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Acta Cryst. (2009). E65, m1689    [ doi:10.1107/S1600536809050107 ]

[N'-(5-Chloro-2-oxidobenzylidene-[kappa]O)-3-hydroxy-2-naphthohydrazidato-[kappa]2N',O2]diphenyltin(IV)

S. M. Lee, K. M. Lo, H. M. Ali and S. W. Ng

Abstract top

The SnIV atom in the title compound, [Sn(C6H5)2(C18H11ClN2O3)], is O,N,O'-chelated by the deprotonated Schiff base ligand and further bonded by two phenyl rings in a distorted cis-C2SnNO2 trigonal-bipyramidal geometry [C-Sn-C = 125.7 (2)°]. The two phenyl rings are oriented at a dihedral angle of 55.2 (3)°. Intramolecular O-H...N hydrogen bonding is present in the crystal structure.

Related literature top

For the Sn(CH3)2(C18H11ClN2O3) analog, see: Lee et al. (2009).

Experimental top

The Schiff base was prepared by the condensation of 3-hydroxy-2-naphthoylhydrazide and 5-chlorobenzaldehyde. The Schiff base (0.5 g, 1.5 mmol) and diphenyltin dichloride (0.52 g, 1.5 mmol) in a mixture (1:1) of methanol/chloroform was heated for 1 h. The filtered solution yielded the yellow crystals when allowed to evaporate slowly.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The hydroxy H-atom was located in a difference Fourier map and was refined with a distance restraint of O–H 0.84±0.01 Å.

The final difference Fourier map had a peak in the vicinity of Sn1.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Sn(C6H5)2(C18H11ClN2O3) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[N'-(5-Chloro-2-oxidobenzylidene-κO)-3-hydroxy-2- naphthohydrazidato-κ2N',O2]diphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C18H11ClN2O3)]Z = 2
Mr = 611.63F(000) = 612
Triclinic, P1Dx = 1.611 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5690 (4) ÅCell parameters from 2361 reflections
b = 10.9788 (4) Åθ = 2.5–26.8°
c = 11.8319 (4) ŵ = 1.16 mm−1
α = 68.381 (2)°T = 140 K
β = 82.450 (2)°Block, yellow
γ = 82.672 (2)°0.30 × 0.25 × 0.20 mm
V = 1260.60 (8) Å3
Data collection top
Bruker SMART APEX
diffractometer		4280 independent reflections
Radiation source: fine-focus sealed tube3563 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→12
Tmin = 0.798, Tmax = 1.000k = −12→13
6070 measured reflectionsl = −14→14
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0736P)2 + 1.6275P]
where P = (Fo2 + 2Fc2)/3
4280 reflections(Δ/σ)max = 0.001
338 parametersΔρmax = 1.39 e Å−3
1 restraintΔρmin = −0.70 e Å−3
Crystal data top
[Sn(C6H5)2(C18H11ClN2O3)]γ = 82.672 (2)°
Mr = 611.63V = 1260.60 (8) Å3
Triclinic, P1Z = 2
a = 10.5690 (4) ÅMo Kα radiation
b = 10.9788 (4) ŵ = 1.16 mm−1
c = 11.8319 (4) ÅT = 140 K
α = 68.381 (2)°0.30 × 0.25 × 0.20 mm
β = 82.450 (2)°
Data collection top
Bruker SMART APEX
diffractometer		4280 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3563 reflections with I > 2σ(I)
Tmin = 0.798, Tmax = 1.000Rint = 0.026
6070 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126Δρmax = 1.39 e Å−3
S = 1.05Δρmin = −0.70 e Å−3
4280 reflectionsAbsolute structure: ?
338 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.70294 (4)0.27373 (3)0.41404 (3)0.02376 (15)
Cl10.26756 (16)0.83455 (15)0.05708 (14)0.0421 (4)
O10.5939 (4)0.3459 (4)0.2678 (4)0.0301 (9)
O20.8166 (3)0.2790 (4)0.5498 (3)0.0260 (8)
O30.8095 (4)0.6332 (4)0.6156 (4)0.0342 (9)
H30.785 (6)0.626 (6)0.554 (4)0.036 (18)*
N10.6825 (4)0.4749 (4)0.4076 (4)0.0227 (9)
N20.7518 (4)0.5023 (4)0.4861 (4)0.0243 (10)
C10.8655 (5)0.1998 (5)0.3241 (5)0.0239 (11)
C20.9726 (5)0.1487 (5)0.3839 (5)0.0280 (12)
H20.97450.14780.46420.034*
C31.0794 (6)0.0977 (6)0.3278 (5)0.0376 (15)
H3A1.15400.06220.36980.045*
C41.0764 (6)0.0992 (6)0.2115 (6)0.0399 (15)
H41.14840.06280.17380.048*
C50.9670 (6)0.1543 (6)0.1480 (5)0.0346 (14)
H50.96590.15690.06700.041*
C60.8606 (6)0.2049 (5)0.2042 (5)0.0306 (13)
H60.78610.24220.16240.037*
C70.5649 (5)0.1587 (5)0.5428 (5)0.0256 (12)
C80.5989 (6)0.0795 (5)0.6585 (5)0.0297 (13)
H80.68250.07850.68040.036*
C90.5098 (6)0.0019 (6)0.7421 (6)0.0396 (15)
H90.5329−0.05260.82110.047*
C100.3894 (6)0.0032 (6)0.7117 (6)0.0403 (16)
H100.3294−0.05050.76970.048*
C110.3539 (6)0.0823 (6)0.5971 (6)0.0415 (16)
H110.26950.08470.57650.050*
C120.4438 (5)0.1581 (6)0.5126 (6)0.0314 (13)
H120.42120.21020.43280.038*
C130.5173 (5)0.4566 (5)0.2272 (5)0.0227 (11)
C140.4279 (5)0.4645 (6)0.1468 (5)0.0297 (12)
H140.41960.38940.12750.036*
C150.3527 (6)0.5769 (6)0.0957 (5)0.0336 (13)
H150.29280.58000.04130.040*
C160.3640 (6)0.6880 (6)0.1234 (5)0.0311 (13)
C170.4479 (6)0.6835 (6)0.2032 (5)0.0307 (13)
H170.45390.75930.22210.037*
C180.5258 (5)0.5677 (5)0.2580 (5)0.0244 (11)
C190.6084 (5)0.5730 (5)0.3425 (5)0.0266 (12)
H190.60910.65510.35200.032*
C200.8181 (5)0.3960 (5)0.5544 (5)0.0247 (12)
C210.8990 (5)0.4095 (5)0.6409 (5)0.0235 (11)
C220.8891 (5)0.5257 (5)0.6705 (5)0.0248 (11)
C230.9596 (5)0.5304 (5)0.7572 (5)0.0286 (12)
H230.94850.60590.77980.034*
C241.0496 (6)0.4240 (5)0.8146 (5)0.0296 (13)
C251.1290 (6)0.4294 (6)0.8994 (5)0.0338 (13)
H251.11990.50420.92290.041*
C261.2191 (6)0.3278 (6)0.9484 (5)0.0384 (15)
H261.27260.33371.00440.046*
C271.2331 (6)0.2150 (6)0.9166 (5)0.0353 (14)
H271.29630.14550.95010.042*
C281.1540 (5)0.2065 (6)0.8362 (5)0.0307 (13)
H281.16180.12910.81660.037*
C291.0625 (5)0.3094 (5)0.7826 (5)0.0244 (11)
C300.9820 (5)0.3049 (5)0.6981 (5)0.0264 (12)
H300.98560.22680.68040.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0256 (2)0.0222 (2)0.0264 (2)−0.00428 (14)−0.00185 (14)−0.01152 (15)
Cl10.0500 (10)0.0377 (8)0.0378 (8)0.0106 (7)−0.0166 (7)−0.0129 (7)
O10.034 (2)0.026 (2)0.040 (2)0.0033 (17)−0.0167 (18)−0.0194 (17)
O20.024 (2)0.0249 (19)0.033 (2)0.0014 (15)−0.0118 (16)−0.0122 (16)
O30.046 (3)0.027 (2)0.035 (2)0.0013 (19)−0.0153 (19)−0.0158 (18)
N10.022 (2)0.025 (2)0.023 (2)−0.0039 (18)−0.0017 (18)−0.0104 (19)
N20.026 (2)0.024 (2)0.027 (2)−0.0042 (19)−0.0062 (19)−0.0121 (19)
C10.015 (3)0.020 (3)0.037 (3)−0.004 (2)0.003 (2)−0.011 (2)
C20.020 (3)0.031 (3)0.028 (3)0.004 (2)−0.004 (2)−0.007 (2)
C30.026 (3)0.042 (4)0.036 (3)0.011 (3)−0.007 (3)−0.006 (3)
C40.041 (4)0.040 (3)0.035 (3)−0.002 (3)0.010 (3)−0.014 (3)
C50.039 (4)0.037 (3)0.027 (3)−0.008 (3)0.001 (3)−0.011 (3)
C60.038 (3)0.026 (3)0.030 (3)−0.014 (2)0.003 (2)−0.011 (2)
C70.022 (3)0.028 (3)0.032 (3)−0.003 (2)0.005 (2)−0.019 (2)
C80.030 (3)0.027 (3)0.036 (3)−0.002 (2)0.001 (2)−0.017 (2)
C90.049 (4)0.030 (3)0.040 (4)−0.005 (3)0.006 (3)−0.016 (3)
C100.039 (4)0.037 (3)0.050 (4)−0.017 (3)0.017 (3)−0.024 (3)
C110.033 (4)0.045 (4)0.062 (4)−0.017 (3)0.012 (3)−0.038 (3)
C120.027 (3)0.035 (3)0.038 (3)−0.002 (2)0.000 (2)−0.022 (3)
C130.014 (3)0.027 (3)0.025 (3)0.002 (2)−0.002 (2)−0.009 (2)
C140.024 (3)0.034 (3)0.034 (3)0.001 (2)−0.010 (2)−0.014 (3)
C150.030 (3)0.035 (3)0.033 (3)0.002 (3)−0.013 (2)−0.007 (3)
C160.032 (3)0.031 (3)0.026 (3)−0.003 (3)0.003 (2)−0.008 (2)
C170.035 (3)0.033 (3)0.027 (3)−0.005 (3)0.002 (2)−0.015 (2)
C180.019 (3)0.033 (3)0.020 (3)−0.006 (2)0.000 (2)−0.008 (2)
C190.028 (3)0.027 (3)0.028 (3)−0.004 (2)0.001 (2)−0.014 (2)
C200.018 (3)0.035 (3)0.026 (3)−0.011 (2)0.005 (2)−0.016 (2)
C210.017 (3)0.029 (3)0.027 (3)−0.008 (2)0.001 (2)−0.012 (2)
C220.025 (3)0.026 (3)0.024 (3)−0.008 (2)0.001 (2)−0.009 (2)
C230.036 (3)0.025 (3)0.027 (3)−0.007 (2)0.000 (2)−0.011 (2)
C240.041 (3)0.030 (3)0.019 (3)−0.016 (3)0.003 (2)−0.007 (2)
C250.044 (4)0.033 (3)0.026 (3)−0.015 (3)0.003 (3)−0.010 (2)
C260.042 (4)0.044 (4)0.028 (3)−0.012 (3)−0.007 (3)−0.007 (3)
C270.028 (3)0.035 (3)0.031 (3)0.001 (3)−0.006 (2)0.001 (3)
C280.027 (3)0.038 (3)0.027 (3)−0.006 (2)−0.001 (2)−0.011 (2)
C290.016 (3)0.030 (3)0.023 (3)−0.001 (2)−0.002 (2)−0.005 (2)
C300.026 (3)0.030 (3)0.026 (3)−0.003 (2)−0.003 (2)−0.013 (2)
Geometric parameters (Å, °) top
Sn1—O12.057 (4)C11—C121.391 (8)
Sn1—O22.150 (3)C11—H110.9500
Sn1—N12.166 (4)C12—H120.9500
Sn1—C12.131 (5)C13—C141.400 (7)
Sn1—C72.124 (5)C13—C181.411 (8)
Cl1—C161.763 (6)C14—C151.359 (8)
O1—C131.336 (6)C14—H140.9500
O2—C201.308 (6)C15—C161.397 (8)
O3—C221.360 (7)C15—H150.9500
O3—H30.838 (10)C16—C171.361 (8)
N1—C191.304 (7)C17—C181.407 (8)
N1—N21.389 (6)C17—H170.9500
N2—C201.323 (7)C18—C191.433 (8)
C1—C21.361 (7)C19—H190.9500
C1—C61.407 (8)C20—C211.475 (7)
C2—C31.394 (8)C21—C301.367 (8)
C2—H20.9500C21—C221.431 (7)
C3—C41.375 (9)C22—C231.364 (8)
C3—H3A0.9500C23—C241.426 (8)
C4—C51.408 (9)C23—H230.9500
C4—H40.9500C24—C251.411 (8)
C5—C61.389 (8)C24—C291.427 (8)
C5—H50.9500C25—C261.373 (9)
C6—H60.9500C25—H250.9500
C7—C121.375 (8)C26—C271.406 (9)
C7—C81.390 (8)C26—H260.9500
C8—C91.389 (8)C27—C281.381 (8)
C8—H80.9500C27—H270.9500
C9—C101.364 (9)C28—C291.404 (8)
C9—H90.9500C28—H280.9500
C10—C111.385 (10)C29—C301.413 (7)
C10—H100.9500C30—H300.9500
O1—Sn1—C797.47 (19)O1—C13—C18123.0 (5)
O1—Sn1—C196.68 (18)C14—C13—C18118.5 (5)
C7—Sn1—C1125.67 (19)C15—C14—C13121.6 (5)
O1—Sn1—O2157.66 (14)C15—C14—H14119.2
C7—Sn1—O294.59 (18)C13—C14—H14119.2
C1—Sn1—O291.41 (18)C14—C15—C16119.7 (5)
O1—Sn1—N184.68 (15)C14—C15—H15120.2
C7—Sn1—N1111.96 (17)C16—C15—H15120.2
C1—Sn1—N1121.43 (17)C17—C16—C15120.5 (5)
O2—Sn1—N173.37 (15)C17—C16—Cl1119.4 (4)
C13—O1—Sn1131.1 (3)C15—C16—Cl1120.1 (5)
C20—O2—Sn1114.2 (3)C16—C17—C18120.7 (5)
C22—O3—H3109 (4)C16—C17—H17119.6
C19—N1—N2115.6 (4)C18—C17—H17119.6
C19—N1—Sn1127.8 (4)C17—C18—C13118.9 (5)
N2—N1—Sn1116.6 (3)C17—C18—C19116.0 (5)
C20—N2—N1111.8 (4)C13—C18—C19125.1 (5)
C2—C1—C6121.1 (5)N1—C19—C18125.7 (5)
C2—C1—Sn1119.2 (4)N1—C19—H19117.2
C6—C1—Sn1119.6 (4)C18—C19—H19117.2
C1—C2—C3120.3 (5)O2—C20—N2123.9 (5)
C1—C2—H2119.8O2—C20—C21117.6 (5)
C3—C2—H2119.8N2—C20—C21118.4 (5)
C4—C3—C2119.7 (6)C30—C21—C22119.4 (5)
C4—C3—H3A120.1C30—C21—C20118.5 (5)
C2—C3—H3A120.1C22—C21—C20122.0 (5)
C3—C4—C5120.3 (6)O3—C22—C23118.0 (5)
C3—C4—H4119.8O3—C22—C21122.0 (5)
C5—C4—H4119.8C23—C22—C21120.0 (5)
C6—C5—C4119.8 (6)C22—C23—C24121.2 (5)
C6—C5—H5120.1C22—C23—H23119.4
C4—C5—H5120.1C24—C23—H23119.4
C5—C6—C1118.6 (6)C25—C24—C23122.3 (5)
C5—C6—H6120.7C25—C24—C29118.8 (5)
C1—C6—H6120.7C23—C24—C29118.8 (5)
C12—C7—C8119.4 (5)C26—C25—C24120.8 (6)
C12—C7—Sn1121.2 (4)C26—C25—H25119.6
C8—C7—Sn1119.4 (4)C24—C25—H25119.6
C9—C8—C7119.5 (6)C25—C26—C27120.7 (6)
C9—C8—H8120.2C25—C26—H26119.6
C7—C8—H8120.2C27—C26—H26119.6
C10—C9—C8120.6 (6)C28—C27—C26119.3 (5)
C10—C9—H9119.7C28—C27—H27120.3
C8—C9—H9119.7C26—C27—H27120.3
C9—C10—C11120.5 (6)C27—C28—C29121.5 (6)
C9—C10—H10119.8C27—C28—H28119.3
C11—C10—H10119.8C29—C28—H28119.3
C10—C11—C12118.9 (6)C28—C29—C30122.9 (5)
C10—C11—H11120.5C28—C29—C24118.8 (5)
C12—C11—H11120.5C30—C29—C24118.3 (5)
C7—C12—C11121.0 (6)C21—C30—C29122.1 (5)
C7—C12—H12119.5C21—C30—H30119.0
C11—C12—H12119.5C29—C30—H30119.0
O1—C13—C14118.4 (5)
C7—Sn1—O1—C1392.8 (5)Sn1—O1—C13—C14−162.6 (4)
C1—Sn1—O1—C13−139.8 (5)Sn1—O1—C13—C1820.0 (8)
O2—Sn1—O1—C13−29.3 (7)O1—C13—C14—C15−175.7 (5)
N1—Sn1—O1—C13−18.7 (5)C18—C13—C14—C151.9 (8)
O1—Sn1—O2—C208.6 (6)C13—C14—C15—C160.0 (9)
C7—Sn1—O2—C20−113.9 (4)C14—C15—C16—C17−1.4 (9)
C1—Sn1—O2—C20120.1 (4)C14—C15—C16—Cl1179.7 (5)
N1—Sn1—O2—C20−2.3 (3)C15—C16—C17—C180.8 (8)
O1—Sn1—N1—C199.4 (4)Cl1—C16—C17—C18179.8 (4)
C7—Sn1—N1—C19−86.5 (5)C16—C17—C18—C131.1 (8)
C1—Sn1—N1—C19104.0 (5)C16—C17—C18—C19−178.6 (5)
O2—Sn1—N1—C19−174.8 (5)O1—C13—C18—C17175.0 (5)
O1—Sn1—N1—N2−173.9 (3)C14—C13—C18—C17−2.4 (8)
C7—Sn1—N1—N290.2 (4)O1—C13—C18—C19−5.2 (8)
C1—Sn1—N1—N2−79.3 (4)C14—C13—C18—C19177.3 (5)
O2—Sn1—N1—N21.9 (3)N2—N1—C19—C18−178.3 (5)
C19—N1—N2—C20175.9 (5)Sn1—N1—C19—C18−1.6 (8)
Sn1—N1—N2—C20−1.2 (5)C17—C18—C19—N1176.1 (5)
O1—Sn1—C1—C2175.0 (4)C13—C18—C19—N1−3.7 (9)
C7—Sn1—C1—C2−80.8 (5)Sn1—O2—C20—N22.8 (6)
O2—Sn1—C1—C215.9 (4)Sn1—O2—C20—C21−177.0 (3)
N1—Sn1—C1—C287.2 (5)N1—N2—C20—O2−1.1 (7)
O1—Sn1—C1—C6−4.8 (4)N1—N2—C20—C21178.7 (4)
C7—Sn1—C1—C699.4 (4)O2—C20—C21—C309.5 (7)
O2—Sn1—C1—C6−163.9 (4)N2—C20—C21—C30−170.4 (5)
N1—Sn1—C1—C6−92.6 (4)O2—C20—C21—C22−167.7 (5)
C6—C1—C2—C3−1.3 (8)N2—C20—C21—C2212.5 (7)
Sn1—C1—C2—C3178.9 (4)C30—C21—C22—O3179.2 (5)
C1—C2—C3—C40.0 (9)C20—C21—C22—O3−3.7 (8)
C2—C3—C4—C51.3 (9)C30—C21—C22—C23−1.6 (8)
C3—C4—C5—C6−1.4 (9)C20—C21—C22—C23175.5 (5)
C4—C5—C6—C10.2 (8)O3—C22—C23—C24−177.0 (5)
C2—C1—C6—C51.2 (8)C21—C22—C23—C243.8 (8)
Sn1—C1—C6—C5−179.0 (4)C22—C23—C24—C25176.3 (5)
O1—Sn1—C7—C12−3.0 (4)C22—C23—C24—C29−1.9 (8)
C1—Sn1—C7—C12−106.8 (4)C23—C24—C25—C26−176.8 (5)
O2—Sn1—C7—C12158.1 (4)C29—C24—C25—C261.5 (8)
N1—Sn1—C7—C1284.2 (4)C24—C25—C26—C27−1.0 (9)
O1—Sn1—C7—C8175.0 (4)C25—C26—C27—C28−0.7 (9)
C1—Sn1—C7—C871.2 (5)C26—C27—C28—C291.9 (9)
O2—Sn1—C7—C8−23.8 (4)C27—C28—C29—C30178.6 (5)
N1—Sn1—C7—C8−97.7 (4)C27—C28—C29—C24−1.4 (8)
C12—C7—C8—C9−0.5 (8)C25—C24—C29—C28−0.3 (8)
Sn1—C7—C8—C9−178.6 (4)C23—C24—C29—C28178.0 (5)
C7—C8—C9—C10−0.3 (8)C25—C24—C29—C30179.7 (5)
C8—C9—C10—C11−0.2 (9)C23—C24—C29—C30−2.0 (7)
C9—C10—C11—C121.4 (9)C22—C21—C30—C29−2.5 (8)
C8—C7—C12—C111.8 (8)C20—C21—C30—C29−179.7 (5)
Sn1—C7—C12—C11179.8 (4)C28—C29—C30—C21−175.7 (5)
C10—C11—C12—C7−2.2 (8)C24—C29—C30—C214.3 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N20.84 (1)1.90 (4)2.622 (6)144 (6)
Table 1
Selected geometric parameters (Å) top
Sn1—O12.057 (4)Sn1—C12.131 (5)
Sn1—O22.150 (3)Sn1—C72.124 (5)
Sn1—N12.166 (4)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N20.84 (1)1.90 (4)2.622 (6)144 (6)
Acknowledgements top

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Lee, S. M., Lo, K. M., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, m816.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.