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

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ISSN: 2056-9890

Tetra­aqua­bis­­(2-methyl-1H-benzimidazolium-1,3-di­acetato-κO)cobalt(II) tetra­hydrate

aCollege of Chemistry and Chemical Engineering, Huaihua University, Huaihua 418008, People's Republic of China, and bWuling Electric Power Group Corporation, Changsha 410000, People's Republic of China
*Correspondence e-mail: xiulingfeng2001@sina.com

(Received 9 July 2011; accepted 19 July 2011; online 2 August 2011)

In the title compound, [Co(C12H11N2O4)2(H2O)4]·4H2O, the CoII atom lies on an inversion center and is octa­hedrally coordinated by six O atoms from four water mol­ecules and two monodentate zwitterionic 2-methyl­benzimidazolium-1,3-diacetate ligands. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. ππ inter­actions between the imidazole and benzene rings [centroid–centroid distance = 3.9031 (17) Å] consolidate the crystal packing.

Related literature

For general background to coordination polymers, see: Kitagawa et al. (2004[Kitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334-2375.]); Robson (2000[Robson, R. (2000). J. Chem. Soc. Dalton Trans. pp. 3735-3744.]). For a related structure, see: Lian et al. (2009[Lian, H.-C., Ni, Q.-L., Jiang, X.-F., Cen, Z.-M. & Lin, J.-H. (2009). Acta Cryst. E65, m1091.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C12H11N2O4)2(H2O)4]·4H2O

  • Mr = 697.51

  • Monoclinic, P 21 /n

  • a = 7.2930 (7) Å

  • b = 21.240 (2) Å

  • c = 9.8123 (11) Å

  • β = 104.907 (1)°

  • V = 1468.8 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.67 mm−1

  • T = 298 K

  • 0.30 × 0.21 × 0.14 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.825, Tmax = 0.912

  • 7434 measured reflections

  • 2594 independent reflections

  • 1922 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.103

  • S = 0.96

  • 2594 reflections

  • 205 parameters

  • H-atom parameters constrained

  • Δρmax = 1.03 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5D⋯O4i 0.85 1.89 2.742 (3) 180
O5—H5E⋯O7ii 0.85 1.86 2.706 (3) 179
O6—H6C⋯O4iii 0.85 2.05 2.847 (3) 156
O6—H6D⋯O2 0.85 1.85 2.614 (2) 149
O7—H7C⋯O1iv 0.85 2.02 2.859 (3) 170
O7—H7D⋯O8v 0.85 1.96 2.797 (3) 170
O8—H8F⋯O4i 0.85 1.96 2.793 (3) 168
O8—H8G⋯O3vi 0.85 2.03 2.863 (3) 169
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y+1, -z+1; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) -x+2, -y+1, -z+1; (v) x, y, z-1; (vi) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Coordination polymers have attracted much interest due to their potential applications in many areas such as catalysis, molecular adsorption, magnetism properties and non-linear optics (Kitagawa et al., 2004; Robson, 2000). We report herein the structure of the title compound based on a flexible ligand 1-acetoxy-2-methylbenzimidazole-3-acetate acid (Lian et al., 2009).

The asymmetric unit of the title compound (Fig. 1) contains half of the complex molecule and two uncoordinated water molecules. The CoII atom lies on an inversion center and is octahedrally coordinated by six O atoms from four water molecules and two 2-methylbenzimidazolium-1,3-diacetate ligands. In the crystal structure, intra- and intermolecular O—H···O hydrogen bonds link the molecules into a three-dimensional network (Fig. 2). ππ interactions between the imidazole and benzene rings [centroid–centroid distance = 3.9031 (17) Å] consolidate the crystal packing.

Related literature top

For general background to coordination polymers, see: Kitagawa et al. (2004); Robson (2000). For a related structure, see: Lian et al. (2009).

Experimental top

A methanol solution (6 ml) of Co(CH3COO)2.4H2O (0.6 mmol) was slowly added to an aqueous solution (8 ml) of 1-acetoxy-2-methylbenzimidazole-3-acetate acid (0.4 mmol) at room temperature. Red block crystals were obtained after two months in 30% yield based on Co.

Refinement top

H atoms of water molecules were located in difference Fourier maps and refined as riding atoms, with a distance restraint of O—H = 0.85 Å and Uiso(H) = 1.2Ueq(O). H atoms bonded to C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.97 (methylene) and 0.96 (methyl) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C). The highest residual electron density was found at 1.43 Å from H8F atom and the deepest hole at 0.80 Å from Co1 atom.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) 1-x, 1-y, 1-z.]
[Figure 2] Fig. 2. The packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
Tetraaquabis(2-methyl-1H-benzimidazolium- 1,3-diacetato-κO)cobalt(II) tetrahydrate top
Crystal data top
[Co(C12H11N2O4)2(H2O)4]·4H2OF(000) = 730
Mr = 697.51Dx = 1.577 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2105 reflections
a = 7.2930 (7) Åθ = 2.9–24.1°
b = 21.240 (2) ŵ = 0.67 mm1
c = 9.8123 (11) ÅT = 298 K
β = 104.907 (1)°Block, red
V = 1468.8 (3) Å30.30 × 0.21 × 0.14 mm
Z = 2
Data collection top
Bruker APEX CCD
diffractometer
2594 independent reflections
Radiation source: fine-focus sealed tube1922 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.825, Tmax = 0.912k = 2225
7434 measured reflectionsl = 911
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0577P)2]
where P = (Fo2 + 2Fc2)/3
2594 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 1.03 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Co(C12H11N2O4)2(H2O)4]·4H2OV = 1468.8 (3) Å3
Mr = 697.51Z = 2
Monoclinic, P21/nMo Kα radiation
a = 7.2930 (7) ŵ = 0.67 mm1
b = 21.240 (2) ÅT = 298 K
c = 9.8123 (11) Å0.30 × 0.21 × 0.14 mm
β = 104.907 (1)°
Data collection top
Bruker APEX CCD
diffractometer
2594 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1922 reflections with I > 2σ(I)
Tmin = 0.825, Tmax = 0.912Rint = 0.038
7434 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 0.96Δρmax = 1.03 e Å3
2594 reflectionsΔρmin = 0.29 e Å3
205 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.50000.50000.50000.02777 (17)
N10.9890 (3)0.69581 (10)0.5346 (2)0.0260 (5)
N20.9847 (3)0.79831 (10)0.5396 (2)0.0271 (5)
O10.7555 (2)0.55086 (8)0.57519 (19)0.0330 (5)
O20.6575 (2)0.63795 (9)0.4517 (2)0.0360 (5)
O30.6708 (3)0.87653 (10)0.4610 (2)0.0436 (5)
O40.8026 (3)0.94740 (9)0.6224 (2)0.0420 (5)
O50.4298 (3)0.51633 (9)0.6890 (2)0.0378 (5)
H5D0.51330.49510.74740.045*
H5E0.32100.50520.69670.045*
O60.3338 (2)0.57873 (8)0.4121 (2)0.0362 (5)
H6C0.28910.57050.32510.043*
H6D0.40990.60940.41640.043*
O70.9160 (3)0.52003 (10)0.2867 (2)0.0486 (6)
H7C1.01780.49930.31800.058*
H7D0.90760.53000.20140.058*
O80.8449 (3)0.56024 (10)1.0065 (2)0.0514 (6)
H8F0.81270.52610.96150.062*
H8G0.94240.57480.98520.062*
C10.9848 (4)0.74613 (12)0.6159 (3)0.0261 (6)
C20.9827 (4)0.78113 (12)0.4026 (3)0.0270 (6)
C30.9845 (4)0.71627 (12)0.3987 (3)0.0270 (6)
C40.9742 (4)0.68298 (14)0.2765 (3)0.0334 (7)
H40.97520.63920.27480.040*
C50.9624 (4)0.71819 (15)0.1572 (3)0.0391 (7)
H5A0.95470.69780.07210.047*
C60.9615 (4)0.78393 (15)0.1605 (3)0.0411 (8)
H6A0.95320.80610.07730.049*
C70.9727 (4)0.81696 (14)0.2830 (3)0.0367 (7)
H70.97340.86070.28530.044*
C80.9780 (4)0.74391 (14)0.7636 (3)0.0373 (7)
H8A1.04810.77870.81380.056*
H8B1.03290.70510.80540.056*
H8C0.84840.74640.76860.056*
C90.7804 (4)0.60450 (12)0.5301 (3)0.0259 (6)
C100.9814 (4)0.63010 (12)0.5744 (3)0.0294 (6)
H10A1.02960.62610.67580.035*
H10B1.06210.60540.53030.035*
C110.8025 (4)0.89776 (13)0.5524 (3)0.0303 (6)
C120.9927 (4)0.86308 (12)0.5904 (3)0.0319 (6)
H12A1.08230.88640.55190.038*
H12B1.04090.86280.69220.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0247 (3)0.0239 (3)0.0339 (3)0.0009 (2)0.0062 (2)0.0047 (2)
N10.0230 (11)0.0213 (12)0.0321 (13)0.0029 (9)0.0042 (10)0.0030 (9)
N20.0252 (12)0.0210 (12)0.0336 (13)0.0013 (9)0.0049 (10)0.0016 (9)
O10.0307 (10)0.0249 (11)0.0408 (11)0.0050 (8)0.0043 (9)0.0085 (8)
O20.0251 (10)0.0307 (11)0.0479 (12)0.0007 (9)0.0017 (9)0.0102 (9)
O30.0330 (11)0.0439 (13)0.0475 (13)0.0033 (10)0.0014 (10)0.0140 (10)
O40.0455 (12)0.0305 (12)0.0453 (13)0.0092 (9)0.0030 (10)0.0110 (9)
O50.0300 (11)0.0438 (13)0.0394 (12)0.0004 (9)0.0090 (9)0.0057 (9)
O60.0323 (11)0.0297 (11)0.0431 (12)0.0013 (9)0.0035 (9)0.0052 (8)
O70.0363 (12)0.0547 (14)0.0568 (14)0.0068 (10)0.0155 (11)0.0069 (11)
O80.0426 (13)0.0466 (14)0.0690 (16)0.0077 (11)0.0219 (11)0.0166 (11)
C10.0209 (14)0.0255 (15)0.0300 (15)0.0009 (11)0.0032 (11)0.0014 (11)
C20.0225 (14)0.0250 (15)0.0339 (15)0.0003 (11)0.0079 (11)0.0017 (11)
C30.0208 (14)0.0271 (15)0.0327 (15)0.0001 (11)0.0062 (11)0.0013 (11)
C40.0291 (15)0.0314 (17)0.0403 (17)0.0002 (12)0.0096 (13)0.0041 (13)
C50.0359 (17)0.050 (2)0.0338 (17)0.0012 (14)0.0128 (13)0.0035 (14)
C60.0379 (18)0.051 (2)0.0366 (18)0.0008 (15)0.0137 (14)0.0141 (14)
C70.0329 (16)0.0305 (17)0.0480 (19)0.0010 (13)0.0126 (14)0.0099 (13)
C80.0368 (17)0.0397 (18)0.0335 (17)0.0052 (13)0.0058 (13)0.0014 (13)
C90.0296 (15)0.0227 (15)0.0274 (14)0.0018 (12)0.0108 (12)0.0013 (11)
C100.0267 (15)0.0223 (15)0.0367 (16)0.0007 (11)0.0039 (12)0.0035 (11)
C110.0326 (16)0.0272 (16)0.0309 (16)0.0010 (12)0.0078 (13)0.0033 (12)
C120.0281 (15)0.0239 (15)0.0421 (17)0.0015 (12)0.0059 (12)0.0047 (12)
Geometric parameters (Å, º) top
Co1—O52.0758 (19)O8—H8F0.8500
Co1—O5i2.0758 (19)O8—H8G0.8501
Co1—O6i2.1146 (17)C1—C81.464 (4)
Co1—O62.1146 (17)C2—C31.378 (4)
Co1—O12.1157 (17)C2—C71.384 (4)
Co1—O1i2.1157 (17)C3—C41.377 (4)
N1—C11.339 (3)C4—C51.373 (4)
N1—C31.395 (3)C4—H40.9300
N1—C101.454 (3)C5—C61.397 (4)
N2—C11.338 (3)C5—H5A0.9300
N2—C21.390 (3)C6—C71.376 (4)
N2—C121.459 (3)C6—H6A0.9300
O1—C91.252 (3)C7—H70.9300
O2—C91.243 (3)C8—H8A0.9600
O3—C111.219 (3)C8—H8B0.9600
O4—C111.258 (3)C8—H8C0.9600
O5—H5D0.8500C9—C101.518 (3)
O5—H5E0.8500C10—H10A0.9700
O6—H6C0.8500C10—H10B0.9700
O6—H6D0.8500C11—C121.530 (4)
O7—H7C0.8500C12—H12A0.9700
O7—H7D0.8501C12—H12B0.9700
O5—Co1—O5i180.0C2—C3—N1106.4 (2)
O5—Co1—O6i90.84 (7)C5—C4—C3116.1 (3)
O5i—Co1—O6i89.16 (8)C5—C4—H4122.0
O5—Co1—O689.16 (8)C3—C4—H4122.0
O5i—Co1—O690.84 (7)C4—C5—C6121.6 (3)
O6i—Co1—O6180.0C4—C5—H5A119.2
O5—Co1—O190.03 (8)C6—C5—H5A119.2
O5i—Co1—O189.97 (8)C7—C6—C5122.0 (3)
O6i—Co1—O184.29 (7)C7—C6—H6A119.0
O6—Co1—O195.71 (7)C5—C6—H6A119.0
O5—Co1—O1i89.97 (8)C6—C7—C2116.0 (3)
O5i—Co1—O1i90.03 (8)C6—C7—H7122.0
O6i—Co1—O1i95.71 (7)C2—C7—H7122.0
O6—Co1—O1i84.29 (7)C1—C8—H8A109.5
O1—Co1—O1i180.00 (8)C1—C8—H8B109.5
C1—N1—C3108.8 (2)H8A—C8—H8B109.5
C1—N1—C10126.7 (2)C1—C8—H8C109.5
C3—N1—C10124.2 (2)H8A—C8—H8C109.5
C1—N2—C2108.8 (2)H8B—C8—H8C109.5
C1—N2—C12126.5 (2)O2—C9—O1126.3 (2)
C2—N2—C12124.6 (2)O2—C9—C10117.5 (2)
C9—O1—Co1122.42 (16)O1—C9—C10116.2 (2)
Co1—O5—H5D102.5N1—C10—C9111.6 (2)
Co1—O5—H5E118.9N1—C10—H10A109.3
H5D—O5—H5E108.4C9—C10—H10A109.3
Co1—O6—H6C106.2N1—C10—H10B109.3
Co1—O6—H6D106.7C9—C10—H10B109.3
H6C—O6—H6D106.5H10A—C10—H10B108.0
H7C—O7—H7D108.6O3—C11—O4127.0 (3)
H8F—O8—H8G108.7O3—C11—C12119.6 (2)
N2—C1—N1108.9 (2)O4—C11—C12113.4 (2)
N2—C1—C8125.9 (2)N2—C12—C11114.6 (2)
N1—C1—C8125.2 (2)N2—C12—H12A108.6
C3—C2—C7121.7 (3)C11—C12—H12A108.6
C3—C2—N2106.9 (2)N2—C12—H12B108.6
C7—C2—N2131.4 (3)C11—C12—H12B108.6
C4—C3—C2122.6 (2)H12A—C12—H12B107.6
C4—C3—N1130.9 (3)
O5—Co1—O1—C9107.6 (2)C10—N1—C3—C40.6 (4)
O5i—Co1—O1—C972.4 (2)C1—N1—C3—C21.6 (3)
O6i—Co1—O1—C9161.6 (2)C10—N1—C3—C2176.4 (2)
O6—Co1—O1—C918.4 (2)C2—C3—C4—C50.1 (4)
C2—N2—C1—N11.9 (3)N1—C3—C4—C5176.7 (3)
C12—N2—C1—N1175.9 (2)C3—C4—C5—C60.2 (4)
C2—N2—C1—C8177.1 (3)C4—C5—C6—C70.1 (4)
C12—N2—C1—C85.1 (4)C5—C6—C7—C20.7 (4)
C3—N1—C1—N22.2 (3)C3—C2—C7—C61.0 (4)
C10—N1—C1—N2176.8 (2)N2—C2—C7—C6176.0 (3)
C3—N1—C1—C8176.8 (2)Co1—O1—C9—O29.4 (4)
C10—N1—C1—C82.2 (4)Co1—O1—C9—C10169.50 (17)
C1—N2—C2—C30.9 (3)C1—N1—C10—C995.3 (3)
C12—N2—C2—C3177.0 (2)C3—N1—C10—C978.6 (3)
C1—N2—C2—C7176.4 (3)O2—C9—C10—N19.7 (3)
C12—N2—C2—C75.7 (4)O1—C9—C10—N1171.3 (2)
C7—C2—C3—C40.8 (4)C1—N2—C12—C11102.4 (3)
N2—C2—C3—C4176.8 (2)C2—N2—C12—C1180.1 (3)
C7—C2—C3—N1178.1 (2)O3—C11—C12—N215.7 (4)
N2—C2—C3—N10.5 (3)O4—C11—C12—N2164.9 (2)
C1—N1—C3—C4175.4 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5D···O4ii0.851.892.742 (3)180
O5—H5E···O7i0.851.862.706 (3)179
O6—H6C···O4iii0.852.052.847 (3)156
O6—H6D···O20.851.852.614 (2)149
O7—H7C···O1iv0.852.022.859 (3)170
O7—H7D···O8v0.851.962.797 (3)170
O8—H8F···O4ii0.851.962.793 (3)168
O8—H8G···O3vi0.852.032.863 (3)169
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+3/2, y1/2, z+3/2; (iii) x1/2, y+3/2, z1/2; (iv) x+2, y+1, z+1; (v) x, y, z1; (vi) x+1/2, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Co(C12H11N2O4)2(H2O)4]·4H2O
Mr697.51
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.2930 (7), 21.240 (2), 9.8123 (11)
β (°) 104.907 (1)
V3)1468.8 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.67
Crystal size (mm)0.30 × 0.21 × 0.14
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.825, 0.912
No. of measured, independent and
observed [I > 2σ(I)] reflections
7434, 2594, 1922
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.103, 0.96
No. of reflections2594
No. of parameters205
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.03, 0.29

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5D···O4i0.851.892.742 (3)180
O5—H5E···O7ii0.851.862.706 (3)179
O6—H6C···O4iii0.852.052.847 (3)156
O6—H6D···O20.851.852.614 (2)149
O7—H7C···O1iv0.852.022.859 (3)170
O7—H7D···O8v0.851.962.797 (3)170
O8—H8F···O4i0.851.962.793 (3)168
O8—H8G···O3vi0.852.032.863 (3)169
Symmetry codes: (i) x+3/2, y1/2, z+3/2; (ii) x+1, y+1, z+1; (iii) x1/2, y+3/2, z1/2; (iv) x+2, y+1, z+1; (v) x, y, z1; (vi) x+1/2, y+3/2, z+1/2.
 

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334–2375.  Web of Science CrossRef CAS Google Scholar
First citationLian, H.-C., Ni, Q.-L., Jiang, X.-F., Cen, Z.-M. & Lin, J.-H. (2009). Acta Cryst. E65, m1091.  CSD CrossRef IUCr Journals Google Scholar
First citationRobson, R. (2000). J. Chem. Soc. Dalton Trans. pp. 3735–3744.  Web of Science CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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