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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1645–m1646.
Published online 2010 November 24. doi:  10.1107/S1600536810046738
PMCID: PMC3011489

Bis(dicyclo­hexyl­ammonium) μ-oxalato-κ4 O 1,O 2:O 1′,O 2′-bis­[aqua­(oxalato-κ2 O 1,O 2)diphenyl­stannate(IV)]

Abstract

The structure of the title compound, (C12H24N)2[Sn2(C6H5)4(C2O4)3(H2O)2], consists of a bischelating oxalate ion, located on an inversion center, which is linked to two SnPh2 groups. The coordination sphere of the Sn(IV) ion is completed by a monochelating oxalate anion and a water mol­ecule. The Sn(IV) atoms are thus seven-coordinated. The discrete binuclear units are further connected by hydrogen bonds, leading to a supra­molecular crystal structure. The asymmetric unit contains one half dianion and one (Cy2NH2)+ cation.

Related literature

For background to organotin(IV) chemistry, see: Ballmann et al. (2009 [triangle]); Diallo et al. (2007 [triangle]); Diassé-Sarr et al. (1997 [triangle]); Ng et al. (1992 [triangle]); Singh et al. (2008 [triangle]); de Sousa et al. (2007 [triangle]); Wang et al. (2009 [triangle]); Xanthopoulou et al. (2007 [triangle], 2008 [triangle]); Zia-ur-Rahman et al. (2007 [triangle]). For related Sn(IV) structures, see: Diop et al. (2002 [triangle], 2003 [triangle]).

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Object name is e-66-m1645-scheme1.jpg

Experimental

Crystal data

  • (C12H24N)2[Sn2(C6H5)4(C2O4)3(H2O)2]
  • M r = 1210.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1645-efi1.jpg
  • a = 13.1725 (4) Å
  • b = 14.6121 (4) Å
  • c = 14.1139 (4) Å
  • β = 100.869 (2)°
  • V = 2667.88 (13) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.00 mm−1
  • T = 150 K
  • 0.2 × 0.2 × 0.2 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SORTAV; Blessing, 1995 [triangle]) T min = 0.825, T max = 0.825
  • 48411 measured reflections
  • 6114 independent reflections
  • 4069 reflections with I > 2σ(I)
  • R int = 0.126

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.082
  • S = 1.01
  • 6114 reflections
  • 341 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.72 e Å−3

Data collection: COLLECT (Nonius, 2000 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO (Otwinowski & Minor, 1997 [triangle]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046738/bh2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046738/bh2310Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

In the dynamic of our research work on organotin(IV) chemistry (Diallo et al., 2007; Diassé-Sarr et al., 1997) because of several applications found (Xanthopoulou et al., 2007, 2008; Zia-ur-Rahman et al., 2007; Singh et al., 2008; Wang et al., 2009; Ballmann et al., 2009; de Sousa et al., 2007) and our interest in the coordinating behaviour of oxyanions in this family of compounds, we had yet reported the crystal structures of C2O4(SnPh3)2 (Diop et al., 2003) and SO4(SnPh3)2.H2O (Diop et al., 2002) and have initiated here the study of the interactions between (Cy2NH2)2C2O4.2H2O and C2O4(SnPh3)2 which has yielded the studied compound.

The asymmetric unit consists of one half of the molecule, located about an inversion centre at the mid-point of the C3—C3i bond (symmetry code i: -x, 1 - y, -z). In its units structure two SnPh2 residues are linked by a central bichelating oxalate ion [O5O6:O5O6] and every SnPh2 residue is then linked to another monochelating anion [O1, O2]. A water molecule completes the tin centre coordination to seven, which can be described as a distorted trans-C2SnO5 pentagonal bipyramidal geometry [C—Sn—C angle: 168.75 (13)°]. Within the bridging carboxylate all the C—O bonds are equal within experimental error, implying complete delocalization of double-bond character within this residue. The bond lengths C1—O1 and C2—O2, [1.273 (4) Å], and C2—O3, C1—O4 [1.225 (4) and 1.247 (4) Å] indicate respectively a single and double bond character; the bond length C1—O4 results from involvement of O4 in two distinct hydrogen bonds. Among the Sn—O bonds, Sn1—O6 is notably longer, O6 being the only oxygen of this kind involved in hydrogen bonding.

Every moiety is then connected to its neighbour by three types of hydrogen bonds: one O—H···O type involving an H atom of the water molecule and one O atom of monochelating oxalate [O7—H7B···O4], one N—H···O contact involving one O atom of the bichelating oxalate anion and the cation [N—H1B···O6] and a third bifurcated one also involving the cation [N—H1A···O3 and N—H1A···O4], giving a supramolecular crystal structure.

A similar structure, bearing butyl groups in place of phenyl, was previously reported (Ng et al., 1992).

Experimental

Crystals of the title compound were obtained by allowing (Cy2NH2)2C2O4.2H2O (90 mmol in 15 ml e thanol) to react with C2O4(SnPh3)2 (45 mmol in 15 ml e thanol). The mixture was stirred during several hours and slow solvent evaporation afforded crystals suitable for X-rays studies.

Refinement

All C–bonded H atoms were placed in idealized positions (C—H in the range 0.95 to 1.00 Å), while H atoms bonded to N and O atoms were considered as free atoms. Isotropic displacement parameters for H atoms were calculated from Ueq of their parent atoms.

Figures

Fig. 1.
A part of the crystal structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed bonds represent hydrogen bonds.

Crystal data

(C12H24N)2[Sn2(C6H5)4(C2O4)3(H2O)2]F(000) = 1244
Mr = 1210.52Dx = 1.507 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 29450 reflections
a = 13.1725 (4) Åθ = 2.9–27.5°
b = 14.6121 (4) ŵ = 1.00 mm1
c = 14.1139 (4) ÅT = 150 K
β = 100.869 (2)°Irregular, colourless
V = 2667.88 (13) Å30.2 × 0.2 × 0.2 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer6114 independent reflections
Radiation source: fine-focus sealed tube4069 reflections with I > 2σ(I)
graphiteRint = 0.126
293 2.0 degree images with [var phi] and ω scansθmax = 27.5°, θmin = 4.1°
Absorption correction: multi-scan (SORTAV;Blessing, 1995)h = −17→17
Tmin = 0.825, Tmax = 0.825k = −18→18
48411 measured reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0335P)2 + 0.6086P] where P = (Fo2 + 2Fc2)/3
6114 reflections(Δ/σ)max = 0.001
341 parametersΔρmax = 0.54 e Å3
2 restraintsΔρmin = −0.72 e Å3
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Sn0.208644 (18)0.515508 (15)0.133115 (17)0.02034 (8)
O10.27245 (18)0.37817 (14)0.16466 (16)0.0235 (5)
O20.35282 (17)0.53257 (14)0.24319 (16)0.0242 (5)
O30.47106 (18)0.45574 (15)0.34724 (17)0.0285 (6)
O40.38762 (18)0.29623 (15)0.26721 (17)0.0275 (6)
O50.09563 (17)0.41884 (14)0.04184 (16)0.0230 (5)
O60.06436 (17)0.60103 (14)0.04207 (15)0.0210 (5)
O70.2413 (2)0.67274 (16)0.18266 (19)0.0292 (6)
H7A0.292 (2)0.669 (3)0.233 (2)0.052 (14)*
H7B0.197 (3)0.712 (3)0.202 (3)0.074 (16)*
N−0.0015 (2)0.2042 (2)−0.0277 (2)0.0214 (6)
H1A−0.019 (3)0.170 (2)−0.076 (3)0.027 (10)*
H1B−0.027 (3)0.261 (3)−0.044 (3)0.038 (11)*
C10.3500 (3)0.3702 (2)0.2332 (2)0.0216 (8)
C20.3979 (3)0.4602 (2)0.2795 (2)0.0211 (7)
C30.0088 (3)0.4480 (2)−0.0001 (2)0.0196 (7)
C40.1110 (3)0.5052 (2)0.2372 (2)0.0225 (7)
C50.0459 (3)0.5767 (2)0.2523 (3)0.0277 (8)
H50.04670.63210.21720.033*
C6−0.0202 (3)0.5686 (3)0.3177 (3)0.0331 (9)
H6−0.06320.61850.32770.040*
C7−0.0237 (3)0.4886 (3)0.3681 (3)0.0356 (9)
H7−0.06900.48280.41270.043*
C80.0399 (3)0.4162 (3)0.3531 (3)0.0359 (9)
H80.03800.36070.38800.043*
C90.1059 (3)0.4239 (2)0.2882 (3)0.0295 (8)
H90.14820.37350.27810.035*
C100.2855 (3)0.5464 (2)0.0178 (3)0.0276 (8)
C110.3816 (3)0.5881 (3)0.0352 (3)0.0453 (11)
H110.41360.60270.09950.054*
C120.4320 (4)0.6091 (4)−0.0408 (4)0.0664 (15)
H120.49790.6378−0.02760.080*
C130.3872 (4)0.5888 (3)−0.1337 (3)0.0533 (13)
H130.42200.6032−0.18500.064*
C140.2922 (4)0.5477 (3)−0.1528 (3)0.0485 (11)
H140.26090.5336−0.21740.058*
C150.2416 (3)0.5266 (3)−0.0778 (3)0.0377 (9)
H150.17560.4981−0.09190.045*
C160.1143 (2)0.2108 (2)−0.0052 (2)0.0218 (7)
H160.13440.25020.05330.026*
C170.1521 (3)0.2565 (2)−0.0890 (2)0.0256 (8)
H17A0.13380.2183−0.14760.031*
H17B0.11800.3168−0.10240.031*
C180.2684 (3)0.2693 (2)−0.0643 (3)0.0308 (9)
H18A0.28630.3099−0.00750.037*
H18B0.29270.2986−0.11920.037*
C190.3215 (3)0.1774 (3)−0.0425 (3)0.0355 (9)
H19A0.39690.1869−0.02310.043*
H19B0.30920.1392−0.10150.043*
C200.2811 (3)0.1276 (3)0.0380 (3)0.0327 (9)
H20A0.31340.06630.04710.039*
H20B0.30180.16210.09900.039*
C210.1647 (3)0.1171 (2)0.0165 (3)0.0270 (8)
H21A0.14130.08940.07270.032*
H21B0.14390.0761−0.03960.032*
C22−0.0561 (3)0.1646 (2)0.0476 (2)0.0234 (8)
H22−0.03230.10010.06130.028*
C23−0.1710 (3)0.1642 (3)0.0064 (3)0.0332 (9)
H23A−0.18470.1254−0.05210.040*
H23B−0.19420.2272−0.01230.040*
C24−0.2322 (3)0.1273 (3)0.0812 (3)0.0368 (10)
H24A−0.30710.13030.05420.044*
H24B−0.21370.06230.09530.044*
C25−0.2087 (3)0.1823 (3)0.1736 (3)0.0371 (9)
H25A−0.24620.15570.22160.045*
H25B−0.23300.24610.16070.045*
C26−0.0935 (3)0.1823 (3)0.2141 (3)0.0402 (10)
H26A−0.07060.11900.23210.048*
H26B−0.07950.22030.27320.048*
C27−0.0316 (3)0.2196 (3)0.1407 (2)0.0324 (9)
H27A−0.04940.28480.12710.039*
H27B0.04330.21580.16780.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn0.01965 (13)0.01890 (12)0.02124 (13)0.00066 (11)0.00070 (8)0.00046 (11)
O10.0233 (14)0.0203 (12)0.0240 (13)0.0026 (10)−0.0033 (11)−0.0020 (10)
O20.0238 (13)0.0161 (13)0.0292 (13)0.0016 (9)−0.0043 (10)0.0021 (10)
O30.0284 (14)0.0251 (13)0.0266 (14)−0.0012 (10)−0.0089 (11)0.0018 (10)
O40.0286 (14)0.0193 (13)0.0314 (14)0.0034 (10)−0.0025 (11)0.0037 (10)
O50.0225 (13)0.0177 (12)0.0262 (13)0.0014 (10)−0.0020 (11)−0.0027 (10)
O60.0217 (13)0.0192 (12)0.0201 (12)0.0006 (10)−0.0009 (10)−0.0002 (10)
O70.0260 (16)0.0237 (14)0.0353 (16)0.0013 (11)−0.0007 (13)−0.0018 (12)
N0.0246 (17)0.0186 (17)0.0208 (17)−0.0001 (12)0.0042 (14)−0.0004 (14)
C10.021 (2)0.0227 (19)0.0225 (19)0.0008 (14)0.0082 (16)−0.0007 (15)
C20.0206 (19)0.0233 (19)0.0203 (18)−0.0011 (14)0.0060 (15)−0.0010 (14)
C30.023 (2)0.0193 (17)0.0166 (16)0.0008 (14)0.0031 (14)−0.0021 (13)
C40.0218 (17)0.027 (2)0.0175 (17)−0.0008 (14)−0.0009 (13)−0.0022 (14)
C50.024 (2)0.029 (2)0.028 (2)0.0001 (15)−0.0010 (16)0.0000 (15)
C60.021 (2)0.045 (2)0.033 (2)−0.0008 (17)0.0036 (17)−0.0033 (18)
C70.029 (2)0.048 (2)0.032 (2)−0.0127 (18)0.0105 (17)−0.0046 (19)
C80.036 (2)0.038 (2)0.034 (2)−0.0119 (18)0.0066 (19)0.0024 (18)
C90.031 (2)0.027 (2)0.031 (2)−0.0032 (16)0.0058 (17)−0.0017 (16)
C100.029 (2)0.0265 (19)0.029 (2)0.0055 (15)0.0077 (16)0.0054 (15)
C110.030 (2)0.070 (3)0.036 (2)−0.007 (2)0.0053 (19)0.008 (2)
C120.033 (3)0.105 (4)0.065 (4)−0.011 (3)0.017 (3)0.019 (3)
C130.050 (3)0.072 (3)0.045 (3)0.015 (2)0.028 (2)0.016 (2)
C140.069 (3)0.048 (3)0.031 (2)0.004 (2)0.015 (2)0.0013 (19)
C150.048 (3)0.035 (2)0.033 (2)−0.0038 (18)0.0124 (19)−0.0001 (18)
C160.0198 (19)0.0236 (18)0.0212 (18)0.0027 (14)0.0020 (15)0.0001 (14)
C170.029 (2)0.0263 (19)0.0211 (19)0.0022 (15)0.0042 (16)0.0009 (15)
C180.026 (2)0.040 (2)0.028 (2)0.0013 (16)0.0100 (17)0.0019 (17)
C190.024 (2)0.045 (2)0.036 (2)0.0081 (17)0.0031 (17)−0.0076 (18)
C200.027 (2)0.035 (2)0.034 (2)0.0090 (16)−0.0025 (17)−0.0011 (17)
C210.028 (2)0.0224 (19)0.029 (2)0.0033 (15)0.0002 (16)−0.0016 (15)
C220.027 (2)0.0194 (18)0.0237 (19)0.0025 (14)0.0054 (16)0.0037 (14)
C230.030 (2)0.042 (2)0.028 (2)−0.0047 (17)0.0056 (17)−0.0043 (17)
C240.026 (2)0.049 (2)0.037 (2)−0.0064 (18)0.0085 (18)−0.0029 (19)
C250.032 (2)0.047 (2)0.035 (2)−0.0018 (18)0.0132 (18)−0.0056 (19)
C260.038 (3)0.058 (3)0.026 (2)−0.010 (2)0.0104 (18)−0.0021 (19)
C270.030 (2)0.043 (2)0.023 (2)−0.0064 (17)0.0038 (17)−0.0043 (17)

Geometric parameters (Å, °)

Sn—C102.121 (3)C13—C141.368 (6)
Sn—C42.132 (3)C13—H130.9500
Sn—O12.189 (2)C14—C151.388 (5)
Sn—O22.229 (2)C14—H140.9500
Sn—O52.269 (2)C15—H150.9500
Sn—O72.416 (2)C16—C171.522 (4)
Sn—O62.430 (2)C16—C211.527 (4)
O1—C11.273 (4)C16—H161.0000
O2—C21.273 (4)C17—C181.517 (5)
O3—C21.225 (4)C17—H17A0.9900
O4—C11.247 (4)C17—H17B0.9900
O5—C31.259 (4)C18—C191.518 (5)
O6—C3i1.256 (4)C18—H18A0.9900
O7—H7A0.886 (19)C18—H18B0.9900
O7—H7B0.896 (19)C19—C201.527 (5)
N—C161.500 (4)C19—H19A0.9900
N—C221.507 (4)C19—H19B0.9900
N—H1A0.85 (4)C20—C211.514 (5)
N—H1B0.91 (4)C20—H20A0.9900
C1—C21.548 (5)C20—H20B0.9900
C3—O6i1.256 (4)C21—H21A0.9900
C3—C3i1.537 (7)C21—H21B0.9900
C4—C51.394 (5)C22—C231.516 (5)
C4—C91.397 (5)C22—C271.522 (5)
C5—C61.389 (5)C22—H221.0000
C5—H50.9500C23—C241.540 (5)
C6—C71.373 (5)C23—H23A0.9900
C6—H60.9500C23—H23B0.9900
C7—C81.390 (5)C24—C251.514 (5)
C7—H70.9500C24—H24A0.9900
C8—C91.382 (5)C24—H24B0.9900
C8—H80.9500C25—C261.518 (5)
C9—H90.9500C25—H25A0.9900
C10—C111.385 (5)C25—H25B0.9900
C10—C151.394 (5)C26—C271.534 (5)
C11—C121.398 (6)C26—H26A0.9900
C11—H110.9500C26—H26B0.9900
C12—C131.366 (7)C27—H27A0.9900
C12—H120.9500C27—H27B0.9900
C10—Sn—C4168.75 (13)C14—C15—C10121.4 (4)
C10—Sn—O197.50 (11)C14—C15—H15119.3
C4—Sn—O193.06 (10)C10—C15—H15119.3
C10—Sn—O292.53 (12)N—C16—C17109.4 (3)
C4—Sn—O294.18 (11)N—C16—C21111.8 (3)
O1—Sn—O273.55 (8)C17—C16—C21110.9 (3)
C10—Sn—O593.06 (12)N—C16—H16108.2
C4—Sn—O586.04 (10)C17—C16—H16108.2
O1—Sn—O574.35 (8)C21—C16—H16108.2
O2—Sn—O5147.87 (8)C18—C17—C16109.9 (3)
C10—Sn—O786.30 (11)C18—C17—H17A109.7
C4—Sn—O788.01 (10)C16—C17—H17A109.7
O1—Sn—O7140.57 (9)C18—C17—H17B109.7
O2—Sn—O767.06 (8)C16—C17—H17B109.7
O5—Sn—O7144.90 (8)H17A—C17—H17B108.2
C10—Sn—O685.62 (11)C17—C18—C19110.2 (3)
C4—Sn—O683.54 (10)C17—C18—H18A109.6
O1—Sn—O6144.21 (8)C19—C18—H18A109.6
O2—Sn—O6142.15 (7)C17—C18—H18B109.6
O5—Sn—O669.87 (8)C19—C18—H18B109.6
O7—Sn—O675.09 (8)H18A—C18—H18B108.1
C1—O1—Sn117.4 (2)C18—C19—C20111.1 (3)
C2—O2—Sn117.3 (2)C18—C19—H19A109.4
C3—O5—Sn119.8 (2)C20—C19—H19A109.4
C3i—O6—Sn114.2 (2)C18—C19—H19B109.4
Sn—O7—H7A104 (3)C20—C19—H19B109.4
Sn—O7—H7B127 (3)H19A—C19—H19B108.0
H7A—O7—H7B103 (4)C21—C20—C19112.4 (3)
C16—N—C22118.5 (3)C21—C20—H20A109.1
C16—N—H1A108 (2)C19—C20—H20A109.1
C22—N—H1A105 (2)C21—C20—H20B109.1
C16—N—H1B108 (2)C19—C20—H20B109.1
C22—N—H1B109 (2)H20A—C20—H20B107.9
H1A—N—H1B108 (3)C20—C21—C16109.6 (3)
O4—C1—O1125.1 (3)C20—C21—H21A109.8
O4—C1—C2118.2 (3)C16—C21—H21A109.8
O1—C1—C2116.6 (3)C20—C21—H21B109.8
O3—C2—O2126.6 (3)C16—C21—H21B109.8
O3—C2—C1118.9 (3)H21A—C21—H21B108.2
O2—C2—C1114.4 (3)N—C22—C23107.8 (3)
O6i—C3—O5125.2 (3)N—C22—C27110.8 (3)
O6i—C3—C3i117.5 (4)C23—C22—C27111.5 (3)
O5—C3—C3i117.2 (4)N—C22—H22108.9
C5—C4—C9117.9 (3)C23—C22—H22108.9
C5—C4—Sn121.4 (2)C27—C22—H22108.9
C9—C4—Sn120.6 (2)C22—C23—C24110.6 (3)
C6—C5—C4121.3 (3)C22—C23—H23A109.5
C6—C5—H5119.4C24—C23—H23A109.5
C4—C5—H5119.4C22—C23—H23B109.5
C7—C6—C5120.2 (3)C24—C23—H23B109.5
C7—C6—H6119.9H23A—C23—H23B108.1
C5—C6—H6119.9C25—C24—C23110.9 (3)
C6—C7—C8119.4 (3)C25—C24—H24A109.5
C6—C7—H7120.3C23—C24—H24A109.5
C8—C7—H7120.3C25—C24—H24B109.5
C9—C8—C7120.7 (3)C23—C24—H24B109.5
C9—C8—H8119.7H24A—C24—H24B108.1
C7—C8—H8119.7C24—C25—C26110.5 (3)
C8—C9—C4120.6 (3)C24—C25—H25A109.5
C8—C9—H9119.7C26—C25—H25A109.5
C4—C9—H9119.7C24—C25—H25B109.5
C11—C10—C15117.5 (3)C26—C25—H25B109.5
C11—C10—Sn120.6 (3)H25A—C25—H25B108.1
C15—C10—Sn121.9 (3)C25—C26—C27111.5 (3)
C10—C11—C12120.7 (4)C25—C26—H26A109.3
C10—C11—H11119.6C27—C26—H26A109.3
C12—C11—H11119.6C25—C26—H26B109.3
C13—C12—C11120.5 (4)C27—C26—H26B109.3
C13—C12—H12119.7H26A—C26—H26B108.0
C11—C12—H12119.7C22—C27—C26110.0 (3)
C12—C13—C14119.8 (4)C22—C27—H27A109.7
C12—C13—H13120.1C26—C27—H27A109.7
C14—C13—H13120.1C22—C27—H27B109.7
C13—C14—C15120.0 (4)C26—C27—H27B109.7
C13—C14—H14120.0H27A—C27—H27B108.2
C15—C14—H14120.0

Symmetry codes: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7B···O4ii0.90 (4)1.77 (4)2.663 (3)175 (4)
N—H1A···O3iii0.84 (4)2.12 (3)2.910 (4)155 (3)
N—H1A···O4iii0.84 (4)2.37 (4)2.986 (4)130 (3)
N—H1B···O6i0.91 (4)2.08 (4)2.960 (4)164 (4)

Symmetry codes: (ii) −x+1/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (i) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2310).

References

  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • Ballmann, J., Fuchs, M. G. G., Dechert, S., John, M. & Meyer, F. (2009). Inorg. Chem.48, 90–99. [PubMed]
  • Blessing, R. H. (1995). Acta Cryst. A51, 33–38. [PubMed]
  • Diallo, W., Diop, C. A. K., Diop, L., Mahon, M. F., Molloy, K. C., Russo, U., Biesemans, M. & Willem, R. (2007). J. Organomet. Chem.692, 2187–2192.
  • Diassé-Sarr, A., Diop, L., Mahon, M. F. & Molloy, K. C. (1997). Main Group Met. Chem.20, 223–229.
  • Diop, C. A. K., Diop, L. & Toscano, A. R. (2002). Main Group Met. Chem.25, 327–328.
  • Diop, L., Mahieu, B., Mahon, M. F., Molloy, K. C. & Okio, K. Y. A. (2003). Appl. Organomet. Chem.17, 881–882.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Ng, S. W., Das, V. G. K., Gielen, M. & Tiekink, E. R. T. (1992). Appl. Organomet. Chem.6, 19–25.
  • Nonius (2000). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Singh, N., Kumar, A., Molloy, K. C. & Kociok-Köhn, G. (2008). Acta Cryst. E64, m115.
  • Sousa, G. F. de, Deflon, V. M., Manso, L. C. C., Ellena, J. E., Mascarenhas, Y. P., Lang, E. S., Gatto, C. C. & Mahieu, B. (2007). Transition Met. Chem.32, 649–655.
  • Wang, Z., Zhao, G. & Tian, L. (2009). Acta Cryst. E65, m528. [PMC free article] [PubMed]
  • Xanthopoulou, M. N., Hadjikakou, S. K., Hadjiliadis, N., Kubicki, M., Skoulika, S., Bakas, T., baril, M. & Butler, I. S. (2007). Inorg. Chem.46, 1187–1195. [PubMed]
  • Xanthopoulou, M. N., Kourkoumelis, N., Hadjikakou, S. K., Hadjiliadis, N., Kubicki, M., Karkabounas, S. & Bakas, T. (2008). Polyhedron, 27, 3318–3324.
  • Zia-ur-Rahman, Ali, S., Muhammed, N. & Meetsma, A. (2007). Acta Cryst. E63, m89–m90.

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