center, has a distorted octahedral coordination comprising two water ligands, two O-atom donors from formate ligands and two N-atom donors from the 2,4,6-tris(4-pyridyl)-1,3,5-triazine ligands. These ligands bridge the Ni^II complex units, forming zigzag chains along the c axis. Adjacent chains are linked by O—H⋯O hydrogen bonds, forming a three-dimensional supramolecular network.

Related literature

For the structures and properties of coordination compounds with 2,4,6-tris(4-pyridyl)-1,3,5-triazine as a ligand, see: Abrahams et al. (1999 ); Barrios et al. (2007 ); Batten et al. (1995 ); Dybtsev et al. (2004 ). 2~2~O ligand should bind through the O atom

Experimental

Crystal data

[Ni(CHO₂)₂(C₁₈H₁₂N₆)(H₂O)₂]
M_r = 497.11
Monoclinic, C 2/c
a = 24.725 (5) Å
b = 10.969 (2) Å
c = 7.4196 (15) Å
β = 90.23 (3)°
V = 2012.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 K
0.15 × 0.10 × 0.10 mm

Data collection

Rigaku SCX-mini diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.836, T_max = 1.000
10365 measured reflections
2302 independent reflections
1937 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.078
S = 1.05
2302 reflections
153 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H6⋯O2ⁱ	0.86	1.96	2.818 (2)	177
O3—H7⋯O2ⁱⁱ	0.83	1.95	2.777 (2)	174
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012281/bq2289sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012281/bq2289Isup2.hkl

checkCIF report

Comment top

As an interesting polydentate nitrogen donor ligand, 2,4,6-tris(4-pyridyl)-1,3,5-triazine has attracted increasing attention in the synthesis of novel transition metal complexes with novel topology and properties (Abrahams et al., 1999; Dybtsev et al., 2004; Barrios et al., 2007; Batten et al., 1995). Our interest in 2,4,6-tris(4-pyridyl)-1,3,5-triazine transition metal complexes prompts us to report the title compound (I).

As shown in Fig. 1, in the title compound, [Ni(C₁₈H₁₂N₆)(H₂O)₂(HCOO)₂]n, the Ni^II ion, lying on a crystallographic inversion center, has a distorted octahedral coordination sphere comprising two water ligands, two O-atom donors from formate ligands and two N-atom donors from the 2,4,6-tris(4-pyridyl)-1,3,5-triazine ligands. These ligands bridge the Ni^II complex units to form zigzag chains along c axis (Fig. 2). Adjacent chains are linked by O—H···O hydrogen bonds (Table 1), forming a three-dimensional supramolecular network (Fig. 3).

Related literature top

For the structures and properties of coordination compounds with 2,4,6-tris(4-pyridyl)-1,3,5-triazine as a ligand, see: Abrahams et al. (1999); Barrios et al. (2007); Batten et al. (1995); Dybtsev et al. (2004).

Experimental top

A mixture of Ni(HCOO)₂.2H₂O (0.15 mmol), 2,4,6-tris(4-pyridyl)-1,3,5-triazine (0.05 mmol), and 10 ml H₂O were put in a 23-ml Teflon liner reactor and heated at 413 K in oven for 72 h. The resulting solution was slowly cooled to room temperature to yield single crystals of the title compound.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: publCIF (Westrip, 2010).

Figures top

	Fig. 1. A fragment of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) (-x, -y, -z + 1.5); (ii) (-x + 1/2, -y + 1.5, -z + 2).
	Fig. 2. A view of the title structure along the c axis, showing the zigzag chain.
	Fig. 3. The crystal packing of the title compound. O—H···O hydrogen bonds are shown as dashed lines.

catena-Poly[[diaquabis(formato-κO)nickel(II)]-µ- 2,4,6-tris(4-pyridyl)-1,3,5-triazine-κ²N²:N⁴] top

Crystal data top

[Ni(CHO₂)₂(C₁₈H₁₂N₆)(H₂O)₂]	F(000) = 1024
M_r = 497.11	D_x = 1.641 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9569 reflections
a = 24.725 (5) Å	θ = 3.1–27.5°
b = 10.969 (2) Å	µ = 1.02 mm⁻¹
c = 7.4196 (15) Å	T = 293 K
β = 90.23 (3)°	Block, green
V = 2012.2 (7) Å³	0.15 × 0.10 × 0.10 mm
Z = 4

Data collection top

Rigaku SCX-mini diffractometer	2302 independent reflections
Radiation source: fine-focus sealed tube	1937 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −31→32
T_min = 0.836, T_max = 1.000	k = −14→14
10365 measured reflections	l = −9→9

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0334P)² + 2.3183P] where P = (F_o² + 2F_c²)/3
2302 reflections	(Δ/σ)_max = 0.001
153 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Ni(CHO₂)₂(C₁₈H₁₂N₆)(H₂O)₂]	V = 2012.2 (7) Å³
M_r = 497.11	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 24.725 (5) Å	µ = 1.02 mm⁻¹
b = 10.969 (2) Å	T = 293 K
c = 7.4196 (15) Å	0.15 × 0.10 × 0.10 mm
β = 90.23 (3)°

Data collection top

Rigaku SCX-mini diffractometer	2302 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1937 reflections with I > 2σ(I)
T_min = 0.836, T_max = 1.000	R_int = 0.040
10365 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.05	Δρ_max = 0.33 e Å⁻³
2302 reflections	Δρ_min = −0.28 e Å⁻³
153 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
Ni1	0.2500	0.7500	1.0000	0.01798 (11)
O1	0.22888 (6)	0.64439 (12)	0.78618 (18)	0.0263 (3)
O2	0.19168 (7)	0.61015 (14)	0.5190 (2)	0.0337 (4)
O3	0.29896 (6)	0.86926 (12)	0.85264 (19)	0.0263 (3)
H6	0.3027	0.9430	0.8884	0.039*
H7	0.3001	0.8711	0.7403	0.039*
N1	0.18044 (6)	0.86186 (14)	0.9633 (2)	0.0204 (4)
N2	0.04510 (7)	1.19452 (15)	0.8071 (2)	0.0251 (4)
N3	0.0000	1.0076 (2)	0.7500	0.0245 (5)
N4	0.0000	1.6408 (2)	0.7500	0.0428 (7)
C1	0.13264 (8)	0.81007 (18)	0.9265 (3)	0.0241 (4)
H1	0.1299	0.7257	0.9355	0.029*
C2	0.08733 (8)	0.87491 (18)	0.8760 (3)	0.0248 (4)
H2	0.0551	0.8349	0.8495	0.030*
C3	0.09060 (8)	1.00126 (18)	0.8654 (3)	0.0210 (4)
C4	0.13930 (8)	1.05662 (18)	0.9086 (3)	0.0239 (4)
H4	0.1427	1.1410	0.9053	0.029*
C5	0.18282 (8)	0.98373 (18)	0.9569 (3)	0.0240 (4)
H5	0.2154	1.0215	0.9864	0.029*
C6	0.04255 (8)	1.07256 (18)	0.8045 (3)	0.0208 (4)
C7	0.0000	1.2503 (3)	0.7500	0.0229 (6)
C8	0.0000	1.3860 (3)	0.7500	0.0252 (6)
C9	−0.04675 (9)	1.4505 (2)	0.7877 (3)	0.0327 (5)
H9	−0.0791	1.4101	0.8097	0.039*
C10	−0.04418 (10)	1.5768 (2)	0.7918 (4)	0.0400 (6)
H10	−0.0750	1.6194	0.8257	0.048*
C11	0.20837 (8)	0.67816 (19)	0.6412 (3)	0.0246 (4)
H11	0.2052	0.7617	0.6226	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01931 (18)	0.01621 (18)	0.01840 (18)	0.00276 (15)	−0.00433 (12)	−0.00092 (15)
O1	0.0344 (8)	0.0217 (7)	0.0227 (7)	0.0047 (6)	−0.0086 (6)	−0.0032 (6)
O2	0.0428 (9)	0.0349 (9)	0.0233 (8)	0.0010 (7)	−0.0093 (7)	−0.0037 (7)
O3	0.0350 (8)	0.0216 (7)	0.0224 (7)	−0.0013 (6)	0.0005 (6)	0.0019 (6)
N1	0.0188 (8)	0.0193 (8)	0.0231 (8)	0.0024 (7)	−0.0044 (6)	0.0001 (7)
N2	0.0212 (9)	0.0180 (8)	0.0362 (10)	0.0011 (7)	−0.0062 (7)	−0.0005 (7)
N3	0.0193 (12)	0.0187 (12)	0.0353 (14)	0.000	−0.0059 (10)	0.000
N4	0.0506 (19)	0.0189 (14)	0.059 (2)	0.000	−0.0079 (15)	0.000
C1	0.0238 (10)	0.0154 (10)	0.0332 (11)	−0.0003 (8)	−0.0034 (8)	0.0014 (8)
C2	0.0191 (10)	0.0196 (10)	0.0357 (12)	−0.0029 (8)	−0.0057 (8)	0.0002 (9)
C3	0.0192 (9)	0.0210 (10)	0.0226 (10)	0.0023 (8)	−0.0023 (8)	−0.0013 (8)
C4	0.0228 (10)	0.0159 (9)	0.0330 (11)	0.0000 (8)	−0.0052 (8)	−0.0007 (8)
C5	0.0181 (10)	0.0222 (10)	0.0316 (11)	−0.0020 (8)	−0.0050 (8)	−0.0036 (9)
C6	0.0178 (9)	0.0196 (10)	0.0249 (10)	0.0007 (8)	−0.0012 (8)	−0.0009 (8)
C7	0.0224 (13)	0.0167 (13)	0.0297 (14)	0.000	−0.0021 (11)	0.000
C8	0.0285 (15)	0.0185 (14)	0.0284 (15)	0.000	−0.0066 (12)	0.000
C9	0.0278 (11)	0.0236 (11)	0.0466 (14)	0.0024 (9)	−0.0025 (10)	0.0023 (10)
C10	0.0407 (14)	0.0256 (12)	0.0536 (16)	0.0108 (11)	−0.0052 (12)	−0.0010 (11)
C11	0.0275 (11)	0.0234 (10)	0.0228 (10)	0.0023 (8)	−0.0015 (8)	0.0002 (8)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	2.0309 (14)	C1—C2	1.378 (3)
Ni1—O1	2.0309 (14)	C1—H1	0.9300
Ni1—O3ⁱ	2.0934 (14)	C2—C3	1.391 (3)
Ni1—O3	2.0935 (14)	C2—H2	0.9300
Ni1—N1	2.1293 (16)	C3—C4	1.385 (3)
Ni1—N1ⁱ	2.1294 (16)	C3—C6	1.491 (3)
O1—C11	1.244 (2)	C4—C5	1.387 (3)
O2—C11	1.244 (2)	C4—H4	0.9300
O3—H6	0.8557	C5—H5	0.9300
O3—H7	0.8343	C7—N2ⁱⁱ	1.339 (2)
N1—C1	1.338 (3)	C7—C8	1.489 (4)
N1—C5	1.339 (3)	C8—C9ⁱⁱ	1.385 (3)
N2—C7	1.339 (2)	C8—C9	1.385 (3)
N2—C6	1.339 (3)	C9—C10	1.387 (3)
N3—C6ⁱⁱ	1.332 (2)	C9—H9	0.9300
N3—C6	1.332 (2)	C10—H10	0.9300
N4—C10	1.336 (3)	C11—H11	0.9300
N4—C10ⁱⁱ	1.336 (3)

O1ⁱ—Ni1—O1	180.0	C1—C2—H2	120.6
O1ⁱ—Ni1—O3ⁱ	95.50 (6)	C3—C2—H2	120.6
O1—Ni1—O3ⁱ	84.50 (6)	C4—C3—C2	118.34 (18)
O1ⁱ—Ni1—O3	84.50 (6)	C4—C3—C6	122.08 (18)
O1—Ni1—O3	95.50 (6)	C2—C3—C6	119.57 (18)
O3ⁱ—Ni1—O3	180.0	C3—C4—C5	118.69 (18)
O1ⁱ—Ni1—N1	88.64 (6)	C3—C4—H4	120.7
O1—Ni1—N1	91.36 (6)	C5—C4—H4	120.7
O3ⁱ—Ni1—N1	87.62 (6)	N1—C5—C4	123.41 (18)
O3—Ni1—N1	92.38 (6)	N1—C5—H5	118.3
O1ⁱ—Ni1—N1ⁱ	91.36 (6)	C4—C5—H5	118.3
O1—Ni1—N1ⁱ	88.64 (6)	N3—C6—N2	125.14 (19)
O3ⁱ—Ni1—N1ⁱ	92.39 (6)	N3—C6—C3	116.04 (18)
O3—Ni1—N1ⁱ	87.61 (6)	N2—C6—C3	118.82 (17)
N1—Ni1—N1ⁱ	180.0	N2ⁱⁱ—C7—N2	125.7 (3)
C11—O1—Ni1	127.47 (13)	N2ⁱⁱ—C7—C8	117.17 (13)
Ni1—O3—H6	119.3	N2—C7—C8	117.17 (13)
Ni1—O3—H7	124.0	C9ⁱⁱ—C8—C9	118.5 (3)
H6—O3—H7	106.4	C9ⁱⁱ—C8—C7	120.74 (14)
C1—N1—C5	117.10 (16)	C9—C8—C7	120.74 (14)
C1—N1—Ni1	119.57 (13)	C8—C9—C10	118.5 (2)
C5—N1—Ni1	122.98 (13)	C8—C9—H9	120.8
C7—N2—C6	114.35 (18)	C10—C9—H9	120.8
C6ⁱⁱ—N3—C6	115.4 (2)	N4—C10—C9	123.8 (2)
C10—N4—C10ⁱⁱ	116.6 (3)	N4—C10—H10	118.1
N1—C1—C2	123.56 (18)	C9—C10—H10	118.1
N1—C1—H1	118.2	O2—C11—O1	125.8 (2)
C2—C1—H1	118.2	O2—C11—H11	117.1
C1—C2—C3	118.84 (18)	O1—C11—H11	117.1

O3ⁱ—Ni1—O1—C11	125.73 (18)	C3—C4—C5—N1	0.3 (3)
O3—Ni1—O1—C11	−54.27 (18)	C6ⁱⁱ—N3—C6—N2	−0.22 (15)
N1—Ni1—O1—C11	38.26 (18)	C6ⁱⁱ—N3—C6—C3	−179.8 (2)
N1ⁱ—Ni1—O1—C11	−141.74 (18)	C7—N2—C6—N3	0.4 (3)
O1ⁱ—Ni1—N1—C1	−137.13 (16)	C7—N2—C6—C3	180.00 (15)
O1—Ni1—N1—C1	42.87 (16)	C4—C3—C6—N3	173.55 (17)
O3ⁱ—Ni1—N1—C1	−41.57 (15)	C2—C3—C6—N3	−5.0 (3)
O3—Ni1—N1—C1	138.43 (15)	C4—C3—C6—N2	−6.1 (3)
O1ⁱ—Ni1—N1—C5	49.91 (16)	C2—C3—C6—N2	175.33 (19)
O1—Ni1—N1—C5	−130.09 (16)	C6—N2—C7—N2ⁱⁱ	−0.19 (13)
O3ⁱ—Ni1—N1—C5	145.47 (16)	C6—N2—C7—C8	179.82 (13)
O3—Ni1—N1—C5	−34.53 (16)	N2ⁱⁱ—C7—C8—C9ⁱⁱ	−145.57 (15)
C5—N1—C1—C2	2.8 (3)	N2—C7—C8—C9ⁱⁱ	34.43 (15)
Ni1—N1—C1—C2	−170.57 (17)	N2ⁱⁱ—C7—C8—C9	34.43 (15)
N1—C1—C2—C3	−1.2 (3)	N2—C7—C8—C9	−145.57 (15)
C1—C2—C3—C4	−0.9 (3)	C9ⁱⁱ—C8—C9—C10	−2.10 (17)
C1—C2—C3—C6	177.77 (19)	C7—C8—C9—C10	177.90 (17)
C2—C3—C4—C5	1.3 (3)	C10ⁱⁱ—N4—C10—C9	−2.33 (18)
C6—C3—C4—C5	−177.31 (19)	C8—C9—C10—N4	4.5 (4)
C1—N1—C5—C4	−2.3 (3)	Ni1—O1—C11—O2	−173.47 (16)
Ni1—N1—C5—C4	170.79 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H6···O2ⁱⁱⁱ	0.86	1.96	2.818 (2)	177
O3—H7···O2^iv	0.83	1.95	2.777 (2)	174

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

Experimental details

Crystal data
Chemical formula	[Ni(CHO₂)₂(C₁₈H₁₂N₆)(H₂O)₂]
M_r	497.11
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	24.725 (5), 10.969 (2), 7.4196 (15)
β (°)	90.23 (3)
V (Å³)	2012.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku SCX-mini diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.836, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10365, 2302, 1937
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.078, 1.05
No. of reflections	2302
No. of parameters	153
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.28

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H6···O2ⁱ	0.86	1.96	2.818 (2)	177
O3—H7···O2ⁱⁱ	0.83	1.95	2.777 (2)	174

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China [project approval No. 20974053].

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