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Acta Cryst. (2011). E67, m662    [ doi:10.1107/S1600536811015728 ]

Aquabis(4-chlorobenzyl)bis(nicotinato-[kappa]2O,O')tin(IV)

T. C. Keng, K. M. Lo and S. W. Ng

Abstract top

In the title molecule, [Sn(C7H6Cl)2(C6H4NO2)2(H2O)], the O atoms of the two chelating nicotinate groups and the O atom of the coordinated water molecule comprise the pentagonal plane of the trans-C2SnO5 pentagonal-bipyramid [C-Sn-C = 178.62 (11) °] surrounding the SnIV atom. In the crystal, adjacent molecules are linked by O-H...N hydrogen bonds, generating a chain running along the body diagonal of the triclinic unit cell.

Comment top

Nicotinic acid affords a large number of compounds with organotins. For the diorganotin system in particular, the nicotinate ion can behave as an O,O'-chelate, but when two ions bind to a diorganotin cation, there is some space in the coordination polyhedron to admit a small ligand such as a water molecule (Tiekink, 1991; 1994). The bromo analog of the title compound (Scheme I) exists as a dinuclear compound as the N atom engages in coordination (Keng et al., 2010). The O atoms of the two chelating nicotinate groups and the O atom of the coordinated water molecule comprise the pentagonal plane of the trans-C2SnO5 pentagonal-bipyramid [C–Sn–C 178.6 (1) °] surrounding the SnIV atom in title compound (Fig. 1). The N atom does not engage in binding to an adjacent metal center. Instead, both N atoms serve as hydrogen bond acceptors (Table 1). Adjacent molecules are linked by O–H···N hydrogen bonds to generate a chain along [1 - 1 1].

Related literature top

For the direct synthesis of the organotin chloride reactant, see: Sisido et al. (1961). For the dinuclear bromo analog, see: Keng et al. (2010). For a review of the crystal structures of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Di(4-chlorobenzyl)tin oxide was prepared by the base hydrolysis of di(4-chlorobenzyl)tin dichloride with 10% sodium hydroxide. The diorganotin dichloride was synthesized by the direct reaction of 4-chlorobenzyl chloride and metallic tin according to a literature procedure (Sisido et al., 1961). The diorganotin oxide (0.39 g, 1 mmol) and nicotinic acid (0.25 g, 2 mmol) were heated in ethanol (100 ml) for an hour until the oxide dissolved. The solution was filtered; slow evaporation of the filtrate gave colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5 times Ueq(C,O).

The final difference Fourier map had a peak in the vicinity of Sn1 as well as a hole in the vicinity of the same atom. The peaks/holes affected the the weighting scheme, which had a somewhat large value as the first parameter but a small value for the second parameter. The weighting scheme could be marginally improved by lowering the 2θ limit to 50 °.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 Sn(H2O)(C7H6Cl)2(C6H4NO2)2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Packing diagram.
Aquabis(4-chlorobenzyl)bis(nicotinato-κ2O,O')tin(IV) top
Crystal data top
[Sn(C7H6Cl)2(C6H4NO2)2(H2O)]Z = 2
Mr = 632.05F(000) = 632
Triclinic, P1Dx = 1.670 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0219 (1) ÅCell parameters from 9937 reflections
b = 10.5929 (1) Åθ = 2.5–28.4°
c = 14.5866 (2) ŵ = 1.27 mm−1
α = 79.6490 (5)°T = 100 K
β = 87.6290 (5)°Block, colorless
γ = 66.5051 (4)°0.35 × 0.30 × 0.25 mm
V = 1256.93 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer		5673 independent reflections
Radiation source: fine-focus sealed tube5416 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.665, Tmax = 0.742k = −13→13
11404 measured reflectionsl = −18→18
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1028P)2 + 1.3179P]
where P = (Fo2 + 2Fc2)/3
5673 reflections(Δ/σ)max = 0.001
326 parametersΔρmax = 2.51 e Å−3
0 restraintsΔρmin = −1.96 e Å−3
Crystal data top
[Sn(C7H6Cl)2(C6H4NO2)2(H2O)]γ = 66.5051 (4)°
Mr = 632.05V = 1256.93 (3) Å3
Triclinic, P1Z = 2
a = 9.0219 (1) ÅMo Kα radiation
b = 10.5929 (1) ŵ = 1.27 mm−1
c = 14.5866 (2) ÅT = 100 K
α = 79.6490 (5)°0.35 × 0.30 × 0.25 mm
β = 87.6290 (5)°
Data collection top
Bruker SMART APEX
diffractometer		5673 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5416 reflections with I > 2σ(I)
Tmin = 0.665, Tmax = 0.742Rint = 0.022
11404 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.133Δρmax = 2.51 e Å−3
S = 1.07Δρmin = −1.96 e Å−3
5673 reflectionsAbsolute structure: ?
326 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.63205 (2)0.308637 (17)0.300723 (11)0.01463 (11)
Cl10.23192 (13)0.32379 (11)−0.10807 (6)0.0365 (2)
Cl21.16041 (10)0.23720 (10)0.67438 (6)0.02660 (19)
O10.5519 (3)0.3053 (2)0.45081 (15)0.0183 (4)
O20.7813 (3)0.1357 (2)0.42515 (15)0.0172 (4)
O30.3946 (3)0.5014 (2)0.27412 (15)0.0198 (4)
O40.5422 (3)0.4480 (2)0.15155 (15)0.0170 (4)
O1W0.8289 (3)0.1801 (2)0.21474 (15)0.0202 (4)
H10.91730.14540.24520.030*
H20.83640.23140.16530.030*
N10.8693 (3)−0.0102 (3)0.71325 (18)0.0180 (5)
N20.1562 (3)0.7425 (3)−0.02511 (18)0.0191 (5)
C10.5052 (4)0.1792 (4)0.2843 (2)0.0213 (6)
H1A0.58140.07990.29900.026*
H1B0.41820.19410.32990.026*
C20.4330 (4)0.2070 (3)0.1894 (2)0.0195 (6)
C30.5243 (4)0.1420 (4)0.1180 (2)0.0225 (6)
H30.63080.07300.13230.027*
C40.4630 (4)0.1761 (4)0.0277 (2)0.0268 (7)
H40.52760.1323−0.01990.032*
C50.3059 (5)0.2749 (4)0.0068 (2)0.0251 (7)
C60.2098 (4)0.3362 (4)0.0761 (3)0.0247 (7)
H60.10120.40090.06190.030*
C70.2735 (4)0.3024 (3)0.1670 (2)0.0207 (6)
H70.20740.34480.21460.025*
C80.7636 (4)0.4347 (3)0.3155 (2)0.0204 (6)
H8A0.83470.43270.26180.025*
H8B0.68530.53270.31260.025*
C90.8648 (4)0.3911 (3)0.4032 (2)0.0176 (6)
C101.0255 (4)0.2947 (3)0.4075 (2)0.0188 (6)
H101.07310.26110.35260.023*
C111.1167 (4)0.2473 (3)0.4901 (2)0.0205 (6)
H111.22550.18080.49230.025*
C121.0476 (4)0.2978 (3)0.5691 (2)0.0180 (6)
C130.8903 (4)0.3960 (3)0.5674 (2)0.0190 (6)
H130.84520.43160.62210.023*
C140.7993 (4)0.4417 (3)0.4843 (2)0.0184 (6)
H140.69070.50840.48260.022*
C150.4151 (4)0.5225 (3)0.1867 (2)0.0162 (5)
C160.2813 (3)0.6374 (3)0.1270 (2)0.0150 (5)
C170.1543 (4)0.7338 (3)0.1676 (2)0.0180 (6)
H170.15380.73050.23320.022*
C180.0282 (4)0.8350 (3)0.1102 (2)0.0208 (6)
H18−0.05970.90350.13530.025*
C190.0336 (4)0.8336 (3)0.0151 (2)0.0197 (6)
H19−0.05450.9010−0.02370.024*
C200.2787 (4)0.6464 (3)0.0306 (2)0.0192 (6)
H200.36730.58180.00320.023*
C210.6771 (3)0.1968 (3)0.48055 (19)0.0141 (5)
C220.6982 (4)0.1403 (3)0.5829 (2)0.0155 (5)
C230.5673 (4)0.1831 (3)0.6405 (2)0.0191 (6)
H230.46500.25060.61570.023*
C240.5882 (4)0.1257 (4)0.7348 (2)0.0193 (6)
H240.50060.15190.77560.023*
C250.7402 (4)0.0293 (3)0.7676 (2)0.0191 (6)
H250.7543−0.01120.83190.023*
C260.8467 (4)0.0453 (3)0.6216 (2)0.0166 (5)
H260.93630.01810.58220.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01514 (15)0.01586 (15)0.00806 (15)−0.00249 (10)−0.00275 (9)0.00174 (9)
Cl10.0496 (5)0.0521 (6)0.0153 (4)−0.0313 (5)−0.0098 (4)0.0043 (4)
Cl20.0204 (4)0.0416 (5)0.0149 (4)−0.0118 (3)−0.0048 (3)0.0020 (3)
O10.0197 (10)0.0194 (10)0.0089 (10)−0.0026 (8)−0.0024 (7)0.0030 (8)
O20.0180 (10)0.0174 (10)0.0124 (10)−0.0041 (8)−0.0009 (8)−0.0004 (8)
O30.0190 (10)0.0217 (10)0.0101 (10)−0.0008 (8)−0.0013 (8)0.0017 (8)
O40.0175 (10)0.0173 (10)0.0122 (10)−0.0039 (8)−0.0021 (8)0.0005 (8)
O1W0.0174 (10)0.0237 (11)0.0095 (9)0.0003 (8)−0.0043 (8)0.0028 (8)
N10.0192 (12)0.0180 (11)0.0116 (12)−0.0035 (9)−0.0051 (9)0.0022 (9)
N20.0208 (12)0.0206 (12)0.0119 (12)−0.0060 (10)−0.0045 (9)0.0029 (10)
C10.0223 (15)0.0242 (15)0.0148 (15)−0.0090 (13)−0.0055 (12)0.0038 (12)
C20.0222 (15)0.0215 (14)0.0161 (15)−0.0115 (12)−0.0025 (11)0.0009 (11)
C30.0233 (15)0.0241 (15)0.0204 (16)−0.0100 (12)−0.0018 (12)−0.0027 (12)
C40.0326 (17)0.0342 (18)0.0211 (16)−0.0198 (15)0.0022 (13)−0.0078 (14)
C50.0357 (18)0.0303 (17)0.0152 (15)−0.0216 (15)−0.0060 (13)0.0025 (13)
C60.0237 (15)0.0241 (15)0.0233 (17)−0.0096 (13)−0.0088 (13)0.0054 (13)
C70.0215 (14)0.0224 (14)0.0169 (15)−0.0089 (12)−0.0023 (11)0.0008 (12)
C80.0264 (16)0.0196 (14)0.0111 (14)−0.0074 (12)−0.0052 (12)0.0047 (11)
C90.0229 (14)0.0177 (13)0.0127 (14)−0.0097 (12)−0.0026 (11)0.0008 (11)
C100.0213 (14)0.0202 (14)0.0146 (14)−0.0084 (12)0.0018 (11)−0.0027 (11)
C110.0186 (14)0.0212 (14)0.0208 (15)−0.0069 (11)0.0009 (11)−0.0035 (12)
C120.0189 (14)0.0222 (14)0.0122 (14)−0.0091 (12)−0.0035 (11)0.0020 (11)
C130.0226 (15)0.0202 (14)0.0151 (14)−0.0097 (12)0.0010 (11)−0.0027 (11)
C140.0209 (14)0.0168 (13)0.0146 (14)−0.0060 (11)−0.0023 (11)0.0012 (11)
C150.0193 (13)0.0154 (13)0.0121 (13)−0.0063 (11)−0.0026 (10)0.0013 (10)
C160.0156 (13)0.0168 (13)0.0103 (13)−0.0058 (11)−0.0030 (10)0.0030 (10)
C170.0197 (13)0.0180 (13)0.0115 (13)−0.0043 (11)−0.0017 (10)0.0022 (11)
C180.0193 (14)0.0182 (13)0.0172 (15)−0.0014 (11)−0.0005 (11)0.0014 (11)
C190.0178 (13)0.0182 (13)0.0165 (15)−0.0030 (11)−0.0071 (11)0.0051 (11)
C200.0215 (14)0.0199 (14)0.0117 (14)−0.0048 (11)−0.0014 (11)0.0004 (11)
C210.0151 (12)0.0152 (12)0.0081 (13)−0.0044 (10)−0.0031 (10)0.0043 (10)
C220.0196 (13)0.0168 (13)0.0091 (13)−0.0072 (11)−0.0017 (10)0.0005 (10)
C230.0178 (13)0.0201 (14)0.0138 (14)−0.0039 (11)−0.0019 (10)0.0022 (11)
C240.0210 (15)0.0252 (15)0.0093 (14)−0.0080 (12)0.0018 (11)−0.0002 (11)
C250.0225 (14)0.0216 (14)0.0106 (13)−0.0081 (12)−0.0037 (11)0.0028 (11)
C260.0183 (13)0.0154 (12)0.0135 (13)−0.0047 (11)−0.0012 (10)−0.0003 (10)
Geometric parameters (Å, °) top
Sn1—C82.151 (3)C7—H70.9500
Sn1—C12.153 (3)C8—C91.494 (4)
Sn1—O1W2.254 (2)C8—H8A0.9900
Sn1—O12.276 (2)C8—H8B0.9900
Sn1—O32.281 (2)C9—C141.398 (4)
Sn1—O22.346 (2)C9—C101.397 (4)
Sn1—O42.368 (2)C10—C111.385 (4)
Sn1—C212.653 (3)C10—H100.9500
Sn1—C152.666 (3)C11—C121.378 (4)
Cl1—C51.739 (3)C11—H110.9500
Cl2—C121.749 (3)C12—C131.383 (4)
O1—C211.269 (4)C13—C141.390 (4)
O2—C211.264 (4)C13—H130.9500
O3—C151.273 (4)C14—H140.9500
O4—C151.255 (4)C15—C161.494 (4)
O1W—H10.8400C16—C171.391 (4)
O1W—H20.8400C16—C201.393 (4)
N1—C251.347 (4)C17—C181.389 (4)
N1—C261.349 (4)C17—H170.9500
N2—C191.340 (4)C18—C191.388 (4)
N2—C201.341 (4)C18—H180.9500
C1—C21.483 (4)C19—H190.9500
C1—H1A0.9900C20—H200.9500
C1—H1B0.9900C21—C221.496 (4)
C2—C71.400 (4)C22—C261.382 (4)
C2—C31.404 (5)C22—C231.391 (4)
C3—C41.380 (5)C23—C241.387 (4)
C3—H30.9500C23—H230.9500
C4—C51.392 (5)C24—C251.384 (4)
C4—H40.9500C24—H240.9500
C5—C61.381 (5)C25—H250.9500
C6—C71.395 (5)C26—H260.9500
C6—H60.9500
C8—Sn1—C1178.62 (11)C2—C7—H7119.4
C8—Sn1—O1W90.93 (11)C9—C8—Sn1115.3 (2)
C1—Sn1—O1W87.70 (11)C9—C8—H8A108.5
C8—Sn1—O192.45 (10)Sn1—C8—H8A108.5
C1—Sn1—O188.51 (11)C9—C8—H8B108.5
O1W—Sn1—O1140.24 (8)Sn1—C8—H8B108.5
C8—Sn1—O391.45 (11)H8A—C8—H8B107.5
C1—Sn1—O389.65 (11)C14—C9—C10118.2 (3)
O1W—Sn1—O3137.17 (8)C14—C9—C8120.8 (3)
O1—Sn1—O382.34 (8)C10—C9—C8121.0 (3)
C8—Sn1—O291.61 (10)C11—C10—C9121.2 (3)
C1—Sn1—O288.10 (10)C11—C10—H10119.4
O1W—Sn1—O283.33 (8)C9—C10—H10119.4
O1—Sn1—O256.98 (8)C12—C11—C10119.1 (3)
O3—Sn1—O2139.30 (8)C12—C11—H11120.5
C8—Sn1—O487.44 (10)C10—C11—H11120.5
C1—Sn1—O492.48 (10)C11—C12—C13121.5 (3)
O1W—Sn1—O480.87 (8)C11—C12—Cl2119.6 (2)
O1—Sn1—O4138.86 (8)C13—C12—Cl2118.8 (2)
O3—Sn1—O456.55 (8)C12—C13—C14118.9 (3)
O2—Sn1—O4164.15 (8)C12—C13—H13120.6
C8—Sn1—C2191.62 (10)C14—C13—H13120.6
C1—Sn1—C2188.76 (11)C13—C14—C9121.1 (3)
O1W—Sn1—C21111.77 (8)C13—C14—H14119.5
O1—Sn1—C2128.55 (8)C9—C14—H14119.5
O3—Sn1—C21110.90 (8)O4—C15—O3121.3 (3)
O2—Sn1—C2128.44 (8)O4—C15—C16121.0 (3)
O4—Sn1—C21167.35 (9)O3—C15—C16117.7 (3)
C8—Sn1—C1590.37 (10)O4—C15—Sn162.65 (16)
C1—Sn1—C1590.20 (11)O3—C15—Sn158.73 (15)
O1W—Sn1—C15108.75 (8)C16—C15—Sn1174.4 (2)
O1—Sn1—C15110.83 (8)C17—C16—C20119.1 (3)
O3—Sn1—C1528.49 (8)C17—C16—C15120.2 (3)
O2—Sn1—C15167.73 (9)C20—C16—C15120.6 (3)
O4—Sn1—C1528.09 (9)C18—C17—C16118.5 (3)
C21—Sn1—C15139.38 (9)C18—C17—H17120.8
C21—O1—Sn192.46 (17)C16—C17—H17120.8
C21—O2—Sn189.38 (17)C19—C18—C17118.4 (3)
C15—O3—Sn192.78 (18)C19—C18—H18120.8
C15—O4—Sn189.26 (18)C17—C18—H18120.8
Sn1—O1W—H1109.5N2—C19—C18123.8 (3)
Sn1—O1W—H2109.5N2—C19—H19118.1
H1—O1W—H2109.5C18—C19—H19118.1
C25—N1—C26117.6 (3)N2—C20—C16122.7 (3)
C19—N2—C20117.5 (3)N2—C20—H20118.7
C2—C1—Sn1113.9 (2)C16—C20—H20118.7
C2—C1—H1A108.8O2—C21—O1121.1 (3)
Sn1—C1—H1A108.8O2—C21—C22120.1 (3)
C2—C1—H1B108.8O1—C21—C22118.7 (3)
Sn1—C1—H1B108.8O2—C21—Sn162.18 (15)
H1A—C1—H1B107.7O1—C21—Sn158.99 (14)
C7—C2—C3117.6 (3)C22—C21—Sn1177.4 (2)
C7—C2—C1121.3 (3)C26—C22—C23119.1 (3)
C3—C2—C1121.0 (3)C26—C22—C21120.9 (3)
C4—C3—C2121.5 (3)C23—C22—C21120.0 (3)
C4—C3—H3119.2C24—C23—C22119.0 (3)
C2—C3—H3119.2C24—C23—H23120.5
C3—C4—C5119.5 (3)C22—C23—H23120.5
C3—C4—H4120.3C25—C24—C23118.2 (3)
C5—C4—H4120.3C25—C24—H24120.9
C6—C5—C4120.6 (3)C23—C24—H24120.9
C6—C5—Cl1120.0 (3)N1—C25—C24123.5 (3)
C4—C5—Cl1119.5 (3)N1—C25—H25118.2
C5—C6—C7119.5 (3)C24—C25—H25118.2
C5—C6—H6120.3N1—C26—C22122.5 (3)
C7—C6—H6120.3N1—C26—H26118.8
C6—C7—C2121.2 (3)C22—C26—H26118.8
C6—C7—H7119.4
C8—Sn1—O1—C21−88.89 (19)C12—C13—C14—C9−0.7 (5)
C1—Sn1—O1—C2190.13 (19)C10—C9—C14—C13−1.0 (4)
O1W—Sn1—O1—C215.5 (2)C8—C9—C14—C13176.6 (3)
O3—Sn1—O1—C21179.97 (18)Sn1—O4—C15—O33.8 (3)
O2—Sn1—O1—C211.43 (16)Sn1—O4—C15—C16−175.1 (2)
O4—Sn1—O1—C21−177.81 (15)Sn1—O3—C15—O4−3.9 (3)
C15—Sn1—O1—C21179.78 (17)Sn1—O3—C15—C16175.0 (2)
C8—Sn1—O2—C2190.45 (19)C8—Sn1—C15—O483.86 (19)
C1—Sn1—O2—C21−90.90 (19)C1—Sn1—C15—O4−94.88 (19)
O1W—Sn1—O2—C21−178.80 (18)O1W—Sn1—C15—O4−7.25 (19)
O1—Sn1—O2—C21−1.44 (16)O1—Sn1—C15—O4176.63 (16)
O3—Sn1—O2—C21−3.7 (2)O3—Sn1—C15—O4176.2 (3)
O4—Sn1—O2—C21176.7 (2)O2—Sn1—C15—O4−176.8 (3)
C15—Sn1—O2—C21−8.7 (5)C21—Sn1—C15—O4176.79 (15)
C8—Sn1—O3—C1588.09 (19)C8—Sn1—C15—O3−92.37 (19)
C1—Sn1—O3—C15−91.08 (19)C1—Sn1—C15—O388.88 (19)
O1W—Sn1—O3—C15−4.9 (2)O1W—Sn1—C15—O3176.52 (17)
O1—Sn1—O3—C15−179.63 (18)O1—Sn1—C15—O30.40 (19)
O2—Sn1—O3—C15−177.75 (15)O2—Sn1—C15—O36.9 (5)
O4—Sn1—O3—C152.13 (16)O4—Sn1—C15—O3−176.2 (3)
C21—Sn1—O3—C15−179.61 (17)C21—Sn1—C15—O30.6 (2)
C8—Sn1—O4—C15−95.59 (19)O4—C15—C16—C17−169.0 (3)
C1—Sn1—O4—C1585.78 (19)O3—C15—C16—C1712.1 (4)
O1W—Sn1—O4—C15173.05 (18)O4—C15—C16—C2013.6 (4)
O1—Sn1—O4—C15−4.8 (2)O3—C15—C16—C20−165.4 (3)
O3—Sn1—O4—C15−2.15 (16)C20—C16—C17—C180.6 (4)
O2—Sn1—O4—C15177.5 (2)C15—C16—C17—C18−176.9 (3)
C21—Sn1—O4—C15−9.6 (4)C16—C17—C18—C191.1 (4)
O1W—Sn1—C1—C2−73.1 (2)C20—N2—C19—C181.0 (5)
O1—Sn1—C1—C2146.5 (2)C17—C18—C19—N2−2.0 (5)
O3—Sn1—C1—C264.2 (2)C19—N2—C20—C160.9 (5)
O2—Sn1—C1—C2−156.5 (2)C17—C16—C20—N2−1.7 (4)
O4—Sn1—C1—C27.7 (2)C15—C16—C20—N2175.8 (3)
C21—Sn1—C1—C2175.1 (2)Sn1—O2—C21—O12.5 (3)
C15—Sn1—C1—C235.7 (2)Sn1—O2—C21—C22−178.6 (2)
Sn1—C1—C2—C7−92.4 (3)Sn1—O1—C21—O2−2.6 (3)
Sn1—C1—C2—C385.4 (3)Sn1—O1—C21—C22178.5 (2)
C7—C2—C3—C43.5 (5)C8—Sn1—C21—O2−90.37 (18)
C1—C2—C3—C4−174.3 (3)C1—Sn1—C21—O288.30 (19)
C2—C3—C4—C5−1.4 (5)O1W—Sn1—C21—O21.28 (19)
C3—C4—C5—C6−1.7 (5)O1—Sn1—C21—O2177.5 (3)
C3—C4—C5—Cl1177.0 (3)O3—Sn1—C21—O2177.45 (16)
C4—C5—C6—C72.5 (5)O4—Sn1—C21—O2−175.9 (3)
Cl1—C5—C6—C7−176.2 (2)C15—Sn1—C21—O2177.16 (15)
C5—C6—C7—C2−0.2 (5)C8—Sn1—C21—O192.15 (19)
C3—C2—C7—C6−2.7 (5)C1—Sn1—C21—O1−89.18 (19)
C1—C2—C7—C6175.1 (3)O1W—Sn1—C21—O1−176.20 (16)
O1W—Sn1—C8—C9−95.9 (2)O3—Sn1—C21—O1−0.03 (19)
O1—Sn1—C8—C944.4 (2)O2—Sn1—C21—O1−177.5 (3)
O3—Sn1—C8—C9126.8 (2)O4—Sn1—C21—O16.6 (5)
O2—Sn1—C8—C9−12.6 (2)C15—Sn1—C21—O1−0.3 (2)
O4—Sn1—C8—C9−176.8 (2)O2—C21—C22—C2616.9 (4)
C21—Sn1—C8—C915.9 (2)O1—C21—C22—C26−164.2 (3)
C15—Sn1—C8—C9155.3 (2)O2—C21—C22—C23−163.0 (3)
Sn1—C8—C9—C14−87.8 (3)O1—C21—C22—C2315.9 (4)
Sn1—C8—C9—C1089.7 (3)C26—C22—C23—C24−2.1 (4)
C14—C9—C10—C111.7 (4)C21—C22—C23—C24177.8 (3)
C8—C9—C10—C11−175.9 (3)C22—C23—C24—C250.9 (5)
C9—C10—C11—C12−0.8 (5)C26—N1—C25—C24−1.7 (5)
C10—C11—C12—C13−0.9 (5)C23—C24—C25—N11.0 (5)
C10—C11—C12—Cl2179.2 (2)C25—N1—C26—C220.4 (4)
C11—C12—C13—C141.6 (5)C23—C22—C26—N11.4 (4)
Cl2—C12—C13—C14−178.5 (2)C21—C22—C26—N1−178.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1···N1i0.841.932.721 (3)158
O1w—H2···N2ii0.842.012.754 (3)146
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1···N1i0.841.932.721 (3)158
O1w—H2···N2ii0.842.012.754 (3)146
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z.
Acknowledgements top

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

references
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