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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m282.
Published online 2010 February 13. doi:  10.1107/S1600536810004848
PMCID: PMC2983653

Poly[tris­(2,5-dimethyl­benzene-1,4-­dicarboxyl­ato)bis­(pyridine)trizinc(II)]

Abstract

The asymmetric unit of the title polymeric compound, [Zn3(C10H8O4)3(C5H5N)2]n or [Zn3(dmbdc)3(py)2]n (dmbdc = 2,5-dimethyl­benzene­dicarboxyl­ate; py = pyridine) contains two Zn(II) ions, one of which is located on an inversion centre, one and a half 2,5-dimethyl­benzene­dicarboxyl­ate ligands and one pyridine ligand. Each ZnO6 octa­hedron is sandwiched between two ZnO4N square-pyramids, forming a trinuclear zinc secondary building unit (SBU); each SBU is further linked by six 2,5-dimethyl­benzene­dicarboxyl­ate ligands with six adjacent trinuclear zinc SBU’s, forming a two-dimensional layer structure with a (3,6) net. One of the three zinc ions is octa­hedrally coordinated and the other two are square-pyramidally coordinated. The coordination modes for 2,5-dimethyl­benzene­dicarboxyl­ates are bis­(bidentate) or bidentate-tridentate.

Related literature

For the potential applications of metal-organic frameworks formed from terephthalic acid and its derivatives, see Wang et al. (2007 [triangle]); Grzesiak et al. (2006 [triangle]); Rosi et al. (2005 [triangle]); Burrows et al. (2005 [triangle]); Liao et al. (2006 [triangle]); Yang et al. (2002 [triangle]); Eddaoudi et al. (2002 [triangle]). For related structures, see: Wang et al. (2008 [triangle]); Zhou et al. (2009 [triangle]).

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Object name is e-66-0m282-scheme1.jpg

Experimental

Crystal data

  • [Zn3(C10H8O4)3(C5H5N)2]
  • M r = 930.80
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m282-efi1.jpg
  • a = 22.3372 (15) Å
  • b = 10.2643 (7) Å
  • c = 16.9261 (11) Å
  • β = 105.140 (1)°
  • V = 3746.0 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.97 mm−1
  • T = 299 K
  • 0.12 × 0.08 × 0.07 mm

Data collection

  • Bruker SMART APEX area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.798, T max = 0.874
  • 16107 measured reflections
  • 4487 independent reflections
  • 3559 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.156
  • S = 1.08
  • 4487 reflections
  • 262 parameters
  • H-atom parameters constrained
  • Δρmax = 0.74 e Å−3
  • Δρmin = −0.63 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: ORTEPII (Johnson, 1976 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810004848/bv2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004848/bv2132Isup2.hkl

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

Acknowledgments

We are grateful for financial support by the National Natural Science Foundation of China (grant No. 20471049) and Xiamen University.

supplementary crystallographic information

Comment

Terephthalic acid and its derivatives have been used to construct metal-organic frameworks. Some of these compounds display interesting structures and have potential applications (Wang et al., 2007; Grzesiak et al., 2006; Rosi et al., 2005; Burrows et al., 2005; Liao et al., 2006; Yang et al., 2002; Eddaoudi et al.,2002; Zhou et al., 2009). In this paper we report a coordination polymer [Zn3(dmbdc)3(py)2]n, 1 (dmbdc=2,5-dimethylbenzenedicarboxylate; py=pyridine) synthesized by hydrothermal reaction.

The structure of 1 contains trinuclear zinc SBU's (SBU = Secondary Building Unit) (Fig. 1), in which each ZnO6 octahedron sandwiched between two ZnO4N square-pyramids. The three Zn ions exhibit two different coordination geometries: Zn1 coordinates to four oxygen atoms from three carboxylates in the plane and a nitrogen atom from py (py = pyridine) at the apex giving a distorted square-pyramidal geometry; Zn2 atom is coordinated by six oxygen atoms from six dmbdc anions (dmbdc=2,5-dimethylbenzenedicarboxylate) to constitute a slightly distorted octahedral environment. Coordination polymers with similar but different trinuclear zinc SBU's have been reported in recent years (Wang et al., 2008). There are two coordination modes for the dmbdc in the structure of 1, one is bis(bidentate), and the other one adopts bidentate and tridentate for each of its carboxyl groups. However, each trinuclear zinc SBU is further linked by six dmbdc ligands to six adjacent trinuclear zinc SBU's to form a two-dimensional sheet with a (3,6) net parallel to bc plane (Fig. 2). The two-dimensional sheets are further packed in an ABAB··· mode along b axis (Fig. 3). Coordinated pyridine molecules lie in the both sides of trinuclear zinc SBU's respectively.

Experimental

A suspension of 2,5-dimethylbenzenedicarboxylic acid (H2dmbdc, 0.097 g, 0.50 mmol) in H2O (12 ml), pyridine was slowly added to the solution until pH was adjusted to 7, then Zn(NO3)2.6H2O (0.15 g, 0.50 mmol) was added. The mixture was placed in a 20 ml Teflon-lined vessel, heated to 120°C at the rate of 0.2°C/min, and kept at 120°C for 3 days, then slowly cooled down to room temperature at the rate of 0.1°C/min. Colorless platelet crystals (0.062 g, yield 40%) were separated by filtration, washed with deionized water and dried in air. Elemental Analysis: C40H34N2O12Zn3, found (calc.) C 51.52 (51.61), H 3.66 (3.69), N 2.99 (3.01). FTIR (KBr, cm-1): 3454 (m), 3031 (w), 2961 (m), 2739 (w), 1922 (w), 1820 (m),1452 (m), 1399 (s), 1347 (m), 1158 (m), 1074 (s), 918 (s), 797 (versus).

Refinement

The aromatic H atoms were generated geometrically (C—H 0.93 Å) and were allowed to ride on their parent atoms in the riding model approximations, with their temperature factors set to 1.2 times those of the parent atoms. The methyl H atoms were generated geometrically (C—H 0.96 Å) and were allowed to ride on their parent atoms in the riding model approximations, with their temperature factors set to 1.5 times those of the parent atoms.

Figures

Fig. 1.
The connection of the trinuclear zinc SBU's. (Hydrogen atoms are omitted for clarity.)
Fig. 2.
A perspective view of the two-dimensional (3, 6) net of 1 on bc plane. (Hydrogen atoms are omitted for clarity.)
Fig. 3.
View of two-dimensional (3, 6) net of 1 stacked by ABAB mode along b axis. (Hydrogen atoms are omitted for clarity.)

Crystal data

[Zn3(C10H8O4)3(C5H5N)2]F(000) = 1896
Mr = 930.80Dx = 1.650 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2781 reflections
a = 22.3372 (15) Åθ = 2.2–25.0°
b = 10.2643 (7) ŵ = 1.97 mm1
c = 16.9261 (11) ÅT = 299 K
β = 105.140 (1)°Block, colorless
V = 3746.0 (4) Å30.12 × 0.08 × 0.07 mm
Z = 4

Data collection

Bruker SMART APEX area-detector diffractometer4487 independent reflections
Radiation source: fine-focus sealed tube3559 reflections with I > 2σ(I)
graphiteRint = 0.059
[var phi] and ω scanθmax = 28.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −28→30
Tmin = 0.798, Tmax = 0.874k = −13→13
16107 measured reflectionsl = −21→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0282P)2 + 12.5564P] where P = (Fo2 + 2Fc2)/3
4487 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = −0.62 e Å3

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
Zn10.40381 (2)0.67147 (5)0.55736 (3)0.02859 (17)
Zn20.25000.75000.50000.02465 (19)
O10.40247 (16)0.7797 (3)0.4622 (2)0.0379 (8)
O20.31369 (15)0.8673 (3)0.4686 (2)0.0347 (7)
O30.29594 (17)1.2435 (4)0.12228 (19)0.0425 (9)
O40.39737 (16)1.2197 (4)0.1478 (2)0.0426 (9)
O50.37531 (18)0.4905 (4)0.5713 (3)0.0557 (11)
O60.30025 (18)0.5819 (3)0.4821 (2)0.0444 (9)
N10.49686 (18)0.6283 (4)0.5907 (3)0.0397 (10)
C10.3588 (2)0.9476 (5)0.3687 (3)0.0309 (10)
C20.4095 (2)0.9664 (5)0.3361 (3)0.0368 (11)
C30.4018 (2)1.0506 (5)0.2701 (3)0.0362 (11)
H3A0.43541.06450.24830.043*
C40.3476 (2)1.1143 (4)0.2354 (3)0.0297 (9)
C50.2970 (2)1.0983 (5)0.2683 (3)0.0310 (9)
C60.3049 (2)1.0147 (5)0.3343 (3)0.0325 (10)
H6A0.27161.00310.35700.039*
C70.3581 (2)0.8590 (4)0.4383 (3)0.0297 (9)
C80.4722 (3)0.9037 (8)0.3691 (5)0.074 (2)
H8A0.50090.93820.34090.111*
H8B0.46860.81120.36080.111*
H8C0.48710.92180.42650.111*
C90.3457 (2)1.1994 (4)0.1631 (3)0.0308 (10)
C100.2367 (3)1.1692 (6)0.2392 (4)0.0521 (15)
H10A0.20901.14240.27090.078*
H10B0.21871.14930.18250.078*
H10C0.24391.26130.24540.078*
C110.3226 (2)0.4861 (5)0.5232 (3)0.0400 (12)
C120.2872 (2)0.3605 (4)0.5142 (3)0.0322 (10)
C130.2293 (2)0.3618 (4)0.4598 (3)0.0363 (11)
H13A0.21540.43920.43270.044*
C140.3094 (2)0.2458 (5)0.5566 (3)0.0381 (11)
C150.3713 (3)0.2313 (6)0.6163 (4)0.0630 (18)
H15A0.37680.14270.63510.095*
H15B0.37380.28810.66210.095*
H15C0.40330.25370.59030.095*
C160.5188 (3)0.5242 (8)0.6329 (6)0.103 (4)
H16A0.49110.46430.64470.124*
C170.5805 (4)0.5003 (10)0.6601 (8)0.134 (5)
H17A0.59440.42560.69060.161*
C180.6214 (3)0.5840 (8)0.6433 (6)0.081 (2)
H18A0.66380.57000.66340.098*
C190.6002 (3)0.6877 (7)0.5972 (4)0.0612 (17)
H19A0.62740.74530.58210.073*
C200.5379 (3)0.7074 (6)0.5725 (4)0.0536 (15)
H20A0.52340.78080.54110.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0302 (3)0.0257 (3)0.0305 (3)−0.0001 (2)0.0090 (2)0.0002 (2)
Zn20.0236 (4)0.0256 (4)0.0249 (3)−0.0023 (3)0.0067 (3)−0.0003 (3)
O10.0374 (18)0.0410 (19)0.0380 (18)0.0055 (15)0.0149 (15)0.0153 (15)
O20.0362 (18)0.0304 (17)0.0437 (19)−0.0038 (14)0.0213 (15)0.0055 (14)
O30.042 (2)0.060 (2)0.0234 (15)0.0153 (17)0.0050 (15)0.0087 (16)
O40.0374 (19)0.053 (2)0.0365 (18)−0.0024 (16)0.0089 (15)0.0189 (16)
O50.042 (2)0.035 (2)0.087 (3)−0.0140 (17)0.011 (2)−0.007 (2)
O60.065 (2)0.0217 (16)0.058 (2)−0.0018 (16)0.038 (2)−0.0008 (16)
N10.028 (2)0.037 (2)0.052 (3)0.0043 (17)0.0073 (18)0.002 (2)
C10.029 (2)0.036 (2)0.030 (2)−0.0017 (18)0.0097 (18)0.0038 (19)
C20.031 (2)0.040 (3)0.044 (3)0.004 (2)0.018 (2)0.009 (2)
C30.032 (2)0.045 (3)0.036 (2)0.002 (2)0.016 (2)0.009 (2)
C40.030 (2)0.031 (2)0.026 (2)−0.0008 (18)0.0042 (18)0.0016 (18)
C50.027 (2)0.033 (2)0.031 (2)−0.0005 (18)0.0057 (18)0.0025 (19)
C60.029 (2)0.035 (2)0.037 (2)0.0010 (19)0.0134 (19)0.004 (2)
C70.031 (2)0.026 (2)0.033 (2)−0.0048 (18)0.0113 (19)0.0013 (18)
C80.041 (3)0.100 (5)0.092 (5)0.031 (4)0.037 (3)0.060 (5)
C90.036 (3)0.028 (2)0.027 (2)−0.0017 (19)0.0062 (19)−0.0019 (18)
C100.036 (3)0.070 (4)0.051 (3)0.013 (3)0.014 (2)0.020 (3)
C110.045 (3)0.027 (2)0.055 (3)−0.005 (2)0.027 (3)−0.011 (2)
C120.032 (2)0.021 (2)0.049 (3)−0.0012 (17)0.019 (2)−0.0027 (19)
C130.034 (2)0.023 (2)0.053 (3)0.0055 (18)0.012 (2)0.007 (2)
C140.033 (2)0.031 (2)0.050 (3)0.0039 (19)0.009 (2)0.002 (2)
C150.042 (3)0.049 (4)0.084 (5)0.002 (3)−0.008 (3)0.014 (3)
C160.047 (4)0.083 (6)0.166 (9)0.003 (4)0.006 (5)0.071 (6)
C170.045 (4)0.109 (7)0.231 (13)0.015 (5)0.006 (6)0.098 (9)
C180.037 (3)0.081 (5)0.121 (7)0.012 (4)0.010 (4)−0.002 (5)
C190.038 (3)0.078 (5)0.069 (4)−0.011 (3)0.015 (3)−0.014 (4)
C200.043 (3)0.059 (4)0.059 (4)−0.006 (3)0.014 (3)0.007 (3)

Geometric parameters (Å, °)

Zn1—O4i1.931 (3)C4—C91.496 (6)
Zn1—O11.950 (3)C5—C61.384 (6)
Zn1—O51.998 (4)C5—C101.495 (7)
Zn1—N12.055 (4)C6—H6A0.9300
Zn1—C112.588 (5)C8—H8A0.9600
Zn2—O22.037 (3)C8—H8B0.9600
Zn2—O2ii2.037 (3)C8—H8C0.9600
Zn2—O3iii2.057 (3)C10—H10A0.9600
Zn2—O3i2.057 (3)C10—H10B0.9600
Zn2—O62.123 (3)C10—H10C0.9600
Zn2—O6ii2.123 (3)C11—C121.500 (6)
O1—C71.265 (6)C12—C131.378 (7)
O2—C71.233 (5)C12—C141.401 (7)
O3—C91.231 (6)C13—C14vi1.385 (7)
O3—Zn2iv2.057 (3)C13—H13A0.9300
O4—C91.264 (6)C14—C13vi1.385 (7)
O4—Zn1v1.931 (3)C14—C151.492 (7)
O5—C111.245 (6)C15—H15A0.9600
O6—C111.233 (6)C15—H15B0.9600
N1—C161.308 (8)C15—H15C0.9600
N1—C201.320 (7)C16—C171.356 (10)
C1—C61.378 (6)C16—H16A0.9300
C1—C21.395 (6)C17—C181.337 (11)
C1—C71.492 (6)C17—H17A0.9300
C2—C31.387 (7)C18—C191.332 (10)
C2—C81.511 (7)C18—H18A0.9300
C3—C41.367 (6)C19—C201.359 (8)
C3—H3A0.9300C19—H19A0.9300
C4—C51.393 (6)C20—H20A0.9300
O4i—Zn1—O1109.70 (17)O2—C7—C1117.6 (4)
O4i—Zn1—O5110.64 (18)O1—C7—C1118.4 (4)
O1—Zn1—O5133.67 (17)C2—C8—H8A109.5
O4i—Zn1—N1100.73 (17)C2—C8—H8B109.5
O1—Zn1—N198.40 (16)H8A—C8—H8B109.5
O5—Zn1—N195.60 (17)C2—C8—H8C109.5
O4i—Zn1—C11114.20 (16)H8A—C8—H8C109.5
O1—Zn1—C11112.05 (17)H8B—C8—H8C109.5
O5—Zn1—C1127.91 (16)O3—C9—O4124.3 (4)
N1—Zn1—C11120.16 (17)O3—C9—C4120.2 (4)
O2—Zn2—O2ii180.00 (18)O4—C9—C4115.5 (4)
O2—Zn2—O3iii87.46 (14)C5—C10—H10A109.5
O2ii—Zn2—O3iii92.54 (14)C5—C10—H10B109.5
O2—Zn2—O3i92.54 (14)H10A—C10—H10B109.5
O2ii—Zn2—O3i87.46 (14)C5—C10—H10C109.5
O3iii—Zn2—O3i180.000 (1)H10A—C10—H10C109.5
O2—Zn2—O690.67 (13)H10B—C10—H10C109.5
O2ii—Zn2—O689.33 (13)O6—C11—O5121.0 (5)
O3iii—Zn2—O688.47 (15)O6—C11—C12120.2 (5)
O3i—Zn2—O691.53 (15)O5—C11—C12118.8 (5)
O2—Zn2—O6ii89.33 (13)O6—C11—Zn172.3 (3)
O2ii—Zn2—O6ii90.67 (13)O5—C11—Zn148.7 (2)
O3iii—Zn2—O6ii91.53 (15)C12—C11—Zn1167.2 (4)
O3i—Zn2—O6ii88.47 (15)C13—C12—C14119.8 (4)
O6—Zn2—O6ii180.0 (2)C13—C12—C11116.0 (4)
C7—O1—Zn1118.2 (3)C14—C12—C11124.3 (5)
C7—O2—Zn2139.4 (3)C12—C13—C14vi123.7 (4)
C9—O3—Zn2iv135.7 (3)C12—C13—H13A118.2
C9—O4—Zn1v121.2 (3)C14vi—C13—H13A118.2
C11—O5—Zn1103.4 (3)C13vi—C14—C12116.6 (5)
C11—O6—Zn2136.0 (3)C13vi—C14—C15118.4 (5)
C16—N1—C20116.5 (5)C12—C14—C15125.0 (5)
C16—N1—Zn1122.3 (4)C14—C15—H15A109.5
C20—N1—Zn1121.2 (4)C14—C15—H15B109.5
C6—C1—C2118.3 (4)H15A—C15—H15B109.5
C6—C1—C7116.7 (4)C14—C15—H15C109.5
C2—C1—C7125.1 (4)H15A—C15—H15C109.5
C3—C2—C1117.6 (4)H15B—C15—H15C109.5
C3—C2—C8118.1 (4)N1—C16—C17122.5 (7)
C1—C2—C8124.4 (4)N1—C16—H16A118.8
C4—C3—C2123.6 (4)C17—C16—H16A118.8
C4—C3—H3A118.2C18—C17—C16120.0 (8)
C2—C3—H3A118.2C18—C17—H17A120.0
C3—C4—C5119.5 (4)C16—C17—H17A120.0
C3—C4—C9117.6 (4)C19—C18—C17118.8 (7)
C5—C4—C9122.9 (4)C19—C18—H18A120.6
C6—C5—C4116.7 (4)C17—C18—H18A120.6
C6—C5—C10118.8 (4)C18—C19—C20118.5 (7)
C4—C5—C10124.5 (4)C18—C19—H19A120.7
C1—C6—C5124.3 (4)C20—C19—H19A120.7
C1—C6—H6A117.8N1—C20—C19123.7 (6)
C5—C6—H6A117.8N1—C20—H20A118.2
O2—C7—O1124.0 (4)C19—C20—H20A118.2

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2132).

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