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The crystal structure of chlorido­{[mu]-2-[(2-oxido­benzylidene)amino]­ethanolato-[kappa]4O,N,O':O'}{2-[(2-oxido­benzylidene)am­ino]­ethanolato-[kappa]3O,N,O'}tri­vinyl­ditin(IV), [Sn2(C2H3)3(C9H9NO2)2Cl], is disordered above 178 K. A doubling of the unit-cell volume is observed on cooling. The asymmetric unit at 93 K contains two ordered mol­ecules. The phase transition corresponds to an order-disorder transition of one vinyl group bound to the SnIV atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113027194/yp3047sup1.cif
Contains datablocks III-HT, III-LT, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113027194/yp3047III-HTsup2.hkl
Contains datablock III-HT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113027194/yp3047III-LTsup3.hkl
Contains datablock III-LT

CCDC references: 964524; 964525

Computing details top

For both compounds, data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(III-HT) Chlorido{µ-2-[(2-oxidobenzylidene)amino]ethan-1-olato-κ4O,N,O':O'}{2-[(2-oxidobenzylidene)amino]ethan-1-olato-κ3O,N,O'}trivinylditin(IV) top
Crystal data top
[Sn2(C2H3)3(C9H9NO2)2Cl]F(000) = 1336
Mr = 680.31Dx = 1.722 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5961 reflections
a = 12.5649 (3) Åθ = 2.6–27.3°
b = 15.9508 (4) ŵ = 2.04 mm1
c = 13.3525 (3) ÅT = 273 K
β = 101.335 (1)°Prism, pale yellow
V = 2623.91 (10) Å30.26 × 0.24 × 0.13 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6341 independent reflections
Radiation source: sealed tube4378 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
φ and ω scansθmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.620, Tmax = 0.778k = 1921
23707 measured reflectionsl = 1717
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0335P)2 + 1.1976P]
where P = (Fo2 + 2Fc2)/3
6341 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.71 e Å3
12 restraintsΔρmin = 0.60 e Å3
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.30253 (2)0.516017 (17)0.11957 (2)0.04689 (9)
O10.2873 (2)0.39519 (16)0.1888 (2)0.0522 (7)
O20.3305 (3)0.60157 (19)0.0070 (3)0.0739 (10)
N10.3438 (3)0.4264 (2)0.0118 (3)0.0519 (9)
C10.2915 (4)0.3243 (3)0.1236 (3)0.0665 (14)
H1A0.22000.31340.08280.080*
H1B0.31480.27490.16440.080*
C20.3690 (4)0.3429 (3)0.0560 (3)0.0615 (12)
H2A0.44280.34160.09500.074*
H2B0.36240.30120.00220.074*
C30.3305 (3)0.4368 (3)0.0858 (3)0.0512 (10)
H30.33570.38890.12440.061*
C40.3087 (4)0.5130 (3)0.1409 (3)0.0500 (10)
C50.3132 (4)0.5918 (3)0.0925 (4)0.0568 (11)
C60.3022 (4)0.6621 (3)0.1555 (5)0.0762 (16)
H60.30890.71510.12590.091*
C70.2819 (4)0.6556 (4)0.2600 (5)0.0800 (16)
H70.27350.70400.29950.096*
C80.2737 (4)0.5779 (4)0.3077 (4)0.0709 (14)
H80.25810.57360.37850.085*
C90.2892 (4)0.5083 (3)0.2478 (3)0.0601 (12)
H90.28680.45590.27880.072*
C100.1359 (4)0.5412 (3)0.0955 (4)0.0659 (13)
H100.09170.49740.10860.079*
C11A0.092 (2)0.6041 (14)0.0676 (16)0.092 (6)0.40
H11A0.06400.61230.00150.110*0.40
H11B0.08510.64590.11450.110*0.40
C11B0.0829 (12)0.5926 (9)0.0223 (10)0.085 (4)0.60
H11C0.06010.64510.03960.102*0.60
H11D0.06920.57540.04560.102*0.60
C120.4311 (4)0.5658 (3)0.2269 (4)0.0606 (12)
H120.45910.53430.28470.073*
C130.4739 (5)0.6393 (4)0.2161 (5)0.0883 (18)
H13A0.44720.67180.15880.106*
H13B0.53100.65900.26560.106*
Sn20.28086 (2)0.374990 (17)0.34778 (2)0.03992 (8)
Cl10.25599 (10)0.37708 (7)0.52536 (8)0.0566 (3)
O30.2459 (2)0.25149 (17)0.3247 (2)0.0548 (7)
O40.2547 (2)0.50265 (16)0.3312 (2)0.0450 (7)
N20.1008 (3)0.3760 (2)0.3038 (3)0.0506 (9)
C140.1372 (4)0.2300 (3)0.3237 (4)0.0746 (15)
H14A0.12620.22570.39340.089*
H14B0.12200.17560.29160.089*
C150.0596 (4)0.2939 (3)0.2670 (4)0.0724 (14)
H15A0.05640.28930.19400.087*
H15B0.01270.28530.28040.087*
C160.0388 (3)0.4335 (3)0.3252 (3)0.0546 (11)
H160.03490.42130.31570.066*
C170.0724 (3)0.5148 (3)0.3624 (3)0.0457 (10)
C180.1782 (3)0.5462 (3)0.3641 (3)0.0444 (9)
C190.2028 (4)0.6273 (3)0.3991 (4)0.0579 (12)
H190.27090.64970.39820.070*
C200.1266 (5)0.6749 (3)0.4352 (4)0.0713 (14)
H200.14490.72850.46000.086*
C210.0240 (5)0.6445 (3)0.4351 (4)0.0718 (15)
H210.02650.67720.45970.086*
C220.0027 (4)0.5658 (3)0.3984 (3)0.0593 (12)
H220.07230.54560.39720.071*
C230.4523 (4)0.3710 (3)0.3806 (4)0.0700 (14)
H230.49150.34160.33990.084*
C24A0.5041 (15)0.4161 (11)0.4687 (14)0.103 (6)0.45
H24A0.54960.38820.52160.124*0.45
H24B0.49240.47340.47340.124*0.45
C24B0.5121 (11)0.3584 (9)0.4588 (12)0.095 (4)0.55
H24C0.53330.40240.50420.114*0.55
H24D0.53820.30460.47530.114*0.55
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0608 (2)0.03569 (16)0.04775 (17)0.00116 (13)0.01928 (13)0.00800 (12)
O10.080 (2)0.0393 (16)0.0408 (15)0.0020 (14)0.0216 (14)0.0036 (12)
O20.125 (3)0.0411 (18)0.066 (2)0.0052 (18)0.042 (2)0.0045 (15)
N10.080 (3)0.0367 (19)0.044 (2)0.0037 (17)0.0252 (18)0.0057 (15)
C10.112 (4)0.042 (3)0.048 (3)0.001 (3)0.023 (3)0.010 (2)
C20.093 (4)0.039 (2)0.059 (3)0.013 (2)0.031 (3)0.004 (2)
C30.068 (3)0.042 (2)0.049 (2)0.002 (2)0.025 (2)0.0096 (19)
C40.056 (3)0.050 (3)0.048 (2)0.001 (2)0.020 (2)0.000 (2)
C50.069 (3)0.046 (3)0.062 (3)0.005 (2)0.029 (2)0.009 (2)
C60.092 (4)0.049 (3)0.100 (4)0.006 (3)0.050 (3)0.008 (3)
C70.078 (4)0.082 (4)0.088 (4)0.012 (3)0.035 (3)0.037 (3)
C80.060 (3)0.098 (4)0.057 (3)0.005 (3)0.016 (2)0.019 (3)
C90.062 (3)0.067 (3)0.053 (3)0.001 (2)0.015 (2)0.001 (2)
C100.063 (3)0.062 (3)0.072 (3)0.008 (3)0.011 (3)0.002 (3)
C11A0.101 (10)0.079 (9)0.091 (10)0.026 (7)0.012 (8)0.009 (8)
C11B0.100 (7)0.067 (6)0.079 (7)0.008 (5)0.005 (6)0.008 (6)
C120.056 (3)0.063 (3)0.066 (3)0.008 (2)0.020 (2)0.017 (2)
C130.079 (4)0.078 (4)0.108 (5)0.027 (3)0.018 (3)0.016 (3)
Sn20.04462 (16)0.03744 (15)0.03827 (14)0.00138 (12)0.00955 (11)0.00247 (11)
Cl10.0726 (7)0.0593 (7)0.0401 (5)0.0077 (6)0.0167 (5)0.0007 (5)
O30.070 (2)0.0382 (16)0.0558 (17)0.0031 (14)0.0124 (15)0.0050 (13)
O40.0477 (16)0.0372 (15)0.0538 (17)0.0017 (12)0.0185 (13)0.0001 (12)
N20.047 (2)0.047 (2)0.056 (2)0.0037 (17)0.0051 (16)0.0009 (16)
C140.092 (4)0.049 (3)0.078 (4)0.016 (3)0.005 (3)0.004 (3)
C150.065 (3)0.061 (3)0.085 (4)0.017 (3)0.000 (3)0.011 (3)
C160.041 (2)0.063 (3)0.058 (3)0.000 (2)0.006 (2)0.014 (2)
C170.049 (2)0.044 (2)0.048 (2)0.009 (2)0.0178 (19)0.0115 (18)
C180.053 (2)0.041 (2)0.041 (2)0.0108 (19)0.0135 (18)0.0097 (17)
C190.070 (3)0.040 (2)0.067 (3)0.006 (2)0.020 (2)0.006 (2)
C200.099 (4)0.042 (3)0.078 (4)0.017 (3)0.029 (3)0.001 (2)
C210.089 (4)0.061 (3)0.077 (3)0.037 (3)0.043 (3)0.022 (3)
C220.057 (3)0.063 (3)0.064 (3)0.017 (2)0.027 (2)0.023 (2)
C230.048 (3)0.080 (4)0.083 (4)0.016 (3)0.015 (3)0.012 (3)
C24A0.087 (11)0.112 (14)0.088 (11)0.005 (12)0.040 (8)0.008 (12)
C24B0.060 (7)0.117 (12)0.099 (10)0.005 (9)0.007 (6)0.010 (10)
Geometric parameters (Å, º) top
Sn1—C122.093 (4)C13—H13A0.9300
Sn1—C102.094 (5)C13—H13B0.9300
Sn1—O22.110 (3)Sn2—O32.029 (3)
Sn1—O12.162 (3)Sn2—O42.068 (3)
Sn1—N12.163 (3)Sn2—C232.113 (5)
O1—C11.434 (5)Sn2—N22.223 (3)
Sn2—O12.164 (3)Sn2—Cl12.4520 (10)
O2—C51.313 (5)O3—C141.405 (6)
N1—C31.291 (5)O4—C181.329 (4)
N1—C21.466 (5)N2—C161.271 (5)
C1—C21.482 (6)N2—C151.457 (5)
C1—H1A0.9700C14—C151.508 (7)
C1—H1B0.9700C14—H14A0.9700
C2—H2A0.9700C14—H14B0.9700
C2—H2B0.9700C15—H15A0.9700
C3—C41.419 (6)C15—H15B0.9700
C3—H30.9300C16—C171.424 (6)
C4—C91.403 (6)C16—H160.9300
C4—C51.409 (6)C17—C221.400 (6)
C5—C61.393 (7)C17—C181.416 (6)
C6—C71.372 (7)C18—C191.390 (6)
C6—H60.9300C19—C201.380 (6)
C7—C81.388 (8)C19—H190.9300
C7—H70.9300C20—C211.376 (7)
C8—C91.359 (7)C20—H200.9300
C8—H80.9300C21—C221.365 (7)
C9—H90.9300C21—H210.9300
C10—C11A1.17 (2)C22—H220.9300
C10—C11B1.347 (14)C23—C24B1.178 (14)
C10—H100.9300C23—C24A1.422 (16)
C11A—H11A0.9300C23—H230.9300
C11A—H11B0.9300C24A—H24A0.9300
C11B—H11C0.9300C24A—H24B0.9300
C11B—H11D0.9300C24B—H24C0.9300
C12—C131.311 (6)C24B—H24D0.9300
C12—H120.9300
C12—Sn1—C10130.24 (18)H13A—C13—H13B120.0
C12—Sn1—O291.61 (18)O3—Sn2—O4156.21 (12)
C10—Sn1—O293.90 (18)O3—Sn2—C23100.61 (17)
C12—Sn1—O199.59 (16)O4—Sn2—C23100.70 (16)
C10—Sn1—O193.84 (17)O3—Sn2—O192.55 (11)
O2—Sn1—O1157.24 (11)O4—Sn2—O177.53 (10)
C12—Sn1—N1116.88 (15)C23—Sn2—O188.56 (17)
C10—Sn1—N1112.86 (17)O3—Sn2—N277.76 (12)
O2—Sn1—N181.85 (12)O4—Sn2—N280.37 (12)
O1—Sn1—N175.42 (11)C23—Sn2—N2176.50 (18)
C1—O1—Sn1115.2 (2)O1—Sn2—N288.42 (12)
C1—O1—Sn2119.4 (2)O3—Sn2—Cl195.45 (8)
Sn1—O1—Sn2125.13 (12)O4—Sn2—Cl192.43 (8)
C5—O2—Sn1128.8 (3)C23—Sn2—Cl196.79 (16)
C3—N1—C2119.9 (3)O1—Sn2—Cl1169.39 (8)
C3—N1—Sn1125.9 (3)N2—Sn2—Cl186.48 (10)
C2—N1—Sn1113.1 (2)C14—O3—Sn2114.8 (3)
O1—C1—C2108.6 (4)C18—O4—Sn2126.1 (2)
O1—C1—H1A110.0C16—N2—C15122.1 (4)
C2—C1—H1A110.0C16—N2—Sn2125.6 (3)
O1—C1—H1B110.0C15—N2—Sn2111.0 (3)
C2—C1—H1B110.0O3—C14—C15111.8 (4)
H1A—C1—H1B108.4O3—C14—H14A109.3
N1—C2—C1108.1 (4)C15—C14—H14A109.3
N1—C2—H2A110.1O3—C14—H14B109.3
C1—C2—H2A110.1C15—C14—H14B109.3
N1—C2—H2B110.1H14A—C14—H14B107.9
C1—C2—H2B110.1N2—C15—C14106.6 (4)
H2A—C2—H2B108.4N2—C15—H15A110.4
N1—C3—C4127.3 (4)C14—C15—H15A110.4
N1—C3—H3116.3N2—C15—H15B110.4
C4—C3—H3116.3C14—C15—H15B110.4
C9—C4—C5119.9 (4)H15A—C15—H15B108.6
C9—C4—C3117.3 (4)N2—C16—C17125.7 (4)
C5—C4—C3122.7 (4)N2—C16—H16117.2
O2—C5—C6119.5 (5)C17—C16—H16117.2
O2—C5—C4123.6 (4)C22—C17—C18118.9 (4)
C6—C5—C4116.8 (4)C22—C17—C16118.4 (4)
C7—C6—C5122.0 (5)C18—C17—C16122.7 (4)
C7—C6—H6119.0O4—C18—C19118.1 (4)
C5—C6—H6119.0O4—C18—C17123.2 (4)
C6—C7—C8121.1 (5)C19—C18—C17118.7 (4)
C6—C7—H7119.4C20—C19—C18120.4 (5)
C8—C7—H7119.4C20—C19—H19119.8
C9—C8—C7118.0 (5)C18—C19—H19119.8
C9—C8—H8121.0C21—C20—C19121.3 (5)
C7—C8—H8121.0C21—C20—H20119.3
C8—C9—C4122.1 (5)C19—C20—H20119.3
C8—C9—H9119.0C22—C21—C20119.2 (4)
C4—C9—H9119.0C22—C21—H21120.4
C11A—C10—Sn1127.4 (13)C20—C21—H21120.4
C11B—C10—Sn1124.4 (8)C21—C22—C17121.5 (4)
C11A—C10—H10116.3C21—C22—H22119.2
C11B—C10—H10111.4C17—C22—H22119.2
Sn1—C10—H10116.3C24B—C23—Sn2129.5 (8)
C10—C11A—H11A120.0C24A—C23—Sn2116.0 (9)
C10—C11A—H11B120.0C24B—C23—H2396.5
H11A—C11A—H11B120.0C24A—C23—H23122.0
C10—C11B—H11C120.0Sn2—C23—H23122.0
C10—C11B—H11D120.0C23—C24A—H24A120.0
H11C—C11B—H11D120.0C23—C24A—H24B120.0
C13—C12—Sn1122.8 (4)H24A—C24A—H24B120.0
C13—C12—H12118.6C23—C24B—H24C120.0
Sn1—C12—H12118.6C23—C24B—H24D120.0
C12—C13—H13A120.0H24C—C24B—H24D120.0
C12—C13—H13B120.0
C12—Sn1—O1—C1126.3 (3)C1—O1—Sn2—O4171.5 (3)
C10—Sn1—O1—C1101.8 (3)Sn1—O1—Sn2—O414.26 (16)
O2—Sn1—O1—C17.8 (5)C1—O1—Sn2—C2387.2 (3)
N1—Sn1—O1—C110.8 (3)Sn1—O1—Sn2—C2387.0 (2)
C12—Sn1—O1—Sn248.1 (2)C1—O1—Sn2—N291.0 (3)
C10—Sn1—O1—Sn283.8 (2)Sn1—O1—Sn2—N294.75 (18)
O2—Sn1—O1—Sn2166.6 (3)C1—O1—Sn2—Cl1152.3 (4)
N1—Sn1—O1—Sn2163.6 (2)Sn1—O1—Sn2—Cl133.5 (6)
C12—Sn1—O2—C5149.6 (4)O4—Sn2—O3—C1440.6 (4)
C10—Sn1—O2—C579.9 (4)C23—Sn2—O3—C14166.2 (3)
O1—Sn1—O2—C529.7 (6)O1—Sn2—O3—C14104.8 (3)
N1—Sn1—O2—C532.6 (4)N2—Sn2—O3—C1417.0 (3)
C12—Sn1—N1—C3115.1 (4)Cl1—Sn2—O3—C1468.2 (3)
C10—Sn1—N1—C363.4 (4)O3—Sn2—O4—C1866.4 (4)
O2—Sn1—N1—C327.4 (4)C23—Sn2—O4—C18140.4 (3)
O1—Sn1—N1—C3151.4 (4)O1—Sn2—O4—C18133.5 (3)
C12—Sn1—N1—C276.9 (3)N2—Sn2—O4—C1843.0 (3)
C10—Sn1—N1—C2104.6 (3)Cl1—Sn2—O4—C1843.0 (3)
O2—Sn1—N1—C2164.6 (3)O3—Sn2—N2—C16157.5 (4)
O1—Sn1—N1—C216.6 (3)O4—Sn2—N2—C1631.9 (4)
Sn1—O1—C1—C235.5 (5)O1—Sn2—N2—C16109.5 (4)
Sn2—O1—C1—C2139.3 (3)Cl1—Sn2—N2—C1661.2 (4)
C3—N1—C2—C1128.6 (4)O3—Sn2—N2—C159.6 (3)
Sn1—N1—C2—C140.2 (5)O4—Sn2—N2—C15161.0 (3)
O1—C1—C2—N148.1 (5)O1—Sn2—N2—C1583.3 (3)
C2—N1—C3—C4178.2 (4)Cl1—Sn2—N2—C15106.0 (3)
Sn1—N1—C3—C414.5 (7)Sn2—O3—C14—C1541.0 (5)
N1—C3—C4—C9175.4 (4)C16—N2—C15—C14136.3 (5)
N1—C3—C4—C58.9 (7)Sn2—N2—C15—C1431.3 (5)
Sn1—O2—C5—C6158.7 (3)O3—C14—C15—N246.9 (6)
Sn1—O2—C5—C423.7 (7)C15—N2—C16—C17179.3 (4)
C9—C4—C5—O2179.6 (4)Sn2—N2—C16—C1713.6 (6)
C3—C4—C5—O24.7 (7)N2—C16—C17—C22169.4 (4)
C9—C4—C5—C62.7 (7)N2—C16—C17—C1810.8 (7)
C3—C4—C5—C6172.9 (4)Sn2—O4—C18—C19145.0 (3)
O2—C5—C6—C7178.6 (5)Sn2—O4—C18—C1737.0 (5)
C4—C5—C6—C73.6 (7)C22—C17—C18—O4179.6 (4)
C5—C6—C7—C81.5 (8)C16—C17—C18—O40.1 (6)
C6—C7—C8—C91.7 (8)C22—C17—C18—C191.6 (6)
C7—C8—C9—C42.5 (7)C16—C17—C18—C19178.1 (4)
C5—C4—C9—C80.3 (7)O4—C18—C19—C20179.3 (4)
C3—C4—C9—C8176.2 (4)C17—C18—C19—C202.6 (6)
C12—Sn1—C10—C11A65.9 (14)C18—C19—C20—C211.7 (7)
O2—Sn1—C10—C11A29.5 (13)C19—C20—C21—C220.1 (8)
O1—Sn1—C10—C11A171.9 (13)C20—C21—C22—C171.1 (7)
N1—Sn1—C10—C11A112.3 (13)C18—C17—C22—C210.2 (6)
C12—Sn1—C10—C11B99.8 (8)C16—C17—C22—C21180.0 (4)
O2—Sn1—C10—C11B4.3 (8)O3—Sn2—C23—C24B85.0 (11)
O1—Sn1—C10—C11B154.2 (8)O4—Sn2—C23—C24B105.7 (11)
N1—Sn1—C10—C11B78.5 (8)O1—Sn2—C23—C24B177.3 (11)
C10—Sn1—C12—C1379.3 (5)Cl1—Sn2—C23—C24B11.9 (11)
O2—Sn1—C12—C1317.2 (4)O3—Sn2—C23—C24A131.5 (10)
O1—Sn1—C12—C13177.3 (4)O4—Sn2—C23—C24A59.1 (10)
N1—Sn1—C12—C1398.9 (4)O1—Sn2—C23—C24A136.1 (10)
C1—O1—Sn2—O313.4 (3)Cl1—Sn2—C23—C24A34.7 (10)
Sn1—O1—Sn2—O3172.42 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···Cl1i0.932.863.637 (5)142
C2—H2B···O3ii0.972.673.510 (6)146
C3—H3···O3ii0.932.543.328 (5)143
Symmetry codes: (i) x, y, z1; (ii) x, y+1/2, z1/2.
(III-LT) Chlorido{µ-2-[(2-oxidobenzylidene)amino]ethan-1-olato-κ4O,N,O':O'}{2-[(2-oxidobenzylidene)amino]ethan-1-olato-κ3O,N,O'}trivinylditin(IV) top
Crystal data top
[Sn2(C2H3)3(C9H9NO2)2Cl]F(000) = 2672
Mr = 680.31Dx = 1.772 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9924 reflections
a = 13.2848 (3) Åθ = 2.5–34.8°
b = 15.7966 (4) ŵ = 2.10 mm1
c = 25.7287 (6) ÅT = 93 K
β = 109.176 (1)°Prism, pale yellow
V = 5099.7 (2) Å30.26 × 0.24 × 0.13 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
12288 independent reflections
Radiation source: fine-focus sealed tube9971 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.612, Tmax = 0.772k = 2020
46297 measured reflectionsl = 3333
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0227P)2 + 4.9213P]
where P = (Fo2 + 2Fc2)/3
12288 reflections(Δ/σ)max = 0.003
595 parametersΔρmax = 1.21 e Å3
0 restraintsΔρmin = 0.88 e Å3
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.549813 (17)0.534661 (14)0.648549 (9)0.01411 (5)
Sn20.312288 (17)0.389744 (14)0.642427 (9)0.01301 (5)
Cl10.12061 (6)0.38946 (5)0.63071 (3)0.01894 (17)
O10.47299 (17)0.41165 (14)0.64314 (9)0.0176 (5)
O20.67731 (18)0.62136 (14)0.65933 (10)0.0209 (5)
O30.31995 (18)0.26281 (14)0.63131 (9)0.0182 (5)
O40.31214 (17)0.51690 (13)0.62207 (9)0.0152 (5)
N10.6799 (2)0.44533 (17)0.67493 (11)0.0159 (6)
N20.2620 (2)0.37979 (17)0.55130 (11)0.0157 (6)
C10.5432 (3)0.3401 (2)0.65044 (14)0.0190 (7)
H1A0.55220.32470.61490.023*
H1B0.51280.29080.66390.023*
C20.6490 (3)0.3635 (2)0.69160 (14)0.0187 (7)
H2A0.64310.36760.72890.022*
H2B0.70300.32000.69220.022*
C30.7714 (3)0.4520 (2)0.66762 (13)0.0169 (7)
H30.81290.40190.67210.020*
C40.8165 (3)0.5277 (2)0.65345 (13)0.0162 (7)
C50.7704 (3)0.6088 (2)0.65215 (13)0.0173 (7)
C60.8292 (3)0.6790 (2)0.64388 (15)0.0237 (8)
H60.80210.73450.64440.028*
C70.9254 (3)0.6684 (2)0.63509 (14)0.0234 (8)
H70.96260.71670.62900.028*
C80.9691 (3)0.5881 (2)0.63499 (14)0.0225 (8)
H81.03480.58140.62820.027*
C90.9157 (3)0.5196 (2)0.64482 (14)0.0189 (7)
H90.94600.46480.64590.023*
C100.4896 (3)0.5546 (2)0.56298 (14)0.0195 (7)
H100.42410.52830.54270.023*
C110.5381 (3)0.6020 (2)0.53577 (15)0.0253 (8)
H11A0.60360.62910.55500.030*
H11B0.50720.60880.49710.030*
C120.5065 (3)0.5916 (2)0.71216 (13)0.0184 (7)
H120.45950.56220.72690.022*
C130.5422 (3)0.6666 (2)0.73220 (15)0.0273 (8)
H13A0.58920.69690.71800.033*
H13B0.52100.69040.76090.033*
C140.2649 (3)0.2343 (2)0.57758 (14)0.0222 (8)
H14A0.18790.22980.57250.027*
H14B0.29090.17720.57240.027*
C150.2808 (3)0.2946 (2)0.53447 (14)0.0217 (7)
H15A0.35410.28960.53310.026*
H15B0.22980.28130.49760.026*
C160.2026 (3)0.4327 (2)0.51718 (13)0.0179 (7)
H160.17200.41530.47990.021*
C170.1791 (3)0.5171 (2)0.53151 (13)0.0144 (7)
C180.2353 (3)0.5558 (2)0.58261 (13)0.0147 (7)
C190.2115 (3)0.6395 (2)0.59099 (14)0.0181 (7)
H190.25210.66780.62380.022*
C200.1301 (3)0.6819 (2)0.55245 (14)0.0200 (7)
H200.11400.73850.55960.024*
C210.0710 (3)0.6433 (2)0.50321 (15)0.0216 (7)
H210.01340.67230.47730.026*
C220.0974 (3)0.5629 (2)0.49285 (14)0.0188 (7)
H220.05960.53730.45860.023*
C230.3655 (3)0.4022 (2)0.72923 (14)0.0219 (8)
H230.43210.37820.75010.026*
C240.3089 (3)0.4424 (3)0.75503 (15)0.0323 (9)
H24A0.24220.46670.73470.039*
H24B0.33480.44700.79400.039*
Sn30.018842 (17)1.000517 (14)0.345004 (9)0.01500 (5)
Sn40.221667 (17)0.860189 (14)0.359981 (9)0.01325 (5)
Cl20.41239 (6)0.86687 (5)0.37278 (3)0.01977 (17)
O50.05779 (17)0.87819 (14)0.35584 (9)0.0165 (5)
O60.14574 (19)1.08758 (15)0.32863 (10)0.0224 (5)
O70.21999 (18)0.73729 (14)0.38281 (9)0.0186 (5)
O80.21394 (18)0.99057 (14)0.36727 (9)0.0174 (5)
N30.1487 (2)0.91014 (17)0.32389 (11)0.0175 (6)
N40.2651 (2)0.87111 (18)0.45077 (11)0.0168 (6)
C250.0099 (3)0.8069 (2)0.35397 (14)0.0187 (7)
H25A0.01720.79760.39060.022*
H25B0.02130.75530.34360.022*
C260.1177 (3)0.8247 (2)0.31191 (15)0.0204 (7)
H26A0.11350.82240.27420.025*
H26B0.17060.78240.31490.025*
C270.2405 (3)0.9209 (2)0.33044 (13)0.0179 (7)
H270.28390.87210.32710.021*
C280.2830 (3)0.9995 (2)0.34233 (14)0.0186 (7)
C290.2351 (3)1.0788 (2)0.33999 (13)0.0172 (7)
C300.2891 (3)1.1516 (2)0.34756 (15)0.0245 (8)
H300.26111.20580.34400.029*
C310.3822 (3)1.1459 (3)0.36011 (14)0.0267 (8)
H310.41551.19620.36660.032*
C320.4281 (3)1.0676 (2)0.36338 (14)0.0248 (8)
H320.49221.06420.37210.030*
C330.3796 (3)0.9962 (2)0.35384 (14)0.0221 (8)
H330.41160.94280.35500.026*
C340.0382 (3)1.0274 (2)0.42993 (14)0.0235 (8)
H340.09090.99100.45300.028*
C350.0059 (4)1.0907 (3)0.45281 (18)0.0461 (12)
H35A0.04671.12840.43090.055*
H35B0.03511.09920.49140.055*
C360.0268 (3)1.0489 (2)0.27989 (13)0.0190 (7)
H360.06471.01330.26300.023*
C370.0045 (3)1.1269 (2)0.26182 (15)0.0275 (8)
H37A0.03341.16330.27830.033*
H37B0.02631.14680.23230.033*
C380.2736 (3)0.7213 (2)0.43907 (14)0.0232 (8)
H38A0.35130.71860.44580.028*
H38B0.25060.66580.44920.028*
C390.2500 (3)0.7902 (2)0.47467 (14)0.0223 (8)
H39A0.17590.78510.47490.027*
H39B0.29910.78560.51300.027*
C400.3133 (3)0.9329 (2)0.48066 (14)0.0193 (7)
H400.33860.92480.51940.023*
C410.3321 (3)1.0144 (2)0.45987 (14)0.0176 (7)
C420.2834 (3)1.0388 (2)0.40405 (14)0.0171 (7)
C430.3082 (3)1.1182 (2)0.38777 (15)0.0218 (7)
H430.27551.13610.35080.026*
C440.3799 (3)1.1717 (2)0.42475 (16)0.0250 (8)
H440.39691.22490.41250.030*
C450.4273 (3)1.1480 (2)0.47958 (16)0.0258 (8)
H450.47591.18490.50480.031*
C460.4027 (3)1.0706 (2)0.49659 (14)0.0229 (8)
H460.43411.05460.53400.027*
C470.1661 (3)0.8460 (2)0.27306 (14)0.0213 (7)
H470.09140.84060.25540.026*
C480.2265 (3)0.8441 (3)0.24207 (16)0.0376 (11)
H48A0.30160.84930.25820.045*
H48B0.19530.83750.20340.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01062 (11)0.01293 (11)0.01778 (11)0.00204 (8)0.00330 (9)0.00089 (9)
Sn20.01083 (11)0.01327 (11)0.01486 (11)0.00067 (8)0.00414 (8)0.00037 (8)
Cl10.0122 (4)0.0214 (4)0.0236 (4)0.0016 (3)0.0064 (3)0.0024 (3)
O10.0088 (11)0.0176 (13)0.0262 (13)0.0011 (9)0.0055 (10)0.0004 (10)
O20.0111 (12)0.0148 (13)0.0369 (15)0.0006 (9)0.0080 (10)0.0044 (10)
O30.0179 (12)0.0144 (12)0.0216 (12)0.0017 (9)0.0057 (10)0.0014 (9)
O40.0141 (11)0.0113 (12)0.0178 (11)0.0003 (9)0.0019 (9)0.0003 (9)
N10.0112 (13)0.0132 (14)0.0224 (15)0.0018 (10)0.0042 (11)0.0015 (11)
N20.0182 (14)0.0134 (14)0.0165 (14)0.0019 (11)0.0071 (11)0.0023 (11)
C10.0155 (17)0.0138 (17)0.0296 (19)0.0019 (13)0.0102 (15)0.0001 (14)
C20.0136 (16)0.0159 (17)0.0258 (18)0.0046 (13)0.0054 (14)0.0075 (14)
C30.0122 (16)0.0158 (17)0.0197 (17)0.0021 (13)0.0012 (13)0.0016 (13)
C40.0093 (15)0.0203 (18)0.0167 (16)0.0020 (13)0.0010 (12)0.0014 (13)
C50.0128 (16)0.0175 (17)0.0196 (17)0.0003 (13)0.0025 (13)0.0027 (13)
C60.0204 (18)0.0173 (18)0.028 (2)0.0006 (14)0.0010 (15)0.0004 (15)
C70.0176 (18)0.024 (2)0.0256 (19)0.0065 (15)0.0034 (15)0.0008 (15)
C80.0145 (17)0.033 (2)0.0196 (17)0.0017 (15)0.0046 (14)0.0024 (15)
C90.0149 (17)0.0204 (19)0.0210 (17)0.0036 (13)0.0054 (14)0.0001 (14)
C100.0179 (17)0.0204 (19)0.0193 (17)0.0013 (13)0.0046 (14)0.0008 (14)
C110.034 (2)0.0179 (19)0.0228 (18)0.0016 (16)0.0081 (16)0.0019 (15)
C120.0149 (17)0.0212 (19)0.0174 (16)0.0019 (13)0.0032 (13)0.0027 (13)
C130.027 (2)0.027 (2)0.026 (2)0.0004 (16)0.0064 (16)0.0053 (16)
C140.028 (2)0.0147 (18)0.0255 (19)0.0004 (14)0.0105 (16)0.0024 (14)
C150.028 (2)0.0141 (18)0.0254 (19)0.0011 (14)0.0123 (16)0.0021 (14)
C160.0184 (17)0.0195 (18)0.0152 (16)0.0049 (14)0.0048 (13)0.0007 (13)
C170.0146 (16)0.0117 (16)0.0188 (16)0.0005 (12)0.0079 (13)0.0025 (12)
C180.0124 (15)0.0155 (17)0.0177 (16)0.0021 (12)0.0071 (13)0.0019 (12)
C190.0210 (18)0.0157 (17)0.0190 (17)0.0006 (13)0.0085 (14)0.0006 (13)
C200.0253 (19)0.0122 (17)0.0263 (19)0.0030 (14)0.0134 (15)0.0035 (14)
C210.0142 (17)0.0230 (19)0.0260 (19)0.0032 (14)0.0044 (14)0.0091 (15)
C220.0148 (17)0.0199 (19)0.0195 (17)0.0033 (13)0.0028 (14)0.0052 (14)
C230.0236 (19)0.0216 (19)0.0164 (17)0.0002 (14)0.0012 (14)0.0028 (14)
C240.030 (2)0.048 (3)0.0207 (19)0.0011 (19)0.0103 (17)0.0008 (17)
Sn30.01362 (11)0.01276 (11)0.01892 (11)0.00165 (9)0.00573 (9)0.00031 (9)
Sn40.01175 (11)0.01319 (11)0.01467 (11)0.00046 (8)0.00413 (8)0.00020 (8)
Cl20.0135 (4)0.0195 (4)0.0272 (4)0.0010 (3)0.0080 (3)0.0016 (3)
O50.0113 (11)0.0115 (12)0.0264 (13)0.0031 (9)0.0057 (10)0.0001 (9)
O60.0185 (13)0.0153 (13)0.0352 (14)0.0017 (10)0.0112 (11)0.0045 (10)
O70.0194 (12)0.0139 (12)0.0215 (12)0.0001 (9)0.0053 (10)0.0035 (10)
O80.0137 (11)0.0173 (13)0.0190 (12)0.0005 (9)0.0023 (9)0.0015 (9)
N30.0131 (14)0.0151 (15)0.0226 (15)0.0018 (11)0.0034 (12)0.0008 (11)
N40.0147 (14)0.0188 (15)0.0163 (14)0.0013 (11)0.0043 (11)0.0014 (11)
C250.0142 (16)0.0136 (17)0.0270 (19)0.0037 (13)0.0052 (14)0.0022 (14)
C260.0165 (17)0.0140 (17)0.0291 (19)0.0012 (13)0.0052 (15)0.0012 (14)
C270.0138 (16)0.0197 (18)0.0195 (17)0.0036 (13)0.0045 (13)0.0049 (14)
C280.0133 (16)0.0226 (19)0.0185 (16)0.0022 (14)0.0032 (13)0.0014 (14)
C290.0163 (17)0.0198 (18)0.0141 (16)0.0009 (13)0.0030 (13)0.0016 (13)
C300.028 (2)0.0179 (19)0.0258 (19)0.0048 (15)0.0057 (16)0.0021 (15)
C310.023 (2)0.033 (2)0.0212 (18)0.0136 (16)0.0046 (15)0.0044 (16)
C320.0173 (18)0.039 (2)0.0167 (17)0.0057 (16)0.0032 (14)0.0033 (15)
C330.0129 (17)0.032 (2)0.0196 (17)0.0003 (15)0.0032 (14)0.0012 (15)
C340.0213 (19)0.028 (2)0.0219 (18)0.0022 (15)0.0086 (15)0.0004 (15)
C350.065 (3)0.040 (3)0.027 (2)0.019 (2)0.006 (2)0.0042 (19)
C360.0172 (17)0.0210 (18)0.0171 (16)0.0023 (13)0.0032 (14)0.0020 (14)
C370.030 (2)0.025 (2)0.026 (2)0.0039 (16)0.0068 (16)0.0045 (16)
C380.0213 (18)0.023 (2)0.0253 (19)0.0003 (15)0.0078 (15)0.0069 (15)
C390.0248 (19)0.0229 (19)0.0192 (17)0.0007 (15)0.0073 (15)0.0066 (14)
C400.0145 (17)0.0256 (19)0.0156 (16)0.0049 (14)0.0021 (13)0.0007 (14)
C410.0127 (16)0.0155 (18)0.0235 (18)0.0024 (13)0.0047 (14)0.0040 (13)
C420.0105 (15)0.0183 (17)0.0232 (17)0.0028 (13)0.0063 (13)0.0035 (14)
C430.0192 (18)0.0168 (18)0.0280 (19)0.0019 (14)0.0060 (15)0.0012 (14)
C440.0194 (18)0.0142 (18)0.043 (2)0.0005 (14)0.0121 (17)0.0054 (16)
C450.0117 (17)0.024 (2)0.038 (2)0.0008 (14)0.0027 (15)0.0162 (17)
C460.0141 (17)0.029 (2)0.0218 (18)0.0027 (15)0.0003 (14)0.0098 (15)
C470.0245 (19)0.0201 (19)0.0166 (17)0.0026 (14)0.0032 (14)0.0015 (14)
C480.037 (2)0.057 (3)0.0196 (19)0.018 (2)0.0096 (18)0.0030 (19)
Geometric parameters (Å, º) top
Sn1—C102.105 (3)Sn3—C362.104 (3)
Sn1—C122.107 (3)Sn3—C342.108 (4)
Sn1—O22.124 (2)Sn3—O62.108 (2)
Sn1—N12.161 (3)Sn3—O52.159 (2)
Sn1—O12.178 (2)Sn3—N32.167 (3)
Sn2—O32.033 (2)Sn4—O72.030 (2)
Sn2—O42.076 (2)Sn4—O82.074 (2)
Sn2—C232.119 (3)Sn4—C472.124 (3)
Sn2—O12.157 (2)Sn4—O52.163 (2)
Sn2—N22.222 (3)Sn4—N42.221 (3)
Sn2—Cl12.4639 (10)Sn4—Cl22.4477 (10)
O1—C11.438 (4)O5—C251.431 (4)
O2—C51.324 (4)O6—C291.320 (4)
O3—C141.409 (4)O7—C381.410 (4)
O4—C181.330 (4)O8—C421.324 (4)
N1—C31.294 (4)N3—C271.295 (4)
N1—C21.462 (4)N3—C261.472 (4)
N2—C161.279 (4)N4—C401.277 (4)
N2—C151.460 (4)N4—C391.460 (4)
C1—C21.502 (5)C25—C261.512 (5)
C1—H1A0.9900C25—H25A0.9900
C1—H1B0.9900C25—H25B0.9900
C2—H2A0.9900C26—H26A0.9900
C2—H2B0.9900C26—H26B0.9900
C3—C41.436 (5)C27—C281.438 (5)
C3—H30.9500C27—H270.9500
C4—C91.413 (4)C28—C331.410 (5)
C4—C51.415 (5)C28—C291.414 (5)
C5—C61.413 (5)C29—C301.403 (5)
C6—C71.379 (5)C30—C311.379 (5)
C6—H60.9500C30—H300.9500
C7—C81.395 (5)C31—C321.394 (6)
C7—H70.9500C31—H310.9500
C8—C91.363 (5)C32—C331.361 (5)
C8—H80.9500C32—H320.9500
C9—H90.9500C33—H330.9500
C10—C111.327 (5)C34—C351.302 (5)
C10—H100.9500C34—H340.9500
C11—H11A0.9500C35—H35A0.9500
C11—H11B0.9500C35—H35B0.9500
C12—C131.317 (5)C36—C371.315 (5)
C12—H120.9500C36—H360.9500
C13—H13A0.9500C37—H37A0.9500
C13—H13B0.9500C37—H37B0.9500
C14—C151.528 (5)C38—C391.521 (5)
C14—H14A0.9900C38—H38A0.9900
C14—H14B0.9900C38—H38B0.9900
C15—H15A0.9900C39—H39A0.9900
C15—H15B0.9900C39—H39B0.9900
C16—C171.444 (5)C40—C411.447 (5)
C16—H160.9500C40—H400.9500
C17—C221.408 (4)C41—C461.406 (5)
C17—C181.420 (4)C41—C421.421 (5)
C18—C191.393 (5)C42—C431.396 (5)
C19—C201.377 (5)C43—C441.390 (5)
C19—H190.9500C43—H430.9500
C20—C211.393 (5)C44—C451.394 (5)
C20—H200.9500C44—H440.9500
C21—C221.367 (5)C45—C461.375 (5)
C21—H210.9500C45—H450.9500
C22—H220.9500C46—H460.9500
C23—C241.318 (5)C47—C481.304 (5)
C23—H230.9500C47—H470.9500
C24—H24A0.9500C48—H48A0.9500
C24—H24B0.9500C48—H48B0.9500
C10—Sn1—C12129.90 (13)C36—Sn3—C34130.76 (14)
C10—Sn1—O293.02 (12)C36—Sn3—O691.41 (12)
C12—Sn1—O291.88 (12)C34—Sn3—O693.85 (12)
C10—Sn1—N1114.62 (12)C36—Sn3—O5100.43 (11)
C12—Sn1—N1115.43 (12)C34—Sn3—O593.03 (12)
O2—Sn1—N181.89 (10)O6—Sn3—O5157.20 (9)
C10—Sn1—O193.31 (11)C36—Sn3—N3116.99 (12)
C12—Sn1—O1100.88 (11)C34—Sn3—N3112.23 (13)
O2—Sn1—O1156.97 (8)O6—Sn3—N382.01 (10)
N1—Sn1—O175.34 (9)O5—Sn3—N375.26 (9)
O3—Sn2—O4156.21 (9)O7—Sn4—O8156.62 (9)
O3—Sn2—C23103.03 (11)O7—Sn4—C4799.81 (11)
O4—Sn2—C2398.52 (11)O8—Sn4—C47100.95 (11)
O3—Sn2—O193.69 (9)O7—Sn4—O591.92 (9)
O4—Sn2—O176.46 (9)O8—Sn4—O578.17 (8)
C23—Sn2—O189.38 (12)C47—Sn4—O588.05 (12)
O3—Sn2—N278.07 (9)O7—Sn4—N478.10 (10)
O4—Sn2—N280.05 (9)O8—Sn4—N480.29 (10)
C23—Sn2—N2177.70 (12)C47—Sn4—N4174.74 (12)
O1—Sn2—N288.53 (10)O5—Sn4—N487.20 (10)
O3—Sn2—Cl194.50 (7)O7—Sn4—Cl296.40 (7)
O4—Sn2—Cl193.19 (7)O8—Sn4—Cl291.42 (7)
C23—Sn2—Cl195.91 (11)C47—Sn4—Cl297.62 (11)
O1—Sn2—Cl1169.00 (6)O5—Sn4—Cl2168.97 (6)
N2—Sn2—Cl185.99 (8)N4—Sn4—Cl287.44 (8)
C1—O1—Sn2118.19 (19)C25—O5—Sn3115.81 (18)
C1—O1—Sn1115.03 (18)C25—O5—Sn4120.59 (19)
Sn2—O1—Sn1125.83 (10)Sn3—O5—Sn4123.24 (10)
C5—O2—Sn1128.8 (2)C29—O6—Sn3127.3 (2)
C14—O3—Sn2114.83 (19)C38—O7—Sn4114.8 (2)
C18—O4—Sn2125.2 (2)C42—O8—Sn4126.3 (2)
C3—N1—C2118.8 (3)C27—N3—C26119.2 (3)
C3—N1—Sn1126.4 (2)C27—N3—Sn3125.9 (2)
C2—N1—Sn1113.4 (2)C26—N3—Sn3113.7 (2)
C16—N2—C15121.7 (3)C40—N4—C39121.8 (3)
C16—N2—Sn2125.6 (2)C40—N4—Sn4126.7 (2)
C15—N2—Sn2110.9 (2)C39—N4—Sn4110.5 (2)
O1—C1—C2108.3 (3)O5—C25—C26108.4 (3)
O1—C1—H1A110.0O5—C25—H25A110.0
C2—C1—H1A110.0C26—C25—H25A110.0
O1—C1—H1B110.0O5—C25—H25B110.0
C2—C1—H1B110.0C26—C25—H25B110.0
H1A—C1—H1B108.4H25A—C25—H25B108.4
N1—C2—C1107.4 (3)N3—C26—C25106.6 (3)
N1—C2—H2A110.2N3—C26—H26A110.4
C1—C2—H2A110.2C25—C26—H26A110.4
N1—C2—H2B110.2N3—C26—H26B110.4
C1—C2—H2B110.2C25—C26—H26B110.4
H2A—C2—H2B108.5H26A—C26—H26B108.6
N1—C3—C4126.5 (3)N3—C27—C28126.4 (3)
N1—C3—H3116.8N3—C27—H27116.8
C4—C3—H3116.8C28—C27—H27116.8
C9—C4—C5119.8 (3)C33—C28—C29119.7 (3)
C9—C4—C3116.9 (3)C33—C28—C27117.5 (3)
C5—C4—C3123.1 (3)C29—C28—C27122.8 (3)
O2—C5—C6119.4 (3)O6—C29—C30118.8 (3)
O2—C5—C4123.3 (3)O6—C29—C28123.5 (3)
C6—C5—C4117.2 (3)C30—C29—C28117.6 (3)
C7—C6—C5121.2 (3)C31—C30—C29121.1 (4)
C7—C6—H6119.4C31—C30—H30119.4
C5—C6—H6119.4C29—C30—H30119.4
C6—C7—C8121.3 (3)C30—C31—C32121.1 (3)
C6—C7—H7119.4C30—C31—H31119.5
C8—C7—H7119.4C32—C31—H31119.5
C9—C8—C7118.6 (3)C33—C32—C31118.8 (3)
C9—C8—H8120.7C33—C32—H32120.6
C7—C8—H8120.7C31—C32—H32120.6
C8—C9—C4121.8 (3)C32—C33—C28121.7 (4)
C8—C9—H9119.1C32—C33—H33119.2
C4—C9—H9119.1C28—C33—H33119.2
C11—C10—Sn1123.6 (3)C35—C34—Sn3124.3 (3)
C11—C10—H10118.2C35—C34—H34117.8
Sn1—C10—H10118.2Sn3—C34—H34117.8
C10—C11—H11A120.0C34—C35—H35A120.0
C10—C11—H11B120.0C34—C35—H35B120.0
H11A—C11—H11B120.0H35A—C35—H35B120.0
C13—C12—Sn1122.2 (3)C37—C36—Sn3122.1 (3)
C13—C12—H12118.9C37—C36—H36119.0
Sn1—C12—H12118.9Sn3—C36—H36119.0
C12—C13—H13A120.0C36—C37—H37A120.0
C12—C13—H13B120.0C36—C37—H37B120.0
H13A—C13—H13B120.0H37A—C37—H37B120.0
O3—C14—C15111.2 (3)O7—C38—C39110.8 (3)
O3—C14—H14A109.4O7—C38—H38A109.5
C15—C14—H14A109.4C39—C38—H38A109.5
O3—C14—H14B109.4O7—C38—H38B109.5
C15—C14—H14B109.4C39—C38—H38B109.5
H14A—C14—H14B108.0H38A—C38—H38B108.1
N2—C15—C14106.4 (3)N4—C39—C38106.8 (3)
N2—C15—H15A110.5N4—C39—H39A110.4
C14—C15—H15A110.5C38—C39—H39A110.4
N2—C15—H15B110.5N4—C39—H39B110.4
C14—C15—H15B110.5C38—C39—H39B110.4
H15A—C15—H15B108.6H39A—C39—H39B108.6
N2—C16—C17124.4 (3)N4—C40—C41124.8 (3)
N2—C16—H16117.8N4—C40—H40117.6
C17—C16—H16117.8C41—C40—H40117.6
C22—C17—C18118.8 (3)C46—C41—C42119.3 (3)
C22—C17—C16118.4 (3)C46—C41—C40118.1 (3)
C18—C17—C16122.8 (3)C42—C41—C40122.6 (3)
O4—C18—C19118.5 (3)O8—C42—C43118.7 (3)
O4—C18—C17123.1 (3)O8—C42—C41123.1 (3)
C19—C18—C17118.4 (3)C43—C42—C41118.2 (3)
C20—C19—C18121.0 (3)C44—C43—C42121.1 (3)
C20—C19—H19119.5C44—C43—H43119.4
C18—C19—H19119.5C42—C43—H43119.4
C19—C20—C21121.1 (3)C43—C44—C45120.7 (3)
C19—C20—H20119.4C43—C44—H44119.7
C21—C20—H20119.4C45—C44—H44119.7
C22—C21—C20118.7 (3)C46—C45—C44119.0 (3)
C22—C21—H21120.7C46—C45—H45120.5
C20—C21—H21120.7C44—C45—H45120.5
C21—C22—C17121.9 (3)C45—C46—C41121.6 (3)
C21—C22—H22119.1C45—C46—H46119.2
C17—C22—H22119.1C41—C46—H46119.2
C24—C23—Sn2121.9 (3)C48—C47—Sn4125.1 (3)
C24—C23—H23119.1C48—C47—H47117.4
Sn2—C23—H23119.1Sn4—C47—H47117.4
C23—C24—H24A120.0C47—C48—H48A120.0
C23—C24—H24B120.0C47—C48—H48B120.0
H24A—C24—H24B120.0H48A—C48—H48B120.0
O3—Sn2—O1—C115.4 (2)C36—Sn3—O5—C25126.1 (2)
O4—Sn2—O1—C1173.5 (2)C34—Sn3—O5—C25101.5 (2)
C23—Sn2—O1—C187.6 (2)O6—Sn3—O5—C256.0 (4)
N2—Sn2—O1—C193.4 (2)N3—Sn3—O5—C2510.7 (2)
Cl1—Sn2—O1—C1153.4 (3)C36—Sn3—O5—Sn447.00 (15)
O3—Sn2—O1—Sn1176.31 (13)C34—Sn3—O5—Sn485.41 (15)
O4—Sn2—O1—Sn118.24 (12)O6—Sn3—O5—Sn4167.16 (18)
C23—Sn2—O1—Sn180.67 (15)N3—Sn3—O5—Sn4162.39 (15)
N2—Sn2—O1—Sn198.36 (14)O7—Sn4—O5—C2516.3 (2)
Cl1—Sn2—O1—Sn138.3 (4)O8—Sn4—O5—C25175.0 (2)
C10—Sn1—O1—C1105.2 (2)C47—Sn4—O5—C2583.4 (2)
C12—Sn1—O1—C1123.1 (2)N4—Sn4—O5—C2594.3 (2)
O2—Sn1—O1—C10.5 (4)Cl2—Sn4—O5—C25155.3 (3)
N1—Sn1—O1—C19.4 (2)O7—Sn4—O5—Sn3170.85 (13)
C10—Sn1—O1—Sn286.18 (15)O8—Sn4—O5—Sn312.20 (12)
C12—Sn1—O1—Sn245.53 (16)C47—Sn4—O5—Sn389.40 (15)
O2—Sn1—O1—Sn2168.07 (18)N4—Sn4—O5—Sn392.86 (13)
N1—Sn1—O1—Sn2159.22 (15)Cl2—Sn4—O5—Sn331.9 (4)
C10—Sn1—O2—C582.3 (3)C36—Sn3—O6—C29154.0 (3)
C12—Sn1—O2—C5147.6 (3)C34—Sn3—O6—C2975.0 (3)
N1—Sn1—O2—C532.2 (3)O5—Sn3—O6—C2932.3 (4)
O1—Sn1—O2—C523.5 (4)N3—Sn3—O6—C2936.9 (3)
O4—Sn2—O3—C1440.3 (3)O8—Sn4—O7—C3840.1 (4)
C23—Sn2—O3—C14165.3 (2)C47—Sn4—O7—C38167.6 (2)
O1—Sn2—O3—C14104.4 (2)O5—Sn4—O7—C38104.1 (2)
N2—Sn2—O3—C1416.7 (2)N4—Sn4—O7—C3817.3 (2)
Cl1—Sn2—O3—C1468.2 (2)Cl2—Sn4—O7—C3868.7 (2)
O3—Sn2—O4—C1869.0 (3)O7—Sn4—O8—C4266.2 (4)
C23—Sn2—O4—C18136.2 (2)C47—Sn4—O8—C42141.6 (3)
O1—Sn2—O4—C18136.5 (2)O5—Sn4—O8—C42132.7 (3)
N2—Sn2—O4—C1845.7 (2)N4—Sn4—O8—C4243.6 (3)
Cl1—Sn2—O4—C1839.7 (2)Cl2—Sn4—O8—C4243.6 (2)
C10—Sn1—N1—C360.6 (3)C36—Sn3—N3—C27116.3 (3)
C12—Sn1—N1—C3117.2 (3)C34—Sn3—N3—C2762.2 (3)
O2—Sn1—N1—C329.0 (3)O6—Sn3—N3—C2728.8 (3)
O1—Sn1—N1—C3147.5 (3)O5—Sn3—N3—C27149.4 (3)
C10—Sn1—N1—C2105.8 (2)C36—Sn3—N3—C2676.6 (2)
C12—Sn1—N1—C276.4 (2)C34—Sn3—N3—C26105.0 (2)
O2—Sn1—N1—C2164.6 (2)O6—Sn3—N3—C26164.1 (2)
O1—Sn1—N1—C218.9 (2)O5—Sn3—N3—C2617.8 (2)
O3—Sn2—N2—C16154.2 (3)O7—Sn4—N4—C40158.8 (3)
O4—Sn2—N2—C1635.2 (3)O8—Sn4—N4—C4030.1 (3)
C23—Sn2—N2—C1687 (3)C47—Sn4—N4—C40134.2 (12)
O1—Sn2—N2—C16111.7 (3)O5—Sn4—N4—C40108.6 (3)
Cl1—Sn2—N2—C1658.7 (3)Cl2—Sn4—N4—C4061.7 (3)
O3—Sn2—N2—C1510.6 (2)O7—Sn4—N4—C3910.1 (2)
O4—Sn2—N2—C15160.0 (2)O8—Sn4—N4—C39161.0 (2)
C23—Sn2—N2—C15108 (3)C47—Sn4—N4—C3957.0 (13)
O1—Sn2—N2—C1583.5 (2)O5—Sn4—N4—C3982.5 (2)
Cl1—Sn2—N2—C15106.0 (2)Cl2—Sn4—N4—C39107.2 (2)
Sn2—O1—C1—C2135.0 (2)Sn3—O5—C25—C2635.9 (3)
Sn1—O1—C1—C234.5 (3)Sn4—O5—C25—C26137.4 (2)
C3—N1—C2—C1125.0 (3)C27—N3—C26—C25127.0 (3)
Sn1—N1—C2—C142.5 (3)Sn3—N3—C26—C2541.1 (3)
O1—C1—C2—N149.0 (3)O5—C25—C26—N348.6 (3)
C2—N1—C3—C4177.4 (3)C26—N3—C27—C28179.9 (3)
Sn1—N1—C3—C416.9 (5)Sn3—N3—C27—C2813.4 (5)
N1—C3—C4—C9177.0 (3)N3—C27—C28—C33173.3 (3)
N1—C3—C4—C58.1 (5)N3—C27—C28—C2910.1 (5)
Sn1—O2—C5—C6159.4 (2)Sn3—O6—C29—C30154.1 (2)
Sn1—O2—C5—C422.0 (5)Sn3—O6—C29—C2829.2 (4)
C9—C4—C5—O2179.3 (3)C33—C28—C29—O6178.9 (3)
C3—C4—C5—O25.8 (5)C27—C28—C29—O62.4 (5)
C9—C4—C5—C62.1 (5)C33—C28—C29—C302.1 (5)
C3—C4—C5—C6172.8 (3)C27—C28—C29—C30174.4 (3)
O2—C5—C6—C7178.6 (3)O6—C29—C30—C31179.3 (3)
C4—C5—C6—C72.7 (5)C28—C29—C30—C313.8 (5)
C5—C6—C7—C81.1 (5)C29—C30—C31—C322.8 (5)
C6—C7—C8—C91.2 (5)C30—C31—C32—C330.1 (5)
C7—C8—C9—C41.9 (5)C31—C32—C33—C281.8 (5)
C5—C4—C9—C80.2 (5)C29—C28—C33—C320.6 (5)
C3—C4—C9—C8175.3 (3)C27—C28—C33—C32177.3 (3)
C12—Sn1—C10—C11100.7 (3)C36—Sn3—C34—C3584.2 (4)
O2—Sn1—C10—C115.7 (3)O6—Sn3—C34—C3511.0 (4)
N1—Sn1—C10—C1176.8 (3)O5—Sn3—C34—C35169.3 (4)
O1—Sn1—C10—C11152.2 (3)N3—Sn3—C34—C3594.0 (4)
C10—Sn1—C12—C1380.9 (3)C34—Sn3—C36—C3771.2 (3)
O2—Sn1—C12—C1314.6 (3)O6—Sn3—C36—C3725.1 (3)
N1—Sn1—C12—C1396.6 (3)O5—Sn3—C36—C37174.5 (3)
O1—Sn1—C12—C13175.4 (3)N3—Sn3—C36—C37106.9 (3)
Sn2—O3—C14—C1540.9 (3)Sn4—O7—C38—C3941.5 (3)
C16—N2—C15—C14133.0 (3)C40—N4—C39—C38137.1 (3)
Sn2—N2—C15—C1432.4 (3)Sn4—N4—C39—C3832.4 (3)
O3—C14—C15—N247.6 (4)O7—C38—C39—N448.0 (4)
C15—N2—C16—C17178.6 (3)C39—N4—C40—C41179.3 (3)
Sn2—N2—C16—C1715.4 (5)Sn4—N4—C40—C4111.5 (5)
N2—C16—C17—C22168.2 (3)N4—C40—C41—C46168.6 (3)
N2—C16—C17—C1812.3 (5)N4—C40—C41—C4210.6 (5)
Sn2—O4—C18—C19144.7 (2)Sn4—O8—C42—C43142.1 (3)
Sn2—O4—C18—C1737.7 (4)Sn4—O8—C42—C4139.5 (4)
C22—C17—C18—O4178.6 (3)C46—C41—C42—O8178.1 (3)
C16—C17—C18—O41.9 (5)C40—C41—C42—O82.7 (5)
C22—C17—C18—C193.8 (5)C46—C41—C42—C430.3 (5)
C16—C17—C18—C19175.7 (3)C40—C41—C42—C43178.9 (3)
O4—C18—C19—C20177.5 (3)O8—C42—C43—C44179.5 (3)
C17—C18—C19—C204.8 (5)C41—C42—C43—C441.1 (5)
C18—C19—C20—C211.9 (5)C42—C43—C44—C451.5 (5)
C19—C20—C21—C222.1 (5)C43—C44—C45—C460.5 (5)
C20—C21—C22—C173.0 (5)C44—C45—C46—C410.9 (5)
C18—C17—C22—C210.0 (5)C42—C41—C46—C451.3 (5)
C16—C17—C22—C21179.5 (3)C40—C41—C46—C45177.9 (3)
O3—Sn2—C23—C24126.3 (3)O7—Sn4—C47—C4898.9 (4)
O4—Sn2—C23—C2463.8 (3)O8—Sn4—C47—C4892.0 (4)
O1—Sn2—C23—C24140.1 (3)O5—Sn4—C47—C48169.5 (4)
N2—Sn2—C23—C24115 (3)N4—Sn4—C47—C48165.0 (11)
Cl1—Sn2—C23—C2430.3 (3)Cl2—Sn4—C47—C481.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O7i0.952.573.277 (4)131
C2—H2B···O7i0.992.623.379 (4)133
C27—H27···O3ii0.952.503.345 (4)148
C26—H26B···O3ii0.992.863.720 (4)146
C33—H33···Cl2iii0.952.803.596 (4)143
C9—H9···Cl1iv0.952.753.523 (3)139
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x1, y, z; (iv) x+1, y, z.
 

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