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Acta Cryst. (2011). E67, m156-m157    [ doi:10.1107/S1600536810054437 ]

Methyl(phenyl)bis(quinoline-2-carboxylato-[kappa]2N,O)tin(IV) monohydrate

M. Vafaee, M. M. Amini and S. W. Ng

Abstract top

The SnIV atom in each of the two independent molecules in the asymmetric unit of the title compound, [Sn(CH3)(C6H5)(C10H6NO2)2]·H2O, is N,O-chelated by two quinoline-2-carboxylate ions; the dative Sn-N bonds are significantly longer than the covalent Sn-O bonds. The two O and two N atoms comprise a trapezoid, and the diorganotin skeleton is bent over the longer N-N edge [C-Sn-C = 144.2 (1) and 144.5 (1)° in the two independent molecules]. The uncoordinated water molecules serve to connect the skew-trapezoidal bipyramidal tin-bearing molecules, generating a linear chain motif running along the ac diagonal. The crystal studied was a non-merohedral twin having a minor component of 33.2 (1)%.

Comment top

The anion of quinoline-2-carboxylic acid N,O-chelates to diorganotin(IV) cations to confer a six-coordinate geometry to the tin atom. The geometry is better described as a skew-trapezoidal bipyramid. The reported compounds having two identical organic radicals bound to tin (see: Chen et al., 2006; Dakternieks et al., 2003a, 2003b; Kuang et al., 2008a, 2008b; Wang et al., 2004; Yin et al., 2005; Zhang et al., 2006). The mixed-organyl compound, Sn(CH3)(C6H5)(C10H6NO2)2.H2O (Scheme I) is an example of a diorganotin quinoline-2-carboxylate having different organic groups; the synthesis of the parent diorganotin dichloride is a non-trivial synthesis. There are two independent molecules in the asymmetric unit. In both, the tin atom is N,O-chelated by two carboxylate ions; the dative Sn–N bond is significantly longer than the covalent Sn–O bond. The two O and two N atoms comprise a trapezoid, and the diorganotin skeleton is bent over the longer N–N edge (Table 1, (Fig. 1). The lattice water molecules serve to connect the skew-trapezoidal bipyramidal tin-bearing molecules to generate a linear chain motif (Fig. 2).

Related literature top

For other diorganotin bis(quinoline-2-carboxylates), see: Chen et al. (2006); Dakternieks et al. (2003a,b); Kuang et al. (2008a,b); Wang et al. (2004); Yin et al. (2005); Zhang et al. (2006).

Experimental top

Sodium quinoline-2-carboxylate was prepared by reacting sodium hydroxide and quinoline-2-carboxylic acid in toluene and removing of water in a Dean-Stark trap. The compound (0.20 g, 1 mmol) and methylphenyltin dichloride (0.35 g, 1 mmol) were stirred in a small volume of toluene at room temperature for an hour. The solid that formed was collected and recrystalized from methanol.

Refinement top

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.98 Å) and included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). The water H-atoms were also placed in calculated positions on the basis of hydrogen bonding interactions, with O–H set at 0.84 Å; their temperature factors were tied by a factor of 1.5 times. The final difference Fourier map had a peak in the vicinity of Sn2.

The crystal studied is a non-merohedral twin. The two twin domains were found by using CELL_NOW. The frames were integrated simultaneously by using TWINABS (Bruker, 2009). The minor component refined to 33.2 (1)%.

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 the two independent formula units of Sn(CH3)(C6H5)(C10H6NO2)2.H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Hydrogen-bonded chain structure.
Methyl(phenyl)bis(quinoline-2-carboxylato-κ2N,O)tin(IV) monohydrate top
Crystal data top
[Sn(CH3)(C6H5)(C10H6NO2)2]·H2OZ = 4
Mr = 573.16F(000) = 1152
Triclinic, P1Dx = 1.660 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1645 (5) ÅCell parameters from 3873 reflections
b = 13.9747 (6) Åθ = 2.3–28.3°
c = 17.0047 (8) ŵ = 1.16 mm−1
α = 103.8670 (6)°T = 100 K
β = 95.3560 (7)°Prism, colorless
γ = 99.0625 (7)°0.15 × 0.10 × 0.05 mm
V = 2294.0 (2) Å3
Data collection top
Bruker SMART APEX
diffractometer		11013 independent reflections
Radiation source: fine-focus sealed tube8760 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(TWINABS; Bruker, 2009)		h = −13→12
Tmin = 0.846, Tmax = 0.944k = −18→17
13450 measured reflectionsl = 0→22
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) = 0.101H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0569P)2]
where P = (Fo2 + 2Fc2)/3
11013 reflections(Δ/σ)max = 0.001
634 parametersΔρmax = 1.26 e Å−3
0 restraintsΔρmin = −0.75 e Å−3
Crystal data top
[Sn(CH3)(C6H5)(C10H6NO2)2]·H2Oγ = 99.0625 (7)°
Mr = 573.16V = 2294.0 (2) Å3
Triclinic, P1Z = 4
a = 10.1645 (5) ÅMo Kα radiation
b = 13.9747 (6) ŵ = 1.16 mm−1
c = 17.0047 (8) ÅT = 100 K
α = 103.8670 (6)°0.15 × 0.10 × 0.05 mm
β = 95.3560 (7)°
Data collection top
Bruker SMART APEX
diffractometer		11013 independent reflections
Absorption correction: multi-scan
(TWINABS; Bruker, 2009)		8760 reflections with I > 2σ(I)
Tmin = 0.846, Tmax = 0.944Rint = 0.028
13450 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.101Δρmax = 1.26 e Å−3
S = 1.07Δρmin = −0.75 e Å−3
11013 reflectionsAbsolute structure: ?
634 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.41077 (2)0.201996 (17)0.167572 (14)0.01248 (7)
Sn20.86475 (2)0.207815 (17)0.668056 (14)0.01286 (7)
O10.2924 (2)0.15333 (18)0.24844 (14)0.0156 (5)
O20.2587 (3)0.0812 (2)0.34970 (16)0.0226 (6)
O30.2166 (2)0.21193 (19)0.12076 (15)0.0180 (5)
O40.0655 (2)0.24855 (19)0.03525 (15)0.0198 (6)
O50.7572 (2)0.14924 (18)0.74893 (14)0.0160 (5)
O60.7364 (3)0.0812 (2)0.85284 (15)0.0222 (6)
O70.6652 (2)0.20711 (19)0.62455 (15)0.0172 (5)
O80.5004 (2)0.24978 (19)0.55227 (15)0.0199 (5)
O1W0.2494 (3)0.1263 (2)0.52532 (17)0.0306 (7)
H1W10.23990.10750.47400.046*
H1W20.32420.16520.54140.046*
O2W−0.1866 (3)0.1123 (2)0.02681 (16)0.0253 (6)
H2W1−0.11250.15200.03490.038*
H2W2−0.21680.0989−0.02310.038*
N10.5542 (3)0.1471 (2)0.26831 (16)0.0126 (6)
N20.4156 (3)0.2811 (2)0.04111 (17)0.0133 (6)
N31.0246 (3)0.1538 (2)0.76648 (17)0.0127 (6)
N40.8479 (3)0.2890 (2)0.54278 (17)0.0152 (6)
C10.4553 (4)0.0806 (3)0.0820 (2)0.0170 (7)
H1A0.40420.07370.02850.026*
H1B0.43070.01900.09950.026*
H1C0.55170.09220.07800.026*
C20.4859 (3)0.3512 (3)0.2381 (2)0.0142 (7)
C30.4313 (4)0.3852 (3)0.3102 (2)0.0190 (8)
H30.36380.34140.32620.023*
C40.4761 (4)0.4835 (3)0.3588 (2)0.0207 (8)
H40.43810.50610.40740.025*
C50.5747 (4)0.5474 (3)0.3366 (2)0.0226 (8)
H50.60220.61470.36860.027*
C60.6333 (4)0.5135 (3)0.2678 (2)0.0247 (9)
H60.70500.55670.25460.030*
C70.5895 (4)0.4180 (3)0.2180 (2)0.0219 (8)
H70.62910.39670.16990.026*
C80.3337 (3)0.1119 (3)0.3054 (2)0.0146 (7)
C90.4796 (3)0.1039 (2)0.3154 (2)0.0141 (7)
C100.5301 (4)0.0553 (3)0.3709 (2)0.0179 (7)
H100.47180.02470.40200.021*
C110.6637 (4)0.0521 (3)0.3800 (2)0.0174 (7)
H110.69940.01790.41660.021*
C120.7490 (3)0.1006 (3)0.3340 (2)0.0149 (7)
C130.8910 (4)0.1051 (3)0.3419 (2)0.0190 (8)
H130.93280.07730.38130.023*
C140.9666 (4)0.1483 (3)0.2940 (2)0.0202 (8)
H141.06060.14890.29880.024*
C150.9072 (4)0.1927 (3)0.2371 (2)0.0203 (8)
H150.96200.22290.20410.024*
C160.7725 (4)0.1931 (3)0.2284 (2)0.0180 (7)
H160.73400.22390.19010.022*
C170.6905 (3)0.1472 (2)0.2772 (2)0.0143 (7)
C180.1825 (4)0.2494 (3)0.0607 (2)0.0158 (7)
C190.2928 (3)0.2959 (3)0.0211 (2)0.0155 (7)
C200.2613 (4)0.3494 (3)−0.0358 (2)0.0189 (8)
H200.17190.3595−0.04710.023*
C210.3605 (4)0.3867 (3)−0.0745 (2)0.0212 (8)
H210.34120.4244−0.11240.025*
C220.4925 (4)0.3695 (3)−0.0584 (2)0.0166 (7)
C230.6027 (4)0.4037 (3)−0.0975 (2)0.0217 (8)
H230.58970.4434−0.13470.026*
C240.7252 (4)0.3804 (3)−0.0822 (2)0.0216 (8)
H240.79690.4026−0.10950.026*
C250.7464 (4)0.3223 (3)−0.0252 (2)0.0206 (8)
H250.83260.3062−0.01470.025*
C260.6448 (4)0.2897 (3)0.0145 (2)0.0190 (8)
H260.66030.25080.05200.023*
C270.5161 (4)0.3138 (2)−0.0002 (2)0.0152 (7)
C280.9242 (4)0.0934 (2)0.5824 (2)0.0152 (7)
H28A0.86680.07980.52990.023*
H28B0.91570.03250.60190.023*
H28C1.01810.11450.57540.023*
C290.9229 (4)0.3589 (3)0.7386 (2)0.0145 (7)
C301.0373 (4)0.3907 (3)0.7967 (2)0.0206 (8)
H301.09420.34450.80330.025*
C311.0698 (4)0.4887 (3)0.8452 (2)0.0237 (9)
H311.14900.50930.88400.028*
C320.9867 (4)0.5561 (3)0.8369 (2)0.0219 (8)
H321.00870.62310.87010.026*
C330.8723 (4)0.5264 (3)0.7808 (2)0.0205 (8)
H330.81490.57260.77550.025*
C340.8404 (4)0.4280 (3)0.7314 (2)0.0189 (8)
H340.76150.40800.69240.023*
C350.8066 (4)0.1124 (3)0.8058 (2)0.0158 (7)
C360.9541 (3)0.1074 (2)0.8130 (2)0.0130 (7)
C371.0090 (4)0.0569 (3)0.8658 (2)0.0158 (7)
H370.95270.02300.89610.019*
C381.1431 (4)0.0562 (3)0.8737 (2)0.0160 (7)
H381.18210.02270.90970.019*
C391.2237 (4)0.1072 (3)0.8266 (2)0.0144 (7)
C401.3655 (4)0.1122 (3)0.8324 (2)0.0172 (7)
H401.40970.08380.87040.021*
C411.4375 (3)0.1576 (3)0.7837 (2)0.0175 (7)
H411.53140.15820.78620.021*
C421.3746 (3)0.2036 (3)0.7296 (2)0.0183 (8)
H421.42710.23620.69690.022*
C431.2386 (3)0.2024 (3)0.7232 (2)0.0148 (7)
H431.19730.23340.68600.018*
C441.1604 (3)0.1547 (2)0.7724 (2)0.0126 (7)
C450.6194 (4)0.2467 (3)0.5688 (2)0.0169 (7)
C460.7199 (3)0.2916 (3)0.5223 (2)0.0154 (7)
C470.6736 (4)0.3338 (3)0.4599 (2)0.0176 (7)
H470.58050.33350.44760.021*
C480.7653 (4)0.3754 (3)0.4173 (2)0.0183 (8)
H480.73670.40540.37580.022*
C490.9024 (4)0.3727 (3)0.4362 (2)0.0167 (7)
C501.0024 (4)0.4138 (3)0.3954 (2)0.0205 (8)
H500.97800.44600.35440.025*
C511.1345 (4)0.4080 (3)0.4141 (2)0.0210 (8)
H511.20110.43530.38580.025*
C521.1709 (4)0.3611 (3)0.4756 (2)0.0213 (8)
H521.26240.35680.48820.026*
C531.0764 (4)0.3216 (3)0.5173 (2)0.0215 (8)
H531.10240.28980.55820.026*
C540.9403 (3)0.3284 (3)0.4993 (2)0.0142 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.00909 (12)0.01302 (12)0.01558 (13)0.00170 (9)0.00211 (9)0.00426 (9)
Sn20.00969 (13)0.01338 (12)0.01618 (13)0.00100 (9)0.00245 (9)0.00557 (9)
O10.0116 (12)0.0182 (12)0.0189 (12)0.0018 (10)0.0035 (10)0.0082 (10)
O20.0175 (14)0.0297 (15)0.0245 (14)0.0029 (11)0.0085 (11)0.0132 (12)
O30.0123 (13)0.0244 (14)0.0189 (13)0.0035 (10)0.0020 (10)0.0086 (11)
O40.0134 (13)0.0215 (13)0.0235 (14)0.0044 (10)−0.0034 (10)0.0053 (11)
O50.0089 (12)0.0236 (13)0.0185 (13)0.0023 (10)0.0024 (10)0.0112 (10)
O60.0200 (14)0.0267 (14)0.0221 (14)0.0018 (11)0.0077 (11)0.0106 (11)
O70.0096 (12)0.0241 (13)0.0209 (13)0.0011 (10)0.0006 (10)0.0135 (11)
O80.0121 (13)0.0254 (14)0.0239 (14)0.0030 (11)0.0016 (10)0.0103 (11)
O1W0.0236 (16)0.0369 (17)0.0289 (16)−0.0037 (13)0.0011 (12)0.0106 (13)
O2W0.0203 (14)0.0314 (15)0.0254 (14)0.0016 (12)0.0041 (11)0.0113 (12)
N10.0131 (15)0.0151 (14)0.0113 (14)0.0041 (11)0.0022 (11)0.0057 (11)
N20.0154 (15)0.0136 (14)0.0124 (14)0.0025 (11)0.0014 (11)0.0068 (11)
N30.0117 (15)0.0148 (14)0.0131 (14)0.0039 (11)0.0021 (11)0.0049 (11)
N40.0141 (15)0.0157 (15)0.0159 (15)0.0029 (12)0.0012 (11)0.0045 (12)
C10.0173 (19)0.0160 (17)0.0175 (17)0.0041 (14)0.0028 (14)0.0030 (14)
C20.0137 (18)0.0158 (17)0.0154 (17)0.0067 (14)−0.0001 (13)0.0069 (14)
C30.0107 (18)0.0181 (18)0.027 (2)0.0018 (14)0.0020 (14)0.0046 (15)
C40.0125 (18)0.0225 (19)0.024 (2)0.0071 (15)−0.0011 (15)0.0000 (16)
C50.026 (2)0.0130 (17)0.026 (2)0.0051 (15)−0.0056 (16)0.0027 (15)
C60.029 (2)0.0179 (19)0.026 (2)−0.0044 (16)−0.0012 (17)0.0120 (16)
C70.024 (2)0.0187 (19)0.0208 (19)0.0007 (16)0.0026 (15)0.0031 (15)
C80.0112 (17)0.0146 (17)0.0176 (17)0.0009 (13)0.0011 (13)0.0044 (14)
C90.0139 (18)0.0114 (16)0.0156 (17)0.0022 (13)−0.0002 (13)0.0016 (13)
C100.0195 (19)0.0150 (17)0.0187 (18)0.0011 (14)0.0021 (14)0.0050 (14)
C110.024 (2)0.0150 (17)0.0131 (17)0.0033 (15)−0.0014 (14)0.0044 (14)
C120.0133 (18)0.0159 (17)0.0149 (17)0.0058 (14)−0.0013 (13)0.0023 (14)
C130.0134 (18)0.0213 (19)0.0200 (18)0.0076 (15)−0.0061 (14)0.0012 (15)
C140.0126 (18)0.0190 (18)0.026 (2)0.0039 (14)0.0013 (15)−0.0007 (15)
C150.0154 (19)0.0178 (18)0.026 (2)0.0004 (15)0.0046 (15)0.0028 (15)
C160.0171 (19)0.0155 (17)0.0206 (18)0.0021 (14)0.0015 (14)0.0042 (14)
C170.0139 (18)0.0137 (17)0.0146 (17)0.0035 (14)−0.0006 (13)0.0025 (13)
C180.0145 (18)0.0128 (16)0.0190 (18)0.0034 (14)0.0023 (14)0.0013 (14)
C190.0133 (18)0.0143 (17)0.0171 (17)0.0022 (14)0.0011 (14)0.0013 (14)
C200.0139 (18)0.0207 (19)0.0245 (19)0.0045 (15)0.0005 (15)0.0102 (16)
C210.025 (2)0.0185 (19)0.0203 (19)0.0034 (16)−0.0017 (15)0.0068 (15)
C220.0172 (19)0.0155 (17)0.0172 (17)0.0045 (14)0.0003 (14)0.0042 (14)
C230.029 (2)0.0187 (19)0.0190 (19)0.0023 (16)0.0028 (16)0.0094 (15)
C240.025 (2)0.0207 (19)0.0180 (18)−0.0011 (16)0.0078 (15)0.0049 (15)
C250.0184 (19)0.025 (2)0.0191 (18)0.0051 (16)0.0042 (15)0.0056 (15)
C260.0168 (19)0.0162 (18)0.0231 (19)0.0002 (14)0.0010 (15)0.0057 (15)
C270.0159 (18)0.0107 (16)0.0166 (17)−0.0023 (13)0.0002 (14)0.0027 (13)
C280.0176 (18)0.0155 (17)0.0132 (16)0.0014 (14)0.0042 (13)0.0054 (14)
C290.0161 (18)0.0147 (17)0.0147 (16)0.0032 (14)0.0069 (13)0.0056 (14)
C300.0176 (19)0.0175 (18)0.027 (2)0.0066 (15)0.0016 (15)0.0044 (15)
C310.018 (2)0.0145 (18)0.034 (2)0.0012 (15)−0.0005 (16)0.0008 (16)
C320.026 (2)0.0114 (17)0.027 (2)0.0027 (15)0.0066 (16)0.0038 (15)
C330.024 (2)0.0170 (18)0.026 (2)0.0102 (15)0.0050 (16)0.0099 (15)
C340.0191 (19)0.0221 (19)0.0182 (18)0.0068 (15)0.0017 (14)0.0087 (15)
C350.0151 (18)0.0151 (17)0.0167 (17)0.0013 (14)0.0040 (14)0.0037 (14)
C360.0163 (18)0.0098 (15)0.0124 (16)−0.0005 (13)0.0030 (13)0.0033 (13)
C370.0188 (19)0.0137 (17)0.0152 (17)0.0001 (14)0.0036 (14)0.0055 (14)
C380.0197 (19)0.0138 (17)0.0141 (17)0.0025 (14)0.0008 (14)0.0036 (13)
C390.0182 (18)0.0133 (16)0.0127 (16)0.0062 (14)0.0013 (13)0.0038 (13)
C400.0176 (19)0.0152 (17)0.0180 (18)0.0054 (14)−0.0020 (14)0.0030 (14)
C410.0069 (17)0.0186 (18)0.0240 (19)0.0034 (14)0.0009 (14)−0.0003 (15)
C420.0075 (17)0.0211 (18)0.0236 (19)−0.0004 (14)0.0029 (14)0.0023 (15)
C430.0124 (18)0.0157 (17)0.0161 (17)0.0007 (13)0.0028 (13)0.0049 (14)
C440.0110 (17)0.0125 (16)0.0134 (16)0.0035 (13)−0.0010 (13)0.0019 (13)
C450.0156 (19)0.0138 (17)0.0185 (18)0.0000 (14)0.0015 (14)0.0008 (14)
C460.0130 (18)0.0146 (17)0.0176 (17)0.0018 (14)0.0014 (14)0.0031 (14)
C470.0130 (18)0.0190 (18)0.0206 (18)0.0057 (14)0.0014 (14)0.0029 (15)
C480.022 (2)0.0160 (17)0.0181 (18)0.0049 (15)0.0005 (15)0.0071 (14)
C490.0187 (19)0.0120 (16)0.0185 (18)0.0017 (14)0.0044 (14)0.0020 (14)
C500.019 (2)0.0185 (18)0.025 (2)0.0031 (15)0.0030 (15)0.0081 (16)
C510.022 (2)0.0183 (18)0.0218 (19)−0.0014 (15)0.0044 (15)0.0065 (15)
C520.0130 (19)0.029 (2)0.0215 (19)0.0021 (15)0.0029 (15)0.0070 (16)
C530.0127 (19)0.026 (2)0.026 (2)0.0035 (15)−0.0023 (15)0.0074 (16)
C540.0108 (17)0.0133 (16)0.0173 (17)0.0009 (13)0.0032 (13)0.0021 (13)
Geometric parameters (Å, °) top
Sn1—O12.074 (2)C18—C191.502 (5)
Sn1—C12.093 (3)C19—C201.400 (5)
Sn1—O32.097 (2)C20—C211.359 (5)
Sn1—C22.121 (3)C20—H200.9500
Sn1—N12.483 (3)C21—C221.413 (5)
Sn1—N22.644 (3)C21—H210.9500
Sn2—O52.072 (2)C22—C271.424 (5)
Sn2—O72.091 (2)C22—C231.431 (5)
Sn2—C282.096 (3)C23—C241.353 (5)
Sn2—C292.123 (3)C23—H230.9500
Sn2—N32.548 (3)C24—C251.429 (5)
Sn2—N42.647 (3)C24—H240.9500
O1—C81.311 (4)C25—C261.364 (5)
O2—C81.222 (4)C25—H250.9500
O3—C181.298 (4)C26—C271.415 (5)
O4—C181.224 (4)C26—H260.9500
O5—C351.297 (4)C28—H28A0.9800
O6—C351.231 (4)C28—H28B0.9800
O7—C451.293 (4)C28—H28C0.9800
O8—C451.226 (4)C29—C301.392 (5)
O1W—H1W10.8401C29—C341.394 (5)
O1W—H1W20.8407C30—C311.389 (5)
O2W—H2W10.8407C30—H300.9500
O2W—H2W20.8406C31—C321.384 (5)
N1—C91.334 (4)C31—H310.9500
N1—C171.379 (4)C32—C331.373 (5)
N2—C191.324 (4)C32—H320.9500
N2—C271.374 (4)C33—C341.399 (5)
N3—C361.328 (4)C33—H330.9500
N3—C441.373 (4)C34—H340.9500
N4—C461.323 (4)C35—C361.506 (5)
N4—C541.376 (4)C36—C371.398 (5)
C1—H1A0.9800C37—C381.359 (5)
C1—H1B0.9800C37—H370.9500
C1—H1C0.9800C38—C391.425 (5)
C2—C31.402 (5)C38—H380.9500
C2—C71.417 (5)C39—C441.423 (5)
C3—C41.402 (5)C39—C401.424 (5)
C3—H30.9500C40—C411.358 (5)
C4—C51.377 (5)C40—H400.9500
C4—H40.9500C41—C421.404 (5)
C5—C61.379 (5)C41—H410.9500
C5—H50.9500C42—C431.374 (5)
C6—C71.378 (5)C42—H420.9500
C6—H60.9500C43—C441.414 (5)
C7—H70.9500C43—H430.9500
C8—C91.502 (5)C45—C461.499 (5)
C9—C101.393 (5)C46—C471.410 (5)
C10—C111.362 (5)C47—C481.374 (5)
C10—H100.9500C47—H470.9500
C11—C121.422 (5)C48—C491.409 (5)
C11—H110.9500C48—H480.9500
C12—C171.424 (5)C49—C501.409 (5)
C12—C131.427 (5)C49—C541.413 (5)
C13—C141.351 (5)C50—C511.370 (5)
C13—H130.9500C50—H500.9500
C14—C151.407 (5)C51—C521.412 (5)
C14—H140.9500C51—H510.9500
C15—C161.365 (5)C52—C531.370 (5)
C15—H150.9500C52—H520.9500
C16—C171.417 (5)C53—C541.412 (5)
C16—H160.9500C53—H530.9500
O1—Sn1—C1111.11 (12)C21—C20—C19119.0 (3)
O1—Sn1—O376.84 (9)C21—C20—H20120.5
C1—Sn1—O3103.41 (12)C19—C20—H20120.5
O1—Sn1—C298.68 (11)C20—C21—C22120.0 (3)
C1—Sn1—C2144.5 (1)C20—C21—H21120.0
O3—Sn1—C2101.75 (11)C22—C21—H21120.0
O1—Sn1—N171.06 (9)C21—C22—C27117.6 (3)
C1—Sn1—N184.82 (11)C21—C22—C23124.0 (3)
O3—Sn1—N1147.65 (9)C27—C22—C23118.4 (3)
C2—Sn1—N187.16 (11)C24—C23—C22121.1 (3)
O1—Sn1—N2145.43 (9)C24—C23—H23119.5
C1—Sn1—N281.50 (11)C22—C23—H23119.5
O3—Sn1—N268.83 (9)C23—C24—C25119.9 (3)
C2—Sn1—N284.72 (11)C23—C24—H24120.1
N1—Sn1—N2143.44 (9)C25—C24—H24120.1
O5—Sn2—O776.83 (9)C26—C25—C24121.0 (3)
O5—Sn2—C28110.72 (12)C26—C25—H25119.5
O7—Sn2—C28105.40 (12)C24—C25—H25119.5
O5—Sn2—C2999.13 (11)C25—C26—C27120.1 (3)
O7—Sn2—C29100.21 (12)C25—C26—H26120.0
C28—Sn2—C29144.2 (1)C27—C26—H26120.0
O5—Sn2—N370.49 (9)N2—C27—C26119.1 (3)
O7—Sn2—N3146.93 (9)N2—C27—C22121.3 (3)
C28—Sn2—N382.07 (11)C26—C27—C22119.6 (3)
C29—Sn2—N389.99 (11)Sn2—C28—H28A109.5
O5—Sn2—N4144.85 (9)Sn2—C28—H28B109.5
O7—Sn2—N468.19 (9)H28A—C28—H28B109.5
C28—Sn2—N482.64 (11)Sn2—C28—H28C109.5
C29—Sn2—N484.11 (11)H28A—C28—H28C109.5
N3—Sn2—N4144.65 (9)H28B—C28—H28C109.5
C8—O1—Sn1125.0 (2)C30—C29—C34118.0 (3)
C18—O3—Sn1127.6 (2)C30—C29—Sn2122.1 (3)
C35—O5—Sn2125.8 (2)C34—C29—Sn2119.8 (3)
C45—O7—Sn2129.0 (2)C31—C30—C29121.2 (3)
H1W1—O1W—H1W2108.1C31—C30—H30119.4
H2W1—O2W—H2W2108.2C29—C30—H30119.4
C9—N1—C17118.2 (3)C32—C31—C30119.9 (4)
C9—N1—Sn1110.9 (2)C32—C31—H31120.1
C17—N1—Sn1130.6 (2)C30—C31—H31120.1
C19—N2—C27118.3 (3)C33—C32—C31120.1 (3)
C19—N2—Sn1107.7 (2)C33—C32—H32120.0
C27—N2—Sn1133.8 (2)C31—C32—H32120.0
C36—N3—C44118.1 (3)C32—C33—C34120.0 (3)
C36—N3—Sn2109.4 (2)C32—C33—H33120.0
C44—N3—Sn2132.1 (2)C34—C33—H33120.0
C46—N4—C54117.6 (3)C29—C34—C33120.8 (3)
C46—N4—Sn2108.1 (2)C29—C34—H34119.6
C54—N4—Sn2134.3 (2)C33—C34—H34119.6
Sn1—C1—H1A109.5O6—C35—O5121.9 (3)
Sn1—C1—H1B109.5O6—C35—C36120.0 (3)
H1A—C1—H1B109.5O5—C35—C36118.2 (3)
Sn1—C1—H1C109.5N3—C36—C37124.0 (3)
H1A—C1—H1C109.5N3—C36—C35115.4 (3)
H1B—C1—H1C109.5C37—C36—C35120.6 (3)
C3—C2—C7117.9 (3)C38—C37—C36119.8 (3)
C3—C2—Sn1117.8 (3)C38—C37—H37120.1
C7—C2—Sn1124.2 (2)C36—C37—H37120.1
C4—C3—C2120.3 (4)C37—C38—C39118.3 (3)
C4—C3—H3119.8C37—C38—H38120.8
C2—C3—H3119.8C39—C38—H38120.8
C5—C4—C3120.4 (3)C44—C39—C40119.1 (3)
C5—C4—H4119.8C44—C39—C38118.8 (3)
C3—C4—H4119.8C40—C39—C38122.1 (3)
C4—C5—C6119.9 (3)C41—C40—C39120.1 (3)
C4—C5—H5120.1C41—C40—H40120.0
C6—C5—H5120.1C39—C40—H40120.0
C7—C6—C5121.0 (4)C40—C41—C42120.7 (3)
C7—C6—H6119.5C40—C41—H41119.7
C5—C6—H6119.5C42—C41—H41119.7
C6—C7—C2120.5 (3)C43—C42—C41121.2 (3)
C6—C7—H7119.8C43—C42—H42119.4
C2—C7—H7119.8C41—C42—H42119.4
O2—C8—O1122.5 (3)C42—C43—C44119.5 (3)
O2—C8—C9120.2 (3)C42—C43—H43120.2
O1—C8—C9117.3 (3)C44—C43—H43120.2
N1—C9—C10124.0 (3)N3—C44—C43119.7 (3)
N1—C9—C8115.0 (3)N3—C44—C39120.9 (3)
C10—C9—C8121.0 (3)C43—C44—C39119.4 (3)
C11—C10—C9119.4 (3)O8—C45—O7124.1 (3)
C11—C10—H10120.3O8—C45—C46118.8 (3)
C9—C10—H10120.3O7—C45—C46117.1 (3)
C10—C11—C12119.0 (3)N4—C46—C47123.9 (3)
C10—C11—H11120.5N4—C46—C45117.4 (3)
C12—C11—H11120.5C47—C46—C45118.8 (3)
C11—C12—C17118.6 (3)C48—C47—C46119.0 (3)
C11—C12—C13123.2 (3)C48—C47—H47120.5
C17—C12—C13118.2 (3)C46—C47—H47120.5
C14—C13—C12120.7 (3)C47—C48—C49118.9 (3)
C14—C13—H13119.6C47—C48—H48120.5
C12—C13—H13119.6C49—C48—H48120.5
C13—C14—C15120.5 (3)C50—C49—C48122.3 (3)
C13—C14—H14119.8C50—C49—C54119.2 (3)
C15—C14—H14119.8C48—C49—C54118.5 (3)
C16—C15—C14121.4 (4)C51—C50—C49120.8 (4)
C16—C15—H15119.3C51—C50—H50119.6
C14—C15—H15119.3C49—C50—H50119.6
C15—C16—C17119.3 (3)C50—C51—C52119.6 (3)
C15—C16—H16120.3C50—C51—H51120.2
C17—C16—H16120.3C52—C51—H51120.2
N1—C17—C16119.5 (3)C53—C52—C51121.1 (3)
N1—C17—C12120.6 (3)C53—C52—H52119.4
C16—C17—C12119.8 (3)C51—C52—H52119.4
O4—C18—O3123.2 (3)C52—C53—C54119.8 (4)
O4—C18—C19118.9 (3)C52—C53—H53120.1
O3—C18—C19117.9 (3)C54—C53—H53120.1
N2—C19—C20123.7 (3)N4—C54—C53118.5 (3)
N2—C19—C18116.9 (3)N4—C54—C49122.1 (3)
C20—C19—C18119.4 (3)C53—C54—C49119.4 (3)
C1—Sn1—O1—C870.7 (3)Sn1—O3—C18—O4177.0 (2)
O3—Sn1—O1—C8170.2 (3)Sn1—O3—C18—C19−3.0 (4)
C2—Sn1—O1—C8−89.6 (3)C27—N2—C19—C20−4.8 (5)
N1—Sn1—O1—C8−5.7 (2)Sn1—N2—C19—C20170.8 (3)
N2—Sn1—O1—C8177.1 (2)C27—N2—C19—C18173.5 (3)
O1—Sn1—O3—C18173.7 (3)Sn1—N2—C19—C18−11.0 (3)
C1—Sn1—O3—C18−77.4 (3)O4—C18—C19—N2−169.4 (3)
C2—Sn1—O3—C1877.4 (3)O3—C18—C19—N210.6 (5)
N1—Sn1—O3—C18−179.1 (2)O4—C18—C19—C209.0 (5)
N2—Sn1—O3—C18−2.2 (3)O3—C18—C19—C20−171.0 (3)
O7—Sn2—O5—C35173.0 (3)N2—C19—C20—C211.6 (5)
C28—Sn2—O5—C3571.3 (3)C18—C19—C20—C21−176.6 (3)
C29—Sn2—O5—C35−88.6 (3)C19—C20—C21—C221.3 (5)
N3—Sn2—O5—C35−1.8 (3)C20—C21—C22—C27−0.9 (5)
N4—Sn2—O5—C35178.7 (2)C20—C21—C22—C23178.5 (4)
O5—Sn2—O7—C45170.8 (3)C21—C22—C23—C24−176.7 (3)
C28—Sn2—O7—C45−81.0 (3)C27—C22—C23—C242.7 (5)
C29—Sn2—O7—C4573.7 (3)C22—C23—C24—C25−1.2 (5)
N3—Sn2—O7—C45179.8 (2)C23—C24—C25—C260.0 (6)
N4—Sn2—O7—C45−5.6 (3)C24—C25—C26—C27−0.4 (5)
O1—Sn1—N1—C97.5 (2)C19—N2—C27—C26−173.6 (3)
C1—Sn1—N1—C9−106.9 (2)Sn1—N2—C27—C2612.2 (5)
O3—Sn1—N1—C90.1 (3)C19—N2—C27—C225.1 (5)
C2—Sn1—N1—C9107.7 (2)Sn1—N2—C27—C22−169.0 (2)
N2—Sn1—N1—C9−175.09 (19)C25—C26—C27—N2−179.3 (3)
O1—Sn1—N1—C17−178.5 (3)C25—C26—C27—C222.0 (5)
C1—Sn1—N1—C1767.1 (3)C21—C22—C27—N2−2.3 (5)
O3—Sn1—N1—C17174.1 (2)C23—C22—C27—N2178.3 (3)
C2—Sn1—N1—C17−78.3 (3)C21—C22—C27—C26176.4 (3)
N2—Sn1—N1—C17−1.1 (4)C23—C22—C27—C26−3.0 (5)
O1—Sn1—N2—C190.1 (3)O5—Sn2—C29—C3085.4 (3)
C1—Sn1—N2—C19115.3 (2)O7—Sn2—C29—C30163.6 (3)
O3—Sn1—N2—C197.2 (2)C28—Sn2—C29—C30−61.1 (4)
C2—Sn1—N2—C19−97.5 (2)N3—Sn2—C29—C3015.2 (3)
N1—Sn1—N2—C19−175.5 (2)N4—Sn2—C29—C30−129.9 (3)
O1—Sn1—N2—C27174.7 (3)O5—Sn2—C29—C34−90.1 (3)
C1—Sn1—N2—C27−70.2 (3)O7—Sn2—C29—C34−12.0 (3)
O3—Sn1—N2—C27−178.2 (3)C28—Sn2—C29—C34123.3 (3)
C2—Sn1—N2—C2777.0 (3)N3—Sn2—C29—C34−160.4 (3)
N1—Sn1—N2—C27−1.0 (4)N4—Sn2—C29—C3454.6 (3)
O5—Sn2—N3—C366.1 (2)C34—C29—C30—C31−1.0 (6)
O7—Sn2—N3—C36−3.2 (3)Sn2—C29—C30—C31−176.6 (3)
C28—Sn2—N3—C36−109.3 (2)C29—C30—C31—C320.9 (6)
C29—Sn2—N3—C36105.7 (2)C30—C31—C32—C33−0.1 (6)
N4—Sn2—N3—C36−174.48 (19)C31—C32—C33—C34−0.6 (6)
O5—Sn2—N3—C44178.0 (3)C30—C29—C34—C330.3 (5)
O7—Sn2—N3—C44168.7 (2)Sn2—C29—C34—C33176.0 (3)
C28—Sn2—N3—C4462.6 (3)C32—C33—C34—C290.5 (6)
C29—Sn2—N3—C44−82.3 (3)Sn2—O5—C35—O6178.2 (2)
N4—Sn2—N3—C44−2.6 (4)Sn2—O5—C35—C36−2.4 (4)
O5—Sn2—N4—C46−2.0 (3)C44—N3—C36—C37−2.0 (5)
O7—Sn2—N4—C464.0 (2)Sn2—N3—C36—C37171.2 (3)
C28—Sn2—N4—C46113.8 (2)C44—N3—C36—C35177.9 (3)
C29—Sn2—N4—C46−99.5 (2)Sn2—N3—C36—C35−8.9 (3)
N3—Sn2—N4—C46178.9 (2)O6—C35—C36—N3−172.1 (3)
O5—Sn2—N4—C54176.2 (3)O5—C35—C36—N38.5 (4)
O7—Sn2—N4—C54−177.8 (3)O6—C35—C36—C377.8 (5)
C28—Sn2—N4—C54−67.9 (3)O5—C35—C36—C37−171.7 (3)
C29—Sn2—N4—C5478.7 (3)N3—C36—C37—C382.2 (5)
N3—Sn2—N4—C54−2.9 (4)C35—C36—C37—C38−177.6 (3)
O1—Sn1—C2—C3−8.0 (3)C36—C37—C38—C39−0.5 (5)
C1—Sn1—C2—C3−155.3 (3)C37—C38—C39—C44−1.2 (5)
O3—Sn1—C2—C370.3 (3)C37—C38—C39—C40178.6 (3)
N1—Sn1—C2—C3−78.3 (3)C44—C39—C40—C41−3.3 (5)
N2—Sn1—C2—C3137.4 (3)C38—C39—C40—C41177.0 (3)
O1—Sn1—C2—C7170.6 (3)C39—C40—C41—C422.7 (5)
C1—Sn1—C2—C723.3 (4)C40—C41—C42—C43−1.3 (5)
O3—Sn1—C2—C7−111.1 (3)C41—C42—C43—C440.6 (5)
N1—Sn1—C2—C7100.3 (3)C36—N3—C44—C43179.3 (3)
N2—Sn1—C2—C7−44.0 (3)Sn2—N3—C44—C437.9 (4)
C7—C2—C3—C42.0 (5)C36—N3—C44—C390.1 (5)
Sn1—C2—C3—C4−179.3 (3)Sn2—N3—C44—C39−171.2 (2)
C2—C3—C4—C5−0.5 (6)C42—C43—C44—N3179.7 (3)
C3—C4—C5—C6−2.4 (6)C42—C43—C44—C39−1.2 (5)
C4—C5—C6—C73.7 (6)C40—C39—C44—N3−178.4 (3)
C5—C6—C7—C2−2.2 (6)C38—C39—C44—N31.4 (5)
C3—C2—C7—C6−0.7 (5)C40—C39—C44—C432.5 (5)
Sn1—C2—C7—C6−179.3 (3)C38—C39—C44—C43−177.7 (3)
Sn1—O1—C8—O2−177.3 (2)Sn2—O7—C45—O8−173.4 (2)
Sn1—O1—C8—C93.2 (4)Sn2—O7—C45—C466.3 (4)
C17—N1—C9—C10−2.6 (5)C54—N4—C46—C47−1.2 (5)
Sn1—N1—C9—C10172.2 (3)Sn2—N4—C46—C47177.3 (3)
C17—N1—C9—C8176.8 (3)C54—N4—C46—C45178.8 (3)
Sn1—N1—C9—C8−8.4 (3)Sn2—N4—C46—C45−2.7 (3)
O2—C8—C9—N1−174.8 (3)O8—C45—C46—N4178.5 (3)
O1—C8—C9—N14.6 (4)O7—C45—C46—N4−1.2 (5)
O2—C8—C9—C104.6 (5)O8—C45—C46—C47−1.4 (5)
O1—C8—C9—C10−175.9 (3)O7—C45—C46—C47178.9 (3)
N1—C9—C10—C111.3 (5)N4—C46—C47—C48−0.2 (5)
C8—C9—C10—C11−178.1 (3)C45—C46—C47—C48179.8 (3)
C9—C10—C11—C121.5 (5)C46—C47—C48—C491.2 (5)
C10—C11—C12—C17−2.8 (5)C47—C48—C49—C50−179.9 (3)
C10—C11—C12—C13177.2 (3)C47—C48—C49—C54−0.8 (5)
C11—C12—C13—C14177.0 (3)C48—C49—C50—C51−178.6 (3)
C17—C12—C13—C14−3.0 (5)C54—C49—C50—C512.4 (5)
C12—C13—C14—C152.0 (5)C49—C50—C51—C52−0.7 (5)
C13—C14—C15—C16−0.2 (5)C50—C51—C52—C53−0.3 (6)
C14—C15—C16—C17−0.6 (5)C51—C52—C53—C54−0.5 (6)
C9—N1—C17—C16−179.5 (3)C46—N4—C54—C53−176.7 (3)
Sn1—N1—C17—C166.8 (4)Sn2—N4—C54—C535.2 (5)
C9—N1—C17—C121.2 (5)C46—N4—C54—C491.6 (5)
Sn1—N1—C17—C12−172.4 (2)Sn2—N4—C54—C49−176.5 (2)
C15—C16—C17—N1−179.7 (3)C52—C53—C54—N4−179.3 (3)
C15—C16—C17—C12−0.4 (5)C52—C53—C54—C492.3 (5)
C11—C12—C17—N11.4 (5)C50—C49—C54—N4178.5 (3)
C13—C12—C17—N1−178.6 (3)C48—C49—C54—N4−0.6 (5)
C11—C12—C17—C16−177.8 (3)C50—C49—C54—C53−3.2 (5)
C13—C12—C17—C162.2 (5)C48—C49—C54—C53177.7 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O20.842.092.914 (4)167
O1w—H1w2···O80.841.952.777 (4)167
O2w—H2w1···O40.842.082.911 (4)171
O2w—H2w2···O6i0.842.072.898 (4)171
Symmetry codes: (i) x−1, y, z−1.
Table 1
Selected geometric parameters (Å, °) top
Sn1—O12.074 (2)Sn2—O52.072 (2)
Sn1—C12.093 (3)Sn2—O72.091 (2)
Sn1—O32.097 (2)Sn2—C282.096 (3)
Sn1—C22.121 (3)Sn2—C292.123 (3)
Sn1—N12.483 (3)Sn2—N32.548 (3)
Sn1—N22.644 (3)Sn2—N42.647 (3)
C1—Sn1—C2144.5 (1)C28—Sn2—C29144.2 (1)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O20.842.092.914 (4)167
O1w—H1w2···O80.841.952.777 (4)167
O2w—H2w1···O40.842.082.911 (4)171
O2w—H2w2···O6i0.842.072.898 (4)171
Symmetry codes: (i) x−1, y, z−1.
Acknowledgements top

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

references
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