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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 6| June 2012| Pages m719-m720

N-(2,6-Diiso­propyl­phen­yl)-N-{3-[(2,6-diiso­propyl­phen­yl)imino]­butan-2-yl}aza­nide tri­chloridostannate(II)

aSchool of Chemical Engineering and Environment, Beijing Institue of Technology, Beijing 100081, People's Republic of China, and bSchool of Chemistry and Chemical Engineering, Central South University, Chang Sha, Hunan, 410083, People's Republic of China
*Correspondence e-mail: maxiaoli@bit.edu.cn

(Received 27 February 2012; accepted 4 April 2012; online 2 May 2012)

In the title compound, (C28H43N2)[SnCl3], two pairs of molecular species are present in the asymmetric unit. The employed α-diimine opens up, forming a highly asymmetric ammonium that has its protons at one of the N atoms [N—C= 1.264 (4) and 1.516 (4) Å]. One of the C=N double bonds was oxidized to C—N, which is consistent with the bond length of 1.516 (4) Å. Meanwhile SnIV was reduced to SnII. The (SnCl)3 anion is trigonal–pyramidal. In the crystal, mol­ecules are linked by C—H⋯Cl, N—H⋯Cl, N—H⋯N and C—H⋯N bonds. The crystal studied was twinned by pseudo-merohedry.

Related literature

For related α-diimine ligand complexes, see: Rake et al. (2001[Rake, B., Zulch, F., Ding, Y., Prust, J., Roesky, H. W., Noltemeyer, M. & Schmidt, H. G. (2001). Z. Anorg. Allg. Chem. 5, 836-840.]); Hinchliffe et al. (2007[Hinchliffe, A., Mair, F. S., McInnes, E. J., Pritchard, R. G. & Warrenb, J. E. (2007). Dalton Trans. 24, 222-233.]); Baker et al. (2008[Baker, R. J., Cameron Jones, C., Mills, D. P., Pierce, G. A. & Waugh, M. (2008). Inorg. Chim. Acta, 361, 427-435.]); Yang et al. (2010[Yang, D., Pi, C., Ding, Y. & Zheng, W. (2010). Acta Cryst. E66, m1681.]); Gao et al. (2011[Gao, J., Liu, Y. Y., Zhao, Y. X., Yang, X. J. & Sui, Y. X. (2011). Organometallics, 22, 6071-6077.]); Liu et al. (2011[Liu, Y. Y., Zhao, Y. X., Yang, X. J., Li, S. G., Gao, J., Yang, P. J., Xia, Y. N. & Wu, B. (2011). Organometallics, 6, 1599-1606.]). For similar ionic complexes, see: Hill & Hitchcock (2002[Hill, M. S. & Hitchcock, P. B. (2002). Organometallics, 21, 3258-3262.]); Nie et al. (2010[Nie, M. F., Li, M. & Li, G. X. (2010). J. Mol. Struct. 977, 45-50.]).

[Scheme 1]

Experimental

Crystal data
  • (C28H43Cl3N2)[SnCl3]

  • Mr = 632.68

  • Triclinic, [P \overline 1]

  • a = 13.373 (3) Å

  • b = 13.383 (3) Å

  • c = 18.303 (4) Å

  • α = 89.31 (3)°

  • β = 88.73 (3)°

  • γ = 73.67 (3)°

  • V = 3142.7 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.09 mm−1

  • T = 153 K

  • 0.27 × 0.19 × 0.06 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.758, Tmax = 0.938

  • 26733 measured reflections

  • 11362 independent reflections

  • 8991 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.085

  • S = 1.05

  • 11362 reflections

  • 646 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.73 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Selected geometric parameters (Å, °)

Sn1—Cl1 2.4498 (12)
Sn1—Cl2 2.4824 (13)
Sn1—Cl3 2.4959 (13)
Sn2—Cl4 2.4647 (14)
Sn2—Cl5 2.4949 (13)
Sn2—Cl6 2.5001 (12)
Cl1—Sn1—Cl2 94.54 (5)
Cl1—Sn1—Cl3 92.63 (5)
Cl2—Sn1—Cl3 91.06 (4)
Cl4—Sn2—Cl5 95.23 (5)
Cl4—Sn2—Cl6 94.23 (5)
Cl5—Sn2—Cl6 90.53 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2B⋯Cl2 0.94 (4) 2.49 (4) 3.214 (3) 133 (3)
N2—H2B⋯Cl3 0.94 (4) 2.74 (3) 3.478 (3) 136 (3)
N4—H4D⋯N3 0.93 (4) 1.97 (3) 2.560 (4) 120 (3)
N2—H2A⋯N1 0.83 (4) 1.95 (4) 2.569 (4) 131 (3)
C11—H11⋯N2 1.00 2.50 2.917 (5) 105
C14—H14⋯N2 1.00 2.44 2.948 (5) 111
C23—H23⋯N1 1.00 2.38 2.883 (4) 110
C26—H26⋯N1 1.00 2.50 2.939 (5) 106
C39—H39⋯N4 1.00 2.46 2.951 (5) 110
C42—H42⋯N4 1.00 2.50 2.897 (5) 103
C51—H51⋯N3 1.00 2.41 2.920 (5) 111
C54—H54⋯N3 1.00 2.40 2.892 (5) 110
N4—H4E⋯Cl5i 0.90 (4) 2.38 (4) 3.194 (3) 151 (3)
C31—H31⋯Cl6i 1.00 2.80 3.470 (4) 125
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Recently, complexes supported by α-diimine ligands have attracted considerable interest (Liu et al., 2011). The steric and electronic properties of such ligands can be readily modified by attaching variable substituents on the carbon and nitrogen atoms of the NCCN backbone. In addition, as redox-active ligands, they can take one or two electrons to form the mono- and dianionic species upon reduction, which makes them particularly useful in the synthesis of subvalent metal complexes. On the other hand, tin chloride complexes with lithium salt of diimine ligands have been evidenced to be a reactive species (Rake et al., 2001). Herein, we report on a novel ionic complex which was synthesized by the reaction of [C(Me)NAr]2Li with tintetrachloride in THF at room temperature.

The molecular species of the title compound, (C28H43N2)[SnCl3] is shown in Fig. 1.

Related literature top

For related α-diimine ligand complexes, see: Rake et al. (2001); Hinchliffe et al. (2007); Baker et al. (2008); Yang et al. (2010); Gao et al. (2011); Liu et al. (2011). For similar ionic complexes, see: Hill & Hitchcock (2002); Nie et al. (2010).

Experimental top

All manipulations were carried out under an argon atmosphere using standard Schlenk techniques. Hexane and THF was dried over sodium and freshly distilled prior to use. [(2,6-iPr2C6H3)-NC(Me)]2(404 mg, 1 mmol) was dissolved in THF (10 ml) with lithium powder (40 mg, 4 mmol) added. The resultant suspension was stirred at room temperature for three days to give an red suspension. Then it was filtered and the filtrate added to a solution of SnCl4 (0.12 ml, 1.0 mmol) in THF (10 ml) at 273 K over 5 min. The resultant solution was warmed to room temperature and stirred for 16 h.

Volatiles were removed in vacuo. The residue was extracted by hexane (10 ml), and the extract was placed at 275 K to give colorless crystals overnight.

Refinement top

C—H were included in the riding model approximation with C—H distances 0.95–0.98 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C)(methyl). H atoms that bond with N2 are obtained by difference Fourier method, and the X, Y, Z, Ueq take part in the minimum correction.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of (I) at the 50% probability
[Figure 2] Fig. 2. Packing diagrams showing the hydrogen bonds of (I)
N-(2,6-Diisopropylphenyl)-N-{3-[(2,6-diisopropylphenyl)imino] butan-2-yl}azanide trichloridostannate(II) top
Crystal data top
(C28H43Cl3N2)[SnCl3]Z = 4
Mr = 632.68F(000) = 1304
Triclinic, P1Dx = 1.337 Mg m3
a = 13.373 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.383 (3) ÅCell parameters from 8932 reflections
c = 18.303 (4) Åθ = 2.5–29.1°
α = 89.31 (3)°µ = 1.09 mm1
β = 88.73 (3)°T = 153 K
γ = 73.67 (3)°Platelet, colorless
V = 3142.7 (12) Å30.27 × 0.19 × 0.06 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
11362 independent reflections
Radiation source: Rotating Anode8991 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 28.5714 pixels mm-1θmax = 25.4°, θmin = 2.5°
phi and ω scansh = 1616
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
k = 1616
Tmin = 0.758, Tmax = 0.938l = 1922
26733 measured reflections
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) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0352P)2 + 0.0722P]
where P = (Fo2 + 2Fc2)/3
11362 reflections(Δ/σ)max = 0.001
646 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
(C28H43Cl3N2)[SnCl3]γ = 73.67 (3)°
Mr = 632.68V = 3142.7 (12) Å3
Triclinic, P1Z = 4
a = 13.373 (3) ÅMo Kα radiation
b = 13.383 (3) ŵ = 1.09 mm1
c = 18.303 (4) ÅT = 153 K
α = 89.31 (3)°0.27 × 0.19 × 0.06 mm
β = 88.73 (3)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
11362 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
8991 reflections with I > 2σ(I)
Tmin = 0.758, Tmax = 0.938Rint = 0.039
26733 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.73 e Å3
11362 reflectionsΔρmin = 0.40 e Å3
646 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*/Ueq
N10.2928 (2)0.3213 (2)1.01001 (14)0.0191 (6)
N20.2250 (2)0.1623 (2)1.03448 (16)0.0198 (6)
H2A0.210 (3)0.222 (3)1.0177 (19)0.024*
H2B0.243 (3)0.123 (3)0.9913 (19)0.024*
C10.4750 (3)0.2407 (3)1.0461 (2)0.0387 (10)
H1A0.51730.17581.02410.058*
H1B0.49150.24161.09800.058*
H1C0.49020.30001.02110.058*
C20.3621 (3)0.2480 (3)1.03892 (18)0.0230 (8)
C30.3257 (3)0.1591 (3)1.07200 (18)0.0222 (8)
H30.37880.09151.06120.027*
C40.3104 (3)0.1719 (3)1.15396 (19)0.0375 (10)
H4A0.25960.23901.16460.056*
H4B0.37700.16971.17620.056*
H4C0.28470.11541.17410.056*
C50.1411 (3)0.1316 (3)1.07545 (18)0.0213 (8)
C60.1508 (3)0.0269 (3)1.08659 (19)0.0236 (8)
C70.0696 (3)0.0012 (3)1.1246 (2)0.0322 (9)
H70.07330.06991.13330.039*
C80.0162 (3)0.0783 (3)1.1497 (2)0.0360 (10)
H80.07050.05991.17600.043*
C90.0232 (3)0.1805 (3)1.1367 (2)0.0343 (10)
H90.08350.23231.15330.041*
C100.0558 (3)0.2114 (3)1.09947 (19)0.0266 (8)
C110.0413 (3)0.3256 (3)1.0823 (2)0.0388 (10)
H110.11200.33611.07480.047*
C120.0136 (4)0.3970 (4)1.1434 (3)0.0712 (18)
H12A0.01770.46931.13030.107*
H12B0.02540.37801.18850.107*
H12C0.08410.39001.15070.107*
C130.0170 (4)0.3528 (4)1.0106 (3)0.0710 (16)
H13A0.08660.34291.01650.107*
H13B0.02160.30740.97170.107*
H13C0.02350.42560.99770.107*
C140.2419 (3)0.0602 (3)1.0577 (2)0.0320 (9)
H140.28940.02761.02930.038*
C150.3045 (3)0.1245 (4)1.1196 (3)0.0511 (12)
H15A0.33200.07931.15030.077*
H15B0.36240.17961.09880.077*
H15C0.25910.15581.14920.077*
C160.2034 (4)0.1287 (3)1.0058 (2)0.0520 (13)
H16A0.16110.16611.03320.078*
H16B0.26320.17900.98280.078*
H16C0.16100.08520.96800.078*
C170.3129 (3)0.4138 (3)0.98089 (19)0.0230 (8)
C180.3158 (3)0.4944 (3)1.02787 (19)0.0268 (8)
C190.3233 (3)0.5874 (3)0.9960 (2)0.0346 (10)
H190.32600.64331.02670.041*
C200.3269 (3)0.6003 (3)0.9212 (2)0.0372 (10)
H200.33060.66490.90090.045*
C210.3249 (3)0.5193 (3)0.8761 (2)0.0298 (9)
H210.32800.52840.82460.036*
C220.3186 (3)0.4243 (3)0.90450 (19)0.0243 (8)
C230.3202 (3)0.3344 (3)0.85387 (19)0.0274 (9)
H230.32190.27210.88500.033*
C240.2231 (3)0.3572 (3)0.8082 (2)0.0439 (11)
H24A0.21980.41770.77660.066*
H24B0.16130.37200.84040.066*
H24C0.22550.29670.77790.066*
C250.4176 (3)0.3077 (4)0.8056 (2)0.0496 (12)
H25A0.41750.24900.77400.074*
H25B0.47940.28850.83620.074*
H25C0.41890.36820.77530.074*
C260.3094 (3)0.4850 (3)1.1107 (2)0.0364 (10)
H260.32370.40941.12320.044*
C270.3890 (4)0.5257 (5)1.1487 (3)0.0625 (15)
H27A0.45770.49681.12540.094*
H27B0.39190.50491.20030.094*
H27C0.36930.60181.14500.094*
C280.2009 (4)0.5401 (6)1.1394 (3)0.087 (2)
H28A0.18330.61391.12570.130*
H28B0.19890.53371.19280.130*
H28C0.15040.50841.11840.130*
N30.1739 (2)0.7210 (2)0.47112 (15)0.0253 (7)
N40.3336 (2)0.7892 (2)0.45414 (16)0.0219 (7)
H4D0.264 (3)0.815 (3)0.4670 (18)0.026*
H4E0.361 (3)0.782 (3)0.499 (2)0.026*
C290.2606 (3)0.5360 (3)0.4427 (3)0.0482 (12)
H29A0.27720.51280.39220.072*
H29B0.19450.52360.45830.072*
H29C0.31630.49730.47470.072*
C300.2512 (3)0.6492 (3)0.44730 (19)0.0269 (8)
C310.3449 (3)0.6842 (3)0.41958 (19)0.0256 (8)
H310.41050.63360.43670.031*
C320.3468 (3)0.6885 (3)0.33626 (19)0.0390 (11)
H32A0.40740.71030.31910.058*
H32B0.28290.73860.31930.058*
H32C0.35120.61940.31690.058*
C330.3721 (3)0.8670 (3)0.41295 (17)0.0221 (8)
C340.2987 (3)0.9464 (3)0.37668 (19)0.0283 (9)
C350.3364 (3)1.0177 (3)0.3369 (2)0.0365 (10)
H350.28921.07350.31210.044*
C360.4414 (3)1.0083 (3)0.3332 (2)0.0400 (11)
H360.46611.05640.30440.048*
C370.5105 (3)0.9311 (3)0.3701 (2)0.0350 (10)
H370.58250.92730.36760.042*
C380.4780 (3)0.8575 (3)0.41172 (19)0.0269 (9)
C390.5576 (3)0.7762 (3)0.4546 (2)0.0306 (9)
H390.51860.73890.48700.037*
C400.6292 (3)0.6954 (3)0.4047 (2)0.0412 (11)
H40A0.68130.64600.43410.062*
H40B0.66450.73040.36950.062*
H40C0.58790.65800.37840.062*
C410.6196 (3)0.8268 (4)0.5034 (2)0.0475 (12)
H41A0.57170.88140.53250.071*
H41B0.66490.85740.47320.071*
H41C0.66240.77410.53610.071*
C420.1818 (3)0.9585 (3)0.3833 (2)0.0345 (10)
H420.17200.88750.39000.041*
C430.1376 (4)1.0223 (4)0.4515 (3)0.0597 (14)
H43A0.14831.09160.44690.089*
H43B0.17330.98700.49480.089*
H43C0.06281.02920.45640.089*
C440.1224 (4)1.0079 (5)0.3153 (3)0.0707 (17)
H44A0.15320.96730.27210.106*
H44B0.12701.07940.30950.106*
H44C0.04921.00870.32080.106*
C450.0797 (3)0.6984 (3)0.4974 (2)0.0288 (9)
C460.0697 (3)0.6795 (3)0.5714 (2)0.0318 (9)
C470.0238 (3)0.6636 (3)0.5970 (3)0.0440 (11)
H470.03230.65010.64750.053*
C480.1034 (3)0.6671 (4)0.5504 (3)0.0511 (13)
H480.16650.65580.56850.061*
C490.0918 (3)0.6870 (4)0.4773 (3)0.0507 (12)
H490.14740.68850.44550.061*
C500.0012 (3)0.7051 (3)0.4484 (2)0.0409 (11)
C510.0082 (4)0.7292 (5)0.3680 (2)0.0593 (15)
H510.07670.74450.35990.071*
C520.0079 (5)0.6372 (6)0.3193 (3)0.103 (2)
H52A0.05710.61830.32760.155*
H52B0.06720.57770.33130.155*
H52C0.01340.65680.26790.155*
C530.0770 (5)0.8262 (5)0.3458 (3)0.085 (2)
H53A0.07590.88410.37780.128*
H53B0.14500.81240.35020.128*
H53C0.06470.84470.29500.128*
C540.1554 (3)0.6767 (3)0.6251 (2)0.0370 (10)
H540.21880.67970.59610.044*
C550.1837 (4)0.5760 (4)0.6691 (3)0.0624 (16)
H55A0.20290.51660.63580.094*
H55B0.12380.57200.69960.094*
H55C0.24270.57430.70040.094*
C560.1249 (4)0.7720 (4)0.6742 (3)0.0615 (14)
H56A0.05970.77430.70050.092*
H56B0.11540.83510.64430.092*
H56C0.18010.76780.70940.092*
Sn10.31180 (2)0.04625 (2)0.801093 (14)0.03007 (8)
Cl10.31358 (9)0.13535 (8)0.82219 (5)0.0395 (3)
Cl20.15041 (7)0.11946 (8)0.87502 (5)0.0316 (2)
Cl30.42191 (8)0.04716 (8)0.90928 (5)0.0355 (2)
Sn20.56678 (2)0.31401 (2)0.305800 (14)0.03553 (9)
Cl40.38313 (10)0.31164 (10)0.30677 (7)0.0557 (3)
Cl50.62937 (8)0.15329 (8)0.38171 (5)0.0360 (2)
Cl60.54589 (8)0.42447 (8)0.41740 (6)0.0396 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0224 (16)0.0168 (15)0.0169 (15)0.0036 (13)0.0009 (12)0.0003 (11)
N20.0233 (16)0.0176 (16)0.0200 (16)0.0080 (14)0.0001 (12)0.0008 (13)
C10.027 (2)0.036 (3)0.054 (3)0.0110 (19)0.0061 (19)0.011 (2)
C20.0220 (19)0.024 (2)0.0232 (19)0.0069 (16)0.0001 (15)0.0024 (15)
C30.0228 (19)0.0189 (19)0.025 (2)0.0062 (15)0.0035 (15)0.0053 (14)
C40.049 (3)0.048 (3)0.022 (2)0.022 (2)0.0114 (18)0.0068 (18)
C50.0203 (19)0.027 (2)0.0210 (18)0.0134 (16)0.0010 (14)0.0013 (15)
C60.025 (2)0.024 (2)0.0237 (19)0.0102 (16)0.0012 (15)0.0005 (15)
C70.040 (2)0.028 (2)0.035 (2)0.0191 (19)0.0028 (18)0.0049 (17)
C80.029 (2)0.049 (3)0.036 (2)0.023 (2)0.0043 (18)0.0012 (19)
C90.025 (2)0.037 (2)0.039 (2)0.0077 (18)0.0060 (17)0.0010 (18)
C100.024 (2)0.028 (2)0.027 (2)0.0064 (17)0.0003 (16)0.0006 (16)
C110.026 (2)0.030 (2)0.059 (3)0.0067 (18)0.013 (2)0.003 (2)
C120.066 (4)0.033 (3)0.110 (5)0.010 (3)0.042 (3)0.018 (3)
C130.072 (4)0.045 (3)0.096 (4)0.017 (3)0.026 (3)0.033 (3)
C140.040 (2)0.018 (2)0.038 (2)0.0094 (18)0.0069 (18)0.0002 (16)
C150.042 (3)0.040 (3)0.062 (3)0.003 (2)0.010 (2)0.007 (2)
C160.082 (4)0.029 (3)0.044 (3)0.014 (2)0.000 (2)0.007 (2)
C170.0173 (18)0.0172 (19)0.035 (2)0.0048 (15)0.0013 (15)0.0010 (15)
C180.027 (2)0.021 (2)0.031 (2)0.0055 (16)0.0009 (16)0.0023 (16)
C190.046 (3)0.023 (2)0.037 (2)0.0133 (19)0.0020 (19)0.0032 (17)
C200.044 (3)0.020 (2)0.050 (3)0.0136 (19)0.001 (2)0.0064 (18)
C210.035 (2)0.023 (2)0.029 (2)0.0048 (17)0.0038 (17)0.0051 (16)
C220.0219 (19)0.023 (2)0.026 (2)0.0029 (16)0.0013 (15)0.0039 (15)
C230.035 (2)0.025 (2)0.022 (2)0.0091 (17)0.0017 (16)0.0022 (15)
C240.051 (3)0.028 (2)0.055 (3)0.014 (2)0.011 (2)0.005 (2)
C250.043 (3)0.052 (3)0.051 (3)0.010 (2)0.006 (2)0.021 (2)
C260.058 (3)0.022 (2)0.031 (2)0.014 (2)0.001 (2)0.0053 (17)
C270.056 (3)0.090 (4)0.043 (3)0.022 (3)0.015 (2)0.004 (3)
C280.063 (4)0.166 (7)0.032 (3)0.034 (4)0.011 (3)0.001 (3)
N30.0205 (16)0.0298 (18)0.0243 (17)0.0050 (14)0.0023 (13)0.0023 (13)
N40.0187 (16)0.0280 (18)0.0185 (16)0.0056 (14)0.0002 (13)0.0027 (13)
C290.031 (2)0.033 (3)0.078 (3)0.006 (2)0.007 (2)0.009 (2)
C300.0202 (19)0.030 (2)0.029 (2)0.0040 (17)0.0051 (15)0.0018 (16)
C310.0203 (19)0.024 (2)0.032 (2)0.0044 (16)0.0041 (15)0.0032 (16)
C320.046 (3)0.047 (3)0.026 (2)0.015 (2)0.0031 (18)0.0132 (19)
C330.026 (2)0.026 (2)0.0135 (18)0.0061 (16)0.0020 (14)0.0010 (14)
C340.029 (2)0.029 (2)0.025 (2)0.0061 (17)0.0006 (16)0.0004 (16)
C350.038 (2)0.033 (2)0.030 (2)0.0027 (19)0.0005 (18)0.0074 (18)
C360.050 (3)0.043 (3)0.032 (2)0.021 (2)0.006 (2)0.0045 (19)
C370.032 (2)0.045 (3)0.030 (2)0.016 (2)0.0067 (18)0.0014 (19)
C380.025 (2)0.033 (2)0.022 (2)0.0077 (17)0.0020 (15)0.0002 (16)
C390.020 (2)0.043 (3)0.029 (2)0.0099 (18)0.0005 (16)0.0068 (17)
C400.035 (2)0.041 (3)0.047 (3)0.009 (2)0.0041 (19)0.004 (2)
C410.038 (3)0.069 (3)0.032 (2)0.008 (2)0.0073 (19)0.008 (2)
C420.026 (2)0.037 (2)0.034 (2)0.0024 (18)0.0051 (17)0.0041 (18)
C430.043 (3)0.068 (4)0.063 (3)0.008 (3)0.019 (2)0.015 (3)
C440.036 (3)0.100 (5)0.064 (4)0.000 (3)0.015 (2)0.029 (3)
C450.021 (2)0.028 (2)0.039 (2)0.0096 (17)0.0029 (16)0.0004 (17)
C460.023 (2)0.027 (2)0.043 (2)0.0050 (17)0.0016 (17)0.0076 (17)
C470.034 (3)0.044 (3)0.052 (3)0.009 (2)0.004 (2)0.012 (2)
C480.026 (2)0.046 (3)0.084 (4)0.016 (2)0.004 (2)0.008 (3)
C490.028 (2)0.055 (3)0.072 (4)0.015 (2)0.010 (2)0.006 (3)
C500.031 (2)0.046 (3)0.047 (3)0.013 (2)0.0053 (19)0.007 (2)
C510.037 (3)0.099 (5)0.046 (3)0.024 (3)0.013 (2)0.005 (3)
C520.107 (6)0.126 (7)0.065 (4)0.012 (5)0.009 (4)0.034 (4)
C530.088 (5)0.112 (6)0.053 (4)0.024 (4)0.018 (3)0.023 (3)
C540.022 (2)0.047 (3)0.038 (2)0.0047 (19)0.0019 (17)0.0096 (19)
C550.039 (3)0.081 (4)0.058 (3)0.002 (3)0.004 (2)0.037 (3)
C560.042 (3)0.079 (4)0.058 (3)0.007 (3)0.009 (2)0.014 (3)
Sn10.03446 (16)0.02990 (16)0.02429 (15)0.00683 (12)0.00233 (11)0.00216 (11)
Cl10.0544 (7)0.0267 (5)0.0357 (6)0.0082 (5)0.0009 (5)0.0073 (4)
Cl20.0278 (5)0.0343 (6)0.0322 (5)0.0078 (4)0.0010 (4)0.0046 (4)
Cl30.0310 (5)0.0292 (5)0.0438 (6)0.0036 (4)0.0073 (4)0.0031 (4)
Sn20.0515 (2)0.02828 (16)0.02560 (15)0.00912 (14)0.00069 (12)0.00350 (11)
Cl40.0585 (8)0.0537 (8)0.0571 (7)0.0174 (6)0.0257 (6)0.0044 (6)
Cl50.0477 (6)0.0322 (6)0.0275 (5)0.0101 (5)0.0022 (4)0.0011 (4)
Cl60.0354 (6)0.0382 (6)0.0432 (6)0.0063 (5)0.0001 (5)0.0188 (5)
Geometric parameters (Å, º) top
N1—C21.264 (4)N4—C311.516 (4)
N1—C171.433 (4)N4—H4D0.93 (4)
N2—C51.484 (4)N4—H4E0.90 (4)
N2—C31.516 (4)C29—C301.486 (5)
N2—H2A0.83 (4)C29—H29A0.9800
N2—H2B0.94 (4)C29—H29B0.9800
C1—C21.494 (5)C29—H29C0.9800
C1—H1A0.9800C30—C311.531 (5)
C1—H1B0.9800C31—C321.525 (5)
C1—H1C0.9800C31—H311.0000
C2—C31.521 (5)C32—H32A0.9800
C3—C41.515 (5)C32—H32B0.9800
C3—H31.0000C32—H32C0.9800
C4—H4A0.9800C33—C381.385 (5)
C4—H4B0.9800C33—C341.400 (5)
C4—H4C0.9800C34—C351.391 (5)
C5—C61.383 (5)C34—C421.528 (5)
C5—C101.392 (5)C35—C361.374 (6)
C6—C71.398 (5)C35—H350.9500
C6—C141.519 (5)C36—C371.361 (6)
C7—C81.384 (5)C36—H360.9500
C7—H70.9500C37—C381.395 (5)
C8—C91.364 (6)C37—H370.9500
C8—H80.9500C38—C391.517 (5)
C9—C101.399 (5)C39—C411.519 (5)
C9—H90.9500C39—C401.525 (5)
C10—C111.516 (5)C39—H391.0000
C11—C121.515 (6)C40—H40A0.9800
C11—C131.529 (6)C40—H40B0.9800
C11—H111.0000C40—H40C0.9800
C12—H12A0.9800C41—H41A0.9800
C12—H12B0.9800C41—H41B0.9800
C12—H12C0.9800C41—H41C0.9800
C13—H13A0.9800C42—C431.531 (5)
C13—H13B0.9800C42—C441.532 (6)
C13—H13C0.9800C42—H421.0000
C14—C161.523 (5)C43—H43A0.9800
C14—C151.528 (6)C43—H43B0.9800
C14—H141.0000C43—H43C0.9800
C15—H15A0.9800C44—H44A0.9800
C15—H15B0.9800C44—H44B0.9800
C15—H15C0.9800C44—H44C0.9800
C16—H16A0.9800C45—C461.385 (5)
C16—H16B0.9800C45—C501.403 (5)
C16—H16C0.9800C46—C471.397 (5)
C17—C181.398 (5)C46—C541.518 (5)
C17—C221.406 (5)C47—C481.369 (6)
C18—C191.396 (5)C47—H470.9500
C18—C261.523 (5)C48—C491.375 (6)
C19—C201.379 (5)C48—H480.9500
C19—H190.9500C49—C501.393 (6)
C20—C211.378 (5)C49—H490.9500
C20—H200.9500C50—C511.514 (6)
C21—C221.391 (5)C51—C531.524 (7)
C21—H210.9500C51—C521.529 (8)
C22—C231.523 (5)C51—H511.0000
C23—C241.515 (5)C52—H52A0.9800
C23—C251.517 (5)C52—H52B0.9800
C23—H231.0000C52—H52C0.9800
C24—H24A0.9800C53—H53A0.9800
C24—H24B0.9800C53—H53B0.9800
C24—H24C0.9800C53—H53C0.9800
C25—H25A0.9800C54—C551.521 (6)
C25—H25B0.9800C54—C561.523 (6)
C25—H25C0.9800C54—H541.0000
C26—C271.511 (6)C55—H55A0.9800
C26—C281.516 (7)C55—H55B0.9800
C26—H261.0000C55—H55C0.9800
C27—H27A0.9800C56—H56A0.9800
C27—H27B0.9800C56—H56B0.9800
C27—H27C0.9800C56—H56C0.9800
C28—H28A0.9800Sn1—Cl12.4498 (12)
C28—H28B0.9800Sn1—Cl22.4824 (13)
C28—H28C0.9800Sn1—Cl32.4959 (13)
N3—C301.271 (4)Sn2—Cl42.4647 (14)
N3—C451.447 (4)Sn2—Cl52.4949 (13)
N4—C331.477 (4)Sn2—Cl62.5001 (12)
C2—N1—C17123.2 (3)C31—N4—H4D106 (2)
C5—N2—C3119.9 (3)C33—N4—H4E109 (2)
C5—N2—H2A117 (2)C31—N4—H4E111 (2)
C3—N2—H2A100 (3)H4D—N4—H4E99 (3)
C5—N2—H2B111 (2)C30—C29—H29A109.5
C3—N2—H2B107 (2)C30—C29—H29B109.5
H2A—N2—H2B101 (3)H29A—C29—H29B109.5
C2—C1—H1A109.5C30—C29—H29C109.5
C2—C1—H1B109.5H29A—C29—H29C109.5
H1A—C1—H1B109.5H29B—C29—H29C109.5
C2—C1—H1C109.5N3—C30—C29127.6 (3)
H1A—C1—H1C109.5N3—C30—C31115.7 (3)
H1B—C1—H1C109.5C29—C30—C31116.7 (3)
N1—C2—C1127.2 (3)N4—C31—C32112.9 (3)
N1—C2—C3116.3 (3)N4—C31—C30106.0 (3)
C1—C2—C3116.5 (3)C32—C31—C30110.1 (3)
C4—C3—N2111.9 (3)N4—C31—H31109.3
C4—C3—C2110.6 (3)C32—C31—H31109.3
N2—C3—C2106.0 (3)C30—C31—H31109.3
C4—C3—H3109.4C31—C32—H32A109.5
N2—C3—H3109.4C31—C32—H32B109.5
C2—C3—H3109.4H32A—C32—H32B109.5
C3—C4—H4A109.5C31—C32—H32C109.5
C3—C4—H4B109.5H32A—C32—H32C109.5
H4A—C4—H4B109.5H32B—C32—H32C109.5
C3—C4—H4C109.5C38—C33—C34123.5 (3)
H4A—C4—H4C109.5C38—C33—N4118.9 (3)
H4B—C4—H4C109.5C34—C33—N4117.6 (3)
C6—C5—C10123.9 (3)C35—C34—C33116.9 (3)
C6—C5—N2118.9 (3)C35—C34—C42121.0 (4)
C10—C5—N2117.2 (3)C33—C34—C42122.1 (3)
C5—C6—C7117.2 (3)C36—C35—C34120.7 (4)
C5—C6—C14123.9 (3)C36—C35—H35119.7
C7—C6—C14118.9 (3)C34—C35—H35119.7
C8—C7—C6120.6 (4)C37—C36—C35120.8 (4)
C8—C7—H7119.7C37—C36—H36119.6
C6—C7—H7119.7C35—C36—H36119.6
C9—C8—C7120.3 (3)C36—C37—C38121.5 (4)
C9—C8—H8119.9C36—C37—H37119.2
C7—C8—H8119.9C38—C37—H37119.2
C8—C9—C10121.9 (4)C33—C38—C37116.5 (4)
C8—C9—H9119.1C33—C38—C39124.2 (3)
C10—C9—H9119.1C37—C38—C39119.3 (3)
C5—C10—C9116.2 (3)C38—C39—C41111.1 (4)
C5—C10—C11123.9 (3)C38—C39—C40111.8 (3)
C9—C10—C11119.8 (3)C41—C39—C40111.3 (3)
C12—C11—C10113.1 (3)C38—C39—H39107.5
C12—C11—C13111.2 (4)C41—C39—H39107.5
C10—C11—C13108.9 (4)C40—C39—H39107.5
C12—C11—H11107.8C39—C40—H40A109.5
C10—C11—H11107.8C39—C40—H40B109.5
C13—C11—H11107.8H40A—C40—H40B109.5
C11—C12—H12A109.5C39—C40—H40C109.5
C11—C12—H12B109.5H40A—C40—H40C109.5
H12A—C12—H12B109.5H40B—C40—H40C109.5
C11—C12—H12C109.5C39—C41—H41A109.5
H12A—C12—H12C109.5C39—C41—H41B109.5
H12B—C12—H12C109.5H41A—C41—H41B109.5
C11—C13—H13A109.5C39—C41—H41C109.5
C11—C13—H13B109.5H41A—C41—H41C109.5
H13A—C13—H13B109.5H41B—C41—H41C109.5
C11—C13—H13C109.5C34—C42—C43109.2 (3)
H13A—C13—H13C109.5C34—C42—C44112.8 (3)
H13B—C13—H13C109.5C43—C42—C44110.7 (4)
C6—C14—C16110.2 (3)C34—C42—H42108.0
C6—C14—C15111.9 (3)C43—C42—H42108.0
C16—C14—C15111.2 (4)C44—C42—H42108.0
C6—C14—H14107.8C42—C43—H43A109.5
C16—C14—H14107.8C42—C43—H43B109.5
C15—C14—H14107.8H43A—C43—H43B109.5
C14—C15—H15A109.5C42—C43—H43C109.5
C14—C15—H15B109.5H43A—C43—H43C109.5
H15A—C15—H15B109.5H43B—C43—H43C109.5
C14—C15—H15C109.5C42—C44—H44A109.5
H15A—C15—H15C109.5C42—C44—H44B109.5
H15B—C15—H15C109.5H44A—C44—H44B109.5
C14—C16—H16A109.5C42—C44—H44C109.5
C14—C16—H16B109.5H44A—C44—H44C109.5
H16A—C16—H16B109.5H44B—C44—H44C109.5
C14—C16—H16C109.5C46—C45—C50122.5 (3)
H16A—C16—H16C109.5C46—C45—N3118.4 (3)
H16B—C16—H16C109.5C50—C45—N3118.9 (3)
C18—C17—C22121.9 (3)C45—C46—C47118.0 (4)
C18—C17—N1119.7 (3)C45—C46—C54122.6 (3)
C22—C17—N1118.0 (3)C47—C46—C54119.3 (4)
C19—C18—C17117.4 (3)C48—C47—C46120.9 (4)
C19—C18—C26119.8 (3)C48—C47—H47119.5
C17—C18—C26122.9 (3)C46—C47—H47119.5
C20—C19—C18121.8 (4)C47—C48—C49119.9 (4)
C20—C19—H19119.1C47—C48—H48120.1
C18—C19—H19119.1C49—C48—H48120.1
C21—C20—C19119.7 (4)C48—C49—C50122.1 (4)
C21—C20—H20120.1C48—C49—H49119.0
C19—C20—H20120.1C50—C49—H49119.0
C20—C21—C22121.2 (4)C49—C50—C45116.5 (4)
C20—C21—H21119.4C49—C50—C51120.8 (4)
C22—C21—H21119.4C45—C50—C51122.6 (4)
C21—C22—C17118.0 (3)C50—C51—C53111.0 (4)
C21—C22—C23120.5 (3)C50—C51—C52112.5 (5)
C17—C22—C23121.5 (3)C53—C51—C52110.7 (5)
C24—C23—C25110.8 (3)C50—C51—H51107.5
C24—C23—C22111.8 (3)C53—C51—H51107.5
C25—C23—C22110.9 (3)C52—C51—H51107.5
C24—C23—H23107.7C51—C52—H52A109.5
C25—C23—H23107.7C51—C52—H52B109.5
C22—C23—H23107.7H52A—C52—H52B109.5
C23—C24—H24A109.5C51—C52—H52C109.5
C23—C24—H24B109.5H52A—C52—H52C109.5
H24A—C24—H24B109.5H52B—C52—H52C109.5
C23—C24—H24C109.5C51—C53—H53A109.5
H24A—C24—H24C109.5C51—C53—H53B109.5
H24B—C24—H24C109.5H53A—C53—H53B109.5
C23—C25—H25A109.5C51—C53—H53C109.5
C23—C25—H25B109.5H53A—C53—H53C109.5
H25A—C25—H25B109.5H53B—C53—H53C109.5
C23—C25—H25C109.5C46—C54—C55111.6 (4)
H25A—C25—H25C109.5C46—C54—C56110.6 (3)
H25B—C25—H25C109.5C55—C54—C56111.8 (4)
C27—C26—C28109.9 (4)C46—C54—H54107.5
C27—C26—C18112.7 (3)C55—C54—H54107.5
C28—C26—C18110.9 (4)C56—C54—H54107.5
C27—C26—H26107.7C54—C55—H55A109.5
C28—C26—H26107.7C54—C55—H55B109.5
C18—C26—H26107.7H55A—C55—H55B109.5
C26—C27—H27A109.5C54—C55—H55C109.5
C26—C27—H27B109.5H55A—C55—H55C109.5
H27A—C27—H27B109.5H55B—C55—H55C109.5
C26—C27—H27C109.5C54—C56—H56A109.5
H27A—C27—H27C109.5C54—C56—H56B109.5
H27B—C27—H27C109.5H56A—C56—H56B109.5
C26—C28—H28A109.5C54—C56—H56C109.5
C26—C28—H28B109.5H56A—C56—H56C109.5
H28A—C28—H28B109.5H56B—C56—H56C109.5
C26—C28—H28C109.5Cl1—Sn1—Cl294.54 (5)
H28A—C28—H28C109.5Cl1—Sn1—Cl392.63 (5)
H28B—C28—H28C109.5Cl2—Sn1—Cl391.06 (4)
C30—N3—C45121.1 (3)Cl4—Sn2—Cl595.23 (5)
C33—N4—C31118.6 (3)Cl4—Sn2—Cl694.23 (5)
C33—N4—H4D112 (2)Cl5—Sn2—Cl690.53 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···Cl20.94 (4)2.49 (4)3.214 (3)133 (3)
N2—H2B···Cl30.94 (4)2.74 (3)3.478 (3)136 (3)
N4—H4D···N30.93 (4)1.97 (3)2.560 (4)120 (3)
N2—H2A···N10.83 (4)1.95 (4)2.569 (4)131 (3)
C11—H11···N21.002.502.917 (5)105
C14—H14···N21.002.442.948 (5)111
C23—H23···N11.002.382.883 (4)110
C26—H26···N11.002.502.939 (5)106
C39—H39···N41.002.462.951 (5)110
C42—H42···N41.002.502.897 (5)103
C51—H51···N31.002.412.920 (5)111
C54—H54···N31.002.402.892 (5)110
N4—H4E···Cl5i0.90 (4)2.38 (4)3.194 (3)151 (3)
C31—H31···Cl6i1.002.803.470 (4)125
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula(C28H43Cl3N2)[SnCl3]
Mr632.68
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)13.373 (3), 13.383 (3), 18.303 (4)
α, β, γ (°)89.31 (3), 88.73 (3), 73.67 (3)
V3)3142.7 (12)
Z4
Radiation typeMo Kα
µ (mm1)1.09
Crystal size (mm)0.27 × 0.19 × 0.06
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2007)
Tmin, Tmax0.758, 0.938
No. of measured, independent and
observed [I > 2σ(I)] reflections
26733, 11362, 8991
Rint0.039
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.085, 1.05
No. of reflections11362
No. of parameters646
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.73, 0.40

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Sn1—Cl12.4498 (12)Sn2—Cl42.4647 (14)
Sn1—Cl22.4824 (13)Sn2—Cl52.4949 (13)
Sn1—Cl32.4959 (13)Sn2—Cl62.5001 (12)
Cl1—Sn1—Cl294.54 (5)Cl4—Sn2—Cl595.23 (5)
Cl1—Sn1—Cl392.63 (5)Cl4—Sn2—Cl694.23 (5)
Cl2—Sn1—Cl391.06 (4)Cl5—Sn2—Cl690.53 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···Cl20.94 (4)2.49 (4)3.214 (3)133 (3)
N2—H2B···Cl30.94 (4)2.74 (3)3.478 (3)136 (3)
N4—H4D···N30.93 (4)1.97 (3)2.560 (4)120 (3)
N2—H2A···N10.83 (4)1.95 (4)2.569 (4)131 (3)
C11—H11···N21.002.502.917 (5)104.5
C14—H14···N21.002.442.948 (5)110.5
C23—H23···N11.002.382.883 (4)110.1
C26—H26···N11.002.502.939 (5)106.4
C39—H39···N41.002.462.951 (5)109.7
C42—H42···N41.002.502.897 (5)103.1
C51—H51···N31.002.412.920 (5)111.0
C54—H54···N31.002.402.892 (5)109.8
N4—H4E···Cl5i0.90 (4)2.38 (4)3.194 (3)151 (3)
C31—H31···Cl6i1.002.803.470 (4)124.9
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21001016, 20901009 and 20902112) and the Program of NCET-10–0050.

References

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Volume 68| Part 6| June 2012| Pages m719-m720
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