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

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Pages m209-m210

Poly[[aqua­(μ4-1H-benzimidazole-5,6-di­carboxyl­ato-κ4N3:O5:O5′:O6)(N,N-di­methyl­formamide-κO)cadmium(II)] dihydrate]

aCollege of Food Science and Technology, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China, bCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China, and cCollege of Agriculture, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
*Correspondence e-mail: songwd60@163.com

(Received 17 January 2010; accepted 25 January 2010; online 30 January 2010)

In the title compound, {[Cd(C9H4N2O4)(C3H7NO)(H2O)]·2H2O}n, the CdII atom is coordinated by one N atom and three O atoms from four different 1H-benzimidazole-5,6-dicarboxyl­ate (Hbidc) ligands, one O atom from one dimethyl­formamide ligand, and one O atom from a water mol­ecule in a distorted octa­hedral geometry. The Hbidc ligands connect the Cd atoms into a two-dimensional network parallel to (001). N—H⋯O and O—H⋯O hydrogen bonds involving the water molecules are observed in the crystal structure.

Related literature

For related structures of 1H-benzimidazole-5,6-dicarboxyl­ate complexes, see: Song, Wang, Hu et al. (2009[Song, W.-D., Wang, H., Hu, S.-W., Qin, P.-W. & Li, S.-J. (2009). Acta Cryst. E65, m701.]); Song, Wang, Li et al. (2009[Song, W.-D., Wang, H., Li, S.-J., Qin, P.-W. & Hu, S.-W. (2009). Acta Cryst. E65, m702.]); Song, Wang, Qin et al. (2009[Song, W.-D., Wang, H., Qin, P.-W., Li, S.-J. & Hu, S.-W. (2009). Acta Cryst. E65, m672.]); Wang et al. (2009[Wang, H., Song, W.-D., Li, S.-J., Miao, D.-L. & Liu, J. (2009). Acta Cryst. E65, m1423.]).

[Scheme 1]

Experimental

Crystal data
  • [Cd(C9H4N2O4)(C3H7NO)(H2O)]·2H2O

  • Mr = 443.69

  • Triclinic, [P \overline 1]

  • a = 7.7729 (16) Å

  • b = 9.1648 (18) Å

  • c = 11.458 (2) Å

  • α = 102.76 (3)°

  • β = 97.70 (3)°

  • γ = 94.96 (3)°

  • V = 783.2 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.44 mm−1

  • T = 293 K

  • 0.29 × 0.25 × 0.21 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Private communication to the Molecular Structure Corporation, The Woodlands, Texas, USA.]) Tmin = 0.680, Tmax = 0.752

  • 6197 measured reflections

  • 2800 independent reflections

  • 1539 reflections with I > 2σ(I)

  • Rint = 0.121

Refinement
  • R[F2 > 2σ(F2)] = 0.086

  • wR(F2) = 0.223

  • S = 1.14

  • 2800 reflections

  • 219 parameters

  • 9 restraints

  • H-atom parameters constrained

  • Δρmax = 2.12 e Å−3

  • Δρmin = −1.80 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1W⋯O2i 0.84 1.92 2.757 (11) 177
O1W—H2W⋯O4ii 0.84 1.85 2.649 (12) 159
O2W—H3W⋯O1W 0.84 2.16 2.888 (9) 145
O2W—H4W⋯O1 0.84 2.00 2.811 (11) 162
O3W—H5W⋯O2i 0.84 2.11 2.810 (12) 140
O3W—H6W⋯O2Wiii 0.84 2.29 2.766 (14) 117
N2—H2⋯O2Wiv 0.86 2.18 2.970 (16) 152
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z+1; (iii) -x+1, -y, -z+2; (iv) x, y+1, z.

Data collection: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalStructure; data reduction: CrystalStructure; 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

From the structural point of view, 1H-benzimidazole-5,6-dicarboxylic acid (H3bidc) possesses two N atoms of imidazole ring and four O atoms of carboxylate groups and might be used as versatile linker in constructing coordination polymers with abundant hydrogen bonds. Based on this idea, a series of coordination polymers fomed by this ligand have been reported by us: catena-poly[[diaqua(1,10-phenanthroline-κ2N,N')nickel(II)]- µ-Hbidc-κ2N3:O6] (Song, Wang, Hu et al., 2009), pentaaqua(Hbidc-κN3)cobalt(II) pentahydrate (Song, Wang, Li et al., 2009), pentaaqua(Hbidc-κN3)nickel(II) pentahydrate (Song, Wang, Qin et al., 2009), and tetraaquabis(Hbidc-κN3)cobalt(II) dimethylformamide disolvate dihydrate (Wang et al., 2009). In the present paper, we report the title complex.

As shown in Fig. 1, the CdII atom exhibits an octahedral coordination geometry, defined by three O atoms from three different Hbidc ligands, one N atom from another Hbidc ligand, one O atom from a dimethylformamide ligand and one O atom from a water molecule. The equatorial plane is defined by O1W, O10, N1i and O3iii atoms, while O1 and O4ii occupy the axial positions [symmetry codes: (i) -x, 1-y, 1-z; (ii) 1+x, y, z; (iii) -x, -y, 1-z]. Two solvent water molecules are present in the asymmetic unit. O—H···O and N—H···O hydrogen bonds are observed in the crystal structure with hydrogen-bond geometry in the normal range (Fig. 2 and Table 1).

Related literature top

For related structures of 1H-benzimidazole-5,6-dicarboxylate complexes, see: Song, Wang, Hu et al. (2009); Song, Wang, Li et al. (2009); Song, Wang, Qin et al. (2009); Wang et al. (2009).

Experimental top

A dimethylformamide solution (20 ml) containing CdCl2(0.1 mmol) and H3bidc (0.2 mmol) was stirred for a few minutes in air, and then left to stand at room temperature. Colorless crystals were obtained in a few weeks.

Refinement top

C- and N-bound H atoms were placed at calculated positions and treated as riding on the parent atoms, with C—H = 0.93 (CH), 0.96 (CH3), N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C, N). The water H-atoms were located in a difference Fourier map and refined as riding, with a distance restraint of O—H = 0.84 Å and with Uiso(H) = 1.5Ueq(O). The highest residual electron density was found 1.07 Å from Cd1 and the deepest hole 0.97 Å from Cd1.

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2002); cell refinement: CrystalStructure (Rigaku/MSC, 2002); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing the 30% probability displacement ellipsoids. [Symmetry codes: (i) -x, 1-y, 1-z; (ii) 1+x, y, z; (iii) -x, -y,1-z.]
[Figure 2] Fig. 2. A view of the crystal packing. Hydrogen bonds are shown as dashed lines.
Poly[[aqua(µ4-1H-benzimidazole-5,6-dicarboxylato- κ4N3:O5:O5':O6)(N,N- dimethylformamide-κO)cadmium(II)] dihydrate] top
Crystal data top
[Cd(C9H4N2O4)(C3H7NO)(H2O)]·2H2OZ = 2
Mr = 443.69F(000) = 444
Triclinic, P1Dx = 1.881 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7729 (16) ÅCell parameters from 3441 reflections
b = 9.1648 (18) Åθ = 3.3–27.4°
c = 11.458 (2) ŵ = 1.44 mm1
α = 102.76 (3)°T = 293 K
β = 97.70 (3)°Block, colorless
γ = 94.96 (3)°0.29 × 0.25 × 0.21 mm
V = 783.2 (3) Å3
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
2800 independent reflections
Radiation source: fine-focus sealed tube1539 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.121
ω scansθmax = 25.2°, θmin = 3.3°
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
h = 97
Tmin = 0.680, Tmax = 0.752k = 1010
6197 measured reflectionsl = 1313
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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.223H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0683P)2 + 2.7388P]
where P = (Fo2 + 2Fc2)/3
2800 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 2.12 e Å3
9 restraintsΔρmin = 1.80 e Å3
Crystal data top
[Cd(C9H4N2O4)(C3H7NO)(H2O)]·2H2Oγ = 94.96 (3)°
Mr = 443.69V = 783.2 (3) Å3
Triclinic, P1Z = 2
a = 7.7729 (16) ÅMo Kα radiation
b = 9.1648 (18) ŵ = 1.44 mm1
c = 11.458 (2) ÅT = 293 K
α = 102.76 (3)°0.29 × 0.25 × 0.21 mm
β = 97.70 (3)°
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
2800 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
1539 reflections with I > 2σ(I)
Tmin = 0.680, Tmax = 0.752Rint = 0.121
6197 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0869 restraints
wR(F2) = 0.223H-atom parameters constrained
S = 1.14Δρmax = 2.12 e Å3
2800 reflectionsΔρmin = 1.80 e Å3
219 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.32811 (14)0.19007 (13)0.58926 (9)0.0427 (4)
O10.1397 (12)0.1778 (11)0.7248 (7)0.043 (2)
O20.1244 (11)0.1608 (11)0.7803 (8)0.043 (2)
O1W0.5202 (9)0.0812 (8)0.7112 (7)0.045 (3)
O100.4501 (13)0.4197 (11)0.7028 (8)0.048 (3)
N10.1716 (14)0.7274 (13)0.5549 (9)0.037 (3)
N20.0418 (16)0.7573 (12)0.7100 (10)0.046 (3)
H20.12470.80190.76760.055*
N30.6296 (17)0.5826 (15)0.8605 (11)0.057 (4)
C10.0542 (18)0.8220 (17)0.6334 (13)0.044 (4)
H10.03820.92450.63620.053*
C20.1506 (16)0.5900 (15)0.5837 (12)0.035 (3)
C30.2450 (15)0.4482 (15)0.5278 (10)0.031 (3)
H30.33530.43700.46330.037*
C40.1988 (17)0.3261 (16)0.5722 (11)0.037 (3)
C50.0634 (17)0.3421 (14)0.6700 (11)0.033 (3)
C60.0295 (17)0.4860 (17)0.7241 (12)0.045 (4)
H60.12030.49990.78870.054*
C70.0192 (16)0.6032 (16)0.6778 (10)0.033 (3)
C80.0144 (18)0.2164 (15)0.7258 (12)0.039 (3)
C110.758 (3)0.606 (2)0.9664 (14)0.086 (6)
H11A0.76490.51230.99070.128*
H11B0.72500.67931.03060.128*
H11C0.86930.64070.94910.128*
C120.587 (2)0.713 (2)0.8183 (16)0.077 (6)
H12A0.56130.68680.73130.116*
H12B0.68350.79070.84450.116*
H12C0.48590.74770.85060.116*
C100.560 (2)0.4477 (19)0.7957 (13)0.054 (4)
H100.59750.36550.82260.065*
O3W0.7681 (13)0.2252 (9)1.0089 (11)0.127 (6)
H5W0.84650.21240.96500.190*
H6W0.69980.14460.98910.190*
O2W0.2935 (7)0.0032 (12)0.8739 (9)0.080 (4)
H3W0.39060.02070.85220.120*
H4W0.22730.05100.83640.120*
C90.2912 (17)0.1756 (17)0.5120 (11)0.036 (3)
O30.2155 (12)0.0562 (10)0.5048 (7)0.041 (2)
O40.4532 (9)0.1698 (8)0.4625 (7)0.043 (2)
H1W0.62790.10810.73150.065*
H2W0.49820.00840.67110.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0451 (7)0.0367 (7)0.0457 (6)0.0036 (5)0.0070 (4)0.0115 (5)
O10.040 (6)0.042 (6)0.043 (5)0.015 (5)0.005 (4)0.013 (4)
O20.033 (5)0.041 (6)0.059 (6)0.002 (5)0.007 (4)0.024 (5)
O1W0.040 (5)0.038 (6)0.049 (5)0.017 (5)0.006 (4)0.004 (5)
O100.054 (6)0.044 (7)0.039 (5)0.003 (5)0.005 (5)0.006 (5)
N10.035 (6)0.030 (7)0.042 (6)0.000 (6)0.000 (5)0.006 (5)
N20.056 (8)0.023 (7)0.053 (7)0.007 (6)0.011 (6)0.002 (6)
N30.062 (9)0.034 (8)0.064 (8)0.003 (7)0.009 (7)0.004 (7)
C10.048 (9)0.035 (9)0.064 (9)0.014 (7)0.021 (8)0.031 (8)
C20.030 (7)0.029 (8)0.057 (8)0.011 (6)0.020 (6)0.020 (7)
C30.025 (6)0.043 (9)0.023 (6)0.010 (6)0.001 (5)0.010 (6)
C40.035 (8)0.040 (9)0.034 (7)0.009 (7)0.003 (6)0.009 (6)
C50.045 (8)0.022 (7)0.033 (7)0.002 (6)0.006 (6)0.008 (6)
C60.032 (8)0.055 (10)0.043 (8)0.006 (7)0.007 (6)0.016 (7)
C70.029 (7)0.047 (9)0.029 (7)0.016 (7)0.003 (5)0.016 (6)
C80.041 (9)0.027 (8)0.043 (8)0.011 (7)0.010 (6)0.002 (6)
C110.105 (16)0.080 (15)0.052 (10)0.008 (12)0.028 (10)0.001 (10)
C120.083 (14)0.063 (14)0.078 (12)0.011 (11)0.036 (10)0.013 (10)
C100.065 (11)0.049 (11)0.049 (9)0.012 (9)0.009 (8)0.009 (8)
O3W0.171 (17)0.126 (15)0.085 (10)0.006 (12)0.049 (10)0.020 (10)
O2W0.075 (8)0.090 (10)0.088 (8)0.009 (7)0.027 (7)0.041 (8)
C90.037 (8)0.044 (9)0.030 (7)0.006 (7)0.008 (6)0.015 (6)
O30.056 (6)0.028 (6)0.039 (5)0.000 (5)0.011 (4)0.005 (4)
O40.044 (6)0.037 (6)0.041 (5)0.009 (5)0.008 (4)0.001 (4)
Geometric parameters (Å, º) top
Cd1—N1i2.226 (11)C3—C41.382 (19)
Cd1—O102.266 (9)C3—H30.9300
Cd1—O12.287 (8)C4—C51.404 (18)
Cd1—O3ii2.314 (9)C4—C91.472 (18)
Cd1—O1W2.344 (9)C5—C61.414 (18)
Cd1—O4iii2.373 (7)C5—C81.489 (19)
O1—C81.278 (16)C6—C71.359 (19)
O2—C81.261 (14)C6—H60.9300
O1W—H1W0.8380C11—H11A0.9600
O1W—H2W0.8382C11—H11B0.9600
O10—C101.236 (17)C11—H11C0.9600
N1—C11.301 (17)C12—H12A0.9600
N1—C21.388 (17)C12—H12B0.9600
N2—C11.346 (17)C12—H12C0.9600
N2—C71.400 (17)C10—H100.9300
N2—H20.8600O3W—H5W0.8411
N3—C101.320 (19)O3W—H6W0.8398
N3—C111.426 (19)O2W—H3W0.8389
N3—C121.43 (2)O2W—H4W0.8393
C1—H10.9300C9—O31.279 (16)
C2—C71.359 (18)C9—O41.302 (14)
C2—C31.407 (17)
N1i—Cd1—O1096.6 (4)C3—C4—C9118.6 (11)
N1i—Cd1—O1103.1 (4)C5—C4—C9119.8 (13)
O10—Cd1—O189.6 (3)C4—C5—C6119.5 (13)
N1i—Cd1—O3ii90.6 (4)C4—C5—C8123.9 (12)
O10—Cd1—O3ii172.6 (3)C6—C5—C8116.6 (12)
O1—Cd1—O3ii86.9 (3)C7—C6—C5117.3 (12)
N1i—Cd1—O1W169.1 (3)C7—C6—H6121.3
O10—Cd1—O1W88.5 (3)C5—C6—H6121.3
O1—Cd1—O1W86.5 (3)C6—C7—C2124.0 (13)
O3ii—Cd1—O1W84.8 (3)C6—C7—N2132.0 (12)
N1i—Cd1—O4iii85.9 (3)C2—C7—N2103.9 (12)
O10—Cd1—O4iii93.7 (3)O2—C8—O1123.0 (14)
O1—Cd1—O4iii170.0 (3)O2—C8—C5117.4 (13)
O3ii—Cd1—O4iii88.7 (3)O1—C8—C5119.3 (11)
O1W—Cd1—O4iii84.1 (3)N3—C11—H11A109.5
C8—O1—Cd1130.4 (8)N3—C11—H11B109.5
H1W—O1W—H2W112.2H11A—C11—H11B109.5
C10—O10—Cd1127.5 (11)N3—C11—H11C109.5
C1—N1—C2103.9 (12)H11A—C11—H11C109.5
C1—N1—Cd1i118.8 (10)H11B—C11—H11C109.5
C2—N1—Cd1i137.1 (9)N3—C12—H12A109.5
C1—N2—C7106.8 (11)N3—C12—H12B109.5
C1—N2—H2126.6H12A—C12—H12B109.5
C7—N2—H2126.6N3—C12—H12C109.5
C10—N3—C11123.2 (15)H12A—C12—H12C109.5
C10—N3—C12119.1 (14)H12B—C12—H12C109.5
C11—N3—C12117.5 (15)O10—C10—N3126.5 (16)
N1—C1—N2113.5 (13)O10—C10—H10116.7
N1—C1—H1123.2N3—C10—H10116.7
N2—C1—H1123.2H5W—O3W—H6W105.9
C7—C2—N1111.8 (12)H3W—O2W—H4W103.7
C7—C2—C3120.0 (13)O3—C9—O4121.1 (12)
N1—C2—C3128.2 (13)O3—C9—C4122.1 (12)
C4—C3—C2117.7 (11)O4—C9—C4116.8 (13)
C4—C3—H3121.2C9—O3—Cd1ii128.7 (8)
C2—C3—H3121.2C9—O4—Cd1iv118.5 (7)
C3—C4—C5121.6 (12)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O2iii0.841.922.757 (11)177
O1W—H2W···O4ii0.841.852.649 (12)159
O2W—H3W···O1W0.842.162.888 (9)145
O2W—H4W···O10.842.002.811 (11)162
O3W—H5W···O2iii0.842.112.810 (12)140
O3W—H6W···O2Wv0.842.292.766 (14)117
N2—H2···O2Wvi0.862.182.970 (16)152
Symmetry codes: (ii) x, y, z+1; (iii) x+1, y, z; (v) x+1, y, z+2; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Cd(C9H4N2O4)(C3H7NO)(H2O)]·2H2O
Mr443.69
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.7729 (16), 9.1648 (18), 11.458 (2)
α, β, γ (°)102.76 (3), 97.70 (3), 94.96 (3)
V3)783.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.44
Crystal size (mm)0.29 × 0.25 × 0.21
Data collection
DiffractometerRigaku/MSC Mercury CCD
diffractometer
Absorption correctionMulti-scan
(REQAB; Jacobson, 1998)
Tmin, Tmax0.680, 0.752
No. of measured, independent and
observed [I > 2σ(I)] reflections
6197, 2800, 1539
Rint0.121
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.086, 0.223, 1.14
No. of reflections2800
No. of parameters219
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.12, 1.80

Computer programs: CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O2i0.841.922.757 (11)177
O1W—H2W···O4ii0.841.852.649 (12)159
O2W—H3W···O1W0.842.162.888 (9)145
O2W—H4W···O10.842.002.811 (11)162
O3W—H5W···O2i0.842.112.810 (12)140
O3W—H6W···O2Wiii0.842.292.766 (14)117
N2—H2···O2Wiv0.862.182.970 (16)152
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x+1, y, z+2; (iv) x, y+1, z.
 

Acknowledgements

The authors acknowledge Guang Dong Ocean University for supporting this work.

References

First citationJacobson, R. (1998). REQAB. Private communication to the Molecular Structure Corporation, The Woodlands, Texas, USA.
First citationJohnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
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Volume 66| Part 2| February 2010| Pages m209-m210
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