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

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Octa-n-butyl­bis­(μ2-4-chloro-3,5-di­nitro­benzoato-κ2O:O′)bis­­(4-chloro-3,5-di­nitro­benzoato-κO)di-μ3-oxo-tetra­tin(IV)

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and bSchool of Chemistry, University of Manchester, Manchester M13 9PL, England
*Correspondence e-mail: drsa54@yahoo.com

(Received 9 June 2006; accepted 27 June 2006; online 6 July 2006)

The title compound, [Sn4O2(C7H2ClN2O6)4(C4H9)8], is a centrosymmetric dimer of an oxoditin(IV) complex. Two dibutyl­bis[4-chloro-3,5-dinitro­benzoate]tin(IV) units con­taining monodentate and bridging bidentate carboxyl­ate ligands are connected to the central Sn2O2 core. Each Sn atom adopts a distorted trigonal–bipyramidal geometry, with Sn—C distances lying in the narrow range 2.119 (3)–2.135 (3) Å, while Sn—O distances range between 2.037 (2) and 2.286 (2) Å.

Comment

There have been several reports dealing with the impact of organotin chemistry in the biosphere (Gielen, 1994[Gielen, M. (1994). Main Group Met. Chem. 17, 1-8.]; Ng et al., 1991[Ng, S. W., Kuthubutheen, A. J., Arifin, Z., Wei, C., Kumar Das, V. G., Schulze, B, Molloy, K. C., Yip, W.-H. & Mak, T. C. W. (1991). J. Organomet. Chem. 403, 101-109.]). Exploration of the structure–activity relationships of such systems has led to numerous reports in recent years (Gielen, 1994[Gielen, M. (1994). Main Group Met. Chem. 17, 1-8.]; Selvaratnam et al., 1994[Selvaratnam, S., Lo, K. M. & Das, V. G. K. (1994). J. Organomet. Chem. 464, 143-148.]; McManus et al., 1994[McManus, J., Cunningham, D. & Hynes, M. J. (1994). J. Organomet. Chem. 468, 87-92.]). The structural chemistry of organotin carboxylic acid esters has been extensively explored because of the rich diversity of structural motifs (Tiekink, 1994[Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71-116.]). Among organotin carboxyl­ates, dimeric distannoxanes comprise the most inter­esting class with respect to their structural chemistry. Reports on crystallographic studies show that these compounds may adopt a variety of structural modes depending on the nature of organic substituents at the Sn atom or carboxyl­ate ligand (Danish et al., 1996[Danish, M., Ali, S., Mazhar, M. & Badshah, A. (1996). Main Group Met. Chem. 19, 121-131.]). There have been numerous crystallographic reports on these compounds describing their dimeric nature and there are at least five distinct structural types known for them (Tiekink, 1991[Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-16.]). In continuation of our studies of organotin(IV) carboxyl­ates (Sadiq-ur-Rehman et al., 2006[Sadiq-ur-Rehman, Ali, S., Shahzadi, S. & Parvez, M. (2006). Acta Cryst. E62, m910-m911.]), we have synthesized the title compound (I)[link], the crystal structure of which is reported here.

[Scheme 1]

The structure of (I)[link] is composed of a centrosymmetric dimer of oxoditin units (Fig. 1[link]). The endocyclic Sn—O distance in the central core [Sn1—O7 of 2.286 (2) Å] and the endocyclic distance [Sn1—O1 = 2.188 (2) Å] are quite similar to those observed in the tetra­butyl­bis(N-phthaloylglycinato)distannoxane dimer (Parvez et al., 2000[Parvez, M., Bhatti, M. H., Ali, S., Mazhar, M. & Qureshi, S. I. (2000). Acta Cryst. C56, 327-328.]) and the tetra­butyl­bis(N-phthaloylphenyl­alaninato)distannoxane dimer (Hans et al., 2002[Hans, K., Parvez, M., Ahmad, F., Ali, S., Mazhar, M. & Munir, A. (2002). Acta Cryst. E58, m441-m443.]). Both independent Sn atoms in (I)[link] are in a five-coordinate O3C2Sn distorted trigonal–bipyramidal geometry. The carboxyl­ate ligand shows different modes of coordination with Sn. Firstly, it acts as monodentate, coordinated to Sn1 via O1; the Sn1⋯O2 distance is 2.883 (2) Å, i.e. too long to be considered bonding [likewise, the Sn2⋯O1 distance of 2.913 (2) Å]. In the other coordination mode, the ligand bridges two Sn atoms in a bidentate fashion, thus resulting in a six-membered Sn1—O7—C8—O8—Sn2i—O13 ring [symmetry code: (i) −x, −y, −z]. The Sn—C distances lie in the very narrow range 2.119 (3)–2.135 (3) Å, while the Sn—O distances range between 2.037 (2) and 2.286 (2) Å (Table 1[link]).

[Figure 1]
Figure 1
Structure of (I)[link]. Displacement ellipsoids are drawn at the 50% probability level. The atoms labelled with A are at the symmetry position (−x, −y, −z). H atoms have been omitted. For clarity, only one component of the disordered butyl group (C15–C18) is shown.

Experimental

A mixture of 3,5-dinitro-4-chloro­benzoic acid (2 g, 1 mmol) and di-n-butyl­tin oxide (2.02 g, 1 mmol) was refluxed in dry toluene (150 ml) for 5–6 h using a Dean and Stark trap. The reaction mixture was cooled to room temperature and solvent was evaporated under reduced pressure. The solid product was recrystallized from chloro­form, resulting in rod-shaped crystals of (I)[link] (yield 85%, m.p. 513–514 K).

Crystal data
  • [Sn4O2(C7H2ClN2O6)4(C4H9)8]

  • Mr = 1945.88

  • Triclinic, [P \overline 1]

  • a = 12.1784 (11) Å

  • b = 12.5143 (12) Å

  • c = 13.5682 (12) Å

  • α = 104.597 (1)°

  • β = 110.770 (1)°

  • γ = 95.960 (1)°

  • V = 1827.9 (3) Å3

  • Z = 1

  • Dx = 1.768 Mg m−3

  • Mo Kα radiation

  • μ = 1.58 mm−1

  • T = 100 (2) K

  • Rod, colourless

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.571, Tmax = 0.743

  • 14580 measured reflections

  • 7352 independent reflections

  • 6497 reflections with I > 2σ(I)

  • Rint = 0.030

  • θmax = 26.5°

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.086

  • S = 1.02

  • 7352 reflections

  • 482 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0514P)2 + 0.862P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.001

  • Δρmax = 1.61 e Å−3

  • Δρmin = −1.47 e Å−3

Table 1
Selected geometric parameters (Å, °)

Sn1—O13 2.0391 (19)
Sn1—C19 2.124 (3)
Sn1—C15 2.135 (3)
Sn1—O1 2.188 (2)
Sn1—O7 2.286 (2)
Sn2—O13i 2.0372 (19)
Sn2—C23 2.119 (3)
Sn2—C27 2.125 (3)
Sn2—O13 2.1708 (19)
Sn2—O8i 2.276 (2)
Sn2⋯Sn2i 3.2908 (5)
O13—Sn1—C19 106.03 (10)
O13—Sn1—C15 108.78 (10)
C19—Sn1—C15 144.19 (12)
O13—Sn1—O1 83.08 (8)
C19—Sn1—O1 99.15 (10)
C15—Sn1—O1 93.09 (10)
O13—Sn1—O7 89.89 (8)
C19—Sn1—O7 86.80 (10)
C15—Sn1—O7 85.19 (11)
O1—Sn1—O7 171.81 (8)
O13i—Sn2—C23 108.48 (10)
O13i—Sn2—C27 114.33 (10)
C23—Sn2—C27 136.69 (12)
O13i—Sn2—O13 77.16 (8)
C23—Sn2—O13 97.19 (10)
C27—Sn2—O13 98.24 (10)
O13i—Sn2—O8i 91.86 (8)
C23—Sn2—O8i 89.20 (10)
C27—Sn2—O8i 83.31 (10)
O13—Sn2—O8i 168.58 (8)
Symmetry code: (i) -x, -y, -z.

H atoms were included in calculated positions using the riding model, with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for methyl groups. In one of the butyl groups (C15–C18), atoms C16 and C17 are disordered over two sites (C16/C17 and C16A/C17A); the occupancies refined to 0.496 (15) and 0.504 (15), respectively, and were fixed at 0.5 for the final cycles of refinement. The highest residual density peak is located 0.95 Å from atom Sn2 and the deepest hole is located 0.98 Å from atom Sn1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 2001[Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Octa-n-butylbis(µ2-4-chloro-3,5-dinitrobenzoato-κ2O:O')bis(4-chloro- 3,5-dinitrobenzoato-κO)di-µ3-oxo-tetratin(IV) top
Crystal data top
[Sn4O2(C7H2ClN2O6)4(C4H9)8]Z = 1
Mr = 1945.88F(000) = 972
Triclinic, P1Dx = 1.768 Mg m3
a = 12.1784 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5143 (12) ÅCell parameters from 7196 reflections
c = 13.5682 (12) Åθ = 2.5–26.5°
α = 104.597 (1)°µ = 1.58 mm1
β = 110.770 (1)°T = 100 K
γ = 95.960 (1)°Rod, colourless
V = 1827.9 (3) Å30.40 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
7352 independent reflections
Radiation source: fine-focus sealed tube6497 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1515
Tmin = 0.571, Tmax = 0.743k = 1515
14580 measured reflectionsl = 1616
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0514P)2 + 0.862P]
where P = (Fo2 + 2Fc2)/3
7352 reflections(Δ/σ)max = 0.001
482 parametersΔρmax = 1.61 e Å3
0 restraintsΔρmin = 1.47 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.186221 (17)0.253668 (16)0.122415 (16)0.01147 (7)
Sn20.027218 (17)0.018653 (16)0.112909 (16)0.01035 (7)
Cl10.01669 (8)0.36631 (7)0.69264 (7)0.02520 (19)
Cl20.45592 (7)0.35195 (7)0.38525 (7)0.02411 (18)
O10.13859 (19)0.23175 (17)0.25822 (17)0.0145 (4)
O20.24963 (19)0.40626 (18)0.34197 (18)0.0186 (5)
O30.1447 (2)0.63958 (19)0.6391 (2)0.0255 (5)
O40.1710 (2)0.5649 (2)0.7714 (2)0.0308 (6)
O50.1153 (3)0.0890 (2)0.4346 (2)0.0396 (7)
O60.0075 (2)0.1239 (2)0.6087 (2)0.0308 (6)
O70.2093 (2)0.26123 (18)0.03587 (18)0.0194 (5)
O80.15698 (19)0.08706 (18)0.15554 (18)0.0176 (5)
O90.4734 (2)0.5540 (2)0.0914 (2)0.0286 (6)
O100.3987 (2)0.5486 (2)0.2633 (2)0.0274 (6)
O110.3030 (2)0.1292 (2)0.5220 (2)0.0298 (6)
O120.3576 (2)0.0202 (2)0.4196 (2)0.0276 (6)
O130.07587 (17)0.09778 (16)0.03868 (16)0.0119 (4)
N10.1459 (2)0.5598 (2)0.6743 (2)0.0184 (6)
N20.0361 (2)0.1466 (2)0.5220 (2)0.0187 (6)
N30.4189 (2)0.5049 (2)0.1891 (2)0.0175 (6)
N40.3303 (2)0.1077 (2)0.4353 (2)0.0191 (6)
C10.1812 (3)0.3254 (3)0.3390 (2)0.0137 (6)
C20.1381 (3)0.3335 (3)0.4312 (3)0.0146 (6)
C30.1615 (3)0.4372 (3)0.5100 (3)0.0153 (6)
H30.20680.50210.50720.018*
C40.1184 (3)0.4461 (3)0.5932 (3)0.0151 (6)
C50.0508 (3)0.3531 (3)0.6002 (3)0.0166 (6)
C60.0321 (3)0.2503 (3)0.5212 (3)0.0162 (6)
C70.0727 (3)0.2397 (3)0.4367 (3)0.0146 (6)
H70.05570.16820.38280.018*
C80.2047 (2)0.1898 (2)0.1208 (2)0.0120 (6)
C90.2660 (3)0.2319 (3)0.1876 (2)0.0131 (6)
C100.3160 (3)0.3458 (3)0.1589 (3)0.0145 (6)
H10A0.31330.39860.09610.017*
C110.3698 (3)0.3818 (3)0.2229 (2)0.0148 (6)
C120.3781 (3)0.3081 (3)0.3143 (3)0.0163 (6)
C130.3281 (3)0.1939 (3)0.3396 (3)0.0161 (6)
C140.2737 (3)0.1564 (3)0.2773 (2)0.0152 (6)
H140.24130.07810.29640.018*
C150.0822 (3)0.3791 (3)0.0976 (3)0.0177 (7)
H15A0.00040.34030.04200.021*0.50
H15B0.07470.41500.16810.021*0.50
C160.1275 (6)0.4707 (6)0.0605 (7)0.0198 (14)0.50
H16A0.07790.52840.06280.024*0.50
H16B0.11770.43830.01740.024*0.50
C170.2593 (7)0.5278 (6)0.1315 (7)0.0220 (16)0.50
H17A0.30960.47080.12860.026*0.50
H17B0.26980.56030.20960.026*0.50
C180.3029 (4)0.6251 (3)0.0896 (3)0.0321 (9)
H18A0.38790.65940.13600.048*0.50
H18B0.25490.68280.09450.048*0.50
H18C0.29290.59310.01240.048*0.50
H15C0.02610.35600.01870.021*0.50
H15D0.03350.38270.14280.021*0.50
C16A0.1605 (6)0.5005 (6)0.1290 (7)0.0201 (14)0.50
H16C0.10580.55360.11770.024*0.50
H16D0.21290.52470.20910.024*0.50
C17A0.2387 (7)0.5117 (6)0.0658 (8)0.0246 (16)0.50
H17C0.29800.46340.08200.030*0.50
H17D0.18750.48200.01450.030*0.50
H18D0.38700.63450.13900.048*0.50
H18E0.26590.67970.12560.048*0.50
H18F0.29930.63790.02030.048*0.50
C190.3640 (3)0.2258 (3)0.1793 (3)0.0166 (6)
H19A0.36020.14550.14290.020*
H19B0.41130.27170.15240.020*
C200.4341 (3)0.2511 (3)0.3031 (3)0.0186 (7)
H20A0.38630.20990.33300.022*
H20B0.44720.33300.34060.022*
C210.5552 (3)0.2169 (3)0.3284 (3)0.0218 (7)
H21A0.59940.25220.29190.026*
H21B0.54160.13390.29680.026*
C220.6319 (3)0.2518 (4)0.4523 (3)0.0303 (8)
H22A0.64210.33340.48480.045*
H22B0.71080.23320.46400.045*
H22C0.59210.21140.48780.045*
C230.1182 (3)0.0223 (3)0.2289 (3)0.0157 (6)
H23A0.19390.02470.23820.019*
H23B0.11100.00140.30140.019*
C240.1273 (3)0.1455 (3)0.1987 (3)0.0165 (6)
H24A0.14020.16610.12890.020*
H24B0.05070.19370.18590.020*
C250.2304 (3)0.1686 (3)0.2899 (3)0.0188 (7)
H25A0.21810.14580.35990.023*
H25B0.22740.25090.26990.023*
C260.3545 (3)0.1071 (3)0.3097 (3)0.0229 (7)
H26A0.36800.12960.24100.034*
H26B0.41570.12690.36790.034*
H26C0.35970.02530.33280.034*
C270.1432 (3)0.1336 (3)0.1186 (3)0.0154 (6)
H27A0.14850.15160.19190.018*
H27B0.10670.20480.11230.018*
C280.2705 (3)0.0910 (3)0.0283 (3)0.0155 (6)
H28A0.26780.08880.04420.019*
H28B0.30180.01300.02410.019*
C290.3550 (3)0.1654 (3)0.0506 (3)0.0205 (7)
H29A0.31750.24510.06580.025*
H29B0.36610.15900.11790.025*
C300.4784 (3)0.1352 (3)0.0454 (3)0.0233 (7)
H30A0.46860.14410.11170.035*
H30B0.52890.18550.02540.035*
H30C0.51670.05670.06050.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01090 (11)0.01017 (12)0.01361 (12)0.00227 (8)0.00649 (8)0.00355 (8)
Sn20.00895 (11)0.01034 (11)0.01277 (12)0.00108 (8)0.00595 (8)0.00414 (8)
Cl10.0278 (4)0.0263 (4)0.0256 (4)0.0011 (3)0.0203 (4)0.0033 (4)
Cl20.0225 (4)0.0313 (5)0.0255 (4)0.0012 (3)0.0167 (3)0.0129 (4)
O10.0155 (11)0.0149 (11)0.0153 (11)0.0001 (9)0.0091 (9)0.0051 (9)
O20.0185 (11)0.0171 (12)0.0203 (12)0.0032 (9)0.0113 (9)0.0033 (9)
O30.0248 (13)0.0165 (12)0.0315 (14)0.0029 (10)0.0101 (11)0.0032 (11)
O40.0393 (15)0.0257 (14)0.0228 (14)0.0040 (12)0.0155 (12)0.0004 (11)
O50.0429 (17)0.0287 (15)0.0322 (15)0.0214 (13)0.0130 (13)0.0010 (12)
O60.0269 (14)0.0370 (15)0.0385 (15)0.0030 (12)0.0159 (12)0.0255 (13)
O70.0226 (12)0.0162 (11)0.0205 (12)0.0034 (9)0.0122 (10)0.0054 (10)
O80.0184 (11)0.0146 (11)0.0236 (12)0.0025 (9)0.0137 (10)0.0069 (9)
O90.0353 (14)0.0179 (12)0.0244 (13)0.0069 (11)0.0085 (11)0.0027 (10)
O100.0307 (14)0.0219 (13)0.0293 (13)0.0057 (11)0.0099 (11)0.0148 (11)
O110.0300 (14)0.0369 (15)0.0203 (13)0.0040 (12)0.0108 (11)0.0054 (11)
O120.0297 (14)0.0231 (13)0.0349 (14)0.0055 (11)0.0194 (12)0.0075 (11)
O130.0117 (10)0.0093 (10)0.0139 (10)0.0050 (8)0.0074 (8)0.0015 (8)
N10.0131 (13)0.0207 (15)0.0193 (14)0.0009 (11)0.0079 (11)0.0022 (12)
N20.0164 (14)0.0154 (14)0.0265 (15)0.0002 (11)0.0130 (12)0.0050 (12)
N30.0143 (13)0.0187 (14)0.0212 (15)0.0020 (11)0.0090 (11)0.0086 (12)
N40.0115 (13)0.0222 (15)0.0226 (15)0.0010 (11)0.0097 (11)0.0030 (12)
C10.0114 (14)0.0181 (16)0.0156 (15)0.0028 (12)0.0073 (12)0.0093 (13)
C20.0101 (14)0.0189 (16)0.0174 (15)0.0013 (12)0.0076 (12)0.0075 (13)
C30.0113 (14)0.0150 (15)0.0197 (16)0.0005 (12)0.0070 (12)0.0059 (13)
C40.0110 (14)0.0164 (16)0.0163 (15)0.0009 (12)0.0051 (12)0.0035 (13)
C50.0149 (15)0.0221 (17)0.0161 (15)0.0028 (13)0.0092 (12)0.0075 (13)
C60.0125 (15)0.0156 (16)0.0199 (16)0.0008 (12)0.0058 (12)0.0068 (13)
C70.0099 (14)0.0156 (16)0.0173 (15)0.0010 (12)0.0057 (12)0.0044 (13)
C80.0052 (13)0.0142 (15)0.0170 (15)0.0004 (11)0.0043 (11)0.0068 (12)
C90.0070 (13)0.0149 (15)0.0171 (15)0.0004 (11)0.0031 (11)0.0081 (12)
C100.0114 (14)0.0189 (16)0.0158 (15)0.0021 (12)0.0065 (12)0.0085 (13)
C110.0106 (14)0.0133 (15)0.0183 (16)0.0039 (12)0.0033 (12)0.0074 (13)
C120.0115 (14)0.0240 (17)0.0158 (15)0.0002 (13)0.0062 (12)0.0107 (13)
C130.0097 (14)0.0217 (17)0.0159 (15)0.0001 (12)0.0059 (12)0.0043 (13)
C140.0084 (14)0.0175 (16)0.0171 (15)0.0021 (12)0.0039 (12)0.0048 (13)
C150.0183 (16)0.0145 (16)0.0198 (16)0.0039 (13)0.0057 (13)0.0072 (13)
C160.022 (4)0.014 (3)0.019 (4)0.002 (3)0.005 (3)0.004 (3)
C170.020 (4)0.014 (4)0.027 (4)0.005 (3)0.008 (4)0.003 (4)
C180.035 (2)0.026 (2)0.041 (2)0.0011 (17)0.0214 (18)0.0126 (18)
C16A0.022 (4)0.013 (3)0.025 (4)0.001 (3)0.010 (3)0.005 (3)
C17A0.022 (4)0.014 (4)0.038 (5)0.000 (3)0.014 (4)0.006 (4)
C190.0125 (15)0.0155 (16)0.0228 (17)0.0008 (12)0.0100 (13)0.0048 (13)
C200.0139 (15)0.0232 (17)0.0217 (17)0.0015 (13)0.0088 (13)0.0103 (14)
C210.0195 (17)0.0227 (18)0.0256 (18)0.0044 (14)0.0097 (14)0.0106 (15)
C220.0163 (17)0.046 (2)0.033 (2)0.0088 (16)0.0083 (15)0.0207 (18)
C230.0147 (15)0.0143 (15)0.0171 (15)0.0014 (12)0.0048 (12)0.0062 (13)
C240.0138 (15)0.0161 (16)0.0203 (16)0.0004 (12)0.0077 (13)0.0065 (13)
C250.0176 (16)0.0212 (17)0.0224 (17)0.0055 (13)0.0097 (13)0.0117 (14)
C260.0175 (17)0.0287 (19)0.0281 (18)0.0051 (14)0.0118 (14)0.0138 (15)
C270.0100 (14)0.0158 (15)0.0210 (16)0.0001 (12)0.0075 (12)0.0060 (13)
C280.0115 (14)0.0172 (16)0.0192 (16)0.0017 (12)0.0072 (12)0.0071 (13)
C290.0138 (15)0.0229 (18)0.0251 (18)0.0046 (13)0.0072 (13)0.0083 (15)
C300.0107 (15)0.031 (2)0.0315 (19)0.0037 (14)0.0080 (14)0.0149 (16)
Geometric parameters (Å, º) top
Sn1—O132.0391 (19)C16—C171.528 (10)
Sn1—C192.124 (3)C16—H16A0.9900
Sn1—C152.135 (3)C16—H16B0.9900
Sn1—O12.188 (2)C17—C181.585 (8)
Sn1—O72.286 (2)C17—H17A0.9900
Sn2—O13i2.0372 (19)C17—H17B0.9900
Sn2—C232.119 (3)C18—H18A0.9800
Sn2—C272.125 (3)C18—H18B0.9800
Sn2—O132.1708 (19)C18—H18C0.9800
Sn2—O8i2.276 (2)C18—H18D0.9800
Sn2—Sn2i3.2908 (5)C18—H18E0.9800
Cl1—C51.712 (3)C18—H18F0.9800
Cl2—C121.712 (3)C16A—C17A1.508 (11)
O1—C11.291 (4)C16A—H16C0.9900
O2—C11.225 (4)C16A—H16D0.9900
O3—N11.210 (3)C17A—H17C0.9900
O4—N11.225 (4)C17A—H17D0.9900
O5—N21.213 (4)C19—C201.520 (4)
O6—N21.219 (4)C19—H19A0.9900
O7—C81.247 (4)C19—H19B0.9900
O8—C81.249 (4)C20—C211.523 (4)
O8—Sn2i2.276 (2)C20—H20A0.9900
O9—N31.206 (3)C20—H20B0.9900
O10—N31.226 (3)C21—C221.524 (5)
O11—N41.212 (4)C21—H21A0.9900
O12—N41.223 (4)C21—H21B0.9900
O13—Sn2i2.0373 (19)C22—H22A0.9800
N1—C41.483 (4)C22—H22B0.9800
N2—C61.470 (4)C22—H22C0.9800
N3—C111.483 (4)C23—C241.520 (4)
N4—C131.474 (4)C23—H23A0.9900
C1—C21.504 (4)C23—H23B0.9900
C2—C71.383 (4)C24—C251.531 (4)
C2—C31.384 (4)C24—H24A0.9900
C3—C41.390 (4)C24—H24B0.9900
C3—H30.9500C25—C261.522 (4)
C4—C51.397 (4)C25—H25A0.9900
C5—C61.389 (4)C25—H25B0.9900
C6—C71.384 (4)C26—H26A0.9800
C7—H70.9500C26—H26B0.9800
C8—C91.515 (4)C26—H26C0.9800
C9—C141.379 (4)C27—C281.530 (4)
C9—C101.388 (4)C27—H27A0.9900
C10—C111.388 (4)C27—H27B0.9900
C10—H10A0.9500C28—C291.515 (4)
C11—C121.390 (4)C28—H28A0.9900
C12—C131.398 (4)C28—H28B0.9900
C13—C141.381 (4)C29—C301.531 (4)
C14—H140.9500C29—H29A0.9900
C15—C161.492 (7)C29—H29B0.9900
C15—H15A0.9900C30—H30A0.9800
C15—H15B0.9900C30—H30B0.9800
C15—H15C0.9900C30—H30C0.9800
C15—H15D0.9900
O13—Sn1—C19106.03 (10)C15—C16—H16B108.9
O13—Sn1—C15108.78 (10)C17—C16—H16B108.9
C19—Sn1—C15144.19 (12)H16A—C16—H16B107.7
O13—Sn1—O183.08 (8)C16—C17—C18111.4 (6)
C19—Sn1—O199.15 (10)C16—C17—H17A109.3
C15—Sn1—O193.09 (10)C18—C17—H17A109.3
O13—Sn1—O789.89 (8)C16—C17—H17B109.3
C19—Sn1—O786.80 (10)C18—C17—H17B109.3
C15—Sn1—O785.19 (11)H17A—C17—H17B108.0
O1—Sn1—O7171.81 (8)C17—C18—H18A109.5
O13i—Sn2—C23108.48 (10)C17—C18—H18B109.5
O13i—Sn2—C27114.33 (10)H18A—C18—H18B109.5
C23—Sn2—C27136.69 (12)C17—C18—H18C109.5
O13i—Sn2—O1377.16 (8)H18A—C18—H18C109.5
C23—Sn2—O1397.19 (10)H18B—C18—H18C109.5
C27—Sn2—O1398.24 (10)C17A—C18—H18D109.5
O13i—Sn2—O8i91.86 (8)C17A—C18—H18E109.5
C23—Sn2—O8i89.20 (10)H18D—C18—H18E109.5
C27—Sn2—O8i83.31 (10)C17A—C18—H18F109.5
O13—Sn2—O8i168.58 (8)H18D—C18—H18F109.5
O13i—Sn2—Sn2i40.03 (5)H18E—C18—H18F109.5
C23—Sn2—Sn2i106.19 (9)C17A—C16A—H16C108.2
C27—Sn2—Sn2i110.47 (9)C17A—C16A—H16D108.2
O13—Sn2—Sn2i37.13 (5)H16C—C16A—H16D107.4
O8i—Sn2—Sn2i131.81 (6)C16A—C17A—H17C108.4
C1—O1—Sn1108.57 (18)C16A—C17A—H17D108.4
C8—O7—Sn1135.05 (19)H17C—C17A—H17D107.5
C8—O8—Sn2i133.1 (2)C20—C19—Sn1118.8 (2)
Sn2i—O13—Sn1136.33 (10)C20—C19—H19A107.6
Sn2i—O13—Sn2102.84 (8)Sn1—C19—H19A107.6
Sn1—O13—Sn2120.82 (9)C20—C19—H19B107.6
O3—N1—O4125.8 (3)Sn1—C19—H19B107.6
O3—N1—C4117.0 (3)H19A—C19—H19B107.0
O4—N1—C4117.2 (3)C19—C20—C21111.8 (3)
O5—N2—O6125.2 (3)C19—C20—H20A109.2
O5—N2—C6116.6 (3)C21—C20—H20A109.2
O6—N2—C6118.2 (3)C19—C20—H20B109.2
O9—N3—O10125.5 (3)C21—C20—H20B109.2
O9—N3—C11117.7 (3)H20A—C20—H20B107.9
O10—N3—C11116.8 (3)C20—C21—C22112.6 (3)
O11—N4—O12126.3 (3)C20—C21—H21A109.1
O11—N4—C13117.1 (3)C22—C21—H21A109.1
O12—N4—C13116.5 (3)C20—C21—H21B109.1
O2—C1—O1124.0 (3)C22—C21—H21B109.1
O2—C1—C2120.0 (3)H21A—C21—H21B107.8
O1—C1—C2116.0 (3)C21—C22—H22A109.5
C7—C2—C3119.5 (3)C21—C22—H22B109.5
C7—C2—C1121.1 (3)H22A—C22—H22B109.5
C3—C2—C1119.4 (3)C21—C22—H22C109.5
C2—C3—C4119.7 (3)H22A—C22—H22C109.5
C2—C3—H3120.1H22B—C22—H22C109.5
C4—C3—H3120.1C24—C23—Sn2115.5 (2)
C3—C4—C5122.1 (3)C24—C23—H23A108.4
C3—C4—N1116.9 (3)Sn2—C23—H23A108.4
C5—C4—N1121.0 (3)C24—C23—H23B108.4
C6—C5—C4116.2 (3)Sn2—C23—H23B108.4
C6—C5—Cl1121.3 (2)H23A—C23—H23B107.5
C4—C5—Cl1122.2 (2)C23—C24—C25111.9 (3)
C7—C6—C5122.7 (3)C23—C24—H24A109.2
C7—C6—N2116.5 (3)C25—C24—H24A109.2
C5—C6—N2120.8 (3)C23—C24—H24B109.2
C2—C7—C6119.7 (3)C25—C24—H24B109.2
C2—C7—H7120.1H24A—C24—H24B107.9
C6—C7—H7120.1C26—C25—C24114.0 (3)
O7—C8—O8127.0 (3)C26—C25—H25A108.7
O7—C8—C9116.4 (3)C24—C25—H25A108.7
O8—C8—C9116.5 (3)C26—C25—H25B108.7
C14—C9—C10119.3 (3)C24—C25—H25B108.7
C14—C9—C8119.9 (3)H25A—C25—H25B107.6
C10—C9—C8120.7 (3)C25—C26—H26A109.5
C11—C10—C9119.2 (3)C25—C26—H26B109.5
C11—C10—H10A120.4H26A—C26—H26B109.5
C9—C10—H10A120.4C25—C26—H26C109.5
C10—C11—C12122.8 (3)H26A—C26—H26C109.5
C10—C11—N3116.4 (3)H26B—C26—H26C109.5
C12—C11—N3120.7 (3)C28—C27—Sn2114.8 (2)
C11—C12—C13116.2 (3)C28—C27—H27A108.6
C11—C12—Cl2122.2 (2)Sn2—C27—H27A108.6
C13—C12—Cl2121.4 (2)C28—C27—H27B108.6
C14—C13—C12121.9 (3)Sn2—C27—H27B108.6
C14—C13—N4116.8 (3)H27A—C27—H27B107.5
C12—C13—N4121.3 (3)C29—C28—C27112.0 (3)
C9—C14—C13120.5 (3)C29—C28—H28A109.2
C9—C14—H14119.8C27—C28—H28A109.2
C13—C14—H14119.8C29—C28—H28B109.2
C16—C15—Sn1117.4 (3)C27—C28—H28B109.2
C16—C15—H15A107.9H28A—C28—H28B107.9
Sn1—C15—H15A107.9C28—C29—C30113.5 (3)
C16—C15—H15B107.9C28—C29—H29A108.9
Sn1—C15—H15B107.9C30—C29—H29A108.9
H15A—C15—H15B107.2C28—C29—H29B108.9
C16A—C15—H15C108.9C30—C29—H29B108.9
Sn1—C15—H15C108.9H29A—C29—H29B107.7
C16A—C15—H15D108.9C29—C30—H30A109.5
Sn1—C15—H15D108.9C29—C30—H30B109.5
H15C—C15—H15D107.7H30A—C30—H30B109.5
C15—C16—C17113.3 (6)C29—C30—H30C109.5
C15—C16—H16A108.9H30A—C30—H30C109.5
C17—C16—H16A108.9H30B—C30—H30C109.5
O13—Sn1—O1—C1172.38 (19)Sn2i—O8—C8—O713.9 (5)
C19—Sn1—O1—C182.4 (2)Sn2i—O8—C8—C9167.43 (18)
C15—Sn1—O1—C163.8 (2)O7—C8—C9—C14174.6 (3)
O7—Sn1—O1—C1141.4 (5)O8—C8—C9—C144.1 (4)
O13—Sn1—O7—C827.5 (3)O7—C8—C9—C104.7 (4)
C19—Sn1—O7—C878.6 (3)O8—C8—C9—C10176.5 (3)
C15—Sn1—O7—C8136.3 (3)C14—C9—C10—C111.6 (4)
O1—Sn1—O7—C858.2 (7)C8—C9—C10—C11179.0 (3)
C19—Sn1—O13—Sn2i76.86 (17)C9—C10—C11—C121.1 (5)
C15—Sn1—O13—Sn2i94.65 (17)C9—C10—C11—N3178.7 (3)
O1—Sn1—O13—Sn2i174.43 (16)O9—N3—C11—C1042.5 (4)
O7—Sn1—O13—Sn2i9.78 (15)O10—N3—C11—C10136.3 (3)
C19—Sn1—O13—Sn2103.91 (13)O9—N3—C11—C12137.7 (3)
C15—Sn1—O13—Sn284.58 (14)O10—N3—C11—C1243.5 (4)
O1—Sn1—O13—Sn26.34 (10)C10—C11—C12—C130.3 (5)
O7—Sn1—O13—Sn2169.46 (11)N3—C11—C12—C13179.5 (3)
O13i—Sn2—O13—Sn2i0.0C10—C11—C12—Cl2174.3 (2)
C23—Sn2—O13—Sn2i107.39 (11)N3—C11—C12—Cl25.9 (4)
C27—Sn2—O13—Sn2i113.20 (11)C11—C12—C13—C140.0 (5)
O8i—Sn2—O13—Sn2i16.2 (4)Cl2—C12—C13—C14174.6 (2)
O13i—Sn2—O13—Sn1179.46 (17)C11—C12—C13—N4179.5 (3)
C23—Sn2—O13—Sn173.15 (13)Cl2—C12—C13—N45.9 (4)
C27—Sn2—O13—Sn166.25 (13)O11—N4—C13—C14134.2 (3)
O8i—Sn2—O13—Sn1163.3 (3)O12—N4—C13—C1444.5 (4)
Sn2i—Sn2—O13—Sn1179.46 (17)O11—N4—C13—C1245.3 (4)
Sn1—O1—C1—O28.7 (4)O12—N4—C13—C12136.0 (3)
Sn1—O1—C1—C2169.0 (2)C10—C9—C14—C131.4 (4)
O2—C1—C2—C7172.2 (3)C8—C9—C14—C13179.2 (3)
O1—C1—C2—C710.0 (4)C12—C13—C14—C90.6 (5)
O2—C1—C2—C39.6 (4)N4—C13—C14—C9178.9 (3)
O1—C1—C2—C3168.2 (3)O13—Sn1—C15—C16129.3 (4)
C7—C2—C3—C40.5 (5)C19—Sn1—C15—C1636.7 (5)
C1—C2—C3—C4177.8 (3)O1—Sn1—C15—C16147.0 (4)
C2—C3—C4—C50.3 (5)O7—Sn1—C15—C1641.0 (4)
C2—C3—C4—N1179.6 (3)Sn1—C15—C16—C1750.5 (7)
O3—N1—C4—C337.1 (4)C15—C16—C17—C18179.5 (5)
O4—N1—C4—C3141.0 (3)O13—Sn1—C19—C20112.1 (2)
O3—N1—C4—C5142.2 (3)C15—Sn1—C19—C2081.7 (3)
O4—N1—C4—C539.7 (4)O1—Sn1—C19—C2026.8 (2)
C3—C4—C5—C61.8 (5)O7—Sn1—C19—C20158.9 (2)
N1—C4—C5—C6178.9 (3)Sn1—C19—C20—C21175.1 (2)
C3—C4—C5—Cl1172.5 (2)C19—C20—C21—C22174.5 (3)
N1—C4—C5—Cl16.8 (4)O13i—Sn2—C23—C2424.4 (2)
C4—C5—C6—C72.8 (5)C27—Sn2—C23—C24146.7 (2)
Cl1—C5—C6—C7171.6 (2)O13—Sn2—C23—C24103.2 (2)
C4—C5—C6—N2179.0 (3)O8i—Sn2—C23—C2467.3 (2)
Cl1—C5—C6—N26.6 (4)Sn2i—Sn2—C23—C2466.3 (2)
O5—N2—C6—C747.5 (4)Sn2—C23—C24—C25176.8 (2)
O6—N2—C6—C7131.0 (3)C23—C24—C25—C2664.2 (4)
O5—N2—C6—C5130.8 (3)O13i—Sn2—C27—C2823.0 (2)
O6—N2—C6—C550.7 (4)C23—Sn2—C27—C28147.6 (2)
C3—C2—C7—C60.4 (5)O13—Sn2—C27—C28102.6 (2)
C1—C2—C7—C6178.6 (3)O8i—Sn2—C27—C2866.0 (2)
C5—C6—C7—C22.1 (5)Sn2i—Sn2—C27—C2866.3 (2)
N2—C6—C7—C2179.6 (3)Sn2—C27—C28—C29168.3 (2)
Sn1—O7—C8—O818.7 (5)C27—C28—C29—C30172.0 (3)
Sn1—O7—C8—C9159.9 (2)
Symmetry code: (i) x, y, z.
 

Acknowledgements

AR thanks the Higher Education Commission, Islamabad, Pakistan, for financial suport under the PhD Fellowship Scheme Batch-II (PIN Code: 042-111621-PS2-179).

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