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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1105.
Published online 2008 August 6. doi:  10.1107/S1600536808024008
PMCID: PMC2960619

Poly[aqua­[μ2-1,1′-(butane-1,4-di­yl)diimidazole](μ2-naphthalene-1,4-dicarboxyl­ato)nickel(II)]

Abstract

In the title compound, [Ni(C12H6O4)(C10H14N4)(H2O)]n, the coordination polyhedron around each NiII atom is a distorted cis-NiN2O4 octa­hedron. The naphthalene-1,4-dicarboxyl­ate and 1,1′-(butane-1,4-di­yl)diimidazole ligands bridge the Ni centres to form a two-dimensional (4,4)-network, and O—H(...)O hydrogen bonds complete the structure.

Related literature

For general background, see: Batten & Robson (1998 [triangle]). For a related structure, see: Ma et al., (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1105-scheme1.jpg

Experimental

Crystal data

  • [Ni(C12H6O4)(C10H14N4)(H2O)]
  • M r = 481.15
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1105-efi3.jpg
  • a = 12.4213 (12) Å
  • b = 13.2543 (13) Å
  • c = 13.4328 (13) Å
  • β = 107.361 (2)°
  • V = 2110.8 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.96 mm−1
  • T = 293 (2) K
  • 0.19 × 0.17 × 0.15 mm

Data collection

  • Bruker APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.827, T max = 0.866
  • 11720 measured reflections
  • 4157 independent reflections
  • 2982 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.097
  • S = 1.05
  • 4157 reflections
  • 297 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024008/hb2770sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024008/hb2770Isup2.hkl

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

Acknowledgments

The author thanks Beihua University for supporting this work.

supplementary crystallographic information

Comment

Metal-organic frameworks are currently of great interest because of their interesting structures and potential applications. So far, some interesting interpenetrated or entangled metal-organic networks with bis(imidazole)-containing ligands have been documented (Batten & Robson, 1998). Flexible ligands such as 1,1'-(1,4-butanediyl)bis(imidazole) (L) have been less explored to date (Ma et al., 2003). In this work, we selected 1,4-naphthalenedicarboxylic acid (H2ndc) and L as linkers, generating a new coordination polymer, [Ni(ndc)(L)(H2O)], (I), which is reported here.

In compound (I) each NiII atom is six-coordinated by two N atoms from two different L ligands, and four O atoms from three carboxylate oxygen atoms (one bidentate, one monodentate) and one water molecule in a distorted cis-NiN2O4 octohedral coordination sphere (Fig. 1). The two neighbouring NiII atoms are bridged by the ndc and L ligands to form a two-dimensional (4,4) network (Fig. 2) and O—H···O hydrogen bonds arising from the water molecule (Table 2) complete the structure.

Experimental

A mixture of H2ndc (0.5 mmol), L (0.5 mmol), NaOH (1 mmol) and NiCl2.6H2O (0.5 mmol) was suspended in 12 ml of deionized water and sealed in a 20-ml Teflon-lined autoclave. Upon heating at 433 K for one week, the autoclave was slowly cooled to room temperature. Green blocks of (I) were collected, washed with deionized water and dried.

Refinement

The H atoms on C atoms were generated geometrically and refined as riding with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C). The water H atoms were located in a difference Fourier map and refined with the O—H distance restrained to 0.85±0.01 Å.

Figures

Fig. 1.
The structure of (I), with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. Symmetry codes: (i) x, y - 1, z; (ii) 1/2 + x, 0.5 - y, z - 1/2.
Fig. 2.
View of part of the polymeric layer structure of (I).

Crystal data

[Ni(C12H6O4)(C10H14N4)(H2O)]F000 = 1000
Mr = 481.15Dx = 1.514 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4157 reflections
a = 12.4213 (12) Åθ = 1.9–26.1º
b = 13.2543 (13) ŵ = 0.96 mm1
c = 13.4328 (13) ÅT = 293 (2) K
β = 107.361 (2)ºBlock, green
V = 2110.8 (4) Å30.19 × 0.17 × 0.15 mm
Z = 4

Data collection

Bruker APEX CCD diffractometer4157 independent reflections
Radiation source: fine-focus sealed tube2982 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
T = 293(2) Kθmax = 26.1º
ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 1998)h = −9→15
Tmin = 0.827, Tmax = 0.866k = −16→14
11720 measured reflectionsl = −16→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097  w = 1/[σ2(Fo2) + (0.0253P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4157 reflectionsΔρmax = 0.54 e Å3
297 parametersΔρmin = −0.40 e Å3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
C10.2969 (3)0.1196 (2)0.2222 (3)0.0208 (8)
C20.2145 (3)0.1584 (2)0.2758 (2)0.0190 (8)
C30.2114 (3)0.2586 (2)0.2946 (3)0.0264 (9)
H30.25830.30190.27210.032*
C40.1392 (3)0.2986 (2)0.3472 (3)0.0238 (8)
H40.13990.36770.35970.029*
C50.0674 (3)0.2376 (2)0.3805 (2)0.0203 (8)
C6−0.0034 (3)0.2829 (2)0.4420 (3)0.0218 (8)
C70.0636 (3)0.1328 (2)0.3576 (2)0.0180 (7)
C80.1382 (3)0.0919 (2)0.3055 (2)0.0172 (7)
C90.1306 (3)−0.0118 (2)0.2806 (3)0.0256 (8)
H90.1795−0.03930.24730.031*
C100.0536 (3)−0.0723 (3)0.3042 (3)0.0281 (9)
H100.0497−0.14040.28680.034*
C11−0.0196 (3)−0.0320 (3)0.3546 (3)0.0312 (9)
H11−0.0722−0.07380.37060.037*
C12−0.0157 (3)0.0664 (2)0.3806 (3)0.0257 (8)
H12−0.06570.09140.41410.031*
C130.1710 (3)0.2460 (3)−0.1581 (3)0.0335 (10)
H130.16440.1937−0.20560.040*
C140.1151 (4)0.3340 (3)−0.1787 (3)0.0430 (11)
H140.06440.3537−0.24180.052*
C150.2219 (3)0.3312 (3)−0.0198 (3)0.0310 (9)
H150.25810.35100.04840.037*
C160.1118 (3)0.4914 (2)−0.0714 (3)0.0274 (9)
H16A0.12680.50240.00290.033*
H16B0.03110.4976−0.10390.033*
C170.1715 (3)0.5711 (2)−0.1149 (3)0.0296 (9)
H17A0.14980.5648−0.19030.036*
H17B0.25230.5605−0.08820.036*
C180.1434 (3)0.6771 (2)−0.0863 (3)0.0293 (9)
H18A0.06220.6862−0.10830.035*
H18B0.17050.6855−0.01120.035*
C190.1971 (3)0.7560 (2)−0.1379 (3)0.0293 (9)
H19A0.27540.7381−0.12770.035*
H19B0.15900.7559−0.21230.035*
C200.1050 (3)0.9021 (3)−0.0704 (3)0.0395 (11)
H200.03530.8734−0.07490.047*
C210.2746 (3)0.9270 (2)−0.0777 (3)0.0238 (8)
H210.34360.9163−0.08980.029*
N40.2477 (2)1.01080 (19)−0.0399 (2)0.0212 (7)
C230.1402 (3)0.9948 (3)−0.0365 (3)0.0378 (10)
H230.09731.0419−0.01370.045*
N10.2384 (2)0.2446 (2)−0.0581 (2)0.0224 (7)
N20.1476 (2)0.38862 (19)−0.0887 (2)0.0232 (7)
N30.1920 (2)0.8579 (2)−0.0970 (2)0.0240 (7)
O1−0.05860 (18)0.36339 (16)0.40707 (17)0.0227 (5)
O20.3062 (2)0.17401 (16)0.14730 (18)0.0266 (6)
O1W0.4733 (2)0.04150 (17)0.12115 (19)0.0208 (6)
O3−0.00731 (19)0.24467 (16)0.52507 (17)0.0265 (6)
O40.35191 (19)0.04171 (16)0.25344 (18)0.0257 (6)
Ni10.35134 (4)0.13565 (3)0.01819 (3)0.02231 (14)
HW120.495 (2)−0.0135 (16)0.107 (2)0.020 (10)*
HW110.440 (3)0.034 (2)0.166 (2)0.053 (15)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.023 (2)0.0180 (19)0.0236 (19)−0.0040 (15)0.0094 (15)−0.0067 (15)
C20.025 (2)0.0174 (19)0.0172 (18)0.0032 (14)0.0099 (15)0.0011 (14)
C30.034 (2)0.0166 (19)0.037 (2)−0.0033 (16)0.0226 (18)0.0027 (16)
C40.033 (2)0.0108 (18)0.033 (2)0.0005 (15)0.0184 (18)−0.0043 (15)
C50.024 (2)0.0201 (19)0.0198 (19)0.0018 (15)0.0110 (15)0.0017 (15)
C60.023 (2)0.0178 (19)0.028 (2)−0.0063 (15)0.0133 (17)−0.0083 (16)
C70.0207 (18)0.0162 (18)0.0187 (17)0.0009 (14)0.0085 (14)0.0007 (14)
C80.0238 (19)0.0136 (17)0.0162 (17)0.0012 (14)0.0088 (15)0.0009 (13)
C90.030 (2)0.021 (2)0.030 (2)0.0018 (16)0.0157 (17)−0.0013 (16)
C100.034 (2)0.0147 (19)0.039 (2)−0.0018 (16)0.0167 (19)−0.0041 (16)
C110.037 (2)0.022 (2)0.041 (2)−0.0094 (17)0.021 (2)−0.0018 (17)
C120.030 (2)0.025 (2)0.028 (2)−0.0024 (16)0.0182 (17)−0.0027 (16)
C130.047 (3)0.023 (2)0.029 (2)0.0090 (18)0.0076 (19)−0.0050 (17)
C140.057 (3)0.035 (2)0.026 (2)0.019 (2)−0.004 (2)0.0003 (18)
C150.035 (2)0.024 (2)0.027 (2)0.0056 (17)−0.0011 (18)−0.0046 (16)
C160.027 (2)0.019 (2)0.037 (2)0.0056 (15)0.0124 (18)−0.0005 (16)
C170.030 (2)0.020 (2)0.039 (2)0.0018 (16)0.0105 (18)−0.0001 (17)
C180.029 (2)0.020 (2)0.039 (2)0.0005 (16)0.0105 (18)0.0004 (17)
C190.033 (2)0.020 (2)0.036 (2)−0.0053 (16)0.0123 (18)−0.0043 (17)
C200.025 (2)0.025 (2)0.074 (3)−0.0038 (17)0.023 (2)−0.005 (2)
C210.019 (2)0.024 (2)0.031 (2)−0.0005 (15)0.0100 (16)0.0025 (16)
N40.0213 (17)0.0140 (15)0.0293 (17)−0.0003 (12)0.0092 (13)−0.0001 (13)
C230.025 (2)0.023 (2)0.071 (3)−0.0001 (17)0.023 (2)−0.011 (2)
N10.0244 (17)0.0182 (16)0.0264 (17)0.0042 (12)0.0104 (14)0.0006 (13)
N20.0265 (17)0.0127 (16)0.0304 (17)0.0036 (12)0.0086 (14)0.0024 (12)
N30.0238 (17)0.0149 (16)0.0341 (17)−0.0021 (13)0.0099 (14)−0.0015 (13)
O10.0282 (14)0.0136 (12)0.0333 (14)0.0018 (10)0.0196 (11)0.0008 (11)
O20.0385 (16)0.0226 (14)0.0284 (14)0.0093 (11)0.0246 (12)0.0068 (11)
O1W0.0230 (15)0.0157 (14)0.0277 (15)0.0028 (11)0.0138 (12)−0.0024 (11)
O30.0388 (16)0.0215 (13)0.0276 (14)0.0028 (11)0.0226 (12)0.0014 (11)
O40.0309 (15)0.0202 (14)0.0316 (14)0.0091 (11)0.0178 (12)0.0062 (11)
Ni10.0259 (3)0.0180 (2)0.0269 (3)0.0016 (2)0.0137 (2)0.0008 (2)

Geometric parameters (Å, °)

C1—O41.240 (4)C16—C171.505 (5)
C1—O21.270 (4)C16—H16A0.9700
C1—C21.508 (4)C16—H16B0.9700
C2—C31.356 (4)C17—C181.525 (4)
C2—C81.434 (4)C17—H17A0.9700
C3—C41.400 (4)C17—H17B0.9700
C3—H30.9300C18—C191.515 (4)
C4—C51.375 (4)C18—H18A0.9700
C4—H40.9300C18—H18B0.9700
C5—C71.420 (4)C19—N31.466 (4)
C5—C61.500 (4)C19—H19A0.9700
C6—O31.240 (4)C19—H19B0.9700
C6—O11.279 (4)C20—C231.338 (5)
C7—C121.421 (4)C20—N31.368 (4)
C7—C81.424 (4)C20—H200.9300
C8—C91.412 (4)C21—N41.306 (4)
C9—C101.356 (4)C21—N31.341 (4)
C9—H90.9300C21—H210.9300
C10—C111.392 (5)N4—C231.367 (4)
C10—H100.9300N4—Ni1i2.099 (3)
C11—C121.347 (4)C23—H230.9300
C11—H110.9300O1—Ni1ii2.116 (2)
C12—H120.9300O1W—HW120.819 (16)
C13—C141.343 (5)O1W—HW110.83 (4)
C13—N11.355 (4)O3—Ni1ii2.347 (2)
C13—H130.9300Ni1—O1W2.125 (2)
C14—N21.363 (4)Ni1—O22.040 (2)
C14—H140.9300Ni1—O1iii2.116 (2)
C15—N11.299 (4)Ni1—O3iii2.347 (2)
C15—N21.334 (4)Ni1—N12.060 (3)
C15—H150.9300Ni1—N4iv2.099 (3)
C16—N21.472 (4)
O4—C1—O2124.8 (3)H17A—C17—H17B107.9
O4—C1—C2120.4 (3)C19—C18—C17110.8 (3)
O2—C1—C2114.8 (3)C19—C18—H18A109.5
C3—C2—C8119.5 (3)C17—C18—H18A109.5
C3—C2—C1118.9 (3)C19—C18—H18B109.5
C8—C2—C1121.5 (3)C17—C18—H18B109.5
C2—C3—C4121.6 (3)H18A—C18—H18B108.1
C2—C3—H3119.2N3—C19—C18113.0 (3)
C4—C3—H3119.2N3—C19—H19A109.0
C5—C4—C3121.1 (3)C18—C19—H19A109.0
C5—C4—H4119.5N3—C19—H19B109.0
C3—C4—H4119.5C18—C19—H19B109.0
C4—C5—C7119.2 (3)H19A—C19—H19B107.8
C4—C5—C6119.1 (3)C23—C20—N3106.2 (3)
C7—C5—C6121.7 (3)C23—C20—H20126.9
O3—C6—O1120.7 (3)N3—C20—H20126.9
O3—C6—C5121.2 (3)N4—C21—N3112.7 (3)
O1—C6—C5118.1 (3)N4—C21—H21123.6
C5—C7—C12122.5 (3)N3—C21—H21123.6
C5—C7—C8119.6 (3)C21—N4—C23104.3 (3)
C12—C7—C8117.8 (3)C21—N4—Ni1i128.0 (2)
C9—C8—C7118.6 (3)C23—N4—Ni1i127.4 (2)
C9—C8—C2122.4 (3)C20—C23—N4110.8 (3)
C7—C8—C2118.9 (3)C20—C23—H23124.6
C10—C9—C8121.5 (3)N4—C23—H23124.6
C10—C9—H9119.2C15—N1—C13104.8 (3)
C8—C9—H9119.2C15—N1—Ni1126.0 (2)
C9—C10—C11119.7 (3)C13—N1—Ni1129.1 (2)
C9—C10—H10120.2C15—N2—C14105.8 (3)
C11—C10—H10120.2C15—N2—C16126.7 (3)
C12—C11—C10121.3 (3)C14—N2—C16127.5 (3)
C12—C11—H11119.4C21—N3—C20106.0 (3)
C10—C11—H11119.4C21—N3—C19125.8 (3)
C11—C12—C7121.1 (3)C20—N3—C19128.1 (3)
C11—C12—H12119.5C6—O1—Ni1ii94.87 (19)
C7—C12—H12119.5C1—O2—Ni1130.1 (2)
C14—C13—N1110.2 (3)Ni1—O1W—HW12126 (2)
C14—C13—H13124.9Ni1—O1W—HW1197 (3)
N1—C13—H13124.9HW12—O1W—HW11110 (2)
C13—C14—N2106.3 (3)C6—O3—Ni1ii85.3 (2)
C13—C14—H14126.9O2—Ni1—N185.93 (10)
N2—C14—H14126.9O2—Ni1—N4iv102.65 (10)
N1—C15—N2112.9 (3)N1—Ni1—N4iv96.70 (11)
N1—C15—H15123.6O2—Ni1—O1iii159.34 (9)
N2—C15—H15123.6N1—Ni1—O1iii94.01 (10)
N2—C16—C17112.4 (3)N4iv—Ni1—O1iii97.87 (10)
N2—C16—H16A109.1O2—Ni1—O1W85.20 (9)
C17—C16—H16A109.1N1—Ni1—O1W169.33 (10)
N2—C16—H16B109.1N4iv—Ni1—O1W91.03 (10)
C17—C16—H16B109.1O1iii—Ni1—O1W92.20 (9)
H16A—C16—H16B107.9O2—Ni1—O3iii100.97 (9)
C16—C17—C18111.9 (3)N1—Ni1—O3iii86.35 (10)
C16—C17—H17A109.2N4iv—Ni1—O3iii156.33 (9)
C18—C17—H17A109.2O1iii—Ni1—O3iii58.47 (8)
C16—C17—H17B109.2O1W—Ni1—O3iii89.53 (8)
C18—C17—H17B109.2

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—HW12···O1v0.819 (16)1.847 (18)2.661 (3)172 (3)
O1W—HW11···O40.83 (4)1.83 (4)2.651 (3)169 (3)

Symmetry codes: (v) −x+1/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2770).

References

  • Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed.37, 1460–1494.
  • Bruker (1998). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ma, J.-F., Yang, J., Zheng, G.-L., Li, L. & Liu, J.-F. (2003). Inorg. Chem.42, 7531–7534. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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