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

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ISSN: 2056-9890

Bis(2,2′-bi­pyridine-κ2N,N′)di­chloridocadmium(II)

aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 November 2010; accepted 25 November 2010; online 30 November 2010)

The CdII atom in the title compound, [CdCl2(C10H8N2)2] exists in a distorted octa­hedral geometry [N—Cd—N = 148.29 (17)°]; the Cl atoms are cis with respect to each other.

Related literature

For polymeric dichlorido(2,2′-bipyridine)­cadmium, see: Zhou et al. (2003[Zhou, Y.-F., Xu, Y., Yuan, D.-Q. & Hong, M.-C. (2003). Acta Cryst. E59, m821-m823.]).

[Scheme 1]

Experimental

Crystal data
  • [CdCl2(C10H8N2)2]

  • Mr = 495.67

  • Monoclinic, P 21 /c

  • a = 8.7477 (2) Å

  • b = 14.3541 (5) Å

  • c = 15.8723 (5) Å

  • β = 98.775 (1)°

  • V = 1969.68 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.39 mm−1

  • T = 293 K

  • 0.18 × 0.15 × 0.12 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.788, Tmax = 0.851

  • 31202 measured reflections

  • 4497 independent reflections

  • 3047 reflections with I > 2σ(I)

  • Rint = 0.056

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.186

  • S = 1.17

  • 4497 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 1.61 e Å−3

  • Δρmin = −1.04 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The hydrothermal reaction of cadmium chloride and 2,2'-bipyridine yields the 1:1 adduct, which exists as a chlorine-bridged chain polymer. The cadmium atom exists in an octahedral geometry (Zhou et al., 2003). In the present 1:2 adduct (Scheme I, Fig. 1), the geometry is also an octahedron but the molecule exists as a discrete entity, without any bridging.

Related literature top

For polymeric dichlorido(2,2'-bipyridine)cadmium, see: Zhou et al. (2003).

Experimental top

Cadmium chloride (0.1 mmol), 2,2'-bipyridine (0.1 mmol) and benzoic acid (0.2 mmol) were dissolved in a water-ethanol-DMF mixture (15 ml). The solution was heated in a 25 ml, Teflon-lined, stainless-steel bomb at 383 K for 3 days. The cool solution was filtered and the solvent allowed to evaporate. Colorless crystals separated from solution after a few days.

Refinement top

Hydrogen atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

Structure description top

The hydrothermal reaction of cadmium chloride and 2,2'-bipyridine yields the 1:1 adduct, which exists as a chlorine-bridged chain polymer. The cadmium atom exists in an octahedral geometry (Zhou et al., 2003). In the present 1:2 adduct (Scheme I, Fig. 1), the geometry is also an octahedron but the molecule exists as a discrete entity, without any bridging.

For polymeric dichlorido(2,2'-bipyridine)cadmium, see: Zhou et al. (2003).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of CdCl2(C10H8N2)2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Bis(2,2'-bipyridine-κ2N,N')dichloridocadmium(II) top
Crystal data top
[CdCl2(C10H8N2)2]F(000) = 984
Mr = 495.67Dx = 1.671 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 18413 reflections
a = 8.7477 (2) Åθ = 3.1–27.4°
b = 14.3541 (5) ŵ = 1.39 mm1
c = 15.8723 (5) ÅT = 293 K
β = 98.775 (1)°Block, colorless
V = 1969.68 (10) Å30.18 × 0.15 × 0.12 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4497 independent reflections
Radiation source: fine-focus sealed tube3047 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.000 pixels mm-1θmax = 27.4°, θmin = 3.1°
ω scansh = 1110
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1818
Tmin = 0.788, Tmax = 0.851l = 2020
31202 measured reflections
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)] = 0.053H-atom parameters constrained
wR(F2) = 0.186 w = 1/[σ2(Fo2) + (0.1002P)2 + 1.1952P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max = 0.001
4497 reflectionsΔρmax = 1.61 e Å3
245 parametersΔρmin = 1.04 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0073 (12)
Crystal data top
[CdCl2(C10H8N2)2]V = 1969.68 (10) Å3
Mr = 495.67Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.7477 (2) ŵ = 1.39 mm1
b = 14.3541 (5) ÅT = 293 K
c = 15.8723 (5) Å0.18 × 0.15 × 0.12 mm
β = 98.775 (1)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4497 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3047 reflections with I > 2σ(I)
Tmin = 0.788, Tmax = 0.851Rint = 0.056
31202 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.186H-atom parameters constrained
S = 1.17Δρmax = 1.61 e Å3
4497 reflectionsΔρmin = 1.04 e Å3
245 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.69488 (4)0.77175 (3)0.53520 (3)0.0434 (2)
Cl10.4692 (2)0.77680 (12)0.41696 (13)0.0690 (5)
Cl20.6158 (2)0.88210 (14)0.64297 (14)0.0766 (6)
N10.9503 (6)0.7787 (3)0.6172 (3)0.0471 (12)
N20.8703 (5)0.8562 (3)0.4634 (3)0.0445 (11)
N30.7797 (6)0.6284 (4)0.4710 (3)0.0504 (12)
N40.6420 (5)0.6347 (4)0.6118 (3)0.0492 (12)
C10.9828 (8)0.7475 (5)0.6967 (4)0.0565 (16)
H10.90280.72150.72130.068*
C21.1294 (9)0.7513 (5)0.7455 (5)0.0645 (19)
H21.14650.73010.80150.077*
C31.2469 (9)0.7873 (5)0.7080 (5)0.068 (2)
H31.34700.78920.73790.081*
C41.2168 (7)0.8207 (5)0.6260 (5)0.0622 (17)
H41.29610.84550.60010.075*
C51.0667 (6)0.8170 (4)0.5820 (4)0.0463 (13)
C61.0215 (6)0.8603 (4)0.4967 (4)0.0455 (13)
C71.1268 (7)0.9075 (5)0.4553 (4)0.0576 (16)
H71.23090.90930.47870.069*
C81.0756 (8)0.9521 (5)0.3786 (4)0.0661 (19)
H81.14500.98380.35000.079*
C90.9192 (9)0.9489 (5)0.3451 (4)0.0652 (18)
H90.88080.97890.29440.078*
C100.8230 (8)0.8991 (5)0.3903 (4)0.0548 (15)
H100.71850.89560.36780.066*
C110.8480 (8)0.6289 (5)0.4022 (4)0.0635 (18)
H110.86910.68610.37900.076*
C120.8900 (9)0.5483 (7)0.3628 (5)0.080 (2)
H120.93750.55130.31430.096*
C130.8595 (9)0.4645 (6)0.3976 (5)0.079 (3)
H130.88720.40920.37330.095*
C140.7875 (8)0.4625 (5)0.4688 (5)0.066 (2)
H140.76630.40600.49310.080*
C150.7461 (7)0.5474 (4)0.5046 (4)0.0493 (14)
C160.6667 (6)0.5509 (4)0.5800 (4)0.0470 (14)
C170.6114 (8)0.4700 (5)0.6166 (5)0.0648 (18)
H170.62670.41160.59390.078*
C180.5352 (8)0.4779 (6)0.6858 (5)0.074 (2)
H180.49800.42510.71000.089*
C190.5145 (8)0.5644 (6)0.7189 (5)0.068 (2)
H190.46470.57160.76620.081*
C200.5707 (7)0.6415 (5)0.6792 (4)0.0584 (16)
H200.55730.70040.70140.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0380 (3)0.0474 (3)0.0449 (3)0.00430 (17)0.00717 (18)0.00333 (18)
Cl10.0532 (9)0.0678 (11)0.0776 (12)0.0016 (8)0.0165 (9)0.0071 (9)
Cl20.0647 (10)0.0750 (12)0.0984 (14)0.0204 (9)0.0392 (10)0.0371 (11)
N10.041 (3)0.056 (3)0.042 (3)0.001 (2)0.001 (2)0.001 (2)
N20.038 (2)0.050 (3)0.045 (3)0.008 (2)0.0037 (19)0.003 (2)
N30.051 (3)0.055 (3)0.045 (3)0.002 (2)0.008 (2)0.001 (2)
N40.047 (3)0.051 (3)0.050 (3)0.009 (2)0.006 (2)0.001 (2)
C10.044 (3)0.071 (4)0.053 (4)0.005 (3)0.000 (3)0.001 (3)
C20.072 (5)0.060 (4)0.055 (4)0.008 (3)0.011 (4)0.005 (3)
C30.055 (4)0.064 (4)0.078 (5)0.002 (3)0.013 (4)0.003 (4)
C40.038 (3)0.067 (4)0.080 (5)0.012 (3)0.001 (3)0.003 (4)
C50.036 (3)0.046 (3)0.057 (3)0.004 (2)0.005 (2)0.004 (3)
C60.043 (3)0.049 (3)0.047 (3)0.001 (2)0.015 (2)0.011 (3)
C70.050 (3)0.059 (4)0.067 (4)0.018 (3)0.020 (3)0.001 (3)
C80.075 (5)0.064 (4)0.066 (4)0.021 (4)0.032 (4)0.001 (3)
C90.083 (5)0.061 (4)0.053 (4)0.006 (4)0.014 (3)0.004 (3)
C100.058 (4)0.061 (4)0.044 (3)0.009 (3)0.006 (3)0.009 (3)
C110.071 (4)0.066 (4)0.059 (4)0.005 (4)0.024 (3)0.009 (3)
C120.078 (5)0.092 (7)0.070 (5)0.013 (5)0.016 (4)0.030 (5)
C130.072 (5)0.080 (6)0.083 (6)0.024 (4)0.003 (4)0.042 (5)
C140.066 (4)0.047 (4)0.080 (5)0.008 (3)0.007 (4)0.014 (3)
C150.045 (3)0.046 (3)0.054 (3)0.002 (3)0.003 (3)0.006 (3)
C160.039 (3)0.045 (3)0.052 (3)0.005 (2)0.007 (2)0.005 (3)
C170.062 (4)0.049 (4)0.079 (5)0.011 (3)0.002 (4)0.018 (3)
C180.057 (4)0.076 (5)0.085 (5)0.018 (4)0.001 (4)0.037 (5)
C190.054 (4)0.092 (6)0.054 (4)0.015 (4)0.002 (3)0.018 (4)
C200.054 (3)0.075 (5)0.049 (3)0.011 (3)0.017 (3)0.001 (3)
Geometric parameters (Å, º) top
Cd1—N22.378 (5)C7—C81.388 (9)
Cd1—N42.394 (5)C7—H70.9300
Cd1—N12.410 (5)C8—C91.391 (10)
Cd1—N32.461 (5)C8—H80.9300
Cd1—Cl22.5049 (18)C9—C101.385 (9)
Cd1—Cl12.5087 (18)C9—H90.9300
N1—C11.327 (8)C10—H100.9300
N1—C51.351 (8)C11—C121.392 (10)
N2—C101.323 (7)C11—H110.9300
N2—C61.349 (7)C12—C131.366 (13)
N3—C111.322 (8)C12—H120.9300
N3—C151.330 (8)C13—C141.375 (10)
N4—C201.322 (8)C13—H130.9300
N4—C161.335 (8)C14—C151.415 (9)
C1—C21.395 (10)C14—H140.9300
C1—H10.9300C15—C161.472 (10)
C2—C31.365 (11)C16—C171.417 (9)
C2—H20.9300C17—C181.374 (11)
C3—C41.375 (10)C17—H170.9300
C3—H30.9300C18—C191.370 (12)
C4—C51.391 (8)C18—H180.9300
C4—H40.9300C19—C201.399 (10)
C5—C61.487 (8)C19—H190.9300
C6—C71.387 (8)C20—H200.9300
N2—Cd1—N4148.29 (17)C7—C6—C5122.2 (5)
N2—Cd1—N167.98 (16)C6—C7—C8119.5 (6)
N4—Cd1—N189.69 (16)C6—C7—H7120.2
N2—Cd1—N388.30 (17)C8—C7—H7120.2
N4—Cd1—N367.48 (19)C7—C8—C9119.1 (6)
N1—Cd1—N386.83 (16)C7—C8—H8120.5
N2—Cd1—Cl2105.71 (13)C9—C8—H8120.5
N4—Cd1—Cl294.47 (13)C10—C9—C8117.4 (6)
N1—Cd1—Cl286.28 (13)C10—C9—H9121.3
N3—Cd1—Cl2160.70 (13)C8—C9—H9121.3
N2—Cd1—Cl196.80 (12)N2—C10—C9124.1 (6)
N4—Cd1—Cl1102.28 (12)N2—C10—H10117.9
N1—Cd1—Cl1164.08 (14)C9—C10—H10117.9
N3—Cd1—Cl188.10 (12)N3—C11—C12123.4 (8)
Cl2—Cd1—Cl1102.99 (7)N3—C11—H11118.3
C1—N1—C5117.7 (5)C12—C11—H11118.3
C1—N1—Cd1123.1 (4)C13—C12—C11118.0 (7)
C5—N1—Cd1119.2 (4)C13—C12—H12121.0
C10—N2—C6118.7 (5)C11—C12—H12121.0
C10—N2—Cd1121.3 (4)C12—C13—C14119.5 (7)
C6—N2—Cd1120.0 (4)C12—C13—H13120.3
C11—N3—C15119.5 (6)C14—C13—H13120.3
C11—N3—Cd1122.7 (5)C13—C14—C15119.4 (7)
C15—N3—Cd1117.7 (4)C13—C14—H14120.3
C20—N4—C16119.7 (6)C15—C14—H14120.3
C20—N4—Cd1120.2 (5)N3—C15—C14120.3 (6)
C16—N4—Cd1119.6 (4)N3—C15—C16117.2 (5)
N1—C1—C2124.1 (7)C14—C15—C16122.5 (6)
N1—C1—H1118.0N4—C16—C17119.9 (6)
C2—C1—H1118.0N4—C16—C15117.4 (5)
C3—C2—C1117.5 (7)C17—C16—C15122.6 (6)
C3—C2—H2121.2C18—C17—C16119.9 (7)
C1—C2—H2121.2C18—C17—H17120.1
C2—C3—C4119.8 (7)C16—C17—H17120.1
C2—C3—H3120.1C19—C18—C17119.3 (7)
C4—C3—H3120.1C19—C18—H18120.3
C3—C4—C5119.4 (6)C17—C18—H18120.3
C3—C4—H4120.3C18—C19—C20117.9 (7)
C5—C4—H4120.3C18—C19—H19121.0
N1—C5—C4121.5 (6)C20—C19—H19121.0
N1—C5—C6115.8 (5)N4—C20—C19123.2 (7)
C4—C5—C6122.7 (6)N4—C20—H20118.4
N2—C6—C7121.2 (6)C19—C20—H20118.4
N2—C6—C5116.5 (5)
N2—Cd1—N1—C1173.2 (5)Cd1—N1—C5—C4178.5 (5)
N4—Cd1—N1—C129.9 (5)C1—N1—C5—C6173.5 (5)
N3—Cd1—N1—C197.4 (5)Cd1—N1—C5—C65.6 (7)
Cl2—Cd1—N1—C164.6 (5)C3—C4—C5—N12.1 (10)
Cl1—Cd1—N1—C1169.0 (4)C3—C4—C5—C6173.6 (6)
N2—Cd1—N1—C55.8 (4)C10—N2—C6—C70.7 (9)
N4—Cd1—N1—C5151.1 (4)Cd1—N2—C6—C7178.7 (5)
N3—Cd1—N1—C583.6 (4)C10—N2—C6—C5175.5 (5)
Cl2—Cd1—N1—C5114.4 (4)Cd1—N2—C6—C55.0 (7)
Cl1—Cd1—N1—C512.0 (8)N1—C5—C6—N20.4 (8)
N4—Cd1—N2—C10136.8 (5)C4—C5—C6—N2176.3 (6)
N1—Cd1—N2—C10175.0 (5)N1—C5—C6—C7175.8 (6)
N3—Cd1—N2—C1097.8 (5)C4—C5—C6—C70.1 (10)
Cl2—Cd1—N2—C1095.7 (5)N2—C6—C7—C80.6 (10)
Cl1—Cd1—N2—C109.9 (5)C5—C6—C7—C8175.4 (6)
N4—Cd1—N2—C642.7 (6)C6—C7—C8—C90.3 (11)
N1—Cd1—N2—C65.6 (4)C7—C8—C9—C101.2 (11)
N3—Cd1—N2—C681.7 (4)C6—N2—C10—C90.2 (10)
Cl2—Cd1—N2—C684.9 (4)Cd1—N2—C10—C9179.6 (5)
Cl1—Cd1—N2—C6169.5 (4)C8—C9—C10—N21.1 (11)
N2—Cd1—N3—C1120.4 (5)C15—N3—C11—C121.1 (11)
N4—Cd1—N3—C11179.4 (5)Cd1—N3—C11—C12176.8 (6)
N1—Cd1—N3—C1188.4 (5)N3—C11—C12—C130.4 (12)
Cl2—Cd1—N3—C11157.7 (4)C11—C12—C13—C140.8 (12)
Cl1—Cd1—N3—C1176.5 (5)C12—C13—C14—C150.1 (11)
N2—Cd1—N3—C15163.8 (4)C11—N3—C15—C142.0 (9)
N4—Cd1—N3—C154.8 (4)Cd1—N3—C15—C14178.0 (4)
N1—Cd1—N3—C1595.7 (4)C11—N3—C15—C16178.6 (5)
Cl2—Cd1—N3—C1526.5 (7)Cd1—N3—C15—C162.6 (7)
Cl1—Cd1—N3—C1599.4 (4)C13—C14—C15—N31.6 (10)
N2—Cd1—N4—C20138.8 (4)C13—C14—C15—C16179.0 (6)
N1—Cd1—N4—C2095.0 (5)C20—N4—C16—C172.3 (9)
N3—Cd1—N4—C20178.3 (5)Cd1—N4—C16—C17169.2 (4)
Cl2—Cd1—N4—C208.7 (5)C20—N4—C16—C15179.8 (5)
Cl1—Cd1—N4—C2095.6 (4)Cd1—N4—C16—C158.3 (7)
N2—Cd1—N4—C1649.8 (6)N3—C15—C16—N43.6 (8)
N1—Cd1—N4—C1693.6 (4)C14—C15—C16—N4175.8 (5)
N3—Cd1—N4—C166.9 (4)N3—C15—C16—C17173.8 (5)
Cl2—Cd1—N4—C16179.8 (4)C14—C15—C16—C176.8 (10)
Cl1—Cd1—N4—C1675.9 (4)N4—C16—C17—C181.2 (9)
C5—N1—C1—C20.5 (10)C15—C16—C17—C18178.6 (6)
Cd1—N1—C1—C2179.6 (5)C16—C17—C18—C190.4 (10)
N1—C1—C2—C31.7 (11)C17—C18—C19—C201.0 (10)
C1—C2—C3—C42.1 (11)C16—N4—C20—C191.8 (10)
C2—C3—C4—C50.3 (11)Cd1—N4—C20—C19169.6 (5)
C1—N1—C5—C42.5 (9)C18—C19—C20—N40.1 (11)

Experimental details

Crystal data
Chemical formula[CdCl2(C10H8N2)2]
Mr495.67
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.7477 (2), 14.3541 (5), 15.8723 (5)
β (°) 98.775 (1)
V3)1969.68 (10)
Z4
Radiation typeMo Kα
µ (mm1)1.39
Crystal size (mm)0.18 × 0.15 × 0.12
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.788, 0.851
No. of measured, independent and
observed [I > 2σ(I)] reflections
31202, 4497, 3047
Rint0.056
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.186, 1.17
No. of reflections4497
No. of parameters245
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.61, 1.04

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903) and the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), Heilongjiang University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhou, Y.-F., Xu, Y., Yuan, D.-Q. & Hong, M.-C. (2003). Acta Cryst. E59, m821–m823.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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