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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 6| June 2011| Pages m715-m716

catena-Poly[[[bis­­(3-hy­dr­oxy­adamantane-1-carboxyl­ato-κO1)(3-hy­dr­oxy­adamantane-1-carb­­oxy­lic acid-κO1)zinc(II)]-μ2-4,4′-bi­pyridine] monohydrate]

aCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and bZhejiang Normal University Xingzhi College, Jinhua, Zhejiang 321004, People's Republic of China
*Correspondence e-mail: sky53@zjnu.cn

(Received 22 April 2011; accepted 30 April 2011; online 7 May 2011)

In the title coordination polymer, {[Zn(C11H15O3)2(C10H8N2)(C11H16O3)]·H2O}n, the ZnII ion is five coordinated by two N atoms from two 4,4′-bipyridine (4,4′-bpy) mol­ecules and three O atoms from two 3-hy­droxy­adamantane-1-carboxyl­ate anions (L) and one 3-hy­droxy­adamantane-1-carb­oxy­lic acid (HL) mol­ecule. The resulting coordination polyhedron is a near regular ZnN2O3 trigonal bipyramid, with the N atoms in axial sites. The 4,4′-bpy mol­ecules [dihedral angle between the aromatic rings = 17.2 (2)°] act as bridges, connecting the metal ions into an infinite polymeric chain propagating in [[\overline{1}]01]. O—H⋯O hydrogen bonds help to consolidate the packing.

Related literature

For background to adamantane-1-carb­oxy­lic acid complexes, see: Zhu et al. (2005[Zhu, Z.-L., Feng, Y.-L., Lin, H. & Chin, J. (2005). Rare Earth Soc. 23, 641-644.]); Milios et al. (2007[Milios, C. J., Inglis, R. & Bagai, R. (2007). Chem. Commun. 33, 3476-3478.]); Korlyukov et al. (2008[Korlyukov, A. A., Komissarov, E. A. & Antipin, M. Y. (2008). J. Mol. Struct. 875, 135-142.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C11H15O3)2(C10H8N2)(C11H16O3)]·H2O

  • Mr = 826.27

  • Monoclinic, C c

  • a = 17.8778 (2) Å

  • b = 16.6364 (2) Å

  • c = 13.2655 (1) Å

  • β = 92.642 (1)°

  • V = 3941.26 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.69 mm−1

  • T = 296 K

  • 0.34 × 0.23 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.826, Tmax = 0.904

  • 26431 measured reflections

  • 6904 independent reflections

  • 6188 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.094

  • S = 1.04

  • 6904 reflections

  • 506 parameters

  • 4 restraints

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.33 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3423 Friedel pairs

  • Flack parameter: 0.202 (9)

Table 1
Selected bond lengths (Å)

Zn1—O2 2.016 (3)
Zn1—O8 2.036 (3)
Zn1—O4 2.065 (3)
Zn1—N2i 2.138 (3)
Zn1—N1 2.174 (4)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O9—H9A⋯O1ii 0.82 2.05 2.872 (4) 178
O6—H6A⋯O3iii 0.82 2.00 2.812 (4) 169
O3—H3A⋯O9iv 0.82 1.99 2.790 (4) 165
O1W—H1WA⋯O6 0.85 2.19 3.013 (9) 163
O5—H5C⋯O7 0.85 1.67 2.447 (3) 151
O1W—H1WB⋯O7v 0.85 2.44 3.287 (9) 179
Symmetry codes: (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x, -y+1, z-{\script{1\over 2}}]; (iv) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (v) [x, -y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The fascinating structures of adamantane-1- carboxylic acid complexes coupled with their special functionality catch a lot of chemists' interests (Zhu et al.,2005; Milios et al.,2007; Korlyukov et al.,2008). To the best of our knowledge, the polymer complex using 4,4'-bipyridine as the linker and 3-hydroxyadamantane-1- carboxylic acid as filling agent has not been reported up to the present time. As an extension of our work in this field, we describe a new ZnII complex.

The structure of complex (1) was shown in Fig.1 and the coordination environment of ZnII was shown in Fig. 2.In the coordination compound poly, [Zn(C10H8N2).(C11H15O3)2.(C11H16O3)]n.n(H20), each ZnII ion is five coordinated by two N atoms from two 4,4'-bpy molecules and three O atoms from two 3-hydroxyadamantane-1-carboxylic anions (L) and one 3-hydroxy-1-adamantanecarboxylic acid (HL). The 4,4'-bpy molecules act as bidentate bridges,connecting the ZnII ions centres in a distorted trigonal-bipyramidal geometry into an infinite polymeric chain.The coordination geometry around ZnII seems to be classified as a trigonal bipyramid; O2, O4 and O8 atoms form the equatorial trigonal plane indicated by the angle of O2—Zn1—O4, O2—Zn1—O8 and O8—Zn1—O4 being 140.19 (11)°,102.42 (11)° and 117.37 (8)°, respectively. The axial position occupy N1 and N2 atoms; N1—Zn—N2 is the only combination with bonding angle close to 180 degrees. The Zn—O and Zn—N bond distances are listed in Table1.

The hydrogen bonds and π···π weak non-covalent interactions lend stability to the structure. The hydrogen bonds are listed in Table 2 and the stacking plot of this compound is shown in Fig.3.

Related literature top

For background to adamantane-1-carboxylic acid complexes, see: Zhu et al. (2005); Milios et al. (2007); Korlyukov et al. (2008).

Experimental top

Reagents and solvents used were of commercially available quality and without purified before using. A mixture of 3-hydroxyadamantane-1-carboxylic acid (0.3924 g, 2 mmol), Zn(OH)2 (0.0994 g, 1 mmol), 4,4'-bipyridine (0.1562 g, 1 mmol) and water (16 ml) was sealed in a 25 ml stainless steel reactor and heated at 160 K for 2 d and then cooled to room temperature over 3 d. The resulting colourless crystals were obtained and collected by filtration, washed with water, and dried in air (yield 33%).

Refinement top

The structure was solved by direct methods and successive Fourier difference synthesis. The H atoms bonded to C atoms were positioned geometrically and refined using a riding model [aliphatic C—H =0.96 Å (Uiso(H) = 1.5Ueq(C)), aromatic C—H = 0.93 Å (Uiso(H) = 1.2Ueq(C))]. H atoms bonded to O atoms were located in difference Fourier maps and refined with O—H distance restraints of 0.83 (2) and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, showing displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The coordination environment of the ZnII atom, showing the octahedral structurem.
[Figure 3] Fig. 3. The stacking plot of the title compound, showing H-bond interactions (dashed lines) and π···π stacking interactions.
catena-Poly[[[bis(3-hydroxyadamantane-1-carboxylato- κO1)(3-hydroxyadamantane-1-carboxylic acid-κO1)zinc(II)]- µ2-4,4'-bipyridine] monohydrate] top
Crystal data top
[Zn(C11H15O3)2(C10H8N2)(C11H16O3)]·H2OF(000) = 1752
Mr = 826.27Dx = 1.392 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 5047 reflections
a = 17.8778 (2) Åθ = 2.3–25.0°
b = 16.6364 (2) ŵ = 0.69 mm1
c = 13.2655 (1) ÅT = 296 K
β = 92.642 (1)°Block, colourless
V = 3941.26 (7) Å30.34 × 0.23 × 0.15 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
6904 independent reflections
Radiation source: fine-focus sealed tube6188 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ϕ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2121
Tmin = 0.826, Tmax = 0.904k = 1819
26431 measured reflectionsl = 1515
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0484P)2 + 1.9133P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.010
6904 reflectionsΔρmax = 0.28 e Å3
506 parametersΔρmin = 0.33 e Å3
4 restraintsAbsolute structure: Flack (1983), 3423 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.202 (9)
Crystal data top
[Zn(C11H15O3)2(C10H8N2)(C11H16O3)]·H2OV = 3941.26 (7) Å3
Mr = 826.27Z = 4
Monoclinic, CcMo Kα radiation
a = 17.8778 (2) ŵ = 0.69 mm1
b = 16.6364 (2) ÅT = 296 K
c = 13.2655 (1) Å0.34 × 0.23 × 0.15 mm
β = 92.642 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
6904 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6188 reflections with I > 2σ(I)
Tmin = 0.826, Tmax = 0.904Rint = 0.051
26431 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.094Δρmax = 0.28 e Å3
S = 1.04Δρmin = 0.33 e Å3
6904 reflectionsAbsolute structure: Flack (1983), 3423 Friedel pairs
506 parametersAbsolute structure parameter: 0.202 (9)
4 restraints
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*/Ueq
Zn10.40049 (2)0.236430 (19)0.71677 (3)0.03051 (11)
N10.49072 (19)0.23781 (19)0.6124 (3)0.0342 (8)
O40.33507 (14)0.17132 (17)0.6136 (2)0.0402 (7)
O10.34888 (16)0.35868 (16)0.6198 (2)0.0550 (7)
C60.6136 (2)0.2535 (2)0.4895 (3)0.0315 (9)
C70.4819 (2)0.2425 (3)0.5126 (3)0.0451 (11)
H7A0.43360.24080.48360.054*
C80.6799 (2)0.2591 (2)0.4261 (3)0.0284 (9)
C90.3480 (2)0.6166 (2)0.7172 (3)0.0366 (8)
C100.7489 (2)0.2815 (2)0.4668 (3)0.0356 (9)
H10A0.75460.29540.53460.043*
C130.5609 (3)0.2407 (3)0.6506 (3)0.0468 (12)
H13A0.56890.23760.72030.056*
C140.54545 (18)0.0765 (2)0.9012 (2)0.0318 (7)
C150.3374 (2)0.5255 (2)0.7198 (3)0.0369 (9)
H15A0.29330.51090.67840.044*
H15B0.32960.50840.78840.044*
C160.6481 (2)0.1194 (3)1.0717 (3)0.0467 (10)
H16A0.63690.17621.07710.056*
H16B0.68590.10581.12360.056*
O90.74338 (14)0.14821 (19)0.9501 (2)0.0595 (8)
H9A0.77270.14530.99930.089*
O20.42651 (15)0.35127 (16)0.7520 (2)0.0451 (6)
C190.6213 (3)0.2479 (3)0.5933 (4)0.0510 (13)
H19A0.66890.24900.62450.061*
O50.38659 (15)0.05103 (16)0.6003 (2)0.0524 (7)
H5C0.42190.06110.64350.079*
C230.3919 (2)0.3914 (2)0.6833 (3)0.0413 (9)
C240.61765 (18)0.1252 (2)0.8871 (3)0.0360 (8)
H24A0.63610.11480.82070.043*
H24B0.60690.18220.89200.043*
C250.3097 (2)0.1414 (2)0.3941 (3)0.0370 (8)
H25A0.30580.19720.41470.044*
H25B0.36110.13120.37760.044*
C260.2442 (3)0.0157 (2)0.3534 (4)0.0623 (14)
H26A0.24910.07180.33200.075*
O80.46501 (15)0.17339 (19)0.8196 (2)0.0432 (7)
C310.6747 (3)0.2418 (3)0.3243 (4)0.0467 (12)
H31A0.62900.22720.29330.056*
C320.5637 (2)0.0133 (2)0.8930 (3)0.0448 (9)
H32A0.51880.04480.90220.054*
H32B0.58130.02500.82650.054*
C330.5409 (2)0.2496 (3)0.4499 (3)0.0440 (10)
H33A0.53160.25180.38040.053*
C340.28800 (19)0.0859 (2)0.4816 (3)0.0345 (8)
C350.2579 (2)0.1262 (2)0.3016 (3)0.0410 (8)
C360.5172 (2)0.0942 (3)1.0063 (3)0.0430 (9)
H36A0.50590.15101.01210.052*
H36B0.47160.06421.01630.052*
C370.6940 (2)0.0121 (2)0.9582 (3)0.0459 (9)
H37A0.71200.00120.89170.055*
H37B0.73280.00341.00790.055*
C380.1781 (2)0.1421 (2)0.3269 (3)0.0497 (10)
H38A0.14530.13310.26770.060*
H38B0.17270.19770.34740.060*
C420.1637 (3)0.0001 (3)0.3796 (4)0.0777 (17)
H42A0.13050.01070.32130.093*
H42B0.15010.03570.43370.093*
C430.4178 (2)0.5102 (3)0.5727 (3)0.0538 (10)
H43A0.37490.49490.52950.065*
H43B0.46180.48420.54740.065*
C450.3601 (2)0.6431 (2)0.6105 (3)0.0499 (10)
H45A0.36730.70080.60890.060*
H45B0.31600.63030.56800.060*
C460.2954 (3)0.0014 (2)0.4472 (3)0.0524 (11)
H46A0.34700.01240.43190.063*
H46B0.28170.03730.50090.063*
C470.5774 (2)0.0703 (3)1.0867 (3)0.0518 (11)
H47A0.55910.08111.15400.062*
C480.2070 (2)0.1033 (3)0.5065 (3)0.0502 (10)
H48A0.20210.15900.52690.060*
H48B0.19270.06940.56190.060*
C510.5954 (3)0.0193 (3)1.0770 (3)0.0564 (12)
H51A0.63300.03461.12850.068*
H51B0.55070.05081.08690.068*
C540.2659 (3)0.0384 (2)0.2694 (3)0.0588 (12)
H54A0.23390.02810.20970.071*
H54B0.31720.02780.25290.071*
C550.34004 (18)0.1055 (2)0.5728 (2)0.0310 (7)
C560.40623 (18)0.4824 (2)0.6804 (3)0.0373 (8)
O60.28053 (17)0.17504 (18)0.21918 (19)0.0573 (7)
H6A0.27910.22260.23530.086*
C590.4852 (2)0.5973 (2)0.7440 (4)0.0578 (13)
H59A0.52910.61200.78710.069*
C670.67741 (19)0.1016 (2)0.9682 (3)0.0409 (9)
C40.4164 (2)0.6388 (2)0.7831 (3)0.0504 (11)
H4A0.40920.62240.85210.060*
H4B0.42350.69660.78220.060*
C50.4746 (2)0.5069 (3)0.7476 (4)0.0523 (11)
H5A0.46750.49010.81660.063*
H5B0.51900.48040.72450.063*
C180.4279 (3)0.6016 (3)0.5697 (4)0.0606 (12)
H18A0.43470.61910.50020.073*
C210.6240 (2)0.0364 (2)0.9738 (3)0.0519 (10)
H21A0.63550.09380.96810.062*
C120.4973 (3)0.6246 (3)0.6368 (5)0.0763 (17)
H12A0.54150.59900.61190.092*
H12B0.50470.68240.63530.092*
C220.1556 (2)0.0865 (3)0.4123 (4)0.0629 (13)
H22A0.10350.09690.42790.075*
N20.80564 (18)0.26537 (18)0.3092 (2)0.0287 (7)
C110.7389 (3)0.2465 (3)0.2685 (4)0.0477 (12)
H11A0.73470.23580.19960.057*
O30.28231 (15)0.65761 (16)0.7492 (2)0.0498 (7)
H3A0.27770.64980.80960.075*
C270.48627 (19)0.1019 (2)0.8201 (3)0.0324 (8)
O70.46364 (17)0.04954 (18)0.7576 (2)0.0600 (8)
C20.8096 (2)0.2832 (2)0.4060 (3)0.0346 (9)
H2A0.85600.29770.43510.041*
O1W0.4470 (4)0.1457 (5)0.2261 (7)0.208 (3)
H1WA0.40190.16020.21370.312*
H1WB0.45170.09530.23440.312*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02855 (17)0.03075 (18)0.03260 (18)0.0000 (2)0.00535 (12)0.0010 (2)
N10.0286 (19)0.0376 (19)0.0367 (19)0.0029 (14)0.0051 (11)0.0037 (14)
O40.0350 (15)0.0427 (17)0.0420 (15)0.0039 (13)0.0075 (12)0.0146 (13)
O10.0441 (16)0.0421 (16)0.078 (2)0.0102 (13)0.0111 (14)0.0143 (15)
C60.038 (2)0.0271 (19)0.030 (2)0.0022 (15)0.0033 (17)0.0004 (15)
C70.028 (2)0.076 (3)0.031 (2)0.0024 (18)0.0029 (16)0.0126 (19)
C80.026 (2)0.032 (2)0.028 (2)0.0012 (15)0.0053 (16)0.0020 (14)
C90.0324 (19)0.032 (2)0.045 (2)0.0044 (15)0.0072 (16)0.0033 (16)
C100.032 (2)0.049 (2)0.0253 (18)0.0004 (17)0.0025 (15)0.0017 (16)
C130.040 (3)0.076 (3)0.024 (2)0.013 (2)0.0011 (18)0.0085 (19)
C140.0260 (17)0.0367 (19)0.0321 (17)0.0032 (14)0.0049 (14)0.0056 (14)
C150.0301 (19)0.040 (2)0.040 (2)0.0002 (15)0.0053 (15)0.0010 (16)
C160.045 (2)0.052 (3)0.041 (2)0.0021 (19)0.0161 (18)0.0019 (19)
O90.0358 (15)0.079 (2)0.0625 (18)0.0204 (14)0.0140 (13)0.0203 (15)
O20.0511 (17)0.0302 (14)0.0541 (17)0.0002 (12)0.0042 (13)0.0011 (13)
C190.029 (2)0.090 (4)0.034 (2)0.021 (2)0.0011 (19)0.012 (2)
O50.0559 (16)0.0543 (17)0.0440 (15)0.0203 (13)0.0290 (12)0.0091 (13)
C230.0284 (18)0.037 (2)0.059 (3)0.0026 (17)0.0120 (18)0.0052 (18)
C240.0297 (18)0.042 (2)0.0355 (19)0.0047 (15)0.0045 (14)0.0057 (16)
C250.039 (2)0.038 (2)0.0338 (18)0.0016 (16)0.0054 (15)0.0026 (15)
C260.088 (4)0.029 (2)0.065 (3)0.002 (2)0.046 (3)0.006 (2)
O80.0407 (17)0.049 (2)0.0394 (15)0.0108 (13)0.0000 (11)0.0060 (12)
C310.028 (2)0.077 (3)0.034 (2)0.015 (2)0.0000 (18)0.013 (2)
C320.050 (2)0.033 (2)0.049 (2)0.0037 (16)0.0169 (18)0.0032 (16)
C330.028 (2)0.076 (3)0.0282 (19)0.0044 (18)0.0003 (15)0.0115 (18)
C340.0327 (18)0.035 (2)0.0344 (19)0.0031 (15)0.0096 (15)0.0009 (16)
C350.050 (2)0.037 (2)0.0350 (19)0.0001 (17)0.0116 (16)0.0002 (15)
C360.0321 (19)0.063 (3)0.034 (2)0.0002 (18)0.0014 (16)0.0060 (19)
C370.040 (2)0.051 (2)0.045 (2)0.0116 (17)0.0165 (17)0.0024 (18)
C380.050 (2)0.047 (2)0.050 (2)0.0072 (19)0.0202 (19)0.0004 (19)
C420.082 (4)0.065 (3)0.081 (3)0.039 (3)0.051 (3)0.022 (3)
C430.055 (2)0.053 (3)0.055 (2)0.004 (2)0.017 (2)0.003 (2)
C450.058 (3)0.039 (2)0.052 (2)0.0048 (19)0.0014 (19)0.0067 (19)
C460.071 (3)0.030 (2)0.053 (2)0.0039 (18)0.034 (2)0.0004 (17)
C470.047 (2)0.082 (3)0.0253 (18)0.002 (2)0.0054 (16)0.0063 (19)
C480.036 (2)0.071 (3)0.043 (2)0.006 (2)0.0040 (17)0.013 (2)
C510.049 (2)0.065 (3)0.054 (3)0.007 (2)0.017 (2)0.030 (2)
C540.081 (3)0.047 (2)0.045 (2)0.014 (2)0.032 (2)0.0174 (19)
C550.0309 (18)0.039 (2)0.0232 (17)0.0029 (15)0.0012 (14)0.0022 (15)
C560.0292 (19)0.0337 (19)0.049 (2)0.0010 (14)0.0008 (16)0.0007 (15)
O60.080 (2)0.0559 (17)0.0351 (14)0.0023 (15)0.0072 (13)0.0070 (13)
C590.034 (2)0.034 (2)0.104 (4)0.0015 (18)0.018 (2)0.008 (2)
C670.0300 (18)0.050 (2)0.042 (2)0.0058 (16)0.0042 (16)0.0049 (18)
C40.049 (2)0.031 (2)0.069 (3)0.0017 (18)0.019 (2)0.003 (2)
C50.033 (2)0.040 (2)0.083 (3)0.0045 (17)0.013 (2)0.005 (2)
C180.072 (3)0.044 (2)0.068 (3)0.003 (2)0.025 (2)0.012 (2)
C210.058 (3)0.036 (2)0.059 (3)0.0014 (19)0.022 (2)0.0099 (19)
C120.048 (3)0.044 (3)0.139 (5)0.008 (2)0.026 (3)0.014 (3)
C220.034 (2)0.089 (4)0.063 (3)0.014 (2)0.018 (2)0.014 (3)
N20.0252 (18)0.0339 (18)0.0274 (17)0.0012 (13)0.0046 (12)0.0020 (13)
C110.038 (3)0.077 (3)0.029 (2)0.016 (2)0.0085 (19)0.0156 (19)
O30.0445 (15)0.0465 (16)0.0580 (17)0.0159 (13)0.0004 (12)0.0042 (13)
C270.0278 (18)0.040 (2)0.0298 (18)0.0000 (15)0.0022 (14)0.0055 (15)
O70.0702 (19)0.0553 (18)0.0512 (17)0.0053 (15)0.0338 (15)0.0030 (14)
C20.0252 (18)0.048 (2)0.0304 (19)0.0002 (16)0.0010 (15)0.0030 (17)
O1W0.178 (6)0.206 (8)0.245 (9)0.019 (5)0.065 (6)0.016 (6)
Geometric parameters (Å, º) top
Zn1—O22.016 (3)C34—C461.530 (5)
Zn1—O82.036 (3)C35—O61.435 (4)
Zn1—O42.065 (3)C35—C381.504 (5)
Zn1—N2i2.138 (3)C35—C541.531 (5)
Zn1—N12.174 (4)C36—C471.533 (5)
N1—C71.329 (6)C36—H36A0.9700
N1—C131.332 (6)C36—H36B0.9700
O4—C551.227 (4)C37—C211.510 (6)
O1—C231.240 (5)C37—C671.525 (5)
C6—C191.381 (7)C37—H37A0.9700
C6—C331.381 (6)C37—H37B0.9700
C6—C81.489 (4)C38—C221.531 (6)
C7—C331.377 (6)C38—H38A0.9700
C7—H7A0.9300C38—H38B0.9700
C8—C101.374 (6)C42—C221.513 (8)
C8—C311.379 (6)C42—H42A0.9700
C9—O31.438 (4)C42—H42B0.9700
C9—C451.508 (6)C43—C561.525 (5)
C9—C41.515 (5)C43—C181.533 (6)
C9—C151.529 (5)C43—H43A0.9700
C10—C21.383 (5)C43—H43B0.9700
C10—H10A0.9300C45—C181.516 (6)
C13—C191.353 (7)C45—H45A0.9700
C13—H13A0.9300C45—H45B0.9700
C14—C271.533 (4)C46—H46A0.9700
C14—C361.534 (5)C46—H46B0.9700
C14—C321.534 (5)C47—C511.532 (7)
C14—C241.543 (4)C47—H47A0.9800
C15—C561.537 (5)C48—C221.543 (6)
C15—H15A0.9700C48—H48A0.9700
C15—H15B0.9700C48—H48B0.9700
C16—C671.521 (5)C51—C211.511 (6)
C16—C471.525 (6)C51—H51A0.9700
C16—H16A0.9700C51—H51B0.9700
C16—H16B0.9700C54—H54A0.9700
O9—C671.441 (4)C54—H54B0.9700
O9—H9A0.8200C56—C51.535 (5)
O2—C231.267 (4)O6—H6A0.8200
C19—H19A0.9300C59—C51.517 (6)
O5—C551.272 (4)C59—C121.518 (7)
O5—H5C0.8499C59—C41.522 (6)
C23—C561.536 (5)C59—H59A0.9800
C24—C671.532 (5)C4—H4A0.9700
C24—H24A0.9700C4—H4B0.9700
C24—H24B0.9700C5—H5A0.9700
C25—C351.524 (5)C5—H5B0.9700
C25—C341.546 (5)C18—C121.541 (7)
C25—H25A0.9700C18—H18A0.9800
C25—H25B0.9700C21—H21A0.9800
C26—C541.498 (7)C12—H12A0.9700
C26—C421.518 (8)C12—H12B0.9700
C26—C461.529 (5)C22—H22A0.9800
C26—H26A0.9800N2—C21.316 (5)
O8—C271.248 (5)N2—C111.324 (6)
C31—C111.397 (7)N2—Zn1ii2.138 (3)
C31—H31A0.9300C11—H11A0.9300
C32—C211.533 (5)O3—H3A0.8200
C32—H32A0.9700C27—O71.257 (4)
C32—H32B0.9700C2—H2A0.9300
C33—H33A0.9300O1W—H1WA0.8499
C34—C551.527 (4)O1W—H1WB0.8499
C34—C481.527 (5)
O2—Zn1—O8102.42 (12)H38A—C38—H38B108.2
O2—Zn1—O4140.19 (12)C22—C42—C26109.4 (4)
O8—Zn1—O4117.37 (9)C22—C42—H42A109.8
O2—Zn1—N2i93.50 (11)C26—C42—H42A109.8
O8—Zn1—N2i92.77 (11)C22—C42—H42B109.8
O4—Zn1—N2i86.13 (11)C26—C42—H42B109.8
O2—Zn1—N188.14 (11)H42A—C42—H42B108.2
O8—Zn1—N191.03 (12)C56—C43—C18110.2 (3)
O4—Zn1—N189.88 (12)C56—C43—H43A109.6
N2i—Zn1—N1175.44 (16)C18—C43—H43A109.6
C7—N1—C13116.3 (4)C56—C43—H43B109.6
C7—N1—Zn1125.3 (3)C18—C43—H43B109.6
C13—N1—Zn1118.2 (3)H43A—C43—H43B108.1
C55—O4—Zn1135.3 (2)C9—C45—C18110.7 (3)
C19—C6—C33115.1 (4)C9—C45—H45A109.5
C19—C6—C8121.5 (4)C18—C45—H45A109.5
C33—C6—C8123.3 (3)C9—C45—H45B109.5
N1—C7—C33123.3 (4)C18—C45—H45B109.5
N1—C7—H7A118.4H45A—C45—H45B108.1
C33—C7—H7A118.4C26—C46—C34109.5 (3)
C10—C8—C31117.4 (4)C26—C46—H46A109.8
C10—C8—C6121.2 (3)C34—C46—H46A109.8
C31—C8—C6121.4 (3)C26—C46—H46B109.8
O3—C9—C45107.0 (3)C34—C46—H46B109.8
O3—C9—C4111.3 (3)H46A—C46—H46B108.2
C45—C9—C4108.9 (4)C16—C47—C51109.3 (4)
O3—C9—C15111.1 (3)C16—C47—C36109.2 (3)
C45—C9—C15109.5 (3)C51—C47—C36109.7 (3)
C4—C9—C15109.1 (3)C16—C47—H47A109.5
C8—C10—C2119.4 (3)C51—C47—H47A109.5
C8—C10—H10A120.3C36—C47—H47A109.5
C2—C10—H10A120.3C34—C48—C22109.0 (4)
N1—C13—C19123.4 (5)C34—C48—H48A109.9
N1—C13—H13A118.3C22—C48—H48A109.9
C19—C13—H13A118.3C34—C48—H48B109.9
C27—C14—C36109.8 (3)C22—C48—H48B109.9
C27—C14—C32111.2 (3)H48A—C48—H48B108.3
C36—C14—C32109.4 (3)C21—C51—C47110.0 (3)
C27—C14—C24108.9 (3)C21—C51—H51A109.7
C36—C14—C24108.7 (3)C47—C51—H51A109.7
C32—C14—C24108.8 (3)C21—C51—H51B109.7
C9—C15—C56110.7 (3)C47—C51—H51B109.7
C9—C15—H15A109.5H51A—C51—H51B108.2
C56—C15—H15A109.5C26—C54—C35109.6 (3)
C9—C15—H15B109.5C26—C54—H54A109.8
C56—C15—H15B109.5C35—C54—H54A109.8
H15A—C15—H15B108.1C26—C54—H54B109.8
C67—C16—C47109.7 (3)C35—C54—H54B109.8
C67—C16—H16A109.7H54A—C54—H54B108.2
C47—C16—H16A109.7O4—C55—O5124.7 (3)
C67—C16—H16B109.7O4—C55—C34119.1 (3)
C47—C16—H16B109.7O5—C55—C34116.2 (3)
H16A—C16—H16B108.2C43—C56—C5109.0 (3)
C67—O9—H9A109.5C43—C56—C23110.6 (3)
C23—O2—Zn1103.4 (2)C5—C56—C23112.1 (3)
C13—C19—C6121.4 (4)C43—C56—C15108.8 (3)
C13—C19—H19A119.3C5—C56—C15107.9 (3)
C6—C19—H19A119.3C23—C56—C15108.3 (3)
C55—O5—H5C120.7C35—O6—H6A109.5
O1—C23—O2121.6 (4)C5—C59—C12110.5 (4)
O1—C23—C56120.9 (4)C5—C59—C4109.6 (4)
O2—C23—C56117.4 (3)C12—C59—C4109.6 (4)
C67—C24—C14109.9 (3)C5—C59—H59A109.1
C67—C24—H24A109.7C12—C59—H59A109.1
C14—C24—H24A109.7C4—C59—H59A109.1
C67—C24—H24B109.7O9—C67—C16111.4 (3)
C14—C24—H24B109.7O9—C67—C37110.3 (3)
H24A—C24—H24B108.2C16—C67—C37110.2 (3)
C35—C25—C34109.9 (3)O9—C67—C24107.1 (3)
C35—C25—H25A109.7C16—C67—C24109.0 (3)
C34—C25—H25A109.7C37—C67—C24108.7 (3)
C35—C25—H25B109.7C9—C4—C59109.7 (3)
C34—C25—H25B109.7C9—C4—H4A109.7
H25A—C25—H25B108.2C59—C4—H4A109.7
C54—C26—C42110.3 (4)C9—C4—H4B109.7
C54—C26—C46110.3 (4)C59—C4—H4B109.7
C42—C26—C46109.0 (4)H4A—C4—H4B108.2
C54—C26—H26A109.1C59—C5—C56110.0 (3)
C42—C26—H26A109.1C59—C5—H5A109.7
C46—C26—H26A109.1C56—C5—H5A109.7
C27—O8—Zn1131.1 (3)C59—C5—H5B109.7
C8—C31—C11119.2 (4)C56—C5—H5B109.7
C8—C31—H31A120.4H5A—C5—H5B108.2
C11—C31—H31A120.4C45—C18—C43110.2 (3)
C21—C32—C14109.8 (3)C45—C18—C12108.5 (4)
C21—C32—H32A109.7C43—C18—C12108.9 (4)
C14—C32—H32A109.7C45—C18—H18A109.7
C21—C32—H32B109.7C43—C18—H18A109.7
C14—C32—H32B109.7C12—C18—H18A109.7
H32A—C32—H32B108.2C37—C21—C51109.9 (3)
C7—C33—C6120.5 (4)C37—C21—C32109.3 (3)
C7—C33—H33A119.8C51—C21—C32109.2 (4)
C6—C33—H33A119.8C37—C21—H21A109.5
C55—C34—C48109.7 (3)C51—C21—H21A109.5
C55—C34—C46112.3 (3)C32—C21—H21A109.5
C48—C34—C46109.9 (3)C59—C12—C18108.8 (4)
C55—C34—C25107.6 (3)C59—C12—H12A109.9
C48—C34—C25108.8 (3)C18—C12—H12A109.9
C46—C34—C25108.4 (3)C59—C12—H12B109.9
O6—C35—C38112.0 (3)C18—C12—H12B109.9
O6—C35—C25109.7 (3)H12A—C12—H12B108.3
C38—C35—C25109.8 (3)C42—C22—C38109.4 (4)
O6—C35—C54107.1 (3)C42—C22—C48110.1 (4)
C38—C35—C54109.4 (3)C38—C22—C48108.9 (4)
C25—C35—C54108.8 (3)C42—C22—H22A109.5
C47—C36—C14109.4 (3)C38—C22—H22A109.5
C47—C36—H36A109.8C48—C22—H22A109.5
C14—C36—H36A109.8C2—N2—C11117.3 (4)
C47—C36—H36B109.8C2—N2—Zn1ii123.6 (3)
C14—C36—H36B109.8C11—N2—Zn1ii119.1 (3)
H36A—C36—H36B108.2N2—C11—C31122.9 (4)
C21—C37—C67110.1 (3)N2—C11—H11A118.5
C21—C37—H37A109.6C31—C11—H11A118.5
C67—C37—H37A109.6C9—O3—H3A109.5
C21—C37—H37B109.6O8—C27—O7124.7 (3)
C67—C37—H37B109.6O8—C27—C14117.8 (3)
H37A—C37—H37B108.1O7—C27—C14117.5 (3)
C35—C38—C22110.0 (3)N2—C2—C10123.7 (4)
C35—C38—H38A109.7N2—C2—H2A118.1
C22—C38—H38A109.7C10—C2—H2A118.1
C35—C38—H38B109.7H1WA—O1W—H1WB113.0
C22—C38—H38B109.7
O2—Zn1—N1—C7104.9 (3)C42—C26—C54—C3559.7 (4)
O8—Zn1—N1—C7152.7 (3)C46—C26—C54—C3560.7 (5)
O4—Zn1—N1—C735.3 (3)O6—C35—C54—C26179.0 (3)
O2—Zn1—N1—C1369.4 (3)C38—C35—C54—C2659.5 (4)
O8—Zn1—N1—C1333.0 (3)C25—C35—C54—C2660.5 (4)
O4—Zn1—N1—C13150.4 (3)Zn1—O4—C55—O513.2 (6)
O2—Zn1—O4—C55148.0 (3)Zn1—O4—C55—C34166.1 (3)
O8—Zn1—O4—C5530.1 (4)C48—C34—C55—O451.1 (4)
N2i—Zn1—O4—C55121.2 (4)C46—C34—C55—O4173.6 (3)
N1—Zn1—O4—C5561.0 (3)C25—C34—C55—O467.1 (4)
C13—N1—C7—C330.2 (6)C48—C34—C55—O5129.6 (3)
Zn1—N1—C7—C33174.7 (3)C46—C34—C55—O57.0 (5)
C19—C6—C8—C1018.6 (5)C25—C34—C55—O5112.2 (3)
C33—C6—C8—C10164.7 (4)C18—C43—C56—C559.3 (4)
C19—C6—C8—C31161.2 (5)C18—C43—C56—C23177.0 (3)
C33—C6—C8—C3115.6 (5)C18—C43—C56—C1558.1 (4)
C31—C8—C10—C22.1 (6)O1—C23—C56—C4343.9 (5)
C6—C8—C10—C2177.7 (3)O2—C23—C56—C43135.1 (3)
C7—N1—C13—C190.0 (7)O1—C23—C56—C5165.8 (4)
Zn1—N1—C13—C19174.9 (4)O2—C23—C56—C513.2 (5)
O3—C9—C15—C56177.1 (3)O1—C23—C56—C1575.2 (4)
C45—C9—C15—C5659.2 (4)O2—C23—C56—C15105.8 (4)
C4—C9—C15—C5659.9 (4)C9—C15—C56—C4358.9 (4)
O8—Zn1—O2—C23174.5 (2)C9—C15—C56—C559.2 (4)
O4—Zn1—O2—C233.7 (3)C9—C15—C56—C23179.2 (3)
N2i—Zn1—O2—C2391.9 (2)C47—C16—C67—O9178.7 (3)
N1—Zn1—O2—C2383.9 (2)C47—C16—C67—C3758.5 (4)
N1—C13—C19—C60.6 (8)C47—C16—C67—C2460.7 (4)
C33—C6—C19—C131.3 (7)C21—C37—C67—O9178.1 (3)
C8—C6—C19—C13178.3 (4)C21—C37—C67—C1658.5 (4)
Zn1—O2—C23—O15.4 (4)C21—C37—C67—C2460.9 (4)
Zn1—O2—C23—C56173.6 (2)C14—C24—C67—O9179.3 (3)
C27—C14—C24—C67179.3 (3)C14—C24—C67—C1660.1 (4)
C36—C14—C24—C6759.6 (4)C14—C24—C67—C3760.0 (4)
C32—C14—C24—C6759.4 (4)O3—C9—C4—C59177.4 (3)
O2—Zn1—O8—C27160.3 (3)C45—C9—C4—C5959.8 (4)
O4—Zn1—O8—C2718.4 (4)C15—C9—C4—C5959.7 (5)
N2i—Zn1—O8—C27105.5 (3)C5—C59—C4—C960.6 (5)
N1—Zn1—O8—C2772.0 (3)C12—C59—C4—C960.7 (5)
C10—C8—C31—C111.0 (6)C12—C59—C5—C5660.0 (5)
C6—C8—C31—C11178.8 (4)C4—C59—C5—C5660.8 (5)
C27—C14—C32—C21178.9 (3)C43—C56—C5—C5958.5 (5)
C36—C14—C32—C2159.7 (4)C23—C56—C5—C59178.6 (4)
C24—C14—C32—C2159.0 (4)C15—C56—C5—C5959.5 (5)
N1—C7—C33—C61.0 (7)C9—C45—C18—C4358.6 (5)
C19—C6—C33—C71.5 (6)C9—C45—C18—C1260.6 (5)
C8—C6—C33—C7178.4 (4)C56—C43—C18—C4558.4 (5)
C35—C25—C34—C55178.3 (3)C56—C43—C18—C1260.5 (4)
C35—C25—C34—C4859.5 (4)C67—C37—C21—C5158.9 (4)
C35—C25—C34—C4659.9 (4)C67—C37—C21—C3260.9 (4)
C34—C25—C35—O6177.2 (3)C47—C51—C21—C3759.7 (4)
C34—C25—C35—C3859.3 (4)C47—C51—C21—C3260.2 (4)
C34—C25—C35—C5460.3 (4)C14—C32—C21—C3760.1 (4)
C27—C14—C36—C47178.7 (3)C14—C32—C21—C5160.3 (4)
C32—C14—C36—C4759.0 (4)C5—C59—C12—C1860.4 (5)
C24—C14—C36—C4759.7 (4)C4—C59—C12—C1860.4 (5)
O6—C35—C38—C22177.8 (3)C45—C18—C12—C5959.9 (5)
C25—C35—C38—C2260.1 (4)C43—C18—C12—C5960.1 (5)
C54—C35—C38—C2259.3 (4)C26—C42—C22—C3858.9 (4)
C54—C26—C42—C2259.9 (5)C26—C42—C22—C4860.7 (5)
C46—C26—C42—C2261.3 (5)C35—C38—C22—C4259.5 (4)
O3—C9—C45—C18179.1 (3)C35—C38—C22—C4860.8 (5)
C4—C9—C45—C1860.5 (4)C34—C48—C22—C4259.0 (5)
C15—C9—C45—C1858.7 (4)C34—C48—C22—C3861.0 (5)
C54—C26—C46—C3460.5 (5)C2—N2—C11—C312.5 (7)
C42—C26—C46—C3460.8 (5)Zn1ii—N2—C11—C31176.4 (4)
C55—C34—C46—C26177.8 (3)C8—C31—C11—N21.4 (8)
C48—C34—C46—C2659.8 (5)Zn1—O8—C27—O78.5 (6)
C25—C34—C46—C2659.0 (4)Zn1—O8—C27—C14170.1 (2)
C67—C16—C47—C5158.8 (4)C36—C14—C27—O857.2 (4)
C67—C16—C47—C3661.2 (4)C32—C14—C27—O8178.4 (3)
C14—C36—C47—C1660.7 (5)C24—C14—C27—O861.7 (4)
C14—C36—C47—C5159.1 (4)C36—C14—C27—O7124.1 (4)
C55—C34—C48—C22177.8 (3)C32—C14—C27—O72.9 (5)
C46—C34—C48—C2258.3 (4)C24—C14—C27—O7117.0 (4)
C25—C34—C48—C2260.3 (4)C11—N2—C2—C101.4 (6)
C16—C47—C51—C2159.6 (4)Zn1ii—N2—C2—C10177.5 (3)
C36—C47—C51—C2160.1 (4)C8—C10—C2—N20.9 (6)
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9A···O1iii0.822.052.872 (4)178
O6—H6A···O3iv0.822.002.812 (4)169
O3—H3A···O9v0.821.992.790 (4)165
O1W—H1WA···O60.852.193.013 (9)163
O5—H5C···O70.851.672.447 (3)151
O1W—H1WB···O7vi0.852.443.287 (9)179
Symmetry codes: (iii) x+1/2, y+1/2, z+1/2; (iv) x, y+1, z1/2; (v) x1/2, y+1/2, z; (vi) x, y, z1/2.

Experimental details

Crystal data
Chemical formula[Zn(C11H15O3)2(C10H8N2)(C11H16O3)]·H2O
Mr826.27
Crystal system, space groupMonoclinic, Cc
Temperature (K)296
a, b, c (Å)17.8778 (2), 16.6364 (2), 13.2655 (1)
β (°) 92.642 (1)
V3)3941.26 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.69
Crystal size (mm)0.34 × 0.23 × 0.15
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.826, 0.904
No. of measured, independent and
observed [I > 2σ(I)] reflections
26431, 6904, 6188
Rint0.051
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.094, 1.04
No. of reflections6904
No. of parameters506
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.33
Absolute structureFlack (1983), 3423 Friedel pairs
Absolute structure parameter0.202 (9)

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Zn1—O22.016 (3)Zn1—N2i2.138 (3)
Zn1—O82.036 (3)Zn1—N12.174 (4)
Zn1—O42.065 (3)
Symmetry code: (i) x1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9A···O1ii0.822.052.872 (4)178
O6—H6A···O3iii0.822.002.812 (4)169
O3—H3A···O9iv0.821.992.790 (4)165
O1W—H1WA···O60.852.193.013 (9)163
O5—H5C···O70.851.672.447 (3)151
O1W—H1WB···O7v0.852.443.287 (9)179
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z1/2; (iv) x1/2, y+1/2, z; (v) x, y, z1/2.
 

References

First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationKorlyukov, A. A., Komissarov, E. A. & Antipin, M. Y. (2008). J. Mol. Struct. 875, 135–142.  CSD CrossRef CAS
First citationMilios, C. J., Inglis, R. & Bagai, R. (2007). Chem. Commun. 33, 3476–3478.  CSD CrossRef
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 citationZhu, Z.-L., Feng, Y.-L., Lin, H. & Chin, J. (2005). Rare Earth Soc. 23, 641–644.  CAS

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Volume 67| Part 6| June 2011| Pages m715-m716
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