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Acta Cryst. (2010). E66, m1430    [ doi:10.1107/S1600536810041577 ]

Tetrakis(1H-imidazole-[kappa]N3)(2-phenylpropanedioato-[kappa]2O1,O3)nickel(II)

K.-L. Zhang, G.-W. Diao and S. W. Ng

Abstract top

In the title complex, [Ni(C9H6O4)(C3H4N2)4], the NiII ion is O,O'-chelated by the phenylmalonato ligand and coordinated by four imidazole ligands in a slightly distorted octahedral geometry. In the crystal structure, symmetry-related molecules are linked by N-H...O hydrogen bonds, generating a three-dimensional network.

Comment top

We have previously reported the crystal structure of the tetrakis(imidazole) adduct of cobalt(II) phenylmalonate. The structure features the carboxylate-chelated cobalt(II) atom bonded to four N-heterocycles; each of these has a nitrogen-donor site that enables the octahedrally coordinated mononuclear molecule to connect with each other to form a three-dimensional network (Zhang et al., 2007). The nickel analog (Fig. 1) is isostructural, the two compounds crystallizing with similar unit cell dimensions.

Related literature top

For the cobalt(II) analog, see: Zhang et al. (2007).

Experimental top

Imidazole (0.339 g. 0.56 mmol) was dissolved in methanol (10 ml) and to the solution was added nickel nitrate hexahydrate (0.480 g, 1.65 mmol) dissolved in water (6 ml). To the clear soluiton was added phenylmalonic acid (0.300 g, 1.65 mmol) and sodium hydroxide (0.120 g, 3.30 mmol) dissolved in water (10 ml). The filtered solution was set aside for the growth of green crystals over several days; yield 50%. CH&N elemental analysis. Calc. for C21H22N8NiO4: C 49.53, H 4.36, N 22.00%. Found: C 49.61, H 4.49, N 21.91%.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C).

The imidazolium H-atoms were similarly treated (N–H 0.88 Å; Uiso(H) 1.2Ueq(N)).

The crystal has several voids but these are too small (20Å3) to accomodate a solvent molecule.

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, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ni(C3H4N2)4(C9H6O4) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Tetrakis(1H-imidazole-κN3)(2-phenylpropanedioato- κ2O1,O3)nickel(II) top
Crystal data top
[Ni(C9H6O4)(C3H4N2)4]F(000) = 1056
Mr = 509.18Dx = 1.438 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2481 reflections
a = 8.5358 (8) Åθ = 2.6–21.7°
b = 13.3148 (12) ŵ = 0.87 mm−1
c = 20.6996 (19) ÅT = 293 K
V = 2352.6 (4) Å3Prism, green
Z = 40.25 × 0.20 × 0.15 mm
Data collection top
Bruker SMART APEX
diffractometer		5516 independent reflections
Radiation source: fine-focus sealed tube4013 reflections with I > 2σ(I)
graphiteRint = 0.051
ω scansθmax = 27.8°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.812, Tmax = 0.881k = −17→17
15962 measured reflectionsl = −19→27
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0326P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
5516 reflectionsΔρmax = 0.41 e Å−3
307 parametersΔρmin = −0.31 e Å−3
0 restraintsAbsolute structure: Flack (1983), 2344 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.082 (13)
Crystal data top
[Ni(C9H6O4)(C3H4N2)4]V = 2352.6 (4) Å3
Mr = 509.18Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.5358 (8) ŵ = 0.87 mm−1
b = 13.3148 (12) ÅT = 293 K
c = 20.6996 (19) Å0.25 × 0.20 × 0.15 mm
Data collection top
Bruker SMART APEX
diffractometer		5516 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4013 reflections with I > 2σ(I)
Tmin = 0.812, Tmax = 0.881Rint = 0.051
15962 measured reflectionsθmax = 27.8°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.086Δρmax = 0.41 e Å−3
S = 0.98Δρmin = −0.31 e Å−3
5516 reflectionsAbsolute structure: Flack (1983), 2344 Friedel pairs
307 parametersFlack parameter: 0.082 (13)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.66167 (4)0.40568 (3)0.336577 (18)0.02636 (10)
O10.8851 (2)0.40575 (17)0.29819 (9)0.0324 (4)
O21.0679 (2)0.37546 (16)0.22649 (12)0.0433 (6)
O30.5823 (2)0.41866 (15)0.24132 (9)0.0323 (5)
O40.6203 (3)0.43579 (17)0.13674 (11)0.0515 (7)
N10.6652 (3)0.24683 (16)0.33088 (13)0.0338 (6)
N20.5969 (3)0.0939 (2)0.30389 (16)0.0597 (9)
H20.53880.04320.29080.072*
N30.4310 (2)0.4058 (2)0.37002 (11)0.0301 (5)
N40.1739 (3)0.4091 (2)0.36620 (12)0.0388 (6)
H40.07820.41100.35040.047*
N50.6703 (3)0.56328 (16)0.33579 (12)0.0312 (5)
N60.7570 (3)0.7169 (2)0.32201 (14)0.0424 (8)
H60.81800.76670.30980.051*
N70.7489 (3)0.4034 (2)0.43160 (11)0.0324 (6)
N80.8143 (4)0.4576 (2)0.52810 (14)0.0500 (8)
H80.83590.49910.55990.060*
C10.9291 (3)0.3761 (2)0.24304 (17)0.0300 (7)
C20.8045 (3)0.3333 (2)0.19607 (15)0.0343 (8)
H2A0.76620.27130.21610.041*
C30.6602 (3)0.4033 (2)0.19068 (14)0.0315 (6)
C40.8732 (3)0.3022 (2)0.13164 (16)0.0361 (8)
C50.8607 (4)0.2032 (3)0.11128 (17)0.0468 (9)
H50.80550.15690.13600.056*
C60.9301 (5)0.1738 (3)0.0545 (2)0.0635 (12)
H6A0.92020.10750.04100.076*
C71.0126 (5)0.2392 (4)0.0179 (2)0.0683 (13)
H71.06020.2173−0.01990.082*
C81.0264 (5)0.3368 (3)0.0363 (2)0.0643 (12)
H8A1.08310.38170.01100.077*
C90.9556 (4)0.3689 (3)0.09264 (17)0.0471 (9)
H90.96320.43600.10470.057*
C100.5503 (4)0.1886 (2)0.31110 (17)0.0450 (9)
H100.44880.21080.30310.054*
C110.7919 (4)0.1839 (2)0.3360 (2)0.0493 (9)
H110.89200.20360.34840.059*
C120.7502 (4)0.0899 (3)0.3204 (2)0.0626 (12)
H120.81390.03330.32080.075*
C130.3064 (3)0.4087 (2)0.33245 (16)0.0361 (7)
H130.31060.41020.28760.043*
C140.3722 (3)0.4050 (3)0.43166 (15)0.0391 (7)
H140.43180.40400.46930.047*
C150.2137 (4)0.4060 (3)0.42918 (17)0.0446 (8)
H150.14540.40480.46420.054*
C160.7835 (4)0.6195 (2)0.31334 (16)0.0383 (8)
H160.87280.59410.29350.046*
C170.5650 (4)0.6304 (2)0.36077 (17)0.0427 (9)
H170.47050.61320.38020.051*
C180.6178 (4)0.7249 (2)0.35329 (17)0.0426 (9)
H180.56900.78370.36680.051*
C190.7768 (4)0.4830 (3)0.46802 (16)0.0392 (8)
H190.77090.54890.45330.047*
C200.7710 (5)0.3241 (3)0.47194 (18)0.0585 (12)
H200.75900.25710.46040.070*
C210.8133 (6)0.3571 (3)0.53140 (18)0.0682 (13)
H210.83680.31790.56730.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02413 (16)0.02630 (16)0.02864 (19)−0.00065 (17)−0.00168 (18)−0.00153 (19)
O10.0262 (10)0.0397 (11)0.0312 (11)−0.0002 (10)0.0005 (9)−0.0080 (11)
O20.0255 (11)0.0565 (15)0.0479 (15)0.0019 (10)0.0034 (11)−0.0166 (12)
O30.0296 (10)0.0422 (13)0.0252 (11)0.0041 (10)0.0009 (9)−0.0002 (10)
O40.0486 (14)0.0700 (17)0.0359 (14)0.0183 (12)0.0071 (12)0.0217 (12)
N10.0380 (13)0.0312 (13)0.0322 (15)−0.0052 (12)−0.0028 (18)0.0004 (11)
N20.0581 (18)0.0281 (14)0.093 (3)−0.0143 (16)−0.0013 (17)−0.0146 (18)
N30.0258 (11)0.0332 (12)0.0313 (14)−0.0023 (13)−0.0017 (11)−0.0005 (14)
N40.0232 (11)0.0497 (15)0.0436 (15)0.0030 (15)−0.0003 (13)0.0011 (15)
N50.0278 (12)0.0303 (12)0.0356 (14)−0.0031 (10)0.0006 (17)−0.0003 (11)
N60.0387 (15)0.0343 (15)0.054 (2)−0.0088 (13)−0.0008 (14)0.0059 (15)
N70.0331 (12)0.0349 (13)0.0291 (14)0.0015 (13)−0.0029 (11)−0.0033 (15)
N80.064 (2)0.053 (2)0.0330 (18)0.0026 (18)−0.0074 (17)−0.0125 (15)
C10.0243 (15)0.0255 (16)0.040 (2)0.0061 (12)−0.0016 (14)−0.0010 (13)
C20.0326 (18)0.0358 (17)0.0346 (18)−0.0004 (14)0.0001 (15)0.0012 (15)
C30.0283 (13)0.0343 (14)0.0319 (15)−0.0006 (18)0.0009 (14)−0.0023 (15)
C40.0273 (16)0.049 (2)0.0322 (17)0.0077 (15)−0.0009 (14)−0.0051 (16)
C50.0362 (18)0.051 (2)0.053 (2)0.0041 (18)−0.0058 (18)−0.0053 (18)
C60.064 (3)0.069 (3)0.057 (3)0.018 (2)−0.007 (2)−0.031 (2)
C70.075 (3)0.088 (3)0.042 (3)0.032 (3)−0.001 (2)−0.013 (2)
C80.060 (3)0.088 (3)0.045 (3)0.018 (2)0.015 (2)0.015 (2)
C90.052 (2)0.048 (2)0.042 (2)0.0090 (17)0.0023 (19)0.0043 (17)
C100.0379 (18)0.0350 (18)0.062 (3)−0.0055 (15)0.0071 (17)−0.0004 (17)
C110.0431 (19)0.0379 (18)0.067 (3)0.0085 (14)−0.018 (2)−0.004 (2)
C120.056 (2)0.0342 (19)0.098 (4)0.006 (2)−0.009 (2)−0.003 (3)
C130.0293 (14)0.0416 (16)0.0374 (17)−0.0031 (14)−0.0022 (14)−0.0015 (19)
C140.0350 (16)0.0509 (18)0.0313 (17)0.0019 (18)−0.0008 (14)0.0026 (18)
C150.0366 (16)0.056 (2)0.041 (2)0.0009 (19)0.0089 (15)0.006 (2)
C160.0365 (17)0.0314 (19)0.047 (2)0.0011 (13)0.0027 (15)−0.0013 (15)
C170.0347 (17)0.0400 (18)0.053 (2)0.0016 (14)0.0081 (17)0.0003 (16)
C180.0430 (19)0.0261 (16)0.059 (3)0.0068 (14)0.0016 (17)0.0031 (15)
C190.0401 (19)0.044 (2)0.034 (2)−0.0004 (16)−0.0038 (16)−0.0028 (17)
C200.102 (3)0.038 (2)0.036 (2)0.003 (2)−0.020 (2)0.0050 (17)
C210.112 (4)0.057 (3)0.036 (2)0.006 (3)−0.025 (3)0.0050 (19)
Geometric parameters (Å, °) top
Ni1—O12.0662 (18)C2—C41.515 (4)
Ni1—N32.087 (2)C2—C31.549 (4)
Ni1—O32.092 (2)C2—H2A0.9800
Ni1—N52.100 (2)C4—C51.388 (5)
Ni1—N72.103 (2)C4—C91.391 (4)
Ni1—N12.118 (2)C5—C61.372 (5)
O1—C11.265 (4)C5—H50.9300
O2—C11.234 (3)C6—C71.352 (6)
O3—C31.258 (3)C6—H6A0.9300
O4—C31.245 (3)C7—C81.359 (5)
N1—C101.316 (4)C7—H70.9300
N1—C111.373 (4)C8—C91.382 (5)
N2—C101.330 (4)C8—H8A0.9300
N2—C121.353 (4)C9—H90.9300
N2—H20.8800C10—H100.9300
N3—C131.318 (3)C11—C121.340 (5)
N3—C141.371 (4)C11—H110.9300
N4—C131.329 (3)C12—H120.9300
N4—C151.348 (4)C13—H130.9300
N4—H40.8800C14—C151.355 (4)
N5—C161.308 (4)C14—H140.9300
N5—C171.369 (4)C15—H150.9300
N6—C161.329 (4)C16—H160.9300
N6—C181.357 (4)C17—C181.345 (4)
N6—H60.8800C17—H170.9300
N7—C191.323 (4)C18—H180.9300
N7—C201.359 (4)C19—H190.9300
N8—C191.328 (4)C20—C211.356 (5)
N8—C211.339 (4)C20—H200.9300
N8—H80.8800C21—H210.9300
C1—C21.550 (4)
O1—Ni1—N3176.75 (9)C5—C4—C2119.8 (3)
O1—Ni1—O386.37 (7)C9—C4—C2122.2 (3)
N3—Ni1—O390.39 (8)C6—C5—C4119.9 (4)
O1—Ni1—N587.95 (9)C6—C5—H5120.1
N3—Ni1—N591.98 (10)C4—C5—H5120.1
O3—Ni1—N585.50 (9)C7—C6—C5121.4 (4)
O1—Ni1—N791.88 (8)C7—C6—H6A119.3
N3—Ni1—N791.36 (9)C5—C6—H6A119.3
O3—Ni1—N7175.72 (9)C6—C7—C8120.3 (4)
N5—Ni1—N790.54 (10)C6—C7—H7119.9
O1—Ni1—N188.05 (10)C8—C7—H7119.9
N3—Ni1—N191.88 (10)C7—C8—C9119.6 (4)
O3—Ni1—N191.98 (9)C7—C8—H8A120.2
N5—Ni1—N1175.40 (10)C9—C8—H8A120.2
N7—Ni1—N191.87 (10)C8—C9—C4120.9 (4)
C1—O1—Ni1128.36 (18)C8—C9—H9119.5
C3—O3—Ni1126.92 (18)C4—C9—H9119.5
C10—N1—C11104.6 (2)N1—C10—N2111.8 (3)
C10—N1—Ni1126.6 (2)N1—C10—H10124.1
C11—N1—Ni1128.0 (2)N2—C10—H10124.1
C10—N2—C12107.3 (3)C12—C11—N1110.0 (3)
C10—N2—H2126.3C12—C11—H11125.0
C12—N2—H2126.3N1—C11—H11125.0
C13—N3—C14104.7 (2)C11—C12—N2106.3 (4)
C13—N3—Ni1124.44 (19)C11—C12—H12126.8
C14—N3—Ni1130.84 (18)N2—C12—H12126.8
C13—N4—C15107.1 (2)N3—C13—N4112.1 (3)
C13—N4—H4126.5N3—C13—H13123.9
C15—N4—H4126.5N4—C13—H13123.9
C16—N5—C17104.2 (3)C15—C14—N3109.3 (3)
C16—N5—Ni1126.9 (2)C15—C14—H14125.4
C17—N5—Ni1128.8 (2)N3—C14—H14125.4
C16—N6—C18106.8 (3)N4—C15—C14106.8 (3)
C16—N6—H6126.6N4—C15—H15126.6
C18—N6—H6126.6C14—C15—H15126.6
C19—N7—C20104.3 (3)N5—C16—N6112.7 (3)
C19—N7—Ni1125.8 (2)N5—C16—H16123.7
C20—N7—Ni1129.4 (2)N6—C16—H16123.7
C19—N8—C21107.5 (3)C18—C17—N5110.3 (3)
C19—N8—H8126.2C18—C17—H17124.8
C21—N8—H8126.2N5—C17—H17124.8
O2—C1—O1122.5 (3)C17—C18—N6106.0 (3)
O2—C1—C2118.9 (3)C17—C18—H18127.0
O1—C1—C2118.5 (3)N6—C18—H18127.0
C4—C2—C3114.1 (2)N7—C19—N8111.9 (3)
C4—C2—C1112.8 (2)N7—C19—H19124.1
C3—C2—C1111.7 (2)N8—C19—H19124.1
C4—C2—H2A105.8C21—C20—N7110.1 (3)
C3—C2—H2A105.8C21—C20—H20125.0
C1—C2—H2A105.8N7—C20—H20125.0
O4—C3—O3123.1 (3)N8—C21—C20106.2 (4)
O4—C3—C2119.4 (3)N8—C21—H21126.9
O3—C3—C2117.2 (3)C20—C21—H21126.9
C5—C4—C9118.0 (3)
O3—Ni1—O1—C1−28.3 (3)Ni1—O3—C3—O4−161.4 (2)
N5—Ni1—O1—C1−113.9 (3)Ni1—O3—C3—C223.8 (4)
N7—Ni1—O1—C1155.7 (3)C4—C2—C3—O4−6.3 (4)
N1—Ni1—O1—C163.9 (3)C1—C2—C3—O4123.0 (3)
O1—Ni1—O3—C315.1 (2)C4—C2—C3—O3168.7 (3)
N3—Ni1—O3—C3−164.7 (2)C1—C2—C3—O3−61.9 (4)
N5—Ni1—O3—C3103.4 (2)C3—C2—C4—C5−111.2 (3)
N1—Ni1—O3—C3−72.8 (2)C1—C2—C4—C5120.0 (3)
O1—Ni1—N1—C10−137.2 (3)C3—C2—C4—C971.8 (4)
N3—Ni1—N1—C1039.6 (3)C1—C2—C4—C9−57.1 (4)
O3—Ni1—N1—C10−50.9 (3)C9—C4—C5—C60.6 (5)
N7—Ni1—N1—C10131.0 (3)C2—C4—C5—C6−176.6 (3)
O1—Ni1—N1—C1130.7 (3)C4—C5—C6—C70.8 (6)
N3—Ni1—N1—C11−152.6 (3)C5—C6—C7—C8−1.1 (7)
O3—Ni1—N1—C11117.0 (3)C6—C7—C8—C90.1 (7)
N7—Ni1—N1—C11−61.1 (3)C7—C8—C9—C41.4 (6)
O3—Ni1—N3—C132.8 (3)C5—C4—C9—C8−1.7 (5)
N5—Ni1—N3—C1388.3 (3)C2—C4—C9—C8175.4 (3)
N7—Ni1—N3—C13178.9 (3)C11—N1—C10—N20.3 (4)
N1—Ni1—N3—C13−89.2 (3)Ni1—N1—C10—N2170.4 (2)
O3—Ni1—N3—C14−175.9 (3)C12—N2—C10—N10.5 (4)
N5—Ni1—N3—C14−90.4 (3)C10—N1—C11—C12−1.0 (4)
N7—Ni1—N3—C140.2 (3)Ni1—N1—C11—C12−171.0 (3)
N1—Ni1—N3—C1492.1 (3)N1—C11—C12—N21.3 (5)
O1—Ni1—N5—C163.4 (3)C10—N2—C12—C11−1.1 (5)
N3—Ni1—N5—C16−173.4 (3)C14—N3—C13—N4−0.4 (4)
O3—Ni1—N5—C16−83.1 (3)Ni1—N3—C13—N4−179.4 (2)
N7—Ni1—N5—C1695.3 (3)C15—N4—C13—N3−0.2 (4)
O1—Ni1—N5—C17−173.2 (3)C13—N3—C14—C150.8 (4)
N3—Ni1—N5—C1710.1 (3)Ni1—N3—C14—C15179.7 (2)
O3—Ni1—N5—C17100.3 (3)C13—N4—C15—C140.7 (4)
N7—Ni1—N5—C17−81.3 (3)N3—C14—C15—N4−1.0 (4)
O1—Ni1—N7—C1992.3 (2)C17—N5—C16—N6−0.3 (4)
N3—Ni1—N7—C19−87.6 (3)Ni1—N5—C16—N6−177.6 (2)
N5—Ni1—N7—C194.4 (3)C18—N6—C16—N51.1 (4)
N1—Ni1—N7—C19−179.5 (3)C16—N5—C17—C18−0.5 (4)
O1—Ni1—N7—C20−96.5 (3)Ni1—N5—C17—C18176.7 (2)
N3—Ni1—N7—C2083.5 (3)N5—C17—C18—N61.2 (4)
N5—Ni1—N7—C20175.5 (3)C16—N6—C18—C17−1.3 (4)
N1—Ni1—N7—C20−8.4 (3)C20—N7—C19—N8−0.1 (4)
Ni1—O1—C1—O2−176.5 (2)Ni1—N7—C19—N8172.8 (2)
Ni1—O1—C1—C2−0.1 (4)C21—N8—C19—N70.9 (5)
O2—C1—C2—C4−4.3 (4)C19—N7—C20—C21−0.6 (5)
O1—C1—C2—C4179.1 (3)Ni1—N7—C20—C21−173.2 (3)
O2—C1—C2—C3−134.4 (3)C19—N8—C21—C20−1.2 (6)
O1—C1—C2—C349.0 (4)N7—C20—C21—N81.2 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.882.062.943 (3)176
N4—H4···O1ii0.881.972.839 (3)168
N6—H6···O2iii0.881.902.774 (3)172
N8—H8···O4iv0.881.852.718 (3)169
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+3/2, −y+1, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.882.062.943 (3)176
N4—H4···O1ii0.881.972.839 (3)168
N6—H6···O2iii0.881.902.774 (3)172
N8—H8···O4iv0.881.852.718 (3)169
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+3/2, −y+1, z+1/2.
Acknowledgements top

We thank the Key Laboratory of Environmental Material and Environmental Engineering of Jiangsu Province, Yangzhou University and the University of Malaya for supporting this study.

references
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