metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Poly[4,4′-imino­dipyridinium [di-μ4-isophthalato-κ4O:O′:O′′:O′′-di-μ3-iso­phthal­ato-κ3O:O′:O′′;κ4O:O′:O′′,O′′′-trizinc(II)] dihydrate]

aLyman Briggs College, Department of Chemistry, Michigan State University, East Lansing, MI 48825, USA
*Correspondence e-mail: laduca@msu.edu

(Received 14 November 2008; accepted 17 November 2008; online 22 November 2008)

In the title compound, {(C10H11N3)[Zn3(C8H4O4)4]·2H2O}n, divalent Zn atoms are linked into trinuclear units featuring tetra­hedral, octa­hedral and distorted tetrahedral, octahedral and square-pyramidal coordination geometries. These trinuclear units are connected by isopthalate dianions into [Zn3(isophthalate)4]n2n anionic layers, which aggregate into the three-dimensional structure via hydrogen-bonding pathways mediated by doubly protonated 4,4′-imino­dipyridinium cations and water mol­ecules of crystallization. One solvent water mol­ecule was found to be disordered over two positions, each with a 50% site-occupancy factor.

Related literature

For divalent metal phthalate/4,4′-imino­dipyridinium coordin­ation polymers, see: Braverman et al. (2007[Braverman, M. A., Supkowski, R. M. & LaDuca, R. L. (2007). Inorg. Chim. Acta, 360, 2353-2362.]). For the preparation of 4,4′-dipyridylamine, see: Zapf et al. (1998[Zapf, P. J., LaDuca, R. L., Rarig, R. S., Johnson, K. M. III & Zubieta, J. (1998). Inorg. Chem. 37, 3411-3414.]).

[Scheme 1]

Experimental

Crystal data
  • (C10H11N3)[Zn3(C8H4O4)4]·2H2O

  • Mr = 1061.81

  • Triclinic, [P \overline 1]

  • a = 9.5780 (13) Å

  • b = 10.2149 (14) Å

  • c = 21.246 (3) Å

  • α = 78.801 (2)°

  • β = 86.868 (2)°

  • γ = 87.773 (2)°

  • V = 2035.2 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.84 mm−1

  • T = 173 (2) K

  • 0.54 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART 1K diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.617, Tmax = 0.802

  • 24469 measured reflections

  • 9553 independent reflections

  • 8108 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.081

  • S = 1.07

  • 9553 reflections

  • 619 parameters

  • 6 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.92 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1A⋯O8i 0.863 (18) 1.921 (19) 2.778 (3) 172 (4)
O1W—H1B⋯O4 0.863 (18) 1.874 (19) 2.733 (3) 174 (4)
N1—H1N⋯O2WA 0.901 (19) 2.03 (3) 2.808 (6) 144 (4)
N1—H1N⋯O2WBii 0.901 (19) 1.96 (3) 2.757 (5) 147 (4)
N2—H2N⋯O1Wiii 0.862 (17) 1.893 (18) 2.754 (3) 176 (3)
N3—H3N⋯O12iv 0.880 (17) 1.93 (2) 2.764 (3) 157 (3)
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+2, -z; (iii) x-1, y, z; (iv) -x-1, -y+1, -z+1.

Data collection: SMART (Bruker, 2006[Bruker (2006). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalMaker (Palmer, 2007[Palmer, D. (2007). CrystalMaker. CrystalMaker Software Ltd, Bicester, Oxfordshire, England.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Recently, we reported Co and Ni phthalate 1-D coordination polymers containing the hydrogen-bonding capable, dipodal tethering ligand 4,4'-dipyridylamine (dpa) (Braverman et al., 2007). In an attempt to extend this chemistry into a zinc isophthalate coordination polymer system, colourless crystals of the title compound, (I), were obtained.

The asymmetric unit of (I) contains three divalent Zn atoms, four crystallographically distinct doubly deprotonated isophthalate dianions, one doubly protonated H2dpa2+ dication and two water molecules of crystallization, one of which is disordered equally over two positions, Fig. 1. The Zn atoms are linked into a trinuclear cluster by bridging carboxylate groups and O atoms from the isophthalate ions, in which Zn2, Zn1 and Zn3 adopt tetrahedral, octahedral and distorted square pyramidal coordination geometries, respectively.

Each trinuclear unit is linked to two others along the a-axis by two sets of two exotetradentate isophthalate dianions, which bridge two Zn atoms through a carboxylate bridge and two other Zn atoms through a single O atom connection. The trinuclear units also conjoin along the b-axis. Here, each trinuclear unit again connects to two others, via two sets of two crystallographically distinct exotridentate isophthalate dianions. One of these adopts a bis-bridging/chelating binding mode, while the other possesses a bis-bridging/monodentate binding mode. The resulting [Zn3(isophthalate)4]n2n- anionic layers contain incipient voids occupied by H2dpa2+ dications and water molecules of crystallization, Fig. 2. These layers are arranged parallel to the bc-plane. Abutting [Zn3(isophthalate)4]n2n- layers aggregate into the 3-D structure through hydrogen-bonding patterns between the protonated pyridyl-N atoms of the H2dpa2+ dications, carboxylate-O atoms and water molecules of crystallization, Table 1 and Fig. 3.

Related literature top

For divalent metal phthalate/4,4'-iminodipyridinium coordination polymers, see: Braverman et al. (2007). For the preparation of 4,4'-dipyridylamine, see: Zapf et al. (1998).

Experimental top

All chemicals were obtained commercially with the exception of 4,4'-dipyridylamine which was prepared according to a literature procedure (Zapf et al., 1998). Zinc chloride dihydrate (64 mg, 0.37 mmol), isophthalic acid (62 mg, 0.37 mmol) and 4,4'-dipyridylamine (127 mg, 0.74 mmol) were placed into H2O (10 ml ) in a 23 ml Teflon-lined Parr acid digestion bomb. The bomb was heated at 393 K for 72 h and was then allowed to cool to room temperature. Colourless crystals of (I) were obtained along with a white powdery solid.

Refinement top

All H atoms bound to C atoms were placed in calculated positions, with C—H = 0.93 Å and refined in riding mode with Uiso = 1.2Ueq(C). The H atoms bound to O atoms were found via a Fourier difference map, restrained at fixed positions or with O—H = 0.85 Å, and refined with Uiso=1.2Ueq(O). The H atoms bound to N atoms were found via a Fourier difference map, restrained with N—H = 0.91 Å (for pyridyl N atoms) or with N—H = 0.89 Å (for the amine N atom), and refined with Uiso=1.2Ueq(N). See Table 1 for O-H and N-H distances. One water molecule was found to be disorderd over two sites, each with equal weight; the H atoms could not be located.

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2007); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Coordination environment of (I), showing 50% probability ellipsoids and atom numbering scheme. Most hydrogen atom positions are shown as gray sticks. Unligated water molecules are not shown. Color codes: gray Zn, light blue N, red O, black C, pink H. Symmetry codes: (i) x - 1, y, z; (ii) x + 1, y, z; (iii) x, y - 1, z; (iv) x, y + 1, z
[Figure 2] Fig. 2. A single [Zn3(isophthalate)4]n2n- anionic layer in (I), showing [H2dpa]2+ cations within the incipient cavities in blue. Water molecules of crystallization are depicted in orange.
[Figure 3] Fig. 3. Packing diagram illustrating the AB layer stacking pattern, which forms the 3-D crystal structure of (I) through hydrogen bonding mediated by the protonated pyridyl groups and the amine groups of the [H2dpa]2+ cations. Hydrogen bonding is shown as dashed lines. The oxygen atoms of the water molecules of crystallization are shown in orange.
Poly[4,4'-iminodipyridinium [di-µ4-isophthalato-κ4O:O':O'':O''-di-µ3-isophthalato- κ3O:O':O'';κ4O:O':O'',O'''-trizinc(II)] dihydrate] top
Crystal data top
(C10H11N3)[Zn3(C8H4O4)4]·2H2OZ = 2
Mr = 1061.81F(000) = 1072
Triclinic, P1Dx = 1.729 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5780 (13) ÅCell parameters from 24469 reflections
b = 10.2149 (14) Åθ = 2.0–28.3°
c = 21.246 (3) ŵ = 1.84 mm1
α = 78.801 (2)°T = 173 K
β = 86.868 (2)°Block, colourless
γ = 87.773 (2)°0.54 × 0.20 × 0.12 mm
V = 2035.2 (5) Å3
Data collection top
Bruker SMART 1K
diffractometer
9553 independent reflections
Radiation source: fine-focus sealed tube8108 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.617, Tmax = 0.802k = 1313
24469 measured reflectionsl = 2827
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0267P)2 + 2.909P]
where P = (Fo2 + 2Fc2)/3
9553 reflections(Δ/σ)max < 0.001
619 parametersΔρmax = 0.92 e Å3
6 restraintsΔρmin = 0.54 e Å3
Crystal data top
(C10H11N3)[Zn3(C8H4O4)4]·2H2Oγ = 87.773 (2)°
Mr = 1061.81V = 2035.2 (5) Å3
Triclinic, P1Z = 2
a = 9.5780 (13) ÅMo Kα radiation
b = 10.2149 (14) ŵ = 1.84 mm1
c = 21.246 (3) ÅT = 173 K
α = 78.801 (2)°0.54 × 0.20 × 0.12 mm
β = 86.868 (2)°
Data collection top
Bruker SMART 1K
diffractometer
9553 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
8108 reflections with I > 2σ(I)
Tmin = 0.617, Tmax = 0.802Rint = 0.024
24469 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0346 restraints
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.92 e Å3
9553 reflectionsΔρmin = 0.54 e Å3
619 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
xyzUiso*/UeqOcc. (<1)
Zn10.19902 (3)0.26767 (3)0.246490 (13)0.01234 (6)
Zn20.26205 (3)0.12585 (3)0.120459 (13)0.01308 (7)
Zn30.12868 (3)0.40139 (3)0.372471 (12)0.01223 (7)
O10.25397 (19)0.31307 (16)0.07148 (8)0.0198 (4)
O1W0.3318 (2)0.7891 (3)0.26301 (11)0.0473 (7)
H1A0.263 (3)0.747 (4)0.2846 (15)0.057*
H1B0.304 (4)0.816 (4)0.2245 (10)0.057*
O20.24293 (18)0.39914 (16)0.16108 (8)0.0163 (3)
O2WB0.0297 (4)1.2705 (5)0.01008 (17)0.0353 (10)0.50
O30.3008 (2)1.01970 (17)0.04816 (8)0.0221 (4)
O2WA0.0059 (6)0.9448 (6)0.0086 (2)0.0554 (17)0.50
O40.2498 (2)0.89274 (18)0.14176 (8)0.0238 (4)
O50.16648 (18)0.22390 (16)0.42778 (8)0.0176 (4)
O60.15301 (18)0.14730 (16)0.33667 (8)0.0167 (3)
O70.12225 (19)0.47631 (16)0.43426 (8)0.0177 (4)
O80.1139 (2)0.33392 (17)0.34139 (8)0.0214 (4)
O90.01511 (17)0.36945 (17)0.24508 (8)0.0181 (4)
O100.06132 (17)0.39961 (17)0.34319 (8)0.0169 (3)
O110.71777 (16)0.41254 (16)0.30577 (8)0.0149 (3)
O120.58193 (19)0.4146 (2)0.38758 (8)0.0268 (4)
O130.45204 (17)0.12092 (17)0.15619 (8)0.0181 (4)
O140.38613 (17)0.17370 (17)0.25117 (8)0.0179 (4)
O150.9879 (2)0.1151 (2)0.11281 (9)0.0270 (4)
O161.11797 (17)0.12825 (16)0.19406 (8)0.0156 (3)
N10.1435 (3)0.8121 (4)0.11834 (13)0.0565 (10)
H1N0.096 (4)0.819 (4)0.0802 (13)0.068*
N20.3877 (2)0.7558 (2)0.28617 (10)0.0184 (4)
H2N0.4749 (19)0.770 (3)0.2783 (14)0.022*
N30.3498 (2)0.6593 (2)0.48259 (11)0.0261 (5)
H3N0.346 (3)0.635 (3)0.5245 (9)0.031*
C10.2898 (3)0.5447 (2)0.06242 (11)0.0159 (5)
C20.2758 (3)0.6576 (2)0.09009 (11)0.0158 (5)
H20.24430.64970.13280.019*
C30.3089 (3)0.7831 (2)0.05381 (11)0.0162 (5)
C40.3613 (3)0.7939 (2)0.00916 (12)0.0214 (5)
H40.38630.87670.03300.026*
C50.3764 (3)0.6809 (3)0.03659 (12)0.0250 (6)
H50.41200.68810.07870.030*
C60.3384 (3)0.5574 (3)0.00129 (12)0.0225 (5)
H60.34550.48270.02040.027*
C70.2587 (2)0.4086 (2)0.10189 (11)0.0146 (5)
C80.2853 (3)0.9050 (2)0.08303 (12)0.0163 (5)
C110.1663 (2)0.0103 (2)0.43341 (11)0.0142 (4)
C120.1514 (2)0.1155 (2)0.40159 (11)0.0148 (5)
H120.14660.09850.35710.018*
C130.1436 (2)0.2461 (2)0.43602 (11)0.0139 (4)
C140.1530 (3)0.2708 (2)0.50250 (11)0.0179 (5)
H140.14700.35770.52580.021*
C150.1712 (3)0.1665 (2)0.53413 (12)0.0216 (5)
H150.17960.18370.57840.026*
C160.1768 (3)0.0366 (2)0.49976 (12)0.0200 (5)
H160.18770.03330.52120.024*
C170.1636 (2)0.1306 (2)0.39605 (11)0.0135 (4)
C180.1254 (2)0.3577 (2)0.40070 (11)0.0138 (4)
C210.2241 (2)0.4197 (2)0.26180 (11)0.0133 (4)
C220.3393 (2)0.4109 (2)0.30544 (11)0.0138 (4)
H220.32640.38840.34930.017*
C230.4731 (2)0.4356 (2)0.28326 (11)0.0136 (4)
C240.4919 (3)0.4767 (2)0.21774 (11)0.0159 (5)
H240.58120.49780.20300.019*
C250.3769 (3)0.4861 (2)0.17443 (11)0.0168 (5)
H250.38950.51370.13070.020*
C260.2433 (3)0.4545 (2)0.19603 (11)0.0162 (5)
H260.16710.45660.16680.019*
C270.0791 (2)0.3933 (2)0.28499 (11)0.0140 (4)
C280.5976 (2)0.4193 (2)0.32967 (11)0.0150 (5)
C310.0791 (3)0.7817 (4)0.17389 (15)0.0416 (8)
H310.01810.77410.17310.050*
C320.1520 (3)0.7618 (3)0.23121 (13)0.0246 (6)
H320.10540.74070.26930.030*
C330.2983 (3)0.7733 (2)0.23259 (12)0.0184 (5)
C340.3620 (3)0.8093 (3)0.17313 (13)0.0246 (6)
H340.45880.82020.17230.030*
C350.2832 (4)0.8282 (4)0.11717 (14)0.0387 (8)
H350.32590.85220.07810.046*
C360.2372 (3)0.6433 (3)0.44465 (13)0.0270 (6)
H360.15370.61130.46320.032*
C370.2419 (3)0.6728 (3)0.37923 (13)0.0253 (6)
H370.16250.65960.35370.030*
C380.3657 (3)0.7229 (2)0.35070 (12)0.0173 (5)
C390.4817 (3)0.7387 (3)0.39210 (13)0.0327 (7)
H390.56640.77170.37520.039*
C400.4708 (3)0.7060 (4)0.45719 (14)0.0376 (8)
H400.54860.71620.48420.045*
C410.6209 (2)0.1089 (2)0.23487 (11)0.0134 (4)
C420.7377 (2)0.1208 (2)0.19237 (11)0.0140 (4)
H420.72640.14280.14830.017*
C430.8713 (2)0.0996 (2)0.21573 (11)0.0140 (4)
C440.8875 (2)0.0575 (2)0.28136 (12)0.0158 (5)
H440.97660.04090.29700.019*
C450.7707 (3)0.0402 (2)0.32346 (11)0.0174 (5)
H450.78160.00850.36710.021*
C460.6379 (3)0.0698 (2)0.30081 (12)0.0166 (5)
H460.56040.06380.32940.020*
C470.4750 (2)0.1373 (2)0.21204 (11)0.0137 (4)
C480.9977 (2)0.1169 (2)0.17032 (12)0.0159 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01115 (13)0.01362 (13)0.01198 (13)0.00081 (10)0.00085 (10)0.00242 (10)
Zn20.01370 (14)0.01262 (13)0.01368 (13)0.00055 (10)0.00062 (10)0.00445 (10)
Zn30.01145 (13)0.01246 (13)0.01351 (13)0.00087 (10)0.00011 (10)0.00432 (10)
O10.0310 (10)0.0129 (8)0.0157 (8)0.0005 (7)0.0012 (7)0.0039 (7)
O1W0.0225 (11)0.0826 (19)0.0267 (12)0.0079 (12)0.0048 (9)0.0168 (12)
O20.0202 (9)0.0156 (8)0.0124 (8)0.0043 (7)0.0009 (7)0.0010 (6)
O2WB0.032 (2)0.065 (3)0.0106 (17)0.002 (2)0.0014 (16)0.0108 (18)
O30.0345 (11)0.0132 (8)0.0194 (9)0.0016 (7)0.0004 (8)0.0051 (7)
O2WA0.045 (3)0.099 (5)0.026 (3)0.019 (4)0.005 (2)0.020 (3)
O40.0344 (11)0.0198 (9)0.0183 (9)0.0018 (8)0.0026 (8)0.0081 (7)
O50.0249 (9)0.0117 (8)0.0170 (8)0.0014 (7)0.0015 (7)0.0042 (6)
O60.0215 (9)0.0150 (8)0.0134 (8)0.0041 (7)0.0018 (7)0.0013 (6)
O70.0257 (9)0.0121 (8)0.0158 (8)0.0008 (7)0.0003 (7)0.0039 (6)
O80.0312 (10)0.0185 (9)0.0152 (8)0.0039 (8)0.0011 (7)0.0043 (7)
O90.0120 (8)0.0227 (9)0.0184 (9)0.0038 (7)0.0024 (7)0.0025 (7)
O100.0113 (8)0.0234 (9)0.0170 (8)0.0015 (7)0.0014 (6)0.0060 (7)
O110.0106 (8)0.0171 (8)0.0174 (8)0.0016 (6)0.0007 (6)0.0043 (7)
O120.0174 (9)0.0480 (12)0.0158 (9)0.0067 (8)0.0021 (7)0.0078 (8)
O130.0141 (8)0.0237 (9)0.0174 (8)0.0005 (7)0.0016 (7)0.0061 (7)
O140.0129 (8)0.0211 (9)0.0205 (9)0.0025 (7)0.0023 (7)0.0064 (7)
O150.0216 (10)0.0446 (12)0.0166 (9)0.0027 (8)0.0013 (7)0.0103 (8)
O160.0112 (8)0.0150 (8)0.0214 (9)0.0012 (6)0.0010 (7)0.0062 (7)
N10.0381 (17)0.114 (3)0.0187 (13)0.0153 (18)0.0111 (12)0.0176 (16)
N20.0169 (10)0.0220 (11)0.0156 (10)0.0020 (8)0.0008 (8)0.0015 (8)
N30.0263 (12)0.0364 (13)0.0147 (11)0.0025 (10)0.0025 (9)0.0020 (10)
C10.0201 (12)0.0134 (11)0.0130 (11)0.0002 (9)0.0001 (9)0.0000 (9)
C20.0182 (12)0.0160 (11)0.0130 (11)0.0010 (9)0.0008 (9)0.0030 (9)
C30.0194 (12)0.0141 (11)0.0157 (11)0.0004 (9)0.0014 (9)0.0044 (9)
C40.0323 (15)0.0115 (11)0.0185 (12)0.0001 (10)0.0038 (11)0.0005 (9)
C50.0417 (17)0.0186 (13)0.0131 (12)0.0007 (11)0.0081 (11)0.0020 (10)
C60.0365 (15)0.0153 (12)0.0158 (12)0.0008 (11)0.0035 (11)0.0051 (9)
C70.0138 (11)0.0135 (11)0.0158 (11)0.0007 (9)0.0016 (9)0.0007 (9)
C80.0165 (12)0.0143 (11)0.0193 (12)0.0007 (9)0.0044 (9)0.0056 (9)
C110.0153 (11)0.0122 (11)0.0150 (11)0.0001 (9)0.0004 (9)0.0024 (9)
C120.0146 (11)0.0157 (11)0.0139 (11)0.0001 (9)0.0007 (9)0.0021 (9)
C130.0135 (11)0.0132 (11)0.0155 (11)0.0006 (8)0.0000 (9)0.0039 (9)
C140.0252 (13)0.0124 (11)0.0152 (11)0.0012 (9)0.0012 (10)0.0011 (9)
C150.0362 (15)0.0177 (12)0.0106 (11)0.0022 (11)0.0013 (10)0.0016 (9)
C160.0314 (14)0.0150 (11)0.0150 (11)0.0022 (10)0.0011 (10)0.0061 (9)
C170.0101 (11)0.0136 (11)0.0163 (11)0.0013 (8)0.0001 (9)0.0016 (9)
C180.0118 (11)0.0128 (11)0.0170 (11)0.0020 (8)0.0025 (9)0.0041 (9)
C210.0123 (11)0.0111 (10)0.0166 (11)0.0007 (8)0.0004 (9)0.0032 (9)
C220.0151 (11)0.0152 (11)0.0116 (10)0.0018 (9)0.0012 (9)0.0030 (9)
C230.0133 (11)0.0121 (10)0.0158 (11)0.0022 (8)0.0015 (9)0.0040 (9)
C240.0132 (11)0.0165 (11)0.0181 (12)0.0010 (9)0.0018 (9)0.0032 (9)
C250.0191 (12)0.0203 (12)0.0110 (11)0.0017 (9)0.0024 (9)0.0020 (9)
C260.0148 (11)0.0173 (11)0.0168 (11)0.0018 (9)0.0035 (9)0.0047 (9)
C270.0138 (11)0.0093 (10)0.0188 (11)0.0023 (8)0.0003 (9)0.0024 (9)
C280.0138 (11)0.0143 (11)0.0169 (11)0.0011 (9)0.0012 (9)0.0036 (9)
C310.0277 (16)0.069 (2)0.0312 (17)0.0091 (16)0.0051 (13)0.0172 (16)
C320.0250 (14)0.0270 (14)0.0231 (13)0.0051 (11)0.0018 (11)0.0071 (11)
C330.0265 (13)0.0106 (11)0.0186 (12)0.0045 (9)0.0011 (10)0.0035 (9)
C340.0292 (15)0.0229 (13)0.0214 (13)0.0001 (11)0.0023 (11)0.0032 (10)
C350.0403 (19)0.058 (2)0.0184 (14)0.0066 (16)0.0017 (13)0.0067 (14)
C360.0232 (14)0.0327 (15)0.0224 (13)0.0026 (11)0.0030 (11)0.0010 (11)
C370.0216 (13)0.0315 (15)0.0202 (13)0.0056 (11)0.0014 (11)0.0001 (11)
C380.0199 (12)0.0151 (11)0.0166 (12)0.0025 (9)0.0016 (10)0.0022 (9)
C390.0151 (13)0.061 (2)0.0211 (14)0.0032 (13)0.0022 (11)0.0054 (13)
C400.0201 (15)0.069 (2)0.0217 (14)0.0003 (14)0.0023 (11)0.0058 (14)
C410.0126 (11)0.0103 (10)0.0180 (11)0.0003 (8)0.0035 (9)0.0033 (9)
C420.0162 (11)0.0131 (11)0.0135 (11)0.0024 (9)0.0013 (9)0.0039 (9)
C430.0136 (11)0.0118 (10)0.0175 (11)0.0010 (8)0.0002 (9)0.0055 (9)
C440.0141 (11)0.0147 (11)0.0200 (12)0.0013 (9)0.0067 (9)0.0046 (9)
C450.0214 (13)0.0175 (12)0.0135 (11)0.0026 (10)0.0030 (9)0.0026 (9)
C460.0164 (12)0.0164 (11)0.0172 (12)0.0019 (9)0.0020 (9)0.0043 (9)
C470.0122 (11)0.0098 (10)0.0183 (11)0.0022 (8)0.0009 (9)0.0008 (9)
C480.0142 (11)0.0143 (11)0.0194 (12)0.0011 (9)0.0016 (9)0.0046 (9)
Geometric parameters (Å, º) top
Zn1—O141.9980 (17)C6—H60.9300
Zn1—O92.0089 (17)C11—C121.391 (3)
Zn1—O22.0705 (16)C11—C161.391 (3)
Zn1—O62.1005 (16)C11—C171.503 (3)
Zn1—O16i2.1607 (16)C12—C131.394 (3)
Zn1—O11ii2.3100 (16)C12—H120.9300
Zn2—O11.9927 (17)C13—C141.393 (3)
Zn2—O132.0048 (17)C13—C181.502 (3)
Zn2—O16i2.0314 (17)C14—C151.387 (3)
Zn2—O3iii2.0559 (17)C14—H140.9300
Zn2—O4iii2.3422 (18)C15—C161.386 (3)
Zn3—O101.9569 (16)C15—H150.9300
Zn3—O11ii1.9766 (16)C16—H160.9300
Zn3—O7iv1.9773 (16)C21—C261.394 (3)
Zn3—O51.9917 (17)C21—C221.396 (3)
O1—C71.274 (3)C21—C271.496 (3)
O1W—H1A0.863 (18)C22—C231.386 (3)
O1W—H1B0.863 (18)C22—H220.9300
O2—C71.244 (3)C23—C241.393 (3)
O3—C81.268 (3)C23—C281.499 (3)
O4—C81.259 (3)C24—C251.390 (3)
O5—C171.272 (3)C24—H240.9300
O6—C171.249 (3)C25—C261.388 (3)
O7—C181.281 (3)C25—H250.9300
O8—C181.246 (3)C26—H260.9300
O9—C271.253 (3)C31—C321.354 (4)
O10—C271.272 (3)C31—H310.9300
O11—C281.293 (3)C32—C331.401 (4)
O12—C281.239 (3)C32—H320.9300
O13—C471.262 (3)C33—C341.411 (4)
O14—C471.254 (3)C34—C351.358 (4)
O15—C481.234 (3)C34—H340.9300
O16—C481.301 (3)C35—H350.9300
N1—C311.339 (4)C36—C371.367 (4)
N1—C351.343 (4)C36—H360.9300
N1—H1N0.901 (19)C37—C381.396 (4)
N2—C381.373 (3)C37—H370.9300
N2—C331.374 (3)C38—C391.403 (4)
N2—H2N0.862 (17)C39—C401.367 (4)
N3—C361.335 (4)C39—H390.9300
N3—C401.337 (4)C40—H400.9300
N3—H3N0.880 (17)C41—C421.392 (3)
C1—C61.390 (3)C41—C461.397 (3)
C1—C21.392 (3)C41—C471.503 (3)
C1—C71.509 (3)C42—C431.392 (3)
C2—C31.400 (3)C42—H420.9300
C2—H20.9300C43—C441.393 (3)
C3—C41.388 (3)C43—C481.500 (3)
C3—C81.500 (3)C44—C451.388 (3)
C4—C51.390 (4)C44—H440.9300
C4—H40.9300C45—C461.386 (3)
C5—C61.387 (3)C45—H450.9300
C5—H50.9300C46—H460.9300
O14—Zn1—O9176.55 (7)C15—C14—C13120.3 (2)
O14—Zn1—O296.23 (7)C15—C14—H14119.9
O9—Zn1—O284.01 (7)C13—C14—H14119.9
O14—Zn1—O685.68 (7)C16—C15—C14120.0 (2)
O9—Zn1—O693.84 (7)C16—C15—H15120.0
O2—Zn1—O6175.51 (6)C14—C15—H15120.0
O14—Zn1—O16i91.83 (7)C15—C16—C11120.3 (2)
O9—Zn1—O16i91.61 (7)C15—C16—H16119.8
O2—Zn1—O16i90.24 (6)C11—C16—H16119.8
O6—Zn1—O16i93.76 (6)O6—C17—O5125.0 (2)
O14—Zn1—O11ii88.41 (6)O6—C17—C11117.7 (2)
O9—Zn1—O11ii88.14 (7)O5—C17—C11117.3 (2)
O2—Zn1—O11ii91.68 (6)O8—C18—O7122.5 (2)
O6—Zn1—O11ii84.30 (6)O8—C18—C13120.5 (2)
O16i—Zn1—O11ii178.03 (6)O7—C18—C13117.0 (2)
O1—Zn2—O13100.18 (7)C26—C21—C22120.1 (2)
O1—Zn2—O16i103.26 (7)C26—C21—C27119.4 (2)
O13—Zn2—O16i107.64 (7)C22—C21—C27120.6 (2)
O1—Zn2—O3iii101.82 (7)C23—C22—C21119.9 (2)
O13—Zn2—O3iii101.12 (7)C23—C22—H22120.0
O16i—Zn2—O3iii137.35 (7)C21—C22—H22120.0
O1—Zn2—O4iii159.21 (7)C22—C23—C24120.0 (2)
O13—Zn2—O4iii92.86 (7)C22—C23—C28120.1 (2)
O16i—Zn2—O4iii87.90 (6)C24—C23—C28119.9 (2)
O3iii—Zn2—O4iii59.44 (6)C25—C24—C23119.9 (2)
O10—Zn3—O11ii116.47 (7)C25—C24—H24120.1
O10—Zn3—O7iv106.51 (7)C23—C24—H24120.1
O11ii—Zn3—O7iv119.79 (7)C26—C25—C24120.4 (2)
O10—Zn3—O5107.06 (7)C26—C25—H25119.8
O11ii—Zn3—O5102.47 (7)C24—C25—H25119.8
O7iv—Zn3—O5102.88 (7)C25—C26—C21119.6 (2)
C7—O1—Zn2118.93 (15)C25—C26—H26120.2
H1A—O1W—H1B106 (3)C21—C26—H26120.2
C7—O2—Zn1143.82 (16)O9—C27—O10125.5 (2)
C8—O3—Zn2iv96.33 (14)O9—C27—C21117.3 (2)
C8—O4—Zn2iv83.55 (14)O10—C27—C21117.2 (2)
C17—O5—Zn3111.28 (15)O12—C28—O11123.6 (2)
C17—O6—Zn1146.85 (15)O12—C28—C23119.8 (2)
C18—O7—Zn3iii106.38 (14)O11—C28—C23116.6 (2)
C27—O9—Zn1137.38 (16)N1—C31—C32121.6 (3)
C27—O10—Zn3119.50 (15)N1—C31—H31119.2
C28—O11—Zn3i111.44 (14)C32—C31—H31119.2
C28—O11—Zn1i131.84 (15)C31—C32—C33119.4 (3)
Zn3i—O11—Zn1i98.76 (7)C31—C32—H32120.3
C47—O13—Zn2124.81 (15)C33—C32—H32120.3
C47—O14—Zn1136.38 (16)N2—C33—C32126.9 (2)
C48—O16—Zn2ii105.49 (14)N2—C33—C34115.8 (2)
C48—O16—Zn1ii133.79 (15)C32—C33—C34117.3 (2)
Zn2ii—O16—Zn1ii103.84 (7)C35—C34—C33120.6 (3)
C31—N1—C35121.3 (3)C35—C34—H34119.7
C31—N1—H1N122 (3)C33—C34—H34119.7
C35—N1—H1N117 (3)N1—C35—C34119.8 (3)
C38—N2—C33132.6 (2)N1—C35—H35120.1
C38—N2—H2N113 (2)C34—C35—H35120.1
C33—N2—H2N115 (2)N3—C36—C37121.5 (3)
C36—N3—C40120.4 (2)N3—C36—H36119.3
C36—N3—H3N120 (2)C37—C36—H36119.3
C40—N3—H3N119 (2)C36—C37—C38120.0 (3)
C6—C1—C2119.4 (2)C36—C37—H37120.0
C6—C1—C7120.1 (2)C38—C37—H37120.0
C2—C1—C7120.4 (2)N2—C38—C37127.0 (2)
C1—C2—C3120.2 (2)N2—C38—C39116.1 (2)
C1—C2—H2119.9C37—C38—C39116.9 (2)
C3—C2—H2119.9C40—C39—C38120.3 (3)
C4—C3—C2119.8 (2)C40—C39—H39119.8
C4—C3—C8120.6 (2)C38—C39—H39119.8
C2—C3—C8119.7 (2)N3—C40—C39120.9 (3)
C3—C4—C5119.9 (2)N3—C40—H40119.6
C3—C4—H4120.0C39—C40—H40119.6
C5—C4—H4120.0C42—C41—C46119.8 (2)
C6—C5—C4120.1 (2)C42—C41—C47121.9 (2)
C6—C5—H5119.9C46—C41—C47118.2 (2)
C4—C5—H5119.9C43—C42—C41120.1 (2)
C5—C6—C1120.4 (2)C43—C42—H42120.0
C5—C6—H6119.8C41—C42—H42120.0
C1—C6—H6119.8C42—C43—C44119.8 (2)
O2—C7—O1125.9 (2)C42—C43—C48120.3 (2)
O2—C7—C1117.3 (2)C44—C43—C48119.9 (2)
O1—C7—C1116.8 (2)C45—C44—C43120.0 (2)
O4—C8—O3120.6 (2)C45—C44—H44120.0
O4—C8—C3119.8 (2)C43—C44—H44120.0
O3—C8—C3119.6 (2)C46—C45—C44120.3 (2)
O4—C8—Zn2iv66.84 (13)C46—C45—H45119.9
O3—C8—Zn2iv53.82 (12)C44—C45—H45119.9
C3—C8—Zn2iv173.03 (18)C45—C46—C41119.8 (2)
C12—C11—C16119.6 (2)C45—C46—H46120.1
C12—C11—C17119.5 (2)C41—C46—H46120.1
C16—C11—C17120.9 (2)O14—C47—O13125.8 (2)
C11—C12—C13120.3 (2)O14—C47—C41116.3 (2)
C11—C12—H12119.8O13—C47—C41117.9 (2)
C13—C12—H12119.8O15—C48—O16121.4 (2)
C14—C13—C12119.5 (2)O15—C48—C43120.8 (2)
C14—C13—C18121.2 (2)O16—C48—C43117.8 (2)
C12—C13—C18119.4 (2)
O13—Zn2—O1—C762.52 (19)Zn3iii—O7—C18—C13170.95 (16)
O16i—Zn2—O1—C748.50 (19)C14—C13—C18—O8178.4 (2)
O3iii—Zn2—O1—C7166.28 (18)C12—C13—C18—O81.7 (3)
O4iii—Zn2—O1—C7169.47 (18)C14—C13—C18—O71.6 (3)
C8iii—Zn2—O1—C7171.67 (16)C12—C13—C18—O7178.3 (2)
O14—Zn1—O2—C774.6 (3)C26—C21—C22—C230.6 (3)
O9—Zn1—O2—C7108.8 (3)C27—C21—C22—C23180.0 (2)
O16i—Zn1—O2—C717.2 (3)C21—C22—C23—C243.7 (3)
O11ii—Zn1—O2—C7163.2 (3)C21—C22—C23—C28176.8 (2)
O10—Zn3—O5—C1763.03 (17)C22—C23—C24—C253.4 (3)
O11ii—Zn3—O5—C1760.01 (16)C28—C23—C24—C25177.2 (2)
O7iv—Zn3—O5—C17175.06 (15)C23—C24—C25—C260.1 (4)
O14—Zn1—O6—C1782.3 (3)C24—C25—C26—C213.2 (4)
O9—Zn1—O6—C1794.3 (3)C22—C21—C26—C252.9 (3)
O16i—Zn1—O6—C17173.8 (3)C27—C21—C26—C25176.6 (2)
O11ii—Zn1—O6—C176.6 (3)Zn1—O9—C27—O1029.2 (4)
O2—Zn1—O9—C27155.4 (2)Zn1—O9—C27—C21152.36 (18)
O6—Zn1—O9—C2720.6 (2)Zn3—O10—C27—O910.4 (3)
O16i—Zn1—O9—C27114.5 (2)Zn3—O10—C27—C21168.02 (15)
O11ii—Zn1—O9—C2763.5 (2)C26—C21—C27—O918.2 (3)
O11ii—Zn3—O10—C276.36 (19)C22—C21—C27—O9162.4 (2)
O7iv—Zn3—O10—C27142.94 (16)C26—C21—C27—O10160.4 (2)
O5—Zn3—O10—C27107.54 (17)C22—C21—C27—O1019.0 (3)
O1—Zn2—O13—C4797.71 (19)Zn3i—O11—C28—O122.3 (3)
O16i—Zn2—O13—C479.8 (2)Zn1i—O11—C28—O12122.5 (2)
O3iii—Zn2—O13—C47157.96 (18)Zn3i—O11—C28—C23176.84 (15)
O4iii—Zn2—O13—C4798.55 (18)Zn1i—O11—C28—C2358.3 (3)
C8iii—Zn2—O13—C47127.97 (19)C22—C23—C28—O1216.8 (3)
O2—Zn1—O14—C4737.1 (2)C24—C23—C28—O12162.7 (2)
O6—Zn1—O14—C47147.0 (2)C22—C23—C28—O11164.0 (2)
O16i—Zn1—O14—C4753.3 (2)C24—C23—C28—O1116.5 (3)
O11ii—Zn1—O14—C47128.6 (2)C35—N1—C31—C322.1 (6)
C6—C1—C2—C30.7 (4)N1—C31—C32—C330.1 (5)
C7—C1—C2—C3178.0 (2)C38—N2—C33—C320.5 (4)
C1—C2—C3—C42.6 (4)C38—N2—C33—C34179.2 (2)
C1—C2—C3—C8176.4 (2)C31—C32—C33—N2179.6 (3)
C2—C3—C4—C52.1 (4)C31—C32—C33—C341.8 (4)
C8—C3—C4—C5176.9 (2)N2—C33—C34—C35179.5 (3)
C3—C4—C5—C60.4 (4)C32—C33—C34—C351.7 (4)
C4—C5—C6—C12.3 (4)C31—N1—C35—C342.1 (6)
C2—C1—C6—C51.8 (4)C33—C34—C35—N10.2 (5)
C7—C1—C6—C5175.6 (2)C40—N3—C36—C370.4 (5)
Zn1—O2—C7—O12.7 (4)N3—C36—C37—C381.0 (4)
Zn1—O2—C7—C1178.93 (18)C33—N2—C38—C3713.3 (4)
Zn2—O1—C7—O213.8 (3)C33—N2—C38—C39168.3 (3)
Zn2—O1—C7—C1164.62 (16)C36—C37—C38—N2179.2 (3)
C6—C1—C7—O2165.9 (2)C36—C37—C38—C390.8 (4)
C2—C1—C7—O211.4 (3)N2—C38—C39—C40178.7 (3)
C6—C1—C7—O112.6 (3)C37—C38—C39—C400.1 (4)
C2—C1—C7—O1170.1 (2)C36—N3—C40—C390.3 (5)
Zn2iv—O4—C8—O32.6 (2)C38—C39—C40—N30.5 (5)
Zn2iv—O4—C8—C3177.7 (2)C46—C41—C42—C432.9 (3)
Zn2iv—O3—C8—O43.0 (3)C47—C41—C42—C43177.0 (2)
Zn2iv—O3—C8—C3177.37 (19)C41—C42—C43—C444.5 (3)
C4—C3—C8—O4173.6 (2)C41—C42—C43—C48177.9 (2)
C2—C3—C8—O47.3 (4)C42—C43—C44—C451.8 (3)
C4—C3—C8—O36.7 (4)C48—C43—C44—C45179.4 (2)
C2—C3—C8—O3172.4 (2)C43—C44—C45—C462.6 (3)
C16—C11—C12—C131.5 (4)C44—C45—C46—C414.2 (4)
C17—C11—C12—C13175.4 (2)C42—C41—C46—C451.5 (3)
C11—C12—C13—C140.9 (3)C47—C41—C46—C45178.7 (2)
C11—C12—C13—C18179.1 (2)Zn1—O14—C47—O1320.3 (4)
C12—C13—C14—C150.6 (4)Zn1—O14—C47—C41160.78 (16)
C18—C13—C14—C15179.4 (2)Zn2—O13—C47—O148.5 (3)
C13—C14—C15—C161.5 (4)Zn2—O13—C47—C41170.41 (15)
C14—C15—C16—C110.9 (4)C42—C41—C47—O14153.6 (2)
C12—C11—C16—C150.6 (4)C46—C41—C47—O1426.3 (3)
C17—C11—C16—C15176.3 (2)C42—C41—C47—O1327.4 (3)
Zn1—O6—C17—O532.2 (4)C46—C41—C47—O13152.7 (2)
Zn1—O6—C17—C11150.8 (2)Zn2ii—O16—C48—O154.2 (3)
Zn3—O5—C17—O67.0 (3)Zn1ii—O16—C48—O15123.4 (2)
Zn3—O5—C17—C11170.05 (15)Zn2ii—O16—C48—C43173.05 (16)
C12—C11—C17—O62.6 (3)Zn1ii—O16—C48—C4359.4 (3)
C16—C11—C17—O6179.5 (2)C42—C43—C48—O1519.1 (3)
C12—C11—C17—O5174.6 (2)C44—C43—C48—O15158.5 (2)
C16—C11—C17—O52.3 (3)C42—C43—C48—O16163.6 (2)
Zn3iii—O7—C18—O89.1 (3)C44—C43—C48—O1618.8 (3)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y1, z; (iv) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O8iv0.86 (2)1.92 (2)2.778 (3)172 (4)
O1W—H1B···O40.86 (2)1.87 (2)2.733 (3)174 (4)
N1—H1N···O2WA0.90 (2)2.03 (3)2.808 (6)144 (4)
N1—H1N···O2WBv0.90 (2)1.96 (3)2.757 (5)147 (4)
N2—H2N···O1Wi0.86 (2)1.89 (2)2.754 (3)176 (3)
N3—H3N···O12vi0.88 (2)1.93 (2)2.764 (3)157 (3)
Symmetry codes: (i) x1, y, z; (iv) x, y+1, z; (v) x, y+2, z; (vi) x1, y+1, z+1.

Experimental details

Crystal data
Chemical formula(C10H11N3)[Zn3(C8H4O4)4]·2H2O
Mr1061.81
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.5780 (13), 10.2149 (14), 21.246 (3)
α, β, γ (°)78.801 (2), 86.868 (2), 87.773 (2)
V3)2035.2 (5)
Z2
Radiation typeMo Kα
µ (mm1)1.84
Crystal size (mm)0.54 × 0.20 × 0.12
Data collection
DiffractometerBruker SMART 1K
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.617, 0.802
No. of measured, independent and
observed [I > 2σ(I)] reflections
24469, 9553, 8108
Rint0.024
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.081, 1.07
No. of reflections9553
No. of parameters619
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.92, 0.54

Computer programs: SMART (Bruker, 2006), SAINT-Plus (Bruker, 2006), SAINT-Plus (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalMaker (Palmer, 2007).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O8i0.863 (18)1.921 (19)2.778 (3)172 (4)
O1W—H1B···O40.863 (18)1.874 (19)2.733 (3)174 (4)
N1—H1N···O2WA0.901 (19)2.03 (3)2.808 (6)144 (4)
N1—H1N···O2WBii0.901 (19)1.96 (3)2.757 (5)147 (4)
N2—H2N···O1Wiii0.862 (17)1.893 (18)2.754 (3)176 (3)
N3—H3N···O12iv0.880 (17)1.93 (2)2.764 (3)157 (3)
Symmetry codes: (i) x, y+1, z; (ii) x, y+2, z; (iii) x1, y, z; (iv) x1, y+1, z+1.
 

Acknowledgements

We gratefully acknowledge the donors of the American Chemical Society Petroleum Research Fund and Michigan State University for funding this work.

References

First citationBraverman, M. A., Supkowski, R. M. & LaDuca, R. L. (2007). Inorg. Chim. Acta, 360, 2353–2362.  Web of Science CSD CrossRef CAS
First citationBruker (2006). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationPalmer, D. (2007). CrystalMaker. CrystalMaker Software Ltd, Bicester, Oxfordshire, England.
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationZapf, P. J., LaDuca, R. L., Rarig, R. S., Johnson, K. M. III & Zubieta, J. (1998). Inorg. Chem. 37, 3411–3414.  Web of Science CSD CrossRef CAS

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