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Acta Cryst. (2008). E64, m98    [ doi:10.1107/S1600536807064471 ]

[N-(5-Chloro-2-oxidobenzylidene)valinato-[kappa]3O,N,O']dicyclohexyltin(IV)

J.-P. Li and L.-J. Tian

Abstract top

The tin atom of the title compound, [Sn(C6H11)2(C12H12ClNO3)], adopts a distorted SnNC2O2 trigonal-bipyramidal geometry, and forms five- and six-membered chelate rings with the tridentate ligand.

Comment top

The organotin complexes with Schiff bases derived from α-amino acids continue to receives attention due to their biological activities (Beltran et al., 2003; Dakternieks et al., 1998; Tian et al., 2005, 2006, 2007). The structures of two dicyclohexyltin complexes with the Schiff base ligand, [N-(5-chloro-2-oxidophenylmethylene)isoleucinato]dicyclohexyltin (Tian et al., 2004) and [N-(3,5-dibromo-2-oxidophenylmethylene)alaninato]dicyclohexyltin (Tian et al., 2007) have been reported. As a continuation of these studies, the structure of the title compound, (I), is now described.

The coordination geometry about the tin atom in (I) is that of a distorted trigonal bipyramid with two cyclohexyl groups and the imino N1 atom occupying the equatorial positions and the axial positions being occupied by phenoxide O1 atom and a unidentate carboxylate O2 atom (Fig. 1). The bond length of Sn—O1 was shorter than that of Sn—O2 and the bond angle O1—Sn—O2 was 155.75 (12) °. The monodentate mode of coordination of carboxylate is reflected in the disparate C9—O2 and C9—O3 bond lengths of 1.282 (5) and 1.221 (6) Å, respectively. The distances of bonds around the tin atom were comparable to those observed in the dicyclohexyltin complexes mentioned above.

Related literature top

For related literature, see: Beltran et al. (2003); Dakternieks et al. (1998); Tian et al. (2004, 2005, 2006, 2007).

Experimental top

The title compound was synthesized by the reaction of dicyclohexyltin dichloride (0.71 g, 2 mmol) with potassium N-(5-chlorosalicylidene)valinate (0.59 g, 2 mmol) in the presence of Et3N (0.20 g, 2 mmol) in 40 ml me thanol. The reaction mixture was refluxed for 3 h and filtered. The yellow solid obtained, (I), by removal of solvent under reduce pressure was recrystallized from dichloromethane-petroleum ether (60–90) (1:1, V/V) and crystals of (I) were obtained from chloroform-hexane (1:1, V/V) by slow evaporation at room temperature (yield 67%, m.p. 439–440 K).

Refinement top

One cyclohexyl group (C19–C24) is disordered over two positions. The site occupancy factors were refined with sum constrained to 1, converging to 0.708 (10) for atoms C19–C24 and 0.292 (10) for atoms C19'–C24'. For the cyclohexyl rings, the carbon-carbon distance was constrained to 1.52 (1) Å and 1,3-related distance to 2.50 (2) Å. The C19 and C19' atoms were constrained to occupy the same position, and the temperature factors for each pair of atoms were set to equal. H atoms were placed at calculated positions and were included in the refinement in the riding-model approximation, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, and C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for methine H atoms.

Computing details top

Data collection: SMART (Bruker, 2002); 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The structure of (I) with displacement ellipsoids are drawn at the 30% probability level. For cyclohexyl group C19–C24, the minor disordered component has been omitted for clarity.
[N-(5-Chloro-2-oxidobenzylidene)valinato-κ3O,N,O']dicyclohexyltin(IV) top
Crystal data top
[Sn(C6H11)2(C12H12ClNO3)]F000 = 1104
Mr = 538.66Dx = 1.472 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2430 reflections
a = 9.9830 (18) Åθ = 2.6–19.8º
b = 10.7284 (19) ŵ = 1.19 mm−1
c = 22.705 (4) ÅT = 295 (2) K
β = 91.759 (3)ºPrism, yellow
V = 2430.6 (7) Å30.11 × 0.08 × 0.05 mm
Z = 4
Data collection top
Bruker SMART APEX detector
diffractometer		4754 independent reflections
Radiation source: fine-focus sealed tube3608 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
T = 295(2) Kθmax = 26.0º
φ and ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −12→12
Tmin = 0.881, Tmax = 0.943k = −13→13
17254 measured reflectionsl = −27→27
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.104  w = 1/[σ2(Fo2) + (0.0425P)2 + 0.1331P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4754 reflectionsΔρmax = 0.62 e Å−3
287 parametersΔρmin = −0.80 e Å−3
24 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Sn(C6H11)2(C12H12ClNO3)]V = 2430.6 (7) Å3
Mr = 538.66Z = 4
Monoclinic, P21/nMo Kα
a = 9.9830 (18) ŵ = 1.19 mm−1
b = 10.7284 (19) ÅT = 295 (2) K
c = 22.705 (4) Å0.11 × 0.08 × 0.05 mm
β = 91.759 (3)º
Data collection top
Bruker SMART APEX detector
diffractometer		4754 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		3608 reflections with I > 2σ(I)
Tmin = 0.881, Tmax = 0.943Rint = 0.063
17254 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04724 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.04Δρmax = 0.62 e Å−3
4754 reflectionsΔρmin = −0.80 e Å−3
287 parameters
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)
Sn11.12598 (3)0.20087 (3)0.854731 (14)0.03571 (12)
N11.1870 (3)0.3911 (3)0.83569 (15)0.0337 (8)
O11.0335 (3)0.2897 (3)0.92506 (14)0.0471 (8)
O21.2493 (3)0.1893 (3)0.77824 (14)0.0482 (8)
O31.3868 (4)0.2863 (3)0.71861 (15)0.0581 (10)
Cl10.75627 (17)0.76889 (14)0.93223 (7)0.0752 (5)
C10.9725 (5)0.3979 (4)0.9241 (2)0.0399 (11)
C20.8670 (5)0.4189 (4)0.9628 (2)0.0472 (12)
H20.84100.35480.98750.057*
C30.8021 (5)0.5305 (5)0.9648 (2)0.0512 (13)
H30.73240.54190.99050.061*
C40.8407 (5)0.6271 (4)0.9284 (2)0.0478 (13)
C50.9418 (5)0.6126 (4)0.8906 (2)0.0454 (12)
H50.96710.67880.86690.054*
C61.0087 (4)0.4973 (4)0.88714 (18)0.0342 (10)
C71.1167 (4)0.4896 (4)0.84753 (19)0.0382 (11)
H71.13920.56260.82810.046*
C81.3004 (4)0.4043 (4)0.79714 (19)0.0386 (11)
H81.28140.47320.76990.046*
C91.3146 (5)0.2848 (4)0.7611 (2)0.0407 (11)
C101.4318 (5)0.4346 (4)0.8325 (2)0.0462 (12)
H101.50420.43590.80430.055*
C111.4686 (5)0.3373 (5)0.8786 (2)0.0574 (14)
H11A1.47260.25670.86030.086*
H11B1.40220.33640.90830.086*
H11C1.55450.35710.89650.086*
C121.4268 (5)0.5636 (5)0.8605 (2)0.0634 (16)
H12A1.40410.62430.83080.095*
H12B1.51280.58330.87810.095*
H12C1.36040.56450.89020.095*
C131.2432 (4)0.0796 (4)0.9097 (2)0.0391 (11)
H131.30210.13140.93490.047*
C141.3322 (5)−0.0079 (4)0.8743 (2)0.0499 (13)
H14A1.2764−0.05750.84760.060*
H14B1.39250.04120.85100.060*
C151.4130 (6)−0.0934 (5)0.9149 (3)0.0662 (16)
H15A1.4647−0.15050.89150.079*
H15B1.4754−0.04400.93880.079*
C161.3243 (6)−0.1665 (5)0.9545 (3)0.0728 (18)
H16A1.3794−0.21630.98140.087*
H16B1.2690−0.22290.93080.087*
C171.2343 (6)−0.0816 (5)0.9898 (2)0.0666 (16)
H17A1.1739−0.13191.01250.080*
H17B1.2889−0.03231.01710.080*
C181.1540 (5)0.0037 (4)0.9497 (2)0.0502 (13)
H18A1.10190.06000.97330.060*
H18B1.0920−0.04550.92560.060*
C190.9504 (4)0.1411 (5)0.8079 (2)0.0554 (14)0.708 (10)
H19A0.97790.06740.78580.066*0.708 (10)
C200.8944 (8)0.2290 (7)0.7624 (4)0.055 (2)0.708 (10)
H20A0.96330.24790.73460.066*0.708 (10)
H20B0.87000.30620.78150.066*0.708 (10)
C210.7723 (9)0.1776 (11)0.7290 (4)0.077 (3)0.708 (10)
H21A0.73440.24220.70370.092*0.708 (10)
H21B0.79960.10910.70420.092*0.708 (10)
C220.6677 (9)0.1328 (13)0.7698 (6)0.081 (3)0.708 (10)
H22A0.59760.09100.74680.098*0.708 (10)
H22B0.62790.20430.78860.098*0.708 (10)
C230.7204 (8)0.0447 (10)0.8168 (4)0.072 (3)0.708 (10)
H23A0.7417−0.03460.79880.087*0.708 (10)
H23B0.65090.03010.84490.087*0.708 (10)
C240.8441 (8)0.0943 (10)0.8492 (4)0.071 (3)0.708 (10)
H24A0.88240.02870.87390.085*0.708 (10)
H24B0.81830.16210.87480.085*0.708 (10)
C19'0.9504 (4)0.1411 (5)0.8079 (2)0.0554 (14)0.292 (10)
H19B0.98250.11010.77020.066*0.292 (10)
C20'0.8588 (15)0.2491 (12)0.7912 (9)0.055 (2)0.292 (10)
H20C0.82890.28850.82700.066*0.292 (10)
H20D0.90960.31040.76980.066*0.292 (10)
C21'0.737 (2)0.212 (2)0.7539 (10)0.077 (3)0.292 (10)
H21C0.67690.28240.74950.092*0.292 (10)
H21D0.76490.18760.71500.092*0.292 (10)
C22'0.6640 (17)0.105 (2)0.7817 (17)0.081 (3)0.292 (10)
H22C0.62410.13320.81770.098*0.292 (10)
H22D0.59210.07710.75510.098*0.292 (10)
C23'0.7553 (19)−0.0043 (17)0.7958 (12)0.072 (3)0.292 (10)
H23C0.7850−0.04050.75930.087*0.292 (10)
H23D0.7055−0.06750.81640.087*0.292 (10)
C24'0.8766 (18)0.0332 (17)0.8333 (10)0.071 (3)0.292 (10)
H24C0.84790.05520.87240.085*0.292 (10)
H24D0.9369−0.03740.83720.085*0.292 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0373 (2)0.02864 (17)0.04125 (19)0.00125 (14)0.00194 (13)−0.00021 (15)
N10.035 (2)0.033 (2)0.034 (2)0.0053 (16)0.0086 (16)0.0009 (16)
O10.056 (2)0.0334 (18)0.053 (2)0.0095 (15)0.0164 (17)0.0055 (15)
O20.063 (2)0.0366 (19)0.046 (2)−0.0013 (16)0.0115 (17)−0.0090 (15)
O30.071 (3)0.057 (2)0.048 (2)0.0110 (19)0.0197 (19)−0.0038 (18)
Cl10.0850 (11)0.0588 (9)0.0823 (11)0.0411 (8)0.0093 (9)−0.0086 (8)
C10.043 (3)0.034 (3)0.043 (3)0.002 (2)−0.001 (2)−0.003 (2)
C20.048 (3)0.041 (3)0.053 (3)−0.003 (2)0.018 (2)−0.001 (2)
C30.045 (3)0.055 (3)0.055 (3)0.005 (2)0.012 (2)−0.015 (3)
C40.048 (3)0.042 (3)0.052 (3)0.016 (2)−0.006 (3)−0.007 (2)
C50.052 (3)0.039 (3)0.045 (3)0.007 (2)−0.002 (2)−0.002 (2)
C60.038 (3)0.031 (2)0.034 (2)0.0065 (19)0.004 (2)−0.0007 (19)
C70.043 (3)0.029 (2)0.042 (3)0.000 (2)0.001 (2)0.002 (2)
C80.043 (3)0.034 (2)0.039 (3)−0.001 (2)0.009 (2)0.005 (2)
C90.047 (3)0.040 (3)0.035 (3)0.012 (2)−0.001 (2)−0.002 (2)
C100.041 (3)0.044 (3)0.054 (3)−0.007 (2)0.011 (2)−0.005 (2)
C110.052 (3)0.056 (3)0.063 (4)−0.002 (3)−0.007 (3)0.002 (3)
C120.067 (4)0.050 (3)0.073 (4)−0.012 (3)0.003 (3)−0.009 (3)
C130.043 (3)0.027 (2)0.047 (3)0.001 (2)−0.001 (2)0.001 (2)
C140.047 (3)0.051 (3)0.052 (3)0.010 (2)0.012 (2)0.005 (2)
C150.059 (4)0.059 (4)0.082 (4)0.026 (3)0.015 (3)0.008 (3)
C160.087 (5)0.052 (3)0.079 (4)0.027 (3)0.009 (4)0.018 (3)
C170.085 (4)0.054 (3)0.062 (4)0.016 (3)0.014 (3)0.014 (3)
C180.054 (3)0.039 (3)0.058 (3)0.008 (2)0.016 (3)0.009 (2)
C190.040 (3)0.063 (3)0.063 (4)−0.007 (3)−0.006 (3)−0.006 (3)
C200.059 (5)0.072 (5)0.033 (5)−0.011 (4)−0.009 (4)0.005 (4)
C210.075 (6)0.097 (8)0.055 (7)−0.017 (5)−0.026 (5)0.011 (5)
C220.049 (4)0.109 (8)0.086 (8)−0.004 (4)−0.016 (4)0.002 (6)
C230.050 (5)0.081 (8)0.085 (8)−0.019 (5)−0.004 (5)0.006 (5)
C240.050 (5)0.086 (8)0.076 (6)−0.020 (5)−0.015 (4)0.028 (6)
C19'0.040 (3)0.063 (3)0.063 (4)−0.007 (3)−0.006 (3)−0.006 (3)
C20'0.059 (5)0.072 (5)0.033 (5)−0.011 (4)−0.009 (4)0.005 (4)
C21'0.075 (6)0.097 (8)0.055 (7)−0.017 (5)−0.026 (5)0.011 (5)
C22'0.049 (4)0.109 (8)0.086 (8)−0.004 (4)−0.016 (4)0.002 (6)
C23'0.050 (5)0.081 (8)0.085 (8)−0.019 (5)−0.004 (5)0.006 (5)
C24'0.050 (5)0.086 (8)0.076 (6)−0.020 (5)−0.015 (4)0.028 (6)
Geometric parameters (Å, °) top
Sn1—O12.098 (3)C15—H15A0.9700
Sn1—C192.122 (4)C15—H15B0.9700
Sn1—C132.128 (4)C16—C171.525 (7)
Sn1—O22.163 (3)C16—H16A0.9700
Sn1—N12.177 (4)C16—H16B0.9700
N1—C71.301 (5)C17—C181.504 (6)
N1—C81.459 (5)C17—H17A0.9700
O1—C11.311 (5)C17—H17B0.9700
O2—C91.282 (5)C18—H18A0.9700
O3—C91.221 (6)C18—H18B0.9700
Cl1—C41.742 (5)C19—C201.494 (7)
C1—C21.409 (6)C19—C241.524 (7)
C1—C61.411 (6)C19—H19A0.9800
C2—C31.363 (6)C20—C211.519 (7)
C2—H20.9300C20—H20A0.9700
C3—C41.387 (7)C20—H20B0.9700
C3—H30.9300C21—C221.496 (8)
C4—C51.354 (6)C21—H21A0.9700
C5—C61.410 (6)C21—H21B0.9700
C5—H50.9300C22—C231.509 (8)
C6—C71.428 (6)C22—H22A0.9700
C7—H70.9300C22—H22B0.9700
C8—C91.530 (6)C23—C241.515 (7)
C8—C101.552 (6)C23—H23A0.9700
C8—H80.9800C23—H23B0.9700
C10—C111.516 (7)C24—H24A0.9700
C10—C121.525 (6)C24—H24B0.9700
C10—H100.9800C20'—C21'1.515 (9)
C11—H11A0.9600C20'—H20C0.9700
C11—H11B0.9600C20'—H20D0.9700
C11—H11C0.9600C21'—C22'1.510 (10)
C12—H12A0.9600C21'—H21C0.9700
C12—H12B0.9600C21'—H21D0.9700
C12—H12C0.9600C22'—C23'1.510 (10)
C13—C181.527 (6)C22'—H22C0.9700
C13—C141.535 (6)C22'—H22D0.9700
C13—H130.9800C23'—C24'1.513 (10)
C14—C151.516 (6)C23'—H23C0.9700
C14—H14A0.9700C23'—H23D0.9700
C14—H14B0.9700C24'—H24C0.9700
C15—C161.502 (7)C24'—H24D0.9700
O1—Sn1—C1998.23 (17)H15A—C15—H15B108.0
O1—Sn1—C1394.51 (15)C15—C16—C17111.7 (5)
C19—Sn1—C13122.71 (18)C15—C16—H16A109.3
O1—Sn1—O2155.75 (12)C17—C16—H16A109.3
C19—Sn1—O293.54 (17)C15—C16—H16B109.3
C13—Sn1—O296.83 (15)C17—C16—H16B109.3
O1—Sn1—N181.80 (12)H16A—C16—H16B107.9
C19—Sn1—N1114.56 (16)C18—C17—C16110.9 (5)
C13—Sn1—N1122.50 (15)C18—C17—H17A109.5
O2—Sn1—N174.02 (12)C16—C17—H17A109.5
C7—N1—C8118.6 (4)C18—C17—H17B109.5
C7—N1—Sn1124.3 (3)C16—C17—H17B109.5
C8—N1—Sn1115.9 (3)H17A—C17—H17B108.1
C1—O1—Sn1127.2 (3)C17—C18—C13112.0 (4)
C9—O2—Sn1120.4 (3)C17—C18—H18A109.2
O1—C1—C2119.1 (4)C13—C18—H18A109.2
O1—C1—C6123.4 (4)C17—C18—H18B109.2
C2—C1—C6117.4 (4)C13—C18—H18B109.2
C3—C2—C1121.8 (5)H18A—C18—H18B107.9
C3—C2—H2119.1C20—C19—C24112.4 (5)
C1—C2—H2119.1C20—C19—Sn1116.2 (4)
C2—C3—C4119.7 (5)C24—C19—Sn1111.7 (4)
C2—C3—H3120.2C20—C19—H19A105.1
C4—C3—H3120.2C24—C19—H19A105.1
C5—C4—C3121.2 (4)Sn1—C19—H19A105.1
C5—C4—Cl1120.2 (4)C19—C20—C21113.2 (6)
C3—C4—Cl1118.6 (4)C19—C20—H20A108.9
C4—C5—C6120.0 (5)C21—C20—H20A108.9
C4—C5—H5120.0C19—C20—H20B108.9
C6—C5—H5120.0C21—C20—H20B108.9
C5—C6—C1120.0 (4)H20A—C20—H20B107.8
C5—C6—C7117.0 (4)C22—C21—C20111.8 (7)
C1—C6—C7122.9 (4)C22—C21—H21A109.2
N1—C7—C6126.9 (4)C20—C21—H21A109.2
N1—C7—H7116.6C22—C21—H21B109.2
C6—C7—H7116.6C20—C21—H21B109.2
N1—C8—C9109.1 (4)H21A—C21—H21B107.9
N1—C8—C10111.7 (4)C21—C22—C23113.9 (7)
C9—C8—C10111.2 (4)C21—C22—H22A108.8
N1—C8—H8108.3C23—C22—H22A108.8
C9—C8—H8108.3C21—C22—H22B108.8
C10—C8—H8108.3C23—C22—H22B108.8
O3—C9—O2124.6 (4)H22A—C22—H22B107.7
O3—C9—C8118.6 (4)C22—C23—C24112.7 (7)
O2—C9—C8116.8 (4)C22—C23—H23A109.1
C11—C10—C12110.4 (4)C24—C23—H23A109.1
C11—C10—C8113.4 (4)C22—C23—H23B109.1
C12—C10—C8111.6 (4)C24—C23—H23B109.1
C11—C10—H10107.1H23A—C23—H23B107.8
C12—C10—H10107.1C23—C24—C19112.9 (6)
C8—C10—H10107.1C23—C24—H24A109.0
C10—C11—H11A109.5C19—C24—H24A109.0
C10—C11—H11B109.5C23—C24—H24B109.0
H11A—C11—H11B109.5C19—C24—H24B109.0
C10—C11—H11C109.5H24A—C24—H24B107.8
H11A—C11—H11C109.5C21'—C20'—H20C108.8
H11B—C11—H11C109.5C21'—C20'—H20D108.8
C10—C12—H12A109.5H20C—C20'—H20D107.7
C10—C12—H12B109.5C22'—C21'—C20'110.9 (12)
H12A—C12—H12B109.5C22'—C21'—H21C109.5
C10—C12—H12C109.5C20'—C21'—H21C109.5
H12A—C12—H12C109.5C22'—C21'—H21D109.5
H12B—C12—H12C109.5C20'—C21'—H21D109.5
C18—C13—C14110.0 (4)H21C—C21'—H21D108.0
C18—C13—Sn1110.8 (3)C23'—C22'—C21'112.4 (14)
C14—C13—Sn1112.6 (3)C23'—C22'—H22C109.1
C18—C13—H13107.8C21'—C22'—H22C109.1
C14—C13—H13107.8C23'—C22'—H22D109.1
Sn1—C13—H13107.8C21'—C22'—H22D109.1
C15—C14—C13111.0 (4)H22C—C22'—H22D107.9
C15—C14—H14A109.4C22'—C23'—C24'112.4 (13)
C13—C14—H14A109.4C22'—C23'—H23C109.1
C15—C14—H14B109.4C24'—C23'—H23C109.1
C13—C14—H14B109.4C22'—C23'—H23D109.1
H14A—C14—H14B108.0C24'—C23'—H23D109.1
C16—C15—C14111.5 (4)H23C—C23'—H23D107.8
C16—C15—H15A109.3C23'—C24'—H24C109.1
C14—C15—H15A109.3C23'—C24'—H24D109.1
C16—C15—H15B109.3H24C—C24'—H24D107.8
C14—C15—H15B109.3
O1—Sn1—N1—C7−31.2 (3)C10—C8—C9—O3−70.2 (5)
C19—Sn1—N1—C764.1 (4)N1—C8—C9—O2−14.2 (5)
C13—Sn1—N1—C7−121.4 (3)C10—C8—C9—O2109.4 (5)
O2—Sn1—N1—C7150.7 (4)N1—C8—C10—C1158.1 (5)
O1—Sn1—N1—C8161.1 (3)C9—C8—C10—C11−64.0 (5)
C19—Sn1—N1—C8−103.5 (3)N1—C8—C10—C12−67.3 (5)
C13—Sn1—N1—C871.0 (3)C9—C8—C10—C12170.6 (4)
O2—Sn1—N1—C8−17.0 (3)O1—Sn1—C13—C1856.4 (3)
C19—Sn1—O1—C1−75.0 (4)C19—Sn1—C13—C18−46.4 (4)
C13—Sn1—O1—C1161.0 (4)O2—Sn1—C13—C18−145.1 (3)
O2—Sn1—O1—C143.2 (6)N1—Sn1—C13—C18139.5 (3)
N1—Sn1—O1—C138.8 (4)O1—Sn1—C13—C14180.0 (3)
O1—Sn1—O2—C94.6 (5)C19—Sn1—C13—C1477.2 (4)
C19—Sn1—O2—C9123.7 (4)O2—Sn1—C13—C14−21.5 (3)
C13—Sn1—O2—C9−112.7 (3)N1—Sn1—C13—C14−96.9 (3)
N1—Sn1—O2—C99.2 (3)C18—C13—C14—C15−55.4 (5)
Sn1—O1—C1—C2150.7 (3)Sn1—C13—C14—C15−179.5 (4)
Sn1—O1—C1—C6−30.9 (6)C13—C14—C15—C1656.0 (6)
O1—C1—C2—C3178.3 (4)C14—C15—C16—C17−55.6 (7)
C6—C1—C2—C3−0.2 (7)C15—C16—C17—C1854.9 (7)
C1—C2—C3—C4−0.5 (8)C16—C17—C18—C13−55.4 (6)
C2—C3—C4—C50.1 (8)C14—C13—C18—C1755.8 (6)
C2—C3—C4—Cl1−179.8 (4)Sn1—C13—C18—C17−179.1 (4)
C3—C4—C5—C60.8 (7)O1—Sn1—C19—C2090.7 (5)
Cl1—C4—C5—C6−179.2 (4)C13—Sn1—C19—C20−168.5 (5)
C4—C5—C6—C1−1.5 (7)O2—Sn1—C19—C20−68.0 (5)
C4—C5—C6—C7−178.3 (4)N1—Sn1—C19—C206.0 (6)
O1—C1—C6—C5−177.2 (4)O1—Sn1—C19—C24−40.1 (6)
C2—C1—C6—C51.2 (6)C13—Sn1—C19—C2460.7 (6)
O1—C1—C6—C7−0.6 (7)O2—Sn1—C19—C24161.2 (6)
C2—C1—C6—C7177.8 (4)N1—Sn1—C19—C24−124.8 (6)
C8—N1—C7—C6−175.4 (4)C24—C19—C20—C21−51.9 (9)
Sn1—N1—C7—C617.3 (6)Sn1—C19—C20—C21177.6 (5)
C5—C6—C7—N1−176.5 (4)C19—C20—C21—C2252.2 (11)
C1—C6—C7—N16.8 (7)C20—C21—C22—C23−51.0 (14)
C7—N1—C8—C9−146.8 (4)C21—C22—C23—C2450.0 (14)
Sn1—N1—C8—C921.6 (4)C22—C23—C24—C19−48.9 (11)
C7—N1—C8—C1089.9 (5)C20—C19—C24—C2350.3 (9)
Sn1—N1—C8—C10−101.7 (3)Sn1—C19—C24—C23−177.0 (6)
Sn1—O2—C9—O3179.7 (4)C20'—C21'—C22'—C23'−53 (3)
Sn1—O2—C9—C80.1 (5)C21'—C22'—C23'—C24'54 (3)
N1—C8—C9—O3166.2 (4)
Acknowledgements top

The authors thank the Science Foundation of Shandong Province and Qufu Normal University for supporting this work.

references
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