metal-organic compounds
Poly[μ2-benzene-1,3-dicarboxylato-κ2O:O′-μ2-1,3-di-4-pyridylpropane-κ2N:N′-zinc(II)]
aCollege of Chemistry and Materials, Fujian Normal University, Fuzhou 350007, People's Republic of China, bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, People's Republic of China, and cConjugate and Medicinal Chemistry Laboratory, Department of Radiology, Brigham and Women's Hospital and Harvard Medical School, Boston, MA 02115, USA
*Correspondence e-mail: dym@fjnu.edu.cn
The title compound, [Zn(C8H4O4)(C13H14N2)]n, was obtained by the hydrothermal reaction of Zn(OAc)2·H2O with 1,3-di-4-pyridylpropane (bpp) and isophthalic acid (H2ip). The ZnII ion is coordinated by two bpp and two ip ligands in a distorted tetrahedral environment. Each ligand coordinates in a bridging mode to connect ZnII ions into a three-dimensional diamondoid-type structure.
Related literature
For related literature, see: Dai et al. (2005); Evans et al. (1999); Tang et al. (2004); Fujita et al. (1994).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808001621/lh2583sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808001621/lh2583Isup2.hkl
A mixture of Zn(Ac)2 H2O (1.00 mmol, 0.22 g), bpp (1.00 mmol, 0.19 g), H2ip (1.00 mmol, 0.16 g) and H2O (15 ml) was vigorous stirring until the pH was adjusted to 6 by adding 10% NaOH. This mixture was heated at 433 K for 3 days in a sealed 25 ml Teflon-lined stainless steel vessel under autogenous pressure. After cooling to room temperature at 50 K h-1, orange prism-shaped crystals were isolated, which were washed with ethanol and dried in air.
H atoms were positioned geometrically and refined using a riding model [C—H 0.93–0.97Å and Uiso(H) = 1.2Ueq(C)].
Data collection: SMART (Siemens, 1996); cell
SAINT (Siemens, 1997); data reduction: SAINT (Siemens, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Zn(C8H4O4)(C13H14N2)] | F(000) = 880 |
Mr = 427.76 | Dx = 1.507 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4994 reflections |
a = 11.0418 (13) Å | θ = 3.2–27.5° |
b = 11.1924 (14) Å | µ = 1.33 mm−1 |
c = 16.8687 (17) Å | T = 293 K |
β = 115.249 (7)° | Prism, orange |
V = 1885.5 (4) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 4328 independent reflections |
Radiation source: fine-focus sealed tube | 3887 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.733, Tmax = 0.875 | k = −11→14 |
14111 measured reflections | l = −21→21 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0695P)2 + 1.1112P] where P = (Fo2 + 2Fc2)/3 |
4328 reflections | (Δ/σ)max = 0.002 |
254 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
[Zn(C8H4O4)(C13H14N2)] | V = 1885.5 (4) Å3 |
Mr = 427.76 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.0418 (13) Å | µ = 1.33 mm−1 |
b = 11.1924 (14) Å | T = 293 K |
c = 16.8687 (17) Å | 0.30 × 0.20 × 0.10 mm |
β = 115.249 (7)° |
Bruker SMART CCD diffractometer | 4328 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3887 reflections with I > 2σ(I) |
Tmin = 0.733, Tmax = 0.875 | Rint = 0.020 |
14111 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.73 e Å−3 |
4328 reflections | Δρmin = −0.76 e Å−3 |
254 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.21026 (3) | 1.06213 (2) | 0.850451 (16) | 0.03187 (11) | |
O1 | 0.1788 (2) | 0.88899 (17) | 0.71665 (12) | 0.0485 (5) | |
O2 | 0.2385 (2) | 1.07900 (15) | 0.74443 (11) | 0.0405 (4) | |
O3 | 0.2086 (3) | 1.3428 (2) | 0.50730 (17) | 0.0828 (9) | |
O4 | 0.22045 (18) | 1.27148 (16) | 0.38941 (11) | 0.0412 (4) | |
N1 | 0.0122 (2) | 1.02485 (18) | 0.81573 (13) | 0.0346 (4) | |
N2 | 0.3207 (2) | 0.92958 (18) | 0.93261 (13) | 0.0379 (5) | |
C1 | 0.1641 (2) | 1.0385 (2) | 0.43263 (15) | 0.0375 (5) | |
H1A | 0.1559 | 1.0490 | 0.3759 | 0.045* | |
C2 | 0.1551 (2) | 0.9102 (2) | 0.54416 (16) | 0.0354 (5) | |
H2A | 0.1387 | 0.8354 | 0.5616 | 0.042* | |
C3 | −0.0341 (3) | 0.9129 (2) | 0.81017 (17) | 0.0388 (5) | |
H3A | 0.0255 | 0.8498 | 0.8201 | 0.047* | |
C4 | −0.4016 (3) | 0.9562 (3) | 0.7578 (2) | 0.0491 (7) | |
H4A | −0.4054 | 0.9442 | 0.8137 | 0.059* | |
H4B | −0.4533 | 1.0272 | 0.7313 | 0.059* | |
C5 | −0.1657 (3) | 0.8869 (2) | 0.79050 (16) | 0.0410 (5) | |
H5A | −0.1931 | 0.8078 | 0.7875 | 0.049* | |
C6 | −0.2578 (2) | 0.9791 (2) | 0.77504 (15) | 0.0370 (5) | |
C7 | 0.1420 (3) | 0.9271 (2) | 0.45968 (17) | 0.0407 (6) | |
H7A | 0.1182 | 0.8632 | 0.4207 | 0.049* | |
C8 | 0.2136 (2) | 1.1160 (2) | 0.57552 (14) | 0.0333 (5) | |
H8A | 0.2380 | 1.1798 | 0.6146 | 0.040* | |
C9 | 0.1985 (2) | 1.1341 (2) | 0.49008 (14) | 0.0332 (5) | |
C10 | 0.2109 (3) | 1.2590 (2) | 0.46194 (16) | 0.0403 (5) | |
C11 | 0.2035 (2) | 0.9872 (2) | 0.69431 (14) | 0.0322 (5) | |
C12 | 0.4479 (2) | 0.7383 (2) | 1.04535 (15) | 0.0353 (5) | |
C13 | 0.1929 (2) | 1.0050 (2) | 0.60318 (14) | 0.0302 (4) | |
C14 | 0.3843 (5) | 0.8270 (3) | 1.0680 (2) | 0.0765 (12) | |
H14A | 0.3829 | 0.8252 | 1.1227 | 0.092* | |
C15 | 0.3220 (5) | 0.9198 (3) | 1.0112 (2) | 0.0780 (13) | |
H15A | 0.2790 | 0.9782 | 1.0290 | 0.094* | |
C16 | 0.3822 (3) | 0.8432 (3) | 0.91049 (19) | 0.0596 (9) | |
H16A | 0.3829 | 0.8469 | 0.8556 | 0.072* | |
C17 | 0.4451 (3) | 0.7481 (3) | 0.96411 (18) | 0.0575 (8) | |
H17A | 0.4862 | 0.6900 | 0.9446 | 0.069* | |
C18 | −0.0769 (3) | 1.1138 (2) | 0.79964 (17) | 0.0413 (5) | |
H18A | −0.0472 | 1.1921 | 0.8027 | 0.050* | |
C19 | −0.4686 (3) | 0.8497 (2) | 0.69901 (16) | 0.0424 (6) | |
H19A | −0.4147 | 0.7790 | 0.7231 | 0.051* | |
H19B | −0.5554 | 0.8365 | 0.6990 | 0.051* | |
C20 | 0.5127 (2) | 0.6335 (2) | 1.10512 (16) | 0.0393 (5) | |
H20A | 0.5996 | 0.6190 | 1.1055 | 0.047* | |
H20B | 0.4582 | 0.5630 | 1.0811 | 0.047* | |
C21 | −0.2100 (3) | 1.0941 (2) | 0.77886 (18) | 0.0429 (6) | |
H21A | −0.2682 | 1.1586 | 0.7673 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.03897 (18) | 0.03055 (17) | 0.02643 (16) | −0.00058 (10) | 0.01427 (12) | 0.00286 (9) |
O1 | 0.0735 (13) | 0.0335 (9) | 0.0400 (9) | −0.0039 (9) | 0.0257 (9) | 0.0072 (8) |
O2 | 0.0602 (11) | 0.0360 (9) | 0.0325 (8) | −0.0046 (8) | 0.0266 (8) | −0.0023 (7) |
O3 | 0.166 (3) | 0.0358 (11) | 0.0722 (15) | −0.0180 (14) | 0.0749 (18) | −0.0039 (11) |
O4 | 0.0501 (10) | 0.0401 (9) | 0.0381 (9) | 0.0086 (8) | 0.0233 (8) | 0.0138 (7) |
N1 | 0.0386 (10) | 0.0289 (9) | 0.0346 (9) | −0.0028 (8) | 0.0139 (8) | −0.0002 (8) |
N2 | 0.0436 (11) | 0.0367 (11) | 0.0306 (10) | 0.0021 (8) | 0.0131 (9) | 0.0055 (8) |
C1 | 0.0402 (12) | 0.0450 (13) | 0.0271 (10) | 0.0023 (10) | 0.0143 (9) | 0.0005 (10) |
C2 | 0.0417 (12) | 0.0290 (11) | 0.0362 (11) | −0.0001 (9) | 0.0173 (10) | 0.0000 (9) |
C3 | 0.0459 (13) | 0.0282 (11) | 0.0433 (13) | 0.0008 (10) | 0.0198 (11) | 0.0017 (10) |
C4 | 0.0458 (14) | 0.0557 (17) | 0.0506 (15) | −0.0129 (12) | 0.0250 (13) | −0.0232 (13) |
C5 | 0.0525 (14) | 0.0300 (12) | 0.0417 (13) | −0.0090 (10) | 0.0213 (11) | −0.0047 (10) |
C6 | 0.0410 (12) | 0.0406 (13) | 0.0301 (10) | −0.0072 (10) | 0.0160 (9) | −0.0095 (10) |
C7 | 0.0514 (15) | 0.0356 (13) | 0.0346 (12) | −0.0032 (10) | 0.0180 (11) | −0.0090 (10) |
C8 | 0.0411 (12) | 0.0304 (11) | 0.0301 (10) | −0.0019 (9) | 0.0167 (9) | −0.0020 (9) |
C9 | 0.0369 (11) | 0.0338 (12) | 0.0306 (10) | 0.0009 (9) | 0.0160 (9) | 0.0043 (9) |
C10 | 0.0510 (14) | 0.0363 (13) | 0.0370 (12) | −0.0009 (10) | 0.0221 (11) | 0.0055 (10) |
C11 | 0.0365 (11) | 0.0316 (11) | 0.0301 (10) | 0.0039 (9) | 0.0157 (9) | 0.0031 (9) |
C12 | 0.0342 (11) | 0.0348 (12) | 0.0343 (11) | 0.0005 (9) | 0.0121 (9) | 0.0042 (9) |
C13 | 0.0324 (10) | 0.0300 (11) | 0.0296 (10) | 0.0029 (8) | 0.0146 (8) | 0.0019 (8) |
C14 | 0.145 (4) | 0.0503 (18) | 0.0402 (15) | 0.042 (2) | 0.046 (2) | 0.0145 (13) |
C15 | 0.148 (4) | 0.0481 (17) | 0.0414 (16) | 0.046 (2) | 0.044 (2) | 0.0115 (13) |
C16 | 0.0671 (19) | 0.078 (2) | 0.0407 (14) | 0.0318 (17) | 0.0300 (14) | 0.0196 (14) |
C17 | 0.0651 (18) | 0.069 (2) | 0.0436 (14) | 0.0355 (16) | 0.0278 (14) | 0.0143 (14) |
C18 | 0.0454 (13) | 0.0274 (12) | 0.0484 (14) | −0.0035 (10) | 0.0175 (11) | −0.0010 (10) |
C19 | 0.0398 (13) | 0.0458 (14) | 0.0429 (13) | −0.0119 (11) | 0.0190 (11) | −0.0146 (11) |
C20 | 0.0399 (13) | 0.0367 (13) | 0.0417 (12) | 0.0067 (10) | 0.0179 (10) | 0.0076 (10) |
C21 | 0.0429 (14) | 0.0339 (12) | 0.0493 (14) | 0.0026 (11) | 0.0172 (12) | −0.0044 (11) |
Zn1—O2 | 1.9511 (17) | C5—H5A | 0.9300 |
Zn1—O4i | 1.9621 (17) | C6—C21 | 1.383 (4) |
Zn1—N2 | 2.041 (2) | C7—H7A | 0.9300 |
Zn1—N1 | 2.051 (2) | C8—C9 | 1.393 (3) |
O1—C11 | 1.230 (3) | C8—C13 | 1.381 (3) |
O2—C11 | 1.281 (3) | C8—H8A | 0.9300 |
O3—C10 | 1.218 (3) | C9—C10 | 1.501 (3) |
O4—C10 | 1.279 (3) | C11—C13 | 1.504 (3) |
O4—Zn1ii | 1.9621 (17) | C12—C14 | 1.361 (4) |
N1—C18 | 1.343 (3) | C12—C17 | 1.362 (3) |
N1—C3 | 1.342 (3) | C12—C20 | 1.513 (3) |
N2—C16 | 1.323 (4) | C14—C15 | 1.381 (4) |
N2—C15 | 1.324 (4) | C14—H14A | 0.9300 |
C1—C9 | 1.384 (3) | C15—H15A | 0.9300 |
C1—C7 | 1.384 (4) | C16—C17 | 1.377 (4) |
C1—H1A | 0.9300 | C16—H16A | 0.9300 |
C2—C7 | 1.383 (3) | C17—H17A | 0.9300 |
C2—C13 | 1.392 (3) | C18—C21 | 1.376 (4) |
C2—H2A | 0.9300 | C18—H18A | 0.9300 |
C3—C5 | 1.376 (4) | C19—C20iii | 1.519 (3) |
C3—H3A | 0.9300 | C19—H19A | 0.9700 |
C4—C19 | 1.524 (3) | C19—H19B | 0.9700 |
C4—C6 | 1.509 (4) | C20—C19iv | 1.519 (3) |
C4—H4A | 0.9700 | C20—H20A | 0.9700 |
C4—H4B | 0.9700 | C20—H20B | 0.9700 |
C5—C6 | 1.393 (4) | C21—H21A | 0.9300 |
O2—Zn1—O4i | 101.92 (7) | C1—C9—C10 | 122.2 (2) |
O2—Zn1—N2 | 114.19 (8) | O3—C10—O4 | 123.3 (2) |
O4i—Zn1—N2 | 122.01 (8) | O3—C10—C9 | 119.3 (2) |
O2—Zn1—N1 | 109.01 (8) | O4—C10—C9 | 117.4 (2) |
O4i—Zn1—N1 | 100.98 (8) | O1—C11—O2 | 123.9 (2) |
N2—Zn1—N1 | 107.55 (8) | O1—C11—C13 | 120.0 (2) |
C11—O2—Zn1 | 113.99 (14) | O2—C11—C13 | 116.04 (19) |
C10—O4—Zn1ii | 114.07 (17) | C14—C12—C17 | 115.5 (2) |
C18—N1—C3 | 117.0 (2) | C14—C12—C20 | 122.2 (2) |
C18—N1—Zn1 | 120.43 (17) | C17—C12—C20 | 122.3 (2) |
C3—N1—Zn1 | 122.55 (17) | C8—C13—C2 | 119.1 (2) |
C16—N2—C15 | 115.7 (2) | C8—C13—C11 | 120.8 (2) |
C16—N2—Zn1 | 124.72 (18) | C2—C13—C11 | 120.0 (2) |
C15—N2—Zn1 | 119.2 (2) | C12—C14—C15 | 121.2 (3) |
C9—C1—C7 | 120.0 (2) | C12—C14—H14A | 119.4 |
C9—C1—H1A | 120.0 | C15—C14—H14A | 119.4 |
C7—C1—H1A | 120.0 | N2—C15—C14 | 123.1 (3) |
C7—C2—C13 | 120.1 (2) | N2—C15—H15A | 118.4 |
C7—C2—H2A | 120.0 | C14—C15—H15A | 118.4 |
C13—C2—H2A | 120.0 | N2—C16—C17 | 123.7 (2) |
N1—C3—C5 | 123.1 (2) | N2—C16—H16A | 118.1 |
N1—C3—H3A | 118.5 | C17—C16—H16A | 118.1 |
C5—C3—H3A | 118.5 | C16—C17—C12 | 120.8 (3) |
C19—C4—C6 | 115.9 (2) | C16—C17—H17A | 119.6 |
C19—C4—H4A | 108.3 | C12—C17—H17A | 119.6 |
C6—C4—H4A | 108.3 | N1—C18—C21 | 122.9 (2) |
C19—C4—H4B | 108.3 | N1—C18—H18A | 118.5 |
C6—C4—H4B | 108.3 | C21—C18—H18A | 118.5 |
H4A—C4—H4B | 107.4 | C20iii—C19—C4 | 113.2 (2) |
C3—C5—C6 | 120.0 (2) | C20iii—C19—H19A | 108.9 |
C3—C5—H5A | 120.0 | C4—C19—H19A | 108.9 |
C6—C5—H5A | 120.0 | C20iii—C19—H19B | 108.9 |
C5—C6—C21 | 116.6 (2) | C4—C19—H19B | 108.9 |
C5—C6—C4 | 122.3 (2) | H19A—C19—H19B | 107.7 |
C21—C6—C4 | 121.1 (2) | C12—C20—C19iv | 114.5 (2) |
C2—C7—C1 | 120.5 (2) | C12—C20—H20A | 108.6 |
C2—C7—H7A | 119.8 | C19iv—C20—H20A | 108.6 |
C1—C7—H7A | 119.8 | C12—C20—H20B | 108.6 |
C9—C8—C13 | 121.1 (2) | C19iv—C20—H20B | 108.6 |
C9—C8—H8A | 119.5 | H20A—C20—H20B | 107.6 |
C13—C8—H8A | 119.5 | C18—C21—C6 | 120.4 (2) |
C8—C9—C1 | 119.2 (2) | C18—C21—H21A | 119.8 |
C8—C9—C10 | 118.4 (2) | C6—C21—H21A | 119.8 |
Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) x, −y+5/2, z−1/2; (iii) x−1, −y+3/2, z−1/2; (iv) x+1, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C8H4O4)(C13H14N2)] |
Mr | 427.76 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.0418 (13), 11.1924 (14), 16.8687 (17) |
β (°) | 115.249 (7) |
V (Å3) | 1885.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.33 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.733, 0.875 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14111, 4328, 3887 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.115, 1.04 |
No. of reflections | 4328 |
No. of parameters | 254 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.73, −0.76 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1997), SHELXTL (Sheldrick, 2008).
Zn1—O2 | 1.9511 (17) | Zn1—N2 | 2.041 (2) |
Zn1—O4i | 1.9621 (17) | Zn1—N1 | 2.051 (2) |
O2—Zn1—O4i | 101.92 (7) | O2—Zn1—N1 | 109.01 (8) |
O2—Zn1—N2 | 114.19 (8) | O4i—Zn1—N1 | 100.98 (8) |
O4i—Zn1—N2 | 122.01 (8) | N2—Zn1—N1 | 107.55 (8) |
Symmetry code: (i) x, −y+5/2, z+1/2. |
Acknowledgements
This work was financially supported by the Youth Talent Foundation of Fujian Province (2006F3010330083).
References
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A large family of coordination polymers has been developed recently owing to their potential applications as functional solid materials and their intriguing architectures or topologies (Evans et al., 1999; Fujita et al., 1994). It is now well understood that the hydrothermal crystallization of metal centers with multidentate N– or O-donor ligands, which possess more rich coordination sites and a wide variety of shapes to facilitate the formation of various networks, is one of the useful approaches to assembly desired new materials. An impressive literature of one-, two- and three-dimensional frameworks based on these ligands (Dai et al., 2005,Tang et al., 2004) with various structural motifs, such as helical, brick wall, ladder, honeycomb, square grid, parquet, and diamondoid, have been reported to date. Here we report the synthesis and crystal structure of the title compound (I).
In (I) [Fig. 1] each ZnII ion coordinates to two pyridine N atoms of two bpp ligands and two carboxylate groups of two ip ligands, in monodentate modes, giving a distorted tetrahedral coordination environment. Both bpp and ip ligands coordinate in bridging modes to for a three-dimensional diamondoid structure with Zn···Zn separations of 9.425 and 12.745Å and formimg cavities within the structure (Fig. 2).